#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:23:17 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284258 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246754.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_7246754
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         'C8 H8 O3, C5 H9 N O2'
_chemical_formula_sum            'C13 H17 N O5'
_chemical_formula_weight         267.27
_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     'dual space'
_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                103.74(2)
_cell_angle_beta                 99.820(18)
_cell_angle_gamma                105.63(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0962(13)
_cell_length_b                   8.306(2)
_cell_length_c                   12.120(3)
_cell_measurement_reflns_used    1521
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8760
_cell_measurement_theta_min      2.6540
_cell_volume                     646.9(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'60 images, ΔΦ 3.0° '
'60 images, ΔΦ 3.0° (2nd orientation)'
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8814
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.212
_diffrn_reflns_theta_min         2.668
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79878
_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    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0590
_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)+(0.0841P)²+0.3023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2040
_reflns_number_total             2534
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00226h2.cif
_cod_data_source_block           Alex_RS-DL
_cod_depositor_comments
'Adding full bibliography for 7246740--7246756.cif.'
_cod_database_code               7246754
_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, -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 0.4929(3) -0.0376(2) 0.64126(16) 0.0380(4) Uani 1 1 d . . . . .
H1A H 0.457208 -0.136378 0.582607 0.046 Uiso 1 1 calc R U . . .
H1AB H 0.547509 0.051534 0.615536 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6427(4) -0.0434(4) 0.7425(2) 0.0497(6) Uani 1 1 d . . . . .
H2A H 0.690304 -0.142451 0.719619 0.060 Uiso 1 1 calc R U . . .
H2AB H 0.757856 0.063295 0.770705 0.060 Uiso 1 1 calc R U . . .
C3 C 0.5305(5) -0.0616(4) 0.8348(3) 0.0647(8) Uani 1 1 d . . . . .
H3A H 0.621030 -0.007972 0.912639 0.078 Uiso 1 1 calc R U . . .
H3AB H 0.462068 -0.183858 0.825495 0.078 Uiso 1 1 calc R U . . .
C4 C 0.3798(5) 0.0340(4) 0.8145(2) 0.0603(7) Uani 1 1 d . . . . .
H4A H 0.267265 -0.004061 0.848168 0.072 Uiso 1 1 calc R U . . .
H4AB H 0.443401 0.159702 0.848301 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3105(3) -0.0155(3) 0.6824(2) 0.0411(5) Uani 1 1 d . . . . .
H5 H 0.204219 -0.129948 0.654836 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2287(3) 0.1125(3) 0.6334(2) 0.0421(5) Uani 1 1 d . . . . .
O7 O 0.2985(3) 0.1568(2) 0.55247(16) 0.0498(5) Uani 1 1 d . . . . .
O8 O 0.1017(3) 0.1593(3) 0.67848(19) 0.0661(6) Uani 1 1 d . . . . .
C11 C 0.1461(11) 0.484(3) 0.2460(9) 0.0404(13) Uani 0.733(13) 1 d D U P A 1
C12 C 0.3307(10) 0.4932(19) 0.2203(7) 0.0487(10) Uani 0.733(13) 1 d D U P A 1
H12 H 0.449130 0.548528 0.279773 0.058 Uiso 0.733(13) 1 calc R U P A 1
C13 C 0.3412(11) 0.4208(12) 0.1068(6) 0.0602(15) Uani 0.733(13) 1 d D U P A 1
H13 H 0.466410 0.426537 0.091330 0.072 Uiso 0.733(13) 1 calc R U P A 1
C14 C 0.1716(13) 0.3422(11) 0.0187(5) 0.0793(18) Uani 0.733(13) 1 d D U P A 1
H14 H 0.179251 0.291169 -0.056791 0.095 Uiso 0.733(13) 1 calc R U P A 1
C15 C -0.0117(11) 0.3384(10) 0.0415(5) 0.0910(19) Uani 0.733(13) 1 d D U P A 1
H15 H -0.128604 0.287626 -0.019332 0.109 Uiso 0.733(13) 1 calc R U P A 1
C16 C -0.0248(9) 0.4099(9) 0.1551(5) 0.0667(14) Uani 0.733(13) 1 d D U P A 1
H16 H -0.150066 0.407263 0.169386 0.080 Uiso 0.733(13) 1 calc R U P A 1
C11B C 0.171(3) 0.485(9) 0.251(3) 0.0404(13) Uani 0.267(13) 1 d D . P A 2
C12B C 0.368(3) 0.514(6) 0.2400(19) 0.0487(10) Uani 0.267(13) 1 d D . P A 2
H12B H 0.475486 0.575321 0.305410 0.058 Uiso 0.267(13) 1 calc R U P A 2
C13B C 0.404(2) 0.452(4) 0.132(2) 0.0602(15) Uani 0.267(13) 1 d D . P A 2
H13B H 0.535740 0.481104 0.123006 0.072 Uiso 0.267(13) 1 calc R U P A 2
C14B C 0.249(3) 0.349(3) 0.0387(16) 0.0793(18) Uani 0.267(13) 1 d D . P A 2
H14B H 0.273368 0.314287 -0.034895 0.095 Uiso 0.267(13) 1 calc R U P A 2
C15B C 0.056(3) 0.295(3) 0.0519(14) 0.0910(19) Uani 0.267(13) 1 d D . P A 2
H15B H -0.048141 0.214075 -0.009972 0.109 Uiso 0.267(13) 1 calc R U P A 2
C16B C 0.019(2) 0.364(2) 0.1598(14) 0.0667(14) Uani 0.267(13) 1 d D . P A 2
H16B H -0.111531 0.326918 0.169914 0.080 Uiso 0.267(13) 1 calc R U P A 2
C17 C 0.1304(3) 0.5656(3) 0.3679(2) 0.0366(5) Uani 1 1 d . . . . .
