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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/7/24/67/7246753.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_7246753
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 H7 F O3, C5 H9 N O2'
_chemical_formula_sum            'C13 H16 F N O5'
_chemical_formula_weight         285.27
_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
_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                102.89(4)
_cell_angle_beta                 101.66(6)
_cell_angle_gamma                103.44(4)
_cell_formula_units_Z            2
_cell_length_a                   7.406(5)
_cell_length_b                   8.459(2)
_cell_length_c                   12.281(7)
_cell_measurement_reflns_used    286
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      18.1940
_cell_measurement_theta_min      3.2740
_cell_volume                     702.8(7)
_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 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'65 images, ΔΦ 3.0° '
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1060
_diffrn_reflns_av_unetI/netI     0.1494
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2190
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        18.845
_diffrn_reflns_theta_max         18.845
_diffrn_reflns_theta_min         2.993
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93501
_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    1.348
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1647
_refine_ls_R_factor_gt           0.0706
_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)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1526
_reflns_Friedel_coverage         0.000
_reflns_number_gt                525
_reflns_number_total             1057
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00226h2.cif
_cod_data_source_block           alex_Lena_Ltar
_cod_depositor_comments
'Adding full bibliography for 7246740--7246756.cif.'
_cod_database_code               7246753
_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 0.9872(12) -0.0455(9) 0.6398(6) 0.063(2) Uani 1 1 d . . . . .
H1A H 1.033582 0.040067 0.612570 0.075 Uiso 1 1 calc R U . . .
H1AB H 0.949526 -0.141184 0.582316 0.075 Uiso 1 1 calc R U . . .
C2 C 1.1418(15) -0.0547(13) 0.7389(10) 0.077(3) Uani 1 1 d . . . . .
H2A H 1.171701 -0.161488 0.719394 0.093 Uiso 1 1 calc R U . . .
H2AB H 1.258762 0.037206 0.755362 0.093 Uiso 1 1 calc R U . . .
C3 C 1.0596(18) -0.0398(17) 0.8410(10) 0.117(5) Uani 1 1 d . . . . .
H3A H 1.157840 0.031180 0.910919 0.141 Uiso 1 1 calc R U . . .
H3AB H 1.011497 -0.150767 0.851440 0.141 Uiso 1 1 calc R U . . .
C4 C 0.8982(17) 0.0380(13) 0.8174(10) 0.084(4) Uani 1 1 d . . . . .
H4A H 0.945817 0.160633 0.845925 0.101 Uiso 1 1 calc R U . . .
H4AB H 0.799699 -0.001807 0.854443 0.101 Uiso 1 1 calc R U . . .
C5 C 0.8182(14) -0.0189(11) 0.6861(9) 0.055(3) Uani 1 1 d . . . . .
H5 H 0.719539 -0.128481 0.664230 0.066 Uiso 1 1 calc R U . . .
O7 O 0.7929(9) 0.1544(7) 0.5517(6) 0.063(2) Uani 1 1 d . . . . .
C6 C 0.7276(17) 0.1064(12) 0.6317(10) 0.059(3) Uani 1 1 d . . . . .
O8 O 0.5982(11) 0.1444(9) 0.6752(6) 0.088(3) Uani 1 1 d . . . . .
F11 F 0.3242(12) 0.3731(11) 0.1624(7) 0.160(4) Uani 1 1 d . . . . .
C12 C 0.510(2) 0.3983(19) 0.1512(17) 0.091(4) Uani 1 1 d . . . . .
C13 C 0.534(3) 0.3277(18) 0.0410(14) 0.128(6) Uani 1 1 d . . . . .
H13 H 0.427274 0.265177 -0.021013 0.153 Uiso 1 1 calc R U . . .
C14 C 0.718(4) 0.353(2) 0.0274(16) 0.119(6) Uani 1 1 d . . . . .
H14 H 0.737401 0.308820 -0.044360 0.143 Uiso 1 1 calc R U . . .
C15 C 0.876(2) 0.4460(19) 0.1217(17) 0.094(5) Uani 1 1 d . . . . .
H15 H 1.000027 0.464969 0.112794 0.112 Uiso 1 1 calc R U . . .
C16 C 0.847(2) 0.5107(12) 0.2304(11) 0.069(4) Uani 1 1 d . . . . .
H16 H 0.953517 0.568359 0.293178 0.083 Uiso 1 1 calc R U . . .
C17 C 0.662(2) 0.4915(14) 0.2476(12) 0.056(3) Uani 1 1 d . . . . .
C18 C 0.6328(14) 0.5703(12) 0.3647(9) 0.058(3) Uani 1 1 d . . . . .
H18 H 0.493939 0.543567 0.356837 0.070 Uiso 1 1 calc R U . . .
O19 O 0.7125(8) 0.7526(7) 0.4025(5) 0.061(2) Uani 1 1 d . . . . .
H19 H 0.628193 0.796299 0.382431 0.092 Uiso 1 1 calc R U . . .
C20 C 0.7235(16) 0.4961(13) 0.4611(11) 0.053(3) Uani 1 1 d . . . . .
O21 O 0.8382(11) 0.5836(8) 0.5520(6) 0.070(2) Uani 1 1 d . . . . .
