# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_p20180704c
_database_code_depnum_ccdc_archive 'CCDC 1996461'
loop_
_audit_author_name
_audit_author_address
'Shixuan Cao'
;Nankai University
China
;
_audit_update_record             
;
2020-04-12 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;
_audit_creation_date             2018-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
(S)-3-(2-benzoylbenzyl)-3-hydroxy-1-methylindolin-2-one
_chemical_formula_moiety         'C23 H19 N O3'
_chemical_formula_sum            'C23 H19 N O3'
_chemical_formula_weight         357.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H19NO3
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                   6.04785(4)
_cell_length_b                   13.36306(6)
_cell_length_c                   21.94319(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1773.400(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17283
_cell_measurement_temperature    295.15
_cell_measurement_theta_max      78.7710
_cell_measurement_theta_min      3.8840
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.783
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21423
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.186
_diffrn_reflns_theta_min         3.873
_diffrn_ambient_temperature      295.15
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -139.00  40.00   0.50    0.50    --  -49.30  -9.00-174.00  358
  2  ω   -199.00 -21.00   0.50    4.00    -- -110.00  -9.00-174.00  356
  3  ω   -199.00 -21.00   0.50    4.00    -- -110.00   9.00   0.00  356
  4  ω    -83.00  40.00   0.50    0.50    --  -49.30  38.00 120.00  246
  5  ω   -139.00 -17.00   0.50    0.50    --  -49.30 -64.00 -95.38  244
  6  ω   -144.00 -21.00   0.50    4.00    -- -110.00  72.00-180.00  246
  7  ω   -144.00 -21.00   0.50    4.00    -- -110.00  72.00 -90.00  246
  8  ω   -199.00 -80.00   0.50    4.00    -- -110.00 -47.00 -51.72  238
  9  ω   -199.00 -89.00   0.50    4.00    -- -110.00 -47.00  65.09  220
 10  ω   -142.00 -21.00   0.50    4.00    -- -110.00  72.00-150.00  242
 11  ω   -197.00-107.00   0.50    4.00    -- -110.00 -42.00  41.50  180
 12  ω   -199.00 -80.00   0.50    4.00    -- -110.00 -49.00 -28.38  238
 13  ω   -142.00 -79.00   0.50    4.00    -- -110.00  72.00  90.00  126
 14  ω   -123.00 -97.00   0.50    4.00    -- -110.00  72.00 150.00   52
 15  ω   -144.00 -22.00   0.50    4.00    -- -110.00  72.00 120.00  244
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0020242000
_diffrn_orient_matrix_UB_12      0.1118232000
_diffrn_orient_matrix_UB_13      0.0170916000
_diffrn_orient_matrix_UB_21      -0.0302698000
_diffrn_orient_matrix_UB_22      0.0279691000
_diffrn_orient_matrix_UB_23      -0.0676030000
_diffrn_orient_matrix_UB_31      -0.2528671000
_diffrn_orient_matrix_UB_32      -0.0024387000
_diffrn_orient_matrix_UB_33      0.0082369000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                3657
_reflns_number_total             3749
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 1512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       0.0056(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3749
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.065
_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/[σ²(Fo²)+(0.0372P)²+0.1873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0720
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.0340(2) 0.68875(9) 0.48240(5) 0.0516(3) Uani 1 1 d . . . . .
O2 O 0.4836(2) 0.61779(8) 0.45635(5) 0.0448(3) Uani 1 1 d . . . . .
H2 H 0.5123 0.6677 0.4766 0.067 Uiso 1 1 calc GR . . . .
O3 O 0.2695(2) 0.54229(10) 0.30212(6) 0.0509(3) Uani 1 1 d . . . . .
N1 N 0.0934(2) 0.59833(9) 0.57025(6) 0.0384(3) Uani 1 1 d . . . . .
C1 C 0.1324(3) 0.62453(11) 0.51140(7) 0.0374(3) Uani 1 1 d . . . . .
C2 C 0.3250(3) 0.55962(10) 0.48712(6) 0.0340(3) Uani 1 1 d . . . . .
C3 C 0.4050(3) 0.50982(10) 0.54483(6) 0.0344(3) Uani 1 1 d . . . . .
C4 C 0.2573(3) 0.53246(10) 0.59173(7) 0.0361(3) Uani 1 1 d . . . . .
C5 C 0.2853(4) 0.49602(12) 0.65013(7) 0.0448(4) Uani 1 1 d . . . . .
H5 H 0.1848 0.5110 0.6809 0.054 Uiso 1 1 calc R . . . .
C6 C 0.4687(4) 0.43628(12) 0.66135(8) 0.0505(4) Uani 1 1 d . . . . .
H6 H 0.4910 0.4106 0.7003 0.061 Uiso 1 1 calc R . . . .
C7 C 0.6184(3) 0.41432(12) 0.61591(9) 0.0499(4) Uani 1 1 d . . . . .
H7 H 0.7409 0.3747 0.6246 0.060 Uiso 1 1 calc R . . . .
C8 C 0.5877(3) 0.45112(12) 0.55675(8) 0.0420(3) Uani 1 1 d . . . . .
H8 H 0.6886 0.4363 0.5261 0.050 Uiso 1 1 calc R . . . .
C9 C -0.0740(3) 0.64574(13) 0.60796(8) 0.0447(4) Uani 1 1 d . . . . .
