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#$Date: 2023-06-05 07:23:17 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284258 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246740.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_7246740
loop_
_publ_author_name
'Zhou, Fuli'
'Body, Carole'
'Robeyns, Koen'
'Leyssens, Tom'
'Shemchuk, Oleksii'
_publ_section_title
;
 On the pairwise cocrystallization of racemic compounds
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3060
_journal_page_last               3065
_journal_paper_doi               10.1039/D3CE00226H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C5 H11 N O3'
_chemical_formula_weight         133.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'dual space'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-17 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.68(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.468(4)
_cell_length_b                   5.3181(19)
_cell_length_c                   12.162(5)
_cell_measurement_reflns_used    758
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.4680
_cell_measurement_theta_min      3.4380
_cell_volume                     655.0(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'40 images, ΔΦ 5.0° '
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3271
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        22.439
_diffrn_reflns_theta_max         22.439
_diffrn_reflns_theta_min         3.463
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       rod
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         828
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0513
_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)+(0.0587P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                554
_reflns_number_total             828
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00226h2.cif
_cod_data_source_block           alex_DL-Pro_H2O
_cod_depositor_comments
'Adding full bibliography for 7246740--7246756.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C5 H9 N O2, H2 O'
_cod_database_code               7246740
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N1 N 0.6127(3) 0.7798(5) 0.4411(2) 0.0294(8) Uani 1 1 d D U . . .
H1A H 0.547517 0.687569 0.454830 0.035 Uiso 0.877(12) 1 calc R U P A 1
H1B H 0.579929 0.928649 0.414597 0.035 Uiso 0.877(12) 1 calc R U P A 1
H1C H 0.537581 0.707661 0.445834 0.035 Uiso 0.123(12) 1 calc R U P A 2
H1D H 0.598358 0.942207 0.424920 0.035 Uiso 0.123(12) 1 calc R U P A 2
C2 C 0.7195(5) 0.8142(15) 0.5486(4) 0.043(2) Uani 0.877(12) 1 d D U P A 1
H2A H 0.728871 0.666005 0.596487 0.051 Uiso 0.877(12) 1 calc R U P A 1
H2B H 0.702284 0.959047 0.591174 0.051 Uiso 0.877(12) 1 calc R U P A 1
C3 C 0.8398(5) 0.8544(13) 0.5042(4) 0.0435(17) Uani 0.877(12) 1 d D U P A 1
H3A H 0.919994 0.816802 0.562099 0.052 Uiso 0.877(12) 1 calc R U P A 1
H3B H 0.844039 1.026332 0.478682 0.052 Uiso 0.877(12) 1 calc R U P A 1
C4 C 0.8207(5) 0.6708(13) 0.4050(5) 0.0417(19) Uani 0.877(12) 1 d D U P A 1
H4A H 0.857818 0.507713 0.431081 0.050 Uiso 0.877(12) 1 calc R U P A 1
H4B H 0.863127 0.733212 0.348157 0.050 Uiso 0.877(12) 1 calc R U P A 1
C2B C 0.720(2) 0.743(14) 0.5481(16) 0.045(8) Uani 0.123(12) 1 d D U P A 2
H2C H 0.698112 0.604030 0.591798 0.054 Uiso 0.123(12) 1 calc R U P A 2
H2D H 0.730291 0.893740 0.594588 0.054 Uiso 0.123(12) 1 calc R U P A 2
C3B C 0.844(3) 0.688(10) 0.512(3) 0.046(7) Uani 0.123(12) 1 d D U P A 2
H3C H 0.867985 0.512088 0.523981 0.056 Uiso 0.123(12) 1 calc R U P A 2
H3D H 0.916828 0.789845 0.555264 0.056 Uiso 0.123(12) 1 calc R U P A 2
C4B C 0.812(2) 0.755(9) 0.386(2) 0.034(8) Uani 0.123(12) 1 d D U P A 2
H4C H 0.868608 0.668317 0.346827 0.040 Uiso 0.123(12) 1 calc R U P A 2
H4D H 0.814848 0.934668 0.373803 0.040 Uiso 0.123(12) 1 calc R U P A 2
C5 C 0.6701(4) 0.6511(6) 0.3555(3) 0.0295(10) Uani 1 1 d D U . . .
H5 H 0.643807 0.738480 0.282247 0.035 Uiso 0.877(12) 1 calc R U P A 1
H5B H 0.627283 0.730692 0.282790 0.035 Uiso 0.123(12) 1 calc R U P A 2
C6 C 0.6260(4) 0.3744(7) 0.3416(3) 0.0311(10) Uani 1 1 d . . . . .
O7 O 0.5606(3) 0.2898(4) 0.4082(2) 0.0374(8) Uani 1 1 d . . . . .
