#------------------------------------------------------------------------------
#$Date: 2018-02-21 09:25:40 +0200 (Wed, 21 Feb 2018) $
#$Revision: 206532 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/89/1548972.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1548972
loop_
_publ_author_name
'Aarthi, R.'
'Thiruvalluvar, A.'
'Ramachandra Raja, C.'
_publ_section_title
;
 (4-Methylphenyl)methanaminium bromide hemihydrate
;
_journal_coeditor_code           HB4211
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x180270
_journal_paper_doi               10.1107/S2414314618002705
_journal_volume                  3
_journal_year                    2018
_chemical_formula_iupac          'C8 H12 N1 +, Br -, 0.5(H2 O)'
_chemical_formula_moiety         'C8 H12 N1 +, Br -, 0.5H2 O'
_chemical_formula_sum            'C8 H13 Br N O0.5'
_chemical_formula_weight         211.10
_chemical_name_systematic
;
(4-Methylphenyl)methanaminium bromide hemihydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 98.430(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.7456(18)
_cell_length_b                   5.0266(3)
_cell_length_c                   12.0636(7)
_cell_measurement_reflns_used    7215
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.17
_cell_measurement_theta_min      3.38
_cell_volume                     1844.24(19)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF
(Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker KappaCCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11261
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.207
_diffrn_reflns_theta_min         3.480
_exptl_absorpt_coefficient_mu    4.396
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.514
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0282
_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)+(0.0267P)²+2.3541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                2129
_reflns_number_total             2479
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4211sup1.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C8 H13 Br1 N1 O0.5'
_cod_database_code               1548972
_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   0.668
_shelx_estimated_absorpt_t_max   0.810
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.27703(8) 1.1301(4) 0.6636(2) 0.0494(6) Uani d 1
H H1A 0.286021 1.299079 0.637653 0.074 Uiso calc 1
H H1B 0.275755 1.140043 0.742564 0.074 Uiso calc 1
H H1C 0.248504 1.085224 0.624468 0.074 Uiso calc 1
C C2 0.30965(6) 0.9198(4) 0.64201(18) 0.0340(4) Uani d 1
C C3 0.31078(7) 0.8211(4) 0.53533(18) 0.0406(4) Uani d 1
H H3 0.291045 0.886455 0.475733 0.049 Uiso calc 1
C C4 0.34066(7) 0.6273(4) 0.51557(17) 0.0399(4) Uani d 1
H H4 0.340822 0.565059 0.443038 0.048 Uiso calc 1
C C5 0.37039(6) 0.5248(4) 0.60273(17) 0.0321(4) Uani d 1
C C6 0.36998(7) 0.6264(4) 0.70908(17) 0.0385(4) Uani d 1
H H6 0.390104 0.563229 0.768332 0.046 Uiso calc 1
C C7 0.34002(7) 0.8212(4) 0.72890(18) 0.0402(4) Uani d 1
H H7 0.340289 0.886252 0.801160 0.048 Uiso calc 1
C C8 0.40117(7) 0.3025(4) 0.5831(2) 0.0427(5) Uani d 1
H H8A 0.400833 0.169245 0.641177 0.051 Uiso calc 1
H H8B 0.390675 0.219026 0.511705 0.051 Uiso calc 1
N N1 0.44665(6) 0.3933(4) 0.58300(18) 0.0420(4) Uani d 1
Br Br1 0.44849(2) 0.86079(4) 0.38999(2) 0.04217(8) Uani d 1
O O1 0.500000 0.2903(5) 0.250000 0.0548(6) Uani d 1
H H1 0.4840(11) 0.196(6) 0.286(3) 0.096(13) Uiso d 1
H H1D 0.4466(9) 0.520(4) 0.5282(17) 0.065(8) Uiso d 1
H H1E 0.4585(9) 0.465(5) 0.6483(14) 0.063(8) Uiso d 1
H H1F 0.4636(9) 0.255(4) 0.566(2) 0.072(9) Uiso d 1
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'
N N 0.0061 0.0033 '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'
O O 0.0106 0.0060 '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_site_symmetry_3
_geom_angle
C2 C1 H1A . 109.5
C2 C1 H1B . 109.5
H1A C1 H1B . 109.5
C2 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
C3 C2 C7 . 117.90(18)
C3 C2 C1 . 121.4(2)
C7 C2 C1 . 120.7(2)
C4 C3 C2 . 121.34(19)
C4 C3 H3 . 119.3
C2 C3 H3 . 119.3
C3 C4 C5 . 120.75(18)
C3 C4 H4 . 119.6
C5 C4 H4 . 119.6
C6 C5 C4 . 118.12(18)
C6 C5 C8 . 120.76(19)
C4 C5 C8 . 121.08(19)
C5 C6 C7 . 121.11(19)
C5 C6 H6 . 119.4
C7 C6 H6 . 119.4
C6 C7 C2 . 120.74(19)
C6 C7 H7 . 119.6
C2 C7 H7 . 119.6
N1 C8 C5 . 112.91(17)
N1 C8 H8A . 109.0
C5 C8 H8A . 109.0
N1 C8 H8B . 109.0
C5 C8 H8B . 109.0
H8A C8 H8B . 107.8
C8 N1 H1D . 108.4(18)
C8 N1 H1E . 113.0(18)
H1D N1 H1E . 108.0(19)
C8 N1 H1F . 109.8(19)
H1D N1 H1F . 107.9(19)
H1E N1 H1F . 110(2)
H1 O1 H1 2_655 112(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.506(3)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
C2 C3 . 1.384(3)
C2 C7 . 1.389(3)
C3 C4 . 1.384(3)
C3 H3 . 0.9300
C4 C5 . 1.387(3)
C4 H4 . 0.9300
C5 C6 . 1.383(3)
C5 C8 . 1.505(3)
C6 C7 . 1.389(3)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 N1 . 1.471(3)
C8 H8A . 0.9700
C8 H8B . 0.9700
N1 H1D . 0.919(15)
N1 H1E . 0.895(15)
N1 H1F . 0.909(15)
O1 H1 . 0.848(17)
O1 H1 2_655 0.848(17)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 Br1 1_545 0.848(17) 2.450(19) 3.2870(17) 169(3) yes
N1 H1D Br1 . 0.919(15) 2.396(16) 3.314(2) 178(2) yes
N1 H1E O1 5_666 0.895(15) 2.045(19) 2.883(3) 155(2) yes
N1 H1F Br1 1_545 0.909(15) 2.89(2) 3.554(2) 131(2) yes
N1 H1F Br1 5_666 0.909(15) 2.74(3) 3.4383(17) 134(2) yes
C8 H8B Br1 1_545 0.97 3.05 3.670(2) 123 yes
C1 H1A Cg1 1_565 0.96 2.73 3.634(2) 157 yes
C8 H8A Cg1 1_545 0.97 2.90 3.530(2) 123 yes
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
C7 C2 C3 C4 1.0(3)
C1 C2 C3 C4 -179.8(2)
C2 C3 C4 C5 0.3(3)
C3 C4 C5 C6 -1.6(3)
C3 C4 C5 C8 176.30(19)
C4 C5 C6 C7 1.5(3)
C8 C5 C6 C7 -176.38(19)
C5 C6 C7 C2 -0.2(3)
C3 C2 C7 C6 -1.1(3)
C1 C2 C7 C6 179.71(19)
C6 C5 C8 N1 -77.2(3)
C4 C5 C8 N1 105.0(2)

_cod_database_fobs_code 1548972
