# 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. 
# 
#######################################################################

data_exp_3975_auto
_database_code_depnum_ccdc_archive 'CCDC 2265065'
loop_
_audit_author_name
_audit_author_address
Frank CCDC
_audit_update_record             
;
2023-05-24 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2023-05-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 N2 O2'
_chemical_formula_sum            'C24 H18 N2 O2'
_chemical_formula_weight         366.40
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1'
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                   9.6789(2)
_cell_length_b                   9.7371(2)
_cell_length_c                   10.6182(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.927(2)
_cell_angle_gamma                90
_cell_volume                     998.36(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8107
_cell_measurement_temperature    297.64(10)
_cell_measurement_theta_max      75.7970
_cell_measurement_theta_min      4.1420
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12022
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.305
_diffrn_reflns_theta_min         4.173
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.64(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     86.00 163.00   0.50    0.27    --  106.01  77.00   0.00  154
  2  ω    142.00 175.00   0.50    0.27    --  106.01  77.00 -30.00   66
  3  ω     96.00 177.00   0.50    0.27    --  106.01  77.00  90.00  162
  4  ω    130.00 155.00   0.50    0.27    --  106.01  61.00 -30.00   50
  5  ω     92.00 132.00   0.50    0.27    --  106.01  77.00 -30.00   80
  6  ω     41.00  84.00   0.50    0.07    --   47.30  61.00  63.00   86
  7  ω    110.00 135.00   0.50    0.27    --  106.01  61.00  63.00   50
  8  ω     90.00 122.00   0.50    0.27    --  106.01  61.00 -30.00   64
  9  ω    119.00 173.00   0.50    0.27    --  106.01  61.00-150.00  108
 10  ω    131.00 168.00   0.50    0.27    --  106.01  61.00-180.00   74
 11  ω     93.00 126.00   0.50    0.27    --  106.01  61.00-180.00   66
 12  ω    104.00 134.00   0.50    0.27    --  106.01  45.00-150.00   60
 13  ω    124.00 149.00   0.50    0.27    --  106.01  45.00-180.00   50
 14  ω     93.00 119.00   0.50    0.27    --  106.01  45.00-180.00   52
 15  ω    122.00 159.00   0.50    0.27    --  106.01  15.00  60.00   74
 16  ω     37.00 123.00   0.50    0.07    --   47.30  19.00-120.00  172
 17  ω    -26.00  24.00   0.50    0.07    --   47.30 -19.00 -60.00  100
 18  ω     15.00  41.00   0.50    0.07    --   47.30 -61.00 -75.00   52
 19  ω     37.00  72.00   0.50    0.27    --  106.01 -61.00  60.00   70
 20  ω     33.00  64.00   0.50    0.27    --  106.01 -61.00 -75.00   62
 21  ω     34.00  59.00   0.50    0.27    --  106.01 -61.00-120.00   50
 22  ω     38.00  73.00   0.50    0.27    --  106.01 -61.00 -30.00   70
 23  ω     38.00  68.00   0.50    0.27    --  106.01 -61.00 150.00   60
 24  ω    -23.00  28.00   0.50    0.07    --  -47.30  19.00-120.00  102
 25  ω    -23.00  28.00   0.50    0.07    --  -47.30  19.00-180.00  102
 26  ω    -44.00 -19.00   0.50    0.07    --  -47.30  61.00  63.00   50
 27  ω     -5.00  20.00   0.50    0.07    --  -47.30  19.00  60.00   50
 28  ω   -102.00 -38.00   0.50    0.27    -- -102.00  77.00 -60.00  128
 29  ω    -69.00 -29.00   0.50    0.27    -- -102.00  61.00-180.00   80
 30  ω    -69.00 -30.00   0.50    0.27    -- -102.00  61.00 -90.00   78
 31  ω    -68.00 -30.00   0.50    0.27    -- -102.00  61.00  30.00   76
 32  ω    -59.00 -30.00   0.50    0.27    -- -102.00  61.00  63.00   58
 33  ω   -119.00 -35.00   0.50    0.07    --  -47.30 -37.00  90.00  168
 34  ω   -147.00 -86.00   0.50    0.27    -- -102.00 -61.00 150.00  122
 35  ω    -90.00 -64.00   0.50    0.07    --  -47.30 -61.00 -75.00   52
 36  ω   -141.00 -88.00   0.50    0.27    -- -102.00 -61.00 -75.00  106
 37  ω   -108.00 -79.00   0.50    0.27    -- -102.00 -77.00-150.00   58
 38  ω   -110.00 -85.00   0.50    0.27    -- -102.00 -61.00-180.00   50
 39  ω   -151.00-125.00   0.50    0.27    -- -102.00 -61.00-180.00   52
 40  ω   -165.00-119.00   0.50    0.27    -- -102.00 -77.00-150.00   92
 41  ω   -164.00-139.00   0.50    0.27    -- -102.00 -45.00   0.00   50
 42  ω   -129.00-103.00   0.50    0.27    -- -102.00 -45.00   0.00   52
 43  ω   -135.00 -94.00   0.50    0.27    -- -102.00 -45.00 150.00   82
 44  ω   -119.00 -71.00   0.50    0.07    --  -47.30-125.00  90.00   96
;
_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      -0.1097911000
_diffrn_orient_matrix_UB_12      -0.1126932000
_diffrn_orient_matrix_UB_13      -0.0266230000
_diffrn_orient_matrix_UB_21      -0.0426629000
_diffrn_orient_matrix_UB_22      0.0118837000
_diffrn_orient_matrix_UB_23      0.1366773000
_diffrn_orient_matrix_UB_31      -0.1076149000
_diffrn_orient_matrix_UB_32      0.1104728000
_diffrn_orient_matrix_UB_33      -0.0418109000
_diffrn_oxdiff_digest_frames     
;
01b3c7103d07bd1fe28ef371eb8a4dd6fe00038fd1d
;
_diffrn_oxdiff_digest_hkl        
;
01b7f6ea6739cd77c9ec33e5234b78bfabcdc8
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                3577
_reflns_number_total             3963
_reflns_odcompleteness_completeness 99.84
_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 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 1476 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3963
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.063
_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)+(0.0816P)²+0.0225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1253
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24)
2.d :
 C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.9193(4) 0.7673(3) 0.9004(2) 0.1320(10) Uani 1 1 d . . . . .
