# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_hadi1611
_database_code_depnum_ccdc_archive 'CCDC 2000644'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2021-12-28 downloaded from the CCDC.
;

_audit_creation_date             2019-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Br4 N2 O2 Zn'
_chemical_formula_sum            'C30 H24 Br4 N2 O2 Zn'
_chemical_formula_weight         829.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?

_chemical_oxdiff_usercomment     (R)+Br2+Zn
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.2155(3)
_cell_length_b                   10.9297(3)
_cell_length_c                   12.9935(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.622(3)
_cell_angle_gamma                90
_cell_volume                     1390.14(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13802
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      29.9690
_cell_measurement_theta_min      2.9630
_shelx_estimated_absorpt_T_max   0.618
_shelx_estimated_absorpt_T_min   0.287
_exptl_absorpt_coefficient_mu    6.665
_exptl_absorpt_correction_T_max  0.606
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0495
1 0 -1 0.0335
0 -1 1 0.0817
0 1 -1 0.1107
-1 1 0 0.0862
0 1 1 0.0729
-4 -5 -2 0.0700
0 1 0 0.0727
5 2 5 0.1250

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08

_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14589
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.480
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  77.00   0.50    8.00    --    3.35  57.00 -60.00  184
  2  ω     38.00  84.00   0.50    8.00    --    3.35 178.00 120.00   92
  3  ω    -44.00 -14.00   0.50    8.00    --   -4.60 105.00-139.58   60
  4  ω    -44.00 -15.00   0.50    8.00    --   -4.60 106.00  -9.07   58
  5  ω    -50.00 -24.00   0.50    8.00    --   -4.60 116.00 106.92   52
  6  ω    -77.00   5.00   0.50    8.00    --    3.35 -19.00 150.00  164
  7  ω    -27.00  39.00   0.50    8.00    --    3.35 -99.00 150.00  132
  8  ω    -27.00  31.00   0.50    8.00    --   -4.60 -99.00 120.00  116
  9  ω    -27.00  31.00   0.50    8.00    --   -4.60 -99.00 -30.00  116
 10  ω    -77.00  40.00   0.50    8.00    --    3.35  -3.00-132.30  234
 11  ω    -75.00  21.00   0.50    8.00    --    3.35 -38.00 -30.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0615214000
_diffrn_orient_matrix_UB_12      0.0295872000
_diffrn_orient_matrix_UB_13      -0.0283379000
_diffrn_orient_matrix_UB_21      0.0339096000
_diffrn_orient_matrix_UB_22      0.0573679000
_diffrn_orient_matrix_UB_23      0.0087837000
_diffrn_orient_matrix_UB_31      0.0176903000
_diffrn_orient_matrix_UB_32      -0.0069202000
_diffrn_orient_matrix_UB_33      -0.0486331000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2800
_reflns_number_total             2841

_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0138
_refine_ls_R_factor_gt           0.0134
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0217P)²+0.4120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0330
_refine_ls_wR_factor_ref         0.0332
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.44541(2) 0.77403(2) 0.82739(2) 0.01961(7) Uani 1 1 d . . . . .
Br2 Br 0.83106(3) 0.42289(3) 1.05141(2) 0.02596(9) Uani 1 1 d . . . . .
C1 C 0.6025(3) 0.6257(2) 0.7279(2) 0.0141(5) Uani 1 1 d . . . . .
C2 C 0.5835(3) 0.6568(2) 0.8281(2) 0.0150(5) Uani 1 1 d . . . . .
C3 C 0.6522(3) 0.6016(3) 0.9243(2) 0.0177(5) Uani 1 1 d . . . . .
H3 H 0.636537 0.626661 0.989737 0.021 Uiso 1 1 calc R . . . .
C4 C 0.7447(3) 0.5087(3) 0.9229(2) 0.0179(5) Uani 1 1 d . . . . .
C5 C 0.7695(3) 0.4740(3) 0.8289(2) 0.0170(5) Uani 1 1 d . . . . .
H5 H 0.833621 0.410861 0.829524 0.020 Uiso 1 1 calc R . . . .
C6 C 0.7002(3) 0.5315(2) 0.7310(2) 0.0150(5) Uani 1 1 d . . . . .
C7 C 0.7399(3) 0.4920(2) 0.6375(2) 0.0154(5) Uani 1 1 d . . . . .
H7 H 0.817930 0.440566 0.650927 0.019 Uiso 1 1 calc R . . . .
C8 C 0.7522(3) 0.4777(3) 0.4593(2) 0.0172(5) Uani 1 1 d . . . . .
H8 H 0.831124 0.425014 0.497628 0.021 Uiso 1 1 calc R . . . .
C9 C 0.6551(3) 0.4002(3) 0.3732(2) 0.0161(5) Uani 1 1 d . . . . .
C10 C 0.5917(3) 0.3006(3) 0.4054(2) 0.0255(7) Uani 1 1 d . . . . .
H10 H 0.609522 0.283371 0.479832 0.031 Uiso 1 1 calc R . . . .
C11 C 0.5034(4) 0.2265(3) 0.3312(3) 0.0323(7) Uani 1 1 d . . . . .
H11 H 0.459189 0.160020 0.354563 0.039 Uiso 1 1 calc R . . . .
C12 C 0.4793(3) 0.2494(3) 0.2223(3) 0.0308(7) Uani 1 1 d . . . . .
H12 H 0.417912 0.198976 0.170970 0.037 Uiso 1 1 calc R . . . .
C13 C 0.5447(3) 0.3456(3) 0.1887(2) 0.0256(7) Uani 1 1 d . . . . .
H13 H 0.530448 0.359515 0.114138 0.031 Uiso 1 1 calc R . . . .
C14 C 0.6313(3) 0.4221(3) 0.2636(2) 0.0198(5) Uani 1 1 d . . . . .
H14 H 0.674215 0.489288 0.240136 0.024 Uiso 1 1 calc R . . . .
C15 C 0.8086(3) 0.5900(3) 0.4169(2) 0.0231(6) Uani 1 1 d . . . . .
H15A H 0.732806 0.641835 0.377006 0.035 Uiso 1 1 calc GR . . . .
H15B H 0.862297 0.563993 0.369173 0.035 Uiso 1 1 calc GR . . . .
H15C H 0.867094 0.636276 0.477301 0.035 Uiso 1 1 calc GR . . . .
N1 N 0.6818(2) 0.5187(2) 0.53888(17) 0.0151(4) Uani 1 1 d . . . . .
O1 O 0.53222(19) 0.68137(18) 0.64056(14) 0.0163(4) Uani 1 1 d . . . . .
Zn1 Zn 0.500000 0.60961(4) 0.500000 0.01410(10) Uani 1 2 d S T P . .


_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 C2 1.904(3) . ?
Br2 C4 1.899(3) . ?
C1 C2 1.412(4) . ?
C1 C6 1.427(4) . ?
C1 O1 1.307(3) . ?
C2 C3 1.384(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(4) . ?
C4 C5 1.370(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(4) . ?
C6 C7 1.452(4) . ?
C7 H7 0.9500 . ?
C7 N1 1.282(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.523(4) . ?
C8 C15 1.525(4) . ?
C8 N1 1.488(3) . ?
C9 C10 1.390(4) . ?
C9 C14 1.395(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Zn1 2.038(2) . ?
O1 Zn1 1.9275(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 115.3(2) . . ?
O1 C1 C2 120.2(2) . . ?
O1 C1 C6 124.5(2) . . ?
C1 C2 Br1 117.05(18) . . ?
C3 C2 Br1 118.78(19) . . ?
C3 C2 C1 124.0(2) . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.5(2) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 Br2 119.7(2) . . ?
C5 C4 Br2 119.3(2) . . ?
C5 C4 C3 120.9(2) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 123.4(2) . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 C7 115.7(2) . . ?
C6 C7 H7 116.3 . . ?
N1 C7 C6 127.5(2) . . ?
N1 C7 H7 116.3 . . ?
C9 C8 H8 108.0 . . ?
C9 C8 C15 114.6(2) . . ?
C15 C8 H8 108.0 . . ?
N1 C8 H8 108.0 . . ?
N1 C8 C9 109.6(2) . . ?
N1 C8 C15 108.5(2) . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 C14 118.8(3) . . ?
C14 C9 C8 122.8(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.1(3) . . ?
C13 C14 H14 120.0 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 116.6(2) . . ?
C7 N1 Zn1 119.16(18) . . ?
C8 N1 Zn1 124.20(16) . . ?
C1 O1 Zn1 122.41(17) . . ?
N1 Zn1 N1 121.64(13) . 2_656 ?
O1 Zn1 N1 109.25(8) . 2_656 ?
O1 Zn1 N1 109.25(8) 2_656 . ?
O1 Zn1 N1 93.84(8) . . ?
O1 Zn1 N1 93.84(8) 2_656 2_656 ?
O1 Zn1 O1 131.98(12) . 2_656 ?

