# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ver0-23274_sn22-27_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2dgqn8
_database_code_depnum_ccdc_archive 'CCDC 2218690'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2022-xnmf7 2022
loop_
_audit_author_name
_audit_author_address
'Natalia S. Soldatova'
;Tomsk Polytechnic University
Russia
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        (S)-4-isopropyl-3-(p-tolyl)oxazolidin-2-one
_chemical_formula_moiety         'C13 H17 N O2'
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.27
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H17 N O2'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.5182(2)
_cell_length_b                   12.3029(5)
_cell_length_c                   14.3881(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1153.82(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2489
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.6610
_cell_measurement_theta_min      3.2800
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4051
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.989
_diffrn_reflns_theta_min         2.831
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2096
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -40.00   1.00   93.41    --  -23.46-178.00-150.00   47
  2  ω    -77.00 -24.00   1.00   93.41    --  -23.46 -38.00  60.00   53
  3  ω     20.00  80.00   1.00   93.41    --   24.40  57.00  30.00   60
  4  ω     51.00  80.00   1.00   93.41    --   24.40 178.00 120.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0012073000
_diffrn_orient_matrix_UB_12      -0.0000419000
_diffrn_orient_matrix_UB_13      -0.0492803000
_diffrn_orient_matrix_UB_21      -0.0810828000
_diffrn_orient_matrix_UB_22      -0.0385158000
_diffrn_orient_matrix_UB_23      -0.0003691000
_diffrn_orient_matrix_UB_31      -0.0726418000
_diffrn_orient_matrix_UB_32      0.0428859000
_diffrn_orient_matrix_UB_33      -0.0004053000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.598
_reflns_Friedel_fraction_full    0.867
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                1984
_reflns_number_total             2128
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.048
_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)+(0.0451P)²+0.0625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0879
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13)
1.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
1.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3)
1.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O9 O 1.1223(2) 0.43480(12) 0.33280(10) 0.0202(4) Uani 1 1 d . . . . .
O12 O 0.9303(2) 0.36972(13) 0.21549(10) 0.0233(4) Uani 1 1 d . . . . .
N7 N 0.8769(3) 0.54222(14) 0.27668(11) 0.0156(4) Uani 1 1 d . . . . .
C8 C 0.9682(3) 0.44317(17) 0.26900(14) 0.0164(5) Uani 1 1 d . . . . .
C1 C 0.6985(3) 0.57553(17) 0.22683(13) 0.0142(4) Uani 1 1 d . . . . .
C6 C 0.5476(3) 0.50173(18) 0.19982(13) 0.0162(5) Uani 1 1 d . . . . .
H6 H 0.5622 0.4267 0.2141 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3479(3) 0.64778(18) 0.13054(14) 0.0175(5) Uani 1 1 d . . . . .
C11 C 0.9607(3) 0.60686(18) 0.35407(13) 0.0154(5) Uani 1 1 d . . . . .
H11 H 1.0054 0.6796 0.3305 0.018 Uiso 1 1 calc R U . . .
C2 C 0.6730(3) 0.68548(18) 0.20682(14) 0.0175(5) Uani 1 1 d . . . . .
H2 H 0.7743 0.7366 0.2255 0.021 Uiso 1 1 calc R U . . .
C13 C 0.8028(3) 0.62194(18) 0.43220(13) 0.0155(5) Uani 1 1 d . . . . .
H13 H 0.6833 0.6617 0.4050 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3754(3) 0.53820(18) 0.15187(13) 0.0172(5) Uani 1 1 d . . . . .
H5 H 0.2741 0.4872 0.1332 0.021 Uiso 1 1 calc R U . . .
C10 C 1.1500(3) 0.53830(18) 0.37871(15) 0.0205(5) Uani 1 1 d . . . . .
H10A H 1.2767 0.5743 0.3565 0.025 Uiso 1 1 calc R U . . .
H10B H 1.1601 0.5282 0.4468 0.025 Uiso 1 1 calc R U . . .
C14 C 0.8928(3) 0.69444(18) 0.50845(15) 0.0190(5) Uani 1 1 d . . . . .
H14A H 1.0194 0.6617 0.5322 0.028 Uiso 1 1 calc R U . . .
H14B H 0.7934 0.7016 0.5592 0.028 Uiso 1 1 calc R U . . .
H14C H 0.9230 0.7664 0.4827 0.028 Uiso 1 1 calc R U . . .
C15 C 0.7216(4) 0.51463(19) 0.47050(15) 0.0209(5) Uani 1 1 d . . . . .
H15A H 0.6523 0.4744 0.4208 0.031 Uiso 1 1 calc R U . . .
