# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_20220730c_auto
_database_code_depnum_ccdc_archive 'CCDC 2235178'
loop_
_audit_author_name
_audit_author_address
'Guo Yawen'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-01-09 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
(3R)-1,3-dimethyl-3-(2-methyl-2-nitro-3-phenylpropyl)indolin-2-one
_chemical_formula_moiety         'C20 H22 N2 O3'
_chemical_formula_sum            'C20 H22 N2 O3'
_chemical_formula_weight         338.39
_chemical_melting_point          457
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      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                   8.1551(9)
_cell_length_b                   11.4451(13)
_cell_length_c                   11.4726(13)
_cell_angle_alpha                62.610(11)
_cell_angle_beta                 70.408(10)
_cell_angle_gamma                87.885(9)
_cell_volume                     886.86(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25961
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.4510
_cell_measurement_theta_min      4.3420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       9
_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            32637
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.835
_diffrn_reflns_theta_min         4.394
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3327
_reflns_number_total             3536
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0116(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.057
_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)+(0.0387P)²+0.3165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0872
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B)
1.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C24(H24), C21(H21), C2(H2), C22(H22), C23(H23), C4(H4), C5(H5),
 C3(H3)
1.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O13 O 0.30016(10) 0.54349(7) 0.01503(8) 0.02307(19) Uani 1 1 d . . . . .
O14 O 0.07509(10) 0.57496(8) 0.15807(8) 0.0259(2) Uani 1 1 d . . . . .
O17 O 0.51555(13) 0.90063(8) 0.17303(9) 0.0326(2) Uani 1 1 d . . . . .
C25 C 0.09732(14) 0.74367(10) -0.20107(11) 0.0202(2) Uani 1 1 d . . . . .
H25 H 0.138887 0.659997 -0.175702 0.024 Uiso 1 1 calc R U . . .
N12 N 0.22115(11) 0.61268(9) 0.06563(9) 0.0177(2) Uani 1 1 d . . . . .
C16 C 0.19306(14) 0.82286(11) 0.08141(11) 0.0211(2) Uani 1 1 d . . . . .
H16A H 0.082988 0.830927 0.063139 0.032 Uiso 1 1 calc R U . . .
H16B H 0.252271 0.911541 0.047265 0.032 Uiso 1 1 calc R U . . .
H16C H 0.167420 0.770125 0.182749 0.032 Uiso 1 1 calc R U . . .
C7 C 0.51604(14) 0.69062(10) 0.16191(11) 0.0189(2) Uani 1 1 d . . . . .
N9 N 0.34995(13) 0.70801(9) 0.36413(10) 0.0231(2) Uani 1 1 d . . . . .
C11 C 0.31138(13) 0.75475(10) 0.00571(11) 0.0173(2) Uani 1 1 d . . . . .
C10 C 0.49432(13) 0.74525(10) 0.01814(11) 0.0184(2) Uani 1 1 d . . . . .
H10A H 0.561416 0.835804 -0.041819 0.022 Uiso 1 1 calc R U . . .
H10B H 0.553761 0.690055 -0.024781 0.022 Uiso 1 1 calc R U . . .
C24 C -0.04624(15) 0.76526(11) -0.24479(11) 0.0229(2) Uani 1 1 d . . . . .
H24 H -0.101877 0.696355 -0.248710 0.027 Uiso 1 1 calc R U . . .
C1 C 0.31610(14) 0.57529(11) 0.39621(11) 0.0196(2) Uani 1 1 d . . . . .
C19 C 0.71458(14) 0.68455(13) 0.13437(12) 0.0269(3) Uani 1 1 d . . . . .
H19A H 0.752796 0.620779 0.099353 0.040 Uiso 1 1 calc R U . . .
H19B H 0.735612 0.656336 0.222155 0.040 Uiso 1 1 calc R U . . .
H19C H 0.781066 0.772706 0.064175 0.040 Uiso 1 1 calc R U . . .
C20 C 0.18097(14) 0.84320(10) -0.19399(10) 0.0183(2) Uani 1 1 d . . . . .
C21 C 0.11508(16) 0.96435(11) -0.22985(13) 0.0258(3) Uani 1 1 d . . . . .
H21 H 0.168729 1.032915 -0.224203 0.031 Uiso 1 1 calc R U . . .
C15 C 0.34245(14) 0.82419(10) -0.15337(11) 0.0184(2) Uani 1 1 d . . . . .
H15A H 0.411729 0.912698 -0.197550 0.022 Uiso 1 1 calc R U . . .
H15B H 0.415528 0.771989 -0.194569 0.022 Uiso 1 1 calc R U . . .
C2 C 0.21007(15) 0.47152(12) 0.52226(12) 0.0252(3) Uani 1 1 d . . . . .
H2 H 0.145158 0.484831 0.600061 0.030 Uiso 1 1 calc R U . . .
C22 C -0.02791(16) 0.98604(12) -0.27369(13) 0.0285(3) Uani 1 1 d . . . . .
H22 H -0.071108 1.069070 -0.297735 0.034 Uiso 1 1 calc R U . . .
C6 C 0.40931(13) 0.55895(10) 0.27906(11) 0.0181(2) Uani 1 1 d . . . . .
C23 C -0.10803(15) 0.88672(12) -0.28251(12) 0.0242(2) Uani 1 1 d . . . . .
H23 H -0.204375 0.902136 -0.314170 0.029 Uiso 1 1 calc R U . . .
C4 C 0.29667(16) 0.32736(11) 0.41653(13) 0.0274(3) Uani 1 1 d . . . . .
H4 H 0.290230 0.240864 0.425179 0.033 Uiso 1 1 calc R U . . .
C5 C 0.40100(15) 0.43431(11) 0.28923(12) 0.0223(2) Uani 1 1 d . . . . .
H5 H 0.465118 0.421352 0.211022 0.027 Uiso 1 1 calc R U . . .
C3 C 0.20240(16) 0.34673(12) 0.53042(12) 0.0286(3) Uani 1 1 d . . . . .
H3 H 0.131087 0.273089 0.615787 0.034 Uiso 1 1 calc R U . . .
C8 C 0.46250(15) 0.78226(11) 0.22870(12) 0.0225(2) Uani 1 1 d . . . . .
C18 C 0.28631(19) 0.75644(14) 0.46600(13) 0.0336(3) Uani 1 1 d . . . . .
H18A H 0.157504 0.741038 0.504476 0.050 Uiso 1 1 calc R U . . .
H18B H 0.327159 0.851850 0.419866 0.050 Uiso 1 1 calc R U . . .
H18C H 0.331332 0.709097 0.542372 0.050 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
O13 N12 1.2303(12) . ?
O14 N12 1.2245(12) . ?
O17 C8 1.2216(14) . ?
C25 H25 0.9500 . ?
C25 C24 1.3935(16) . ?
C25 C20 1.3961(15) . ?
N12 C11 1.5422(13) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 C11 1.5160(14) . ?
C7 C10 1.5433(14) . ?
C7 C19 1.5476(15) . ?
C7 C6 1.5112(15) . ?
C7 C8 1.5359(15) . ?
N9 C1 1.4027(14) . ?
N9 C8 1.3656(15) . ?
N9 C18 1.4527(14) . ?
C11 C10 1.5409(14) . ?
C11 C15 1.5482(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C24 H24 0.9500 . ?
C24 C23 1.3837(16) . ?
C1 C2 1.3807(16) . ?
C1 C6 1.3981(15) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.3960(15) . ?
C20 C15 1.5152(14) . ?
C21 H21 0.9500 . ?
C21 C22 1.3898(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.3900(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3909(17) . ?
C6 C5 1.3791(15) . ?
C23 H23 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.3978(16) . ?
C4 C3 1.3884(18) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C24 C25 H25 119.5 . . ?
C24 C25 C20 120.97(10) . . ?
C20 C25 H25 119.5 . . ?
O13 N12 C11 117.39(8) . . ?
O14 N12 O13 123.28(9) . . ?
O14 N12 C11 119.32(8) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
C10 C7 C19 106.70(8) . . ?
C6 C7 C10 117.68(9) . . ?
C6 C7 C19 110.50(9) . . ?
C6 C7 C8 102.02(8) . . ?
C8 C7 C10 113.02(9) . . ?
C8 C7 C19 106.44(9) . . ?
C1 N9 C18 124.03(10) . . ?
C8 N9 C1 111.09(9) . . ?
C8 N9 C18 124.65(10) . . ?
N12 C11 C15 105.67(8) . . ?
C16 C11 N12 109.06(8) . . ?
C16 C11 C10 114.20(8) . . ?
C16 C11 C15 112.64(9) . . ?
C10 C11 N12 108.19(8) . . ?
C10 C11 C15 106.65(8) . . ?
C7 C10 H10A 107.0 . . ?
C7 C10 H10B 107.0 . . ?
C11 C10 C7 121.50(9) . . ?
C11 C10 H10A 107.0 . . ?
C11 C10 H10B 107.0 . . ?
H10A C10 H10B 106.7 . . ?
C25 C24 H24 119.9 . . ?
C23 C24 C25 120.22(10) . . ?
C23 C24 H24 119.9 . . ?
C2 C1 N9 127.66(10) . . ?
C2 C1 C6 122.52(10) . . ?
C6 C1 N9 109.81(9) . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
C7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C15 121.86(9) . . ?
C21 C20 C25 118.14(10) . . ?
C21 C20 C15 119.97(9) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.91(10) . . ?
C22 C21 H21 119.5 . . ?
C11 C15 H15A 108.0 . . ?
C11 C15 H15B 108.0 . . ?
C20 C15 C11 117.04(9) . . ?
C20 C15 H15A 108.0 . . ?
C20 C15 H15B 108.0 . . ?
H15A C15 H15B 107.3 . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.13(11) . . ?
C3 C2 H2 121.4 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.29(11) . . ?
C23 C22 H22 119.9 . . ?
C1 C6 C7 108.53(9) . . ?
C5 C6 C7 131.75(10) . . ?
C5 C6 C1 119.56(10) . . ?
C24 C23 C22 119.44(10) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.42(11) . . ?
C6 C5 C4 118.89(10) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.44(11) . . ?
C4 C3 H3 119.3 . . ?
O17 C8 C7 126.33(10) . . ?
O17 C8 N9 125.13(11) . . ?
N9 C8 C7 108.48(9) . . ?
N9 C18 H18A 109.5 . . ?
N9 C18 H18B 109.5 . . ?
N9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O13 N12 C11 C16 179.85(8) . . . . ?
O13 N12 C11 C10 -55.40(11) . . . . ?
O13 N12 C11 C15 58.52(11) . . . . ?
O14 N12 C11 C16 1.18(12) . . . . ?
O14 N12 C11 C10 125.93(9) . . . . ?
O14 N12 C11 C15 -120.15(10) . . . . ?
C25 C24 C23 C22 -1.29(17) . . . . ?
C25 C20 C21 C22 -1.09(17) . . . . ?
C25 C20 C15 C11 -85.02(12) . . . . ?
N12 C11 C10 C7 -71.33(11) . . . . ?
N12 C11 C15 C20 63.84(11) . . . . ?
C16 C11 C10 C7 50.31(13) . . . . ?
C16 C11 C15 C20 -55.14(12) . . . . ?
C7 C6 C5 C4 175.76(10) . . . . ?
N9 C1 C2 C3 -177.55(10) . . . . ?
N9 C1 C6 C7 1.40(12) . . . . ?
N9 C1 C6 C5 177.26(9) . . . . ?
C10 C7 C6 C1 -126.60(10) . . . . ?
C10 C7 C6 C5 58.23(15) . . . . ?
