#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:37:24 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179589 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/54/4505407.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_4505407
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 N2,1.5(C H Cl3)'
_chemical_formula_sum            'C24.5 H17.5 Br2 Cl4.5 N2'
_chemical_formula_weight         659.3
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source
'International Tables for X-ray Crystallography, Vol. IV'
_audit_creation_method           'RAELSPUB and manual entry'
_cell_angle_alpha                90
_cell_angle_beta                 112.50(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.682(9)
_cell_length_b                   10.403(5)
_cell_length_c                   16.961(8)
_cell_measurement_reflns_used    10
_cell_measurement_temperature    294
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     5165(4)
_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  0.033
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3753
_diffrn_reflns_theta_max         23
_diffrn_standards_decay_%        21
_diffrn_standards_interval_time  30min
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    3.595
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(DeMeulenaer & Tompa, 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.70
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2600.0
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.79
_refine_diff_density_min         -1.04
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.45
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1615
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0.003
_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         0.062
_reflns_number_gt                1615
_reflns_number_total             3604
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg049927rsi20040518_065158.cif
_cod_data_source_block           DRB221_(8)2(chloroform)3
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4505407
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 x,-y,1/2+z
3 -x,-y,-z
4 -x,y,1/2-z
5 1/2+x,1/2+y,z
6 1/2+x,1/2-y,1/2+z
7 1/2-x,1/2-y,-z
8 1/2-x,1/2+y,1/2-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 0.26616(4) 0.37302(13) 0.08697(7) 0.0752(5) Uani Br 1.0
Br2 0.48279(4) 0.36368(13) 0.35263(8) 0.0789(5) Uani Br 1.0
N1 0.3146(3) 0.6457(8) 0.0661(5) 0.055(1) Uani N 1.0
N2 0.4372(3) 0.6437(9) 0.3709(5) 0.071(1) Uani N 1.0
C1 0.3432(3) 0.4140(10) 0.2447(6) 0.058(1) Uani C 1.0
C2 0.3121(3) 0.4897(10) 0.1677(6) 0.057(1) Uani C 1.0
C3 0.3367(3) 0.5546(10) 0.1176(6) 0.050(2) Uani C 1.0
