# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_30decam
_database_code_depnum_ccdc_archive 'CCDC 1508071'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 Cl6 Cu2 N8 O2'
_chemical_formula_weight         794.28

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_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                   8.5142(15)
_cell_length_b                   11.569(2)
_cell_length_c                   14.932(3)
_cell_angle_alpha                99.351(1)
_cell_angle_beta                 96.856(2)
_cell_angle_gamma                90.793(3)
_cell_volume                     1440.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4922
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block-type
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796
_exptl_absorpt_coefficient_mu    2.075
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6582
_exptl_absorpt_correction_T_max  0.7064
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7377
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4922
_reflns_number_gt                4237
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0984P)²+0.5017P] 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         4922
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.14574(5) 0.47131(4) 0.92945(3) 0.01289(18) Uani 1 1 d . . .
Cu2 Cu 0.32409(5) 0.97038(4) 0.92882(3) 0.01321(18) Uani 1 1 d . . .
Cl2 Cl -0.04951(11) 0.60430(8) 0.93290(7) 0.0147(2) Uani 1 1 d . . .
Cl4 Cl 0.52579(11) 1.10183(8) 0.92925(7) 0.0153(2) Uani 1 1 d . . .
Cl3 Cl 0.33148(11) 0.61353(8) 0.99025(7) 0.0179(3) Uani 1 1 d . . .
Cl1B Cl 0.22377(12) 1.06576(8) 0.73446(7) 0.0188(3) Uani 1 1 d . . .
Cl5 Cl 0.16697(12) 1.11321(8) 0.98689(8) 0.0198(3) Uani 1 1 d . . .
Cl1A Cl 0.16868(12) 0.58325(8) 0.74383(7) 0.0186(3) Uani 1 1 d . . .
N9B N 0.5569(4) 0.7260(3) 0.7559(2) 0.0139(7) Uani 1 1 d . . .
O1B O 0.1545(3) 0.8498(2) 0.9268(2) 0.0180(6) Uani 1 1 d . . .
H4W H 0.0535 0.8636 0.9312 0.027 Uiso 1 1 d R . .
H3W H 0.1673 0.7733 0.9214 0.027 Uiso 1 1 d R . .
N3A N -0.1856(4) 0.3009(3) 0.5987(2) 0.0202(8) Uani 1 1 d . . .
N9A N -0.1612(4) 0.2308(3) 0.7449(2) 0.0149(7) Uani 1 1 d . . .
N1A N -0.0263(4) 0.4767(3) 0.6044(2) 0.0185(8) Uani 1 1 d . . .
O1A O 0.3080(3) 0.3497(2) 0.9270(2) 0.0173(6) Uani 1 1 d . . .
H2W H 0.4077 0.3631 0.9369 0.026 Uiso 1 1 d R . .
H1W H 0.2888 0.2760 0.9158 0.026 Uiso 1 1 d R . .
N3B N 0.5272(4) 0.7845(3) 0.6060(2) 0.0185(8) Uani 1 1 d . . .
N7B N 0.4118(4) 0.8612(3) 0.8295(2) 0.0158(7) Uani 1 1 d . . .
N1B N 0.3708(4) 0.9562(3) 0.6020(2) 0.0198(8) Uani 1 1 d . . .
N7A N 0.0146(4) 0.3662(3) 0.8259(2) 0.0133(7) Uani 1 1 d . . .
C15A C -0.0712(5) -0.1609(4) 0.7254(3) 0.0222(10) Uani 1 1 d . . .
H15A H -0.0408 -0.2112 0.7665 0.027 Uiso 1 1 calc R . .
C8A C -0.0745(5) 0.2722(3) 0.8273(3) 0.0163(9) Uani 1 1 d . . .
H8A H -0.0779 0.2376 0.8791 0.020 Uiso 1 1 calc R . .
C5B C 0.4099(4) 0.8791(3) 0.7395(3) 0.0127(8) Uani 1 1 d . . .
C6B C 0.3442(5) 0.9596(3) 0.6881(3) 0.0147(8) Uani 1 1 d . . .
C10A C -0.2725(5) 0.1290(4) 0.7233(3) 0.0203(9) Uani 1 1 d . . .
H10A H -0.3544 0.1420 0.6753 0.024 Uiso 1 1 calc R . .
H10B H -0.3229 0.1213 0.7770 0.024 Uiso 1 1 calc R . .
C12A C -0.1604(5) -0.0105(4) 0.6025(3) 0.0187(9) Uani 1 1 d . . .
H12A H -0.1903 0.0396 0.5612 0.022 Uiso 1 1 calc R . .
C11B C 0.5560(5) 0.5126(3) 0.7042(3) 0.0153(9) Uani 1 1 d . . .
C2A C -0.1308(5) 0.3889(4) 0.5632(3) 0.0221(10) Uani 1 1 d . . .
H2A H -0.1688 0.3908 0.5024 0.027 Uiso 1 1 calc R . .
C4A C -0.1272(5) 0.3049(3) 0.6864(3) 0.0143(8) Uani 1 1 d . . .
C6A C 0.0303(5) 0.4757(4) 0.6901(3) 0.0163(9) Uani 1 1 d . . .
C15B C 0.4440(5) 0.3300(4) 0.7320(3) 0.0214(10) Uani 1 1 d . . .
H15B H 0.4322 0.2767 0.7714 0.026 Uiso 1 1 calc R . .
C16A C -0.1472(5) -0.0586(4) 0.7542(3) 0.0186(9) Uani 1 1 d . . .
H16A H -0.1684 -0.0407 0.8145 0.022 Uiso 1 1 calc R . .
C12B C 0.4765(5) 0.4916(4) 0.6157(3) 0.0183(9) Uani 1 1 d . . .
H12B H 0.4863 0.5457 0.5768 0.022 Uiso 1 1 calc R . .
C11A C -0.1919(5) 0.0175(3) 0.6928(3) 0.0152(9) Uani 1 1 d . . .
C5A C -0.0182(5) 0.3906(3) 0.7374(3) 0.0143(8) Uani 1 1 d . . .
C14B C 0.3670(5) 0.3099(4) 0.6431(3) 0.0223(10) Uani 1 1 d . . .
H14B H 0.3046 0.2421 0.6224 0.027 Uiso 1 1 calc R . .
C4B C 0.5009(5) 0.7954(3) 0.6936(3) 0.0147(8) Uani 1 1 d . . .
C10B C 0.6556(5) 0.6239(3) 0.7372(3) 0.0182(9) Uani 1 1 d . . .
H10C H 0.7238 0.6157 0.7925 0.022 Uiso 1 1 calc R . .
H10D H 0.7224 0.6363 0.6911 0.022 Uiso 1 1 calc R . .
C8B C 0.5022(5) 0.7694(3) 0.8358(3) 0.0160(9) Uani 1 1 d . . .
H8B H 0.5254 0.7383 0.8893 0.019 Uiso 1 1 calc R . .
C16B C 0.5398(5) 0.4320(4) 0.7615(3) 0.0188(9) Uani 1 1 d . . .
H16B H 0.5932 0.4455 0.8205 0.023 Uiso 1 1 calc R . .
C14A C -0.0402(5) -0.1885(4) 0.6350(3) 0.0234(10) Uani 1 1 d . . .
H14A H 0.0100 -0.2574 0.6158 0.028 Uiso 1 1 calc R . .
C13B C 0.3830(5) 0.3905(4) 0.5854(3) 0.0197(9) Uani 1 1 d . . .
H13B H 0.3309 0.3767 0.5261 0.024 Uiso 1 1 calc R . .
C2B C 0.4597(5) 0.8695(4) 0.5662(3) 0.0188(9) Uani 1 1 d . . .
H2B H 0.4762 0.8688 0.5057 0.023 Uiso 1 1 calc R . .
C13A C -0.0840(5) -0.1137(4) 0.5740(3) 0.0218(10) Uani 1 1 d . . .
H13A H -0.0627 -0.1320 0.5138 0.026 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 O1A 1.985(3) . ?
Cu1 N7A 2.013(3) . ?
Cu1 Cl3 2.2654(11) . ?
Cu1 Cl2 2.2801(10) . ?
Cu1 Cl2 2.5744(11) 2_567 ?
Cu2 O1B 1.988(3) . ?
Cu2 N7B 2.009(3) . ?
Cu2 Cl5 2.2681(11) . ?
Cu2 Cl4 2.2767(11) . ?
Cu2 Cl4 2.6041(11) 2_677 ?
Cl2 Cu1 2.5744(11) 2_567 ?
Cl4 Cu2 2.6041(11) 2_677 ?
Cl1B C6B 1.723(4) . ?
Cl1A C6A 1.729(4) . ?
N9B C8B 1.355(5) . ?
N9B C4B 1.374(5) . ?
N9B C10B 1.468(5) . ?
N3A C2A 1.326(6) . ?
N3A C4A 1.338(5) . ?
N9A C8A 1.368(5) . ?
N9A C4A 1.370(5) . ?
N9A C10A 1.470(5) . ?
N1A C6A 1.315(5) . ?
N1A C2A 1.358(6) . ?
N3B C2B 1.333(5) . ?
N3B C4B 1.339(5) . ?
N7B C8B 1.329(5) . ?
N7B C5B 1.390(5) . ?
N1B C6B 1.326(5) . ?
N1B C2B 1.343(6) . ?
N7A C8A 1.323(5) . ?
N7A C5A 1.392(5) . ?
C15A C16A 1.389(6) . ?
C15A C14A 1.392(7) . ?
C5B C6B 1.383(6) . ?
C5B C4B 1.393(5) . ?
C10A C11A 1.500(6) . ?
C12A C11A 1.393(6) . ?
C12A C13A 1.397(6) . ?
C11B C16B 1.380(6) . ?
C11B C12B 1.393(6) . ?
C11B C10B 1.511(5) . ?
C4A C5A 1.409(6) . ?
C6A C5A 1.386(6) . ?
C15B C14B 1.391(6) . ?
C15B C16B 1.404(6) . ?
C16A C11A 1.396(6) . ?
C12B C13B 1.387(6) . ?
C14B C13B 1.385(6) . ?
C14A C13A 1.379(6) . ?

