# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1824815'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H13 N2 O2), Cl4 Co'
_chemical_formula_sum            'C36 H26 Cl4 Co N4 O4'
_chemical_formula_weight         779.34

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'
Co Co 0.3494 0.9721 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8831(4)
_cell_length_b                   14.6869(8)
_cell_length_c                   14.5239(8)
_cell_angle_alpha                102.504(2)
_cell_angle_beta                 100.890(2)
_cell_angle_gamma                92.406(2)
_cell_volume                     1606.07(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    67905
_cell_measurement_theta_min      2.267
_cell_measurement_theta_max      26.373

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.033
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_F_000             794
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.917
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67905
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6564
_reflns_number_gt                5247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0518P)²+1.5160P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6564
_refine_ls_number_parameters     546
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.79637(8) 0.55721(4) -0.03453(4) 0.02346(14) Uani 1 1 d . U . . .
Cl2 Cl 0.73499(8) 0.81064(4) -0.01097(5) 0.02772(15) Uani 1 1 d . U . . .
Cl3 Cl 1.14894(8) 0.74542(5) 0.09276(5) 0.03132(16) Uani 1 1 d . U . . .
Cl4 Cl 0.77354(12) 0.69627(6) 0.20389(6) 0.0512(2) Uani 1 1 d . U . . .
Co1 Co 0.85912(4) 0.70293(2) 0.06731(2) 0.02347(11) Uani 1 1 d . U . . .
O1 O 0.3259(2) 0.03478(13) 0.21502(13) 0.0284(4) Uani 1 1 d . U . . .
O3 O 0.3067(2) 0.33612(14) 0.28886(13) 0.0310(4) Uani 1 1 d . U . . .
O2 O 0.8705(2) 0.00806(13) 0.36687(13) 0.0266(4) Uani 1 1 d . U . . .
O4 O 0.8503(2) 0.28424(14) 0.42044(14) 0.0326(4) Uani 1 1 d . U . . .
N2 N 0.5942(2) 0.01641(14) 0.29392(14) 0.0188(4) Uani 1 1 d . U . . .
N4 N 0.5757(3) 0.30694(14) 0.35663(14) 0.0194(4) Uani 1 1 d . U . . .
N1 N 0.8757(3) 0.12159(15) 0.05052(15) 0.0238(5) Uani 1 1 d . U . . .
N3 N 0.8452(3) 0.42276(16) 0.11279(15) 0.0261(5) Uani 1 1 d . U . . .
C5 C 0.9744(3) 0.07346(19) 0.10531(18) 0.0253(5) Uani 1 1 d . U . . .
C1 C 0.7041(3) 0.12112(18) 0.04410(17) 0.0235(5) Uani 1 1 d . U . . .
C20 C 0.5910(3) 0.36282(18) 0.14803(18) 0.0247(5) Uani 1 1 d . U . . .
C18 C 0.5180(3) 0.10872(16) 0.46982(17) 0.0176(5) Uani 1 1 d . U . . .
C4 C 0.8981(3) 0.01994(18) 0.15596(18) 0.0244(5) Uani 1 1 d . U . . .
C6 C 0.6325(3) -0.04133(18) 0.20455(18) 0.0232(5) Uani 1 1 d . U . . .
C19 C 0.6717(3) 0.41516(19) 0.09856(19) 0.0270(6) Uani 1 1 d . U . . .
C8 C 0.3915(3) 0.09734(16) 0.38394(18) 0.0200(5) Uani 1 1 d . U . . .
C12 C 0.4767(3) 0.15121(16) 0.55923(18) 0.0208(5) Uani 1 1 d . U . . .
C3 C 0.7201(3) 0.01706(16) 0.15040(16) 0.0196(5) Uani 1 1 d . U . . .
C7 C 0.4300(3) 0.04832(17) 0.29139(17) 0.0204(5) Uani 1 1 d . U . . .
C11 C 0.3091(4) 0.18217(17) 0.5598(2) 0.0264(6) Uani 1 1 d . U . . .
C21 C 0.6896(3) 0.31711(16) 0.21125(17) 0.0206(5) Uani 1 1 d . U . . .
C27 C 0.2278(3) 0.41426(18) 0.4692(2) 0.0245(5) Uani 1 1 d . U . . .
C9 C 0.2313(3) 0.12984(18) 0.3878(2) 0.0239(5) Uani 1 1 d . U . . .
C34 C 0.6801(3) 0.35230(17) 0.53091(18) 0.0216(5) Uani 1 1 d . U . . .
C14 C 0.7663(4) 0.13254(18) 0.64018(18) 0.0266(6) Uani 1 1 d . U . . .
C28 C 0.1947(4) 0.44787(18) 0.5617(2) 0.0280(6) Uani 1 1 d . U . . .
C30 C 0.4840(4) 0.41909(17) 0.63387(18) 0.0257(5) Uani 1 1 d . U . . .
C2 C 0.6238(3) 0.06974(17) 0.09417(17) 0.0215(5) Uani 1 1 d . U . . .
C36 C 0.5175(3) 0.38496(16) 0.54040(17) 0.0199(5) Uani 1 1 d . U . . .
C25 C 0.4145(3) 0.34168(16) 0.36199(17) 0.0203(5) Uani 1 1 d . U . . .
C16 C 0.6853(3) 0.07831(16) 0.46768(17) 0.0187(5) Uani 1 1 d . U . . .
C22 C 0.8695(3) 0.32735(19) 0.22340(18) 0.0249(5) Uani 1 1 d . U . . .
C15 C 0.8073(3) 0.09066(18) 0.55142(18) 0.0229(5) Uani 1 1 d . U . . .
C10 C 0.1912(3) 0.17210(18) 0.4758(2) 0.0278(6) Uani 1 1 d . U . . .
C32 C 0.7732(4) 0.3889(2) 0.7036(2) 0.0336(6) Uani 1 1 d . U . . .
C26 C 0.3863(3) 0.38217(16) 0.45917(17) 0.0191(5) Uani 1 1 d . U . . .
C13 C 0.6057(4) 0.16159(18) 0.64395(19) 0.0261(6) Uani 1 1 d . U . . .
C35 C 0.7130(3) 0.31274(17) 0.43497(18) 0.0214(5) Uani 1 1 d . U . . .
C23 C 0.9450(4) 0.3807(2) 0.17319(18) 0.0280(6) Uani 1 1 d . U . . .
C33 C 0.8059(4) 0.35462(19) 0.6118(2) 0.0285(6) Uani 1 1 d . U . . .
C17 C 0.7284(3) 0.03264(16) 0.37579(17) 0.0181(5) Uani 1 1 d . U . . .
C29 C 0.3183(4) 0.44897(19) 0.6413(2) 0.0309(6) Uani 1 1 d . U . . .
C31 C 0.6158(4) 0.4200(2) 0.7149(2) 0.0327(6) Uani 1 1 d . U . . .
C24 C 0.6014(4) 0.25602(18) 0.26228(18) 0.0234(5) Uani 1 1 d . U . . .
H5 H 1.099(4) 0.0790(18) 0.1049(19) 0.022(7) Uiso 1 1 d . . . . .
H2 H 0.502(3) 0.0720(17) 0.0898(18) 0.015(6) Uiso 1 1 d . . . . .
H1 H 0.650(4) 0.1619(19) 0.001(2) 0.028(7) Uiso 1 1 d . . . . .
H22 H 0.943(3) 0.2983(18) 0.2668(19) 0.021(7) Uiso 1 1 d . . . . .
H19 H 0.609(4) 0.4492(19) 0.054(2) 0.025(7) Uiso 1 1 d . . . . .
H20 H 0.469(4) 0.355(2) 0.136(2) 0.028(7) Uiso 1 1 d . . . . .
H23 H 1.065(4) 0.389(2) 0.178(2) 0.040(9) Uiso 1 1 d . . . . .
H3N H 0.896(4) 0.452(2) 0.075(2) 0.030(8) Uiso 1 1 d . . . . .
H1N H 0.929(4) 0.156(2) 0.016(2) 0.034(8) Uiso 1 1 d . . . . .
H4 H 0.966(4) -0.014(2) 0.193(2) 0.038(8) Uiso 1 1 d . . . . .
H24A H 0.671(3) 0.2041(18) 0.2755(17) 0.016(6) Uiso 1 1 d . . . . .
H6A H 0.708(3) -0.0897(18) 0.2220(17) 0.013(6) Uiso 1 1 d . . . . .
H6B H 0.531(4) -0.0710(19) 0.1669(19) 0.022(7) Uiso 1 1 d . . . . .
H24B H 0.486(4) 0.230(2) 0.226(2) 0.032(8) Uiso 1 1 d . . . . .
H10 H 0.079(4) 0.1938(19) 0.4734(19) 0.027(7) Uiso 1 1 d . . . . .
H15 H 0.916(4) 0.0728(18) 0.5485(18) 0.020(7) Uiso 1 1 d . . . . .
H14 H 0.848(4) 0.1396(19) 0.695(2) 0.026(7) Uiso 1 1 d . . . . .
H13 H 0.579(4) 0.1901(19) 0.704(2) 0.026(7) Uiso 1 1 d . . . . .
H32 H 0.858(4) 0.388(2) 0.757(2) 0.035(8) Uiso 1 1 d . . . . .
H33 H 0.903(4) 0.332(2) 0.602(2) 0.026(8) Uiso 1 1 d . . . . .
H11 H 0.288(4) 0.213(2) 0.620(3) 0.053(10) Uiso 1 1 d . . . . .
H9 H 0.154(4) 0.125(2) 0.331(2) 0.032(8) Uiso 1 1 d . . . . .
H28 H 0.077(4) 0.469(2) 0.568(2) 0.038(8) Uiso 1 1 d . . . . .
H27 H 0.143(4) 0.4138(19) 0.413(2) 0.024(7) Uiso 1 1 d . . . . .
H31 H 0.591(4) 0.440(2) 0.780(2) 0.042(9) Uiso 1 1 d . . . . .
H29 H 0.298(4) 0.466(2) 0.700(2) 0.042(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
Cl1 Co1 2.2971(7) . ?
Cl2 Co1 2.2893(7) . ?
Cl3 Co1 2.2819(7) . ?
Cl4 Co1 2.2324(8) . ?
O1 C7 1.221(3) . ?
O3 C25 1.213(3) . ?
O2 C17 1.213(3) . ?
O4 C35 1.215(3) . ?
N2 C7 1.392(3) . ?
N2 C17 1.404(3) . ?
N2 C6 1.479(3) . ?
N4 C25 1.399(3) . ?
N4 C35 1.399(3) . ?
N4 C24 1.467(3) . ?
N1 C1 1.338(3) . ?
N1 C5 1.339(3) . ?
N3 C23 1.336(3) . ?
N3 C19 1.340(3) . ?
C5 C4 1.378(4) . ?
C1 C2 1.368(4) . ?
C20 C19 1.372(4) . ?
C20 C21 1.392(4) . ?
C18 C16 1.413(3) . ?
C18 C8 1.416(3) . ?
C18 C12 1.417(3) . ?
C4 C3 1.388(3) . ?
C6 C3 1.510(3) . ?
C8 C9 1.376(3) . ?
C8 C7 1.473(3) . ?
C12 C11 1.416(4) . ?
C12 C13 1.416(4) . ?
C3 C2 1.390(3) . ?
C11 C10 1.362(4) . ?
C21 C22 1.393(4) . ?
C21 C24 1.506(3) . ?
C27 C26 1.376(3) . ?
C27 C28 1.404(4) . ?
C9 C10 1.395(4) . ?
C34 C33 1.380(4) . ?
C34 C36 1.408(3) . ?
C34 C35 1.465(3) . ?
C14 C13 1.360(4) . ?
C14 C15 1.405(4) . ?
C28 C29 1.361(4) . ?
C30 C29 1.412(4) . ?
C30 C31 1.413(4) . ?
C30 C36 1.420(3) . ?
C36 C26 1.406(3) . ?
C25 C26 1.470(3) . ?
C16 C15 1.373(3) . ?
C16 C17 1.466(3) . ?
C22 C23 1.368(4) . ?
C32 C31 1.366(4) . ?
C32 C33 1.396(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
Cl4 Co1 Cl3 112.04(3) . . ?
Cl4 Co1 Cl2 115.38(3) . . ?
Cl3 Co1 Cl2 103.38(3) . . ?
Cl4 Co1 Cl1 107.82(3) . . ?
Cl3 Co1 Cl1 109.50(3) . . ?
Cl2 Co1 Cl1 108.57(3) . . ?
C7 N2 C17 125.3(2) . . ?
C7 N2 C6 118.5(2) . . ?
C17 N2 C6 116.13(19) . . ?
C25 N4 C35 125.3(2) . . ?
C25 N4 C24 117.8(2) . . ?
C35 N4 C24 116.8(2) . . ?
C1 N1 C5 122.3(2) . . ?
C23 N3 C19 122.8(2) . . ?
N1 C5 C4 119.6(2) . . ?
N1 C1 C2 119.9(2) . . ?
C19 C20 C21 119.8(2) . . ?
C16 C18 C8 120.9(2) . . ?
C16 C18 C12 119.5(2) . . ?
C8 C18 C12 119.6(2) . . ?
C5 C4 C3 119.7(2) . . ?
N2 C6 C3 111.7(2) . . ?
N3 C19 C20 119.4(2) . . ?
C9 C8 C18 119.7(2) . . ?
C9 C8 C7 120.3(2) . . ?
C18 C8 C7 120.0(2) . . ?
C11 C12 C13 123.0(2) . . ?
C11 C12 C18 118.6(2) . . ?
C13 C12 C18 118.4(2) . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 C6 121.0(2) . . ?
C2 C3 C6 120.4(2) . . ?
O1 C7 N2 120.0(2) . . ?
O1 C7 C8 123.3(2) . . ?
N2 C7 C8 116.7(2) . . ?
C10 C11 C12 120.4(2) . . ?
C20 C21 C22 118.4(2) . . ?
C20 C21 C24 120.0(2) . . ?
C22 C21 C24 121.5(2) . . ?
C26 C27 C28 119.7(2) . . ?
C8 C9 C10 120.5(2) . . ?
C33 C34 C36 120.1(2) . . ?
C33 C34 C35 120.1(2) . . ?
C36 C34 C35 119.7(2) . . ?
C13 C14 C15 120.3(2) . . ?
C29 C28 C27 120.5(3) . . ?
C29 C30 C31 123.0(3) . . ?
C29 C30 C36 118.1(2) . . ?
C31 C30 C36 118.9(2) . . ?
C1 C2 C3 119.9(2) . . ?
C26 C36 C34 121.3(2) . . ?
C26 C36 C30 119.4(2) . . ?
C34 C36 C30 119.3(2) . . ?
O3 C25 N4 119.9(2) . . ?
O3 C25 C26 123.9(2) . . ?
N4 C25 C26 116.2(2) . . ?
C15 C16 C18 120.3(2) . . ?
C15 C16 C17 119.8(2) . . ?
C18 C16 C17 119.9(2) . . ?
C23 C22 C21 120.0(2) . . ?
C16 C15 C14 120.3(2) . . ?
C11 C10 C9 121.0(2) . . ?
C31 C32 C33 120.6(3) . . ?
C27 C26 C36 120.8(2) . . ?
C27 C26 C25 118.8(2) . . ?
C36 C26 C25 120.3(2) . . ?
C14 C13 C12 121.2(2) . . ?
O4 C35 N4 119.1(2) . . ?
O4 C35 C34 123.8(2) . . ?
N4 C35 C34 117.0(2) . . ?
N3 C23 C22 119.6(2) . . ?
C34 C33 C32 120.5(3) . . ?
O2 C17 N2 118.9(2) . . ?
O2 C17 C16 124.3(2) . . ?
N2 C17 C16 116.8(2) . . ?
C28 C29 C30 121.5(3) . . ?
C32 C31 C30 120.6(3) . . ?
N4 C24 C21 112.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C5 C4 1.2(4) . . . . ?
C5 N1 C1 C2 -0.4(4) . . . . ?
N1 C5 C4 C3 -0.6(4) . . . . ?
C7 N2 C6 C3 95.4(3) . . . . ?
C17 N2 C6 C3 -86.0(3) . . . . ?
C23 N3 C19 C20 0.5(4) . . . . ?
C21 C20 C19 N3 -0.9(4) . . . . ?
C16 C18 C8 C9 -178.3(2) . . . . ?
C12 C18 C8 C9 1.7(3) . . . . ?
C16 C18 C8 C7 3.6(3) . . . . ?
C12 C18 C8 C7 -176.4(2) . . . . ?
C16 C18 C12 C11 179.3(2) . . . . ?
C8 C18 C12 C11 -0.7(3) . . . . ?
C16 C18 C12 C13 -0.1(3) . . . . ?
C8 C18 C12 C13 179.9(2) . . . . ?
C5 C4 C3 C2 -0.7(4) . . . . ?
C5 C4 C3 C6 179.6(2) . . . . ?
N2 C6 C3 C4 100.8(3) . . . . ?
N2 C6 C3 C2 -78.8(3) . . . . ?
C17 N2 C7 O1 175.8(2) . . . . ?
C6 N2 C7 O1 -5.7(3) . . . . ?
C17 N2 C7 C8 -4.5(3) . . . . ?
C6 N2 C7 C8 174.0(2) . . . . ?
C9 C8 C7 O1 0.6(4) . . . . ?
C18 C8 C7 O1 178.8(2) . . . . ?
C9 C8 C7 N2 -179.1(2) . . . . ?
C18 C8 C7 N2 -0.9(3) . . . . ?
C13 C12 C11 C10 178.6(2) . . . . ?
C18 C12 C11 C10 -0.7(4) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
C19 C20 C21 C24 -177.2(2) . . . . ?
C18 C8 C9 C10 -1.4(4) . . . . ?
C7 C8 C9 C10 176.8(2) . . . . ?
C26 C27 C28 C29 0.0(4) . . . . ?
N1 C1 C2 C3 -1.0(4) . . . . ?
C4 C3 C2 C1 1.5(4) . . . . ?
C6 C3 C2 C1 -178.9(2) . . . . ?
C33 C34 C36 C26 -179.1(2) . . . . ?
C35 C34 C36 C26 -1.3(3) . . . . ?
C33 C34 C36 C30 -0.8(4) . . . . ?
C35 C34 C36 C30 177.0(2) . . . . ?
C29 C30 C36 C26 0.1(3) . . . . ?
C31 C30 C36 C26 178.9(2) . . . . ?
C29 C30 C36 C34 -178.3(2) . . . . ?
C31 C30 C36 C34 0.5(4) . . . . ?
C35 N4 C25 O3 177.1(2) . . . . ?
C24 N4 C25 O3 -6.2(3) . . . . ?
C35 N4 C25 C26 -3.9(3) . . . . ?
C24 N4 C25 C26 172.9(2) . . . . ?
C8 C18 C16 C15 179.3(2) . . . . ?
C12 C18 C16 C15 -0.6(3) . . . . ?
C8 C18 C16 C17 -1.2(3) . . . . ?
C12 C18 C16 C17 178.8(2) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C24 C21 C22 C23 177.6(2) . . . . ?
C18 C16 C15 C14 0.8(4) . . . . ?
C17 C16 C15 C14 -178.6(2) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C12 C11 C10 C9 1.1(4) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C28 C27 C26 C36 -1.8(4) . . . . ?
C28 C27 C26 C25 176.1(2) . . . . ?
C34 C36 C26 C27 180.0(2) . . . . ?
C30 C36 C26 C27 1.7(3) . . . . ?
C34 C36 C26 C25 2.2(3) . . . . ?
C30 C36 C26 C25 -176.2(2) . . . . ?
O3 C25 C26 C27 1.4(4) . . . . ?
N4 C25 C26 C27 -177.6(2) . . . . ?
O3 C25 C26 C36 179.3(2) . . . . ?
N4 C25 C26 C36 0.3(3) . . . . ?
C15 C14 C13 C12 -0.5(4) . . . . ?
C11 C12 C13 C14 -178.7(2) . . . . ?
C18 C12 C13 C14 0.7(4) . . . . ?
C25 N4 C35 O4 -176.1(2) . . . . ?
C24 N4 C35 O4 7.1(3) . . . . ?
C25 N4 C35 C34 4.7(3) . . . . ?
C24 N4 C35 C34 -172.0(2) . . . . ?
C33 C34 C35 O4 -3.3(4) . . . . ?
C36 C34 C35 O4 178.9(2) . . . . ?
C33 C34 C35 N4 175.8(2) . . . . ?
C36 C34 C35 N4 -2.0(3) . . . . ?
C19 N3 C23 C22 -0.1(4) . . . . ?
C21 C22 C23 N3 0.1(4) . . . . ?
C36 C34 C33 C32 0.2(4) . . . . ?
C35 C34 C33 C32 -177.6(2) . . . . ?
C31 C32 C33 C34 0.6(4) . . . . ?
C7 N2 C17 O2 -173.6(2) . . . . ?
C6 N2 C17 O2 7.9(3) . . . . ?
C7 N2 C17 C16 6.8(3) . . . . ?
C6 N2 C17 C16 -171.7(2) . . . . ?
C15 C16 C17 O2 -3.8(4) . . . . ?
C18 C16 C17 O2 176.7(2) . . . . ?
C15 C16 C17 N2 175.7(2) . . . . ?
C18 C16 C17 N2 -3.8(3) . . . . ?
C27 C28 C29 C30 1.8(4) . . . . ?
C31 C30 C29 C28 179.5(3) . . . . ?
C36 C30 C29 C28 -1.8(4) . . . . ?
C33 C32 C31 C30 -0.8(4) . . . . ?
C29 C30 C31 C32 179.0(3) . . . . ?
C36 C30 C31 C32 0.3(4) . . . . ?
C25 N4 C24 C21 96.4(3) . . . . ?
C35 N4 C24 C21 -86.6(3) . . . . ?
C20 C21 C24 N4 -92.0(3) . . . . ?
C22 C21 C24 N4 89.9(3) . . . . ?

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
C5 H5 Cl2 0.98(3) 2.77(3) 3.448(3) 127.0(19) 2_765
C5 H5 O1 0.98(3) 2.38(3) 3.065(3) 127(2) 1_655
C2 H2 Cl2 0.95(3) 2.85(2) 3.548(3) 131.6(19) 2_665
C2 H2 O1 0.95(3) 2.62(3) 3.272(3) 126.2(19) .
C1 H1 Cl3 1.01(3) 2.77(3) 3.391(3) 120.5(19) 2_765
C22 H22 O4 0.95(3) 2.52(3) 3.091(3) 118.4(19) .
C19 H19 Cl1 0.97(3) 2.79(3) 3.368(3) 118.9(19) .
C20 H20 Cl1 0.95(3) 2.84(3) 3.558(3) 134(2) 2_665
C20 H20 Cl2 0.95(3) 2.91(3) 3.518(3) 123(2) 2_665
C23 H23 Cl1 0.94(3) 2.76(3) 3.352(3) 122(2) 2_765
C23 H23 O3 0.94(3) 2.52(3) 3.195(3) 129(2) 1_655
N3 H3N Cl1 0.90(3) 2.50(3) 3.195(2) 134(2) .
N3 H3N Cl1 0.90(3) 2.60(3) 3.263(2) 131(2) 2_765
N1 H1N Cl2 0.93(3) 2.69(3) 3.376(2) 131(2) 2_765
N1 H1N Cl3 0.93(3) 2.38(3) 3.134(2) 138(2) 2_765

_refine_diff_density_max         0.636
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.085

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1824823'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N2 O2, Cl'
_chemical_formula_sum            'C18 H13 Cl N2 O2'
_chemical_formula_weight         324.75

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3112(7)
_cell_length_b                   7.7033(7)
_cell_length_c                   13.0401(12)
_cell_angle_alpha                79.183(3)
_cell_angle_beta                 86.649(3)
_cell_angle_gamma                88.692(3)
_cell_volume                     720.09(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9578
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      26.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8086
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20729
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.692
_diffrn_reflns_theta_max         26.580
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3005
_reflns_number_gt                2459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0384P)²+0.2609P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3005
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.10982(5) 0.76694(5) 1.04081(3) 0.02538(13) Uani 1 1 d . . . . .
O1 O 0.85654(16) 0.85822(14) 0.64744(9) 0.0270(3) Uani 1 1 d . . . . .
O2 O 0.62993(16) 0.31092(14) 0.76879(8) 0.0265(3) Uani 1 1 d . . . . .
N1 N 0.2763(2) 0.85807(19) 0.91835(10) 0.0265(3) Uani 1 1 d . . . . .
N2 N 0.75124(17) 0.58153(16) 0.70732(9) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.4209(2) 0.9586(2) 0.88104(13) 0.0279(4) Uani 1 1 d . . . . .
C2 C 0.5786(2) 0.8819(2) 0.84674(12) 0.0239(4) Uani 1 1 d . . . . .
C3 C 0.5866(2) 0.7004(2) 0.85023(11) 0.0187(3) Uani 1 1 d . . . . .
C4 C 0.4311(2) 0.6014(2) 0.88703(12) 0.0216(3) Uani 1 1 d . . . . .
C5 C 0.2767(2) 0.6830(2) 0.92136(12) 0.0252(4) Uani 1 1 d . . . . .
C6 C 0.7593(2) 0.6122(2) 0.81528(12) 0.0204(3) Uani 1 1 d . . . . .
C17 C 0.6867(2) 0.41837(19) 0.69359(12) 0.0185(3) Uani 1 1 d . . . . .
C16 C 0.6918(2) 0.38670(19) 0.58530(12) 0.0173(3) Uani 1 1 d . . . . .
C15 C 0.6367(2) 0.2260(2) 0.56678(13) 0.0220(3) Uani 1 1 d . . . . .
C14 C 0.6464(2) 0.1929(2) 0.46449(14) 0.0254(4) Uani 1 1 d . . . . .
C13 C 0.7084(2) 0.3179(2) 0.38264(13) 0.0242(4) Uani 1 1 d . . . . .
C12 C 0.7647(2) 0.4851(2) 0.39790(12) 0.0207(3) Uani 1 1 d . . . . .
C11 C 0.8301(2) 0.6192(2) 0.31505(13) 0.0244(4) Uani 1 1 d . . . . .
C10 C 0.8869(2) 0.7770(2) 0.33436(13) 0.0248(4) Uani 1 1 d . . . . .
C9 C 0.8807(2) 0.8093(2) 0.43703(12) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.8160(2) 0.68286(19) 0.51950(12) 0.0174(3) Uani 1 1 d . . . . .
C7 C 0.8113(2) 0.71816(19) 0.62675(12) 0.0185(3) Uani 1 1 d . . . . .
C18 C 0.7569(2) 0.5186(2) 0.50171(12) 0.0170(3) Uani 1 1 d . . . . .
H11 H 0.837(2) 0.595(2) 0.2470(14) 0.028(5) Uiso 1 1 d . . . . .
H15 H 0.594(2) 0.140(2) 0.6246(13) 0.021(4) Uiso 1 1 d . . . . .
H9 H 0.922(2) 0.920(2) 0.4505(12) 0.019(4) Uiso 1 1 d . . . . .
H6A H 0.864(2) 0.685(2) 0.8178(13) 0.022(4) Uiso 1 1 d . . . . .
H10 H 0.934(2) 0.867(2) 0.2784(14) 0.025(4) Uiso 1 1 d . . . . .
H14 H 0.613(3) 0.075(3) 0.4536(14) 0.034(5) Uiso 1 1 d . . . . .
H6B H 0.778(2) 0.496(2) 0.8593(13) 0.023(4) Uiso 1 1 d . . . . .
H4 H 0.429(2) 0.479(2) 0.8886(13) 0.020(4) Uiso 1 1 d . . . . .
H1 H 0.407(3) 1.086(3) 0.8806(14) 0.033(5) Uiso 1 1 d . . . . .
H2 H 0.681(2) 0.950(2) 0.8245(13) 0.024(4) Uiso 1 1 d . . . . .
H13 H 0.717(3) 0.294(2) 0.3142(15) 0.032(5) Uiso 1 1 d . . . . .
H5 H 0.169(3) 0.619(2) 0.9499(14) 0.028(5) Uiso 1 1 d . . . . .
H1N H 0.177(3) 0.905(3) 0.9440(15) 0.037(5) 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
O1 C7 1.2174(18) . ?
O2 C17 1.2176(18) . ?
N1 C1 1.338(2) . ?
N1 C5 1.342(2) . ?
N1 H1N 0.88(2) . ?
N2 C17 1.3986(19) . ?
N2 C7 1.3988(19) . ?
N2 C6 1.4751(19) . ?
C1 C2 1.373(2) . ?
C1 H1 0.980(19) . ?
C2 C3 1.390(2) . ?
C2 H2 0.924(18) . ?
C3 C4 1.393(2) . ?
C3 C6 1.508(2) . ?
C4 C5 1.373(2) . ?
C4 H4 0.940(17) . ?
C5 H5 0.954(19) . ?
C6 H6A 0.963(18) . ?
C6 H6B 0.978(18) . ?
C17 C16 1.476(2) . ?
C16 C15 1.378(2) . ?
C16 C18 1.412(2) . ?
C15 C14 1.402(2) . ?
C15 H15 0.949(17) . ?
C14 C13 1.360(2) . ?
C14 H14 0.986(19) . ?
C13 C12 1.413(2) . ?
C13 H13 0.941(19) . ?
C12 C11 1.416(2) . ?
C12 C18 1.423(2) . ?
C11 C10 1.365(2) . ?
C11 H11 0.939(18) . ?
C10 C9 1.405(2) . ?
C10 H10 0.960(18) . ?
C9 C8 1.378(2) . ?
C9 H9 0.958(17) . ?
C8 C18 1.410(2) . ?
C8 C7 1.472(2) . ?