N1 N 0.6051(2) 0.3020(3) 0.47089(17) 0.0763(5) Uani 1 1 d . . . . .
H1 H 0.6064 0.3197 0.3916 0.092 Uiso 1 1 calc R . . . .
N2 N 0.9182(2) 0.6463(3) 0.92538(19) 0.0801(6) Uani 1 1 d . . . . .
C1 C 0.7726(3) 0.5073(2) 0.6199(2) 0.0721(6) Uani 1 1 d . . . . .
H1A H 0.7307 0.5401 0.5444 0.087 Uiso 1 1 calc R . . . .
O2 O 0.9486(3) 0.6018(3) 1.03022(18) 0.1089(8) Uani 1 1 d . . . . .
C2 C 0.8204(3) 0.5987(3) 0.7116(2) 0.0744(6) Uani 1 1 d . . . . .
H2 H 0.8131 0.6929 0.6980 0.089 Uiso 1 1 calc R . . . .
C3 C 0.4811(2) 0.3123(3) 0.5262(2) 0.0697(5) Uani 1 1 d . . . . .
C4 C 0.7859(2) 0.3665(2) 0.63853(19) 0.0639(5) Uani 1 1 d . . . . .
C5 C 0.3775(3) 0.4119(3) 0.3291(2) 0.0759(6) Uani 1 1 d . . . . .
C6 C 0.3890(3) 0.4474(3) 0.2229(2) 0.0804(6) Uani 1 1 d . . . . .
C7 C 0.7333(2) 0.2629(3) 0.5393(2) 0.0714(5) Uani 1 1 d . . . . .
H7 H 0.7163 0.1766 0.5832 0.086 Uiso 1 1 calc R . . . .
C8 C 0.4016(3) 0.4961(3) 0.0967(2) 0.0789(6) Uani 1 1 d . . . . .
C9 C 0.8792(2) 0.5481(3) 0.82390(19) 0.0650(5) Uani 1 1 d . . . . .
C10 C 0.8429(3) 0.2338(3) 0.4441(3) 0.0846(7) Uani 1 1 d . . . . .
H10A H 0.9299 0.2114 0.4903 0.101 Uiso 1 1 calc R . . . .
H10B H 0.8142 0.1541 0.3941 0.101 Uiso 1 1 calc R . . . .
C11 C 0.8512(3) 0.3200(3) 0.7511(2) 0.0752(6) Uani 1 1 d . . . . .
H11 H 0.8644 0.2262 0.7634 0.090 Uiso 1 1 calc R . . . .
C12 C 0.3650(3) 0.3665(3) 0.4564(2) 0.0721(5) Uani 1 1 d . . . . .
C13 C 0.4644(3) 0.2669(3) 0.6499(2) 0.0855(7) Uani 1 1 d . . . . .
H13 H 0.5396 0.2302 0.6978 0.103 Uiso 1 1 calc R . . . .
C14 C 0.8969(3) 0.4105(3) 0.8448(2) 0.0768(6) Uani 1 1 d . . . . .
H14 H 0.9389 0.3786 0.9206 0.092 Uiso 1 1 calc R . . . .
C15 C 0.3380(4) 0.2762(4) 0.7006(3) 0.1002(9) Uani 1 1 d . . . . .
H15 H 0.3289 0.2467 0.7830 0.120 Uiso 1 1 calc R . . . .
C16 C 0.2244(3) 0.3285(4) 0.6316(3) 0.0991(9) Uani 1 1 d . . . . .
H16 H 0.1391 0.3335 0.6668 0.119 Uiso 1 1 calc R . . . .
C17 C 0.8654(3) 0.3476(4) 0.3597(3) 0.0898(8) Uani 1 1 d . . . . .
C18 C 0.2381(3) 0.3733(3) 0.5101(3) 0.0863(7) Uani 1 1 d . . . . .
H18 H 0.1614 0.4085 0.4633 0.104 Uiso 1 1 calc R . . . .
C19 C 0.2888(4) 0.5469(5) 0.0283(3) 0.1116(12) Uani 1 1 d . . . . .
H19 H 0.2034 0.5482 0.0633 0.134 Uiso 1 1 calc R . . . .
C20 C 0.8795(4) 0.4383(6) 0.2904(3) 0.1173(12) Uani 1 1 d . . . . .
H20 H 0.8908 0.5108 0.2350 0.141 Uiso 1 1 calc R . . . .
C21 C 0.2999(5) 0.5962(6) -0.0919(3) 0.1263(14) Uani 1 1 d . . . . .
H21 H 0.2221 0.6315 -0.1369 0.152 Uiso 1 1 calc R . . . .
C22 C 0.5219(4) 0.4844(8) 0.0393(4) 0.149(2) Uani 1 1 d . . . . .
H22 H 0.5986 0.4439 0.0819 0.179 Uiso 1 1 calc R . . . .
C23 C 0.5309(5) 0.5325(10) -0.0825(5) 0.173(3) Uani 1 1 d . . . . .
H23 H 0.6135 0.5220 -0.1214 0.208 Uiso 1 1 calc R . . . .
C24 C 0.4231(5) 0.5940(6) -0.1454(4) 0.1263(14) Uani 1 1 d . . . . .
H24 H 0.4326 0.6341 -0.2239 0.152 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.208(4) . ?
N1 H1 0.8600 . ?
