#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/97/2229747.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_2229747
loop_
_publ_author_name
'Li, Jian'
_publ_section_title
;
 2-Methylanilinium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate
 methanol monosolvate
;
_journal_coeditor_code           LH5212
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o900
_journal_paper_doi               10.1107/S1600536811008543
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C7 H10 N +, C9 H3 Br4 O4 -, C H4 O'
_chemical_formula_moiety         'C7 H10 N +, C9 H3 Br4 O4 -, C H4 O'
_chemical_formula_sum            'C17 H17 Br4 N O5'
_chemical_formula_weight         634.96
_chemical_name_systematic
;
2-Methylanilinium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol
monosolvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3710(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1909(8)
_cell_length_b                   13.5551(12)
_cell_length_c                   19.5082(16)
_cell_measurement_reflns_used    2873
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.864
_cell_measurement_theta_min      2.573
_cell_volume                     2165.9(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10672
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    7.459
_exptl_absorpt_correction_T_max  0.2292
_exptl_absorpt_correction_T_min  0.1543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.587
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0371
_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)+(0.0232P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                2507
_reflns_number_total             3811
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5212.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229747
_cod_database_fobs_code          2229747
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.03655(7) 0.49170(4) 0.40325(2) 0.03923(16) Uani d . 1 . .
Br Br2 0.02019(8) 0.40894(4) 0.24560(2) 0.05302(19) Uani d . 1 . .
Br Br3 0.15610(7) 0.18668(4) 0.20996(2) 0.05158(18) Uani d . 1 . .
Br Br4 0.29944(7) 0.04678(4) 0.33723(3) 0.05207(19) Uani d . 1 . .
N N1 0.3657(5) 0.8858(3) 0.05060(18) 0.0390(11) Uani d . 1 . .
H H1A 0.3027 0.8481 0.0241 0.058 Uiso calc R 1 . .
H H1B 0.4659 0.8882 0.0333 0.058 Uiso calc R 1 . .
H H1C 0.3243 0.9464 0.0524 0.058 Uiso calc R 1 . .
O O1 0.1935(5) 0.0866(3) 0.49814(18) 0.0577(11) Uani d . 1 . .
O O2 0.4329(5) 0.1646(3) 0.5033(2) 0.0712(13) Uani d . 1 . .
O O3 0.1279(4) 0.3275(2) 0.55173(15) 0.0374(9) Uani d . 1 . .
O O4 0.3365(4) 0.4141(2) 0.51013(15) 0.0386(9) Uani d . 1 . .
O O5 0.8267(5) 0.2644(3) 0.5294(2) 0.0714(12) Uani d . 1 . .
H H5 0.9166 0.2887 0.5373 0.107 Uiso calc R 1 . .
C C1 0.3034(8) 0.1514(4) 0.4786(2) 0.0398(14) Uani d . 1 . .
C C2 0.2195(6) 0.3546(3) 0.5050(2) 0.0268(11) Uani d . 1 . .
C C3 0.2381(5) 0.2138(3) 0.4200(2) 0.0265(11) Uani d . 1 . .
C C4 0.1913(5) 0.3107(3) 0.4340(2) 0.0242(11) Uani d . 1 . .
C C5 0.1213(6) 0.3663(3) 0.3820(2) 0.0293(12) Uani d . 1 . .
C C6 0.1100(6) 0.3289(3) 0.3151(2) 0.0297(12) Uani d . 1 . .
C C7 0.1649(6) 0.2341(4) 0.3009(2) 0.0315(12) Uani d . 1 . .
C C8 0.2249(6) 0.1765(3) 0.3535(2) 0.0326(12) Uani d . 1 . .
C C9 0.2418(9) 0.0245(5) 0.5563(3) 0.104(3) Uani d . 1 . .
H H9A 0.3277 -0.0193 0.5425 0.156 Uiso calc R 1 . .
H H9B 0.1496 -0.0134 0.5712 0.156 Uiso calc R 1 . .
H H9C 0.2798 0.0654 0.5932 0.156 Uiso calc R 1 . .
C C10 0.3726(6) 0.8439(4) 0.1201(3) 0.0410(14) Uani d . 1 . .
C C11 0.4507(7) 0.8936(4) 0.1712(3) 0.0450(15) Uani d . 1 . .