H9A H -0.0042 0.6906 0.6362 0.067 Uiso 1 1 calc GR . . . .
H9B H -0.1540 0.5954 0.6301 0.067 Uiso 1 1 calc GR . . . .
H9C H -0.1745 0.6825 0.5825 0.067 Uiso 1 1 calc GR . . . .
C10 C 0.2292(3) 0.48472(11) 0.44005(7) 0.0370(3) Uani 1 1 d . . . . .
H10A H 0.1250 0.4406 0.4602 0.044 Uiso 1 1 calc R . . . .
H10B H 0.1500 0.5213 0.4088 0.044 Uiso 1 1 calc R . . . .
C11 C 0.4092(3) 0.42288(10) 0.41074(6) 0.0350(3) Uani 1 1 d . . . . .
C12 C 0.5344(3) 0.45976(10) 0.36202(6) 0.0341(3) Uani 1 1 d . . . . .
C13 C 0.7223(3) 0.40832(12) 0.34238(8) 0.0458(4) Uani 1 1 d . . . . .
H13 H 0.8111 0.4357 0.3121 0.055 Uiso 1 1 calc R . . . .
C14 C 0.7772(4) 0.31674(13) 0.36771(9) 0.0532(5) Uani 1 1 d . . . . .
H14 H 0.9024 0.2827 0.3545 0.064 Uiso 1 1 calc R . . . .
C15 C 0.6461(4) 0.27644(12) 0.41246(8) 0.0532(5) Uani 1 1 d . . . . .
H15 H 0.6779 0.2134 0.4281 0.064 Uiso 1 1 calc R . . . .
C16 C 0.4658(3) 0.32980(12) 0.43450(7) 0.0462(4) Uani 1 1 d . . . . .
H16 H 0.3812 0.3027 0.4658 0.055 Uiso 1 1 calc R . . . .
C17 C 0.4571(2) 0.54550(11) 0.32321(6) 0.0346(3) Uani 1 1 d . . . . .
C18 C 0.6116(3) 0.62759(11) 0.30713(6) 0.0351(3) Uani 1 1 d . . . . .
C19 C 0.7958(3) 0.64848(12) 0.34281(8) 0.0414(4) Uani 1 1 d . . . . .
H19 H 0.8260 0.6095 0.3769 0.050 Uiso 1 1 calc R . . . .
C20 C 0.9337(3) 0.72670(14) 0.32781(10) 0.0524(4) Uani 1 1 d . . . . .
H20 H 1.0563 0.7408 0.3519 0.063 Uiso 1 1 calc R . . . .
C21 C 0.8897(4) 0.78440(14) 0.27682(9) 0.0565(5) Uani 1 1 d . . . . .
H21 H 0.9838 0.8368 0.2665 0.068 Uiso 1 1 calc R . . . .
C22 C 0.7075(4) 0.76466(13) 0.24130(8) 0.0547(5) Uani 1 1 d . . . . .
H22 H 0.6789 0.8037 0.2071 0.066 Uiso 1 1 calc R . . . .
C23 C 0.5671(3) 0.68699(12) 0.25623(7) 0.0449(4) Uani 1 1 d . . . . .
H23 H 0.4430 0.6743 0.2324 0.054 Uiso 1 1 calc R . . . .


_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
O1 C1 1.2228(19) . ?
O2 H2 0.8200 . ?
O2 C2 1.4073(18) . ?
O3 C17 1.226(2) . ?
N1 C1 1.359(2) . ?
N1 C4 1.407(2) . ?
N1 C9 1.453(2) . ?
C1 C2 1.547(2) . ?
C2 C3 1.510(2) . ?
C2 C10 1.550(2) . ?
C3 C4 1.396(2) . ?
C3 C8 1.380(2) . ?
C4 C5 1.381(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.400(2) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.510(2) . ?
C11 C12 1.400(2) . ?
C11 C16 1.391(2) . ?
C12 C13 1.396(2) . ?
C12 C17 1.502(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.484(2) . ?
C18 C19 1.390(2) . ?
C18 C23 1.396(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(3) . ?
C23 H23 0.9300 . ?

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
C2 O2 H2 109.5 . . ?
C1 N1 C4 110.95(13) . . ?
C1 N1 C9 123.35(14) . . ?
C4 N1 C9 124.96(13) . . ?
O1 C1 N1 126.23(15) . . ?
O1 C1 C2 125.50(14) . . ?
N1 C1 C2 108.26(13) . . ?
O2 C2 C1 111.64(12) . . ?
O2 C2 C3 115.29(13) . . ?
O2 C2 C10 106.95(12) . . ?
C1 C2 C10 108.08(13) . . ?
C3 C2 C1 101.51(11) . . ?
C3 C2 C10 113.20(12) . . ?
C4 C3 C2 108.53(13) . . ?
C8 C3 C2 131.76(14) . . ?
C8 C3 C4 119.72(14) . . ?
C3 C4 N1 109.83(13) . . ?
C5 C4 N1 128.16(15) . . ?
C5 C4 C3 121.95(15) . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.71(16) . . ?
C6 C5 H5 121.1 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.25(16) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.58(17) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 118.77(16) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.3 . . ?
C2 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C2 111.59(13) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C12 C11 C10 121.49(13) . . ?
C16 C11 C10 120.46(14) . . ?