C10 C7 C8 O17 -52.61(15) . . . . ?
C10 C7 C8 N9 129.84(9) . . . . ?
C10 C11 C15 C20 178.82(8) . . . . ?
C24 C25 C20 C21 0.98(16) . . . . ?
C24 C25 C20 C15 -177.06(9) . . . . ?
C1 N9 C8 O17 -179.43(11) . . . . ?
C1 N9 C8 C7 -1.84(12) . . . . ?
C1 C2 C3 C4 -0.28(17) . . . . ?
C1 C6 C5 C4 1.03(16) . . . . ?
C19 C7 C10 C11 175.07(9) . . . . ?
C19 C7 C6 C1 110.55(10) . . . . ?
C19 C7 C6 C5 -64.62(14) . . . . ?
C19 C7 C8 O17 64.19(14) . . . . ?
C19 C7 C8 N9 -113.36(10) . . . . ?
C20 C25 C24 C23 0.20(16) . . . . ?
C20 C21 C22 C23 0.02(18) . . . . ?
C21 C20 C15 C11 96.97(12) . . . . ?
C21 C22 C23 C24 1.19(18) . . . . ?
C15 C11 C10 C7 175.40(9) . . . . ?
C15 C20 C21 C22 177.00(10) . . . . ?
C2 C1 C6 C7 -177.98(10) . . . . ?
C2 C1 C6 C5 -2.12(16) . . . . ?
C6 C7 C10 C11 50.30(14) . . . . ?
C6 C7 C8 O17 -179.95(11) . . . . ?
C6 C7 C8 N9 2.50(11) . . . . ?
C6 C1 C2 C3 1.71(16) . . . . ?
C5 C4 C3 C2 -0.73(18) . . . . ?
C3 C4 C5 C6 0.34(17) . . . . ?
C8 C7 C10 C11 -68.28(12) . . . . ?
C8 C7 C6 C1 -2.32(11) . . . . ?
C8 C7 C6 C5 -177.48(11) . . . . ?
C8 N9 C1 C2 179.63(11) . . . . ?
C8 N9 C1 C6 0.30(12) . . . . ?
C18 N9 C1 C2 4.99(18) . . . . ?
C18 N9 C1 C6 -174.35(10) . . . . ?
C18 N9 C8 O17 -4.82(18) . . . . ?
C18 N9 C8 C7 172.77(10) . . . . ?

_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_20220416b_auto
_database_code_depnum_ccdc_archive 'CCDC 2235177'
loop_
_audit_author_name
_audit_author_address
'Guo Yawen'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-01-09 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 N2 O3'
_chemical_formula_sum            'C14 H18 N2 O3'
_chemical_formula_weight         262.30
_chemical_melting_point          367
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.3740(4)
_cell_length_b                   6.6672(3)
_cell_length_c                   15.1512(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.804(4)
_cell_angle_gamma                90
_cell_volume                     1335.07(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3925
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.6830
_cell_measurement_theta_min      4.7640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11615
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.350
_diffrn_reflns_theta_min         4.109
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1859
_reflns_number_total             2637
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      1.030
_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)+(0.1377P)²+0.3462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.2162
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
1.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C3(H3)
1.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C15(H15A,H15B,
 H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O17 O 0.52368(13) 0.3792(3) 0.38967(13) 0.0354(5) Uani 1 1 d . . . . .
O13 O 0.80406(15) -0.0221(3) 0.59697(14) 0.0395(6) Uani 1 1 d . . . . .
O14 O 0.85995(14) 0.2525(3) 0.66201(15) 0.0405(6) Uani 1 1 d . . . . .
N9 N 0.64967(15) 0.1910(3) 0.34246(15) 0.0272(5) Uani 1 1 d . . . . .
N12 N 0.79153(15) 0.1486(4) 0.62260(15) 0.0300(6) Uani 1 1 d . . . . .
C1 C 0.75590(18) 0.1755(4) 0.36416(18) 0.0261(6) Uani 1 1 d . . . . .
C6 C 0.79114(18) 0.3107(4) 0.43236(18) 0.0268(6) Uani 1 1 d . . . . .
C10 C 0.68778(19) 0.4343(4) 0.55482(18) 0.0280(6) Uani 1 1 d . . . . .
H10A H 0.743236 0.517001 0.586904 0.034 Uiso 1 1 calc R U . . .
H10B H 0.623977 0.507446 0.557874 0.034 Uiso 1 1 calc R U . . .
C8 C 0.61287(18) 0.3320(4) 0.39420(18) 0.0276(6) Uani 1 1 d . . . . .
C18 C 0.58804(19) 0.0761(4) 0.27329(18) 0.0301(6) Uani 1 1 d . . . . .
H18A H 0.612252 0.097597 0.216157 0.045 Uiso 1 1 calc R U . . .
H18B H 0.517430 0.119819 0.268303 0.045 Uiso 1 1 calc R U . . .
H18C H 0.592748 -0.066708 0.288619 0.045 Uiso 1 1 calc R U . . .
C11 C 0.68407(17) 0.2401(4) 0.60814(18) 0.0288(6) Uani 1 1 d . . . . .
C5 C 0.89379(19) 0.3243(4) 0.46251(19) 0.0307(6) Uani 1 1 d . . . . .
H5 H 0.918946 0.416458 0.508384 0.037 Uiso 1 1 calc R U . . .
C2 C 0.82002(19) 0.0517(4) 0.32567(18) 0.0284(6) Uani 1 1 d . . . . .
H2 H 0.794755 -0.040482 0.279811 0.034 Uiso 1 1 calc R U . . .
C4 C 0.95992(19) 0.2008(4) 0.4247(2) 0.0323(6) Uani 1 1 d . . . . .
H4 H 1.030513 0.208170 0.445571 0.039 Uiso 1 1 calc R U . . .
C7 C 0.70225(18) 0.4290(4) 0.45586(18) 0.0276(6) Uani 1 1 d . . . . .
C16 C 0.6612(2) 0.2896(5) 0.7011(2) 0.0345(7) Uani 1 1 d . . . . .
H16A H 0.660388 0.165728 0.735818 0.052 Uiso 1 1 calc R U . . .
H16B H 0.595022 0.355301 0.696224 0.052 Uiso 1 1 calc R U . . .
H16C H 0.713489 0.379787 0.731238 0.052 Uiso 1 1 calc R U . . .
C19 C 0.7077(2) 0.6482(4) 0.4248(2) 0.0337(7) Uani 1 1 d . . . . .
H19A H 0.767276 0.713269 0.458509 0.051 Uiso 1 1 calc R U . . .
H19B H 0.646502 0.719708 0.435154 0.051 Uiso 1 1 calc R U . . .
H19C H 0.712638 0.650988 0.360940 0.051 Uiso 1 1 calc R U . . .
C15 C 0.61082(19) 0.0849(4) 0.5632(2) 0.0329(7) Uani 1 1 d . . . . .
H15A H 0.630531 0.046808 0.505775 0.049 Uiso 1 1 calc R U . . .
H15B H 0.542335 0.141221 0.553119 0.049 Uiso 1 1 calc R U . . .
H15C H 0.612172 -0.033764 0.601493 0.049 Uiso 1 1 calc R U . . .
C3 C 0.92418(19) 0.0677(4) 0.3572(2) 0.0323(7) Uani 1 1 d . . . . .
H3 H 0.970589 -0.013824 0.331754 0.039 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
O17 C8 1.225(3) . ?
O13 N12 1.223(3) . ?
O14 N12 1.227(3) . ?
N9 C1 1.412(3) . ?
N9 C8 1.363(4) . ?
N9 C18 1.449(3) . ?
N12 C11 1.546(3) . ?
C1 C6 1.398(4) . ?
C1 C2 1.382(4) . ?
C6 C5 1.382(4) . ?
C6 C7 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.531(4) . ?
C10 C7 1.541(4) . ?
C8 C7 1.542(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C11 C16 1.523(4) . ?
C11 C15 1.513(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.394(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.406(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(4) . ?
C7 C19 1.540(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 H3 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 N9 C18 124.8(2) . . ?
C8 N9 C1 110.8(2) . . ?
C8 N9 C18 124.4(2) . . ?
O13 N12 O14 123.5(2) . . ?
O13 N12 C11 119.5(2) . . ?
O14 N12 C11 117.0(2) . . ?
C6 C1 N9 109.8(2) . . ?
C2 C1 N9 127.8(2) . . ?
C2 C1 C6 122.4(2) . . ?
C1 C6 C7 108.8(2) . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C7 131.6(3) . . ?
H10A C10 H10B 106.8 . . ?
C11 C10 H10A 107.1 . . ?
C11 C10 H10B 107.1 . . ?
C11 C10 C7 120.9(2) . . ?
C7 C10 H10A 107.1 . . ?
C7 C10 H10B 107.1 . . ?
O17 C8 N9 125.4(2) . . ?
O17 C8 C7 125.7(2) . . ?
N9 C8 C7 108.8(2) . . ?
N9 C18 H18A 109.5 . . ?
N9 C18 H18B 109.5 . . ?
N9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C11 N12 107.70(19) . . ?
C16 C11 N12 105.6(2) . . ?
C16 C11 C10 109.4(2) . . ?
C15 C11 N12 108.5(2) . . ?
C15 C11 C10 114.3(2) . . ?
C15 C11 C16 110.9(2) . . ?
C6 C5 H5 120.5 . . ?
C6 C5 C4 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C6 C7 C10 117.4(2) . . ?
C6 C7 C8 101.7(2) . . ?
C6 C7 C19 110.3(2) . . ?
C10 C7 C8 113.4(2) . . ?
C19 C7 C10 107.1(2) . . ?
C19 C7 C8 106.3(2) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
C7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?

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
O17 C8 C7 C6 179.9(3) . . . . ?
O17 C8 C7 C10 52.9(4) . . . . ?
O17 C8 C7 C19 -64.6(3) . . . . ?
O13 N12 C11 C10 -123.1(3) . . . . ?
O13 N12 C11 C16 120.1(3) . . . . ?
O13 N12 C11 C15 1.1(3) . . . . ?
O14 N12 C11 C10 58.7(3) . . . . ?
O14 N12 C11 C16 -58.1(3) . . . . ?
O14 N12 C11 C15 -177.0(2) . . . . ?
N9 C1 C6 C5 -178.3(2) . . . . ?
N9 C1 C6 C7 -1.8(3) . . . . ?
N9 C1 C2 C3 178.1(2) . . . . ?
N9 C8 C7 C6 -2.8(3) . . . . ?
N9 C8 C7 C10 -129.9(2) . . . . ?
N9 C8 C7 C19 112.6(2) . . . . ?
C1 N9 C8 O17 179.2(3) . . . . ?
C1 N9 C8 C7 2.0(3) . . . . ?
C1 C6 C5 C4 -0.7(4) . . . . ?
C1 C6 C7 C10 127.1(3) . . . . ?
C1 C6 C7 C8 2.7(3) . . . . ?
C1 C6 C7 C19 -109.8(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C6 C5 C4 C3 0.8(4) . . . . ?
C8 N9 C1 C6 -0.1(3) . . . . ?
C8 N9 C1 C2 -179.1(3) . . . . ?
C18 N9 C1 C6 178.6(2) . . . . ?
C18 N9 C1 C2 -0.4(4) . . . . ?
C18 N9 C8 O17 0.5(4) . . . . ?
C18 N9 C8 C7 -176.8(2) . . . . ?
C11 C10 C7 C6 -52.6(3) . . . . ?
C11 C10 C7 C8 65.7(3) . . . . ?
C11 C10 C7 C19 -177.3(2) . . . . ?
