#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:37:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180479 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/48/7214895.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_7214895
loop_
_publ_author_name
'Yufit, Dmitry S.'
'Zubatyuk, Roman'
'Shishkin, Oleg V.'
'Howard, Judith A. K.'
_publ_section_title
;
 Low-melting molecular complexes. Halogen bonds in molecular complexes of
 bromoform
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              8222
_journal_paper_doi               10.1039/c2ce26191j
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C H Br3, C6 H10 O'
_chemical_formula_sum            'C7 H11 Br3 O'
_chemical_formula_weight         350.89
_chemical_melting_point          224
_chemical_name_systematic
;
molecular complex of bromoform with cyclohexanone (1:1)
;
_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'
_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_date             2011-06-28
_audit_creation_method
;
Olex2 1.1-beta
(compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.210(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4762(9)
_cell_length_b                   15.787(2)
_cell_length_c                   8.3158(11)
_cell_measurement_reflns_used    1847
_cell_measurement_temperature    210
_cell_measurement_theta_max      24.11
_cell_measurement_theta_min      2.57
_cell_volume                     1104.0(2)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      210
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8404
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.42
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           10.0
_diffrn_source_power             0.3
_diffrn_source_target            Mo
_diffrn_source_voltage           30.0
_exptl_absorpt_coefficient_mu    10.913
_exptl_absorpt_correction_T_max  0.1001
_exptl_absorpt_correction_T_min  0.0005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.1173 before and 0.0289 after correction.
The Ratio of minimum to maximum transmission is 0.004995004995.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            'dull white colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   white
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         2500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1636
_reflns_number_total             2500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26191j.txt
_cod_data_source_block           I_bh1
_cod_database_code               7214895
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
Br1 Br 0.50671(6) 0.39060(3) 0.59423(6) 0.05756(17) Uani 1 1 d .
Br2 Br 0.12990(6) 0.39976(3) 0.57371(6) 0.05824(17) Uani 1 1 d .
Br3 Br 0.29172(7) 0.28946(4) 0.32189(7) 0.0753(2) Uani 1 1 d .
O1 O 0.1539(4) 0.5540(3) 0.2215(5) 0.0796(12) Uani 1 1 d .
C1 C 0.1580(6) 0.5742(3) 0.0802(6) 0.0553(12) Uani 1 1 d .
C1S C 0.3086(6) 0.3902(3) 0.4535(6) 0.0478(11) Uani 1 1 d .
H1S H 0.3077 0.4393 0.3813 0.057 Uiso 1 1 calc R
C2 C 0.2563(8) 0.5277(4) -0.0242(8) 0.0801(18) Uani 1 1 d .
H2A H 0.1878 0.4942 -0.1020 0.096 Uiso 1 1 calc R
H2B H 0.3261 0.4891 0.0419 0.096 Uiso 1 1 calc R
C3 C 0.3554(8) 0.5865(5) -0.1140(8) 0.0842(19) Uani 1 1 d .
H3A H 0.4389 0.6110 -0.0377 0.101 Uiso 1 1 calc R
H3B H 0.4055 0.5541 -0.1928 0.101 Uiso 1 1 calc R
C4 C 0.2586(7) 0.6565(4) -0.1997(6) 0.0747(17) Uani 1 1 d .
H4A H 0.3280 0.6948 -0.2491 0.090 Uiso 1 1 calc R
H4B H 0.1829 0.6328 -0.2850 0.090 Uiso 1 1 calc R
C5 C 0.1725(8) 0.7038(4) -0.0838(8) 0.091(2) Uani 1 1 d .
H5A H 0.1071 0.7470 -0.1422 0.109 Uiso 1 1 calc R
H5B H 0.2492 0.7321 -0.0054 0.109 Uiso 1 1 calc R
C6 C 0.0676(7) 0.6471(4) 0.0057(8) 0.0775(17) Uani 1 1 d .
H6A H 0.0250 0.6796 0.0893 0.093 Uiso 1 1 calc R
H6B H -0.0211 0.6268 -0.0695 0.093 Uiso 1 1 calc R
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
Br1 0.0541(3) 0.0548(3) 0.0616(3) 0.0012(2) -0.0014(3) -0.0015(2)
Br2 0.0559(3) 0.0619(3) 0.0589(3) -0.0003(2) 0.0148(3) 0.0018(2)
Br3 0.0795(4) 0.0758(4) 0.0720(4) -0.0311(3) 0.0147(3) -0.0107(3)
O1 0.068(3) 0.109(3) 0.061(2) 0.014(2) 0.009(2) -0.004(2)
C1 0.044(3) 0.066(3) 0.055(3) 0.001(3) 0.004(2) -0.003(2)
C1S 0.047(3) 0.048(3) 0.048(3) 0.002(2) 0.004(2) -0.004(2)
C2 0.088(4) 0.074(4) 0.083(4) -0.003(3) 0.029(4) 0.024(3)
C3 0.070(4) 0.106(5) 0.083(4) -0.008(4) 0.033(3) 0.019(4)
C4 0.075(4) 0.097(5) 0.054(3) 0.012(3) 0.015(3) -0.001(3)
C5 0.110(5) 0.060(4) 0.110(5) 0.016(3) 0.046(4) 0.013(3)
C6 0.066(3) 0.085(4) 0.088(4) 0.011(3) 0.034(3) 0.022(3)
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'
O O 0.0106 0.0060 '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
O1 C1 C2 121.6(5)
O1 C1 C6 122.1(5)
C2 C1 C6 116.3(5)
Br1 C1S Br2 111.6(2)
Br1 C1S Br3 110.2(2)
Br1 C1S H1S 108.1
Br2 C1S Br3 110.7(2)
Br2 C1S H1S 108.1
Br3 C1S H1S 108.1
C1 C2 H2A 109.2
C1 C2 H2B 109.2
C1 C2 C3 112.1(5)
H2A C2 H2B 107.9
C3 C2 H2A 109.2
C3 C2 H2B 109.2
C2 C3 H3A 109.1
C2 C3 H3B 109.1
H3A C3 H3B 107.8
C4 C3 C2 112.5(5)
C4 C3 H3A 109.1
C4 C3 H3B 109.1
C3 C4 H4A 109.6
C3 C4 H4B 109.6
H4A C4 H4B 108.1
C5 C4 C3 110.3(5)
C5 C4 H4A 109.6
C5 C4 H4B 109.6
C4 C5 H5A 109.0
C4 C5 H5B 109.0
C4 C5 C6 112.8(5)
H5A C5 H5B 107.8
C6 C5 H5A 109.0
C6 C5 H5B 109.0
C1 C6 C5 111.1(5)
C1 C6 H6A 109.4
C1 C6 H6B 109.4
C5 C6 H6A 109.4
C5 C6 H6B 109.4
H6A C6 H6B 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1S 1.922(5)
Br2 C1S 1.923(5)
Br3 C1S 1.926(5)
O1 C1 1.222(6)
C1 C2 1.473(7)
C1 C6 1.475(8)
C1S H1S 0.9800
C2 H2A 0.9700
C2 H2B 0.9700
C2 C3 1.511(8)
C3 H3A 0.9700
C3 H3B 0.9700
C3 C4 1.501(9)
C4 H4A 0.9700
C4 H4B 0.9700
C4 C5 1.482(8)
C5 H5A 0.9700
C5 H5B 0.9700
C5 C6 1.521(8)
C6 H6A 0.9700
C6 H6B 0.9700
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1S H1S O1 0.98 2.51 3.391(6) 149.1
