#------------------------------------------------------------------------------
#$Date: 2024-05-05 04:06:02 +0300 (Sun, 05 May 2024) $
#$Revision: 291537 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/28/7132825.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7132825
loop_
_publ_author_name
'Samanta, Arup'
'Behera, Prativa'
'Chaubey, Amit'
'Mondal, Avijit'
'Pal, Debjyoti'
'Mohar, Kailash'
'Roy, Lisa'
'Srimani, Dipankar'
_publ_section_title
;
 Experimental and theoretical insights for designing Zn²⁺
 complexes to trigger chemo-selective hetero-coupling of alcohols.
;
_journal_issue                   30
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4056
_journal_page_last               4059
_journal_paper_doi               10.1039/d4cc00864b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C12 H11 Br2 N3 Zn'
_chemical_formula_sum            'C12 H11 Br2 N3 Zn'
_chemical_formula_weight         422.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-01-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-01-24 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                77.783(10)
_cell_angle_beta                 85.879(13)
_cell_angle_gamma                77.735(11)
_cell_formula_units_Z            2
_cell_length_a                   7.8069(14)
_cell_length_b                   7.8757(8)
_cell_length_c                   11.9902(16)
_cell_measurement_reflns_used    1114
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.7070
_cell_measurement_theta_min      2.7010
_cell_volume                     703.79(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2760
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.879
_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 -44.00   1.00   16.47    --  -17.33-178.00  90.00   26
  2  ω    -20.00  21.00   1.00   16.47    --  -17.33 -99.00 -30.00   41
  3  ω    -19.00  24.00   1.00   16.47    --  -17.33 -99.00 150.00   43
  4  ω     35.00  94.00   1.00   16.47    --   20.92-178.00   0.00   59
  5  ω     -4.00  82.00   1.00   16.47    --   20.92  38.00 150.00   86
  6  ω    -40.00  65.00   1.00   16.47    --   20.92 -19.00 -60.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0506358000
_diffrn_orient_matrix_UB_12      -0.0637217000
_diffrn_orient_matrix_UB_13      0.0253824000
_diffrn_orient_matrix_UB_21      0.0713547000
_diffrn_orient_matrix_UB_22      -0.0479406000
_diffrn_orient_matrix_UB_23      0.0346631000
_diffrn_orient_matrix_UB_31      -0.0315628000
_diffrn_orient_matrix_UB_32      0.0499507000
_diffrn_orient_matrix_UB_33      0.0426692000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.1732
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5082
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.679
_diffrn_reflns_theta_min         2.671
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    7.407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.993
_exptl_crystal_description       Block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.238
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3204
_refine_ls_number_restraints     116
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.1565
_refine_ls_R_factor_gt           0.0817
_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)+(0.0735P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.2279
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1409
_reflns_number_total             3204
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00864b2.cif
_cod_data_source_block           as-ph-1
_cod_depositor_comments
'Adding full bibliography for 7132825--7132828.cif.'
_cod_database_code               7132825
_shelx_shelxl_version_number     2019/1
_chemical_oxdiff_formula         ZnNCBrH
_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.
;
_diffrn_oxdiff_ac4_digest_frames
;
01b4f329f3d147bbe36155cf741d32914b00027cde7
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C1-C2 = C4-C5 = C5-C6
 1.37 with sigma of 0.02
 C1-C6
 1.38 with sigma of 0.02
 C2-C3 = C3-C4
 1.36 with sigma of 0.02
 C1-C5
 2.38 with sigma of 0.04
 C2-C4
 2.36 with sigma of 0.04
 C1-C3 = C3-C5 = C4-C6
 2.37 with sigma of 0.04
 C1-C2 \\sim C2-C3 \\sim C3-C4 \\sim C4-C5 \\sim C5-C6 \\sim C6-C1
 with sigma of 0.02
 C1-C5 \\sim C1-C3 \\sim C5-C3 \\sim C4-C2 \\sim C4-C6 \\sim C6-C2
 with sigma of 0.04
3. Restrained planarity
 C1, C2, C3, C4, C5, C6
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C1(H1), C2(H2A), C3(H3),
  C4(H4), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.869
_oxdiff_exptl_absorpt_empirical_full_min 0.242
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.88920(18) 0.08344(14) 0.83601(12) 0.0679(5) Uani 1 1 d . . . . .
