#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/68/2216829.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_2216829
loop_
_publ_author_name
'Betz, Richard'
'Klüfers, Peter'
_publ_section_title
;
 1-Bromomethyl-2-iodobenzene
;
_journal_coeditor_code           XU2334
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4753
_journal_page_last               o4753
_journal_paper_doi               10.1107/S1600536807058151
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H6 Br I'
_chemical_formula_moiety         'C7 H6 Br I'
_chemical_formula_sum            'C7 H6 Br I'
_chemical_formula_weight         296.93
_chemical_melting_point          55
_chemical_name_common            ortho-Iodo-benzylbromide
_chemical_name_systematic
;
1-Bromomethyl-2-iodobenzene
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_cell_angle_alpha                90.00
_cell_angle_beta                 114.777(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7569(2)
_cell_length_b                   12.0237(4)
_cell_length_c                   8.5351(3)
_cell_measurement_reflns_used    8472
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     815.94(5)
_computing_cell_refinement       'Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'COLLECT (Nonius, 2004)'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997) and Spek (2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13178
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    8.733
_exptl_absorpt_correction_T_max  0.497
_exptl_absorpt_correction_T_min  0.398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.053
_refine_diff_density_min         -0.585
_refine_ls_extinction_coef       0.0034(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0252P)²+0.4328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0560
_reflns_number_gt                1514
_reflns_number_total             1867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu2334.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216829
_cod_database_fobs_code          2216829
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_type_symbol
_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
I I 0.76744(3) 0.499318(17) 0.15316(3) 0.04592(11) Uani d . 1
Br Br 1.17131(4) 0.30304(3) 0.28843(4) 0.04037(12) Uani d . 1
C C1 0.8186(4) 0.2499(3) 0.1176(4) 0.0325(7) Uani d . 1
C C2 0.7165(3) 0.3295(2) 0.1485(4) 0.0307(6) Uani d . 1
C C3 0.5795(4) 0.2968(3) 0.1788(4) 0.0367(7) Uani d . 1
H H3 0.5108 0.3515 0.1978 0.053(4) Uiso calc R 1
C C4 0.5423(4) 0.1859(3) 0.1815(4) 0.0432(8) Uani d . 1
H H4 0.4485 0.1640 0.2028 0.053(4) Uiso calc R 1
C C5 0.6414(4) 0.1067(3) 0.1530(4) 0.0459(8) Uani d . 1
H H5 0.6166 0.0300 0.1562 0.053(4) Uiso calc R 1
C C6 0.7761(4) 0.1380(3) 0.1202(4) 0.0415(8) Uani d . 1
H H6 0.8419 0.0823 0.0988 0.053(4) Uiso calc R 1
C C7 0.9624(4) 0.2805(3) 0.0772(4) 0.0448(8) Uani d . 1
H H71 0.9349 0.3498 0.0080 0.053(4) Uiso calc R 1
H H72 0.9806 0.2209 0.0068 0.053(4) Uiso calc R 1
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
I 0.03819(15) 0.03381(16) 0.06009(18) -0.00073(8) 0.01501(12) 0.00094(10)
Br 0.02986(17) 0.0446(2) 0.0481(2) -0.00055(14) 0.01776(14) 0.00128(16)
C1 0.0297(14) 0.0391(18) 0.0231(15) 0.0033(13) 0.0056(12) -0.0024(12)
C2 0.0270(13) 0.0325(16) 0.0268(14) 0.0022(12) 0.0055(11) -0.0004(12)
C3 0.0277(14) 0.0436(19) 0.0352(16) 0.0028(13) 0.0096(12) -0.0013(14)
C4 0.0305(15) 0.048(2) 0.0440(19) -0.0097(14) 0.0083(14) 0.0045(16)
C5 0.0412(18) 0.0363(19) 0.0441(19) -0.0057(15) 0.0022(14) 0.0029(16)
C6 0.0404(17) 0.039(2) 0.0325(17) 0.0094(14) 0.0025(14) -0.0098(14)
C7 0.0368(17) 0.065(2) 0.0339(17) 0.0104(16) 0.0164(14) 0.0043(16)
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
_geom_angle_publ_flag
C6 C1 C2 117.1(3) ?
C6 C1 C7 120.0(3) ?
C2 C1 C7 122.9(3) ?
C3 C2 C1 120.7(3) ?
C3 C2 I 117.9(2) ?
C1 C2 I 121.4(2) ?
C4 C3 C2 120.5(3) ?
C4 C3 H3 119.7 n
C2 C3 H3 119.7 n
C3 C4 C5 119.8(3) ?
C3 C4 H4 120.1 n
C5 C4 H4 120.1 n
C6 C5 C4 120.3(3) ?
C6 C5 H5 119.8 n
C4 C5 H5 119.8 n
C5 C6 C1 121.6(3) ?
C5 C6 H6 119.2 n
C1 C6 H6 119.2 n
C1 C7 Br 111.9(2) ?
C1 C7 H71 109.2 n
Br C7 H71 109.2 n
C1 C7 H72 109.2 n
Br C7 H72 109.2 n
H71 C7 H72 107.9 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
I C2 2.087(3) ?
Br C7 1.977(3) ?
C1 C6 1.400(5) ?
C1 C2 1.408(4) ?
C1 C7 1.484(4) ?
C2 C3 1.385(4) ?
C3 C4 1.376(5) ?
C3 H3 0.9500 n
C4 C5 1.377(5) ?
C4 H4 0.9500 n
C5 C6 1.374(5) ?
C5 H5 0.9500 n
C6 H6 0.9500 n
C7 H71 0.9900 n
C7 H72 0.9900 n
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
Br I 3.6943(5) 2_745
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
C6 C1 C2 C3 -0.4(4)
C7 C1 C2 C3 177.3(3)
C6 C1 C2 I 178.8(2)
C7 C1 C2 I -3.4(4)
C1 C2 C3 C4 0.9(4)
I C2 C3 C4 -178.4(2)
C2 C3 C4 C5 -0.3(5)
C3 C4 C5 C6 -0.7(5)
C4 C5 C6 C1 1.2(5)
C2 C1 C6 C5 -0.6(4)
C7 C1 C6 C5 -178.4(3)
C6 C1 C7 Br -95.8(3)
C2 C1 C7 Br 86.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9601348