H17 H -0.013893 0.535320 0.365576 0.044 Uiso 0.733(13) 1 calc R U P A 1
H17B H -0.015891 0.530747 0.359697 0.044 Uiso 0.267(13) 1 calc R U P A 2
O18 O 0.2112(2) 0.75127(18) 0.40453(15) 0.0419(4) Uani 1 1 d . . . . .
H18 H 0.109(4) 0.7980(17) 0.384(2) 0.063 Uiso 1 1 calc R U . . .
C19 C 0.2270(3) 0.4969(3) 0.4610(2) 0.0356(5) Uani 1 1 d . . . . .
O20 O 0.1554(3) 0.32516(19) 0.43065(16) 0.0452(4) Uani 1 1 d . . . . .
H20 H 0.207(4) 0.2899(15) 0.484(3) 0.068 Uiso 1 1 calc R U . . .
O21 O 0.3462(3) 0.5895(2) 0.55177(15) 0.0467(4) Uani 1 1 d . . . . .
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
C2 N1 C5 108.32(18) . . ?
C2 N1 H1A 110.0 . . ?
C5 N1 H1A 110.0 . . ?
C2 N1 H1AB 110.0 . . ?
C5 N1 H1AB 110.0 . . ?
H1A N1 H1AB 108.4 . . ?
C3 C2 N1 105.2(2) . . ?
C3 C2 H2A 110.7 . . ?
N1 C2 H2A 110.7 . . ?
C3 C2 H2AB 110.7 . . ?
N1 C2 H2AB 110.7 . . ?
H2A C2 H2AB 108.8 . . ?
C2 C3 C4 103.7(2) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3AB 111.0 . . ?
C4 C3 H3AB 111.0 . . ?
H3A C3 H3AB 109.0 . . ?
C5 C4 C3 103.8(2) . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4AB 111.0 . . ?
C3 C4 H4AB 111.0 . . ?
H4A C4 H4AB 109.0 . . ?
N1 C5 C4 104.02(19) . . ?
N1 C5 C6 112.17(18) . . ?
C4 C5 C6 116.01(19) . . ?
N1 C5 H5 108.1 . . ?
C4 C5 H5 108.1 . . ?
C6 C5 H5 108.1 . . ?
O8 C6 O7 128.1(2) . . ?
O8 C6 C5 115.5(2) . . ?
O7 C6 C5 116.40(19) . . ?
C16 C11 C12 118.1(5) . . ?
C16 C11 C17 119.8(5) . . ?
C12 C11 C17 121.9(5) . . ?
C11 C12 C13 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 120.4(5) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16B C11B C12B 118.0(13) . . ?
C16B C11B C17 121.2(15) . . ?
C12B C11B C17 120.2(13) . . ?
C11B C12B C13B 120.1(11) . . ?
C11B C12B H12B 119.9 . . ?
C13B C12B H12B 119.9 . . ?
C14B C13B C12B 120.2(11) . . ?
C14B C13B H13B 119.9 . . ?
C12B C13B H13B 119.9 . . ?
C13B C14B C15B 120.5(10) . . ?
C13B C14B H14B 119.7 . . ?
C15B C14B H14B 119.7 . . ?
C14B C15B C16B 119.0(10) . . ?
C14B C15B H15B 120.5 . . ?