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
Br1 C2 C3 C4 174.6(2) . . . . ?
Br2 C4 C5 C6 176.2(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C1 C6 C7 N1 -11.9(4) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C2 C1 C6 C7 -176.1(2) . . . . ?
C2 C1 O1 Zn1 -156.90(19) . . . . ?
C2 C3 C4 Br2 -175.5(2) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 176.8(2) . . . . ?
C5 C6 C7 N1 170.8(3) . . . . ?
C6 C1 C2 Br1 -175.82(19) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C6 C1 O1 Zn1 22.6(3) . . . . ?
C6 C7 N1 C8 173.3(3) . . . . ?
C6 C7 N1 Zn1 -8.0(4) . . . . ?
C8 C9 C10 C11 -179.6(3) . . . . ?
C8 C9 C14 C13 177.9(2) . . . . ?
C9 C8 N1 C7 124.4(3) . . . . ?
C9 C8 N1 Zn1 -54.3(3) . . . . ?
C9 C10 C11 C12 1.5(5) . . . . ?
C10 C9 C14 C13 0.5(4) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C11 C12 C13 C14 -2.1(5) . . . . ?
C12 C13 C14 C9 1.6(4) . . . . ?
C14 C9 C10 C11 -2.0(4) . . . . ?
C15 C8 C9 C10 -175.7(3) . . . . ?
C15 C8 C9 C14 6.8(4) . . . . ?
C15 C8 N1 C7 -109.8(3) . . . . ?
C15 C8 N1 Zn1 71.6(3) . . . . ?
N1 C8 C9 C10 -53.5(3) . . . . ?
N1 C8 C9 C14 129.0(3) . . . . ?
O1 C1 C2 Br1 3.7(3) . . . . ?
O1 C1 C2 C3 179.2(3) . . . . ?
O1 C1 C6 C5 -178.5(2) . . . . ?
O1 C1 C6 C7 4.4(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_hadi2011
_database_code_depnum_ccdc_archive 'CCDC 2000653'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2021-12-28 downloaded from the CCDC.
;

_audit_creation_date             2019-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Br2 Cl2 N2 O2 Zn'
_chemical_formula_sum            'C30 H24 Br2 Cl2 N2 O2 Zn'
_chemical_formula_weight         740.60
_chemical_absolute_configuration ad
_chemical_melting_point          ?

_chemical_oxdiff_usercomment     'sample S'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.2247(2)
_cell_length_b                   10.8940(3)
_cell_length_c                   12.9214(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.216(3)
_cell_angle_gamma                90
_cell_volume                     1374.80(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6125
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.1140
_cell_measurement_theta_min      4.8590
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.348
_exptl_absorpt_coefficient_mu    6.697
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0215
1 0 -1 0.0085
2 5 3 0.0902
-2 -5 -3 0.0700
3 -5 2 0.0622
-3 5 -2 0.0475

_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03

_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8416
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.427
_diffrn_reflns_theta_min         4.872
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -13.00   1.00    1.00    --  -41.44 -57.00   0.00  101
  2  ω    -82.00  39.00   1.00    1.00    --  -41.44  19.00 -30.00  121
  3  ω    -70.00  32.00   1.00    1.00    --  -41.44  57.00-180.00  102
  4  ω     23.00  97.00   1.00    1.00    --   41.44-125.00 -60.00   74
  5  ω     23.00  97.00   1.00    1.00    --   41.44-125.00  60.00   74
  6  ω     17.00 116.00   1.00    1.00    --   41.44  37.00  30.00   99
  7  ω      1.00  82.00   1.00    1.00    --   41.44 -99.00 -30.00   81
  8  ω    100.00 178.00   1.00    3.00    --  112.00 111.00  60.00   78
  9  ω     39.00 138.00   1.00    3.00    --  112.00 -45.00 120.00   99
 10  ω     59.00 178.00   1.00    3.00    --  112.00  15.00  60.00  119
 11  ω     29.00 110.00   1.00    3.00    --  112.00 -94.00 -30.00   81
 12  ω     59.00 178.00   1.00    3.00    --  112.00  15.00 -60.00  119
 13  ω     36.00 113.00   1.00    3.00    --  112.00-111.00 -60.00   77
 14  ω     86.00 178.00   1.00    3.00    --  112.00  45.00-150.00   92
 15  ω     86.00 178.00   1.00    3.00    --  112.00  45.00  90.00   92
 16  ω     29.00 110.00   1.00    3.00    --  112.00 -94.00-150.00   81
 17  ω     84.00 178.00   1.00    3.00    --  112.00  30.00 -30.00   94
 18  ω     79.00 178.00   1.00    3.00    --  112.00  77.00   0.00   99
 19  ω     39.00 138.00   1.00    3.00    --  112.00 -45.00  30.00   99
 20  ω     83.00 178.00   1.00    3.00    --  112.00  61.00  60.00   95
 21  ω     36.00 113.00   1.00    3.00    --  112.00-111.00-150.00   77
 22  ω     36.00 113.00   1.00    3.00    --  112.00-111.00 -90.00   77
 23  ω     84.00 178.00   1.00    3.00    --  112.00  30.00 150.00   94
 24  ω     79.00 178.00   1.00    3.00    --  112.00  77.00 -30.00   99
 25  ω     86.00 178.00   1.00    3.00    --  112.00  45.00  60.00   92
 26  ω     84.00 178.00   1.00    3.00    --  112.00  30.00  60.00   94
 27  ω     36.00 140.00   1.00    3.00    --  112.00 -30.00 -90.00  104
 28  ω     79.00 153.00   1.00    3.00    --  112.00  77.00  30.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1161669000
_diffrn_orient_matrix_UB_12      -0.0525164000
_diffrn_orient_matrix_UB_13      -0.0402140000
_diffrn_orient_matrix_UB_21      0.0341028000
_diffrn_orient_matrix_UB_22      -0.0937495000
_diffrn_orient_matrix_UB_23      0.0935349000
_diffrn_orient_matrix_UB_31      -0.1011876000
_diffrn_orient_matrix_UB_32      -0.0917049000
_diffrn_orient_matrix_UB_33      -0.0723943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2732
_reflns_number_total             2762

