data_ras1305
_audit_creation_date "13-08-21"
_audit_creation_method CRYSTALS_ver_14.40
_audit_update_record
;
2013-08-21 - Report on C19 H16 Cu N4 O3
by Anthony C. Willis
for Rasoul Vafazadeh
2013-08-21 - passes checkcif tests with minor warnings
;
_oxford_structure_analysis_title 'transform axes for std sp gp'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 19.8983(10)
_cell_length_b 8.4055(3)
_cell_length_c 20.8417(10)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 3485.9(3)
_symmetry_cell_setting 'orthorhombic'
_symmetry_space_group_name_H-M 'P b c a '
_symmetry_space_group_name_Hall '-P 2ac 2ab '
loop_
_symmetry_equiv_pos_as_xyz
'x,y,z'
'-x,-y,-z'
'-x+1/2,y+1/2,z'
'x+1/2,-y+1/2,-z'
'x,-y+1/2,z+1/2'
'-x,y+1/2,-z+1/2'
'-x+1/2,-y,z+1/2'
'x+1/2,y,-z+1/2'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687
0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424
0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966
1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975
1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239
0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 8
# Given Formula = C19 H16 Cu1 N4 O3
# Dc = 1.57 Fooo = 1688.00 Mu = 12.82 M = 411.91
# Found Formula = C19 H16 Cu1 N4 O3
# Dc = 1.57 FOOO = 1688.00 Mu = 12.82 M = 411.91
_chemical_formula_sum 'C19 H16 Cu N4 O3'
_chemical_formula_moiety 'C19 H16 Cu N4 O3'
_chemical_compound_source ' Yazd University '
_chemical_formula_weight 411.91
_cell_measurement_reflns_used 60581
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 25
_cell_measurement_temperature 200
_exptl_crystal_description 'needle'
_exptl_crystal_colour 'green'
_exptl_crystal_size_min 0.010
_exptl_crystal_size_mid 0.040
_exptl_crystal_size_max 0.540
_exptl_crystal_density_diffrn 1.570
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 1688
_exptl_absorpt_coefficient_mu 1.282
# Sheldrick geometric approximatio 0.95 0.99
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.67 # 0.99*9.49/14.06 scalepack ; 0.95
_exptl_absorpt_correction_T_max 0.99
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_device 'Area'
_diffrn_radiation_monochromator 'graphite'
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method ' \f and \w scans with CCD '
_diffrn_special_details
;
CCD data collecting conditions-
phi and omega scans of width 0.8 deg at rate 88 sec/frame,
crystal-detector distance 40mm,
multiple scan sets so over 95 percent of data collected with 4-fold
redundancy or more.
;
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'COLLECT (Nonius, 2001).'
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics
;
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 200
_diffrn_reflns_number 33860
_reflns_number_total 3058
_diffrn_reflns_av_R_equivalents 0.144 # scalepack
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 3058
# Theoretical number of reflections is about 6147
_diffrn_reflns_theta_min 2.806
_diffrn_reflns_theta_max 25.010
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.010
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_h_max 23
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 24
_reflns_limit_h_min 0
_reflns_limit_h_max 23
_reflns_limit_k_min 0
_reflns_limit_k_max 10
_reflns_limit_l_min 0
_reflns_limit_l_max 24
_oxford_diffrn_Wilson_B_factor 2.27
_oxford_diffrn_Wilson_scale 128.26
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -1.48
_refine_diff_density_max 1.39
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 3058
_refine_ls_number_restraints 0
_refine_ls_number_parameters 244
_oxford_refine_ls_R_factor_ref 0.1523
_refine_ls_wR_factor_ref 0.1195
_refine_ls_goodness_of_fit_ref 0.9703
_refine_ls_shift/su_max 0.0003297
_refine_ls_shift/su_mean 0.0000229
# The values computed with all filters except I/sigma
_oxford_reflns_number_all 3058
_refine_ls_R_factor_all 0.1523
_refine_ls_wR_factor_all 0.1195
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 1540
_refine_ls_R_factor_gt 0.0554
_refine_ls_wR_factor_gt 0.0901
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration '.'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 9.61P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# 1. SUBMISSION DETAILS
_publ_requested_journal ' test '
_publ_requested_category fm
_publ_contact_author_name ' Anthony C. Willis '
_publ_contact_author_address
;
Research School of Chemistry,
Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_letter
;
ENTER TEXT OF LETTER
;
_publ_requested_coeditor_name ?