C5 C6 C7 C10 -56.8(4) . . . . ?
C5 C6 C7 C8 178.7(3) . . . . ?
C5 C6 C7 C19 66.2(4) . . . . ?
C5 C4 C3 C2 -0.8(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C1 C6 C7 177.3(2) . . . . ?
C7 C6 C5 C4 -176.3(3) . . . . ?
C7 C10 C11 N12 70.0(3) . . . . ?
C7 C10 C11 C16 -175.7(2) . . . . ?
C7 C10 C11 C15 -50.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2235872'
loop_
_audit_author_name
_audit_author_address
'Guo Yawen'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        
(R)-3-((2,2-dimethyl-5-nitro-1,3-dioxan-5-yl)methyl)-1,3-dimethylindolin-2-one
_chemical_formula_moiety         'C17 H22 N2 O5'
_chemical_formula_sum            'C17 H22 N2 O5'
_chemical_formula_weight         334.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1N1
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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.2000(3)
_cell_length_b                   12.8987(3)
_cell_length_c                   12.6329(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1662.07(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5583
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.8520
_cell_measurement_theta_min      5.5230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_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  0.0759
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10868
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.631
_diffrn_reflns_theta_min         3.426
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  28.00   0.50    0.06    --   47.03 -19.00-150.00  110
  2  ω     44.00  72.00   0.50    0.22    --  104.75 -61.00 -90.00   56
  3  ω     34.00  61.00   0.50    0.22    --  104.75 -61.00   0.00   54
  4  ω     32.00  83.00   0.50    0.22    --  104.75 -77.00 150.00  102
  5  ω     91.00 156.00   0.50    0.22    --  104.75  15.00 120.00  130
  6  ω     99.00 150.00   0.50    0.22    --  104.75 104.00  97.00  102
  7  ω     -2.00  80.00   0.50    0.06    --   47.03-104.00  -3.00  164
  8  ω     47.00  72.00   0.50    0.22    --  104.75-104.00  -3.00   50
  9  ω    -21.00   4.00   0.50    0.06    --  -47.03  19.00 120.00   50
 10  ω    -68.00 -30.00   0.50    0.22    -- -102.00  61.00 120.00   76
 11  ω    -69.00 -44.00   0.50    0.22    -- -102.00  61.00  60.00   50
 12  ω    -67.00 -30.00   0.50    0.22    -- -102.00  61.00  30.00   74
 13  ω    -75.00 -30.00   0.50    0.22    -- -102.00  77.00 -60.00   90
 14  ω    -64.00 -39.00   0.50    0.22    -- -102.00  61.00-120.00   50
 15  ω    -59.00 -29.00   0.50    0.22    -- -102.00  61.00-150.00   60
 16  ω   -169.00 -90.00   0.50    0.22    -- -102.00 -15.00-120.00  158
 17  ω   -108.00 -60.00   0.50    0.22    -- -102.00 104.00  97.00   96
 18  ω    -49.00 -23.00   0.50    0.06    --  -47.03 104.00  97.00   52
 19  ω   -126.00 -94.00   0.50    0.22    -- -102.00 -45.00-120.00   64
 20  ω   -171.00-145.00   0.50    0.22    -- -102.00 -45.00-120.00   52
 21  ω   -148.00 -83.00   0.50    0.22    -- -102.00-104.00  -3.00  130
 22  ω   -114.00 -76.00   0.50    0.06    --  -47.03-125.00 150.00   76
 23  ω   -104.00 -72.00   0.50    0.06    --  -47.03-125.00 120.00   64
 24  ω   -119.00 -73.00   0.50    0.06    --  -47.03-125.00 -60.00   92
 25  ω   -103.00 -77.00   0.50    0.06    --  -47.03-125.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0394261000
_diffrn_orient_matrix_UB_12      -0.0842272000
_diffrn_orient_matrix_UB_13      -0.0804026000
_diffrn_orient_matrix_UB_21      0.0825906000
_diffrn_orient_matrix_UB_22      0.0542824000
_diffrn_orient_matrix_UB_23      -0.0857046000
_diffrn_orient_matrix_UB_31      0.1202595000
_diffrn_orient_matrix_UB_32      -0.0648978000
_diffrn_orient_matrix_UB_33      0.0325156000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                2671
_reflns_number_total             3147
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1009 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.031
_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)+(0.0334P)²+0.2613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1072
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C15(H15A,H15B)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7)
1.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.5032(3) 0.99611(19) 0.3906(2) 0.0322(5) Uani 1 1 d . . . . .
N1 N 0.6539(3) 0.8763(2) 0.4471(2) 0.0285(6) Uani 1 1 d . . . . .
C1 C 0.5397(3) 0.9301(2) 0.4534(3) 0.0266(7) Uani 1 1 d . . . . .
O2 O 0.2781(2) 0.58569(16) 0.4514(2) 0.0311(5) Uani 1 1 d . . . . .
N2 N 0.3394(3) 0.7856(2) 0.3550(2) 0.0288(6) Uani 1 1 d . . . . .
C2 C 0.4676(3) 0.8982(3) 0.5546(3) 0.0265(7) Uani 1 1 d . . . . .
O3 O 0.0928(2) 0.68019(17) 0.4039(2) 0.0305(5) Uani 1 1 d . . . . .
C3 C 0.5561(3) 0.8135(3) 0.5965(3) 0.0272(7) Uani 1 1 d . . . . .
O4 O 0.4458(3) 0.7459(2) 0.3338(2) 0.0393(6) Uani 1 1 d . . . . .
C4 C 0.5457(4) 0.7526(3) 0.6864(3) 0.0294(7) Uani 1 1 d . . . . .
H4 H 0.472557 0.759333 0.732374 0.035 Uiso 1 1 calc R U . . .
O5 O 0.2755(3) 0.8372(2) 0.2918(2) 0.0409(7) Uani 1 1 d . . . . .
C5 C 0.6448(4) 0.6812(3) 0.7080(3) 0.0323(8) Uani 1 1 d . . . . .
H5 H 0.639030 0.638275 0.768901 0.039 Uiso 1 1 calc R U . . .
C6 C 0.7521(4) 0.6728(3) 0.6407(3) 0.0329(8) Uani 1 1 d . . . . .
H6 H 0.819165 0.624199 0.656633 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7634(4) 0.7341(3) 0.5504(3) 0.0325(8) Uani 1 1 d . . . . .
H7 H 0.836675 0.728110 0.504307 0.039 Uiso 1 1 calc R U . . .
C8 C 0.6639(3) 0.8038(2) 0.5306(3) 0.0274(7) Uani 1 1 d . . . . .
C9 C 0.7388(4) 0.8806(3) 0.3555(3) 0.0336(8) Uani 1 1 d . . . . .
H9A H 0.711017 0.828481 0.303797 0.050 Uiso 1 1 calc R U . . .
H9B H 0.829352 0.866672 0.377270 0.050 Uiso 1 1 calc R U . . .
H9C H 0.733695 0.949722 0.323495 0.050 Uiso 1 1 calc R U . . .
C10 C 0.4674(4) 0.9931(3) 0.6294(3) 0.0322(8) Uani 1 1 d . . . . .
H10A H 0.557747 1.016220 0.641243 0.048 Uiso 1 1 calc R U . . .
H10B H 0.427661 0.973736 0.697225 0.048 Uiso 1 1 calc R U . . .
H10C H 0.416742 1.049402 0.597219 0.048 Uiso 1 1 calc R U . . .
C11 C 0.3238(3) 0.8691(2) 0.5336(3) 0.0263(7) Uani 1 1 d . . . . .
H11A H 0.282446 0.929645 0.498958 0.032 Uiso 1 1 calc R U . . .
H11B H 0.281182 0.861293 0.603531 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2860(3) 0.7731(2) 0.4679(3) 0.0249(7) Uani 1 1 d . . . . .
C13 C 0.3322(3) 0.6693(2) 0.5106(3) 0.0289(7) Uani 1 1 d . . . . .
H13A H 0.429077 0.666054 0.507218 0.035 Uiso 1 1 calc R U . . .
H13B H 0.305739 0.662698 0.585647 0.035 Uiso 1 1 calc R U . . .
C14 C 0.1384(3) 0.5839(2) 0.4457(3) 0.0293(7) Uani 1 1 d . . . . .
C15 C 0.1365(3) 0.7693(2) 0.4605(3) 0.0274(7) Uani 1 1 d . . . . .
H15A H 0.098938 0.768330 0.532771 0.033 Uiso 1 1 calc R U . . .
H15B H 0.104551 0.832600 0.424403 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1056(4) 0.5025(3) 0.3650(3) 0.0396(9) Uani 1 1 d . . . . .
H16A H 0.142642 0.522126 0.296364 0.059 Uiso 1 1 calc R U . . .
H16B H 0.010108 0.496268 0.358810 0.059 Uiso 1 1 calc R U . . .
H16C H 0.142467 0.435793 0.387344 0.059 Uiso 1 1 calc R U . . .
C17 C 0.0756(4) 0.5605(3) 0.5522(3) 0.0398(9) Uani 1 1 d . . . . .
H17A H 0.110805 0.495228 0.579979 0.060 Uiso 1 1 calc R U . . .
H17B H -0.019524 0.554317 0.543448 0.060 Uiso 1 1 calc R U . . .
H17C H 0.095129 0.616810 0.601814 0.060 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
O1 C1 1.221(4) . ?
N1 C1 1.358(4) . ?
N1 C8 1.413(4) . ?
N1 C9 1.446(5) . ?
C1 C2 1.531(5) . ?
O2 C13 1.423(4) . ?
O2 C14 1.427(4) . ?
N2 O4 1.229(4) . ?
N2 O5 1.226(4) . ?
N2 C12 1.535(4) . ?
C2 C3 1.514(5) . ?
C2 C10 1.547(5) . ?
C2 C11 1.536(5) . ?
O3 C14 1.427(4) . ?
O3 C15 1.426(4) . ?
C3 C4 1.384(5) . ?
C3 C8 1.385(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.540(5) . ?
C12 C13 1.518(5) . ?
C12 C15 1.529(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C16 1.501(5) . ?
C14 C17 1.521(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C1 N1 C8 110.9(3) . . ?
C1 N1 C9 122.8(3) . . ?
C8 N1 C9 125.4(3) . . ?
O1 C1 N1 125.4(3) . . ?
O1 C1 C2 125.6(3) . . ?
N1 C1 C2 108.9(3) . . ?
C13 O2 C14 115.2(2) . . ?
O4 N2 C12 118.1(3) . . ?
O5 N2 O4 123.6(3) . . ?
O5 N2 C12 118.3(3) . . ?
C1 C2 C10 107.4(3) . . ?
C1 C2 C11 112.3(3) . . ?
C3 C2 C1 101.5(3) . . ?
C3 C2 C10 111.0(3) . . ?
C3 C2 C11 117.0(3) . . ?
C11 C2 C10 107.3(3) . . ?
C15 O3 C14 114.5(3) . . ?
C4 C3 C2 130.6(3) . . ?
C4 C3 C8 120.2(3) . . ?
C8 C3 C2 109.2(3) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.5(3) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 121.4 . . ?
C8 C7 C6 117.2(3) . . ?
C8 C7 H7 121.4 . . ?
C3 C8 N1 109.4(3) . . ?
C7 C8 N1 128.3(3) . . ?
C7 C8 C3 122.3(3) . . ?
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 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 106.9 . . ?
C2 C11 H11B 106.9 . . ?
C2 C11 C12 121.9(3) . . ?
H11A C11 H11B 106.7 . . ?
C12 C11 H11A 106.9 . . ?