N1 C3 1.375(3) . ?
N1 C7 1.445(3) . ?
N2 O2 1.212(3) . ?
N2 C9 1.470(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.376(3) . ?
C1 C4 1.389(3) . ?
C2 H2 0.9300 . ?
C2 C9 1.377(3) . ?
C3 C12 1.406(4) . ?
C3 C13 1.406(3) . ?
C4 C7 1.521(3) . ?
C4 C11 1.389(3) . ?
C5 C6 1.192(4) . ?
C5 C12 1.435(4) . ?
C6 C8 1.434(4) . ?
C7 H7 0.9800 . ?
C7 C10 1.541(4) . ?
C8 C19 1.361(4) . ?
C8 C22 1.356(5) . ?
C9 C14 1.366(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C17 1.451(5) . ?
C11 H11 0.9300 . ?
C11 C14 1.379(4) . ?
C12 C18 1.391(4) . ?
C13 H13 0.9300 . ?
C13 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.376(5) . ?
C16 H16 0.9300 . ?
C16 C18 1.377(5) . ?
C17 C20 1.164(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C21 1.375(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C24 1.356(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.341(7) . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 H1 118.4 . . ?
C3 N1 C7 123.27(18) . . ?
C7 N1 H1 118.4 . . ?
O1 N2 O2 123.0(2) . . ?
O1 N2 C9 118.6(2) . . ?
O2 N2 C9 118.3(2) . . ?
C2 C1 H1A 119.5 . . ?
C2 C1 C4 120.94(19) . . ?
C4 C1 H1A 119.5 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C9 118.7(2) . . ?
C9 C2 H2 120.7 . . ?
N1 C3 C12 119.5(2) . . ?
N1 C3 C13 122.4(2) . . ?
C12 C3 C13 118.1(2) . . ?
C1 C4 C7 122.17(18) . . ?
C11 C4 C1 118.5(2) . . ?
C11 C4 C7 119.4(2) . . ?
C6 C5 C12 178.8(3) . . ?
C5 C6 C8 177.5(3) . . ?
N1 C7 C4 114.1(2) . . ?
N1 C7 H7 107.4 . . ?
N1 C7 C10 108.9(2) . . ?
C4 C7 H7 107.4 . . ?
C4 C7 C10 111.3(2) . . ?
C10 C7 H7 107.4 . . ?
C19 C8 C6 120.2(3) . . ?
C22 C8 C6 121.4(3) . . ?
C22 C8 C19 118.2(3) . . ?
C2 C9 N2 118.2(2) . . ?
C14 C9 N2 119.69(19) . . ?
C14 C9 C2 122.1(2) . . ?
C7 C10 H10A 108.8 . . ?
C7 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C17 C10 C7 113.8(2) . . ?
C17 C10 H10A 108.8 . . ?
C17 C10 H10B 108.8 . . ?
C4 C11 H11 119.4 . . ?
C14 C11 C4 121.1(2) . . ?
C14 C11 H11 119.4 . . ?
C3 C12 C5 119.7(2) . . ?
C18 C12 C3 119.9(2) . . ?
C18 C12 C5 120.4(2) . . ?
C3 C13 H13 119.7 . . ?
C15 C13 C3 120.5(3) . . ?
C15 C13 H13 119.7 . . ?
C9 C14 C11 118.6(2) . . ?
C9 C14 H14 120.7 . . ?
C11 C14 H14 120.7 . . ?
C13 C15 H15 119.5 . . ?
C13 C15 C16 121.1(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C18 119.5(3) . . ?
C18 C16 H16 120.3 . . ?
C20 C17 C10 178.0(4) . . ?
C12 C18 H18 119.6 . . ?
C16 C18 C12 120.9(3) . . ?
C16 C18 H18 119.6 . . ?
C8 C19 H19 119.6 . . ?
C8 C19 C21 120.7(3) . . ?
C21 C19 H19 119.6 . . ?
C17 C20 H20 180.0 . . ?
C19 C21 H21 119.6 . . ?
C24 C21 C19 120.7(4) . . ?
C24 C21 H21 119.6 . . ?
C8 C22 H22 119.9 . . ?
C8 C22 C23 120.1(4) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.3 . . ?
C24 C23 C22 121.4(4) . . ?
C24 C23 H23 119.3 . . ?
C21 C24 H24 120.8 . . ?
C23 C24 C21 118.3(4) . . ?
C23 C24 H24 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C9 C2 -12.3(4) . . . . ?
O1 N2 C9 C14 170.3(3) . . . . ?
N1 C3 C12 C5 -0.7(3) . . . . ?
N1 C3 C12 C18 177.9(2) . . . . ?
N1 C3 C13 C15 -178.5(3) . . . . ?
N1 C7 C10 C17 56.1(3) . . . . ?
N2 C9 C14 C11 175.8(2) . . . . ?
C1 C2 C9 N2 -174.5(2) . . . . ?
C1 C2 C9 C14 2.9(4) . . . . ?
C1 C4 C7 N1 -37.0(3) . . . . ?
C1 C4 C7 C10 86.8(3) . . . . ?
C1 C4 C11 C14 2.7(4) . . . . ?
O2 N2 C9 C2 168.1(3) . . . . ?
O2 N2 C9 C14 -9.3(4) . . . . ?
C2 C1 C4 C7 179.6(2) . . . . ?
C2 C1 C4 C11 -1.3(4) . . . . ?
C2 C9 C14 C11 -1.5(4) . . . . ?
C3 N1 C7 C4 -66.2(3) . . . . ?
C3 N1 C7 C10 168.7(2) . . . . ?
C3 C12 C18 C16 0.5(4) . . . . ?
C3 C13 C15 C16 0.8(5) . . . . ?
C4 C1 C2 C9 -1.4(4) . . . . ?
C4 C7 C10 C17 -70.6(3) . . . . ?