C16 C11 C12 117.89(15) . . ?
C11 C12 C17 122.23(14) . . ?
C13 C12 C11 120.17(14) . . ?
C13 C12 C17 116.98(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.44(17) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.70(18) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.07(15) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.43(16) . . ?
C15 C16 H16 119.3 . . ?
O3 C17 C12 118.37(14) . . ?
O3 C17 C18 121.25(14) . . ?
C18 C17 C12 120.20(13) . . ?
C19 C18 C17 121.28(13) . . ?
C19 C18 C23 119.41(15) . . ?
C23 C18 C17 119.28(15) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.21(16) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.96(19) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.35(17) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.18(17) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 120.1 . . ?
C22 C23 C18 119.89(17) . . ?
C22 C23 H23 120.1 . . ?

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
O1 C1 C2 O2 46.6(2) . . . . ?
O1 C1 C2 C3 169.97(16) . . . . ?
O1 C1 C2 C10 -70.74(19) . . . . ?
O2 C2 C3 C4 128.56(13) . . . . ?
O2 C2 C3 C8 -50.9(2) . . . . ?
O2 C2 C10 C11 55.76(16) . . . . ?
O3 C17 C18 C19 161.27(15) . . . . ?
O3 C17 C18 C23 -16.7(2) . . . . ?
N1 C1 C2 O2 -132.90(13) . . . . ?
N1 C1 C2 C3 -9.55(15) . . . . ?
N1 C1 C2 C10 109.74(14) . . . . ?
N1 C4 C5 C6 -176.07(15) . . . . ?
C1 N1 C4 C3 -3.01(17) . . . . ?
C1 N1 C4 C5 174.16(16) . . . . ?
C1 C2 C3 C4 7.74(15) . . . . ?
C1 C2 C3 C8 -171.72(16) . . . . ?
C1 C2 C10 C11 176.09(11) . . . . ?
C2 C3 C4 N1 -3.57(16) . . . . ?
C2 C3 C4 C5 179.06(14) . . . . ?
C2 C3 C8 C7 -179.63(15) . . . . ?
C2 C10 C11 C12 -81.83(17) . . . . ?
C2 C10 C11 C16 93.51(17) . . . . ?
C3 C2 C10 C11 -72.30(16) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 N1 C1 O1 -171.41(16) . . . . ?
C4 N1 C1 C2 8.11(17) . . . . ?
C4 C3 C8 C7 1.0(2) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C3 0.0(2) . . . . ?
C8 C3 C4 N1 175.96(13) . . . . ?
C8 C3 C4 C5 -1.4(2) . . . . ?
C9 N1 C1 O1 -0.9(3) . . . . ?
C9 N1 C1 C2 178.66(14) . . . . ?
C9 N1 C4 C3 -173.38(14) . . . . ?
C9 N1 C4 C5 3.8(3) . . . . ?
C10 C2 C3 C4 -107.84(14) . . . . ?
C10 C2 C3 C8 72.7(2) . . . . ?
C10 C11 C12 C13 169.45(15) . . . . ?
C10 C11 C12 C17 -19.8(2) . . . . ?
C10 C11 C16 C15 -172.98(16) . . . . ?
C11 C12 C13 C14 4.9(3) . . . . ?
C11 C12 C17 O3 -50.05(19) . . . . ?
C11 C12 C17 C18 134.72(15) . . . . ?
C12 C11 C16 C15 2.5(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C12 C17 C18 C19 -23.6(2) . . . . ?
C12 C17 C18 C23 158.42(13) . . . . ?
C13 C12 C17 O3 121.00(17) . . . . ?
C13 C12 C17 C18 -54.24(19) . . . . ?
C13 C14 C15 C16 -3.4(3) . . . . ?
C14 C15 C16 C11 2.2(3) . . . . ?
C16 C11 C12 C13 -6.0(2) . . . . ?
C16 C11 C12 C17 164.76(14) . . . . ?
C17 C12 C13 C14 -166.35(17) . . . . ?
C17 C18 C19 C20 -178.35(15) . . . . ?
C17 C18 C23 C22 178.97(15) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C18 C23 C22 1.0(2) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C18 -0.8(3) . . . . ?
C23 C18 C19 C20 -0.4(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 1.568
_oxdiff_exptl_absorpt_empirical_full_min 0.692
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane, ethyl acetate'
####################################################################### 
# 
# 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_r20190214b1
_database_code_depnum_ccdc_archive 'CCDC 1996463'
loop_
_audit_author_name
_audit_author_address
'Shixuan Cao'
;Nankai University
China
;
_audit_update_record             
;
2020-04-12 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-10-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
1-methyl-1'-phenyl-4'H-spiro[indoline-3,3'-isoquinolin]-2-one
_chemical_formula_moiety         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39
_chemical_melting_point          ?
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4653(17)
_cell_length_b                   10.802(2)
_cell_length_c                   11.181(2)
_cell_angle_alpha                82.97(3)
_cell_angle_beta                 67.84(3)
_cell_angle_gamma                69.97(3)
_cell_volume                     889.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2436
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8148
_cell_measurement_theta_min      2.7422
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10578
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.770
_diffrn_reflns_theta_min         1.967
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1863
_reflns_number_total             4134
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.064
_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)+(0.0103P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0862
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.28773(15) 0.45937(11) 0.07003(11) 0.0331(3) Uani 1 1 d . . . . .