_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.9935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0589
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.44569(3) 0.22714(4) 0.82837(3) 0.02831(11) Uani 1 1 d . . . . .
C1 C 0.6037(4) 0.3756(3) 0.7297(3) 0.0230(7) Uani 1 1 d . . . . .
C2 C 0.5846(4) 0.3439(4) 0.8308(3) 0.0242(7) Uani 1 1 d . . . . .
C3 C 0.6534(4) 0.3995(4) 0.9274(3) 0.0281(7) Uani 1 1 d . . . . .
H3 H 0.637233 0.374623 0.992994 0.034 Uiso 1 1 calc R . . . .
C4 C 0.7468(4) 0.4923(4) 0.9275(3) 0.0283(7) Uani 1 1 d . . . . .
C5 C 0.7724(4) 0.5271(4) 0.8327(3) 0.0266(7) Uani 1 1 d . . . . .
H5 H 0.837116 0.590008 0.833724 0.032 Uiso 1 1 calc R . . . .
C6 C 0.7023(4) 0.4693(3) 0.7340(3) 0.0233(7) Uani 1 1 d . . . . .
C7 C 0.7426(4) 0.5085(3) 0.6403(3) 0.0239(7) Uani 1 1 d . . . . .
H7 H 0.821069 0.559747 0.654279 0.029 Uiso 1 1 calc R . . . .
C8 C 0.7535(4) 0.5207(4) 0.4604(3) 0.0255(7) Uani 1 1 d . . . . .
H8 H 0.833791 0.572565 0.499000 0.031 Uiso 1 1 calc R . . . .
C9 C 0.6568(4) 0.5992(3) 0.3740(3) 0.0252(7) Uani 1 1 d . . . . .
C10 C 0.6328(4) 0.5779(4) 0.2627(3) 0.0293(8) Uani 1 1 d . . . . .
H10 H 0.675927 0.510832 0.238992 0.035 Uiso 1 1 calc R . . . .
C11 C 0.5460(4) 0.6550(4) 0.1874(3) 0.0349(9) Uani 1 1 d . . . . .
H11 H 0.531543 0.641343 0.112181 0.042 Uiso 1 1 calc R . . . .
C12 C 0.4807(5) 0.7512(4) 0.2209(4) 0.0417(10) Uani 1 1 d . . . . .
H12 H 0.419374 0.802088 0.168882 0.050 Uiso 1 1 calc R . . . .
C13 C 0.5045(5) 0.7738(4) 0.3308(4) 0.0421(10) Uani 1 1 d . . . . .
H13 H 0.460182 0.840383 0.354137 0.050 Uiso 1 1 calc R . . . .
C14 C 0.5933(4) 0.6985(4) 0.4063(3) 0.0332(9) Uani 1 1 d . . . . .
H14 H 0.611044 0.715225 0.481378 0.040 Uiso 1 1 calc R . . . .
C15 C 0.8073(4) 0.4071(4) 0.4185(3) 0.0318(8) Uani 1 1 d . . . . .
H15A H 0.871457 0.363908 0.479096 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.854497 0.431291 0.365820 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.730657 0.352620 0.383488 0.048 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.82853(10) 0.56931(11) 1.04749(7) 0.0388(2) Uani 1 1 d . . . . .
N1 N 0.6834(3) 0.4815(3) 0.5409(2) 0.0226(6) Uani 1 1 d . . . . .
O1 O 0.5334(3) 0.3194(3) 0.6417(2) 0.0257(5) Uani 1 1 d . . . . .
Zn1 Zn 0.500000 0.39209(6) 0.500000 0.02228(15) Uani 1 2 d S T P . .


_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 C2 1.900(4) . ?
C1 C2 1.420(5) . ?
C1 C6 1.424(5) . ?
C1 O1 1.303(4) . ?
C2 C3 1.378(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(6) . ?
C4 C5 1.381(5) . ?
C4 Cl1 1.743(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.413(5) . ?
C6 C7 1.452(5) . ?
C7 H7 0.9500 . ?
C7 N1 1.282(5) . ?
C8 H8 1.0000 . ?
C8 C9 1.518(5) . ?
C8 C15 1.518(6) . ?
C8 N1 1.489(4) . ?
C9 C10 1.404(5) . ?
C9 C14 1.388(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(6) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Zn1 2.039(3) . ?
O1 Zn1 1.930(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
C2 C1 C6 115.3(3) . . ?
O1 C1 C2 119.8(3) . . ?
O1 C1 C6 124.9(3) . . ?
C1 C2 Br1 117.0(3) . . ?
C3 C2 Br1 119.2(3) . . ?
C3 C2 C1 123.7(3) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 Cl1 120.0(3) . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 Cl1 119.4(3) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(4) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 123.4(3) . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 C7 115.3(3) . . ?
C6 C7 H7 116.5 . . ?
N1 C7 C6 126.9(3) . . ?
N1 C7 H7 116.5 . . ?
C9 C8 H8 107.9 . . ?
C9 C8 C15 115.0(3) . . ?
C15 C8 H8 107.9 . . ?
N1 C8 H8 107.9 . . ?
N1 C8 C9 109.4(3) . . ?
N1 C8 C15 108.4(3) . . ?
C10 C9 C8 122.6(3) . . ?
C14 C9 C8 118.6(3) . . ?
C14 C9 C10 118.8(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.1(4) . . ?
C13 C14 H14 119.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 116.9(3) . . ?
C7 N1 Zn1 119.7(2) . . ?
C8 N1 Zn1 123.5(2) . . ?
C1 O1 Zn1 122.1(2) . . ?
N1 Zn1 N1 122.95(18) 2_656 . ?
O1 Zn1 N1 93.36(11) . . ?
O1 Zn1 N1 93.36(11) 2_656 2_656 ?
O1 Zn1 N1 109.45(11) . 2_656 ?
O1 Zn1 N1 109.45(11) 2_656 . ?
O1 Zn1 O1 131.59(17) . 2_656 ?

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
Br1 C2 C3 C4 -174.6(3) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C1 C6 C7 N1 11.8(6) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
C2 C1 C6 C7 175.9(3) . . . . ?
C2 C1 O1 Zn1 156.6(3) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C2 C3 C4 Cl1 176.7(3) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C4 C5 C6 C7 -176.9(4) . . . . ?
C5 C6 C7 N1 -170.7(4) . . . . ?
C6 C1 C2 Br1 176.0(3) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C6 C1 O1 Zn1 -23.7(5) . . . . ?
C6 C7 N1 C8 -172.9(3) . . . . ?
C6 C7 N1 Zn1 8.3(5) . . . . ?
C8 C9 C10 C11 -178.2(3) . . . . ?
C8 C9 C14 C13 179.7(4) . . . . ?
C9 C8 N1 C7 -123.9(4) . . . . ?
C9 C8 N1 Zn1 54.8(4) . . . . ?
C9 C10 C11 C12 -1.3(6) . . . . ?
C10 C9 C14 C13 1.9(6) . . . . ?
C10 C11 C12 C13 1.8(7) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
C12 C13 C14 C9 -1.4(7) . . . . ?
C14 C9 C10 C11 -0.5(6) . . . . ?
C15 C8 C9 C10 -8.1(5) . . . . ?
C15 C8 C9 C14 174.2(3) . . . . ?
C15 C8 N1 C7 110.0(4) . . . . ?
C15 C8 N1 Zn1 -71.3(3) . . . . ?
Cl1 C4 C5 C6 -177.2(3) . . . . ?
N1 C8 C9 C10 -130.3(4) . . . . ?
N1 C8 C9 C14 52.0(4) . . . . ?
O1 C1 C2 Br1 -4.3(5) . . . . ?
O1 C1 C2 C3 -179.3(4) . . . . ?
O1 C1 C6 C5 178.8(3) . . . . ?
O1 C1 C6 C7 -3.9(6) . . . . ?


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

data_hadi2111
_database_code_depnum_ccdc_archive 'CCDC 2000648'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2021-12-28 downloaded from the CCDC.
;

_audit_creation_date             2019-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Br2 Cl2 N2 O2 Zn'
_chemical_formula_sum            'C30 H24 Br2 Cl2 N2 O2 Zn'
_chemical_formula_weight         740.60
_chemical_absolute_configuration ad
_chemical_melting_point          ?

_chemical_oxdiff_usercomment     'sample R'

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'
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.21573(14)
_cell_length_b                   10.88240(13)
_cell_length_c                   12.90981(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.2179(14)
_cell_angle_gamma                90
_cell_volume                     1370.89(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15930
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      32.6740
_cell_measurement_theta_min      3.2910
_shelx_estimated_absorpt_T_max   0.713
_shelx_estimated_absorpt_T_min   0.223
_exptl_absorpt_coefficient_mu    4.038
_exptl_absorpt_correction_T_max  0.735
_exptl_absorpt_correction_T_min  0.304
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0458
-1 0 1 0.0418
3 -3 5 0.0955
-3 0 -5 0.1235
-2 -5 -4 0.2188
-1 1 0 0.1205
3 0 5 0.1448
1 1 0 0.2122
-3 -5 0 0.2063
-1 0 0 0.0808
-2 -1 5 0.0564

