# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_TW51F
_database_code_depnum_ccdc_archive 'CCDC 1050957'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C19 H14.68 Cu N6.16 O4.32, C19 H13.32 Cu N6.84 O5.68, N O3, H2 O'
_chemical_formula_sum            'C38 H30 Cu2 N14 O14'
_chemical_formula_weight         1033.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   34.3062(8)
_cell_length_b                   6.9284(2)
_cell_length_c                   17.0628(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.2650(10)
_cell_angle_gamma                90
_cell_volume                     3930.56(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9792
_cell_measurement_theta_min      5.32
_cell_measurement_theta_max      72.33

_exptl_crystal_description       Plate
_exptl_crystal_colour            Pale_Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_F_000             2104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    2.143
_shelx_estimated_absorpt_T_min   0.693
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6806
_exptl_absorpt_correction_T_max  0.8432
_exptl_absorpt_process_details   'TWINABS V2012/1 (Sheldrick, 2012)'
_exptl_absorpt_special_details   'TWINABS V2012/1 (Sheldrick, 2012)'
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6410
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.658
_diffrn_reflns_theta_max         72.286
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             6410
_reflns_number_gt                6369
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.982

_reflns_special_details          
; 
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 

  
_computing_data_collection        'Apex2 (2013.10-2) (Bruker, 2013)' 
_computing_cell_refinement        'SAINT (8.34a) (Bruker, 2013)' 
_computing_data_reduction         'SAINT (8.34a) (Bruker, 2013)' 
_computing_structure_solution     'SHELXT (Sheldrick, 2014)' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details 

 Refined as a 4-component twin. - 2 components with racemic twinning.
 
 090_ALERT_3_B Poor Data / Parameter Ratio (Zmax > 18) ........       5.81 Note
Data/Parameter ratio is calculated after merging for difference map and here
Friedel's law is not applicable so there are, in fact, 6410 data/639 parameters
which produces a 10.03 data/param ratio.

#===============================================================================
341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0073 Ang.
911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         81 Report
Single reflections that also occur in composites have been omitted by Twinabs.
;

_refine_special_details          
;
Structural determination and Refinement:

All crystallographic calculations were performed on an Intel Xeon E5-1620v2
at 3.70GHz an eight core processor and 16GB of extended memory.   Data
collected were corrected for Lorentz and polarization effects with Saint(1)
and absorption using Blessings method and merged as incorporated with the
program Sadabs(2,3). The SHELXTL(4) program package was now implemented to
determine based upon intensity statistics, the non-centrosymmetric monoclinic
space group Cc (no. 9). The structure was determined by direct methods with a
majority of the non-hydrogen atoms from the two molecules of interest being
located directly using the program XT(5). Refinement of the structure was
achieved using the program XL(6). Difference-Fourier least-squares refinement
cycles were required to locate the remaining non-hydrogen atoms. Refinement
converged to approximately RF=16% for all observed data. It was evident from
the outset that the structure possessed more than a single domain when
examining the individual frames so reflections were thresholded in APEX(1)
and these reflections were input into Cellnow(7) that determined the twin
relationship between the two components and generated the orientation
matrices for the components and output a useable multiple matrice input file
for the integration program SAINT(1). Saint was run five times using the
output optimized merged matrix file from the previous run. Data collected
were now corrected for absorption using TWINABS(2,3,8) and Blessings method
and merged generating both HKLF4 and HKLF5 format files. Convergence of the
structure proceeded quickly using the HKLF5 format file while not well using
the HKLF4 format file. Due to the absolute structure parameters indicating
approximately 30% of the opposite hand for each component Twinabs was run
again and produced both components and their racemates.  All of the full
occupancy non-hydrogen atoms were refined anisotropically and using the HKLF5
determined the percentage of the four domains being present as follows:
0.19:0.29:0.38:0.14 as indicated from the batch scale factors. The final
structure was refined with the four component HKLF5 file. An odd disorder was
optimized between the two molecules wherein their overall composition is 1:1
for NO3 and OH2 groups but disordered over the two molecules in an 84:16
manner.  A single NO3 group was also located along with a water molecule that
had one hydrogen located from a difference-map and the other manually
calculated and allowed to refine with SADI instructions, O-H 0.84. All of
the hydrogen atoms within the two molecules of interest were idealized
throughout the final convergence cycles. The final structure was refined to
convergence with R(F)=3.58%, wR(F2)=9.56%, GOF=1.042 for all 6410 reflections
[R(F)=3.56, (F2)=9.53 those 6369 with Fo > 4sigma(Fo)]. A final difference-
Fourier map was featureless indicating that the structure is therefore both
correct and complete.


References:

1.	Bruker (2013) SMART APEX (2013-10.6) and (2012) SAINT (Version 8.34a).
Bruker AXS Inc., Madison, Wisconsin, USA.

2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H.
(1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2012/1) Siemens Area Detector Absorption
Correction Universitt Gttingen: Gttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Siemens Analytical X-ray
Instruments Inc., Madison, Wisconsin, USA.

5.	Sheldrick, G. M., (2014). SHELXT2014. Universitt Gttingen: Gttingen,
Germany.

6.	Sheldrick, G. M., SHELXL2014/7 structure refined program - unpublished.

7.	Sheldrick, G.M., CELLNOW, Twin matrix determination program, Universitt
Gttingen: Gttingen, Germany, Version 2008/3.

8.	Sheldrick, G.M., TWINABS Version 2012/1An Empirical Correction for
Absorption Anisotropy applied to Twinned crystals. Universitt Gttingen:
Gttingen, Germany.


;



