#------------------------------------------------------------------------------
#$Date: 2015-05-13 11:33:30 +0300 (Wed, 13 May 2015) $
#$Revision: 136163 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/71/7117162.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_7117162
loop_
_publ_author_name
'Fanny Frausto'
'Zachary C. Smith'
'Terry E. Haas'
'Samuel W. Thomas III'
_publ_section_title
;
 Two-dimensional bricklayer arrangements of tolans using halogen bonding
 interactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              8825
_journal_paper_doi               10.1039/C5cc02225H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C15 H8 Br N'
_chemical_formula_weight         282.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-03-16 deposited with the CCDC.
2015-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.893(4)
_cell_length_b                   7.5409(14)
_cell_length_c                   17.168(3)
_cell_measurement_temperature    100(2)
_cell_volume                     2316.5(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'omega, phi scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14475
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.031
_diffrn_reflns_theta_min         2.276
_diffrn_source                   'Mo sealed tube'
_exptl_absorpt_coefficient_mu    3.522
_exptl_absorpt_correction_T_max  0.7960
_exptl_absorpt_correction_T_min  0.3760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.297
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         2029
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.297
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0314
_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)+(0.0287P)²+7.4239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0782
_reflns_Friedel_coverage         0.943
_reflns_friedel_fraction_full    1.000
_reflns_friedel_fraction_max     1.000
_reflns_number_gt                1783
_reflns_number_total             2029
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc02225h2.cif
_cod_data_source_block           FF022715MC_Fdd_f
_cod_database_code               7117162
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.376
_shelx_estimated_absorpt_t_max   0.796
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
Br01 Br 0.2500 0.2500 0.91468(2) 0.01614(13) Uani 1 2 d S T P . .
C002 C 0.2500 0.2500 0.1580(6) 0.024(2) Uani 1 2 d S T P . .
C003 C 0.2500 0.2500 0.5595(4) 0.0158(15) Uani 1 2 d S T P . .
C004 C 0.2500 0.2500 0.4041(5) 0.0126(17) Uani 1 2 d S T P . .
C005 C 0.2500 0.2500 0.4883(3) 0.0175(11) Uani 1 2 d S T P . .
C006 C 0.1831(2) 0.2260(5) 0.6835(2) 0.0145(7) Uani 1 1 d . . . . .
H006 H 0.1376 0.2083 0.6559 0.017 Uiso 1 1 calc R U . . .
C007 C 0.1827(2) 0.2278(7) 0.7644(2) 0.0157(9) Uani 1 1 d . . . . .
H007 H 0.1373 0.2141 0.7923 0.019 Uiso 1 1 calc R U . . .
C008 C 0.1842(2) 0.2878(5) 0.3644(2) 0.0153(8) Uani 1 1 d . . . . .
H008 H 0.1397 0.3142 0.3923 0.018 Uiso 1 1 calc R U . . .
C009 C 0.2500 0.2500 0.8038(3) 0.0136(9) Uani 1 2 d S T P . .
N00A N 0.2500 0.2500 0.0944(4) 0.0302(14) Uani 1 2 d S T P . .
C00B C 0.2500 0.2500 0.2428(5) 0.0153(16) Uani 1 2 d S T P . .
C00C C 0.1839(2) 0.2868(5) 0.2832(2) 0.0146(8) Uani 1 1 d . . . . .
H00C H 0.1391 0.3109 0.2554 0.018 Uiso 1 1 calc R U . . .
C00E C 0.2500 0.2500 0.6423(4) 0.0152(16) Uani 1 2 d S T P . .
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
N00A C002 C00B 180.0 . .
C005 C003 C00E 180.0 . .
C008 C004 C008 121.2(7) . 14
C008 C004 C005 119.4(4) . .
C008 C004 C005 119.4(4) 14 .
C003 C005 C004 180.0 . .
C007 C006 C00E 120.5(4) . .
C007 C006 H006 119.8 . .
C00E C006 H006 119.8 . .
C006 C007 C009 118.9(4) . .
C006 C007 H007 120.5 . .
C009 C007 H007 120.5 . .
C004 C008 C00C 119.5(5) . .
C004 C008 H008 120.2 . .
C00C C008 H008 120.2 . .
C007 C009 C007 121.8(6) 14 .
C007 C009 Br01 119.1(3) 14 .
C007 C009 Br01 119.1(3) . .
C00C C00B C00C 120.5(6) 14 .
C00C C00B C002 119.7(3) 14 .
C00C C00B C002 119.7(3) . .
C008 C00C C00B 119.6(4) . .
C008 C00C H00C 120.2 . .
C00B C00C H00C 120.2 . .
C006 C00E C006 119.4(6) . 14
C006 C00E C003 120.3(3) . .
C006 C00E C003 120.3(3) 14 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br01 C009 1.903(6) .
C002 N00A 1.092(13) .
C002 C00B 1.454(12) .
C003 C005 1.221(10) .
C003 C00E 1.421(10) .
C004 C008 1.391(6) .
C004 C008 1.391(6) 14
C004 C005 1.445(10) .
C006 C007 1.389(5) .
C006 C00E 1.403(5) .
C006 H006 0.9500 .
C007 C009 1.391(5) .
C007 H007 0.9500 .
C008 C00C 1.394(6) .
C008 H008 0.9500 .
C009 C007 1.391(5) 14
C00B C00C 1.399(6) 14
C00B C00C 1.399(6) .
C00C H00C 0.9500 .
C00E C006 1.403(5) 14
