# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_cyp-539-22_auto
_database_code_depnum_ccdc_archive 'CCDC 2382179'
loop_
_audit_author_name
_audit_author_address
'Qinhua Song'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-10-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
(5S,6aS,7R,9R,9aS,13S)-12-benzyl-13-phenyl-5,6,6a,8,9,9a-hexahydro-7,9-methano-5,7-(methanoiminomethano)cyclopenta[h]quinolin-11-one
_chemical_formula_moiety         'C28 H26 N2 O'
_chemical_formula_sum            'C28 H26 N2 O'
_chemical_formula_weight         406.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.95607(12)
_cell_length_b                   12.99588(14)
_cell_length_c                   14.67188(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.3520(10)
_cell_angle_gamma                90
_cell_volume                     2088.45(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5176
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8110
_cell_measurement_theta_min      4.9830
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8029
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.960
_diffrn_reflns_theta_min         4.546
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -18.00   1.00    3.00    --  -41.76 -38.00  90.00   82
  2  ω   -105.00 -17.00   1.00    3.00    --  -41.76 -38.00-180.00   88
  3  ω    -80.00 -42.00   1.00    3.00    --  -41.76 125.00 -90.00   38
  4  ω    125.00 173.00   1.00    6.00    --  106.05 125.00-120.00   48
  5  ω     36.00 112.00   1.00    6.00    --  106.05-125.00 -60.00   76
  6  ω     68.00 108.00   1.00    6.00    --  106.05-125.00  30.00   40
  7  ω     79.00 171.00   1.00    6.00    --  106.05  30.00-180.00   92
  8  ω     80.00 174.00   1.00    6.00    --  106.05  30.00  90.00   94
  9  ω     36.00 112.00   1.00    6.00    --  106.05 -45.00 120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0844381000
_diffrn_orient_matrix_UB_12      0.0005252000
_diffrn_orient_matrix_UB_13      0.0854418000
_diffrn_orient_matrix_UB_21      0.1122606000
_diffrn_orient_matrix_UB_22      -0.0077043000
_diffrn_orient_matrix_UB_23      -0.0609395000
_diffrn_orient_matrix_UB_31      0.0069158000
_diffrn_orient_matrix_UB_32      0.1182906000
_diffrn_orient_matrix_UB_33      -0.0043411000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3598
_reflns_number_total             4055
_reflns_odcompleteness_completeness 99.90
_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 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.037
_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)+(0.0575P)²+0.3624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1102
_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:
 C10(H10), C9(H9), C7(H7), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C8(H8A,H8B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C24(H24), C3(H3), C27(H27), C18(H18), C22(H22), C1(H1), C2(H2),
 C20(H20), C25(H25), C21(H21), C26(H26), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.74856(9) 0.62555(7) 0.35816(7) 0.0512(2) Uani 1 1 d . . . . .
N2 N 0.71493(9) 0.45421(7) 0.34409(7) 0.0362(2) Uani 1 1 d . . . . .
N1 N 0.31145(11) 0.41354(11) 0.08864(8) 0.0567(3) Uani 1 1 d . . . . .
C23 C 0.59065(10) 0.29455(9) 0.36517(8) 0.0360(3) Uani 1 1 d . . . . .
C10 C 0.67021(10) 0.35628(9) 0.30134(8) 0.0342(2) Uani 1 1 d . . . . .
H10 H 0.7448 0.3147 0.2998 0.041 Uiso 1 1 calc R U . . .
C4 C 0.48862(11) 0.34395(10) 0.16868(8) 0.0406(3) Uani 1 1 d . . . . .
C11 C 0.68925(11) 0.55447(9) 0.32354(8) 0.0381(3) Uani 1 1 d . . . . .
C9 C 0.62367(11) 0.35325(10) 0.19756(8) 0.0388(3) Uani 1 1 d . . . . .
H9 H 0.6618 0.2915 0.1725 0.047 Uiso 1 1 calc R U . . .
C17 C 0.93462(10) 0.41711(10) 0.38871(9) 0.0397(3) Uani 1 1 d . . . . .
C15 C 0.45757(11) 0.53018(10) 0.28886(9) 0.0406(3) Uani 1 1 d . . . . .
H15A H 0.4458 0.4566 0.2815 0.049 Uiso 1 1 calc R U . . .
H15B H 0.4315 0.5541 0.3479 0.049 Uiso 1 1 calc R U . . .
C28 C 0.52014(11) 0.33794(11) 0.43226(9) 0.0433(3) Uani 1 1 d . . . . .
H28 H 0.5219 0.4087 0.4416 0.052 Uiso 1 1 calc R U . . .
C5 C 0.42324(12) 0.42525(11) 0.12665(8) 0.0447(3) Uani 1 1 d . . . . .
C16 C 0.80529(11) 0.43633(10) 0.41812(8) 0.0411(3) Uani 1 1 d . . . . .
H16A H 0.7790 0.3776 0.4534 0.049 Uiso 1 1 calc R U . . .
H16B H 0.8056 0.4957 0.4582 0.049 Uiso 1 1 calc R U . . .
C12 C 0.58461(11) 0.57096(9) 0.25957(9) 0.0411(3) Uani 1 1 d . . . . .
C7 C 0.60552(12) 0.53818(11) 0.15954(9) 0.0459(3) Uani 1 1 d . . . . .
H7 H 0.6453 0.5951 0.1280 0.055 Uiso 1 1 calc R U . . .
C8 C 0.67814(12) 0.44138(11) 0.14427(9) 0.0466(3) Uani 1 1 d . . . . .
H8A H 0.7623 0.4521 0.1640 0.056 Uiso 1 1 calc R U . . .
H8B H 0.6771 0.4247 0.0798 0.056 Uiso 1 1 calc R U . . .
C6 C 0.47031(12) 0.53428(11) 0.12785(9) 0.0492(3) Uani 1 1 d . . . . .
H6 H 0.4568 0.5687 0.0690 0.059 Uiso 1 1 calc R U . . .
C24 C 0.59011(13) 0.18798(10) 0.35603(10) 0.0485(3) Uani 1 1 d . . . . .
H24 H 0.6401 0.1573 0.3135 0.058 Uiso 1 1 calc R U . . .
C3 C 0.43073(14) 0.24895(11) 0.17074(10) 0.0519(3) Uani 1 1 d . . . . .
H3 H 0.4709 0.1927 0.1967 0.062 Uiso 1 1 calc R U . . .