H15B H 0.6241 0.5292 0.5208 0.031 Uiso 1 1 calc R U . . .
H15C H 0.8361 0.4713 0.4945 0.031 Uiso 1 1 calc R U . . .
C3 C 0.4995(3) 0.72023(18) 0.15957(15) 0.0181(5) Uani 1 1 d . . . . .
H3 H 0.4835 0.7955 0.1466 0.022 Uiso 1 1 calc R U . . .
C16 C 0.1646(3) 0.6867(2) 0.07620(16) 0.0256(5) Uani 1 1 d . . . . .
H16A H 0.2018 0.6940 0.0105 0.038 Uiso 1 1 calc R U . . .
H16B H 0.1201 0.7574 0.1003 0.038 Uiso 1 1 calc R U . . .
H16C H 0.0526 0.6341 0.0825 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O9 C8 1.364(2) . ?
O9 C10 1.446(3) . ?
O12 C8 1.213(3) . ?
N7 C8 1.361(3) . ?
N7 C1 1.427(3) . ?
N7 C11 1.473(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.393(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.392(3) . ?
C4 C5 1.394(3) . ?
C4 C3 1.395(3) . ?
C4 C16 1.506(3) . ?
C11 H11 1.0000 . ?
C11 C13 1.535(3) . ?
C11 C10 1.536(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.531(3) . ?
C13 C15 1.525(3) . ?
C5 H5 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 H3 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 O9 C10 109.45(16) . . ?
C8 N7 C1 124.96(18) . . ?
C8 N7 C11 112.50(17) . . ?
C1 N7 C11 121.82(17) . . ?
O12 C8 O9 121.40(19) . . ?
O12 C8 N7 129.0(2) . . ?
N7 C8 O9 109.57(18) . . ?
C6 C1 N7 121.89(19) . . ?
C2 C1 N7 118.69(19) . . ?
C2 C1 C6 119.4(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C16 121.6(2) . . ?
C3 C4 C16 121.0(2) . . ?
N7 C11 H11 109.6 . . ?
N7 C11 C13 111.71(16) . . ?
N7 C11 C10 100.12(17) . . ?
C13 C11 H11 109.6 . . ?
C13 C11 C10 115.84(17) . . ?
C10 C11 H11 109.6 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C11 C13 H13 107.1 . . ?
C14 C13 C11 109.78(16) . . ?
C14 C13 H13 107.1 . . ?
C15 C13 C11 113.12(18) . . ?
C15 C13 H13 107.1 . . ?
C15 C13 C14 112.23(17) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
O9 C10 C11 106.12(16) . . ?
O9 C10 H10A 110.5 . . ?
O9 C10 H10B 110.5 . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C3 H3 119.1 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N7 C1 C6 C5 179.53(17) . . . . ?
N7 C1 C2 C3 -179.10(17) . . . . ?
N7 C11 C13 C14 -177.01(17) . . . . ?
N7 C11 C13 C15 56.8(2) . . . . ?
N7 C11 C10 O9 -14.43(19) . . . . ?
C8 O9 C10 C11 13.6(2) . . . . ?
C8 N7 C1 C6 30.4(3) . . . . ?
C8 N7 C1 C2 -151.2(2) . . . . ?
C8 N7 C11 C13 -111.8(2) . . . . ?
C8 N7 C11 C10 11.4(2) . . . . ?
C1 N7 C8 O9 -174.08(16) . . . . ?
C1 N7 C8 O12 6.6(3) . . . . ?
C1 N7 C11 C13 58.9(2) . . . . ?
C1 N7 C11 C10 -177.92(17) . . . . ?
C1 C6 C5 C4 -0.7(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C11 N7 C8 O9 -3.7(2) . . . . ?
C11 N7 C8 O12 177.0(2) . . . . ?
C11 N7 C1 C6 -139.1(2) . . . . ?
C11 N7 C1 C2 39.3(3) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C13 C11 C10 O9 105.8(2) . . . . ?
C5 C4 C3 C2 0.8(3) . . . . ?
C10 O9 C8 O12 172.74(19) . . . . ?
C10 O9 C8 N7 -6.6(2) . . . . ?
C10 C11 C13 C14 69.2(2) . . . . ?
C10 C11 C13 C15 -57.0(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C16 C4 C5 C6 178.18(19) . . . . ?