N1 N 0.39888(17) 0.27570(13) -0.06011(12) 0.0245(3) Uani 1 1 d . . . . .
N2 N 0.15718(17) 0.26074(13) 0.25551(12) 0.0230(3) Uani 1 1 d . . . . .
C1 C 0.3557(2) 0.16011(16) -0.05748(14) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.4473(2) 0.05639(17) -0.14555(16) 0.0307(4) Uani 1 1 d . . . . .
H2 H 0.550330 0.057508 -0.219219 0.037 Uiso 1 1 calc R . . . .
C3 C 0.3809(2) -0.05003(17) -0.12095(17) 0.0343(5) Uani 1 1 d . . . . .
H3 H 0.440012 -0.122808 -0.179192 0.041 Uiso 1 1 calc R . . . .
C4 C 0.2306(2) -0.05121(17) -0.01336(17) 0.0344(5) Uani 1 1 d . . . . .
H4 H 0.187960 -0.124381 0.000661 0.041 Uiso 1 1 calc R . . . .
C5 C 0.1404(2) 0.05436(17) 0.07547(16) 0.0288(4) Uani 1 1 d . . . . .
H5 H 0.038201 0.052899 0.149781 0.035 Uiso 1 1 calc R . . . .
C6 C 0.2040(2) 0.16029(16) 0.05187(15) 0.0213(4) Uani 1 1 d . . . . .
C7 C 0.1382(2) 0.28746(16) 0.12714(14) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.2820(2) 0.35383(17) 0.04560(15) 0.0239(4) Uani 1 1 d . . . . .
C9 C 0.5536(2) 0.30542(17) -0.15762(15) 0.0354(5) Uani 1 1 d . . . . .
H9A H 0.527980 0.334874 -0.236784 0.053 Uiso 1 1 calc GR . . . .
H9B H 0.659743 0.226086 -0.176221 0.053 Uiso 1 1 calc GR . . . .
H9C H 0.576851 0.375234 -0.125286 0.053 Uiso 1 1 calc GR . . . .
C10 C -0.0493(2) 0.38026(16) 0.13361(14) 0.0248(4) Uani 1 1 d . . . . .
H10A H -0.059596 0.471613 0.148633 0.030 Uiso 1 1 calc R . . . .
H10B H -0.062242 0.377778 0.049643 0.030 Uiso 1 1 calc R . . . .
C11 C -0.1990(2) 0.34309(15) 0.23912(15) 0.0221(4) Uani 1 1 d . . . . .
C12 C -0.3645(2) 0.35975(16) 0.22955(16) 0.0277(4) Uani 1 1 d . . . . .
H12 H -0.383762 0.390797 0.151327 0.033 Uiso 1 1 calc R . . . .
C13 C -0.5019(2) 0.33123(17) 0.33384(17) 0.0344(5) Uani 1 1 d . . . . .
H13 H -0.614457 0.343286 0.326480 0.041 Uiso 1 1 calc R . . . .
C14 C -0.4750(2) 0.28529(18) 0.44832(17) 0.0384(5) Uani 1 1 d . . . . .
H14 H -0.569613 0.267464 0.519848 0.046 Uiso 1 1 calc R . . . .
C15 C -0.3081(2) 0.26532(17) 0.45806(16) 0.0323(4) Uani 1 1 d . . . . .
H15 H -0.288784 0.232421 0.535897 0.039 Uiso 1 1 calc R . . . .
C16 C -0.1690(2) 0.29371(15) 0.35326(15) 0.0229(4) Uani 1 1 d . . . . .
C17 C 0.0144(2) 0.26731(15) 0.35614(14) 0.0217(4) Uani 1 1 d . . . . .
C18 C 0.0414(2) 0.24125(16) 0.48336(14) 0.0233(4) Uani 1 1 d . . . . .
C19 C -0.0466(2) 0.33770(17) 0.57981(15) 0.0289(4) Uani 1 1 d . . . . .
H19 H -0.128142 0.419118 0.566369 0.035 Uiso 1 1 calc R . . . .
C20 C -0.0161(2) 0.31573(18) 0.69593(15) 0.0343(5) Uani 1 1 d . . . . .
H20 H -0.073454 0.383092 0.760072 0.041 Uiso 1 1 calc R . . . .
C21 C 0.0979(2) 0.19576(19) 0.71754(16) 0.0362(5) Uani 1 1 d . . . . .
H21 H 0.117000 0.180038 0.797262 0.043 Uiso 1 1 calc R . . . .
C22 C 0.1843(2) 0.09835(19) 0.62290(16) 0.0402(5) Uani 1 1 d . . . . .
H22 H 0.262091 0.015781 0.638062 0.048 Uiso 1 1 calc R . . . .
C23 C 0.1573(2) 0.12139(17) 0.50566(16) 0.0345(5) Uani 1 1 d . . . . .
H23 H 0.218430 0.054923 0.440551 0.041 Uiso 1 1 calc R . . . .


_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
O1 C8 1.2250(18) . ?
N1 C1 1.410(2) . ?
N1 C8 1.371(2) . ?
N1 C9 1.460(2) . ?
N2 C7 1.4866(19) . ?
N2 C17 1.2910(19) . ?
C1 C2 1.387(2) . ?