C27 C 0.44669(12) 0.27624(14) 0.48584(10) 0.0568(4) Uani 1 1 d . . . . .
H27 H 0.3991 0.3061 0.5304 0.068 Uiso 1 1 calc R U . . .
C13 C 0.41312(13) 0.59553(11) 0.20775(11) 0.0512(3) Uani 1 1 d . . . . .
C18 C 0.98124(13) 0.45834(11) 0.31012(11) 0.0535(3) Uani 1 1 d . . . . .
H18 H 0.9319 0.4993 0.2726 0.064 Uiso 1 1 calc R U . . .
C22 C 1.01068(13) 0.35754(13) 0.44373(10) 0.0562(4) Uani 1 1 d . . . . .
H22 H 0.9812 0.3298 0.4973 0.067 Uiso 1 1 calc R U . . .
C1 C 0.25933(14) 0.32036(15) 0.09344(11) 0.0621(4) Uani 1 1 d . . . . .
H1 H 0.1818 0.3117 0.0673 0.074 Uiso 1 1 calc R U . . .
C14 C 0.51437(14) 0.67310(11) 0.23970(12) 0.0575(4) Uani 1 1 d . . . . .
H14A H 0.5478 0.7152 0.1917 0.069 Uiso 1 1 calc R U . . .
H14B H 0.4951 0.7133 0.2932 0.069 Uiso 1 1 calc R U . . .
C2 C 0.31397(15) 0.23733(13) 0.13462(11) 0.0604(4) Uani 1 1 d . . . . .
H2 H 0.2735 0.1746 0.1382 0.072 Uiso 1 1 calc R U . . .
C20 C 1.17489(13) 0.37906(14) 0.34175(14) 0.0663(5) Uani 1 1 d . . . . .
H20 H 1.2550 0.3659 0.3258 0.080 Uiso 1 1 calc R U . . .
C25 C 0.51683(16) 0.12675(13) 0.40883(12) 0.0630(4) Uani 1 1 d . . . . .
H25 H 0.5166 0.0557 0.4009 0.076 Uiso 1 1 calc R U . . .
C21 C 1.13004(14) 0.33866(15) 0.42008(12) 0.0674(5) Uani 1 1 d . . . . .
H21 H 1.1800 0.2983 0.4577 0.081 Uiso 1 1 calc R U . . .
C26 C 0.44408(14) 0.17116(14) 0.47319(12) 0.0642(4) Uani 1 1 d . . . . .
H26 H 0.3933 0.1304 0.5080 0.077 Uiso 1 1 calc R U . . .
C19 C 1.10100(15) 0.43926(13) 0.28663(14) 0.0671(4) Uani 1 1 d . . . . .
H19 H 1.1314 0.4673 0.2334 0.081 Uiso 1 1 calc R U . . .
H13 H 0.3272(16) 0.6158(13) 0.1987(12) 0.062(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.2321(15) . ?
N2 C10 1.4963(14) . ?
N2 C11 1.3652(15) . ?
N2 C16 1.4707(15) . ?
N1 C5 1.3424(17) . ?
N1 C1 1.341(2) . ?
C23 C10 1.5229(16) . ?
C23 C28 1.3855(17) . ?
C23 C24 1.3915(18) . ?
C10 H10 0.9800 . ?
C10 C9 1.5947(16) . ?
C4 C9 1.5342(17) . ?
C4 C5 1.4103(19) . ?
C4 C3 1.3885(19) . ?
C11 C12 1.4801(17) . ?
C9 H9 0.9800 . ?
C9 C8 1.5170(18) . ?
C17 C16 1.5117(17) . ?
C17 C18 1.380(2) . ?
C17 C22 1.3834(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C12 1.5592(17) . ?
C15 C13 1.5321(18) . ?
C28 H28 0.9300 . ?
C28 C27 1.392(2) . ?
C5 C6 1.508(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C12 C7 1.5503(19) . ?
C12 C13 2.0353(18) . ?
C12 C14 1.5584(18) . ?
C7 H7 0.9800 . ?
C7 C8 1.508(2) . ?
C7 C6 1.5430(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 H6 0.9800 . ?
C6 C13 1.560(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.381(2) . ?
C27 H27 0.9300 . ?
C27 C26 1.378(3) . ?
C13 C14 1.563(2) . ?
C13 H13 0.984(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(2) . ?
C22 H22 0.9300 . ?
C22 C21 1.383(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.368(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C2 H2 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.365(3) . ?
C20 C19 1.375(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(2) . ?
C21 H21 0.9300 . ?
C26 H26 0.9300 . ?
C19 H19 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
C11 N2 C10 130.95(10) . . ?
C11 N2 C16 116.46(10) . . ?
C16 N2 C10 112.53(9) . . ?
C1 N1 C5 117.77(14) . . ?
C28 C23 C10 124.01(11) . . ?
C28 C23 C24 118.19(12) . . ?
C24 C23 C10 117.79(11) . . ?
N2 C10 C23 112.14(9) . . ?
N2 C10 H10 102.3 . . ?
N2 C10 C9 121.03(9) . . ?
C23 C10 H10 102.3 . . ?
C23 C10 C9 113.54(9) . . ?
C9 C10 H10 102.3 . . ?
C5 C4 C9 122.56(11) . . ?
C3 C4 C9 120.14(12) . . ?
C3 C4 C5 116.62(12) . . ?
O1 C11 N2 121.37(11) . . ?
O1 C11 C12 123.09(11) . . ?
N2 C11 C12 115.52(10) . . ?
C10 C9 H9 104.4 . . ?
C4 C9 C10 123.38(10) . . ?
C4 C9 H9 104.4 . . ?
C8 C9 C10 110.65(10) . . ?
C8 C9 C4 107.80(10) . . ?
C8 C9 H9 104.4 . . ?
C18 C17 C16 122.83(12) . . ?
C18 C17 C22 118.36(12) . . ?
C22 C17 C16 118.80(12) . . ?
H15A C15 H15B 112.0 . . ?
C12 C15 H15A 114.9 . . ?
C12 C15 H15B 114.9 . . ?
C13 C15 H15A 114.9 . . ?
C13 C15 H15B 114.9 . . ?
C13 C15 C12 82.35(10) . . ?
C23 C28 H28 119.8 . . ?
C23 C28 C27 120.41(14) . . ?
C27 C28 H28 119.8 . . ?
N1 C5 C4 123.07(13) . . ?
N1 C5 C6 114.82(12) . . ?
C4 C5 C6 121.94(11) . . ?
N2 C16 C17 115.75(10) . . ?