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0775P)²+1.0845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2646 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.02(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6410
_refine_ls_number_parameters     639
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.66661(2) 0.76312(9) 0.56376(4) 0.02361(17) Uani 1 1 d D . . . .
C1 C 0.68369(13) 0.8759(7) 0.7414(3) 0.0287(9) Uani 1 1 d . . . . .
H1 H 0.7115 0.8664 0.7434 0.034 Uiso 1 1 calc R U . . .
N1 N 0.65674(12) 0.8470(6) 0.6714(2) 0.0256(8) Uani 1 1 d . . . . .
C2 C 0.67175(14) 0.9196(7) 0.8114(3) 0.0304(9) Uani 1 1 d . . . . .
H2 H 0.6917 0.9334 0.8608 0.036 Uiso 1 1 calc R U . . .
N2 N 0.63295(12) 0.9430(7) 0.8113(2) 0.0304(8) Uani 1 1 d . . . . .
C3 C 0.60622(13) 0.9191(7) 0.7406(3) 0.0268(9) Uani 1 1 d . . . . .
H3 H 0.5785 0.9372 0.7382 0.032 Uiso 1 1 calc R U . . .
C4 C 0.61721(14) 0.8688(7) 0.6702(3) 0.0249(9) Uani 1 1 d . . . . .
C5 C 0.58963(14) 0.8304(6) 0.5909(3) 0.0219(8) Uani 1 1 d . . . . .
N5 N 0.60865(14) 0.7827(6) 0.5340(3) 0.0236(8) Uani 1 1 d . . . . .
C6 C 0.54786(14) 0.8368(6) 0.5730(3) 0.0221(8) Uani 1 1 d . . . . .
H6 H 0.5344 0.8733 0.6131 0.026 Uiso 1 1 calc R U . . .
C7 C 0.52611(14) 0.7890(7) 0.4953(3) 0.0216(9) Uani 1 1 d . . . . .
C8 C 0.54681(18) 0.7365(6) 0.4374(3) 0.0247(10) Uani 1 1 d . . . . .
H8 H 0.5325 0.7034 0.3841 0.030 Uiso 1 1 calc R U . . .
C9 C 0.58855(17) 0.7335(6) 0.4589(3) 0.0224(10) Uani 1 1 d . . . . .
C10 C 0.61574(13) 0.6732(7) 0.4080(3) 0.0240(9) Uani 1 1 d . . . . .
N10 N 0.65544(11) 0.6762(6) 0.4470(2) 0.0258(8) Uani 1 1 d . . . . .
C11 C 0.60369(13) 0.6186(7) 0.3275(3) 0.0263(9) Uani 1 1 d . . . . .
H11 H 0.5758 0.6146 0.3020 0.032 Uiso 1 1 calc R U . . .
N11 N 0.62998(12) 0.5715(6) 0.2847(2) 0.0305(8) Uani 1 1 d . . . . .
C12 C 0.66922(14) 0.5790(7) 0.3236(3) 0.0297(9) Uani 1 1 d . . . . .
H12 H 0.6888 0.5509 0.2944 0.036 Uiso 1 1 calc R U . . .
C13 C 0.68181(14) 0.6266(7) 0.4049(3) 0.0289(9) Uani 1 1 d . . . . .
H13 H 0.7097 0.6238 0.4310 0.035 Uiso 1 1 calc R U . . .
C14 C 0.48140(14) 0.7893(6) 0.4770(3) 0.0229(8) Uani 1 1 d . . . . .
C15 C 0.46269(16) 0.7353(6) 0.5380(3) 0.0233(10) Uani 1 1 d . . . . .
H15 H 0.4785 0.7004 0.5900 0.028 Uiso 1 1 calc R U . . .
C16 C 0.42069(16) 0.7328(6) 0.5223(3) 0.0240(10) Uani 1 1 d . . . . .
H16 H 0.4079 0.6925 0.5630 0.029 Uiso 1 1 calc R U . . .
C17 C 0.39801(15) 0.7895(7) 0.4472(3) 0.0263(9) Uani 1 1 d . . . . .
H17 H 0.3695 0.7898 0.4370 0.032 Uiso 1 1 calc R U . . .
C18 C 0.41595(13) 0.8458(7) 0.3867(3) 0.0258(9) Uani 1 1 d . . . . .
H18 H 0.3999 0.8861 0.3357 0.031 Uiso 1 1 calc R U . . .
C19 C 0.45818(14) 0.8429(6) 0.4010(3) 0.0240(8) Uani 1 1 d . . . . .
H19 H 0.4707 0.8773 0.3592 0.029 Uiso 1 1 calc R U . . .
O19 O 0.72076(9) 0.6484(5) 0.6099(2) 0.0284(7) Uani 1 1 d . . . . .
N20 N 0.71470(14) 0.4778(6) 0.6360(3) 0.0277(9) Uani 1 1 d . . . . .
O20 O 0.74337(11) 0.3842(6) 0.6736(2) 0.0371(8) Uani 1 1 d . . . . .
O21 O 0.67954(10) 0.4161(6) 0.6206(3) 0.0392(9) Uani 1 1 d . . . . .
O22 O 0.69140(13) 1.0421(6) 0.5452(3) 0.0395(8) Uani 0.84 1 d D . P A 1
H22A H 0.6760 1.1350 0.5277 0.047 Uiso 0.84 1 calc R U P A 1
H22B H 0.7164 1.0574 0.5554 0.047 Uiso 0.84 1 calc R U P A 1
O22B O 0.69140(13) 1.0421(6) 0.5452(3) 0.0395(8) Uani 0.16 1 d . . P A 2
N22 N 0.7124(5) 1.083(2) 0.5186(12) 0.018(4) Uiso 0.16 1 d D . P A 2
O23 O 0.7179(10) 1.252(3) 0.499(2) 0.047(7) Uiso 0.16 1 d D . P A 2
O24 O 0.7334(7) 0.945(3) 0.5063(17) 0.046(6) Uiso 0.16 1 d D . P A 2
Cu31 Cu 0.82199(2) 0.76146(9) 0.43051(4) 0.02545(18) Uani 1 1 d D . . . .
C31 C 0.81550(14) 0.5607(8) 0.5839(3) 0.0284(9) Uani 1 1 d . . . . .
H31 H 0.7872 0.5560 0.5618 0.034 Uiso 1 1 calc R U . . .
N31 N 0.83898(12) 0.6381(6) 0.5409(2) 0.0252(7) Uani 1 1 d . . . . .
C32 C 0.83173(17) 0.4866(7) 0.6607(3) 0.0297(11) Uani 1 1 d . . . . .
H32 H 0.8142 0.4343 0.6904 0.036 Uiso 1 1 calc R U . . .
N32 N 0.87171(14) 0.4867(5) 0.6943(3) 0.0270(9) Uani 1 1 d . . . . .
C33 C 0.89495(13) 0.5637(7) 0.6507(3) 0.0269(8) Uani 1 1 d . . . . .
H33 H 0.9232 0.5664 0.6727 0.032 Uiso 1 1 calc R U . . .
C34 C 0.87926(13) 0.6406(7) 0.5739(3) 0.0240(9) Uani 1 1 d . . . . .
C35 C 0.90301(16) 0.7208(7) 0.5206(3) 0.0234(9) Uani 1 1 d . . . . .
N35 N 0.87984(13) 0.7850(6) 0.4502(3) 0.0235(8) Uani 1 1 d . . . . .
C36 C 0.94512(16) 0.7243(6) 0.5357(3) 0.0237(9) Uani 1 1 d . . . . .
H36 H 0.9616 0.6828 0.5862 0.028 Uiso 1 1 calc R U . . .
C37 C 0.96217(15) 0.7912(7) 0.4740(3) 0.0239(9) Uani 1 1 d . . . . .
C38 C 0.93709(14) 0.8534(6) 0.4005(3) 0.0231(8) Uani 1 1 d . . . . .
H38 H 0.9482 0.8970 0.3578 0.028 Uiso 1 1 calc R U . . .
C39 C 0.89574(14) 0.8500(6) 0.3914(3) 0.0254(9) Uani 1 1 d . . . . .
C40 C 0.86457(14) 0.9118(6) 0.3195(3) 0.0258(9) Uani 1 1 d . . . . .
N40 N 0.82626(12) 0.8872(6) 0.3258(2) 0.0284(8) Uani 1 1 d . . . . .
C41 C 0.87163(18) 0.9917(6) 0.2493(3) 0.0303(11) Uani 1 1 d . . . . .
H41 H 0.8986 1.0056 0.2451 0.036 Uiso 1 1 calc R U . . .
N41 N 0.84175(14) 1.0495(7) 0.1879(3) 0.0359(9) Uani 1 1 d . . . . .
C42 C 0.80437(18) 1.0269(8) 0.1961(3) 0.0353(11) Uani 1 1 d . . . . .
H42 H 0.7825 1.0682 0.1536 0.042 Uiso 1 1 calc R U . . .
C43 C 0.79638(15) 0.9449(8) 0.2647(3) 0.0319(9) Uani 1 1 d . . . . .
H43 H 0.7693 0.9299 0.2681 0.038 Uiso 1 1 calc R U . . .
C44 C 1.00655(15) 0.7903(7) 0.4868(3) 0.0242(9) Uani 1 1 d . . . . .
C45 C 1.03187(14) 0.8302(7) 0.5621(3) 0.0259(9) Uani 1 1 d . . . . .
H45 H 1.0206 0.8617 0.6061 0.031 Uiso 1 1 calc R U . . .
C46 C 1.07355(15) 0.8247(7) 0.5739(3) 0.0287(9) Uani 1 1 d . . . . .
H46 H 1.0906 0.8535 0.6255 0.034 Uiso 1 1 calc R U . . .
C47 C 1.08995(16) 0.7766(7) 0.5096(4) 0.0298(11) Uani 1 1 d . . . . .
H47 H 1.1183 0.7721 0.5175 0.036 Uiso 1 1 calc R U . . .
C48 C 1.06515(18) 0.7350(6) 0.4338(4) 0.0281(11) Uani 1 1 d . . . . .
H48 H 1.0765 0.7007 0.3903 0.034 Uiso 1 1 calc R U . . .
C49 C 1.02340(18) 0.7442(6) 0.4224(3) 0.0253(10) Uani 1 1 d . . . . .
H49 H 1.0064 0.7190 0.3704 0.030 Uiso 1 1 calc R U . . .
N50 N 0.78170(13) 0.4495(7) 0.3495(3) 0.0299(8) Uani 1 1 d . . . . .
O50 O 0.77246(10) 0.5986(6) 0.3862(2) 0.0327(7) Uani 1 1 d . . . . .
O51 O 0.81547(10) 0.4380(6) 0.3374(2) 0.0316(7) Uani 1 1 d . . . . .
O52 O 0.75588(14) 0.3225(7) 0.3281(3) 0.0471(10) Uani 1 1 d . . . . .
O53 O 0.8014(7) 1.0450(15) 0.4552(15) 0.0354(9) Uani 0.16 1 d D . P B 2
H53A H 0.8181 1.1348 0.4699 0.042 Uiso 0.16 1 calc R U P B 2
H53B H 0.7768 1.0654 0.4501 0.042 Uiso 0.16 1 calc R U P B 2
O53B O 0.77283(13) 0.9232(7) 0.4616(3) 0.0354(9) Uani 0.84 1 d . . P B 1
N53 N 0.78423(15) 1.0883(8) 0.4901(3) 0.0288(10) Uani 0.84 1 d D . P B 1
O54 O 0.81912(14) 1.1433(7) 0.4930(3) 0.0419(10) Uani 0.84 1 d D . P B 1
O55 O 0.76042(15) 1.1952(8) 0.5147(4) 0.0448(11) Uani 0.84 1 d . . P B 1
N61 N 0.48572(13) 0.4370(6) 0.2343(2) 0.0281(8) Uani 1 1 d . . . . .
O61 O 0.52094(11) 0.4226(6) 0.2275(2) 0.0351(8) Uani 1 1 d . . . . .
O62 O 0.47160(13) 0.5993(6) 0.2466(3) 0.0448(10) Uani 1 1 d . . . . .
O63 O 0.46399(11) 0.2888(5) 0.2308(2) 0.0283(7) Uani 1 1 d . . . . .
O71 O 0.51231(11) 0.9483(6) 0.2231(2) 0.0349(8) Uani 1 1 d D . . . .
H71 H 0.495(2) 1.027(12) 0.229(7) 0.08(3) Uiso 1 1 d D . . . .
H72 H 0.503(3) 0.841(7) 0.233(7) 0.08(3) Uiso 1 1 d D . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N5 1.932(5) . ?
Cu1 O19 1.995(3) . ?
Cu1 N10 2.026(4) . ?
Cu1 N1 2.033(4) . ?
Cu1 O22B 2.166(4) . ?
Cu1 O22 2.166(4) . ?
C1 N1 1.332(6) . ?
C1 C2 1.388(7) . ?
C1 H1 0.9500 . ?
N1 C4 1.359(6) . ?
C2 N2 1.341(6) . ?
C2 H2 0.9500 . ?
N2 C3 1.334(6) . ?
C3 C4 1.390(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.471(6) . ?
C5 N5 1.338(7) . ?
C5 C6 1.390(6) . ?
N5 C9 1.341(7) . ?
C6 C7 1.391(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(7) . ?
C7 C14 1.488(6) . ?
C8 C9 1.388(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.483(7) . ?
C10 N10 1.361(6) . ?
C10 C11 1.385(7) . ?
N10 C13 1.331(6) . ?
C11 N11 1.334(6) . ?
C11 H11 0.9500 . ?
N11 C12 1.347(6) . ?
C12 C13 1.388(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.396(6) . ?
C14 C15 1.401(7) . ?
C15 C16 1.399(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.409(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
O19 N20 1.298(6) . ?
N20 O20 1.220(6) . ?
N20 O21 1.245(6) . ?
O22 H22A 0.8400 . ?
O22 H22B 0.8400 . ?
O22B N22 0.981(16) . ?
N22 O24 1.245(14) . ?
N22 O23 1.248(14) . ?
Cu31 N35 1.936(5) . ?
Cu31 N31 2.019(4) . ?
Cu31 N40 2.025(4) . ?
Cu31 O50 2.025(4) . ?
Cu31 O53 2.164(6) . ?
Cu31 O53B 2.196(4) . ?
C31 N31 1.329(6) . ?
C31 C32 1.390(8) . ?
C31 H31 0.9500 . ?
N31 C34 1.358(6) . ?
C32 N32 1.350(7) . ?
C32 H32 0.9500 . ?
N32 C33 1.328(7) . ?
C33 C34 1.395(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.471(7) . ?
C35 N35 1.342(7) . ?
C35 C36 1.404(8) . ?
N35 C39 1.333(7) . ?
C36 C37 1.403(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.403(7) . ?
C37 C44 1.484(7) . ?
C38 C39 1.389(7) . ?
C38 H38 0.9500 . ?
C39 C40 1.479(6) . ?
C40 N40 1.356(6) . ?
C40 C41 1.393(7) . ?
N40 C43 1.331(6) . ?
C41 N41 1.334(7) . ?
C41 H41 0.9500 . ?
N41 C42 1.333(8) . ?
C42 C43 1.388(8) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C45 1.390(7) . ?
C44 C49 1.399(7) . ?
C45 C46 1.394(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.392(8) . ?
C46 H46 0.9500 . ?
C47 C48 1.391(8) . ?
C47 H47 0.9500 . ?
C48 C49 1.399(9) . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
N50 O51 1.228(6) . ?
N50 O52 1.238(6) . ?
N50 O50 1.288(6) . ?
O53 H53A 0.8400 . ?
O53 H53B 0.8400 . ?
O53B N53 1.267(7) . ?
N53 O54 1.246(7) . ?
N53 O55 1.249(7) . ?
N61 O61 1.246(6) . ?
N61 O63 1.261(5) . ?
N61 O62 1.263(6) . ?
O71 H71 0.840(14) . ?
O71 H72 0.840(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cu1 O19 158.36(16) . . ?