_publ_contact_author_phone ' 61 2 6125 4109 '
_publ_contact_author_fax ' 61 2 6125 0750 '
_publ_contact_author_email ' willis@rsc.anu.edu.au '
#=============================================================================
# 2. PROCESSING SUMMARY (IUCr Office Use Only)
_journal_date_recd_electronic ?
_journal_date_to_coeditor ?
_journal_date_from_coeditor ?
_journal_date_accepted ?
_journal_date_printers_first ?
_journal_date_printers_final ?
_journal_date_proofs_out ?
_journal_date_proofs_in ?
_journal_coeditor_name ?
_journal_coeditor_code ?
_journal_coeditor_notes
;
?
;
_journal_techeditor_code ?
_journal_techeditor_notes
;
?
;
_journal_coden_ASTM ?
_journal_name_full ?
_journal_year ?
_journal_volume ?
_journal_issue ?
_journal_page_first ?
_journal_page_last ?
_journal_suppl_publ_number ?
_journal_suppl_publ_pages ?
#=============================================================================
# 3. TITLE AND AUTHOR LIST
_publ_section_title
;
Crystal structure of
[Cu(C~19~H~16~N~4~O~3~)]
--- ras1305
;
# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.
loop_
_publ_author_name
_publ_author_address
'N. Hasanzadeh '
;
Department of Chemistry,
Yazd University,
Yazd, Iran
;
'Rasoul Vafazadeh '
;
Department of Chemistry,
Yazd University,
Yazd, Iran
;
' Anthony C. Willis '
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
#==============================================================================
# 4. TEXT
_publ_section_abstract #Text of the abstract
;
The crystal structure of
[Cu(C~19~H~16~N~4~O~3~)]
is reported.
;
_publ_section_comment #Text of the paper
;
The crystallographic asymmetric unit consists of one
[Cu(C~19~H~16~N~4~O~3~)] molecule.
;
_publ_section_acknowledgements # Acknowledgments
;
;
_publ_section_figure_captions #Captions to figures
;
?
;
_publ_section_exptl_refinement
# see also _refine_ls_hydrogen for refinement keywords.
;
;
_publ_section_exptl_prep
;
The compound was prepared by NH and RV
and was recrystallised from ???.
The sample identification was H1-new.
;
_refine_special_details #Text of the paper
;
Crystals of this compound were obtained as very thin needles
which diffracted only weakly.
Even with long exposure times, the number of
reflections with intensities above background
is limited.
The observation:parameter ratio is therefore lower than we would like
but the identity of the compound is clearly established, nonetheless.
There do not appear to be any significant refinement anomalies.
Owing to the poor quality of the data,
hydrogen atoms
were not reliably observed in difference electron density maps
prior to their inclusion.
H atoms attached to C were added at calculated positions
and then were refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98\%A) and
U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom),
after which the positions were refined with riding constraints
and the displacement parameters were held fixed.
There is some doubt as to whether or not
there should be H atoms on N1 and N4.
There were no peaks in the final
difference electron density map at these locations, but with such weak
intensity data this is no real proof.
The C---N---N angles, however, are about 109\%, which seems more
consistent with a tetrahedral geometry (i.e. a N with a lone-pair
of electrons) than a trigonal geometry.
The C---N---N angle for compounds we have studied
where the H is clearly observed tend to be about 115\%.
The peaks in the final difference electron density map
are of similar intensity and are situated randomly through the structure.
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M. C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435--?.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J.
(2003). J. Appl. Cryst. 36, 1487--?.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Molecular Structure Corporation. (1992-1997). teXsan.
Single Crystal Structure Analysis Software. Version 1.8.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Johnson, C.K. (1976).
ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138,
Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cu1 Cu 0.72681(3) 0.50795(9) 0.31568(3) 0.0400 1.0000 Uani . . . . . .
O1 O 0.66920(17) 0.3906(4) 0.37284(18) 0.0417 1.0000 Uani . . . . . .