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
O1A Cu1 N7A 88.34(12) . . ?
O1A Cu1 Cl3 91.14(9) . . ?
N7A Cu1 Cl3 154.33(10) . . ?
O1A Cu1 Cl2 177.25(8) . . ?
N7A Cu1 Cl2 90.02(9) . . ?
Cl3 Cu1 Cl2 91.30(4) . . ?
O1A Cu1 Cl2 88.37(9) . 2_567 ?
N7A Cu1 Cl2 100.22(10) . 2_567 ?
Cl3 Cu1 Cl2 105.42(4) . 2_567 ?
Cl2 Cu1 Cl2 89.75(4) . 2_567 ?
O1B Cu2 N7B 88.25(13) . . ?
O1B Cu2 Cl5 90.54(9) . . ?
N7B Cu2 Cl5 155.64(10) . . ?
O1B Cu2 Cl4 177.41(9) . . ?
N7B Cu2 Cl4 89.53(10) . . ?
Cl5 Cu2 Cl4 92.03(4) . . ?
O1B Cu2 Cl4 88.77(9) . 2_677 ?
N7B Cu2 Cl4 99.16(10) . 2_677 ?
Cl5 Cu2 Cl4 105.14(4) . 2_677 ?
Cl4 Cu2 Cl4 90.26(4) . 2_677 ?
Cu1 Cl2 Cu1 90.25(4) . 2_567 ?
Cu2 Cl4 Cu2 89.74(4) . 2_677 ?
C8B N9B C4B 106.8(3) . . ?
C8B N9B C10B 127.7(3) . . ?
C4B N9B C10B 125.5(3) . . ?
C2A N3A C4A 112.5(4) . . ?
C8A N9A C4A 106.4(3) . . ?
C8A N9A C10A 127.1(4) . . ?
C4A N9A C10A 126.4(3) . . ?
C6A N1A C2A 117.2(4) . . ?
C2B N3B C4B 111.1(3) . . ?
C8B N7B C5B 104.8(3) . . ?
C8B N7B Cu2 129.3(3) . . ?
C5B N7B Cu2 125.2(3) . . ?
C6B N1B C2B 117.3(4) . . ?
C8A N7A C5A 105.0(3) . . ?
C8A N7A Cu1 129.7(3) . . ?
C5A N7A Cu1 124.7(3) . . ?
C16A C15A C14A 120.2(4) . . ?
N7A C8A N9A 113.2(4) . . ?
C6B C5B N7B 135.6(4) . . ?
C6B C5B C4B 115.1(4) . . ?
N7B C5B C4B 109.3(3) . . ?
N1B C6B C5B 121.0(4) . . ?
N1B C6B Cl1B 118.5(3) . . ?
C5B C6B Cl1B 120.5(3) . . ?
N9A C10A C11A 112.1(3) . . ?
C11A C12A C13A 120.1(4) . . ?
C16B C11B C12B 119.3(4) . . ?
C16B C11B C10B 120.7(4) . . ?
C12B C11B C10B 120.0(4) . . ?
N3A C2A N1A 128.1(4) . . ?
N3A C4A N9A 128.3(4) . . ?
N3A C4A C5A 125.3(4) . . ?
N9A C4A C5A 106.4(3) . . ?
N1A C6A C5A 121.5(4) . . ?
N1A C6A Cl1A 118.6(3) . . ?
C5A C6A Cl1A 119.9(3) . . ?
C14B C15B C16B 119.0(4) . . ?
C15A C16A C11A 120.0(4) . . ?
C13B C12B C11B 120.4(4) . . ?
C12A C11A C16A 119.5(4) . . ?
C12A C11A C10A 119.9(4) . . ?
C16A C11A C10A 120.6(4) . . ?
C6A C5A N7A 135.7(4) . . ?
C6A C5A C4A 115.4(4) . . ?
N7A C5A C4A 108.9(3) . . ?
C13B C14B C15B 120.3(4) . . ?
N3B C4B N9B 127.0(4) . . ?
N3B C4B C5B 126.8(4) . . ?
N9B C4B C5B 106.2(3) . . ?
N9B C10B C11B 111.6(3) . . ?
N7B C8B N9B 112.8(4) . . ?
C11B C16B C15B 121.0(4) . . ?
C13A C14A C15A 120.0(4) . . ?
C14B C13B C12B 120.2(4) . . ?
N3B C2B N1B 128.6(4) . . ?
C14A C13A C12A 120.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.727
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.167
####################################################################### 
# 
# 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_elisha3_0m
_database_code_depnum_ccdc_archive 'CCDC 1508073'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 Cl5 Cu2 N8 O2'
_chemical_formula_weight         673.75

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   12.7021(5)
_cell_length_b                   14.1024(7)
_cell_length_c                   15.5620(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.4300(10)
_cell_angle_gamma                90.00
_cell_volume                     2628.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6516
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      28.3

_exptl_crystal_description       cube
_exptl_crystal_colour            blue-green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    2.158
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6482
_exptl_absorpt_correction_T_max  0.6974
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22297
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         28.32
_reflns_number_total             6516
_reflns_number_gt                6058
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0229P)²+1.6372P] 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         6516
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0500
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.004
_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 0.780993(14) 0.768725(12) 0.995438(11) 0.01158(4) Uani 1 1 d . . .
Cu2 Cu 0.952306(13) 1.117635(11) 1.041053(10) 0.01057(4) Uani 1 1 d . . .
Cl1 Cl 0.89854(3) 0.66560(3) 0.96306(2) 0.01983(7) Uani 1 1 d . . .
Cl2 Cl 0.90665(3) 0.92800(2) 1.01319(2) 0.01089(6) Uani 1 1 d . . .
Cl3 Cl 0.68141(3) 0.57193(2) 1.05304(2) 0.01750(7) Uani 1 1 d . . .
Cl4 Cl 0.84430(3) 1.17971(2) 0.90792(2) 0.01427(7) Uani 1 1 d . . .
Cl5 Cl 0.63546(3) 0.84446(2) 1.02111(2) 0.01651(7) Uani 1 1 d . . .
O1S O 0.71788(12) 0.65033(10) 0.74203(9) 0.0273(3) Uani 1 1 d . . .
O2S O 0.71303(10) 0.78822(9) 0.86381(7) 0.0207(2) Uani 1 1 d . . .
N12A N 0.82889(10) 1.14451(8) 1.09311(8) 0.0124(2) Uani 1 1 d . . .
N1S N 0.06402(13) 0.99927(11) 0.71131(11) 0.0301(3) Uani 1 1 d . . .
N3S N 0.48597(13) 0.33996(12) 0.77597(10) 0.0329(3) Uani 1 1 d . . .
C11A C 0.82470(11) 1.22604(10) 1.13758(9) 0.0126(2) Uani 1 1 d . . .
C10A C 1.07692(11) 0.79143(10) 1.34425(9) 0.0130(2) Uani 1 1 d . . .
H2A H 1.0560 0.7968 1.3986 0.016 Uiso 1 1 calc R . .
H2B H 1.0970 0.8541 1.3291 0.016 Uiso 1 1 calc R . .
N9A N 0.98192(9) 0.75506(8) 1.26868(7) 0.0111(2) Uani 1 1 d . . .
C4A C 0.92463(11) 0.67244(9) 1.26555(9) 0.0101(2) Uani 1 1 d . . .
N3A N 0.93675(10) 0.60733(8) 1.33056(8) 0.0112(2) Uani 1 1 d . . .
C2A C 0.86825(11) 0.53271(10) 1.30301(9) 0.0134(3) Uani 1 1 d . . .
H3 H 0.8742 0.4853 1.3459 0.016 Uiso 1 1 calc R . .
N1A N 0.79236(10) 0.51913(8) 1.22058(8) 0.0144(2) Uani 1 1 d . . .
C6A C 0.78077(11) 0.58616(10) 1.15810(9) 0.0125(2) Uani 1 1 d . . .
C5A C 0.84738(11) 0.66641(9) 1.17751(9) 0.0111(2) Uani 1 1 d . . .
N7A N 0.85813(10) 0.74518(8) 1.12817(8) 0.0114(2) Uani 1 1 d . . .
C8A C 0.93936(11) 0.79522(10) 1.18458(9) 0.0119(2) Uani 1 1 d . . .
H1 H 0.9651 0.8521 1.1687 0.014 Uiso 1 1 calc R . .
C16A C 0.73469(12) 1.24851(11) 1.16504(10) 0.0180(3) Uani 1 1 d . . .
H8 H 0.7337 1.3050 1.1955 0.022 Uiso 1 1 calc R . .
C15A C 0.64598(13) 1.18547(12) 1.14643(10) 0.0221(3) Uani 1 1 d . . .
H5 H 0.5842 1.1995 1.1635 0.027 Uiso 1 1 calc R . .
C14A C 0.65092(12) 1.10156(11) 1.10212(11) 0.0202(3) Uani 1 1 d . . .
H6 H 0.5929 1.0579 1.0898 0.024 Uiso 1 1 calc R . .
C13A C 0.74327(12) 1.08313(10) 1.07627(10) 0.0165(3) Uani 1 1 d . . .
H7 H 0.7462 1.0266 1.0464 0.020 Uiso 1 1 calc R . .
C2S C 0.17043(17) 0.93280(13) 0.60833(15) 0.0359(4) Uani 1 1 d . . .
H10 H 0.2479 0.9493 0.6344 0.054 Uiso 1 1 calc R . .
H11 H 0.1404 0.9600 0.5486 0.054 Uiso 1 1 calc R . .
H9 H 0.1630 0.8651 0.6041 0.054 Uiso 1 1 calc R . .
C1S C 0.10968(14) 0.96923(11) 0.66586(12) 0.0245(3) Uani 1 1 d . . .
C6S C 0.58261(15) 0.32272(14) 0.94989(11) 0.0285(4) Uani 1 1 d . . .
H12 H 0.6532 0.2917 0.9614 0.043 Uiso 1 1 calc R . .
H13 H 0.5364 0.2854 0.9748 0.043 Uiso 1 1 calc R . .
H14 H 0.5943 0.3842 0.9780 0.043 Uiso 1 1 calc R . .
C5S C 0.52794(13) 0.33312(12) 0.85235(11) 0.0224(3) Uani 1 1 d . . .
N2S N 0.50722(17) 0.58823(16) 0.86230(13) 0.0508(5) Uani 1 1 d . . .
C3S C 0.47676(15) 0.57930(14) 0.78529(13) 0.0325(4) Uani 1 1 d . . .
C4S C 0.43719(16) 0.56724(14) 0.68647(12) 0.0323(4) Uani 1 1 d . . .
H16 H 0.4320 0.5009 0.6720 0.048 Uiso 1 1 calc R . .
H17 H 0.4886 0.5969 0.6615 0.048 Uiso 1 1 calc R . .
H18 H 0.3650 0.5960 0.6609 0.048 Uiso 1 1 calc R . .
H1S H 0.700(2) 0.6534(18) 0.6922(19) 0.046(7) Uiso 1 1 d . . .
H2S H 0.773(3) 0.616(2) 0.760(2) 0.064(9) Uiso 1 1 d . . .
H3S H 0.6507(19) 0.8067(15) 0.8463(14) 0.025(5) Uiso 1 1 d . . .
H4S H 0.7169(19) 0.7439(17) 0.8316(16) 0.036(6) Uiso 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
Cu1 O2S 1.9597(11) . ?
Cu1 N7A 1.9976(11) . ?
Cu1 Cl1 2.2581(4) . ?
Cu1 Cl5 2.2822(4) . ?
Cu1 Cl2 2.7158(4) . ?
Cu2 N12A 2.0255(12) . ?
Cu2 N3A 2.0312(11) 2_757 ?
Cu2 Cl4 2.2472(4) . ?
Cu2 Cl2 2.3114(3) 3_777 ?
Cu2 Cl2 2.7402(4) . ?
Cl2 Cu2 2.3114(4) 3_777 ?
Cl3 C6A 1.7127(13) . ?
O1S H1S 0.73(3) . ?
O1S H2S 0.82(3) . ?
O2S H3S 0.79(2) . ?
O2S H4S 0.81(2) . ?
N12A C13A 1.3458(18) . ?
N12A C11A 1.3521(17) . ?
N1S C1S 1.135(2) . ?
N3S C5S 1.133(2) . ?
C11A C16A 1.384(2) . ?
C11A C10A 1.5023(19) 2_757 ?
C10A N9A 1.4691(17) . ?
C10A C11A 1.5023(19) 2_747 ?
C10A H2A 0.9700 . ?
C10A H2B 0.9700 . ?
N9A C8A 1.3620(17) . ?
N9A C4A 1.3659(17) . ?
C4A N3A 1.3368(16) . ?
C4A C5A 1.3973(18) . ?
N3A C2A 1.3416(18) . ?
N3A Cu2 2.0312(11) 2_747 ?
C2A N1A 1.3374(18) . ?
C2A H3 0.9300 . ?
N1A C6A 1.3287(18) . ?
C6A C5A 1.3849(19) . ?
C5A N7A 1.3827(17) . ?
N7A C8A 1.3155(18) . ?
C8A H1 0.9300 . ?
C16A C15A 1.388(2) . ?
C16A H8 0.9300 . ?
C15A C14A 1.381(2) . ?
C15A H5 0.9300 . ?
C14A C13A 1.385(2) . ?
C14A H6 0.9300 . ?
C13A H7 0.9300 . ?
C2S C1S 1.456(3) . ?
C2S H10 0.9600 . ?
C2S H11 0.9600 . ?
C2S H9 0.9600 . ?
C6S C5S 1.451(2) . ?
C6S H12 0.9600 . ?
C6S H13 0.9600 . ?
C6S H14 0.9600 . ?
N2S C3S 1.137(3) . ?
C3S C4S 1.460(3) . ?
C4S H16 0.9600 . ?
C4S H17 0.9600 . ?
C4S H18 0.9600 . ?