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
C1 N1 C5 122.40(15) . . ?
C1 N1 H1N 120.6(13) . . ?
C5 N1 H1N 116.9(13) . . ?
C17 N2 C7 125.25(13) . . ?
C17 N2 C6 117.74(12) . . ?
C7 N2 C6 117.00(12) . . ?
N1 C1 C2 119.82(16) . . ?
N1 C1 H1 116.5(11) . . ?
C2 C1 H1 123.7(11) . . ?
C1 C2 C3 119.83(16) . . ?
C1 C2 H2 119.8(11) . . ?
C3 C2 H2 120.3(11) . . ?
C2 C3 C4 118.42(15) . . ?
C2 C3 C6 120.93(15) . . ?
C4 C3 C6 120.65(14) . . ?
C5 C4 C3 119.94(16) . . ?
C5 C4 H4 118.6(10) . . ?
C3 C4 H4 121.5(10) . . ?
N1 C5 C4 119.56(16) . . ?
N1 C5 H5 117.8(11) . . ?
C4 C5 H5 122.6(11) . . ?
N2 C6 C3 111.61(13) . . ?
N2 C6 H6A 108.1(10) . . ?
C3 C6 H6A 110.1(10) . . ?
N2 C6 H6B 106.4(10) . . ?
C3 C6 H6B 111.2(10) . . ?
H6A C6 H6B 109.2(15) . . ?
O2 C17 N2 120.14(14) . . ?
O2 C17 C16 123.28(14) . . ?
N2 C17 C16 116.58(13) . . ?
C15 C16 C18 120.34(14) . . ?
C15 C16 C17 119.48(14) . . ?
C18 C16 C17 120.15(13) . . ?
C16 C15 C14 119.83(15) . . ?
C16 C15 H15 118.3(10) . . ?
C14 C15 H15 121.8(10) . . ?
C13 C14 C15 120.93(15) . . ?
C13 C14 H14 120.6(11) . . ?
C15 C14 H14 118.4(11) . . ?
C14 C13 C12 121.15(15) . . ?
C14 C13 H13 120.6(11) . . ?
C12 C13 H13 118.2(11) . . ?
C13 C12 C11 123.09(15) . . ?
C13 C12 C18 118.13(14) . . ?
C11 C12 C18 118.78(14) . . ?
C10 C11 C12 120.74(15) . . ?
C10 C11 H11 121.2(11) . . ?
C12 C11 H11 118.1(11) . . ?
C11 C10 C9 120.44(15) . . ?
C11 C10 H10 120.7(10) . . ?
C9 C10 H10 118.8(10) . . ?
C8 C9 C10 120.49(15) . . ?
C8 C9 H9 119.2(10) . . ?
C10 C9 H9 120.3(10) . . ?
C9 C8 C18 120.20(14) . . ?
C9 C8 C7 119.92(14) . . ?
C18 C8 C7 119.88(13) . . ?
O1 C7 N2 119.68(14) . . ?
O1 C7 C8 123.29(14) . . ?
N2 C7 C8 117.02(13) . . ?
C8 C18 C16 121.04(14) . . ?
C8 C18 C12 119.34(14) . . ?
C16 C18 C12 119.62(14) . . ?

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
C5 N1 C1 C2 -1.8(3) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C1 C2 C3 C6 -178.65(15) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C6 C3 C4 C5 178.14(14) . . . . ?
C1 N1 C5 C4 1.3(3) . . . . ?
C3 C4 C5 N1 0.5(2) . . . . ?
C17 N2 C6 C3 -92.60(16) . . . . ?
C7 N2 C6 C3 88.17(16) . . . . ?
C2 C3 C6 N2 -98.37(17) . . . . ?
C4 C3 C6 N2 81.74(18) . . . . ?
C7 N2 C17 O2 -176.79(14) . . . . ?
C6 N2 C17 O2 4.1(2) . . . . ?
C7 N2 C17 C16 3.2(2) . . . . ?
C6 N2 C17 C16 -176.00(13) . . . . ?
O2 C17 C16 C15 -2.5(2) . . . . ?
N2 C17 C16 C15 177.54(13) . . . . ?
O2 C17 C16 C18 179.03(14) . . . . ?
N2 C17 C16 C18 -0.9(2) . . . . ?
C18 C16 C15 C14 0.4(2) . . . . ?
C17 C16 C15 C14 -178.06(14) . . . . ?
C16 C15 C14 C13 -0.5(2) . . . . ?
C15 C14 C13 C12 -0.1(3) . . . . ?
C14 C13 C12 C11 179.99(16) . . . . ?
C14 C13 C12 C18 0.8(2) . . . . ?
C13 C12 C11 C10 -178.43(15) . . . . ?
C18 C12 C11 C10 0.8(2) . . . . ?
C12 C11 C10 C9 -0.2(2) . . . . ?
C11 C10 C9 C8 -0.5(2) . . . . ?
C10 C9 C8 C18 0.6(2) . . . . ?
C10 C9 C8 C7 179.65(14) . . . . ?
C17 N2 C7 O1 176.47(14) . . . . ?
C6 N2 C7 O1 -4.4(2) . . . . ?
C17 N2 C7 C8 -3.5(2) . . . . ?
C6 N2 C7 C8 175.66(13) . . . . ?
C9 C8 C7 O1 2.6(2) . . . . ?
C18 C8 C7 O1 -178.37(14) . . . . ?
C9 C8 C7 N2 -177.42(14) . . . . ?
C18 C8 C7 N2 1.6(2) . . . . ?
C9 C8 C18 C16 179.40(14) . . . . ?
C7 C8 C18 C16 0.4(2) . . . . ?
C9 C8 C18 C12 -0.1(2) . . . . ?
C7 C8 C18 C12 -179.08(13) . . . . ?
C15 C16 C18 C8 -179.18(14) . . . . ?
C17 C16 C18 C8 -0.7(2) . . . . ?
C15 C16 C18 C12 0.3(2) . . . . ?
C17 C16 C18 C12 178.73(13) . . . . ?
C13 C12 C18 C8 178.62(14) . . . . ?
C11 C12 C18 C8 -0.6(2) . . . . ?
C13 C12 C18 C16 -0.9(2) . . . . ?
C11 C12 C18 C16 179.89(14) . . . . ?

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
C4 H4 O2 0.940(17) 2.586(17) 3.222(2) 125.3(13) .
C1 H1 Cl1 0.980(19) 2.669(19) 3.3168(18) 123.9(14) 2_577
C1 H1 O2 0.980(19) 2.589(19) 3.206(2) 121.1(14) 1_565
C5 H5 Cl1 0.954(19) 2.641(18) 3.2572(17) 122.7(13) .
N1 H1N Cl1 0.88(2) 2.53(2) 3.1868(15) 131.9(16) .
N1 H1N Cl1 0.88(2) 2.61(2) 3.2328(15) 128.9(16) 2_577
C4 H4 O2 0.940(17) 2.586(17) 3.222(2) 125.3(13) .
C1 H1 Cl1 0.980(19) 2.669(19) 3.3168(18) 123.9(14) 2_577
C1 H1 O2 0.980(19) 2.589(19) 3.206(2) 121.1(14) 1_565
C5 H5 Cl1 0.954(19) 2.641(18) 3.2572(17) 122.7(13) .
N1 H1N Cl1 0.88(2) 2.53(2) 3.1868(15) 131.9(16) .
N1 H1N Cl1 0.88(2) 2.61(2) 3.2328(15) 128.9(16) 2_577

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1824820'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H13 N2 O2), Cl4 Hg'
_chemical_formula_sum            'C36 H26 Cl4 Hg N4 O4 '
_chemical_formula_weight         921.00
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'
Hg Hg -2.3894 9.2266 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8598(4)
_cell_length_b                   14.7496(9)
_cell_length_c                   14.7874(8)
_cell_angle_alpha                102.704(2)
_cell_angle_beta                 101.054(2)
_cell_angle_gamma                93.104(2)
_cell_volume                     1632.97(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9741
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      33.80

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.063
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    5.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6202
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56440
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6690
_reflns_number_gt                6023
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0080P)²+27.3202P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6690
_refine_ls_number_parameters     528
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.7936(2) 0.54584(13) -0.04274(13) 0.0306(2) Uani 1 1 d . U . . .
Cl2 Cl 0.7385(2) 0.81774(13) -0.01897(13) 0.0306(2) Uani 1 1 d . U . . .
Cl3 Cl 1.1787(2) 0.75735(13) 0.09361(13) 0.0306(2) Uani 1 1 d . U . . .
Cl4 Cl 0.7644(2) 0.68653(13) 0.21287(13) 0.0306(2) Uani 1 1 d . U . . .
Hg1 Hg 0.86519(4) 0.70448(2) 0.07438(2) 0.02542(9) Uani 1 1 d . U . . .
O1 O 0.3223(6) 0.0343(4) 0.2191(3) 0.0254(10) Uani 1 1 d . U . . .
O3 O 0.3009(6) 0.3347(4) 0.2871(3) 0.0256(10) Uani 1 1 d . U . . .
O2 O 0.8678(6) 0.0058(3) 0.3695(3) 0.0235(10) Uani 1 1 d . U . . .
O4 O 0.8469(6) 0.2806(4) 0.4138(3) 0.0265(11) Uani 1 1 d . U . . .
N2 N 0.5906(7) 0.0147(4) 0.2973(4) 0.0165(10) Uani 1 1 d . U . . .
N4 N 0.5716(7) 0.3057(3) 0.3522(4) 0.0150(10) Uani 1 1 d . U . . .
N1 N 0.8710(8) 0.1147(4) 0.0552(4) 0.0221(12) Uani 1 1 d . U . . .
N3 N 0.8421(7) 0.4196(4) 0.1104(4) 0.0201(11) Uani 1 1 d . U . . .
C5 C 0.9703(9) 0.0679(5) 0.1099(5) 0.0236(14) Uani 1 1 d . U . . .
C1 C 0.6990(9) 0.1147(5) 0.0497(5) 0.0196(13) Uani 1 1 d . U . . .
C20 C 0.5864(9) 0.3624(5) 0.1476(5) 0.0201(13) Uani 1 1 d . U . . .
C18 C 0.5181(8) 0.1091(4) 0.4702(4) 0.0147(11) Uani 1 1 d . U . . .
C4 C 0.8933(9) 0.0161(5) 0.1610(5) 0.0229(13) Uani 1 1 d . U . . .
C6 C 0.6259(9) -0.0442(5) 0.2095(5) 0.0205(13) Uani 1 1 d . U . . .
C19 C 0.6688(9) 0.4137(5) 0.0986(5) 0.0226(14) Uani 1 1 d . U . . .
C8 C 0.3905(8) 0.0976(4) 0.3857(5) 0.0158(11) Uani 1 1 d . U . . .
C12 C 0.4772(8) 0.1520(4) 0.5585(5) 0.0185(12) Uani 1 1 d . U . . .
C3 C 0.7147(8) 0.0128(4) 0.1559(4) 0.0169(12) Uani 1 1 d . U . . .
C7 C 0.4265(8) 0.0480(4) 0.2943(5) 0.0177(12) Uani 1 1 d . U . . .
C11 C 0.3102(9) 0.1836(4) 0.5584(5) 0.0225(13) Uani 1 1 d . U . . .
C21 C 0.6845(8) 0.3159(4) 0.2081(4) 0.0166(12) Uani 1 1 d . U . . .
C27 C 0.2286(9) 0.4140(4) 0.4659(5) 0.0191(12) Uani 1 1 d . U . . .
C9 C 0.2303(8) 0.1305(5) 0.3889(5) 0.0212(13) Uani 1 1 d . U . . .
C34 C 0.6813(8) 0.3507(4) 0.5240(4) 0.0176(12) Uani 1 1 d . U . . .
C14 C 0.7676(9) 0.1332(5) 0.6388(5) 0.0232(14) Uani 1 1 d . U . . .
C28 C 0.1989(9) 0.4493(5) 0.5575(5) 0.0240(14) Uani 1 1 d . U . . .
C30 C 0.4898(9) 0.4197(4) 0.6266(5) 0.0206(13) Uani 1 1 d . U . . .
C2 C 0.6181(8) 0.0643(4) 0.0995(4) 0.0180(12) Uani 1 1 d . U . . .
C36 C 0.5190(8) 0.3840(4) 0.5344(4) 0.0151(11) Uani 1 1 d . U . . .
C25 C 0.4113(8) 0.3405(4) 0.3586(4) 0.0154(12) Uani 1 1 d . U . . .
C16 C 0.6849(8) 0.0782(4) 0.4685(4) 0.0148(11) Uani 1 1 d . U . . .
C22 C 0.8647(9) 0.3246(5) 0.2193(5) 0.0196(13) Uani 1 1 d . U . . .
C15 C 0.8071(8) 0.0907(4) 0.5514(5) 0.0189(12) Uani 1 1 d . U . . .
C10 C 0.1907(9) 0.1736(5) 0.4760(5) 0.0234(14) Uani 1 1 d . U . . .
C32 C 0.7801(10) 0.3899(5) 0.6943(5) 0.0283(15) Uani 1 1 d . U . . .
C26 C 0.3858(8) 0.3814(4) 0.4550(4) 0.0150(11) Uani 1 1 d . U . . .
C13 C 0.6066(9) 0.1633(5) 0.6422(5) 0.0223(13) Uani 1 1 d . U . . .
C35 C 0.7102(8) 0.3103(4) 0.4286(5) 0.0173(12) Uani 1 1 d . U . . .
C23 C 0.9422(9) 0.3774(5) 0.1691(5) 0.0225(14) Uani 1 1 d . U . . .
C33 C 0.8091(9) 0.3534(5) 0.6031(5) 0.0215(13) Uani 1 1 d . U . . .
C17 C 0.7258(8) 0.0316(4) 0.3781(4) 0.0156(12) Uani 1 1 d . U . . .
C29 C 0.3263(10) 0.4517(5) 0.6358(5) 0.0242(14) Uani 1 1 d . U . . .
C31 C 0.6247(10) 0.4215(5) 0.7063(5) 0.0272(15) Uani 1 1 d . U . . .
C24 C 0.5950(9) 0.2551(4) 0.2586(5) 0.0182(12) Uani 1 1 d . U . . .
H1N H 0.919(10) 0.149(6) 0.024(6) 0.03(2) Uiso 1 1 d . . . . .
H3N H 0.896(12) 0.452(6) 0.079(6) 0.04(3) Uiso 1 1 d . . . . .
H1 H 0.642(8) 0.152(5) 0.010(5) 0.009(16) Uiso 1 1 d . . . . .
H19 H 0.612(9) 0.442(5) 0.057(5) 0.013(17) Uiso 1 1 d . . . . .
H2 H 0.500(10) 0.066(5) 0.097(5) 0.018(18) Uiso 1 1 d . . . . .
H20 H 0.469(10) 0.360(5) 0.140(5) 0.024(19) Uiso 1 1 d . . . . .
H5 H 1.083(10) 0.074(5) 0.108(5) 0.02(2) Uiso 1 1 d . . . . .
H22 H 0.935(11) 0.295(6) 0.254(6) 0.03(2) Uiso 1 1 d . . . . .
H23 H 1.065(12) 0.384(6) 0.172(6) 0.04(2) Uiso 1 1 d . . . . .
H4 H 0.959(11) -0.017(6) 0.196(6) 0.04(2) Uiso 1 1 d . . . . .
H24B H 0.666(8) 0.204(5) 0.269(5) 0.011(16) Uiso 1 1 d . . . . .
H6A H 0.699(9) -0.094(5) 0.228(5) 0.019(18) Uiso 1 1 d . . . . .
H6B H 0.517(9) -0.077(5) 0.175(5) 0.016(17) Uiso 1 1 d . . . . .
H24A H 0.487(9) 0.232(5) 0.224(5) 0.012(16) Uiso 1 1 d . . . . .
H9 H 0.149(10) 0.122(5) 0.332(5) 0.021(19) Uiso 1 1 d . . . . .
H32 H 0.865(10) 0.383(5) 0.742(6) 0.02(2) Uiso 1 1 d . . . . .
H15 H 0.916(10) 0.070(5) 0.548(5) 0.020(18) Uiso 1 1 d . . . . .
H29 H 0.305(10) 0.473(5) 0.700(6) 0.03(2) Uiso 1 1 d . . . . .
H31 H 0.605(10) 0.437(6) 0.768(6) 0.03(2) Uiso 1 1 d . . . . .
H27 H 0.141(10) 0.410(5) 0.411(6) 0.03(2) Uiso 1 1 d . . . . .
H33 H 0.910(10) 0.330(5) 0.593(5) 0.020(18) Uiso 1 1 d . . . . .
H28 H 0.086(10) 0.471(5) 0.565(5) 0.03(2) Uiso 1 1 d . . . . .
H10 H 0.076(11) 0.196(6) 0.477(6) 0.03(2) Uiso 1 1 d . . . . .
H13 H 0.580(10) 0.192(6) 0.699(6) 0.03(2) Uiso 1 1 d . . . . .
H11 H 0.280(10) 0.211(6) 0.617(6) 0.03(2) Uiso 1 1 d . . . . .
H14 H 0.859(11) 0.145(6) 0.694(6) 0.04(2) 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
Cl1 Hg1 2.5481(19) . ?
Cl2 Hg1 2.5210(18) . ?
Cl3 Hg1 2.4873(18) . ?
Cl4 Hg1 2.3935(17) . ?
O1 C7 1.218(8) . ?
O3 C25 1.216(8) . ?
O2 C17 1.219(7) . ?
O4 C35 1.222(8) . ?
N2 C7 1.402(8) . ?
N2 C17 1.405(8) . ?
N2 C6 1.478(8) . ?
N4 C25 1.398(8) . ?
N4 C35 1.398(8) . ?
N4 C24 1.471(8) . ?
N1 C1 1.338(9) . ?
N1 C5 1.343(9) . ?
N1 H1N 0.87(8) . ?
N3 C19 1.336(9) . ?
N3 C23 1.337(9) . ?
N3 H3N 0.88(9) . ?
C5 C4 1.378(10) . ?
C5 H5 0.89(8) . ?
C1 C2 1.368(9) . ?
C1 H1 0.96(7) . ?
C20 C19 1.372(9) . ?
C20 C21 1.388(9) . ?
C20 H20 0.91(8) . ?
C18 C16 1.414(8) . ?
C18 C8 1.416(9) . ?
C18 C12 1.424(9) . ?
C4 C3 1.389(9) . ?
C4 H4 0.90(9) . ?
C6 C3 1.504(9) . ?
C6 H6A 1.01(7) . ?
C6 H6B 0.95(7) . ?
C19 H19 0.89(7) . ?
C8 C9 1.379(9) . ?
C8 C7 1.475(9) . ?
C12 C13 1.415(10) . ?
C12 C11 1.416(9) . ?
C3 C2 1.395(9) . ?
C11 C10 1.363(10) . ?
C11 H11 0.95(8) . ?
C21 C22 1.389(9) . ?
C21 C24 1.512(8) . ?
C27 C26 1.375(9) . ?
C27 C28 1.409(9) . ?
C27 H27 0.95(8) . ?
C9 C10 1.406(10) . ?
C9 H9 0.94(7) . ?
C34 C33 1.379(9) . ?
C34 C36 1.415(9) . ?
C34 C35 1.471(9) . ?
C14 C13 1.370(10) . ?
C14 C15 1.406(10) . ?
C14 H14 0.95(9) . ?
C28 C29 1.371(10) . ?
C28 H28 0.97(8) . ?
C30 C29 1.413(10) . ?
C30 C36 1.416(9) . ?
C30 C31 1.421(10) . ?
C2 H2 0.92(7) . ?
C36 C26 1.407(9) . ?
C25 C26 1.477(8) . ?
C16 C15 1.375(9) . ?
C16 C17 1.465(9) . ?
C22 C23 1.379(9) . ?
C22 H22 0.88(9) . ?
C15 H15 0.93(7) . ?
C10 H10 0.98(8) . ?
C32 C31 1.360(11) . ?
C32 C33 1.404(10) . ?
C32 H32 0.90(8) . ?
C13 H13 0.92(8) . ?
C23 H23 0.96(9) . ?
C33 H33 0.91(7) . ?
C29 H29 0.98(8) . ?
C31 H31 0.94(8) . ?
C24 H24B 0.99(7) . ?
C24 H24A 0.91(7) . ?

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
Cl4 Hg1 Cl3 117.69(6) . . ?
Cl4 Hg1 Cl2 120.63(6) . . ?
Cl3 Hg1 Cl2 98.12(6) . . ?
Cl4 Hg1 Cl1 105.98(6) . . ?
Cl3 Hg1 Cl1 109.12(6) . . ?
Cl2 Hg1 Cl1 104.30(6) . . ?
C7 N2 C17 125.1(5) . . ?
C7 N2 C6 118.3(5) . . ?
C17 N2 C6 116.5(5) . . ?
C25 N4 C35 125.4(5) . . ?
C25 N4 C24 118.0(5) . . ?
C35 N4 C24 116.5(5) . . ?
C1 N1 C5 122.4(6) . . ?
C1 N1 H1N 117(5) . . ?
C5 N1 H1N 120(5) . . ?
C19 N3 C23 122.7(6) . . ?
C19 N3 H3N 120(6) . . ?
C23 N3 H3N 117(6) . . ?
N1 C5 C4 119.4(6) . . ?
N1 C5 H5 114(5) . . ?
C4 C5 H5 127(5) . . ?
N1 C1 C2 119.9(6) . . ?
N1 C1 H1 115(4) . . ?
C2 C1 H1 125(4) . . ?
C19 C20 C21 119.5(6) . . ?
C19 C20 H20 119(5) . . ?
C21 C20 H20 122(5) . . ?
C16 C18 C8 121.1(6) . . ?
C16 C18 C12 119.5(6) . . ?
C8 C18 C12 119.4(6) . . ?
C5 C4 C3 120.1(7) . . ?
C5 C4 H4 120(6) . . ?
C3 C4 H4 120(6) . . ?
N2 C6 C3 111.5(5) . . ?
N2 C6 H6A 108(4) . . ?
C3 C6 H6A 112(4) . . ?
N2 C6 H6B 106(4) . . ?
C3 C6 H6B 115(4) . . ?
H6A C6 H6B 105(6) . . ?
N3 C19 C20 119.9(6) . . ?
N3 C19 H19 117(4) . . ?
C20 C19 H19 123(4) . . ?
C9 C8 C18 120.1(6) . . ?
C9 C8 C7 119.7(6) . . ?
C18 C8 C7 120.2(5) . . ?
C13 C12 C11 122.9(6) . . ?
C13 C12 C18 118.6(6) . . ?
C11 C12 C18 118.5(6) . . ?
C4 C3 C2 118.2(6) . . ?
C4 C3 C6 121.6(6) . . ?
C2 C3 C6 120.3(6) . . ?
O1 C7 N2 119.8(6) . . ?
O1 C7 C8 123.8(6) . . ?
N2 C7 C8 116.3(5) . . ?
C10 C11 C12 121.2(6) . . ?
C10 C11 H11 119(5) . . ?
C12 C11 H11 119(5) . . ?
C20 C21 C22 118.9(6) . . ?
C20 C21 C24 120.0(6) . . ?
C22 C21 C24 121.1(6) . . ?
C26 C27 C28 119.9(6) . . ?
C26 C27 H27 118(5) . . ?
C28 C27 H27 122(5) . . ?
C8 C9 C10 120.4(6) . . ?
C8 C9 H9 118(4) . . ?
C10 C9 H9 122(4) . . ?
C33 C34 C36 120.1(6) . . ?
C33 C34 C35 120.4(6) . . ?
C36 C34 C35 119.5(5) . . ?
C13 C14 C15 120.3(6) . . ?
C13 C14 H14 122(5) . . ?
C15 C14 H14 118(5) . . ?
C29 C28 C27 120.3(6) . . ?
C29 C28 H28 120(5) . . ?
C27 C28 H28 119(5) . . ?
C29 C30 C36 118.6(6) . . ?
C29 C30 C31 122.3(6) . . ?
C36 C30 C31 119.1(6) . . ?
C1 C2 C3 120.0(6) . . ?
C1 C2 H2 119(4) . . ?
C3 C2 H2 121(4) . . ?
C26 C36 C34 121.3(6) . . ?
C26 C36 C30 119.5(6) . . ?
C34 C36 C30 119.2(6) . . ?
O3 C25 N4 120.0(6) . . ?
O3 C25 C26 123.6(6) . . ?
N4 C25 C26 116.4(5) . . ?
C15 C16 C18 120.1(6) . . ?
C15 C16 C17 120.2(6) . . ?
C18 C16 C17 119.7(5) . . ?
C23 C22 C21 119.7(6) . . ?
C23 C22 H22 116(5) . . ?
C21 C22 H22 124(5) . . ?
C16 C15 C14 120.6(6) . . ?
C16 C15 H15 119(4) . . ?
C14 C15 H15 121(5) . . ?
C11 C10 C9 120.4(6) . . ?
C11 C10 H10 121(5) . . ?
C9 C10 H10 119(5) . . ?
C31 C32 C33 120.7(7) . . ?
C31 C32 H32 124(5) . . ?
C33 C32 H32 115(5) . . ?
C27 C26 C36 120.8(6) . . ?
C27 C26 C25 119.0(6) . . ?
C36 C26 C25 120.2(5) . . ?
C14 C13 C12 120.9(6) . . ?
C14 C13 H13 121(5) . . ?
C12 C13 H13 118(5) . . ?
O4 C35 N4 119.5(6) . . ?
O4 C35 C34 123.4(6) . . ?
N4 C35 C34 117.1(5) . . ?
N3 C23 C22 119.3(6) . . ?
N3 C23 H23 117(5) . . ?
C22 C23 H23 123(5) . . ?
C34 C33 C32 120.4(7) . . ?
C34 C33 H33 117(5) . . ?
C32 C33 H33 122(5) . . ?
O2 C17 N2 118.7(6) . . ?
O2 C17 C16 124.2(6) . . ?
N2 C17 C16 117.2(5) . . ?
C28 C29 C30 121.0(6) . . ?
C28 C29 H29 121(5) . . ?
C30 C29 H29 118(5) . . ?
C32 C31 C30 120.5(7) . . ?
C32 C31 H31 118(5) . . ?
C30 C31 H31 121(5) . . ?
N4 C24 C21 113.2(5) . . ?
N4 C24 H24B 107(4) . . ?
C21 C24 H24B 109(4) . . ?
N4 C24 H24A 107(4) . . ?
C21 C24 H24A 111(4) . . ?
H24B C24 H24A 110(6) . . ?

