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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/7/24/67/7246752.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_7246752
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_moiety         'C5 H8 O4, C5 H9 N O2'
_chemical_formula_sum            'C10 H17 N O6'
_chemical_formula_weight         247.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-03-09 deposited with the CCDC.	2023-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8806(18)
_cell_length_b                   9.6156(19)
_cell_length_c                   25.364(6)
_cell_measurement_reflns_used    1660
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      20.4730
_cell_measurement_theta_min      2.5910
_cell_volume                     2409.8(9)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'143 images, ΔΦ 1.2° '
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1096
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7426
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        20.944
_diffrn_reflns_theta_max         20.944
_diffrn_reflns_theta_min         2.613
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21080
_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            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0819
_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)+(0.0470P)²+6.3277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1773
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1015
_reflns_number_total             1270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00226h2.cif
_cod_data_source_block           alex_fl171
_cod_depositor_comments
'Adding full bibliography for 7246740--7246756.cif.'
_cod_original_cell_volume        2409.8(8)
_cod_database_code               7246752
_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+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_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 0.4876(4) 0.3680(4) 0.79463(17) 0.0351(12) Uani 1 1 d . . . . .
H1A H 0.542819 0.435868 0.784335 0.042 Uiso 1 1 calc R U . . .
H1B H 0.527142 0.286884 0.787746 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4597(6) 0.3803(7) 0.8526(2) 0.0504(18) Uani 1 1 d . . . . .
H3A H 0.523983 0.326245 0.872910 0.060 Uiso 1 1 calc R U . . .
H3B H 0.463818 0.476569 0.863918 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3228(8) 0.3248(11) 0.8582(3) 0.090(3) Uani 1 1 d . . . . .
H4A H 0.278248 0.365395 0.888578 0.109 Uiso 1 1 calc R U . . .
H4B H 0.325283 0.224635 0.862530 0.109 Uiso 1 1 calc R U . . .
C5 C 0.2496(7) 0.3626(7) 0.8088(2) 0.058(2) Uani 1 1 d . . . . .
H5A H 0.200735 0.449248 0.813425 0.070 Uiso 1 1 calc R U . . .
H5B H 0.185310 0.290420 0.799434 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3562(6) 0.3780(6) 0.7658(2) 0.0370(16) Uani 1 1 d . . . . .
H00C H 0.348706 0.299558 0.741299 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3458(7) 0.5152(6) 0.7345(2) 0.0354(15) Uani 1 1 d . . . . .
O8 O 0.4448(4) 0.5955(4) 0.73588(17) 0.0532(13) Uani 1 1 d . . . . .
O9 O 0.2363(4) 0.5329(4) 0.71064(15) 0.0417(11) Uani 1 1 d . . . . .
C10 C 0.1660(6) 0.8962(5) 0.5810(2) 0.0360(15) Uani 1 1 d . . . . .
H10 H 0.239044 0.950074 0.597276 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1665(6) 0.7517(6) 0.6047(2) 0.0371(15) Uani 1 1 d . . . . .
O12 O 0.1018(5) 0.6548(4) 0.58725(18) 0.0594(14) Uani 1 1 d . . . . .
O13 O 0.2386(4) 0.7438(4) 0.64786(16) 0.0472(12) Uani 1 1 d . . . . .
H13 H 0.227204 0.667514 0.661632 0.071 Uiso 1 1 calc R U . . .
C14 C 0.0301(6) 0.9649(6) 0.5953(3) 0.0522(18) Uani 1 1 d . . . . .
H14A H 0.029180 1.058977 0.582735 0.078 Uiso 1 1 calc R U . . .
H14B H 0.018944 0.964504 0.632949 0.078 Uiso 1 1 calc R U . . .
H14C H -0.042635 0.913879 0.579318 0.078 Uiso 1 1 calc R U . . .
C15 C 0.1865(6) 0.8974(6) 0.5215(2) 0.0446(17) Uani 1 1 d . . . . .
H15A H 0.120794 0.835864 0.505273 0.054 Uiso 1 1 calc R U . . .
H15B H 0.170269 0.990564 0.508309 0.054 Uiso 1 1 calc R U . . .