C16 C4 C3 C2 -177.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.774
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_evk-548_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2dgqp9
_database_code_depnum_ccdc_archive 'CCDC 2218691'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2022-xnmf7 2022
loop_
_audit_author_name
_audit_author_address
'Natalia S. Soldatova'
;Tomsk Polytechnic University
Russia
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        (S)-4-(tert-butyl)-3-phenyloxazolidin-2-one
_chemical_formula_moiety         'C13 H17 N O2'
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.27
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H17 N O2 '
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.2495(2)
_cell_length_b                   12.5730(3)
_cell_length_c                   15.1106(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1187.31(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5479
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.9380
_cell_measurement_theta_min      4.5540
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6810
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        64.985
_diffrn_reflns_theta_max         64.985
_diffrn_reflns_theta_min         4.575
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -56.00   0.50    0.84    --  -35.49-163.00  -8.00  100
  2  ω    -58.00   9.00   0.50    0.84    --  -35.49  52.00  -1.00  134
  3  ω    -72.00 -47.00   0.50    0.84    --  -35.49 116.00-130.00   50
  4  ω     32.00  57.00   0.50    0.84    --   35.49-163.00  -8.00   50
  5  ω     60.00  94.00   0.50    0.84    --   35.49  52.00  -1.00   68
  6  ω     81.00 106.00   0.50    0.84    --   35.49-163.00  -8.00   50
  7  ω     23.00  54.00   0.50    0.84    --   35.49  52.00  -1.00   62
  8  ω      8.00  45.00   0.50    0.84    --   35.49  69.00 154.00   74
  9  ω     89.00 115.00   0.50    3.36    --  100.00 163.00  18.00   52
 10  ω     73.00 140.00   0.50    3.36    --  100.00  69.00 154.00  134
 11  ω     77.00 128.00   0.50    3.36    --  100.00  52.00  -1.00  102
 12  ω     60.00  86.00   0.50    3.36    --  100.00 -69.00  22.00   52
 13  ω     77.00 112.00   0.50    3.36    --  100.00 -52.00-146.00   70
 14  ω     65.00  91.00   0.50    3.36    --  100.00-116.00 141.00   52
 15  ω    -73.00  -6.00   0.50    0.84    --  -35.49 104.00   0.00  134
 16  ω    -38.00  -8.00   0.50    0.84    --  -35.49 116.00-130.00   60
 17  ω    -79.00 -54.00   0.50    0.84    --  -35.49 -69.00  22.00   50
 18  ω     23.00  48.00   0.50    0.84    --   35.49-138.00-120.00   50
 19  ω      4.00  42.00   0.50    0.84    --   35.49-116.00 141.00   76
 20  ω     83.00 121.00   0.50    3.36    --  100.00  77.00 120.00   76
 21  ω    110.00 156.00   0.50    3.36    --  100.00 107.00-180.00   92
 22  ω     90.00 149.00   0.50    3.36    --  100.00  91.00  90.00  118
 23  ω     55.00 107.00   0.50    3.36    --  100.00 -45.00-180.00  104
 24  ω     88.00 156.00   0.50    3.36    --  100.00 107.00-120.00  136
 25  ω     85.00 143.00   0.50    3.36    --  100.00  91.00 -90.00  116
 26  ω    127.00 154.00   0.50    3.36    --  100.00  77.00 120.00   54
 27  ω     86.00 157.00   0.50    3.36    --  100.00  37.00  60.00  142
 28  ω    -33.00  -7.00   0.50    0.84    --   35.49 -69.00  22.00   52
 29  ω      0.00  26.00   0.50    0.84    --  -35.49  32.00-150.00   52
 30  ω   -107.00 -81.00   0.50    0.84    --  -35.49 -32.00 120.00   52
 31  ω    -43.00 -17.00   0.50    0.84    --  -35.49 -32.00 120.00   52
 32  ω    -49.00  -9.00   0.50    0.84    --  -35.49  32.00-150.00   80
 33  ω     61.00 105.00   0.50    0.84    --   35.49  43.00 150.00   88
 34  ω     53.00 103.00   0.50    0.84    --   35.49  65.00 -90.00  100
 35  ω     -9.00  27.00   0.50    0.84    --   35.49 -32.00   0.00   72
 36  ω     17.00  49.00   0.50    0.84    --   35.49  43.00 150.00   64
 37  ω     18.00  44.00   0.50    0.84    --   35.49  43.00 -90.00   52
 38  ω     75.00 105.00   0.50    0.84    --   35.49  43.00 -90.00   60