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
C1 N1 C5 C4 1.3(10) . . . . ?
C5 N1 C1 C2 -1.3(10) . . . . ?
N1 C5 C4 C3 -0.1(10) . . . . ?
C7 N2 C6 C3 94.7(7) . . . . ?
C17 N2 C6 C3 -86.2(7) . . . . ?
C23 N3 C19 C20 -0.4(10) . . . . ?
C21 C20 C19 N3 -0.8(10) . . . . ?
C16 C18 C8 C9 -178.3(5) . . . . ?
C12 C18 C8 C9 2.2(9) . . . . ?
C16 C18 C8 C7 3.4(8) . . . . ?
C12 C18 C8 C7 -176.1(5) . . . . ?
C16 C18 C12 C13 0.7(8) . . . . ?
C8 C18 C12 C13 -179.7(5) . . . . ?
C16 C18 C12 C11 179.1(5) . . . . ?
C8 C18 C12 C11 -1.3(8) . . . . ?
C5 C4 C3 C2 -1.2(10) . . . . ?
C5 C4 C3 C6 179.0(6) . . . . ?
N2 C6 C3 C4 100.4(7) . . . . ?
N2 C6 C3 C2 -79.5(7) . . . . ?
C17 N2 C7 O1 175.3(6) . . . . ?
C6 N2 C7 O1 -5.7(9) . . . . ?
C17 N2 C7 C8 -5.5(8) . . . . ?
C6 N2 C7 C8 173.4(5) . . . . ?
C9 C8 C7 O1 0.6(9) . . . . ?
C18 C8 C7 O1 178.9(6) . . . . ?
C9 C8 C7 N2 -178.5(5) . . . . ?
C18 C8 C7 N2 -0.2(8) . . . . ?
C13 C12 C11 C10 178.2(6) . . . . ?
C18 C12 C11 C10 -0.1(9) . . . . ?
C19 C20 C21 C22 1.6(10) . . . . ?
C19 C20 C21 C24 -176.9(6) . . . . ?
C18 C8 C9 C10 -1.6(9) . . . . ?
C7 C8 C9 C10 176.7(6) . . . . ?
C26 C27 C28 C29 0.3(10) . . . . ?
N1 C1 C2 C3 -0.1(9) . . . . ?
C4 C3 C2 C1 1.3(9) . . . . ?
C6 C3 C2 C1 -178.9(6) . . . . ?
C33 C34 C36 C26 -179.5(6) . . . . ?
C35 C34 C36 C26 -1.5(9) . . . . ?
C33 C34 C36 C30 -0.2(9) . . . . ?
C35 C34 C36 C30 177.7(5) . . . . ?
C29 C30 C36 C26 0.1(9) . . . . ?
C31 C30 C36 C26 179.6(6) . . . . ?
C29 C30 C36 C34 -179.2(6) . . . . ?
C31 C30 C36 C34 0.3(9) . . . . ?
C35 N4 C25 O3 178.3(6) . . . . ?
C24 N4 C25 O3 -5.4(8) . . . . ?
C35 N4 C25 C26 -2.9(8) . . . . ?
C24 N4 C25 C26 173.3(5) . . . . ?
C8 C18 C16 C15 179.6(6) . . . . ?
C12 C18 C16 C15 -0.9(8) . . . . ?
C8 C18 C16 C17 -1.3(8) . . . . ?
C12 C18 C16 C17 178.2(5) . . . . ?
C20 C21 C22 C23 -1.2(9) . . . . ?
C24 C21 C22 C23 177.2(6) . . . . ?
C18 C16 C15 C14 0.7(9) . . . . ?
C17 C16 C15 C14 -178.3(6) . . . . ?
C13 C14 C15 C16 -0.5(10) . . . . ?
C12 C11 C10 C9 0.7(10) . . . . ?
C8 C9 C10 C11 0.1(10) . . . . ?
C28 C27 C26 C36 -0.9(9) . . . . ?
C28 C27 C26 C25 177.1(6) . . . . ?
C34 C36 C26 C27 180.0(6) . . . . ?
C30 C36 C26 C27 0.7(9) . . . . ?
C34 C36 C26 C25 2.0(9) . . . . ?
C30 C36 C26 C25 -177.3(5) . . . . ?
O3 C25 C26 C27 0.8(9) . . . . ?
N4 C25 C26 C27 -177.9(5) . . . . ?
O3 C25 C26 C36 178.8(6) . . . . ?
N4 C25 C26 C36 0.1(8) . . . . ?
C15 C14 C13 C12 0.3(10) . . . . ?
C11 C12 C13 C14 -178.8(6) . . . . ?
C18 C12 C13 C14 -0.5(9) . . . . ?
C25 N4 C35 O4 -177.2(6) . . . . ?
C24 N4 C35 O4 6.6(8) . . . . ?
C25 N4 C35 C34 3.4(9) . . . . ?
C24 N4 C35 C34 -172.9(5) . . . . ?
C33 C34 C35 O4 -2.5(10) . . . . ?
C36 C34 C35 O4 179.5(6) . . . . ?
C33 C34 C35 N4 176.9(6) . . . . ?
C36 C34 C35 N4 -1.0(8) . . . . ?
C19 N3 C23 C22 0.8(10) . . . . ?
C21 C22 C23 N3 0.1(10) . . . . ?
C36 C34 C33 C32 -0.5(10) . . . . ?
C35 C34 C33 C32 -178.5(6) . . . . ?
C31 C32 C33 C34 1.3(10) . . . . ?
C7 N2 C17 O2 -173.4(6) . . . . ?
C6 N2 C17 O2 7.6(8) . . . . ?
C7 N2 C17 C16 7.6(8) . . . . ?
C6 N2 C17 C16 -171.4(5) . . . . ?
C15 C16 C17 O2 -3.8(9) . . . . ?
C18 C16 C17 O2 177.2(6) . . . . ?
C15 C16 C17 N2 175.2(5) . . . . ?
C18 C16 C17 N2 -3.9(8) . . . . ?
C27 C28 C29 C30 0.5(10) . . . . ?
C36 C30 C29 C28 -0.7(9) . . . . ?
C31 C30 C29 C28 179.8(6) . . . . ?
C33 C32 C31 C30 -1.2(11) . . . . ?
C29 C30 C31 C32 179.9(6) . . . . ?
C36 C30 C31 C32 0.4(10) . . . . ?
C25 N4 C24 C21 96.4(7) . . . . ?
C35 N4 C24 C21 -87.0(7) . . . . ?
C20 C21 C24 N4 -91.2(7) . . . . ?
C22 C21 C24 N4 90.4(7) . . . . ?

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
N1 H1N Cl2 0.87(8) 2.73(8) 3.352(6) 129(6) 2_765
N1 H1N Cl3 0.87(8) 2.48(8) 3.183(6) 137(7) 2_765
N3 H3N Cl1 0.88(9) 2.54(9) 3.216(6) 134(7) .
N3 H3N Cl1 0.88(9) 2.60(9) 3.259(6) 132(7) 2_765
C1 H1 Cl3 0.96(7) 2.77(6) 3.364(7) 121(5) 2_765
C19 H19 Cl1 0.89(7) 2.85(7) 3.391(7) 121(5) .
C2 H2 Cl2 0.92(7) 2.86(7) 3.530(7) 131(5) 2_665
C2 H2 O1 0.92(7) 2.59(7) 3.245(8) 128(5) .
C20 H20 Cl1 0.91(8) 2.87(8) 3.570(7) 134(6) 2_665
C5 H5 Cl2 0.89(8) 2.77(8) 3.414(7) 131(6) 2_765
C5 H5 O1 0.89(8) 2.44(8) 3.049(8) 126(6) 1_655
C22 H22 O4 0.88(9) 2.64(8) 3.112(8) 115(6) .
C23 H23 Cl1 0.96(9) 2.74(9) 3.355(7) 122(6) 2_765
C23 H23 O3 0.96(9) 2.52(9) 3.191(8) 127(7) 1_655

_refine_diff_density_max         5.769
_refine_diff_density_min         -7.498
_refine_diff_density_rms         0.179

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1824817'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H13 N2 O2), Cl4 Zn'
_chemical_formula_sum            'C36 H26 Cl4 N4 O4 Zn'
_chemical_formula_weight         785.80

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'
Zn Zn 0.2839 1.4301 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9049(10)
_cell_length_b                   14.7046(18)
_cell_length_c                   14.5448(19)
_cell_angle_alpha                102.479(6)
_cell_angle_beta                 100.932(6)
_cell_angle_gamma                92.276(6)
_cell_volume                     1615.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9778
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.59

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.086
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6528
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50547
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             6334
_reflns_number_gt                5168
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+15.2687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6334
_refine_ls_number_parameters     442
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1704
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.79702(17) 0.55763(9) -0.03447(10) 0.0187(3) Uani 1 1 d . U . . .
Cl2 Cl 0.73472(19) 0.81025(10) -0.01090(11) 0.0240(3) Uani 1 1 d . U . . .
Cl3 Cl 1.14932(19) 0.74438(12) 0.09281(11) 0.0277(4) Uani 1 1 d . U . . .
Cl4 Cl 0.7732(3) 0.69728(14) 0.20449(13) 0.0449(5) Uani 1 1 d . U . . .
Zn1 Zn 0.85899(9) 0.70332(5) 0.06876(5) 0.01944(19) Uani 1 1 d . U . . .
O1 O 0.3260(5) 0.0348(3) 0.2142(3) 0.0244(9) Uani 1 1 d . U . . .
O3 O 0.3065(5) 0.3364(3) 0.2889(3) 0.0255(9) Uani 1 1 d . U . . .
O2 O 0.8703(5) 0.0083(3) 0.3665(3) 0.0217(9) Uani 1 1 d . U . . .
O4 O 0.8500(5) 0.2847(3) 0.4210(3) 0.0279(10) Uani 1 1 d . U . . .
N2 N 0.5943(6) 0.0165(3) 0.2933(3) 0.0150(9) Uani 1 1 d . U . . .
N4 N 0.5749(6) 0.3074(3) 0.3569(3) 0.0148(9) Uani 1 1 d . U . . .
N1 N 0.8749(6) 0.1219(3) 0.0499(3) 0.0203(10) Uani 1 1 d . U . . .
H1N H 0.9229 0.1540 0.0176 0.024 Uiso 1 1 calc . U . . .
N3 N 0.8446(6) 0.4223(3) 0.1121(3) 0.0200(10) Uani 1 1 d . U . . .
H3N H 0.8935 0.4551 0.0806 0.024 Uiso 1 1 calc . U . . .
C5 C 0.9744(8) 0.0736(4) 0.1043(4) 0.0228(12) Uani 1 1 d . U . . .
H5 H 1.0932 0.0759 0.1077 0.027 Uiso 1 1 calc R U . . .
C1 C 0.7044(8) 0.1220(4) 0.0440(4) 0.0189(11) Uani 1 1 d . U . . .
H1 H 0.6400 0.1567 0.0057 0.023 Uiso 1 1 calc R U . . .
C20 C 0.5907(7) 0.3627(4) 0.1486(4) 0.0208(12) Uani 1 1 d . U . . .
H20 H 0.4708 0.3576 0.1399 0.025 Uiso 1 1 calc R U . . .
C18 C 0.5177(7) 0.1079(4) 0.4690(4) 0.0133(10) Uani 1 1 d . U . . .
C4 C 0.8981(7) 0.0202(4) 0.1554(4) 0.0197(12) Uani 1 1 d . U . . .
H4 H 0.9655 -0.0140 0.1930 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6322(7) -0.0407(4) 0.2039(4) 0.0195(11) Uani 1 1 d . U . . .
H6A H 0.5250 -0.0714 0.1626 0.023 Uiso 1 1 calc R U . . .
H6B H 0.7057 -0.0888 0.2196 0.023 Uiso 1 1 calc R U . . .
C19 C 0.6728(7) 0.4155(4) 0.0989(4) 0.0205(12) Uani 1 1 d . U . . .
H19 H 0.6079 0.4460 0.0564 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3925(7) 0.0977(4) 0.3833(4) 0.0146(10) Uani 1 1 d . U . . .
C12 C 0.4761(7) 0.1514(4) 0.5586(4) 0.0179(11) Uani 1 1 d . U . . .
C3 C 0.7209(7) 0.0178(4) 0.1504(4) 0.0161(11) Uani 1 1 d . U . . .
C7 C 0.4288(7) 0.0479(4) 0.2909(4) 0.0157(11) Uani 1 1 d . U . . .
C11 C 0.3097(8) 0.1814(4) 0.5590(5) 0.0228(12) Uani 1 1 d . U . . .
H11 H 0.2801 0.2081 0.6172 0.027 Uiso 1 1 calc R U . . .
C21 C 0.6905(7) 0.3179(4) 0.2113(4) 0.0173(11) Uani 1 1 d . U . . .
C27 C 0.2270(7) 0.4137(4) 0.4693(4) 0.0193(12) Uani 1 1 d . U . . .
H27 H 0.1415 0.4123 0.4153 0.023 Uiso 1 1 calc R U . . .
C9 C 0.2313(7) 0.1293(4) 0.3866(5) 0.0212(12) Uani 1 1 d . U . . .
H9 H 0.1494 0.1224 0.3299 0.025 Uiso 1 1 calc R U . . .
C34 C 0.6808(7) 0.3525(4) 0.5316(4) 0.0185(11) Uani 1 1 d . U . . .
C14 C 0.7656(8) 0.1327(4) 0.6398(4) 0.0229(12) Uani 1 1 d . U . . .
H14 H 0.8485 0.1411 0.6962 0.027 Uiso 1 1 calc R U . . .
C28 C 0.1951(8) 0.4477(4) 0.5618(5) 0.0243(13) Uani 1 1 d . U . . .
H28 H 0.0884 0.4697 0.5686 0.029 Uiso 1 1 calc R U . . .
C30 C 0.4832(8) 0.4195(4) 0.6338(4) 0.0209(12) Uani 1 1 d . U . . .
C2 C 0.6237(7) 0.0707(4) 0.0945(4) 0.0195(12) Uani 1 1 d . U . . .
H2 H 0.5051 0.0714 0.0913 0.023 Uiso 1 1 calc R U . . .
C36 C 0.5170(7) 0.3847(4) 0.5405(4) 0.0158(11) Uani 1 1 d . U . . .
C25 C 0.4142(7) 0.3413(4) 0.3616(4) 0.0150(11) Uani 1 1 d . U . . .
C16 C 0.6845(7) 0.0787(4) 0.4670(4) 0.0138(10) Uani 1 1 d . U . . .
C22 C 0.8693(7) 0.3267(4) 0.2232(4) 0.0188(11) Uani 1 1 d . U . . .
H22 H 0.9374 0.2969 0.2652 0.023 Uiso 1 1 calc R U . . .
C15 C 0.8077(7) 0.0903(4) 0.5514(4) 0.0188(11) Uani 1 1 d . U . . .
H15 H 0.9173 0.0702 0.5495 0.023 Uiso 1 1 calc R U . . .
C10 C 0.1898(7) 0.1719(4) 0.4750(5) 0.0220(12) Uani 1 1 d . U . . .
H10 H 0.0813 0.1936 0.4766 0.026 Uiso 1 1 calc R U . . .
C32 C 0.7735(8) 0.3894(4) 0.7041(4) 0.0281(14) Uani 1 1 d . U . . .
H32 H 0.8596 0.3921 0.7582 0.034 Uiso 1 1 calc R U . . .
C26 C 0.3854(7) 0.3826(4) 0.4592(4) 0.0154(11) Uani 1 1 d . U . . .
C13 C 0.6052(8) 0.1615(4) 0.6435(4) 0.0200(12) Uani 1 1 d . U . . .
H13 H 0.5795 0.1883 0.7028 0.024 Uiso 1 1 calc R U . . .
C35 C 0.7124(7) 0.3127(4) 0.4347(4) 0.0184(11) Uani 1 1 d . U . . .
C23 C 0.9447(8) 0.3795(5) 0.1730(4) 0.0239(13) Uani 1 1 d . U . . .
H23 H 1.0644 0.3860 0.1807 0.029 Uiso 1 1 calc R U . . .
C33 C 0.8061(8) 0.3542(4) 0.6116(4) 0.0239(12) Uani 1 1 d . U . . .
H33 H 0.9127 0.3321 0.6047 0.029 Uiso 1 1 calc R U . . .
C17 C 0.7277(7) 0.0320(4) 0.3749(4) 0.0143(10) Uani 1 1 d . U . . .
C29 C 0.3174(8) 0.4490(4) 0.6414(5) 0.0258(13) Uani 1 1 d . U . . .
H29 H 0.2917 0.4696 0.7019 0.031 Uiso 1 1 calc R U . . .
C31 C 0.6159(9) 0.4195(4) 0.7144(4) 0.0267(13) Uani 1 1 d . U . . .
H31 H 0.5949 0.4407 0.7760 0.032 Uiso 1 1 calc R U . . .
C24 C 0.6018(8) 0.2564(4) 0.2627(4) 0.0197(12) Uani 1 1 d . U . . .
H24A H 0.4908 0.2302 0.2226 0.024 Uiso 1 1 calc R U . . .
H24B H 0.6715 0.2050 0.2716 0.024 Uiso 1 1 calc R U . . .


_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 Zn1 2.3090(16) . ?
Cl2 Zn1 2.2931(16) . ?
Cl3 Zn1 2.2909(16) . ?
Cl4 Zn1 2.2233(17) . ?
O1 C7 1.222(7) . ?
O3 C25 1.213(7) . ?
O2 C17 1.214(6) . ?
O4 C35 1.215(7) . ?
N2 C17 1.401(7) . ?
N2 C7 1.401(7) . ?
N2 C6 1.478(7) . ?
N4 C25 1.391(7) . ?
N4 C35 1.399(7) . ?
N4 C24 1.471(7) . ?
N1 C1 1.334(7) . ?
N1 C5 1.341(8) . ?
N1 H1N 0.8600 . ?
N3 C19 1.331(7) . ?
N3 C23 1.349(8) . ?
N3 H3N 0.8600 . ?
C5 C4 1.385(8) . ?
C5 H5 0.9300 . ?
C1 C2 1.376(8) . ?
C1 H1 0.9300 . ?
C20 C21 1.384(8) . ?
C20 C19 1.387(8) . ?
C20 H20 0.9300 . ?
C18 C16 1.407(7) . ?
C18 C8 1.412(8) . ?
C18 C12 1.426(7) . ?
C4 C3 1.387(8) . ?
C4 H4 0.9300 . ?
C6 C3 1.512(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C19 H19 0.9300 . ?
C8 C9 1.379(8) . ?
C8 C7 1.471(8) . ?
C12 C11 1.405(8) . ?
C12 C13 1.421(8) . ?
C3 C2 1.394(8) . ?
C11 C10 1.373(9) . ?
C11 H11 0.9300 . ?
C21 C22 1.389(8) . ?
C21 C24 1.519(7) . ?
C27 C26 1.373(8) . ?
C27 C28 1.404(8) . ?
C27 H27 0.9300 . ?
C9 C10 1.408(8) . ?
C9 H9 0.9300 . ?
C34 C33 1.372(8) . ?
C34 C36 1.415(8) . ?
C34 C35 1.477(8) . ?
C14 C13 1.360(9) . ?
C14 C15 1.409(8) . ?
C14 H14 0.9300 . ?
C28 C29 1.357(9) . ?
C28 H28 0.9300 . ?
C30 C29 1.413(9) . ?
C30 C31 1.417(9) . ?
C30 C36 1.422(8) . ?
C2 H2 0.9300 . ?
C36 C26 1.414(8) . ?
C25 C26 1.482(7) . ?
C16 C15 1.387(8) . ?
C16 C17 1.476(7) . ?
C22 C23 1.366(8) . ?
C22 H22 0.9300 . ?
C15 H15 0.9300 . ?
C10 H10 0.9300 . ?
C32 C31 1.362(9) . ?
C32 C33 1.410(9) . ?
C32 H32 0.9300 . ?
C13 H13 0.9300 . ?
C23 H23 0.9300 . ?
C33 H33 0.9300 . ?
C29 H29 0.9300 . ?
C31 H31 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

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
Cl4 Zn1 Cl3 112.63(7) . . ?
Cl4 Zn1 Cl2 115.52(7) . . ?
Cl3 Zn1 Cl2 103.52(6) . . ?
Cl4 Zn1 Cl1 108.46(7) . . ?
Cl3 Zn1 Cl1 108.65(6) . . ?
Cl2 Zn1 Cl1 107.75(6) . . ?
C17 N2 C7 125.4(5) . . ?
C17 N2 C6 116.2(4) . . ?
C7 N2 C6 118.3(4) . . ?
C25 N4 C35 126.1(5) . . ?
C25 N4 C24 117.8(5) . . ?
C35 N4 C24 116.0(4) . . ?
C1 N1 C5 122.7(5) . . ?
C1 N1 H1N 118.7 . . ?
C5 N1 H1N 118.7 . . ?
C19 N3 C23 122.4(5) . . ?
C19 N3 H3N 118.8 . . ?
C23 N3 H3N 118.8 . . ?
N1 C5 C4 119.2(5) . . ?
N1 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C1 C2 120.0(5) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C21 C20 C19 118.8(5) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C16 C18 C8 121.0(5) . . ?
C16 C18 C12 119.5(5) . . ?
C8 C18 C12 119.5(5) . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N2 C6 C3 111.7(5) . . ?
N2 C6 H6A 109.3 . . ?
C3 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C3 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N3 C19 C20 119.9(5) . . ?
N3 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C9 C8 C18 120.1(5) . . ?
C9 C8 C7 119.4(5) . . ?
C18 C8 C7 120.3(5) . . ?
C11 C12 C13 123.1(5) . . ?
C11 C12 C18 118.7(5) . . ?
C13 C12 C18 118.2(5) . . ?
C4 C3 C2 118.8(5) . . ?
C4 C3 C6 121.5(5) . . ?
C2 C3 C6 119.7(5) . . ?
O1 C7 N2 119.6(5) . . ?
O1 C7 C8 124.1(5) . . ?
N2 C7 C8 116.3(5) . . ?
C10 C11 C12 121.2(5) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C20 C21 C22 119.6(5) . . ?
C20 C21 C24 119.3(5) . . ?
C22 C21 C24 121.1(5) . . ?
C26 C27 C28 119.5(6) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C8 C9 C10 120.5(6) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C33 C34 C36 120.9(5) . . ?
C33 C34 C35 120.2(5) . . ?
C36 C34 C35 118.9(5) . . ?
C13 C14 C15 120.8(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C29 C28 C27 121.1(6) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C29 C30 C31 123.5(6) . . ?
C29 C30 C36 118.4(5) . . ?
C31 C30 C36 118.1(6) . . ?
C1 C2 C3 119.5(5) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C34 C36 C26 121.8(5) . . ?
C34 C36 C30 119.2(5) . . ?
C26 C36 C30 119.0(5) . . ?
O3 C25 N4 120.6(5) . . ?
O3 C25 C26 123.3(5) . . ?
N4 C25 C26 116.1(5) . . ?
C15 C16 C18 120.7(5) . . ?
C15 C16 C17 119.4(5) . . ?
C18 C16 C17 119.9(5) . . ?
C23 C22 C21 119.6(5) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C31 C32 C33 120.1(6) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C27 C26 C36 120.9(5) . . ?
C27 C26 C25 119.1(5) . . ?
C36 C26 C25 119.8(5) . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
O4 C35 N4 120.0(5) . . ?
O4 C35 C34 122.9(5) . . ?
N4 C35 C34 117.1(5) . . ?
N3 C23 C22 119.6(5) . . ?
N3 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C34 C33 C32 120.1(6) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
O2 C17 N2 119.4(5) . . ?
O2 C17 C16 123.9(5) . . ?
N2 C17 C16 116.7(4) . . ?
C28 C29 C30 121.0(6) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C32 C31 C30 121.7(6) . . ?
C32 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
N4 C24 C21 112.9(5) . . ?
N4 C24 H24A 109.0 . . ?
C21 C24 H24A 109.0 . . ?
N4 C24 H24B 109.0 . . ?
C21 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?

