#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:33:35 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290821 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/27/7132701.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_7132701
loop_
_publ_author_name
'Koch, Katelyn N.'
'Teo, Aaron J.'
'Wheeler, Kraig A.'
_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_formula_moiety         'C13 H16 Cl N O3'
_chemical_formula_sum            'C13 H16 Cl N O3'
_chemical_formula_weight         269.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 105.680(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5014(4)
_cell_length_b                   16.7568(8)
_cell_length_c                   10.0698(5)
_cell_measurement_reflns_used    7898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      5.27
_cell_volume                     1381.12(12)
_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      100.00
_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 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ 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  0.0793
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17953
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         5.271
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5559
_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    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0607
_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)+(0.0610P)²+1.7607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1570
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1936
_reflns_number_total             2515
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc06212k2.cif
_cod_data_source_block           22kaw09_a
_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               7132701
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Cl1 Cl 0.14619(10) 0.54674(6) 0.41018(11) 0.0576(3) Uani 1 1 d . . . . .
O1 O 0.6088(3) 0.23468(14) 0.6907(2) 0.0410(5) Uani 1 1 d . . . . .
O2 O 0.7092(3) 0.02678(15) 0.5883(3) 0.0507(6) Uani 1 1 d . . . . .
H2 H 0.627(5) -0.011(3) 0.563(4) 0.061 Uiso 1 1 d . U . . .
O3 O 0.4981(3) 0.09213(13) 0.4506(2) 0.0440(6) Uani 1 1 d . . . . .
N1 N 0.6695(3) 0.23256(16) 0.4880(3) 0.0340(6) Uani 1 1 d . . . . .
H1 H 0.641(4) 0.246(2) 0.410(4) 0.041 Uiso 1 1 d . U . . .
C1 C 0.5911(4) 0.26437(19) 0.5757(3) 0.0346(7) Uani 1 1 d . . . . .
C2 C 0.4838(4) 0.33504(18) 0.5298(3) 0.0323(7) Uani 1 1 d . . . . .
C3 C 0.3927(4) 0.3625(2) 0.6165(3) 0.0396(7) Uani 1 1 d . . . . .
H3 H 0.401973 0.336316 0.701938 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2887(4) 0.4273(2) 0.5803(4) 0.0453(8) Uani 1 1 d . . . . .
H4 H 0.226841 0.445424 0.640107 0.054 Uiso 1 1 calc R U . . .
C5 C 0.2761(4) 0.4654(2) 0.4562(4) 0.0440(8) Uani 1 1 d . . . . .
C6 C 0.3660(4) 0.4398(2) 0.3683(3) 0.0435(8) Uani 1 1 d . . . . .
H6 H 0.356634 0.466401 0.283181 0.052 Uiso 1 1 calc R U . . .
C7 C 0.4699(4) 0.3751(2) 0.4060(3) 0.0400(7) Uani 1 1 d . . . . .
H7 H 0.532536 0.357674 0.346308 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6401(4) 0.08976(19) 0.5173(3) 0.0360(7) Uani 1 1 d . . . . .
C9 C 0.7579(4) 0.15791(18) 0.5241(3) 0.0353(7) Uani 1 1 d . . . . .
H9 H 0.829886 0.162102 0.620472 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8650(4) 0.1411(2) 0.4262(3) 0.0371(7) Uani 1 1 d . . . . .
H10A H 0.895246 0.083887 0.432995 0.045 Uiso 1 1 calc R U . . .
H10B H 0.799840 0.151426 0.330324 0.045 Uiso 1 1 calc R U . . .
C11 C 1.0201(4) 0.1908(2) 0.4556(3) 0.0403(7) Uani 1 1 d . . . . .
H11 H 0.992911 0.247127 0.473586 0.048 Uiso 1 1 calc R U . . .
C12 C 1.0922(5) 0.1896(3) 0.3313(4) 0.0530(9) Uani 1 1 d . . . . .
H12A H 1.119495 0.134646 0.312925 0.079 Uiso 1 1 calc R U . . .
