# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2208029'
loop_
_audit_author_name
_audit_author_address
lidongyang
;Jining University
China
;
_audit_update_record             
;
2022-11-07 deposited with the CCDC.	2022-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 Br4 N2 Zn'
_chemical_formula_sum            'C14 H20 Br4 N2 Zn'
_chemical_formula_weight         601.33

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   27.5957(4)
_cell_length_b                   8.22990(10)
_cell_length_c                   17.9221(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.3750(10)
_cell_angle_gamma                90
_cell_volume                     4045.12(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9587
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      28.56

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   0.547
_exptl_transmission_factor_max   0.717
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    10.899
_shelx_estimated_absorpt_T_min   0.208
_shelx_estimated_absorpt_T_max   0.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   '(J. Appl. Cryst. 2013, 46, 252-254)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10010
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.223
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3549
_reflns_number_gt                3248
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²+4.0314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3549
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42454(2) 0.65497(6) 0.71418(3) 0.06102(16) Uani 1 1 d . . . . .
Br2 Br 0.29233(2) 0.60580(7) 0.60563(3) 0.06936(18) Uani 1 1 d . . . . .
Br3 Br 0.34711(2) 1.03708(5) 0.64773(2) 0.05256(15) Uani 1 1 d . . . . .
Br4 Br 0.40326(2) 0.76189(6) 0.49871(2) 0.05876(16) Uani 1 1 d . . . . .
Zn1 Zn 0.36636(2) 0.75994(6) 0.61477(3) 0.04285(16) Uani 1 1 d . . . . .
C1 C 0.47843(16) 1.0771(5) 0.6107(2) 0.0556(10) Uani 1 1 d . . . . .
H1 H 0.454034 1.021331 0.581113 0.067 Uiso 1 1 calc R U . . .
C2 C 0.51328(19) 0.9930(6) 0.6541(3) 0.0633(11) Uani 1 1 d . . . . .
H2 H 0.512513 0.880008 0.654737 0.076 Uiso 1 1 calc R U . . .
C3 C 0.54948(17) 1.0747(7) 0.6967(3) 0.0676(13) Uani 1 1 d . . . . .
H3 H 0.573864 1.018094 0.725824 0.081 Uiso 1 1 calc R U . . .
C4 C 0.54943(17) 1.2397(7) 0.6960(3) 0.0670(13) Uani 1 1 d . . . . .
H4 H 0.573757 1.296745 0.725054 0.080 Uiso 1 1 calc R U . . .
C5 C 0.51391(17) 1.3214(6) 0.6529(3) 0.0593(11) Uani 1 1 d . . . . .
H5 H 0.513793 1.434375 0.652979 0.071 Uiso 1 1 calc R U . . .
C6 C 0.4406(2) 1.3294(7) 0.5626(3) 0.0714(13) Uani 1 1 d . . . . .
H6A H 0.441821 1.443376 0.576345 0.086 Uiso 1 1 calc R U . . .
H6B H 0.408854 1.287475 0.571194 0.086 Uiso 1 1 calc R U . . .
C7 C 0.4472(2) 1.3127(8) 0.4809(3) 0.0777(14) Uani 1 1 d . . . . .
H7A H 0.422958 1.376498 0.451514 0.116 Uiso 1 1 calc R U . . .
H7B H 0.443693 1.200702 0.466360 0.116 Uiso 1 1 calc R U . . .
H7C H 0.479074 1.350315 0.472638 0.116 Uiso 1 1 calc R U . . .
N1 N 0.47893(12) 1.2400(4) 0.61015(18) 0.0488(8) Uani 1 1 d . . . . .
C8 C 0.29347(18) 0.4007(6) 0.4261(2) 0.0641(11) Uani 1 1 d . . . . .
H8 H 0.282412 0.492955 0.448938 0.077 Uiso 1 1 calc R U . . .
C9 C 0.30779(19) 0.2702(7) 0.4685(3) 0.0687(13) Uani 1 1 d . . . . .
H9 H 0.307474 0.273595 0.520333 0.082 Uiso 1 1 calc R U . . .
