#------------------------------------------------------------------------------
#$Date: 2020-09-26 04:31:25 +0300 (Sat, 26 Sep 2020) $
#$Revision: 256785 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/13/7241313.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_7241313
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            'C11 H8 Br N5'
_chemical_formula_weight         290.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                 98.283(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4811(3)
_cell_length_b                   7.2879(3)
_cell_length_c                   19.9293(12)
_cell_measurement_reflns_used    7945
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      37.3289
_cell_measurement_theta_min      3.3252
_cell_volume                     1075.24(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.939
_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  0.0988
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         31.963
_diffrn_reflns_theta_min         3.476
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Agilent Technologies,2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0538
_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)+(0.0264P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.1082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2296
_reflns_number_total             3494
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01272f2.cif
_cod_data_source_block           EE15_RB1
_cod_original_cell_volume        1075.25(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241313
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.56208(4) 0.57165(5) 0.71346(2) 0.02137(12) Uani 1 1 d . . . . .
N1 N 0.2766(4) 0.3072(4) 0.61679(15) 0.0185(7) Uani 1 1 d . . . . .
N2 N 0.3254(4) 0.1983(4) 0.56865(16) 0.0191(7) Uani 1 1 d . . . . .
C3 C 0.3136(4) 0.2883(5) 0.50876(18) 0.0176(8) Uani 1 1 d . . . . .
C3A C 0.2537(4) 0.4663(5) 0.51841(18) 0.0152(7) Uani 1 1 d . . . . .
C4 C 0.2072(4) 0.6235(5) 0.4779(2) 0.0206(8) Uani 1 1 d . . . . .
H4 H 0.218499 0.623647 0.431043 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1460(4) 0.7741(5) 0.50769(19) 0.0194(8) Uani 1 1 d . . . . .
H5 H 0.111919 0.880063 0.481162 0.023 Uiso 1 1 calc R U . . .
C6 C 0.1322(4) 0.7749(5) 0.57842(19) 0.0183(8) Uani 1 1 d . . . . .
H6 H 0.090179 0.882048 0.598347 0.022 Uiso 1 1 calc R U . . .
C7 C 0.1781(4) 0.6255(5) 0.61761(19) 0.0166(8) Uani 1 1 d . . . . .
N8 N 0.2346(4) 0.4713(4) 0.58595(15) 0.0145(6) Uani 1 1 d . . . . .
N11 N 0.1553(4) 0.6239(4) 0.82900(16) 0.0206(7) Uani 1 1 d . . . . .
C12 C 0.0154(5) 0.6549(5) 0.78025(19) 0.0206(8) Uani 1 1 d . . . . .
H12 H -0.096669 0.682911 0.795001 0.025 Uiso 1 1 calc R U . . .
N13 N 0.0159(4) 0.6507(4) 0.71328(16) 0.0195(7) Uani 1 1 d . . . . .
C14 C 0.1767(5) 0.6189(5) 0.69211(19) 0.0163(7) Uani 1 1 d . . . . .
C15 C 0.3295(4) 0.5922(5) 0.73895(19) 0.0166(7) Uani 1 1 d . . . . .
C16 C 0.3133(5) 0.5929(5) 0.80712(19) 0.0173(7) Uani 1 1 d . . . . .
H16 H 0.417520 0.570714 0.839374 0.021 Uiso 1 1 calc R U . . .
C21 C 0.3565(5) 0.1996(5) 0.44576(19) 0.0221(8) Uani 1 1 d . . . . .
H21A H 0.466017 0.254814 0.432846 0.029 Uiso 1 1 calc R U . . .
H21B H 0.255569 0.217558 0.409163 0.029 Uiso 1 1 calc R U . . .
H21C H 0.376129 0.067966 0.453762 0.029 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'
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 N1 N8 105.5(3) . . ?
N1 N2 C3 110.8(3) . . ?
N2 C3 C3A 108.1(3) . . ?
N2 C3 C21 122.6(3) . . ?
C3A C3 C21 129.3(3) . . ?
N8 C3A C3 103.9(3) . . ?
N8 C3A C4 119.0(3) . . ?
C3 C3A C4 137.0(3) . . ?
C5 C4 C3A 118.4(4) . . ?
C4 C5 C6 120.8(3) . . ?
C7 C6 C5 121.1(3) . . ?
C6 C7 N8 117.3(3) . . ?
C6 C7 C14 124.3(3) . . ?
N8 C7 C14 118.4(3) . . ?
N1 N8 C3A 111.7(3) . . ?
N1 N8 C7 125.0(3) . . ?
C3A N8 C7 123.3(3) . . ?
C16 N11 C12 115.3(3) . . ?
N13 C12 N11 127.3(3) . . ?
C12 N13 C14 116.5(3) . . ?
N13 C14 C15 120.0(3) . . ?
N13 C14 C7 116.2(3) . . ?
C15 C14 C7 123.7(3) . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 Br1 118.7(3) . . ?
C14 C15 Br1 122.3(3) . . ?
N11 C16 C15 121.9(3) . . ?
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 C15 1.888(3) . ?
N1 N2 1.336(4) . ?
N1 N8 1.361(4) . ?
N2 C3 1.354(4) . ?
C3 C3A 1.395(5) . ?
C3 C21 1.488(5) . ?
C3A N8 1.374(4) . ?
C3A C4 1.416(5) . ?
C4 C5 1.358(5) . ?
C5 C6 1.428(5) . ?
C6 C7 1.355(5) . ?
C7 N8 1.384(4) . ?
C7 C14 1.487(5) . ?
N11 C16 1.337(4) . ?
N11 C12 1.341(5) . ?
C12 N13 1.336(5) . ?
N13 C14 1.351(4) . ?
C14 C15 1.381(5) . ?
C15 C16 1.381(5) . ?
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
C12 H12 Br1 0.95 2.94 3.513(4) 120.3 1_455 yes
C12 H12 N1 0.95 2.53 3.392(5) 150.9 2_556 yes
C16 H16 N2 0.95 2.63 3.478(5) 149.1 2_656 yes