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
O2S Cu1 N7A 176.53(5) . . ?
O2S Cu1 Cl1 87.20(4) . . ?
N7A Cu1 Cl1 89.45(3) . . ?
O2S Cu1 Cl5 90.94(4) . . ?
N7A Cu1 Cl5 92.52(3) . . ?
Cl1 Cu1 Cl5 167.073(15) . . ?
O2S Cu1 Cl2 91.72(4) . . ?
N7A Cu1 Cl2 87.87(3) . . ?
Cl1 Cu1 Cl2 98.367(13) . . ?
Cl5 Cu1 Cl2 94.474(13) . . ?
N12A Cu2 N3A 89.77(5) . 2_757 ?
N12A Cu2 Cl4 88.82(3) . . ?
N3A Cu2 Cl4 161.04(3) 2_757 . ?
N12A Cu2 Cl2 174.41(3) . 3_777 ?
N3A Cu2 Cl2 88.33(3) 2_757 3_777 ?
Cl4 Cu2 Cl2 94.671(13) . 3_777 ?
N12A Cu2 Cl2 95.43(3) . . ?
N3A Cu2 Cl2 97.29(3) 2_757 . ?
Cl4 Cu2 Cl2 101.662(12) . . ?
Cl2 Cu2 Cl2 79.597(12) 3_777 . ?
Cu2 Cl2 Cu1 103.490(12) 3_777 . ?
Cu2 Cl2 Cu2 100.403(12) 3_777 . ?
Cu1 Cl2 Cu2 155.441(13) . . ?
H1S O1S H2S 109(3) . . ?
Cu1 O2S H3S 116.7(15) . . ?
Cu1 O2S H4S 116.2(16) . . ?
H3S O2S H4S 108(2) . . ?
C13A N12A C11A 118.67(12) . . ?
C13A N12A Cu2 118.99(10) . . ?
C11A N12A Cu2 122.09(9) . . ?
N12A C11A C16A 122.00(13) . . ?
N12A C11A C10A 116.52(12) . 2_757 ?
C16A C11A C10A 121.48(13) . 2_757 ?
N9A C10A C11A 110.28(11) . 2_747 ?
N9A C10A H2A 109.6 . . ?
C11A C10A H2A 109.6 2_747 . ?
N9A C10A H2B 109.6 . . ?
C11A C10A H2B 109.6 2_747 . ?
H2A C10A H2B 108.1 . . ?
C8A N9A C4A 106.50(11) . . ?
C8A N9A C10A 125.58(11) . . ?
C4A N9A C10A 127.76(11) . . ?
N3A C4A N9A 129.28(12) . . ?
N3A C4A C5A 124.52(12) . . ?
N9A C4A C5A 106.19(11) . . ?
C4A N3A C2A 113.44(11) . . ?
C4A N3A Cu2 124.25(9) . 2_747 ?
C2A N3A Cu2 122.31(9) . 2_747 ?
N1A C2A N3A 127.06(12) . . ?
N1A C2A H3 116.5 . . ?
N3A C2A H3 116.5 . . ?
C6A N1A C2A 117.98(12) . . ?
N1A C6A C5A 120.72(12) . . ?
N1A C6A Cl3 118.84(10) . . ?
C5A C6A Cl3 120.45(10) . . ?
N7A C5A C6A 134.54(12) . . ?
N7A C5A C4A 109.19(11) . . ?
C6A C5A C4A 116.26(12) . . ?
C8A N7A C5A 105.12(11) . . ?
C8A N7A Cu1 127.36(9) . . ?
C5A N7A Cu1 127.06(9) . . ?
N7A C8A N9A 112.99(12) . . ?
N7A C8A H1 123.5 . . ?
N9A C8A H1 123.5 . . ?
C11A C16A C15A 119.05(14) . . ?
C11A C16A H8 120.5 . . ?
C15A C16A H8 120.5 . . ?
C14A C15A C16A 118.96(14) . . ?
C14A C15A H5 120.5 . . ?
C16A C15A H5 120.5 . . ?
C15A C14A C13A 119.28(14) . . ?
C15A C14A H6 120.4 . . ?
C13A C14A H6 120.4 . . ?
N12A C13A C14A 122.02(14) . . ?
N12A C13A H7 119.0 . . ?
C14A C13A H7 119.0 . . ?
C1S C2S H10 109.5 . . ?
C1S C2S H11 109.5 . . ?
H10 C2S H11 109.5 . . ?
C1S C2S H9 109.5 . . ?
H10 C2S H9 109.5 . . ?
H11 C2S H9 109.5 . . ?
N1S C1S C2S 178.44(19) . . ?
C5S C6S H12 109.5 . . ?
C5S C6S H13 109.5 . . ?
H12 C6S H13 109.5 . . ?
C5S C6S H14 109.5 . . ?
H12 C6S H14 109.5 . . ?
H13 C6S H14 109.5 . . ?
N3S C5S C6S 178.9(2) . . ?
N2S C3S C4S 179.6(3) . . ?
C3S C4S H16 109.5 . . ?
C3S C4S H17 109.5 . . ?
H16 C4S H17 109.5 . . ?
C3S C4S H18 109.5 . . ?
H16 C4S H18 109.5 . . ?
H17 C4S H18 109.5 . . ?

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
O2S Cu1 Cl2 Cu2 -76.67(4) . . . 3_777 ?
N7A Cu1 Cl2 Cu2 99.89(3) . . . 3_777 ?
Cl1 Cu1 Cl2 Cu2 10.757(15) . . . 3_777 ?
Cl5 Cu1 Cl2 Cu2 -167.746(13) . . . 3_777 ?
O2S Cu1 Cl2 Cu2 89.69(5) . . . . ?
N7A Cu1 Cl2 Cu2 -93.76(5) . . . . ?
Cl1 Cu1 Cl2 Cu2 177.11(3) . . . . ?
Cl5 Cu1 Cl2 Cu2 -1.39(3) . . . . ?
N12A Cu2 Cl2 Cu2 -177.41(3) . . . 3_777 ?
N3A Cu2 Cl2 Cu2 -86.94(3) 2_757 . . 3_777 ?
Cl4 Cu2 Cl2 Cu2 92.674(14) . . . 3_777 ?
Cl2 Cu2 Cl2 Cu2 0.0 3_777 . . 3_777 ?
N12A Cu2 Cl2 Cu1 16.08(5) . . . . ?
N3A Cu2 Cl2 Cu1 106.55(4) 2_757 . . . ?
Cl4 Cu2 Cl2 Cu1 -73.84(3) . . . . ?
Cl2 Cu2 Cl2 Cu1 -166.51(4) 3_777 . . . ?
N3A Cu2 N12A C13A -117.11(11) 2_757 . . . ?
Cl4 Cu2 N12A C13A 81.79(10) . . . . ?
Cl2 Cu2 N12A C13A -47.0(4) 3_777 . . . ?
Cl2 Cu2 N12A C13A -19.81(10) . . . . ?
N3A Cu2 N12A C11A 68.68(11) 2_757 . . . ?
Cl4 Cu2 N12A C11A -92.41(10) . . . . ?
Cl2 Cu2 N12A C11A 138.8(3) 3_777 . . . ?
Cl2 Cu2 N12A C11A 165.99(10) . . . . ?
C13A N12A C11A C16A -0.8(2) . . . . ?
Cu2 N12A C11A C16A 173.37(10) . . . . ?
C13A N12A C11A C10A 179.20(12) . . . 2_757 ?
Cu2 N12A C11A C10A -6.58(16) . . . 2_757 ?
C11A C10A N9A C8A -111.04(14) 2_747 . . . ?
C11A C10A N9A C4A 63.65(17) 2_747 . . . ?
C8A N9A C4A N3A 178.97(13) . . . . ?
C10A N9A C4A N3A 3.5(2) . . . . ?
C8A N9A C4A C5A -0.38(14) . . . . ?
C10A N9A C4A C5A -175.87(12) . . . . ?
N9A C4A N3A C2A -177.96(13) . . . . ?
C5A C4A N3A C2A 1.28(19) . . . . ?
N9A C4A N3A Cu2 1.7(2) . . . 2_747 ?
C5A C4A N3A Cu2 -179.04(10) . . . 2_747 ?
C4A N3A C2A N1A -0.5(2) . . . . ?
Cu2 N3A C2A N1A 179.80(11) 2_747 . . . ?
N3A C2A N1A C6A -0.9(2) . . . . ?
C2A N1A C6A C5A 1.5(2) . . . . ?
C2A N1A C6A Cl3 -178.17(10) . . . . ?
N1A C6A C5A N7A 177.69(14) . . . . ?
Cl3 C6A C5A N7A -2.6(2) . . . . ?
N1A C6A C5A C4A -0.82(19) . . . . ?
Cl3 C6A C5A C4A 178.87(10) . . . . ?
N3A C4A C5A N7A -179.55(12) . . . . ?
N9A C4A C5A N7A -0.16(15) . . . . ?
N3A C4A C5A C6A -0.7(2) . . . . ?
N9A C4A C5A C6A 178.72(11) . . . . ?
C6A C5A N7A C8A -177.94(15) . . . . ?
C4A C5A N7A C8A 0.65(15) . . . . ?
C6A C5A N7A Cu1 -5.3(2) . . . . ?
C4A C5A N7A Cu1 173.30(9) . . . . ?
O2S Cu1 N7A C8A 79.8(8) . . . . ?
Cl1 Cu1 N7A C8A 95.06(11) . . . . ?
Cl5 Cu1 N7A C8A -97.72(11) . . . . ?
Cl2 Cu1 N7A C8A -3.33(11) . . . . ?
O2S Cu1 N7A C5A -91.2(8) . . . . ?
Cl1 Cu1 N7A C5A -76.00(11) . . . . ?
Cl5 Cu1 N7A C5A 91.22(11) . . . . ?
Cl2 Cu1 N7A C5A -174.40(11) . . . . ?
C5A N7A C8A N9A -0.92(15) . . . . ?
Cu1 N7A C8A N9A -173.54(9) . . . . ?
C4A N9A C8A N7A 0.84(15) . . . . ?
C10A N9A C8A N7A 176.46(12) . . . . ?
N12A C11A C16A C15A 0.0(2) . . . . ?
C10A C11A C16A C15A 179.97(13) 2_757 . . . ?
C11A C16A C15A C14A 0.9(2) . . . . ?
C16A C15A C14A C13A -0.9(2) . . . . ?
C11A N12A C13A C14A 0.8(2) . . . . ?
Cu2 N12A C13A C14A -173.62(11) . . . . ?
C15A C14A C13A N12A 0.1(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
C13A H7 Cl2 0.93 2.66 3.3781(15) 135.0 .
C13A H7 Cl5 0.93 2.89 3.6275(15) 137.0 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_5aprb_0m
_database_code_depnum_ccdc_archive 'CCDC 1508065'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Cl N5'
_chemical_formula_weight         245.67

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   4.12060(10)
_cell_length_b                   12.0535(4)
_cell_length_c                   21.2191(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1053.90(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2623
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      28.3

