#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/25/2202540.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_2202540
loop_
_publ_author_name
'Chen, Can-Yu'
'Wei, Zan-Bin'
'Zhou, Zhao-Hui'
'Ng, Seik Weng'
_publ_section_title
;
 Morpholinium dihydrogen citrate hydrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1030
_journal_page_last               o1032
_journal_paper_doi               10.1107/S1600536803013874
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C4 H10 N O , C6 H7 O7, H2 O'
_chemical_formula_sum            'C10 H19 N O9'
_chemical_formula_weight         297.26
_chemical_name_systematic
;
 Morpholinium dihydrogen citrate dihydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3774(6)
_cell_length_b                   12.4823(7)
_cell_length_c                   18.4370(10)
_cell_measurement_reflns_used    4726
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      2.4
_cell_volume                     2618.4(2)
_computing_cell_refinement       SAINT
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker AXS area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.028
_diffrn_reflns_av_sigmaI/netI    0.018
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12407
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.15
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.14
_refine_ls_R_factor_all          0.061
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0711P)²+1.4573P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.139
_refine_ls_wR_factor_ref         0.143
_reflns_number_gt                2103
_reflns_number_total             2305
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cm6050.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2618.3(2)
_cod_database_code               2202540
_cod_database_fobs_code          2202540
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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
_atom_site_type_symbol
O1 0.7018(2) 0.4461(2) 0.32430(10) 0.0458(5) Uani d . 1 . . O
O2 0.8506(2) 0.5350(2) 0.27680(10) 0.0370(4) Uani d . 1 . . O
O3 0.7367(2) 0.5590(2) 0.66230(10) 0.0451(5) Uani d D 1 . . O
O4 0.6867(2) 0.4115(2) 0.60370(10) 0.0516(6) Uani d . 1 . . O
O5 0.9106(2) 0.36940(10) 0.48910(10) 0.0424(5) Uani d D 1 . . O
O6 0.7354(2) 0.30100(10) 0.46100(10) 0.0379(5) Uani d . 1 . . O
O7 0.63570(10) 0.49840(10) 0.45610(10) 0.0290(4) Uani d D 1 . . O
O8 0.3538(2) 0.2267(2) 0.24040(10) 0.0481(5) Uani d . 1 . . O
O1w 0.9859(2) 0.1797(2) 0.50150(10) 0.0497(6) Uani d D 1 . . O
N1 0.5971(2) 0.2640(2) 0.25740(10) 0.0371(5) Uani d D 1 . . N
C1 0.7892(2) 0.5054(2) 0.32950(10) 0.0266(5) Uani d . 1 . . C
C2 0.8230(2) 0.5481(2) 0.40410(10) 0.0273(5) Uani d . 1 . . C
C3 0.7591(2) 0.4941(2) 0.46780(10) 0.0244(5) Uani d . 1 . . C
C4 0.7850(2) 0.5521(2) 0.53880(10) 0.0269(5) Uani d . 1 . . C
C5 0.7300(2) 0.4999(2) 0.60410(10) 0.0280(5) Uani d . 1 . . C
C6 0.7983(2) 0.3765(2) 0.47270(10) 0.0258(5) Uani d . 1 . . C
C7 0.5131(2) 0.2781(2) 0.31810(10) 0.0420(6) Uani d . 1 . . C
C8 0.4100(2) 0.2064(2) 0.3076(2) 0.0479(7) Uani d . 1 . . C
C9 0.4334(2) 0.2074(2) 0.1824(2) 0.0464(7) Uani d . 1 . . C
C10 0.5379(2) 0.2798(2) 0.18650(10) 0.0409(6) Uani d . 1 . . C
H3o 0.708(3) 0.526(3) 0.699(2) 0.090(10) Uiso d D 1 . . H
H5o 0.930(3) 0.3030(10) 0.491(2) 0.060(10) Uiso d D 1 . . H
H7o 0.626(3) 0.476(3) 0.4130(10) 0.060(10) Uiso d D 1 . . H
H1w1 1.0590(10) 0.168(3) 0.502(2) 0.060(10) Uiso d D 1 . . H
H1w2 0.950(3) 0.125(2) 0.485(2) 0.080(10) Uiso d D 1 . . H
H1n1 0.628(3) 0.2020(10) 0.260(2) 0.060(10) Uiso d D 1 . . H
H1n2 0.653(2) 0.307(2) 0.265(2) 0.060(10) Uiso d D 1 . . H
H2a 0.8068 0.6243 0.4056 0.033 Uiso calc R 1 . . H
H2b 0.9070 0.5388 0.4107 0.033 Uiso calc R 1 . . H