C C12 0.4626(8) 0.8472(5) 0.2352(3) 0.0645(19) Uani d . 1 . .
H H12 0.5158 0.8790 0.2712 0.077 Uiso calc R 1 . .
C C13 0.3973(9) 0.7565(6) 0.2453(3) 0.078(2) Uani d . 1 . .
H H13 0.4090 0.7263 0.2878 0.094 Uiso calc R 1 . .
C C14 0.3140(9) 0.7084(5) 0.1937(4) 0.080(2) Uani d . 1 . .
H H14 0.2653 0.6475 0.2017 0.096 Uiso calc R 1 . .
C C15 0.3040(7) 0.7521(4) 0.1297(3) 0.0584(17) Uani d . 1 . .
H H15 0.2517 0.7199 0.0936 0.070 Uiso calc R 1 . .
C C16 0.5220(7) 0.9958(4) 0.1608(3) 0.0619(17) Uani d . 1 . .
H H16A 0.5957 0.9947 0.1227 0.093 Uiso calc R 1 . .
H H16B 0.5799 1.0156 0.2015 0.093 Uiso calc R 1 . .
H H16C 0.4354 1.0418 0.1516 0.093 Uiso calc R 1 . .
C C17 0.7840(9) 0.2058(7) 0.5817(4) 0.159(5) Uani d . 1 . .
H H17A 0.8389 0.1435 0.5776 0.238 Uiso calc R 1 . .
H H17B 0.6681 0.1954 0.5806 0.238 Uiso calc R 1 . .
H H17C 0.8145 0.2365 0.6242 0.238 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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 N1 H1A . . 109.5 ?
C10 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C10 N1 H1C . . 109.5 ?
H1A N1 H1C . . 109.5 ?
H1B N1 H1C . . 109.5 ?
C1 O1 C9 . . 115.2(5) ?
C17 O5 H5 . . 109.5 ?
O2 C1 O1 . . 126.9(5) ?
O2 C1 C3 . . 122.4(5) ?
O1 C1 C3 . . 110.6(5) ?
O3 C2 O4 . . 126.6(4) ?
O3 C2 C4 . . 117.7(4) ?
O4 C2 C4 . . 115.7(4) ?
C4 C3 C8 . . 120.1(4) ?
C4 C3 C1 . . 118.3(4) ?
C8 C3 C1 . . 121.6(4) ?
C5 C4 C3 . . 118.9(4) ?
C5 C4 C2 . . 120.8(4) ?
C3 C4 C2 . . 120.3(4) ?
C4 C5 C6 . . 120.6(4) ?
C4 C5 Br1 . . 118.8(3) ?
C6 C5 Br1 . . 120.6(3) ?
C7 C6 C5 . . 120.0(4) ?
C7 C6 Br2 . . 121.0(3) ?
C5 C6 Br2 . . 119.0(3) ?
C8 C7 C6 . . 119.4(4) ?
C8 C7 Br3 . . 121.2(4) ?
C6 C7 Br3 . . 119.4(3) ?
C7 C8 C3 . . 120.8(4) ?
C7 C8 Br4 . . 121.1(3) ?
C3 C8 Br4 . . 118.0(3) ?
O1 C9 H9A . . 109.5 ?
O1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C15 . . 122.6(5) ?
C11 C10 N1 . . 120.0(5) ?
C15 C10 N1 . . 117.4(5) ?
C10 C11 C12 . . 117.4(5) ?
C10 C11 C16 . . 122.3(5) ?
C12 C11 C16 . . 120.3(6) ?
C13 C12 C11 . . 120.7(6) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C14 . . 121.2(6) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C13 C14 C15 . . 118.9(6) ?
C13 C14 H14 . . 120.6 ?
C15 C14 H14 . . 120.6 ?
C10 C15 C14 . . 119.2(6) ?
C10 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C11 C16 H16A . . 109.5 ?
C11 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C11 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O5 C17 H17A . . 109.5 ?
O5 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O5 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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
Br1 C5 . 1.883(5) ?
Br2 C6 . 1.883(4) ?
Br3 C7 . 1.889(4) ?
Br4 C8 . 1.889(5) ?
N1 C10 . 1.471(6) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
N1 H1C . 0.8900 ?
