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#$Date: 2020-09-26 04:31:25 +0300 (Sat, 26 Sep 2020) $
#$Revision: 256785 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/13/7241314.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_7241314
loop_
_publ_author_name
'Ramirez de Arellano, Carmen'
'Adam, Rosa'
'Ballesteros-Garrido, Rafael'
'Abarca, Belén'
'Ballesteros, Rafael'
'Alkorta, Ibon'
'Elguero, Jose'
'Escrivá, Emilio'
_publ_section_title
;
 A C(π-hole)···Cl-Zn tetrel interaction driving a
 metal-organic supramolecular assembly
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01272F
_journal_year                    2020
_chemical_formula_sum            'C22 H16 Br2 Cl4 N10 Zn2'
_chemical_formula_weight         852.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-28 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.054(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3058(5)
_cell_length_b                   12.5506(3)
_cell_length_c                   15.1113(4)
_cell_measurement_reflns_used    25570
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.5875
_cell_measurement_theta_min      2.3866
_cell_volume                     2866.67(14)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies,2011)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies,2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies,2011)'
_computing_molecular_graphics    'CrystalMaker 2.1.5 (1994-2009)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.0267
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Oxford diffraction-Supernova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            61348
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         32.652
_diffrn_reflns_theta_min         2.394
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Agilent Technologies,2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         5055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0186
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0263P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0434
_refine_ls_wR_factor_ref         0.0441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3960
_reflns_number_total             5055
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01272f2.cif
_cod_data_source_block           ra4a250
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7241314
_shelx_shelxl_version_number     2018/3
_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'
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
Zn1 Zn -0.08305(2) 0.22435(2) 0.45463(2) 0.01246(4) Uani 1 1 d . . . . .
Br1 Br 0.11845(2) 0.39488(2) 0.69818(2) 0.01547(4) Uani 1 1 d . . . . .
Cl1 Cl -0.15977(2) 0.11087(3) 0.36187(2) 0.01925(7) Uani 1 1 d . . . . .
Cl2 Cl -0.06908(2) 0.39535(3) 0.42361(3) 0.02229(8) Uani 1 1 d . . . . .
N1 N 0.07092(7) 0.18026(9) 0.58955(7) 0.0134(2) Uani 1 1 d . . . . .
N2 N 0.04113(7) 0.16841(9) 0.50196(7) 0.0133(2) Uani 1 1 d . . . . .
C3 C 0.10582(9) 0.13892(11) 0.45619(9) 0.0136(3) Uani 1 1 d . . . . .
C3A C 0.18329(9) 0.13131(10) 0.51780(8) 0.0127(2) Uani 1 1 d . . . . .
C4 C 0.27247(9) 0.10331(11) 0.51636(9) 0.0159(3) Uani 1 1 d . . . . .
H4 H 0.291841 0.085134 0.461580 0.019 Uiso 1 1 calc R U . . .
C5 C 0.33015(9) 0.10279(11) 0.59464(10) 0.0170(3) Uani 1 1 d . . . . .
H5 H 0.390167 0.083440 0.594737 0.020 Uiso 1 1 calc R U . . .
C6 C 0.30102(9) 0.13110(11) 0.67638(9) 0.0153(3) Uani 1 1 d . . . . .
H6 H 0.341983 0.129903 0.730577 0.018 Uiso 1 1 calc R U . . .
C7 C 0.21562(8) 0.15986(10) 0.67847(8) 0.0118(2) Uani 1 1 d . . . . .
N8 N 0.15772(7) 0.15869(8) 0.59835(7) 0.0108(2) Uani 1 1 d . . . . .
N11 N 0.13459(7) 0.22078(9) 0.92697(7) 0.0133(2) Uani 1 1 d . . . . .
C12 C 0.18243(9) 0.13674(11) 0.90762(9) 0.0161(3) Uani 1 1 d . . . . .
H12 H 0.200970 0.087717 0.954742 0.019 Uiso 1 1 calc R U . . .
N13 N 0.20602(8) 0.11604(9) 0.82919(8) 0.0151(2) Uani 1 1 d . . . . .
C14 C 0.18359(8) 0.18750(10) 0.76302(8) 0.0119(2) Uani 1 1 d . . . . .
C15 C 0.13876(8) 0.28075(10) 0.77924(8) 0.0119(2) Uani 1 1 d . . . . .
C16 C 0.11403(9) 0.29369(11) 0.86277(9) 0.0135(3) Uani 1 1 d . . . . .
H16 H 0.081903 0.355451 0.874633 0.016 Uiso 1 1 calc R U . . .
C21 C 0.09020(10) 0.12070(12) 0.35733(9) 0.0201(3) Uani 1 1 d . . . . .
H21A H 0.047958 0.062193 0.342916 0.030 Uiso 1 1 calc R U . . .
H21B H 0.146219 0.102267 0.337420 0.030 Uiso 1 1 calc R U . . .
H21C H 0.066173 0.185689 0.326763 0.030 Uiso 1 1 calc R 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'
N N 0.0061 0.0033 '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'
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
N2 Zn1 N11 98.63(4) . 2_556 ?
N2 Zn1 Cl1 111.91(3) . . ?
N11 Zn1 Cl1 107.40(3) 2_556 . ?
N2 Zn1 Cl2 106.93(3) . . ?
N11 Zn1 Cl2 105.49(3) 2_556 . ?
Cl1 Zn1 Cl2 123.465(15) . . ?
