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_7132713
_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         'C16 H15 N O3, C13 H17 N O3'
_chemical_formula_sum            'C29 H32 N2 O6'
_chemical_formula_weight         504.56
_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                 108.014(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9173(7)
_cell_length_b                   9.1344(6)
_cell_length_c                   14.1599(10)
_cell_measurement_reflns_used    9907
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.02
_cell_measurement_theta_min      5.85
_cell_volume                     1342.85(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 0.993
_diffrn_measured_fraction_theta_max 0.991
_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  0.0230
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43830
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.007
_diffrn_reflns_theta_min         4.502
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6490
_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    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2479 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5446
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0484P)^2^+0.2443P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                5380
_reflns_number_total             5446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06212k2.cif
_cod_data_source_block           23kaw42
_cod_depositor_comments
;
The following automatic conversions were performed:

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               7132713
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.827
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,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
 C10B-C11B \\sim C10B-C11C
 with sigma of 0.02
 C11B-C12B \\sim C11C-C12C
 with sigma of 0.02
 C11B-C13B \\sim C11C-C13C
 with sigma of 0.02
 C10B-C12B \\sim C10B-C12C
 with sigma of 0.04
 C10B-C13B \\sim C10B-C13C
 with sigma of 0.04
 C12B-C13B \\sim C12C-C13C
 with sigma of 0.04
 N1B-H1B \\sim N1A-H1A
 with sigma of 0.02
 O2A-H2A \\sim O2B-H2B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C11B, C12B, C13B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11C, C12C, C13C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(H10C)=Sof(H10D)=Sof(C13C)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C11C)=
 Sof(H11C)=Sof(C12C)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(H10A)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12A)=Sof(H12B)=
 Sof(H12C)=Sof(C13B)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B), C11B(H11B), C11C(H11C)
5.b Secondary CH2 refined with riding coordinates:
 C10A(H10E,H10F), C10B(H10A,H10B), C10B(H10C,H10D)
5.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C12A(H12G), C13A(H13G),
 C14A(H14A), C15A(H15A), C16A(H16A), C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B),
 C7B(H7B)
5.d Idealised Me refined as rotating group:
 C12B(H12A,H12B,H12C), C13B(H13A,H13B,H13C), C13C(H13D,H13E,H13F), C12C(H12D,
 H12E,H12F)
;
_shelx_res_checksum              8963
_shelx_hkl_checksum              91598
_olex2_submission_special_instructions 'No special instructions were received'