 39  ω    -40.00  10.00   0.50    0.84    --   35.49 -21.00  30.00  100
 40  ω     24.00  50.00   0.50    0.84    --   35.49 -69.00  22.00   52
 41  ω     12.00  37.00   0.50    0.84    --   35.49  65.00 -90.00   50
 42  ω     37.00  63.00   0.50    0.84    --   35.49 -21.00  30.00   52
 43  ω     13.00  43.00   0.50    0.84    --   35.49  54.00 -60.00   60
 44  ω     40.00  78.00   0.50    3.36    --  100.00 -30.00-120.00   76
 45  ω     31.00  57.00   0.50    3.36    --  100.00-107.00  90.00   52
 46  ω     77.00 103.00   0.50    3.36    --  100.00 -91.00-150.00   52
 47  ω    132.00 157.00   0.50    3.36    --  100.00  69.00 -90.00   50
 48  ω     26.00  83.00   0.50    3.36    --  100.00-107.00  60.00  114
 49  ω     75.00 101.00   0.50    3.36    --  100.00  61.00 -90.00   52
 50  ω     25.00  99.00   0.50    3.36    --  100.00 -22.00 150.00  148
 51  ω    125.00 151.00   0.50    3.36    --  100.00 107.00-150.00   52
 52  ω     90.00 116.00   0.50    3.36    --  100.00 107.00 -60.00   52
 53  ω     74.00 100.00   0.50    3.36    --  100.00  69.00 -90.00   52
 54  ω     56.00  82.00   0.50    3.36    --  100.00 -53.00  30.00   52
 55  ω    122.00 149.00   0.50    3.36    --  100.00  30.00 150.00   54
 56  ω     86.00 112.00   0.50    3.36    --  100.00-125.00-180.00   52
 57  ω     75.00 107.00   0.50    3.36    --  100.00-107.00  90.00   64
 58  ω     77.00 102.00   0.50    3.36    --  100.00  53.00 -90.00   50
 59  ω     79.00 104.00   0.50    3.36    --  100.00  45.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0430028000
_diffrn_orient_matrix_UB_12      -0.0035783000
_diffrn_orient_matrix_UB_13      0.1004175000
_diffrn_orient_matrix_UB_21      0.1506175000
_diffrn_orient_matrix_UB_22      -0.0963471000
_diffrn_orient_matrix_UB_23      0.0086642000
_diffrn_orient_matrix_UB_31      0.1903278000
_diffrn_orient_matrix_UB_32      0.0755195000
_diffrn_orient_matrix_UB_33      0.0157136000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                1792
_reflns_number_total             1980
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.082
_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)+(0.0499P)²+0.0574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0969
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C11(H11)
1.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
1.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C3(H3), C4(H4)
1.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O9 O 0.9018(3) 0.36077(13) 0.53808(12) 0.0281(4) Uani 1 1 d . . . . .
O12 O 1.0899(3) 0.45228(14) 0.63876(12) 0.0286(4) Uani 1 1 d . . . . .
N7 N 0.7385(3) 0.49542(16) 0.60510(12) 0.0197(4) Uani 1 1 d . . . . .
C1 C 0.7085(4) 0.57931(18) 0.66735(14) 0.0189(5) Uani 1 1 d . . . . .
C6 C 0.8724(4) 0.65097(19) 0.68456(16) 0.0224(5) Uani 1 1 d . . . . .
H6 H 1.0075 0.6428 0.6566 0.027 Uiso 1 1 calc R U . . .
C8 C 0.9241(4) 0.43930(19) 0.59872(16) 0.0229(5) Uani 1 1 d . . . . .
C5 C 0.8381(4) 0.7345(2) 0.74275(16) 0.0245(6) Uani 1 1 d . . . . .
H5 H 0.9507 0.7831 0.7550 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5791(4) 0.46097(18) 0.53834(15) 0.0212(5) Uani 1 1 d . . . . .
H11 H 0.4392 0.4472 0.5683 0.025 Uiso 1 1 calc R U . . .
C2 C 0.5109(4) 0.59023(19) 0.70952(15) 0.0215(5) Uani 1 1 d . . . . .
H2 H 0.3998 0.5402 0.6992 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4792(5) 0.6751(2) 0.76667(16) 0.0272(6) Uani 1 1 d . . . . .
H3 H 0.3444 0.6836 0.7949 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5447(4) 0.5409(2) 0.46176(15) 0.0247(5) Uani 1 1 d . . . . .
C4 C 0.6408(4) 0.7476(2) 0.78308(16) 0.0269(6) Uani 1 1 d . . . . .
H4 H 0.6167 0.8060 0.8217 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6799(4) 0.3547(2) 0.51108(18) 0.0272(6) Uani 1 1 d . . . . .
H10A H 0.6071 0.2948 0.5411 0.033 Uiso 1 1 calc R U . . .
H10B H 0.6690 0.3444 0.4463 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4419(4) 0.6434(2) 0.49648(16) 0.0283(6) Uani 1 1 d . . . . .
H15A H 0.3124 0.6258 0.5300 0.042 Uiso 1 1 calc R U . . .
H15B H 0.4043 0.6894 0.4465 0.042 Uiso 1 1 calc R U . . .
