#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225658.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_2225658
loop_
_publ_author_name
'Dan, Wenyan'
'Di, Youying'
'He, Donghua'
'Yang, Weiwei'
'Kong, Yuxia'
_publ_section_title
;
 n-Dodecylammonium bromide monohydrate
;
_journal_coeditor_code           LX2141
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o910
_journal_paper_doi               10.1107/S1600536810010123
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H28 N +, Br -, H2 O'
_chemical_formula_moiety         'C12 H28 N +, Br -, H2 O'
_chemical_formula_sum            'C12 H30 Br N O'
_chemical_formula_weight         284.28
_chemical_name_systematic
;
n-Dodecylammonium bromide monohydrate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.798(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7921(5)
_cell_length_b                   42.810(4)
_cell_length_c                   7.8573(8)
_cell_measurement_reflns_used    1266
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9745
_cell_measurement_theta_min      2.8575
_cell_volume                     1551.0(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0943
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4760
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    2.633
_exptl_absorpt_correction_T_max  0.8580
_exptl_absorpt_correction_T_min  0.4043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       acicular
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.241
_refine_ls_abs_structure_details 'Flack (1983), 945 Friedel pairs'
_refine_ls_abs_structure_Flack   0.048(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2644
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0277P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                1665
_reflns_number_total             2644
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2141.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2225658
_cod_database_fobs_code          2225658
loop_
_symmetry_equiv_pos_as_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'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.2086(2) 0.524590(10) 0.38293(16) 0.05643(18) Uani d . 1 . .
O O1 0.8268(12) 0.45062(13) 0.1580(6) 0.0760(15) Uani d D 1 . .
H H1 0.734(13) 0.4485(18) 0.053(6) 0.114 Uiso d D 1 . .
H H2 0.993(11) 0.4589(15) 0.124(9) 0.114 Uiso d D 1 . .
N N1 0.7249(9) 0.46990(8) 0.4809(6) 0.0502(12) Uani d . 1 . .
H H1A 0.8831 0.4731 0.5697 0.075 Uiso calc R 1 . .
H H1B 0.6083 0.4864 0.4696 0.075 Uiso calc R 1 . .
H H1C 0.7755 0.4671 0.3810 0.075 Uiso calc R 1 . .
C C1 0.5729(12) 0.44200(13) 0.5176(8) 0.0496(17) Uani d . 1 . .
H H1D 0.3952 0.4392 0.4238 0.059 Uiso calc R 1 . .
H H1E 0.5212 0.4449 0.6276 0.059 Uiso calc R 1 . .
C C2 0.7567(11) 0.41323(10) 0.5313(7) 0.0480(14) Uani d . 1 . .
H H2A 0.9345 0.4161 0.6249 0.058 Uiso calc R 1 . .
H H2B 0.8084 0.4104 0.4213 0.058 Uiso calc R 1 . .
C C3 0.6028(11) 0.38403(11) 0.5696(7) 0.0496(14) Uani d . 1 . .
H H3A 0.5795 0.3855 0.6881 0.059 Uiso calc R 1 . .
H H3B 0.4108 0.3831 0.4875 0.059 Uiso calc R 1 . .
C C4 0.7635(11) 0.35416(10) 0.5545(7) 0.0466(14) Uani d . 1 . .
H H4A 0.7908 0.3531 0.4367 0.056 Uiso calc R 1 . .
H H4B 0.9540 0.3550 0.6382 0.056 Uiso calc R 1 . .
C C5 0.6137(11) 0.32477(11) 0.5877(7) 0.0484(14) Uani d . 1 . .
H H5A 0.5955 0.3254 0.7076 0.058 Uiso calc R 1 . .
H H5B 0.4194 0.3245 0.5082 0.058 Uiso calc R 1 . .
C C6 0.7625(11) 0.29500(11) 0.5641(7) 0.0488(14) Uani d . 1 . .
H H6A 0.9550 0.2951 0.6458 0.059 Uiso calc R 1 . .
H H6B 0.7859 0.2947 0.4453 0.059 Uiso calc R 1 . .
C C7 0.6105(11) 0.26515(11) 0.5920(7) 0.0454(13) Uani d . 1 . .
H H7A 0.5909 0.2651 0.7117 0.055 Uiso calc R 1 . .
H H7B 0.4168 0.2651 0.5117 0.055 Uiso calc R 1 . .
C C8 0.7621(11) 0.23602(11) 0.5640(7) 0.0484(14) Uani d . 1 . .
H H8A 0.9555 0.2361 0.6447 0.058 Uiso calc R 1 . .
H H8B 0.7827 0.2362 0.4446 0.058 Uiso calc R 1 . .
C C9 0.6128(11) 0.20610(11) 0.5905(7) 0.0495(14) Uani d . 1 . .
H H9A 0.4180 0.2062 0.5116 0.059 Uiso calc R 1 . .
H H9B 0.5957 0.2058 0.7107 0.059 Uiso calc R 1 . .
C C10 0.7642(12) 0.17604(11) 0.5585(7) 0.0508(14) Uani d . 1 . .
H H10A 0.7842 0.1766 0.4389 0.061 Uiso calc R 1 . .
H H10B 0.9579 0.1757 0.6387 0.061 Uiso calc R 1 . .
C C11 0.6143(13) 0.14651(12) 0.5818(8) 0.0592(16) Uani d . 1 . .
