# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

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

data_3a
_database_code_depnum_ccdc_archive 'CCDC 2154066'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2022-02-23 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_audit_creation_date             2020-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N2 O2'
_chemical_formula_sum            'C21 H18 N2 O2'
_chemical_formula_weight         330.37
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.21864(13)
_cell_length_b                   10.5120(2)
_cell_length_c                   22.0152(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1670.57(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3740
_cell_measurement_temperature    293.2(3)
_cell_measurement_theta_max      71.1350
_cell_measurement_theta_min      5.7980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9144
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.315
_diffrn_reflns_theta_min         4.661
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.2(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  37.00   1.00    1.00    --  -34.98  19.00-180.00  110
  2  ω      6.00 104.00   1.00    1.00    --   34.98  77.00-150.00   98
  3  ω      6.00 104.00   1.00    1.00    --   34.98  77.00   0.00   98
  4  ω     23.00  90.00   1.00    1.00    --   34.98-125.00 -60.00   67
  5  ω     23.00  90.00   1.00    1.00    --   34.98-125.00-180.00   67
  6  ω     78.00 176.00   1.00    3.01    --  106.90  77.00 -30.00   98
  7  ω     81.00 178.00   1.00    3.01    --  106.90  30.00  30.00   97
  8  ω     87.00 175.00   1.00    3.01    --  106.90  61.00  60.00   88
  9  ω     38.00 126.00   1.00    3.01    --  106.90 -54.00 -92.00   88
 10  ω     39.00 127.00   1.00    3.01    --  106.90 -61.00 120.00   88
 11  ω     37.00 110.00   1.00    3.01    --  106.90 -94.00  90.00   73
 12  ω     37.00 110.00   1.00    3.01    --  106.90 -94.00 120.00   73
 13  ω     36.00 113.00   1.00    3.01    --  106.90-111.00 -90.00   77
 14  ω    -33.00  20.00   1.00    1.00    --   34.98 -57.00 -30.00   53
 15  ω     16.00 103.00   1.00    1.00    --   34.98  57.00 120.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1300875000
_diffrn_orient_matrix_UB_12      0.0230760000
_diffrn_orient_matrix_UB_13      0.0543922000
_diffrn_orient_matrix_UB_21      0.0490323000
_diffrn_orient_matrix_UB_22      -0.1323338000
_diffrn_orient_matrix_UB_23      0.0254005000
_diffrn_orient_matrix_UB_31      0.1619579000
_diffrn_orient_matrix_UB_32      0.0585871000
_diffrn_orient_matrix_UB_33      0.0359442000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2947
_reflns_number_total             3192
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0654
_refine_ls_restrained_S_all      1.058
_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)+(0.1141P)²+0.0447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1634
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00C(H00C), C00I(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00E), C00H(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00D(H00D), C00F(H00F), C00G(H00G), C00J(H00K),
 C00K(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.6274(3) 0.5975(2) 0.61954(10) 0.0394(5) Uani 1 1 d . . . . .
N002 N 0.4822(3) 0.6442(2) 0.58231(11) 0.0446(5) Uani 1 1 d . . . . .
O003 O 0.3052(4) 0.6227(3) 0.49972(12) 0.0695(7) Uani 1 1 d . . . . .
C004 C 0.4319(4) 0.4317(3) 0.53937(13) 0.0445(6) Uani 1 1 d . . . . .
C005 C 0.4016(4) 0.5728(3) 0.53880(13) 0.0479(6) Uani 1 1 d . . . . .
O006 O 0.4898(5) 0.9544(4) 0.7261(2) 0.1129(15) Uani 1 1 d . . . . .
C007 C 0.4454(6) 0.3697(4) 0.48430(15) 0.0632(9) Uani 1 1 d . . . . .
H007 H 0.4400 0.4161 0.4484 0.076 Uiso 1 1 calc R . . . .
C008 C 0.7982(4) 0.6775(3) 0.70847(14) 0.0457(6) Uani 1 1 d . . . . .
C009 C 0.6246(4) 0.6858(2) 0.67094(12) 0.0407(6) Uani 1 1 d . . . . .
H009 H 0.5203 0.6621 0.6971 0.049 Uiso 1 1 calc R . . . .
C00A C 0.4380(5) 0.3600(3) 0.59241(14) 0.0500(7) Uani 1 1 d . . . . .
H00A H 0.4303 0.4002 0.6300 0.060 Uiso 1 1 calc R . . . .
C00B C 0.9503(4) 0.6077(3) 0.68955(14) 0.0500(7) Uani 1 1 d . . . . .
C00C C 0.4651(4) 0.7843(3) 0.58606(15) 0.0491(7) Uani 1 1 d . . . . .
H00C H 0.5139 0.8257 0.5495 0.059 Uiso 1 1 calc R . . . .
C00D C 0.2718(5) 0.8288(3) 0.60031(19) 0.0593(8) Uani 1 1 d . . . . .
H00D H 0.1698 0.8144 0.5755 0.071 Uiso 1 1 calc R . . . .
C00E C 0.8058(4) 0.6010(3) 0.58731(13) 0.0503(7) Uani 1 1 d . . . . .
H00B H 0.8395 0.6881 0.5778 0.060 Uiso 1 1 calc R . . . .
H00E H 0.7979 0.5533 0.5497 0.060 Uiso 1 1 calc R . . . .
C00F C 0.4556(5) 0.2292(3) 0.58949(18) 0.0620(8) Uani 1 1 d . . . . .
H00F H 0.4561 0.1815 0.6251 0.074 Uiso 1 1 calc R . . . .
C00G C 0.4670(7) 0.2385(4) 0.48222(19) 0.0799(13) Uani 1 1 d . . . . .
H00G H 0.4779 0.1978 0.4449 0.096 Uiso 1 1 calc R . . . .
C00H C 0.9473(5) 0.5426(4) 0.62875(16) 0.0601(8) Uani 1 1 d . . . . .
H00H H 1.0688 0.5488 0.6102 0.072 Uiso 1 1 calc R . . . .
H00I H 0.9191 0.4531 0.6343 0.072 Uiso 1 1 calc R . . . .
C00I C 0.5785(4) 0.8184(3) 0.64192(16) 0.0506(7) Uani 1 1 d . . . . .
H00J H 0.6910 0.8657 0.6313 0.061 Uiso 1 1 calc R . . . .
C00J C 0.2647(5) 0.8916(4) 0.6529(2) 0.0697(10) Uani 1 1 d . . . . .
H00K H 0.1579 0.9268 0.6694 0.084 Uiso 1 1 calc R . . . .
C00K C 0.4725(7) 0.1692(4) 0.5341(2) 0.0725(11) Uani 1 1 d . . . . .
H00L H 0.4876 0.0814 0.5323 0.087 Uiso 1 1 calc R . . . .
C00L C 0.4475(6) 0.8973(3) 0.6809(2) 0.0683(10) Uani 1 1 d . . . . .
C00M C 0.7997(7) 0.7337(4) 0.76600(17) 0.0684(10) Uani 1 1 d . . . . .
H00M H 0.6971 0.7793 0.7794 0.082 Uiso 1 1 calc R . . . .
C00N C 1.1024(5) 0.5954(4) 0.7282(2) 0.0671(9) Uani 1 1 d . . . . .
H00N H 1.2045 0.5480 0.7159 0.080 Uiso 1 1 calc R . . . .
C00O C 0.9524(9) 0.7217(4) 0.8029(2) 0.0884(15) Uani 1 1 d . . . . .
H00O H 0.9535 0.7608 0.8408 0.106 Uiso 1 1 calc R . . . .
C00P C 1.1027(7) 0.6526(5) 0.7843(2) 0.0844(14) Uani 1 1 d . . . . .
H00P H 1.2051 0.6443 0.8097 0.101 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N001 N002 1.418(3) . ?
N001 C009 1.464(3) . ?
N001 C00E 1.471(3) . ?
N002 C005 1.349(4) . ?
N002 C00C 1.480(4) . ?
O003 C005 1.224(4) . ?
C004 C005 1.499(4) . ?
C004 C007 1.380(4) . ?
C004 C00A 1.390(4) . ?
O006 C00L 1.201(5) . ?
C007 H007 0.9300 . ?
C007 C00G 1.389(6) . ?
C008 C009 1.503(4) . ?
C008 C00B 1.385(5) . ?
C008 C00M 1.397(4) . ?
C009 H009 0.9800 . ?
C009 C00I 1.569(4) . ?
C00A H00A 0.9300 . ?
C00A C00F 1.382(5) . ?
C00B C00H 1.504(4) . ?
C00B C00N 1.396(5) . ?
C00C H00C 0.9800 . ?
C00C C00D 1.505(4) . ?
C00C C00I 1.520(5) . ?
C00D H00D 0.9300 . ?
C00D C00J 1.333(6) . ?
C00E H00B 0.9700 . ?
C00E H00E 0.9700 . ?
C00E C00H 1.501(5) . ?
C00F H00F 0.9300 . ?
C00F C00K 1.378(6) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.355(7) . ?
