#------------------------------------------------------------------------------
#$Date: 2015-09-26 05:23:37 +0300 (Sat, 26 Sep 2015) $
#$Revision: 158358 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241104.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_2241104
loop_
_publ_author_name
'Gotoh, Kazuma'
'Tahara, Yuki'
'Ishida, Hiroyuki'
_publ_section_title
;
 Crystal structures of morpholinium hydrogen bromanilate at 130, 145 and
 180K
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1226
_journal_page_last               1229
_journal_paper_doi               10.1107/S2056989015017272
_journal_volume                  71
_journal_year                    2015
_chemical_formula_moiety         'C4 H10 N O +, C6 H Br2 O4 -'
_chemical_formula_sum            'C10 H11 Br2 N O5'
_chemical_formula_weight         385.01
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                93.5239(7)
_cell_angle_beta                 112.9190(7)
_cell_angle_gamma                115.9777(7)
_cell_formula_units_Z            2
_cell_length_a                   8.62293(18)
_cell_length_b                   9.21849(19)
_cell_length_c                   9.4354(2)
_cell_measurement_reflns_used    15916
_cell_measurement_temperature    145.0(10)
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      3.00
_cell_volume                     596.13(2)
_computing_cell_refinement
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_data_collection
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_data_reduction
;
RAPID-AUTO (Rigaku, 2006)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2010) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al., 1994)
;
_diffrn_ambient_temperature      145.0(10)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPIDII'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18176
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.035
_diffrn_reflns_theta_min         3.003
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.832
_exptl_absorpt_correction_T_max  0.292
_exptl_absorpt_correction_T_min  0.098
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.441
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3473
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0175
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0200P)²+0.3611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0422
_refine_ls_wR_factor_ref         0.0457
_reflns_number_gt                3181
_reflns_number_total             3473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5788sup1.cif
_cod_data_source_block           2
_cod_original_cell_volume        596.13(3)
_cod_database_code               2241104
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
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
Br Br1 0.75812(2) 0.69658(2) 0.16087(2) 0.01737(4) Uani d 1
Br Br2 -0.01570(2) 0.16791(2) 0.12324(2) 0.02003(5) Uani d 1
O O1 1.18243(15) 0.98258(14) 0.33190(13) 0.0179(2) Uani d 1
O O2 0.62059(15) 0.76777(13) 0.41035(13) 0.0172(2) Uani d 1
H H2 0.547(5) 0.698(4) 0.323(3) 0.026 Uiso d 0.52(3)
O O3 -0.34653(16) 0.22841(14) -0.08661(15) 0.0227(2) Uani d 1
O O4 0.33774(15) 0.50586(13) 0.19208(13) 0.0175(2) Uani d 1
H H4 0.430(5) 0.603(3) 0.231(5) 0.026 Uiso d 0.48(3)
O O5 0.82422(16) 0.26379(15) 0.42261(14) 0.0219(2) Uani d 1
N N1 0.48734(19) 0.29444(17) 0.32852(17) 0.0183(2) Uani d 1
C C1 1.0922(2) 0.98623(17) 0.40454(17) 0.0131(2) Uani d 1
C C2 0.8905(2) 0.86761(17) 0.35306(17) 0.0138(2) Uani d 1
C C3 0.7975(2) 0.87207(17) 0.44087(17) 0.0133(2) Uani d 1
C C4 -0.1856(2) 0.34979(18) -0.04558(17) 0.0156(3) Uani d 1
C C5 -0.0041(2) 0.35843(17) 0.05629(17) 0.0149(3) Uani d 1