C1 C6 1.399(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.407(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C6 C7 1.520(2) . ?
C7 C8 1.558(2) . ?
C7 C10 1.540(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.505(2) . ?
C11 C12 1.393(2) . ?
C11 C16 1.401(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.399(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.405(2) . ?
C16 C17 1.492(2) . ?
C17 C18 1.503(2) . ?
C18 C19 1.393(2) . ?
C18 C23 1.392(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.395(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.393(2) . ?
C23 H23 0.9500 . ?

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
C1 N1 C9 124.93(14) . . ?
C8 N1 C1 110.96(14) . . ?
C8 N1 C9 124.01(14) . . ?
C17 N2 C7 118.31(13) . . ?
C2 C1 N1 127.33(16) . . ?
C2 C1 C6 122.44(17) . . ?
C6 C1 N1 110.21(14) . . ?
C1 C2 H2 121.5 . . ?
C1 C2 C3 117.00(17) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.27(16) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.96(17) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.30(17) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 108.76(14) . . ?
C5 C6 C1 120.02(16) . . ?
C5 C6 C7 131.22(15) . . ?
N2 C7 C6 111.10(13) . . ?
N2 C7 C8 106.02(12) . . ?
N2 C7 C10 113.42(13) . . ?
C6 C7 C8 101.54(13) . . ?
C6 C7 C10 114.77(13) . . ?
C10 C7 C8 108.91(13) . . ?
O1 C8 N1 125.60(16) . . ?
O1 C8 C7 125.94(15) . . ?
N1 C8 C7 108.45(14) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.1 . . ?
C7 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C7 112.27(13) . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C12 C11 C10 123.28(14) . . ?
C12 C11 C16 119.68(15) . . ?
C16 C11 C10 117.00(14) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.52(16) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.24(16) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.74(16) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.28(16) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 119.50(15) . . ?
C11 C16 C17 118.07(14) . . ?
C15 C16 C17 122.37(15) . . ?
N2 C17 C16 124.81(14) . . ?
N2 C17 C18 115.95(14) . . ?
C16 C17 C18 119.20(13) . . ?
C19 C18 C17 120.47(15) . . ?
C23 C18 C17 120.51(15) . . ?
C23 C18 C19 119.01(15) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.56(16) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.88(17) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.04(16) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.10(17) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.37(17) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?

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
N1 C1 C2 C3 178.55(14) . . . . ?
N1 C1 C6 C5 -178.47(13) . . . . ?
N1 C1 C6 C7 1.17(17) . . . . ?
N2 C7 C8 O1 -62.4(2) . . . . ?
N2 C7 C8 N1 119.07(13) . . . . ?
N2 C7 C10 C11 -46.03(18) . . . . ?
N2 C17 C18 C19 119.40(18) . . . . ?
N2 C17 C18 C23 -59.3(2) . . . . ?
C1 N1 C8 O1 179.01(15) . . . . ?
C1 N1 C8 C7 -2.43(17) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C1 C6 C7 N2 -114.79(14) . . . . ?
C1 C6 C7 C8 -2.41(16) . . . . ?
C1 C6 C7 C10 114.87(15) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C1 C6 C7 179.75(14) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C4 C5 C6 C7 179.85(15) . . . . ?
C5 C6 C7 N2 64.8(2) . . . . ?
C5 C6 C7 C8 177.18(16) . . . . ?
C5 C6 C7 C10 -65.5(2) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C6 C7 C8 O1 -178.54(15) . . . . ?
C6 C7 C8 N1 2.91(16) . . . . ?
C6 C7 C10 C11 83.17(17) . . . . ?
C7 N2 C17 C16 3.1(2) . . . . ?
C7 N2 C17 C18 -179.17(13) . . . . ?
C7 C10 C11 C12 -146.58(15) . . . . ?
C7 C10 C11 C16 35.7(2) . . . . ?
C8 N1 C1 C2 -177.66(15) . . . . ?
C8 N1 C1 C6 0.84(18) . . . . ?
C8 C7 C10 C11 -163.82(13) . . . . ?
C9 N1 C1 C2 -1.2(2) . . . . ?
C9 N1 C1 C6 177.32(14) . . . . ?
C9 N1 C8 O1 2.5(3) . . . . ?
C9 N1 C8 C7 -178.94(13) . . . . ?
C10 C7 C8 O1 60.0(2) . . . . ?
C10 C7 C8 N1 -118.55(15) . . . . ?
C10 C11 C12 C13 -175.88(15) . . . . ?
C10 C11 C16 C15 175.95(14) . . . . ?
C10 C11 C16 C17 -6.9(2) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C11 C16 C17 N2 -14.7(2) . . . . ?
C11 C16 C17 C18 167.56(15) . . . . ?
C12 C11 C16 C15 -1.9(2) . . . . ?
C12 C11 C16 C17 175.27(14) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C14 C15 C16 C17 -176.59(14) . . . . ?
C15 C16 C17 N2 162.36(16) . . . . ?
C15 C16 C17 C18 -15.4(2) . . . . ?
C16 C11 C12 C13 1.8(2) . . . . ?
C16 C17 C18 C19 -62.7(2) . . . . ?
C16 C17 C18 C23 118.59(18) . . . . ?
C17 N2 C7 C6 -103.53(16) . . . . ?
C17 N2 C7 C8 146.97(14) . . . . ?