_exptl_crystal_description       needle-like
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9281
_exptl_absorpt_correction_T_max  0.9406
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10771
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         28.34
_reflns_number_total             2623
_reflns_number_gt                2398
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0357P)²+0.2445P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.94(6)
_refine_ls_number_reflns         2623
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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
Cl1 Cl -0.17813(12) 0.19307(4) 0.05847(2) 0.02063(12) Uani 1 1 d . . .
N1 N -0.1133(4) -0.00031(12) 0.11283(7) 0.0165(3) Uani 1 1 d . . .
N9 N 0.4496(4) 0.12166(13) 0.25104(7) 0.0141(3) Uani 1 1 d . . .
N7 N 0.2721(4) 0.25000(12) 0.18158(7) 0.0179(3) Uani 1 1 d . . .
N15 N 0.3076(4) 0.17819(12) 0.38224(7) 0.0159(3) Uani 1 1 d . . .
N3 N 0.1928(4) -0.04188(12) 0.20661(7) 0.0152(3) Uani 1 1 d . . .
C15 C 0.1418(4) 0.18412(15) 0.43647(8) 0.0171(4) Uani 1 1 d . . .
H15 H 0.0592 0.2527 0.4486 0.021 Uiso 1 1 calc R . .
C6 C -0.0340(4) 0.10564(15) 0.11662(8) 0.0141(4) Uani 1 1 d . . .
C4 C 0.2626(4) 0.06595(14) 0.20825(7) 0.0122(3) Uani 1 1 d . . .
C2 C 0.0033(5) -0.06823(16) 0.15806(8) 0.0184(4) Uani 1 1 d . . .
H2 H -0.0559 -0.1425 0.1549 0.022 Uiso 1 1 calc R . .
C5 C 0.1567(5) 0.14651(13) 0.16515(8) 0.0131(3) Uani 1 1 d . . .
C11 C 0.4206(4) 0.07796(15) 0.36532(8) 0.0137(4) Uani 1 1 d . . .
C12 C 0.3716(5) -0.01643(15) 0.40054(9) 0.0197(4) Uani 1 1 d . . .
H12 H 0.4501 -0.0846 0.3869 0.024 Uiso 1 1 calc R . .
C14 C 0.0867(5) 0.09430(16) 0.47535(9) 0.0202(4) Uani 1 1 d . . .
H14 H -0.0258 0.1025 0.5131 0.024 Uiso 1 1 calc R . .
C8 C 0.4438(5) 0.23078(15) 0.23250(9) 0.0174(4) Uani 1 1 d . . .
H8 H 0.5526 0.2865 0.2543 0.021 Uiso 1 1 calc R . .
C13 C 0.2026(5) -0.00776(16) 0.45689(9) 0.0228(4) Uani 1 1 d . . .
H13 H 0.1681 -0.0701 0.4819 0.027 Uiso 1 1 calc R . .
C10 C 0.6180(4) 0.07459(16) 0.30559(8) 0.0165(4) Uani 1 1 d . . .
H10A H 0.8184 0.1152 0.3123 0.020 Uiso 1 1 calc R . .
H10B H 0.6743 -0.0019 0.2964 0.020 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
Cl1 C6 1.7280(17) . ?
N1 C6 1.321(2) . ?
N1 C2 1.350(2) . ?
N9 C4 1.367(2) . ?
N9 C8 1.373(2) . ?
N9 C10 1.464(2) . ?
N7 C8 1.312(2) . ?
N7 C5 1.380(2) . ?
N15 C15 1.340(2) . ?
N15 C11 1.344(2) . ?
N3 C2 1.331(2) . ?
N3 C4 1.332(2) . ?
C15 C14 1.380(3) . ?
C6 C5 1.386(2) . ?
C4 C5 1.404(2) . ?
C11 C12 1.376(3) . ?
C11 C10 1.507(2) . ?
C12 C13 1.388(3) . ?
C14 C13 1.377(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
C6 N1 C2 117.07(15) . . ?
C4 N9 C8 105.68(15) . . ?
C4 N9 C10 127.01(15) . . ?
C8 N9 C10 127.31(15) . . ?
C8 N7 C5 103.55(15) . . ?
C15 N15 C11 117.00(15) . . ?
C2 N3 C4 112.32(15) . . ?
N15 C15 C14 123.74(17) . . ?
N1 C6 C5 121.96(15) . . ?
N1 C6 Cl1 117.47(13) . . ?
C5 C6 Cl1 120.57(13) . . ?
N3 C4 N9 128.20(15) . . ?
N3 C4 C5 126.24(15) . . ?
N9 C4 C5 105.56(15) . . ?
N3 C2 N1 127.91(17) . . ?
N7 C5 C6 134.80(16) . . ?
N7 C5 C4 110.71(15) . . ?
C6 C5 C4 114.49(15) . . ?
N15 C11 C12 123.19(16) . . ?
N15 C11 C10 115.85(16) . . ?
C12 C11 C10 120.92(16) . . ?
C11 C12 C13 118.65(17) . . ?
C13 C14 C15 118.29(17) . . ?
N7 C8 N9 114.49(16) . . ?
C14 C13 C12 119.11(17) . . ?
N9 C10 C11 113.52(14) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_20octc
_database_code_depnum_ccdc_archive 'CCDC 1508068'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 Cl2 Cu2 N10 O8'
_chemical_formula_weight         854.60

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   14.292(4)
_cell_length_b                   15.123(5)
_cell_length_c                   8.344(6)
_cell_angle_alpha                90.000
_cell_angle_beta                 106.632(5)
_cell_angle_gamma                90.000
_cell_volume                     1728.0(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3021
_cell_measurement_theta_min      4.3
_cell_measurement_theta_max      25.0

_exptl_crystal_description       needle-like
_exptl_crystal_colour            blue-green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             868
_exptl_absorpt_coefficient_mu    1.451
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7408
_exptl_absorpt_correction_T_max  0.7802
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11330
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.26
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3021
_reflns_number_gt                2657
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0289P)²+1.7416P] 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         3021
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0614
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.075221(17) 0.457807(16) 0.09781(3) 0.00909(9) Uani 1 1 d . . .
Cl1 Cl 0.62975(4) 0.32011(4) -0.09665(7) 0.02210(14) Uani 1 1 d . . .
O1 O 0.13203(11) 0.46926(10) -0.08915(19) 0.0165(3) Uani 1 1 d . . .
O4 O -0.12133(11) 0.42319(10) -0.1787(2) 0.0175(3) Uani 1 1 d . . .
N3 N 0.55031(13) 0.42452(12) 0.3541(2) 0.0137(4) Uani 1 1 d . . .
O3 O 0.00635(11) 0.35081(10) -0.01137(19) 0.0156(3) Uani 1 1 d . . .
N1 N 0.66513(13) 0.36600(12) 0.2184(2) 0.0173(4) Uani 1 1 d . . .
O2 O 0.00533(11) 0.54379(10) -0.25334(18) 0.0157(3) Uani 1 1 d . . .
N9 N 0.38766(12) 0.44123(11) 0.1598(2) 0.0112(4) Uani 1 1 d . . .
N7 N 0.41755(13) 0.39123(12) -0.0763(2) 0.0156(4) Uani 1 1 d . . .
N12 N 0.19553(12) 0.38344(11) 0.2799(2) 0.0094(4) Uani 1 1 d . . .
C4 C 0.48459(15) 0.41841(13) 0.2045(3) 0.0106(4) Uani 1 1 d . . .
C10 C 0.33310(15) 0.47754(13) 0.2698(3) 0.0113(4) Uani 1 1 d . . .
H10A H 0.2810 0.5152 0.2049 0.014 Uiso 1 1 calc R . .
H10B H 0.3765 0.5136 0.3557 0.014 Uiso 1 1 calc R . .
C16 C 0.34639(15) 0.36290(14) 0.4936(3) 0.0143(5) Uani 1 1 d . . .
H16 H 0.4104 0.3809 0.5428 0.017 Uiso 1 1 calc R . .
C14 C 0.21179(16) 0.26866(14) 0.4850(3) 0.0150(5) Uani 1 1 d . . .
H14 H 0.1839 0.2212 0.5255 0.018 Uiso 1 1 calc R . .
C6 C 0.59683(16) 0.36128(14) 0.0737(3) 0.0156(5) Uani 1 1 d . . .
C2 C 0.63820(16) 0.39744(15) 0.3498(3) 0.0169(5) Uani 1 1 d . . .
H2 H 0.6874 0.4006 0.4505 0.020 Uiso 1 1 calc R . .
C5 C 0.50140(15) 0.38733(13) 0.0563(3) 0.0125(4) Uani 1 1 d . . .
C15 C 0.30695(16) 0.29350(14) 0.5620(3) 0.0162(5) Uani 1 1 d . . .
H15 H 0.3438 0.2645 0.6575 0.019 Uiso 1 1 calc R . .
C11 C 0.28986(14) 0.40516(13) 0.3517(2) 0.0102(4) Uani 1 1 d . . .
C8 C 0.35251(16) 0.42297(14) -0.0084(3) 0.0149(5) Uani 1 1 d . . .
H8 H 0.2878 0.4324 -0.0691 0.018 Uiso 1 1 calc R . .
C18 C 0.13411(16) 0.50512(16) -0.3650(3) 0.0175(5) Uani 1 1 d . . .
H18A H 0.1466 0.5647 -0.3929 0.026 Uiso 1 1 calc R . .
H18B H 0.0911 0.4769 -0.4612 0.026 Uiso 1 1 calc R . .
H18C H 0.1945 0.4731 -0.3303 0.026 Uiso 1 1 calc R . .
C13 C 0.15885(16) 0.31541(14) 0.3469(3) 0.0133(4) Uani 1 1 d . . .
H13 H 0.0943 0.2991 0.2972 0.016 Uiso 1 1 calc R . .
C20 C -0.11721(17) 0.26765(15) -0.2018(3) 0.0222(5) Uani 1 1 d . . .
H20A H -0.1844 0.2642 -0.2023 0.033 Uiso 1 1 calc R . .
H20B H -0.0815 0.2193 -0.1382 0.033 Uiso 1 1 calc R . .
H20C H -0.1132 0.2645 -0.3146 0.033 Uiso 1 1 calc R . .
C17 C 0.08722(15) 0.50623(13) -0.2250(3) 0.0108(4) Uani 1 1 d . . .
C19 C -0.07418(15) 0.35374(14) -0.1240(3) 0.0119(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
Cu1 O1 1.9617(17) . ?
Cu1 O2 1.9660(16) 3_565 ?
Cu1 O4 1.9682(16) 3_565 ?
Cu1 O3 1.9757(16) . ?
Cu1 N12 2.2437(18) . ?
Cu1 Cu1 2.6281(8) 3_565 ?
Cl1 C6 1.736(2) . ?
O1 C17 1.262(3) . ?
O4 C19 1.261(3) . ?
O4 Cu1 1.9682(16) 3_565 ?
N3 C2 1.332(3) . ?
N3 C4 1.333(3) . ?
O3 C19 1.261(3) . ?
N1 C6 1.320(3) . ?
N1 C2 1.348(3) . ?
O2 C17 1.261(3) . ?
O2 Cu1 1.9660(16) 3_565 ?
N9 C4 1.372(3) . ?
N9 C8 1.377(3) . ?
N9 C10 1.470(3) . ?
N7 C8 1.310(3) . ?
N7 C5 1.380(3) . ?
N12 C13 1.347(3) . ?
N12 C11 1.350(3) . ?
C4 C5 1.406(3) . ?
C10 C11 1.513(3) . ?
C16 C11 1.384(3) . ?
C16 C15 1.389(3) . ?
C14 C15 1.380(3) . ?
C14 C13 1.379(3) . ?
C6 C5 1.387(3) . ?
C18 C17 1.504(3) . ?
C20 C19 1.505(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
O1 Cu1 O2 168.49(6) . 3_565 ?
O1 Cu1 O4 91.01(7) . 3_565 ?
O2 Cu1 O4 89.25(7) 3_565 3_565 ?
O1 Cu1 O3 88.31(7) . . ?
O2 Cu1 O3 89.18(7) 3_565 . ?
O4 Cu1 O3 168.70(6) 3_565 . ?
O1 Cu1 N12 99.86(7) . . ?
O2 Cu1 N12 91.54(7) 3_565 . ?
O4 Cu1 N12 96.30(7) 3_565 . ?
O3 Cu1 N12 94.93(7) . . ?
O1 Cu1 Cu1 85.09(6) . 3_565 ?
O2 Cu1 Cu1 83.48(6) 3_565 3_565 ?
O4 Cu1 Cu1 84.43(5) 3_565 3_565 ?
O3 Cu1 Cu1 84.27(5) . 3_565 ?
N12 Cu1 Cu1 174.96(4) . 3_565 ?
C17 O1 Cu1 122.30(14) . . ?
C19 O4 Cu1 123.10(14) . 3_565 ?
C2 N3 C4 111.75(18) . . ?
C19 O3 Cu1 122.88(14) . . ?
C6 N1 C2 117.04(19) . . ?
C17 O2 Cu1 123.93(14) . 3_565 ?
C4 N9 C8 105.79(17) . . ?
C4 N9 C10 126.81(18) . . ?
C8 N9 C10 127.40(18) . . ?
C8 N7 C5 103.30(18) . . ?
C13 N12 C11 117.36(18) . . ?
C13 N12 Cu1 110.49(13) . . ?
C11 N12 Cu1 130.78(14) . . ?
N3 C4 N9 128.54(19) . . ?
N3 C4 C5 126.48(19) . . ?
N9 C4 C5 104.98(18) . . ?
N9 C10 C11 111.71(17) . . ?
C11 C16 C15 119.6(2) . . ?
C15 C14 C13 118.8(2) . . ?
N1 C6 C5 121.9(2) . . ?
N1 C6 Cl1 117.77(16) . . ?
C5 C6 Cl1 120.35(18) . . ?
N3 C2 N1 128.4(2) . . ?
N7 C5 C6 134.3(2) . . ?
N7 C5 C4 111.28(18) . . ?
C6 C5 C4 114.4(2) . . ?
C14 C15 C16 118.4(2) . . ?
N12 C11 C16 122.13(19) . . ?
N12 C11 C10 117.42(18) . . ?
C16 C11 C10 120.44(18) . . ?
N7 C8 N9 114.65(19) . . ?
N12 C13 C14 123.6(2) . . ?
O2 C17 O1 124.98(19) . . ?
O2 C17 C18 117.09(18) . . ?
O1 C17 C18 117.93(19) . . ?
O4 C19 O3 125.31(19) . . ?
O4 C19 C20 117.04(19) . . ?
O3 C19 C20 117.65(19) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_7octa
_database_code_depnum_ccdc_archive 'CCDC 1508066'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Cl4 Cu N8'
_chemical_formula_weight         527.72

