#------------------------------------------------------------------------------
#$Date: 2022-03-30 09:39:39 +0200 (Wed 30 de Mar de 2022) $
#$Revision: 274105 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/49/8104942.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_8104942
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 1-bromo-4-iodo-benzene, C6H4BrI
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              267
_journal_page_last               268
_journal_paper_doi               10.1515/ncrs-2020-0516
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C6 H4 Br I'
_chemical_formula_sum            'C6 H4 Br I'
_chemical_formula_weight         282.90
_chemical_name_common            1-bromo-4-iodo-benzene
_chemical_name_systematic        1-bromo-4-iodo-benzene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 97.315(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.1704(6)
_cell_length_b                   5.8242(8)
_cell_length_c                   14.929(2)
_cell_measurement_reflns_used    2439
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      2.75
_cell_volume                     359.66(9)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2943
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.026
_diffrn_reflns_theta_min         2.751
_exptl_absorpt_coefficient_mu    9.899
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3898
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS [6]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.612
_exptl_crystal_description       platelet
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.554
_exptl_crystal_size_mid          0.444
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_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     47
_refine_ls_number_reflns         865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0303
_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)+(0.0544P)²+0.5448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                741
_reflns_number_total             865
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL ka091_a.res in P2(1)/c
    ka091.res
    created by SHELXL-2018/3 at 14:20:57 on 27-Aug-2020
REM Old TITL ka091_c in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.068, Rweak 0.001, Alpha 0.012
REM <I/s>   1.083 for   76 systematic absences,  Orientation as input
REM Formula found by SHELXT:  C3 I
CELL  0.71073   4.1704   5.8242  14.9294   90.000   97.315   90.000
ZERR    2.000   0.0006   0.0008   0.0022    0.000    0.005    0.000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C H BR I
UNIT 12 8 2 2

ACTA NOHKL
BOND $H
CONF
FMAP 2
HTAB
L.S. 100
LIST 4
PLAN 20
TEMP -73.140

REM WGHT 0.054400 0.544800
REM WGHT 0.054400 0.544800
REM WGHT 0.054400 0.544800
WGHT    0.054400    0.544800
EXTI    0.013633
FVAR       0.26724
C1    1    0.645001    0.365893    0.569837    11.00000    0.03557    0.03343 =
         0.03727   -0.00629    0.00872   -0.01017
C2    1    0.497967    0.568143    0.589128    11.00000    0.04852    0.03910 =
         0.02964   -0.00790    0.01103   -0.00387
AFIX  43
H2    2    0.496918    0.614045    0.650151    11.00000   -1.20000
AFIX   0
C3    1    0.351907    0.704650    0.520092    11.00000    0.04543    0.03832 =
         0.04010   -0.01003    0.01528   -0.00085
AFIX  43
H3    2    0.250514    0.844592    0.533202    11.00000   -1.20000
AFIX   0
PART 1 10.50000
I1    4    0.862148    0.156291    0.671372    10.50000    0.03727    0.03528 =
         0.03028    0.00691   -0.00025    0.00355
PART 2 10.50000
BR1   3    0.842927    0.183570    0.665084    10.50000    0.03442    0.03299 =
         0.03450    0.01002   -0.00479    0.00240
HKLF 4




REM  ka091_a.res in P2(1)/c
REM wR2 = 0.0982, GooF = S = 1.111, Restrained GooF = 1.111 for all data
REM R1 = 0.0303 for 741 Fo > 4sig(Fo) and 0.0364 for all 865 data
REM 47 parameters refined using 0 restraints

END  
     
WGHT      0.0544      0.5448 

REM Instructions for potential hydrogen bonds
EQIV $2 -x+1, y+1/2, -z+3/2
HTAB C2 I1_$2
EQIV $3 x-1, y+1, z
HTAB C3 I1_$3

