#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:36:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180512 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/81/7218146.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_7218146
loop_
_publ_author_name
'Wang, Lei'
'Hu, Yanjing'
'Xu, Wenyan'
'pang, Yanyan'
'Liu, Faqian'
'Yang, Yu'
_publ_section_title
;
 Investigation of Hydrogen Bonding Patterns in A Series of Multi-component
 Molecular Solids Formed by Tetrabromoterephthalic Acid with Selected
 N-heterocycles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA08452G
_journal_year                    2014
_chemical_formula_moiety         'Br2 C4 O2, C5 H9 N2'
_chemical_formula_sum            'C9 H8 Br2 N2 O2'
_chemical_formula_weight         335.99
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                115.443(10)
_cell_angle_beta                 102.074(9)
_cell_angle_gamma                91.498(8)
_cell_formula_units_Z            2
_cell_length_a                   8.1803(8)
_cell_length_b                   8.7685(7)
_cell_length_c                   8.9983(10)
_cell_measurement_reflns_used    1787
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1560
_cell_measurement_theta_min      2.5770
_cell_volume                     565.01(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3905
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.990
_diffrn_reflns_theta_min         2.568
_exptl_absorpt_coefficient_mu    7.155
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.1079 before and 0.0236 after
correction. The Ratio of minimum to maximum transmission is 0.42976.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.975
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0327P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1913
_reflns_number_total             2429
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra08452g2.cif
_cod_data_source_block           w1
_cod_database_code               7218146
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-2
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C17(H17)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 0.51016(6) 0.72985(4) 0.16383(5) 0.03574(14) Uani 1 1 d .
Br2 Br 0.43255(6) 1.12789(4) 0.37813(5) 0.03488(14) Uani 1 1 d .
O1 O 0.5584(4) 1.4569(3) 0.2865(3) 0.0341(7) Uani 1 1 d .
C4 C 0.4332(5) 1.3496(4) 0.1919(4) 0.0240(8) Uani 1 1 d .
O2 O 0.2835(4) 1.3747(3) 0.1684(3) 0.0361(7) Uani 1 1 d .
C6 C 0.4708(4) 1.0525(4) 0.1595(4) 0.0208(7) Uani 1 1 d .
C7 C 0.5043(5) 0.8872(4) 0.0704(4) 0.0221(8) Uani 1 1 d .
C8 C 0.4680(4) 1.1676(4) 0.0903(4) 0.0203(7) Uani 1 1 d .
N2 N 0.8177(4) 1.3578(4) 0.4394(4) 0.0355(8) Uani 1 1 d .
H2 H 0.7504 1.4055 0.3907 0.043 Uiso 1 1 calc R
N1 N 0.8367(5) 1.3827(4) 0.5995(5) 0.0370(9) Uani 1 1 d .
C11 C 0.9511(6) 1.2896(5) 0.6331(5) 0.0420(11) Uani 1 1 d .
C13 C 0.9192(5) 1.2475(5) 0.3666(5) 0.0372(10) Uani 1 1 d .
C14 C 0.9233(6) 1.1918(6) 0.1874(6) 0.0569(13) Uani 1 1 d .
H14A H 0.8812 1.0728 0.1230 0.085 Uiso 1 1 calc GR
H14B H 1.0372 1.2105 0.1809 0.085 Uiso 1 1 calc GR
H14C H 0.8541 1.2560 0.1420 0.085 Uiso 1 1 calc GR
C17 C 1.0062(6) 1.2039(5) 0.4885(6) 0.0464(12) Uani 1 1 d .
H17 H 1.0874 1.1300 0.4751 0.056 Uiso 1 1 calc R
C19 C 0.9977(8) 1.2908(7) 0.8024(6) 0.0708(17) Uani 1 1 d .
H19A H 1.0934 1.3752 0.8727 0.106 Uiso 1 1 calc GR
H19B H 1.0255 1.1807 0.7892 0.106 Uiso 1 1 calc GR
H19C H 0.9044 1.3171 0.8545 0.106 Uiso 1 1 calc GR
H1 H 0.786(5) 1.456(5) 0.672(5) 0.041(12) Uiso 1 1 d .
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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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
O1 C4 C8 116.6(3) .
O2 C4 O1 127.2(3) .
O2 C4 C8 116.2(3) .
C7 C6 Br2 121.0(2) .
C7 C6 C8 120.6(3) .
C8 C6 Br2 118.4(2) .
C6 C7 Br1 121.0(3) .
C8 C7 Br1 118.2(2) 2_675
C8 C7 C6 120.7(3) 2_675
C6 C8 C4 119.6(3) .
C7 C8 C4 121.7(3) 2_675
C7 C8 C6 118.6(3) 2_675
C13 N2 N1 109.6(3) .
C11 N1 N2 109.3(4) .
N1 C11 C17 107.1(4) .
N1 C11 C19 121.3(4) .
C17 C11 C19 131.6(4) .
N2 C13 C14 122.0(4) .
N2 C13 C17 106.5(4) .
C17 C13 C14 131.4(4) .
C11 C17 C13 107.5(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C7 1.896(3) .
Br2 C6 1.886(3) .
O1 C4 1.247(5) .
C4 O2 1.240(4) .
C4 C8 1.531(4) .
C6 C7 1.391(4) .
C6 C8 1.394(4) .
C7 C8 1.385(5) 2_675
C8 C7 1.385(5) 2_675
N2 N1 1.335(5) .
N2 C13 1.333(5) .
N1 C11 1.330(5) .
C11 C17 1.373(6) .
C11 C19 1.486(7) .
C13 C14 1.479(6) .
C13 C17 1.380(6) .