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
C1 N1 C5 C4 1.1(8) . . . . ?
C5 N1 C1 C2 -0.4(8) . . . . ?
N1 C5 C4 C3 -0.5(9) . . . . ?
C17 N2 C6 C3 -85.7(6) . . . . ?
C7 N2 C6 C3 96.4(6) . . . . ?
C23 N3 C19 C20 -0.2(9) . . . . ?
C21 C20 C19 N3 -0.1(9) . . . . ?
C16 C18 C8 C9 -178.1(5) . . . . ?
C12 C18 C8 C9 -0.2(8) . . . . ?
C16 C18 C8 C7 5.9(8) . . . . ?
C12 C18 C8 C7 -176.2(5) . . . . ?
C16 C18 C12 C11 179.1(5) . . . . ?
C8 C18 C12 C11 1.2(8) . . . . ?
C16 C18 C12 C13 -1.5(8) . . . . ?
C8 C18 C12 C13 -179.4(5) . . . . ?
C5 C4 C3 C2 -0.8(8) . . . . ?
C5 C4 C3 C6 179.1(5) . . . . ?
N2 C6 C3 C4 101.0(6) . . . . ?
N2 C6 C3 C2 -79.2(6) . . . . ?
C17 N2 C7 O1 175.8(5) . . . . ?
C6 N2 C7 O1 -6.6(8) . . . . ?
C17 N2 C7 C8 -2.7(7) . . . . ?
C6 N2 C7 C8 175.0(5) . . . . ?
C9 C8 C7 O1 2.6(8) . . . . ?
C18 C8 C7 O1 178.6(5) . . . . ?
C9 C8 C7 N2 -179.0(5) . . . . ?
C18 C8 C7 N2 -3.0(7) . . . . ?
C13 C12 C11 C10 178.7(5) . . . . ?
C18 C12 C11 C10 -1.9(8) . . . . ?
C19 C20 C21 C22 0.1(8) . . . . ?
C19 C20 C21 C24 -177.3(5) . . . . ?
C18 C8 C9 C10 -0.1(8) . . . . ?
C7 C8 C9 C10 176.0(5) . . . . ?
C26 C27 C28 C29 -1.0(9) . . . . ?
N1 C1 C2 C3 -1.0(8) . . . . ?
C4 C3 C2 C1 1.5(8) . . . . ?
C6 C3 C2 C1 -178.3(5) . . . . ?
C33 C34 C36 C26 -179.3(5) . . . . ?
C35 C34 C36 C26 -2.2(8) . . . . ?
C33 C34 C36 C30 0.3(8) . . . . ?
C35 C34 C36 C30 177.4(5) . . . . ?
C29 C30 C36 C34 -178.4(5) . . . . ?
C31 C30 C36 C34 -0.6(8) . . . . ?
C29 C30 C36 C26 1.2(8) . . . . ?
C31 C30 C36 C26 179.0(5) . . . . ?
C35 N4 C25 O3 176.8(5) . . . . ?
C24 N4 C25 O3 -6.8(8) . . . . ?
C35 N4 C25 C26 -3.1(8) . . . . ?
C24 N4 C25 C26 173.3(4) . . . . ?
C8 C18 C16 C15 179.0(5) . . . . ?
C12 C18 C16 C15 1.1(8) . . . . ?
C8 C18 C16 C17 -3.3(8) . . . . ?
C12 C18 C16 C17 178.8(5) . . . . ?
C20 C21 C22 C23 0.0(9) . . . . ?
C24 C21 C22 C23 177.4(5) . . . . ?
C18 C16 C15 C14 -0.6(8) . . . . ?
C17 C16 C15 C14 -178.4(5) . . . . ?
C13 C14 C15 C16 0.7(9) . . . . ?
C12 C11 C10 C9 1.7(9) . . . . ?
C8 C9 C10 C11 -0.7(9) . . . . ?
C28 C27 C26 C36 -0.3(8) . . . . ?
C28 C27 C26 C25 176.1(5) . . . . ?
C34 C36 C26 C27 179.7(5) . . . . ?
C30 C36 C26 C27 0.1(8) . . . . ?
C34 C36 C26 C25 3.3(8) . . . . ?
C30 C36 C26 C25 -176.3(5) . . . . ?
O3 C25 C26 C27 2.8(8) . . . . ?
N4 C25 C26 C27 -177.3(5) . . . . ?
O3 C25 C26 C36 179.3(5) . . . . ?
N4 C25 C26 C36 -0.8(7) . . . . ?
C15 C14 C13 C12 -1.2(9) . . . . ?
C11 C12 C13 C14 -179.1(5) . . . . ?
C18 C12 C13 C14 1.6(8) . . . . ?
C25 N4 C35 O4 -176.3(5) . . . . ?
C24 N4 C35 O4 7.3(7) . . . . ?
C25 N4 C35 C34 4.2(8) . . . . ?
C24 N4 C35 C34 -172.2(5) . . . . ?
C33 C34 C35 O4 -3.8(9) . . . . ?
C36 C34 C35 O4 179.1(5) . . . . ?
C33 C34 C35 N4 175.7(5) . . . . ?
C36 C34 C35 N4 -1.4(7) . . . . ?
C19 N3 C23 C22 0.3(9) . . . . ?
C21 C22 C23 N3 -0.2(9) . . . . ?
C36 C34 C33 C32 -0.9(9) . . . . ?
C35 C34 C33 C32 -177.9(5) . . . . ?
C31 C32 C33 C34 1.7(9) . . . . ?
C7 N2 C17 O2 -173.7(5) . . . . ?
C6 N2 C17 O2 8.6(7) . . . . ?
C7 N2 C17 C16 5.2(8) . . . . ?
C6 N2 C17 C16 -172.5(5) . . . . ?
C15 C16 C17 O2 -5.5(8) . . . . ?
C18 C16 C17 O2 176.7(5) . . . . ?
C15 C16 C17 N2 175.7(5) . . . . ?
C18 C16 C17 N2 -2.1(7) . . . . ?
C27 C28 C29 C30 2.4(9) . . . . ?
C31 C30 C29 C28 179.8(6) . . . . ?
C36 C30 C29 C28 -2.5(9) . . . . ?
C33 C32 C31 C30 -2.1(9) . . . . ?
C29 C30 C31 C32 179.2(6) . . . . ?
C36 C30 C31 C32 1.5(9) . . . . ?
C25 N4 C24 C21 96.6(6) . . . . ?
C35 N4 C24 C21 -86.6(6) . . . . ?
C20 C21 C24 N4 -91.8(6) . . . . ?
C22 C21 C24 N4 90.9(6) . . . . ?

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
N1 H1N Cl2 0.86 2.76 3.392(5) 131.6 2_765
N1 H1N Cl3 0.86 2.43 3.140(5) 140.7 2_765
N3 H3N Cl1 0.86 2.52 3.199(5) 136.4 .
N3 H3N Cl1 0.86 2.66 3.268(5) 128.7 2_765
C5 H5 Cl2 0.93 2.86 3.454(6) 122.6 2_765
C5 H5 O1 0.93 2.36 3.073(7) 133.3 1_655
C1 H1 Cl3 0.93 2.93 3.397(6) 112.9 2_765
C20 H20 Cl1 0.93 2.86 3.566(6) 133.4 2_665
C20 H20 Cl2 0.93 2.96 3.525(6) 120.3 2_665
C19 H19 Cl1 0.93 2.86 3.378(6) 116.5 .
C2 H2 Cl2 0.93 2.88 3.546(6) 129.6 2_665
C2 H2 O1 0.93 2.61 3.271(7) 128.7 .
C22 H22 O4 0.93 2.53 3.099(7) 119.8 .
C23 H23 Cl1 0.93 2.83 3.361(6) 117.7 2_765
C23 H23 O3 0.93 2.48 3.194(7) 134.0 1_655

_refine_diff_density_max         2.114
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.132

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1824816'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H13 N2 O2), Br4 Co'
_chemical_formula_sum            'C36 H26 Br4 Co N4 O4'
_chemical_formula_weight         957.14

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.933(2)
_cell_length_b                   14.728(4)
_cell_length_c                   14.966(5)
_cell_angle_alpha                102.650(10)
_cell_angle_beta                 100.863(9)
_cell_angle_gamma                93.145(9)
_cell_volume                     1667.0(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8989
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.67

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.907
_exptl_crystal_F_000             938
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    5.356
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49749
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.238
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6816
_reflns_number_gt                4802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0752P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6816
_refine_ls_number_parameters     450
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.78538(6) 0.54881(3) -0.04180(4) 0.02614(15) Uani 1 1 d . U . . .
Br2 Br 0.73258(6) 0.81416(3) -0.01762(4) 0.03014(16) Uani 1 1 d . U . . .
Br3 Br 1.16936(7) 0.74952(4) 0.09334(4) 0.03540(17) Uani 1 1 d . U . . .
Br4 Br 0.77289(9) 0.69421(5) 0.20477(5) 0.0478(2) Uani 1 1 d . U . . .
Co1 Co 0.86424(8) 0.70214(5) 0.06421(5) 0.02481(19) Uani 1 1 d . U . . .
O1 O 0.3283(4) 0.0359(2) 0.2227(3) 0.0309(9) Uani 1 1 d . U . . .
O3 O 0.3116(4) 0.3318(2) 0.2893(3) 0.0337(9) Uani 1 1 d . U . . .
O2 O 0.8666(4) 0.0059(2) 0.3720(2) 0.0271(8) Uani 1 1 d . U . . .
O4 O 0.8514(4) 0.2835(3) 0.4188(3) 0.0367(9) Uani 1 1 d . U . . .
N2 N 0.5920(5) 0.0154(3) 0.3002(3) 0.0202(9) Uani 1 1 d . U . . .
N4 N 0.5793(5) 0.3048(3) 0.3560(3) 0.0201(9) Uani 1 1 d . U . . .
N1 N 0.8776(5) 0.1124(3) 0.0608(3) 0.0293(10) Uani 1 1 d . U . . .
N3 N 0.8521(5) 0.4210(3) 0.1222(3) 0.0304(11) Uani 1 1 d . U . . .
C5 C 0.9739(7) 0.0662(4) 0.1165(4) 0.0316(13) Uani 1 1 d . U . . .
H5 H 1.0927 0.0686 0.1209 0.038 Uiso 1 1 calc R U . . .
C1 C 0.7060(6) 0.1128(4) 0.0530(4) 0.0308(13) Uani 1 1 d . U . . .
H1 H 0.6431 0.1459 0.0143 0.037 Uiso 1 1 calc R U . . .
C20 C 0.5995(7) 0.3646(4) 0.1585(4) 0.0316(13) Uani 1 1 d . U . . .
H20 H 0.4803 0.3619 0.1520 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5184(6) 0.1093(3) 0.4712(4) 0.0199(10) Uani 1 1 d . U . . .
C4 C 0.8955(6) 0.0154(3) 0.1668(4) 0.0275(12) Uani 1 1 d . U . . .
H4 H 0.9607 -0.0174 0.2049 0.033 Uiso 1 1 calc R U . . .
C6 C 0.6284(6) -0.0442(3) 0.2130(4) 0.0275(12) Uani 1 1 d . U . . .
H6A H 0.5209 -0.0754 0.1730 0.033 Uiso 1 1 calc R U . . .
H6B H 0.7003 -0.0918 0.2289 0.033 Uiso 1 1 calc R U . . .
C19 C 0.6801(7) 0.4168(4) 0.1109(4) 0.0346(13) Uani 1 1 d . U . . .
H19 H 0.6166 0.4488 0.0712 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3942(6) 0.0972(3) 0.3868(4) 0.0206(10) Uani 1 1 d . U . . .
C12 C 0.4778(6) 0.1516(3) 0.5579(4) 0.0231(11) Uani 1 1 d . U . . .
C3 C 0.7185(6) 0.0132(3) 0.1605(4) 0.0235(11) Uani 1 1 d . U . . .
C7 C 0.4308(6) 0.0487(3) 0.2978(4) 0.0220(11) Uani 1 1 d . U . . .
C11 C 0.3127(6) 0.1822(3) 0.5576(4) 0.0284(12) Uani 1 1 d . U . . .
H11 H 0.2834 0.2101 0.6139 0.034 Uiso 1 1 calc R U . . .
C21 C 0.6949(7) 0.3152(3) 0.2170(4) 0.0289(12) Uani 1 1 d . U . . .
C27 C 0.2321(6) 0.4112(3) 0.4644(4) 0.0239(11) Uani 1 1 d . U . . .
H27 H 0.1468 0.4086 0.4117 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2334(6) 0.1298(3) 0.3906(4) 0.0265(12) Uani 1 1 d . U . . .
H9 H 0.1516 0.1234 0.3357 0.032 Uiso 1 1 calc R U . . .
C34 C 0.6839(6) 0.3511(3) 0.5259(4) 0.0226(11) Uani 1 1 d . U . . .
C14 C 0.7650(6) 0.1326(3) 0.6369(4) 0.0277(12) Uani 1 1 d . U . . .
H14 H 0.8473 0.1400 0.6919 0.033 Uiso 1 1 calc R U . . .
C28 C 0.2010(7) 0.4467(3) 0.5534(4) 0.0302(12) Uani 1 1 d . U . . .
H28 H 0.0953 0.4688 0.5595 0.036 Uiso 1 1 calc R U . . .
C30 C 0.4877(7) 0.4185(3) 0.6244(4) 0.0265(11) Uani 1 1 d . U . . .
C2 C 0.6256(6) 0.0632(3) 0.1034(4) 0.0286(12) Uani 1 1 d . U . . .
H2 H 0.5072 0.0632 0.0992 0.034 Uiso 1 1 calc R U . . .
C36 C 0.5208(6) 0.3831(3) 0.5348(4) 0.0224(10) Uani 1 1 d . U . . .
C25 C 0.4181(6) 0.3389(3) 0.3614(4) 0.0227(11) Uani 1 1 d . U . . .
C16 C 0.6844(6) 0.0787(3) 0.4692(4) 0.0201(10) Uani 1 1 d . U . . .
C22 C 0.8772(7) 0.3215(4) 0.2261(4) 0.0341(13) Uani 1 1 d . U . . .
H22 H 0.9453 0.2897 0.2642 0.041 Uiso 1 1 calc R U . . .
C15 C 0.8047(6) 0.0906(3) 0.5513(4) 0.0244(11) Uani 1 1 d . U . . .
H15 H 0.9134 0.0705 0.5497 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1946(6) 0.1715(3) 0.4754(4) 0.0296(12) Uani 1 1 d . U . . .
H10 H 0.0866 0.1927 0.4767 0.036 Uiso 1 1 calc R U . . .
C32 C 0.7742(7) 0.3897(4) 0.6937(4) 0.0331(13) Uani 1 1 d . U . . .
H32 H 0.8593 0.3918 0.7464 0.040 Uiso 1 1 calc R U . . .
C26 C 0.3907(6) 0.3798(3) 0.4547(4) 0.0206(10) Uani 1 1 d . U . . .
C13 C 0.6051(7) 0.1629(3) 0.6405(4) 0.0279(12) Uani 1 1 d . U . . .
H13 H 0.5804 0.1912 0.6979 0.034 Uiso 1 1 calc R U . . .
C35 C 0.7145(6) 0.3122(3) 0.4335(4) 0.0244(11) Uani 1 1 d . U . . .
C23 C 0.9486(7) 0.3757(4) 0.1772(4) 0.0365(14) Uani 1 1 d . U . . .
H23 H 1.0676 0.3811 0.1825 0.044 Uiso 1 1 calc R U . . .
C33 C 0.8064(7) 0.3546(3) 0.6046(4) 0.0328(13) Uani 1 1 d . U . . .
H33 H 0.9129 0.3333 0.5987 0.039 Uiso 1 1 calc R U . . .
C17 C 0.7268(6) 0.0324(3) 0.3806(4) 0.0211(10) Uani 1 1 d . U . . .
C29 C 0.3245(7) 0.4495(3) 0.6323(4) 0.0326(13) Uani 1 1 d . U . . .
H29 H 0.3003 0.4719 0.6911 0.039 Uiso 1 1 calc R U . . .
C31 C 0.6177(8) 0.4211(4) 0.7037(4) 0.0387(13) Uani 1 1 d . U . . .
H31 H 0.5971 0.4442 0.7633 0.046 Uiso 1 1 calc R U . . .
C24 C 0.6050(7) 0.2542(3) 0.2665(4) 0.0313(12) Uani 1 1 d . U . . .
H24A H 0.4939 0.2276 0.2272 0.038 Uiso 1 1 calc R U . . .
H24B H 0.6731 0.2029 0.2754 0.038 Uiso 1 1 calc R U . . .
H3N H 0.909(8) 0.453(4) 0.077(4) 0.056(18) Uiso 1 1 d . . . . .
H1N H 0.934(8) 0.142(4) 0.023(4) 0.06(2) 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
Br1 Co1 2.4309(10) . ?
Br2 Co1 2.4299(10) . ?
Br3 Co1 2.4122(11) . ?
Br4 Co1 2.3742(11) . ?
O1 C7 1.226(6) . ?
O3 C25 1.219(6) . ?
O2 C17 1.216(5) . ?
O4 C35 1.227(6) . ?
N2 C7 1.391(6) . ?
N2 C17 1.417(6) . ?
N2 C6 1.492(7) . ?
N4 C35 1.403(6) . ?
N4 C25 1.409(6) . ?
N4 C24 1.440(7) . ?
N1 C5 1.344(7) . ?
N1 C1 1.345(6) . ?
N3 C23 1.330(7) . ?
N3 C19 1.339(7) . ?
C5 C4 1.373(7) . ?
C1 C2 1.371(7) . ?
C20 C19 1.365(7) . ?
C20 C21 1.400(7) . ?
C18 C12 1.414(7) . ?
C18 C8 1.418(7) . ?
C18 C16 1.419(6) . ?
C4 C3 1.387(7) . ?
C6 C3 1.509(7) . ?
C8 C9 1.394(7) . ?
C8 C7 1.457(7) . ?
C12 C11 1.408(7) . ?
C12 C13 1.412(7) . ?
C3 C2 1.382(7) . ?
C11 C10 1.372(8) . ?
C21 C22 1.422(7) . ?
C21 C24 1.512(7) . ?
C27 C26 1.386(7) . ?
C27 C28 1.393(7) . ?
C9 C10 1.381(8) . ?
C34 C33 1.368(7) . ?
C34 C36 1.421(7) . ?
C34 C35 1.447(7) . ?
C14 C13 1.375(7) . ?
C14 C15 1.396(7) . ?
C28 C29 1.376(7) . ?
C30 C36 1.407(7) . ?
C30 C31 1.410(7) . ?
C30 C29 1.413(7) . ?
C36 C26 1.417(7) . ?
C25 C26 1.455(7) . ?
C16 C15 1.377(7) . ?
C16 C17 1.461(7) . ?
C22 C23 1.363(7) . ?
C32 C31 1.372(8) . ?
C32 C33 1.397(8) . ?

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
Br4 Co1 Br3 111.35(4) . . ?
Br4 Co1 Br2 115.65(4) . . ?
Br3 Co1 Br2 103.97(3) . . ?
Br4 Co1 Br1 106.96(4) . . ?
Br3 Co1 Br1 112.29(3) . . ?
Br2 Co1 Br1 106.64(4) . . ?
C7 N2 C17 124.9(4) . . ?
C7 N2 C6 118.8(4) . . ?
C17 N2 C6 116.2(4) . . ?
C35 N4 C25 124.1(4) . . ?
C35 N4 C24 117.3(4) . . ?
C25 N4 C24 118.5(4) . . ?
C5 N1 C1 122.9(5) . . ?
C23 N3 C19 122.9(5) . . ?
N1 C5 C4 119.4(5) . . ?
N1 C1 C2 118.5(5) . . ?
C19 C20 C21 120.5(5) . . ?
C12 C18 C8 120.4(4) . . ?
C12 C18 C16 119.5(5) . . ?
C8 C18 C16 120.1(5) . . ?
C5 C4 C3 119.8(5) . . ?
N2 C6 C3 111.4(4) . . ?
N3 C19 C20 118.9(5) . . ?
C9 C8 C18 118.8(5) . . ?
C9 C8 C7 120.2(5) . . ?
C18 C8 C7 120.9(4) . . ?
C11 C12 C13 122.9(5) . . ?
C11 C12 C18 118.2(5) . . ?
C13 C12 C18 118.8(5) . . ?
C2 C3 C4 118.6(5) . . ?
C2 C3 C6 120.6(4) . . ?
C4 C3 C6 120.8(4) . . ?
O1 C7 N2 119.5(5) . . ?
O1 C7 C8 123.8(4) . . ?
N2 C7 C8 116.8(4) . . ?
C10 C11 C12 120.9(5) . . ?
C20 C21 C22 118.4(5) . . ?
C20 C21 C24 120.5(5) . . ?
C22 C21 C24 121.1(5) . . ?
C26 C27 C28 119.8(5) . . ?
C10 C9 C8 120.6(5) . . ?
C33 C34 C36 119.5(5) . . ?
C33 C34 C35 121.4(5) . . ?
C36 C34 C35 119.1(4) . . ?
C13 C14 C15 120.4(5) . . ?
C29 C28 C27 121.0(5) . . ?
C36 C30 C31 119.1(5) . . ?
C36 C30 C29 119.0(5) . . ?
C31 C30 C29 121.9(5) . . ?
C1 C2 C3 120.9(5) . . ?
C30 C36 C26 119.5(5) . . ?
C30 C36 C34 119.6(5) . . ?
C26 C36 C34 120.9(5) . . ?
O3 C25 N4 118.8(5) . . ?
O3 C25 C26 124.6(4) . . ?
N4 C25 C26 116.6(4) . . ?
C15 C16 C18 119.9(5) . . ?
C15 C16 C17 119.9(4) . . ?
C18 C16 C17 120.2(4) . . ?
C23 C22 C21 117.8(5) . . ?
C16 C15 C14 120.7(5) . . ?
C11 C10 C9 121.1(5) . . ?
C31 C32 C33 120.2(5) . . ?
C27 C26 C36 120.3(5) . . ?
C27 C26 C25 119.0(4) . . ?
C36 C26 C25 120.6(4) . . ?
C14 C13 C12 120.7(5) . . ?
O4 C35 N4 117.8(5) . . ?
O4 C35 C34 123.7(5) . . ?
N4 C35 C34 118.5(4) . . ?
N3 C23 C22 121.6(5) . . ?
C34 C33 C32 121.1(5) . . ?
O2 C17 N2 118.6(5) . . ?
O2 C17 C16 124.7(4) . . ?
N2 C17 C16 116.7(4) . . ?
C28 C29 C30 120.4(5) . . ?
C32 C31 C30 120.5(6) . . ?
N4 C24 C21 112.6(4) . . ?

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
C1 N1 C5 C4 1.3(8) . . . . ?
C5 N1 C1 C2 -0.6(8) . . . . ?
N1 C5 C4 C3 -0.8(8) . . . . ?
C7 N2 C6 C3 95.2(5) . . . . ?
C17 N2 C6 C3 -85.7(5) . . . . ?
C23 N3 C19 C20 0.8(9) . . . . ?
C21 C20 C19 N3 -1.1(8) . . . . ?
C12 C18 C8 C9 1.6(6) . . . . ?
C16 C18 C8 C9 -178.6(4) . . . . ?
C12 C18 C8 C7 -176.2(4) . . . . ?
C16 C18 C8 C7 3.6(6) . . . . ?
C8 C18 C12 C11 -0.9(6) . . . . ?
C16 C18 C12 C11 179.3(4) . . . . ?
C8 C18 C12 C13 -179.7(4) . . . . ?
C16 C18 C12 C13 0.5(6) . . . . ?
C5 C4 C3 C2 -0.3(8) . . . . ?
C5 C4 C3 C6 178.3(5) . . . . ?
N2 C6 C3 C2 -80.9(6) . . . . ?
N2 C6 C3 C4 100.5(5) . . . . ?
C17 N2 C7 O1 174.3(4) . . . . ?
C6 N2 C7 O1 -6.7(6) . . . . ?
C17 N2 C7 C8 -5.9(6) . . . . ?
C6 N2 C7 C8 173.0(4) . . . . ?
C9 C8 C7 O1 1.9(7) . . . . ?
C18 C8 C7 O1 179.7(4) . . . . ?
C9 C8 C7 N2 -177.8(4) . . . . ?
C18 C8 C7 N2 0.0(6) . . . . ?
C13 C12 C11 C10 178.6(4) . . . . ?
C18 C12 C11 C10 -0.2(7) . . . . ?
C19 C20 C21 C22 0.6(8) . . . . ?
C19 C20 C21 C24 -177.4(5) . . . . ?
C18 C8 C9 C10 -1.2(7) . . . . ?
C7 C8 C9 C10 176.6(4) . . . . ?
C26 C27 C28 C29 -1.2(7) . . . . ?
N1 C1 C2 C3 -0.5(8) . . . . ?
C4 C3 C2 C1 0.9(8) . . . . ?
C6 C3 C2 C1 -177.7(5) . . . . ?
C31 C30 C36 C26 179.7(4) . . . . ?
C29 C30 C36 C26 0.5(6) . . . . ?
C31 C30 C36 C34 -0.3(7) . . . . ?
C29 C30 C36 C34 -179.5(4) . . . . ?
C33 C34 C36 C30 0.4(6) . . . . ?
C35 C34 C36 C30 178.2(4) . . . . ?
C33 C34 C36 C26 -179.6(4) . . . . ?
C35 C34 C36 C26 -1.8(6) . . . . ?
C35 N4 C25 O3 177.4(4) . . . . ?
C24 N4 C25 O3 -6.4(6) . . . . ?
C35 N4 C25 C26 -3.3(6) . . . . ?
C24 N4 C25 C26 172.9(4) . . . . ?
C12 C18 C16 C15 -0.2(6) . . . . ?
C8 C18 C16 C15 180.0(4) . . . . ?
C12 C18 C16 C17 178.2(4) . . . . ?
C8 C18 C16 C17 -1.6(6) . . . . ?
C20 C21 C22 C23 0.1(8) . . . . ?
C24 C21 C22 C23 178.1(5) . . . . ?
C18 C16 C15 C14 0.1(7) . . . . ?
C17 C16 C15 C14 -178.4(4) . . . . ?
C13 C14 C15 C16 -0.2(7) . . . . ?
C12 C11 C10 C9 0.5(7) . . . . ?
C8 C9 C10 C11 0.2(7) . . . . ?
C28 C27 C26 C36 0.4(6) . . . . ?
C28 C27 C26 C25 177.2(4) . . . . ?
C30 C36 C26 C27 0.0(6) . . . . ?
C34 C36 C26 C27 180.0(4) . . . . ?
C30 C36 C26 C25 -176.7(4) . . . . ?
C34 C36 C26 C25 3.3(6) . . . . ?
O3 C25 C26 C27 1.7(7) . . . . ?
N4 C25 C26 C27 -177.5(4) . . . . ?
O3 C25 C26 C36 178.5(4) . . . . ?
N4 C25 C26 C36 -0.8(6) . . . . ?
C15 C14 C13 C12 0.5(7) . . . . ?
C11 C12 C13 C14 -179.4(4) . . . . ?
C18 C12 C13 C14 -0.7(6) . . . . ?
C25 N4 C35 O4 -176.7(4) . . . . ?
C24 N4 C35 O4 7.1(6) . . . . ?
C25 N4 C35 C34 4.8(6) . . . . ?
C24 N4 C35 C34 -171.5(4) . . . . ?
C33 C34 C35 O4 -2.8(7) . . . . ?
C36 C34 C35 O4 179.5(4) . . . . ?
C33 C34 C35 N4 175.7(4) . . . . ?
C36 C34 C35 N4 -2.1(6) . . . . ?
C19 N3 C23 C22 -0.1(9) . . . . ?
C21 C22 C23 N3 -0.4(9) . . . . ?
C36 C34 C33 C32 -0.4(7) . . . . ?
C35 C34 C33 C32 -178.1(4) . . . . ?
C31 C32 C33 C34 0.3(7) . . . . ?
C7 N2 C17 O2 -174.1(4) . . . . ?
C6 N2 C17 O2 6.9(6) . . . . ?
C7 N2 C17 C16 7.8(6) . . . . ?
C6 N2 C17 C16 -171.2(4) . . . . ?
C15 C16 C17 O2 -3.3(7) . . . . ?
C18 C16 C17 O2 178.2(4) . . . . ?
C15 C16 C17 N2 174.7(4) . . . . ?
C18 C16 C17 N2 -3.8(6) . . . . ?
C27 C28 C29 C30 1.7(7) . . . . ?
C36 C30 C29 C28 -1.3(7) . . . . ?
C31 C30 C29 C28 179.5(5) . . . . ?
C33 C32 C31 C30 -0.2(8) . . . . ?
C36 C30 C31 C32 0.2(7) . . . . ?
C29 C30 C31 C32 179.4(5) . . . . ?
C35 N4 C24 C21 -86.5(5) . . . . ?
C25 N4 C24 C21 97.0(5) . . . . ?
C20 C21 C24 N4 -88.5(6) . . . . ?
C22 C21 C24 N4 93.6(6) . . . . ?