C4 C11 C14 C9 -1.4(4) . . . . ?
C5 C12 C18 C16 179.2(3) . . . . ?
C6 C8 C19 C21 178.8(4) . . . . ?
C6 C8 C22 C23 -179.9(6) . . . . ?
C7 N1 C3 C12 172.5(2) . . . . ?
C7 N1 C3 C13 -9.3(4) . . . . ?
C7 C4 C11 C14 -178.2(2) . . . . ?
C8 C19 C21 C24 0.7(8) . . . . ?
C8 C22 C23 C24 1.4(12) . . . . ?
C11 C4 C7 N1 143.9(2) . . . . ?
C11 C4 C7 C10 -92.3(3) . . . . ?
C12 C3 C13 C15 -0.3(4) . . . . ?
C13 C3 C12 C5 -179.0(2) . . . . ?
C13 C3 C12 C18 -0.3(4) . . . . ?
C13 C15 C16 C18 -0.6(5) . . . . ?
C15 C16 C18 C12 -0.1(5) . . . . ?
C19 C8 C22 C23 4.6(9) . . . . ?
C19 C21 C24 C23 5.3(9) . . . . ?
C22 C8 C19 C21 -5.7(7) . . . . ?
C22 C23 C24 C21 -6.4(11) . . . . ?

_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 4.506
_oxdiff_exptl_absorpt_empirical_full_min 0.581
####################################################################### 
# 
# 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_exp_4084_auto
_database_code_depnum_ccdc_archive 'CCDC 2267478'
loop_
_audit_author_name
_audit_author_address
N-diphenylmethanimine
;China west normal university
China
;
_audit_update_record             
;
2023-06-05 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2023-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H14 N2 O2)'
_chemical_formula_sum            'C42 H28 N4 O4'
_chemical_formula_weight         652.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1'
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                   24.7258(4)
_cell_length_b                   10.9717(2)
_cell_length_c                   12.8034(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.793(2)
_cell_angle_gamma                90
_cell_volume                     3358.23(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13943
_cell_measurement_temperature    296.4(3)
_cell_measurement_theta_max      75.7270
_cell_measurement_theta_min      3.6760
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
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    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24894
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.874
_diffrn_reflns_theta_min         3.698
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.4(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     72.00  97.00   0.50    0.20    --   47.05 130.00 -26.00   50
  2  ω    101.00 126.00   0.50    0.80    --  106.01 130.00 -26.00   50
  3  ω     98.00 168.00   0.50    0.80    --  106.01  61.00  60.00  140
  4  ω    151.00 178.00   0.50    0.80    --  106.01  30.00 150.00   54
  5  ω     33.00 107.00   0.50    0.80    --  106.01 -94.00-120.00  148
  6  ω     40.00  68.00   0.50    0.20    --   47.05-130.00 -98.00   56
  7  ω     30.00 103.00   0.50    0.20    --   47.05-139.00  87.00  146
  8  ω     33.00  94.00   0.50    0.80    --  106.01-139.00  87.00  122
  9  ω     97.00 127.00   0.50    0.80    --  106.01-139.00  87.00   60
 10  ω     37.00 100.00   0.50    0.80    --  106.01 -94.00  60.00  126
 11  ω     33.00  58.00   0.50    0.80    --  106.01 -61.00  90.00   50
 12  ω    -10.00  28.00   0.50    0.20    --   47.05 -19.00 120.00   76
 13  ω     38.00  64.00   0.50    0.80    --  106.01 -61.00 -60.00   52
 14  ω     39.00  65.00   0.50    0.80    --  106.01 -61.00 -90.00   52
 15  ω     33.00  73.00   0.50    0.80    --  106.01 -61.00-150.00   80
 16  ω      2.00  28.00   0.50    0.20    --   47.05 -19.00-150.00   52
 17  ω     -3.00  28.00   0.50    0.20    --  -47.05  19.00-150.00   62
 18  ω    -69.00 -31.00   0.50    0.80    -- -102.00  61.00-180.00   76
 19  ω    -69.00 -30.00   0.50    0.80    -- -102.00  61.00 -30.00   78
 20  ω   -126.00 -81.00   0.50    0.80    -- -102.00 139.00 147.00   90
 21  ω   -125.00 -95.00   0.50    0.80    -- -102.00 -45.00 150.00   60
 22  ω   -166.00-140.00   0.50    0.80    -- -102.00 -45.00 150.00   52
 23  ω   -175.00-143.00   0.50    0.80    -- -102.00 -30.00  90.00   64
 24  ω   -132.00-107.00   0.50    0.80    -- -102.00 -30.00  90.00   50
 25  ω   -118.00 -71.00   0.50    0.20    --  -47.05-125.00  30.00   94
 26  ω   -107.00 -62.00   0.50    0.20    --  -47.05-139.00  87.00   90
 27  ω   -120.00 -69.00   0.50    0.80    -- -102.00-139.00  87.00  102
 28  ω   -119.00 -74.00   0.50    0.20    --  -47.05-125.00 -60.00   90
 29  ω   -118.00 -93.00   0.50    0.20    --  -47.05-130.00 -98.00   50
;
_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      -0.0570331000
_diffrn_orient_matrix_UB_12      -0.0647313000
_diffrn_orient_matrix_UB_13      -0.0205506000
_diffrn_orient_matrix_UB_21      -0.0294560000
_diffrn_orient_matrix_UB_22      0.1244878000
_diffrn_orient_matrix_UB_23      -0.0060950000
_diffrn_orient_matrix_UB_31      -0.0056757000
_diffrn_orient_matrix_UB_32      0.0046673000
_diffrn_orient_matrix_UB_33      -0.1226076000
_diffrn_oxdiff_digest_frames     
;
0166df35ddcfd2313e33c6a15a8b373977000465873
;
_diffrn_oxdiff_digest_hkl        
;
01f3d280b492f29e702e6b9ee27e874c5c61c2
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5846
_reflns_number_total             6683
_reflns_odcompleteness_completeness 99.92
_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 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.00051(18)
_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   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0918
_refine_ls_restrained_S_all      1.083
_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)+(0.1027P)²+3.5891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2592
_refine_ls_wR_factor_ref         0.2629
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C15(H15), C17(H17), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
 C38(H38), C39(H39), C40(H40), C41(H41), C42(H42)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
N1 N 0.41143(11) 0.7191(3) 1.0966(2) 0.0579(7) Uani 1 1 d . . . . .