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   14.861(8)
_cell_length_b                   14.801(8)
_cell_length_c                   10.073(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.679(9)
_cell_angle_gamma                90.00
_cell_volume                     2111.0(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3694
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      25

_exptl_crystal_description       block-type
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1068
_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7250
_exptl_absorpt_correction_T_max  0.7663
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10428
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         24.71
_reflns_number_total             3572
_reflns_number_gt                3064
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0608P)²+2.2477P] 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         3572
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.22957(3) 0.66521(3) 1.36429(4) 0.01664(14) Uani 1 1 d . . .
Cl3 Cl 0.15551(5) 0.55948(5) 1.45265(8) 0.0220(2) Uani 1 1 d . . .
Cl1B Cl 0.39660(6) 0.65320(5) 1.19849(8) 0.0198(2) Uani 1 1 d . . .
Cl1A Cl 0.22802(5) 0.47249(5) 1.16452(8) 0.0209(2) Uani 1 1 d . . .
Cl2 Cl 0.26156(5) 0.81519(5) 1.38127(8) 0.0195(2) Uani 1 1 d . . .
N9B N 0.46210(18) 0.60425(17) 1.7007(3) 0.0167(6) Uani 1 1 d . . .
N3A N 0.00266(19) 0.61570(18) 0.8314(3) 0.0189(6) Uani 1 1 d . . .
N9A N 0.02771(18) 0.73923(17) 0.9975(3) 0.0179(6) Uani 1 1 d . . .
N3B N 0.59936(18) 0.58956(17) 1.6186(3) 0.0175(6) Uani 1 1 d . . .
N7B N 0.35305(18) 0.63430(17) 1.4993(3) 0.0167(6) Uani 1 1 d . . .
N1B N 0.56123(18) 0.60998(17) 1.3721(3) 0.0186(6) Uani 1 1 d . . .
N7A N 0.13798(18) 0.67531(17) 1.1759(3) 0.0169(6) Uani 1 1 d . . .
N1A N 0.10015(19) 0.48650(18) 0.9222(3) 0.0212(6) Uani 1 1 d . . .
C2B C 0.6206(2) 0.5917(2) 1.5001(3) 0.0187(7) Uani 1 1 d . . .
C6A C 0.1385(2) 0.5276(2) 1.0420(3) 0.0183(7) Uani 1 1 d . . .
C4A C 0.0423(2) 0.6539(2) 0.9551(3) 0.0167(7) Uani 1 1 d . . .
C4B C 0.5088(2) 0.6064(2) 1.6019(3) 0.0167(7) Uani 1 1 d . . .
C10B C 0.5053(2) 0.5820(2) 1.8488(3) 0.0196(7) Uani 1 1 d . . .
H10A H 0.5398 0.5257 1.8561 0.023 Uiso 1 1 calc R . .
H10B H 0.4558 0.5733 1.8920 0.023 Uiso 1 1 calc R . .
C5B C 0.4399(2) 0.6254(2) 1.4759(3) 0.0155(7) Uani 1 1 d . . .
C6B C 0.4719(2) 0.6275(2) 1.3608(3) 0.0169(7) Uani 1 1 d . . .
C11B C 0.5718(3) 0.6551(2) 1.9267(4) 0.0280(8) Uani 1 1 d . . .
H11A H 0.6137 0.6725 1.8738 0.034 Uiso 1 1 calc R . .
H11B H 0.5356 0.7079 1.9364 0.034 Uiso 1 1 calc R . .
C10A C -0.0389(2) 0.8076(2) 0.9168(3) 0.0200(7) Uani 1 1 d . . .
H10C H -0.0281 0.8159 0.8274 0.024 Uiso 1 1 calc R . .
H10D H -0.0266 0.8648 0.9661 0.024 Uiso 1 1 calc R . .
C8A C 0.0865(2) 0.7484(2) 1.1275(3) 0.0178(7) Uani 1 1 d . . .
C11A C -0.1413(2) 0.7814(2) 0.8931(3) 0.0210(7) Uani 1 1 d . . .
H11C H -0.1816 0.8282 0.8384 0.025 Uiso 1 1 calc R . .
H11D H -0.1543 0.7260 0.8392 0.025 Uiso 1 1 calc R . .
C5A C 0.1107(2) 0.6139(2) 1.0672(3) 0.0159(7) Uani 1 1 d . . .
C8B C 0.3701(2) 0.6208(2) 1.6335(3) 0.0168(7) Uani 1 1 d . . .
C12A C -0.1663(2) 0.7679(2) 1.0259(4) 0.0277(8) Uani 1 1 d . . .
H12A H -0.2317 0.7515 1.0038 0.042 Uiso 1 1 calc R . .
H12B H -0.1552 0.8229 1.0788 0.042 Uiso 1 1 calc R . .
H12C H -0.1279 0.7206 1.0796 0.042 Uiso 1 1 calc R . .
C12B C 0.6298(3) 0.6227(3) 2.0698(4) 0.0336(9) Uani 1 1 d . . .
H12D H 0.6719 0.6699 2.1165 0.050 Uiso 1 1 calc R . .
H12E H 0.6659 0.5706 2.0604 0.050 Uiso 1 1 calc R . .
H12F H 0.5885 0.6071 2.1232 0.050 Uiso 1 1 calc R . .
C2A C 0.0344(2) 0.5328(2) 0.8236(4) 0.0215(7) Uani 1 1 d . . .
H2A H 0.009(2) 0.502(2) 0.739(3) 0.014(8) Uiso 1 1 d . . .
H8B H 0.325(2) 0.620(2) 1.675(3) 0.014(8) Uiso 1 1 d . . .
H8A H 0.095(2) 0.801(2) 1.175(4) 0.014(8) Uiso 1 1 d . . .
H2B H 0.686(3) 0.581(2) 1.503(3) 0.021(9) Uiso 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
Cu1 N7A 1.976(3) . ?
Cu1 N7B 1.977(3) . ?
Cu1 Cl3 2.2466(11) . ?
Cu1 Cl2 2.2658(14) . ?
Cl1B C6B 1.720(3) . ?
Cl1A C6A 1.720(3) . ?
N9B C8B 1.351(4) . ?
N9B C4B 1.376(4) . ?
N9B C10B 1.471(4) . ?
N3A C2A 1.325(4) . ?
N3A C4A 1.332(4) . ?
N9A C8A 1.343(4) . ?
N9A C4A 1.372(4) . ?
N9A C10A 1.475(4) . ?
N3B C2B 1.325(4) . ?
N3B C4B 1.328(4) . ?
N7B C8B 1.313(4) . ?
N7B C5B 1.387(4) . ?
N1B C6B 1.324(4) . ?
N1B C2B 1.350(4) . ?
N7A C8A 1.329(4) . ?
N7A C5A 1.385(4) . ?
N1A C6A 1.317(4) . ?
N1A C2A 1.350(4) . ?
C6A C5A 1.390(5) . ?
C4A C5A 1.399(4) . ?
C4B C5B 1.396(4) . ?
C10B C11B 1.514(5) . ?
C5B C6B 1.380(4) . ?
C11B C12B 1.515(5) . ?
C10A C11A 1.518(4) . ?
C11A C12A 1.506(5) . ?

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
N7A Cu1 N7B 154.47(11) . . ?
N7A Cu1 Cl3 98.95(9) . . ?
N7B Cu1 Cl3 91.74(9) . . ?
N7A Cu1 Cl2 93.78(8) . . ?
N7B Cu1 Cl2 92.58(8) . . ?
Cl3 Cu1 Cl2 140.29(4) . . ?
C8B N9B C4B 106.8(3) . . ?
C8B N9B C10B 127.8(3) . . ?
C4B N9B C10B 125.3(3) . . ?
C2A N3A C4A 112.6(3) . . ?
C8A N9A C4A 106.2(3) . . ?
C8A N9A C10A 126.7(3) . . ?
C4A N9A C10A 127.1(3) . . ?
C2B N3B C4B 113.0(3) . . ?
C8B N7B C5B 105.2(3) . . ?
C8B N7B Cu1 126.3(2) . . ?
C5B N7B Cu1 128.5(2) . . ?
C6B N1B C2B 118.0(3) . . ?
C8A N7A C5A 104.2(3) . . ?
C8A N7A Cu1 124.4(2) . . ?
C5A N7A Cu1 131.3(2) . . ?
C6A N1A C2A 117.1(3) . . ?
N3B C2B N1B 126.9(3) . . ?
N1A C6A C5A 121.4(3) . . ?
N1A C6A Cl1A 117.6(2) . . ?
C5A C6A Cl1A 120.9(2) . . ?
N3A C4A N9A 127.9(3) . . ?
N3A C4A C5A 125.6(3) . . ?
N9A C4A C5A 106.4(3) . . ?
N3B C4B N9B 128.2(3) . . ?
N3B C4B C5B 126.0(3) . . ?
N9B C4B C5B 105.7(3) . . ?
N9B C10B C11B 112.4(3) . . ?
C6B C5B N7B 135.7(3) . . ?
C6B C5B C4B 115.1(3) . . ?
N7B C5B C4B 109.1(3) . . ?
N1B C6B C5B 121.0(3) . . ?
N1B C6B Cl1B 118.1(2) . . ?
C5B C6B Cl1B 120.9(2) . . ?
C12B C11B C10B 111.1(3) . . ?
N9A C10A C11A 112.6(3) . . ?
N7A C8A N9A 114.0(3) . . ?
C12A C11A C10A 113.6(3) . . ?
N7A C5A C6A 135.6(3) . . ?
N7A C5A C4A 109.1(3) . . ?
C6A C5A C4A 115.1(3) . . ?
N7B C8B N9B 113.1(3) . . ?
N3A C2A N1A 128.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_20nova_a
_database_code_depnum_ccdc_archive 'CCDC 1508067'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H9 Cl N4'
_chemical_formula_weight         196.64

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

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

_cell_length_a                   15.60(1)
_cell_length_b                   6.591(6)
_cell_length_c                   16.80(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1728(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1504
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      25.0

_exptl_crystal_description       needle-like
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9180
_exptl_absorpt_correction_T_max  0.9322
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7912
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1504
_reflns_number_gt                1155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0964P)²+0.0000P] 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         1504
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
Cl1 Cl 0.19060(4) 0.19003(9) 0.08772(4) 0.0210(3) Uani 1 1 d . . .
N7 N 0.02184(14) 0.2355(3) 0.20117(14) 0.0179(5) Uani 1 1 d . . .
N9 N 0.02633(14) 0.2715(3) 0.33585(13) 0.0163(5) Uani 1 1 d . . .
N3 N 0.18089(15) 0.2778(3) 0.35467(14) 0.0192(6) Uani 1 1 d . . .
N1 N 0.25743(16) 0.2384(3) 0.23049(12) 0.0189(6) Uani 1 1 d . . .
C5 C 0.10603(17) 0.2417(3) 0.22735(14) 0.0156(6) Uani 1 1 d . . .
C8 C -0.02252(19) 0.2537(4) 0.26794(15) 0.0179(6) Uani 1 1 d . . .
H8 H -0.0821 0.2544 0.2689 0.021 Uiso 1 1 calc R . .
C10 C -0.00478(18) 0.3037(4) 0.41721(15) 0.0185(7) Uani 1 1 d . . .
H10A H -0.0252 0.4421 0.4226 0.022 Uiso 1 1 calc R . .
H10B H 0.0421 0.2848 0.4543 0.022 Uiso 1 1 calc R . .
C11 C -0.07652(17) 0.1584(4) 0.43755(15) 0.0206(6) Uani 1 1 d . . .
H11A H -0.0550 0.0204 0.4351 0.025 Uiso 1 1 calc R . .
H11B H -0.1218 0.1717 0.3983 0.025 Uiso 1 1 calc R . .
C6 C 0.18439(17) 0.2270(4) 0.18941(16) 0.0168(6) Uani 1 1 d . . .
C2 C 0.25125(19) 0.2633(4) 0.31039(16) 0.0201(6) Uani 1 1 d . . .
H2 H 0.3029 0.2713 0.3378 0.024 Uiso 1 1 calc R . .
C4 C 0.10986(16) 0.2662(3) 0.31067(16) 0.0162(6) Uani 1 1 d . . .
C12 C -0.11366(19) 0.1979(4) 0.52078(16) 0.0240(7) Uani 1 1 d . . .
H12A H -0.0683 0.1943 0.5594 0.036 Uiso 1 1 calc R . .
H12B H -0.1553 0.0954 0.5332 0.036 Uiso 1 1 calc R . .
H12C H -0.1406 0.3289 0.5218 0.036 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
Cl1 C6 1.729(4) . ?
N7 C8 1.324(4) . ?
N7 C5 1.386(4) . ?
N9 C4 1.370(4) . ?
N9 C8 1.377(4) . ?
N9 C10 1.466(4) . ?
N3 C2 1.329(4) . ?
N3 C4 1.334(4) . ?
N1 C6 1.334(4) . ?
N1 C2 1.356(4) . ?
C5 C6 1.382(4) . ?
C5 C4 1.411(4) . ?
C10 C11 1.512(4) . ?
C11 C12 1.536(4) . ?

