The competition between halogen bonds (Br⋯O) and C–H⋯O hydrogen bonds: the structure of the acetone–bromine complex revisited
Jones, R. H.; Knight, K. S.; Marshall, W. G.; Coles, S. J.; Horton, P. N.; Pitak, M. B.; CrystEngComm 15 (2013) 8572–; doi:10.1039/c3ce41472h

data_7211202
_publ_section_title
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 The competition between halogen bonds (Br&#x22EF;O) and C--H&#x22EF;O
 hydrogen bonds: the structure of the acetone--bromine complex revisited
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_journal_issue                   42
_journal_name_full               CrystEngComm
_journal_page_first              8572
_journal_paper_doi               10.1039/c3ce41472h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C3 D6 Br2 O1'
_chemical_formula_sum            'C3 Br2 D6 O'
_chemical_formula_weight         223.92
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 102.173(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5755(4)
_cell_length_b                   7.3774(4)
_cell_length_c                   12.0168(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    110
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     656.49(6)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3227
_diffrn_reflns_theta_full        26.972
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         3.469
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.229
_exptl_absorpt_correction_T_max  0.2040
_exptl_absorpt_correction_T_min  0.1251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.55
_refine_diff_density_min         -1.32
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     39
_refine_ls_number_reflns         668
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.0009737
_refine_ls_shift/su_mean         0.0000947
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 40.9 43.4 30.5 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0788
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0726
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                681
_reflns_number_total             748
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.67
_oxford_diffrn_Wilson_scale      5.18
_oxford_refine_ls_r_factor_ref   0.0301
_oxford_refine_ls_scale          0.4431(10)
_oxford_reflns_number_all        748
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            c3ce41472h.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_original_formula_sum        'C3 D6 Br2 O1'
_cod_database_code               7211202
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT BR   (    1 ,X'S,U'S)  UNTIL C    (    2 ) 
CONT D    (    1 ,X'S,U[ISO])  UNTIL D    (    3 ) 
EQUIV D(1,U[ISO]) UNTIL D(3) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            3 H ON SP 3 
ANGLE 109.54, 6.0 = 
CONT C(1) TO C ( 2) TO D(1) 
CONT C(1) TO C ( 2) TO D(2) 
CONT C(1) TO C ( 2) TO D(3) 
ANGLE 0.0, 6.0 = MEAN D(1) TO C ( 2) TO D(2) 
CONT D(1) TO C ( 2) TO D(3) 
CONT D(2) TO C ( 2) TO D(3) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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