Br2 Br 0.48474(18) 0.01495(13) 0.67040(12) 0.0656(5) Uani 1 1 d . . . . .
Zn1 Zn 0.61606(18) 0.19621(14) 0.75444(11) 0.0487(4) Uani 1 1 d . . . . .
N3 N 0.4401(12) 0.3281(10) 0.8543(7) 0.044(2) Uani 1 1 d . . . . .
N1 N 0.6095(11) 0.4603(10) 0.6651(7) 0.0379(19) Uani 1 1 d . . . . .
N2 N 0.5240(13) 0.5689(10) 0.7342(7) 0.051(3) Uani 1 1 d . . . . .
H2 H 0.529051 0.679492 0.719210 0.061 Uiso 1 1 calc R U . . .
C8 C 0.4304(14) 0.5026(14) 0.8273(10) 0.047(3) Uani 1 1 d . . . . .
C7 C 0.6751(13) 0.5383(10) 0.5732(9) 0.041(2) Uani 1 1 d . . . . .
H7 H 0.659514 0.661093 0.561256 0.049 Uiso 1 1 calc R U . . .
C9 C 0.3266(15) 0.6161(13) 0.8925(9) 0.049(3) Uani 1 1 d . . . . .
H9 H 0.319367 0.737995 0.871810 0.058 Uiso 1 1 calc R U . . .
C10 C 0.2376(16) 0.5475(16) 0.9850(10) 0.058(3) Uani 1 1 d . . . . .
H10 H 0.173558 0.619957 1.031855 0.070 Uiso 1 1 calc R U . . .
C11 C 0.2432(18) 0.3622(17) 1.0099(11) 0.069(4) Uani 1 1 d . . . . .
H11 H 0.178231 0.311557 1.071145 0.083 Uiso 1 1 calc R U . . .
C12 C 0.3470(17) 0.2586(15) 0.9414(10) 0.058(3) Uani 1 1 d . . . . .
H12 H 0.351471 0.136918 0.957116 0.070 Uiso 1 1 calc R U . . .
C1 C 0.8002(15) 0.2731(11) 0.4870(8) 0.056(3) Uani 1 1 d D U . . .
H1 H 0.752098 0.199898 0.546730 0.068 Uiso 1 1 calc R U . . .
C2 C 0.8975(14) 0.2010(13) 0.4022(8) 0.065(4) Uani 1 1 d D U . . .
H2A H 0.915161 0.079719 0.404671 0.078 Uiso 1 1 calc R U . . .
C3 C 0.9682(14) 0.3077(12) 0.3145(8) 0.056(3) Uani 1 1 d D U . . .
H3 H 1.033622 0.258647 0.256858 0.067 Uiso 1 1 calc R U . . .
C4 C 0.9443(15) 0.4838(13) 0.3103(9) 0.059(3) Uani 1 1 d D U . . .
H4 H 0.995374 0.554851 0.250870 0.071 Uiso 1 1 calc R U . . .
C5 C 0.8447(14) 0.5583(12) 0.3937(8) 0.047(3) Uani 1 1 d D U . . .
H5 H 0.825383 0.680178 0.389191 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7727(14) 0.4519(10) 0.4847(8) 0.044(2) Uani 1 1 d D U . . .
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Zn1 Br2 119.56(6) . . ?
N3 Zn1 Br1 113.5(3) . . ?
N3 Zn1 Br2 110.6(2) . . ?
N3 Zn1 N1 80.3(3) . . ?