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
C8 N7 C5 102.9(2) . . ?
C4 N9 C8 105.6(2) . . ?
C4 N9 C10 127.3(2) . . ?
C8 N9 C10 127.0(2) . . ?
C2 N3 C4 111.8(3) . . ?
C6 N1 C2 117.3(2) . . ?
C6 C5 N7 133.6(3) . . ?
C6 C5 C4 115.4(2) . . ?
N7 C5 C4 111.0(2) . . ?
N7 C8 N9 114.9(3) . . ?
N9 C10 C11 111.4(2) . . ?
C10 C11 C12 112.2(2) . . ?
N1 C6 C5 120.8(3) . . ?
N1 C6 Cl1 118.1(2) . . ?
C5 C6 Cl1 121.0(2) . . ?
N3 C2 N1 128.4(3) . . ?
N3 C4 N9 128.1(3) . . ?
N3 C4 C5 126.3(2) . . ?
N9 C4 C5 105.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_25novbm
_database_code_depnum_ccdc_archive 'CCDC 1508069'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '9-benzyl 6-chloro purine'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 Cl1 N4'
_chemical_formula_sum            'C12 H9 Cl N4'
_chemical_formula_weight         244.68

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P121/n1

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

_cell_length_a                   4.8996(8)
_cell_length_b                   24.168(4)
_cell_length_c                   9.3291(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.474(3)
_cell_angle_gamma                90.00
_cell_volume                     1102.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2710
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.3

_exptl_crystal_description       hexagonal
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area Detector'
_diffrn_measurement_method       'Phi-Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7161
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         28.31
_reflns_number_total             2710
_reflns_number_gt                2081
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT+ 6.45  (Bruker, 2003)'
_computing_structure_solution    Sir92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'diamond 3.1d'
_computing_publication_material  ?

_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)+(0.1181P)²+1.4159P] 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         2710
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.2173
_refine_ls_wR_factor_gt          0.1519
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Cl1 Cl 0.75245(17) 0.64782(3) 0.73121(9) 0.0338(3) Uani 1 1 d . . .
N3 N 1.2268(5) 0.49322(11) 0.6401(3) 0.0258(5) Uani 1 1 d . . .
N1 N 1.1214(5) 0.58995(11) 0.6052(3) 0.0284(6) Uani 1 1 d . . .
N7 N 0.7016(5) 0.52596(10) 0.8768(3) 0.0238(5) Uani 1 1 d . . .
N9 N 0.9421(5) 0.45087(10) 0.8154(3) 0.0232(5) Uani 1 1 d . . .
C6 C 0.9341(6) 0.58805(12) 0.7005(3) 0.0251(6) Uani 1 1 d . . .
C13 C 0.5178(7) 0.28969(12) 0.9302(4) 0.0310(7) Uani 1 1 d . . .
H13 H 0.4541 0.2749 1.0139 0.037 Uiso 1 1 calc R . .
C10 C 1.0493(6) 0.39371(12) 0.8227(4) 0.0282(6) Uani 1 1 d . . .
H10A H 1.1586 0.3888 0.9120 0.034 Uiso 1 1 calc R . .
H10B H 1.1670 0.3877 0.7442 0.034 Uiso 1 1 calc R . .
C5 C 0.8794(6) 0.53989(11) 0.7735(3) 0.0221(6) Uani 1 1 d . . .
C14 C 0.4034(7) 0.27286(12) 0.7979(4) 0.0310(7) Uani 1 1 d . . .
H14 H 0.2641 0.2466 0.7927 0.037 Uiso 1 1 calc R . .
C15 C 0.4977(7) 0.29534(13) 0.6730(4) 0.0317(7) Uani 1 1 d . . .
H15 H 0.4208 0.2843 0.5840 0.038 Uiso 1 1 calc R . .
C2 C 1.2585(6) 0.54301(14) 0.5810(3) 0.0287(7) Uani 1 1 d . . .
H2 H 1.3925 0.5455 0.5148 0.034 Uiso 1 1 calc R . .
C12 C 0.7266(6) 0.32847(13) 0.9386(3) 0.0290(6) Uani 1 1 d . . .
H12 H 0.8035 0.3392 1.0279 0.035 Uiso 1 1 calc R . .
C4 C 1.0329(6) 0.49344(12) 0.7354(3) 0.0233(6) Uani 1 1 d . . .
C11 C 0.8218(6) 0.35143(11) 0.8141(3) 0.0248(6) Uani 1 1 d . . .
C8 C 0.7483(6) 0.47277(12) 0.8971(3) 0.0235(6) Uani 1 1 d . . .
H8 H 0.6558 0.4518 0.9623 0.028 Uiso 1 1 calc R . .
C16 C 0.7061(7) 0.33422(12) 0.6809(3) 0.0280(6) Uani 1 1 d . . .
H16 H 0.7694 0.3490 0.5970 0.034 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
Cl1 C6 1.730(3) . ?
N3 C2 1.336(4) . ?
N3 C4 1.340(4) . ?
N1 C6 1.317(4) . ?
N1 C2 1.344(4) . ?
N7 C8 1.317(4) . ?
N7 C5 1.379(4) . ?
N9 C4 1.361(4) . ?
N9 C8 1.361(4) . ?
N9 C10 1.478(4) . ?
C6 C5 1.383(4) . ?
C13 C14 1.385(5) . ?
C13 C12 1.386(4) . ?
C13 H13 0.9300 . ?
C10 C11 1.511(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 C4 1.409(4) . ?
C14 C15 1.390(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(4) . ?
C15 H15 0.9300 . ?
C2 H2 0.9300 . ?
C12 C11 1.393(4) . ?
C12 H12 0.9300 . ?
C11 C16 1.398(4) . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?

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
C2 N3 C4 112.0(3) . . ?
C6 N1 C2 117.4(3) . . ?
C8 N7 C5 103.1(2) . . ?
C4 N9 C8 106.0(2) . . ?
C4 N9 C10 127.2(2) . . ?
C8 N9 C10 126.6(2) . . ?
N1 C6 C5 121.7(3) . . ?
N1 C6 Cl1 118.0(2) . . ?
C5 C6 Cl1 120.3(2) . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N9 C10 C11 111.8(2) . . ?
N9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
N7 C5 C6 134.3(3) . . ?
N7 C5 C4 110.6(2) . . ?
C6 C5 C4 115.1(3) . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
N3 C2 N1 128.2(3) . . ?
N3 C2 H2 115.9 . . ?
N1 C2 H2 115.9 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N3 C4 N9 129.0(3) . . ?
N3 C4 C5 125.6(3) . . ?
N9 C4 C5 105.5(2) . . ?
C12 C11 C16 119.0(3) . . ?
C12 C11 C10 120.6(3) . . ?
C16 C11 C10 120.4(3) . . ?
N7 C8 N9 114.8(2) . . ?
N7 C8 H8 122.6 . . ?
N9 C8 H8 122.6 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?

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 N1 C6 C5 0.1(4) . . . . ?
C2 N1 C6 Cl1 -179.2(2) . . . . ?
C4 N9 C10 C11 -134.9(3) . . . . ?
C8 N9 C10 C11 51.3(4) . . . . ?
C8 N7 C5 C6 178.3(3) . . . . ?
C8 N7 C5 C4 -0.6(3) . . . . ?
N1 C6 C5 N7 179.5(3) . . . . ?
Cl1 C6 C5 N7 -1.3(5) . . . . ?
N1 C6 C5 C4 -1.6(4) . . . . ?
Cl1 C6 C5 C4 177.6(2) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C4 N3 C2 N1 -0.9(4) . . . . ?
C6 N1 C2 N3 1.3(5) . . . . ?
C14 C13 C12 C11 0.7(5) . . . . ?
C2 N3 C4 N9 179.4(3) . . . . ?
C2 N3 C4 C5 -1.0(4) . . . . ?
C8 N9 C4 N3 178.8(3) . . . . ?
C10 N9 C4 N3 4.0(5) . . . . ?
C8 N9 C4 C5 -1.0(3) . . . . ?
C10 N9 C4 C5 -175.7(3) . . . . ?
N7 C5 C4 N3 -178.7(3) . . . . ?
C6 C5 C4 N3 2.1(4) . . . . ?
N7 C5 C4 N9 1.0(3) . . . . ?
C6 C5 C4 N9 -178.1(2) . . . . ?
C13 C12 C11 C16 -0.8(4) . . . . ?
C13 C12 C11 C10 180.0(3) . . . . ?
N9 C10 C11 C12 -96.2(3) . . . . ?
N9 C10 C11 C16 84.7(3) . . . . ?
C5 N7 C8 N9 0.0(3) . . . . ?
C4 N9 C8 N7 0.6(3) . . . . ?
C10 N9 C8 N7 175.5(3) . . . . ?
C14 C15 C16 C11 -0.4(5) . . . . ?
C12 C11 C16 C15 0.7(4) . . . . ?
C10 C11 C16 C15 179.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.124
####################################################################### 
# 
# 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_27augf_0m
_database_code_depnum_ccdc_archive 'CCDC 1508070'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H9 Cl5 Cu2 N4 O'
_chemical_formula_weight         481.52