C C6 0.1731(2) 0.49685(18) 0.10257(17) 0.0154(3) Uani d 1
C C7 0.6812(2) 0.42735(19) 0.45871(19) 0.0191(3) Uani d 1
H H7A 0.6639 0.4839 0.5393 0.023 Uiso calc 1
H H7B 0.7495 0.5128 0.4135 0.023 Uiso calc 1
C C8 0.8006(2) 0.3479(2) 0.53709(19) 0.0204(3) Uani d 1
H H8A 0.9300 0.4358 0.6228 0.025 Uiso calc 1
H H8B 0.7349 0.2667 0.5868 0.025 Uiso calc 1
C C9 0.6387(2) 0.1307(2) 0.3035(2) 0.0227(3) Uani d 1
H H9A 0.5748 0.0515 0.3556 0.027 Uiso calc 1
H H9B 0.6567 0.0683 0.2278 0.027 Uiso calc 1
C C10 0.5097(2) 0.1977(2) 0.21235(19) 0.0212(3) Uani d 1
H H10A 0.5687 0.2716 0.1545 0.025 Uiso calc 1
H H10B 0.3806 0.1034 0.1327 0.025 Uiso calc 1
H H1A 0.425(3) 0.342(3) 0.278(3) 0.024(5) Uiso d 1
H H1B 0.422(3) 0.224(3) 0.365(3) 0.030(6) 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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, 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
C3 O2 H2 . 118(3)
C6 O4 H4 . 113(3)
C8 O5 C9 . 109.77(12)
C7 N1 C10 . 110.93(12)
C7 N1 H1A . 108.5(14)
C10 N1 H1A . 108.6(14)
C7 N1 H1B . 111.9(16)
C10 N1 H1B . 106.6(15)
H1A N1 H1B . 110(2)
O1 C1 C2 . 124.48(13)
O1 C1 C3 2_776 117.39(12)
C2 C1 C3 2_776 118.13(12)
C3 C2 C1 . 122.62(13)
C3 C2 Br1 . 120.30(11)
C1 C2 Br1 . 117.03(10)
O2 C3 C2 . 127.87(13)
O2 C3 C1 2_776 112.96(12)
C2 C3 C1 2_776 119.17(12)
O3 C4 C5 . 124.23(13)
O3 C4 C6 2_565 118.58(13)
C5 C4 C6 2_565 117.19(12)
C6 C5 C4 . 122.86(13)
C6 C5 Br2 . 119.20(11)
C4 C5 Br2 . 117.92(10)
O4 C6 C5 . 123.68(13)
O4 C6 C4 2_565 116.36(12)
C5 C6 C4 2_565 119.95(13)
N1 C7 C8 . 109.23(12)
N1 C7 H7A . 109.8
C8 C7 H7A . 109.8
N1 C7 H7B . 109.8
C8 C7 H7B . 109.8
H7A C7 H7B . 108.3
O5 C8 C7 . 110.62(13)
O5 C8 H8A . 109.5
C7 C8 H8A . 109.5
O5 C8 H8B . 109.5
C7 C8 H8B . 109.5
H8A C8 H8B . 108.1
O5 C9 C10 . 111.19(13)
O5 C9 H9A . 109.4
C10 C9 H9A . 109.4
O5 C9 H9B . 109.4
C10 C9 H9B . 109.4
H9A C9 H9B . 108.0
N1 C10 C9 . 108.74(13)
N1 C10 H10A . 109.9
C9 C10 H10A . 109.9
N1 C10 H10B . 109.9
C9 C10 H10B . 109.9
H10A C10 H10B . 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C2 . 1.8807(14)
Br2 C5 . 1.8775(14)
O1 C1 . 1.2298(17)
O2 C3 . 1.2937(17)
O2 H2 . 0.82(3)
O3 C4 . 1.2231(18)
O4 C6 . 1.2997(18)
O4 H4 . 0.82(3)
O5 C8 . 1.4201(19)
O5 C9 . 1.428(2)
N1 C7 . 1.492(2)
N1 C10 . 1.493(2)
N1 H1A . 0.86(3)
N1 H1B . 0.85(3)
C1 C2 . 1.4377(19)
C1 C3 2_776 1.5282(19)
C2 C3 . 1.3684(19)
C4 C5 . 1.446(2)
C4 C6 2_565 1.518(2)
C5 C6 . 1.363(2)
C7 C8 . 1.509(2)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 C10 . 1.510(2)
C9 H9A . 0.9900
C9 H9B . 0.9900
C10 H10A . 0.9900
C10 H10B . 0.9900
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
N1 H1A O4 . 0.86(3) 2.04(3) 2.888(2) 166(2) y
N1 H1B O1 1_445 0.85(3) 2.17(3) 2.938(2) 151(2) y
N1 H1B O2 2_666 0.85(3) 2.29(3) 2.959(2) 136(2) y
O2 H2 O4 . 0.82(3) 1.77(3) 2.5174(16) 153(4) y
O2 H2 O3 2_565 0.82(3) 2.58(3) 3.0628(17) 120(3) y
O4 H4 O2 . 0.82(3) 1.79(4) 2.5174(16) 147(4) y
C7 H7A O4 2_666 0.99 2.54 3.394(2) 145 y
C10 H10B Br2 2_555 0.99 2.90 3.8905(17) 175 y
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_4
_geom_torsion
O1 C1 C2 C3 . . 177.25(14)
C3 C1 C2 C3 2_776 . -3.4(2)
O1 C1 C2 Br1 . . -0.21(19)
C3 C1 C2 Br1 2_776 . 179.18(9)
C1 C2 C3 O2 . . -176.36(13)
Br1 C2 C3 O2 . . 1.0(2)
C1 C2 C3 C1 . 2_776 3.4(2)
Br1 C2 C3 C1 . 2_776 -179.22(9)
O3 C4 C5 C6 . . -178.65(15)
C6 C4 C5 C6 2_565 . 0.5(2)
O3 C4 C5 Br2 . . 2.6(2)
C6 C4 C5 Br2 2_565 . -178.23(10)
C4 C5 C6 O4 . . -178.92(13)
Br2 C5 C6 O4 . . -0.2(2)
C4 C5 C6 C4 . 2_565 -0.6(2)
Br2 C5 C6 C4 . 2_565 178.19(10)
C10 N1 C7 C8 . . -54.81(16)
C9 O5 C8 C7 . . -62.38(16)
N1 C7 C8 O5 . . 58.53(17)
C8 O5 C9 C10 . . 62.43(17)
C7 N1 C10 C9 . . 54.27(17)
O5 C9 C10 N1 . . -57.89(18)

_cod_database_fobs_code 2241104