_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09

_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15540
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.804
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  94.00   0.80    5.00    --   18.72  77.00 150.00  135
  2  ω    -20.00  60.00   0.80    5.00    --   18.72 -99.00  30.00  100
  3  ω     -9.00  91.00   0.80    5.00    --   18.72  57.00  60.00  125
  4  ω    -47.00  53.00   0.80    5.00    --  -19.19  57.00-120.00  125
  5  ω   -106.00 -56.40   0.80    5.00    --  -19.19 178.00   0.00   62
  6  ω    -75.00 -23.00   0.80    5.00    --  -19.19 125.00   1.00   65
  7  ω    -94.00   4.40   0.80    5.00    --  -19.19 -37.00 -90.00  123
  8  ω     -6.00  92.40   0.80    5.00    --   18.72  37.00 -60.00  123
  9  ω    -20.00  60.00   0.80    5.00    --   18.72 -99.00 -60.00  100
 10  ω   -108.00 -58.40   0.80    5.00    --  -19.19-178.00  30.00   62
 11  ω    -95.00   0.20   0.80    5.00    --  -19.19 -77.00 120.00  119
 12  ω    -47.00  53.00   0.80    5.00    --  -19.19  57.00  60.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0589671000
_diffrn_orient_matrix_UB_12      0.0071762000
_diffrn_orient_matrix_UB_13      0.0453550000
_diffrn_orient_matrix_UB_21      0.0418419000
_diffrn_orient_matrix_UB_22      0.0017909000
_diffrn_orient_matrix_UB_23      -0.0351329000
_diffrn_orient_matrix_UB_31      -0.0076891000
_diffrn_orient_matrix_UB_32      0.0647339000
_diffrn_orient_matrix_UB_33      -0.0040519000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2781
_reflns_number_total             2801

_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2801
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0185
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²+1.0171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0472
_refine_ls_wR_factor_ref         0.0473
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.55429(3) 0.77269(3) 0.17164(2) 0.02107(9) Uani 1 1 d . . . . .
C1 C 0.3965(3) 0.6243(3) 0.2701(2) 0.0151(6) Uani 1 1 d . . . . .
C2 C 0.4151(3) 0.6556(3) 0.1692(3) 0.0170(6) Uani 1 1 d . . . . .
C3 C 0.3466(3) 0.6002(3) 0.0723(2) 0.0204(6) Uani 1 1 d . . . . .
H3 H 0.362918 0.624753 0.006602 0.024 Uiso 1 1 calc R . . . .
C4 C 0.2532(3) 0.5076(3) 0.0728(3) 0.0206(6) Uani 1 1 d . . . . .
C5 C 0.2279(3) 0.4729(3) 0.1673(3) 0.0190(6) Uani 1 1 d . . . . .
H5 H 0.163230 0.409779 0.166207 0.023 Uiso 1 1 calc R . . . .
C6 C 0.2974(3) 0.5305(3) 0.2660(2) 0.0158(6) Uani 1 1 d . . . . .
C7 C 0.2574(3) 0.4915(3) 0.3596(3) 0.0172(6) Uani 1 1 d . . . . .
H7 H 0.178755 0.440424 0.345797 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2463(3) 0.4790(3) 0.5396(3) 0.0182(6) Uani 1 1 d . . . . .
H8 H 0.166067 0.426875 0.501058 0.022 Uiso 1 1 calc R . . . .
C9 C 0.3433(3) 0.4009(3) 0.6265(3) 0.0181(6) Uani 1 1 d . . . . .
C10 C 0.4071(4) 0.3016(3) 0.5938(3) 0.0255(8) Uani 1 1 d . . . . .
H10 H 0.389937 0.285334 0.518708 0.031 Uiso 1 1 calc R . . . .
C11 C 0.4952(4) 0.2262(4) 0.6694(3) 0.0348(9) Uani 1 1 d . . . . .
H11 H 0.538845 0.159121 0.645951 0.042 Uiso 1 1 calc R . . . .
C12 C 0.5197(4) 0.2485(3) 0.7789(3) 0.0335(9) Uani 1 1 d . . . . .
H12 H 0.581324 0.197785 0.830991 0.040 Uiso 1 1 calc R . . . .
C13 C 0.4540(4) 0.3449(4) 0.8121(3) 0.0282(8) Uani 1 1 d . . . . .
H13 H 0.468689 0.358957 0.887320 0.034 Uiso 1 1 calc R . . . .
C14 C 0.3668(3) 0.4215(3) 0.7367(3) 0.0217(7) Uani 1 1 d . . . . .
H14 H 0.323044 0.488234 0.760508 0.026 Uiso 1 1 calc R . . . .
C15 C 0.1923(3) 0.5929(3) 0.5815(3) 0.0243(7) Uani 1 1 d . . . . .
H15A H 0.269417 0.645171 0.620228 0.036 Uiso 1 1 calc GR . . . .
H15B H 0.140466 0.568408 0.631007 0.036 Uiso 1 1 calc GR . . . .
H15C H 0.132286 0.638604 0.520338 0.036 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.17142(9) 0.43063(9) -0.04758(6) 0.0314(2) Uani 1 1 d . . . . .
N1 N 0.3167(3) 0.5186(2) 0.4590(2) 0.0162(5) Uani 1 1 d . . . . .
O1 O 0.4665(2) 0.6803(2) 0.35848(18) 0.0182(4) Uani 1 1 d . . . . .
Zn1 Zn 0.500000 0.60782(4) 0.500000 0.01507(12) Uani 1 2 d S T P . .


_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 C2 1.902(3) . ?
C1 C2 1.412(4) . ?
C1 C6 1.428(4) . ?
C1 O1 1.305(4) . ?
C2 C3 1.379(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(5) . ?
C4 C5 1.374(5) . ?
C4 Cl1 1.745(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(4) . ?
C6 C7 1.450(4) . ?
C7 H7 0.9500 . ?
C7 N1 1.280(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.518(4) . ?
C8 C15 1.520(5) . ?
C8 N1 1.492(4) . ?
C9 C10 1.390(5) . ?
C9 C14 1.390(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Zn1 2.036(3) . ?
O1 Zn1 1.926(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
C2 C1 C6 115.2(3) . . ?
O1 C1 C2 120.4(3) . . ?
O1 C1 C6 124.4(3) . . ?
C1 C2 Br1 116.8(2) . . ?
C3 C2 Br1 119.0(2) . . ?
C3 C2 C1 124.1(3) . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 Cl1 119.5(3) . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 Cl1 119.5(3) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 123.3(3) . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 C7 115.7(3) . . ?
C6 C7 H7 116.5 . . ?
N1 C7 C6 127.1(3) . . ?
N1 C7 H7 116.5 . . ?
C9 C8 H8 108.0 . . ?
C9 C8 C15 114.8(3) . . ?
C15 C8 H8 108.0 . . ?
N1 C8 H8 108.0 . . ?
N1 C8 C9 109.4(3) . . ?
N1 C8 C15 108.3(3) . . ?
C10 C9 C8 118.2(3) . . ?
C14 C9 C8 122.9(3) . . ?
C14 C9 C10 118.8(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 116.8(3) . . ?
C7 N1 Zn1 119.7(2) . . ?
C8 N1 Zn1 123.5(2) . . ?
C1 O1 Zn1 122.41(19) . . ?
N1 Zn1 N1 123.00(15) . 2_656 ?
O1 Zn1 N1 93.28(10) 2_656 2_656 ?
O1 Zn1 N1 93.28(10) . . ?
O1 Zn1 N1 109.50(10) 2_656 . ?
O1 Zn1 N1 109.50(10) . 2_656 ?
O1 Zn1 O1 131.61(14) 2_656 . ?

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
Br1 C2 C3 C4 174.8(2) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 N1 -11.8(5) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
C2 C1 C6 C7 -175.8(3) . . . . ?
C2 C1 O1 Zn1 -156.5(2) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 Cl1 -176.8(3) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C4 C5 C6 C7 176.7(3) . . . . ?
C5 C6 C7 N1 170.6(3) . . . . ?
C6 C1 C2 Br1 -176.2(2) . . . . ?
C6 C1 C2 C3 -1.3(5) . . . . ?
C6 C1 O1 Zn1 24.1(4) . . . . ?
C6 C7 N1 C8 173.1(3) . . . . ?
C6 C7 N1 Zn1 -8.2(4) . . . . ?
C8 C9 C10 C11 -179.2(3) . . . . ?
C8 C9 C14 C13 178.3(3) . . . . ?
C9 C8 N1 C7 124.2(3) . . . . ?
C9 C8 N1 Zn1 -54.4(3) . . . . ?
C9 C10 C11 C12 0.6(6) . . . . ?
C10 C9 C14 C13 0.9(5) . . . . ?
C10 C11 C12 C13 1.1(6) . . . . ?
C11 C12 C13 C14 -1.8(6) . . . . ?
C12 C13 C14 C9 0.8(5) . . . . ?
C14 C9 C10 C11 -1.6(5) . . . . ?
C15 C8 C9 C10 -174.1(3) . . . . ?
C15 C8 C9 C14 8.5(4) . . . . ?
C15 C8 N1 C7 -109.9(3) . . . . ?
C15 C8 N1 Zn1 71.4(3) . . . . ?
Cl1 C4 C5 C6 177.3(2) . . . . ?
N1 C8 C9 C10 -52.1(4) . . . . ?
N1 C8 C9 C14 130.5(3) . . . . ?
O1 C1 C2 Br1 4.4(4) . . . . ?
O1 C1 C2 C3 179.3(3) . . . . ?
O1 C1 C6 C5 -178.9(3) . . . . ?
O1 C1 C6 C7 3.6(5) . . . . ?