C17 N2 C7 C10 27.5(2) . . . . ?
C17 C18 C19 C20 -177.34(15) . . . . ?
C17 C18 C23 C22 178.93(15) . . . . ?
C18 C19 C20 C21 -2.1(3) . . . . ?
C19 C18 C23 C22 0.2(3) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C22 C23 C18 -1.1(3) . . . . ?
C23 C18 C19 C20 1.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p20190508b
_database_code_depnum_ccdc_archive 'CCDC 1996462'
loop_
_audit_author_name
_audit_author_address
'Shixuan Cao'
;Nankai University
China
;
_audit_update_record             
;
2020-04-12 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-05-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(S)-3-((R)-1-(2-benzoylphenyl)ethyl)-3-hydroxy-1-methylindolin-2-one
_chemical_formula_moiety         'C24 H21 N O3'
_chemical_formula_sum            'C24 H21 N O3'
_chemical_formula_weight         371.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H21NO3
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                   6.53150(10)
_cell_length_b                   13.40120(10)
_cell_length_c                   21.6517(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1895.17(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9627
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      78.6960
_cell_measurement_theta_min      3.8990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14063
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.676
_diffrn_reflns_theta_min         3.879
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50    0.50    --    5.00   8.00  -4.00  356
  2  ω    -84.00  94.00   0.50    0.50    --    5.00  -8.00 179.00  356
  3  ω   -140.00  39.00   0.50    0.50    --  -50.10  -8.00 179.00  358
  4  ω   -199.00 -72.00   0.50    0.50    -- -110.00   8.00  -4.00  254
  5  ω   -134.00-109.00   0.50    0.50    -- -110.00  -8.00 179.00   50
  6  ω     -9.00  33.00   0.50    0.50    --  -50.10  57.00 -30.00   84
  7  ω    -76.00 -50.00   0.50    0.50    --  -50.10  57.00 -30.00   52
  8  ω    -77.00  39.00   0.50    0.50    --  -50.10  57.00-120.00  232
  9  ω   -199.00-114.00   0.50    0.50    -- -110.00 -44.00  56.21  170
 10  ω   -133.00 -86.00   0.50    0.50    -- -110.00  57.00-180.00   94
 11  ω   -198.00-121.00   0.50    0.50    -- -110.00 -57.00 120.00  154
 12  ω   -135.00 -33.00   0.50    0.50    -- -110.00  72.00 150.00  204
 13  ω   -199.00 -97.00   0.50    0.50    -- -110.00 -57.00-180.00  204
 14  ω    -95.00 -69.00   0.50    0.50    -- -110.00  72.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0010870000
_diffrn_orient_matrix_UB_12      0.0959177000
_diffrn_orient_matrix_UB_13      -0.0391957000
_diffrn_orient_matrix_UB_21      -0.0239367000
_diffrn_orient_matrix_UB_22      -0.0630755000
_diffrn_orient_matrix_UB_23      -0.0590681000
_diffrn_orient_matrix_UB_31      -0.2346191000
_diffrn_orient_matrix_UB_32      0.0060023000
_diffrn_orient_matrix_UB_33      0.0062097000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                3654
_reflns_number_total             3823
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(11)
_refine_ls_extinction_coef       0.0049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.066
_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)+(0.0461P)²+0.1195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0875
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.9038(3) 0.69642(10) 0.51797(6) 0.0551(4) Uani 1 1 d . . . . .
O2 O 0.4857(3) 0.61772(10) 0.53840(6) 0.0508(4) Uani 1 1 d . . . . .
O3 O 0.6907(2) 0.56820(15) 0.70013(7) 0.0635(4) Uani 1 1 d . . . . .
N1 N 0.8711(3) 0.60234(11) 0.42974(7) 0.0438(4) Uani 1 1 d . . . . .
C1 C 0.8216(3) 0.63048(13) 0.48795(8) 0.0418(4) Uani 1 1 d . . . . .
C2 C 0.6461(3) 0.56302(13) 0.51109(8) 0.0390(4) Uani 1 1 d . . . . .
C3 C 0.5879(3) 0.50847(12) 0.45252(7) 0.0386(4) Uani 1 1 d . . . . .
C4 C 0.7299(3) 0.53229(13) 0.40691(8) 0.0400(4) Uani 1 1 d . . . . .
C5 C 0.7181(4) 0.49294(14) 0.34777(8) 0.0500(5) Uani 1 1 d . . . . .
H5 H 0.815816 0.507978 0.317960 0.060 Uiso 1 1 calc R . . . .
C6 C 0.5546(4) 0.43028(14) 0.33487(9) 0.0544(5) Uani 1 1 d . . . . .
H6 H 0.542454 0.402963 0.295556 0.065 Uiso 1 1 calc R . . . .
C7 C 0.4101(4) 0.40758(15) 0.37890(10) 0.0554(5) Uani 1 1 d . . . . .
H7 H 0.300631 0.366276 0.368851 0.067 Uiso 1 1 calc R . . . .
C8 C 0.4268(3) 0.44631(14) 0.43875(9) 0.0474(4) Uani 1 1 d . . . . .
H8 H 0.330348 0.430224 0.468738 0.057 Uiso 1 1 calc R . . . .
C9 C 1.0417(4) 0.64339(16) 0.39493(9) 0.0519(5) Uani 1 1 d . . . . .