O2 O 0.66081(17) 0.6106(4) 0.26319(17) 0.0386 1.0000 Uani . . . . . .
O3 O 0.95135(18) 0.5415(5) 0.3132(2) 0.0577 1.0000 Uani . . . . . .
N1 N 0.7708(2) 0.2727(5) 0.4001(2) 0.0395 1.0000 Uani . . . . . .
N2 N 0.7958(2) 0.3865(5) 0.3579(2) 0.0361 1.0000 Uani . . . . . .
N3 N 0.7876(2) 0.6278(5) 0.2621(2) 0.0354 1.0000 Uani . . . . . .
N4 N 0.7554(3) 0.7279(6) 0.2189(2) 0.0434 1.0000 Uani . . . . . .
C1 C 0.6016(3) 0.2182(7) 0.4658(3) 0.0444 1.0000 Uani . . . . . .
C2 C 0.5697(3) 0.1318(7) 0.5132(3) 0.0546 1.0000 Uani . . . . . .
C3 C 0.6041(4) 0.0256(8) 0.5514(3) 0.0600 1.0000 Uani . . . . . .
C4 C 0.6722(3) 0.0063(8) 0.5419(3) 0.0564 1.0000 Uani . . . . . .
C5 C 0.7049(3) 0.0922(7) 0.4948(3) 0.0458 1.0000 Uani . . . . . .
C6 C 0.6706(3) 0.1982(7) 0.4562(3) 0.0375 1.0000 Uani . . . . . .
C7 C 0.7047(3) 0.2932(7) 0.4060(3) 0.0350 1.0000 Uani . . . . . .
C8 C 0.8607(3) 0.3974(7) 0.3517(3) 0.0369 1.0000 Uani . . . . . .
C9 C 0.9077(3) 0.2895(7) 0.3871(3) 0.0508 1.0000 Uani . . . . . .
C10 C 0.8904(3) 0.5242(7) 0.3099(3) 0.0420 1.0000 Uani . . . . . .
C11 C 0.8530(3) 0.6312(7) 0.2640(3) 0.0401 1.0000 Uani . . . . . .
C12 C 0.8943(3) 0.7415(7) 0.2229(3) 0.0519 1.0000 Uani . . . . . .
C13 C 0.6895(3) 0.7035(7) 0.2231(3) 0.0368 1.0000 Uani . . . . . .
C14 C 0.6459(3) 0.7948(7) 0.1784(3) 0.0386 1.0000 Uani . . . . . .
C15 C 0.6735(3) 0.8868(7) 0.1295(3) 0.0499 1.0000 Uani . . . . . .
C16 C 0.6314(3) 0.9714(8) 0.0886(3) 0.0588 1.0000 Uani . . . . . .
C17 C 0.5625(3) 0.9618(7) 0.0955(3) 0.0567 1.0000 Uani . . . . . .
C18 C 0.5356(3) 0.8709(7) 0.1438(3) 0.0543 1.0000 Uani . . . . . .
C19 C 0.5764(3) 0.7864(7) 0.1845(3) 0.0437 1.0000 Uani . . . . . .
H11 H 0.5778 0.2894 0.4403 0.0528 1.0000 Uiso R . . . . .
H21 H 0.5241 0.1458 0.5195 0.0659 1.0000 Uiso R . . . . .
H31 H 0.5815 -0.0308 0.5831 0.0718 1.0000 Uiso R . . . . .
H41 H 0.6957 -0.0638 0.5677 0.0678 1.0000 Uiso R . . . . .
H51 H 0.7509 0.0789 0.4890 0.0548 1.0000 Uiso R . . . . .
H91 H 0.9528 0.3110 0.3750 0.0762 1.0000 Uiso R . . . . .
H92 H 0.9034 0.3046 0.4326 0.0762 1.0000 Uiso R . . . . .
H93 H 0.8978 0.1809 0.3774 0.0758 1.0000 Uiso R . . . . .
H121 H 0.9384 0.6979 0.2177 0.0783 1.0000 Uiso R . . . . .
H122 H 0.8966 0.8434 0.2427 0.0779 1.0000 Uiso R . . . . .