N5 Cu1 N10 80.16(17) . . ?
O19 Cu1 N10 101.64(15) . . ?
N5 Cu1 N1 80.09(17) . . ?
O19 Cu1 N1 95.95(15) . . ?
N10 Cu1 N1 160.13(16) . . ?
N5 Cu1 O22B 108.33(17) . . ?
O19 Cu1 O22B 93.00(16) . . ?
N10 Cu1 O22B 96.14(17) . . ?
N1 Cu1 O22B 92.07(16) . . ?
N5 Cu1 O22 108.33(17) . . ?
O19 Cu1 O22 93.00(16) . . ?
N10 Cu1 O22 96.14(17) . . ?
N1 Cu1 O22 92.07(16) . . ?
N1 C1 C2 121.1(4) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 N1 C4 117.8(4) . . ?
C1 N1 Cu1 128.2(3) . . ?
C4 N1 Cu1 113.9(3) . . ?
N2 C2 C1 122.0(4) . . ?
N2 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C3 N2 C2 116.5(4) . . ?
N2 C3 C4 122.8(4) . . ?
N2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
N1 C4 C3 119.8(4) . . ?
N1 C4 C5 114.1(4) . . ?
C3 C4 C5 126.2(4) . . ?
N5 C5 C6 120.6(4) . . ?
N5 C5 C4 113.2(4) . . ?
C6 C5 C4 126.2(4) . . ?
C5 N5 C9 121.9(5) . . ?
C5 N5 Cu1 118.7(3) . . ?
C9 N5 Cu1 119.1(4) . . ?
C5 C6 C7 118.9(4) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C8 119.2(4) . . ?
C6 C7 C14 118.8(4) . . ?
C8 C7 C14 121.9(4) . . ?
C9 C8 C7 119.2(5) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N5 C9 C8 120.2(5) . . ?
N5 C9 C10 112.4(5) . . ?
C8 C9 C10 127.4(5) . . ?
N10 C10 C11 120.5(4) . . ?
N10 C10 C9 114.1(4) . . ?
C11 C10 C9 125.5(4) . . ?
C13 N10 C10 117.6(4) . . ?
C13 N10 Cu1 128.2(3) . . ?
C10 N10 Cu1 114.2(3) . . ?
N11 C11 C10 122.2(4) . . ?
N11 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 N11 C12 116.7(4) . . ?
N11 C12 C13 121.9(4) . . ?
N11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
N10 C13 C12 121.0(4) . . ?
N10 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C19 C14 C15 120.0(4) . . ?
C19 C14 C7 121.2(4) . . ?
C15 C14 C7 118.8(4) . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 119.4(5) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.4(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 119.6(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 119.5(4) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
N20 O19 Cu1 106.6(3) . . ?
O20 N20 O21 122.8(5) . . ?
O20 N20 O19 119.2(4) . . ?
O21 N20 O19 118.0(4) . . ?
Cu1 O22 H22A 120.0 . . ?
Cu1 O22 H22B 120.0 . . ?
H22A O22 H22B 120.0 . . ?
N22 O22B Cu1 133.1(10) . . ?
O22B N22 O24 112.3(18) . . ?
O22B N22 O23 125(2) . . ?
O24 N22 O23 123(2) . . ?
N35 Cu31 N31 79.96(17) . . ?
N35 Cu31 N40 79.82(17) . . ?
N31 Cu31 N40 159.73(17) . . ?
N35 Cu31 O50 147.34(16) . . ?
N31 Cu31 O50 97.77(15) . . ?
N40 Cu31 O50 98.45(16) . . ?
N35 Cu31 O53 105.0(7) . . ?
N31 Cu31 O53 103.6(7) . . ?
N40 Cu31 O53 83.1(6) . . ?
O50 Cu31 O53 107.1(7) . . ?
N35 Cu31 O53B 136.91(17) . . ?
N31 Cu31 O53B 93.03(17) . . ?
N40 Cu31 O53B 102.73(17) . . ?
O50 Cu31 O53B 75.55(16) . . ?
N31 C31 C32 120.9(4) . . ?
N31 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C31 N31 C34 118.0(4) . . ?
C31 N31 Cu31 127.7(3) . . ?
C34 N31 Cu31 114.3(3) . . ?
N32 C32 C31 122.0(5) . . ?
N32 C32 H32 119.0 . . ?
C31 C32 H32 119.0 . . ?
C33 N32 C32 116.7(4) . . ?
N32 C33 C34 122.3(4) . . ?
N32 C33 H33 118.9 . . ?
C34 C33 H33 118.9 . . ?
N31 C34 C33 120.2(4) . . ?
N31 C34 C35 114.3(4) . . ?
C33 C34 C35 125.5(4) . . ?
N35 C35 C36 121.0(5) . . ?
N35 C35 C34 112.5(4) . . ?
C36 C35 C34 126.5(5) . . ?
C39 N35 C35 121.6(5) . . ?
C39 N35 Cu31 119.3(4) . . ?
C35 N35 Cu31 118.9(4) . . ?
C37 C36 C35 117.9(5) . . ?
C37 C36 H36 121.0 . . ?
C35 C36 H36 121.0 . . ?
C36 C37 C38 119.7(5) . . ?
C36 C37 C44 119.4(5) . . ?
C38 C37 C44 120.9(4) . . ?
C39 C38 C37 118.6(4) . . ?
C39 C38 H38 120.7 . . ?
C37 C38 H38 120.7 . . ?
N35 C39 C38 121.2(4) . . ?
N35 C39 C40 112.1(4) . . ?
C38 C39 C40 126.7(4) . . ?
N40 C40 C41 119.7(4) . . ?
N40 C40 C39 114.5(4) . . ?
C41 C40 C39 125.8(5) . . ?
C43 N40 C40 118.3(4) . . ?
C43 N40 Cu31 127.7(4) . . ?
C40 N40 Cu31 114.0(3) . . ?
N41 C41 C40 122.1(5) . . ?
N41 C41 H41 118.9 . . ?
C40 C41 H41 118.9 . . ?
C42 N41 C41 117.1(5) . . ?
N41 C42 C43 122.1(5) . . ?
N41 C42 H42 118.9 . . ?
C43 C42 H42 118.9 . . ?
N40 C43 C42 120.6(5) . . ?
N40 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C45 C44 C49 119.1(5) . . ?
C45 C44 C37 121.3(4) . . ?
C49 C44 C37 119.6(5) . . ?
C44 C45 C46 120.9(4) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C47 C46 C45 119.5(4) . . ?
C47 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C48 C47 C46 120.6(5) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C47 C48 C49 119.4(5) . . ?
C47 C48 H48 120.3 . . ?
C49 C48 H48 120.3 . . ?
C48 C49 C44 120.5(5) . . ?
C48 C49 H49 119.7 . . ?
C44 C49 H49 119.7 . . ?
O51 N50 O52 122.7(5) . . ?
O51 N50 O50 119.3(4) . . ?
O52 N50 O50 118.0(5) . . ?
N50 O50 Cu31 110.1(3) . . ?
Cu31 O53 H53A 120.0 . . ?
Cu31 O53 H53B 120.0 . . ?
H53A O53 H53B 120.0 . . ?
N53 O53B Cu31 111.8(3) . . ?
O54 N53 O55 120.4(5) . . ?
O54 N53 O53B 119.6(5) . . ?
O55 N53 O53B 119.9(5) . . ?
O61 N61 O63 120.4(4) . . ?
O61 N61 O62 120.5(4) . . ?
O63 N61 O62 119.1(4) . . ?
H71 O71 H72 103(10) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C4 2.4(7) . . . . ?
C2 C1 N1 Cu1 -175.2(4) . . . . ?
N1 C1 C2 N2 -2.9(8) . . . . ?
C1 C2 N2 C3 1.0(7) . . . . ?
C2 N2 C3 C4 1.3(7) . . . . ?
C1 N1 C4 C3 -0.2(7) . . . . ?
Cu1 N1 C4 C3 177.7(4) . . . . ?
C1 N1 C4 C5 -178.9(4) . . . . ?
Cu1 N1 C4 C5 -1.0(5) . . . . ?
N2 C3 C4 N1 -1.7(7) . . . . ?
N2 C3 C4 C5 176.8(5) . . . . ?
N1 C4 C5 N5 -0.6(6) . . . . ?
C3 C4 C5 N5 -179.2(5) . . . . ?
N1 C4 C5 C6 178.2(4) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C6 C5 N5 C9 -2.2(7) . . . . ?
C4 C5 N5 C9 176.7(4) . . . . ?
C6 C5 N5 Cu1 -176.8(3) . . . . ?
C4 C5 N5 Cu1 2.1(5) . . . . ?
N5 C5 C6 C7 1.3(6) . . . . ?
C4 C5 C6 C7 -177.5(4) . . . . ?
C5 C6 C7 C8 -0.2(7) . . . . ?
C5 C6 C7 C14 177.9(4) . . . . ?
C6 C7 C8 C9 0.0(7) . . . . ?
C14 C7 C8 C9 -178.0(4) . . . . ?
C5 N5 C9 C8 1.9(7) . . . . ?
Cu1 N5 C9 C8 176.5(3) . . . . ?
C5 N5 C9 C10 -176.0(4) . . . . ?
Cu1 N5 C9 C10 -1.3(5) . . . . ?
C7 C8 C9 N5 -0.8(6) . . . . ?
C7 C8 C9 C10 176.7(4) . . . . ?
N5 C9 C10 N10 0.9(6) . . . . ?
C8 C9 C10 N10 -176.8(4) . . . . ?
N5 C9 C10 C11 -178.5(5) . . . . ?
C8 C9 C10 C11 3.8(8) . . . . ?
C11 C10 N10 C13 0.5(7) . . . . ?
C9 C10 N10 C13 -179.0(4) . . . . ?
C11 C10 N10 Cu1 179.3(4) . . . . ?
C9 C10 N10 Cu1 -0.2(5) . . . . ?
N10 C10 C11 N11 -1.5(7) . . . . ?
C9 C10 C11 N11 177.9(4) . . . . ?
C10 C11 N11 C12 0.1(7) . . . . ?
C11 N11 C12 C13 2.2(7) . . . . ?
C10 N10 C13 C12 1.8(7) . . . . ?
Cu1 N10 C13 C12 -176.8(4) . . . . ?
N11 C12 C13 N10 -3.3(8) . . . . ?
C6 C7 C14 C19 146.1(4) . . . . ?
C8 C7 C14 C19 -35.9(7) . . . . ?
C6 C7 C14 C15 -33.6(6) . . . . ?
C8 C7 C14 C15 144.4(5) . . . . ?
C19 C14 C15 C16 0.8(7) . . . . ?
C7 C14 C15 C16 -179.5(4) . . . . ?
C14 C15 C16 C17 -2.0(7) . . . . ?
C15 C16 C17 C18 1.1(7) . . . . ?
C16 C17 C18 C19 0.9(7) . . . . ?
C15 C14 C19 C18 1.2(7) . . . . ?
C7 C14 C19 C18 -178.5(4) . . . . ?
C17 C18 C19 C14 -2.1(7) . . . . ?
Cu1 O19 N20 O20 -173.5(4) . . . . ?
Cu1 O19 N20 O21 7.1(5) . . . . ?
Cu1 O22B N22 O24 -15(3) . . . . ?
Cu1 O22B N22 O23 165(2) . . . . ?
C32 C31 N31 C34 0.7(7) . . . . ?
C32 C31 N31 Cu31 -177.8(4) . . . . ?
N31 C31 C32 N32 -1.1(8) . . . . ?
C31 C32 N32 C33 0.8(7) . . . . ?
C32 N32 C33 C34 -0.2(7) . . . . ?
C31 N31 C34 C33 -0.1(6) . . . . ?
Cu31 N31 C34 C33 178.6(3) . . . . ?
C31 N31 C34 C35 177.3(4) . . . . ?
Cu31 N31 C34 C35 -3.9(5) . . . . ?
N32 C33 C34 N31 -0.2(7) . . . . ?
N32 C33 C34 C35 -177.3(4) . . . . ?
N31 C34 C35 N35 2.9(6) . . . . ?
C33 C34 C35 N35 -179.8(5) . . . . ?
N31 C34 C35 C36 -173.6(5) . . . . ?
C33 C34 C35 C36 3.7(8) . . . . ?
C36 C35 N35 C39 1.7(7) . . . . ?
C34 C35 N35 C39 -175.0(4) . . . . ?
C36 C35 N35 Cu31 176.2(3) . . . . ?
C34 C35 N35 Cu31 -0.5(5) . . . . ?
N35 C35 C36 C37 -2.0(7) . . . . ?
C34 C35 C36 C37 174.2(4) . . . . ?
C35 C36 C37 C38 0.6(7) . . . . ?
C35 C36 C37 C44 -177.8(4) . . . . ?
C36 C37 C38 C39 1.1(7) . . . . ?
C44 C37 C38 C39 179.5(4) . . . . ?
C35 N35 C39 C38 0.2(7) . . . . ?
Cu31 N35 C39 C38 -174.4(3) . . . . ?
C35 N35 C39 C40 179.6(4) . . . . ?
Cu31 N35 C39 C40 5.1(5) . . . . ?
C37 C38 C39 N35 -1.6(6) . . . . ?
C37 C38 C39 C40 179.1(4) . . . . ?
N35 C39 C40 N40 -1.4(6) . . . . ?
C38 C39 C40 N40 178.0(4) . . . . ?
N35 C39 C40 C41 177.8(4) . . . . ?
C38 C39 C40 C41 -2.8(7) . . . . ?
C41 C40 N40 C43 -1.4(7) . . . . ?
C39 C40 N40 C43 177.9(5) . . . . ?
C41 C40 N40 Cu31 178.2(3) . . . . ?
C39 C40 N40 Cu31 -2.5(5) . . . . ?
N40 C40 C41 N41 1.4(7) . . . . ?
C39 C40 C41 N41 -177.8(5) . . . . ?
C40 C41 N41 C42 -0.3(8) . . . . ?
C41 N41 C42 C43 -0.8(8) . . . . ?
C40 N40 C43 C42 0.5(8) . . . . ?
Cu31 N40 C43 C42 -179.1(4) . . . . ?
N41 C42 C43 N40 0.7(9) . . . . ?
C36 C37 C44 C45 -36.0(7) . . . . ?
C38 C37 C44 C45 145.6(5) . . . . ?
C36 C37 C44 C49 142.5(4) . . . . ?
C38 C37 C44 C49 -35.9(7) . . . . ?
C49 C44 C45 C46 0.0(7) . . . . ?
C37 C44 C45 C46 178.5(4) . . . . ?
C44 C45 C46 C47 -0.7(7) . . . . ?
C45 C46 C47 C48 0.3(7) . . . . ?
C46 C47 C48 C49 0.8(7) . . . . ?
C47 C48 C49 C44 -1.5(6) . . . . ?
C45 C44 C49 C48 1.1(7) . . . . ?
C37 C44 C49 C48 -177.5(4) . . . . ?
O51 N50 O50 Cu31 -8.8(5) . . . . ?
O52 N50 O50 Cu31 170.8(4) . . . . ?
Cu31 O53B N53 O54 4.0(7) . . . . ?
Cu31 O53B N53 O55 -176.4(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O52 0.95 2.24 2.899(6) 126. 2_565
C2 H2 N22 0.95 2.61 3.47(2) 150. 2_575
C3 H3 O71 0.95 2.36 3.292(6) 167. 2_575
C6 H6 O71 0.95 2.51 3.435(6) 163. 2_575
C11 H11 O61 0.95 2.40 3.229(6) 146. .
C13 H13 O24 0.95 2.60 3.08(3) 112. .
C13 H13 O50 0.95 2.46 3.209(6) 135. .
O22 H22A O21 0.84 2.50 2.966(6) 116. 1_565
O22 H22B O55 0.84 2.05 2.758(6) 142. .
C32 H32 O20 0.95 2.40 3.173(6) 138. .
C38 H38 O63 0.95 2.48 3.278(5) 142. 3
C41 H41 O62 0.95 2.58 3.521(7) 170. 3
O53 H53B O24 0.84 2.13 2.77(3) 133. .
O71 H71 O63 0.840(14) 2.10(4) 2.905(6) 161(10) 1_565
O71 H72 O62 0.840(14) 2.04(2) 2.870(6) 170(10) .