####################################################################### 
# 
# 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_hadi2711
_database_code_depnum_ccdc_archive 'CCDC 2000646'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2021-12-28 downloaded from the CCDC.
;

_audit_creation_date             2019-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Cl4 N2 O2 Zn'
_chemical_formula_sum            'C30 H24 Cl4 N2 O2 Zn'
_chemical_formula_weight         651.68
_chemical_absolute_configuration ad
_chemical_melting_point          ?

_chemical_oxdiff_usercomment     'sample R'

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.08126(12)
_cell_length_b                   10.86962(12)
_cell_length_c                   12.76560(16)
_cell_angle_alpha                90
_cell_angle_beta                 106.5627(13)
_cell_angle_gamma                90
_cell_volume                     1340.81(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    18826
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      32.0700
_cell_measurement_theta_min      2.8130
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.721
_exptl_absorpt_coefficient_mu    1.348
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.0562
-1 0 -1 0.0422
-1 0 1 0.0439
1 0 -1 0.0439
3 -5 0 0.1042
0 1 1 0.0937
0 -5 -2 0.1215
1 5 -2 0.1116
-5 5 3 0.0821
5 2 0 0.0821
-5 3 1 0.0668
0 4 -5 0.0963

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09

_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_min         2.506
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00   5.00   0.50   12.00    --   26.33 -19.00   0.00  150
  2  ω    -27.00  31.00   0.50   12.00    --  -27.27 -99.00 -90.00  116
  3  ω    -58.00  44.00   0.50   12.00    --   26.33 -57.00   0.00  204
  4  ω    -21.00 111.00   0.50   12.00    --   26.33  57.00-120.00  264
  5  ω     38.00 115.00   0.50   12.00    --   26.33 178.00 -90.00  154
  6  ω    -44.00  27.00   0.50   12.00    --  -27.27 -92.00  86.00  142
  7  ω    -58.00  44.00   0.50   12.00    --   26.33 -57.00 -90.00  204
  8  ω    -22.00 115.00   0.50   12.00    --   26.33  77.00  30.00  274
  9  ω     58.00 113.00   0.50   12.00    --   26.33 144.00  80.00  110
 10  ω     38.00 115.00   0.50   12.00    --   26.33 178.00 150.00  154
 11  ω    -22.00 115.00   0.50   12.00    --   26.33  77.00-120.00  274
 12  ω    -70.00   5.00   0.50   12.00    --   26.33 -19.00 -60.00  150
 13  ω    -65.00  62.00   0.50   12.00    --  -27.27  38.00-180.00  254
 14  ω    -65.00  22.00   0.50   12.00    --   26.33 -38.00-150.00  174
 15  ω    -70.00   5.00   0.50   12.00    --   26.33 -19.00 120.00  150
 16  ω   -128.00 -59.00   0.50   12.00    --  -27.27-178.00  90.00  138
 17  ω   -118.00 -76.00   0.50   12.00    --  -27.27 -38.00   0.00   84
 18  ω   -127.00 -57.00   0.50   12.00    --  -27.27 178.00 -60.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0398164000
_diffrn_orient_matrix_UB_12      0.0383939000
_diffrn_orient_matrix_UB_13      0.0422783000
_diffrn_orient_matrix_UB_21      -0.0248252000
_diffrn_orient_matrix_UB_22      0.0525948000
_diffrn_orient_matrix_UB_23      -0.0325782000
_diffrn_orient_matrix_UB_31      -0.0564808000
_diffrn_orient_matrix_UB_32      0.0039966000
_diffrn_orient_matrix_UB_33      0.0226172000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4059
_reflns_number_total             4106

_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1895 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         4106
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0189
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.2485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0512
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1 C 0.60377(15) 0.62766(15) 0.73065(12) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.58476(17) 0.65989(17) 0.83326(13) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.65378(17) 0.60412(19) 0.93058(13) 0.0236(3) Uani 1 1 d . . . . .
H3 H 0.637653 0.629159 0.997200 0.028 Uiso 1 1 calc R . . . .
C4 C 0.74765(18) 0.51031(17) 0.92937(14) 0.0237(3) Uani 1 1 d . . . . .
C5 C 0.77277(17) 0.47549(16) 0.83348(13) 0.0219(3) Uani 1 1 d . . . . .
H5 H 0.837986 0.412223 0.834044 0.026 Uiso 1 1 calc R . . . .
C6 C 0.70259(16) 0.53284(15) 0.73423(13) 0.0191(3) Uani 1 1 d . . . . .
C7 C 0.74354(16) 0.49383(15) 0.63964(13) 0.0197(3) Uani 1 1 d . . . . .
H7 H 0.822782 0.442334 0.653226 0.024 Uiso 1 1 calc R . . . .
C8 C 0.75542(16) 0.48144(16) 0.45769(13) 0.0213(3) Uani 1 1 d . . . . .
H8 H 0.836805 0.429726 0.496065 0.026 Uiso 1 1 calc R . . . .
C9 C 0.65803(17) 0.40307(15) 0.37105(14) 0.0206(3) Uani 1 1 d . . . . .
C10 C 0.5928(2) 0.30392(18) 0.40510(16) 0.0287(4) Uani 1 1 d . . . . .
H10 H 0.610693 0.287469 0.480945 0.034 Uiso 1 1 calc R . . . .
C11 C 0.5025(2) 0.2292(2) 0.32982(19) 0.0357(4) Uani 1 1 d . . . . .
H11 H 0.457884 0.162606 0.354103 0.043 Uiso 1 1 calc R . . . .
C12 C 0.4771(2) 0.2516(2) 0.21898(18) 0.0350(4) Uani 1 1 d . . . . .
H12 H 0.413781 0.201382 0.167104 0.042 Uiso 1 1 calc R . . . .
C13 C 0.5442(2) 0.34727(19) 0.18442(16) 0.0300(4) Uani 1 1 d . . . . .
H13 H 0.528941 0.361330 0.108448 0.036 Uiso 1 1 calc R . . . .
C14 C 0.63411(19) 0.42330(17) 0.25999(14) 0.0244(3) Uani 1 1 d . . . . .
H14 H 0.679264 0.489318 0.235377 0.029 Uiso 1 1 calc R . . . .
C15 C 0.80886(19) 0.5957(2) 0.41361(15) 0.0292(4) Uani 1 1 d . . . . .
H15A H 0.730613 0.648371 0.376577 0.044 Uiso 1 1 calc GR . . . .
H15B H 0.859170 0.571163 0.361651 0.044 Uiso 1 1 calc GR . . . .
H15C H 0.871147 0.641167 0.474260 0.044 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.45933(4) 0.76988(4) 0.83272(3) 0.02622(9) Uani 1 1 d . . . . .
Cl2 Cl 0.82945(5) 0.43316(5) 1.04970(4) 0.03437(11) Uani 1 1 d . . . . .
N1 N 0.68443(14) 0.52122(13) 0.53928(11) 0.0192(2) Uani 1 1 d . . . . .
O1 O 0.53374(13) 0.68435(11) 0.64268(10) 0.0218(2) Uani 1 1 d . . . . .
Zn1 Zn 0.500000 0.61154(2) 0.500000 0.01853(7) Uani 1 2 d S T P . .