N2 C16 H16A 108.3 . . ?
N2 C16 H16B 108.3 . . ?
C17 C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C11 C12 C15 117.33(11) . . ?
C11 C12 C7 115.53(10) . . ?
C11 C12 C13 162.56(11) . . ?
C11 C12 C14 127.85(11) . . ?
C15 C12 C13 48.25(7) . . ?
C7 C12 C15 108.69(10) . . ?
C7 C12 C13 81.10(9) . . ?
C7 C12 C14 98.07(11) . . ?
C14 C12 C15 84.32(10) . . ?
C14 C12 C13 49.39(8) . . ?
C12 C7 H7 108.5 . . ?
C8 C7 C12 117.40(11) . . ?
C8 C7 H7 108.5 . . ?
C8 C7 C6 115.72(12) . . ?
C6 C7 C12 97.58(10) . . ?
C6 C7 H7 108.5 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C7 C8 C9 109.74(10) . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C5 C6 C7 111.10(11) . . ?
C5 C6 H6 112.0 . . ?
C5 C6 C13 110.18(11) . . ?
C7 C6 H6 112.0 . . ?
C7 C6 C13 99.00(11) . . ?
C13 C6 H6 112.0 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.38(14) . . ?
C25 C24 H24 119.3 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.55(15) . . ?
C2 C3 H3 119.7 . . ?
C28 C27 H27 119.8 . . ?
C26 C27 C28 120.33(14) . . ?
C26 C27 H27 119.8 . . ?
C15 C13 C12 49.40(7) . . ?
C15 C13 C6 100.07(10) . . ?
C15 C13 C14 85.08(10) . . ?
C15 C13 H13 122.6(10) . . ?
C12 C13 H13 164.7(10) . . ?
C6 C13 C12 79.46(8) . . ?
C6 C13 C14 105.05(12) . . ?
C6 C13 H13 115.8(10) . . ?
C14 C13 C12 49.21(7) . . ?
C14 C13 H13 122.5(10) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.61(15) . . ?
C19 C18 H18 119.7 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.87(15) . . ?
C21 C22 H22 119.6 . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.57(13) . . ?
C2 C1 H1 118.2 . . ?
C12 C14 C13 81.40(10) . . ?
C12 C14 H14A 115.0 . . ?
C12 C14 H14B 115.0 . . ?
C13 C14 H14A 115.0 . . ?
C13 C14 H14B 115.0 . . ?
H14A C14 H14B 112.1 . . ?
C3 C2 H2 120.8 . . ?
C1 C2 C3 118.35(15) . . ?
C1 C2 H2 120.8 . . ?
C21 C20 H20 120.2 . . ?
C21 C20 C19 119.69(14) . . ?
C19 C20 H20 120.2 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.79(15) . . ?
C26 C25 H25 120.1 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.28(16) . . ?
C20 C21 H21 119.9 . . ?
C27 C26 H26 120.1 . . ?
C25 C26 C27 119.81(14) . . ?
C25 C26 H26 120.1 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.19(16) . . ?
C20 C19 H19 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C11 C12 C15 -118.58(13) . . . . ?
O1 C11 C12 C7 111.15(14) . . . . ?
O1 C11 C12 C13 -87.4(4) . . . . ?
O1 C11 C12 C14 -13.5(2) . . . . ?
N2 C10 C9 C4 -106.51(13) . . . . ?
N2 C10 C9 C8 23.25(14) . . . . ?
N2 C11 C12 C15 59.87(15) . . . . ?
N2 C11 C12 C7 -70.40(14) . . . . ?
N2 C11 C12 C13 91.0(3) . . . . ?
N2 C11 C12 C14 164.98(13) . . . . ?
N1 C5 C6 C7 -171.68(12) . . . . ?
N1 C5 C6 C13 79.62(14) . . . . ?
N1 C1 C2 C3 -2.1(2) . . . . ?
C23 C10 C9 C4 31.36(15) . . . . ?
C23 C10 C9 C8 161.13(10) . . . . ?
C23 C28 C27 C26 0.5(2) . . . . ?
C23 C24 C25 C26 -1.2(2) . . . . ?
C10 N2 C11 O1 -169.32(11) . . . . ?
C10 N2 C11 C12 12.19(18) . . . . ?
C10 N2 C16 C17 81.24(13) . . . . ?
C10 C23 C28 C27 177.84(11) . . . . ?
C10 C23 C24 C25 -177.43(13) . . . . ?
C10 C9 C8 C7 -81.93(12) . . . . ?
C4 C9 C8 C7 55.69(13) . . . . ?
C4 C5 C6 C7 12.92(18) . . . . ?
C4 C5 C6 C13 -95.77(14) . . . . ?
C4 C3 C2 C1 2.8(2) . . . . ?
C11 N2 C10 C23 -113.03(13) . . . . ?
C11 N2 C10 C9 25.38(17) . . . . ?
C11 N2 C16 C17 -96.46(13) . . . . ?
C11 C12 C7 C8 38.34(16) . . . . ?
C11 C12 C7 C6 162.55(11) . . . . ?
C11 C12 C14 C13 -157.70(14) . . . . ?
C9 C4 C5 N1 169.53(12) . . . . ?
C9 C4 C5 C6 -15.46(19) . . . . ?
C9 C4 C3 C2 -172.11(12) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C17 C22 C21 C20 0.2(3) . . . . ?
C15 C12 C7 C8 -95.97(13) . . . . ?
C15 C12 C7 C6 28.23(12) . . . . ?
C15 C12 C14 C13 -37.23(10) . . . . ?
C15 C13 C14 C12 37.95(10) . . . . ?
C28 C23 C10 N2 28.90(15) . . . . ?
C28 C23 C10 C9 -112.75(12) . . . . ?
C28 C23 C24 C25 3.3(2) . . . . ?
C28 C27 C26 C25 1.7(2) . . . . ?
C5 N1 C1 C2 -0.1(2) . . . . ?
C5 C4 C9 C10 110.85(14) . . . . ?
C5 C4 C9 C8 -20.09(15) . . . . ?
C5 C4 C3 C2 -1.3(2) . . . . ?
C5 C6 C13 C15 59.45(13) . . . . ?
C5 C6 C13 C12 104.59(10) . . . . ?
C5 C6 C13 C14 147.01(11) . . . . ?
C16 N2 C10 C23 69.70(12) . . . . ?
C16 N2 C10 C9 -151.89(10) . . . . ?
C16 N2 C11 O1 7.86(17) . . . . ?