H123 H 0.8737 0.7520 0.1815 0.0778 1.0000 Uiso R . . . . .
H151 H 0.7195 0.8911 0.1250 0.0600 1.0000 Uiso R . . . . .
H161 H 0.6500 1.0331 0.0569 0.0710 1.0000 Uiso R . . . . .
H171 H 0.5348 1.0191 0.0678 0.0678 1.0000 Uiso R . . . . .
H181 H 0.4889 0.8679 0.1493 0.0648 1.0000 Uiso R . . . . .
H191 H 0.5582 0.7217 0.2158 0.0516 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0250(3) 0.0459(4) 0.0492(4) 0.0043(4) 0.0015(4) -0.0019(4)
O1 0.022(2) 0.051(3) 0.053(3) 0.006(2) -0.002(2) 0.001(2)
O2 0.026(2) 0.046(2) 0.044(2) 0.006(2) -0.0014(19) -0.007(2)
O3 0.022(2) 0.075(3) 0.076(3) 0.003(3) -0.004(2) -0.009(2)
N1 0.028(3) 0.044(3) 0.047(3) 0.002(3) -0.002(2) -0.004(3)
N2 0.028(3) 0.034(3) 0.046(3) -0.004(3) -0.004(2) -0.002(2)
N3 0.027(3) 0.035(3) 0.044(3) -0.007(2) 0.003(2) -0.003(2)
N4 0.032(3) 0.049(3) 0.049(3) 0.005(3) 0.006(3) -0.001(2)
C1 0.036(4) 0.052(4) 0.045(4) 0.003(3) -0.004(3) -0.008(3)
C2 0.041(4) 0.063(5) 0.061(5) 0.000(4) 0.011(4) -0.013(4)
C3 0.068(5) 0.065(5) 0.047(4) 0.004(4) 0.003(4) -0.022(4)
C4 0.060(4) 0.060(4) 0.049(4) 0.017(4) -0.012(3) -0.010(5)
C5 0.040(4) 0.052(4) 0.045(4) 0.002(3) -0.005(3) -0.004(3)
C6 0.034(3) 0.044(4) 0.035(4) 0.001(3) -0.001(3) -0.004(3)
C7 0.025(3) 0.042(4) 0.038(4) -0.008(3) -0.007(3) -0.003(3)
C8 0.025(3) 0.040(4) 0.046(4) -0.011(3) -0.004(3) 0.002(3)
C9 0.024(3) 0.071(5) 0.058(4) -0.002(4) -0.008(3) -0.001(3)
C10 0.027(3) 0.053(4) 0.046(4) -0.014(4) 0.002(3) -0.003(3)
C11 0.037(4) 0.033(3) 0.050(4) -0.005(3) 0.009(3) 0.002(3)
C12 0.035(4) 0.051(4) 0.070(5) -0.001(4) 0.013(4) -0.004(3)
C13 0.041(4) 0.027(4) 0.042(4) -0.008(3) 0.005(3) 0.001(3)
C14 0.040(3) 0.040(3) 0.035(4) 0.003(3) 0.002(3) 0.001(3)
C15 0.049(4) 0.049(4) 0.052(4) 0.005(4) 0.005(4) 0.004(3)
C16 0.058(4) 0.067(5) 0.052(4) 0.014(4) 0.008(4) 0.003(4)
C17 0.053(4) 0.063(5) 0.055(4) 0.009(4) -0.010(4) 0.007(4)
C18 0.044(4) 0.060(5) 0.059(5) 0.005(4) -0.010(4) 0.000(4)
C19 0.033(3) 0.051(4) 0.048(4) 0.003(4) 0.000(3) -0.007(3)
_refine_ls_extinction_method
'None'
_oxford_refine_ls_scale 0.08855(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 . O1 . 1.925(4) yes
Cu1 . O2 . 1.915(4) yes
Cu1 . N2 . 1.923(4) yes
Cu1 . N3 . 1.930(4) yes
O1 . C7 . 1.283(6) yes
O2 . C13 . 1.277(6) yes
O3 . C10 . 1.224(6) yes
N1 . N2 . 1.391(6) yes
N1 . C7 . 1.331(6) yes
N2 . C8 . 1.301(6) yes
N3 . N4 . 1.389(6) yes
N3 . C11 . 1.302(6) yes
N4 . C13 . 1.332(7) yes