C00H H00H 0.9700 . ?
C00H H00I 0.9700 . ?
C00I H00J 0.9800 . ?
C00I C00L 1.523(5) . ?
C00J H00K 0.9300 . ?
C00J C00L 1.458(6) . ?
C00K H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00O 1.376(7) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.374(7) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.369(8) . ?
C00P H00P 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N002 N001 C009 102.5(2) . . ?
N002 N001 C00E 111.1(2) . . ?
C009 N001 C00E 111.6(2) . . ?
N001 N002 C00C 112.0(2) . . ?
C005 N002 N001 122.5(2) . . ?
C005 N002 C00C 123.9(3) . . ?
C007 C004 C005 118.0(3) . . ?
C007 C004 C00A 118.7(3) . . ?
C00A C004 C005 123.2(3) . . ?
N002 C005 C004 118.8(2) . . ?
O003 C005 N002 120.4(3) . . ?
O003 C005 C004 120.8(3) . . ?
C004 C007 H007 119.8 . . ?
C004 C007 C00G 120.4(3) . . ?
C00G C007 H007 119.8 . . ?
C00B C008 C009 121.8(3) . . ?
C00B C008 C00M 119.4(3) . . ?
C00M C008 C009 118.7(3) . . ?
N001 C009 C008 112.1(2) . . ?
N001 C009 H009 107.6 . . ?
N001 C009 C00I 104.6(2) . . ?
C008 C009 H009 107.6 . . ?
C008 C009 C00I 116.9(2) . . ?
C00I C009 H009 107.6 . . ?
C004 C00A H00A 119.9 . . ?
C00F C00A C004 120.2(3) . . ?
C00F C00A H00A 119.9 . . ?
C008 C00B C00H 119.9(3) . . ?
C008 C00B C00N 119.3(3) . . ?
C00N C00B C00H 120.8(3) . . ?
N002 C00C H00C 111.5 . . ?
N002 C00C C00D 113.5(3) . . ?
N002 C00C C00I 103.6(2) . . ?
C00D C00C H00C 111.5 . . ?
C00D C00C C00I 104.9(3) . . ?
C00I C00C H00C 111.5 . . ?
C00C C00D H00D 124.1 . . ?
C00J C00D C00C 111.8(3) . . ?
C00J C00D H00D 124.1 . . ?
N001 C00E H00B 110.3 . . ?
N001 C00E H00E 110.3 . . ?
N001 C00E C00H 107.0(2) . . ?
H00B C00E H00E 108.6 . . ?
C00H C00E H00B 110.3 . . ?
C00H C00E H00E 110.3 . . ?
C00A C00F H00F 119.9 . . ?
C00K C00F C00A 120.3(3) . . ?
C00K C00F H00F 119.9 . . ?
C007 C00G H00G 119.7 . . ?
C00K C00G C007 120.6(3) . . ?
C00K C00G H00G 119.7 . . ?
C00B C00H H00H 109.4 . . ?
C00B C00H H00I 109.4 . . ?
C00E C00H C00B 111.3(3) . . ?
C00E C00H H00H 109.4 . . ?
C00E C00H H00I 109.4 . . ?
H00H C00H H00I 108.0 . . ?
C009 C00I H00J 111.9 . . ?
C00C C00I C009 103.5(2) . . ?
C00C C00I H00J 111.9 . . ?
C00C C00I C00L 104.5(3) . . ?
C00L C00I C009 112.7(3) . . ?
C00L C00I H00J 111.9 . . ?
C00D C00J H00K 124.6 . . ?
C00D C00J C00L 110.7(3) . . ?
C00L C00J H00K 124.6 . . ?
C00F C00K H00L 120.1 . . ?
C00G C00K C00F 119.8(4) . . ?
C00G C00K H00L 120.1 . . ?
O006 C00L C00I 125.5(4) . . ?
O006 C00L C00J 127.0(4) . . ?
C00J C00L C00I 107.5(3) . . ?
C008 C00M H00M 119.9 . . ?
C00O C00M C008 120.2(4) . . ?
C00O C00M H00M 119.9 . . ?
C00B C00N H00N 119.7 . . ?
C00P C00N C00B 120.6(4) . . ?
C00P C00N H00N 119.7 . . ?
C00M C00O H00O 119.8 . . ?
C00P C00O C00M 120.5(4) . . ?
C00P C00O H00O 119.8 . . ?
C00N C00P H00P 120.0 . . ?
C00O C00P C00N 120.0(4) . . ?
C00O C00P H00P 120.0 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2020-10-10
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.900
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 2154069'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2022-02-23 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_audit_creation_date             2021-12-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H30 N2 O4'
_chemical_formula_sum            'C26 H30 N2 O4'
_chemical_formula_weight         434.52
_chemical_absolute_configuration ad
_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           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                   9.2049(5)
_cell_length_b                   9.6660(5)
_cell_length_c                   12.7809(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.970(2)
_cell_angle_gamma                90
_cell_volume                     1128.77(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      70.177
_cell_measurement_theta_min      4.574
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.759
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1533 before and 0.0893 after correction.
The Ratio of minimum to maximum transmission is 0.6610.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22485
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.741
_diffrn_reflns_theta_min         4.840
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4108
_reflns_number_total             4155
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1894 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.089
_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)+(0.0682P)²+0.0816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.0983
_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 Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C21(H21), C22(H22), C23(H23),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C12(H12A,H12B,H12C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47125(17) 0.45564(16) 0.74615(11) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.44224(14) 0.45191(15) 0.57662(10) 0.0216(3) Uani 1 1 d . . . . .
O3 O 0.40712(18) 0.65473(17) 0.65880(12) 0.0308(4) Uani 1 1 d . . . . .
O4 O 0.62666(18) 0.61443(18) 0.12934(11) 0.0325(4) Uani 1 1 d . . . . .
N1 N 0.69216(18) 0.55038(19) 0.29656(13) 0.0229(4) Uani 1 1 d . . . . .
N2 N 0.80385(17) 0.52291(19) 0.38094(13) 0.0215(4) Uani 1 1 d . . . . .
C1 C 0.3612(3) 0.5816(4) 0.88528(19) 0.0489(8) Uani 1 1 d . . . . .
H1A H 0.3305 0.6602 0.8395 0.073 Uiso 1 1 calc R U . . .
H1B H 0.3788 0.6130 0.9586 0.073 Uiso 1 1 calc R U . . .
H1C H 0.2840 0.5112 0.8786 0.073 Uiso 1 1 calc R U . . .
C2 C 0.5002(2) 0.5205(2) 0.85324(15) 0.0260(4) Uani 1 1 d . . . . .
C3 C 0.4375(2) 0.5341(2) 0.66216(15) 0.0205(4) Uani 1 1 d . . . . .
C4 C 0.4347(2) 0.5257(2) 0.47739(14) 0.0198(4) Uani 1 1 d . . . . .
H4 H 0.3657 0.6053 0.4790 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5833(2) 0.5804(2) 0.45327(14) 0.0183(4) Uani 1 1 d . . . . .
H5 H 0.6095 0.6686 0.4919 0.022 Uiso 1 1 calc R U . . .
C6 C 0.5571(2) 0.6045(2) 0.33267(14) 0.0202(4) Uani 1 1 d . . . . .
H6 H 0.5437 0.7050 0.3156 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7192(2) 0.5633(2) 0.19497(16) 0.0237(4) Uani 1 1 d . . . . .
C8 C 0.8623(2) 0.5132(2) 0.16487(15) 0.0242(4) Uani 1 1 d . . . . .
C9 C 0.9258(2) 0.5910(3) 0.09048(16) 0.0284(5) Uani 1 1 d . . . . .
H9 H 0.8800 0.6740 0.0638 0.034 Uiso 1 1 calc R U . . .
C10 C 1.0549(2) 0.5483(3) 0.05526(17) 0.0340(5) Uani 1 1 d . . . . .
H10 H 1.0990 0.6032 0.0061 0.041 Uiso 1 1 calc R U . . .
C11 C 1.1199(3) 0.4248(3) 0.09206(18) 0.0353(6) Uani 1 1 d . . . . .
H11 H 1.2081 0.3948 0.0676 0.042 Uiso 1 1 calc R U . . .
C12 C 0.5532(4) 0.3989(3) 0.92202(18) 0.0467(7) Uani 1 1 d . . . . .
H12A H 0.4769 0.3278 0.9176 0.070 Uiso 1 1 calc R U . . .
H12B H 0.5754 0.4299 0.9952 0.070 Uiso 1 1 calc R U . . .
H12C H 0.6417 0.3604 0.8977 0.070 Uiso 1 1 calc R U . . .
C13 C 0.7155(2) 0.4770(2) 0.46387(15) 0.0188(4) Uani 1 1 d . . . . .
H13 H 0.6765 0.3826 0.4445 0.023 Uiso 1 1 calc R U . . .
C14 C 0.4192(2) 0.5199(2) 0.29129(15) 0.0244(4) Uani 1 1 d . . . . .
H14A H 0.3372 0.5824 0.2661 0.029 Uiso 1 1 calc R U . . .