C10 C 0.32286(19) 0.1320(7) 0.4345(3) 0.0747(14) Uani 1 1 d . . . . .
H10 H 0.331254 0.039213 0.462610 0.090 Uiso 1 1 calc R U . . .
C11 C 0.32531(19) 0.1329(6) 0.3582(3) 0.0721(13) Uani 1 1 d . . . . .
H11 H 0.336245 0.041974 0.334266 0.087 Uiso 1 1 calc R U . . .
C12 C 0.31132(17) 0.2709(6) 0.3181(3) 0.0595(11) Uani 1 1 d . . . . .
H12 H 0.313340 0.273948 0.266623 0.071 Uiso 1 1 calc R U . . .
C13 C 0.27956(18) 0.5472(6) 0.3061(3) 0.0685(12) Uani 1 1 d . . . . .
H13A H 0.265940 0.513448 0.256268 0.082 Uiso 1 1 calc R U . . .
H13B H 0.254426 0.605027 0.329085 0.082 Uiso 1 1 calc R U . . .
C14 C 0.3206(2) 0.6548(7) 0.3001(4) 0.0913(18) Uani 1 1 d . . . . .
H14A H 0.343928 0.601581 0.272551 0.137 Uiso 1 1 calc R U . . .
H14B H 0.335590 0.681737 0.349443 0.137 Uiso 1 1 calc R U . . .
H14C H 0.309353 0.752342 0.274331 0.137 Uiso 1 1 calc R U . . .
N2 N 0.29491(12) 0.3997(4) 0.35233(19) 0.0518(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Zn1 2.4212(6) . ?
Br2 Zn1 2.3950(7) . ?
Br3 Zn1 2.4296(6) . ?
Br4 Zn1 2.4154(6) . ?
C1 N1 1.341(5) . ?
C1 C2 1.358(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.343(6) . ?
C5 H5 0.9300 . ?
C6 N1 1.479(6) . ?
C6 C7 1.501(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N2 1.327(5) . ?
C8 C9 1.350(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(7) . ?
C11 H11 0.9300 . ?
C12 N2 1.330(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.450(7) . ?
C13 N2 1.504(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br2 Zn1 Br4 112.50(2) . . ?
Br2 Zn1 Br1 110.62(3) . . ?
Br4 Zn1 Br1 109.12(3) . . ?
Br2 Zn1 Br3 107.82(3) . . ?
Br4 Zn1 Br3 109.12(2) . . ?
Br1 Zn1 Br3 107.52(2) . . ?
N1 C1 C2 120.4(4) . . ?
N1 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 119.8(5) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 120.4(4) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C7 111.2(4) . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 N1 C5 120.1(4) . . ?
C1 N1 C6 119.6(4) . . ?
C5 N1 C6 120.2(4) . . ?
N2 C8 C9 121.1(5) . . ?
N2 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C10 119.4(5) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 118.9(5) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N2 C12 C11 120.4(4) . . ?
N2 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 N2 111.0(4) . . ?
C14 C13 H13A 109.4 . . ?
N2 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
N2 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 N2 C12 121.0(4) . . ?
C8 N2 C13 120.4(4) . . ?
C12 N2 C13 118.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.9(7) . . . . ?
C1 C2 C3 C4 1.2(7) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
C3 C4 C5 N1 -0.7(7) . . . . ?
C2 C1 N1 C5 -0.3(6) . . . . ?
C2 C1 N1 C6 -179.9(4) . . . . ?
C4 C5 N1 C1 1.1(6) . . . . ?
C4 C5 N1 C6 -179.3(4) . . . . ?
C7 C6 N1 C1 -71.3(6) . . . . ?
C7 C6 N1 C5 109.1(5) . . . . ?
N2 C8 C9 C10 -1.8(8) . . . . ?
C8 C9 C10 C11 3.3(8) . . . . ?
C9 C10 C11 C12 -1.8(8) . . . . ?
C10 C11 C12 N2 -1.2(7) . . . . ?
C9 C8 N2 C12 -1.2(7) . . . . ?
C9 C8 N2 C13 -179.0(5) . . . . ?
C11 C12 N2 C8 2.7(7) . . . . ?
C11 C12 N2 C13 -179.4(4) . . . . ?
C14 C13 N2 C8 89.9(6) . . . . ?
C14 C13 N2 C12 -88.1(6) . . . . ?

_refine_diff_density_max         0.679
_refine_diff_density_min         -1.586
_refine_diff_density_rms         0.239