N2 N1 N8 104.69(10) . . ?
N1 N2 C3 112.03(11) . . ?
N1 N2 Zn1 117.42(8) . . ?
C3 N2 Zn1 129.24(9) . . ?
N2 C3 C3A 107.07(11) . . ?
N2 C3 C21 122.79(12) . . ?
C3A C3 C21 130.15(12) . . ?
N8 C3A C3 104.07(11) . . ?
N8 C3A C4 118.98(12) . . ?
C3 C3A C4 136.94(12) . . ?
C5 C4 C3A 118.96(12) . . ?
C4 C5 C6 120.31(13) . . ?
C7 C6 C5 121.31(13) . . ?
C6 C7 N8 117.53(12) . . ?
C6 C7 C14 122.14(12) . . ?
N8 C7 C14 120.29(11) . . ?
N1 N8 C3A 112.13(10) . . ?
N1 N8 C7 124.93(10) . . ?
C3A N8 C7 122.90(11) . . ?
C16 N11 C12 117.05(11) . . ?
C16 N11 Zn1 122.41(9) . 2_556 ?
C12 N11 Zn1 120.09(9) . 2_556 ?
N13 C12 N11 125.94(12) . . ?
C12 N13 C14 117.54(12) . . ?
N13 C14 C15 120.15(11) . . ?
N13 C14 C7 113.86(11) . . ?
C15 C14 C7 125.89(11) . . ?
C16 C15 C14 118.08(12) . . ?
C16 C15 Br1 117.68(10) . . ?
C14 C15 Br1 124.02(10) . . ?
N11 C16 C15 121.05(12) . . ?
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
Zn1 N2 2.0467(11) . ?
Zn1 N11 2.0663(11) 2_556 ?
Zn1 Cl1 2.2032(4) . ?
Zn1 Cl2 2.2142(4) . ?
Br1 C15 1.8785(13) . ?
N1 N2 1.3386(15) . ?
N1 N8 1.3418(15) . ?
N2 C3 1.3459(17) . ?
C3 C3A 1.3909(18) . ?
C3 C21 1.4928(18) . ?
C3A N8 1.3795(16) . ?
C3A C4 1.4129(19) . ?
C4 C5 1.360(2) . ?
C5 C6 1.4226(19) . ?
C6 C7 1.3612(18) . ?
C7 N8 1.3833(16) . ?
C7 C14 1.4799(17) . ?
N11 C16 1.3347(16) . ?
N11 C12 1.3422(17) . ?
C12 N13 1.3180(17) . ?
N13 C14 1.3470(16) . ?
C14 C15 1.3977(18) . ?
C15 C16 1.3832(17) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 Br1 0.95 2.97 3.8732(13) 159.3 7_556 yes
C5 H5 Cl2 0.95 2.81 3.7106(14) 159.0 7_556 yes
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
N8 N1 N2 C3 0.82(14) . . . . ?
N8 N1 N2 Zn1 -167.30(8) . . . . ?
N1 N2 C3 C3A -0.23(15) . . . . ?
Zn1 N2 C3 C3A 166.12(9) . . . . ?
N1 N2 C3 C21 -179.78(12) . . . . ?
Zn1 N2 C3 C21 -13.43(19) . . . . ?
N2 C3 C3A N8 -0.44(14) . . . . ?
C21 C3 C3A N8 179.06(14) . . . . ?
N2 C3 C3A C4 178.55(15) . . . . ?
C21 C3 C3A C4 -1.9(3) . . . . ?
N8 C3A C4 C5 0.89(19) . . . . ?
C3 C3A C4 C5 -178.00(15) . . . . ?
C3A C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 N8 1.2(2) . . . . ?
C5 C6 C7 C14 178.76(12) . . . . ?
N2 N1 N8 C3A -1.13(14) . . . . ?
N2 N1 N8 C7 -179.18(12) . . . . ?
C3 C3A N8 N1 0.99(14) . . . . ?
C4 C3A N8 N1 -178.22(11) . . . . ?
C3 C3A N8 C7 179.09(12) . . . . ?
C4 C3A N8 C7 -0.13(19) . . . . ?
C6 C7 N8 N1 176.96(12) . . . . ?
C14 C7 N8 N1 -0.69(19) . . . . ?
C6 C7 N8 C3A -0.89(19) . . . . ?
C14 C7 N8 C3A -178.54(12) . . . . ?
C16 N11 C12 N13 -4.8(2) . . . . ?
Zn1 N11 C12 N13 167.73(11) 2_556 . . . ?
N11 C12 N13 C14 3.0(2) . . . . ?
C12 N13 C14 C15 1.45(19) . . . . ?
C12 N13 C14 C7 177.82(12) . . . . ?
C6 C7 C14 N13 -49.00(17) . . . . ?
N8 C7 C14 N13 128.54(13) . . . . ?
C6 C7 C14 C15 127.12(15) . . . . ?
N8 C7 C14 C15 -55.34(18) . . . . ?
N13 C14 C15 C16 -3.75(19) . . . . ?
C7 C14 C15 C16 -179.65(12) . . . . ?
N13 C14 C15 Br1 170.81(10) . . . . ?
C7 C14 C15 Br1 -5.08(19) . . . . ?
C12 N11 C16 C15 2.05(19) . . . . ?
Zn1 N11 C16 C15 -170.25(9) 2_556 . . . ?
C14 C15 C16 N11 1.93(19) . . . . ?
Br1 C15 C16 N11 -172.99(10) . . . . ?