O22 O 0.6450(8) 0.3289(8) 0.4293(5) 0.065(2) Uani 1 1 d . . . . .
H22 H 0.704216 0.287606 0.473819 0.097 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'
F F 0.0171 0.0103 '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 C2 108.0(7) . . ?
C5 N1 H1A 110.1 . . ?
C2 N1 H1A 110.1 . . ?
C5 N1 H1AB 110.1 . . ?
C2 N1 H1AB 110.1 . . ?
H1A N1 H1AB 108.4 . . ?
C3 C2 N1 105.9(8) . . ?
C3 C2 H2A 110.6 . . ?
N1 C2 H2A 110.6 . . ?
C3 C2 H2AB 110.6 . . ?
N1 C2 H2AB 110.6 . . ?
H2A C2 H2AB 108.7 . . ?
C2 C3 C4 107.3(9) . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3AB 110.3 . . ?
C4 C3 H3AB 110.3 . . ?
H3A C3 H3AB 108.5 . . ?
C3 C4 C5 105.1(8) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4AB 110.7 . . ?
C5 C4 H4AB 110.7 . . ?
H4A C4 H4AB 108.8 . . ?
N1 C5 C4 104.8(8) . . ?
N1 C5 C6 110.8(9) . . ?
C4 C5 C6 115.9(8) . . ?
N1 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
C6 C5 H5 108.4 . . ?
O8 C6 O7 129.4(10) . . ?
O8 C6 C5 113.1(10) . . ?
O7 C6 C5 117.5(10) . . ?
F11 C12 C17 118.5(15) . . ?
F11 C12 C13 117.8(18) . . ?
C17 C12 C13 123.7(14) . . ?
C14 C13 C12 118.7(16) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 119.7(18) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.0(16) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 122.3(12) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C12 C17 C16 115.5(12) . . ?
C12 C17 C18 122.9(14) . . ?
C16 C17 C18 121.6(14) . . ?
O19 C18 C17 112.4(8) . . ?
O19 C18 C20 108.7(8) . . ?
C17 C18 C20 111.8(8) . . ?
O19 C18 H18 107.9 . . ?
C17 C18 H18 107.9 . . ?
C20 C18 H18 107.9 . . ?
C18 O19 H19 109.5 . . ?
O21 C20 O22 127.5(10) . . ?
O21 C20 C18 123.2(9) . . ?
O22 C20 C18 109.1(10) . . ?
C20 O22 H22 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 C5 1.517(10) . ?
N1 C2 1.523(10) . ?
N1 H1A 0.8900 . ?
N1 H1AB 0.8900 . ?
C2 C3 1.495(12) . ?
C2 H2A 0.9700 . ?
C2 H2AB 0.9700 . ?
C3 C4 1.502(12) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.523(11) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.576(12) . ?
C5 H5 0.9800 . ?
O7 C6 1.282(11) . ?
C6 O8 1.257(11) . ?
F11 C12 1.382(13) . ?
C12 C17 1.386(15) . ?
C12 C13 1.415(16) . ?
C13 C14 1.385(17) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.404(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.405(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.524(12) . ?
C18 O19 1.445(9) . ?
C18 C20 1.566(12) . ?
C18 H18 0.9800 . ?
O19 H19 0.8200 . ?
C20 O21 1.213(10) . ?
C20 O22 1.331(10) . ?
O22 H22 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 2.0(11) . . . . ?
N1 C2 C3 C4 -19.8(12) . . . . ?
C2 C3 C4 C5 29.9(13) . . . . ?
C2 N1 C5 C4 16.0(9) . . . . ?
C2 N1 C5 C6 141.7(8) . . . . ?
C3 C4 C5 N1 -27.9(11) . . . . ?
C3 C4 C5 C6 -150.3(10) . . . . ?
N1 C5 C6 O8 -174.0(9) . . . . ?
C4 C5 C6 O8 -54.7(13) . . . . ?
N1 C5 C6 O7 6.1(12) . . . . ?
C4 C5 C6 O7 125.3(11) . . . . ?
F11 C12 C13 C14 179.2(13) . . . . ?
C17 C12 C13 C14 -1(2) . . . . ?
C12 C13 C14 C15 1(2) . . . . ?
C13 C14 C15 C16 1(2) . . . . ?
C14 C15 C16 C17 -2.6(17) . . . . ?
F11 C12 C17 C16 179.3(9) . . . . ?
C13 C12 C17 C16 -1.0(17) . . . . ?
F11 C12 C17 C18 -1.3(16) . . . . ?
C13 C12 C17 C18 178.4(11) . . . . ?
C15 C16 C17 C12 2.5(14) . . . . ?
C15 C16 C17 C18 -176.9(9) . . . . ?
C12 C17 C18 O19 -119.5(10) . . . . ?
C16 C17 C18 O19 59.8(11) . . . . ?
C12 C17 C18 C20 117.9(11) . . . . ?
C16 C17 C18 C20 -62.7(12) . . . . ?
O19 C18 C20 O21 1.4(14) . . . . ?
C17 C18 C20 O21 126.0(12) . . . . ?
O19 C18 C20 O22 177.4(7) . . . . ?
C17 C18 C20 O22 -58.0(11) . . . . ?