REM Highest difference peak  0.802,  deepest hole -0.905,  1-sigma level  0.169
Q1    1   0.8616  0.1719  0.7110  11.00000  0.05    0.80
Q2    1   0.6932  0.1739  0.6095  11.00000  0.05    0.76
Q3    1   0.3460  0.6508  0.4789  11.00000  0.05    0.65
Q4    1   0.8386  0.1766  0.6202  11.00000  0.05    0.62
Q5    1   0.5509  0.6699  0.5337  11.00000  0.05    0.55
Q6    1   0.3616  0.5923  0.5463  11.00000  0.05    0.49
Q7    1   0.6041  0.3198  0.5670  11.00000  0.05    0.47
Q8    1   0.3574  0.9068  0.5595  11.00000  0.05    0.46
Q9    1   0.1447  0.8498  0.5034  11.00000  0.05    0.41
Q10   1   0.3840  0.3006  0.5739  11.00000  0.05    0.41
Q11   1   0.1468  0.6828  0.6581  11.00000  0.05    0.41
Q12   1   1.0703  0.0937  0.6003  11.00000  0.05    0.40
Q13   1   0.4302  0.4357  0.5636  11.00000  0.05    0.39
Q14   1   0.3206  0.7572  0.5480  11.00000  0.05    0.39
Q15   1   1.0666  0.2612  0.6019  11.00000  0.05    0.38
Q16   1   0.1590  0.4482  0.5748  11.00000  0.05    0.38
Q17   1   0.7726  0.5152  0.7486  11.00000  0.05    0.37
Q18   1   0.3289  0.5192  0.6722  11.00000  0.05    0.36
Q19   1   0.7471  0.5648  0.5132  11.00000  0.05    0.36
Q20   1   0.8143 -0.0430  0.7276  11.00000  0.05    0.35
;
_cod_data_source_file            suppl_j_ncrs-2020-0516_suppl.cif
_cod_data_source_block           g
_cod_original_cell_volume        359.67(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104942
_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   0.043
_shelx_estimated_absorpt_t_max   0.275
loop_
_space_group_symop_operation_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_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
C1 C 0.6450(12) 0.3659(8) 0.5698(4) 0.0351(10) Uani 1 1 d . . . . .
C2 C 0.4980(13) 0.5681(9) 0.5891(3) 0.0386(11) Uani 1 1 d . . . . .
H2 H 0.496918 0.614045 0.650151 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3519(14) 0.7046(9) 0.5201(4) 0.0404(12) Uani 1 1 d . . . . .
H3 H 0.250514 0.844592 0.533202 0.049 Uiso 1 1 calc R U . . .
I1 I 0.862(2) 0.1563(17) 0.6714(5) 0.0347(9) Uani 0.5 1 d . . P A 1
Br1 Br 0.843(3) 0.184(3) 0.6651(8) 0.0348(13) Uani 0.5 1 d . . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.036(2) 0.033(2) 0.037(3) -0.0063(19) 0.009(2) -0.0102(18)
C2 0.049(3) 0.039(2) 0.030(2) -0.0079(19) 0.011(2) -0.004(2)
C3 0.045(3) 0.038(3) 0.040(3) -0.010(2) 0.015(2) -0.001(2)
I1 0.0373(11) 0.035(2) 0.0303(10) 0.0069(12) -0.0002(9) 0.0035(9)
Br1 0.0344(13) 0.033(3) 0.0345(18) 0.0100(13) -0.0048(9) 0.0024(15)
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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C3 120.6(5) . 3_666
C2 C1 Br1 119.3(6) . .
C3 C1 Br1 120.1(6) 3_666 .
C2 C1 I1 121.2(4) . .
C3 C1 I1 118.2(4) 3_666 .
C1 C2 C3 120.2(5) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
C2 C3 C1 119.2(5) . 3_666
C2 C3 H3 120.4 . .
C1 C3 H3 120.4 3_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.375(7) .
C1 C3 1.406(7) 3_666
C1 Br1 1.879(15) .
C1 I1 2.064(11) .
C2 C3 1.380(8) .
C2 H2 0.9500 .
C3 H3 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 C1 C2 C3 -0.1(8) 3_666 . . .
Br1 C1 C2 C3 179.9(6) . . . .
I1 C1 C2 C3 -179.5(5) . . . .
C1 C2 C3 C1 0.1(8) . . . 3_666