C16 N2 C11 C12 -170.62(10) . . . . ?
C16 C17 C18 C19 179.32(14) . . . . ?
C16 C17 C22 C21 -179.39(14) . . . . ?
C12 C15 C13 C6 66.62(10) . . . . ?
C12 C15 C13 C14 -37.82(10) . . . . ?
C12 C7 C8 C9 52.85(15) . . . . ?
C12 C7 C6 C5 -100.19(12) . . . . ?
C12 C7 C6 C13 15.62(12) . . . . ?
C7 C12 C14 C13 70.89(11) . . . . ?
C7 C6 C13 C15 -57.08(12) . . . . ?
C7 C6 C13 C12 -11.94(9) . . . . ?
C7 C6 C13 C14 30.49(12) . . . . ?
C8 C7 C6 C5 25.22(16) . . . . ?
C8 C7 C6 C13 141.03(11) . . . . ?
C6 C7 C8 C9 -61.65(14) . . . . ?
C6 C13 C14 C12 -61.17(12) . . . . ?
C24 C23 C10 N2 -150.32(11) . . . . ?
C24 C23 C10 C9 68.03(14) . . . . ?
C24 C23 C28 C27 -2.94(18) . . . . ?
C24 C25 C26 C27 -1.3(2) . . . . ?
C3 C4 C9 C10 -78.89(16) . . . . ?
C3 C4 C9 C8 150.18(12) . . . . ?
C3 C4 C5 N1 -1.06(19) . . . . ?
C3 C4 C5 C6 173.95(12) . . . . ?
C13 C15 C12 C11 168.00(12) . . . . ?
C13 C15 C12 C7 -58.62(11) . . . . ?
C13 C15 C12 C14 38.00(10) . . . . ?
C13 C12 C7 C8 -136.11(11) . . . . ?
C13 C12 C7 C6 -11.91(9) . . . . ?
C18 C17 C16 N2 29.63(18) . . . . ?
C18 C17 C22 C21 -0.8(2) . . . . ?
C22 C17 C16 N2 -151.83(12) . . . . ?
C22 C17 C18 C19 0.8(2) . . . . ?
C1 N1 C5 C4 1.8(2) . . . . ?
C1 N1 C5 C6 -173.57(13) . . . . ?
C14 C12 C7 C8 177.33(11) . . . . ?
C14 C12 C7 C6 -58.47(11) . . . . ?
C21 C20 C19 C18 -0.4(3) . . . . ?
C19 C20 C21 C22 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.265
_oxdiff_exptl_absorpt_empirical_full_min 0.542
####################################################################### 
# 
# 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_579-4a_auto
_database_code_depnum_ccdc_archive 'CCDC 2382181'
loop_
_audit_author_name
_audit_author_address
'Qinhua Song'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;
_audit_creation_date             2024-08-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H28 N2 O'
_chemical_formula_sum            'C29 H28 N2 O'
_chemical_formula_weight         420.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.93903(16)
_cell_length_b                   12.54235(16)
_cell_length_c                   15.9418(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.8562(13)
_cell_angle_gamma                90
_cell_volume                     2175.81(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4717
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9410
_cell_measurement_theta_min      4.4860
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8184
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.900
_diffrn_reflns_theta_min         4.495
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -14.00   1.00    2.00    --  -41.51 -57.00  60.00  100
  2  ω    -30.00  61.00   1.00    2.00    --   41.51 -38.00  90.00   91
  3  ω    -26.00  13.00   1.00    2.00    --   41.51 -38.00-180.00   39
  4  ω     40.00  65.00   1.00    2.00    --   41.51 -38.00-180.00   25
  5  ω     33.00 117.00   1.00    4.00    --  105.74 -45.00   0.00   84
  6  ω     41.00 107.00   1.00    4.00    --  105.74 -94.00   0.00   66
  7  ω     39.00 132.00   1.00    4.00    --  105.74 -45.00-180.00   93
  8  ω     79.00 173.00   1.00    4.00    --  105.74  30.00   0.00   94
  9  ω    139.00 165.00   1.00    4.00    --  105.74  77.00-150.00   26
 10  ω    139.00 165.00   1.00    4.00    --  105.74  77.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1386652000
_diffrn_orient_matrix_UB_12      -0.0224122000
_diffrn_orient_matrix_UB_13      0.0017679000
_diffrn_orient_matrix_UB_21      0.0033522000
_diffrn_orient_matrix_UB_22      -0.0371737000
_diffrn_orient_matrix_UB_23      0.0923331000
_diffrn_orient_matrix_UB_31      -0.0280831000
_diffrn_orient_matrix_UB_32      -0.1149249000
_diffrn_orient_matrix_UB_33      -0.0301985000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3692
_reflns_number_total             4230
_reflns_odcompleteness_completeness 99.85
_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 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.4030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1131
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C14(H14), C13(H13), C11(H11), C12(H12), C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C22(H22A,H22B), C8(H8A,H8B)
1.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C24(H24), C20(H20), C2(H2), C28(H28), C3(H3), C25(H25), C26(H26),
 C17(H17), C27(H27), C4(H4), C19(H19), C18(H18)
1.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24951(10) 0.63640(8) 0.61911(7) 0.0543(3) Uani 1 1 d . . . . .
N2 N 0.28452(9) 0.45893(8) 0.63897(7) 0.0358(2) Uani 1 1 d . . . . .
N1 N 0.70504(12) 0.42968(11) 0.88485(8) 0.0527(3) Uani 1 1 d . . . . .
C15 C 0.40778(11) 0.29095(10) 0.63200(8) 0.0362(3) Uani 1 1 d . . . . .
C9 C 0.42122(12) 0.58428(10) 0.71458(8) 0.0365(3) Uani 1 1 d . . . . .
C14 C 0.33096(11) 0.36055(9) 0.68477(8) 0.0335(3) Uani 1 1 d . . . . .
H14 H 0.2558 0.3183 0.6858 0.040 Uiso 1 1 calc R U . . .
C1 C 0.51878(12) 0.35388(10) 0.81381(8) 0.0373(3) Uani 1 1 d . . . . .
C13 C 0.38199(11) 0.36425(10) 0.78195(8) 0.0352(3) Uani 1 1 d . . . . .
H13 H 0.3436 0.3027 0.8066 0.042 Uiso 1 1 calc R U . . .
C11 C 0.40621(12) 0.55700(10) 0.80807(8) 0.0379(3) Uani 1 1 d . . . . .
