#------------------------------------------------------------------------------
#$Date: 2015-09-26 05:23:37 +0300 (Sat, 26 Sep 2015) $
#$Revision: 158358 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241105.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_2241105
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                93.5321(7)
_cell_angle_beta                 112.9738(7)
_cell_angle_gamma                115.9508(7)
_cell_formula_units_Z            2
_cell_length_a                   8.62824(17)
_cell_length_b                   9.23087(18)
_cell_length_c                   9.46007(19)
_cell_measurement_reflns_used    15838
_cell_measurement_temperature    180.0(10)
_cell_measurement_theta_max      30.12
_cell_measurement_theta_min      3.00
_cell_volume                     598.67(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      180.0(10)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0260
_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            18199
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.803
_exptl_absorpt_correction_T_max  0.294
_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    2.136
_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         0.585
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0185
_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)+(0.0216P)²+0.3489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0444
_refine_ls_wR_factor_ref         0.0476
_reflns_number_gt                3188
_reflns_number_total             3487
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5788sup1.cif
_cod_data_source_block           3
_cod_original_cell_volume        598.67(3)
_cod_database_code               2241105
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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 0.75874(2) 0.69709(2) 0.16160(2) 0.02126(5) Uani d 1
Br Br2 -0.01629(2) 0.16834(2) 0.12298(2) 0.02440(5) Uani d 1
O O1 1.18225(16) 0.98340(14) 0.33207(13) 0.0212(2) Uani d 1
O O2 0.62107(15) 0.76749(14) 0.41043(13) 0.0205(2) Uani d 1
H H2 0.550(6) 0.702(5) 0.321(3) 0.031 Uiso d 0.50(3)
O O3 -0.34638(16) 0.22923(14) -0.08655(16) 0.0275(2) Uani d 1
O O4 0.33726(16) 0.50565(14) 0.19202(13) 0.0209(2) Uani d 1
H H4 0.426(5) 0.604(3) 0.231(5) 0.031 Uiso d 0.50(3)
O O5 0.82325(17) 0.26349(16) 0.42251(15) 0.0266(2) Uani d 1
N N1 0.48719(19) 0.29464(18) 0.32897(17) 0.0216(3) Uani d 1
C C1 1.0921(2) 0.98669(17) 0.40464(17) 0.0155(2) Uani d 1
C C2 0.8904(2) 0.86771(17) 0.35338(17) 0.0158(2) Uani d 1
C C3 0.7977(2) 0.87190(17) 0.44099(17) 0.0157(2) Uani d 1
C C4 -0.1853(2) 0.35010(18) -0.04556(18) 0.0185(3) Uani d 1
C C5 -0.0045(2) 0.35849(17) 0.05607(17) 0.0175(3) Uani d 1
C C6 0.1728(2) 0.49667(18) 0.10245(17) 0.0180(3) Uani d 1
C C7 0.6809(2) 0.42714(19) 0.4585(2) 0.0227(3) Uani d 1
H H7A 0.6639 0.4840 0.5389 0.027 Uiso calc 1
H H7B 0.7492 0.5122 0.4133 0.027 Uiso calc 1
C C8 0.7997(2) 0.3474(2) 0.53683(19) 0.0250(3) Uani d 1
H H8A 0.9291 0.4350 0.6226 0.030 Uiso calc 1