H4a 0.8694 0.5551 0.5457 0.032 Uiso calc R 1 . . H
H4b 0.7564 0.6251 0.5352 0.032 Uiso calc R 1 . . H
H7a 0.4871 0.3521 0.3200 0.050 Uiso calc R 1 . . H
H7b 0.5515 0.2613 0.3637 0.050 Uiso calc R 1 . . H
H8a 0.4357 0.1323 0.3092 0.058 Uiso calc R 1 . . H
H8b 0.3544 0.2173 0.3468 0.058 Uiso calc R 1 . . H
H9a 0.3933 0.2185 0.1366 0.056 Uiso calc R 1 . . H
H9b 0.4593 0.1334 0.1841 0.056 Uiso calc R 1 . . H
H10a 0.5920 0.2636 0.1474 0.049 Uiso calc R 1 . . H
H10b 0.5132 0.3538 0.1817 0.049 Uiso calc R 1 . . H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C8 O8 C9 109.9(2) yes
O1 C1 O2 124.2(2) yes
O1 C1 C2 118.7(2) yes
O2 C1 C2 117.2(2) yes
C1 C2 C3 114.6(2) yes
O7 C3 C2 109.6(2) yes
O7 C3 C4 107.7(2) yes
C2 C3 C4 110.9(2) yes
O7 C3 C6 109.4(2) yes
C2 C3 C6 109.0(2) yes
C4 C3 C6 110.3(2) yes
C3 C4 C5 113.6(2) yes
O3 C5 O4 123.1(2) yes
O3 C5 C4 112.8(2) yes
O4 C5 C4 124.1(2) yes
O5 C6 O6 124.4(2) yes
O5 C6 C3 111.1(2) yes
O6 C6 C3 124.4(2) yes
N1 C7 C8 109.8(2) yes
O8 C8 C7 111.1(2) yes
O8 C9 C10 111.4(2) yes
N1 C10 C9 109.0(2) yes
C5 O3 H3o 110(3) no
C6 O5 H5o 109(2) no
C3 O7 H7o 105(2) no
H1w1 O1w H1w2 109(4) no
C7 N1 H1n1 109(2) no
C10 N1 H1n1 111(2) no
C7 N1 H1n2 107(2) no
C10 N1 H1n2 113(2) no
H1n1 N1 H1n2 106(3) no
C1 C2 H2a 108.6 no
C3 C2 H2a 108.6 no
C1 C2 H2b 108.6 no
C3 C2 H2b 108.6 no
H2a C2 H2b 107.6 no
C5 C4 H4a 108.8 no
C3 C4 H4a 108.8 no
C5 C4 H4b 108.8 no
C3 C4 H4b 108.8 no
H4a C4 H4b 107.7 no
N1 C7 H7a 109.7 no
C8 C7 H7a 109.7 no
N1 C7 H7b 109.7 no
C8 C7 H7b 109.7 no
H7a C7 H7b 108.2 no
O8 C8 H8a 109.4 no
C7 C8 H8a 109.4 no
O8 C8 H8b 109.4 no
C7 C8 H8b 109.4 no
H8a C8 H8b 108.0 no
O8 C9 H9a 109.3 no
C10 C9 H9a 109.3 no
O8 C9 H9b 109.3 no
C10 C9 H9b 109.3 no
H9a C9 H9b 108.0 no
N1 C10 H10a 109.9 no
C9 C10 H10a 109.9 no
N1 C10 H10b 109.9 no
C9 C10 H10b 109.9 no
H10a C10 H10b 108.3 no
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
O1 C1 . 1.243(3) yes
O2 C1 . 1.253(3) yes
O3 C5 . 1.304(3) yes
O4 C5 . 1.207(3) yes
O5 C6 . 1.316(3) yes
O6 C6 . 1.203(3) yes
O7 C3 . 1.421(3) yes
O8 C8 . 1.418(3) yes
O8 C9 . 1.421(3) yes
N1 C7 . 1.482(3) yes
N1 C10 . 1.484(3) yes
C1 C2 . 1.524(3) yes
C2 C3 . 1.536(3) yes
C3 C4 . 1.525(3) yes
C3 C6 . 1.536(3) yes
C4 C5 . 1.505(3) yes
C7 C8 . 1.489(4) yes
C9 C10 . 1.496(4) yes
O3 H3o . 0.850(10) no
O5 H5o . 0.860(10) no
O7 H7o . 0.850(10) no
O1w H1w1 . 0.850(10) no
O1w H1w2 . 0.850(10) no
N1 H1n1 . 0.850(10) no
N1 H1n2 . 0.850(10) no
C2 H2a . 0.97 no
C2 H2b . 0.97 no
C4 H4a . 0.97 no
C4 H4b . 0.97 no
C7 H7a . 0.97 no
C7 H7b . 0.97 no
C8 H8a . 0.97 no
C8 H8b . 0.97 no
C9 H9a . 0.97 no
C9 H9b . 0.97 no
C10 H10a . 0.97 no
C10 H10b . 0.97 no
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
O3 H3o O2 2_665 0.850(10) 1.760(10) 2.612(2) 176(4) yes
O5 H5o O1w . 0.860(10) 1.680(10) 2.529(3) 172(4) yes
O7 H7o O1 . 0.850(10) 1.89(2) 2.625(2) 144(3) yes
N1 H1n2 O1 . 0.850(10) 2.13(2) 2.847(3) 143(3) yes
N1 H1n1 O2 8_755 0.850(10) 2.12(2) 2.942(3) 162(3) yes
O1w H1w1 O6 4_556 0.850(10) 2.16(2) 2.932(3) 152(3) yes
O1w H1w2 O7 8_755 0.850(10) 1.930(10) 2.782(3) 175(4) yes
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
_geom_torsion_publ_flag
O1 C1 C2 C3 11.9(3) no
O2 C1 C2 C3 -169.8(2) no
C1 C2 C3 O7 -53.2(2) no
C1 C2 C3 C4 -171.9(2) no
C1 C2 C3 C6 66.5(2) no
O7 C3 C4 C5 63.2(2) no
C2 C3 C4 C5 -177.0(2) no
C6 C3 C4 C5 -56.1(3) no
C3 C4 C5 O4 12.2(3) no
C3 C4 C5 O3 -169.6(2) no
O7 C3 C6 O6 6.8(3) no
C4 C3 C6 O6 125.1(2) no
C2 C3 C6 O6 -113.0(2) no
O7 C3 C6 O5 -175.1(2) no
C4 C3 C6 O5 -56.9(2) no
C2 C3 C6 O5 65.1(2) no
C10 N1 C7 C8 54.3(3) no
C9 O8 C8 C7 61.1(3) no
N1 C7 C8 O8 -57.6(3) no
C8 O8 C9 C10 -61.4(3) no
C7 N1 C10 C9 -54.1(3) no
O8 C9 C10 N1 57.7(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131666