H11 H 0.3698 0.6190 0.8335 0.045 Uiso 1 1 calc R U . . .
C23 C 0.06215(12) 0.41298(10) 0.59978(8) 0.0388(3) Uani 1 1 d . . . . .
C12 C 0.33025(12) 0.45980(10) 0.82532(8) 0.0389(3) Uani 1 1 d . . . . .
H12 H 0.2460 0.4718 0.7998 0.047 Uiso 1 1 calc R U . . .
C21 C 0.31137(12) 0.56441(10) 0.65441(8) 0.0374(3) Uani 1 1 d . . . . .
C5 C 0.59032(12) 0.44031(11) 0.84716(8) 0.0396(3) Uani 1 1 d . . . . .
C10 C 0.54669(11) 0.53870(11) 0.69241(8) 0.0385(3) Uani 1 1 d . . . . .
H10A H 0.5582 0.4630 0.7029 0.046 Uiso 1 1 calc R U . . .
H10B H 0.5696 0.5593 0.6375 0.046 Uiso 1 1 calc R U . . .
C6 C 0.54395(12) 0.55347(11) 0.84015(8) 0.0410(3) Uani 1 1 d . . . . .
H6 H 0.5615 0.5925 0.8933 0.049 Uiso 1 1 calc R U . . .
C16 C 0.47519(12) 0.32898(12) 0.56946(9) 0.0428(3) Uani 1 1 d . . . . .
H16 H 0.4722 0.4011 0.5557 0.051 Uiso 1 1 calc R U . . .
C22 C 0.18697(12) 0.43537(12) 0.57102(8) 0.0415(3) Uani 1 1 d . . . . .
H22A H 0.2118 0.3740 0.5398 0.050 Uiso 1 1 calc R U . . .
H22B H 0.1796 0.4954 0.5325 0.050 Uiso 1 1 calc R U . . .
C24 C -0.01421(13) 0.33828(12) 0.55667(9) 0.0466(3) Uani 1 1 d . . . . .
H24 H 0.0134 0.3006 0.5120 0.056 Uiso 1 1 calc R U . . .
C20 C 0.40951(14) 0.18151(12) 0.64763(10) 0.0471(3) Uani 1 1 d . . . . .
H20 H 0.3613 0.1540 0.6872 0.056 Uiso 1 1 calc R U . . .
C7 C 0.59659(13) 0.61165(11) 0.76552(9) 0.0438(3) Uani 1 1 d . . . . .
C2 C 0.57215(14) 0.25343(12) 0.82413(9) 0.0468(3) Uani 1 1 d . . . . .
H2 H 0.5278 0.1935 0.8048 0.056 Uiso 1 1 calc R U . . .
C28 C 0.01900(13) 0.46718(12) 0.66646(10) 0.0489(4) Uani 1 1 d . . . . .
H28 H 0.0689 0.5175 0.6960 0.059 Uiso 1 1 calc R U . . .
C8 C 0.49321(14) 0.69054(11) 0.73087(10) 0.0476(3) Uani 1 1 d . . . . .
H8A H 0.4627 0.7368 0.7728 0.057 Uiso 1 1 calc R U . . .
H8B H 0.5095 0.7293 0.6805 0.057 Uiso 1 1 calc R U . . .
C3 C 0.69016(15) 0.24169(14) 0.86271(10) 0.0545(4) Uani 1 1 d . . . . .
H3 H 0.7265 0.1747 0.8687 0.065 Uiso 1 1 calc R U . . .
C25 C -0.13099(14) 0.31937(13) 0.57963(11) 0.0538(4) Uani 1 1 d . . . . .
H25 H -0.1816 0.2697 0.5499 0.065 Uiso 1 1 calc R U . . .
C26 C -0.17248(14) 0.37363(13) 0.64614(12) 0.0556(4) Uani 1 1 d . . . . .
H26 H -0.2508 0.3605 0.6616 0.067 Uiso 1 1 calc R U . . .
C29 C 0.32596(16) 0.44162(14) 0.91984(9) 0.0556(4) Uani 1 1 d . . . . .
H29A H 0.2774 0.3796 0.9284 0.083 Uiso 1 1 calc R U . . .
H29B H 0.2899 0.5026 0.9441 0.083 Uiso 1 1 calc R U . . .
H29C H 0.4079 0.4313 0.9464 0.083 Uiso 1 1 calc R U . . .
C17 C 0.54754(13) 0.26000(15) 0.52696(10) 0.0548(4) Uani 1 1 d . . . . .
H17 H 0.5933 0.2865 0.4855 0.066 Uiso 1 1 calc R U . . .
C27 C -0.09743(14) 0.44746(13) 0.68970(12) 0.0574(4) Uani 1 1 d . . . . .
H27 H -0.1250 0.4842 0.7348 0.069 Uiso 1 1 calc R U . . .
C4 C 0.75260(15) 0.33135(15) 0.89195(11) 0.0584(4) Uani 1 1 d . . . . .
H4 H 0.8321 0.3234 0.9180 0.070 Uiso 1 1 calc R U . . .
C19 C 0.48132(17) 0.11310(14) 0.60557(12) 0.0604(4) Uani 1 1 d . . . . .
H19 H 0.4821 0.0405 0.6175 0.072 Uiso 1 1 calc R U . . .
C18 C 0.55178(15) 0.15304(16) 0.54587(11) 0.0624(5) Uani 1 1 d . . . . .
H18 H 0.6020 0.1078 0.5185 0.075 Uiso 1 1 calc R U . . .
H7 H 0.6857(15) 0.6307(12) 0.7748(10) 0.043(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.2297(16) . ?
N2 C14 1.4961(15) . ?
N2 C21 1.3720(16) . ?
N2 C22 1.4710(16) . ?
N1 C5 1.3416(18) . ?
N1 C4 1.339(2) . ?
C15 C14 1.5231(17) . ?
C15 C16 1.3840(18) . ?
C15 C20 1.395(2) . ?
C9 C11 1.5540(18) . ?
C9 C21 1.4802(18) . ?
C9 C10 1.5602(18) . ?
C9 C7 2.0346(19) . ?
C9 C8 1.5563(18) . ?
C14 H14 0.9800 . ?
C14 C13 1.5929(17) . ?
C1 C13 1.5358(18) . ?
C1 C5 1.4090(19) . ?
C1 C2 1.3913(19) . ?
C13 H13 0.9800 . ?
C13 C12 1.5214(17) . ?
C11 H11 0.9800 . ?
C11 C12 1.5162(18) . ?