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   6.089(4)
_cell_length_b                   14.910(5)
_cell_length_c                   16.172(6)
_cell_angle_alpha                90.000
_cell_angle_beta                 95.488(5)
_cell_angle_gamma                90.000
_cell_volume                     1461.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2571
_cell_measurement_theta_min      4.2
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block-type
_exptl_crystal_colour            blue-green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    3.820
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.4870
_exptl_absorpt_correction_T_max  0.5305
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11425
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.24
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2571
_reflns_number_gt                2140
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0303P)²+1.2635P] 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         2571
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.82003(6) 0.04146(2) 0.76185(2) 0.00923(12) Uani 1 1 d . . .
Cl03 Cl 1.12215(13) 0.02260(5) 0.69048(5) 0.01242(18) Uani 1 1 d . . .
Cl04 Cl 1.03258(13) -0.02302(5) 0.87204(5) 0.01234(19) Uani 1 1 d . . .
Cl05 Cl 0.59067(13) -0.09906(5) 0.71160(5) 0.01125(18) Uani 1 1 d . . .
Cl2 Cl 0.56371(13) 0.08270(5) 0.84855(5) 0.01128(18) Uani 1 1 d . . .
Cl1 Cl 0.89506(13) 0.25418(5) 0.75325(5) 0.01498(19) Uani 1 1 d . . .
C4 C 0.4444(5) 0.2281(2) 0.56246(19) 0.0088(7) Uani 1 1 d . . .
C2 C 0.5484(5) 0.0926(2) 0.6049(2) 0.0108(7) Uani 1 1 d . . .
H2 H 0.5403 0.0306 0.5992 0.013 Uiso 1 1 calc R . .
C5 C 0.5750(5) 0.2684(2) 0.62693(19) 0.0084(7) Uani 1 1 d . . .
C6 C 0.7008(5) 0.2125(2) 0.67968(19) 0.0098(7) Uani 1 1 d . . .
C13 C -0.0845(6) 0.1182(2) 0.4717(2) 0.0181(8) Uani 1 1 d . . .
H13A H -0.0912 0.0659 0.5060 0.027 Uiso 1 1 calc R . .
H13B H 0.0417 0.1142 0.4406 0.027 Uiso 1 1 calc R . .
H13C H -0.2162 0.1219 0.4342 0.027 Uiso 1 1 calc R . .
C10 C 0.1764(5) 0.2875(2) 0.4451(2) 0.0122(7) Uani 1 1 d . . .
H10A H 0.2105 0.2364 0.4115 0.015 Uiso 1 1 calc R . .
H10B H 0.1772 0.3409 0.4108 0.015 Uiso 1 1 calc R . .
C8 C 1.5871(5) -0.1268(2) 0.9459(2) 0.0104(7) Uani 1 1 d . . .
H8 H 1.6342 -0.0704 0.9646 0.013 Uiso 1 1 calc R . .
N7 N 1.4460(4) -0.13961(17) 0.87987(16) 0.0099(6) Uani 1 1 d . . .
O12 O -0.0662(4) 0.19629(14) 0.52289(13) 0.0125(5) Uani 1 1 d . . .
N1 N 0.6806(4) 0.12372(17) 0.67086(16) 0.0092(6) Uani 1 1 d . . .
N9 N 0.3436(4) 0.29598(17) 0.51614(16) 0.0088(6) Uani 1 1 d . . .
N3 N 0.4298(4) 0.13972(17) 0.54791(16) 0.0098(6) Uani 1 1 d . . .
C11 C -0.0503(5) 0.2754(2) 0.4754(2) 0.0133(7) Uani 1 1 d . . .
H11A H -0.0828 0.3268 0.5089 0.016 Uiso 1 1 calc R . .
H11B H -0.1600 0.2733 0.4278 0.016 Uiso 1 1 calc R . .
Cu2 Cu 1.32662(6) -0.05211(2) 0.79472(2) 0.00913(12) Uiso 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
Cu1 N1 2.037(3) . ?
Cu1 Cl2 2.2800(13) . ?
Cu1 Cl03 2.2808(16) . ?
Cu1 Cl04 2.3095(11) . ?
Cu1 Cl05 2.6044(12) . ?
Cl03 Cu2 2.2872(11) . ?
Cl04 Cu2 2.3207(15) . ?
Cl05 Cu2 2.3011(13) 1_455 ?
Cl2 Cu2 2.5771(12) 1_455 ?
Cl1 C6 1.712(3) . ?
C4 N3 1.340(4) . ?
C4 N9 1.370(4) . ?
C4 C5 1.386(4) . ?
C2 N3 1.318(4) . ?
C2 N1 1.355(4) . ?
C5 C6 1.373(4) . ?
C5 N7 1.381(4) 2_756 ?
C6 N1 1.335(4) . ?
C13 O12 1.427(4) . ?
C10 N9 1.466(4) . ?
C10 C11 1.519(4) . ?
C8 N7 1.319(4) . ?
C8 N9 1.352(4) 2_746 ?
N7 C5 1.381(4) 2_746 ?
N7 Cu2 1.984(3) . ?
O12 C11 1.416(4) . ?
N9 C8 1.352(4) 2_756 ?
Cu2 Cl05 2.3011(13) 1_655 ?
Cu2 Cl2 2.5771(12) 1_655 ?

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 Cl2 91.11(8) . . ?
N1 Cu1 Cl03 90.53(8) . . ?
Cl2 Cu1 Cl03 167.74(3) . . ?
N1 Cu1 Cl04 166.38(8) . . ?
Cl2 Cu1 Cl04 90.22(5) . . ?
Cl03 Cu1 Cl04 85.39(5) . . ?
N1 Cu1 Cl05 94.87(8) . . ?
Cl2 Cu1 Cl05 91.76(5) . . ?
Cl03 Cu1 Cl05 100.21(5) . . ?
Cl04 Cu1 Cl05 98.63(4) . . ?
Cu1 Cl03 Cu2 95.48(5) . . ?
Cu1 Cl04 Cu2 93.80(5) . . ?
Cu2 Cl05 Cu1 87.52(5) 1_455 . ?
Cu1 Cl2 Cu2 88.64(5) . 1_455 ?
N3 C4 N9 127.7(3) . . ?
N3 C4 C5 125.6(3) . . ?
N9 C4 C5 106.6(3) . . ?
N3 C2 N1 127.8(3) . . ?
C6 C5 N7 134.0(3) . 2_756 ?
C6 C5 C4 116.8(3) . . ?
N7 C5 C4 109.2(3) 2_756 . ?
N1 C6 C5 119.7(3) . . ?
N1 C6 Cl1 119.0(2) . . ?
C5 C6 Cl1 121.3(2) . . ?
N9 C10 C11 110.0(3) . . ?
N7 C8 N9 113.3(3) . 2_746 ?
C8 N7 C5 104.8(3) . 2_746 ?
C8 N7 Cu2 129.4(2) . . ?
C5 N7 Cu2 125.0(2) 2_746 . ?
C11 O12 C13 111.8(2) . . ?
C6 N1 C2 117.7(3) . . ?
C6 N1 Cu1 119.4(2) . . ?
C2 N1 Cu1 122.5(2) . . ?
C8 N9 C4 106.1(3) 2_756 . ?
C8 N9 C10 126.3(3) 2_756 . ?
C4 N9 C10 127.3(3) . . ?
C2 N3 C4 112.2(3) . . ?
O12 C11 C10 112.7(3) . . ?
N7 Cu2 Cl03 165.79(8) . . ?
N7 Cu2 Cl05 88.59(8) . 1_655 ?
Cl03 Cu2 Cl05 94.54(5) . 1_655 ?
N7 Cu2 Cl04 89.95(8) . . ?
Cl03 Cu2 Cl04 84.98(5) . . ?
Cl05 Cu2 Cl04 171.79(3) 1_655 . ?
N7 Cu2 Cl2 97.02(8) . 1_655 ?
Cl03 Cu2 Cl2 96.72(4) . 1_655 ?
Cl05 Cu2 Cl2 91.98(5) 1_655 1_655 ?
Cl04 Cu2 Cl2 96.22(5) . 1_655 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_77_0m
_database_code_depnum_ccdc_archive 'CCDC 1508072'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;
_audit_creation_date             2016-12-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H10 Cl Cu N7 O7'
_chemical_formula_sum            'C11 H10 Cl Cu N7 O7'
_chemical_formula_weight         451.24
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.3161(7)
_cell_length_b                   26.987(2)
_cell_length_c                   13.2722(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.640(1)
_cell_angle_gamma                90
_cell_volume                     3268.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.18
_exptl_absorpt_coefficient_mu    1.556
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6346
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
'(North et al., 1968)'
wR2(int) was 0.1379 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.8510.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            blue-green
_exptl_crystal_density_diffrn    1.8341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             1820.7616
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27937
_diffrn_reflns_theta_full        25.0266
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         4.14
_diffrn_measured_fraction_theta_full 0.9938
_diffrn_measured_fraction_theta_max 0.9938
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              32
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4806
_reflns_number_total             5727
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.3986
_refine_diff_density_min         -0.3975
_refine_diff_density_rms         0.0879
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             4.9245
_refine_ls_goodness_of_fit_ref   1.0770
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     488
_refine_ls_number_reflns         5727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.0770
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+3.1829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0875
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O2W(H2Wa,H2Wb), O1W(H1Wa,H1Wb)
2.b Secondary CH2 refined with riding coordinates:
 C10A(H10c,H10d), C10B(H10a,H10b)
2.c Aromatic/amide H refined with riding coordinates:
 C4AA(H4AA), C16A(H16A), C16B(H16B), C13B(H13B), C14A(H14A), C2B(H2B),
 C15A(H15A), C8B(H8B), C13A(H13A), C15B(H15B), C14B(H14B), C0AA(H0AA)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Cu1B Cu 1.50875(4) 0.040257(14) 1.21958(3) 0.03142(11) Uani 1.000000 .
Cu1A Cu 0.90986(4) 0.267484(15) 1.28746(3) 0.04103(12) Uani 1.000000 .
Cl1B Cl 0.87042(8) 0.07063(4) 0.92068(7) 0.0478(2) Uani 1.000000 .
Cl1A Cl 1.40190(9) 0.17019(3) 1.06438(8) 0.0524(2) Uani 1.000000 .
O2W O 1.6311(2) 0.08005(9) 1.11492(17) 0.0435(6) Uani 1.000000 .
H2Wa H 1.5908(19) 0.0743(9) 1.05269(17) 0.0652(9) Uiso 1.000000 GR
H2Wb H 1.7192(8) 0.0698(8) 1.1262(15) 0.0652(9) Uiso 1.000000 GR
N9B N 1.1637(2) 0.05677(10) 1.26976(19) 0.0337(6) Uani 1.000000 .
N9A N 1.2541(3) 0.30503(9) 1.2646(2) 0.0355(6) Uani 1.000000 .
O4A O 1.5269(3) -0.01891(9) 1.13485(19) 0.0501(6) Uani 1.000000 .
N7B N 0.9393(3) 0.06777(11) 1.1716(2) 0.0404(7) Uani 1.000000 .
O3A O 1.7062(2) 0.02683(10) 1.29978(17) 0.0475(6) Uani 1.000000 .
N3B N 1.3027(2) 0.04839(9) 1.13440(19) 0.0307(6) Uani 1.000000 .
N7A N 1.4303(3) 0.27246(10) 1.1907(2) 0.0422(7) Uani 1.000000 .
O3C O 1.8407(3) 0.00111(11) 1.43996(19) 0.0637(8) Uani 1.000000 .
N4S N 1.4852(3) -0.05898(11) 1.1665(2) 0.0413(7) Uani 1.000000 .
N12A N 0.9247(3) 0.33492(10) 1.2265(2) 0.0388(6) Uani 1.000000 .
N2S N 0.7678(3) 0.30044(11) 1.4287(2) 0.0427(7) Uani 1.000000 .
N3A N 1.0718(3) 0.23955(10) 1.2224(2) 0.0372(6) Uani 1.000000 .
N1A N 1.1562(3) 0.17266(10) 1.1308(2) 0.0476(7) Uani 1.000000 .
C5B C 1.0410(3) 0.06189(11) 1.1099(2) 0.0306(7) Uani 1.000000 .
N1B N 1.1530(3) 0.05516(10) 0.9667(2) 0.0376(6) Uani 1.000000 .
O1W O 0.7230(3) 0.23834(11) 1.1688(2) 0.0720(9) Uani 1.000000 .
H1Wa H 0.6433(5) 0.2429(14) 1.1892(15) 0.1080(13) Uiso 1.000000 GR
H1Wb H 0.735(2) 0.2075(3) 1.160(2) 0.1080(13) Uiso 1.000000 GR
O1A O 0.9132(3) 0.20522(11) 1.3662(2) 0.0649(8) Uani 1.000000 .
C6B C 1.0341(3) 0.06216(11) 1.0060(2) 0.0329(7) Uani 1.000000 .
O4B O 1.4893(3) -0.09695(10) 1.1158(2) 0.0631(7) Uani 1.000000 .
O3B O 1.6079(3) 0.00544(13) 1.4267(2) 0.0755(10) Uani 1.000000 .
N12B N 1.4827(3) 0.09693(10) 1.31279(19) 0.0331(6) Uani 1.000000 .
C1AA C 1.2009(3) 0.26112(11) 1.2221(2) 0.0319(7) Uani 1.000000 .
N3S N 1.7177(3) 0.01047(11) 1.3909(2) 0.0385(6) Uani 1.000000 .
C2AA C 1.3102(3) 0.24145(11) 1.1768(2) 0.0319(7) Uani 1.000000 .
N1S N 1.0294(5) 0.20008(18) 1.4375(3) 0.0784(13) Uani 1.000000 .
O1C O 1.1240(4) 0.23252(15) 1.4482(3) 0.0844(10) Uani 1.000000 .
O4C O 1.4346(5) -0.05818(13) 1.2444(3) 0.0965(12) Uani 1.000000 .
C4B C 1.1805(3) 0.05493(11) 1.1705(2) 0.0285(6) Uani 1.000000 .
C4AA C 1.3921(3) 0.30934(13) 1.2439(3) 0.0447(8) Uani 1.000000 .
H4AA H 1.4532(3) 0.33615(13) 1.2657(3) 0.0537(10) Uiso 1.000000 R
C11A C 1.0480(3) 0.36290(12) 1.2475(2) 0.0370(7) Uani 1.000000 .
C3AA C 1.2795(3) 0.19642(12) 1.1296(3) 0.0375(7) Uani 1.000000 .
C10A C 1.1772(3) 0.34046(12) 1.3190(3) 0.0390(8) Uani 1.000000 .
H10c H 1.1440(3) 0.32364(12) 1.3747(3) 0.0468(9) Uiso 1.000000 R
H10d H 1.2443(3) 0.36653(12) 1.3486(3) 0.0468(9) Uiso 1.000000 R
C10B C 1.2800(3) 0.05272(13) 1.3625(2) 0.0385(8) Uani 1.000000 .
H10a H 1.2364(3) 0.05071(13) 1.4228(2) 0.0462(9) Uiso 1.000000 R
H10b H 1.3359(3) 0.02266(13) 1.3591(2) 0.0462(9) Uiso 1.000000 R
O2A O 0.7400(3) 0.29190(12) 1.3434(3) 0.0727(8) Uani 1.000000 .
C16A C 1.0543(4) 0.40899(13) 1.2053(3) 0.0486(9) Uani 1.000000 .
H16A H 1.1403(4) 0.42742(13) 1.2205(3) 0.0583(11) Uiso 1.000000 R
C16B C 1.3681(4) 0.13590(15) 1.4359(3) 0.0515(9) Uani 1.000000 .
H16B H 1.2972(4) 0.13540(15) 1.4762(3) 0.0618(11) Uiso 1.000000 R
C13B C 1.5732(3) 0.13586(13) 1.3193(3) 0.0431(8) Uani 1.000000 .
H13B H 1.6449(3) 0.13579(13) 1.2796(3) 0.0517(10) Uiso 1.000000 R
C14A C 0.8076(5) 0.40019(16) 1.1199(3) 0.0604(11) Uani 1.000000 .
H14A H 0.7239(5) 0.41233(16) 1.0767(3) 0.0724(13) Uiso 1.000000 R
C11B C 1.3804(3) 0.09673(12) 1.3718(2) 0.0355(7) Uani 1.000000 .
C2B C 1.2800(3) 0.04817(12) 1.0317(2) 0.0365(7) Uani 1.000000 .
H2B H 1.3614(3) 0.04255(12) 1.0027(2) 0.0438(9) Uiso 1.000000 R
C15A C 0.9323(5) 0.42792(15) 1.1401(3) 0.0593(10) Uani 1.000000 .
H15A H 0.9351(5) 0.45906(15) 1.1106(3) 0.0711(13) Uiso 1.000000 R
C8B C 1.0161(3) 0.06445(14) 1.2653(3) 0.0415(8) Uani 1.000000 .
H8B H 0.9752(3) 0.06702(14) 1.3235(3) 0.0498(10) Uiso 1.000000 R
C13A C 0.8067(4) 0.35415(15) 1.1639(3) 0.0533(9) Uani 1.000000 .
H13A H 0.7209(4) 0.33558(15) 1.1497(3) 0.0640(11) Uiso 1.000000 R
C15B C 1.4603(5) 0.17548(16) 1.4402(3) 0.0636(11) Uani 1.000000 .
H15B H 1.4519(5) 0.20221(16) 1.4829(3) 0.0763(13) Uiso 1.000000 R
C14B C 1.5651(4) 0.17564(15) 1.3813(3) 0.0554(10) Uani 1.000000 .
H14B H 1.6293(4) 0.20220(15) 1.3835(3) 0.0665(12) Uiso 1.000000 R
C0AA C 1.0591(4) 0.19514(13) 1.1767(3) 0.0476(9) Uani 1.000000 .
H0AA H 0.9726(4) 0.17795(13) 1.1770(3) 0.0571(11) Uiso 1.000000 R
O1B O 1.0413(4) 0.16273(19) 1.4887(4) 0.151(2) Uani 1.000000 .
O2C O 0.8955(5) 0.30862(19) 1.4714(3) 0.1286(16) Uani 1.000000 .
O2B O 0.6723(6) 0.3086(2) 1.4793(3) 0.146(2) Uani 1.000000 .