H12B H 1.191189 0.222484 0.351548 0.079 Uiso 1 1 calc R U . . .
H12C H 1.011881 0.211014 0.250216 0.079 Uiso 1 1 calc R U . . .
C13 C 1.1479(4) 0.1595(2) 0.5816(4) 0.0518(9) Uani 1 1 d . . . . .
H13A H 1.102504 0.159296 0.661281 0.078 Uiso 1 1 calc R U . . .
H13B H 1.244429 0.194093 0.600950 0.078 Uiso 1 1 calc R U . . .
H13C H 1.178986 0.105115 0.563566 0.078 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C8 O2 H2 102(3) . . ?
C1 N1 H1 118(3) . . ?
C1 N1 C9 119.2(3) . . ?
C9 N1 H1 120(3) . . ?
O1 C1 N1 119.9(3) . . ?
O1 C1 C2 121.4(3) . . ?
N1 C1 C2 118.7(3) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 C7 118.4(3) . . ?
C7 C2 C1 123.9(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 Cl1 119.4(3) . . ?
C4 C5 C6 121.0(3) . . ?
C6 C5 Cl1 119.6(3) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
O2 C8 C9 112.8(3) . . ?
O3 C8 O2 123.8(3) . . ?
O3 C8 C9 123.3(3) . . ?
N1 C9 C8 110.4(2) . . ?
N1 C9 H9 108.8 . . ?
N1 C9 C10 110.7(3) . . ?
C8 C9 H9 108.8 . . ?
C8 C9 C10 109.4(2) . . ?
C10 C9 H9 108.8 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.0(3) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11 108.8 . . ?
C10 C11 C12 110.5(3) . . ?
C10 C11 C13 111.1(3) . . ?
C12 C11 H11 108.8 . . ?
C13 C11 H11 108.8 . . ?
C13 C11 C12 108.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
Cl1 C5 1.737(4) . ?
O1 C1 1.232(4) . ?
O2 H2 0.92(4) . ?
O2 C8 1.320(4) . ?
O3 C8 1.213(4) . ?
N1 H1 0.79(4) . ?
N1 C1 1.351(4) . ?
N1 C9 1.454(4) . ?
C1 C2 1.490(4) . ?
C2 C3 1.392(4) . ?
C2 C7 1.393(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(5) . ?
C5 C6 1.384(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.508(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.538(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.520(4) . ?
C11 H11 1.0000 . ?
C11 C12 1.535(4) . ?
C11 C13 1.522(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.92(4) 1.71(4) 2.619(3) 167(4) 3_656 yes
N1 H1 O1 0.79(4) 2.17(4) 2.948(3) 167(4) 4_565 yes
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
Cl1 C5 C6 C7 179.7(3) . . . . ?
O1 C1 C2 C3 -5.4(4) . . . . ?
O1 C1 C2 C7 174.5(3) . . . . ?
O2 C8 C9 N1 -160.1(3) . . . . ?
O2 C8 C9 C10 77.9(3) . . . . ?
O3 C8 C9 N1 21.7(4) . . . . ?
O3 C8 C9 C10 -100.3(4) . . . . ?
N1 C1 C2 C3 174.3(3) . . . . ?
N1 C1 C2 C7 -5.8(4) . . . . ?
N1 C9 C10 C11 76.2(3) . . . . ?
C1 N1 C9 C8 70.0(3) . . . . ?
C1 N1 C9 C10 -168.7(3) . . . . ?
C1 C2 C3 C4 -179.3(3) . . . . ?
C1 C2 C7 C6 179.1(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C2 C7 C6 -1.0(5) . . . . ?
C3 C4 C5 Cl1 -179.9(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C2 0.6(5) . . . . ?
C7 C2 C3 C4 0.9(5) . . . . ?
C8 C9 C10 C11 -162.0(3) . . . . ?
C9 N1 C1 O1 7.4(4) . . . . ?
C9 N1 C1 C2 -172.3(2) . . . . ?
C9 C10 C11 C12 -163.0(3) . . . . ?
C9 C10 C11 C13 76.1(4) . . . . ?
