#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/54/4505408.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_4505408
loop_
_publ_author_name
'Alshahateet, Solhe F.'
'Bishop, Roger'
'Craig, Donald C.'
'Scudder, Marcia L.'
_publ_section_title
;
 Role of Double C−H···N Weak Hydrogen Bonding
 Motifs inN-Heteroaromatic Inclusion Chemistry
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              837
_journal_paper_doi               10.1021/cg049927r
_journal_volume                  4
_journal_year                    2004
_chemical_formula_moiety         'C23 H16 Br2 N2'
_chemical_formula_sum            'C23 H16 Br2 N2'
_chemical_formula_weight         480.2
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source
'International Tables for X-ray Crystallography, Vol. IV'
_audit_creation_method           'RAELSPUB and manual entry'
_cell_angle_alpha                102.68(2)
_cell_angle_beta                 93.93(3)
_cell_angle_gamma                117.32(3)
_cell_formula_units_Z            2
_cell_length_a                   10.222(7)
_cell_length_b                   10.354(7)
_cell_length_c                   10.498(8)
_cell_measurement_reflns_used    10
_cell_measurement_temperature    294
_cell_measurement_theta_max      13
_cell_measurement_theta_min      12
_cell_volume                     944.5(12)
_computing_cell_refinement       'CAD4 Version 5.0, 1989'
_computing_data_collection       'CAD4 Version 5.0, 1989'
_computing_data_reduction        'Local program'
_computing_molecular_graphics    'ORTEP-II, (Johnson, 1976)'
_computing_publication_material  'Local programs'
_computing_structure_refinement  'RAELS, (Rae, 1989)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3515
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  30min
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    4.257
_exptl_absorpt_correction_T_max  0.61
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(DeMeulenaer & Tompa, 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.69
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476.0
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.80
_refine_diff_density_min         -0.74
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.69
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2385
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0004F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.049
_reflns_number_gt                2385
_reflns_number_total             3316
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg049927rsi20040518_065258.cif
_cod_data_source_block           DRB223_apohost
_cod_original_cell_volume        944.5(8)
_cod_database_code               4505408