C1 . C2 . 1.380(8) yes
C1 . C6 . 1.397(7) yes
C1 . H11 . 0.930 no
C2 . C3 . 1.378(8) yes
C2 . H21 . 0.924 no
C3 . C4 . 1.378(8) yes
C3 . H31 . 0.931 no
C4 . C5 . 1.381(7) yes
C4 . H41 . 0.925 no
C5 . C6 . 1.380(7) yes
C5 . H51 . 0.932 no
C6 . C7 . 1.483(7) yes
C8 . C9 . 1.498(7) yes
C8 . C10 . 1.497(8) yes
C9 . H91 . 0.950 no
C9 . H92 . 0.959 no
C9 . H93 . 0.956 no
C10 . C11 . 1.509(8) yes
C11 . C12 . 1.506(7) yes
C12 . H121 . 0.957 no
C12 . H122 . 0.952 no
C12 . H123 . 0.960 no
C13 . C14 . 1.486(8) yes
C14 . C15 . 1.393(7) yes
C14 . C19 . 1.391(7) yes
C15 . C16 . 1.391(8) yes
C15 . H151 . 0.921 no
C16 . C17 . 1.381(8) yes
C16 . H161 . 0.918 no
C17 . C18 . 1.372(8) yes
C17 . H171 . 0.931 no
C18 . C19 . 1.374(8) yes
C18 . H181 . 0.935 no
C19 . H191 . 0.923 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . Cu1 . O2 . 100.13(15) yes
O1 . Cu1 . N2 . 82.52(17) yes
O2 . Cu1 . N2 . 171.86(18) yes
O1 . Cu1 . N3 . 177.03(17) yes
O2 . Cu1 . N3 . 82.19(17) yes
N2 . Cu1 . N3 . 95.43(19) yes
Cu1 . O1 . C7 . 109.4(3) yes
Cu1 . O2 . C13 . 110.1(4) yes
N2 . N1 . C7 . 108.8(5) yes
N1 . N2 . Cu1 . 113.5(3) yes
N1 . N2 . C8 . 117.8(5) yes
Cu1 . N2 . C8 . 128.7(4) yes
Cu1 . N3 . N4 . 113.7(3) yes
Cu1 . N3 . C11 . 128.3(4) yes
N4 . N3 . C11 . 117.9(5) yes
N3 . N4 . C13 . 108.6(5) yes
C2 . C1 . C6 . 119.3(6) yes
C2 . C1 . H11 . 121.0 no
C6 . C1 . H11 . 119.7 no
C1 . C2 . C3 . 121.7(6) yes
C1 . C2 . H21 . 119.0 no
C3 . C2 . H21 . 119.2 no
C2 . C3 . C4 . 118.8(6) yes
C2 . C3 . H31 . 120.0 no
C4 . C3 . H31 . 121.2 no
C3 . C4 . C5 . 120.2(6) yes
C3 . C4 . H41 . 119.2 no
C5 . C4 . H41 . 120.6 no
C4 . C5 . C6 . 121.2(6) yes
C4 . C5 . H51 . 119.5 no
C6 . C5 . H51 . 119.3 no
C1 . C6 . C5 . 118.7(5) yes
C1 . C6 . C7 . 119.1(5) yes
C5 . C6 . C7 . 122.1(5) yes
C6 . C7 . N1 . 116.7(5) yes
C6 . C7 . O1 . 118.1(4) yes
N1 . C7 . O1 . 125.2(5) yes
N2 . C8 . C9 . 121.9(5) yes
N2 . C8 . C10 . 120.0(5) yes
C9 . C8 . C10 . 118.1(5) yes
C8 . C9 . H91 . 110.1 no
C8 . C9 . H92 . 110.6 no
H91 . C9 . H92 . 108.8 no
C8 . C9 . H93 . 110.2 no
H91 . C9 . H93 . 108.6 no
H92 . C9 . H93 . 108.6 no
C8 . C10 . O3 . 116.3(5) yes
C8 . C10 . C11 . 126.8(4) yes
O3 . C10 . C11 . 116.9(5) yes
C10 . C11 . N3 . 119.9(5) yes
C10 . C11 . C12 . 117.3(5) yes
N3 . C11 . C12 . 122.8(6) yes
C11 . C12 . H121 . 109.2 no
C11 . C12 . H122 . 109.5 no
H121 . C12 . H122 . 110.4 no
C11 . C12 . H123 . 109.7 no