O1 C1 . 1.315(6) ?
O1 C9 . 1.464(6) ?
O2 C1 . 1.176(6) ?
O3 C2 . 1.239(5) ?
O4 C2 . 1.256(5) ?
O5 C17 . 1.341(7) ?
O5 H5 . 0.8200 ?
C1 C3 . 1.517(6) ?
C2 C4 . 1.525(6) ?
C3 C4 . 1.395(6) ?
C3 C8 . 1.397(6) ?
C4 C5 . 1.385(6) ?
C5 C6 . 1.403(6) ?
C6 C7 . 1.390(6) ?
C7 C8 . 1.376(6) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.359(7) ?
C10 C15 . 1.379(7) ?
C11 C12 . 1.402(7) ?
C11 C16 . 1.518(7) ?
C12 C13 . 1.356(8) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.377(9) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.383(8) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 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 O5 2_655 0.89 1.87 2.756(6) 178
N1 H1B O4 2_655 0.89 1.87 2.746(5) 170
O5 H5 O3 1_655 0.82 1.83 2.645(5) 173
C15 H15 O5 2_655 0.93 2.55 3.281(7) 135
C17 H17B O2 . 0.96 2.47 3.296(9) 144
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
C9 O1 C1 O2 . . . . -0.9(8) ?
C9 O1 C1 C3 . . . . -178.0(4) ?
O2 C1 C3 C4 . . . . -72.0(7) ?
O1 C1 C3 C4 . . . . 105.2(5) ?
O2 C1 C3 C8 . . . . 107.7(6) ?
O1 C1 C3 C8 . . . . -75.1(6) ?
C8 C3 C4 C5 . . . . 4.5(7) ?
C1 C3 C4 C5 . . . . -175.7(4) ?
C8 C3 C4 C2 . . . . -174.5(4) ?
C1 C3 C4 C2 . . . . 5.2(7) ?
O3 C2 C4 C5 . . . . 106.2(5) ?
O4 C2 C4 C5 . . . . -74.8(6) ?
O3 C2 C4 C3 . . . . -74.8(6) ?
O4 C2 C4 C3 . . . . 104.2(5) ?
C3 C4 C5 C6 . . . . -5.2(7) ?
C2 C4 C5 C6 . . . . 173.8(4) ?
C3 C4 C5 Br1 . . . . 173.1(3) ?
C2 C4 C5 Br1 . . . . -7.8(6) ?
C4 C5 C6 C7 . . . . 1.9(7) ?
Br1 C5 C6 C7 . . . . -176.4(3) ?
C4 C5 C6 Br2 . . . . -178.0(3) ?
Br1 C5 C6 Br2 . . . . 3.7(5) ?
C5 C6 C7 C8 . . . . 2.2(7) ?
Br2 C6 C7 C8 . . . . -177.9(4) ?
C5 C6 C7 Br3 . . . . -177.7(3) ?
Br2 C6 C7 Br3 . . . . 2.2(6) ?
C6 C7 C8 C3 . . . . -2.9(7) ?
Br3 C7 C8 C3 . . . . 177.0(3) ?
C6 C7 C8 Br4 . . . . 179.5(3) ?
Br3 C7 C8 Br4 . . . . -0.6(6) ?
C4 C3 C8 C7 . . . . -0.5(7) ?
C1 C3 C8 C7 . . . . 179.8(5) ?
C4 C3 C8 Br4 . . . . 177.2(3) ?
C1 C3 C8 Br4 . . . . -2.5(6) ?
C15 C10 C11 C12 . . . . 1.1(8) ?
N1 C10 C11 C12 . . . . -176.0(4) ?
C15 C10 C11 C16 . . . . -178.3(5) ?
N1 C10 C11 C16 . . . . 4.6(8) ?
C10 C11 C12 C13 . . . . -0.4(8) ?
C16 C11 C12 C13 . . . . 179.1(6) ?
C11 C12 C13 C14 . . . . -1.7(10) ?
C12 C13 C14 C15 . . . . 3.0(10) ?
C11 C10 C15 C14 . . . . 0.2(8) ?
N1 C10 C15 C14 . . . . 177.4(5) ?
C13 C14 C15 C10 . . . . -2.2(9) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656599