_refine_diff_density_max         0.608
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.067



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF2345FFFACEMI
_database_code_depnum_ccdc_archive 'CCDC 1050958'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 N7 O6 Zn'
_chemical_formula_sum            'C19 H13 N7 O6 Zn'
_chemical_formula_weight         500.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   15.8793(19)
_cell_length_b                   16.956(2)
_cell_length_c                   7.1252(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1918.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9743
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.52

_exptl_crystal_description       Rod
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    1.338
_shelx_estimated_absorpt_T_min   0.637
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.7324
_exptl_absorpt_correction_T_max  0.9242
_exptl_absorpt_process_details   'SADABS 2014/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16953
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.757
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4413
_reflns_number_gt                4334
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
 JAMES C FETTINGER
;

_computing_data_collection       'Apex2 (2013.10-2) (Bruker, 2013)'
_computing_cell_refinement       'SAINT (8.34a) (Bruker, 2013)'
_computing_data_reduction        'SAINT (8.34a) (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+0.4811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1968 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.002(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     311
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0182
_refine_ls_wR_factor_ref         0.0504
_refine_ls_wR_factor_gt          0.0502
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.67159(2) 0.81523(2) 0.52172(5) 0.01214(7) Uani 1 1 d . . . . .
C1 C 0.52799(14) 0.92129(12) 0.7042(3) 0.0165(4) Uani 1 1 d . . . . .
H1 H 0.5634 0.9655 0.6819 0.016(6) Uiso 1 1 calc R . . . .
N1 N 0.55312(11) 0.84951(10) 0.6504(2) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.45040(15) 0.93214(13) 0.7927(3) 0.0196(4) Uani 1 1 d . . . . .
H2 H 0.4338 0.9841 0.8258 0.025(7) Uiso 1 1 calc R . . . .
N2 N 0.39872(13) 0.87275(12) 0.8327(3) 0.0211(4) Uani 1 1 d . . . . .
C3 C 0.42533(15) 0.80024(14) 0.7814(3) 0.0183(4) Uani 1 1 d . . . . .
H3 H 0.3909 0.7559 0.8094 0.020(7) Uiso 1 1 calc R . . . .
C4 C 0.50147(13) 0.78822(12) 0.6889(3) 0.0131(4) Uani 1 1 d . . . . .
C5 C 0.53239(12) 0.70902(12) 0.6285(3) 0.0117(4) Uani 1 1 d . . . . .
N5 N 0.61217(11) 0.70925(10) 0.5665(2) 0.0115(3) Uani 1 1 d . . . . .
C6 C 0.48497(13) 0.64027(12) 0.6336(3) 0.0135(4) Uani 1 1 d . . . . .
H6 H 0.4282 0.6414 0.6754 0.021(7) Uiso 1 1 calc R . . . .
C7 C 0.52189(13) 0.56927(11) 0.5765(3) 0.0120(4) Uani 1 1 d . . . . .
C8 C 0.60669(11) 0.56999(10) 0.5191(4) 0.0124(3) Uani 1 1 d . . . . .
H8 H 0.6344 0.5225 0.4845 0.017(6) Uiso 1 1 calc R . . . .
C9 C 0.64905(11) 0.64160(10) 0.5142(4) 0.0116(3) Uani 1 1 d . . . . .
C10 C 0.73593(13) 0.65169(12) 0.4409(3) 0.0118(4) Uani 1 1 d . . . . .
N10 N 0.76042(11) 0.72712(10) 0.4100(2) 0.0128(3) Uani 1 1 d . . . . .
C11 C 0.79016(14) 0.58913(13) 0.4003(3) 0.0155(4) Uani 1 1 d . . . . .
H11 H 0.7722 0.5368 0.4266 0.018(7) Uiso 1 1 calc R . . . .
N11 N 0.86670(11) 0.60042(11) 0.3255(3) 0.0180(4) Uani 1 1 d . . . . .
C12 C 0.88840(15) 0.67519(14) 0.2894(3) 0.0182(4) Uani 1 1 d . . . . .
H12 H 0.9414 0.6855 0.2327 0.011(7) Uiso 1 1 calc R . . . .
C13 C 0.83584(13) 0.73825(13) 0.3320(3) 0.0162(4) Uani 1 1 d . . . . .
H13 H 0.8540 0.7904 0.3050 0.018(7) Uiso 1 1 calc R . . . .
C14 C 0.47200(13) 0.49518(11) 0.5686(3) 0.0133(4) Uani 1 1 d . . . . .
C15 C 0.38677(12) 0.49720(11) 0.5181(4) 0.0162(3) Uani 1 1 d . . . . .
H15 H 0.3603 0.5463 0.4932 0.031(8) Uiso 1 1 calc R . . . .
C16 C 0.34058(13) 0.42756(13) 0.5044(4) 0.0184(4) Uani 1 1 d . . . . .
H16 H 0.2829 0.4293 0.4690 0.017(7) Uiso 1 1 calc R . . . .
C17 C 0.37880(14) 0.35557(12) 0.5422(3) 0.0191(4) Uani 1 1 d . . . . .
H17 H 0.3475 0.3080 0.5320 0.030(7) Uiso 1 1 calc R . . . .
C18 C 0.46351(15) 0.35337(12) 0.5955(3) 0.0182(4) Uani 1 1 d . . . . .
H18 H 0.4893 0.3043 0.6238 0.023(7) Uiso 1 1 calc R . . . .
C19 C 0.51013(13) 0.42247(12) 0.6073(3) 0.0146(4) Uani 1 1 d . . . . .
H19 H 0.5679 0.4204 0.6416 0.015(6) Uiso 1 1 calc R . . . .
N21 N 0.63480(11) 0.88138(11) 0.1901(3) 0.0155(4) Uani 1 1 d . . . . .
O21 O 0.68469(10) 0.90225(10) 0.3247(2) 0.0194(3) Uani 1 1 d . . . . .
O22 O 0.62798(11) 0.92281(9) 0.0500(2) 0.0229(4) Uani 1 1 d . . . . .
O23 O 0.59467(11) 0.81841(9) 0.2124(3) 0.0210(3) Uani 1 1 d . . . . .
N24 N 0.76598(11) 0.84723(12) 0.8381(3) 0.0171(4) Uani 1 1 d . . . . .
O24 O 0.74806(11) 0.88269(10) 0.6830(2) 0.0217(3) Uani 1 1 d . . . . .
O25 O 0.73663(11) 0.78033(10) 0.8633(3) 0.0243(4) Uani 1 1 d . . . . .
O26 O 0.81257(11) 0.88036(11) 0.9513(3) 0.0265(4) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O24 2.0257(17) . ?
Zn1 O21 2.0473(17) . ?
Zn1 N5 2.0546(17) . ?
Zn1 N1 2.1720(18) . ?
Zn1 N10 2.2036(18) . ?
C1 N1 1.337(3) . ?
C1 C2 1.396(3) . ?
C1 H1 0.9500 . ?
N1 C4 1.352(3) . ?
C2 N2 1.330(3) . ?
C2 H2 0.9500 . ?
N2 C3 1.350(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.493(3) . ?
C5 N5 1.342(3) . ?
C5 C6 1.388(3) . ?
N5 C9 1.341(2) . ?
C6 C7 1.399(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(3) . ?
C7 C14 1.486(3) . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.485(3) . ?
C10 N10 1.355(3) . ?
C10 C11 1.397(3) . ?
N10 C13 1.334(3) . ?
C11 N11 1.341(3) . ?
C11 H11 0.9500 . ?
N11 C12 1.339(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.401(3) . ?
C14 C19 1.401(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N21 O22 1.226(2) . ?
N21 O23 1.253(2) . ?
N21 O21 1.293(2) . ?
N24 O26 1.231(3) . ?
N24 O25 1.240(3) . ?
N24 O24 1.290(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O24 Zn1 O21 85.48(7) . . ?
O24 Zn1 N5 132.93(7) . . ?
O21 Zn1 N5 141.58(7) . . ?
O24 Zn1 N1 97.38(7) . . ?
O21 Zn1 N1 100.64(7) . . ?
N5 Zn1 N1 76.75(7) . . ?
O24 Zn1 N10 101.78(7) . . ?
O21 Zn1 N10 100.13(7) . . ?
N5 Zn1 N10 75.94(7) . . ?
N1 Zn1 N10 152.67(7) . . ?
N1 C1 C2 120.8(2) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 N1 C4 117.42(19) . . ?
C1 N1 Zn1 128.55(15) . . ?
C4 N1 Zn1 113.91(14) . . ?
N2 C2 C1 122.8(2) . . ?
N2 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 N2 C3 116.0(2) . . ?
N2 C3 C4 122.2(2) . . ?
N2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
N1 C4 C3 120.7(2) . . ?
N1 C4 C5 115.68(18) . . ?
C3 C4 C5 123.6(2) . . ?
N5 C5 C6 121.56(18) . . ?
N5 C5 C4 113.75(18) . . ?
C6 C5 C4 124.69(18) . . ?
C9 N5 C5 120.09(17) . . ?
C9 N5 Zn1 120.30(13) . . ?
C5 N5 Zn1 119.17(14) . . ?
C5 C6 C7 119.18(18) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C8 118.55(17) . . ?
C6 C7 C14 121.00(18) . . ?
C8 C7 C14 120.40(17) . . ?
C9 C8 C7 118.58(17) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
N5 C9 C8 121.97(17) . . ?
N5 C9 C10 113.89(16) . . ?
C8 C9 C10 124.04(17) . . ?
N10 C10 C11 120.42(18) . . ?
N10 C10 C9 115.63(17) . . ?
C11 C10 C9 123.93(18) . . ?
C13 N10 C10 117.33(18) . . ?
C13 N10 Zn1 129.00(15) . . ?
C10 N10 Zn1 113.43(13) . . ?
N11 C11 C10 122.2(2) . . ?
N11 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C12 N11 C11 116.42(19) . . ?
N11 C12 C13 122.1(2) . . ?
N11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
N10 C13 C12 121.4(2) . . ?
N10 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C19 119.31(18) . . ?
C15 C14 C7 120.27(18) . . ?
C19 C14 C7 120.40(18) . . ?
C16 C15 C14 120.39(19) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.05(19) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.76(18) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
O22 N21 O23 123.14(19) . . ?
O22 N21 O21 120.08(18) . . ?
O23 N21 O21 116.78(18) . . ?
N21 O21 Zn1 104.42(12) . . ?
O26 N24 O25 123.3(2) . . ?
O26 N24 O24 118.79(19) . . ?
O25 N24 O24 117.91(18) . . ?
N24 O24 Zn1 110.79(13) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C4 -1.4(3) . . . . ?
C2 C1 N1 Zn1 -177.23(15) . . . . ?
N1 C1 C2 N2 1.8(3) . . . . ?
C1 C2 N2 C3 -0.4(3) . . . . ?
C2 N2 C3 C4 -1.3(3) . . . . ?
C1 N1 C4 C3 -0.1(3) . . . . ?
Zn1 N1 C4 C3 176.26(17) . . . . ?
C1 N1 C4 C5 -179.30(18) . . . . ?
Zn1 N1 C4 C5 -2.9(2) . . . . ?
N2 C3 C4 N1 1.6(4) . . . . ?
N2 C3 C4 C5 -179.3(2) . . . . ?
N1 C4 C5 N5 8.2(3) . . . . ?
C3 C4 C5 N5 -170.9(2) . . . . ?
N1 C4 C5 C6 -171.7(2) . . . . ?
C3 C4 C5 C6 9.2(3) . . . . ?
C6 C5 N5 C9 -2.5(3) . . . . ?
C4 C5 N5 C9 177.56(19) . . . . ?
C6 C5 N5 Zn1 169.91(15) . . . . ?
C4 C5 N5 Zn1 -10.0(2) . . . . ?
N5 C5 C6 C7 1.4(3) . . . . ?
C4 C5 C6 C7 -178.69(19) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C5 C6 C7 C14 -176.20(18) . . . . ?
C6 C7 C8 C9 -2.6(3) . . . . ?
C14 C7 C8 C9 174.8(2) . . . . ?
C5 N5 C9 C8 1.0(3) . . . . ?
Zn1 N5 C9 C8 -171.36(18) . . . . ?
C5 N5 C9 C10 177.42(18) . . . . ?
Zn1 N5 C9 C10 5.1(3) . . . . ?
C7 C8 C9 N5 1.6(4) . . . . ?
C7 C8 C9 C10 -174.5(2) . . . . ?
N5 C9 C10 N10 -9.8(3) . . . . ?
C8 C9 C10 N10 166.5(2) . . . . ?
N5 C9 C10 C11 171.7(2) . . . . ?
C8 C9 C10 C11 -12.0(4) . . . . ?
C11 C10 N10 C13 3.1(3) . . . . ?
C9 C10 N10 C13 -175.5(2) . . . . ?
C11 C10 N10 Zn1 -171.82(15) . . . . ?
C9 C10 N10 Zn1 9.6(2) . . . . ?
N10 C10 C11 N11 -1.8(3) . . . . ?
C9 C10 C11 N11 176.6(2) . . . . ?
C10 C11 N11 C12 -0.7(3) . . . . ?
C11 N11 C12 C13 1.9(3) . . . . ?
C10 N10 C13 C12 -1.9(3) . . . . ?
Zn1 N10 C13 C12 172.03(17) . . . . ?
N11 C12 C13 N10 -0.6(4) . . . . ?
C6 C7 C14 C15 34.4(3) . . . . ?
C8 C7 C14 C15 -143.0(2) . . . . ?
C6 C7 C14 C19 -147.0(2) . . . . ?
C8 C7 C14 C19 35.6(3) . . . . ?
C19 C14 C15 C16 -0.8(3) . . . . ?
C7 C14 C15 C16 177.8(2) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
C17 C18 C19 C14 1.0(3) . . . . ?
C15 C14 C19 C18 0.0(3) . . . . ?
C7 C14 C19 C18 -178.59(19) . . . . ?
O22 N21 O21 Zn1 179.26(15) . . . . ?
O23 N21 O21 Zn1 -0.2(2) . . . . ?
O26 N24 O24 Zn1 179.46(16) . . . . ?
O25 N24 O24 Zn1 1.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 N24 0.95 2.65 3.580(3) 165 3_465
C3 H3 O25 0.95 2.56 3.345(3) 141 3_465
C8 H8 O26 0.95 2.56 3.495(3) 167 4_644
C11 H11 O22 0.95 2.65 3.283(3) 125 4_645
C12 H12 O23 0.95 2.44 3.323(3) 155 3_565