_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
C1 C2 1.421(2) . ?
C1 C6 1.425(2) . ?
C1 O1 1.2989(19) . ?
C2 C3 1.379(2) . ?
C2 Cl1 1.7388(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(3) . ?
C4 C5 1.372(2) . ?
C4 Cl2 1.7380(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(2) . ?
C6 C7 1.447(2) . ?
C7 H7 0.9500 . ?
C7 N1 1.285(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.515(2) . ?
C8 C15 1.524(3) . ?
C8 N1 1.486(2) . ?
C9 C10 1.395(2) . ?
C9 C14 1.386(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Zn1 2.0348(13) . ?
O1 Zn1 1.9251(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 115.19(14) . . ?
O1 C1 C2 119.82(14) . . ?
O1 C1 C6 124.99(14) . . ?
C1 C2 Cl1 117.06(12) . . ?
C3 C2 C1 123.79(15) . . ?
C3 C2 Cl1 119.03(13) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.76(15) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Cl2 119.71(13) . . ?
C5 C4 C3 120.67(15) . . ?
C5 C4 Cl2 119.58(14) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.49(16) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 123.26(14) . . ?
C5 C6 C1 121.09(14) . . ?
C5 C6 C7 115.56(15) . . ?
C6 C7 H7 116.5 . . ?
N1 C7 C6 127.08(15) . . ?
N1 C7 H7 116.5 . . ?
C9 C8 H8 108.2 . . ?
C9 C8 C15 114.37(14) . . ?
C15 C8 H8 108.2 . . ?
N1 C8 H8 108.2 . . ?
N1 C8 C9 109.51(13) . . ?
N1 C8 C15 108.24(14) . . ?
C10 C9 C8 118.17(15) . . ?
C14 C9 C8 123.04(16) . . ?
C14 C9 C10 118.76(16) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.83(18) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.01(19) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.58(19) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.51(18) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 120.26(18) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 116.89(14) . . ?
C7 N1 Zn1 119.29(11) . . ?
C8 N1 Zn1 123.81(10) . . ?
C1 O1 Zn1 121.93(11) . . ?
N1 Zn1 N1 122.31(8) . 2_656 ?
O1 Zn1 N1 93.59(5) . . ?
O1 Zn1 N1 93.59(5) 2_656 2_656 ?
O1 Zn1 N1 109.51(5) . 2_656 ?
O1 Zn1 N1 109.52(5) 2_656 . ?
O1 Zn1 O1 131.45(7) 2_656 . ?

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 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 N1 -12.3(3) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C2 C1 C6 C7 -175.29(15) . . . . ?
C2 C1 O1 Zn1 -156.80(12) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C2 C3 C4 Cl2 -176.74(13) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 C7 176.40(16) . . . . ?
C5 C6 C7 N1 171.10(16) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C1 C2 Cl1 -176.99(12) . . . . ?
C6 C1 O1 Zn1 23.6(2) . . . . ?
C6 C7 N1 C8 173.23(16) . . . . ?
C6 C7 N1 Zn1 -8.1(2) . . . . ?
C8 C9 C10 C11 179.81(19) . . . . ?
C8 C9 C14 C13 179.45(16) . . . . ?
C9 C8 N1 C7 123.73(16) . . . . ?
C9 C8 N1 Zn1 -54.85(17) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C9 C14 C13 1.4(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 C14 -1.8(3) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
C14 C9 C10 C11 -2.0(3) . . . . ?
C15 C8 C9 C10 -173.37(15) . . . . ?
C15 C8 C9 C14 8.6(2) . . . . ?
C15 C8 N1 C7 -110.98(17) . . . . ?
C15 C8 N1 Zn1 70.45(16) . . . . ?
Cl1 C2 C3 C4 175.83(14) . . . . ?
Cl2 C4 C5 C6 176.96(13) . . . . ?
N1 C8 C9 C10 -51.7(2) . . . . ?
N1 C8 C9 C14 130.23(16) . . . . ?
O1 C1 C2 C3 179.51(16) . . . . ?
O1 C1 C2 Cl1 3.4(2) . . . . ?
O1 C1 C6 C5 -179.32(15) . . . . ?
O1 C1 C6 C7 4.3(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_hadi2211
_database_code_depnum_ccdc_archive 'CCDC 2000652'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2021-12-28 downloaded from the CCDC.
;

_audit_creation_date             2019-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Cl4 N2 O2 Zn'
_chemical_formula_sum            'C30 H24 Cl4 N2 O2 Zn'
_chemical_formula_weight         651.68
_chemical_absolute_configuration ad
_chemical_melting_point          ?

_chemical_oxdiff_usercomment     'sample (S)'

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.0890(3)
_cell_length_b                   10.8821(3)
_cell_length_c                   12.7748(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.586(3)
_cell_angle_gamma                90
_cell_volume                     1344.19(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7318
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      29.1820
_cell_measurement_theta_min      3.3110
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.705
_exptl_absorpt_coefficient_mu    1.344
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0560
-1 0 1 0.0280
5 -5 -1 0.0884
-5 0 -3 0.0336
1 5 3 0.0787
5 5 3 0.0922
3 -5 1 0.0900

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08

_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12841
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.818
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  83.00   0.80   12.50    --    9.77  37.00-180.00  120
  2  ω    -20.00  48.80   0.80   12.50    --    9.77 -99.00   0.00   86
  3  ω    -77.00  95.00   0.80   12.50    --    9.77   0.00 150.00  215
  4  ω    -37.00  59.00   0.80   12.50    --  -10.39  57.00 150.00  120
  5  ω    -64.00 -26.40   0.80   12.50    --    9.77 -77.00  30.00   47
  6  ω    -20.00  48.80   0.80   12.50    --    9.77 -99.00  90.00   86
  7  ω    -20.00  48.80   0.80   12.50    --    9.77 -99.00 -90.00   86
  8  ω    -20.00  29.60   0.80   12.50    --  -10.39 -99.00 -30.00   62
  9  ω    -20.00  29.60   0.80   12.50    --  -10.39 -99.00-120.00   62
 10  ω    -83.00  11.40   0.80   12.50    --  -10.39 -37.00-180.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0478085000
_diffrn_orient_matrix_UB_12      -0.0488246000
_diffrn_orient_matrix_UB_13      0.0172919000
_diffrn_orient_matrix_UB_21      0.0329004000
_diffrn_orient_matrix_UB_22      0.0166555000
_diffrn_orient_matrix_UB_23      -0.0401426000
_diffrn_orient_matrix_UB_31      0.0448672000
_diffrn_orient_matrix_UB_32      0.0398651000
_diffrn_orient_matrix_UB_33      0.0379898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2628
_reflns_number_total             2754

_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1194 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+0.9673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0572
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1 C 0.3963(3) 0.3723(3) 0.2696(2) 0.0165(6) Uani 1 1 d . . . . .
C2 C 0.4149(3) 0.3406(3) 0.1665(3) 0.0181(7) Uani 1 1 d . . . . .
C3 C 0.3462(3) 0.3955(4) 0.0698(2) 0.0218(6) Uani 1 1 d . . . . .
H3 H 0.361910 0.370154 0.003202 0.026 Uiso 1 1 calc R . . . .
C4 C 0.2527(3) 0.4893(3) 0.0709(3) 0.0214(7) Uani 1 1 d . . . . .
C5 C 0.2278(3) 0.5241(3) 0.1669(2) 0.0198(7) Uani 1 1 d . . . . .
H5 H 0.162653 0.587306 0.166349 0.024 Uiso 1 1 calc R . . . .
C6 C 0.2976(3) 0.4670(3) 0.2655(2) 0.0173(6) Uani 1 1 d . . . . .
C7 C 0.2567(3) 0.5056(3) 0.3606(3) 0.0177(6) Uani 1 1 d . . . . .
H7 H 0.177105 0.556526 0.346992 0.021 Uiso 1 1 calc R . . . .
C8 C 0.2444(3) 0.5187(3) 0.5424(2) 0.0186(7) Uani 1 1 d . . . . .
H8 H 0.162928 0.570192 0.504097 0.022 Uiso 1 1 calc R . . . .
C9 C 0.3421(3) 0.5970(3) 0.6288(3) 0.0190(7) Uani 1 1 d . . . . .
C10 C 0.3661(4) 0.5770(3) 0.7402(3) 0.0218(7) Uani 1 1 d . . . . .
H10 H 0.321072 0.511189 0.765102 0.026 Uiso 1 1 calc R . . . .
C11 C 0.4556(4) 0.6530(3) 0.8149(3) 0.0276(8) Uani 1 1 d . . . . .
H11 H 0.470941 0.638920 0.890808 0.033 Uiso 1 1 calc R . . . .
C12 C 0.5224(4) 0.7479(4) 0.7812(3) 0.0329(9) Uani 1 1 d . . . . .
H12 H 0.585564 0.797958 0.833266 0.039 Uiso 1 1 calc R . . . .
C13 C 0.4967(4) 0.7705(3) 0.6699(3) 0.0333(9) Uani 1 1 d . . . . .
H13 H 0.540981 0.837120 0.645430 0.040 Uiso 1 1 calc R . . . .
C14 C 0.4072(4) 0.6960(3) 0.5956(3) 0.0271(8) Uani 1 1 d . . . . .
H14 H 0.389378 0.712378 0.519778 0.033 Uiso 1 1 calc R . . . .
C15 C 0.1915(4) 0.4040(4) 0.5863(3) 0.0265(8) Uani 1 1 d . . . . .
H15A H 0.130166 0.358165 0.525584 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.140412 0.428202 0.637774 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.270041 0.352055 0.623881 0.040 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.54057(8) 0.22978(8) 0.16732(6) 0.02408(19) Uani 1 1 d . . . . .
Cl2 Cl 0.17053(10) 0.56646(9) -0.04968(7) 0.0327(2) Uani 1 1 d . . . . .
N1 N 0.3158(3) 0.4789(2) 0.4607(2) 0.0165(5) Uani 1 1 d . . . . .
O1 O 0.4660(2) 0.3154(2) 0.35729(17) 0.0191(5) Uani 1 1 d . . . . .
Zn1 Zn 0.500000 0.38832(4) 0.500000 0.01672(14) Uani 1 2 d S T P . .