O8 O 0.6619(3) 0.2503(4) 0.2666(2) 0.0434(9) Uani 1 1 d . . . . .
O11 O 0.9203(4) 0.1881(6) 0.2285(3) 0.0634(10) Uani 1 1 d G . . . .
H11A H 0.953602 0.328506 0.232777 0.095 Uiso 1 1 d G U . . .
H11B H 0.845420 0.212686 0.235536 0.095 Uiso 1 1 d G U . . .
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
_geom_angle_publ_flag
C5 N1 C2B 101.7(15) . . ?
C5 N1 C2 108.7(3) . . ?
C5 N1 H1A 109.9 . . ?
C2 N1 H1A 109.9 . . ?
C5 N1 H1B 109.9 . . ?
C2 N1 H1B 109.9 . . ?
H1A N1 H1B 108.3 . . ?
C5 N1 H1C 111.4 . . ?
C2B N1 H1C 111.4 . . ?
C5 N1 H1D 111.4 . . ?
C2B N1 H1D 111.4 . . ?
H1C N1 H1D 109.3 . . ?
N1 C2 C3 102.2(3) . . ?
N1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C2 C3 C4 103.8(4) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 105.6(4) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
N1 C2B C3B 106.6(15) . . ?
N1 C2B H2C 110.4 . . ?
C3B C2B H2C 110.4 . . ?
N1 C2B H2D 110.4 . . ?
C3B C2B H2D 110.4 . . ?
H2C C2B H2D 108.6 . . ?
C2B C3B C4B 104.9(14) . . ?
C2B C3B H3C 110.8 . . ?
C4B C3B H3C 110.8 . . ?
C2B C3B H3D 110.8 . . ?
C4B C3B H3D 110.8 . . ?
H3C C3B H3D 108.8 . . ?
C3B C4B C5 97(2) . . ?
C3B C4B H4C 112.4 . . ?
C5 C4B H4C 112.4 . . ?
C3B C4B H4D 112.4 . . ?
C5 C4B H4D 112.4 . . ?
H4C C4B H4D 110.0 . . ?
N1 C5 C6 110.6(3) . . ?
N1 C5 C4B 101.4(16) . . ?
C6 C5 C4B 127.9(19) . . ?
N1 C5 C4 104.4(3) . . ?
C6 C5 C4 110.9(4) . . ?
N1 C5 H5 110.3 . . ?
C6 C5 H5 110.3 . . ?
C4 C5 H5 110.3 . . ?
N1 C5 H5B 105.0 . . ?
C6 C5 H5B 105.0 . . ?
C4B C5 H5B 105.0 . . ?
O8 C6 O7 125.8(3) . . ?
O8 C6 C5 116.4(3) . . ?
O7 C6 C5 117.7(3) . . ?
H11A O11 H11B 104.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.494(4) . ?
N1 C2B 1.499(11) . ?
N1 C2 1.500(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
C2 C3 1.507(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.525(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.542(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2B C3B 1.505(12) . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C3B C4B 1.524(12) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4B C5 1.539(11) . ?
C4B H4C 0.9700 . ?
C4B H4D 0.9700 . ?
C5 C6 1.539(5) . ?
C5 H5 0.9800 . ?
C5 H5B 0.9800 . ?
C6 O8 1.258(4) . ?
C6 O7 1.268(4) . ?
O11 H11A 0.8200 . ?
O11 H11B 0.8200 . ?
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
_geom_torsion_publ_flag
C5 N1 C2 C3 33.4(5) . . . . ?
N1 C2 C3 C4 -39.1(6) . . . . ?
C2 C3 C4 C5 31.4(7) . . . . ?
C5 N1 C2B C3B 20(4) . . . . ?
N1 C2B C3B C4B 13(5) . . . . ?
C2B C3B C4B C5 -39(5) . . . . ?
C2B N1 C5 C6 92(3) . . . . ?
C2 N1 C5 C6 105.4(4) . . . . ?
C2B N1 C5 C4B -46(3) . . . . ?
C2 N1 C5 C4 -13.9(5) . . . . ?
C3B C4B C5 N1 53(3) . . . . ?
C3B C4B C5 C6 -75(3) . . . . ?
C3 C4 C5 N1 -10.9(7) . . . . ?
C3 C4 C5 C6 -130.0(5) . . . . ?
N1 C5 C6 O8 175.9(3) . . . . ?
C4B C5 C6 O8 -60.0(15) . . . . ?
C4 C5 C6 O8 -68.8(5) . . . . ?
N1 C5 C6 O7 -6.0(5) . . . . ?
C4B C5 C6 O7 118.1(15) . . . . ?
C4 C5 C6 O7 109.3(4) . . . . ?
