#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/19/2231991.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_2231991
loop_
_publ_author_name
'Padayachy, Kamentheren'
'Mgcima, Zolani'
'Fernandes, Manuel A.'
'Marques, Helder M.'
'de Sousa, Alvaro S.'
_publ_section_title
;
 Hydrogen-bond interactions in morpholinium bromide
;
_journal_coeditor_code           LR2027
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2594
_journal_paper_doi               10.1107/S1600536811035598
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C4 H10 N O +, Br -'
_chemical_formula_moiety         'C4 H10 N O +, Br -'
_chemical_formula_sum            'C4 H10 Br N O'
_chemical_formula_weight         168.04
_chemical_name_common            'Morpholine Hydrobromide'
_chemical_name_systematic
;
morpholinium bromide
;
_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                 100.312(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1247(2)
_cell_length_b                   10.3063(3)
_cell_length_c                   10.1141(3)
_cell_measurement_reflns_used    5677
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.85
_cell_volume                     628.12(3)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2005)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON, (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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  0.2101
_diffrn_reflns_av_sigmaI/netI    0.0809
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11662
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    6.435
_exptl_absorpt_correction_T_max  0.5951
_exptl_absorpt_correction_T_min  0.1828
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(face indexed absorption corrections carried out with XPREP; Sheldrick,
2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.069
_refine_diff_density_min         -1.379
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                1314
_reflns_number_total             1516
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL 8m_alv14_0s in P2(1)/c
CELL  0.71073   6.1247  10.3063  10.1141   90.000  100.312   90.000
ZERR     4.00   0.0002   0.0003   0.0003    0.000    0.002    0.000
LATT   1
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O    BR
UNIT  16   40   4    4    4
MERG   2
OMIT    -2.00  56.00
FMAP   2
PLAN    5
SIZE     0.09   0.20   0.40
ACTA
HTAB    2.00000
BOND   $H
CONF
L.S.   4
TEMP  -100.00
WGHT    0.051800
FVAR       0.15627
BR1   5    0.749040    0.119712    0.072841    11.00000    0.01535    0.03323 =
         0.02418   -0.00764    0.00118   -0.00109
O1    4    0.248868    0.109405    0.469409    11.00000    0.03584    0.03006 =
         0.01266    0.00039    0.00308    0.00095
N1    3    0.281253    0.083037    0.193657    11.00000    0.01594    0.02893 =
         0.01471   -0.00132    0.00212    0.00179
AFIX  23
H1A   2    0.373928    0.075761    0.131797    11.00000   -1.20000
H1B   2    0.137181    0.080825    0.148018    11.00000   -1.20000
AFIX   0
C1    1    0.322771    0.208233    0.265738    11.00000    0.02595    0.02204 =
         0.02377    0.00095    0.00145   -0.00547
AFIX  23
H1C   2    0.278829    0.280741    0.202352    11.00000   -1.20000
H1D   2    0.483079    0.216981    0.302603    11.00000   -1.20000
AFIX   0
C4    1    0.319879   -0.028043    0.289286    11.00000    0.02741    0.02382 =
         0.02133   -0.00039    0.00137    0.00420
AFIX  23
H4A   2    0.480105   -0.034665    0.327225    11.00000   -1.20000
H4B   2    0.273159   -0.109806    0.241040    11.00000   -1.20000
AFIX   0
C2    1    0.192583    0.214866    0.378083    11.00000    0.03365    0.02463 =
         0.02251   -0.00470    0.00176    0.00504
AFIX  23
H2A   2    0.224116    0.297984    0.426830    11.00000   -1.20000
H2B   2    0.031912    0.211907    0.340447    11.00000   -1.20000
AFIX   0