C4 0.3808(3) 0.5121(9) 0.1265(6) 0.049(2) Uani C 1.0
C5 0.4066(3) 0.4113(9) 0.1935(6) 0.052(2) Uani C 1.0
C6 0.4388(3) 0.4842(10) 0.2717(6) 0.059(1) Uani C 1.0
C7 0.4149(4) 0.5531(10) 0.3206(6) 0.059(1) Uani C 1.0
C8 0.3695(4) 0.5130(10) 0.3104(6) 0.058(1) Uani C 1.0
C9 0.3746(4) 0.3281(9) 0.2183(6) 0.056(2) Uani C 1.0
C10 0.3347(4) 0.7057(10) 0.0166(6) 0.058(1) Uani C 1.0
C11 0.3115(4) 0.8058(10) -0.0348(7) 0.071(2) Uani C 1.0
C12 0.3304(5) 0.8683(11) -0.0835(7) 0.083(2) Uani C 1.0
C13 0.3741(5) 0.8320(11) -0.0806(8) 0.085(2) Uani C 1.0
C14 0.3975(4) 0.7336(11) -0.0311(7) 0.074(2) Uani C 1.0
C15 0.3786(4) 0.6676(9) 0.0209(6) 0.059(1) Uani C 1.0
C16 0.4007(3) 0.5703(10) 0.0775(6) 0.054(1) Uani C 1.0
C17 0.4178(5) 0.7029(11) 0.4194(7) 0.079(2) Uani C 1.0
C18 0.4415(5) 0.8070(12) 0.4747(8) 0.100(2) Uani C 1.0
C19 0.4233(6) 0.8724(14) 0.5231(8) 0.116(4) Uani C 1.0
C20 0.3797(6) 0.8328(14) 0.5199(8) 0.112(4) Uani C 1.0
C21 0.3553(5) 0.7359(13) 0.4696(8) 0.096(3) Uani C 1.0
C22 0.3743(4) 0.6689(11) 0.4178(7) 0.077(2) Uani C 1.0
C23 0.3501(4) 0.5723(11) 0.3605(7) 0.069(2) Uani C 1.0
C1Ch1 0.2993(2) 0.8931(6) 0.1780(6) 0.072(4) Uani C 0.90
Cl1Ch1 0.3580(1) 0.8867(6) 0.2299(4) 0.120(3) Uani Cl 0.90
Cl2Ch1 0.2739(2) 0.8333(4) 0.2439(3) 0.102(4) Uani Cl 0.90
Cl3Ch1 0.2825(2) 1.0506(6) 0.1516(6) 0.125(3) Uani Cl 0.90
C1Ch1' 0.3053(13) 0.8734(35) 0.1663(21) 0.082(3) Uani C 0.10
Cl1Ch1' 0.3604(13) 0.9308(77) 0.1976(49) 0.168(8) Uani Cl 0.10
Cl2Ch1 0.2947(18) 0.8294(42) 0.2553(24) 0.086(3) Uani Cl 0.10
Cl3Ch1' 0.2672(18) 0.9916(60) 0.1110(27) 0.113(6) Uani Cl 0.10
C1Ch2 0.5153(3) 0.1258(8) 0.7177(6) 0.101(4) Uani C 0.50
Cl1Ch2 0.5358(4) 0.1779(9) 0.8223(7) 0.191(4) Uani Cl 0.50
Cl2Ch2 0.5278(3) -0.0353(7) 0.7147(6) 0.178(4) Uani Cl 0.50
Cl3Ch2 0.4568(4) 0.1480(11) 0.6721(10) 0.252(4) Uani Cl 0.50
HC1 0.3243 0.3600 0.2676 0.068 Uani H 1.0
HC2 0.2957 0.5568 0.1875 0.063 Uani H 1.0
HC5 0.4250 0.3558 0.1704 0.058 Uani H 1.0
HC6 0.4563 0.5486 0.2525 0.065 Uani H 1.0
H1C9 0.3559 0.2737 0.1686 0.060 Uani H 1.0
H2C9 0.3928 0.2715 0.2672 0.063 Uani H 1.0
HC11 0.2809 0.8323 -0.0363 0.078 Uani H 1.0
HC12 0.3134 0.9402 -0.1215 0.097 Uani H 1.0
HC13 0.3879 0.8802 -0.1159 0.101 Uani H 1.0
HC14 0.4279 0.7076 -0.0310 0.083 Uani H 1.0
HC16 0.4318 0.5424 0.0825 0.062 Uani H 1.0
HC18 0.4725 0.8317 0.4774 0.111 Uani H 1.0
HC19 0.4399 0.9459 0.5598 0.136 Uani H 1.0
HC20 0.3663 0.8789 0.5567 0.129 Uani H 1.0
HC21 0.3246 0.7121 0.4688 0.103 Uani H 1.0
HC23 0.3188 0.5468 0.3561 0.077 Uani H 1.0
HC1Ch1 0.2899 0.8402 0.1248 0.107 Uani H 0.90
HC1Ch1' 0.3015 0.7968 0.1286 0.122 Uani H 0.10
HC1Ch2 0.5301 0.1763 0.6851 0.173 Uani H 0.50