H9A H 0.990323 0.681860 0.360892 0.078 Uiso 1 1 calc GR . . . .
H9B H 1.125280 0.589951 0.379569 0.078 Uiso 1 1 calc GR . . . .
H9C H 1.122183 0.685478 0.421350 0.078 Uiso 1 1 calc GR . . . .
C10 C 0.7369(3) 0.49617(14) 0.56298(8) 0.0414(4) Uani 1 1 d . . . . .
H10 H 0.787839 0.541528 0.594996 0.050 Uiso 1 1 calc R . . . .
C11 C 0.9210(4) 0.43617(18) 0.54073(10) 0.0572(5) Uani 1 1 d . . . . .
H11A H 0.883157 0.397922 0.505022 0.086 Uiso 1 1 calc GR . . . .
H11B H 0.965234 0.391957 0.572961 0.086 Uiso 1 1 calc GR . . . .
H11C H 1.030432 0.480850 0.530202 0.086 Uiso 1 1 calc GR . . . .
C12 C 0.5729(3) 0.43242(13) 0.59323(7) 0.0408(4) Uani 1 1 d . . . . .
C13 C 0.4621(3) 0.46767(13) 0.64421(8) 0.0401(4) Uani 1 1 d . . . . .
C14 C 0.3057(3) 0.41018(15) 0.66984(9) 0.0492(5) Uani 1 1 d . . . . .
H14 H 0.228788 0.435693 0.702355 0.059 Uiso 1 1 calc R . . . .
C15 C 0.2635(4) 0.31568(15) 0.64748(10) 0.0543(5) Uani 1 1 d . . . . .
H15 H 0.160866 0.277184 0.665338 0.065 Uiso 1 1 calc R . . . .
C16 C 0.3747(4) 0.27950(14) 0.59874(10) 0.0574(6) Uani 1 1 d . . . . .
H16 H 0.349002 0.215638 0.583816 0.069 Uiso 1 1 calc R . . . .
C17 C 0.5248(4) 0.33746(14) 0.57165(9) 0.0527(5) Uani 1 1 d . . . . .
H17 H 0.596079 0.312191 0.537905 0.063 Uiso 1 1 calc R . . . .
C18 C 0.5184(3) 0.56017(15) 0.67930(7) 0.0434(4) Uani 1 1 d . . . . .
C19 C 0.3591(3) 0.63668(14) 0.69232(8) 0.0440(4) Uani 1 1 d . . . . .
C20 C 0.1897(3) 0.64901(15) 0.65448(9) 0.0487(5) Uani 1 1 d . . . . .
H20 H 0.169332 0.605991 0.621347 0.058 Uiso 1 1 calc R . . . .
C21 C 0.0513(4) 0.72460(16) 0.66562(11) 0.0593(6) Uani 1 1 d . . . . .
H21 H -0.061140 0.733173 0.639808 0.071 Uiso 1 1 calc R . . . .
C22 C 0.0807(5) 0.78751(17) 0.71541(12) 0.0674(7) Uani 1 1 d . . . . .
H22 H -0.012307 0.838547 0.723085 0.081 Uiso 1 1 calc R . . . .
C23 C 0.2481(5) 0.77497(17) 0.75394(11) 0.0674(7) Uani 1 1 d . . . . .
H23 H 0.265907 0.816860 0.787759 0.081 Uiso 1 1 calc R . . . .
C24 C 0.3874(4) 0.70085(16) 0.74223(9) 0.0567(6) Uani 1 1 d . . . . .
H24 H 0.501122 0.693368 0.767665 0.068 Uiso 1 1 calc R . . . .
H2 H 0.468(4) 0.669(2) 0.5144(12) 0.070(8) Uiso 1 1 d . . . . .


_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
O1 C1 1.221(2) . ?
O2 C2 1.409(2) . ?
O2 H2 0.87(3) . ?
O3 C18 1.217(2) . ?
N1 C1 1.355(2) . ?
N1 C4 1.405(2) . ?
N1 C9 1.454(3) . ?
C1 C2 1.543(3) . ?
C2 C3 1.512(2) . ?
C2 C10 1.555(2) . ?
C3 C4 1.392(2) . ?
C3 C8 1.375(3) . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.400(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9800 . ?
C10 C11 1.524(3) . ?
C10 C12 1.519(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.402(3) . ?
C12 C17 1.392(3) . ?
C13 C14 1.395(3) . ?
C13 C18 1.500(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.488(3) . ?
C19 C20 1.386(3) . ?
C19 C24 1.393(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.379(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.371(4) . ?
C24 H24 0.9300 . ?

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
C2 O2 H2 104.8(19) . . ?
C1 N1 C4 110.91(16) . . ?
C1 N1 C9 124.04(17) . . ?
C4 N1 C9 124.98(16) . . ?
O1 C1 N1 126.27(18) . . ?
O1 C1 C2 125.29(16) . . ?
N1 C1 C2 108.42(15) . . ?
O2 C2 C1 112.57(14) . . ?
O2 C2 C3 114.61(16) . . ?
O2 C2 C10 106.28(13) . . ?
C1 C2 C10 106.78(15) . . ?
C3 C2 C1 101.40(13) . . ?
C3 C2 C10 115.05(14) . . ?
C4 C3 C2 108.45(16) . . ?