C11 C6 1.5416(18) . ?
C23 C22 1.5104(19) . ?
C23 C24 1.3895(19) . ?
C23 C28 1.385(2) . ?
C12 H12 0.9800 . ?
C12 C29 1.5293(19) . ?
C5 C6 1.5075(19) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C7 1.5375(19) . ?
C6 H6 0.9800 . ?
C6 C7 1.555(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.394(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C24 H24 0.9300 . ?
C24 C25 1.385(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.382(2) . ?
C7 C8 1.561(2) . ?
C7 H7 0.999(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(2) . ?
C28 H28 0.9300 . ?
C28 C27 1.385(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.372(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.375(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.377(2) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.375(3) . ?
C27 H27 0.9300 . ?
C4 H4 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.379(3) . ?
C18 H18 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
C21 N2 C14 130.69(11) . . ?
C21 N2 C22 116.86(11) . . ?
C22 N2 C14 112.24(10) . . ?
C4 N1 C5 117.84(14) . . ?
C16 C15 C14 124.40(12) . . ?
C16 C15 C20 117.99(12) . . ?
C20 C15 C14 117.61(12) . . ?
C11 C9 C10 108.54(10) . . ?
C11 C9 C7 80.91(8) . . ?
C11 C9 C8 97.45(10) . . ?
C21 C9 C11 115.23(11) . . ?
C21 C9 C10 117.79(11) . . ?
C21 C9 C7 163.16(11) . . ?
C21 C9 C8 128.01(11) . . ?
C10 C9 C7 48.46(7) . . ?
C8 C9 C10 84.82(10) . . ?
C8 C9 C7 49.34(8) . . ?
N2 C14 C15 112.46(10) . . ?
N2 C14 H14 102.2 . . ?
N2 C14 C13 121.23(10) . . ?
C15 C14 H14 102.2 . . ?
C15 C14 C13 113.30(10) . . ?
C13 C14 H14 102.2 . . ?
C5 C1 C13 122.99(11) . . ?
C2 C1 C13 119.92(12) . . ?
C2 C1 C5 116.23(12) . . ?
C14 C13 H13 104.1 . . ?
C1 C13 C14 123.51(10) . . ?
C1 C13 H13 104.1 . . ?
C12 C13 C14 110.81(10) . . ?
C12 C13 C1 108.15(11) . . ?
C12 C13 H13 104.1 . . ?
C9 C11 H11 108.0 . . ?
C12 C11 C9 117.68(11) . . ?
C12 C11 H11 108.0 . . ?
C12 C11 C6 116.87(11) . . ?
C6 C11 C9 97.42(10) . . ?
C6 C11 H11 108.0 . . ?
C24 C23 C22 119.44(13) . . ?
C28 C23 C22 122.10(12) . . ?
C28 C23 C24 118.42(13) . . ?
C13 C12 H12 108.1 . . ?
C13 C12 C29 112.37(11) . . ?
C11 C12 C13 108.34(10) . . ?
C11 C12 H12 108.1 . . ?
C11 C12 C29 111.79(12) . . ?
C29 C12 H12 108.1 . . ?
O1 C21 N2 121.88(12) . . ?
O1 C21 C9 123.06(12) . . ?
N2 C21 C9 115.05(11) . . ?
N1 C5 C1 123.41(13) . . ?
N1 C5 C6 114.78(12) . . ?
C1 C5 C6 121.78(12) . . ?
C9 C10 H10A 114.9 . . ?
C9 C10 H10B 114.9 . . ?
H10A C10 H10B 112.0 . . ?
C7 C10 C9 82.11(10) . . ?
C7 C10 H10A 114.9 . . ?
C7 C10 H10B 114.9 . . ?
C11 C6 H6 111.8 . . ?
C11 C6 C7 99.12(11) . . ?
C5 C6 C11 111.20(11) . . ?
C5 C6 H6 111.8 . . ?
C5 C6 C7 110.51(11) . . ?
C7 C6 H6 111.8 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.46(14) . . ?
C17 C16 H16 119.8 . . ?
N2 C22 C23 115.09(11) . . ?
N2 C22 H22A 108.5 . . ?
N2 C22 H22B 108.5 . . ?
C23 C22 H22A 108.5 . . ?
C23 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.60(14) . . ?
C25 C24 H24 119.7 . . ?
C15 C20 H20 119.3 . . ?
C19 C20 C15 121.48(15) . . ?
C19 C20 H20 119.3 . . ?
C9 C7 H7 164.7(9) . . ?
C10 C7 C9 49.43(7) . . ?
C10 C7 C6 99.79(10) . . ?
C10 C7 C8 85.44(10) . . ?
C10 C7 H7 121.3(9) . . ?
C6 C7 C9 79.54(8) . . ?
C6 C7 C8 104.87(11) . . ?
C6 C7 H7 115.5(9) . . ?
C8 C7 C9 49.16(7) . . ?
C8 C7 H7 124.1(9) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.76(15) . . ?
C3 C2 H2 119.6 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.85(14) . . ?
C27 C28 H28 119.6 . . ?
C9 C8 C7 81.50(10) . . ?
C9 C8 H8A 115.0 . . ?
C9 C8 H8B 115.0 . . ?
C7 C8 H8A 115.0 . . ?
C7 C8 H8B 115.0 . . ?
H8A C8 H8B 112.1 . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.32(14) . . ?
C4 C3 H3 120.8 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.32(14) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.66(14) . . ?
C27 C26 H26 120.2 . . ?
C12 C29 H29A 109.5 . . ?
C12 C29 H29B 109.5 . . ?
C12 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.48(15) . . ?
C18 C17 H17 119.8 . . ?
C28 C27 H27 119.9 . . ?
C26 C27 C28 120.16(15) . . ?
C26 C27 H27 119.9 . . ?
N1 C4 C3 123.40(14) . . ?
N1 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
C20 C19 H19 120.2 . . ?
C18 C19 C20 119.66(16) . . ?
C18 C19 H19 120.2 . . ?
C17 C18 C19 119.82(14) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 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
N2 C14 C13 C1 -107.63(13) . . . . ?
N2 C14 C13 C12 23.02(15) . . . . ?
N1 C5 C6 C11 -171.79(11) . . . . ?
N1 C5 C6 C7 79.15(15) . . . . ?
C15 C14 C13 C1 30.76(16) . . . . ?
C15 C14 C13 C12 161.41(10) . . . . ?
C15 C16 C17 C18 0.8(2) . . . . ?
C15 C20 C19 C18 -0.9(3) . . . . ?