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
_atom_site_occupancy
Br1 0.28652(6) 0.19188(7) 0.41869(5) 0.0600(2) Uani Br 1.0
Br2 0.63395(7) 0.14549(6) 0.95022(5) 0.0619(2) Uani Br 1.0
N1 0.6517(4) 0.3797(4) 0.4254(4) 0.0386(9) Uani N 1.0
N2 0.7876(4) 0.5111(4) 0.9636(4) 0.0371(9) Uani N 1.0
C1 0.4356(5) 0.2924(5) 0.6935(4) 0.036(1) Uani C 1.0
C2 0.4657(5) 0.3297(5) 0.5628(4) 0.037(1) Uani C 1.0
C3 0.5970(5) 0.3146(5) 0.5188(4) 0.036(1) Uani C 1.0
C4 0.6540(5) 0.2358(5) 0.5788(4) 0.036(1) Uani C 1.0
C5 0.5862(5) 0.1611(5) 0.6842(4) 0.039(1) Uani C 1.0
C6 0.6875(5) 0.2608(5) 0.8190(4) 0.037(1) Uani C 1.0
C7 0.6777(5) 0.4043(5) 0.8674(4) 0.0318(9) Uani C 1.0
C8 0.5617(5) 0.4205(5) 0.8038(4) 0.0312(9) Uani C 1.0
C9 0.4285(5) 0.1393(5) 0.6878(4) 0.041(1) Uani C 1.0
C10 0.7701(5) 0.3695(5) 0.3833(4) 0.037(1) Uani C 1.0
C11 0.8262(5) 0.4325(6) 0.2792(5) 0.048(1) Uani C 1.0
C12 0.9437(5) 0.4221(6) 0.2322(5) 0.050(1) Uani C 1.0
C13 1.0122(6) 0.3543(6) 0.2890(5) 0.051(1) Uani C 1.0
C14 0.9622(5) 0.2931(5) 0.3902(5) 0.047(1) Uani C 1.0
C15 0.8388(5) 0.2975(5) 0.4385(4) 0.037(1) Uani C 1.0
C16 0.7765(5) 0.2308(5) 0.5375(4) 0.038(1) Uani C 1.0
C17 0.7940(5) 0.6480(5) 1.0021(4) 0.037(1) Uani C 1.0
C18 0.9124(6) 0.7649(6) 1.1054(5) 0.055(1) Uani C 1.0
C19 0.9253(7) 0.9064(6) 1.1393(6) 0.064(2) Uani C 1.0
C20 0.8247(7) 0.9370(6) 1.0749(6) 0.059(1) Uani C 1.0
C21 0.7097(6) 0.8289(6) 0.9775(5) 0.049(1) Uani C 1.0
C22 0.6897(5) 0.6797(5) 0.9403(4) 0.036(1) Uani C 1.0
C23 0.5709(5) 0.5601(5) 0.8402(4) 0.037(1) Uani C 1.0
HC1 0.3377 0.2861 0.7093 0.036 Uani H 1.0
HC2 0.4870 0.4363 0.5735 0.037 Uani H 1.0
HC5 0.5817 0.0600 0.6657 0.039 Uani H 1.0
HC6 0.7937 0.2897 0.8108 0.037 Uani H 1.0
H1C9 0.3569 0.0602 0.6058 0.041 Uani H 1.0
H2C9 0.3948 0.1075 0.7683 0.041 Uani H 1.0
HC11 0.7798 0.4850 0.2397 0.048 Uani H 1.0
HC12 0.9803 0.4638 0.1565 0.050 Uani H 1.0
HC13 1.0996 0.3500 0.2553 0.051 Uani H 1.0
HC14 1.0135 0.2451 0.4302 0.047 Uani H 1.0
HC16 0.8222 0.1788 0.5787 0.038 Uani H 1.0
HC18 0.9858 0.7444 1.1531 0.055 Uani H 1.0
HC19 1.0092 0.9891 1.2120 0.064 Uani H 1.0
HC20 0.8377 1.0417 1.1014 0.059 Uani H 1.0
HC21 0.6387 0.8534 0.9315 0.049 Uani H 1.0
HC23 0.4931 0.5773 0.7956 0.037 Uani H 1.0
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C10 117.7(4) 1_555 1_555 1_555 no
C7 N2 C17 118.2(4) 1_555 1_555 1_555 no
C2 C1 C8 107.6(3) 1_555 1_555 1_555 no
C2 C1 C9 109.8(3) 1_555 1_555 1_555 no
C8 C1 C9 111.3(3) 1_555 1_555 1_555 no
Br1 C2 C1 110.3(3) 1_555 1_555 1_555 no
Br1 C2 C3 107.5(3) 1_555 1_555 1_555 no
C1 C2 C3 113.1(4) 1_555 1_555 1_555 no
N1 C3 C2 115.7(4) 1_555 1_555 1_555 no
N1 C3 C4 124.6(4) 1_555 1_555 1_555 no
