Dual space divergence in small molecule quasiracemates: benzoyl leucine and phenylalanine assemblies.
Koch, Katelyn N.; Teo, Aaron J.; Wheeler, Kraig A.; Chemical communications (Cambridge, England) 60 (2024) 2800–2803; doi:10.1039/d3cc06212k

data_7132711
_publ_section_title
;
 Dual space divergence in small molecule quasiracemates: benzoyl leucine
 and phenylalanine assemblies.
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2800
_journal_page_last               2803
_journal_paper_doi               10.1039/d3cc06212k
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H16 F3 N O3, C17 H14 F3 N O3'
_chemical_formula_sum            'C31 H30 F6 N2 O6'
_chemical_formula_weight         640.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-14
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-18 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.871(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.8243(8)
_cell_length_b                   9.1832(5)
_cell_length_c                   13.8585(8)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.74
_cell_measurement_theta_min      3.61
_cell_volume                     1555.27(16)
_computing_cell_refinement       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '\k-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20421
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.859
_diffrn_reflns_theta_min         3.608
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    1.024
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 2235 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6082
_refine_ls_number_restraints     121
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.9984P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                5418
_reflns_number_total             6082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06212k2.cif
_cod_data_source_block           23kaw59
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Dual' was changed to
'dual' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7132699--7132715.cif.
;
_cod_database_code               7132711
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 F2A-C14 \\sim F2-C14 \\sim F3-C14 \\sim F3A-C14 \\sim F1-C14 \\sim F1A-C14
 with sigma of 0.02
 F2A-C5 \\sim F2-C5 \\sim F3-C5 \\sim F3A-C5 \\sim F1-C5 \\sim F1A-C5
 with sigma of 0.02
 F2B-C17A \\sim F2C-C17A \\sim F1C-C17A \\sim F1B-C17A \\sim F3C-C17A \\sim
F3B-C17A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1C) \\sim Ueq, Uanis(F1B) \\sim Ueq, Uanis(F3C) \\sim Ueq, Uanis(F3B)
\\sim Ueq, Uanis(F2C) \\sim Ueq, Uanis(F2B) \\sim Ueq, Uanis(F3) \\sim Ueq,
Uanis(F3A) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.001 and sigma for terminal
atoms of 0.002
4. Same fragment restrains
{F1C, F2C, F3C} sigma for 1-2: 0.02, 1-3: 0.04
as in
{F1B, F2B, F3B}
{F1A, F2A, F3A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{F1A, F2A, F3A}
5. Others
 Fixed Sof: F1(0.5) F2(0.5) F3(0.5) F1A(0.5) F2A(0.5) F3A(0.5) F1C(0.5)
 F2C(0.5) F3C(0.5) F1B(0.5) F2B(0.5) F3B(0.5)
6.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C9A(H9A)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10C,H10D), C10A(H10A,H10B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A)
6.d Idealised Me refined as rotating group:
 C12(H12B,H12C,H12D), C13(H13B,H13C,H13D)
;
_shelx_res_checksum              20547
_shelx_hkl_checksum              12600
_olex2_submission_special_instructions 'No special instructions were received'