H H8B 0.7337 0.2662 0.5861 0.030 Uiso calc 1
C C9 0.6381(2) 0.1310(2) 0.3036(2) 0.0272(3) Uani d 1
H H9A 0.5742 0.0517 0.3552 0.033 Uiso calc 1
H H9B 0.6562 0.0690 0.2279 0.033 Uiso calc 1
C C10 0.5094(2) 0.1980(2) 0.21303(19) 0.0252(3) Uani d 1
H H10A 0.5683 0.2719 0.1554 0.030 Uiso calc 1
H H10B 0.3803 0.1040 0.1335 0.030 Uiso calc 1
H H1A 0.424(3) 0.344(3) 0.277(2) 0.025(5) Uiso d 1
H H1B 0.422(3) 0.223(3) 0.367(3) 0.026(5) 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'
Br Br -0.2901 2.4595 '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'
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 . 117(3)
C6 O4 H4 . 111(3)
C8 O5 C9 . 109.83(12)
C7 N1 C10 . 110.85(12)
C7 N1 H1A . 108.4(14)
C10 N1 H1A . 108.2(14)
C7 N1 H1B . 111.2(14)
C10 N1 H1B . 106.4(14)
H1A N1 H1B . 112(2)
O1 C1 C2 . 124.51(13)
O1 C1 C3 2_776 117.41(12)
C2 C1 C3 2_776 118.08(12)
C3 C2 C1 . 122.63(13)
C3 C2 Br1 . 120.43(11)
C1 C2 Br1 . 116.90(10)
O2 C3 C2 . 127.81(13)
O2 C3 C1 2_776 112.98(12)
C2 C3 C1 2_776 119.21(12)
O3 C4 C5 . 124.27(14)
O3 C4 C6 2_565 118.48(14)
C5 C4 C6 2_565 117.24(12)
C6 C5 C4 . 122.82(13)
C6 C5 Br2 . 119.20(11)
C4 C5 Br2 . 117.98(10)
O4 C6 C5 . 123.69(14)
O4 C6 C4 2_565 116.35(13)
C5 C6 C4 2_565 119.94(13)
N1 C7 C8 . 109.14(13)
N1 C7 H7A . 109.9
C8 C7 H7A . 109.9
N1 C7 H7B . 109.9
C8 C7 H7B . 109.9
H7A C7 H7B . 108.3
O5 C8 C7 . 110.51(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 . 111.18(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 . 108.84(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 . 1.8803(14)
Br2 C5 . 1.8769(14)
O1 C1 . 1.2299(17)
O2 C3 . 1.2931(17)
O2 H2 . 0.82(3)
O3 C4 . 1.2229(18)
O4 C6 . 1.2997(18)
O4 H4 . 0.82(3)
O5 C8 . 1.420(2)
O5 C9 . 1.425(2)
N1 C7 . 1.490(2)
N1 C10 . 1.493(2)
N1 H1A . 0.89(3)
N1 H1B . 0.86(3)
C1 C2 . 1.4394(19)
C1 C3 2_776 1.5283(19)
C2 C3 . 1.367(2)
C4 C5 . 1.442(2)
C4 C6 2_565 1.519(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 . 1.508(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 . 0.89(3) 2.02(3) 2.890(2) 167(2) y
N1 H1B O1 1_445 0.86(3) 2.16(3) 2.938(2) 150(2) y
N1 H1B O2 2_666 0.86(3) 2.28(3) 2.964(2) 136(2) y
O2 H2 O4 . 0.82(3) 1.79(4) 2.5224(16) 148(5) y
O2 H2 O3 2_565 0.82(3) 2.55(4) 3.0678(18) 122(4) y
O4 H4 O2 . 0.82(3) 1.80(4) 2.5224(16) 147(4) y
C7 H7A O4 2_666 0.99 2.55 3.402(2) 145 y
C10 H10B Br2 2_555 0.99 2.91 3.8946(17) 174 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 . . 177.30(14)
C3 C1 C2 C3 2_776 . -3.3(2)
O1 C1 C2 Br1 . . -0.20(19)
C3 C1 C2 Br1 2_776 . 179.24(9)
C1 C2 C3 O2 . . -176.48(14)
Br1 C2 C3 O2 . . 0.9(2)
C1 C2 C3 C1 . 2_776 3.3(2)
Br1 C2 C3 C1 . 2_776 -179.29(9)
O3 C4 C5 C6 . . -178.51(15)
C6 C4 C5 C6 2_565 . 0.5(2)
O3 C4 C5 Br2 . . 2.7(2)
C6 C4 C5 Br2 2_565 . -178.27(10)
C4 C5 C6 O4 . . -178.95(14)
Br2 C5 C6 O4 . . -0.2(2)
C4 C5 C6 C4 . 2_565 -0.5(2)
Br2 C5 C6 C4 . 2_565 178.25(10)
C10 N1 C7 C8 . . -55.03(17)
C9 O5 C8 C7 . . -62.46(17)
N1 C7 C8 O5 . . 58.77(17)
C8 O5 C9 C10 . . 62.31(18)
C7 N1 C10 C9 . . 54.35(17)
O5 C9 C10 N1 . . -57.76(19)

_cod_database_fobs_code 2241105
