#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/72/4507232.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_4507232
loop_
_publ_author_name
'Zieliński, Witold'
'Katrusiak, Andrzej'
_publ_section_title
;
 Hydrogen Bonds NH···N in Compressed Benzimidazole
 Polymorphs
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              696
_journal_paper_doi               10.1021/cg301374z
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C7 H6 N2'
_chemical_formula_sum            'C7 H6 N2'
_chemical_formula_weight         118.14
_chemical_melting_point          443
_chemical_name_common            'benzimidazole phase α'
_chemical_name_systematic
; 
1,3-benzodiazole
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.402(2)
_cell_length_b                   6.798(3)
_cell_length_c                   6.9428(7)
_cell_measurement_reflns_used    1775
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      3.04
_cell_volume                     632.5(3)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2004)'
_computing_data_reduction
'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A.  2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1997)'
_diffrn_ambient_environment      'diamond-anvil cell'
_diffrn_ambient_pressure         60000
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.209
_diffrn_measured_fraction_theta_max 0.209
_diffrn_measurement_device_type  'KUMA KM-4 CCD'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1775
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
 Correction for absorption of the diamond-anvil cell and the sample 
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.086
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(10)
_refine_ls_extinction_coef       0.017(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     24
_refine_ls_number_reflns         290
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0394P)²+0.8302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                262
_reflns_number_total             290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301374z_si_002.cif
_cod_data_source_block           bzima_0.06GPa
_cod_database_code               4507232
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.2566(4) 0.919(2) 0.5641(8) 0.043(2) Uiso 1 1 d D
H1 H 0.2239 0.8608 0.4740 0.15(4) Uiso 1 1 calc R
C2 C 0.2416(5) 1.100(2) 0.6311(9) 0.048(2) Uiso 1 1 d D
H2 H 0.1918 1.1828 0.5847 0.057 Uiso 1 1 calc R
N3 N 0.3044(3) 1.153(3) 0.7702(6) 0.0384(16) Uiso 1 1 d D
C4 C 0.4443(2) 0.9585(17) 0.9154(3) 0.0438(19) Uiso 1 1 d .
H4 H 0.4648 1.0562 1.0004 0.053 Uiso 1 1 calc R
C5 C 0.4941(2) 0.7792(17) 0.9105(3) 0.051(3) Uiso 1 1 d R
H5 H 0.5479 0.7570 0.9922 0.061 Uiso 1 1 calc R
C6 C 0.4635(2) 0.6332(17) 0.7834(3) 0.055(2) Uiso 1 1 d R
H6 H 0.4969 0.5132 0.7801 0.066 Uiso 1 1 calc R
C7 C 0.3831(2) 0.6663(17) 0.6613(3) 0.044(2) Uiso 1 1 d R
H7 H 0.3626 0.5686 0.5763 0.052 Uiso 1 1 calc R
C8 C 0.3333(2) 0.8456(17) 0.6662(3) 0.0316(18) Uiso 1 1 d R
C9 C 0.3639(2) 0.9917(17) 0.7933(3) 0.0331(16) Uiso 1 1 d 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'
N N 0.0061 0.0033 '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
C2 N1 C8 105.9(9)
C2 N1 H1 127.0
C8 N1 H1 127.0
N1 C2 N3 114.0(10)
N1 C2 H2 123.0
N3 C2 H2 123.0
C2 N3 C9 103.9(11)
C5 C4 C9 120.0
C5 C4 H4 120.0
C9 C4 H4 120.0
C4 C5 C6 120.0
C4 C5 H5 120.0
C6 C5 H5 120.0
C7 C6 C5 120.0
C7 C6 H6 120.0
C5 C6 H6 120.0
C6 C7 C8 120.0
C6 C7 H7 120.0
C8 C7 H7 120.0
N1 C8 C9 107.2(8)
N1 C8 C7 132.8(8)
C9 C8 C7 120.0
N3 C9 C8 109.1(4)
N3 C9 C4 131.0(4)
C8 C9 C4 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.333(10)
N1 C8 1.344(9)
N1 H1 0.8600
C2 N3 1.329(7)
C2 H2 0.9300
N3 C9 1.364(17)
C4 C5 1.3898
C4 C9 1.3901
C4 H4 0.9300
C5 C6 1.3901
C5 H5 0.9300
C6 C7 1.3899
C6 H6 0.9300
C7 C8 1.3901
C7 H7 0.9300
C8 C9 1.3900
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 5798
