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#$Date: 2022-07-01 11:06:31 +0300 (Fri, 01 Jul 2022) $
#$Revision: 276480 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105609.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105609
loop_
_publ_author_name
'Liu, Yang'
'Zheng, Xiao-Yuan'
'Qin, Liu-Lei'
'Zhu, Chun-Li'
'Liu, Zunqi'
_publ_section_title
;
 Crystal structure of citric acid--acetonitrile (1/1), C8H11NO7
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              255
_journal_page_last               256
_journal_paper_doi               10.1515/ncrs-2018-0290
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C6 H8 O7, C2 H3 N'
_chemical_formula_sum            'C8 H11 N O7'
_chemical_formula_weight         233.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                110.297(2)
_cell_angle_beta                 101.342(3)
_cell_angle_gamma                104.701(2)
_cell_formula_units_Z            2
_cell_length_a                   5.5944(13)
_cell_length_b                   10.402(3)
_cell_length_c                   10.666(3)
_cell_measurement_reflns_used    3926
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.454
_cell_measurement_theta_min      2.228
_cell_volume                     534.6(2)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012) [4]'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012) [4]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [1]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [1]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015) [3]'
_computing_structure_solution    'ShelXS (Sheldrick, 2008) [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4273
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.098
_diffrn_reflns_theta_max         25.098
_diffrn_reflns_theta_min         3.684
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.132(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0343P)²+0.1932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1791
_reflns_number_total             1900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0290_suppl.cif
_cod_data_source_block           exp_1115
_cod_database_code               8105609
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4), O7(H7)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6344(3) -0.17007(13) 0.11160(12) 0.0530(3) Uani 1 1 d . . . . .
C1 C 0.5393(3) -0.18198(14) 0.20076(13) 0.0311(3) Uani 1 1 d . . . . .
N1 N -0.1228(4) 0.55783(19) 0.1767(2) 0.0725(5) Uani 1 1 d . . . . .
O2 O 0.5859(2) -0.26459(13) 0.26514(13) 0.0508(3) Uani 1 1 d . . . . .
H2 H 0.681723 -0.305487 0.233037 0.076 Uiso 1 1 calc GR . . . .
C2 C 0.3577(3) -0.10645(13) 0.25212(14) 0.0315(3) Uani 1 1 d . . . . .
H2A H 0.309794 -0.133701 0.324403 0.038 Uiso 1 1 calc R . . . .
H2B H 0.200046 -0.139718 0.174617 0.038 Uiso 1 1 calc R . . . .
O3 O 0.71657(17) 0.10159(10) 0.41818(9) 0.0316(2) Uani 1 1 d . . . . .
H3 H 0.815639 0.180677 0.429412 0.047 Uiso 1 1 calc GR . . . .
C3 C 0.4801(2) 0.06086(13) 0.31220(13) 0.0249(3) Uani 1 1 d . . . . .
O4 O 0.3138(2) 0.08143(14) 0.10177(11) 0.0477(3) Uani 1 1 d . . . . .
H4 H 0.346675 0.102617 0.038311 0.072 Uiso 1 1 calc GR . . . .
C4 C 0.5335(3) 0.10849(14) 0.19648(13) 0.0299(3) Uani 1 1 d . . . . .
O5 O 0.7469(2) 0.16162(12) 0.19289(12) 0.0485(3) Uani 1 1 d . . . . .
C5 C 0.2902(2) 0.12614(13) 0.37389(13) 0.0274(3) Uani 1 1 d . . . . .
H5A H 0.124444 0.087547 0.300564 0.033 Uiso 1 1 calc R . . . .
H5B H 0.261514 0.095227 0.447330 0.033 Uiso 1 1 calc R . . . .
O6 O 0.5906(2) 0.36407(10) 0.43320(13) 0.0488(3) Uani 1 1 d . . . . .
C6 C 0.3845(2) 0.28966(14) 0.43387(13) 0.0289(3) Uani 1 1 d . . . . .
O7 O 0.22138(18) 0.34600(10) 0.48584(11) 0.0383(3) Uani 1 1 d . . . . .
H7 H 0.278316 0.435099 0.512809 0.057 Uiso 1 1 calc GR . . . .
C7 C -0.0003(3) 0.48598(18) 0.16316(18) 0.0479(4) Uani 1 1 d . . . . .
C8 C 0.1587(3) 0.39477(18) 0.1450(2) 0.0525(4) Uani 1 1 d . . . . .
H8A H 0.211889 0.387703 0.063319 0.079 Uiso 1 1 calc GR . . . .
H8B H 0.059802 0.298853 0.133036 0.079 Uiso 1 1 calc GR . . . .
H8C H 0.309802 0.437297 0.226611 0.079 Uiso 1 1 calc GR . . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 O2 122.41(12) . .
O1 C1 C2 125.32(12) . .
O2 C1 C2 112.28(11) . .
C1 O2 H2 109.5 . .
C1 C2 H2A 109.1 . .
C1 C2 H2B 109.1 . .
C1 C2 C3 112.44(10) . .
H2A C2 H2B 107.8 . .
C3 C2 H2A 109.1 . .
C3 C2 H2B 109.1 . .
C3 O3 H3 109.5 . .
O3 C3 C2 106.41(10) . .
O3 C3 C4 110.11(10) . .
O3 C3 C5 111.21(10) . .
C4 C3 C2 110.42(10) . .
C4 C3 C5 110.67(10) . .
C5 C3 C2 107.92(10) . .
C4 O4 H4 109.5 . .
O4 C4 C3 111.08(11) . .
O5 C4 C3 123.85(12) . .
O5 C4 O4 125.07(12) . .
C3 C5 H5A 108.9 . .
C3 C5 H5B 108.9 . .
H5A C5 H5B 107.7 . .
C6 C5 C3 113.36(10) . .
C6 C5 H5A 108.9 . .
C6 C5 H5B 108.9 . .
O6 C6 C5 123.57(11) . .
O6 C6 O7 122.88(12) . .
O7 C6 C5 113.55(11) . .
C6 O7 H7 109.5 . .
N1 C7 C8 179.27(19) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2043(17) .
C1 O2 1.3155(17) .
C1 C2 1.5083(18) .
N1 C7 1.128(2) .
O2 H2 0.8200 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C3 1.5354(17) .
O3 H3 0.8200 .
O3 C3 1.4152(15) .
C3 C4 1.5337(17) .
C3 C5 1.5340(16) .
O4 H4 0.8200 .
O4 C4 1.3228(17) .
C4 O5 1.1956(17) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C5 C6 1.4959(18) .
O6 C6 1.2174(16) .
C6 O7 1.3148(15) .
O7 H7 0.8200 .
C7 C8 1.448(2) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -58.45(18) . . . .
C1 C2 C3 O3 -55.13(13) . . . .
C1 C2 C3 C4 64.35(14) . . . .
C1 C2 C3 C5 -174.58(10) . . . .
O2 C1 C2 C3 121.38(13) . . . .
C2 C3 C4 O4 67.55(13) . . . .
C2 C3 C4 O5 -111.76(14) . . . .
C2 C3 C5 C6 -178.89(10) . . . .
O3 C3 C4 O4 -175.24(10) . . . .
O3 C3 C4 O5 5.46(17) . . . .
O3 C3 C5 C6 64.75(13) . . . .
C3 C5 C6 O6 0.48(19) . . . .
C3 C5 C6 O7 179.48(10) . . . .
C4 C3 C5 C6 -57.98(14) . . . .
C5 C3 C4 O4 -51.87(14) . . . .
C5 C3 C4 O5 128.82(13) . . . .