C9 C11 C12 C13 54.41(15) . . . . ?
C9 C11 C12 C29 178.76(11) . . . . ?
C9 C11 C6 C5 -100.22(12) . . . . ?
C9 C11 C6 C7 16.07(11) . . . . ?
C9 C10 C7 C6 67.03(10) . . . . ?
C9 C10 C7 C8 -37.30(9) . . . . ?
C14 N2 C21 O1 -167.35(12) . . . . ?
C14 N2 C21 C9 14.10(19) . . . . ?
C14 N2 C22 C23 76.93(14) . . . . ?
C14 C15 C16 C17 176.99(12) . . . . ?
C14 C15 C20 C19 -176.86(14) . . . . ?
C14 C13 C12 C11 -82.18(12) . . . . ?
C14 C13 C12 C29 153.81(12) . . . . ?
C1 C13 C12 C11 56.07(13) . . . . ?
C1 C13 C12 C29 -67.93(14) . . . . ?
C1 C5 C6 C11 10.20(17) . . . . ?
C1 C5 C6 C7 -98.85(14) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C13 C1 C5 N1 171.24(12) . . . . ?
C13 C1 C5 C6 -10.93(19) . . . . ?
C13 C1 C2 C3 -171.62(13) . . . . ?
C11 C9 C21 O1 110.13(15) . . . . ?
C11 C9 C21 N2 -71.33(15) . . . . ?
C11 C9 C10 C7 -58.67(11) . . . . ?
C11 C9 C8 C7 71.19(10) . . . . ?
C11 C6 C7 C9 -12.31(9) . . . . ?
C11 C6 C7 C10 -57.64(12) . . . . ?
C11 C6 C7 C8 30.21(12) . . . . ?
C23 C24 C25 C26 -0.7(2) . . . . ?
C23 C28 C27 C26 -0.4(2) . . . . ?
C12 C11 C6 C5 26.02(16) . . . . ?
C12 C11 C6 C7 142.30(11) . . . . ?
C21 N2 C14 C15 -113.78(14) . . . . ?
C21 N2 C14 C13 24.92(18) . . . . ?
C21 N2 C22 C23 -98.31(14) . . . . ?
C21 C9 C11 C12 37.04(16) . . . . ?
C21 C9 C11 C6 162.70(11) . . . . ?
C21 C9 C10 C7 168.09(12) . . . . ?
C21 C9 C8 C7 -158.44(14) . . . . ?
C5 N1 C4 C3 0.0(2) . . . . ?
C5 C1 C13 C14 107.89(14) . . . . ?
C5 C1 C13 C12 -23.83(16) . . . . ?
C5 C1 C2 C3 -2.0(2) . . . . ?
C5 C6 C7 C9 104.51(10) . . . . ?
C5 C6 C7 C10 59.18(13) . . . . ?
C5 C6 C7 C8 147.02(11) . . . . ?
C10 C9 C11 C12 -97.52(13) . . . . ?
C10 C9 C11 C6 28.14(12) . . . . ?
C10 C9 C21 O1 -119.64(14) . . . . ?
C10 C9 C21 N2 58.89(15) . . . . ?
C10 C9 C8 C7 -36.88(9) . . . . ?
C10 C7 C8 C9 37.48(9) . . . . ?
C6 C11 C12 C13 -61.01(14) . . . . ?
C6 C11 C12 C29 63.34(15) . . . . ?
C6 C7 C8 C9 -61.46(11) . . . . ?
C16 C15 C14 N2 28.14(17) . . . . ?
C16 C15 C14 C13 -113.95(13) . . . . ?
C16 C15 C20 C19 3.5(2) . . . . ?
C16 C17 C18 C19 1.9(2) . . . . ?
C22 N2 C14 C15 71.83(13) . . . . ?
C22 N2 C14 C13 -149.48(11) . . . . ?
C22 N2 C21 O1 6.84(19) . . . . ?
C22 N2 C21 C9 -171.71(11) . . . . ?
C22 C23 C24 C25 -177.39(13) . . . . ?
C22 C23 C28 C27 177.86(14) . . . . ?
C24 C23 C22 N2 -144.95(12) . . . . ?
C24 C23 C28 C27 0.0(2) . . . . ?
C24 C25 C26 C27 0.3(2) . . . . ?
C20 C15 C14 N2 -151.48(12) . . . . ?
C20 C15 C14 C13 66.44(15) . . . . ?
C20 C15 C16 C17 -3.4(2) . . . . ?
C20 C19 C18 C17 -1.8(3) . . . . ?
C7 C9 C11 C12 -137.87(11) . . . . ?
C7 C9 C11 C6 -12.21(9) . . . . ?
C7 C9 C21 O1 -87.4(4) . . . . ?
C7 C9 C21 N2 91.1(4) . . . . ?
C2 C1 C13 C14 -83.20(15) . . . . ?
C2 C1 C13 C12 145.08(12) . . . . ?
C2 C1 C5 N1 1.95(19) . . . . ?
C2 C1 C5 C6 179.79(12) . . . . ?
C2 C3 C4 N1 -0.1(3) . . . . ?
C28 C23 C22 N2 37.23(18) . . . . ?
C28 C23 C24 C25 0.5(2) . . . . ?
C8 C9 C11 C12 175.47(11) . . . . ?
C8 C9 C11 C6 -58.87(11) . . . . ?
C8 C9 C21 O1 -13.2(2) . . . . ?
C8 C9 C21 N2 165.28(13) . . . . ?
C8 C9 C10 C7 37.47(10) . . . . ?
C25 C26 C27 C28 0.2(3) . . . . ?
C4 N1 C5 C1 -1.0(2) . . . . ?
C4 N1 C5 C6 -178.97(13) . . . . ?