_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
C1 C2 1.426(4) . ?
C1 C6 1.424(4) . ?
C1 O1 1.297(4) . ?
C2 C3 1.369(5) . ?
C2 Cl1 1.747(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(5) . ?
C4 C5 1.373(5) . ?
C4 Cl2 1.743(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(4) . ?
C6 C7 1.452(4) . ?
C7 H7 0.9500 . ?
C7 N1 1.281(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.515(4) . ?
C8 C15 1.525(5) . ?
C8 N1 1.491(4) . ?
C9 C10 1.391(4) . ?
C9 C14 1.389(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.368(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Zn1 2.036(3) . ?
O1 Zn1 1.927(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
C6 C1 C2 114.6(3) . . ?
O1 C1 C2 120.1(3) . . ?
O1 C1 C6 125.3(3) . . ?
C1 C2 Cl1 116.6(2) . . ?
C3 C2 C1 124.2(3) . . ?
C3 C2 Cl1 119.1(2) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Cl2 119.8(2) . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 Cl2 119.6(3) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 122.8(3) . . ?
C5 C6 C1 121.4(3) . . ?
C5 C6 C7 115.7(3) . . ?
C6 C7 H7 116.3 . . ?
N1 C7 C6 127.4(3) . . ?
N1 C7 H7 116.3 . . ?
C9 C8 H8 108.3 . . ?
C9 C8 C15 114.5(3) . . ?
C15 C8 H8 108.3 . . ?
N1 C8 H8 108.3 . . ?
N1 C8 C9 109.3(3) . . ?
N1 C8 C15 108.0(3) . . ?
C10 C9 C8 123.0(3) . . ?
C14 C9 C8 118.6(3) . . ?
C14 C9 C10 118.4(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 116.9(3) . . ?
C7 N1 Zn1 119.2(2) . . ?
C8 N1 Zn1 123.9(2) . . ?
C1 O1 Zn1 121.8(2) . . ?
N1 Zn1 N1 122.11(15) 2_656 . ?
O1 Zn1 N1 93.59(9) 2_656 2_656 ?
O1 Zn1 N1 93.59(9) . . ?
O1 Zn1 N1 109.62(10) . 2_656 ?
O1 Zn1 N1 109.62(10) 2_656 . ?
O1 Zn1 O1 131.37(13) 2_656 . ?

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 C2 C3 C4 0.6(5) . . . . ?
C1 C6 C7 N1 12.8(5) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
C2 C1 C6 C7 175.2(3) . . . . ?
C2 C1 O1 Zn1 156.7(2) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C2 C3 C4 Cl2 176.6(3) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 C7 -176.2(3) . . . . ?
C5 C6 C7 N1 -170.8(3) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C6 C1 C2 Cl1 177.1(2) . . . . ?
C6 C1 O1 Zn1 -23.9(4) . . . . ?
C6 C7 N1 C8 -173.4(3) . . . . ?
C6 C7 N1 Zn1 7.5(4) . . . . ?
C8 C9 C10 C11 -179.3(3) . . . . ?
C8 C9 C14 C13 179.9(3) . . . . ?
C9 C8 N1 C7 -124.0(3) . . . . ?
C9 C8 N1 Zn1 55.0(3) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C9 C14 C13 2.1(5) . . . . ?
C10 C11 C12 C13 1.8(6) . . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
C12 C13 C14 C9 -0.7(6) . . . . ?
C14 C9 C10 C11 -1.5(5) . . . . ?
C15 C8 C9 C10 -9.1(4) . . . . ?
C15 C8 C9 C14 173.2(3) . . . . ?
C15 C8 N1 C7 110.8(3) . . . . ?
C15 C8 N1 Zn1 -70.1(3) . . . . ?
Cl1 C2 C3 C4 -175.9(3) . . . . ?
Cl2 C4 C5 C6 -177.0(2) . . . . ?
N1 C8 C9 C10 -130.4(3) . . . . ?
N1 C8 C9 C14 51.8(4) . . . . ?
O1 C1 C2 C3 -179.9(3) . . . . ?
O1 C1 C2 Cl1 -3.3(4) . . . . ?
O1 C1 C6 C5 179.5(3) . . . . ?
O1 C1 C6 C7 -4.3(5) . . . . ?


####################################################################### 
# 
# 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_hadi1511
_database_code_depnum_ccdc_archive 'CCDC 2000650'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-05-02 deposited with the CCDC.	2021-12-28 downloaded from the CCDC.
;

_audit_creation_date             2019-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Br4 N2 O2 Zn'
_chemical_formula_sum            'C30 H24 Br4 N2 O2 Zn'
_chemical_formula_weight         829.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?

_chemical_oxdiff_usercomment     'sample (S) + Br2 + Zn'

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.2179(3)
_cell_length_b                   10.9275(3)
_cell_length_c                   12.9953(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.617(3)
_cell_angle_gamma                90
_cell_volume                     1390.41(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12710
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      29.8800
_cell_measurement_theta_min      2.9600
_shelx_estimated_absorpt_T_max   0.653
_shelx_estimated_absorpt_T_min   0.232
_exptl_absorpt_coefficient_mu    6.663
_exptl_absorpt_correction_T_max  0.672
_exptl_absorpt_correction_T_min  0.232
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0358
-1 0 1 0.0308
0 -1 -1 0.0950
5 -5 1 0.1157
0 1 -1 0.1065
1 1 0 0.0717
-1 -1 -1 0.1244
5 -2 -2 0.0819
5 0 1 0.1226

_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07

_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14735
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.480
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  85.00   0.50    6.00    --    3.20  19.00  90.00  200
  2  ω    -14.00  83.00   0.50    6.00    --    3.20  38.00 -30.00  194
  3  ω    -15.00  77.00   0.50    6.00    --    3.20  57.00 120.00  184
  4  ω     38.00  84.00   0.50    6.00    --    3.20 178.00 150.00   92
  5  ω     38.00  84.00   0.50    6.00    --    3.20 178.00   0.00   92
  6  ω    -22.00  78.00   0.50    6.00    --    3.20  77.00 -90.00  200
  7  ω    -23.00   6.00   0.50    6.00    --   -4.45  57.00-180.00   58
  8  ω    -78.00  14.00   0.50    6.00    --   -4.45 -57.00-180.00  184
  9  ω     35.00  84.00   0.50    6.00    --    3.20-178.00  90.00   98
 10  ω     35.00  84.00   0.50    6.00    --    3.20-178.00 120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0384985000
_diffrn_orient_matrix_UB_12      0.0053465000
_diffrn_orient_matrix_UB_13      -0.0373570000
_diffrn_orient_matrix_UB_21      -0.0302466000
_diffrn_orient_matrix_UB_22      0.0578642000
_diffrn_orient_matrix_UB_23      -0.0163699000
_diffrn_orient_matrix_UB_31      0.0533587000
_diffrn_orient_matrix_UB_32      0.0288987000
_diffrn_orient_matrix_UB_33      0.0398076000
_diffrn_oxdiff_digest_frames     
;
019823a3565b4ad4e1d9fddddf07eeaaa20140099f1
;
_diffrn_oxdiff_digest_hkl        
;
010a6db731a0d0be731f8d384c384ab2983da5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2727
_reflns_number_total             2839