H15C H 0.5432 0.6805 0.5352 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3869(5) 0.4892(2) 0.39675(18) 0.0336(6) Uani 1 1 d . . . . .
H14A H 0.4549 0.4276 0.3687 0.050 Uiso 1 1 calc R U . . .
H14B H 0.3464 0.5410 0.3512 0.050 Uiso 1 1 calc R U . . .
H14C H 0.2589 0.4661 0.4288 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7549(4) 0.5672(2) 0.41487(18) 0.0318(6) Uani 1 1 d . . . . .
H16A H 0.8537 0.6005 0.4569 0.048 Uiso 1 1 calc R U . . .
H16B H 0.7269 0.6163 0.3659 0.048 Uiso 1 1 calc R U . . .
H16C H 0.8188 0.5017 0.3918 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O9 C8 1.354(3) . ?
O9 C10 1.447(3) . ?
O12 C8 1.211(3) . ?
N7 C1 1.425(3) . ?
N7 C8 1.361(3) . ?
N7 C11 1.482(3) . ?
C1 C6 1.389(4) . ?
C1 C2 1.396(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(4) . ?
C11 H11 1.0000 . ?
C11 C13 1.548(3) . ?
C11 C10 1.534(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C13 C15 1.533(3) . ?
C13 C14 1.536(4) . ?
C13 C16 1.528(4) . ?
C4 H4 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 O9 C10 109.13(19) . . ?
C1 N7 C11 125.3(2) . . ?
C8 N7 C1 122.8(2) . . ?
C8 N7 C11 111.89(19) . . ?
C6 C1 N7 120.5(2) . . ?
C6 C1 C2 120.2(2) . . ?
C2 C1 N7 119.3(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
O9 C8 N7 109.8(2) . . ?
O12 C8 O9 121.6(2) . . ?
O12 C8 N7 128.6(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
N7 C11 H11 109.3 . . ?
N7 C11 C13 114.35(19) . . ?
N7 C11 C10 99.29(19) . . ?
C13 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
C10 C11 C13 115.0(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C15 C13 C11 110.39(19) . . ?
C15 C13 C14 107.8(2) . . ?
C14 C13 C11 107.0(2) . . ?
C16 C13 C11 111.6(2) . . ?
C16 C13 C15 109.7(2) . . ?
C16 C13 C14 110.3(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.2 . . ?
O9 C10 C11 105.77(19) . . ?
O9 C10 H10A 110.6 . . ?
O9 C10 H10B 110.6 . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N7 C1 C6 C5 177.5(2) . . . . ?
N7 C1 C2 C3 -176.8(2) . . . . ?
N7 C11 C13 C15 -66.5(3) . . . . ?
N7 C11 C13 C14 176.5(2) . . . . ?
N7 C11 C13 C16 55.7(3) . . . . ?
N7 C11 C10 O9 -19.6(2) . . . . ?
C1 N7 C8 O9 176.2(2) . . . . ?
C1 N7 C8 O12 -3.6(4) . . . . ?
C1 N7 C11 C13 70.9(3) . . . . ?
C1 N7 C11 C10 -166.2(2) . . . . ?
C1 C6 C5 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C6 C5 C4 C3 1.6(4) . . . . ?
C8 O9 C10 C11 18.2(3) . . . . ?
C8 N7 C1 C6 40.2(3) . . . . ?
C8 N7 C1 C2 -141.3(2) . . . . ?
C8 N7 C11 C13 -107.1(2) . . . . ?
C8 N7 C11 C10 15.8(2) . . . . ?
C11 N7 C1 C6 -137.6(2) . . . . ?
C11 N7 C1 C2 41.0(3) . . . . ?
C11 N7 C8 O9 -5.8(3) . . . . ?
C11 N7 C8 O12 174.4(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C13 C11 C10 O9 102.9(2) . . . . ?
C10 O9 C8 O12 171.6(2) . . . . ?
C10 O9 C8 N7 -8.2(3) . . . . ?
C10 C11 C13 C15 179.5(2) . . . . ?
C10 C11 C13 C14 62.5(3) . . . . ?
