#------------------------------------------------------------------------------
#$Date: 2015-09-26 05:23:37 +0300 (Sat, 26 Sep 2015) $
#$Revision: 158358 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241103.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_2241103
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_iupac          'C4 H10 N O +, C6 H Br2 O4 -'
_chemical_formula_moiety         'C4 H10 N O +, C6 H Br2 O4 -'
_chemical_formula_sum            'C10 H11 Br2 N O5'
_chemical_formula_weight         385.01
_chemical_name_common
;
Morpholinium hydrogen bromanilate
;
_chemical_name_systematic
;
Morpholin-4-ium 2,5-dibromo-4-hydroxy-3,6-dioxocyclohexa-1,4-dien-1-olate
;
_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                93.5208(7)
_cell_angle_beta                 112.9139(7)
_cell_angle_gamma                115.9757(7)
_cell_formula_units_Z            2
_cell_length_a                   8.62046(19)
_cell_length_b                   9.2129(2)
_cell_length_c                   9.4257(2)
_cell_measurement_reflns_used    15996
_cell_measurement_temperature    130.0(10)
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      3.00
_cell_volume                     595.05(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
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al., 1994)
;
_diffrn_ambient_temperature      130.0(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  0.0255
_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            18162
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.026
_diffrn_reflns_theta_min         3.005
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.844
_exptl_absorpt_correction_T_max  0.292
_exptl_absorpt_correction_T_min  0.096
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.149
_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         0.495
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0172
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0195P)²+0.3723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0412
_refine_ls_wR_factor_ref         0.0456
_reflns_number_gt                3183
_reflns_number_total             3468
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5788sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        595.05(3)
_cod_database_code               2241103
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 0.75783(2) 0.69637(2) 0.16055(2) 0.01583(4) Uani d 1
Br Br2 -0.01546(2) 0.16774(2) 0.12333(2) 0.01833(4) Uani d 1
O O1 1.18246(16) 0.98222(14) 0.33171(13) 0.0166(2) Uani d 1
O O2 0.62026(15) 0.76781(13) 0.41041(13) 0.0157(2) Uani d 1
H H2 0.548(5) 0.699(4) 0.323(3) 0.023 Uiso d 0.49(3)
O O3 -0.34652(16) 0.22816(14) -0.08651(15) 0.0209(2) Uani d 1
O O4 0.33771(16) 0.50578(13) 0.19213(13) 0.0164(2) Uani d 1
H H4 0.427(5) 0.603(3) 0.226(5) 0.025 Uiso d 0.51(3)
O O5 0.82461(16) 0.26388(15) 0.42254(14) 0.0201(2) Uani d 1
N N1 0.48737(19) 0.29440(17) 0.32853(17) 0.0170(2) Uani d 1
C C1 1.0924(2) 0.98617(17) 0.40452(17) 0.0123(2) Uani d 1
C C2 0.8902(2) 0.86739(17) 0.35299(17) 0.0124(2) Uani d 1
C C3 0.7974(2) 0.87220(17) 0.44093(17) 0.0126(2) Uani d 1
C C4 -0.1856(2) 0.34950(18) -0.04567(18) 0.0146(3) Uani d 1