C3    1    0.191527   -0.009351    0.400387    11.00000    0.03399    0.02452 =
         0.02304    0.00373    0.00526   -0.00335
AFIX  23
H3A   2    0.030762   -0.009543    0.362780    11.00000   -1.20000
H3B   2    0.222131   -0.082413    0.464579    11.00000   -1.20000
HKLF    4
REM  8m_alv14_0s in P2(1)/c
REM R1 =  0.0388 for   1314 Fo > 4sig(Fo)  and  0.0430 for all   1516 data
REM     64 parameters refined using      0 restraints
END
WGHT      0.0519      0.0000
REM Highest difference peak  1.069,  deepest hole -1.379,  1-sigma level  0.164
Q1    1   0.7549  0.0554  0.1072  11.00000  0.05    1.07
Q2    1   0.6781  0.0400  0.0468  11.00000  0.05    0.88
Q3    1   0.6597  0.2078  0.0448  11.00000  0.05    0.70
Q4    1   0.8240  0.2010  0.0938  11.00000  0.05    0.62
Q5    1   0.7415  0.1860  0.1138  11.00000  0.05    0.56
;
_cod_data_source_file            lr2027.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231991
_cod_database_fobs_code          2231991
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, 1/2-y, 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_symmetry_multiplicity
Br Br1 0.74904(4) 0.11971(3) 0.07284(3) 0.02454(16) Uani d . 1 1
O O1 0.2489(4) 0.10940(17) 0.4694(3) 0.0263(5) Uani d . 1 1
N N1 0.2813(4) 0.0830(2) 0.1937(2) 0.0199(5) Uani d . 1 1
H H1A 0.3739 0.0758 0.1318 0.024 Uiso calc R 1 1
H H1B 0.1372 0.0808 0.1480 0.024 Uiso calc R 1 1
C C1 0.3228(5) 0.2082(3) 0.2657(3) 0.0243(6) Uani d . 1 1
H H1C 0.2788 0.2807 0.2024 0.029 Uiso calc R 1 1
H H1D 0.4831 0.2170 0.3026 0.029 Uiso calc R 1 1
C C4 0.3199(5) -0.0280(3) 0.2893(3) 0.0246(6) Uani d . 1 1
H H4A 0.4801 -0.0347 0.3272 0.029 Uiso calc R 1 1
H H4B 0.2732 -0.1098 0.2410 0.029 Uiso calc R 1 1
C C2 0.1926(5) 0.2149(3) 0.3781(3) 0.0273(6) Uani d . 1 1
H H2A 0.2241 0.2980 0.4268 0.033 Uiso calc R 1 1
H H2B 0.0319 0.2119 0.3404 0.033 Uiso calc R 1 1
C C3 0.1915(5) -0.0094(3) 0.4004(3) 0.0272(6) Uani d . 1 1
H H3A 0.0308 -0.0095 0.3628 0.033 Uiso calc R 1 1
H H3B 0.2221 -0.0824 0.4646 0.033 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0153(2) 0.0332(2) 0.0242(2) -0.00109(9) 0.00118(14) -0.00764(10)
O1 0.0358(13) 0.0301(11) 0.0127(10) 0.0010(8) 0.0031(9) 0.0004(7)
N1 0.0159(11) 0.0289(11) 0.0147(11) 0.0018(8) 0.0021(9) -0.0013(8)
C1 0.0259(14) 0.0220(13) 0.0238(14) -0.0055(10) 0.0014(11) 0.0010(10)
C4 0.0274(14) 0.0238(14) 0.0213(14) 0.0042(10) 0.0014(11) -0.0004(10)
C2 0.0336(16) 0.0246(14) 0.0225(15) 0.0050(11) 0.0018(13) -0.0047(11)
C3 0.0340(15) 0.0245(14) 0.0230(14) -0.0033(11) 0.0053(12) 0.0037(11)
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
C3 O1 C2 109.1(2)
C1 N1 C4 110.9(2)
C1 N1 H1A 109.5
C4 N1 H1A 109.5
C1 N1 H1B 109.5
C4 N1 H1B 109.5
H1A N1 H1B 108.1
N1 C1 C2 110.1(2)
N1 C1 H1C 109.6
C2 C1 H1C 109.6
N1 C1 H1D 109.6
C2 C1 H1D 109.6
H1C C1 H1D 108.1
N1 C4 C3 110.2(2)
N1 C4 H4A 109.6
C3 C4 H4A 109.6
N1 C4 H4B 109.6
C3 C4 H4B 109.6
H4A C4 H4B 108.1
O1 C2 C1 110.8(2)
O1 C2 H2A 109.5
C1 C2 H2A 109.5
O1 C2 H2B 109.5
C1 C2 H2B 109.5
H2A C2 H2B 108.1
O1 C3 C4 111.3(2)
O1 C3 H3A 109.4
C4 C3 H3A 109.4
O1 C3 H3B 109.4
C4 C3 H3B 109.4
H3A C3 H3B 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.422(3)
O1 C2 1.428(3)
N1 C1 1.481(3)
N1 C4 1.490(3)
N1 H1A 0.9200
N1 H1B 0.9200
C1 C2 1.502(4)
C1 H1C 0.9900
C1 H1D 0.9900
C4 C3 1.495(4)
C4 H4A 0.9900
C4 H4B 0.9900
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9900
C3 H3B 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 Br1 . 0.92 2.52 3.331(2) 148 y
N1 H1A Br1 3_655 0.92 2.89 3.389(2) 115 y
N1 H1B Br1 1_455 0.92 2.40 3.292(2) 164 y
C4 H4A O1 3_656 0.99 2.52 3.366(4) 143 y
C1 H1C O1 4_554 0.99 2.59 3.498(4) 152 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
C4 N1 C1 C2 -52.4(3)
C1 N1 C4 C3 52.1(3)
C3 O1 C2 C1 -62.4(3)
N1 C1 C2 O1 57.9(3)
C2 O1 C3 C4 62.3(3)
N1 C4 C3 O1 -57.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10658329