C12 C11 H11B 106.9 . . ?
N2 C12 C11 109.1(3) . . ?
C13 C12 N2 108.3(3) . . ?
C13 C12 C11 116.1(3) . . ?
C13 C12 C15 107.7(3) . . ?
C15 C12 N2 107.5(3) . . ?
C15 C12 C11 107.9(3) . . ?
O2 C13 C12 111.2(3) . . ?
O2 C13 H13A 109.4 . . ?
O2 C13 H13B 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O2 C14 C16 105.6(3) . . ?
O2 C14 C17 112.3(3) . . ?
O3 C14 O2 109.3(2) . . ?
O3 C14 C16 106.6(3) . . ?
O3 C14 C17 111.3(3) . . ?
C16 C14 C17 111.6(3) . . ?
O3 C15 C12 111.6(3) . . ?
O3 C15 H15A 109.3 . . ?
O3 C15 H15B 109.3 . . ?
C12 C15 H15A 109.3 . . ?
C12 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C1 C2 C3 178.6(3) . . . . ?
O1 C1 C2 C10 -64.9(4) . . . . ?
O1 C1 C2 C11 52.9(4) . . . . ?
N1 C1 C2 C3 -4.1(3) . . . . ?
N1 C1 C2 C10 112.4(3) . . . . ?
N1 C1 C2 C11 -129.8(3) . . . . ?
C1 N1 C8 C3 -2.8(4) . . . . ?
C1 N1 C8 C7 178.8(3) . . . . ?
C1 C2 C3 C4 -179.9(3) . . . . ?
C1 C2 C3 C8 2.4(3) . . . . ?
C1 C2 C11 C12 66.4(4) . . . . ?
N2 C12 C13 O2 -64.3(3) . . . . ?
N2 C12 C15 O3 64.6(3) . . . . ?
C2 C3 C4 C5 -178.1(3) . . . . ?
C2 C3 C8 N1 0.0(4) . . . . ?
C2 C3 C8 C7 178.5(3) . . . . ?
C2 C11 C12 N2 -62.0(4) . . . . ?
C2 C11 C12 C13 60.6(4) . . . . ?
C2 C11 C12 C15 -178.5(3) . . . . ?
C3 C2 C11 C12 -50.4(4) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
O4 N2 C12 C11 95.3(3) . . . . ?
O4 N2 C12 C13 -31.9(4) . . . . ?
O4 N2 C12 C15 -147.9(3) . . . . ?
C4 C3 C8 N1 -178.0(3) . . . . ?
C4 C3 C8 C7 0.5(5) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
O5 N2 C12 C11 -82.6(4) . . . . ?
O5 N2 C12 C13 150.2(3) . . . . ?
O5 N2 C12 C15 34.2(4) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C6 C7 C8 N1 177.9(3) . . . . ?
C6 C7 C8 C3 -0.3(5) . . . . ?
C8 N1 C1 O1 -178.3(3) . . . . ?
C8 N1 C1 C2 4.4(3) . . . . ?
C8 C3 C4 C5 -0.7(5) . . . . ?
C9 N1 C1 O1 -9.2(5) . . . . ?
C9 N1 C1 C2 173.6(3) . . . . ?
C9 N1 C8 C3 -171.6(3) . . . . ?
C9 N1 C8 C7 10.0(5) . . . . ?
C10 C2 C3 C4 66.2(5) . . . . ?
C10 C2 C3 C8 -111.4(3) . . . . ?
C10 C2 C11 C12 -175.8(3) . . . . ?
C11 C2 C3 C4 -57.3(5) . . . . ?
C11 C2 C3 C8 125.0(3) . . . . ?
C11 C12 C13 O2 172.6(3) . . . . ?
C11 C12 C15 O3 -177.9(3) . . . . ?
C13 O2 C14 O3 55.8(4) . . . . ?
C13 O2 C14 C16 170.1(3) . . . . ?
C13 O2 C14 C17 -68.1(3) . . . . ?
C13 C12 C15 O3 -51.8(4) . . . . ?
C14 O2 C13 C12 -56.3(4) . . . . ?
C14 O3 C15 C12 56.0(4) . . . . ?
C15 O3 C14 O2 -55.4(4) . . . . ?
C15 O3 C14 C16 -169.1(3) . . . . ?
C15 O3 C14 C17 69.1(4) . . . . ?
C15 C12 C13 O2 51.6(4) . . . . ?

_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 1.257
_oxdiff_exptl_absorpt_empirical_full_min 0.833
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_20220823a_auto
_database_code_depnum_ccdc_archive 'CCDC 2236062'
loop_
_audit_author_name
_audit_author_address
'Guo Yawen'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2022-08-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
3-methyl-3-((1-nitrocyclobutyl)methyl)-1-phenylindolin-2-one
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1N1
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      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                   10.3516(6)
_cell_length_b                   8.7894(3)
_cell_length_c                   10.7156(7)
_cell_angle_alpha                90
_cell_angle_beta                 118.800(8)
_cell_angle_gamma                90
_cell_volume                     854.35(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4450
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1430
_cell_measurement_theta_min      4.7290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8156
_diffrn_reflns_point_group_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.668
_diffrn_reflns_theta_min         4.709
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  73.00   0.50    0.07    --  104.75 -61.00 -30.00   82
  2  ω     32.00  66.00   0.50    0.07    --  104.75 -56.00 -61.00   68
  3  ω     32.00  73.00   0.50    0.07    --  104.75 -61.00-150.00   82
  4  ω     35.00 120.00   0.50    0.05    --   47.03  37.00-120.00  170
  5  ω     25.00 119.00   0.50    0.05    --   47.03  76.00 -64.00  188
  6  ω    -27.00  28.00   0.50    0.05    --   47.03 -19.00 150.00  110
  7  ω     32.00 117.00   0.50    0.07    --  104.75-125.00   0.00  170
  8  ω     32.00 108.00   0.50    0.07    --  104.75 -93.00  70.00  152
  9  ω    -24.00  28.00   0.50    0.05    --  -47.03  19.00  90.00  104
 10  ω   -119.00 -25.00   0.50    0.05    --  -47.03 -76.00 169.00  188
 11  ω   -118.00 -32.00   0.50    0.05    --  -47.03 -57.00  60.00  172
 12  ω   -174.00 -87.00   0.50    0.07    -- -102.00 -56.00 -61.00  174
 13  ω   -119.00 -71.00   0.50    0.05    --  -47.03-125.00  60.00   96
 14  ω   -175.00 -81.00   0.50    0.07    -- -102.00 -94.00  30.00  188
 15  ω   -175.00 -81.00   0.50    0.07    -- -102.00 -93.00  70.00  188
 16  ω   -103.00 -29.00   0.50    0.07    -- -102.00  77.00-150.00  148
 17  ω   -100.00 -29.00   0.50    0.07    -- -102.00  76.00 -64.00  142
 18  ω    -69.00 -29.00   0.50    0.07    -- -102.00  61.00   0.00   80
 19  ω    -62.00 -29.00   0.50    0.07    -- -102.00  56.00  80.00   66
 20  ω    -69.00 -29.00   0.50    0.07    -- -102.00  61.00 120.00   80
 21  ω    -69.00 -29.00   0.50    0.07    -- -102.00  61.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0275240000
_diffrn_orient_matrix_UB_12      0.0894037000
_diffrn_orient_matrix_UB_13      0.1085842000
_diffrn_orient_matrix_UB_21      0.1197399000
_diffrn_orient_matrix_UB_22      0.1155542000
_diffrn_orient_matrix_UB_23      0.0180662000
_diffrn_orient_matrix_UB_31      -0.1173327000
_diffrn_orient_matrix_UB_32      0.0968504000
_diffrn_orient_matrix_UB_33      -0.1216700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.825
_reflns_Friedel_fraction_max     0.747
_reflns_number_gt                2710
_reflns_number_total             3052
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 971 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0048(12)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.059
_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)+(0.0363P)²+0.2377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1112
_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:
 C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C4(H4), C15(H15), C13(H13), C14(H14), C12(H12), C5(H5), C7(H7),
 C6(H6)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_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
O24 O 0.4612(3) 0.6116(3) 0.5346(2) 0.0294(6) Uani 1 1 d . . . . .
O23 O 0.1976(3) 0.1502(3) 0.7057(3) 0.0363(7) Uani 1 1 d . . . . .
O22 O 0.0582(3) 0.3487(4) 0.6251(3) 0.0429(7) Uani 1 1 d . . . . .
N9 N 0.3636(3) 0.6944(3) 0.6753(3) 0.0257(6) Uani 1 1 d . . . . .
N21 N 0.1547(3) 0.2642(3) 0.6305(3) 0.0279(7) Uani 1 1 d . . . . .
C2 C 0.4600(3) 0.4452(4) 0.7194(3) 0.0200(7) Uani 1 1 d . . . . .
C1 C 0.4290(3) 0.5915(4) 0.6296(3) 0.0234(7) Uani 1 1 d . . . . .
C3 C 0.3943(3) 0.4854(4) 0.8138(3) 0.0224(7) Uani 1 1 d . . . . .
C8 C 0.3380(4) 0.6325(4) 0.7820(4) 0.0258(7) Uani 1 1 d . . . . .
C11 C 0.7076(4) 0.5185(4) 0.9268(4) 0.0272(8) Uani 1 1 d . . . . .
H11 H 0.656009 0.574126 0.964927 0.033 Uiso 1 1 calc R U . . .
C16 C 0.3896(3) 0.3059(4) 0.6224(3) 0.0209(7) Uani 1 1 d . . . . .
H16A H 0.429833 0.300413 0.555411 0.025 Uiso 1 1 calc R U . . .
H16B H 0.424125 0.214013 0.683195 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3888(4) 0.4049(4) 0.9218(4) 0.0280(8) Uani 1 1 d . . . . .
H4 H 0.429101 0.305327 0.946053 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6284(4) 0.4345(4) 0.8015(3) 0.0226(7) Uani 1 1 d . . . . .
C15 C 0.7075(4) 0.3526(4) 0.7489(3) 0.0271(8) Uani 1 1 d . . . . .
H15 H 0.656044 0.294022 0.664495 0.033 Uiso 1 1 calc R U . . .
C13 C 0.9371(4) 0.4403(5) 0.9421(4) 0.0355(9) Uani 1 1 d . . . . .
H13 H 1.041805 0.442246 0.989625 0.043 Uiso 1 1 calc R U . . .
C25 C 0.3262(4) 0.8488(4) 0.6202(4) 0.0367(9) Uani 1 1 d . . . . .
H25A H 0.383466 0.876536 0.572715 0.055 Uiso 1 1 calc R U . . .
H25B H 0.349251 0.919294 0.699043 0.055 Uiso 1 1 calc R U . . .
H25C H 0.220752 0.854486 0.551800 0.055 Uiso 1 1 calc R U . . .
C14 C 0.8602(4) 0.3559(5) 0.8186(4) 0.0334(9) Uani 1 1 d . . . . .
H14 H 0.912617 0.300000 0.781424 0.040 Uiso 1 1 calc R U . . .
C17 C 0.1393(4) 0.4152(4) 0.4174(4) 0.0327(9) Uani 1 1 d . . . . .
H17A H 0.037454 0.435734 0.398604 0.039 Uiso 1 1 calc R U . . .
H17B H 0.194817 0.511027 0.430773 0.039 Uiso 1 1 calc R U . . .
C19 C 0.1757(4) 0.1732(4) 0.4165(4) 0.0283(8) Uani 1 1 d . . . . .
H19A H 0.256343 0.103406 0.429604 0.034 Uiso 1 1 calc R U . . .