H14B H 0.4394 0.4593 0.2323 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3811(2) 0.4330(2) 0.38470(15) 0.0234(4) Uani 1 1 d . . . . .
H15A H 0.2745 0.4162 0.3805 0.028 Uiso 1 1 calc R U . . .
H15B H 0.4333 0.3433 0.3888 0.028 Uiso 1 1 calc R U . . .
C16 C 1.0560(3) 0.3455(3) 0.1643(2) 0.0365(5) Uani 1 1 d . . . . .
H16 H 1.0997 0.2604 0.1883 0.044 Uiso 1 1 calc R U . . .
C17 C 0.9284(3) 0.3897(3) 0.20186(17) 0.0299(5) Uani 1 1 d . . . . .
H17 H 0.8861 0.3360 0.2526 0.036 Uiso 1 1 calc R U . . .
C18 C 0.8843(2) 0.6525(2) 0.41147(17) 0.0289(5) Uani 1 1 d . . . . .
H18A H 0.8161 0.7229 0.4338 0.035 Uiso 1 1 calc R U . . .
H18B H 0.9291 0.6897 0.3507 0.035 Uiso 1 1 calc R U . . .
C19 C 1.0020(3) 0.6202(3) 0.5016(2) 0.0349(5) Uani 1 1 d . . . . .
H19A H 1.0823 0.5689 0.4738 0.042 Uiso 1 1 calc R U . . .
H19B H 1.0430 0.7079 0.5323 0.042 Uiso 1 1 calc R U . . .
C20 C 0.9450(2) 0.5355(2) 0.58681(16) 0.0253(4) Uani 1 1 d . . . . .
C21 C 1.0317(2) 0.5182(3) 0.68366(17) 0.0305(5) Uani 1 1 d . . . . .
H21 H 1.1214 0.5673 0.6973 0.037 Uiso 1 1 calc R U . . .
C22 C 0.9885(2) 0.4304(3) 0.76005(17) 0.0306(5) Uani 1 1 d . . . . .
H22 H 1.0483 0.4197 0.8256 0.037 Uiso 1 1 calc R U . . .
C23 C 0.8580(2) 0.3583(2) 0.74031(17) 0.0282(5) Uani 1 1 d . . . . .
H23 H 0.8288 0.2966 0.7917 0.034 Uiso 1 1 calc R U . . .
C24 C 0.7702(2) 0.3766(2) 0.64541(16) 0.0228(4) Uani 1 1 d . . . . .
H24 H 0.6804 0.3274 0.6324 0.027 Uiso 1 1 calc R U . . .
C25 C 0.8113(2) 0.4660(2) 0.56857(15) 0.0202(4) Uani 1 1 d . . . . .
C26 C 0.6197(3) 0.6279(3) 0.85311(19) 0.0316(5) Uani 1 1 d . . . . .
H26A H 0.7040 0.5871 0.8244 0.047 Uiso 1 1 calc R U . . .
H26B H 0.6496 0.6594 0.9254 0.047 Uiso 1 1 calc R U . . .
H26C H 0.5830 0.7067 0.8094 0.047 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 C2 1.499(2) . ?
O1 C3 1.320(3) . ?
O2 C3 1.356(2) . ?
O2 C4 1.449(2) . ?
O3 C3 1.199(3) . ?
O4 C7 1.224(3) . ?
N1 N2 1.422(2) . ?
N1 C6 1.473(2) . ?
N1 C7 1.357(3) . ?
N2 C13 1.480(2) . ?
N2 C18 1.483(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.510(3) . ?
C2 C12 1.512(4) . ?
C2 C26 1.513(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.532(2) . ?
C4 C15 1.519(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.549(2) . ?
C5 C13 1.568(3) . ?
C6 H6 1.0000 . ?
C6 C14 1.549(3) . ?
C7 C8 1.497(3) . ?
C8 C9 1.395(3) . ?
C8 C17 1.396(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(4) . ?
C11 H11 0.9500 . ?
C11 C16 1.385(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C25 1.514(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.534(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.515(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.507(3) . ?
C20 C21 1.399(3) . ?
C20 C25 1.397(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.395(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C3 O1 C2 120.02(17) . . ?
C3 O2 C4 114.48(15) . . ?
N2 N1 C6 112.86(14) . . ?
C7 N1 N2 122.91(16) . . ?
C7 N1 C6 121.76(16) . . ?
N1 N2 C13 100.94(14) . . ?
N1 N2 C18 109.49(16) . . ?
C13 N2 C18 111.41(16) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 110.39(17) . . ?
O1 C2 C12 102.42(18) . . ?
O1 C2 C26 109.55(16) . . ?
C1 C2 C12 111.7(2) . . ?
C1 C2 C26 111.8(2) . . ?
C12 C2 C26 110.5(2) . . ?
O1 C3 O2 106.95(17) . . ?
O3 C3 O1 128.22(19) . . ?
O3 C3 O2 124.83(19) . . ?
O2 C4 H4 108.9 . . ?
O2 C4 C5 113.37(14) . . ?
O2 C4 C15 111.66(17) . . ?
C5 C4 H4 108.9 . . ?
C15 C4 H4 108.9 . . ?
C15 C4 C5 105.07(14) . . ?
C4 C5 H5 111.3 . . ?
C4 C5 C6 102.55(14) . . ?
C4 C5 C13 117.72(16) . . ?
C6 C5 H5 111.3 . . ?
C6 C5 C13 101.96(14) . . ?
C13 C5 H5 111.3 . . ?
N1 C6 C5 102.90(14) . . ?
N1 C6 H6 111.3 . . ?
N1 C6 C14 113.19(16) . . ?
C5 C6 H6 111.3 . . ?
C14 C6 C5 106.42(15) . . ?
C14 C6 H6 111.3 . . ?
O4 C7 N1 119.98(19) . . ?
O4 C7 C8 121.00(18) . . ?
N1 C7 C8 119.01(18) . . ?
C9 C8 C7 117.1(2) . . ?
C9 C8 C17 119.4(2) . . ?
C17 C8 C7 123.4(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.0 . . ?
C16 C11 C10 120.0(2) . . ?
C16 C11 H11 120.0 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C5 103.59(15) . . ?
N2 C13 H13 107.9 . . ?
N2 C13 C25 110.03(15) . . ?
C5 C13 H13 107.9 . . ?
C25 C13 C5 118.90(15) . . ?
C25 C13 H13 107.9 . . ?
C6 C14 H14A 110.5 . . ?
C6 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
C15 C14 C6 106.16(15) . . ?
C15 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
C4 C15 C14 101.60(17) . . ?
C4 C15 H15A 111.5 . . ?
C4 C15 H15B 111.5 . . ?
C14 C15 H15A 111.5 . . ?
C14 C15 H15B 111.5 . . ?
H15A C15 H15B 109.3 . . ?
C11 C16 H16 119.8 . . ?
C11 C16 C17 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C8 C17 H17 120.1 . . ?
C16 C17 C8 119.9(2) . . ?
C16 C17 H17 120.1 . . ?
N2 C18 H18A 110.0 . . ?
N2 C18 H18B 110.0 . . ?
N2 C18 C19 108.28(19) . . ?
H18A C18 H18B 108.4 . . ?
C19 C18 H18A 110.0 . . ?
C19 C18 H18B 110.0 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 C18 112.42(17) . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C21 C20 C19 119.53(19) . . ?
C25 C20 C19 121.19(19) . . ?
C25 C20 C21 119.1(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.70(19) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 121.08(19) . . ?
C25 C24 H24 119.5 . . ?
C20 C25 C13 121.37(18) . . ?
C24 C25 C13 119.15(17) . . ?
C24 C25 C20 119.30(18) . . ?
C2 C26 H26A 109.5 . . ?
C2 C26 H26B 109.5 . . ?
C2 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
O2 C4 C5 C6 160.38(15) . . . . ?
O2 C4 C5 C13 49.5(2) . . . . ?
O2 C4 C15 C14 -166.34(15) . . . . ?
O4 C7 C8 C9 37.6(3) . . . . ?
O4 C7 C8 C17 -138.0(2) . . . . ?
N1 N2 C13 C5 -41.81(18) . . . . ?
N1 N2 C13 C25 -169.93(16) . . . . ?
N1 N2 C18 C19 179.84(16) . . . . ?
N1 C6 C14 C15 104.49(18) . . . . ?
N1 C7 C8 C9 -143.0(2) . . . . ?
N1 C7 C8 C17 41.4(3) . . . . ?
N2 N1 C6 C5 -11.3(2) . . . . ?
N2 N1 C6 C14 -125.76(17) . . . . ?
N2 N1 C7 O4 -164.9(2) . . . . ?
N2 N1 C7 C8 15.6(3) . . . . ?
N2 C13 C25 C20 20.2(2) . . . . ?
N2 C13 C25 C24 -154.88(18) . . . . ?
N2 C18 C19 C20 -47.3(3) . . . . ?
C2 O1 C3 O2 169.77(14) . . . . ?
C2 O1 C3 O3 -10.6(3) . . . . ?