_refine_diff_density_max         1.156
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.151

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1824821'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H13 N2 O2), Cl4 Cu'
_chemical_formula_sum            'C36 H26 Cl4 Cu N4 O4'
_chemical_formula_weight         783.96

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.7660(6)
_cell_length_b                   55.312(4)
_cell_length_c                   7.4689(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.983(2)
_cell_angle_gamma                90
_cell_volume                     3206.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.78

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.535
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.031
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             1596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.064
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5213
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            75027
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -69
_diffrn_reflns_limit_k_max       69
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.209
_diffrn_reflns_theta_max         26.451
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6614
_reflns_number_gt                5393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0100P)²+13.1628P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6614
_refine_ls_number_parameters     494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.263
_refine_ls_restrained_S_all      1.263
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.64543(7) 0.62571(2) 0.60587(7) 0.01608(14) Uani 1 1 d . . . . .
Cl1 Cl 0.35962(15) 0.62130(2) 0.55888(15) 0.0220(3) Uani 1 1 d . . . . .
Cl2 Cl 0.67315(16) 0.65459(2) 0.39848(16) 0.0261(3) Uani 1 1 d . . . . .
Cl3 Cl 0.90778(15) 0.60935(2) 0.57032(15) 0.0249(3) Uani 1 1 d . . . . .
Cl4 Cl 0.64177(15) 0.61740(2) 0.89984(14) 0.0209(3) Uani 1 1 d . . . . .
O1 O -0.3211(5) 0.68717(6) -0.1057(5) 0.0305(9) Uani 1 1 d . . . . .
O2 O 0.1937(4) 0.71051(6) -0.3162(4) 0.0233(8) Uani 1 1 d . . . . .
O3 O 1.1255(4) 0.52506(6) 1.4179(5) 0.0273(8) Uani 1 1 d . . . . .
O4 O 1.6311(4) 0.55546(6) 1.2352(5) 0.0246(8) Uani 1 1 d . . . . .
N3 N 0.2845(5) 0.65070(7) 0.2092(5) 0.0187(9) Uani 1 1 d . . . . .
N4 N -0.0682(5) 0.69901(7) -0.2205(5) 0.0162(8) Uani 1 1 d . . . . .
N1 N 1.0346(6) 0.59526(7) 0.9591(5) 0.0220(9) Uani 1 1 d . . . . .
N2 N 1.3833(5) 0.53986(6) 1.3377(5) 0.0148(8) Uani 1 1 d . . . . .
C19 C 0.3644(6) 0.65939(8) 0.0661(6) 0.0198(10) Uani 1 1 d . . . . .
H19 H 0.4864 0.6606 0.0680 0.024 Uiso 1 1 calc R U . . .
C20 C 0.2692(6) 0.66653(8) -0.0828(6) 0.0187(10) Uani 1 1 d . . . . .
H20 H 0.3251 0.6727 -0.1844 0.022 Uiso 1 1 calc R U . . .
C21 C 0.0919(6) 0.66474(8) -0.0843(6) 0.0174(10) Uani 1 1 d . . . . .
C22 C 0.0123(6) 0.65541(8) 0.0654(6) 0.0173(10) Uani 1 1 d . . . . .
H22 H -0.1096 0.6540 0.0666 0.021 Uiso 1 1 calc R U . . .
C23 C 0.1135(6) 0.64828(8) 0.2116(6) 0.0210(11) Uani 1 1 d . . . . .
H23 H 0.0614 0.6417 0.3139 0.025 Uiso 1 1 calc R U . . .
C24 C -0.0172(6) 0.67326(8) -0.2439(6) 0.0208(10) Uani 1 1 d . . . . .
H24B H 0.0488 0.6716 -0.3543 0.025 Uiso 1 1 calc R U . . .
H24A H -0.1217 0.6631 -0.2570 0.025 Uiso 1 1 calc R U . . .
C35 C -0.2290(6) 0.70375(9) -0.1501(6) 0.0199(10) Uani 1 1 d . . . . .
C34 C -0.2797(6) 0.72931(8) -0.1339(6) 0.0151(9) Uani 1 1 d . . . . .
C33 C -0.4385(6) 0.73543(9) -0.0720(6) 0.0212(11) Uani 1 1 d . . . . .
C32 C -0.4847(6) 0.75976(9) -0.0531(6) 0.0215(11) Uani 1 1 d . . . . .
H32 H -0.5949 0.7638 -0.0104 0.026 Uiso 1 1 calc R U . . .
C31 C -0.3725(6) 0.77784(9) -0.0954(6) 0.0208(11) Uani 1 1 d . . . . .
C30 C -0.2092(6) 0.77235(8) -0.1591(6) 0.0157(10) Uani 1 1 d . . . . .
C36 C -0.1623(6) 0.74770(8) -0.1792(6) 0.0140(9) Uani 1 1 d . . . . .
C29 C -0.0887(6) 0.79043(9) -0.2038(6) 0.0199(10) Uani 1 1 d . . . . .
C28 C 0.0698(7) 0.78429(9) -0.2622(6) 0.0220(11) Uani 1 1 d . . . . .
C27 C 0.1164(6) 0.75996(8) -0.2821(6) 0.0185(10) Uani 1 1 d . . . . .
C26 C 0.0016(6) 0.74195(8) -0.2417(5) 0.0144(9) Uani 1 1 d . . . . .
C25 C 0.0533(6) 0.71633(8) -0.2638(6) 0.0155(10) Uani 1 1 d . . . . .
C5 C 1.2041(6) 0.59887(8) 0.9678(6) 0.0202(10) Uani 1 1 d . . . . .
H5 H 1.2582 0.6079 0.8773 0.024 Uiso 1 1 calc R U . . .
C4 C 1.2996(6) 0.58943(8) 1.1090(6) 0.0193(10) Uani 1 1 d . . . . .
H4 H 1.4205 0.5921 1.1171 0.023 Uiso 1 1 calc R U . . .
C3 C 1.2202(6) 0.57604(8) 1.2402(6) 0.0171(10) Uani 1 1 d . . . . .
C2 C 1.0432(6) 0.57320(9) 1.2267(6) 0.0226(11) Uani 1 1 d . . . . .
H2 H 0.9854 0.5644 1.3158 0.027 Uiso 1 1 calc R U . . .
C1 C 0.9514(6) 0.58309(8) 1.0853(7) 0.0237(11) Uani 1 1 d . . . . .
H1 H 0.8297 0.5814 1.0764 0.028 Uiso 1 1 calc R U . . .
C6 C 1.3265(6) 0.56434(8) 1.3900(6) 0.0182(10) Uani 1 1 d . . . . .
H6A H 1.4286 0.5745 1.4194 0.022 Uiso 1 1 calc R U . . .
H6B H 1.2570 0.5632 1.4984 0.022 Uiso 1 1 calc R U . . .
C17 C 1.5448(6) 0.53760(8) 1.2622(6) 0.0174(10) Uani 1 1 d . . . . .
C16 C 1.6032(6) 0.51285(8) 1.2199(6) 0.0157(10) Uani 1 1 d . . . . .
C15 C 1.7640(6) 0.50936(9) 1.1577(6) 0.0203(10) Uani 1 1 d . . . . .
C14 C 1.8211(7) 0.48581(9) 1.1183(6) 0.0232(11) Uani 1 1 d . . . . .
C13 C 1.7154(7) 0.46651(9) 1.1408(6) 0.0226(11) Uani 1 1 d . . . . .
C12 C 1.5486(6) 0.46929(8) 1.2056(6) 0.0171(10) Uani 1 1 d . . . . .
C18 C 1.4909(6) 0.49304(8) 1.2480(6) 0.0155(10) Uani 1 1 d . . . . .
C11 C 1.4343(7) 0.44969(9) 1.2349(6) 0.0234(11) Uani 1 1 d . . . . .
C10 C 1.2775(7) 0.45336(9) 1.3033(7) 0.0247(12) Uani 1 1 d . . . . .
C9 C 1.2222(6) 0.47689(9) 1.3462(6) 0.0196(10) Uani 1 1 d . . . . .
C8 C 1.3271(6) 0.49633(8) 1.3185(6) 0.0171(10) Uani 1 1 d . . . . .
C7 C 1.2669(6) 0.52090(8) 1.3627(6) 0.0171(10) Uani 1 1 d . . . . .
H1N H 0.964(7) 0.6012(10) 0.864(7) 0.033(15) Uiso 1 1 d . . . . .
H3N H 0.340(7) 0.6467(9) 0.293(7) 0.020(15) Uiso 1 1 d . . . . .
H33 H -0.509(6) 0.7234(9) -0.047(6) 0.015(12) Uiso 1 1 d . . . . .
H27 H 0.224(6) 0.7568(8) -0.324(6) 0.006(11) Uiso 1 1 d . . . . .
H31 H -0.419(6) 0.7946(9) -0.087(6) 0.014(12) Uiso 1 1 d . . . . .
H28 H 0.152(6) 0.7963(9) -0.285(6) 0.017(12) Uiso 1 1 d . . . . .
H29 H -0.127(7) 0.8079(10) -0.185(7) 0.034(15) Uiso 1 1 d . . . . .
H15 H 1.831(6) 0.5219(8) 1.139(6) 0.006(11) Uiso 1 1 d . . . . .
H11 H 1.477(7) 0.4330(10) 1.205(7) 0.034(15) Uiso 1 1 d . . . . .
H13 H 1.757(6) 0.4518(10) 1.114(7) 0.024(14) Uiso 1 1 d . . . . .
H9 H 1.115(7) 0.4794(9) 1.399(7) 0.025(14) Uiso 1 1 d . . . . .
H10 H 1.208(7) 0.4422(10) 1.324(7) 0.037(17) Uiso 1 1 d . . . . .
H14 H 1.940(8) 0.4842(11) 1.072(8) 0.056(19) 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 Cl2 2.2409(12) . ?
Cu1 Cl4 2.2444(12) . ?
Cu1 Cl1 2.2485(13) . ?
Cu1 Cl3 2.2534(13) . ?
O1 C35 1.217(6) . ?
O2 C25 1.215(5) . ?
O3 C7 1.209(6) . ?
O4 C17 1.215(5) . ?
N3 C23 1.336(6) . ?
N3 C19 1.343(6) . ?
N3 H3N 0.78(5) . ?
N4 C25 1.391(6) . ?
N4 C35 1.396(6) . ?
N4 C24 1.490(6) . ?
N1 C5 1.330(6) . ?
N1 C1 1.342(6) . ?
N1 H1N 0.94(6) . ?
N2 C17 1.399(6) . ?
N2 C7 1.401(6) . ?
N2 C6 1.481(6) . ?
C19 C20 1.372(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(6) . ?
C21 C24 1.514(6) . ?
C22 C23 1.381(6) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24B 0.9900 . ?
C24 H24A 0.9900 . ?
C35 C34 1.474(6) . ?
C34 C33 1.374(7) . ?
C34 C36 1.415(6) . ?
C33 C32 1.401(7) . ?
C33 H33 0.88(5) . ?
C32 C31 1.370(7) . ?
C32 H32 0.9500 . ?
C31 C30 1.403(7) . ?
C31 H31 1.00(5) . ?
C30 C29 1.417(7) . ?
C30 C36 1.421(6) . ?
C36 C26 1.407(6) . ?
C29 C28 1.363(7) . ?
C29 H29 1.02(5) . ?
C28 C27 1.403(7) . ?
C28 H28 0.94(5) . ?
C27 C26 1.377(6) . ?
C27 H27 0.92(5) . ?
C26 C25 1.484(6) . ?
C5 C4 1.371(6) . ?
C5 H5 0.9500 . ?
C4 C3 1.390(6) . ?
C4 H4 0.9500 . ?
C3 C2 1.384(7) . ?
C3 C6 1.513(6) . ?
C2 C1 1.368(7) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C17 C16 1.479(6) . ?
C16 C15 1.361(7) . ?
C16 C18 1.421(6) . ?
C15 C14 1.410(7) . ?
C15 H15 0.88(4) . ?
C14 C13 1.361(7) . ?
C14 H14 1.00(7) . ?
C13 C12 1.407(7) . ?
C13 H13 0.90(5) . ?
C12 C11 1.423(7) . ?
C12 C18 1.427(6) . ?
C18 C8 1.406(7) . ?
C11 C10 1.352(8) . ?
C11 H11 1.01(5) . ?
C10 C9 1.411(7) . ?
C10 H10 0.84(6) . ?
C9 C8 1.369(6) . ?
C9 H9 0.94(5) . ?
C8 C7 1.478(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
Cl2 Cu1 Cl4 145.79(5) . . ?
Cl2 Cu1 Cl1 95.01(5) . . ?
Cl4 Cu1 Cl1 94.86(5) . . ?
Cl2 Cu1 Cl3 95.51(5) . . ?
Cl4 Cu1 Cl3 94.31(5) . . ?
Cl1 Cu1 Cl3 146.07(5) . . ?
C23 N3 C19 122.2(4) . . ?
C23 N3 H3N 119(4) . . ?
C19 N3 H3N 119(4) . . ?
C25 N4 C35 125.5(4) . . ?
C25 N4 C24 116.5(4) . . ?
C35 N4 C24 117.9(4) . . ?
C5 N1 C1 122.7(4) . . ?
C5 N1 H1N 122(3) . . ?
C1 N1 H1N 115(3) . . ?
C17 N2 C7 125.4(4) . . ?
C17 N2 C6 117.9(4) . . ?
C7 N2 C6 116.7(4) . . ?
N3 C19 C20 119.9(5) . . ?
N3 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 119.7(4) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 119.3(4) . . ?
C20 C21 C24 121.0(4) . . ?
C22 C21 C24 119.6(4) . . ?
C23 C22 C21 118.9(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
N3 C23 C22 120.0(4) . . ?
N3 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
N4 C24 C21 110.4(4) . . ?
N4 C24 H24B 109.6 . . ?
C21 C24 H24B 109.6 . . ?
N4 C24 H24A 109.6 . . ?
C21 C24 H24A 109.6 . . ?
H24B C24 H24A 108.1 . . ?
O1 C35 N4 120.2(4) . . ?
O1 C35 C34 122.6(5) . . ?
N4 C35 C34 117.2(4) . . ?
C33 C34 C36 119.8(4) . . ?
C33 C34 C35 120.6(4) . . ?
C36 C34 C35 119.6(4) . . ?
C34 C33 C32 120.4(5) . . ?
C34 C33 H33 117(3) . . ?
C32 C33 H33 123(3) . . ?
C31 C32 C33 120.7(5) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C32 C31 C30 120.6(5) . . ?
C32 C31 H31 115(3) . . ?
C30 C31 H31 124(3) . . ?
C31 C30 C29 122.6(4) . . ?
C31 C30 C36 118.8(4) . . ?
C29 C30 C36 118.6(4) . . ?
C26 C36 C34 121.0(4) . . ?
C26 C36 C30 119.4(4) . . ?
C34 C36 C30 119.7(4) . . ?
C28 C29 C30 120.7(4) . . ?
C28 C29 H29 123(3) . . ?
C30 C29 H29 116(3) . . ?
C29 C28 C27 120.8(5) . . ?
C29 C28 H28 121(3) . . ?
C27 C28 H28 119(3) . . ?
C26 C27 C28 120.0(5) . . ?
C26 C27 H27 123(3) . . ?
C28 C27 H27 117(3) . . ?
C27 C26 C36 120.6(4) . . ?
C27 C26 C25 119.1(4) . . ?
C36 C26 C25 120.3(4) . . ?
O2 C25 N4 121.1(4) . . ?
O2 C25 C26 122.6(4) . . ?
N4 C25 C26 116.3(4) . . ?
N1 C5 C4 119.3(4) . . ?
N1 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C2 C3 C4 118.3(4) . . ?
C2 C3 C6 121.3(4) . . ?
C4 C3 C6 120.4(4) . . ?
C1 C2 C3 120.0(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N1 C1 C2 119.5(5) . . ?
N1 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
N2 C6 C3 110.9(4) . . ?
N2 C6 H6A 109.5 . . ?
C3 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O4 C17 N2 120.1(4) . . ?
O4 C17 C16 122.9(4) . . ?
N2 C17 C16 117.0(4) . . ?
C15 C16 C18 121.1(4) . . ?
C15 C16 C17 119.7(4) . . ?
C18 C16 C17 119.2(4) . . ?
C16 C15 C14 120.1(5) . . ?
C16 C15 H15 120(3) . . ?
C14 C15 H15 120(3) . . ?
C13 C14 C15 120.2(5) . . ?
C13 C14 H14 123(4) . . ?
C15 C14 H14 117(4) . . ?
C14 C13 C12 121.5(5) . . ?
C14 C13 H13 117(3) . . ?
C12 C13 H13 121(3) . . ?
C13 C12 C11 123.8(4) . . ?
C13 C12 C18 118.5(4) . . ?
C11 C12 C18 117.7(4) . . ?
C8 C18 C16 121.6(4) . . ?
C8 C18 C12 119.9(4) . . ?
C16 C18 C12 118.6(4) . . ?
C10 C11 C12 121.2(5) . . ?
C10 C11 H11 122(3) . . ?
C12 C11 H11 117(3) . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 124(4) . . ?
C9 C10 H10 116(4) . . ?
C8 C9 C10 120.2(5) . . ?
C8 C9 H9 119(3) . . ?
C10 C9 H9 121(3) . . ?
C9 C8 C18 120.4(4) . . ?
C9 C8 C7 119.6(4) . . ?
C18 C8 C7 120.0(4) . . ?
O3 C7 N2 120.1(4) . . ?
O3 C7 C8 123.3(4) . . ?
N2 C7 C8 116.6(4) . . ?

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
C23 N3 C19 C20 1.2(7) . . . . ?
N3 C19 C20 C21 0.1(7) . . . . ?
C19 C20 C21 C22 -0.7(7) . . . . ?
C19 C20 C21 C24 177.8(4) . . . . ?
C20 C21 C22 C23 0.2(6) . . . . ?
C24 C21 C22 C23 -178.4(4) . . . . ?
C19 N3 C23 C22 -1.7(7) . . . . ?
C21 C22 C23 N3 1.0(7) . . . . ?
C25 N4 C24 C21 81.5(5) . . . . ?
C35 N4 C24 C21 -95.7(5) . . . . ?
C20 C21 C24 N4 -91.4(5) . . . . ?
C22 C21 C24 N4 87.2(5) . . . . ?
C25 N4 C35 O1 -175.1(4) . . . . ?
C24 N4 C35 O1 1.9(6) . . . . ?
C25 N4 C35 C34 5.2(6) . . . . ?
C24 N4 C35 C34 -177.9(4) . . . . ?
O1 C35 C34 C33 -2.1(7) . . . . ?
N4 C35 C34 C33 177.6(4) . . . . ?
O1 C35 C34 C36 176.7(4) . . . . ?
N4 C35 C34 C36 -3.6(6) . . . . ?
C36 C34 C33 C32 -0.2(7) . . . . ?
C35 C34 C33 C32 178.6(4) . . . . ?
C34 C33 C32 C31 -0.1(7) . . . . ?
C33 C32 C31 C30 0.1(7) . . . . ?
C32 C31 C30 C29 -179.7(4) . . . . ?
C32 C31 C30 C36 0.2(7) . . . . ?
C33 C34 C36 C26 179.6(4) . . . . ?
C35 C34 C36 C26 0.8(6) . . . . ?
C33 C34 C36 C30 0.5(6) . . . . ?
C35 C34 C36 C30 -178.3(4) . . . . ?
C31 C30 C36 C26 -179.6(4) . . . . ?
C29 C30 C36 C26 0.3(6) . . . . ?
C31 C30 C36 C34 -0.5(6) . . . . ?
C29 C30 C36 C34 179.4(4) . . . . ?
C31 C30 C29 C28 178.9(5) . . . . ?
C36 C30 C29 C28 -1.0(7) . . . . ?
C30 C29 C28 C27 1.0(7) . . . . ?
C29 C28 C27 C26 -0.2(7) . . . . ?
C28 C27 C26 C36 -0.5(7) . . . . ?
C28 C27 C26 C25 179.9(4) . . . . ?
C34 C36 C26 C27 -178.6(4) . . . . ?
C30 C36 C26 C27 0.4(6) . . . . ?
C34 C36 C26 C25 0.9(6) . . . . ?
C30 C36 C26 C25 180.0(4) . . . . ?
C35 N4 C25 O2 176.3(4) . . . . ?
C24 N4 C25 O2 -0.7(6) . . . . ?
C35 N4 C25 C26 -3.5(6) . . . . ?
C24 N4 C25 C26 179.5(4) . . . . ?
C27 C26 C25 O2 0.1(7) . . . . ?
C36 C26 C25 O2 -179.5(4) . . . . ?
C27 C26 C25 N4 179.9(4) . . . . ?
C36 C26 C25 N4 0.3(6) . . . . ?
C1 N1 C5 C4 1.4(7) . . . . ?
N1 C5 C4 C3 0.7(7) . . . . ?
C5 C4 C3 C2 -1.9(7) . . . . ?
C5 C4 C3 C6 176.3(4) . . . . ?
C4 C3 C2 C1 1.1(7) . . . . ?
C6 C3 C2 C1 -177.0(4) . . . . ?
C5 N1 C1 C2 -2.2(7) . . . . ?
C3 C2 C1 N1 0.8(7) . . . . ?
C17 N2 C6 C3 93.3(5) . . . . ?
C7 N2 C6 C3 -84.6(5) . . . . ?
C2 C3 C6 N2 89.7(5) . . . . ?
C4 C3 C6 N2 -88.4(5) . . . . ?
C7 N2 C17 O4 174.9(4) . . . . ?
C6 N2 C17 O4 -2.7(6) . . . . ?
C7 N2 C17 C16 -5.6(6) . . . . ?
C6 N2 C17 C16 176.8(4) . . . . ?
O4 C17 C16 C15 3.9(7) . . . . ?
N2 C17 C16 C15 -175.5(4) . . . . ?
O4 C17 C16 C18 -177.1(4) . . . . ?
N2 C17 C16 C18 3.5(6) . . . . ?
C18 C16 C15 C14 0.6(7) . . . . ?
C17 C16 C15 C14 179.6(4) . . . . ?
C16 C15 C14 C13 0.5(7) . . . . ?
C15 C14 C13 C12 -0.9(7) . . . . ?
C14 C13 C12 C11 -178.7(5) . . . . ?
C14 C13 C12 C18 0.0(7) . . . . ?
C15 C16 C18 C8 177.6(4) . . . . ?
C17 C16 C18 C8 -1.4(6) . . . . ?
C15 C16 C18 C12 -1.4(6) . . . . ?
C17 C16 C18 C12 179.6(4) . . . . ?
C13 C12 C18 C8 -177.9(4) . . . . ?
C11 C12 C18 C8 0.9(6) . . . . ?
C13 C12 C18 C16 1.1(6) . . . . ?
C11 C12 C18 C16 179.9(4) . . . . ?
C13 C12 C11 C10 177.7(5) . . . . ?
C18 C12 C11 C10 -1.0(7) . . . . ?
C12 C11 C10 C9 0.6(7) . . . . ?
C11 C10 C9 C8 0.1(7) . . . . ?
C10 C9 C8 C18 -0.2(7) . . . . ?
C10 C9 C8 C7 179.5(4) . . . . ?
C16 C18 C8 C9 -179.2(4) . . . . ?
C12 C18 C8 C9 -0.3(6) . . . . ?
C16 C18 C8 C7 1.0(6) . . . . ?
C12 C18 C8 C7 180.0(4) . . . . ?
C17 N2 C7 O3 -174.8(4) . . . . ?
C6 N2 C7 O3 2.8(6) . . . . ?
C17 N2 C7 C8 5.2(6) . . . . ?
C6 N2 C7 C8 -177.2(4) . . . . ?
C9 C8 C7 O3 -2.4(7) . . . . ?
C18 C8 C7 O3 177.4(4) . . . . ?
C9 C8 C7 N2 177.6(4) . . . . ?
C18 C8 C7 N2 -2.7(6) . . . . ?

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
C19 H19 Cl4 0.95 2.97 3.430(5) 110.9 1_554
C19 H19 O1 0.95 2.49 3.192(6) 130.5 1_655
C20 H20 O2 0.95 2.51 3.038(5) 114.8 .
C23 H23 Cl3 0.95 2.91 3.829(5) 164.3 1_455
C5 H5 Cl1 0.95 2.64 3.547(5) 160.5 1_655
C4 H4 Cl4 0.95 2.78 3.490(5) 132.0 1_655
C2 H2 O3 0.95 2.54 3.078(6) 116.3 .
C1 H1 Cl4 0.95 2.78 3.327(5) 117.8 .
C1 H1 O4 0.95 2.44 3.157(6) 132.0 1_455
C6 H6A Cl1 0.99 2.85 3.400(5) 115.9 1_656
N1 H1N Cl3 0.94(6) 2.27(6) 3.132(4) 153(5) .
N1 H1N Cl4 0.94(6) 2.68(5) 3.303(4) 124(4) .
N3 H3N Cl1 0.78(5) 2.43(5) 3.114(4) 147(5) .
N3 H3N Cl2 0.78(5) 2.71(5) 3.295(4) 133(5) .

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.100

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1824824'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N2 O2, Br'
_chemical_formula_sum            'C18 H13 Br N2 O2'
_chemical_formula_weight         369.21

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.5398(16)
_cell_length_b                   7.7569(9)
_cell_length_c                   15.2010(17)
_cell_angle_alpha                90
_cell_angle_beta                 112.641(3)
_cell_angle_gamma                90
_cell_volume                     1473.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9466
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.46

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    2.801
_shelx_estimated_absorpt_T_min   0.347
_shelx_estimated_absorpt_T_max   0.372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3466
_exptl_absorpt_correction_T_max  0.3720
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41090
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.566
_diffrn_reflns_theta_max         26.518
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3052
_reflns_number_gt                2836
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0270P)²+0.8997P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0120(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3052
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0208
_refine_ls_wR_factor_ref         0.0554
_refine_ls_wR_factor_gt          0.0542
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.86177(2) 0.86492(2) 0.30620(2) 0.02101(8) Uani 1 1 d . . . . .
O1 O 0.78869(9) -0.10128(15) 0.58306(9) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.71914(9) 0.41403(15) 0.68747(8) 0.0201(2) Uani 1 1 d . . . . .
N1 N 0.85831(11) 0.51557(19) 0.41620(10) 0.0212(3) Uani 1 1 d . . . . .
N2 N 0.75481(10) 0.15413(16) 0.63816(9) 0.0138(3) Uani 1 1 d . . . . .
C5 C 0.85513(14) 0.5961(2) 0.49265(13) 0.0236(4) Uani 1 1 d . . . . .
C4 C 0.85643(13) 0.5021(2) 0.56981(12) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.86121(11) 0.3233(2) 0.56739(11) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.86555(12) 0.2444(2) 0.48661(12) 0.0179(3) Uani 1 1 d . . . . .
C1 C 0.86322(14) 0.3439(2) 0.41069(12) 0.0216(4) Uani 1 1 d . . . . .
C6 C 0.86220(12) 0.2168(2) 0.65079(11) 0.0167(3) Uani 1 1 d . . . . .
C17 C 0.69028(12) 0.26625(19) 0.66482(10) 0.0140(3) Uani 1 1 d . . . . .
C16 C 0.58867(12) 0.1968(2) 0.66373(10) 0.0136(3) Uani 1 1 d . . . . .
C15 C 0.52304(13) 0.2992(2) 0.69223(11) 0.0175(3) Uani 1 1 d . . . . .
C14 C 0.42473(13) 0.2356(2) 0.68962(12) 0.0211(3) Uani 1 1 d . . . . .
C13 C 0.39392(13) 0.0701(2) 0.66054(12) 0.0197(3) Uani 1 1 d . . . . .
C12 C 0.45975(12) -0.0389(2) 0.63183(10) 0.0154(3) Uani 1 1 d . . . . .
C11 C 0.43128(12) -0.2109(2) 0.60195(11) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.49675(13) -0.3113(2) 0.57377(11) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.59397(13) -0.2469(2) 0.57436(11) 0.0161(3) Uani 1 1 d . . . . .
C8 C 0.62433(12) -0.0804(2) 0.60354(10) 0.0130(3) Uani 1 1 d . . . . .
C7 C 0.72786(12) -0.0151(2) 0.60663(11) 0.0145(3) Uani 1 1 d . . . . .
C18 C 0.55779(11) 0.02629(19) 0.63276(10) 0.0125(3) Uani 1 1 d . . . . .
H9 H 0.6381(16) -0.313(3) 0.5542(14) 0.021(5) Uiso 1 1 d . . . . .
H10 H 0.4770(14) -0.424(2) 0.5546(13) 0.016(4) Uiso 1 1 d . . . . .
H15 H 0.5458(16) 0.414(3) 0.7123(14) 0.022(5) Uiso 1 1 d . . . . .
H6A H 0.9060(16) 0.119(2) 0.6583(14) 0.017(5) Uiso 1 1 d . . . . .
H13 H 0.3282(17) 0.026(3) 0.6581(14) 0.026(5) Uiso 1 1 d . . . . .
H6B H 0.8899(15) 0.279(3) 0.7072(14) 0.019(5) Uiso 1 1 d . . . . .
H11 H 0.3684(17) -0.256(3) 0.6048(15) 0.029(5) Uiso 1 1 d . . . . .
H4 H 0.8520(16) 0.561(3) 0.6227(15) 0.029(5) Uiso 1 1 d . . . . .
H5 H 0.8513(16) 0.717(3) 0.4894(14) 0.027(5) Uiso 1 1 d . . . . .
H14 H 0.3792(17) 0.308(3) 0.7079(15) 0.029(5) Uiso 1 1 d . . . . .
H2 H 0.8694(17) 0.123(3) 0.4818(15) 0.024(5) Uiso 1 1 d . . . . .
H1 H 0.8642(16) 0.297(3) 0.3537(15) 0.029(5) Uiso 1 1 d . . . . .
H1N H 0.855(2) 0.583(3) 0.3697(19) 0.051(7) 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
O1 C7 1.2167(19) . ?
O2 C17 1.2172(19) . ?
N1 C5 1.335(2) . ?
N1 C1 1.338(2) . ?
N1 H1N 0.87(3) . ?
N2 C7 1.397(2) . ?
N2 C17 1.399(2) . ?
N2 C6 1.4739(19) . ?
C5 C4 1.376(2) . ?
C5 H5 0.94(2) . ?
C4 C3 1.390(2) . ?
C4 H4 0.95(2) . ?
C3 C2 1.393(2) . ?
C3 C6 1.509(2) . ?
C2 C1 1.378(2) . ?
C2 H2 0.95(2) . ?
C1 H1 0.94(2) . ?
C6 H6A 0.940(19) . ?
C6 H6B 0.93(2) . ?
C17 C16 1.472(2) . ?
C16 C15 1.380(2) . ?
C16 C18 1.412(2) . ?
C15 C14 1.406(2) . ?
C15 H15 0.95(2) . ?
C14 C13 1.369(3) . ?
C14 H14 0.95(2) . ?
C13 C12 1.414(2) . ?
C13 H13 0.94(2) . ?
C12 C11 1.414(2) . ?
C12 C18 1.416(2) . ?
C11 C10 1.367(2) . ?
C11 H11 0.94(2) . ?
C10 C9 1.405(2) . ?
C10 H10 0.929(19) . ?
C9 C8 1.376(2) . ?
C9 H9 0.92(2) . ?
C8 C18 1.415(2) . ?
C8 C7 1.474(2) . ?