H19B H 0.085512 0.116174 0.397439 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8602(4) 0.5216(4) 0.9959(4) 0.0333(9) Uani 1 1 d . . . . .
H12 H 0.912366 0.579764 1.080420 0.040 Uiso 1 1 calc R U . . .
C18 C 0.2216(4) 0.2958(4) 0.5345(3) 0.0240(7) Uani 1 1 d . . . . .
C5 C 0.3226(4) 0.4733(5) 0.9947(4) 0.0354(9) Uani 1 1 d . . . . .
H5 H 0.318022 0.420010 1.069590 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2701(4) 0.7012(4) 0.8509(4) 0.0331(8) Uani 1 1 d . . . . .
H7 H 0.229702 0.800654 0.826106 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1490(4) 0.3041(4) 0.3113(4) 0.0357(9) Uani 1 1 d . . . . .
H20A H 0.233281 0.323739 0.294097 0.043 Uiso 1 1 calc R U . . .
H20B H 0.055935 0.294413 0.220306 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2634(4) 0.6188(5) 0.9580(4) 0.0369(9) Uani 1 1 d . . . . .
H6 H 0.217255 0.662846 1.007460 0.044 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
O24 C1 1.228(4) . ?
O23 N21 1.227(4) . ?
O22 N21 1.223(4) . ?
N9 C1 1.354(4) . ?
N9 C8 1.402(4) . ?
N9 C25 1.456(4) . ?
N21 C18 1.517(4) . ?
C2 C1 1.545(4) . ?
C2 C3 1.507(5) . ?
C2 C16 1.542(4) . ?
C2 C10 1.532(4) . ?
C3 C8 1.391(5) . ?
C3 C4 1.381(5) . ?
C8 C7 1.380(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.399(5) . ?
C11 C12 1.385(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C18 1.530(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(5) . ?
C10 C15 1.397(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.386(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(6) . ?
C13 C12 1.385(6) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C14 H14 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.540(5) . ?
C17 C20 1.539(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C18 1.552(5) . ?
C19 C20 1.540(5) . ?
C12 H12 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.391(6) . ?
C7 H7 0.9500 . ?
C7 C6 1.386(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C6 H6 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 N9 C8 111.1(3) . . ?
C1 N9 C25 123.9(3) . . ?
C8 N9 C25 125.0(3) . . ?
O23 N21 C18 117.1(3) . . ?
O22 N21 O23 123.7(3) . . ?
O22 N21 C18 119.0(3) . . ?
C3 C2 C1 101.4(3) . . ?
C3 C2 C16 114.8(3) . . ?
C3 C2 C10 112.7(3) . . ?
C16 C2 C1 110.6(2) . . ?
C10 C2 C1 104.2(2) . . ?
C10 C2 C16 112.1(3) . . ?
O24 C1 N9 125.9(3) . . ?
O24 C1 C2 125.4(3) . . ?
N9 C1 C2 108.7(3) . . ?
C8 C3 C2 109.0(3) . . ?
C4 C3 C2 131.0(3) . . ?
C4 C3 C8 120.0(3) . . ?
C3 C8 N9 109.8(3) . . ?
C7 C8 N9 127.8(3) . . ?
C7 C8 C3 122.4(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C12 C11 C10 120.9(3) . . ?
C2 C16 H16A 107.5 . . ?
C2 C16 H16B 107.5 . . ?
H16A C16 H16B 107.0 . . ?
C18 C16 C2 119.3(3) . . ?
C18 C16 H16A 107.5 . . ?
C18 C16 H16B 107.5 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C11 C10 C2 119.8(3) . . ?
C15 C10 C2 121.7(3) . . ?
C15 C10 C11 118.2(3) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.5(3) . . ?
N9 C25 H25A 109.5 . . ?
N9 C25 H25B 109.5 . . ?
N9 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
H17A C17 H17B 111.2 . . ?
C18 C17 H17A 114.0 . . ?
C18 C17 H17B 114.0 . . ?
C20 C17 H17A 114.0 . . ?
C20 C17 H17B 114.0 . . ?
C20 C17 C18 87.8(3) . . ?
H19A C19 H19B 111.3 . . ?
C18 C19 H19A 114.1 . . ?
C18 C19 H19B 114.1 . . ?
C20 C19 H19A 114.1 . . ?
C20 C19 H19B 114.1 . . ?
C20 C19 C18 87.4(3) . . ?
C11 C12 C13 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
N21 C18 C16 110.3(3) . . ?
N21 C18 C17 115.0(3) . . ?
N21 C18 C19 111.4(3) . . ?
C16 C18 C17 118.7(3) . . ?
C16 C18 C19 110.7(3) . . ?
C17 C18 C19 88.7(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C8 C7 H7 121.4 . . ?
C8 C7 C6 117.1(4) . . ?
C6 C7 H7 121.4 . . ?
C17 C20 C19 89.2(3) . . ?
C17 C20 H20A 113.8 . . ?
C17 C20 H20B 113.8 . . ?
C19 C20 H20A 113.8 . . ?
C19 C20 H20B 113.8 . . ?
H20A C20 H20B 111.0 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.2 . . ?

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
O23 N21 C18 C16 -56.5(4) . . . . ?
O23 N21 C18 C17 165.8(3) . . . . ?
O23 N21 C18 C19 66.8(4) . . . . ?
O22 N21 C18 C16 126.3(3) . . . . ?
O22 N21 C18 C17 -11.4(4) . . . . ?
O22 N21 C18 C19 -110.4(3) . . . . ?
N9 C8 C7 C6 -177.2(3) . . . . ?
C2 C3 C8 N9 -1.0(4) . . . . ?
C2 C3 C8 C7 179.8(3) . . . . ?
C2 C3 C4 C5 178.5(3) . . . . ?
C2 C16 C18 N21 -71.5(4) . . . . ?
C2 C16 C18 C17 64.4(4) . . . . ?
C2 C16 C18 C19 164.8(3) . . . . ?
C2 C10 C15 C14 174.1(3) . . . . ?
C1 N9 C8 C3 2.8(4) . . . . ?
C1 N9 C8 C7 -178.0(3) . . . . ?
C1 C2 C3 C8 -0.8(3) . . . . ?
C1 C2 C3 C4 -178.0(3) . . . . ?
C1 C2 C16 C18 -65.4(4) . . . . ?
C1 C2 C10 C11 82.2(3) . . . . ?
C1 C2 C10 C15 -92.4(3) . . . . ?
C3 C2 C1 O24 -178.8(3) . . . . ?
C3 C2 C1 N9 2.5(3) . . . . ?
C3 C2 C16 C18 48.6(4) . . . . ?
C3 C2 C10 C11 -26.8(4) . . . . ?
C3 C2 C10 C15 158.5(3) . . . . ?
C3 C8 C7 C6 1.9(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C8 N9 C1 O24 178.0(3) . . . . ?
C8 N9 C1 C2 -3.3(3) . . . . ?
C8 C3 C4 C5 1.6(5) . . . . ?
C8 C7 C6 C5 0.1(5) . . . . ?
C11 C10 C15 C14 -0.6(5) . . . . ?
C16 C2 C1 O24 -56.6(4) . . . . ?
C16 C2 C1 N9 124.6(3) . . . . ?
C16 C2 C3 C8 -120.1(3) . . . . ?
C16 C2 C3 C4 62.8(4) . . . . ?
C16 C2 C10 C11 -158.1(3) . . . . ?
C16 C2 C10 C15 27.2(4) . . . . ?
C4 C3 C8 N9 176.5(3) . . . . ?
C4 C3 C8 C7 -2.7(5) . . . . ?
C4 C5 C6 C7 -1.1(5) . . . . ?
C10 C2 C1 O24 64.0(4) . . . . ?
C10 C2 C1 N9 -114.7(3) . . . . ?
C10 C2 C3 C8 110.0(3) . . . . ?
C10 C2 C3 C4 -67.1(4) . . . . ?
C10 C2 C16 C18 178.8(3) . . . . ?
C10 C11 C12 C13 -0.5(5) . . . . ?
C10 C15 C14 C13 0.3(5) . . . . ?
C25 N9 C1 O24 -2.4(5) . . . . ?
C25 N9 C1 C2 176.3(3) . . . . ?
C25 N9 C8 C3 -176.8(3) . . . . ?
C25 N9 C8 C7 2.3(5) . . . . ?
C14 C13 C12 C11 0.1(6) . . . . ?
C12 C11 C10 C2 -174.1(3) . . . . ?
C12 C11 C10 C15 0.7(5) . . . . ?
C12 C13 C14 C15 0.0(6) . . . . ?
C18 C17 C20 C19 19.8(3) . . . . ?
C18 C19 C20 C17 -19.7(3) . . . . ?
C20 C17 C18 N21 -132.7(3) . . . . ?
C20 C17 C18 C16 93.3(3) . . . . ?
C20 C17 C18 C19 -19.7(3) . . . . ?
C20 C19 C18 N21 136.1(3) . . . . ?
C20 C19 C18 C16 -100.7(3) . . . . ?
C20 C19 C18 C17 19.7(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 1.191
_oxdiff_exptl_absorpt_empirical_full_min 0.852
####################################################################### 
# 
# 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_20230128a_auto
_database_code_depnum_ccdc_archive 'CCDC 2238530'
loop_
_audit_author_name
_audit_author_address
'Guo Yawen'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-01-28 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_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 0.0181 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9343(3)
_cell_length_b                   19.1994(7)
_cell_length_c                   11.1708(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.627(3)
_cell_angle_gamma                90
_cell_volume                     1701.59(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10537
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3870
_cell_measurement_theta_min      3.9280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16238
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.651
_diffrn_reflns_theta_min         4.580
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3015
_reflns_number_total             3413
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.094
_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)+(0.0552P)²+0.4862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
1.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C12(H12A,H12B)
1.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C23(H23), C19(H19), C5(H5), C21(H21), C8(H8), C7(H7), C22(H22),
 C20(H20)
1.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O17 O 0.84190(12) 0.21261(5) 0.66737(9) 0.0252(2) Uani 1 1 d . . . . .
O24 O 0.32484(11) 0.06991(5) 0.55685(9) 0.0226(2) Uani 1 1 d . . . . .
N15 N 0.71322(14) 0.18030(6) 0.68956(10) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.47610(16) 0.23852(7) 0.47648(11) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.42166(16) 0.11738(7) 0.53152(11) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.63537(16) 0.22318(7) 0.43168(11) 0.0154(3) Uani 1 1 d . . . . .
O16 O 0.59287(13) 0.20482(6) 0.74366(9) 0.0297(3) Uani 1 1 d . . . . .
N10 N 0.36694(13) 0.18373(6) 0.51112(10) 0.0181(3) Uani 1 1 d . . . . .
C6 C 0.68203(17) 0.34574(7) 0.39405(12) 0.0209(3) Uani 1 1 d . . . . .
H6 H 0.750618 0.382017 0.363416 0.025 Uiso 1 1 calc R U . . .
C2 C 0.61012(15) 0.10358(7) 0.52295(11) 0.0159(3) Uani 1 1 d . . . . .
H2 H 0.620885 0.054431 0.494404 0.019 Uiso 1 1 calc R U . . .
C23 C 0.54866(17) 0.13248(7) 0.22581(12) 0.0197(3) Uani 1 1 d . . . . .
H23 H 0.467669 0.166488 0.247693 0.024 Uiso 1 1 calc R U . . .
C25 C 0.18834(17) 0.19916(8) 0.52851(15) 0.0277(3) Uani 1 1 d . . . . .
H25A H 0.175006 0.226563 0.601815 0.042 Uiso 1 1 calc R U . . .