C3 O1 C2 C1 68.2(3) . . . . ?
C3 O1 C2 C12 -172.7(2) . . . . ?
C3 O1 C2 C26 -55.4(3) . . . . ?
C3 O2 C4 C5 83.99(19) . . . . ?
C3 O2 C4 C15 -157.57(15) . . . . ?
C4 O2 C3 O1 -169.11(15) . . . . ?
C4 O2 C3 O3 11.2(3) . . . . ?
C4 C5 C6 N1 -137.34(15) . . . . ?
C4 C5 C6 C14 -18.1(2) . . . . ?
C4 C5 C13 N2 146.75(15) . . . . ?
C4 C5 C13 C25 -90.8(2) . . . . ?
C5 C4 C15 C14 -43.05(19) . . . . ?
C5 C6 C14 C15 -7.8(2) . . . . ?
C5 C13 C25 C20 -98.9(2) . . . . ?
C5 C13 C25 C24 86.0(2) . . . . ?
C6 N1 N2 C13 34.1(2) . . . . ?
C6 N1 N2 C18 -83.47(19) . . . . ?
C6 N1 C7 O4 -4.0(3) . . . . ?
C6 N1 C7 C8 176.58(19) . . . . ?
C6 C5 C13 N2 35.52(18) . . . . ?
C6 C5 C13 C25 157.93(16) . . . . ?
C6 C14 C15 C4 30.71(19) . . . . ?
C7 N1 N2 C13 -163.45(19) . . . . ?
C7 N1 N2 C18 79.0(2) . . . . ?
C7 N1 C6 C5 -174.03(19) . . . . ?
C7 N1 C6 C14 71.5(2) . . . . ?
C7 C8 C9 C10 -177.3(2) . . . . ?
C7 C8 C17 C16 175.4(2) . . . . ?
C8 C9 C10 C11 1.8(3) . . . . ?
C9 C8 C17 C16 -0.1(3) . . . . ?
C9 C10 C11 C16 -0.5(4) . . . . ?
C10 C11 C16 C17 -1.1(4) . . . . ?
C11 C16 C17 C8 1.4(4) . . . . ?
C13 N2 C18 C19 69.1(2) . . . . ?
C13 C5 C6 N1 -15.05(19) . . . . ?
C13 C5 C6 C14 104.20(17) . . . . ?
C15 C4 C5 C6 38.2(2) . . . . ?
C15 C4 C5 C13 -72.7(2) . . . . ?
C17 C8 C9 C10 -1.5(3) . . . . ?
C18 N2 C13 C5 74.34(19) . . . . ?
C18 N2 C13 C25 -53.8(2) . . . . ?
C18 C19 C20 C21 -168.3(2) . . . . ?
C18 C19 C20 C25 16.1(3) . . . . ?
C19 C20 C21 C22 -173.8(2) . . . . ?
C19 C20 C25 C13 -2.2(3) . . . . ?
C19 C20 C25 C24 172.9(2) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C20 C25 C13 -177.83(19) . . . . ?
C21 C20 C25 C24 -2.7(3) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C23 C24 C25 C13 176.85(18) . . . . ?
C23 C24 C25 C20 1.6(3) . . . . ?
C25 C20 C21 C22 1.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6b
_database_code_depnum_ccdc_archive 'CCDC 2154068'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2022-02-23 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_audit_creation_date             2021-11-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O3 S'
_chemical_formula_sum            'C21 H20 N2 O3 S'
_chemical_formula_weight         380.45
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   10.1467(5)
_cell_length_b                   6.1824(2)
_cell_length_c                   15.3256(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.402(2)
_cell_angle_gamma                90
_cell_volume                     922.26(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9286
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.270
_cell_measurement_theta_min      2.817
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1383 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.7700.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31963
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_min         2.092
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3582
_reflns_number_total             4245
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.034
_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)+(0.0440P)²+0.0446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0851
_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 Ternary CH refined with riding coordinates:
 C1(H1), C18(H18), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
S1 S 0.10434(6) 0.26065(9) 0.10654(4) 0.03883(16) Uani 1 1 d . . . . .
O1 O -0.03725(18) 0.3193(3) 0.07215(13) 0.0591(6) Uani 1 1 d . . . . .
O2 O 0.1340(2) 0.0617(3) 0.15671(12) 0.0503(5) Uani 1 1 d . . . . .
O3 O 0.4743(2) 0.8137(4) 0.06213(13) 0.0635(6) Uani 1 1 d . . . . .
C1 C 0.3156(2) 0.4243(4) 0.25717(13) 0.0302(4) Uani 1 1 d . . . . .
H1 H 0.3493 0.2804 0.2473 0.036 Uiso 1 1 calc R U . . .
N2 N 0.4143(2) 0.6117(4) 0.16588(12) 0.0381(5) Uani 1 1 d . . . . .
C22 C 0.3348(4) 0.7177(5) 0.57006(18) 0.0634(9) Uani 1 1 d . . . . .
H22A H 0.2925 0.8557 0.5520 0.095 Uiso 1 1 calc R U . . .
H22B H 0.4326 0.7313 0.5827 0.095 Uiso 1 1 calc R U . . .
H22C H 0.3127 0.6686 0.6237 0.095 Uiso 1 1 calc R U . . .
C2 C 0.2823(3) 0.5565(5) 0.49428(16) 0.0447(6) Uani 1 1 d . . . . .
C3 C 0.3213(2) 0.5720(4) 0.41319(14) 0.0361(5) Uani 1 1 d . . . . .
C4 C 0.2746(2) 0.4175(4) 0.34509(14) 0.0325(5) Uani 1 1 d . . . . .
N5 N 0.42587(19) 0.5812(3) 0.26021(11) 0.0330(4) Uani 1 1 d . . . . .
C6 C 0.5081(3) 0.7294(5) 0.13686(16) 0.0432(6) Uani 1 1 d . . . . .
C7 C 0.6519(2) 0.7404(5) 0.19659(16) 0.0439(6) Uani 1 1 d . . . . .
C8 C 0.7246(3) 0.9304(6) 0.19586(18) 0.0551(7) Uani 1 1 d . . . . .
H8 H 0.6802 1.0502 0.1641 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8616(3) 0.9418(7) 0.2419(2) 0.0708(10) Uani 1 1 d . . . . .
H9 H 0.9096 1.0697 0.2413 0.085 Uiso 1 1 calc R U . . .
C10 C 0.9279(3) 0.7669(9) 0.2885(2) 0.0757(10) Uani 1 1 d . . . . .
H10 H 1.0210 0.7754 0.3190 0.091 Uiso 1 1 calc R U . . .
C11 C 0.7179(3) 0.5646(5) 0.2446(2) 0.0572(7) Uani 1 1 d . . . . .
H11 H 0.6697 0.4376 0.2466 0.069 Uiso 1 1 calc R U . . .
C12 C 0.8573(3) 0.5783(7) 0.2904(2) 0.0728(10) Uani 1 1 d . . . . .
H12 H 0.9026 0.4594 0.3223 0.087 Uiso 1 1 calc R U . . .
C13 C 0.1979(3) 0.3905(5) 0.50438(17) 0.0528(7) Uani 1 1 d . . . . .
H13 H 0.1715 0.3808 0.5576 0.063 Uiso 1 1 calc R U . . .
C14 C 0.1518(3) 0.2382(5) 0.43725(17) 0.0515(7) Uani 1 1 d . . . . .
H14 H 0.0945 0.1272 0.4453 0.062 Uiso 1 1 calc R U . . .
C15 C 0.1905(2) 0.2498(5) 0.35775(15) 0.0421(5) Uani 1 1 d . . . . .
H15 H 0.1602 0.1455 0.3128 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4137(2) 0.7501(5) 0.40016(14) 0.0421(5) Uani 1 1 d . . . . .
H16A H 0.5081 0.7132 0.4315 0.050 Uiso 1 1 calc R U . . .
H16B H 0.3910 0.8821 0.4269 0.050 Uiso 1 1 calc R U . . .
C17 C 0.4008(3) 0.7889(4) 0.30054(15) 0.0397(5) Uani 1 1 d . . . . .
H17A H 0.3095 0.8420 0.2697 0.048 Uiso 1 1 calc R U . . .
H17B H 0.4673 0.8959 0.2942 0.048 Uiso 1 1 calc R U . . .
C18 C 0.1975(2) 0.4863(4) 0.17046(15) 0.0327(5) Uani 1 1 d . . . . .
H18 H 0.1342 0.5898 0.1856 0.039 Uiso 1 1 calc R U . . .
C19 C 0.1881(3) 0.2677(6) 0.02235(16) 0.0528(6) Uani 1 1 d . . . . .
H19 H 0.1773 0.1643 -0.0232 0.063 Uiso 1 1 calc R U . . .
C20 C 0.2685(3) 0.4374(5) 0.03108(16) 0.0521(7) Uani 1 1 d . . . . .
H20 H 0.3211 0.4619 -0.0088 0.062 Uiso 1 1 calc R U . . .