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_JF2351F
_database_code_depnum_ccdc_archive 'CCDC 1050959'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 I2 N5 Zn'
_chemical_formula_sum            'C19 H13 I2 N5 Zn'
_chemical_formula_weight         630.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.9036(2)
_cell_length_b                   14.6668(3)
_cell_length_c                   19.4642(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1970.82(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      70.11

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.125
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    26.440
_shelx_estimated_absorpt_T_min   0.145
_shelx_estimated_absorpt_T_max   0.166
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.0763
_exptl_absorpt_correction_T_max  0.2274
_exptl_absorpt_process_details   'SADABS 2014/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14723
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         6.450
_diffrn_reflns_theta_max         68.231
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3611
_reflns_number_gt                3607
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_exptl_special_details           
;
An orange block with approximate orthogonal dimensions 0.119 x 0.110 x
0.106mm3 was placed and optically centered on the Bruker Duo(1) APEXII CCD
system at 183C(90K).  Indexing of the unit cell used a random set of
reflections collected from three series of 0.5 wide omega-scans, 10 seconds
per frame, and 30 frames per series that were well distributed in reciprocal
space. Data were collected [CuKa] with 0.5 wide scans, variable time per
frame dependent upon detector 2theta angle and varying phi and omega angles
such that nearly all unique reflections were collected at least once.  The
crystal to detector distance was 4.96cm, thus providing a complete sphere of
data to 2thetamax=140.12.
;


_computing_data_collection       'Apex2 (2013.10-2) (Bruker, 2013)'
_computing_cell_refinement       'SAINT (8.34a) (Bruker, 2013)'
_computing_data_reduction        'SAINT (8.34a) (Bruker, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+5.7514P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.417(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3611
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.202
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.79518(13) 1.07022(4) 0.64395(3) 0.03903(18) Uani 0.91 1 d . . P A 1
I2 I 0.28919(11) 0.91854(4) 0.70639(3) 0.03780(18) Uani 0.91 1 d . . P A 1
I1B I 0.522(3) 1.0737(16) 0.6455(11) 0.082(5) Uiso 0.05 1 d . . P A 2
I2B I 1.037(3) 0.9324(15) 0.7126(11) 0.080(5) Uiso 0.05 1 d . . P A 2
I1C I 0.913(3) 1.0803(14) 0.6436(9) 0.050(4) Uiso 0.04 1 d . . P A 3
I1D I 0.411(3) 0.9222(12) 0.7072(9) 0.049(4) Uiso 0.04 1 d . . P A 3
Zn1 Zn 0.65471(17) 0.95222(7) 0.72793(5) 0.0344(3) Uani 1 1 d . . . . .
N1 N 0.7783(13) 0.8273(5) 0.6814(4) 0.0354(16) Uani 1 1 d . . . . .
C1 C 0.8250(15) 0.8127(6) 0.6156(5) 0.040(2) Uani 1 1 d . . . . .
H1 H 0.8118 0.8607 0.5832 0.05(3) Uiso 1 1 calc R . . . .
C2 C 0.8921(16) 0.7287(7) 0.5942(5) 0.045(2) Uani 1 1 d . . . . .
H2 H 0.9215 0.7203 0.5470 0.02(2) Uiso 1 1 calc R . . . .
N3 N 0.9176(14) 0.6587(6) 0.6370(5) 0.047(2) Uani 1 1 d . . . . .
C3 C 0.8728(16) 0.6739(6) 0.7029(5) 0.040(2) Uani 1 1 d . . . . .
H3 H 0.8865 0.6254 0.7349 0.06(3) Uiso 1 1 calc R . . . .
C4 C 0.8069(15) 0.7580(5) 0.7266(4) 0.0358(18) Uani 1 1 d . . . . .
C5 C 0.7627(13) 0.7803(6) 0.7989(4) 0.0338(19) Uani 1 1 d . . . . .
C6 C 0.7553(13) 0.7157(6) 0.8523(5) 0.037(2) Uani 1 1 d . . . . .
H6 H 0.7737 0.6528 0.8429 0.03(2) Uiso 1 1 calc R . . . .
N6 N 0.7285(11) 0.8694(5) 0.8104(4) 0.0341(16) Uani 1 1 d . . . . .
C7 C 0.7207(14) 0.7451(5) 0.9190(4) 0.0325(17) Uani 1 1 d . . . . .
C8 C 0.6931(15) 0.8382(6) 0.9292(4) 0.0345(18) Uani 1 1 d . . . . .
H8 H 0.6738 0.8611 0.9744 0.04(3) Uiso 1 1 calc R . . . .
C9 C 0.6935(14) 0.8980(6) 0.8737(4) 0.0339(18) Uani 1 1 d . . . . .
C10 C 0.6632(13) 0.9971(6) 0.8805(4) 0.0329(19) Uani 1 1 d . . . . .
C11 C 0.6554(15) 1.0446(6) 0.9431(5) 0.040(2) Uani 1 1 d . . . . .
H11 H 0.6692 1.0114 0.9846 0.05(3) Uiso 1 1 calc R . . . .
N11 N 0.6455(11) 1.0421(5) 0.8211(4) 0.0326(15) Uani 1 1 d . . . . .
C12 C 0.6128(17) 1.1774(7) 0.8862(5) 0.045(2) Uani 1 1 d . . . . .
H12 H 0.5944 1.2416 0.8861 0.03(2) Uiso 1 1 calc R . . . .
C13 C 0.6215(15) 1.1322(6) 0.8240(5) 0.040(2) Uani 1 1 d . . . . .
H13 H 0.6101 1.1659 0.7825 0.03(2) Uiso 1 1 calc R . . . .
N13 N 0.6295(15) 1.1342(6) 0.9464(4) 0.048(2) Uani 1 1 d . . . . .
C14 C 0.7052(16) 0.6777(6) 0.9765(4) 0.0325(17) Uani 1 1 d . . . . .
C15 C 0.6788(16) 0.5855(6) 0.9656(5) 0.045(2) Uani 1 1 d . . . . .
H15 H 0.6719 0.5626 0.9200 0.08(4) Uiso 1 1 calc R . . . .
C16 C 0.6626(19) 0.5264(7) 1.0204(5) 0.053(3) Uani 1 1 d . . . . .
H16 H 0.6415 0.4633 1.0123 0.05(3) Uiso 1 1 calc R . . . .
C17 C 0.6768(15) 0.5587(7) 1.0875(5) 0.044(2) Uani 1 1 d . . . . .
H17 H 0.6654 0.5177 1.1250 0.06(4) Uiso 1 1 calc R . . . .
C18 C 0.7069(17) 0.6485(7) 1.0992(5) 0.042(2) Uani 1 1 d . . . . .
H18 H 0.7165 0.6706 1.1449 0.04(3) Uiso 1 1 calc R . . . .
C19 C 0.7238(17) 0.7089(6) 1.0438(5) 0.044(2) Uani 1 1 d . . . . .
H19 H 0.7481 0.7717 1.0521 0.09(5) Uiso 1 1 calc R . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Zn1 2.5705(12) . ?
I2 Zn1 2.6053(14) . ?
I1B Zn1 2.57(2) . ?
I2B Zn1 2.67(2) . ?
I1C Zn1 3.07(2) . ?
I1D Zn1 1.78(2) . ?
Zn1 N6 2.077(7) . ?
Zn1 N1 2.215(7) . ?
Zn1 N11 2.243(7) . ?
N1 C1 1.338(12) . ?
N1 C4 1.358(11) . ?
C1 C2 1.381(14) . ?
C1 H1 0.9500 . ?
C2 N3 1.333(13) . ?
C2 H2 0.9500 . ?
N3 C3 1.338(13) . ?
C3 C4 1.393(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.477(12) . ?
C5 N6 1.346(11) . ?
C5 C6 1.407(12) . ?
C6 C7 1.388(12) . ?
C6 H6 0.9500 . ?
N6 C9 1.324(11) . ?
C7 C8 1.393(12) . ?
C7 C14 1.498(11) . ?
C8 C9 1.392(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.474(12) . ?
C10 N11 1.338(10) . ?
C10 C11 1.403(12) . ?
C11 N13 1.327(12) . ?
C11 H11 0.9500 . ?
N11 C13 1.332(12) . ?
C12 N13 1.339(14) . ?
C12 C13 1.382(14) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.381(13) . ?
C14 C19 1.392(12) . ?
C15 C16 1.379(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.353(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(13) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1D Zn1 N6 105.1(6) . . ?
I1D Zn1 N1 93.8(6) . . ?
N6 Zn1 N1 74.8(3) . . ?
I1D Zn1 N11 107.5(6) . . ?
N6 Zn1 N11 74.1(3) . . ?
N1 Zn1 N11 145.9(3) . . ?
N6 Zn1 I1B 167.7(5) . . ?
N1 Zn1 I1B 117.1(5) . . ?
N11 Zn1 I1B 95.0(5) . . ?
N6 Zn1 I1 142.5(2) . . ?
N1 Zn1 I1 98.7(2) . . ?
N11 Zn1 I1 97.42(18) . . ?
N6 Zn1 I2 104.5(2) . . ?
N1 Zn1 I2 98.7(2) . . ?
N11 Zn1 I2 102.4(2) . . ?
I1 Zn1 I2 113.00(5) . . ?
N6 Zn1 I2B 77.3(5) . . ?
N1 Zn1 I2B 58.9(5) . . ?
N11 Zn1 I2B 100.5(5) . . ?
I1B Zn1 I2B 111.0(7) . . ?
I1D Zn1 I1C 125.3(7) . . ?
N6 Zn1 I1C 129.1(5) . . ?
N1 Zn1 I1C 93.7(4) . . ?
N11 Zn1 I1C 95.1(4) . . ?
C1 N1 C4 117.7(8) . . ?
C1 N1 Zn1 128.1(6) . . ?
C4 N1 Zn1 114.2(6) . . ?
C1 N1 I2B 99.4(8) . . ?
C4 N1 I2B 101.8(8) . . ?
Zn1 N1 I2B 69.9(6) . . ?
N1 C1 C2 120.8(8) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
N3 C2 C1 122.9(9) . . ?
N3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C2 N3 C3 116.1(8) . . ?
N3 C3 C4 122.7(8) . . ?
N3 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
N1 C4 C3 119.7(8) . . ?
N1 C4 C5 115.0(7) . . ?
C3 C4 C5 125.3(8) . . ?
N6 C5 C6 121.6(8) . . ?
N6 C5 C4 114.1(7) . . ?
C6 C5 C4 124.3(8) . . ?
C7 C6 C5 119.2(8) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C9 N6 C5 119.7(7) . . ?
C9 N6 Zn1 119.2(6) . . ?
C5 N6 Zn1 118.8(6) . . ?
C6 C7 C8 117.5(8) . . ?
C6 C7 C14 120.4(7) . . ?
C8 C7 C14 122.1(8) . . ?
C9 C8 C7 120.5(8) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
N6 C9 C8 121.5(8) . . ?
N6 C9 C10 115.0(7) . . ?
C8 C9 C10 123.4(7) . . ?
N11 C10 C11 120.1(8) . . ?
N11 C10 C9 114.9(7) . . ?
C11 C10 C9 125.0(8) . . ?
N13 C11 C10 122.6(9) . . ?
N13 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C13 N11 C10 117.6(8) . . ?
C13 N11 Zn1 128.4(6) . . ?
C10 N11 Zn1 114.0(5) . . ?
N13 C12 C13 122.4(9) . . ?
N13 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
N11 C13 C12 121.3(9) . . ?
N11 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C11 N13 C12 116.0(9) . . ?
C15 C14 C19 118.6(8) . . ?
C15 C14 C7 122.7(8) . . ?
C19 C14 C7 118.6(8) . . ?
C16 C15 C14 120.4(9) . . ?
C16 C15 I1B 124.3(9) . 3_646 ?
C14 C15 I1B 105.5(8) . 3_646 ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.4(9) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 120.0(8) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.9(9) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C14 C19 C18 120.6(9) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 2.7(15) . . . . ?
Zn1 N1 C1 C2 -176.7(8) . . . . ?
I2B N1 C1 C2 111.4(11) . . . . ?
N1 C1 C2 N3 -1.2(17) . . . . ?
C1 C2 N3 C3 0.5(16) . . . . ?
C2 N3 C3 C4 -1.3(16) . . . . ?
C1 N1 C4 C3 -3.4(15) . . . . ?
Zn1 N1 C4 C3 176.1(8) . . . . ?
I2B N1 C4 C3 -110.8(10) . . . . ?
C1 N1 C4 C5 176.8(9) . . . . ?
Zn1 N1 C4 C5 -3.8(11) . . . . ?
I2B N1 C4 C5 69.4(10) . . . . ?
N3 C3 C4 N1 2.8(16) . . . . ?
N3 C3 C4 C5 -177.4(10) . . . . ?
N1 C4 C5 N6 -9.4(12) . . . . ?
C3 C4 C5 N6 170.8(9) . . . . ?
N1 C4 C5 C6 170.5(9) . . . . ?
C3 C4 C5 C6 -9.4(16) . . . . ?
N6 C5 C6 C7 -3.0(14) . . . . ?
C4 C5 C6 C7 177.1(9) . . . . ?
C6 C5 N6 C9 2.3(13) . . . . ?
C4 C5 N6 C9 -177.8(9) . . . . ?
C6 C5 N6 Zn1 -160.5(7) . . . . ?
C4 C5 N6 Zn1 19.4(10) . . . . ?
C5 C6 C7 C8 0.6(14) . . . . ?
C5 C6 C7 C14 177.9(9) . . . . ?
C6 C7 C8 C9 2.3(15) . . . . ?
C14 C7 C8 C9 -174.9(9) . . . . ?
C5 N6 C9 C8 0.7(14) . . . . ?
Zn1 N6 C9 C8 163.5(7) . . . . ?
C5 N6 C9 C10 178.5(8) . . . . ?
Zn1 N6 C9 C10 -18.8(11) . . . . ?
C7 C8 C9 N6 -3.1(15) . . . . ?
C7 C8 C9 C10 179.4(9) . . . . ?
N6 C9 C10 N11 9.9(12) . . . . ?
C8 C9 C10 N11 -172.4(9) . . . . ?
N6 C9 C10 C11 -169.1(9) . . . . ?
C8 C9 C10 C11 8.6(16) . . . . ?
N11 C10 C11 N13 0.4(16) . . . . ?
C9 C10 C11 N13 179.4(10) . . . . ?
C11 C10 N11 C13 0.3(14) . . . . ?
C9 C10 N11 C13 -178.8(9) . . . . ?
C11 C10 N11 Zn1 -178.5(7) . . . . ?
C9 C10 N11 Zn1 2.4(10) . . . . ?
C10 N11 C13 C12 -0.8(15) . . . . ?
Zn1 N11 C13 C12 177.9(8) . . . . ?
N13 C12 C13 N11 0.6(18) . . . . ?
C10 C11 N13 C12 -0.6(17) . . . . ?
C13 C12 N13 C11 0.1(18) . . . . ?
C6 C7 C14 C15 -15.4(16) . . . . ?
C8 C7 C14 C15 161.7(10) . . . . ?
C6 C7 C14 C19 162.6(10) . . . . ?
C8 C7 C14 C19 -20.3(15) . . . . ?
C19 C14 C15 C16 2.9(17) . . . . ?
C7 C14 C15 C16 -179.0(11) . . . . ?
C19 C14 C15 I1B 150.1(10) . . . 3_646 ?
C7 C14 C15 I1B -31.9(13) . . . 3_646 ?
C14 C15 C16 C17 -1.4(18) . . . . ?
I1B C15 C16 C17 -142.2(11) 3_646 . . . ?
C15 C16 C17 C18 0.0(18) . . . . ?
C16 C17 C18 C19 0.0(18) . . . . ?
C15 C14 C19 C18 -3.0(17) . . . . ?
C7 C14 C19 C18 178.9(10) . . . . ?
C17 C18 C19 C14 1.6(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 I2B 0.95 3.06 3.95(2) 159. 3_746
C3 H3 I1C 0.95 2.82 3.61(2) 141. 3_746
C6 H6 I1B 0.95 2.36 2.83(2) 110. 3_646
C6 H6 I1C 0.95 2.43 3.03(3) 122. 3_746
C13 H13 I1B 0.95 3.05 3.64(2) 122. .
C15 H15 I1B 0.95 1.86 2.57(2) 130. 3_646