H25B H 0.125293 0.155479 0.535469 0.042 Uiso 1 1 calc R U . . .
H25C H 0.145066 0.225769 0.459916 0.042 Uiso 1 1 calc R U . . .
C19 C 0.79867(16) 0.06685(7) 0.26971(12) 0.0192(3) Uani 1 1 d . . . . .
H19 H 0.889226 0.055407 0.322464 0.023 Uiso 1 1 calc R U . . .
C5 C 0.73606(16) 0.27720(7) 0.39042(11) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.844062 0.266876 0.359117 0.022 Uiso 1 1 calc R U . . .
C21 C 0.65377(18) 0.05016(7) 0.08212(12) 0.0228(3) Uani 1 1 d . . . . .
H21 H 0.644320 0.027508 0.006744 0.027 Uiso 1 1 calc R U . . .
C8 C 0.42338(17) 0.30781(7) 0.48413(12) 0.0208(3) Uani 1 1 d . . . . .
H8 H 0.316930 0.318654 0.517497 0.025 Uiso 1 1 calc R U . . .
C3 C 0.69781(15) 0.14891(7) 0.42785(11) 0.0152(3) Uani 1 1 d . . . . .
H3 H 0.820737 0.149811 0.448523 0.018 Uiso 1 1 calc R U . . .
C11 C 0.69838(16) 0.10575(7) 0.64688(11) 0.0175(3) Uani 1 1 d . . . . .
C7 C 0.52648(18) 0.36062(7) 0.44302(12) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.490102 0.407649 0.448454 0.027 Uiso 1 1 calc R U . . .
C13 C 0.77202(18) 0.00641(8) 0.71960(13) 0.0251(3) Uani 1 1 d . . . . .
H13A H 0.741086 -0.033778 0.668358 0.030 Uiso 1 1 calc R U . . .
H13B H 0.830635 -0.009222 0.793540 0.030 Uiso 1 1 calc R U . . .
C14 C 0.62439(18) 0.05692(8) 0.74259(12) 0.0232(3) Uani 1 1 d . . . . .
H14A H 0.512367 0.037661 0.721004 0.028 Uiso 1 1 calc R U . . .
H14B H 0.624356 0.076999 0.824217 0.028 Uiso 1 1 calc R U . . .
C12 C 0.86594(17) 0.06496(7) 0.65213(12) 0.0204(3) Uani 1 1 d . . . . .
H12A H 0.955408 0.088004 0.700245 0.025 Uiso 1 1 calc R U . . .
H12B H 0.908285 0.050780 0.572738 0.025 Uiso 1 1 calc R U . . .
C22 C 0.53537(18) 0.09929(8) 0.11566(12) 0.0234(3) Uani 1 1 d . . . . .
H22 H 0.444486 0.110346 0.062944 0.028 Uiso 1 1 calc R U . . .
C18 C 0.68014(16) 0.11609(7) 0.30419(11) 0.0160(3) Uani 1 1 d . . . . .
C20 C 0.78614(18) 0.03435(7) 0.15949(12) 0.0218(3) Uani 1 1 d . . . . .
H20 H 0.868465 0.001099 0.136726 0.026 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
O17 N15 1.2224(15) . ?
O24 C1 1.2270(16) . ?
N15 O16 1.2293(15) . ?
N15 C11 1.5128(17) . ?
C9 C4 1.3957(18) . ?
C9 N10 1.4191(17) . ?
C9 C8 1.3974(19) . ?
C1 N10 1.3642(17) . ?
C1 C2 1.5226(17) . ?
C4 C5 1.3909(18) . ?
C4 C3 1.5104(18) . ?
N10 C25 1.4628(17) . ?
C6 H6 0.9500 . ?
C6 C5 1.385(2) . ?
C6 C7 1.385(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.5447(17) . ?
C2 C11 1.5452(17) . ?
C23 H23 0.9500 . ?
C23 C22 1.3886(19) . ?
C23 C18 1.3907(18) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C18 1.3909(18) . ?
C19 C20 1.3829(19) . ?
C5 H5 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.386(2) . ?
C21 C20 1.387(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.3844(19) . ?
C3 H3 1.0000 . ?
C3 C18 1.5233(17) . ?
C11 C14 1.5429(19) . ?
C11 C12 1.5436(18) . ?
C7 H7 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.544(2) . ?
C13 C12 1.549(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C22 H22 0.9500 . ?
C20 H20 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
O17 N15 O16 124.08(12) . . ?
O17 N15 C11 118.59(11) . . ?
O16 N15 C11 117.32(11) . . ?
C4 C9 N10 119.94(12) . . ?
C4 C9 C8 119.71(12) . . ?
C8 C9 N10 120.33(12) . . ?
O24 C1 N10 122.22(12) . . ?
O24 C1 C2 120.20(12) . . ?
N10 C1 C2 117.58(11) . . ?
C9 C4 C3 120.53(12) . . ?
C5 C4 C9 119.15(12) . . ?
C5 C4 C3 120.33(11) . . ?
C9 N10 C25 118.76(11) . . ?
C1 N10 C9 122.94(11) . . ?
C1 N10 C25 118.29(11) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.02(13) . . ?
C7 C6 H6 120.5 . . ?
C1 C2 H2 105.8 . . ?
C1 C2 C3 113.28(10) . . ?
C1 C2 C11 112.00(10) . . ?
C3 C2 H2 105.8 . . ?
C3 C2 C11 113.45(10) . . ?
C11 C2 H2 105.8 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C18 120.22(13) . . ?
C18 C23 H23 119.9 . . ?
N10 C25 H25A 109.5 . . ?
N10 C25 H25B 109.5 . . ?
N10 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C20 C19 C18 120.73(12) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.32(12) . . ?
C6 C5 H5 119.3 . . ?
C22 C21 H21 120.3 . . ?
C22 C21 C20 119.45(13) . . ?
C20 C21 H21 120.3 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 119.91(12) . . ?
C7 C8 H8 120.0 . . ?
C4 C3 C2 111.23(10) . . ?
C4 C3 H3 107.2 . . ?
C4 C3 C18 112.91(10) . . ?
C2 C3 H3 107.2 . . ?
C18 C3 C2 110.67(10) . . ?
C18 C3 H3 107.2 . . ?
N15 C11 C2 109.93(10) . . ?
N15 C11 C14 112.67(11) . . ?
N15 C11 C12 113.83(10) . . ?
C14 C11 C2 115.62(11) . . ?
C14 C11 C12 89.97(10) . . ?
C12 C11 C2 113.71(11) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.80(13) . . ?
C8 C7 H7 119.6 . . ?
H13A C13 H13B 110.9 . . ?
C14 C13 H13A 113.7 . . ?
C14 C13 H13B 113.7 . . ?
C14 C13 C12 89.71(10) . . ?
C12 C13 H13A 113.7 . . ?
C12 C13 H13B 113.7 . . ?
C11 C14 C13 88.36(10) . . ?
C11 C14 H14A 113.9 . . ?
C11 C14 H14B 113.9 . . ?
C13 C14 H14A 113.9 . . ?
C13 C14 H14B 113.9 . . ?
H14A C14 H14B 111.1 . . ?
C11 C12 C13 88.16(10) . . ?
C11 C12 H12A 114.0 . . ?
C11 C12 H12B 114.0 . . ?
C13 C12 H12A 114.0 . . ?
C13 C12 H12B 114.0 . . ?
H12A C12 H12B 111.2 . . ?
C23 C22 H22 119.8 . . ?
C21 C22 C23 120.45(12) . . ?
C21 C22 H22 119.8 . . ?
C23 C18 C19 118.96(12) . . ?
C23 C18 C3 122.57(12) . . ?
C19 C18 C3 118.45(11) . . ?
C19 C20 C21 120.18(13) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 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
O17 N15 C11 C2 -92.79(13) . . . . ?
O17 N15 C11 C14 136.68(12) . . . . ?
O17 N15 C11 C12 36.08(15) . . . . ?
O24 C1 N10 C9 -177.07(11) . . . . ?
O24 C1 N10 C25 4.37(19) . . . . ?
O24 C1 C2 C3 147.03(12) . . . . ?
O24 C1 C2 C11 -83.10(15) . . . . ?
N15 C11 C14 C13 -130.66(11) . . . . ?
N15 C11 C12 C13 129.57(11) . . . . ?
C9 C4 C5 C6 0.64(19) . . . . ?
C9 C4 C3 C2 -24.95(15) . . . . ?
C9 C4 C3 C18 100.16(13) . . . . ?
C9 C8 C7 C6 0.0(2) . . . . ?
C1 C2 C3 C4 42.45(14) . . . . ?
C1 C2 C3 C18 -83.91(13) . . . . ?
C1 C2 C11 N15 -74.08(13) . . . . ?
C1 C2 C11 C14 54.86(15) . . . . ?
C1 C2 C11 C12 156.98(11) . . . . ?
C4 C9 N10 C1 16.81(18) . . . . ?
C4 C9 N10 C25 -164.64(12) . . . . ?
C4 C9 C8 C7 2.50(19) . . . . ?
C4 C3 C18 C23 -33.23(17) . . . . ?
C4 C3 C18 C19 148.05(12) . . . . ?
O16 N15 C11 C2 86.39(13) . . . . ?
O16 N15 C11 C14 -44.14(15) . . . . ?
O16 N15 C11 C12 -144.73(11) . . . . ?
N10 C9 C4 C5 175.57(11) . . . . ?
N10 C9 C4 C3 -4.37(17) . . . . ?
N10 C9 C8 C7 -175.88(12) . . . . ?
N10 C1 C2 C3 -33.49(16) . . . . ?
N10 C1 C2 C11 96.38(13) . . . . ?
C2 C1 N10 C9 3.46(18) . . . . ?
C2 C1 N10 C25 -175.10(12) . . . . ?
C2 C3 C18 C23 92.18(14) . . . . ?
C2 C3 C18 C19 -86.53(14) . . . . ?
C2 C11 C14 C13 101.75(12) . . . . ?
C2 C11 C12 C13 -103.50(12) . . . . ?
C5 C4 C3 C2 155.11(11) . . . . ?
C5 C4 C3 C18 -79.78(14) . . . . ?
C5 C6 C7 C8 -2.2(2) . . . . ?
C8 C9 C4 C5 -2.82(18) . . . . ?
C8 C9 C4 C3 177.24(11) . . . . ?
C8 C9 N10 C1 -164.81(12) . . . . ?
C8 C9 N10 C25 13.75(18) . . . . ?
C3 C4 C5 C6 -179.42(11) . . . . ?
C3 C2 C11 N15 55.71(14) . . . . ?
C3 C2 C11 C14 -175.35(11) . . . . ?
C3 C2 C11 C12 -73.24(14) . . . . ?
C11 C2 C3 C4 -86.69(12) . . . . ?
C11 C2 C3 C18 146.95(11) . . . . ?
C7 C6 C5 C4 1.9(2) . . . . ?
C14 C11 C12 C13 14.67(10) . . . . ?
C14 C13 C12 C11 -14.65(10) . . . . ?
C12 C11 C14 C13 -14.71(10) . . . . ?
C12 C13 C14 C11 14.66(10) . . . . ?
C22 C23 C18 C19 0.88(19) . . . . ?
C22 C23 C18 C3 -177.83(12) . . . . ?
C22 C21 C20 C19 0.7(2) . . . . ?
C18 C23 C22 C21 -0.7(2) . . . . ?
C18 C19 C20 C21 -0.5(2) . . . . ?
C20 C19 C18 C23 -0.2(2) . . . . ?