H121 . C12 . H123 . 108.8 no
H122 . C12 . H123 . 109.2 no
N4 . C13 . O2 . 125.3(6) yes
N4 . C13 . C14 . 117.0(5) yes
O2 . C13 . C14 . 117.7(5) yes
C13 . C14 . C15 . 121.1(5) yes
C13 . C14 . C19 . 119.7(5) yes
C15 . C14 . C19 . 119.1(6) yes
C14 . C15 . C16 . 119.7(6) yes
C14 . C15 . H151 . 119.2 no
C16 . C15 . H151 . 121.1 no
C15 . C16 . C17 . 120.3(6) yes
C15 . C16 . H161 . 119.1 no
C17 . C16 . H161 . 120.6 no
C16 . C17 . C18 . 119.8(6) yes
C16 . C17 . H171 . 119.5 no
C18 . C17 . H171 . 120.7 no
C17 . C18 . C19 . 120.7(6) yes
C17 . C18 . H181 . 119.5 no
C19 . C18 . H181 . 119.8 no
C14 . C19 . C18 . 120.4(6) yes
C14 . C19 . H191 . 119.0 no
C18 . C19 . H191 . 120.6 no
#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cu1 N1 2.837(4) . 3_655 no
Cu1 N4 3.120(5) . 3_645 no
Cu1 N2 3.332(4) . 3_655 no
Cu1 C7 3.339(6) . 3_655 no
Cu1 N3 3.397(4) . 3_645 no
O1 C11 3.177(7) . 3_645 no
O1 N3 3.308(5) . 3_645 no
O1 N1 3.473(5) . 3_655 no
O1 C10 3.551(7) . 3_645 no
O1 C12 3.596(7) . 3_645 no
O2 C8 3.066(7) . 3_655 no
O2 N2 3.165(5) . 3_655 no
O2 C9 3.285(7) . 3_655 no
O2 C12 3.396(7) . 3_645 no
O2 N1 3.443(5) . 3_655 no
O3 C19 3.230(7) . 8 no
O3 C18 3.359(7) . 8 no
O3 C19 3.478(7) . 3_645 no
N1 N3 3.333(6) . 3_645 no
N1 C5 3.368(7) . 3_655 no
N2 C13 3.216(7) . 3_645 no
N2 C5 3.336(7) . 3_655 no
N2 N4 3.348(6) . 3_645 no
N2 N3 3.387(6) . 3_645 no
N2 C6 3.392(7) . 3_655 no
N2 C7 3.562(7) . 3_655 no
N3 C7 3.309(7) . 3_655 no
N3 C15 3.513(7) . 3_645 no
N3 C14 3.554(7) . 3_645 no
N3 N4 3.583(7) . 3_645 no
C2 C2 3.59(1) . 2_656 no
C6 C8 3.395(9) . 3_645 no
C6 C10 3.593(9) . 3_645 no
C7 C11 3.454(9) . 3_645 no
C7 C10 3.564(9) . 3_645 no
C8 C13 3.292(9) . 3_645 no
C10 C19 3.356(9) . 3_645 no
C10 C14 3.428(9) . 3_645 no
C11 C14 3.343(9) . 3_645 no
C11 C15 3.515(9) . 3_645 no
#------------------------------------------------------------------------------
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cu1 O1 C7 N1 . . . . -2.2(7) no
Cu1 O1 C7 C6 . . . . 176.1(4) no
Cu1 O2 C13 N4 . . . . -1.0(7) no
Cu1 O2 C13 C14 . . . . -179.6(4) no
Cu1 N2 N1 C7 . . . . -8.1(5) no
Cu1 N2 C8 C9 . . . . -178.2(4) no
Cu1 N2 C8 C10 . . . . 3.9(8) no
Cu1 N3 N4 C13 . . . . -5.0(5) no
Cu1 N3 C11 C10 . . . . 4.1(8) no
Cu1 N3 C11 C12 . . . . -174.5(4) no
O1 Cu1 O2 C13 . . . . 176.5(4) no
O1 Cu1 N2 N1 . . . . 5.9(3) no
O1 Cu1 N2 C8 . . . . -174.4(5) no
O1 C7 N1 N2 . . . . 6.9(8) no
O1 C7 C6 C1 . . . . -0.2(8) no