_refine_diff_density_max         0.969
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.122



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gzhang70
_database_code_depnum_ccdc_archive 'CCDC 1050960'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 Co N7 O S2'
_chemical_formula_weight         518.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9547(10)
_cell_length_b                   10.2686(11)
_cell_length_c                   12.4191(13)
_cell_angle_alpha                86.077(4)
_cell_angle_beta                 86.323(4)
_cell_angle_gamma                78.479(4)
_cell_volume                     1114.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7105
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.28

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ORANGE
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             530
_exptl_absorpt_coefficient_mu    0.988
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9077
_exptl_absorpt_correction_T_max  0.9523
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus ROTATING ANODE'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4578
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         26.44
_reflns_number_total             4578
_reflns_number_gt                3755
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0558P)²+0.4706P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4578
_refine_ls_number_parameters     280
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.85991(4) 0.51035(3) 0.21449(2) 0.01873(11) Uani 1 1 d . . .
S1 S 0.55000(9) 0.86864(7) 0.40903(7) 0.0452(2) Uani 1 1 d U . .
S2 S 0.80714(7) 0.69554(6) 0.07640(5) 0.02257(15) Uani 1 1 d . . .
N1 N 0.7124(2) 0.6449(2) 0.30914(15) 0.0216(4) Uani 1 1 d . . .
N2 N 0.9984(2) 0.39253(19) 0.10233(15) 0.0233(4) Uani 1 1 d . . .
N3 N 0.6820(2) 0.39665(19) 0.20843(15) 0.0241(4) Uani 1 1 d . . .
N4 N 0.4533(3) 0.2469(3) 0.2241(2) 0.0440(7) Uani 1 1 d . . .
N5 N 0.8965(2) 0.36860(18) 0.34302(14) 0.0175(4) Uani 1 1 d . . .
N6 N 1.0717(2) 0.53535(18) 0.27929(15) 0.0193(4) Uani 1 1 d . . .
N7 N 1.3481(3) 0.5375(2) 0.37074(19) 0.0332(5) Uani 1 1 d . . .
C1 C 0.6408(3) 0.7373(2) 0.34841(19) 0.0223(5) Uani 1 1 d . . .
C2 C 0.9221(3) 0.6437(2) -0.02922(19) 0.0207(5) Uani 1 1 d . . .
C3 C 0.5754(3) 0.4133(3) 0.1367(2) 0.0369(7) Uani 1 1 d . . .
H3A H 0.5773 0.4780 0.0784 0.044 Uiso 1 1 calc R . .
C4 C 0.4613(4) 0.3393(3) 0.1442(2) 0.0472(8) Uani 1 1 d . . .
H4A H 0.3869 0.3548 0.0912 0.057 Uiso 1 1 calc R . .
C5 C 0.5603(3) 0.2305(3) 0.2955(2) 0.0308(6) Uani 1 1 d . . .
H5A H 0.5586 0.1650 0.3532 0.037 Uiso 1 1 calc R . .
C6 C 0.6751(3) 0.3048(2) 0.28997(18) 0.0223(5) Uani 1 1 d . . .
C7 C 0.7963(3) 0.2890(2) 0.36754(18) 0.0200(5) Uani 1 1 d . . .
C8 C 0.8091(3) 0.2006(2) 0.45769(18) 0.0209(5) Uani 1 1 d . . .
H8A H 0.7354 0.1462 0.4739 0.025 Uiso 1 1 calc R . .
C9 C 0.9309(3) 0.1918(2) 0.52444(18) 0.0202(5) Uani 1 1 d . . .
C10 C 1.0360(3) 0.2744(2) 0.49559(18) 0.0218(5) Uani 1 1 d . . .
H10A H 1.1212 0.2711 0.5381 0.026 Uiso 1 1 calc R . .
C11 C 1.0146(3) 0.3615(2) 0.40408(18) 0.0192(5) Uani 1 1 d . . .
C12 C 1.1188(3) 0.4523(2) 0.36546(18) 0.0200(5) Uani 1 1 d . . .
C13 C 1.2564(3) 0.4544(2) 0.4096(2) 0.0265(5) Uani 1 1 d . . .
H13A H 1.2872 0.3949 0.4697 0.032 Uiso 1 1 calc R . .
C14 C 1.2986(3) 0.6186(2) 0.2868(2) 0.0284(6) Uani 1 1 d . . .
H14A H 1.3593 0.6798 0.2575 0.034 Uiso 1 1 calc R . .
C15 C 1.1635(3) 0.6176(2) 0.2405(2) 0.0232(5) Uani 1 1 d . . .
H15A H 1.1346 0.6765 0.1798 0.028 Uiso 1 1 calc R . .
C16 C 0.9477(3) 0.1003(2) 0.62283(19) 0.0218(5) Uani 1 1 d . . .
C17 C 0.8507(3) 0.0101(3) 0.6472(2) 0.0348(6) Uani 1 1 d . . .
H17A H 0.7746 0.0047 0.5987 0.042 Uiso 1 1 calc R . .
C18 C 0.8640(3) -0.0714(3) 0.7408(2) 0.0419(7) Uani 1 1 d . . .
H18A H 0.7969 -0.1320 0.7562 0.050 Uiso 1 1 calc R . .
C19 C 0.9744(3) -0.0653(3) 0.8122(2) 0.0328(6) Uani 1 1 d . . .
H19A H 0.9820 -0.1202 0.8771 0.039 Uiso 1 1 calc R . .
C20 C 1.0733(3) 0.0208(2) 0.7884(2) 0.0294(6) Uani 1 1 d . . .
H20A H 1.1509 0.0243 0.8362 0.035 Uiso 1 1 calc R . .
C21 C 1.0589(3) 0.1022(2) 0.6945(2) 0.0279(6) Uani 1 1 d . . .
H21A H 1.1278 0.1612 0.6789 0.033 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.081(2) . ?
Co1 N5 2.0815(18) . ?
Co1 N2 2.086(2) . ?
Co1 N3 2.163(2) . ?
Co1 N6 2.175(2) . ?
Co1 S2 2.4657(6) . ?
S1 C1 1.634(3) . ?
S2 C2 1.663(2) . ?
N1 C1 1.153(3) . ?
N2 C2 1.152(3) 2_765 ?
N3 C3 1.325(3) . ?
N3 C6 1.343(3) . ?
N4 C5 1.325(3) . ?
N4 C4 1.334(4) . ?
N5 C11 1.328(3) . ?
N5 C7 1.338(3) . ?
N6 C15 1.338(3) . ?
N6 C12 1.356(3) . ?
N7 C14 1.331(3) . ?
N7 C13 1.344(3) . ?
C2 N2 1.152(3) 2_765 ?
C3 C4 1.385(4) . ?
C3 H3A 0.9500 . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.474(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.397(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.403(3) . ?
C9 C16 1.486(3) . ?
C10 C11 1.396(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.483(3) . ?
C12 C13 1.385(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.375(4) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C21 1.381(3) . ?
C16 C17 1.398(3) . ?
C17 C18 1.383(4) . ?
C17 H17A 0.9500 . ?
C18 C19 1.382(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.377(4) . ?
C19 H19A 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Co1 N5 92.24(7) . . ?
N1 Co1 N2 172.47(7) . . ?
N5 Co1 N2 95.17(7) . . ?
N1 Co1 N3 89.29(8) . . ?
N5 Co1 N3 75.07(7) . . ?
N2 Co1 N3 91.38(8) . . ?
N1 Co1 N6 97.33(7) . . ?
N5 Co1 N6 75.20(7) . . ?
N2 Co1 N6 85.83(8) . . ?
N3 Co1 N6 149.75(7) . . ?
N1 Co1 S2 82.11(5) . . ?
N5 Co1 S2 174.03(5) . . ?
N2 Co1 S2 90.51(5) . . ?
N3 Co1 S2 106.66(6) . . ?
N6 Co1 S2 103.48(5) . . ?
C2 S2 Co1 104.27(8) . . ?
C1 N1 Co1 166.91(18) . . ?
C2 N2 Co1 163.86(17) 2_765 . ?
C3 N3 C6 117.3(2) . . ?
C3 N3 Co1 126.93(16) . . ?
C6 N3 Co1 115.67(16) . . ?
C5 N4 C4 116.2(2) . . ?
C11 N5 C7 119.88(19) . . ?
C11 N5 Co1 120.22(14) . . ?
C7 N5 Co1 119.81(16) . . ?
C15 N6 C12 117.0(2) . . ?
C15 N6 Co1 127.50(16) . . ?
C12 N6 Co1 115.38(14) . . ?
C14 N7 C13 115.9(2) . . ?
N1 C1 S1 175.9(2) . . ?
N2 C2 S2 179.8(2) 2_765 . ?
N3 C3 C4 122.0(2) . . ?
N3 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
N4 C4 C3 121.6(3) . . ?
N4 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?
N4 C5 C6 123.1(2) . . ?
N4 C5 H5A 118.4 . . ?
C6 C5 H5A 118.4 . . ?
N3 C6 C5 119.8(2) . . ?
N3 C6 C7 115.5(2) . . ?
C5 C6 C7 124.6(2) . . ?
N5 C7 C8 121.8(2) . . ?
N5 C7 C6 113.50(19) . . ?
C8 C7 C6 124.7(2) . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C8 C9 C10 117.2(2) . . ?
C8 C9 C16 121.6(2) . . ?
C10 C9 C16 121.2(2) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
N5 C11 C10 121.6(2) . . ?
N5 C11 C12 114.05(19) . . ?
C10 C11 C12 124.3(2) . . ?
N6 C12 C13 120.3(2) . . ?
N6 C12 C11 114.9(2) . . ?
C13 C12 C11 124.7(2) . . ?
N7 C13 C12 122.5(2) . . ?
N7 C13 H13A 118.7 . . ?
C12 C13 H13A 118.7 . . ?
N7 C14 C15 122.8(2) . . ?
N7 C14 H14A 118.6 . . ?
C15 C14 H14A 118.6 . . ?
N6 C15 C14 121.4(2) . . ?
N6 C15 H15A 119.3 . . ?
C14 C15 H15A 119.3 . . ?
C21 C16 C17 117.4(2) . . ?
C21 C16 C9 121.2(2) . . ?
C17 C16 C9 121.4(2) . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C21 119.6(2) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C16 C21 C20 122.1(2) . . ?
C16 C21 H21A 119.0 . . ?
C20 C21 H21A 119.0 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Co1 S2 C2 174.52(10) . . . . ?
N5 Co1 S2 C2 155.4(5) . . . . ?
N2 Co1 S2 C2 -7.00(10) . . . . ?
N3 Co1 S2 C2 -98.60(10) . . . . ?
N6 Co1 S2 C2 78.83(10) . . . . ?
N5 Co1 N1 C1 150.5(9) . . . . ?
N2 Co1 N1 C1 -39.3(12) . . . . ?
N3 Co1 N1 C1 -134.5(9) . . . . ?
N6 Co1 N1 C1 75.1(9) . . . . ?
S2 Co1 N1 C1 -27.6(9) . . . . ?
N1 Co1 N2 C2 36.3(11) . . . 2_765 ?
N5 Co1 N2 C2 -153.5(7) . . . 2_765 ?
N3 Co1 N2 C2 131.4(7) . . . 2_765 ?
N6 Co1 N2 C2 -78.8(7) . . . 2_765 ?
S2 Co1 N2 C2 24.7(7) . . . 2_765 ?
N1 Co1 N3 C3 88.6(2) . . . . ?
N5 Co1 N3 C3 -178.9(2) . . . . ?
N2 Co1 N3 C3 -83.9(2) . . . . ?
N6 Co1 N3 C3 -168.0(2) . . . . ?
S2 Co1 N3 C3 7.0(2) . . . . ?
N1 Co1 N3 C6 -87.38(17) . . . . ?
N5 Co1 N3 C6 5.13(16) . . . . ?
N2 Co1 N3 C6 100.12(17) . . . . ?
N6 Co1 N3 C6 16.0(3) . . . . ?
S2 Co1 N3 C6 -168.93(15) . . . . ?
N1 Co1 N5 C11 -93.82(17) . . . . ?
N2 Co1 N5 C11 87.46(17) . . . . ?
N3 Co1 N5 C11 177.51(18) . . . . ?
N6 Co1 N5 C11 3.16(16) . . . . ?
S2 Co1 N5 C11 -74.9(6) . . . . ?
N1 Co1 N5 C7 82.74(17) . . . . ?
N2 Co1 N5 C7 -95.98(17) . . . . ?
N3 Co1 N5 C7 -5.93(16) . . . . ?
N6 Co1 N5 C7 179.73(18) . . . . ?
S2 Co1 N5 C7 101.7(5) . . . . ?
N1 Co1 N6 C15 -93.63(19) . . . . ?
N5 Co1 N6 C15 176.0(2) . . . . ?
N2 Co1 N6 C15 79.50(19) . . . . ?
N3 Co1 N6 C15 165.09(18) . . . . ?
S2 Co1 N6 C15 -10.03(19) . . . . ?
N1 Co1 N6 C12 90.17(16) . . . . ?
N5 Co1 N6 C12 -0.22(15) . . . . ?
N2 Co1 N6 C12 -96.70(16) . . . . ?
N3 Co1 N6 C12 -11.1(2) . . . . ?
S2 Co1 N6 C12 173.77(14) . . . . ?
Co1 N1 C1 S1 -84(3) . . . . ?
Co1 S2 C2 N2 41(100) . . . 2_765 ?
C6 N3 C3 C4 -0.3(4) . . . . ?
Co1 N3 C3 C4 -176.2(2) . . . . ?
C5 N4 C4 C3 0.2(5) . . . . ?
N3 C3 C4 N4 -0.2(5) . . . . ?
C4 N4 C5 C6 0.5(5) . . . . ?
C3 N3 C6 C5 0.9(4) . . . . ?
Co1 N3 C6 C5 177.31(19) . . . . ?
C3 N3 C6 C7 179.7(2) . . . . ?
Co1 N3 C6 C7 -3.9(3) . . . . ?
N4 C5 C6 N3 -1.1(4) . . . . ?
N4 C5 C6 C7 -179.7(3) . . . . ?
C11 N5 C7 C8 1.9(3) . . . . ?
Co1 N5 C7 C8 -174.66(17) . . . . ?
C11 N5 C7 C6 -177.74(19) . . . . ?
Co1 N5 C7 C6 5.7(3) . . . . ?
N3 C6 C7 N5 -0.9(3) . . . . ?
C5 C6 C7 N5 177.8(2) . . . . ?
N3 C6 C7 C8 179.5(2) . . . . ?
C5 C6 C7 C8 -1.9(4) . . . . ?
N5 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 C9 178.5(2) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C16 178.9(2) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C16 C9 C10 C11 -178.4(2) . . . . ?
C7 N5 C11 C10 -1.4(3) . . . . ?
Co1 N5 C11 C10 175.15(17) . . . . ?
C7 N5 C11 C12 178.14(19) . . . . ?
Co1 N5 C11 C12 -5.3(3) . . . . ?
C9 C10 C11 N5 0.1(3) . . . . ?
C9 C10 C11 C12 -179.4(2) . . . . ?
C15 N6 C12 C13 -0.1(3) . . . . ?
Co1 N6 C12 C13 176.47(18) . . . . ?
C15 N6 C12 C11 -178.92(19) . . . . ?
Co1 N6 C12 C11 -2.3(2) . . . . ?
N5 C11 C12 N6 4.8(3) . . . . ?
C10 C11 C12 N6 -175.6(2) . . . . ?
N5 C11 C12 C13 -173.9(2) . . . . ?
C10 C11 C12 C13 5.7(4) . . . . ?
C14 N7 C13 C12 0.2(4) . . . . ?
N6 C12 C13 N7 0.4(4) . . . . ?
C11 C12 C13 N7 179.0(2) . . . . ?
C13 N7 C14 C15 -1.0(4) . . . . ?
C12 N6 C15 C14 -0.6(3) . . . . ?
Co1 N6 C15 C14 -176.75(18) . . . . ?
N7 C14 C15 N6 1.2(4) . . . . ?
C8 C9 C16 C21 -173.1(2) . . . . ?
C10 C9 C16 C21 6.0(4) . . . . ?
C8 C9 C16 C17 6.2(4) . . . . ?
C10 C9 C16 C17 -174.7(2) . . . . ?
C21 C16 C17 C18 1.5(4) . . . . ?
C9 C16 C17 C18 -177.8(3) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C20 -1.3(5) . . . . ?
C18 C19 C20 C21 1.4(4) . . . . ?
C17 C16 C21 C20 -1.4(4) . . . . ?
C9 C16 C21 C20 177.9(2) . . . . ?
C19 C20 C21 C16 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.076
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_gzhang82
_database_code_depnum_ccdc_archive 'CCDC 1050961'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C38 H26 Fe N10, C4 Co N4 S4, 0.5(C H2 Cl2), H2 O '
_chemical_formula_sum            'C42.50 H29 Cl Co Fe N14 O S4'
_chemical_formula_weight         1030.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0795(11)
_cell_length_b                   11.8223(14)
_cell_length_c                   20.571(2)
_cell_angle_alpha                88.410(4)
_cell_angle_beta                 79.325(3)
_cell_angle_gamma                66.086(3)
_cell_volume                     2199.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9007
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.30