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
C5 N1 C1 122.66(15) . . ?
C5 N1 H1N 114.6(17) . . ?
C1 N1 H1N 122.7(17) . . ?
C7 N2 C17 125.03(13) . . ?
C7 N2 C6 117.95(13) . . ?
C17 N2 C6 116.89(13) . . ?
N1 C5 C4 119.98(16) . . ?
N1 C5 H5 116.2(12) . . ?
C4 C5 H5 123.8(13) . . ?
C5 C4 C3 119.50(16) . . ?
C5 C4 H4 119.1(13) . . ?
C3 C4 H4 121.4(13) . . ?
C4 C3 C2 118.66(15) . . ?
C4 C3 C6 120.65(15) . . ?
C2 C3 C6 120.69(15) . . ?
C1 C2 C3 119.80(16) . . ?
C1 C2 H2 118.5(13) . . ?
C3 C2 H2 121.7(13) . . ?
N1 C1 C2 119.38(16) . . ?
N1 C1 H1 117.4(13) . . ?
C2 C1 H1 123.2(13) . . ?
N2 C6 C3 112.45(12) . . ?
N2 C6 H6A 107.2(12) . . ?
C3 C6 H6A 110.1(12) . . ?
N2 C6 H6B 108.6(12) . . ?
C3 C6 H6B 111.2(12) . . ?
H6A C6 H6B 107.1(17) . . ?
O2 C17 N2 119.95(14) . . ?
O2 C17 C16 123.01(14) . . ?
N2 C17 C16 117.05(13) . . ?
C15 C16 C18 119.99(14) . . ?
C15 C16 C17 119.87(14) . . ?
C18 C16 C17 120.13(13) . . ?
C16 C15 C14 120.43(15) . . ?
C16 C15 H15 118.0(12) . . ?
C14 C15 H15 121.5(12) . . ?
C13 C14 C15 120.35(15) . . ?
C13 C14 H14 119.9(13) . . ?
C15 C14 H14 119.7(13) . . ?
C14 C13 C12 120.69(15) . . ?
C14 C13 H13 121.3(12) . . ?
C12 C13 H13 118.0(13) . . ?
C13 C12 C11 122.49(14) . . ?
C13 C12 C18 118.90(15) . . ?
C11 C12 C18 118.61(14) . . ?
C10 C11 C12 120.57(15) . . ?
C10 C11 H11 121.0(13) . . ?
C12 C11 H11 118.3(13) . . ?
C11 C10 C9 121.00(15) . . ?
C11 C10 H10 119.4(11) . . ?
C9 C10 H10 119.6(11) . . ?
C8 C9 C10 119.90(15) . . ?
C8 C9 H9 118.5(12) . . ?
C10 C9 H9 121.6(12) . . ?
C9 C8 C18 120.19(14) . . ?
C9 C8 C7 119.66(14) . . ?
C18 C8 C7 120.13(14) . . ?
O1 C7 N2 120.02(14) . . ?
O1 C7 C8 123.04(14) . . ?
N2 C7 C8 116.95(13) . . ?
C16 C18 C8 120.65(13) . . ?
C16 C18 C12 119.61(13) . . ?
C8 C18 C12 119.74(14) . . ?

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
C1 N1 C5 C4 -0.3(3) . . . . ?
N1 C5 C4 C3 0.1(3) . . . . ?
C5 C4 C3 C2 0.6(2) . . . . ?
C5 C4 C3 C6 -179.70(15) . . . . ?
C4 C3 C2 C1 -1.1(2) . . . . ?
C6 C3 C2 C1 179.20(15) . . . . ?
C5 N1 C1 C2 -0.3(3) . . . . ?
C3 C2 C1 N1 0.9(2) . . . . ?
C7 N2 C6 C3 99.21(16) . . . . ?
C17 N2 C6 C3 -84.83(17) . . . . ?
C4 C3 C6 N2 96.08(17) . . . . ?
C2 C3 C6 N2 -84.21(18) . . . . ?
C7 N2 C17 O2 -176.86(14) . . . . ?
C6 N2 C17 O2 7.5(2) . . . . ?
C7 N2 C17 C16 3.1(2) . . . . ?
C6 N2 C17 C16 -172.55(12) . . . . ?
O2 C17 C16 C15 -2.2(2) . . . . ?
N2 C17 C16 C15 177.90(13) . . . . ?
O2 C17 C16 C18 177.27(14) . . . . ?
N2 C17 C16 C18 -2.7(2) . . . . ?
C18 C16 C15 C14 -0.8(2) . . . . ?
C17 C16 C15 C14 178.66(14) . . . . ?
C16 C15 C14 C13 1.3(2) . . . . ?
C15 C14 C13 C12 -0.6(2) . . . . ?
C14 C13 C12 C11 179.55(15) . . . . ?
C14 C13 C12 C18 -0.6(2) . . . . ?
C13 C12 C11 C10 179.27(15) . . . . ?
C18 C12 C11 C10 -0.6(2) . . . . ?
C12 C11 C10 C9 0.4(2) . . . . ?
C11 C10 C9 C8 -0.1(2) . . . . ?
C10 C9 C8 C18 -0.1(2) . . . . ?
C10 C9 C8 C7 178.26(14) . . . . ?
C17 N2 C7 O1 178.39(14) . . . . ?
C6 N2 C7 O1 -6.0(2) . . . . ?
C17 N2 C7 C8 -1.4(2) . . . . ?
C6 N2 C7 C8 174.18(13) . . . . ?
C9 C8 C7 O1 1.1(2) . . . . ?
C18 C8 C7 O1 179.47(14) . . . . ?
C9 C8 C7 N2 -179.10(13) . . . . ?
C18 C8 C7 N2 -0.7(2) . . . . ?
C15 C16 C18 C8 -179.85(14) . . . . ?
C17 C16 C18 C8 0.7(2) . . . . ?
C15 C16 C18 C12 -0.4(2) . . . . ?
C17 C16 C18 C12 -179.86(13) . . . . ?
C9 C8 C18 C16 179.37(14) . . . . ?
C7 C8 C18 C16 1.0(2) . . . . ?
C9 C8 C18 C12 0.0(2) . . . . ?
C7 C8 C18 C12 -178.41(13) . . . . ?
C13 C12 C18 C16 1.1(2) . . . . ?
C11 C12 C18 C16 -179.02(13) . . . . ?
C13 C12 C18 C8 -179.48(14) . . . . ?
C11 C12 C18 C8 0.4(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
C6 H6A Br1 0.940(19) 2.98(2) 3.5938(16) 124.2(14) 3_766
C4 H4 O2 0.95(2) 2.62(2) 3.111(2) 112.8(15) .
C5 H5 Br1 0.94(2) 3.07(2) 3.5473(18) 113.6(14) .
C5 H5 O1 0.94(2) 2.38(2) 3.026(2) 125.9(16) 1_565
N1 H1N Br1 0.87(3) 2.41(3) 3.1940(15) 151(2) .
C6 H6A Br1 0.940(19) 2.98(2) 3.5938(16) 124.2(14) 3_766
C4 H4 O2 0.95(2) 2.62(2) 3.111(2) 112.8(15) .
C5 H5 Br1 0.94(2) 3.07(2) 3.5473(18) 113.6(14) .
C5 H5 O1 0.94(2) 2.38(2) 3.026(2) 125.9(16) 1_565
N1 H1N Br1 0.87(3) 2.41(3) 3.1940(15) 151(2) .

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 1824819'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H13 N2 O2), Cd Cl4'
_chemical_formula_sum            'C36 H26 Cd Cl4 N4 O4'
_chemical_formula_weight         832.81

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'
Cd Cd -0.8075 1.2024 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8678(7)
_cell_length_b                   14.7568(13)
_cell_length_c                   14.8082(13)
_cell_angle_alpha                102.750(4)
_cell_angle_beta                 100.866(4)
_cell_angle_gamma                93.071(4)
_cell_volume                     1638.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      26.15

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             836
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.041
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7438
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49156
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.250
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6718
_reflns_number_gt                5111
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0298P)²+1.0921P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6718
_refine_ls_number_parameters     546
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0767
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.79363(9) 0.54692(5) -0.04161(5) 0.02176(17) Uani 1 1 d . U . . .
Cl2 Cl 0.73557(10) 0.81744(5) -0.01706(6) 0.02702(18) Uani 1 1 d . U . . .
Cl3 Cl 1.17580(10) 0.75592(6) 0.09167(6) 0.0337(2) Uani 1 1 d . U . . .
Cl4 Cl 0.77550(14) 0.69065(7) 0.21333(7) 0.0512(3) Uani 1 1 d . U . . .
Cd1 Cd 0.86454(3) 0.70365(2) 0.06984(2) 0.02369(8) Uani 1 1 d . U . . .
O1 O 0.3239(2) 0.03529(14) 0.22000(15) 0.0256(5) Uani 1 1 d . U . . .
O3 O 0.3023(3) 0.33537(15) 0.28720(15) 0.0272(5) Uani 1 1 d . U . . .
O2 O 0.8686(2) 0.00683(14) 0.37015(15) 0.0246(5) Uani 1 1 d . U . . .
O4 O 0.8466(3) 0.28104(15) 0.41459(15) 0.0289(5) Uani 1 1 d . U . . .
N2 N 0.5912(3) 0.01563(16) 0.29801(17) 0.0169(5) Uani 1 1 d . U . . .
N4 N 0.5716(3) 0.30566(15) 0.35269(17) 0.0167(5) Uani 1 1 d . U . . .
N1 N 0.8708(3) 0.11507(18) 0.05530(18) 0.0220(6) Uani 1 1 d . U . . .
N3 N 0.8433(3) 0.42157(18) 0.11305(19) 0.0229(6) Uani 1 1 d . U . . .
C5 C 0.9698(4) 0.0692(2) 0.1103(2) 0.0244(7) Uani 1 1 d . U . . .
C1 C 0.6989(4) 0.1143(2) 0.0488(2) 0.0220(7) Uani 1 1 d . U . . .
C20 C 0.5884(4) 0.3635(2) 0.1494(2) 0.0225(7) Uani 1 1 d . U . . .
C18 C 0.5171(3) 0.10907(18) 0.4707(2) 0.0169(6) Uani 1 1 d . U . . .
C4 C 0.8943(4) 0.0174(2) 0.1614(2) 0.0224(7) Uani 1 1 d . U . . .
C6 C 0.6261(4) -0.0434(2) 0.2102(2) 0.0215(7) Uani 1 1 d . U . . .
C19 C 0.6699(4) 0.4158(2) 0.1011(2) 0.0249(7) Uani 1 1 d . U . . .
C8 C 0.3916(3) 0.09805(18) 0.3866(2) 0.0169(6) Uani 1 1 d . U . . .
C12 C 0.4774(4) 0.15239(19) 0.5591(2) 0.0205(7) Uani 1 1 d . U . . .
C3 C 0.7158(4) 0.01385(19) 0.1563(2) 0.0186(6) Uani 1 1 d . U . . .
C7 C 0.4275(4) 0.04823(19) 0.2950(2) 0.0189(6) Uani 1 1 d . U . . .
C11 C 0.3095(4) 0.1831(2) 0.5586(3) 0.0240(7) Uani 1 1 d . U . . .
C21 C 0.6856(4) 0.31697(19) 0.2097(2) 0.0172(6) Uani 1 1 d . U . . .
C27 C 0.2280(4) 0.4140(2) 0.4660(2) 0.0214(7) Uani 1 1 d . U . . .
C9 C 0.2315(4) 0.1310(2) 0.3901(3) 0.0226(7) Uani 1 1 d . U . . .
C34 C 0.6802(4) 0.35048(19) 0.5248(2) 0.0182(6) Uani 1 1 d . U . . .
C14 C 0.7663(4) 0.1332(2) 0.6389(2) 0.0247(7) Uani 1 1 d . U . . .
C28 C 0.1975(4) 0.4486(2) 0.5572(2) 0.0248(7) Uani 1 1 d . U . . .
C30 C 0.4874(4) 0.41897(19) 0.6269(2) 0.0222(7) Uani 1 1 d . U . . .
C2 C 0.6189(4) 0.06421(19) 0.0997(2) 0.0187(6) Uani 1 1 d . U . . .
C36 C 0.5170(4) 0.38415(18) 0.5346(2) 0.0173(6) Uani 1 1 d . U . . .
C25 C 0.4115(4) 0.34062(19) 0.3590(2) 0.0180(6) Uani 1 1 d . U . . .
C16 C 0.6848(3) 0.07871(18) 0.4693(2) 0.0166(6) Uani 1 1 d . U . . .
C22 C 0.8659(4) 0.3258(2) 0.2211(2) 0.0228(7) Uani 1 1 d . U . . .
C15 C 0.8068(4) 0.0907(2) 0.5516(2) 0.0208(7) Uani 1 1 d . U . . .
C10 C 0.1912(4) 0.1734(2) 0.4764(2) 0.0256(7) Uani 1 1 d . U . . .
C32 C 0.7755(5) 0.3886(2) 0.6947(3) 0.0305(8) Uani 1 1 d . U . . .
C26 C 0.3849(3) 0.38121(18) 0.4547(2) 0.0162(6) Uani 1 1 d . U . . .
C13 C 0.6055(4) 0.1627(2) 0.6420(2) 0.0240(7) Uani 1 1 d . U . . .
C35 C 0.7101(4) 0.31054(19) 0.4297(2) 0.0183(6) Uani 1 1 d . U . . .
C23 C 0.9433(4) 0.3791(2) 0.1717(2) 0.0251(7) Uani 1 1 d . U . . .
C33 C 0.8062(4) 0.3532(2) 0.6034(2) 0.0241(7) Uani 1 1 d . U . . .
C17 C 0.7261(4) 0.03190(19) 0.3783(2) 0.0181(6) Uani 1 1 d . U . . .
C29 C 0.3225(4) 0.4500(2) 0.6351(2) 0.0271(7) Uani 1 1 d . U . . .
C31 C 0.6196(4) 0.4201(2) 0.7058(2) 0.0294(8) Uani 1 1 d . U . . .
C24 C 0.5952(4) 0.2556(2) 0.2593(2) 0.0210(7) Uani 1 1 d . U . . .
H3N H 0.889(4) 0.453(2) 0.081(2) 0.028(9) Uiso 1 1 d . . . . .
H1N H 0.916(4) 0.147(2) 0.023(2) 0.038(10) Uiso 1 1 d . . . . .
H20 H 0.467(4) 0.3589(19) 0.141(2) 0.017(7) Uiso 1 1 d . . . . .
H2 H 0.500(4) 0.0643(18) 0.0969(19) 0.011(7) Uiso 1 1 d . . . . .
H5 H 1.091(4) 0.0778(19) 0.1119(19) 0.014(7) Uiso 1 1 d . . . . .
H23 H 1.068(4) 0.386(2) 0.174(2) 0.022(8) Uiso 1 1 d . . . . .
H1 H 0.640(4) 0.151(2) 0.011(2) 0.017(8) Uiso 1 1 d . . . . .
H22 H 0.943(4) 0.294(2) 0.259(2) 0.025(8) Uiso 1 1 d . . . . .
H4 H 0.966(4) -0.016(2) 0.197(2) 0.028(9) Uiso 1 1 d . . . . .
H19 H 0.610(4) 0.448(2) 0.058(2) 0.020(8) Uiso 1 1 d . . . . .
H6A H 0.517(4) -0.0778(18) 0.1699(19) 0.010(7) Uiso 1 1 d . . . . .
H6B H 0.700(4) -0.088(2) 0.228(2) 0.017(8) Uiso 1 1 d . . . . .
H24A H 0.480(4) 0.229(2) 0.221(2) 0.025(8) Uiso 1 1 d . . . . .
H24B H 0.662(4) 0.202(2) 0.267(2) 0.022(8) Uiso 1 1 d . . . . .
H10 H 0.082(4) 0.194(2) 0.472(2) 0.024(8) Uiso 1 1 d . . . . .
H13 H 0.579(3) 0.1907(19) 0.696(2) 0.013(7) Uiso 1 1 d . . . . .
H29 H 0.298(4) 0.471(2) 0.696(2) 0.027(8) Uiso 1 1 d . . . . .
H14 H 0.844(4) 0.140(2) 0.692(2) 0.025(9) Uiso 1 1 d . . . . .
H33 H 0.907(4) 0.331(2) 0.595(2) 0.020(8) Uiso 1 1 d . . . . .
H15 H 0.916(5) 0.072(2) 0.551(2) 0.037(10) Uiso 1 1 d . . . . .
H28 H 0.088(4) 0.469(2) 0.565(2) 0.032(9) Uiso 1 1 d . . . . .
H9 H 0.154(4) 0.123(2) 0.333(2) 0.021(8) Uiso 1 1 d . . . . .
H27 H 0.144(4) 0.4102(19) 0.414(2) 0.013(8) Uiso 1 1 d . . . . .
H32 H 0.862(4) 0.385(2) 0.745(2) 0.031(9) Uiso 1 1 d . . . . .
H11 H 0.283(4) 0.212(2) 0.617(2) 0.031(9) Uiso 1 1 d . . . . .
H31 H 0.597(4) 0.439(2) 0.766(3) 0.039(10) 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
Cl1 Cd1 2.4928(8) . ?
Cl2 Cd1 2.4798(8) . ?
Cl3 Cd1 2.4669(8) . ?
Cl4 Cd1 2.4020(9) . ?
O1 C7 1.218(4) . ?
O3 C25 1.219(3) . ?
O2 C17 1.218(3) . ?
O4 C35 1.220(3) . ?
N2 C7 1.396(4) . ?
N2 C17 1.403(4) . ?
N2 C6 1.478(4) . ?
N4 C25 1.398(3) . ?
N4 C35 1.407(4) . ?
N4 C24 1.468(4) . ?
N1 C5 1.337(4) . ?
N1 C1 1.337(4) . ?
N1 H1N 0.85(3) . ?
N3 C19 1.338(4) . ?
N3 C23 1.342(4) . ?
N3 H3N 0.84(3) . ?
C5 C4 1.374(4) . ?
C5 H5 0.95(3) . ?
C1 C2 1.373(4) . ?
C1 H1 0.94(3) . ?
C20 C19 1.372(4) . ?
C20 C21 1.386(4) . ?
C20 H20 0.93(3) . ?
C18 C8 1.407(4) . ?
C18 C16 1.418(4) . ?
C18 C12 1.424(4) . ?
C4 C3 1.389(4) . ?
C4 H4 0.94(3) . ?
C6 C3 1.514(4) . ?
C6 H6A 0.99(3) . ?
C6 H6B 0.95(3) . ?
C19 H19 0.94(3) . ?
C8 C9 1.380(4) . ?
C8 C7 1.479(4) . ?
C12 C13 1.408(4) . ?
C12 C11 1.419(4) . ?
C3 C2 1.389(4) . ?
C11 C10 1.360(5) . ?
C11 H11 0.94(3) . ?
C21 C22 1.393(4) . ?
C21 C24 1.512(4) . ?
C27 C26 1.376(4) . ?
C27 C28 1.405(4) . ?
C27 H27 0.90(3) . ?
C9 C10 1.395(5) . ?
C9 H9 0.92(3) . ?
C34 C33 1.371(4) . ?
C34 C36 1.422(4) . ?
C34 C35 1.470(4) . ?
C14 C13 1.365(4) . ?
C14 C15 1.409(4) . ?
C14 H14 0.89(3) . ?
C28 C29 1.364(5) . ?
C28 H28 0.95(3) . ?
C30 C31 1.406(5) . ?
C30 C29 1.416(4) . ?
C30 C36 1.418(4) . ?
C2 H2 0.93(3) . ?
C36 C26 1.411(4) . ?
C25 C26 1.471(4) . ?
C16 C15 1.372(4) . ?
C16 C17 1.476(4) . ?
C22 C23 1.377(4) . ?
C22 H22 0.96(3) . ?
C15 H15 0.92(3) . ?
C10 H10 0.92(3) . ?
C32 C31 1.361(5) . ?
C32 C33 1.409(5) . ?
C32 H32 0.92(3) . ?
C13 H13 0.89(3) . ?
C23 H23 0.98(3) . ?
C33 H33 0.90(3) . ?
C29 H29 0.94(3) . ?
C31 H31 0.93(3) . ?
C24 H24A 0.99(3) . ?
C24 H24B 0.98(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
Cl4 Cd1 Cl3 113.99(3) . . ?
Cl4 Cd1 Cl2 119.12(3) . . ?
Cl3 Cd1 Cl2 99.68(3) . . ?
Cl4 Cd1 Cl1 106.94(3) . . ?
Cl3 Cd1 Cl1 110.12(3) . . ?
Cl2 Cd1 Cl1 106.59(3) . . ?
C7 N2 C17 125.7(2) . . ?
C7 N2 C6 117.9(2) . . ?
C17 N2 C6 116.4(2) . . ?
C25 N4 C35 125.2(2) . . ?
C25 N4 C24 117.8(2) . . ?
C35 N4 C24 116.9(2) . . ?
C5 N1 C1 122.6(3) . . ?
C5 N1 H1N 121(2) . . ?
C1 N1 H1N 117(2) . . ?
C19 N3 C23 122.9(3) . . ?
C19 N3 H3N 117(2) . . ?
C23 N3 H3N 120(2) . . ?
N1 C5 C4 119.8(3) . . ?
N1 C5 H5 115.0(17) . . ?
C4 C5 H5 125.2(17) . . ?
N1 C1 C2 119.3(3) . . ?
N1 C1 H1 117.2(17) . . ?
C2 C1 H1 123.3(17) . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 119.8(17) . . ?
C21 C20 H20 120.1(17) . . ?
C8 C18 C16 121.3(3) . . ?
C8 C18 C12 120.0(3) . . ?
C16 C18 C12 118.8(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 117.8(19) . . ?
C3 C4 H4 122.5(19) . . ?
N2 C6 C3 111.5(2) . . ?
N2 C6 H6A 110.4(15) . . ?
C3 C6 H6A 110.7(16) . . ?
N2 C6 H6B 107.1(17) . . ?
C3 C6 H6B 109.5(16) . . ?
H6A C6 H6B 107(2) . . ?
N3 C19 C20 119.3(3) . . ?
N3 C19 H19 117.0(17) . . ?
C20 C19 H19 123.6(17) . . ?
C9 C8 C18 119.8(3) . . ?
C9 C8 C7 119.7(3) . . ?
C18 C8 C7 120.5(2) . . ?
C13 C12 C11 123.4(3) . . ?
C13 C12 C18 118.8(3) . . ?
C11 C12 C18 117.8(3) . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 C6 119.9(3) . . ?
C4 C3 C6 121.7(3) . . ?
O1 C7 N2 120.2(3) . . ?
O1 C7 C8 123.8(3) . . ?
N2 C7 C8 116.0(3) . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H11 120(2) . . ?
C12 C11 H11 118(2) . . ?
C20 C21 C22 118.8(3) . . ?
C20 C21 C24 120.0(3) . . ?
C22 C21 C24 121.2(3) . . ?
C26 C27 C28 120.1(3) . . ?
C26 C27 H27 118.8(17) . . ?
C28 C27 H27 121.1(17) . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 116.9(18) . . ?
C10 C9 H9 122.5(18) . . ?
C33 C34 C36 120.3(3) . . ?
C33 C34 C35 120.5(3) . . ?
C36 C34 C35 119.2(3) . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 120(2) . . ?
C15 C14 H14 120(2) . . ?
C29 C28 C27 120.5(3) . . ?
C29 C28 H28 119.7(19) . . ?
C27 C28 H28 120(2) . . ?
C31 C30 C29 122.8(3) . . ?
C31 C30 C36 119.4(3) . . ?
C29 C30 C36 117.7(3) . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 120.1(16) . . ?
C3 C2 H2 119.7(16) . . ?
C26 C36 C30 120.2(3) . . ?
C26 C36 C34 121.2(3) . . ?
C30 C36 C34 118.6(3) . . ?
O3 C25 N4 119.8(3) . . ?
O3 C25 C26 123.7(3) . . ?
N4 C25 C26 116.5(3) . . ?
C15 C16 C18 120.8(3) . . ?
C15 C16 C17 120.0(3) . . ?
C18 C16 C17 119.2(3) . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 116.2(18) . . ?
C21 C22 H22 124.1(18) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 121(2) . . ?
C14 C15 H15 119(2) . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 125.0(19) . . ?
C9 C10 H10 114.6(19) . . ?
C31 C32 C33 120.2(3) . . ?
C31 C32 H32 123(2) . . ?
C33 C32 H32 117(2) . . ?
C27 C26 C36 120.1(3) . . ?
C27 C26 C25 119.4(3) . . ?
C36 C26 C25 120.4(2) . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 121.1(19) . . ?
C12 C13 H13 117.5(18) . . ?
O4 C35 N4 119.0(3) . . ?
O4 C35 C34 123.7(3) . . ?
N4 C35 C34 117.3(2) . . ?
N3 C23 C22 119.3(3) . . ?
N3 C23 H23 116.4(17) . . ?
C22 C23 H23 124.2(17) . . ?
C34 C33 C32 120.5(3) . . ?
C34 C33 H33 118.3(19) . . ?
C32 C33 H33 121.2(19) . . ?
O2 C17 N2 119.5(3) . . ?
O2 C17 C16 123.5(3) . . ?
N2 C17 C16 117.0(2) . . ?
C28 C29 C30 121.4(3) . . ?
C28 C29 H29 119.4(19) . . ?
C30 C29 H29 119.2(19) . . ?
C32 C31 C30 121.0(3) . . ?
C32 C31 H31 120(2) . . ?
C30 C31 H31 119(2) . . ?
N4 C24 C21 112.9(2) . . ?
N4 C24 H24A 108.1(17) . . ?
C21 C24 H24A 110.2(18) . . ?
N4 C24 H24B 108.3(17) . . ?
C21 C24 H24B 110.4(17) . . ?
H24A C24 H24B 107(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C5 C4 1.3(5) . . . . ?
C5 N1 C1 C2 -0.4(4) . . . . ?
N1 C5 C4 C3 -0.7(5) . . . . ?
C7 N2 C6 C3 95.3(3) . . . . ?
C17 N2 C6 C3 -86.3(3) . . . . ?
C23 N3 C19 C20 -0.8(5) . . . . ?
C21 C20 C19 N3 -0.2(5) . . . . ?
C16 C18 C8 C9 -178.0(2) . . . . ?
C12 C18 C8 C9 1.3(4) . . . . ?
C16 C18 C8 C7 4.4(4) . . . . ?
C12 C18 C8 C7 -176.4(2) . . . . ?
C8 C18 C12 C13 -179.9(2) . . . . ?
C16 C18 C12 C13 -0.6(4) . . . . ?
C8 C18 C12 C11 0.0(4) . . . . ?
C16 C18 C12 C11 179.3(2) . . . . ?
C5 C4 C3 C2 -0.6(4) . . . . ?
C5 C4 C3 C6 179.1(3) . . . . ?
N2 C6 C3 C2 -80.3(3) . . . . ?
N2 C6 C3 C4 100.0(3) . . . . ?
C17 N2 C7 O1 175.0(2) . . . . ?
C6 N2 C7 O1 -6.7(4) . . . . ?
C17 N2 C7 C8 -4.8(4) . . . . ?
C6 N2 C7 C8 173.5(2) . . . . ?
C9 C8 C7 O1 1.4(4) . . . . ?
C18 C8 C7 O1 179.1(3) . . . . ?
C9 C8 C7 N2 -178.8(2) . . . . ?
C18 C8 C7 N2 -1.1(4) . . . . ?
C13 C12 C11 C10 178.6(3) . . . . ?
C18 C12 C11 C10 -1.3(4) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
C19 C20 C21 C24 -177.0(3) . . . . ?
C18 C8 C9 C10 -1.4(4) . . . . ?
C7 C8 C9 C10 176.3(3) . . . . ?
C26 C27 C28 C29 -0.1(4) . . . . ?
N1 C1 C2 C3 -1.0(4) . . . . ?
C4 C3 C2 C1 1.5(4) . . . . ?
C6 C3 C2 C1 -178.3(3) . . . . ?
C31 C30 C36 C26 179.0(3) . . . . ?
C29 C30 C36 C26 0.0(4) . . . . ?
C31 C30 C36 C34 0.6(4) . . . . ?
C29 C30 C36 C34 -178.4(3) . . . . ?
C33 C34 C36 C26 -179.4(3) . . . . ?
C35 C34 C36 C26 -1.0(4) . . . . ?
C33 C34 C36 C30 -1.0(4) . . . . ?
C35 C34 C36 C30 177.5(2) . . . . ?
C35 N4 C25 O3 177.6(2) . . . . ?
C24 N4 C25 O3 -5.7(4) . . . . ?
C35 N4 C25 C26 -3.3(4) . . . . ?
C24 N4 C25 C26 173.4(2) . . . . ?
C8 C18 C16 C15 179.3(3) . . . . ?
C12 C18 C16 C15 0.0(4) . . . . ?
C8 C18 C16 C17 -2.0(4) . . . . ?
C12 C18 C16 C17 178.7(2) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C24 C21 C22 C23 177.2(3) . . . . ?
C18 C16 C15 C14 0.3(4) . . . . ?
C17 C16 C15 C14 -178.4(2) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C12 C11 C10 C9 1.3(4) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C28 C27 C26 C36 -1.4(4) . . . . ?
C28 C27 C26 C25 176.8(3) . . . . ?
C30 C36 C26 C27 1.4(4) . . . . ?
C34 C36 C26 C27 179.8(2) . . . . ?
C30 C36 C26 C25 -176.8(2) . . . . ?
C34 C36 C26 C25 1.7(4) . . . . ?
O3 C25 C26 C27 1.3(4) . . . . ?
N4 C25 C26 C27 -177.8(2) . . . . ?
O3 C25 C26 C36 179.5(3) . . . . ?
N4 C25 C26 C36 0.4(4) . . . . ?
C15 C14 C13 C12 -0.6(4) . . . . ?
C11 C12 C13 C14 -179.0(3) . . . . ?
C18 C12 C13 C14 0.9(4) . . . . ?
C25 N4 C35 O4 -176.8(2) . . . . ?
C24 N4 C35 O4 6.5(4) . . . . ?
C25 N4 C35 C34 3.9(4) . . . . ?
C24 N4 C35 C34 -172.8(2) . . . . ?
C33 C34 C35 O4 -2.5(4) . . . . ?
C36 C34 C35 O4 179.1(3) . . . . ?
C33 C34 C35 N4 176.8(2) . . . . ?
C36 C34 C35 N4 -1.7(4) . . . . ?
C19 N3 C23 C22 1.0(5) . . . . ?
C21 C22 C23 N3 -0.1(5) . . . . ?
C36 C34 C33 C32 0.5(4) . . . . ?
C35 C34 C33 C32 -177.9(3) . . . . ?
C31 C32 C33 C34 0.3(5) . . . . ?
C7 N2 C17 O2 -173.4(2) . . . . ?
C6 N2 C17 O2 8.3(4) . . . . ?
C7 N2 C17 C16 7.0(4) . . . . ?
C6 N2 C17 C16 -171.2(2) . . . . ?
C15 C16 C17 O2 -4.2(4) . . . . ?
C18 C16 C17 O2 177.1(2) . . . . ?
C15 C16 C17 N2 175.3(2) . . . . ?
C18 C16 C17 N2 -3.4(4) . . . . ?
C27 C28 C29 C30 1.5(5) . . . . ?
C31 C30 C29 C28 179.5(3) . . . . ?
C36 C30 C29 C28 -1.5(4) . . . . ?
C33 C32 C31 C30 -0.7(5) . . . . ?
C29 C30 C31 C32 179.2(3) . . . . ?
C36 C30 C31 C32 0.2(4) . . . . ?
C25 N4 C24 C21 96.4(3) . . . . ?
C35 N4 C24 C21 -86.6(3) . . . . ?
C20 C21 C24 N4 -91.7(3) . . . . ?
C22 C21 C24 N4 90.3(3) . . . . ?