C10 C11 C13 C16 -58.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.257
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_evk-557_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2dgqqb
_database_code_depnum_ccdc_archive 'CCDC 2218692'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2022-xnmf7 2022
loop_
_audit_author_name
_audit_author_address
'Natalia S. Soldatova'
;Tomsk Polytechnic University
Russia
;
_audit_update_record             
;
2022-11-10 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
(S)-3-(4-chlorophenyl)-4-methyloxazolidin-2-one
_chemical_formula_moiety         'C10 H10 Cl N O2'
_chemical_formula_sum            'C10 H10 Cl N O2'
_chemical_formula_weight         211.64
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 Cl N O2 '
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'
Cl Cl 0.3639 0.7018 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.53040(10)
_cell_length_b                   8.5314(2)
_cell_length_c                   10.1412(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.371(2)
_cell_angle_gamma                90
_cell_volume                     477.655(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3147
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.7840
_cell_measurement_theta_min      4.3660
_shelx_estimated_absorpt_T_max   0.754
_shelx_estimated_absorpt_T_min   0.619
_exptl_absorpt_coefficient_mu    3.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0112
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3560
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        64.867
_diffrn_reflns_theta_max         64.867
_diffrn_reflns_theta_min         4.367
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -32.00   0.50    3.20    --  -35.49  73.00  -9.00   50
  2  ω      5.00  31.00   0.50    3.20    --  -35.49  73.00  -9.00   52
  3  ω    120.00 153.00   0.50    9.43    --  100.00  73.00  -9.00   66
  4  ω     40.00 123.00   0.50    9.43    --  100.00 -73.00-138.00  166
  5  ω    -95.00 -49.00   0.50    3.20    --  -35.49 138.00 -30.00   92
  6  ω    -45.00 -16.00   0.50    3.20    --  -35.49 138.00 -30.00   58
  7  ω    -32.00   2.00   0.50    3.20    --   35.49 -65.00 120.00   68
  8  ω     24.00  53.00   0.50    3.20    --   35.49 -43.00 -60.00   58
  9  ω    -21.00  21.00   0.50    3.20    --   35.49 -43.00 -60.00   84
 10  ω     26.00  59.00   0.50    3.20    --   35.49 -89.00-150.00   66
 11  ω    -28.00  -1.00   0.50    3.20    --   35.49 -73.00-138.00   54
 12  ω    -25.00  17.00   0.50    3.20    --   35.49 -89.00-150.00   84
 13  ω      6.00  55.00   0.50    3.20    --   35.49 -65.00 120.00   98
 14  ω      3.00  28.00   0.50    3.20    --   35.49-104.00 150.00   50
 15  ω     39.00  64.00   0.50    3.20    --   35.49 -73.00-138.00   50
 16  ω     39.00  89.00   0.50    3.20    --   35.49-138.00 -90.00  100
 17  ω    118.00 144.00   0.50    9.43    --  100.00  37.00 120.00   52
 18  ω     81.00 115.00   0.50    9.43    --  100.00  37.00 120.00   68
 19  ω     36.00  80.00   0.50    9.43    --  100.00 -45.00  60.00   88
 20  ω     96.00 123.00   0.50    9.43    --  100.00  77.00 120.00   54
 21  ω     43.00  69.00   0.50    9.43    --  100.00-125.00-120.00   52
 22  ω     81.00 125.00   0.50    9.43    --  100.00-149.00  90.00   88
 23  ω    110.00 135.00   0.50    9.43    --  100.00  61.00 -90.00   50
 24  ω    124.00 157.00   0.50    9.43    --  100.00 149.00-180.00   66
 25  ω     33.00 117.00   0.50    9.43    --  100.00 -45.00-150.00  168
 26  ω     87.00 120.00   0.50    9.43    --  100.00 149.00-180.00   66
 27  ω     78.00 156.00   0.50    9.43    --  100.00  53.00-120.00  156
 28  ω     75.00 112.00   0.50    9.43    --  100.00-125.00-120.00   74
 29  ω     83.00 147.00   0.50    9.43    --  100.00  77.00 -30.00  128
 30  ω     74.00 116.00   0.50    9.43    --  100.00  69.00   0.00   84
 31  ω    131.00 156.00   0.50    9.43    --  100.00  69.00   0.00   50
 32  ω     88.00 126.00   0.50    9.43    --  100.00 107.00-120.00   76
 33  ω     88.00 118.00   0.50    9.43    --  100.00 -45.00  60.00   60
 34  ω     87.00 147.00   0.50    9.43    --  100.00  91.00 -60.00  120
 35  ω    -27.00  -1.00   0.50    3.20    --  -35.49  73.00  -9.00   52