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
C2 C1 C8 105.9(9) 1_555 1_555 1_555 no
C2 C1 C9 109.4(8) 1_555 1_555 1_555 no
C8 C1 C9 112.1(8) 1_555 1_555 1_555 no
Br1 C2 C1 109.8(7) 1_555 1_555 1_555 no
Br1 C2 C3 106.5(6) 1_555 1_555 1_555 no
C1 C2 C3 114.1(8) 1_555 1_555 1_555 no
C2 C3 C4 120.0(9) 1_555 1_555 1_555 no
C3 C4 C5 121.3(8) 1_555 1_555 1_555 no
C3 C4 C16 117.6(9) 1_555 1_555 1_555 no
C5 C4 C16 121.0(8) 1_555 1_555 1_555 no
C4 C5 C6 107.1(8) 1_555 1_555 1_555 no
C4 C5 C9 111.9(8) 1_555 1_555 1_555 no
C6 C5 C9 109.8(8) 1_555 1_555 1_555 no
Br2 C6 C5 110.2(7) 1_555 1_555 1_555 no
Br2 C6 C7 106.8(7) 1_555 1_555 1_555 no
C5 C6 C7 113.9(8) 1_555 1_555 1_555 no
C6 C7 C8 119.1(10) 1_555 1_555 1_555 no
C1 C8 C7 121.9(9) 1_555 1_555 1_555 no
C1 C8 C23 120.7(10) 1_555 1_555 1_555 no
C7 C8 C23 117.3(10) 1_555 1_555 1_555 no
C1 C9 C5 109.2(8) 1_555 1_555 1_555 no
C11 C10 C15 121.2(10) 1_555 1_555 1_555 no
C10 C11 C12 119.7(11) 1_555 1_555 1_555 no
C11 C12 C13 120.3(11) 1_555 1_555 1_555 no
C12 C13 C14 121.2(11) 1_555 1_555 1_555 no
C13 C14 C15 119.5(11) 1_555 1_555 1_555 no
C10 C15 C14 118.1(10) 1_555 1_555 1_555 no
C10 C15 C16 117.6(10) 1_555 1_555 1_555 no
C14 C15 C16 124.3(10) 1_555 1_555 1_555 no
C4 C16 C15 121.2(9) 1_555 1_555 1_555 no
C18 C17 C22 117.6(12) 1_555 1_555 1_555 no
C17 C18 C19 122.3(15) 1_555 1_555 1_555 no
C18 C19 C20 117.7(14) 1_555 1_555 1_555 no
C19 C20 C21 123.4(14) 1_555 1_555 1_555 no
C20 C21 C22 118.6(15) 1_555 1_555 1_555 no
C17 C22 C21 120.4(13) 1_555 1_555 1_555 no
C17 C22 C23 117.5(11) 1_555 1_555 1_555 no
C21 C22 C23 122.1(13) 1_555 1_555 1_555 no
C8 C23 C22 119.7(11) 1_555 1_555 1_555 no
Cl1Ch1 C1Ch1 Cl2Ch1 109.6(3) 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 1.985(10) 1_555 1_555 no
Br2 C6 1.984(10) 1_555 1_555 no
C1 C2 1.520(13) 1_555 1_555 no
C1 C8 1.513(13) 1_555 1_555 no
C1 C9 1.528(13) 1_555 1_555 no
C2 C3 1.515(12) 1_555 1_555 no
C3 C4 1.415(12) 1_555 1_555 no
C4 C5 1.532(12) 1_555 1_555 no
C4 C16 1.364(12) 1_555 1_555 no
C5 C6 1.530(12) 1_555 1_555 no
C5 C9 1.510(13) 1_555 1_555 no
C6 C7 1.502(13) 1_555 1_555 no
C7 C8 1.443(13) 1_555 1_555 no
C8 C23 1.371(13) 1_555 1_555 no
C10 C11 1.377(13) 1_555 1_555 no
C10 C15 1.422(13) 1_555 1_555 no
C11 C12 1.355(14) 1_555 1_555 no
C12 C13 1.419(16) 1_555 1_555 no
C13 C14 1.352(14) 1_555 1_555 no
C14 C15 1.417(13) 1_555 1_555 no
C15 C16 1.386(12) 1_555 1_555 no
C17 C18 1.441(15) 1_555 1_555 no
C17 C22 1.413(16) 1_555 1_555 no
C18 C19 1.353(17) 1_555 1_555 no
C19 C20 1.423(20) 1_555 1_555 no
C20 C21 1.356(18) 1_555 1_555 no
C21 C22 1.422(14) 1_555 1_555 no
C22 C23 1.405(14) 1_555 1_555 no
C1Ch1 Cl1Ch1 1.727(4) 1_555 1_555 no