C21 C 0.2725(2) 0.5894(4) 0.10734(15) 0.0373(5) Uani 1 1 d . . . . .
H21 H 0.2329 0.7302 0.0848 0.045 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
S1 O1 1.4302(18) . ?
S1 O2 1.436(2) . ?
S1 C18 1.810(2) . ?
S1 C19 1.734(3) . ?
O3 C6 1.216(3) . ?
C1 H1 0.9800 . ?
C1 C4 1.518(3) . ?
C1 N5 1.472(3) . ?
C1 C18 1.565(3) . ?
N2 N5 1.429(2) . ?
N2 C6 1.369(3) . ?
N2 C21 1.471(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 C2 1.508(4) . ?
C2 C3 1.410(3) . ?
C2 C13 1.373(4) . ?
C3 C4 1.395(3) . ?
C3 C16 1.496(4) . ?
C4 C15 1.391(3) . ?
N5 C17 1.478(3) . ?
C6 C7 1.489(3) . ?
C7 C8 1.388(4) . ?
C7 C11 1.376(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.364(6) . ?
C10 H10 0.9300 . ?
C10 C12 1.373(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.375(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.514(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18 0.9800 . ?
C18 C21 1.529(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.313(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.492(4) . ?
C21 H21 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
O1 S1 O2 116.83(13) . . ?
O1 S1 C18 108.71(11) . . ?
O1 S1 C19 111.81(13) . . ?
O2 S1 C18 111.81(10) . . ?
O2 S1 C19 110.29(15) . . ?
C19 S1 C18 95.32(13) . . ?
C4 C1 H1 107.9 . . ?
C4 C1 C18 115.13(18) . . ?
N5 C1 H1 107.9 . . ?
N5 C1 C4 112.72(17) . . ?
N5 C1 C18 104.97(17) . . ?
C18 C1 H1 107.9 . . ?
N5 N2 C21 113.06(17) . . ?
C6 N2 N5 122.17(19) . . ?
C6 N2 C21 120.12(19) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 C22 H22A 109.5 . . ?
C2 C22 H22B 109.5 . . ?
C2 C22 H22C 109.5 . . ?
C3 C2 C22 120.5(3) . . ?
C13 C2 C22 120.2(2) . . ?
C13 C2 C3 119.3(2) . . ?
C2 C3 C16 120.7(2) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 C16 119.8(2) . . ?
C3 C4 C1 121.6(2) . . ?
C15 C4 C1 118.5(2) . . ?
C15 C4 C3 119.9(2) . . ?
C1 N5 C17 111.49(18) . . ?
N2 N5 C1 102.13(16) . . ?
N2 N5 C17 109.51(18) . . ?
O3 C6 N2 119.7(2) . . ?
O3 C6 C7 121.8(2) . . ?
N2 C6 C7 118.4(2) . . ?
C8 C7 C6 117.6(3) . . ?
C11 C7 C6 122.5(3) . . ?
C11 C7 C8 119.6(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C12 120.1(3) . . ?
C12 C10 H10 120.0 . . ?
C7 C11 H11 120.2 . . ?
C7 C11 C12 119.5(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C12 C11 120.2(4) . . ?
C10 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C2 C13 H13 119.4 . . ?
C2 C13 C14 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C4 C15 H15 120.0 . . ?
C14 C15 C4 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C3 C16 H16A 109.2 . . ?
C3 C16 H16B 109.2 . . ?
C3 C16 C17 111.8(2) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
N5 C17 C16 107.9(2) . . ?
N5 C17 H17A 110.1 . . ?
N5 C17 H17B 110.1 . . ?
C16 C17 H17A 110.1 . . ?
C16 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
S1 C18 H18 110.8 . . ?
C1 C18 S1 115.37(16) . . ?
C1 C18 H18 110.8 . . ?
C21 C18 S1 104.85(15) . . ?
C21 C18 C1 103.94(18) . . ?
C21 C18 H18 110.8 . . ?
S1 C19 H19 124.3 . . ?
C20 C19 S1 111.4(2) . . ?
C20 C19 H19 124.3 . . ?
C19 C20 H20 121.2 . . ?
C19 C20 C21 117.5(2) . . ?
C21 C20 H20 121.2 . . ?
N2 C21 C18 103.23(17) . . ?
N2 C21 C20 110.0(2) . . ?
N2 C21 H21 111.4 . . ?
C18 C21 H21 111.4 . . ?
C20 C21 C18 108.9(2) . . ?
C20 C21 H21 111.4 . . ?

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
S1 C18 C21 N2 -130.80(17) . . . . ?
S1 C18 C21 C20 -13.9(2) . . . . ?
S1 C19 C20 C21 -0.8(4) . . . . ?
O1 S1 C18 C1 143.29(17) . . . . ?
O1 S1 C18 C21 -103.04(17) . . . . ?
O1 S1 C19 C20 105.5(2) . . . . ?
O2 S1 C18 C1 12.8(2) . . . . ?
O2 S1 C18 C21 126.50(15) . . . . ?
O2 S1 C19 C20 -122.8(2) . . . . ?
O3 C6 C7 C8 36.5(4) . . . . ?
O3 C6 C7 C11 -137.1(3) . . . . ?
C1 C4 C15 C14 179.7(2) . . . . ?
C1 N5 C17 C16 67.7(2) . . . . ?
C1 C18 C21 N2 -9.3(2) . . . . ?
C1 C18 C21 C20 107.6(2) . . . . ?
N2 N5 C17 C16 179.93(17) . . . . ?
N2 C6 C7 C8 -146.7(2) . . . . ?
N2 C6 C7 C11 39.7(4) . . . . ?
C22 C2 C3 C4 178.2(2) . . . . ?
C22 C2 C3 C16 -0.9(4) . . . . ?
C22 C2 C13 C14 -178.2(3) . . . . ?
C2 C3 C4 C1 -178.9(2) . . . . ?
C2 C3 C4 C15 -0.1(3) . . . . ?
C2 C3 C16 C17 -158.7(2) . . . . ?
C2 C13 C14 C15 0.2(4) . . . . ?
C3 C2 C13 C14 0.5(4) . . . . ?
C3 C4 C15 C14 0.9(4) . . . . ?
C3 C16 C17 N5 -54.8(3) . . . . ?
C4 C1 N5 N2 -161.42(18) . . . . ?
C4 C1 N5 C17 -44.6(2) . . . . ?
C4 C1 C18 S1 -93.2(2) . . . . ?
C4 C1 C18 C21 152.6(2) . . . . ?
C4 C3 C16 C17 22.3(3) . . . . ?
N5 C1 C4 C3 10.5(3) . . . . ?
N5 C1 C4 C15 -168.3(2) . . . . ?
N5 C1 C18 S1 142.30(16) . . . . ?
N5 C1 C18 C21 28.1(2) . . . . ?
N5 N2 C6 O3 -154.9(3) . . . . ?
N5 N2 C6 C7 28.3(4) . . . . ?
N5 N2 C21 C18 -13.5(3) . . . . ?
N5 N2 C21 C20 -129.6(2) . . . . ?
C6 N2 N5 C1 -172.7(2) . . . . ?
C6 N2 N5 C17 69.0(3) . . . . ?
C6 N2 C21 C18 -169.8(2) . . . . ?
C6 N2 C21 C20 74.0(3) . . . . ?
C6 C7 C8 C9 -173.0(3) . . . . ?
C6 C7 C11 C12 172.2(3) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C7 C11 C12 C10 0.8(5) . . . . ?
C8 C7 C11 C12 -1.3(4) . . . . ?
C8 C9 C10 C12 -0.6(5) . . . . ?
C9 C10 C12 C11 0.1(5) . . . . ?
C11 C7 C8 C9 0.8(4) . . . . ?
C13 C2 C3 C4 -0.6(4) . . . . ?
C13 C2 C3 C16 -179.6(2) . . . . ?
C13 C14 C15 C4 -0.9(4) . . . . ?
C16 C3 C4 C1 0.2(3) . . . . ?
C16 C3 C4 C15 178.9(2) . . . . ?
C18 S1 C19 C20 -7.1(3) . . . . ?
C18 C1 C4 C3 -109.8(2) . . . . ?
C18 C1 C4 C15 71.4(3) . . . . ?
C18 C1 N5 N2 -35.4(2) . . . . ?
C18 C1 N5 C17 81.5(2) . . . . ?
C19 S1 C18 C1 -101.54(19) . . . . ?
C19 S1 C18 C21 12.14(18) . . . . ?
C19 C20 C21 N2 122.8(3) . . . . ?
C19 C20 C21 C18 10.3(3) . . . . ?
C21 N2 N5 C1 31.5(2) . . . . ?
C21 N2 N5 C17 -86.8(2) . . . . ?
C21 N2 C6 O3 -0.7(4) . . . . ?
