Different supramolecular interactions mediated by Br atoms in the crystal structures of three anisole derivatives
Nestler, Robert; Schwarzer, Anke; Gruber, Tobias; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618001997

data_2021010
_publ_section_title
;
 Different supramolecular interactions mediated by Br atoms in the crystal
 structures of three anisole derivatives
;
_journal_coeditor_code           EG3234
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618001997
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C9 H11 Br O3'
_chemical_formula_moiety         'C9 H11 Br O3'
_chemical_formula_sum            'C9 H11 Br O3'
_chemical_formula_weight         247.09
_chemical_melting_point          400.15
_chemical_name_common
;
4-Bromo-2,6-bis(hydroxymethyl)anisole
;
_chemical_name_systematic
;
[5-Bromo-3-(hydroxymethyl)-2-methoxyphenyl]methanol
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1596(7)
_cell_length_b                   16.2514(9)
_cell_length_c                   4.4735(2)
_cell_measurement_reflns_used    5411
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.15
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_cell_volume                     956.71(9)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
XP (Sheldrick, 2008)
;
_computing_publication_material
;
<i>WinGX</i> (Farrugia, 2012), <i>publCIF</i> (Westrip, 2010)
and
<i>SHELXLE</i> (H\"ubschle <i>et al.</i>, 2011)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_limit_h_max       16
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_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4183
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.484
_diffrn_reflns_theta_min         2.507
_exptl_absorpt_coefficient_mu    4.268
_exptl_absorpt_correction_T_max  0.5639
_exptl_absorpt_correction_T_min  0.2833
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2002)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_description       piece
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.822
_refine_diff_density_min         -1.218
_refine_ls_abs_structure_details
;
Classical Flack (1983) method preferred over Parsons because s.u. lower;
<b>??? Friedel pairs</b>
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1904
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0646
_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/[\s^2^(Fo^2^)+(0.1230P)^2^+3.1968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.1903
_reflns_number_gt                1647
_reflns_number_total             1904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            eg3234sup1.cif
_cod_data_source_block           II
_cod_database_code               2021010
_cod_database_fobs_code          2021010
_shelx_estimated_absorpt_t_min   0.250
_shelx_estimated_absorpt_t_max   0.567
_shelx_hkl_checksum              70108
_shelx_res_checksum              36867