 36  ω     -7.00  31.00   0.50    3.20    --  -35.49  54.00 -90.00   76
 37  ω     41.00 103.00   0.50    3.20    --   35.49  43.00  60.00  124
 38  ω    -35.00  -9.00   0.50    3.20    --   35.49 -21.00-150.00   52
 39  ω     69.00 101.00   0.50    3.20    --   35.49  32.00 150.00   64
 40  ω     29.00  55.00   0.50    3.20    --   35.49-138.00  60.00   52
 41  ω     23.00  50.00   0.50    3.20    --   35.49 -21.00-150.00   54
 42  ω     47.00 102.00   0.50    3.20    --   35.49  65.00  90.00  110
 43  ω     28.00  61.00   0.50    3.20    --   35.49  32.00 150.00   66
 44  ω     79.00 157.00   0.50    9.43    --  100.00  53.00  30.00  156
 45  ω     74.00 102.00   0.50    9.43    --  100.00  69.00  60.00   56
 46  ω    119.00 145.00   0.50    9.43    --  100.00  69.00 120.00   52
 47  ω    117.00 143.00   0.50    9.43    --  100.00  69.00  60.00   52
 48  ω     39.00  65.00   0.50    9.43    --  100.00-125.00   0.00   52
 49  ω     82.00 108.00   0.50    9.43    --  100.00-125.00   0.00   52
 50  ω    111.00 147.00   0.50    9.43    --  100.00  45.00  90.00   72
 51  ω     30.00  55.00   0.50    9.43    --  100.00 -30.00-180.00   50
 52  ω     79.00 105.00   0.50    9.43    --  100.00  69.00 120.00   52
 53  ω    116.00 141.00   0.50    9.43    --  100.00 107.00 120.00   50
 54  ω    130.00 155.00   0.50    9.43    --  100.00  -7.00 150.00   50
 55  ω     69.00 120.00   0.50    9.43    --  100.00 -30.00-180.00  102
 56  ω     75.00 107.00   0.50    9.43    --  100.00-107.00-120.00   64
 57  ω     81.00 111.00   0.50    9.43    --  100.00 -77.00  30.00   60
 58  ω     87.00 113.00   0.50    9.43    --  100.00  45.00 150.00   52
 59  ω    116.00 144.00   0.50    9.43    --  100.00  45.00 150.00   56
 60  ω    113.00 152.00   0.50    9.43    --  100.00  53.00  60.00   78
 61  ω     73.00  99.00   0.50    9.43    --  100.00  69.00  90.00   52
 62  ω     29.00  67.00   0.50    9.43    --  100.00 -91.00  30.00   76
 63  ω     81.00 106.00   0.50    9.43    --  100.00 -91.00  30.00   50
 64  ω     27.00  73.00   0.50    9.43    --  100.00-107.00   0.00   92
 65  ω     35.00  61.00   0.50    9.43    --  100.00-125.00 -60.00   52
 66  ω     67.00  93.00   0.50    9.43    --  100.00-125.00 -60.00   52
 67  ω     49.00  75.00   0.50    9.43    --  100.00 -77.00  30.00   52
 68  ω     66.00 116.00   0.50    9.43    --  100.00 -61.00  30.00  100
 69  ω     20.00  46.00   0.50    9.43    --  100.00  -7.00 150.00   52
 70  ω     26.00  68.00   0.50    9.43    --  100.00-107.00-120.00   84
 71  ω     81.00 107.00   0.50    9.43    --  100.00  53.00 120.00   52
 72  ω     80.00 105.00   0.50    9.43    --  100.00  45.00  90.00   50
 73  ω     98.00 145.00   0.50    9.43    --  100.00  37.00  60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0749331000
_diffrn_orient_matrix_UB_12      -0.0395502000
_diffrn_orient_matrix_UB_13      -0.1400594000
_diffrn_orient_matrix_UB_21      -0.1462552000
_diffrn_orient_matrix_UB_22      0.1415174000
_diffrn_orient_matrix_UB_23      -0.0552728000
_diffrn_orient_matrix_UB_31      0.2256245000
_diffrn_orient_matrix_UB_32      0.1049519000
_diffrn_orient_matrix_UB_33      0.0217378000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1591
_reflns_number_total             1613
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1613
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0197
_refine_ls_restrained_S_all      1.054
_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)+(0.0312P)²+0.0971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0523
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C11(H11)
1.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
1.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C3(H3)
1.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl14 Cl 1.06794(8) 0.45962(6) 0.67580(4) 0.02749(16) Uani 1 1 d . . . . .
O9 O 0.1381(3) 0.40392(17) 0.03865(15) 0.0236(4) Uani 1 1 d . . . . .
O12 O 0.3573(3) 0.22414(19) 0.15566(15) 0.0250(4) Uani 1 1 d . . . . .
N7 N 0.3826(3) 0.4899(2) 0.20436(16) 0.0205(4) Uani 1 1 d . . . . .
C8 C 0.3011(4) 0.3602(3) 0.1367(2) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.5449(3) 0.4815(3) 0.31851(18) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.4956(4) 0.5643(3) 0.4322(2) 0.0208(4) Uani 1 1 d . . . . .