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
N3 H3N Cl1 0.84(3) 2.55(3) 3.229(3) 138(3) .
N3 H3N Cl1 0.84(3) 2.67(3) 3.272(3) 130(3) 2_765
N1 H1N Cl2 0.85(3) 2.79(3) 3.389(3) 129(3) 2_765
N1 H1N Cl3 0.85(3) 2.48(3) 3.178(3) 139(3) 2_765
C20 H20 Cl1 0.93(3) 2.90(3) 3.589(3) 132(2) 2_665
C2 H2 Cl2 0.93(3) 2.88(3) 3.537(3) 128(2) 2_665
C2 H2 O1 0.93(3) 2.58(3) 3.245(3) 129(2) .
C5 H5 Cl2 0.95(3) 2.77(3) 3.448(3) 129(2) 2_765
C5 H5 O1 0.95(3) 2.40(3) 3.075(4) 127(2) 1_655
C23 H23 Cl1 0.98(3) 2.74(3) 3.372(3) 123(2) 2_765
C23 H23 O3 0.98(3) 2.51(3) 3.190(4) 127(2) 1_655
C1 H1 Cl3 0.94(3) 2.80(3) 3.361(3) 119(2) 2_765
C22 H22 O4 0.96(3) 2.59(3) 3.108(4) 114(2) .
C19 H19 Cl1 0.94(3) 2.82(3) 3.396(3) 121(2) .

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 1824822'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H13 N2 O2), Br4 Cu'
_chemical_formula_sum            'C36 H26 Br4 Cu N4 O4'
_chemical_formula_weight         961.76

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6700(4)
_cell_length_b                   7.6942(5)
_cell_length_c                   28.2690(19)
_cell_angle_alpha                87.564(3)
_cell_angle_beta                 89.895(2)
_cell_angle_gamma                89.559(2)
_cell_volume                     1666.72(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.00

_exptl_crystal_description       'Thin plate'
_exptl_crystal_colour            brown
_exptl_crystal_size_min          0.054
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_max          0.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_F_000             942.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    5.498
_shelx_estimated_absorpt_T_min   0.246
_shelx_estimated_absorpt_T_max   0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5489
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52474
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.163
_diffrn_reflns_theta_max         28.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8306
_reflns_number_gt                6778
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), 
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0267P)²+24.2233P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8306
_refine_ls_number_parameters     446
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br4 Br -0.02867(8) 0.88137(8) 0.73911(2) 0.01876(14) Uani 1 1 d . U . . .
Br1 Br 0.29931(8) 0.54422(8) 0.75409(2) 0.01809(14) Uani 1 1 d . U . . .
Br2 Br 0.45389(8) 0.88746(8) 0.82414(2) 0.02142(15) Uani 1 1 d . U . . .
Br3 Br 0.37734(9) 1.09081(9) 0.70880(2) 0.02375(15) Uani 1 1 d . U . . .
Cu1 Cu 0.27609(9) 0.84896(9) 0.75592(3) 0.01406(15) Uani 1 1 d . U . . .
O2 O -0.6041(6) 0.5959(7) 0.61810(17) 0.0261(10) Uani 1 1 d . U . . .
O3 O 1.0030(6) -0.0960(6) 0.87620(16) 0.0229(10) Uani 1 1 d . U . . .
O4 O 1.3064(7) 0.3969(6) 0.89922(19) 0.0311(12) Uani 1 1 d . U . . .
O1 O -0.1056(6) 0.8629(7) 0.56964(18) 0.0287(11) Uani 1 1 d . U . . .
N1 N -0.0233(7) 0.2796(7) 0.68546(18) 0.0176(10) Uani 1 1 d . U . . .
H1N H 0.0341 0.1841 0.6942 0.021 Uiso 1 1 calc R U . . .
N3 N 0.6579(7) 0.5030(7) 0.8215(2) 0.0214(11) Uani 1 1 d . U . . .
N4 N 1.1579(6) 0.1481(6) 0.88778(17) 0.0135(9) Uani 1 1 d . U . . .
N2 N -0.3589(7) 0.7379(7) 0.59394(18) 0.0155(10) Uani 1 1 d . U . . .
C2 C -0.0242(8) 0.5587(8) 0.6487(2) 0.0173(12) Uani 1 1 d . U . . .
H2 H 0.0359 0.6506 0.6324 0.021 Uiso 1 1 calc R U . . .
C6 C -0.3008(8) 0.7393(8) 0.6439(2) 0.0187(12) Uani 1 1 d . U . . .
H6A H -0.4036 0.7518 0.6647 0.022 Uiso 1 1 calc R U . . .
H6B H -0.2242 0.8405 0.6481 0.022 Uiso 1 1 calc R U . . .
C17 C -0.5236(8) 0.6663(8) 0.5857(2) 0.0174(11) Uani 1 1 d . U . . .
C21 C 0.9553(8) 0.3148(8) 0.8336(2) 0.0172(12) Uani 1 1 d . U . . .
C19 C 0.6508(8) 0.3339(9) 0.8144(2) 0.0218(13) Uani 1 1 d . U . . .
H19 H 0.5447 0.2817 0.8054 0.026 Uiso 1 1 calc R U . . .
C22 C 0.9567(8) 0.4910(8) 0.8407(2) 0.0183(12) Uani 1 1 d . U . . .
H22 H 1.0611 0.5465 0.8496 0.022 Uiso 1 1 calc R U . . .
C18 C -0.4862(7) 0.7581(7) 0.5005(2) 0.0132(10) Uani 1 1 d . U . . .
C4 C -0.2855(8) 0.4366(9) 0.6815(2) 0.0189(12) Uani 1 1 d . U . . .
H4 H -0.4066 0.4441 0.6884 0.023 Uiso 1 1 calc R U . . .
C26 C 1.1478(7) -0.0829(8) 0.9499(2) 0.0137(11) Uani 1 1 d . U . . .
C24 C 1.1226(8) 0.2073(8) 0.8383(2) 0.0170(12) Uani 1 1 d . U . . .
H24A H 1.1133 0.1046 0.8185 0.020 Uiso 1 1 calc R U . . .
H24B H 1.2217 0.2781 0.8262 0.020 Uiso 1 1 calc R U . . .
C3 C -0.2037(8) 0.5749(8) 0.6581(2) 0.0169(11) Uani 1 1 d . U . . .
C20 C 0.8029(8) 0.2341(8) 0.8205(2) 0.0173(12) Uani 1 1 d . U . . .
H20 H 0.8017 0.1127 0.8157 0.021 Uiso 1 1 calc R U . . .
C35 C 1.2538(8) 0.2567(8) 0.9157(2) 0.0163(11) Uani 1 1 d . U . . .
C36 C 1.2348(7) 0.0273(8) 0.9809(2) 0.0142(11) Uani 1 1 d . U . . .
C1 C 0.0644(8) 0.4091(8) 0.6633(2) 0.0184(12) Uani 1 1 d . U . . .
H1 H 0.1861 0.3982 0.6577 0.022 Uiso 1 1 calc R U . . .
C25 C 1.0964(7) -0.0150(8) 0.9020(2) 0.0142(11) Uani 1 1 d . U . . .
C34 C 1.2860(8) 0.1965(8) 0.9650(2) 0.0157(11) Uani 1 1 d . U . . .
C5 C -0.1941(9) 0.2885(9) 0.6951(2) 0.0207(13) Uani 1 1 d . U . . .
H5 H -0.2512 0.1937 0.7110 0.025 Uiso 1 1 calc R U . . .
C11 C -0.4436(9) 0.8479(9) 0.4175(2) 0.0231(13) Uani 1 1 d . U . . .
H11 H -0.4862 0.8587 0.3860 0.028 Uiso 1 1 calc R U . . .
C23 C 0.8031(8) 0.5861(8) 0.8346(2) 0.0211(13) Uani 1 1 d . U . . .
H23 H 0.8004 0.7074 0.8396 0.025 Uiso 1 1 calc R U . . .
C7 C -0.2490(8) 0.8099(8) 0.5590(2) 0.0176(12) Uani 1 1 d . U . . .
C27 C 1.1055(8) -0.2501(8) 0.9652(2) 0.0191(12) Uani 1 1 d . U . . .
H27 H 1.0482 -0.3244 0.9443 0.023 Uiso 1 1 calc R U . . .
C9 C -0.2167(8) 0.8918(9) 0.4736(2) 0.0216(13) Uani 1 1 d . U . . .
H9 H -0.1034 0.9333 0.4802 0.026 Uiso 1 1 calc R U . . .
C8 C -0.3160(8) 0.8199(8) 0.5101(2) 0.0162(11) Uani 1 1 d . U . . .
C15 C -0.7555(8) 0.6246(8) 0.5271(2) 0.0200(12) Uani 1 1 d . U . . .
H15 H -0.8250 0.5728 0.5516 0.024 Uiso 1 1 calc R U . . .
C16 C -0.5892(8) 0.6818(8) 0.5366(2) 0.0172(11) Uani 1 1 d . U . . .
C31 C 1.3571(8) 0.0838(9) 1.0580(2) 0.0226(13) Uani 1 1 d . U . . .
H31 H 1.3821 0.0466 1.0898 0.027 Uiso 1 1 calc R U . . .
C28 C 1.1468(8) -0.3110(9) 1.0113(2) 0.0207(13) Uani 1 1 d . U . . .
H28 H 1.1184 -0.4267 1.0214 0.025 Uiso 1 1 calc R U . . .
C30 C 1.2736(8) -0.0332(8) 1.0275(2) 0.0181(12) Uani 1 1 d . U . . .
C13 C -0.7215(9) 0.7140(9) 0.4449(2) 0.0231(13) Uani 1 1 d . U . . .
H13 H -0.7679 0.7229 0.4137 0.028 Uiso 1 1 calc R U . . .
C10 C -0.2796(9) 0.9048(9) 0.4273(2) 0.0252(14) Uani 1 1 d . U . . .
H10 H -0.2086 0.9531 0.4026 0.030 Uiso 1 1 calc R U . . .
C12 C -0.5502(8) 0.7737(8) 0.4533(2) 0.0182(12) Uani 1 1 d . U . . .
C33 C 1.3668(8) 0.3037(9) 0.9955(2) 0.0214(13) Uani 1 1 d . U . . .
H33 H 1.4001 0.4175 0.9848 0.026 Uiso 1 1 calc R U . . .
C32 C 1.4010(9) 0.2457(9) 1.0428(2) 0.0253(14) Uani 1 1 d . U . . .
H32 H 1.4553 0.3214 1.0638 0.030 Uiso 1 1 calc R U . . .
C29 C 1.2281(8) -0.2038(9) 1.0420(2) 0.0212(13) Uani 1 1 d . U . . .
H29 H 1.2537 -0.2456 1.0734 0.025 Uiso 1 1 calc R U . . .
C14 C -0.8201(9) 0.6441(9) 0.4808(3) 0.0266(14) Uani 1 1 d . U . . .
H14 H -0.9354 0.6077 0.4744 0.032 Uiso 1 1 calc R U . . .
H3N H 0.559(9) 0.564(8) 0.819(2) 0.005(15) 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
Br4 Cu1 2.3952(9) . ?
Br1 Cu1 2.3529(9) . ?
Br2 Cu1 2.3940(9) . ?
Br3 Cu1 2.3765(10) . ?
O2 C17 1.214(8) . ?
O3 C25 1.217(7) . ?
O4 C35 1.228(8) . ?
O1 C7 1.219(8) . ?
N1 C1 1.339(8) . ?
N1 C5 1.339(8) . ?
N1 H1N 0.8800 . ?
N3 C19 1.326(8) . ?
N3 C23 1.349(9) . ?
N3 H3N 0.89(7) . ?
N4 C35 1.389(8) . ?
N4 C25 1.387(8) . ?
N4 C24 1.478(7) . ?
N2 C7 1.397(8) . ?
N2 C17 1.405(8) . ?
N2 C6 1.482(8) . ?
C2 C1 1.380(9) . ?
C2 C3 1.407(9) . ?
C2 H2 0.9500 . ?
C6 C3 1.503(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C17 C16 1.478(8) . ?
C21 C22 1.379(9) . ?
C21 C20 1.386(9) . ?
C21 C24 1.524(8) . ?
C19 C20 1.398(9) . ?
C19 H19 0.9500 . ?
C22 C23 1.389(9) . ?
C22 H22 0.9500 . ?
C18 C16 1.402(8) . ?
C18 C8 1.423(8) . ?
C18 C12 1.421(8) . ?
C4 C5 1.374(9) . ?
C4 C3 1.384(9) . ?
C4 H4 0.9500 . ?
C26 C27 1.380(9) . ?
C26 C36 1.416(8) . ?
C26 C25 1.484(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C20 H20 0.9500 . ?
C35 C34 1.470(8) . ?
C36 C30 1.412(8) . ?
C36 C34 1.417(9) . ?
C1 H1 0.9500 . ?
C34 C33 1.370(8) . ?
C5 H5 0.9500 . ?
C11 C10 1.368(10) . ?
C11 C12 1.405(9) . ?
C11 H11 0.9500 . ?
C23 H23 0.9500 . ?
C7 C8 1.474(8) . ?
C27 C28 1.403(9) . ?
C27 H27 0.9500 . ?
C9 C8 1.379(9) . ?
C9 C10 1.397(10) . ?
C9 H9 0.9500 . ?
C15 C16 1.383(9) . ?
C15 C14 1.403(9) . ?
C15 H15 0.9500 . ?
C31 C32 1.346(10) . ?
C31 C30 1.429(9) . ?
C31 H31 0.9500 . ?
C28 C29 1.376(10) . ?
C28 H28 0.9500 . ?
C30 C29 1.404(9) . ?
C13 C14 1.360(10) . ?
C13 C12 1.419(9) . ?
C13 H13 0.9500 . ?
C10 H10 0.9500 . ?
C33 C32 1.416(10) . ?
C33 H33 0.9500 . ?
C32 H32 0.9500 . ?
C29 H29 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Cu1 Br3 136.25(4) . . ?
Br1 Cu1 Br2 97.83(3) . . ?
Br3 Cu1 Br2 98.10(4) . . ?
Br1 Cu1 Br4 99.06(3) . . ?
Br3 Cu1 Br4 98.05(3) . . ?
Br2 Cu1 Br4 134.62(4) . . ?
C1 N1 C5 123.2(6) . . ?
C1 N1 H1N 118.4 . . ?
C5 N1 H1N 118.4 . . ?
C19 N3 C23 124.1(6) . . ?
C19 N3 H3N 118(4) . . ?
C23 N3 H3N 118(4) . . ?
C35 N4 C25 125.4(5) . . ?
C35 N4 C24 117.9(5) . . ?
C25 N4 C24 116.7(5) . . ?
C7 N2 C17 125.1(5) . . ?
C7 N2 C6 118.2(5) . . ?
C17 N2 C6 116.7(5) . . ?
C1 C2 C3 119.9(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N2 C6 C3 111.3(5) . . ?
N2 C6 H6A 109.4 . . ?
C3 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C3 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O2 C17 N2 120.1(6) . . ?
O2 C17 C16 123.3(6) . . ?
N2 C17 C16 116.5(5) . . ?
C22 C21 C20 120.4(6) . . ?
C22 C21 C24 120.5(6) . . ?
C20 C21 C24 119.0(6) . . ?
N3 C19 C20 118.6(6) . . ?
N3 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C21 C22 C23 119.0(6) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C16 C18 C8 121.0(5) . . ?
C16 C18 C12 120.3(6) . . ?
C8 C18 C12 118.8(5) . . ?
C5 C4 C3 120.9(6) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C27 C26 C36 119.8(6) . . ?
C27 C26 C25 120.6(5) . . ?
C36 C26 C25 119.5(5) . . ?
N4 C24 C21 112.3(5) . . ?
N4 C24 H24A 109.1 . . ?
C21 C24 H24A 109.1 . . ?
N4 C24 H24B 109.1 . . ?
C21 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
C4 C3 C2 117.8(6) . . ?
C4 C3 C6 121.7(6) . . ?
C2 C3 C6 120.5(6) . . ?
C21 C20 C19 119.1(6) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
O4 C35 N4 120.2(6) . . ?
O4 C35 C34 122.7(6) . . ?
N4 C35 C34 117.1(5) . . ?
C30 C36 C26 119.6(6) . . ?
C30 C36 C34 119.9(5) . . ?
C26 C36 C34 120.4(5) . . ?
N1 C1 C2 119.2(6) . . ?
N1 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
O3 C25 N4 120.8(6) . . ?
O3 C25 C26 122.3(6) . . ?
N4 C25 C26 116.9(5) . . ?
C33 C34 C36 120.0(6) . . ?
C33 C34 C35 119.9(6) . . ?
C36 C34 C35 120.0(5) . . ?
N1 C5 C4 119.1(6) . . ?
N1 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C10 C11 C12 121.1(6) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
N3 C23 C22 118.8(6) . . ?
N3 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
O1 C7 N2 119.9(6) . . ?
O1 C7 C8 123.0(6) . . ?
N2 C7 C8 117.1(5) . . ?
C26 C27 C28 120.4(6) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C8 C9 C10 121.3(6) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C8 C18 119.6(6) . . ?
C9 C8 C7 120.6(6) . . ?
C18 C8 C7 119.7(5) . . ?
C16 C15 C14 119.1(6) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C18 120.5(6) . . ?
C15 C16 C17 119.0(6) . . ?
C18 C16 C17 120.4(6) . . ?
C32 C31 C30 121.4(6) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C29 C28 C27 120.3(6) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C29 C30 C36 119.1(6) . . ?
C29 C30 C31 123.0(6) . . ?
C36 C30 C31 117.9(6) . . ?
C14 C13 C12 120.8(6) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C11 C10 C9 119.9(6) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C11 C12 C13 123.0(6) . . ?
C11 C12 C18 119.3(6) . . ?
C13 C12 C18 117.7(6) . . ?
C34 C33 C32 120.3(6) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C31 C32 C33 120.4(6) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C28 C29 C30 120.7(6) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C13 C14 C15 121.5(6) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C6 C3 -91.8(7) . . . . ?
C17 N2 C6 C3 89.4(7) . . . . ?
C7 N2 C17 O2 174.8(6) . . . . ?
C6 N2 C17 O2 -6.4(9) . . . . ?
C7 N2 C17 C16 -5.0(9) . . . . ?
C6 N2 C17 C16 173.8(5) . . . . ?
C23 N3 C19 C20 -0.6(10) . . . . ?
C20 C21 C22 C23 0.1(9) . . . . ?
C24 C21 C22 C23 177.9(6) . . . . ?
C35 N4 C24 C21 -88.8(6) . . . . ?
C25 N4 C24 C21 93.1(6) . . . . ?
C22 C21 C24 N4 85.1(7) . . . . ?
C20 C21 C24 N4 -97.1(7) . . . . ?
C5 C4 C3 C2 -0.1(9) . . . . ?
C5 C4 C3 C6 -178.8(6) . . . . ?
C1 C2 C3 C4 -0.7(9) . . . . ?
C1 C2 C3 C6 178.0(6) . . . . ?
N2 C6 C3 C4 -96.6(7) . . . . ?
N2 C6 C3 C2 84.8(7) . . . . ?
C22 C21 C20 C19 0.2(9) . . . . ?
C24 C21 C20 C19 -177.5(6) . . . . ?
N3 C19 C20 C21 0.0(10) . . . . ?
C25 N4 C35 O4 177.9(6) . . . . ?
C24 N4 C35 O4 0.0(9) . . . . ?
C25 N4 C35 C34 -2.8(9) . . . . ?
C24 N4 C35 C34 179.3(5) . . . . ?
C27 C26 C36 C30 -1.7(9) . . . . ?
C25 C26 C36 C30 175.8(5) . . . . ?
C27 C26 C36 C34 177.1(6) . . . . ?
C25 C26 C36 C34 -5.3(8) . . . . ?
C5 N1 C1 C2 -1.1(9) . . . . ?
C3 C2 C1 N1 1.3(9) . . . . ?
C35 N4 C25 O3 174.9(6) . . . . ?
C24 N4 C25 O3 -7.2(8) . . . . ?
C35 N4 C25 C26 -4.3(8) . . . . ?
C24 N4 C25 C26 173.6(5) . . . . ?
C27 C26 C25 O3 6.7(9) . . . . ?
C36 C26 C25 O3 -170.8(6) . . . . ?
C27 C26 C25 N4 -174.1(5) . . . . ?
C36 C26 C25 N4 8.4(8) . . . . ?
C30 C36 C34 C33 -2.6(9) . . . . ?
C26 C36 C34 C33 178.6(6) . . . . ?
C30 C36 C34 C35 176.9(5) . . . . ?
C26 C36 C34 C35 -2.0(8) . . . . ?
O4 C35 C34 C33 4.8(9) . . . . ?
N4 C35 C34 C33 -174.5(6) . . . . ?
O4 C35 C34 C36 -174.6(6) . . . . ?
N4 C35 C34 C36 6.1(8) . . . . ?
C1 N1 C5 C4 0.2(9) . . . . ?
C3 C4 C5 N1 0.4(10) . . . . ?
C19 N3 C23 C22 0.9(10) . . . . ?
C21 C22 C23 N3 -0.6(9) . . . . ?
C17 N2 C7 O1 -177.2(6) . . . . ?
C6 N2 C7 O1 4.0(9) . . . . ?
C17 N2 C7 C8 3.6(9) . . . . ?
C6 N2 C7 C8 -175.1(5) . . . . ?
C36 C26 C27 C28 0.7(9) . . . . ?
C25 C26 C27 C28 -176.8(6) . . . . ?
C10 C9 C8 C18 -0.2(10) . . . . ?
C10 C9 C8 C7 -178.9(6) . . . . ?
C16 C18 C8 C9 178.9(6) . . . . ?
C12 C18 C8 C9 -0.6(9) . . . . ?
C16 C18 C8 C7 -2.3(9) . . . . ?
C12 C18 C8 C7 178.2(5) . . . . ?
O1 C7 C8 C9 -0.2(10) . . . . ?
N2 C7 C8 C9 178.9(6) . . . . ?
O1 C7 C8 C18 -178.9(6) . . . . ?
N2 C7 C8 C18 0.2(8) . . . . ?
C14 C15 C16 C18 -0.1(10) . . . . ?
C14 C15 C16 C17 178.0(6) . . . . ?
C8 C18 C16 C15 179.0(6) . . . . ?
C12 C18 C16 C15 -1.5(9) . . . . ?
C8 C18 C16 C17 0.9(9) . . . . ?
C12 C18 C16 C17 -179.6(5) . . . . ?
O2 C17 C16 C15 4.7(10) . . . . ?
N2 C17 C16 C15 -175.5(6) . . . . ?
O2 C17 C16 C18 -177.2(6) . . . . ?
N2 C17 C16 C18 2.6(9) . . . . ?
C26 C27 C28 C29 0.7(9) . . . . ?
C26 C36 C30 C29 1.3(9) . . . . ?
C34 C36 C30 C29 -177.5(6) . . . . ?
C26 C36 C30 C31 -178.2(5) . . . . ?
C34 C36 C30 C31 2.9(8) . . . . ?
C32 C31 C30 C29 179.1(6) . . . . ?
C32 C31 C30 C36 -1.4(9) . . . . ?
C12 C11 C10 C9 -0.9(11) . . . . ?
C8 C9 C10 C11 1.0(11) . . . . ?
C10 C11 C12 C13 179.6(6) . . . . ?
C10 C11 C12 C18 0.1(10) . . . . ?
C14 C13 C12 C11 -179.6(7) . . . . ?
C14 C13 C12 C18 -0.1(10) . . . . ?
C16 C18 C12 C11 -178.9(6) . . . . ?
C8 C18 C12 C11 0.6(9) . . . . ?
C16 C18 C12 C13 1.6(9) . . . . ?
C8 C18 C12 C13 -178.9(6) . . . . ?
C36 C34 C33 C32 0.5(9) . . . . ?
C35 C34 C33 C32 -178.9(6) . . . . ?
C30 C31 C32 C33 -0.7(10) . . . . ?
C34 C33 C32 C31 1.1(10) . . . . ?
C27 C28 C29 C30 -1.1(10) . . . . ?
C36 C30 C29 C28 0.0(9) . . . . ?
C31 C30 C29 C28 179.6(6) . . . . ?
C12 C13 C14 C15 -1.5(11) . . . . ?
C16 C15 C14 C13 1.6(10) . . . . ?