C21 N2 C6 C7 -177.5(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_4a
_database_code_depnum_ccdc_archive 'CCDC 2154067'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2022-02-23 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_audit_creation_date             2021-03-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N2 O2'
_chemical_formula_sum            'C21 H18 N2 O2'
_chemical_formula_weight         330.37
_chemical_absolute_configuration ad
_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           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                   8.2297(3)
_cell_length_b                   9.0042(3)
_cell_length_c                   22.3918(8)
_cell_angle_alpha                90
_cell_angle_beta                 88.206(2)
_cell_angle_gamma                90
_cell_volume                     1658.46(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9766
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.185
_cell_measurement_theta_min      3.95
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.729
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1480 before and 0.0857 after correction.
The Ratio of minimum to maximum transmission is 0.5475.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            43786
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.397
_diffrn_reflns_theta_min         1.974
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5758
_reflns_number_total             6055
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6055
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.050
_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)+(0.0342P)²+0.3828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0868
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C16(H16), C17(H17), C35(H35), C36(H36), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C28(H28A,H28B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C14(H14), C15(H15), C18(H18),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C31(H31), C32(H32),
  C33(H33), C34(H34), C38(H38), C39(H39), C42(H42), C43(H43)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2624(3) 0.7408(3) 0.51410(10) 0.0652(6) Uani 1 1 d . . . . .
O2 O 0.4095(3) 0.9296(3) 0.24556(14) 0.0866(10) Uani 1 1 d . . . . .
O3 O 0.1629(2) 0.4452(2) 0.27794(9) 0.0504(5) Uani 1 1 d . . . . .
O4 O 0.2952(2) 0.0381(2) 0.05219(10) 0.0547(6) Uani 1 1 d . . . . .
N1 N 0.0644(2) 0.8437(2) 0.38222(9) 0.0356(4) Uani 1 1 d . . . . .
N2 N 0.3546(2) 0.2373(2) 0.10750(10) 0.0374(5) Uani 1 1 d . . . . .
N3 N 0.4742(2) 0.3270(2) 0.13477(9) 0.0336(4) Uani 1 1 d . . . . .
C1 C -0.3390(4) 0.7819(4) 0.55020(13) 0.0542(7) Uani 1 1 d . . . . .
H1 H -0.4476 0.7855 0.5658 0.065 Uiso 1 1 calc R U . . .
C2 C -0.3029(3) 0.7038(4) 0.49818(13) 0.0486(7) Uani 1 1 d . . . . .
H2 H -0.3861 0.6503 0.4790 0.058 Uiso 1 1 calc R U . . .
C3 C -0.1463(3) 0.7035(3) 0.47403(12) 0.0414(6) Uani 1 1 d . . . . .
H3 H -0.1233 0.6527 0.4376 0.050 Uiso 1 1 calc R U . . .
C4 C -0.0223(3) 0.7769(3) 0.50265(12) 0.0411(6) Uani 1 1 d . . . . .
C5 C 0.1512(3) 0.7672(3) 0.48056(13) 0.0461(6) Uani 1 1 d . . . . .
N6 N 0.1815(2) 0.7868(3) 0.42132(10) 0.0427(5) Uani 1 1 d . . . . .
C7 C 0.0640(3) 1.0064(3) 0.38124(13) 0.0421(6) Uani 1 1 d . . . . .
H7A H 0.1687 1.0442 0.3644 0.050 Uiso 1 1 calc R U . . .
H7B H 0.0481 1.0461 0.4222 0.050 Uiso 1 1 calc R U . . .
C8 C -0.0740(3) 1.0539(3) 0.34284(12) 0.0408(6) Uani 1 1 d . . . . .
H8A H -0.0744 1.1634 0.3392 0.049 Uiso 1 1 calc R U . . .
H8B H -0.1787 1.0229 0.3619 0.049 Uiso 1 1 calc R U . . .
C9 C -0.0562(3) 0.9849(3) 0.28164(11) 0.0352(5) Uani 1 1 d . . . . .
C10 C -0.1352(3) 1.0475(3) 0.23343(12) 0.0428(6) Uani 1 1 d . . . . .
H10 H -0.2010 1.1331 0.2396 0.051 Uiso 1 1 calc R U . . .
C11 C -0.1192(3) 0.9868(4) 0.17679(13) 0.0493(7) Uani 1 1 d . . . . .
H11 H -0.1761 1.0286 0.1446 0.059 Uiso 1 1 calc R U . . .
C12 C 0.1149(3) 0.7791(3) 0.32407(11) 0.0334(5) Uani 1 1 d . . . . .
H12 H 0.0709 0.6756 0.3236 0.040 Uiso 1 1 calc R U . . .
C13 C 0.0403(3) 0.8596(3) 0.27250(11) 0.0338(5) Uani 1 1 d . . . . .
C14 C 0.0601(3) 0.8017(3) 0.21461(12) 0.0445(6) Uani 1 1 d . . . . .
H14 H 0.1289 0.7183 0.2077 0.053 Uiso 1 1 calc R U . . .
C15 C -0.0198(4) 0.8651(4) 0.16757(13) 0.0518(7) Uani 1 1 d . . . . .
H15 H -0.0061 0.8246 0.1286 0.062 Uiso 1 1 calc R U . . .
C16 C 0.3036(3) 0.7647(3) 0.32426(13) 0.0422(6) Uani 1 1 d . . . . .
H16 H 0.3384 0.6687 0.3054 0.051 Uiso 1 1 calc R U . . .
C17 C 0.3415(3) 0.7639(3) 0.39107(14) 0.0453(6) Uani 1 1 d . . . . .
H17 H 0.3911 0.6675 0.4031 0.054 Uiso 1 1 calc R U . . .
C18 C 0.4581(3) 0.8909(4) 0.3984(2) 0.0676(10) Uani 1 1 d . . . . .
H18 H 0.5014 0.9196 0.4355 0.081 Uiso 1 1 calc R U . . .
C19 C 0.4933(4) 0.9582(4) 0.3467(2) 0.0817(14) Uani 1 1 d . . . . .
H19 H 0.5669 1.0389 0.3421 0.098 Uiso 1 1 calc R U . . .
C20 C 0.4042(3) 0.8920(4) 0.29787(19) 0.0629(10) Uani 1 1 d . . . . .
C21 C -0.0586(4) 0.8504(3) 0.55620(13) 0.0500(7) Uani 1 1 d . . . . .
H21 H 0.0254 0.8981 0.5771 0.060 Uiso 1 1 calc R U . . .
C22 C -0.2177(4) 0.8540(4) 0.57903(14) 0.0563(8) Uani 1 1 d . . . . .
H22 H -0.2423 0.9069 0.6149 0.068 Uiso 1 1 calc R U . . .
C23 C 0.8809(3) 0.0659(4) -0.00269(12) 0.0467(7) Uani 1 1 d . . . . .
H23 H 0.9878 0.0502 -0.0187 0.056 Uiso 1 1 calc R U . . .
C24 C 0.7910(3) -0.0522(3) 0.01908(12) 0.0437(6) Uani 1 1 d . . . . .
H24 H 0.8355 -0.1495 0.0178 0.052 Uiso 1 1 calc R U . . .
C25 C 0.6347(3) -0.0288(3) 0.04301(11) 0.0375(5) Uani 1 1 d . . . . .
H25 H 0.5721 -0.1105 0.0576 0.045 Uiso 1 1 calc R U . . .
C26 C 0.5705(3) 0.1137(3) 0.04559(11) 0.0339(5) Uani 1 1 d . . . . .
C27 C 0.3980(3) 0.1263(3) 0.06885(12) 0.0384(6) Uani 1 1 d . . . . .
C28 C 0.4442(3) 0.4853(3) 0.12356(11) 0.0357(5) Uani 1 1 d . . . . .
H28A H 0.3384 0.5154 0.1420 0.043 Uiso 1 1 calc R U . . .
H28B H 0.4413 0.5043 0.0801 0.043 Uiso 1 1 calc R U . . .
C29 C 0.5807(3) 0.5731(3) 0.15057(11) 0.0370(5) Uani 1 1 d . . . . .
H29A H 0.6839 0.5515 0.1284 0.044 Uiso 1 1 calc R U . . .
H29B H 0.5581 0.6806 0.1468 0.044 Uiso 1 1 calc R U . . .
C30 C 0.5985(3) 0.5344(3) 0.21569(11) 0.0321(5) Uani 1 1 d . . . . .
C31 C 0.6785(3) 0.6314(3) 0.25355(11) 0.0351(5) Uani 1 1 d . . . . .
H31 H 0.7191 0.7232 0.2384 0.042 Uiso 1 1 calc R U . . .
C32 C 0.6995(3) 0.5952(3) 0.31303(12) 0.0412(6) Uani 1 1 d . . . . .
H32 H 0.7561 0.6611 0.3382 0.049 Uiso 1 1 calc R U . . .
C33 C 0.8159(3) 0.2068(3) -0.00137(12) 0.0438(6) Uani 1 1 d . . . . .
H33 H 0.8770 0.2875 -0.0177 0.053 Uiso 1 1 calc R U . . .
C34 C 0.6616(3) 0.2320(3) 0.02363(11) 0.0370(5) Uani 1 1 d . . . . .
H34 H 0.6189 0.3300 0.0256 0.044 Uiso 1 1 calc R U . . .