N2 N 0.55296(13) 0.7757(3) 0.7384(2) 0.0677(8) Uani 1 1 d . . . . .
O1 O 0.56347(13) 0.6737(3) 0.7091(2) 0.0861(8) Uani 1 1 d . . . . .
N3 N 0.09480(12) 0.7270(3) 0.7012(2) 0.0639(7) Uani 1 1 d . . . . .
O2 O 0.56691(15) 0.8706(3) 0.7028(3) 0.0922(9) Uani 1 1 d . . . . .
N4 N -0.04624(13) 0.7750(3) 0.2032(3) 0.0718(8) Uani 1 1 d . . . . .
O3 O -0.05664(15) 0.6739(3) 0.1631(3) 0.0949(9) Uani 1 1 d . . . . .
O4 O -0.06062(15) 0.8679(3) 0.1518(2) 0.0946(10) Uani 1 1 d . . . . .
C1 C 0.37587(13) 0.7399(3) 1.1672(2) 0.0531(7) Uani 1 1 d . . . . .
C2 C 0.45743(14) 0.7966(3) 0.9658(3) 0.0552(7) Uani 1 1 d . . . . .
C3 C -0.01419(14) 0.7838(3) 0.3158(3) 0.0591(8) Uani 1 1 d . . . . .
C4 C 0.13068(14) 0.7491(3) 0.8054(3) 0.0587(8) Uani 1 1 d . . . . .
C5 C 0.51729(14) 0.6819(3) 0.8810(3) 0.0600(8) Uani 1 1 d . . . . .
H5 H 0.536250 0.610521 0.873439 0.072 Uiso 1 1 calc R . . . .
C6 C 0.52079(13) 0.7831(3) 0.8196(3) 0.0564(7) Uani 1 1 d . . . . .
C7 C 0.04930(14) 0.8012(3) 0.5242(3) 0.0611(8) Uani 1 1 d . . . . .
C8 C 0.46305(15) 0.8974(3) 0.9046(3) 0.0619(8) Uani 1 1 d . . . . .
H8 H 0.444930 0.969621 0.912905 0.074 Uiso 1 1 calc R . . . .
C9 C 0.16513(14) 0.6527(3) 0.8548(3) 0.0634(8) Uani 1 1 d . . . . .
C10 C 0.34135(14) 0.6453(3) 1.1835(3) 0.0599(8) Uani 1 1 d . . . . .
C11 C 0.49528(15) 0.8918(3) 0.8312(3) 0.0623(8) Uani 1 1 d . . . . .
H11 H 0.499622 0.959701 0.790674 0.075 Uiso 1 1 calc R . . . .
C12 C 0.37642(17) 0.8485(4) 1.2225(3) 0.0684(9) Uani 1 1 d . . . . .
H12 H 0.399400 0.911833 1.211650 0.082 Uiso 1 1 calc R . . . .
C13 C 0.04250(17) 0.9006(3) 0.4561(3) 0.0706(9) Uani 1 1 d . . . . .
H13 H 0.059874 0.973791 0.481602 0.085 Uiso 1 1 calc R . . . .
C14 C 0.33884(15) 0.5298(3) 1.1291(3) 0.0665(9) Uani 1 1 d . . . . .
C15 C 0.42049(14) 0.8069(3) 1.0389(3) 0.0599(8) Uani 1 1 d . . . . .
H15 H 0.402971 0.881149 1.043025 0.072 Uiso 1 1 calc R . . . .
C16 C 0.17093(15) 0.3198(3) 0.7235(3) 0.0655(9) Uani 1 1 d . . . . .
C17 C 0.02272(17) 0.6919(3) 0.4861(3) 0.0678(9) Uani 1 1 d . . . . .
H17 H 0.026388 0.624779 0.531765 0.081 Uiso 1 1 calc R . . . .
C18 C 0.33332(16) 0.4286(4) 1.0918(3) 0.0697(9) Uani 1 1 d . . . . .
C19 C 0.32611(14) 0.3055(3) 1.0557(3) 0.0645(9) Uani 1 1 d . . . . .
C20 C 0.48499(15) 0.6889(3) 0.9540(3) 0.0622(8) Uani 1 1 d . . . . .
H20 H 0.481577 0.621267 0.995630 0.075 Uiso 1 1 calc R . . . .
C21 C 0.08534(16) 0.8118(3) 0.6339(3) 0.0668(9) Uani 1 1 d . . . . .
H21 H 0.102308 0.886684 0.654899 0.080 Uiso 1 1 calc R . . . .
C22 C -0.00891(16) 0.6832(3) 0.3811(3) 0.0670(9) Uani 1 1 d . . . . .
H22 H -0.026404 0.610346 0.354892 0.080 Uiso 1 1 calc R . . . .
C23 C 0.01074(17) 0.8937(3) 0.3517(3) 0.0688(9) Uani 1 1 d . . . . .
H23 H 0.006112 0.961229 0.306337 0.083 Uiso 1 1 calc R . . . .
C24 C 0.20058(17) 0.6711(4) 0.9583(3) 0.0747(10) Uani 1 1 d . . . . .
H24 H 0.224243 0.608619 0.991378 0.090 Uiso 1 1 calc R . . . .