C20 C19 C18 C3 178.52(12) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2235193'
loop_
_audit_author_name
_audit_author_address
'Guo Yawen'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-01-09 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        
1-methyl-3-((1-nitrocyclobutyl)methyl)-3-(4-nitrophenyl)indolin-2-one
_chemical_formula_moiety         'C20 H19 N3 O5'
_chemical_formula_sum            'C20 H19 N3 O5'
_chemical_formula_weight         381.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.2829(10)
_cell_length_b                   8.1950(5)
_cell_length_c                   12.6580(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.083(6)
_cell_angle_gamma                90
_cell_volume                     1822.30(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9386
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.5130
_cell_measurement_theta_min      5.0240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1376
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.741
_diffrn_reflns_theta_min         5.035
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00 120.00   0.50    0.10    --   47.03  38.00  95.00  170
  2  ω     24.00 119.00   0.50    0.10    --   47.03  77.00-120.00  190
  3  ω     35.00 120.00   0.50    0.10    --   47.03  37.00-180.00  170
  4  ω    -24.00  28.00   0.50    0.10    --  -47.03  19.00-120.00  104
  5  ω    -41.00  26.00   0.50    0.10    --  -47.03  38.00  95.00  134
  6  ω     73.00 106.00   0.50    0.39    --  104.75 -94.00   0.00   66
  7  ω     32.00  91.00   0.50    0.39    --  104.75 -94.00 -30.00  118
  8  ω    -26.00  45.00   0.50    0.10    --   47.03 -38.00 -59.00  142
  9  ω     32.00  68.00   0.50    0.39    --  104.75 -61.00   0.00   72
 10  ω     33.00  68.00   0.50    0.39    --  104.75 -61.00  30.00   70
 11  ω     40.00  65.00   0.50    0.39    --  104.75 -61.00  60.00   50
 12  ω     33.00  65.00   0.50    0.39    --  104.75 -61.00 120.00   64
 13  ω     38.00  73.00   0.50    0.39    --  104.75 -61.00 150.00   70
 14  ω     95.00 143.00   0.50    0.39    --  104.75  15.00  30.00   96
 15  ω    153.00 178.00   0.50    0.39    --  104.75  15.00  30.00   50
 16  ω     92.00 178.00   0.50    0.39    --  104.75  38.00  95.00  172
 17  ω   -103.00 -29.00   0.50    0.39    -- -102.00  77.00-180.00  148
 18  ω    -67.00 -31.00   0.50    0.39    -- -102.00  61.00-120.00   72
 19  ω    -59.00 -29.00   0.50    0.39    -- -102.00  61.00 -90.00   60
 20  ω    -69.00 -29.00   0.50    0.39    -- -102.00  61.00 -60.00   80
 21  ω    -65.00 -29.00   0.50    0.39    -- -102.00  61.00 -30.00   72
 22  ω   -109.00 -70.00   0.50    0.39    -- -102.00 125.00 120.00   78
 23  ω   -118.00 -32.00   0.50    0.10    --  -47.03 -57.00-150.00  172
 24  ω   -120.00 -34.00   0.50    0.10    --  -47.03 -38.00 -59.00  172
 25  ω   -118.00 -32.00   0.50    0.10    --  -47.03 -57.00 150.00  172
 26  ω    -57.00 -30.00   0.50    0.39    -- -102.00 125.00 120.00   54
 27  ω   -175.00 -89.00   0.50    0.39    -- -102.00 -38.00 -59.00  172
 28  ω   -164.00 -81.00   0.50    0.39    -- -102.00 -77.00 -90.00  166
 29  ω   -117.00 -79.00   0.50    0.39    -- -102.00 -77.00-120.00   76
 30  ω   -105.00 -79.00   0.50    0.39    -- -102.00 -77.00-112.49   52
 31  ω   -175.00 -79.00   0.50    0.39    -- -102.00 -77.00-150.00  192
 32  ω   -164.00-138.00   0.50    0.39    -- -102.00 -77.00-112.49   52
 33  ω   -169.00-127.00   0.50    0.39    -- -102.00 -77.00-120.00   84
 34  ω   -105.00 -79.00   0.50    0.39    -- -102.00 -77.00-180.00   52
 35  ω   -164.00 -82.00   0.50    0.39    -- -102.00 -69.00-169.44  164
 36  ω   -175.00 -80.00   0.50    0.39    -- -102.00 -75.00 -86.43  190
 37  ω   -110.00 -84.00   0.50    0.39    -- -102.00 -67.00-151.02   52
 38  ω   -157.00 -85.00   0.50    0.39    -- -102.00 -61.00-150.00  144
 39  ω   -175.00 -85.00   0.50    0.39    -- -102.00 -61.00-120.00  180
 40  ω   -169.00 -88.00   0.50    0.39    -- -102.00 -58.00-157.18  162
 41  ω   -153.00 -91.00   0.50    0.39    -- -102.00 -55.00-167.39  124
 42  ω   -175.00 -85.00   0.50    0.39    -- -102.00 -61.00 150.00  180
 43  ω   -175.00 -82.00   0.50    0.39    -- -102.00 -71.00 177.42  186
 44  ω   -133.00 -81.00   0.50    0.39    -- -102.00 -72.00 171.04  104
 45  ω   -174.00-121.00   0.50    0.39    -- -102.00 -52.00 131.88  106
 46  ω   -119.00 -71.00   0.50    0.10    --  -47.03-125.00  30.00   96
 47  ω   -103.00 -77.00   0.50    0.39    -- -102.00 -83.00-159.37   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0688820000
_diffrn_orient_matrix_UB_12      -0.0880758000
_diffrn_orient_matrix_UB_13      -0.0215448000
_diffrn_orient_matrix_UB_21      -0.0453739000
_diffrn_orient_matrix_UB_22      -0.0265770000
_diffrn_orient_matrix_UB_23      -0.1208425000
_diffrn_orient_matrix_UB_31      0.0297300000
_diffrn_orient_matrix_UB_32      0.1640084000
_diffrn_orient_matrix_UB_33      -0.0311460000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2820
_reflns_number_total             3709
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3709
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.072
_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)+(0.0683P)²+0.3455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C23A-C22 \\sim C23B-C22 \\sim C23B-C20 \\sim C23A-C20
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
C23B \\sim C23A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 1.7A
3. Others
 Sof(H20C)=Sof(H20D)=Sof(H22C)=Sof(H22D)=Sof(C23B)=Sof(H23C)=Sof(H23D)=1-FVAR(1)
 Sof(H20A)=Sof(H20B)=Sof(H22A)=Sof(H22B)=Sof(C23A)=Sof(H23A)=Sof(H23B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C20(H20C,H20D), C22(H22A,H22B), C22(H22C,
 H22D), C23A(H23A,H23B), C23B(H23C,H23D)
4.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C11(H11), C12(H12), C4(H4), C5(H5), C6(H6), C7(H7)
4.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O27 O 0.14876(7) 0.70260(17) 0.28397(11) 0.0338(3) Uani 1 1 d . . . . .
O26 O 0.23508(8) 0.06885(17) 0.20491(12) 0.0384(4) Uani 1 1 d . . . . .
O18 O 0.48542(8) 0.7501(2) 0.73012(11) 0.0409(4) Uani 1 1 d . . . . .
O25 O 0.16022(8) 0.17758(19) 0.05926(11) 0.0412(4) Uani 1 1 d . . . . .
O17 O 0.53569(8) 0.8544(2) 0.61003(12) 0.0425(4) Uani 1 1 d . . . . .
N9 N 0.18516(9) 0.65524(19) 0.12690(13) 0.0306(4) Uani 1 1 d . . . . .
N24 N 0.18377(9) 0.1630(2) 0.15918(13) 0.0319(4) Uani 1 1 d . . . . .
N16 N 0.48635(9) 0.7735(2) 0.63518(13) 0.0329(4) Uani 1 1 d . . . . .
C1 C 0.18805(10) 0.6326(2) 0.23410(15) 0.0290(4) Uani 1 1 d . . . . .
C3 C 0.27843(10) 0.4629(2) 0.18487(14) 0.0285(4) Uani 1 1 d . . . . .
C10 C 0.31030(10) 0.5688(2) 0.37889(15) 0.0294(4) Uani 1 1 d . . . . .
C13 C 0.42565(10) 0.7010(2) 0.54593(15) 0.0301(4) Uani 1 1 d . . . . .
C8 C 0.23953(10) 0.5577(2) 0.09590(15) 0.0287(4) Uani 1 1 d . . . . .
C15 C 0.31617(10) 0.5310(2) 0.48781(15) 0.0303(4) Uani 1 1 d . . . . .
H15 H 0.280022 0.459523 0.504593 0.036 Uiso 1 1 calc R U . . .
C2 C 0.24775(10) 0.4986(2) 0.28199(15) 0.0291(4) Uani 1 1 d . . . . .
C14 C 0.37405(10) 0.5960(2) 0.57252(15) 0.0303(4) Uani 1 1 d . . . . .
H14 H 0.378209 0.569073 0.646962 0.036 Uiso 1 1 calc R U . . .
C19 C 0.20692(10) 0.3533(2) 0.31905(14) 0.0290(4) Uani 1 1 d . . . . .
H19A H 0.246437 0.274149 0.356769 0.035 Uiso 1 1 calc R U . . .
H19B H 0.182616 0.394673 0.374622 0.035 Uiso 1 1 calc R U . . .
C11 C 0.36322(11) 0.6758(2) 0.35577(15) 0.0308(4) Uani 1 1 d . . . . .
H11 H 0.359300 0.703422 0.281507 0.037 Uiso 1 1 calc R U . . .
C12 C 0.42135(11) 0.7426(2) 0.43902(16) 0.0318(4) Uani 1 1 d . . . . .
H12 H 0.457301 0.815097 0.422757 0.038 Uiso 1 1 calc R U . . .
C4 C 0.33781(10) 0.3645(2) 0.17602(16) 0.0317(4) Uani 1 1 d . . . . .
H4 H 0.365025 0.299563 0.236320 0.038 Uiso 1 1 calc R U . . .
C21 C 0.14679(10) 0.2601(2) 0.23317(15) 0.0305(4) Uani 1 1 d . . . . .
C5 C 0.35691(11) 0.3623(2) 0.07730(16) 0.0334(4) Uani 1 1 d . . . . .
H5 H 0.397955 0.296185 0.070160 0.040 Uiso 1 1 calc R U . . .
C6 C 0.31656(11) 0.4561(2) -0.01126(16) 0.0333(4) Uani 1 1 d . . . . .
H6 H 0.330201 0.452165 -0.078381 0.040 Uiso 1 1 calc R U . . .
C7 C 0.25654(11) 0.5555(2) -0.00345(15) 0.0326(4) Uani 1 1 d . . . . .
H7 H 0.228568 0.619078 -0.063973 0.039 Uiso 1 1 calc R U . . .
C20 C 0.07240(11) 0.3427(3) 0.16729(17) 0.0371(5) Uani 1 1 d D . . . .
H20A H 0.071130 0.368616 0.090414 0.045 Uiso 0.751(7) 1 calc R U P A 1
H20B H 0.058082 0.438985 0.204418 0.045 Uiso 0.751(7) 1 calc R U P A 1
H20C H 0.049002 0.293193 0.094410 0.045 Uiso 0.249(7) 1 calc R U P A 2
H20D H 0.075559 0.462941 0.162368 0.045 Uiso 0.249(7) 1 calc R U P A 2
C22 C 0.09803(11) 0.1380(3) 0.27897(17) 0.0371(5) Uani 1 1 d D . . . .