_exptl_crystal_description       BLADE
_exptl_crystal_colour            bronze
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7934
_exptl_absorpt_correction_T_max  0.9512
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37819
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.80
_reflns_number_total             8428
_reflns_number_gt                6421
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0436P)²+2.5346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8428
_refine_ls_number_parameters     592
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.91537(5) 0.77705(4) 0.75301(2) 0.01743(12) Uani 1 1 d . . .
Co1 Co 0.52002(5) 0.32594(4) 0.78459(2) 0.02454(13) Uani 1 1 d . . .
S1 S 0.43118(10) 0.74780(8) 0.77219(5) 0.0291(2) Uani 1 1 d . . .
S2 S 0.20399(11) 0.27399(10) 0.66895(5) 0.0405(3) Uani 1 1 d . . .
S3 S 0.90943(11) 0.18715(10) 0.59992(5) 0.0352(2) Uani 1 1 d . . .
S4 S 0.75015(11) 0.07941(9) 0.95120(5) 0.0378(2) Uani 1 1 d . . .
O1 O 0.8789(3) 0.7648(3) 1.08875(15) 0.0433(7) Uani 1 1 d D . .
H1WB H 0.872(5) 0.803(3) 1.0493(11) 0.052 Uiso 1 1 d D . .
H1WA H 0.905(5) 0.815(3) 1.1072(16) 0.052 Uiso 1 1 d D . .
N1 N 0.9836(3) 0.9028(2) 0.77523(13) 0.0203(6) Uani 1 1 d . . .
N2 N 1.0779(4) 1.0701(3) 0.82236(16) 0.0366(8) Uani 1 1 d . . .
N3 N 1.0024(3) 0.7035(2) 0.82543(13) 0.0190(6) Uani 1 1 d . . .
N4 N 0.8479(3) 0.4022(3) 0.76572(14) 0.0245(6) Uani 1 1 d . . .
N5 N 0.8773(3) 0.6271(2) 0.75433(13) 0.0185(6) Uani 1 1 d . . .
N6 N 1.0873(3) 0.6968(2) 0.68144(13) 0.0193(6) Uani 1 1 d . . .
N7 N 1.3003(3) 0.5828(3) 0.56815(15) 0.0298(7) Uani 1 1 d . . .
N8 N 0.8310(3) 0.8543(2) 0.68080(13) 0.0187(6) Uani 1 1 d . . .
N9 N 0.4176(3) 1.0256(3) 0.85260(14) 0.0279(7) Uani 1 1 d . . .
N10 N 0.7136(3) 0.8765(2) 0.80024(13) 0.0184(6) Uani 1 1 d . . .
N11 N 0.4726(3) 0.5031(3) 0.79510(14) 0.0251(6) Uani 1 1 d . . .
N12 N 0.3383(3) 0.3199(3) 0.76553(16) 0.0319(7) Uani 1 1 d . . .
N13 N 0.6599(3) 0.2649(3) 0.70025(14) 0.0278(7) Uani 1 1 d . . .
N14 N 0.6067(3) 0.2227(3) 0.85399(15) 0.0301(7) Uani 1 1 d . . .
C1 C 0.9669(4) 1.0084(3) 0.74573(17) 0.0246(7) Uani 1 1 d . . .
H1 H 0.9218 1.0270 0.7079 0.030 Uiso 1 1 calc R . .
C2 C 1.0143(4) 1.0910(3) 0.76933(19) 0.0320(9) Uani 1 1 d . . .
H2 H 1.0010 1.1652 0.7470 0.038 Uiso 1 1 calc R . .
C3 C 1.0973(4) 0.9637(3) 0.85083(18) 0.0299(8) Uani 1 1 d . . .
H3 H 1.1449 0.9449 0.8880 0.036 Uiso 1 1 calc R . .
C4 C 1.0509(3) 0.8790(3) 0.82842(16) 0.0214(7) Uani 1 1 d . . .
C5 C 1.0668(3) 0.7605(3) 0.85714(16) 0.0207(7) Uani 1 1 d . . .
C6 C 1.1405(4) 0.7044(3) 0.90711(16) 0.0239(7) Uani 1 1 d . . .
H6 H 1.1861 0.7447 0.9287 0.029 Uiso 1 1 calc R . .
C7 C 1.1479(4) 0.5875(3) 0.92598(16) 0.0231(7) Uani 1 1 d . . .
C8 C 1.0771(3) 0.5319(3) 0.89367(15) 0.0212(7) Uani 1 1 d . . .
H8 H 1.0780 0.4537 0.9062 0.025 Uiso 1 1 calc R . .
C9 C 1.0058(3) 0.5922(3) 0.84340(15) 0.0191(7) Uani 1 1 d . . .
C10 C 0.9323(3) 0.5478(3) 0.80127(15) 0.0193(7) Uani 1 1 d . . .
C11 C 0.9165(3) 0.4364(3) 0.80607(16) 0.0225(7) Uani 1 1 d . . .
H11 H 0.9558 0.3824 0.8393 0.027 Uiso 1 1 calc R . .
C12 C 0.7971(4) 0.4804(3) 0.71940(16) 0.0233(7) Uani 1 1 d . . .
H12 H 0.7497 0.4583 0.6892 0.028 Uiso 1 1 calc R . .
C13 C 0.8103(3) 0.5924(3) 0.71345(16) 0.0221(7) Uani 1 1 d . . .
H13 H 0.7711 0.6453 0.6798 0.026 Uiso 1 1 calc R . .
C14 C 1.2354(4) 0.5205(3) 0.97588(16) 0.0246(7) Uani 1 1 d . . .
C15 C 1.2612(4) 0.5845(3) 1.02523(16) 0.0270(8) Uani 1 1 d . . .
H15 H 1.2185 0.6725 1.0282 0.032 Uiso 1 1 calc R . .
C16 C 1.3489(4) 0.5194(4) 1.06954(17) 0.0306(8) Uani 1 1 d . . .
H16 H 1.3656 0.5632 1.1030 0.037 Uiso 1 1 calc R . .
C17 C 1.4123(4) 0.3921(4) 1.06570(17) 0.0301(8) Uani 1 1 d . . .
H17 H 1.4729 0.3482 1.0962 0.036 Uiso 1 1 calc R . .
C18 C 1.3873(4) 0.3277(3) 1.01697(17) 0.0287(8) Uani 1 1 d . . .
H18 H 1.4306 0.2397 1.0143 0.034 Uiso 1 1 calc R . .
C19 C 1.2996(4) 0.3917(3) 0.97258(17) 0.0270(8) Uani 1 1 d . . .
H19 H 1.2829 0.3472 0.9395 0.032 Uiso 1 1 calc R . .
C20 C 1.2176(3) 0.6041(3) 0.68545(17) 0.0228(7) Uani 1 1 d . . .
H20 H 1.2392 0.5766 0.7276 0.027 Uiso 1 1 calc R . .
C21 C 1.3205(4) 0.5483(3) 0.62885(17) 0.0270(8) Uani 1 1 d . . .
H21 H 1.4106 0.4817 0.6336 0.032 Uiso 1 1 calc R . .
C22 C 1.1714(4) 0.6779(3) 0.56433(17) 0.0265(8) Uani 1 1 d . . .
H22 H 1.1533 0.7075 0.5220 0.032 Uiso 1 1 calc R . .
C23 C 1.0641(3) 0.7344(3) 0.61973(16) 0.0203(7) Uani 1 1 d . . .
C24 C 0.9156(3) 0.8309(3) 0.61936(15) 0.0195(7) Uani 1 1 d . . .
C25 C 0.8599(3) 0.8958(3) 0.56654(16) 0.0226(7) Uani 1 1 d . . .
H25 H 0.9207 0.8798 0.5237 0.027 Uiso 1 1 calc R . .
C26 C 0.7136(4) 0.9851(3) 0.57623(16) 0.0217(7) Uani 1 1 d . . .
C27 C 0.6278(4) 1.0047(3) 0.63989(16) 0.0208(7) Uani 1 1 d . . .
H27 H 0.5278 1.0634 0.6479 0.025 Uiso 1 1 calc R . .
C28 C 0.6890(3) 0.9387(3) 0.69084(15) 0.0179(7) Uani 1 1 d . . .
C29 C 0.6199(3) 0.9478(3) 0.76112(16) 0.0190(7) Uani 1 1 d . . .
C30 C 0.4733(4) 1.0198(3) 0.78804(17) 0.0238(7) Uani 1 1 d . . .
H30 H 0.4098 1.0670 0.7593 0.029 Uiso 1 1 calc R . .
C31 C 0.5111(4) 0.9555(3) 0.89023(17) 0.0296(8) Uani 1 1 d . . .
H31 H 0.4759 0.9566 0.9365 0.036 Uiso 1 1 calc R . .
C32 C 0.6586(4) 0.8809(3) 0.86449(16) 0.0227(7) Uani 1 1 d . . .
H32 H 0.7208 0.8323 0.8933 0.027 Uiso 1 1 calc R . .
C33 C 0.6553(3) 1.0584(3) 0.52074(16) 0.0222(7) Uani 1 1 d . . .
C34 C 0.6966(4) 1.0059(3) 0.45651(17) 0.0268(8) Uani 1 1 d . . .
H34 H 0.7608 0.9208 0.4480 0.032 Uiso 1 1 calc R . .
C35 C 0.6441(4) 1.0780(4) 0.40472(18) 0.0317(9) Uani 1 1 d . . .
H35 H 0.6734 1.0420 0.3609 0.038 Uiso 1 1 calc R . .
C36 C 0.5496(4) 1.2016(4) 0.41657(18) 0.0335(9) Uani 1 1 d . . .
H36 H 0.5141 1.2504 0.3810 0.040 Uiso 1 1 calc R . .
C37 C 0.5066(4) 1.2541(3) 0.48052(18) 0.0315(8) Uani 1 1 d . . .
H37 H 0.4412 1.3390 0.4888 0.038 Uiso 1 1 calc R . .
C38 C 0.5588(4) 1.1831(3) 0.53226(17) 0.0271(8) Uani 1 1 d . . .
H38 H 0.5286 1.2196 0.5760 0.032 Uiso 1 1 calc R . .
C39 C 0.4546(3) 0.6057(3) 0.78536(16) 0.0220(7) Uani 1 1 d . . .
C40 C 0.2818(4) 0.3014(3) 0.72495(18) 0.0266(8) Uani 1 1 d . . .
C41 C 0.7628(4) 0.2335(3) 0.65735(17) 0.0229(7) Uani 1 1 d . . .
C42 C 0.6677(4) 0.1638(3) 0.89431(18) 0.0300(8) Uani 1 1 d . . .
C43 C 0.9846(10) 0.5459(8) 0.4541(5) 0.057(3) Uani 0.50 1 d P . .
H43A H 1.0214 0.6094 0.4377 0.068 Uiso 0.50 1 calc PR . .
H43B H 0.9324 0.5306 0.4213 0.068 Uiso 0.50 1 calc PR . .
Cl1 Cl 0.86508(15) 0.59514(17) 0.53221(9) 0.0978(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 N8 1.878(3) . ?
Fe1 N3 1.881(3) . ?
Fe1 N5 1.958(3) . ?
Fe1 N10 1.964(3) . ?
Fe1 N6 1.968(3) . ?
Fe1 N1 1.968(3) . ?
Co1 N14 1.947(3) . ?
Co1 N11 1.959(3) . ?
Co1 N13 1.964(3) . ?
Co1 N12 1.972(3) . ?
S1 C39 1.621(4) . ?
S2 C40 1.615(4) . ?
S3 C41 1.617(4) . ?
S4 C42 1.637(4) . ?
O1 H1WB 0.919(10) . ?
O1 H1WA 0.857(10) . ?
N1 C1 1.334(4) . ?
N1 C4 1.357(4) . ?
N2 C3 1.330(5) . ?
N2 C2 1.334(5) . ?
N3 C9 1.346(4) . ?
N3 C5 1.355(4) . ?
N4 C12 1.331(4) . ?
N4 C11 1.337(4) . ?
N5 C13 1.337(4) . ?
N5 C10 1.359(4) . ?
N6 C20 1.342(4) . ?
N6 C23 1.363(4) . ?
N7 C21 1.329(4) . ?
N7 C22 1.345(4) . ?
N8 C28 1.353(4) . ?
N8 C24 1.353(4) . ?
N9 C31 1.333(4) . ?
N9 C30 1.335(4) . ?
N10 C32 1.329(4) . ?
N10 C29 1.360(4) . ?
N11 C39 1.168(4) . ?
N12 C40 1.165(4) . ?
N13 C41 1.165(4) . ?
N14 C42 1.166(5) . ?
C1 C2 1.382(5) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.464(5) . ?
C5 C6 1.376(5) . ?
C6 C7 1.401(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(4) . ?
C7 C14 1.477(5) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.468(4) . ?
C10 C11 1.388(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.391(5) . ?
C14 C15 1.404(5) . ?
C15 C16 1.383(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.384(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.470(4) . ?
C24 C25 1.384(4) . ?
C25 C26 1.404(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.397(4) . ?
C26 C33 1.477(5) . ?
C27 C28 1.376(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.470(4) . ?
C29 C30 1.384(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(5) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.392(5) . ?
C33 C38 1.395(5) . ?
C34 C35 1.391(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.386(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.383(5) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C43 Cl1 1.772(10) . ?
C43 Cl1 1.800(9) 2_766 ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
Cl1 C43 1.800(9) 2_766 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N8 Fe1 N3 178.14(11) . . ?
N8 Fe1 N5 100.81(11) . . ?
N3 Fe1 N5 81.03(11) . . ?
N8 Fe1 N10 80.87(11) . . ?
N3 Fe1 N10 99.38(11) . . ?
N5 Fe1 N10 91.85(10) . . ?
N8 Fe1 N6 81.11(11) . . ?
N3 Fe1 N6 98.71(11) . . ?
N5 Fe1 N6 89.03(11) . . ?
N10 Fe1 N6 161.80(11) . . ?
N8 Fe1 N1 97.38(11) . . ?
N3 Fe1 N1 80.79(11) . . ?
N5 Fe1 N1 161.81(11) . . ?
N10 Fe1 N1 91.47(10) . . ?
N6 Fe1 N1 93.34(11) . . ?
N14 Co1 N11 116.52(12) . . ?
N14 Co1 N13 108.21(12) . . ?
N11 Co1 N13 106.91(12) . . ?
N14 Co1 N12 116.76(13) . . ?
N11 Co1 N12 104.42(12) . . ?
N13 Co1 N12 102.81(12) . . ?
H1WB O1 H1WA 96(2) . . ?
C1 N1 C4 117.4(3) . . ?
C1 N1 Fe1 127.8(2) . . ?
C4 N1 Fe1 114.8(2) . . ?
C3 N2 C2 116.6(3) . . ?
C9 N3 C5 120.6(3) . . ?
C9 N3 Fe1 119.6(2) . . ?
C5 N3 Fe1 119.7(2) . . ?
C12 N4 C11 116.3(3) . . ?
C13 N5 C10 117.3(3) . . ?
C13 N5 Fe1 128.0(2) . . ?
C10 N5 Fe1 114.6(2) . . ?
C20 N6 C23 117.0(3) . . ?
C20 N6 Fe1 128.1(2) . . ?
C23 N6 Fe1 114.6(2) . . ?
C21 N7 C22 115.8(3) . . ?
C28 N8 C24 120.2(3) . . ?
C28 N8 Fe1 120.1(2) . . ?
C24 N8 Fe1 119.6(2) . . ?
C31 N9 C30 115.9(3) . . ?
C32 N10 C29 117.1(3) . . ?
C32 N10 Fe1 128.2(2) . . ?
C29 N10 Fe1 114.7(2) . . ?
C39 N11 Co1 164.0(3) . . ?
C40 N12 Co1 145.6(3) . . ?
C41 N13 Co1 165.6(3) . . ?
C42 N14 Co1 174.6(3) . . ?
N1 C1 C2 121.1(3) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
N2 C2 C1 122.2(3) . . ?
N2 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
N2 C3 C4 122.5(3) . . ?
N2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
N1 C4 C3 120.1(3) . . ?
N1 C4 C5 113.9(3) . . ?
C3 C4 C5 126.0(3) . . ?
N3 C5 C6 120.8(3) . . ?
N3 C5 C4 110.8(3) . . ?
C6 C5 C4 128.4(3) . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 118.4(3) . . ?
C6 C7 C14 121.1(3) . . ?
C8 C7 C14 120.3(3) . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N3 C9 C8 121.1(3) . . ?
N3 C9 C10 110.8(3) . . ?
C8 C9 C10 128.0(3) . . ?
N5 C10 C11 120.3(3) . . ?
N5 C10 C9 113.8(3) . . ?
C11 C10 C9 125.9(3) . . ?
N4 C11 C10 122.5(3) . . ?
N4 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
N4 C12 C13 122.8(3) . . ?
N4 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
N5 C13 C12 120.9(3) . . ?
N5 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C19 C14 C15 118.8(3) . . ?
C19 C14 C7 119.9(3) . . ?
C15 C14 C7 121.2(3) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
N6 C20 C21 120.6(3) . . ?
N6 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
N7 C21 C20 123.5(3) . . ?
N7 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?
N7 C22 C23 122.4(3) . . ?
N7 C22 H22 118.8 . . ?
C23 C22 H22 118.8 . . ?
N6 C23 C22 120.6(3) . . ?
N6 C23 C24 113.6(3) . . ?
C22 C23 C24 125.7(3) . . ?
N8 C24 C25 120.5(3) . . ?
N8 C24 C23 110.9(3) . . ?
C25 C24 C23 128.5(3) . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 118.1(3) . . ?
C27 C26 C33 121.6(3) . . ?
C25 C26 C33 120.3(3) . . ?
C28 C27 C26 119.6(3) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
N8 C28 C27 121.5(3) . . ?
N8 C28 C29 110.3(3) . . ?
C27 C28 C29 128.2(3) . . ?
N10 C29 C30 120.4(3) . . ?
N10 C29 C28 113.9(3) . . ?
C30 C29 C28 125.6(3) . . ?
N9 C30 C29 122.8(3) . . ?
N9 C30 H30 118.6 . . ?
C29 C30 H30 118.6 . . ?
N9 C31 C32 122.6(3) . . ?
N9 C31 H31 118.7 . . ?
C32 C31 H31 118.7 . . ?
N10 C32 C31 121.1(3) . . ?
N10 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C34 C33 C38 119.0(3) . . ?
C34 C33 C26 121.2(3) . . ?
C38 C33 C26 119.8(3) . . ?
C35 C34 C33 120.1(3) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C36 C35 C34 120.5(3) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 119.8(3) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C38 C37 C36 120.1(3) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C33 120.6(3) . . ?
C37 C38 H38 119.7 . . ?
C33 C38 H38 119.7 . . ?
N11 C39 S1 179.4(3) . . ?
N12 C40 S2 179.3(3) . . ?
N13 C41 S3 177.7(3) . . ?
N14 C42 S4 178.5(3) . . ?
Cl1 C43 Cl1 105.5(5) . 2_766 ?
Cl1 C43 H43A 110.6 . . ?
Cl1 C43 H43A 110.6 2_766 . ?
Cl1 C43 H43B 110.6 . . ?
Cl1 C43 H43B 110.6 2_766 . ?
H43A C43 H43B 108.8 . . ?
C43 Cl1 C43 74.5(5) . 2_766 ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N8 Fe1 N1 C1 1.1(3) . . . . ?
N3 Fe1 N1 C1 -179.2(3) . . . . ?
N5 Fe1 N1 C1 179.6(3) . . . . ?
N10 Fe1 N1 C1 -79.9(3) . . . . ?
N6 Fe1 N1 C1 82.5(3) . . . . ?
N8 Fe1 N1 C4 178.7(2) . . . . ?
N3 Fe1 N1 C4 -1.5(2) . . . . ?
N5 Fe1 N1 C4 -2.7(5) . . . . ?
N10 Fe1 N1 C4 97.7(2) . . . . ?
N6 Fe1 N1 C4 -99.8(2) . . . . ?
N8 Fe1 N3 C9 -170(3) . . . . ?
N5 Fe1 N3 C9 2.1(2) . . . . ?
N10 Fe1 N3 C9 92.5(2) . . . . ?
N6 Fe1 N3 C9 -85.5(2) . . . . ?
N1 Fe1 N3 C9 -177.5(2) . . . . ?
N8 Fe1 N3 C5 7(4) . . . . ?
N5 Fe1 N3 C5 179.2(2) . . . . ?
N10 Fe1 N3 C5 -90.4(2) . . . . ?
N6 Fe1 N3 C5 91.6(2) . . . . ?
N1 Fe1 N3 C5 -0.4(2) . . . . ?
N8 Fe1 N5 C13 0.6(3) . . . . ?
N3 Fe1 N5 C13 -179.2(3) . . . . ?
N10 Fe1 N5 C13 81.6(3) . . . . ?
N6 Fe1 N5 C13 -80.2(3) . . . . ?
N1 Fe1 N5 C13 -178.0(3) . . . . ?
N8 Fe1 N5 C10 177.6(2) . . . . ?
N3 Fe1 N5 C10 -2.1(2) . . . . ?
N10 Fe1 N5 C10 -101.3(2) . . . . ?
N6 Fe1 N5 C10 96.9(2) . . . . ?
N1 Fe1 N5 C10 -0.9(5) . . . . ?
N8 Fe1 N6 C20 -173.1(3) . . . . ?
N3 Fe1 N6 C20 8.7(3) . . . . ?
N5 Fe1 N6 C20 -72.0(3) . . . . ?
N10 Fe1 N6 C20 -165.0(3) . . . . ?
N1 Fe1 N6 C20 89.9(3) . . . . ?
N8 Fe1 N6 C23 0.8(2) . . . . ?
N3 Fe1 N6 C23 -177.3(2) . . . . ?
N5 Fe1 N6 C23 101.9(2) . . . . ?
N10 Fe1 N6 C23 8.9(5) . . . . ?
N1 Fe1 N6 C23 -96.2(2) . . . . ?
N3 Fe1 N8 C28 -95(3) . . . . ?
N5 Fe1 N8 C28 93.1(2) . . . . ?
N10 Fe1 N8 C28 3.0(2) . . . . ?
N6 Fe1 N8 C28 -179.6(2) . . . . ?
N1 Fe1 N8 C28 -87.4(2) . . . . ?
N3 Fe1 N8 C24 81(4) . . . . ?
N5 Fe1 N8 C24 -91.0(2) . . . . ?
N10 Fe1 N8 C24 178.8(2) . . . . ?
N6 Fe1 N8 C24 -3.7(2) . . . . ?
N1 Fe1 N8 C24 88.5(2) . . . . ?
N8 Fe1 N10 C32 178.3(3) . . . . ?
N3 Fe1 N10 C32 -3.5(3) . . . . ?
N5 Fe1 N10 C32 77.7(3) . . . . ?
N6 Fe1 N10 C32 170.2(3) . . . . ?
N1 Fe1 N10 C32 -84.4(3) . . . . ?
N8 Fe1 N10 C29 -0.7(2) . . . . ?
N3 Fe1 N10 C29 177.4(2) . . . . ?
N5 Fe1 N10 C29 -101.4(2) . . . . ?
N6 Fe1 N10 C29 -8.9(5) . . . . ?
N1 Fe1 N10 C29 96.5(2) . . . . ?
N14 Co1 N11 C39 144.1(9) . . . . ?
N13 Co1 N11 C39 23.0(10) . . . . ?
N12 Co1 N11 C39 -85.5(10) . . . . ?
N14 Co1 N12 C40 -124.1(5) . . . . ?
N11 Co1 N12 C40 105.7(5) . . . . ?
N13 Co1 N12 C40 -5.8(5) . . . . ?
N14 Co1 N13 C41 -57.7(12) . . . . ?
N11 Co1 N13 C41 68.6(12) . . . . ?
N12 Co1 N13 C41 178.2(11) . . . . ?
N11 Co1 N14 C42 -60(3) . . . . ?
N13 Co1 N14 C42 60(3) . . . . ?
N12 Co1 N14 C42 176(3) . . . . ?
C4 N1 C1 C2 -1.1(5) . . . . ?
Fe1 N1 C1 C2 176.5(3) . . . . ?
C3 N2 C2 C1 1.6(6) . . . . ?
N1 C1 C2 N2 -0.2(6) . . . . ?
C2 N2 C3 C4 -1.7(5) . . . . ?
C1 N1 C4 C3 1.0(5) . . . . ?
Fe1 N1 C4 C3 -176.9(3) . . . . ?
C1 N1 C4 C5 -179.1(3) . . . . ?
Fe1 N1 C4 C5 3.0(3) . . . . ?
N2 C3 C4 N1 0.4(5) . . . . ?
N2 C3 C4 C5 -179.5(3) . . . . ?
C9 N3 C5 C6 1.8(5) . . . . ?
Fe1 N3 C5 C6 -175.3(2) . . . . ?
C9 N3 C5 C4 179.1(3) . . . . ?
Fe1 N3 C5 C4 2.1(3) . . . . ?
N1 C4 C5 N3 -3.2(4) . . . . ?
C3 C4 C5 N3 176.7(3) . . . . ?
N1 C4 C5 C6 173.9(3) . . . . ?
C3 C4 C5 C6 -6.2(6) . . . . ?
N3 C5 C6 C7 -0.6(5) . . . . ?
C4 C5 C6 C7 -177.5(3) . . . . ?
C5 C6 C7 C8 -1.1(5) . . . . ?
C5 C6 C7 C14 175.4(3) . . . . ?
C6 C7 C8 C9 1.6(5) . . . . ?
C14 C7 C8 C9 -174.8(3) . . . . ?
C5 N3 C9 C8 -1.2(4) . . . . ?
Fe1 N3 C9 C8 175.9(2) . . . . ?
C5 N3 C9 C10 -178.7(3) . . . . ?
Fe1 N3 C9 C10 -1.6(3) . . . . ?
C7 C8 C9 N3 -0.5(5) . . . . ?
C7 C8 C9 C10 176.5(3) . . . . ?
C13 N5 C10 C11 -0.8(4) . . . . ?
Fe1 N5 C10 C11 -178.1(2) . . . . ?
C13 N5 C10 C9 179.2(3) . . . . ?
Fe1 N5 C10 C9 1.8(3) . . . . ?
N3 C9 C10 N5 -0.2(4) . . . . ?
C8 C9 C10 N5 -177.5(3) . . . . ?
N3 C9 C10 C11 179.8(3) . . . . ?
C8 C9 C10 C11 2.4(5) . . . . ?
C12 N4 C11 C10 1.1(5) . . . . ?
N5 C10 C11 N4 0.0(5) . . . . ?
C9 C10 C11 N4 -180.0(3) . . . . ?
C11 N4 C12 C13 -1.5(5) . . . . ?
C10 N5 C13 C12 0.4(4) . . . . ?
Fe1 N5 C13 C12 177.4(2) . . . . ?
N4 C12 C13 N5 0.7(5) . . . . ?
C6 C7 C14 C19 -149.7(3) . . . . ?
C8 C7 C14 C19 26.7(5) . . . . ?
C6 C7 C14 C15 27.3(5) . . . . ?
C8 C7 C14 C15 -156.3(3) . . . . ?
C19 C14 C15 C16 -0.1(5) . . . . ?
C7 C14 C15 C16 -177.1(3) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C18 C19 C14 0.0(5) . . . . ?
C15 C14 C19 C18 -0.1(5) . . . . ?
C7 C14 C19 C18 177.0(3) . . . . ?
C23 N6 C20 C21 -1.6(4) . . . . ?
Fe1 N6 C20 C21 172.2(2) . . . . ?
C22 N7 C21 C20 0.3(5) . . . . ?
N6 C20 C21 N7 1.4(5) . . . . ?
C21 N7 C22 C23 -1.9(5) . . . . ?
C20 N6 C23 C22 0.2(4) . . . . ?
Fe1 N6 C23 C22 -174.5(2) . . . . ?
C20 N6 C23 C24 176.5(3) . . . . ?
Fe1 N6 C23 C24 1.9(3) . . . . ?
N7 C22 C23 N6 1.7(5) . . . . ?
N7 C22 C23 C24 -174.2(3) . . . . ?
C28 N8 C24 C25 2.2(4) . . . . ?
Fe1 N8 C24 C25 -173.7(2) . . . . ?
C28 N8 C24 C23 -178.6(3) . . . . ?
Fe1 N8 C24 C23 5.6(3) . . . . ?
N6 C23 C24 N8 -4.6(4) . . . . ?
C22 C23 C24 N8 171.5(3) . . . . ?
N6 C23 C24 C25 174.6(3) . . . . ?
C22 C23 C24 C25 -9.3(5) . . . . ?
N8 C24 C25 C26 -1.1(5) . . . . ?
C23 C24 C25 C26 179.8(3) . . . . ?
C24 C25 C26 C27 -0.6(5) . . . . ?
C24 C25 C26 C33 177.4(3) . . . . ?
C25 C26 C27 C28 1.2(5) . . . . ?
C33 C26 C27 C28 -176.7(3) . . . . ?
C24 N8 C28 C27 -1.6(4) . . . . ?
Fe1 N8 C28 C27 174.3(2) . . . . ?
C24 N8 C28 C29 179.9(3) . . . . ?
Fe1 N8 C28 C29 -4.3(3) . . . . ?
C26 C27 C28 N8 -0.2(5) . . . . ?
C26 C27 C28 C29 178.1(3) . . . . ?
C32 N10 C29 C30 -0.9(4) . . . . ?
Fe1 N10 C29 C30 178.3(2) . . . . ?
C32 N10 C29 C28 179.5(3) . . . . ?
Fe1 N10 C29 C28 -1.3(3) . . . . ?
N8 C28 C29 N10 3.4(4) . . . . ?
C27 C28 C29 N10 -175.0(3) . . . . ?
N8 C28 C29 C30 -176.1(3) . . . . ?
C27 C28 C29 C30 5.4(5) . . . . ?
C31 N9 C30 C29 -1.3(5) . . . . ?
N10 C29 C30 N9 1.6(5) . . . . ?
C28 C29 C30 N9 -178.9(3) . . . . ?
C30 N9 C31 C32 0.4(5) . . . . ?
C29 N10 C32 C31 0.0(5) . . . . ?
Fe1 N10 C32 C31 -179.0(2) . . . . ?
N9 C31 C32 N10 0.3(5) . . . . ?
C27 C26 C33 C34 -145.6(3) . . . . ?
C25 C26 C33 C34 36.5(5) . . . . ?
C27 C26 C33 C38 35.4(5) . . . . ?
C25 C26 C33 C38 -142.6(3) . . . . ?
C38 C33 C34 C35 1.2(5) . . . . ?
C26 C33 C34 C35 -177.8(3) . . . . ?
C33 C34 C35 C36 -0.7(5) . . . . ?
C34 C35 C36 C37 -0.1(5) . . . . ?
C35 C36 C37 C38 0.3(5) . . . . ?
C36 C37 C38 C33 0.2(5) . . . . ?
C34 C33 C38 C37 -1.0(5) . . . . ?
C26 C33 C38 C37 178.1(3) . . . . ?
Co1 N11 C39 S1 -110(39) . . . . ?
Co1 N12 C40 S2 93(26) . . . . ?
Co1 N13 C41 S3 44(9) . . . . ?
Co1 N14 C42 S4 -170(10) . . . . ?
Cl1 C43 Cl1 C43 -0.001(1) 2_766 . . 2_766 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.656
_refine_diff_density_min         -0.949
_refine_diff_density_rms         0.079
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_umd313
_database_code_depnum_ccdc_archive 'CCDC 1050962'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H26 Cl6 Cu3 N10'
_chemical_formula_weight         1026.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0764(4)
_cell_length_b                   10.3447(5)
_cell_length_c                   12.0794(6)
_cell_angle_alpha                69.080(3)
_cell_angle_beta                 86.145(3)
_cell_angle_gamma                88.856(3)
_cell_volume                     940.54(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3227
_cell_measurement_theta_min      4.58
_cell_measurement_theta_max      68.26