C25 C 0.16551(16) 0.5395(4) 0.8028(3) 0.0707(10) Uani 1 1 d . . . . .
C26 C 0.30792(16) 0.6627(4) 1.2546(3) 0.0730(10) Uani 1 1 d . . . . .
H26 H 0.284395 0.600180 1.264922 0.088 Uiso 1 1 calc R . . . .
C27 C 0.29992(16) 0.2252(4) 1.1103(3) 0.0709(9) Uani 1 1 d . . . . .
H27 H 0.287137 0.252405 1.168530 0.085 Uiso 1 1 calc R . . . .
C28 C 0.16793(16) 0.4398(4) 0.7646(4) 0.0735(10) Uani 1 1 d . . . . .
C29 C 0.13108(18) 0.8570(4) 0.8608(3) 0.0729(10) Uani 1 1 d . . . . .
H29 H 0.107675 0.920324 0.828749 0.087 Uiso 1 1 calc R . . . .
C30 C 0.34325(19) 0.8642(4) 1.2937(3) 0.0790(11) Uani 1 1 d . . . . .
H30 H 0.343918 0.937425 1.330515 0.095 Uiso 1 1 calc R . . . .
C31 C 0.19464(16) 0.2279(4) 0.7945(3) 0.0727(10) Uani 1 1 d . . . . .
H31 H 0.208467 0.244526 0.867746 0.087 Uiso 1 1 calc R . . . .
C32 C 0.20082(18) 0.7802(5) 1.0115(4) 0.0846(12) Uani 1 1 d . . . . .
H32 H 0.224696 0.790906 1.079918 0.102 Uiso 1 1 calc R . . . .
C33 C 0.19761(18) 0.1100(4) 0.7554(4) 0.0793(11) Uani 1 1 d . . . . .
H33 H 0.212733 0.047621 0.803073 0.095 Uiso 1 1 calc R . . . .
C34 C 0.34550(16) 0.2623(4) 0.9688(4) 0.0793(11) Uani 1 1 d . . . . .
H34 H 0.363584 0.314530 0.931521 0.095 Uiso 1 1 calc R . . . .
C35 C 0.31156(19) 0.0636(4) 0.9945(4) 0.0865(12) Uani 1 1 d . . . . .
H35 H 0.306881 -0.017926 0.974365 0.104 Uiso 1 1 calc R . . . .
C36 C 0.1662(2) 0.8725(4) 0.9645(4) 0.0852(12) Uani 1 1 d . . . . .
H36 H 0.165974 0.945524 1.001151 0.102 Uiso 1 1 calc R . . . .
C37 C 0.29272(19) 0.1046(4) 1.0784(4) 0.0800(11) Uani 1 1 d . . . . .
H37 H 0.274780 0.051292 1.115001 0.096 Uiso 1 1 calc R . . . .
C38 C 0.30894(18) 0.7695(5) 1.3095(3) 0.0838(12) Uani 1 1 d . . . . .
H38 H 0.286675 0.778939 1.357566 0.101 Uiso 1 1 calc R . . . .
C39 C 0.17866(19) 0.0858(5) 0.6485(4) 0.0891(13) Uani 1 1 d . . . . .
H39 H 0.182113 0.007548 0.623133 0.107 Uiso 1 1 calc R . . . .
C40 C 0.1546(2) 0.1749(5) 0.5780(4) 0.0914(14) Uani 1 1 d . . . . .
H40 H 0.141446 0.157033 0.504914 0.110 Uiso 1 1 calc R . . . .
C41 C 0.33745(18) 0.1413(5) 0.9391(4) 0.0875(13) Uani 1 1 d . . . . .
H41 H 0.349734 0.112392 0.880822 0.105 Uiso 1 1 calc R . . . .
C42 C 0.14977(17) 0.2913(4) 0.6146(3) 0.0806(12) Uani 1 1 d . . . . .
H42 H 0.132288 0.351283 0.566342 0.097 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
N1 C1 1.431(4) . ?
N1 C15 1.269(4) . ?
N2 O1 1.229(4) . ?
N2 O2 1.221(4) . ?
N2 C6 1.463(4) . ?
N3 C4 1.422(5) . ?
N3 C21 1.249(5) . ?
N4 O3 1.222(4) . ?
N4 O4 1.216(4) . ?
N4 C3 1.461(5) . ?
C1 C10 1.393(5) . ?
C1 C12 1.384(5) . ?
C2 C8 1.382(5) . ?
C2 C15 1.470(5) . ?
C2 C20 1.392(5) . ?
C3 C22 1.371(5) . ?
C3 C23 1.379(5) . ?
C4 C9 1.403(5) . ?
C4 C29 1.379(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(5) . ?
C5 C20 1.378(5) . ?
C6 C11 1.374(5) . ?
C7 C13 1.380(5) . ?
C7 C17 1.394(5) . ?
C7 C21 1.463(5) . ?
C8 H8 0.9300 . ?
C8 C11 1.380(5) . ?
C9 C24 1.404(6) . ?
C9 C25 1.411(5) . ?
C10 C14 1.440(5) . ?
C10 C26 1.390(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C12 C30 1.383(5) . ?
C13 H13 0.9300 . ?
C13 C23 1.368(5) . ?
C14 C18 1.202(5) . ?
C15 H15 0.9300 . ?
C16 C28 1.426(6) . ?
C16 C31 1.384(5) . ?
C16 C42 1.395(6) . ?
C17 H17 0.9300 . ?
C17 C22 1.375(5) . ?
C18 C19 1.425(5) . ?
C19 C27 1.383(5) . ?
C19 C34 1.403(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C24 C32 1.376(6) . ?
C25 C28 1.206(6) . ?
C26 H26 0.9300 . ?
C26 C38 1.364(6) . ?
C27 H27 0.9300 . ?
C27 C37 1.382(6) . ?