C35 C 0.4563(3) 0.2889(3) 0.19889(11) 0.0322(5) Uani 1 1 d . . . . .
H35 H 0.5150 0.1929 0.2044 0.039 Uiso 1 1 calc R U . . .
C36 C 0.2710(3) 0.2558(3) 0.21018(11) 0.0343(5) Uani 1 1 d . . . . .
H36 H 0.2580 0.1694 0.2380 0.041 Uiso 1 1 calc R U . . .
C37 C 0.1576(3) 0.3802(3) 0.23054(11) 0.0358(5) Uani 1 1 d . . . . .
C38 C 0.0381(3) 0.4032(3) 0.18404(12) 0.0409(6) Uani 1 1 d . . . . .
H38 H -0.0495 0.4719 0.1866 0.049 Uiso 1 1 calc R U . . .
C39 C 0.0703(3) 0.3142(3) 0.13813(13) 0.0439(6) Uani 1 1 d . . . . .
H39 H 0.0106 0.3146 0.1025 0.053 Uiso 1 1 calc R U . . .
C40 C 0.2112(3) 0.2124(3) 0.14842(12) 0.0397(6) Uani 1 1 d . . . . .
H40 H 0.1762 0.1061 0.1478 0.048 Uiso 1 1 calc R U . . .
C41 C 0.5365(3) 0.4015(3) 0.23815(11) 0.0320(5) Uani 1 1 d . . . . .
C42 C 0.5560(3) 0.3680(3) 0.29877(11) 0.0390(6) Uani 1 1 d . . . . .
H42 H 0.5120 0.2783 0.3147 0.047 Uiso 1 1 calc R U . . .
C43 C 0.6382(3) 0.4635(3) 0.33560(12) 0.0442(6) Uani 1 1 d . . . . .
H43 H 0.6524 0.4384 0.3763 0.053 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 C5 1.225(3) . ?
O2 C20 1.219(4) . ?
O3 C37 1.214(3) . ?
O4 C27 1.227(3) . ?
N1 N6 1.418(3) . ?
N1 C7 1.465(3) . ?
N1 C12 1.474(3) . ?
N2 N3 1.425(3) . ?
N2 C27 1.363(3) . ?
N2 C40 1.488(3) . ?
N3 C28 1.470(3) . ?
N3 C35 1.479(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(4) . ?
C1 C22 1.369(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(4) . ?
C4 C5 1.499(4) . ?
C4 C21 1.394(4) . ?
C5 N6 1.354(4) . ?
N6 C17 1.476(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.507(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.507(4) . ?
C9 C10 1.396(4) . ?
C9 C13 1.391(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(4) . ?
C11 H11 0.9500 . ?
C11 C15 1.379(5) . ?
C12 H12 1.0000 . ?
C12 C13 1.510(4) . ?
C12 C16 1.558(3) . ?
C13 C14 1.402(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(4) . ?
C15 H15 0.9500 . ?
C16 H16 1.0000 . ?
C16 C17 1.538(4) . ?
C16 C20 1.522(4) . ?
C17 H17 1.0000 . ?
C17 C18 1.505(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.330(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.462(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.375(4) . ?
C23 C33 1.377(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.394(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(4) . ?
C26 C27 1.501(3) . ?
C26 C34 1.384(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.515(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.511(3) . ?
C30 C31 1.397(3) . ?
C30 C41 1.389(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.387(4) . ?
C32 H32 0.9500 . ?
C32 C43 1.378(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(4) . ?
C34 H34 0.9500 . ?
C35 H35 1.0000 . ?
C35 C36 1.567(3) . ?
C35 C41 1.507(3) . ?
C36 H36 1.0000 . ?
C36 C37 1.519(3) . ?
C36 C40 1.533(4) . ?
C37 C38 1.469(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.324(4) . ?
C39 H39 0.9500 . ?
C39 C40 1.501(4) . ?
C40 H40 1.0000 . ?
C41 C42 1.405(4) . ?
C42 H42 0.9500 . ?
C42 C43 1.383(4) . ?
C43 H43 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
N6 N1 C7 111.9(2) . . ?
N6 N1 C12 102.96(19) . . ?
C7 N1 C12 112.5(2) . . ?
N3 N2 C40 111.51(19) . . ?
C27 N2 N3 121.11(18) . . ?
C27 N2 C40 117.9(2) . . ?
N2 N3 C28 110.75(19) . . ?
N2 N3 C35 103.62(17) . . ?
C28 N3 C35 112.22(19) . . ?
C2 C1 H1 120.1 . . ?
C22 C1 H1 120.1 . . ?
C22 C1 C2 119.8(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 121.7(2) . . ?
C3 C4 C21 118.8(3) . . ?
C21 C4 C5 119.2(3) . . ?
O1 C5 C4 122.1(3) . . ?
O1 C5 N6 120.5(3) . . ?
N6 C5 C4 117.4(2) . . ?
N1 N6 C17 112.4(2) . . ?
C5 N6 N1 123.0(2) . . ?
C5 N6 C17 124.5(2) . . ?
N1 C7 H7A 110.3 . . ?
N1 C7 H7B 110.3 . . ?
N1 C7 C8 107.1(2) . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 H7A 110.3 . . ?
C8 C7 H7B 110.3 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C7 C8 C9 110.4(2) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C10 C9 C8 120.2(2) . . ?
C13 C9 C8 120.4(2) . . ?
C13 C9 C10 119.4(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.3 . . ?
C15 C11 C10 119.3(3) . . ?
C15 C11 H11 120.3 . . ?
N1 C12 H12 106.5 . . ?
N1 C12 C13 112.05(19) . . ?
N1 C12 C16 106.5(2) . . ?
C13 C12 H12 106.5 . . ?
C13 C12 C16 118.11(19) . . ?
C16 C12 H12 106.5 . . ?
C9 C13 C12 121.4(2) . . ?
C9 C13 C14 119.2(2) . . ?
C14 C13 C12 119.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C11 C15 C14 120.6(3) . . ?
C11 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C12 C16 H16 110.0 . . ?
C17 C16 C12 103.6(2) . . ?
C17 C16 H16 110.0 . . ?
C20 C16 C12 117.8(2) . . ?
C20 C16 H16 110.0 . . ?
C20 C16 C17 104.9(3) . . ?
N6 C17 C16 103.9(2) . . ?
N6 C17 H17 111.3 . . ?
N6 C17 C18 114.0(3) . . ?
C16 C17 H17 111.3 . . ?
C18 C17 C16 104.5(3) . . ?
C18 C17 H17 111.3 . . ?
C17 C18 H18 124.0 . . ?
C19 C18 C17 112.0(3) . . ?
C19 C18 H18 124.0 . . ?
C18 C19 H19 124.3 . . ?
C18 C19 C20 111.4(3) . . ?
C20 C19 H19 124.3 . . ?
O2 C20 C16 125.8(4) . . ?
O2 C20 C19 127.0(3) . . ?
C19 C20 C16 107.2(3) . . ?
C4 C21 H21 120.0 . . ?
C22 C21 C4 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C1 C22 C21 120.5(3) . . ?
C1 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C33 120.0(2) . . ?
C33 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 116.0(2) . . ?
C34 C26 C25 119.7(2) . . ?
C34 C26 C27 124.2(2) . . ?
O4 C27 N2 119.9(2) . . ?
O4 C27 C26 120.0(2) . . ?
N2 C27 C26 120.1(2) . . ?
N3 C28 H28A 110.1 . . ?
N3 C28 H28B 110.1 . . ?
N3 C28 C29 107.9(2) . . ?
H28A C28 H28B 108.4 . . ?
C29 C28 H28A 110.1 . . ?
C29 C28 H28B 110.1 . . ?
C28 C29 H29A 109.4 . . ?
C28 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C30 C29 C28 111.1(2) . . ?
C30 C29 H29A 109.4 . . ?
C30 C29 H29B 109.4 . . ?
C31 C30 C29 120.2(2) . . ?
C41 C30 C29 120.2(2) . . ?
C41 C30 C31 119.6(2) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 C30 120.7(2) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 H32 120.0 . . ?
C43 C32 C31 119.9(2) . . ?
C43 C32 H32 120.0 . . ?
C23 C33 H33 119.7 . . ?
C23 C33 C34 120.6(3) . . ?
C34 C33 H33 119.7 . . ?
C26 C34 C33 119.7(2) . . ?
C26 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
N3 C35 H35 106.7 . . ?
N3 C35 C36 105.52(19) . . ?
N3 C35 C41 112.23(19) . . ?
C36 C35 H35 106.7 . . ?
C41 C35 H35 106.7 . . ?
C41 C35 C36 118.40(18) . . ?
C35 C36 H36 109.5 . . ?
C37 C36 C35 119.60(19) . . ?
C37 C36 H36 109.5 . . ?
C37 C36 C40 104.29(19) . . ?
C40 C36 C35 103.97(18) . . ?
C40 C36 H36 109.5 . . ?
O3 C37 C36 125.4(2) . . ?
O3 C37 C38 126.5(2) . . ?