H2 H 0.3527 0.6259 0.4338 0.025 Uiso 1 1 calc R U . . .
C5 C 0.9140(4) 0.3835(3) 0.4261(2) 0.0234(4) Uani 1 1 d . . . . .
H5 H 1.0567 0.3217 0.4247 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7535(4) 0.3914(3) 0.3155(2) 0.0218(4) Uani 1 1 d . . . . .
H6 H 0.7866 0.3351 0.2378 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6549(4) 0.5570(3) 0.5432(2) 0.0218(4) Uani 1 1 d . . . . .
H3 H 0.6217 0.6126 0.6213 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8630(3) 0.4671(3) 0.53822(18) 0.0212(4) Uani 1 1 d . . . . .
C13 C 0.3975(4) 0.7761(3) 0.1558(2) 0.0252(5) Uani 1 1 d . . . . .
H13A H 0.4520 0.8096 0.2451 0.038 Uiso 1 1 calc R U . . .
H13B H 0.3021 0.8600 0.1121 0.038 Uiso 1 1 calc R U . . .
H13C H 0.5386 0.7531 0.1050 0.038 Uiso 1 1 calc R U . . .
C11 C 0.2432(4) 0.6307(3) 0.1639(2) 0.0222(5) Uani 1 1 d . . . . .
H11 H 0.1102 0.6487 0.2248 0.027 Uiso 1 1 calc R U . . .
C10 C 0.1384(4) 0.5739(3) 0.0292(2) 0.0275(5) Uani 1 1 d . . . . .
H10A H -0.0282 0.6142 0.0111 0.033 Uiso 1 1 calc R U . . .
H10B H 0.2403 0.6092 -0.0422 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cl14 C4 1.7462(18) . ?
O9 C8 1.354(3) . ?
O9 C10 1.454(3) . ?
O12 C8 1.214(3) . ?
N7 C8 1.364(3) . ?
N7 C1 1.424(2) . ?
N7 C11 1.472(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C5 C4 1.386(3) . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C11 1.511(3) . ?
C11 H11 1.0000 . ?
C11 C10 1.531(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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 O9 C10 108.66(18) . . ?
C8 N7 C1 122.80(18) . . ?
C8 N7 C11 111.68(17) . . ?
C1 N7 C11 124.18(17) . . ?
O9 C8 N7 109.38(19) . . ?
O12 C8 O9 122.2(2) . . ?
O12 C8 N7 128.4(2) . . ?
C2 C1 N7 120.18(18) . . ?
C6 C1 N7 119.64(17) . . ?
C6 C1 C2 120.17(18) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.16(19) . . ?
C3 C2 H2 119.9 . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.09(19) . . ?
C1 C6 C5 120.06(19) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.90(19) . . ?
C4 C3 H3 120.5 . . ?
C5 C4 Cl14 118.90(16) . . ?
C5 C4 C3 121.61(18) . . ?
C3 C4 Cl14 119.49(16) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
N7 C11 C13 113.40(18) . . ?
N7 C11 H11 110.2 . . ?
N7 C11 C10 98.92(17) . . ?
C13 C11 H11 110.2 . . ?
C13 C11 C10 113.38(19) . . ?
C10 C11 H11 110.2 . . ?
O9 C10 C11 104.98(18) . . ?
O9 C10 H10A 110.8 . . ?
O9 C10 H10B 110.8 . . ?
C11 C10 H10A 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?

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
N7 C1 C2 C3 -179.53(19) . . . . ?
N7 C1 C6 C5 179.47(19) . . . . ?
N7 C11 C10 O9 24.3(2) . . . . ?
C8 O9 C10 C11 -21.5(2) . . . . ?
C8 N7 C1 C2 -131.4(2) . . . . ?
C8 N7 C1 C6 49.2(3) . . . . ?
C8 N7 C11 C13 -141.01(18) . . . . ?
C8 N7 C11 C10 -20.6(2) . . . . ?
C1 N7 C8 O9 176.05(16) . . . . ?
C1 N7 C8 O12 -4.0(3) . . . . ?
C1 N7 C11 C13 51.9(3) . . . . ?
C1 N7 C11 C10 172.25(17) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C3 C4 Cl14 178.79(17) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C5 C4 Cl14 -178.85(17) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C13 C11 C10 O9 144.6(2) . . . . ?
C11 N7 C8 O9 8.7(2) . . . . ?
C11 N7 C8 O12 -171.3(2) . . . . ?
C11 N7 C1 C2 34.3(3) . . . . ?
C11 N7 C1 C6 -145.1(2) . . . . ?
C10 O9 C8 O12 -171.4(2) . . . . ?
C10 O9 C8 N7 8.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.789
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
