#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:58:04 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179908 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/04/7020429.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_7020429
loop_
_publ_author_name
'Barnes, Nicholas A.'
'Godfrey, Stephen M.'
'Ollerenshaw, Ruth T. A.'
'Khan, Rana Z.'
'Pritchard, Robin G.'
_publ_section_title
;
 Structural isomerism in (p-XC(6)H(4))SeCl(3) and (p-XC(6)H(4))SeBr(3) (X
 = F, Cl) compounds. Co-crystallisation of cis- and trans-dimeric forms of
 (p-ClC(6)H(4))SeCl(2)(μ-Cl)(2)(p-ClC(6)H(4))SeCl(2). A new structural
 modification for the "PhSeBr" reagent, Ph(2)Se(2)Br(2),
 containing an elongated Se-Se bond.
;
_journal_issue                   48
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14583
_journal_page_last               14593
_journal_paper_doi               10.1039/c2dt31539d
_journal_volume                  41
_journal_year                    2012
_chemical_compound_source        'synthesis as described'
_chemical_formula_sum            'C6 H4 Br3 Cl Se'
_chemical_formula_weight         430.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-07-04T09:34:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2012-09-13 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 96.9800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.24800(10)
_cell_length_b                   25.3497(5)
_cell_length_c                   10.7265(3)
_cell_measurement_reflns_used    5993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_measurement_wavelength     0.71073
_cell_volume                     1956.22(7)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      -0.101193
_diffrn_orient_matrix_UB_12      -0.166006E-1
_diffrn_orient_matrix_UB_13      -0.587652E-1
_diffrn_orient_matrix_UB_21      -0.935028E-1
_diffrn_orient_matrix_UB_22      0.112886E-1
_diffrn_orient_matrix_UB_23      0.559357E-1
_diffrn_orient_matrix_UB_31      -0.183859E-1
_diffrn_orient_matrix_UB_32      0.33958E-1
_diffrn_orient_matrix_UB_33      -0.473224E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21237
_diffrn_reflns_reduction_process
;
Scaled and merged with Sortav
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         2.94
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    16.301
_exptl_absorpt_correction_T_max  0.7430
_exptl_absorpt_correction_T_min  0.1372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Blessing, R. H. (1995) Acta Cryst., A51, 33-38.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.881
_refine_diff_density_min         -2.76
_refine_diff_density_rms         0.391
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0933P)²+15.1532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.166
_refine_ls_wR_factor_ref         0.1756
_reflns_number_gt                3084
_reflns_number_total             3805
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2dt31539d.txt
_cod_data_source_block           r_p-ClC6H4SeBr3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7020429
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3021(14) 0.5963(5) 0.7272(10) 0.019(2) Uani 1 1 d .
C2 C 0.3148(17) 0.6467(4) 0.7807(11) 0.023(3) Uani 1 1 d .
H2 H 0.3357 0.6509 0.8693 0.028 Uiso 1 1 calc R
C3 C 0.2962(16) 0.6911(5) 0.7009(11) 0.026(3) Uani 1 1 d .
H3 H 0.3059 0.726 0.7336 0.032 Uiso 1 1 calc R
C4 C 0.2629(14) 0.6817(4) 0.5724(10) 0.018(2) Uani 1 1 d .
C5 C 0.2577(15) 0.6327(5) 0.5211(10) 0.019(2) Uani 1 1 d .
H5 H 0.2442 0.6287 0.4324 0.022 Uiso 1 1 calc R
C6 C 0.2723(16) 0.5881(5) 0.5982(9) 0.020(2) Uani 1 1 d .
H6 H 0.2621 0.5535 0.5638 0.024 Uiso 1 1 calc R
C7 C 0.2602(14) 0.3705(5) 0.5684(10) 0.019(2) Uani 1 1 d .
C8 C 0.2345(14) 0.4077(4) 0.4713(9) 0.017(2) Uani 1 1 d .
H8 H 0.2396 0.4445 0.4884 0.02 Uiso 1 1 calc R
C9 C 0.2009(17) 0.3885(5) 0.3477(11) 0.023(2) Uani 1 1 d .
H9 H 0.1772 0.4123 0.2793 0.028 Uiso 1 1 calc R
C10 C 0.2025(15) 0.3352(5) 0.3264(11) 0.020(2) Uani 1 1 d .
C11 C 0.2279(16) 0.2987(5) 0.4238(11) 0.025(3) Uani 1 1 d .
H11 H 0.2244 0.2619 0.4067 0.029 Uiso 1 1 calc R
C12 C 0.2584(15) 0.3170(5) 0.5459(11) 0.021(2) Uani 1 1 d .
H12 H 0.278 0.2929 0.6139 0.025 Uiso 1 1 calc R
Se1 Se 0.32346(14) 0.53532(4) 0.83959(9) 0.0160(3) Uani 1 1 d .
Se2 Se 0.30640(14) 0.39606(4) 0.74114(9) 0.0160(3) Uani 1 1 d .
Br1 Br 0.13628(15) 0.56883(4) 0.98454(10) 0.0202(3) Uani 1 1 d .
Br2 Br 0.03951(15) 0.48416(4) 0.70702(10) 0.0200(3) Uani 1 1 d .