C29 H29 0.9300 . ?
C29 C36 1.399(6) . ?
C30 H30 0.9300 . ?
C30 C38 1.388(6) . ?
C31 H31 0.9300 . ?
C31 C33 1.395(6) . ?
C32 H32 0.9300 . ?
C32 C36 1.363(6) . ?
C33 H33 0.9300 . ?
C33 C39 1.355(7) . ?
C34 H34 0.9300 . ?
C34 C41 1.381(7) . ?
C35 H35 0.9300 . ?
C35 C37 1.353(6) . ?
C35 C41 1.368(7) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C39 C40 1.359(7) . ?
C40 H40 0.9300 . ?
C40 C42 1.376(7) . ?
C41 H41 0.9300 . ?
C42 H42 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
C15 N1 C1 118.4(3) . . ?
O1 N2 C6 117.6(3) . . ?
O2 N2 O1 124.1(3) . . ?
O2 N2 C6 118.3(3) . . ?
C21 N3 C4 118.9(3) . . ?
O3 N4 C3 118.5(3) . . ?
O4 N4 O3 122.2(3) . . ?
O4 N4 C3 119.3(3) . . ?
C10 C1 N1 118.3(3) . . ?
C12 C1 N1 122.2(3) . . ?
C12 C1 C10 119.4(3) . . ?
C8 C2 C15 117.9(3) . . ?
C8 C2 C20 119.7(3) . . ?
C20 C2 C15 122.4(3) . . ?
C22 C3 N4 119.5(3) . . ?
C22 C3 C23 122.4(3) . . ?
C23 C3 N4 118.1(3) . . ?
C9 C4 N3 117.2(3) . . ?
C29 C4 N3 123.3(3) . . ?
C29 C4 C9 119.4(3) . . ?
C6 C5 H5 120.9 . . ?
C6 C5 C20 118.3(3) . . ?
C20 C5 H5 120.9 . . ?
C5 C6 N2 119.0(3) . . ?
C11 C6 N2 118.2(3) . . ?
C11 C6 C5 122.7(3) . . ?
C13 C7 C17 119.2(3) . . ?
C13 C7 C21 119.3(3) . . ?
C17 C7 C21 121.4(3) . . ?
C2 C8 H8 119.7 . . ?
C11 C8 C2 120.6(3) . . ?
C11 C8 H8 119.7 . . ?
C4 C9 C24 118.6(4) . . ?
C4 C9 C25 121.8(3) . . ?
C24 C9 C25 119.6(3) . . ?
C1 C10 C14 122.4(3) . . ?
C26 C10 C1 119.1(4) . . ?
C26 C10 C14 118.6(3) . . ?
C6 C11 C8 118.2(3) . . ?
C6 C11 H11 120.9 . . ?
C8 C11 H11 120.9 . . ?
C1 C12 H12 119.6 . . ?
C30 C12 C1 120.9(4) . . ?
C30 C12 H12 119.6 . . ?
C7 C13 H13 119.3 . . ?
C23 C13 C7 121.4(4) . . ?
C23 C13 H13 119.3 . . ?
C18 C14 C10 172.4(4) . . ?
N1 C15 C2 122.9(3) . . ?
N1 C15 H15 118.5 . . ?
C2 C15 H15 118.5 . . ?
C31 C16 C28 118.9(4) . . ?
C31 C16 C42 118.8(4) . . ?
C42 C16 C28 122.3(4) . . ?
C7 C17 H17 120.0 . . ?
C22 C17 C7 120.1(3) . . ?
C22 C17 H17 120.0 . . ?
C14 C18 C19 175.4(4) . . ?
C27 C19 C18 118.4(4) . . ?
C27 C19 C34 119.0(4) . . ?
C34 C19 C18 122.5(4) . . ?
C2 C20 H20 119.8 . . ?
C5 C20 C2 120.4(3) . . ?
C5 C20 H20 119.8 . . ?
N3 C21 C7 124.3(4) . . ?
N3 C21 H21 117.9 . . ?
C7 C21 H21 117.9 . . ?
C3 C22 C17 118.8(3) . . ?
C3 C22 H22 120.6 . . ?
C17 C22 H22 120.6 . . ?
C3 C23 H23 121.0 . . ?
C13 C23 C3 118.0(3) . . ?
C13 C23 H23 121.0 . . ?
C9 C24 H24 119.5 . . ?
C32 C24 C9 121.0(4) . . ?
C32 C24 H24 119.5 . . ?
C28 C25 C9 175.8(4) . . ?
C10 C26 H26 119.4 . . ?
C38 C26 C10 121.3(4) . . ?
C38 C26 H26 119.4 . . ?
C19 C27 H27 119.9 . . ?
C37 C27 C19 120.1(4) . . ?
C37 C27 H27 119.9 . . ?
C25 C28 C16 177.7(4) . . ?
C4 C29 H29 119.6 . . ?
C4 C29 C36 120.9(4) . . ?
C36 C29 H29 119.6 . . ?
C12 C30 H30 120.3 . . ?
C12 C30 C38 119.4(4) . . ?
C38 C30 H30 120.3 . . ?
C16 C31 H31 120.3 . . ?
C16 C31 C33 119.4(4) . . ?
C33 C31 H31 120.3 . . ?
C24 C32 H32 119.9 . . ?
C36 C32 C24 120.3(4) . . ?
C36 C32 H32 119.9 . . ?
C31 C33 H33 119.7 . . ?
C39 C33 C31 120.5(4) . . ?
C39 C33 H33 119.7 . . ?
C19 C34 H34 120.4 . . ?
C41 C34 C19 119.3(4) . . ?
C41 C34 H34 120.4 . . ?
C37 C35 H35 119.8 . . ?
C37 C35 C41 120.4(4) . . ?
C41 C35 H35 119.8 . . ?
C29 C36 H36 120.1 . . ?