N1 Zn1 Br1 108.8(2) . . ?
N1 Zn1 Br2 117.7(2) . . ?
C8 N3 Zn1 112.5(6) . . ?
C12 N3 Zn1 127.0(7) . . ?
C12 N3 C8 120.4(9) . . ?
N2 N1 Zn1 107.0(5) . . ?
C7 N1 Zn1 137.6(6) . . ?
C7 N1 N2 115.1(7) . . ?
N1 N2 H2 120.0 . . ?
N1 N2 C8 119.9(7) . . ?
C8 N2 H2 120.0 . . ?
N3 C8 N2 118.3(8) . . ?
N3 C8 C9 121.2(9) . . ?
N2 C8 C9 120.5(9) . . ?
N1 C7 H7 117.1 . . ?
N1 C7 C6 125.8(8) . . ?
C6 C7 H7 117.1 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.5(9) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.6(9) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.7(10) . . ?
C12 C11 H11 120.6 . . ?
N3 C12 C11 121.5(10) . . ?
N3 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.9(8) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 C1 119.8(8) . . ?
C3 C2 H2A 120.1 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.7(8) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(8) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(8) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 124.2(8) . . ?
C1 C6 C5 118.3(8) . . ?
C5 C6 C7 117.4(7) . . ?
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 2.328(2) . ?
Br2 Zn1 2.3417(17) . ?
Zn1 N3 2.021(8) . ?
Zn1 N1 2.120(8) . ?
N3 C8 1.331(12) . ?
N3 C12 1.318(12) . ?
N1 N2 1.358(10) . ?
N1 C7 1.272(11) . ?
N2 H2 0.8600 . ?
N2 C8 1.360(12) . ?
C8 C9 1.402(13) . ?
C7 H7 0.9300 . ?
C7 C6 1.463(12) . ?
C9 H9 0.9300 . ?
C9 C10 1.341(14) . ?
C10 H10 0.9300 . ?
C10 C11 1.418(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(14) . ?
C12 H12 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.372(9) . ?
C1 C6 1.374(8) . ?
C2 H2A 0.9300 . ?
C2 C3 1.363(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.350(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(9) . ?
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
Zn1 N3 C8 N2 5.4(14) . . . . ?
Zn1 N3 C8 C9 -174.7(9) . . . . ?
Zn1 N3 C12 C11 173.7(10) . . . . ?
Zn1 N1 N2 C8 -14.0(12) . . . . ?
Zn1 N1 C7 C6 8.4(18) . . . . ?
N3 C8 C9 C10 1.2(19) . . . . ?
N1 N2 C8 N3 6.7(16) . . . . ?
N1 N2 C8 C9 -173.2(10) . . . . ?
N1 C7 C6 C1 3.1(18) . . . . ?
N1 C7 C6 C5 -175.7(11) . . . . ?
N2 N1 C7 C6 -179.9(10) . . . . ?
N2 C8 C9 C10 -178.9(12) . . . . ?
C8 N3 C12 C11 -2.7(19) . . . . ?
C8 C9 C10 C11 -3.8(19) . . . . ?
C7 N1 N2 C8 171.7(11) . . . . ?
C9 C10 C11 C12 3(2) . . . . ?
C10 C11 C12 N3 0(2) . . . . ?
C12 N3 C8 N2 -177.7(11) . . . . ?
C12 N3 C8 C9 2.2(18) . . . . ?
C1 C2 C3 C4 0.4(14) . . . . ?
C2 C1 C6 C7 -178.1(10) . . . . ?
C2 C1 C6 C5 0.6(17) . . . . ?
C2 C3 C4 C5 -1.4(18) . . . . ?
C3 C4 C5 C6 2.1(18) . . . . ?
C4 C5 C6 C7 177.2(11) . . . . ?
C4 C5 C6 C1 -1.7(17) . . . . ?
C6 C1 C2 C3 0.0(14) . . . . ?