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
Cu1B O2W 2.241(2) . ?
Cu1B O4A 1.980(2) . ?
Cu1B O3A 1.964(2) . ?
Cu1B N3B 2.034(2) . ?
Cu1B N12B 2.012(3) . ?
Cu1A N12A 2.008(3) . ?
Cu1A N3A 2.029(3) . ?
Cu1A O1W 2.241(3) . ?
Cu1A O1A 1.975(3) . ?
Cu1A O2A 1.991(3) . ?
Cl1B C6B 1.722(3) . ?
Cl1A C3AA 1.717(3) . ?
N9B C4B 1.358(4) . ?
N9B C10B 1.471(4) . ?
N9B C8B 1.381(4) . ?
N9A C1AA 1.362(4) . ?
N9A C4AA 1.372(4) . ?
N9A C10A 1.468(4) . ?
O4A N4S 1.250(4) . ?
N7B C5B 1.381(4) . ?
N7B C8B 1.307(4) . ?
O3A N3S 1.271(3) . ?
N3B C4B 1.333(4) . ?
N3B C2B 1.337(4) . ?
N7A C2AA 1.379(4) . ?
N7A C4AA 1.310(4) . ?
O3C N3S 1.225(3) . ?
N4S O4B 1.231(4) . ?
N4S O4C 1.219(4) . ?
N12A C11A 1.355(4) . ?
N12A C13A 1.342(4) . ?
N2S O2A 1.134(4) . ?
N2S O2C 1.231(5) . ?
N2S O2B 1.238(4) . ?
N3A C1AA 1.336(4) . ?
N3A C0AA 1.337(4) . ?
N1A C3AA 1.319(4) . ?
N1A C0AA 1.334(4) . ?
C5B C6B 1.367(4) . ?
C5B C4B 1.396(4) . ?
N1B C6B 1.330(4) . ?
N1B C2B 1.329(4) . ?
O1A N1S 1.294(5) . ?
O3B N3S 1.219(3) . ?
N12B C13B 1.339(4) . ?
N12B C11B 1.351(4) . ?
C1AA C2AA 1.389(4) . ?
C2AA C3AA 1.371(4) . ?
N1S O1C 1.230(5) . ?
N1S O1B 1.208(5) . ?
C11A C10A 1.502(4) . ?
C11A C16A 1.370(5) . ?
C10B C11B 1.501(4) . ?
C16A C15A 1.380(5) . ?
C16B C11B 1.377(5) . ?
C16B C15B 1.365(6) . ?
C13B C14B 1.364(5) . ?
C14A C15A 1.362(6) . ?
C14A C13A 1.373(5) . ?
C15B C14B 1.369(6) . ?

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
O4A Cu1B O2W 85.53(9) . . ?
O3A Cu1B O2W 83.47(8) . . ?
O3A Cu1B O4A 88.92(11) . . ?
N3B Cu1B O2W 98.33(9) . . ?
N3B Cu1B O4A 87.16(10) . . ?
N3B Cu1B O3A 175.53(11) . . ?
N12B Cu1B O2W 98.99(9) . . ?
N12B Cu1B O4A 175.47(10) . . ?
N12B Cu1B O3A 91.31(10) . . ?
N12B Cu1B N3B 92.43(10) . . ?
N3A Cu1A N12A 92.73(11) . . ?
O1W Cu1A N12A 98.14(11) . . ?
O1W Cu1A N3A 96.26(10) . . ?
O1A Cu1A N12A 171.54(12) . . ?
O1A Cu1A N3A 88.60(11) . . ?
O1A Cu1A O1W 90.02(13) . . ?
O2A Cu1A N12A 88.55(12) . . ?
O2A Cu1A N3A 175.56(12) . . ?
O2A Cu1A O1W 79.34(12) . . ?
O2A Cu1A O1A 90.75(12) . . ?
C10B N9B C4B 126.8(2) . . ?
C8B N9B C4B 105.8(2) . . ?
C8B N9B C10B 127.3(3) . . ?
C4AA N9A C1AA 105.6(3) . . ?
C10A N9A C1AA 126.6(2) . . ?
C10A N9A C4AA 127.8(3) . . ?
N4S O4A Cu1B 116.0(2) . . ?
C8B N7B C5B 104.3(2) . . ?
N3S O3A Cu1B 118.00(17) . . ?
C4B N3B Cu1B 126.4(2) . . ?
C2B N3B Cu1B 120.26(19) . . ?
C2B N3B C4B 113.3(2) . . ?
C4AA N7A C2AA 103.4(2) . . ?
O4B N4S O4A 119.3(3) . . ?
O4C N4S O4A 118.0(3) . . ?
O4C N4S O4B 122.6(3) . . ?
C11A N12A Cu1A 123.1(2) . . ?
C13A N12A Cu1A 119.1(2) . . ?
C13A N12A C11A 117.8(3) . . ?
O2C N2S O2A 120.1(4) . . ?
O2B N2S O2A 122.3(4) . . ?
O2B N2S O2C 116.9(4) . . ?
C1AA N3A Cu1A 125.9(2) . . ?
C0AA N3A Cu1A 121.3(2) . . ?
C0AA N3A C1AA 112.8(3) . . ?
C0AA N1A C3AA 117.2(3) . . ?
C6B C5B N7B 134.4(3) . . ?
C4B C5B N7B 110.1(3) . . ?
C4B C5B C6B 115.5(3) . . ?
C2B N1B C6B 117.9(3) . . ?
N1S O1A Cu1A 113.5(3) . . ?
C5B C6B Cl1B 121.3(2) . . ?
N1B C6B Cl1B 117.3(2) . . ?
N1B C6B C5B 121.4(3) . . ?
C13B N12B Cu1B 118.9(2) . . ?
C11B N12B Cu1B 122.7(2) . . ?
C11B N12B C13B 118.4(3) . . ?
N3A C1AA N9A 129.1(3) . . ?
C2AA C1AA N9A 105.9(2) . . ?
C2AA C1AA N3A 125.0(3) . . ?
O3C N3S O3A 117.9(3) . . ?
O3B N3S O3A 119.6(2) . . ?
O3B N3S O3C 122.5(3) . . ?
C1AA C2AA N7A 110.8(3) . . ?
C3AA C2AA N7A 133.5(3) . . ?
C3AA C2AA C1AA 115.7(3) . . ?
O1C N1S O1A 118.8(4) . . ?
O1B N1S O1A 118.0(5) . . ?
O1B N1S O1C 123.1(5) . . ?
N3B C4B N9B 128.8(3) . . ?
C5B C4B N9B 106.2(2) . . ?
C5B C4B N3B 125.0(3) . . ?
N7A C4AA N9A 114.2(3) . . ?
C10A C11A N12A 116.3(3) . . ?
C16A C11A N12A 121.7(3) . . ?
C16A C11A C10A 122.0(3) . . ?
N1A C3AA Cl1A 118.3(2) . . ?
C2AA C3AA Cl1A 119.8(2) . . ?
C2AA C3AA N1A 121.8(3) . . ?
C11A C10A N9A 111.1(3) . . ?
C11B C10B N9B 110.6(2) . . ?
N2S O2A Cu1A 113.7(2) . . ?
C15A C16A C11A 119.6(4) . . ?
C15B C16B C11B 119.8(3) . . ?
C14B C13B N12B 123.1(3) . . ?
C13A C14A C15A 119.5(4) . . ?
C10B C11B N12B 117.2(3) . . ?
C16B C11B N12B 120.8(3) . . ?
C16B C11B C10B 122.0(3) . . ?
N1B C2B N3B 126.7(3) . . ?
C14A C15A C16A 118.8(4) . . ?
N7B C8B N9B 113.6(3) . . ?
C14A C13A N12A 122.6(4) . . ?
C14B C15B C16B 119.6(4) . . ?
C15B C14B C13B 118.4(4) . . ?
N1A C0AA N3A 127.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