Br3 Br 0.62166(15) 0.56688(4) 0.95240(10) 0.0191(3) Uani 1 1 d .
Br4 Br 0.54217(16) 0.33430(5) 0.81032(10) 0.0232(3) Uani 1 1 d .
Br5 Br 0.05335(15) 0.34168(4) 0.81291(10) 0.0213(3) Uani 1 1 d .
Br6 Br 0.54972(15) 0.46727(5) 0.68256(10) 0.0208(3) Uani 1 1 d .
Cl1 Cl 0.2339(4) 0.73705(12) 0.4742(3) 0.0266(6) Uani 1 1 d .
Cl2 Cl 0.1640(4) 0.31292(12) 0.1716(2) 0.0248(6) Uani 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 122.7(11)
C6 C1 Se1 119.1(9)
C2 C1 Se1 118.2(8)
C1 C2 C3 118.9(11)
C1 C2 H2 120.5
C3 C2 H2 120.5
C4 C3 C2 117.2(12)
C4 C3 H3 121.4
C2 C3 H3 121.4
C5 C4 C3 123.5(11)
C5 C4 Cl1 119.6(9)
C3 C4 Cl1 116.9(9)
C4 C5 C6 120.3(10)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 117.4(11)
C1 C6 H6 121.3
C5 C6 H6 121.3
C12 C7 C8 122.4(10)
C12 C7 Se2 119.3(8)
C8 C7 Se2 118.2(9)
C7 C8 C9 117.3(10)
C7 C8 H8 121.4
C9 C8 H8 121.4
C10 C9 C8 119.7(11)
C10 C9 H9 120.1
C8 C9 H9 120.1
C9 C10 C11 122.3(11)
C9 C10 Cl2 118.3(9)
C11 C10 Cl2 119.3(9)
C12 C11 C10 118.6(11)
C12 C11 H11 120.7
C10 C11 H11 120.7
C7 C12 C11 119.6(11)
C7 C12 H12 120.2
C11 C12 H12 120.2
C1 Se1 Br1 96.5(3)
C1 Se1 Br3 92.6(3)
Br1 Se1 Br3 95.73(5)
C1 Se1 Br2 93.3(3)
Br1 Se1 Br2 93.33(5)
Br3 Se1 Br2 168.58(6)
C7 Se2 Br4 96.4(3)
C7 Se2 Br5 93.5(3)
Br4 Se2 Br5 93.88(5)
C7 Se2 Br6 92.5(3)
Br4 Se2 Br6 92.80(5)
Br5 Se2 Br6 170.44(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.390(15)
C1 C2 1.397(17)
C1 Se1 1.955(11)
C2 C3 1.412(17)
C2 H2 0.95
C3 C4 1.390(16)
C3 H3 0.95
C4 C5 1.358(16)
C4 Cl1 1.752(11)
C5 C6 1.397(16)
C5 H5 0.95
C6 H6 0.95
C7 C12 1.376(17)
C7 C8 1.401(16)
C7 Se2 1.954(11)
C8 C9 1.406(16)
C8 H8 0.95
C9 C10 1.369(16)
C9 H9 0.95
C10 C11 1.392(17)
C10 Cl2 1.745(11)
C11 C12 1.382(17)
C11 H11 0.95
C12 H12 0.95
Se1 Br1 2.3436(14)
Se1 Br3 2.4779(15)
Se1 Br2 2.6887(15)
Se2 Br4 2.3694(15)
Se2 Br5 2.4899(15)
Se2 Br6 2.6520(15)
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 0.2(17)
Se1 C1 C2 C3 -178.8(9)
C1 C2 C3 C4 1.0(17)
C2 C3 C4 C5 -3.6(17)
C2 C3 C4 Cl1 178.4(9)
C3 C4 C5 C6 4.9(17)
Cl1 C4 C5 C6 -177.1(9)
C2 C1 C6 C5 1.0(17)
Se1 C1 C6 C5 180.0(8)
C4 C5 C6 C1 -3.4(16)
C12 C7 C8 C9 1.8(16)
Se2 C7 C8 C9 -179.8(8)
C7 C8 C9 C10 -2.8(17)
C8 C9 C10 C11 3.1(18)
C8 C9 C10 Cl2 -179.0(9)
C9 C10 C11 C12 -2.1(17)
Cl2 C10 C11 C12 180.0(9)
C8 C7 C12 C11 -0.9(17)
Se2 C7 C12 C11 -179.3(8)
C10 C11 C12 C7 0.9(17)
C6 C1 Se1 Br1 -136.2(8)
C2 C1 Se1 Br1 42.8(9)
C6 C1 Se1 Br3 127.7(8)
C2 C1 Se1 Br3 -53.3(9)
C6 C1 Se1 Br2 -42.5(8)
C2 C1 Se1 Br2 136.5(9)
C12 C7 Se2 Br4 40.4(9)
C8 C7 Se2 Br4 -138.0(8)
C12 C7 Se2 Br5 -53.9(9)
C8 C7 Se2 Br5 127.7(8)
C12 C7 Se2 Br6 133.5(8)
C8 C7 Se2 Br6 -44.9(8)