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
N1 H1N Br4 0.88 2.65 3.361(5) 138.3 1_545
N1 H1N Br3 0.88 2.75 3.442(5) 136.4 1_545
N3 H3N Br1 0.89(7) 2.73(6) 3.353(6) 128(5) .
N3 H3N Br2 0.89(7) 2.62(7) 3.339(6) 139(5) .
C2 H2 O1 0.95 2.59 3.225(8) 124.3 .
C6 H6B Br4 0.99 3.01 3.620(6) 120.9 .
C19 H19 Br1 0.95 3.07 3.537(6) 111.9 .
C22 H22 O4 0.95 2.58 3.216(8) 124.3 .
C4 H4 Br1 0.95 3.03 3.887(6) 150.1 1_455
C24 H24A Br4 0.99 3.09 4.019(6) 157.0 1_645
C24 H24A Br2 0.99 3.09 3.558(6) 110.3 1_645
C24 H24B Br1 0.99 2.89 3.707(6) 140.1 1_655
C1 H1 Br3 0.95 3.08 3.615(6) 117.1 1_545
C1 H1 O2 0.95 2.46 3.170(8) 131.7 1_655
C5 H5 Br4 0.95 3.02 3.548(6) 116.8 1_545
C5 H5 Br3 0.95 2.96 3.646(7) 129.8 1_445
C23 H23 Br2 0.95 3.01 3.534(6) 116.1 .
C23 H23 O3 0.95 2.44 3.166(8) 133.2 1_565

_refine_diff_density_max         1.810
_refine_diff_density_min         -1.093
_refine_diff_density_rms         0.184

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 1824818'
_audit_update_record             
;
2018-02-20 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H13 N2 O2), Br4 Zn'
_chemical_formula_sum            'C36 H26 Br4 N4 O4 Zn'
_chemical_formula_weight         963.62

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9152(3)
_cell_length_b                   14.7377(6)
_cell_length_c                   14.9796(6)
_cell_angle_alpha                102.5410(10)
_cell_angle_beta                 100.9130(10)
_cell_angle_gamma                93.4390(10)
_cell_volume                     1665.52(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9864
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      31.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    5.584
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5506
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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 kappa, Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58279
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6807
_reflns_number_gt                6016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0449P)²+2.0447P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6807
_refine_ls_number_parameters     546
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.78552(4) 0.54942(2) -0.04107(2) 0.01927(8) Uani 1 1 d . U . . .
Br2 Br 0.73230(4) 0.81424(2) -0.01666(2) 0.02278(8) Uani 1 1 d . U . . .
Br3 Br 1.17100(4) 0.74865(2) 0.09251(2) 0.02785(9) Uani 1 1 d . U . . .
Br4 Br 0.77331(5) 0.69591(3) 0.20618(2) 0.03880(10) Uani 1 1 d . U . . .
Zn1 Zn 0.86448(4) 0.70250(2) 0.06590(2) 0.02064(9) Uani 1 1 d . U . . .
O1 O 0.3282(3) 0.03519(15) 0.22230(15) 0.0249(5) Uani 1 1 d . U . . .
O3 O 0.3091(3) 0.33273(16) 0.29013(15) 0.0268(5) Uani 1 1 d . U . . .
O2 O 0.8673(3) 0.00599(15) 0.37176(15) 0.0239(5) Uani 1 1 d . U . . .
O4 O 0.8506(3) 0.28334(17) 0.42038(17) 0.0292(5) Uani 1 1 d . U . . .
N2 N 0.5928(3) 0.01488(16) 0.29959(16) 0.0159(5) Uani 1 1 d . U . . .
N4 N 0.5776(3) 0.30501(16) 0.35724(16) 0.0160(5) Uani 1 1 d . U . . .
N1 N 0.8774(3) 0.11355(18) 0.06074(18) 0.0213(5) Uani 1 1 d . U . . .
N3 N 0.8516(3) 0.42037(18) 0.12185(18) 0.0231(5) Uani 1 1 d . U . . .
C5 C 0.9735(4) 0.0676(2) 0.1160(2) 0.0236(6) Uani 1 1 d . U . . .
C1 C 0.7058(4) 0.1126(2) 0.0532(2) 0.0213(6) Uani 1 1 d . U . . .
C20 C 0.5981(4) 0.3637(2) 0.1588(2) 0.0203(6) Uani 1 1 d . U . . .
C18 C 0.5183(3) 0.10823(18) 0.4701(2) 0.0153(5) Uani 1 1 d . U . . .
C4 C 0.8961(4) 0.0164(2) 0.1666(2) 0.0218(6) Uani 1 1 d . U . . .
C6 C 0.6281(4) -0.0436(2) 0.2135(2) 0.0197(6) Uani 1 1 d . U . . .
C19 C 0.6793(4) 0.4160(2) 0.1109(2) 0.0240(6) Uani 1 1 d . U . . .
C8 C 0.3939(3) 0.09712(18) 0.3869(2) 0.0162(5) Uani 1 1 d . U . . .
C12 C 0.4781(4) 0.15122(18) 0.5569(2) 0.0194(6) Uani 1 1 d . U . . .
C3 C 0.7188(4) 0.01310(19) 0.16035(19) 0.0171(6) Uani 1 1 d . U . . .
C7 C 0.4305(3) 0.04804(19) 0.2967(2) 0.0174(6) Uani 1 1 d . U . . .
C11 C 0.3110(4) 0.1816(2) 0.5563(2) 0.0232(6) Uani 1 1 d . U . . .
C21 C 0.6937(4) 0.31553(19) 0.21675(19) 0.0176(6) Uani 1 1 d . U . . .
C27 C 0.2316(4) 0.4121(2) 0.4648(2) 0.0214(6) Uani 1 1 d . U . . .
C9 C 0.2338(4) 0.1291(2) 0.3892(2) 0.0212(6) Uani 1 1 d . U . . .
C34 C 0.6814(4) 0.35152(19) 0.5268(2) 0.0186(6) Uani 1 1 d . U . . .
C14 C 0.7661(4) 0.1326(2) 0.6364(2) 0.0238(6) Uani 1 1 d . U . . .
C28 C 0.1987(4) 0.4466(2) 0.5540(2) 0.0256(7) Uani 1 1 d . U . . .
C30 C 0.4861(4) 0.4186(2) 0.6255(2) 0.0222(6) Uani 1 1 d . U . . .
C2 C 0.6242(4) 0.0632(2) 0.1030(2) 0.0187(6) Uani 1 1 d . U . . .
C36 C 0.5193(4) 0.38357(18) 0.5352(2) 0.0175(6) Uani 1 1 d . U . . .
C25 C 0.4173(4) 0.33904(19) 0.3616(2) 0.0171(6) Uani 1 1 d . U . . .
C16 C 0.6847(3) 0.07819(18) 0.4686(2) 0.0158(5) Uani 1 1 d . U . . .
C22 C 0.8734(4) 0.3226(2) 0.2265(2) 0.0231(6) Uani 1 1 d . U . . .
C15 C 0.8059(4) 0.0909(2) 0.5508(2) 0.0196(6) Uani 1 1 d . U . . .
C10 C 0.1942(4) 0.1716(2) 0.4749(3) 0.0249(7) Uani 1 1 d . U . . .
C32 C 0.7730(5) 0.3897(2) 0.6950(2) 0.0304(7) Uani 1 1 d . U . . .
C26 C 0.3893(4) 0.38026(18) 0.4555(2) 0.0165(6) Uani 1 1 d . U . . .
C13 C 0.6056(4) 0.1621(2) 0.6394(2) 0.0231(6) Uani 1 1 d . U . . .
C35 C 0.7138(4) 0.31175(19) 0.4336(2) 0.0191(6) Uani 1 1 d . U . . .
C23 C 0.9494(4) 0.3757(2) 0.1778(2) 0.0248(7) Uani 1 1 d . U . . .
C33 C 0.8056(4) 0.3548(2) 0.6054(2) 0.0251(7) Uani 1 1 d . U . . .
C17 C 0.7262(3) 0.03169(19) 0.3792(2) 0.0161(5) Uani 1 1 d . U . . .
C29 C 0.3218(4) 0.4489(2) 0.6322(2) 0.0264(7) Uani 1 1 d . U . . .
C31 C 0.6168(5) 0.4203(2) 0.7047(2) 0.0300(7) Uani 1 1 d . U . . .
C24 C 0.6028(4) 0.2543(2) 0.2662(2) 0.0212(6) Uani 1 1 d . U . . .
H3N H 0.903(5) 0.448(3) 0.085(3) 0.037(11) Uiso 1 1 d . . . . .
H1N H 0.928(5) 0.145(2) 0.028(3) 0.027(9) Uiso 1 1 d . . . . .
H5 H 1.082(5) 0.076(2) 0.118(2) 0.022(9) Uiso 1 1 d . . . . .
H4 H 0.960(4) -0.014(2) 0.202(2) 0.014(8) Uiso 1 1 d . . . . .
H1 H 0.647(4) 0.150(2) 0.014(2) 0.020(8) Uiso 1 1 d . . . . .
H2 H 0.512(4) 0.063(2) 0.099(2) 0.009(7) Uiso 1 1 d . . . . .
H23 H 1.066(5) 0.384(2) 0.183(3) 0.031(10) Uiso 1 1 d . . . . .
H19 H 0.616(5) 0.452(2) 0.071(3) 0.030(9) Uiso 1 1 d . . . . .
H22 H 0.942(5) 0.291(2) 0.262(3) 0.026(9) Uiso 1 1 d . . . . .
H20 H 0.471(5) 0.357(3) 0.148(3) 0.037(10) Uiso 1 1 d . . . . .
H6B H 0.693(4) -0.090(2) 0.227(2) 0.011(7) Uiso 1 1 d . . . . .
H24B H 0.666(4) 0.203(2) 0.273(2) 0.019(8) Uiso 1 1 d . . . . .
H6A H 0.523(4) -0.073(2) 0.177(2) 0.014(8) Uiso 1 1 d . . . . .
H24A H 0.491(5) 0.230(3) 0.229(3) 0.035(10) Uiso 1 1 d . . . . .
H14 H 0.850(4) 0.139(2) 0.688(2) 0.011(7) Uiso 1 1 d . . . . .
H11 H 0.288(4) 0.213(2) 0.616(2) 0.021(8) Uiso 1 1 d . . . . .
H29 H 0.304(4) 0.471(2) 0.693(2) 0.016(8) Uiso 1 1 d . . . . .
H15 H 0.902(5) 0.069(2) 0.547(2) 0.020(9) Uiso 1 1 d . . . . .
H10 H 0.097(5) 0.191(3) 0.469(3) 0.037(11) Uiso 1 1 d . . . . .
H13 H 0.580(4) 0.190(2) 0.691(2) 0.018(8) Uiso 1 1 d . . . . .
H32 H 0.849(5) 0.387(3) 0.747(3) 0.034(10) Uiso 1 1 d . . . . .
H28 H 0.088(5) 0.466(3) 0.560(3) 0.034(10) Uiso 1 1 d . . . . .
H9 H 0.153(4) 0.122(2) 0.336(2) 0.018(8) Uiso 1 1 d . . . . .
H27 H 0.147(5) 0.408(2) 0.412(3) 0.025(9) Uiso 1 1 d . . . . .
H33 H 0.905(5) 0.331(2) 0.599(2) 0.027(9) Uiso 1 1 d . . . . .
H31 H 0.588(5) 0.440(2) 0.766(3) 0.033(10) 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
Br1 Zn1 2.4351(4) . ?
Br2 Zn1 2.4366(4) . ?
Br3 Zn1 2.4137(5) . ?
Br4 Zn1 2.3664(5) . ?
O1 C7 1.218(4) . ?
O3 C25 1.220(4) . ?
O2 C17 1.218(3) . ?
O4 C35 1.219(4) . ?
N2 C7 1.398(4) . ?
N2 C17 1.401(4) . ?
N2 C6 1.472(4) . ?
N4 C35 1.397(4) . ?
N4 C25 1.400(4) . ?
N4 C24 1.462(4) . ?
N1 C5 1.338(4) . ?
N1 C1 1.340(4) . ?
N3 C19 1.338(4) . ?
N3 C23 1.339(4) . ?
C5 C4 1.373(4) . ?
C1 C2 1.366(4) . ?
C20 C19 1.369(4) . ?
C20 C21 1.384(4) . ?
C18 C8 1.407(4) . ?
C18 C16 1.417(4) . ?
C18 C12 1.420(4) . ?
C4 C3 1.386(4) . ?
C6 C3 1.510(4) . ?
C8 C9 1.382(4) . ?
C8 C7 1.477(4) . ?
C12 C13 1.412(4) . ?
C12 C11 1.421(4) . ?
C3 C2 1.393(4) . ?
C11 C10 1.357(5) . ?
C21 C22 1.397(4) . ?
C21 C24 1.515(4) . ?
C27 C26 1.380(4) . ?
C27 C28 1.401(4) . ?
C9 C10 1.402(5) . ?
C34 C33 1.374(4) . ?
C34 C36 1.412(4) . ?
C34 C35 1.469(4) . ?
C14 C13 1.372(5) . ?
C14 C15 1.400(4) . ?
C28 C29 1.367(5) . ?
C30 C31 1.414(5) . ?
C30 C29 1.414(5) . ?
C30 C36 1.419(4) . ?
C36 C26 1.411(4) . ?
C25 C26 1.470(4) . ?
C16 C15 1.379(4) . ?
C16 C17 1.471(4) . ?
C22 C23 1.365(4) . ?
C32 C31 1.363(5) . ?
C32 C33 1.406(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
Br4 Zn1 Br3 112.091(19) . . ?
Br4 Zn1 Br1 107.921(17) . . ?
Br3 Zn1 Br1 111.149(16) . . ?
Br4 Zn1 Br2 115.351(18) . . ?
Br3 Zn1 Br2 103.983(16) . . ?
Br1 Zn1 Br2 106.206(16) . . ?
C7 N2 C17 125.0(2) . . ?
C7 N2 C6 118.5(2) . . ?
C17 N2 C6 116.5(2) . . ?
C35 N4 C25 125.4(2) . . ?
C35 N4 C24 116.8(2) . . ?
C25 N4 C24 117.7(2) . . ?
C5 N1 C1 122.3(3) . . ?
C19 N3 C23 122.9(3) . . ?
N1 C5 C4 119.8(3) . . ?
N1 C1 C2 119.6(3) . . ?
C19 C20 C21 120.1(3) . . ?
C8 C18 C16 120.9(3) . . ?
C8 C18 C12 119.8(3) . . ?
C16 C18 C12 119.4(3) . . ?
C5 C4 C3 119.8(3) . . ?
N2 C6 C3 112.0(2) . . ?
N3 C19 C20 119.1(3) . . ?
C9 C8 C18 120.2(3) . . ?
C9 C8 C7 119.3(3) . . ?
C18 C8 C7 120.4(2) . . ?
C13 C12 C18 118.6(3) . . ?
C13 C12 C11 123.2(3) . . ?
C18 C12 C11 118.2(3) . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 C6 121.5(3) . . ?
C2 C3 C6 120.2(3) . . ?
O1 C7 N2 119.7(3) . . ?
O1 C7 C8 123.8(3) . . ?
N2 C7 C8 116.5(2) . . ?
C10 C11 C12 120.9(3) . . ?
C20 C21 C22 118.9(3) . . ?
C20 C21 C24 119.9(3) . . ?
C22 C21 C24 121.2(3) . . ?
C26 C27 C28 120.0(3) . . ?
C8 C9 C10 119.9(3) . . ?
C33 C34 C36 120.1(3) . . ?
C33 C34 C35 120.4(3) . . ?
C36 C34 C35 119.5(3) . . ?
C13 C14 C15 120.1(3) . . ?
C29 C28 C27 120.5(3) . . ?
C31 C30 C29 122.9(3) . . ?
C31 C30 C36 118.8(3) . . ?
C29 C30 C36 118.3(3) . . ?
C1 C2 C3 120.1(3) . . ?
C26 C36 C34 121.1(3) . . ?
C26 C36 C30 119.5(3) . . ?
C34 C36 C30 119.3(3) . . ?
O3 C25 N4 120.3(3) . . ?
O3 C25 C26 123.5(3) . . ?
N4 C25 C26 116.2(2) . . ?
C15 C16 C18 120.1(3) . . ?
C15 C16 C17 120.2(3) . . ?
C18 C16 C17 119.7(2) . . ?
C23 C22 C21 119.2(3) . . ?
C16 C15 C14 120.7(3) . . ?
C11 C10 C9 120.9(3) . . ?
C31 C32 C33 120.2(3) . . ?
C27 C26 C36 120.5(3) . . ?
C27 C26 C25 119.1(3) . . ?
C36 C26 C25 120.4(3) . . ?
C14 C13 C12 121.1(3) . . ?
O4 C35 N4 119.3(3) . . ?
O4 C35 C34 123.5(3) . . ?
N4 C35 C34 117.2(2) . . ?
N3 C23 C22 119.8(3) . . ?
C34 C33 C32 120.6(3) . . ?
O2 C17 N2 119.2(3) . . ?
O2 C17 C16 123.6(3) . . ?
N2 C17 C16 117.1(2) . . ?
C28 C29 C30 121.2(3) . . ?
C32 C31 C30 120.9(3) . . ?
N4 C24 C21 112.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C5 C4 0.8(5) . . . . ?
C5 N1 C1 C2 -0.2(4) . . . . ?
N1 C5 C4 C3 -0.3(5) . . . . ?
C7 N2 C6 C3 95.2(3) . . . . ?
C17 N2 C6 C3 -85.8(3) . . . . ?
C23 N3 C19 C20 0.0(5) . . . . ?
C21 C20 C19 N3 -0.7(5) . . . . ?
C16 C18 C8 C9 -178.2(2) . . . . ?
C12 C18 C8 C9 0.9(4) . . . . ?
C16 C18 C8 C7 4.1(4) . . . . ?
C12 C18 C8 C7 -176.7(2) . . . . ?
C8 C18 C12 C13 -179.6(2) . . . . ?
C16 C18 C12 C13 -0.5(4) . . . . ?
C8 C18 C12 C11 0.1(4) . . . . ?
C16 C18 C12 C11 179.3(2) . . . . ?
C5 C4 C3 C2 -0.6(4) . . . . ?
C5 C4 C3 C6 178.9(3) . . . . ?
N2 C6 C3 C4 99.7(3) . . . . ?
N2 C6 C3 C2 -80.7(3) . . . . ?
C17 N2 C7 O1 174.6(3) . . . . ?
C6 N2 C7 O1 -6.5(4) . . . . ?
C17 N2 C7 C8 -5.8(4) . . . . ?
C6 N2 C7 C8 173.2(2) . . . . ?
C9 C8 C7 O1 1.6(4) . . . . ?
C18 C8 C7 O1 179.3(3) . . . . ?
C9 C8 C7 N2 -178.0(2) . . . . ?
C18 C8 C7 N2 -0.4(4) . . . . ?
C13 C12 C11 C10 178.4(3) . . . . ?
C18 C12 C11 C10 -1.3(4) . . . . ?
C19 C20 C21 C22 1.1(4) . . . . ?
C19 C20 C21 C24 -177.2(3) . . . . ?
C18 C8 C9 C10 -0.9(4) . . . . ?
C7 C8 C9 C10 176.8(3) . . . . ?
C26 C27 C28 C29 -0.1(5) . . . . ?
N1 C1 C2 C3 -0.7(4) . . . . ?
C4 C3 C2 C1 1.1(4) . . . . ?
C6 C3 C2 C1 -178.4(3) . . . . ?
C33 C34 C36 C26 -179.6(3) . . . . ?
C35 C34 C36 C26 -1.6(4) . . . . ?
C33 C34 C36 C30 -0.3(4) . . . . ?
C35 C34 C36 C30 177.6(2) . . . . ?
C31 C30 C36 C26 179.1(3) . . . . ?
C29 C30 C36 C26 0.2(4) . . . . ?
C31 C30 C36 C34 -0.1(4) . . . . ?
C29 C30 C36 C34 -179.0(3) . . . . ?
C35 N4 C25 O3 177.2(3) . . . . ?
C24 N4 C25 O3 -5.8(4) . . . . ?
C35 N4 C25 C26 -3.6(4) . . . . ?
C24 N4 C25 C26 173.3(2) . . . . ?
C8 C18 C16 C15 179.1(3) . . . . ?
C12 C18 C16 C15 -0.1(4) . . . . ?
C8 C18 C16 C17 -2.2(4) . . . . ?
C12 C18 C16 C17 178.6(2) . . . . ?
C20 C21 C22 C23 -0.8(4) . . . . ?
C24 C21 C22 C23 177.5(3) . . . . ?
C18 C16 C15 C14 0.6(4) . . . . ?
C17 C16 C15 C14 -178.2(3) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C12 C11 C10 C9 1.4(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C28 C27 C26 C36 -1.0(4) . . . . ?
C28 C27 C26 C25 176.3(3) . . . . ?
C34 C36 C26 C27 -179.8(3) . . . . ?
C30 C36 C26 C27 1.0(4) . . . . ?
C34 C36 C26 C25 2.9(4) . . . . ?
C30 C36 C26 C25 -176.3(2) . . . . ?
O3 C25 C26 C27 1.4(4) . . . . ?
N4 C25 C26 C27 -177.7(2) . . . . ?
O3 C25 C26 C36 178.8(3) . . . . ?
N4 C25 C26 C36 -0.4(4) . . . . ?
C15 C14 C13 C12 -0.1(4) . . . . ?
C18 C12 C13 C14 0.5(4) . . . . ?
C11 C12 C13 C14 -179.2(3) . . . . ?
C25 N4 C35 O4 -176.5(3) . . . . ?
C24 N4 C35 O4 6.5(4) . . . . ?
C25 N4 C35 C34 4.9(4) . . . . ?
C24 N4 C35 C34 -172.1(2) . . . . ?
C33 C34 C35 O4 -2.7(4) . . . . ?
C36 C34 C35 O4 179.3(3) . . . . ?
C33 C34 C35 N4 175.9(2) . . . . ?
C36 C34 C35 N4 -2.1(4) . . . . ?
C19 N3 C23 C22 0.2(5) . . . . ?
C21 C22 C23 N3 0.2(5) . . . . ?
C36 C34 C33 C32 0.3(4) . . . . ?
C35 C34 C33 C32 -177.7(3) . . . . ?
C31 C32 C33 C34 0.3(5) . . . . ?
C7 N2 C17 O2 -173.8(3) . . . . ?
C6 N2 C17 O2 7.2(4) . . . . ?
C7 N2 C17 C16 7.6(4) . . . . ?
C6 N2 C17 C16 -171.3(2) . . . . ?
C15 C16 C17 O2 -3.2(4) . . . . ?
C18 C16 C17 O2 178.1(3) . . . . ?
C15 C16 C17 N2 175.3(2) . . . . ?
C18 C16 C17 N2 -3.4(4) . . . . ?
C27 C28 C29 C30 1.4(5) . . . . ?
C31 C30 C29 C28 179.8(3) . . . . ?
C36 C30 C29 C28 -1.4(4) . . . . ?
C33 C32 C31 C30 -0.7(5) . . . . ?
C29 C30 C31 C32 179.5(3) . . . . ?
C36 C30 C31 C32 0.6(5) . . . . ?
C35 N4 C24 C21 -86.2(3) . . . . ?
C25 N4 C24 C21 96.6(3) . . . . ?
C20 C21 C24 N4 -89.1(3) . . . . ?
C22 C21 C24 N4 92.7(3) . . . . ?

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
N3 H3N Br1 0.90(4) 2.71(4) 3.391(3) 133(3) .
N3 H3N Br1 0.90(4) 2.66(4) 3.363(3) 135(3) 2_765
N1 H1N Br2 0.88(4) 2.76(4) 3.435(3) 134(3) 2_765
N1 H1N Br3 0.88(4) 2.67(4) 3.365(3) 136(3) 2_765
C5 H5 Br2 0.86(4) 2.95(3) 3.553(3) 129(3) 2_765
C5 H5 O1 0.86(4) 2.45(4) 3.073(4) 131(3) 1_655
C1 H1 Br2 0.97(3) 3.08(3) 3.670(3) 121(2) 2_665
C1 H1 Br3 0.97(3) 2.92(3) 3.521(3) 121(2) 2_765
C2 H2 Br2 0.88(3) 3.00(3) 3.626(3) 130(2) 2_665
C2 H2 O1 0.88(3) 2.64(3) 3.263(4) 128(2) .
C23 H23 Br1 0.91(4) 2.93(4) 3.485(3) 121(3) 2_765
C23 H23 O3 0.91(4) 2.53(4) 3.194(4) 131(3) 1_655
C19 H19 Br1 0.97(4) 2.89(4) 3.497(3) 121(3) .
C19 H19 Br1 0.97(4) 3.12(4) 3.727(3) 122(3) 2_665
C22 H22 O4 0.91(4) 2.63(4) 3.118(4) 115(3) .
C20 H20 Br1 0.98(4) 2.94(4) 3.659(3) 131(3) 2_665
C20 H20 Br2 0.98(4) 3.00(4) 3.591(3) 120(3) 2_665

_refine_diff_density_max         1.198
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.175

_shelxl_version_number           2013-2