C16B C15B H15B 120.5 . . ?
C11B C16B C15B 120.8(11) . . ?
C11B C16B H16B 119.6 . . ?
C15B C16B H16B 119.6 . . ?
O18 C17 C11 112.8(11) . . ?
O18 C17 C19 108.82(18) . . ?
C11 C17 C19 113.8(11) . . ?
O18 C17 C11B 112(3) . . ?
C19 C17 C11B 109(3) . . ?
O18 C17 H17 107.0 . . ?
C11 C17 H17 107.0 . . ?
C19 C17 H17 107.0 . . ?
O18 C17 H17B 109.1 . . ?
C19 C17 H17B 109.1 . . ?
C11B C17 H17B 109.1 . . ?
C17 O18 H18 109.5 . . ?
O21 C19 O20 125.3(2) . . ?
O21 C19 C17 123.86(19) . . ?
O20 C19 C17 110.77(19) . . ?
C19 O20 H20 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 C2 1.500(3) . ?
N1 C5 1.504(3) . ?
N1 H1A 0.8900 . ?
N1 H1AB 0.8900 . ?
C2 C3 1.492(4) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 C4 1.516(4) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.511(4) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.528(3) . ?
C5 H5 0.9800 . ?
C6 O8 1.232(3) . ?
C6 O7 1.258(3) . ?
C11 C16 1.372(8) . ?
C11 C12 1.384(4) . ?
C11 C17 1.508(7) . ?
C12 C13 1.387(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.350(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C11B C16B 1.371(11) . ?
C11B C12B 1.384(8) . ?
C11B C17 1.530(17) . ?
C12B C13B 1.386(9) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.351(10) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.371(10) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.397(10) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C17 O18 1.419(2) . ?
C17 C19 1.524(3) . ?
C17 H17 0.9800 . ?
C17 H17B 0.9800 . ?
O18 H18 0.94(3) . ?
C19 O21 1.203(3) . ?
C19 O20 1.313(3) . ?
O20 H20 0.84(3) . ?
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 11.3(3) . . . . ?
N1 C2 C3 C4 -31.1(3) . . . . ?
C2 C3 C4 C5 39.5(3) . . . . ?
C2 N1 C5 C4 13.1(2) . . . . ?
C2 N1 C5 C6 139.2(2) . . . . ?
C3 C4 C5 N1 -32.0(3) . . . . ?
C3 C4 C5 C6 -155.7(2) . . . . ?
N1 C5 C6 O8 -168.3(2) . . . . ?
C4 C5 C6 O8 -49.0(3) . . . . ?
N1 C5 C6 O7 11.7(3) . . . . ?
C4 C5 C6 O7 131.1(2) . . . . ?
C16 C11 C12 C13 -3(3) . . . . ?
C17 C11 C12 C13 -178.4(17) . . . . ?
C11 C12 C13 C14 1(2) . . . . ?
C12 C13 C14 C15 1.7(15) . . . . ?
C13 C14 C15 C16 -2.0(11) . . . . ?
C12 C11 C16 C15 3(3) . . . . ?
C17 C11 C16 C15 178.2(14) . . . . ?
C14 C15 C16 C11 -0.5(17) . . . . ?
C16B C11B C12B C13B 14(10) . . . . ?
C17 C11B C12B C13B -175(5) . . . . ?
C11B C12B C13B C14B -6(7) . . . . ?
C12B C13B C14B C15B -4(5) . . . . ?
C13B C14B C15B C16B 7(4) . . . . ?
C12B C11B C16B C15B -11(9) . . . . ?
C17 C11B C16B C15B 178(4) . . . . ?
C14B C15B C16B C11B 1(5) . . . . ?
C16 C11 C17 O18 -108(2) . . . . ?
C12 C11 C17 O18 66(3) . . . . ?
C16 C11 C17 C19 126.9(19) . . . . ?
C12 C11 C17 C19 -58(3) . . . . ?
C16B C11B C17 O18 -129(6) . . . . ?
C12B C11B C17 O18 60(7) . . . . ?
C16B C11B C17 C19 110(6) . . . . ?
C12B C11B C17 C19 -61(7) . . . . ?
O18 C17 C19 O21 2.6(3) . . . . ?
C11 C17 C19 O21 129.3(7) . . . . ?
C11B C17 C19 O21 124.8(18) . . . . ?
O18 C17 C19 O20 179.67(17) . . . . ?
C11 C17 C19 O20 -53.6(7) . . . . ?
C11B C17 C19 O20 -58.1(18) . . . . ?