O1 C7 C6 C5 . . . . -179.1(6) no
O2 Cu1 O1 C7 . . . . 170.0(4) no
O2 Cu1 N3 N4 . . . . 3.8(3) no
O2 Cu1 N3 C11 . . . . -179.9(5) no
O2 C13 N4 N3 . . . . 4.1(8) no
O2 C13 C14 C15 . . . . -173.9(5) no
O2 C13 C14 C19 . . . . 4.9(8) no
O3 C10 C8 N2 . . . . 170.3(5) no
O3 C10 C8 C9 . . . . -7.7(8) no
O3 C10 C11 N3 . . . . -174.4(5) no
O3 C10 C11 C12 . . . . 4.3(8) no
N1 N2 Cu1 N3 . . . . -176.3(3) no
N1 N2 C8 C9 . . . . 1.5(8) no
N1 N2 C8 C10 . . . . -176.4(5) no
N1 C7 C6 C1 . . . . 178.2(5) no
N1 C7 C6 C5 . . . . -0.6(9) no
N2 Cu1 O1 C7 . . . . -2.2(4) no
N2 Cu1 N3 N4 . . . . 175.9(3) no
N2 Cu1 N3 C11 . . . . -7.7(5) no
N2 N1 C7 C6 . . . . -171.4(5) no
N2 C8 C10 C11 . . . . -10.3(9) no
N3 Cu1 O2 C13 . . . . -1.6(4) no
N3 Cu1 N2 C8 . . . . 3.5(5) no
N3 N4 C13 C14 . . . . -177.4(5) no
N3 C11 C10 C8 . . . . 6.2(9) no
N4 N3 C11 C10 . . . . -179.7(5) no
N4 N3 C11 C12 . . . . 1.7(8) no
N4 C13 C14 C15 . . . . 7.4(9) no
N4 C13 C14 C19 . . . . -173.8(5) no
C1 C2 C3 C4 . . . . 0(1) no
C1 C6 C5 C4 . . . . 0.3(9) no
C2 C1 C6 C5 . . . . -0.1(9) no
C2 C1 C6 C7 . . . . -179.0(6) no
C2 C3 C4 C5 . . . . -0(1) no
C3 C2 C1 C6 . . . . -0.2(9) no
C3 C4 C5 C6 . . . . -0(1) no
C4 C5 C6 C7 . . . . 179.2(6) no
C7 N1 N2 C8 . . . . 172.2(5) no
C8 C10 C11 C12 . . . . -175.2(6) no
C9 C8 C10 C11 . . . . 171.7(6) no
C11 N3 N4 C13 . . . . 178.3(5) no
C13 C14 C15 C16 . . . . -179.7(6) no
C13 C14 C19 C18 . . . . 179.6(6) no
C14 C15 C16 C17 . . . . -1.3(9) no
C14 C19 C18 C17 . . . . 1.6(9) no
C15 C14 C19 C18 . . . . -1.6(9) no
C15 C16 C17 C18 . . . . 1.4(9) no
C16 C15 C14 C19 . . . . 1.5(9) no
C16 C17 C18 C19 . . . . -1.5(9) no
#------------------------------------------------------------------------------
_iucr_refine_instruction_details_constraints
;
#
# Punched on 21/08/13 at 14:14:06
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE C ( 1,X'S) H ( 11,X'S)
RIDE C ( 2,X'S) H ( 21,X'S)
RIDE C ( 3,X'S) H ( 31,X'S)
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 51,X'S)
RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S) H ( 93,X'S)
RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) H ( 123,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 171,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 19,X'S) H ( 191,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
#
# Punched on 21/08/13 at 14:14:06
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;
#===END