C16 C 0.3272(7) 0.8520(7) 0.5056(3) 0.0479(18) Uani 1 1 d . . . . .
O17 O 0.4000(5) 0.7815(5) 0.53158(19) 0.0724(16) Uani 1 1 d . . . . .
O18 O 0.3576(5) 0.8948(6) 0.45687(19) 0.0772(18) Uani 1 1 d . . . . .
H18 H 0.431(9) 0.884(9) 0.4519(15) 0.116 Uiso 1 1 calc R 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
C6 N1 C3 108.4(4) . . ?
C6 N1 H1A 110.0 . . ?
C3 N1 H1A 110.0 . . ?
C6 N1 H1B 110.0 . . ?
C3 N1 H1B 110.0 . . ?
H1A N1 H1B 108.4 . . ?
C4 C3 N1 103.7(5) . . ?
C4 C3 H3A 111.0 . . ?
N1 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
N1 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C3 C4 C5 106.1(6) . . ?
C3 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
C3 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C4 C5 C6 106.8(5) . . ?
C4 C5 H5A 110.4 . . ?
C6 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C6 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
N1 C6 C5 104.1(4) . . ?
N1 C6 C7 111.4(5) . . ?
C5 C6 C7 113.9(5) . . ?
N1 C6 H00C 109.1 . . ?
C5 C6 H00C 109.1 . . ?
C7 C6 H00C 109.1 . . ?
O8 C7 O9 127.5(5) . . ?
O8 C7 C6 117.5(5) . . ?
O9 C7 C6 115.0(5) . . ?
C11 C10 C15 113.6(5) . . ?
C11 C10 C14 107.6(5) . . ?
C15 C10 C14 110.3(5) . . ?
C11 C10 H10 108.4 . . ?
C15 C10 H10 108.4 . . ?
C14 C10 H10 108.4 . . ?
O12 C11 O13 123.2(5) . . ?
O12 C11 C10 124.0(6) . . ?
O13 C11 C10 112.8(5) . . ?
C11 O13 H13 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C10 112.7(5) . . ?
C16 C15 H15A 109.1 . . ?
C10 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C10 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
O17 C16 O18 123.6(6) . . ?
O17 C16 C15 124.9(6) . . ?
O18 C16 C15 111.4(6) . . ?
C16 O18 H18 109.5 . . ?
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 C6 1.493(7) . ?
N1 C3 1.499(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C3 C4 1.461(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.492(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.523(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.544(8) . ?
C6 H00C 0.9800 . ?
C7 O8 1.247(7) . ?
C7 O9 1.250(7) . ?
C10 C11 1.514(8) . ?
C10 C15 1.523(8) . ?
C10 C14 1.540(8) . ?
C10 H10 0.9800 . ?
C11 O12 1.213(7) . ?
C11 O13 1.309(7) . ?
O13 H13 0.8200 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.511(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O17 1.189(7) . ?
C16 O18 1.336(7) . ?
O18 H18 0.74(9) . ?
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
C6 N1 C3 C4 28.8(7) . . . . ?
N1 C3 C4 C5 -33.3(8) . . . . ?
C3 C4 C5 C6 26.1(9) . . . . ?
C3 N1 C6 C5 -12.7(6) . . . . ?
C3 N1 C6 C7 110.5(5) . . . . ?
C4 C5 C6 N1 -7.8(7) . . . . ?
C4 C5 C6 C7 -129.4(6) . . . . ?
N1 C6 C7 O8 1.7(7) . . . . ?
C5 C6 C7 O8 119.2(6) . . . . ?
N1 C6 C7 O9 -177.7(5) . . . . ?
C5 C6 C7 O9 -60.3(7) . . . . ?
C15 C10 C11 O12 -48.0(8) . . . . ?
C14 C10 C11 O12 74.4(7) . . . . ?
C15 C10 C11 O13 135.5(5) . . . . ?
C14 C10 C11 O13 -102.1(6) . . . . ?
C11 C10 C15 C16 -68.1(7) . . . . ?
C14 C10 C15 C16 171.0(5) . . . . ?
C10 C15 C16 O17 23.4(9) . . . . ?
C10 C15 C16 O18 -160.1(6) . . . . ?