C38 C37 C36 108.1(2) . . ?
C37 C38 H38 125.0 . . ?
C39 C38 C37 110.0(2) . . ?
C39 C38 H38 125.0 . . ?
C38 C39 H39 123.6 . . ?
C38 C39 C40 112.8(3) . . ?
C40 C39 H39 123.6 . . ?
N2 C40 C36 104.26(19) . . ?
N2 C40 C39 114.5(2) . . ?
N2 C40 H40 111.0 . . ?
C36 C40 H40 111.0 . . ?
C39 C40 C36 104.7(2) . . ?
C39 C40 H40 111.0 . . ?
C30 C41 C35 122.1(2) . . ?
C30 C41 C42 118.9(2) . . ?
C42 C41 C35 119.0(2) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 C41 121.0(2) . . ?
C43 C42 H42 119.5 . . ?
C32 C43 C42 119.8(2) . . ?
C32 C43 H43 120.1 . . ?
C42 C43 H43 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 N6 N1 -168.1(3) . . . . ?
O1 C5 N6 C17 6.6(5) . . . . ?
O3 C37 C38 C39 179.3(3) . . . . ?
N1 N6 C17 C16 -17.4(3) . . . . ?
N1 N6 C17 C18 95.8(3) . . . . ?
N1 C7 C8 C9 -56.0(3) . . . . ?
N1 C12 C13 C9 3.5(3) . . . . ?
N1 C12 C13 C14 -172.5(2) . . . . ?
N1 C12 C16 C17 22.0(3) . . . . ?
N1 C12 C16 C20 -93.3(3) . . . . ?
N2 N3 C28 C29 -176.77(18) . . . . ?
N2 N3 C35 C36 -33.2(2) . . . . ?
N2 N3 C35 C41 -163.47(17) . . . . ?
N3 N2 C27 O4 170.2(3) . . . . ?
N3 N2 C27 C26 -11.1(4) . . . . ?
N3 N2 C40 C36 -16.1(3) . . . . ?
N3 N2 C40 C39 97.8(3) . . . . ?
N3 C28 C29 C30 -54.1(3) . . . . ?
N3 C35 C36 C37 -92.1(2) . . . . ?
N3 C35 C36 C40 23.7(2) . . . . ?
N3 C35 C41 C30 8.4(3) . . . . ?
N3 C35 C41 C42 -168.6(2) . . . . ?
C1 C2 C3 C4 2.3(4) . . . . ?
C2 C1 C22 C21 0.5(5) . . . . ?
C2 C3 C4 C5 174.4(3) . . . . ?
C2 C3 C4 C21 0.2(4) . . . . ?
C3 C4 C5 O1 -132.3(3) . . . . ?
C3 C4 C5 N6 46.8(4) . . . . ?
C3 C4 C21 C22 -2.3(4) . . . . ?
C4 C5 N6 N1 12.7(4) . . . . ?
C4 C5 N6 C17 -172.6(3) . . . . ?
C4 C21 C22 C1 2.0(4) . . . . ?
C5 C4 C21 C22 -176.7(3) . . . . ?
C5 N6 C17 C16 167.4(3) . . . . ?
C5 N6 C17 C18 -79.4(4) . . . . ?
N6 N1 C7 C8 -175.1(2) . . . . ?
N6 N1 C12 C13 -162.61(19) . . . . ?
N6 N1 C12 C16 -32.1(2) . . . . ?
N6 C17 C18 C19 -114.4(3) . . . . ?
C7 N1 N6 C5 85.7(3) . . . . ?
C7 N1 N6 C17 -89.6(3) . . . . ?
C7 N1 C12 C13 -42.0(3) . . . . ?
C7 N1 C12 C16 88.5(2) . . . . ?
C7 C8 C9 C10 -159.2(2) . . . . ?
C7 C8 C9 C13 20.1(3) . . . . ?
C8 C9 C10 C11 179.4(2) . . . . ?
C8 C9 C13 C12 6.7(3) . . . . ?
C8 C9 C13 C14 -177.3(2) . . . . ?
C9 C10 C11 C15 -1.9(4) . . . . ?
C9 C13 C14 C15 -2.3(4) . . . . ?
C10 C9 C13 C12 -174.0(2) . . . . ?
C10 C9 C13 C14 2.0(3) . . . . ?
C10 C11 C15 C14 1.6(4) . . . . ?
C12 N1 N6 C5 -153.3(3) . . . . ?
C12 N1 N6 C17 31.5(3) . . . . ?
C12 N1 C7 C8 69.6(3) . . . . ?
C12 C13 C14 C15 173.8(2) . . . . ?
C12 C16 C17 N6 -3.5(3) . . . . ?
C12 C16 C17 C18 -123.3(2) . . . . ?
C12 C16 C20 O2 -65.9(4) . . . . ?
C12 C16 C20 C19 114.7(3) . . . . ?
C13 C9 C10 C11 0.1(4) . . . . ?
C13 C12 C16 C17 149.0(2) . . . . ?
C13 C12 C16 C20 33.7(4) . . . . ?
C13 C14 C15 C11 0.5(4) . . . . ?
C16 C12 C13 C9 -120.8(2) . . . . ?
C16 C12 C13 C14 63.2(3) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C17 C16 C20 O2 179.5(3) . . . . ?
C17 C16 C20 C19 0.2(3) . . . . ?
C17 C18 C19 C20 1.8(4) . . . . ?
C18 C19 C20 O2 179.4(3) . . . . ?
C18 C19 C20 C16 -1.2(4) . . . . ?
C20 C16 C17 N6 120.6(2) . . . . ?
C20 C16 C17 C18 0.8(3) . . . . ?
C21 C4 C5 O1 41.9(4) . . . . ?
C21 C4 C5 N6 -139.0(3) . . . . ?
C22 C1 C2 C3 -2.6(4) . . . . ?
C23 C24 C25 C26 -0.8(4) . . . . ?
C23 C33 C34 C26 -2.1(4) . . . . ?
C24 C23 C33 C34 2.1(4) . . . . ?
C24 C25 C26 C27 176.6(2) . . . . ?
C24 C25 C26 C34 0.8(4) . . . . ?
C25 C26 C27 O4 -43.5(4) . . . . ?
C25 C26 C27 N2 137.9(3) . . . . ?
C25 C26 C34 C33 0.7(4) . . . . ?
C27 N2 N3 C28 125.3(2) . . . . ?
C27 N2 N3 C35 -114.2(2) . . . . ?
C27 N2 C40 C36 130.8(2) . . . . ?
C27 N2 C40 C39 -115.4(3) . . . . ?
C27 C26 C34 C33 -174.8(2) . . . . ?
C28 N3 C35 C36 86.3(2) . . . . ?
C28 N3 C35 C41 -44.0(2) . . . . ?
C28 C29 C30 C31 -159.9(2) . . . . ?
C28 C29 C30 C41 20.6(3) . . . . ?
C29 C30 C31 C32 -178.2(2) . . . . ?
C29 C30 C41 C35 2.6(3) . . . . ?
C29 C30 C41 C42 179.5(2) . . . . ?
C30 C31 C32 C43 -1.3(4) . . . . ?
C30 C41 C42 C43 -1.3(3) . . . . ?
C31 C30 C41 C35 -176.9(2) . . . . ?
C31 C30 C41 C42 0.0(3) . . . . ?
C31 C32 C43 C42 0.0(4) . . . . ?
C33 C23 C24 C25 -0.6(4) . . . . ?
C34 C26 C27 O4 132.1(3) . . . . ?
C34 C26 C27 N2 -46.5(4) . . . . ?
C35 N3 C28 C29 68.0(2) . . . . ?
C35 C36 C37 O3 -65.0(3) . . . . ?
C35 C36 C37 C38 117.0(2) . . . . ?
C35 C36 C40 N2 -5.2(2) . . . . ?
C35 C36 C40 C39 -125.9(2) . . . . ?
C35 C41 C42 C43 175.7(2) . . . . ?
C36 C35 C41 C30 -115.0(2) . . . . ?
C36 C35 C41 C42 68.1(3) . . . . ?
C36 C37 C38 C39 -2.8(3) . . . . ?
C37 C36 C40 N2 120.8(2) . . . . ?
C37 C36 C40 C39 0.2(2) . . . . ?
C37 C38 C39 C40 3.0(3) . . . . ?
C38 C39 C40 N2 -115.6(3) . . . . ?
C38 C39 C40 C36 -2.0(3) . . . . ?
C40 N2 N3 C28 -89.1(2) . . . . ?
C40 N2 N3 C35 31.4(2) . . . . ?
C40 N2 C27 O4 26.7(4) . . . . ?
C40 N2 C27 C26 -154.6(2) . . . . ?
C40 C36 C37 O3 179.4(2) . . . . ?
C40 C36 C37 C38 1.5(2) . . . . ?
C41 C30 C31 C32 1.2(3) . . . . ?
C41 C35 C36 C37 34.6(3) . . . . ?
C41 C35 C36 C40 150.3(2) . . . . ?
C41 C42 C43 C32 1.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