C8 C3 C2 131.85(17) . . ?
C8 C3 C4 119.68(16) . . ?
C3 C4 N1 109.92(15) . . ?
C5 C4 N1 127.98(18) . . ?
C5 C4 C3 122.04(18) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.34(19) . . ?
C6 C5 H5 121.3 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.51(18) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C3 C8 C7 119.01(19) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10 106.5 . . ?
C11 C10 C2 112.12(15) . . ?
C11 C10 H10 106.5 . . ?
C12 C10 C2 111.50(16) . . ?
C12 C10 H10 106.5 . . ?
C12 C10 C11 113.32(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C10 120.94(17) . . ?
C17 C12 C10 121.92(17) . . ?
C17 C12 C13 117.14(18) . . ?
C12 C13 C18 123.42(17) . . ?
C14 C13 C12 120.34(18) . . ?
C14 C13 C18 115.77(16) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(2) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.29(19) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 118.9 . . ?
C16 C17 C12 122.12(19) . . ?
C16 C17 H17 118.9 . . ?
O3 C18 C13 119.18(19) . . ?
O3 C18 C19 121.03(18) . . ?
C19 C18 C13 119.61(17) . . ?
C20 C19 C18 121.88(16) . . ?
C20 C19 C24 119.4(2) . . ?
C24 C19 C18 118.7(2) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.49(19) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.2(2) . . ?
C23 C24 H24 119.9 . . ?

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
O1 C1 C2 O2 49.0(3) . . . . ?
O1 C1 C2 C3 171.97(19) . . . . ?
O1 C1 C2 C10 -67.2(2) . . . . ?
O2 C2 C3 C4 128.96(16) . . . . ?
O2 C2 C3 C8 -49.4(3) . . . . ?
O2 C2 C10 C11 -177.00(17) . . . . ?
O2 C2 C10 C12 54.73(18) . . . . ?
O3 C18 C19 C20 157.86(19) . . . . ?
O3 C18 C19 C24 -18.8(3) . . . . ?
N1 C1 C2 O2 -132.46(16) . . . . ?
N1 C1 C2 C3 -9.52(19) . . . . ?
N1 C1 C2 C10 111.28(17) . . . . ?
N1 C4 C5 C6 -175.12(18) . . . . ?
C1 N1 C4 C3 -3.5(2) . . . . ?
C1 N1 C4 C5 173.69(19) . . . . ?
C1 C2 C3 C4 7.43(18) . . . . ?
C1 C2 C3 C8 -170.93(18) . . . . ?
C1 C2 C10 C11 -56.6(2) . . . . ?
C1 C2 C10 C12 175.10(14) . . . . ?
C2 C3 C4 N1 -3.11(19) . . . . ?
C2 C3 C4 C5 179.55(17) . . . . ?
C2 C3 C8 C7 178.67(18) . . . . ?
C2 C10 C12 C13 -89.25(19) . . . . ?
C2 C10 C12 C17 90.3(2) . . . . ?
C3 C2 C10 C11 55.0(2) . . . . ?
C3 C2 C10 C12 -73.25(19) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C4 N1 C1 O1 -173.14(19) . . . . ?
C4 N1 C1 C2 8.4(2) . . . . ?
C4 C3 C8 C7 0.5(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C3 1.0(3) . . . . ?
C8 C3 C4 N1 175.49(16) . . . . ?
C8 C3 C4 C5 -1.9(3) . . . . ?
C9 N1 C1 O1 4.0(3) . . . . ?
C9 N1 C1 C2 -174.50(17) . . . . ?
C9 N1 C4 C3 179.44(18) . . . . ?
C9 N1 C4 C5 -3.4(3) . . . . ?
C10 C2 C3 C4 -107.37(17) . . . . ?
C10 C2 C3 C8 74.3(2) . . . . ?
C10 C12 C13 C14 177.15(17) . . . . ?
C10 C12 C13 C18 -11.0(3) . . . . ?
C10 C12 C17 C16 -179.52(19) . . . . ?
C11 C10 C12 C13 143.13(18) . . . . ?
C11 C10 C12 C17 -37.3(2) . . . . ?
C12 C13 C14 C15 3.1(3) . . . . ?
C12 C13 C18 O3 -54.4(2) . . . . ?
C12 C13 C18 C19 130.39(19) . . . . ?
C13 C12 C17 C16 0.1(3) . . . . ?
C13 C14 C15 C16 -1.3(3) . . . . ?
C13 C18 C19 C20 -27.0(3) . . . . ?
C13 C18 C19 C24 156.30(17) . . . . ?
C14 C13 C18 O3 117.8(2) . . . . ?
C14 C13 C18 C19 -57.4(2) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C15 C16 C17 C12 1.7(3) . . . . ?
C17 C12 C13 C14 -2.5(3) . . . . ?
C17 C12 C13 C18 169.42(18) . . . . ?
C18 C13 C14 C15 -169.32(19) . . . . ?
C18 C19 C20 C21 -175.99(18) . . . . ?
C18 C19 C24 C23 177.18(19) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C19 C24 C23 0.4(3) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C24 1.0(4) . . . . ?
C22 C23 C24 C19 -1.3(3) . . . . ?
C24 C19 C20 C21 0.6(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 1.930
_oxdiff_exptl_absorpt_empirical_full_min 0.374