_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0180
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0418
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.44546(3) 0.22578(3) 0.82738(3) 0.02493(10) Uani 1 1 d . . . . .
Br2 Br 0.83108(4) 0.57689(3) 1.05137(3) 0.03137(11) Uani 1 1 d . . . . .
C1 C 0.6022(3) 0.3741(3) 0.7277(3) 0.0192(7) Uani 1 1 d . . . . .
C2 C 0.5836(4) 0.3430(3) 0.8279(3) 0.0210(8) Uani 1 1 d . . . . .
C3 C 0.6519(3) 0.3982(4) 0.9244(3) 0.0235(7) Uani 1 1 d . . . . .
H3 H 0.635827 0.373401 0.989746 0.028 Uiso 1 1 calc R . . . .
C4 C 0.7449(4) 0.4912(3) 0.9229(3) 0.0226(7) Uani 1 1 d . . . . .
C5 C 0.7692(3) 0.5255(3) 0.8289(3) 0.0223(7) Uani 1 1 d . . . . .
H5 H 0.832943 0.588923 0.829454 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7005(3) 0.4679(3) 0.7306(3) 0.0203(7) Uani 1 1 d . . . . .
C7 C 0.7400(4) 0.5074(3) 0.6376(3) 0.0207(7) Uani 1 1 d . . . . .
H7 H 0.818255 0.558583 0.651149 0.025 Uiso 1 1 calc R . . . .
C8 C 0.7522(3) 0.5219(3) 0.4597(3) 0.0220(7) Uani 1 1 d . . . . .
H8 H 0.831181 0.574483 0.498108 0.026 Uiso 1 1 calc R . . . .
C9 C 0.6551(3) 0.5998(3) 0.3731(3) 0.0217(7) Uani 1 1 d . . . . .
C10 C 0.6311(4) 0.5780(4) 0.2637(3) 0.0251(7) Uani 1 1 d . . . . .
H10 H 0.673803 0.510665 0.240135 0.030 Uiso 1 1 calc R . . . .
C11 C 0.5451(4) 0.6543(4) 0.1890(3) 0.0312(9) Uani 1 1 d . . . . .
H11 H 0.531014 0.640188 0.114494 0.037 Uiso 1 1 calc R . . . .
C12 C 0.4799(4) 0.7503(4) 0.2221(4) 0.0354(9) Uani 1 1 d . . . . .
H12 H 0.418813 0.800692 0.170563 0.042 Uiso 1 1 calc R . . . .
C13 C 0.5034(5) 0.7734(4) 0.3312(4) 0.0371(10) Uani 1 1 d . . . . .
H13 H 0.459208 0.840087 0.354240 0.045 Uiso 1 1 calc R . . . .
C14 C 0.5916(4) 0.6989(4) 0.4060(3) 0.0310(9) Uani 1 1 d . . . . .
H14 H 0.608906 0.715707 0.480428 0.037 Uiso 1 1 calc R . . . .
C15 C 0.8085(4) 0.4100(4) 0.4165(3) 0.0277(8) Uani 1 1 d . . . . .
H15A H 0.867267 0.363382 0.476443 0.042 Uiso 1 1 calc GR . . . .
H15B H 0.861758 0.436547 0.368607 0.042 Uiso 1 1 calc GR . . . .
H15C H 0.732615 0.358256 0.376495 0.042 Uiso 1 1 calc GR . . . .
N1 N 0.6817(3) 0.4815(3) 0.5389(2) 0.0208(6) Uani 1 1 d . . . . .
O1 O 0.5326(3) 0.3185(2) 0.6407(2) 0.0219(5) Uani 1 1 d . . . . .
Zn1 Zn 0.500000 0.39020(5) 0.500000 0.01932(13) Uani 1 2 d S T P . .


_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 C2 1.904(4) . ?
Br2 C4 1.897(3) . ?
C1 C2 1.410(5) . ?
C1 C6 1.428(5) . ?
C1 O1 1.302(4) . ?
C2 C3 1.387(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(5) . ?
C4 C5 1.367(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.417(5) . ?
C6 C7 1.445(5) . ?
C7 H7 0.9500 . ?
C7 N1 1.282(5) . ?
C8 H8 1.0000 . ?
C8 C9 1.529(5) . ?
C8 C15 1.526(6) . ?
C8 N1 1.482(5) . ?
C9 C10 1.392(5) . ?
C9 C14 1.392(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(6) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Zn1 2.039(3) . ?
O1 Zn1 1.928(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
C2 C1 C6 115.4(3) . . ?
O1 C1 C2 120.3(3) . . ?
O1 C1 C6 124.3(3) . . ?
C1 C2 Br1 117.0(2) . . ?
C3 C2 Br1 118.5(3) . . ?
C3 C2 C1 124.3(3) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.3(3) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 Br2 119.6(3) . . ?
C5 C4 Br2 119.6(3) . . ?
C5 C4 C3 120.7(3) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 123.8(3) . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 C7 115.9(3) . . ?
C6 C7 H7 116.2 . . ?
N1 C7 C6 127.5(3) . . ?
N1 C7 H7 116.2 . . ?
C9 C8 H8 108.0 . . ?
C15 C8 H8 108.0 . . ?
C15 C8 C9 114.1(3) . . ?
N1 C8 H8 108.0 . . ?
N1 C8 C9 109.6(3) . . ?
N1 C8 C15 109.1(3) . . ?
C10 C9 C8 123.0(3) . . ?
C14 C9 C8 117.9(3) . . ?
C14 C9 C10 119.0(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.9(4) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C8 116.7(3) . . ?
C7 N1 Zn1 119.1(3) . . ?
C8 N1 Zn1 124.2(2) . . ?
C1 O1 Zn1 122.5(2) . . ?
N1 Zn1 N1 121.44(16) . 2_656 ?
O1 Zn1 N1 109.37(12) 2_656 . ?
O1 Zn1 N1 109.37(11) . 2_656 ?
O1 Zn1 N1 93.77(11) 2_656 2_656 ?
O1 Zn1 N1 93.77(11) . . ?
O1 Zn1 O1 132.04(15) . 2_656 ?

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
Br1 C2 C3 C4 -174.8(3) . . . . ?
Br2 C4 C5 C6 -176.4(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C1 C6 C7 N1 11.8(6) . . . . ?
C2 C1 C6 C5 -1.8(5) . . . . ?
C2 C1 C6 C7 176.2(3) . . . . ?
C2 C1 O1 Zn1 156.9(3) . . . . ?
C2 C3 C4 Br2 175.6(3) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 1.3(5) . . . . ?
C4 C5 C6 C7 -176.8(3) . . . . ?
C5 C6 C7 N1 -170.2(3) . . . . ?
C6 C1 C2 Br1 176.2(2) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C6 C1 O1 Zn1 -23.3(4) . . . . ?
C6 C7 N1 C8 -173.0(3) . . . . ?
C6 C7 N1 Zn1 7.5(5) . . . . ?
C8 C9 C10 C11 -178.0(3) . . . . ?
C8 C9 C14 C13 179.5(4) . . . . ?
C9 C8 N1 C7 -124.9(3) . . . . ?
C9 C8 N1 Zn1 54.6(4) . . . . ?
C9 C10 C11 C12 -1.7(6) . . . . ?
C10 C9 C14 C13 1.4(6) . . . . ?
C10 C11 C12 C13 2.0(6) . . . . ?
C11 C12 C13 C14 -0.6(6) . . . . ?
C12 C13 C14 C9 -1.1(6) . . . . ?
C14 C9 C10 C11 0.0(5) . . . . ?
C15 C8 C9 C10 -6.3(5) . . . . ?
C15 C8 C9 C14 175.7(3) . . . . ?
C15 C8 N1 C7 109.6(3) . . . . ?
C15 C8 N1 Zn1 -71.0(3) . . . . ?
N1 C8 C9 C10 -128.9(4) . . . . ?
N1 C8 C9 C14 53.1(4) . . . . ?
O1 C1 C2 Br1 -4.0(4) . . . . ?
O1 C1 C2 C3 -179.2(3) . . . . ?
O1 C1 C6 C5 178.4(3) . . . . ?
O1 C1 C6 C7 -3.6(5) . . . . ?