C32 C36 C29 119.8(4) . . ?
C32 C36 H36 120.1 . . ?
C27 C37 H37 119.7 . . ?
C35 C37 C27 120.6(4) . . ?
C35 C37 H37 119.7 . . ?
C26 C38 C30 119.9(4) . . ?
C26 C38 H38 120.0 . . ?
C30 C38 H38 120.0 . . ?
C33 C39 H39 119.7 . . ?
C33 C39 C40 120.6(4) . . ?
C40 C39 H39 119.7 . . ?
C39 C40 H40 119.9 . . ?
C39 C40 C42 120.2(4) . . ?
C42 C40 H40 119.9 . . ?
C34 C41 H41 119.7 . . ?
C35 C41 C34 120.6(4) . . ?
C35 C41 H41 119.7 . . ?
C16 C42 H42 119.8 . . ?
C40 C42 C16 120.3(4) . . ?
C40 C42 H42 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C10 C14 -2.3(5) . . . . ?
N1 C1 C10 C26 177.9(3) . . . . ?
N1 C1 C12 C30 -177.3(3) . . . . ?
N2 C6 C11 C8 177.4(3) . . . . ?
O1 N2 C6 C5 18.1(5) . . . . ?
O1 N2 C6 C11 -161.9(3) . . . . ?
N3 C4 C9 C24 -179.2(3) . . . . ?
N3 C4 C9 C25 1.6(5) . . . . ?
N3 C4 C29 C36 178.2(4) . . . . ?
O2 N2 C6 C5 -163.0(3) . . . . ?
O2 N2 C6 C11 16.9(5) . . . . ?
N4 C3 C22 C17 178.1(3) . . . . ?
N4 C3 C23 C13 -177.6(3) . . . . ?
O3 N4 C3 C22 -16.5(5) . . . . ?
O3 N4 C3 C23 162.1(4) . . . . ?
O4 N4 C3 C22 165.0(4) . . . . ?
O4 N4 C3 C23 -16.3(5) . . . . ?
C1 N1 C15 C2 178.4(3) . . . . ?
C1 C10 C26 C38 -1.0(5) . . . . ?
C1 C12 C30 C38 -0.1(6) . . . . ?
C2 C8 C11 C6 1.0(5) . . . . ?
C4 N3 C21 C7 -180.0(3) . . . . ?
C4 C9 C24 C32 1.4(6) . . . . ?
C4 C29 C36 C32 0.3(7) . . . . ?
C5 C6 C11 C8 -2.7(5) . . . . ?
C6 C5 C20 C2 -0.9(5) . . . . ?
C7 C13 C23 C3 -0.5(6) . . . . ?
C7 C17 C22 C3 -0.7(6) . . . . ?
C8 C2 C15 N1 178.3(3) . . . . ?
C8 C2 C20 C5 -0.7(5) . . . . ?
C9 C4 C29 C36 1.4(6) . . . . ?
C9 C24 C32 C36 0.3(7) . . . . ?
C10 C1 C12 C30 0.1(5) . . . . ?
C10 C26 C38 C30 1.0(6) . . . . ?
C12 C1 C10 C14 -179.8(3) . . . . ?
C12 C1 C10 C26 0.4(5) . . . . ?
C12 C30 C38 C26 -0.4(6) . . . . ?
C13 C7 C17 C22 1.3(6) . . . . ?
C13 C7 C21 N3 -179.0(4) . . . . ?
C14 C10 C26 C38 179.2(4) . . . . ?
C15 N1 C1 C10 144.9(3) . . . . ?
C15 N1 C1 C12 -37.7(5) . . . . ?
C15 C2 C8 C11 -177.3(3) . . . . ?
C15 C2 C20 C5 177.2(3) . . . . ?
C16 C31 C33 C39 1.5(6) . . . . ?
C17 C7 C13 C23 -0.7(6) . . . . ?
C17 C7 C21 N3 -0.6(6) . . . . ?
C18 C19 C27 C37 -179.3(4) . . . . ?
C18 C19 C34 C41 179.4(4) . . . . ?
C19 C27 C37 C35 0.6(6) . . . . ?
C19 C34 C41 C35 -0.9(7) . . . . ?
C20 C2 C8 C11 0.6(5) . . . . ?
C20 C2 C15 N1 0.5(5) . . . . ?
C20 C5 C6 N2 -177.4(3) . . . . ?
C20 C5 C6 C11 2.6(5) . . . . ?
C21 N3 C4 C9 -144.9(3) . . . . ?
C21 N3 C4 C29 38.2(5) . . . . ?
C21 C7 C13 C23 177.8(4) . . . . ?
C21 C7 C17 C22 -177.1(3) . . . . ?
C22 C3 C23 C13 1.0(6) . . . . ?
C23 C3 C22 C17 -0.4(6) . . . . ?
C24 C32 C36 C29 -1.2(7) . . . . ?
C25 C9 C24 C32 -179.4(4) . . . . ?
C27 C19 C34 C41 0.7(6) . . . . ?
C28 C16 C31 C33 179.8(4) . . . . ?
C28 C16 C42 C40 178.6(4) . . . . ?
C29 C4 C9 C24 -2.2(5) . . . . ?
C29 C4 C9 C25 178.6(3) . . . . ?
C31 C16 C42 C40 -2.7(6) . . . . ?
C31 C33 C39 C40 -2.3(7) . . . . ?
C33 C39 C40 C42 0.6(7) . . . . ?
C34 C19 C27 C37 -0.6(6) . . . . ?
C37 C35 C41 C34 1.0(7) . . . . ?
C39 C40 C42 C16 1.9(7) . . . . ?
C41 C35 C37 C27 -0.8(7) . . . . ?
C42 C16 C31 C33 1.0(6) . . . . ?

_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 1.719
_oxdiff_exptl_absorpt_empirical_full_min 0.621