H22A H 0.091889 0.168818 0.351658 0.045 Uiso 0.751(7) 1 calc R U P A 1
H22B H 0.114234 0.022846 0.278347 0.045 Uiso 0.751(7) 1 calc R U P A 1
H22C H 0.121385 0.105054 0.356219 0.045 Uiso 0.249(7) 1 calc R U P A 2
H22D H 0.080324 0.041973 0.231322 0.045 Uiso 0.249(7) 1 calc R U P A 2
C28 C 0.13180(12) 0.7621(3) 0.05248(17) 0.0382(5) Uani 1 1 d . . . . .
H28A H 0.096785 0.809257 0.090442 0.057 Uiso 1 1 calc R U . . .
H28B H 0.102809 0.699566 -0.011412 0.057 Uiso 1 1 calc R U . . .
H28C H 0.159707 0.849873 0.028060 0.057 Uiso 1 1 calc R U . . .
C23A C 0.02826(15) 0.1855(3) 0.1792(2) 0.0365(8) Uani 0.751(7) 1 d D U P A 1
H23A H 0.019683 0.110358 0.115722 0.044 Uiso 0.751(7) 1 calc R U P A 1
H23B H -0.019453 0.205579 0.199657 0.044 Uiso 0.751(7) 1 calc R U P A 1
C23B C 0.0372(5) 0.2781(10) 0.2649(7) 0.041(3) Uani 0.249(7) 1 d D U P A 2
H23C H 0.045330 0.352562 0.328638 0.049 Uiso 0.249(7) 1 calc R U P A 2
H23D H -0.016332 0.240683 0.239346 0.049 Uiso 0.249(7) 1 calc R U P A 2


_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
O27 C1 1.223(2) . ?
O26 N24 1.228(2) . ?
O18 N16 1.222(2) . ?
O25 N24 1.224(2) . ?
O17 N16 1.230(2) . ?
N9 C1 1.356(2) . ?
N9 C8 1.413(2) . ?
N9 C28 1.448(2) . ?
N24 C21 1.523(2) . ?
N16 C13 1.472(2) . ?
C1 C2 1.549(3) . ?
C3 C8 1.391(3) . ?
C3 C2 1.515(3) . ?
C3 C4 1.382(3) . ?
C10 C15 1.388(3) . ?
C10 C2 1.538(3) . ?
C10 C11 1.396(3) . ?
C13 C14 1.386(3) . ?
C13 C12 1.376(3) . ?
C8 C7 1.377(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.387(3) . ?
C2 C19 1.545(3) . ?
C14 H14 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C21 1.520(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C21 C20 1.541(3) . ?
C21 C22 1.555(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(3) . ?
C7 H7 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 H20C 0.9900 . ?
C20 H20D 0.9900 . ?
C20 C23A 1.549(3) . ?
C20 C23B 1.631(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 H22C 0.9900 . ?
C22 H22D 0.9900 . ?
C22 C23A 1.575(3) . ?
C22 C23B 1.574(8) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C23B H23C 0.9900 . ?
C23B H23D 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
C1 N9 C8 111.40(15) . . ?
C1 N9 C28 124.49(16) . . ?
C8 N9 C28 124.09(16) . . ?
O26 N24 C21 116.73(15) . . ?
O25 N24 O26 123.54(16) . . ?
O25 N24 C21 119.70(16) . . ?
O18 N16 O17 123.38(16) . . ?
O18 N16 C13 118.60(16) . . ?
O17 N16 C13 118.02(15) . . ?
O27 C1 N9 125.93(18) . . ?
O27 C1 C2 125.58(17) . . ?
N9 C1 C2 108.46(15) . . ?
C8 C3 C2 109.16(16) . . ?
C4 C3 C8 119.84(17) . . ?
C4 C3 C2 130.88(17) . . ?
C15 C10 C2 122.98(17) . . ?
C15 C10 C11 118.77(17) . . ?
C11 C10 C2 118.26(16) . . ?
C14 C13 N16 118.92(16) . . ?
C12 C13 N16 118.71(17) . . ?
C12 C13 C14 122.36(17) . . ?
C3 C8 N9 109.42(16) . . ?
C7 C8 N9 127.96(18) . . ?
C7 C8 C3 122.58(18) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 120.97(17) . . ?
C14 C15 H15 119.5 . . ?
C3 C2 C1 101.45(14) . . ?
C3 C2 C10 111.03(15) . . ?
C3 C2 C19 114.61(15) . . ?
C10 C2 C1 109.53(15) . . ?
C10 C2 C19 111.17(15) . . ?
C19 C2 C1 108.53(14) . . ?
C13 C14 C15 118.40(17) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C2 C19 H19A 107.6 . . ?
C2 C19 H19B 107.6 . . ?
H19A C19 H19B 107.0 . . ?
C21 C19 C2 118.97(15) . . ?
C21 C19 H19A 107.6 . . ?
C21 C19 H19B 107.6 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.27(17) . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 118.23(18) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.67(18) . . ?
C5 C4 H4 120.7 . . ?
N24 C21 C20 111.87(16) . . ?
N24 C21 C22 106.91(15) . . ?
C19 C21 N24 110.25(15) . . ?
C19 C21 C20 121.41(17) . . ?
C19 C21 C22 115.61(15) . . ?
C20 C21 C22 88.46(14) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.62(18) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.26(17) . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 117.01(18) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 H7 121.5 . . ?
C21 C20 H20A 113.8 . . ?
C21 C20 H20B 113.8 . . ?
C21 C20 H20C 114.4 . . ?
C21 C20 H20D 114.4 . . ?
C21 C20 C23A 89.29(16) . . ?
C21 C20 C23B 85.5(3) . . ?
H20A C20 H20B 111.0 . . ?
H20C C20 H20D 111.5 . . ?
C23A C20 H20A 113.8 . . ?
C23A C20 H20B 113.8 . . ?
C23B C20 H20C 114.4 . . ?
C23B C20 H20D 114.4 . . ?
C21 C22 H22A 114.0 . . ?
C21 C22 H22B 114.0 . . ?
C21 C22 H22C 114.1 . . ?
C21 C22 H22D 114.1 . . ?
C21 C22 C23A 87.86(16) . . ?
C21 C22 C23B 87.1(3) . . ?
H22A C22 H22B 111.2 . . ?
H22C C22 H22D 111.3 . . ?
C23A C22 H22A 114.0 . . ?
C23A C22 H22B 114.0 . . ?
C23B C22 H22C 114.1 . . ?
C23B C22 H22D 114.1 . . ?
N9 C28 H28A 109.5 . . ?
N9 C28 H28B 109.5 . . ?
N9 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C20 C23A C22 87.45(17) . . ?
C20 C23A H23A 114.1 . . ?
C20 C23A H23B 114.1 . . ?
C22 C23A H23A 114.1 . . ?
C22 C23A H23B 114.1 . . ?
H23A C23A H23B 111.3 . . ?
C20 C23B H23C 114.5 . . ?
C20 C23B H23D 114.5 . . ?
C22 C23B C20 84.7(4) . . ?
C22 C23B H23C 114.5 . . ?
C22 C23B H23D 114.5 . . ?
H23C C23B H23D 111.6 . . ?

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
O27 C1 C2 C3 -178.68(18) . . . . ?
O27 C1 C2 C10 -61.3(2) . . . . ?
O27 C1 C2 C19 60.3(2) . . . . ?
O26 N24 C21 C19 54.8(2) . . . . ?
O26 N24 C21 C20 -166.94(16) . . . . ?
O26 N24 C21 C22 -71.67(19) . . . . ?
O18 N16 C13 C14 -6.3(3) . . . . ?
O18 N16 C13 C12 172.49(18) . . . . ?
O25 N24 C21 C19 -127.49(17) . . . . ?
O25 N24 C21 C20 10.8(2) . . . . ?
O25 N24 C21 C22 106.09(19) . . . . ?
O17 N16 C13 C14 173.48(17) . . . . ?
O17 N16 C13 C12 -7.7(3) . . . . ?
N9 C1 C2 C3 3.20(19) . . . . ?
N9 C1 C2 C10 120.60(16) . . . . ?
N9 C1 C2 C19 -117.86(16) . . . . ?
N9 C8 C7 C6 175.57(17) . . . . ?
N24 C21 C20 C23A 87.64(18) . . . . ?
N24 C21 C20 C23B 135.5(4) . . . . ?
N24 C21 C22 C23A -92.76(18) . . . . ?
N24 C21 C22 C23B -141.4(4) . . . . ?
N16 C13 C14 C15 178.72(17) . . . . ?
N16 C13 C12 C11 -178.91(17) . . . . ?
C1 N9 C8 C3 1.9(2) . . . . ?
C1 N9 C8 C7 -175.53(19) . . . . ?
C1 C2 C19 C21 63.6(2) . . . . ?
C3 C8 C7 C6 -1.6(3) . . . . ?
C3 C2 C19 C21 -49.0(2) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C10 C15 C14 C13 0.6(3) . . . . ?
C10 C2 C19 C21 -175.89(15) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C8 N9 C1 O27 178.63(17) . . . . ?
C8 N9 C1 C2 -3.3(2) . . . . ?
C8 C3 C2 C1 -2.08(19) . . . . ?
C8 C3 C2 C10 -118.39(17) . . . . ?
C8 C3 C2 C19 114.63(17) . . . . ?
C8 C3 C4 C5 -0.4(3) . . . . ?
C15 C10 C2 C1 106.0(2) . . . . ?
C15 C10 C2 C3 -142.81(18) . . . . ?
C15 C10 C2 C19 -14.0(2) . . . . ?
C15 C10 C11 C12 0.7(3) . . . . ?
C2 C3 C8 N9 0.3(2) . . . . ?
C2 C3 C8 C7 177.94(17) . . . . ?
C2 C3 C4 C5 -175.88(19) . . . . ?
C2 C10 C15 C14 179.32(17) . . . . ?
C2 C10 C11 C12 -179.51(17) . . . . ?
C2 C19 C21 N24 69.6(2) . . . . ?
C2 C19 C21 C20 -64.0(2) . . . . ?
C2 C19 C21 C22 -169.00(16) . . . . ?
C14 C13 C12 C11 -0.2(3) . . . . ?
C19 C21 C20 C23A -139.35(19) . . . . ?
C19 C21 C20 C23B -91.4(4) . . . . ?
C19 C21 C22 C23A 144.08(18) . . . . ?
C19 C21 C22 C23B 95.4(4) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
C11 C10 C2 C1 -73.8(2) . . . . ?
C11 C10 C2 C3 37.4(2) . . . . ?
C11 C10 C2 C19 166.28(16) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C4 C3 C8 N9 -176.08(16) . . . . ?
C4 C3 C8 C7 1.5(3) . . . . ?
C4 C3 C2 C1 173.81(19) . . . . ?
C4 C3 C2 C10 57.5(3) . . . . ?
C4 C3 C2 C19 -69.5(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C21 C20 C23A C22 19.73(16) . . . . ?
C21 C20 C23B C22 -27.7(3) . . . . ?
C21 C22 C23A C20 -19.56(17) . . . . ?
C21 C22 C23B C20 27.4(3) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C20 C21 C22 C23A 19.66(17) . . . . ?
C20 C21 C22 C23B -29.0(4) . . . . ?
C22 C21 C20 C23A -19.99(17) . . . . ?
C22 C21 C20 C23B 27.9(3) . . . . ?
C28 N9 C1 O27 -3.0(3) . . . . ?
C28 N9 C1 C2 175.11(17) . . . . ?
C28 N9 C8 C3 -176.46(17) . . . . ?
C28 N9 C8 C7 6.1(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 2.486
_oxdiff_exptl_absorpt_empirical_full_min 0.491