C2 C3 C4 119.7(4) 1_555 1_555 1_555 no
C3 C4 C5 122.8(4) 1_555 1_555 1_555 no
C3 C4 C16 116.6(4) 1_555 1_555 1_555 no
C5 C4 C16 120.6(4) 1_555 1_555 1_555 no
C4 C5 C6 108.3(4) 1_555 1_555 1_555 no
C4 C5 C9 112.3(4) 1_555 1_555 1_555 no
C6 C5 C9 109.2(4) 1_555 1_555 1_555 no
Br2 C6 C5 109.4(3) 1_555 1_555 1_555 no
Br2 C6 C7 109.5(3) 1_555 1_555 1_555 no
C5 C6 C7 112.7(3) 1_555 1_555 1_555 no
N2 C7 C6 115.2(4) 1_555 1_555 1_555 no
N2 C7 C8 124.4(4) 1_555 1_555 1_555 no
C6 C7 C8 120.3(4) 1_555 1_555 1_555 no
C1 C8 C7 122.4(4) 1_555 1_555 1_555 no
C1 C8 C23 120.2(4) 1_555 1_555 1_555 no
C7 C8 C23 117.3(4) 1_555 1_555 1_555 no
C1 C9 C5 107.4(3) 1_555 1_555 1_555 no
N1 C10 C11 118.6(4) 1_555 1_555 1_555 no
N1 C10 C15 122.6(4) 1_555 1_555 1_555 no
C11 C10 C15 118.8(4) 1_555 1_555 1_555 no
C10 C11 C12 120.4(5) 1_555 1_555 1_555 no
C11 C12 C13 120.3(5) 1_555 1_555 1_555 no
C12 C13 C14 121.1(4) 1_555 1_555 1_555 no
C13 C14 C15 120.2(5) 1_555 1_555 1_555 no
C10 C15 C14 119.1(4) 1_555 1_555 1_555 no
C10 C15 C16 117.3(4) 1_555 1_555 1_555 no
C14 C15 C16 123.5(4) 1_555 1_555 1_555 no
C4 C16 C15 121.1(4) 1_555 1_555 1_555 no
N2 C17 C18 118.9(4) 1_555 1_555 1_555 no
N2 C17 C22 122.3(4) 1_555 1_555 1_555 no
C18 C17 C22 118.7(4) 1_555 1_555 1_555 no
C17 C18 C19 119.3(5) 1_555 1_555 1_555 no
C18 C19 C20 121.3(5) 1_555 1_555 1_555 no
C19 C20 C21 121.3(5) 1_555 1_555 1_555 no
C20 C21 C22 119.6(5) 1_555 1_555 1_555 no
C17 C22 C21 119.7(4) 1_555 1_555 1_555 no
C17 C22 C23 117.5(4) 1_555 1_555 1_555 no
C21 C22 C23 122.8(4) 1_555 1_555 1_555 no
C8 C23 C22 120.2(4) 1_555 1_555 1_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.988(4) 1_555 1_555 no
Br2 C6 1.962(4) 1_555 1_555 no
N1 C3 1.322(5) 1_555 1_555 no
N1 C10 1.358(5) 1_555 1_555 no
N2 C7 1.311(5) 1_555 1_555 no
N2 C17 1.354(6) 1_555 1_555 no
C1 C2 1.520(6) 1_555 1_555 no
C1 C8 1.521(6) 1_555 1_555 no
C1 C9 1.541(6) 1_555 1_555 no
C2 C3 1.511(6) 1_555 1_555 no
C3 C4 1.420(6) 1_555 1_555 no
C4 C5 1.513(6) 1_555 1_555 no
C4 C16 1.373(6) 1_555 1_555 no
C5 C6 1.523(6) 1_555 1_555 no
C5 C9 1.526(6) 1_555 1_555 no
C6 C7 1.513(6) 1_555 1_555 no
C7 C8 1.415(6) 1_555 1_555 no
C8 C23 1.368(6) 1_555 1_555 no
C10 C11 1.416(6) 1_555 1_555 no
C10 C15 1.413(6) 1_555 1_555 no
C11 C12 1.369(7) 1_555 1_555 no
C12 C13 1.385(8) 1_555 1_555 no
C13 C14 1.365(7) 1_555 1_555 no
C14 C15 1.408(6) 1_555 1_555 no
C15 C16 1.401(6) 1_555 1_555 no
C17 C18 1.416(6) 1_555 1_555 no
C17 C22 1.409(6) 1_555 1_555 no
C18 C19 1.370(8) 1_555 1_555 no
C19 C20 1.384(8) 1_555 1_555 no
C20 C21 1.343(7) 1_555 1_555 no
C21 C22 1.420(6) 1_555 1_555 no
C22 C23 1.409(6) 1_555 1_555 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145818