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             513
_exptl_absorpt_coefficient_mu    6.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_T_max  0.9399
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus ImuS'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10380
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_sigmaI/netI    0.0937
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         68.34
_reflns_number_total             3440
_reflns_number_gt                2288
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0425P)²+1.1838P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3440
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 1.0000 0.5000 0.0189(3) Uani 1 2 d S . .
Cu2 Cu 0.07600(10) 0.30518(8) 0.81725(7) 0.0201(2) Uani 1 1 d . . .
Cl1 Cl 0.27545(17) 0.99917(14) 0.48216(14) 0.0299(3) Uani 1 1 d . . .
Cl2 Cl -0.13956(17) 0.18774(14) 0.74820(12) 0.0272(3) Uani 1 1 d . . .
Cl3 Cl -0.01283(18) 0.28916(15) 0.99912(11) 0.0293(3) Uani 1 1 d . . .
N1 N -0.0027(5) 0.7931(4) 0.5976(4) 0.0177(10) Uani 1 1 d . . .
N2 N 0.0179(5) 0.5146(4) 0.7294(4) 0.0174(10) Uani 1 1 d . . .
N3 N 0.2123(5) 0.3489(4) 0.6693(4) 0.0164(9) Uani 1 1 d . . .
N4 N 0.2303(6) 0.1366(4) 0.8572(4) 0.0214(10) Uani 1 1 d . . .
N5 N 0.4464(6) -0.0819(5) 0.8818(4) 0.0284(11) Uani 1 1 d . . .
C1 C -0.0651(7) 0.5995(5) 0.7721(5) 0.0220(12) Uani 1 1 d . . .
H1 H -0.1179 0.5636 0.8497 0.026 Uiso 1 1 calc R . .
C2 C -0.0773(7) 0.7403(6) 0.7067(5) 0.0233(13) Uani 1 1 d . . .
H2 H -0.1387 0.7989 0.7395 0.028 Uiso 1 1 calc R . .
C3 C 0.0805(6) 0.7081(5) 0.5536(5) 0.0178(11) Uani 1 1 d . . .
H3 H 0.1328 0.7444 0.4758 0.021 Uiso 1 1 calc R . .
C4 C 0.0926(6) 0.5686(5) 0.6182(4) 0.0151(11) Uani 1 1 d . . .
C5 C 0.1929(6) 0.4692(5) 0.5802(4) 0.0155(11) Uani 1 1 d . . .
C6 C 0.2707(6) 0.4955(5) 0.4693(4) 0.0179(11) Uani 1 1 d . . .
H6 H 0.2528 0.5807 0.4069 0.021 Uiso 1 1 calc R . .
C7 C 0.3768(6) 0.3959(5) 0.4487(4) 0.0165(11) Uani 1 1 d . . .
C8 C 0.4012(6) 0.2749(5) 0.5451(5) 0.0194(12) Uani 1 1 d . . .
H8 H 0.4764 0.2068 0.5366 0.023 Uiso 1 1 calc R . .
C9 C 0.3158(6) 0.2540(5) 0.6531(5) 0.0177(11) Uani 1 1 d . . .
C10 C 0.3313(6) 0.1317(5) 0.7643(5) 0.0188(11) Uani 1 1 d . . .
C11 C 0.4393(7) 0.0237(5) 0.7785(5) 0.0250(13) Uani 1 1 d . . .
H11 H 0.5111 0.0239 0.7128 0.030 Uiso 1 1 calc R . .
C12 C 0.3434(7) -0.0781(6) 0.9710(5) 0.0286(14) Uani 1 1 d . . .
H12 H 0.3435 -0.1529 1.0449 0.034 Uiso 1 1 calc R . .
C13 C 0.2346(7) 0.0325(5) 0.9598(5) 0.0229(12) Uani 1 1 d . . .
H13 H 0.1640 0.0326 1.0259 0.027 Uiso 1 1 calc R . .
C14 C 0.4628(6) 0.4206(5) 0.3308(5) 0.0168(11) Uani 1 1 d . . .
C15 C 0.4563(7) 0.5502(5) 0.2384(5) 0.0241(13) Uani 1 1 d . . .
H15 H 0.3904 0.6218 0.2502 0.029 Uiso 1 1 calc R . .
C16 C 0.5450(7) 0.5747(6) 0.1302(5) 0.0308(14) Uani 1 1 d . . .
H16 H 0.5396 0.6625 0.0685 0.037 Uiso 1 1 calc R . .
C17 C 0.6409(7) 0.4707(6) 0.1127(5) 0.0280(14) Uani 1 1 d . . .
H17 H 0.7046 0.4884 0.0398 0.034 Uiso 1 1 calc R . .
C18 C 0.6447(7) 0.3418(6) 0.2004(5) 0.0269(13) Uani 1 1 d . . .
H18 H 0.7090 0.2701 0.1872 0.032 Uiso 1 1 calc R . .
C19 C 0.5552(7) 0.3166(6) 0.3072(5) 0.0235(12) Uani 1 1 d . . .
H19 H 0.5563 0.2266 0.3662 0.028 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.042(4) . ?
Cu1 N1 2.042(4) 2_576 ?
Cu1 Cl1 2.2207(14) 2_576 ?
Cu1 Cl1 2.2207(14) . ?
Cu2 N3 1.947(4) . ?
Cu2 N4 2.054(4) . ?
Cu2 N2 2.103(4) . ?
Cu2 Cl3 2.2139(15) . ?
Cu2 Cl2 2.4912(16) . ?
N1 C3 1.330(6) . ?
N1 C2 1.338(7) . ?
N2 C1 1.320(6) . ?
N2 C4 1.360(6) . ?
N3 C9 1.335(6) . ?
N3 C5 1.337(6) . ?
N4 C13 1.323(7) . ?
N4 C10 1.358(6) . ?
N5 C12 1.328(7) . ?
N5 C11 1.337(7) . ?
C1 C2 1.392(7) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.380(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.476(7) . ?
C5 C6 1.378(7) . ?
C6 C7 1.406(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(7) . ?
C7 C14 1.479(7) . ?
C8 C9 1.381(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.491(7) . ?
C10 C11 1.372(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.402(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.398(7) . ?
C14 C15 1.407(7) . ?
C15 C16 1.389(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 179.999(1) . 2_576 ?
N1 Cu1 Cl1 89.48(12) . 2_576 ?
N1 Cu1 Cl1 90.52(12) 2_576 2_576 ?
N1 Cu1 Cl1 90.52(12) . . ?
N1 Cu1 Cl1 89.48(12) 2_576 . ?
Cl1 Cu1 Cl1 179.999(1) 2_576 . ?
N3 Cu2 N4 78.90(17) . . ?
N3 Cu2 N2 78.33(17) . . ?
N4 Cu2 N2 153.72(17) . . ?
N3 Cu2 Cl3 161.73(13) . . ?
N4 Cu2 Cl3 99.62(13) . . ?
N2 Cu2 Cl3 97.88(12) . . ?
N3 Cu2 Cl2 92.70(13) . . ?
N4 Cu2 Cl2 92.69(13) . . ?
N2 Cu2 Cl2 101.32(12) . . ?
Cl3 Cu2 Cl2 105.56(6) . . ?
C3 N1 C2 118.6(5) . . ?
C3 N1 Cu1 118.6(3) . . ?
C2 N1 Cu1 122.7(4) . . ?
C1 N2 C4 117.9(4) . . ?
C1 N2 Cu2 128.6(4) . . ?
C4 N2 Cu2 113.1(3) . . ?
C9 N3 C5 119.8(4) . . ?
C9 N3 Cu2 119.8(3) . . ?
C5 N3 Cu2 120.2(4) . . ?
C13 N4 C10 118.3(5) . . ?
C13 N4 Cu2 127.1(4) . . ?
C10 N4 Cu2 114.5(3) . . ?
C12 N5 C11 116.9(5) . . ?
N2 C1 C2 121.9(5) . . ?
N2 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
N1 C2 C1 120.0(5) . . ?
N1 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
N1 C3 C4 121.5(5) . . ?
N1 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
N2 C4 C3 120.1(5) . . ?
N2 C4 C5 114.6(4) . . ?
C3 C4 C5 125.1(5) . . ?
N3 C5 C6 121.6(5) . . ?
N3 C5 C4 112.4(4) . . ?
C6 C5 C4 125.8(5) . . ?
C5 C6 C7 119.9(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 117.0(5) . . ?
C8 C7 C14 121.6(5) . . ?
C6 C7 C14 121.4(5) . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
N3 C9 C8 121.7(5) . . ?
N3 C9 C10 112.2(4) . . ?
C8 C9 C10 126.0(5) . . ?
N4 C10 C11 120.5(5) . . ?
N4 C10 C9 113.7(4) . . ?
C11 C10 C9 125.8(5) . . ?
N5 C11 C10 122.0(5) . . ?
N5 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
N5 C12 C13 122.2(5) . . ?
N5 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
N4 C13 C12 120.0(5) . . ?
N4 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C19 C14 C15 117.4(5) . . ?
C19 C14 C7 121.3(5) . . ?
C15 C14 C7 121.4(5) . . ?
C16 C15 C14 120.9(5) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.4(5) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.0(6) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 121.5(5) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 N1 C3 -30(24) 2_576 . . . ?
Cl1 Cu1 N1 C3 127.3(4) 2_576 . . . ?
Cl1 Cu1 N1 C3 -52.7(4) . . . . ?
N1 Cu1 N1 C2 147(24) 2_576 . . . ?
Cl1 Cu1 N1 C2 -56.3(4) 2_576 . . . ?
Cl1 Cu1 N1 C2 123.7(4) . . . . ?
N3 Cu2 N2 C1 -169.2(5) . . . . ?
N4 Cu2 N2 C1 -138.8(5) . . . . ?
Cl3 Cu2 N2 C1 -7.4(5) . . . . ?
Cl2 Cu2 N2 C1 100.3(5) . . . . ?
N3 Cu2 N2 C4 3.4(3) . . . . ?
N4 Cu2 N2 C4 33.9(6) . . . . ?
Cl3 Cu2 N2 C4 165.3(3) . . . . ?
Cl2 Cu2 N2 C4 -87.0(3) . . . . ?
N4 Cu2 N3 C9 9.1(4) . . . . ?
N2 Cu2 N3 C9 175.8(4) . . . . ?
Cl3 Cu2 N3 C9 96.1(5) . . . . ?
Cl2 Cu2 N3 C9 -83.2(4) . . . . ?
N4 Cu2 N3 C5 -176.3(4) . . . . ?
N2 Cu2 N3 C5 -9.6(4) . . . . ?
Cl3 Cu2 N3 C5 -89.3(6) . . . . ?
Cl2 Cu2 N3 C5 91.4(4) . . . . ?
N3 Cu2 N4 C13 177.3(5) . . . . ?
N2 Cu2 N4 C13 147.0(4) . . . . ?
Cl3 Cu2 N4 C13 15.9(5) . . . . ?
Cl2 Cu2 N4 C13 -90.4(5) . . . . ?
N3 Cu2 N4 C10 -6.2(4) . . . . ?
N2 Cu2 N4 C10 -36.6(6) . . . . ?
Cl3 Cu2 N4 C10 -167.7(3) . . . . ?
Cl2 Cu2 N4 C10 86.0(4) . . . . ?
C4 N2 C1 C2 0.1(8) . . . . ?
Cu2 N2 C1 C2 172.4(4) . . . . ?
C3 N1 C2 C1 0.9(8) . . . . ?
Cu1 N1 C2 C1 -175.5(4) . . . . ?
N2 C1 C2 N1 -0.5(9) . . . . ?
C2 N1 C3 C4 -0.7(8) . . . . ?
Cu1 N1 C3 C4 175.8(4) . . . . ?
C1 N2 C4 C3 0.1(8) . . . . ?
Cu2 N2 C4 C3 -173.4(4) . . . . ?
C1 N2 C4 C5 175.7(5) . . . . ?
Cu2 N2 C4 C5 2.2(5) . . . . ?
N1 C3 C4 N2 0.3(8) . . . . ?
N1 C3 C4 C5 -174.9(5) . . . . ?
C9 N3 C5 C6 3.5(8) . . . . ?
Cu2 N3 C5 C6 -171.1(4) . . . . ?
C9 N3 C5 C4 -172.1(4) . . . . ?
Cu2 N3 C5 C4 13.3(6) . . . . ?
N2 C4 C5 N3 -9.5(6) . . . . ?
C3 C4 C5 N3 165.9(5) . . . . ?
N2 C4 C5 C6 175.1(5) . . . . ?
C3 C4 C5 C6 -9.5(8) . . . . ?
N3 C5 C6 C7 -1.7(8) . . . . ?
C4 C5 C6 C7 173.4(5) . . . . ?
C5 C6 C7 C8 -1.8(8) . . . . ?
C5 C6 C7 C14 -179.8(5) . . . . ?
C6 C7 C8 C9 3.4(8) . . . . ?
C14 C7 C8 C9 -178.5(5) . . . . ?
C5 N3 C9 C8 -1.8(8) . . . . ?
Cu2 N3 C9 C8 172.8(4) . . . . ?
C5 N3 C9 C10 175.6(4) . . . . ?
Cu2 N3 C9 C10 -9.8(6) . . . . ?
C7 C8 C9 N3 -1.8(8) . . . . ?
C7 C8 C9 C10 -178.7(5) . . . . ?
C13 N4 C10 C11 -2.5(8) . . . . ?
Cu2 N4 C10 C11 -179.2(4) . . . . ?
C13 N4 C10 C9 179.8(5) . . . . ?
Cu2 N4 C10 C9 3.0(6) . . . . ?
N3 C9 C10 N4 3.9(6) . . . . ?
C8 C9 C10 N4 -178.8(5) . . . . ?
N3 C9 C10 C11 -173.7(5) . . . . ?
C8 C9 C10 C11 3.6(9) . . . . ?
C12 N5 C11 C10 0.2(9) . . . . ?
N4 C10 C11 N5 1.9(9) . . . . ?
C9 C10 C11 N5 179.4(5) . . . . ?
C11 N5 C12 C13 -1.7(9) . . . . ?
C10 N4 C13 C12 1.0(8) . . . . ?
Cu2 N4 C13 C12 177.3(4) . . . . ?
N5 C12 C13 N4 1.1(9) . . . . ?
C8 C7 C14 C19 8.3(8) . . . . ?
C6 C7 C14 C19 -173.7(5) . . . . ?
C8 C7 C14 C15 -170.9(5) . . . . ?
C6 C7 C14 C15 7.0(8) . . . . ?
C19 C14 C15 C16 -2.9(8) . . . . ?
C7 C14 C15 C16 176.4(5) . . . . ?
C14 C15 C16 C17 0.0(9) . . . . ?
C15 C16 C17 C18 2.2(9) . . . . ?
C16 C17 C18 C19 -1.4(9) . . . . ?
C17 C18 C19 C14 -1.7(9) . . . . ?
C15 C14 C19 C18 3.8(8) . . . . ?
C7 C14 C19 C18 -175.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        68.34
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.119
