#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/72/2207219.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2207219
loop_
_publ_author_name
'Hiremath, Rupa'
'Sarjeant, Amy A.'
'Swift, Jennifer A.'
_publ_section_title
;
 Template-directed growth of p-bromoiodobenzene
;
_journal_coeditor_code           FL6191
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3822
_journal_page_last               o3824
_journal_paper_doi               10.1107/S1600536805033234
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H4 Br I'
_chemical_formula_moiety         'C6 H4 Br I'
_chemical_formula_sum            'C6 H4 Br I'
_chemical_formula_weight         282.90
_chemical_name_systematic
;
p-Bromoiodobenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.301(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.1120(6)
_cell_length_b                   5.7936(8)
_cell_length_c                   14.931(2)
_cell_measurement_reflns_used    2165
_cell_measurement_temperature    110
_cell_measurement_theta_max      32.57
_cell_measurement_theta_min      2.76
_cell_volume                     352.82(9)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2005)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2005)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2000)'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  'Oxford Xcalibur3'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2583
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         4.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_exptl_absorpt_coefficient_mu    10.09099
_exptl_absorpt_correction_T_max  0.65211
_exptl_absorpt_correction_T_min  0.18218
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
'(CrysAlis RED; Oxford Diffraction, 2005; Clark & Reid, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.20000
_exptl_crystal_size_mid          0.09765
_exptl_crystal_size_min          0.01928
_refine_diff_density_max         1.063
_refine_diff_density_min         -0.665
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     46
_refine_ls_number_reflns         882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0342P)²+0.3465P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0568
_refine_ls_wR_factor_ref         0.0590
_reflns_number_gt                772
_reflns_number_total             882
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl6191.cif
_cod_data_source_block           I
_cod_original_cell_volume        352.83(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207219
_cod_database_fobs_code          2207219
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1 0.1417(9) 0.3363(6) 0.3297(2) 0.0208(9) Uani d P 0.50 A 1 I
Br1 0.1468(14) 0.3334(8) 0.3316(4) 0.0221(15) Uani d P 0.50 A 2 Br
C1 0.3551(8) 0.1365(5) 0.4306(3) 0.0225(7) Uani d . 1 . . C
C2 0.5026(9) -0.0694(6) 0.4109(3) 0.0253(7) Uani d . 1 A . C
H2A 0.5016 -0.1164 0.3499 0.030 Uiso calc R 1 . . H
C3 0.6517(8) -0.2062(6) 0.4806(3) 0.0243(7) Uani d . 1 . . C
H3A 0.7572 -0.3461 0.4677 0.029 Uiso calc R 1 A . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.0222(14) 0.0252(15) 0.0152(12) 0.0034(9) 0.0028(8) 0.0026(8)
Br1 0.021(2) 0.017(2) 0.027(2) -0.0040(13) -0.0031(13) 0.0019(13)
C1 0.0220(15) 0.0196(14) 0.0272(18) -0.0050(12) 0.0082(13) -0.0013(12)
C2 0.0305(17) 0.0228(15) 0.0242(17) -0.0048(13) 0.0096(14) -0.0079(13)
C3 0.0240(16) 0.0223(14) 0.0287(19) -0.0006(12) 0.0112(14) -0.0060(13)
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'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C3 . 3_656 121.0(3)
C2 C1 Br1 . . 119.8(3)
C3 C1 Br1 3_656 . 119.1(3)
C2 C1 I1 . . 119.7(3)
C3 C1 I1 3_656 . 119.2(3)
C1 C2 C3 . . 119.7(3)
C1 C2 H2A . . 120.2
C3 C2 H2A . . 120.2
C2 C3 C1 . 3_656 119.3(3)
C2 C3 H3A . . 120.4
C1 C3 H3A 3_656 . 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C1 . 2.012(6)
Br1 C1 . 1.975(7)
C1 C2 . 1.387(5)
C1 C3 3_656 1.390(5)
C2 C3 . 1.388(5)
C2 H2A . 0.9500
C3 C1 3_656 1.390(5)
C3 H3A . 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3 C1 C2 C3 3_656 . -1.3(5)
Br1 C1 C2 C3 . . 179.3(3)
I1 C1 C2 C3 . . 179.6(3)
C1 C2 C3 C1 . 3_656 1.2(5)