H H11A 0.5946 0.1459 0.7014 0.071 Uiso calc R 1 . .
H H11B 0.4205 0.1468 0.5016 0.071 Uiso calc R 1 . .
C C12 0.7623(15) 0.11758(13) 0.5502(9) 0.080(2) Uani d . 1 . .
H H12A 0.7850 0.1179 0.4325 0.121 Uiso calc R 1 . .
H H12B 0.6483 0.0998 0.5634 0.121 Uiso calc R 1 . .
H H12C 0.9496 0.1163 0.6342 0.121 Uiso calc R 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H1 O1 H2 . . 91(5) ?
C1 N1 H1A . . 109.5 ?
C1 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C1 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
N1 C1 C2 . . 111.6(5) ?
N1 C1 H1D . . 109.3 ?
C2 C1 H1D . . 109.3 ?
N1 C1 H1E . . 109.3 ?
C2 C1 H1E . . 109.3 ?
H1D C1 H1E . . 108.0 ?
C1 C2 C3 . . 112.4(4) ?
C1 C2 H2A . . 109.1 ?
C3 C2 H2A . . 109.1 ?
C1 C2 H2B . . 109.1 ?
C3 C2 H2B . . 109.1 ?
H2A C2 H2B . . 107.9 ?
C4 C3 C2 . . 113.2(4) ?
C4 C3 H3A . . 108.9 ?
C2 C3 H3A . . 108.9 ?
C4 C3 H3B . . 108.9 ?
C2 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.8 ?
C5 C4 C3 . . 114.6(4) ?
C5 C4 H4A . . 108.6 ?
C3 C4 H4A . . 108.6 ?
C5 C4 H4B . . 108.6 ?
C3 C4 H4B . . 108.6 ?
H4A C4 H4B . . 107.6 ?
C6 C5 C4 . . 115.1(4) ?
C6 C5 H5A . . 108.5 ?
C4 C5 H5A . . 108.5 ?
C6 C5 H5B . . 108.5 ?
C4 C5 H5B . . 108.5 ?
H5A C5 H5B . . 107.5 ?
C5 C6 C7 . . 115.9(4) ?
C5 C6 H6A . . 108.3 ?
C7 C6 H6A . . 108.3 ?
C5 C6 H6B . . 108.3 ?
C7 C6 H6B . . 108.3 ?
H6A C6 H6B . . 107.4 ?
C8 C7 C6 . . 114.3(4) ?
C8 C7 H7A . . 108.7 ?
C6 C7 H7A . . 108.7 ?
C8 C7 H7B . . 108.7 ?
C6 C7 H7B . . 108.7 ?
H7A C7 H7B . . 107.6 ?
C7 C8 C9 . . 114.9(4) ?
C7 C8 H8A . . 108.5 ?
C9 C8 H8A . . 108.5 ?
C7 C8 H8B . . 108.5 ?
C9 C8 H8B . . 108.5 ?
H8A C8 H8B . . 107.5 ?
C8 C9 C10 . . 115.3(4) ?
C8 C9 H9A . . 108.5 ?
C10 C9 H9A . . 108.5 ?
C8 C9 H9B . . 108.5 ?
C10 C9 H9B . . 108.5 ?
H9A C9 H9B . . 107.5 ?
C11 C10 C9 . . 115.3(4) ?
C11 C10 H10A . . 108.5 ?
C9 C10 H10A . . 108.5 ?
C11 C10 H10B . . 108.5 ?
C9 C10 H10B . . 108.5 ?
H10A C10 H10B . . 107.5 ?
C12 C11 C10 . . 114.8(5) ?
C12 C11 H11A . . 108.6 ?
C10 C11 H11A . . 108.6 ?
C12 C11 H11B . . 108.6 ?
C10 C11 H11B . . 108.6 ?
H11A C11 H11B . . 107.5 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 H1 . 0.83(4) ?
O1 H2 . 0.97(4) ?
N1 C1 . 1.468(7) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
C1 C2 . 1.501(7) ?
C1 H1D . 0.9700 ?
C1 H1E . 0.9700 ?
C2 C3 . 1.522(6) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.514(7) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.506(6) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.496(6) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.516(6) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.490(6) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.509(7) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.532(7) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.490(7) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.481(8) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
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
N1 H1A Br1 2_665 0.89 2.53 3.380(4) 159.4
N1 H1B Br1 . 0.89 2.47 3.340(4) 166.4
N1 H1C O1 . 0.89 1.97 2.834(7) 164.6
O1 H1 Br1 2_564 0.83(4) 2.76(6) 3.329(5) 128(6)
O1 H2 Br1 2_664 0.97(4) 2.49(5) 3.361(5) 149(5)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 179.9(4) ?
C1 C2 C3 C4 . . . . 170.6(5) ?
C2 C3 C4 C5 . . . . -178.7(4) ?
C3 C4 C5 C6 . . . . 177.0(5) ?
C4 C5 C6 C7 . . . . -178.4(4) ?
C5 C6 C7 C8 . . . . 178.9(4) ?
C6 C7 C8 C9 . . . . -179.7(5) ?
C7 C8 C9 C10 . . . . 178.9(4) ?
C8 C9 C10 C11 . . . . -179.1(5) ?
C9 C10 C11 C12 . . . . 179.9(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656055