C C5 -0.0041(2) 0.35821(17) 0.05629(17) 0.0139(3) Uani d 1
C C6 0.1730(2) 0.49677(18) 0.10262(17) 0.0145(3) Uani d 1
C C7 0.6812(2) 0.42756(19) 0.45862(19) 0.0176(3) Uani d 1
H H7A 0.6639 0.4841 0.5393 0.021 Uiso calc 1
H H7B 0.7493 0.5130 0.4132 0.021 Uiso calc 1
C C8 0.8010(2) 0.3481(2) 0.53723(19) 0.0188(3) Uani d 1
H H8A 0.9304 0.4362 0.6229 0.023 Uiso calc 1
H H8B 0.7355 0.2669 0.5872 0.023 Uiso calc 1
C C9 0.6388(2) 0.1307(2) 0.3035(2) 0.0206(3) Uani d 1
H H9A 0.5750 0.0516 0.3557 0.025 Uiso calc 1
H H9B 0.6567 0.0681 0.2277 0.025 Uiso calc 1
C C10 0.5099(2) 0.1976(2) 0.21215(19) 0.0196(3) Uani d 1
H H10A 0.5690 0.2717 0.1543 0.023 Uiso calc 1
H H10B 0.3808 0.1032 0.1324 0.023 Uiso calc 1
H H1A 0.423(3) 0.342(3) 0.277(3) 0.023(5) Uiso d 1
H H1B 0.422(3) 0.223(3) 0.367(3) 0.027(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 . 111(3)
C8 O5 C9 . 109.71(12)
C7 N1 C10 . 110.91(12)
C7 N1 H1A . 109.1(14)
C10 N1 H1A . 108.4(14)
C7 N1 H1B . 111.0(15)
C10 N1 H1B . 107.1(15)
H1A N1 H1B . 110(2)
O1 C1 C2 . 124.43(13)
O1 C1 C3 2_776 117.51(13)
C2 C1 C3 2_776 118.06(12)
C3 C2 C1 . 122.59(13)
C3 C2 Br1 . 120.39(11)
C1 C2 Br1 . 116.98(10)
O2 C3 C2 . 127.82(13)
O2 C3 C1 2_776 112.91(12)
C2 C3 C1 2_776 119.28(12)
O3 C4 C5 . 124.23(14)
O3 C4 C6 2_565 118.64(13)
C5 C4 C6 2_565 117.13(12)
C6 C5 C4 . 122.84(13)
C6 C5 Br2 . 119.19(11)
C4 C5 Br2 . 117.97(10)
O4 C6 C5 . 123.65(14)
O4 C6 C4 2_565 116.29(13)
C5 C6 C4 2_565 120.03(13)
N1 C7 C8 . 109.20(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 . 110.61(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 . 111.23(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 . 108.70(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 . 1.8767(14)
O1 C1 . 1.2295(18)
O2 C3 . 1.2953(17)
O2 H2 . 0.81(3)
O3 C4 . 1.2229(18)
O4 C6 . 1.3002(18)
O4 H4 . 0.82(3)
O5 C8 . 1.4212(19)
O5 C9 . 1.428(2)
N1 C7 . 1.492(2)
N1 C10 . 1.494(2)
N1 H1A . 0.88(3)
N1 H1B . 0.86(3)
C1 C2 . 1.4407(19)
C1 C3 2_776 1.5265(19)
C2 C3 . 1.368(2)
C4 C5 . 1.445(2)
C4 C6 2_565 1.520(2)
C5 C6 . 1.362(2)
C7 C8 . 1.511(2)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 C10 . 1.509(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 . 0.88(3) 2.03(3) 2.886(2) 166(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) 2.27(3) 2.955(2) 137(2) y
O2 H2 O4 . 0.81(3) 1.77(3) 2.5160(16) 152(4) y
O2 H2 O3 2_565 0.81(3) 2.57(3) 3.0613(17) 120(3) y
O4 H4 O2 . 0.82(3) 1.82(4) 2.5160(16) 143(4) y
C7 H7A O4 2_666 0.99 2.53 3.391(2) 145 y
C10 H10B Br2 2_555 0.99 2.90 3.8892(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 . . 177.29(14)
C3 C1 C2 C3 2_776 . -3.3(2)
O1 C1 C2 Br1 . . -0.27(19)
C3 C1 C2 Br1 2_776 . 179.12(9)
C1 C2 C3 O2 . . -176.34(14)
Br1 C2 C3 O2 . . 1.1(2)
C1 C2 C3 C1 . 2_776 3.4(2)
Br1 C2 C3 C1 . 2_776 -179.16(9)
O3 C4 C5 C6 . . -178.49(15)
C6 C4 C5 C6 2_565 . 0.5(2)
O3 C4 C5 Br2 . . 2.7(2)
C6 C4 C5 Br2 2_565 . -178.24(10)
C4 C5 C6 O4 . . -178.83(14)
Br2 C5 C6 O4 . . -0.1(2)
C4 C5 C6 C4 . 2_565 -0.5(2)
Br2 C5 C6 C4 . 2_565 178.22(10)
C10 N1 C7 C8 . . -54.86(16)
C9 O5 C8 C7 . . -62.32(16)
N1 C7 C8 O5 . . 58.54(17)
C8 O5 C9 C10 . . 62.50(17)
C7 N1 C10 C9 . . 54.40(17)
O5 C9 C10 N1 . . -58.02(17)

_cod_database_fobs_code 2241103