_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 1.287
_oxdiff_exptl_absorpt_empirical_full_min 0.684
####################################################################### 
# 
# 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_579-10a_auto
_database_code_depnum_ccdc_archive 'CCDC 2382182'
loop_
_audit_author_name
_audit_author_address
'Qinhua Song'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;
_audit_creation_date             2024-08-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H28 N2 O'
_chemical_formula_sum            'C29 H28 N2 O'
_chemical_formula_weight         420.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O2N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2984(2)
_cell_length_b                   10.9937(4)
_cell_length_c                   11.0879(4)
_cell_angle_alpha                78.304(3)
_cell_angle_beta                 83.684(2)
_cell_angle_gamma                83.676(2)
_cell_volume                     1098.67(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5541
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8710
_cell_measurement_theta_min      4.7920
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7786
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.709
_diffrn_reflns_theta_min         4.088
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.960
_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 -37.00   1.00    2.00    --  -41.51 178.00   0.00   35
  2  ω    -65.00  15.00   1.00    2.00    --  -41.51  38.00-150.00   80
  3  ω   -125.00 -46.00   1.00    2.00    --  -41.51 178.00 -90.00   79
  4  ω    -51.00  31.00   1.00    2.00    --  -41.51  38.00 -90.00   82
  5  ω    -85.00 -18.00   1.00    2.00    --  -41.51 -38.00  60.00   67
  6  ω     99.00 130.00   1.00    2.00    --   41.51 178.00 -90.00   31
  7  ω     62.00 106.00   1.00    4.00    --  105.74 -94.00 -60.00   44
  8  ω     24.00  50.00   1.00    4.00    --  105.74 -94.00 -60.00   26
  9  ω     64.00  98.00   1.00    4.00    --  105.74 -94.00  60.00   34
 10  ω     39.00  76.00   1.00    4.00    --  105.74-125.00-150.00   37
 11  ω     33.00 111.00   1.00    4.00    --  105.74 -45.00 -90.00   78
 12  ω     24.00  55.00   1.00    4.00    --  105.74 -94.00  60.00   31
 13  ω    149.00 176.00   1.00    4.00    --  105.74 125.00 150.00   27
 14  ω    105.00 131.00   1.00    4.00    --  105.74 125.00 150.00   26
 15  ω     76.00 113.00   1.00    4.00    --  105.74-125.00-180.00   37
 16  ω     34.00  93.00   1.00    4.00    --  105.74 -61.00-150.00   59
 17  ω     78.00 178.00   1.00    4.00    --  105.74  30.00 -30.00  100
 18  ω     41.00 123.00   1.00    4.00    --  105.74-138.00 -95.00   82
 19  ω     33.00 116.00   1.00    4.00    --  105.74 -45.00  30.00   83
 20  ω    101.00 126.00   1.00    4.00    --  105.74-143.00  -2.00   25
 21  ω     18.00 122.00   1.00    4.00    --  105.74   0.00 150.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0112709000
_diffrn_orient_matrix_UB_12      -0.1297407000
_diffrn_orient_matrix_UB_13      -0.0346485000
_diffrn_orient_matrix_UB_21      0.0104781000
_diffrn_orient_matrix_UB_22      0.0612254000
_diffrn_orient_matrix_UB_23      -0.1381756000
_diffrn_orient_matrix_UB_31      0.1666660000
_diffrn_orient_matrix_UB_32      -0.0081007000
_diffrn_orient_matrix_UB_33      -0.0018573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3902
_reflns_number_total             4205
_reflns_odcompleteness_completeness 98.84
_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 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0091(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.2156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C6(H6), C11(H11), C14(H14), C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B), C23(H23A,H23B), C8(H8A,H8B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C22(H22), C21(H21), C5(H5), C18(H18), C20(H20), C29(H29),
 C25(H25), C19(H19), C26(H26), C27(H27), C28(H28)
1.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16699(13) 1.00191(8) 0.19582(10) 0.0581(3) Uani 1 1 d . . . . .
N2 N 0.29795(11) 0.82619(9) 0.28586(9) 0.0365(2) Uani 1 1 d . . . . .
N1 N 0.25367(11) 0.38410(9) 0.34067(10) 0.0381(2) Uani 1 1 d . . . . .
C1 C 0.17528(12) 0.49533(10) 0.31728(10) 0.0303(2) Uani 1 1 d . . . . .
C13 C 0.22124(12) 0.59844(10) 0.37853(10) 0.0308(2) Uani 1 1 d . . . . .
C12 C 0.08092(12) 0.67768(11) 0.40579(10) 0.0334(2) Uani 1 1 d . . . . .
H12A H 0.0165 0.6271 0.4653 0.040 Uiso 1 1 calc R U . . .
H12B H 0.1028 0.7458 0.4424 0.040 Uiso 1 1 calc R U . . .
C2 C 0.04564(12) 0.50899(10) 0.25841(10) 0.0310(2) Uani 1 1 d . . . . .
C17 C 0.45098(12) 0.65382(11) 0.20611(11) 0.0350(3) Uani 1 1 d . . . . .
C6 C -0.04259(12) 0.63259(11) 0.22422(11) 0.0343(3) Uani 1 1 d . . . . .
H6 H -0.1470 0.6240 0.2413 0.041 Uiso 1 1 calc R U . . .
C11 C 0.00501(12) 0.73022(10) 0.29022(11) 0.0345(3) Uani 1 1 d . . . . .
H11 H -0.0812 0.7839 0.3121 0.041 Uiso 1 1 calc R U . . .
C3 C 0.00057(13) 0.40392(11) 0.22696(11) 0.0385(3) Uani 1 1 d . . . . .
H3 H -0.0853 0.4102 0.1895 0.046 Uiso 1 1 calc R U . . .
C10 C 0.09468(14) 0.80446(10) 0.17816(11) 0.0372(3) Uani 1 1 d . . . . .
C14 C 0.34407(12) 0.69002(10) 0.31118(10) 0.0324(2) Uani 1 1 d . . . . .
H14 H 0.4082 0.6834 0.3772 0.039 Uiso 1 1 calc R U . . .
C16 C 0.27825(14) 0.53363(12) 0.50293(11) 0.0411(3) Uani 1 1 d . . . . .
H16A H 0.2106 0.4770 0.5475 0.062 Uiso 1 1 calc R U . . .
H16B H 0.2891 0.5952 0.5507 0.062 Uiso 1 1 calc R U . . .
H16C H 0.3707 0.4883 0.4881 0.062 Uiso 1 1 calc R U . . .
C9 C 0.15759(14) 0.71135(11) 0.09202(10) 0.0370(3) Uani 1 1 d . . . . .
H9A H 0.2067 0.7493 0.0139 0.044 Uiso 1 1 calc R U . . .
H9B H 0.2135 0.6374 0.1323 0.044 Uiso 1 1 calc R U . . .
C24 C 0.35264(14) 0.89718(11) 0.47176(12) 0.0402(3) Uani 1 1 d . . . . .
C4 C 0.08204(14) 0.29040(11) 0.25083(13) 0.0429(3) Uani 1 1 d . . . . .
H4 H 0.0531 0.2196 0.2300 0.051 Uiso 1 1 calc R U . . .
C7 C -0.00354(14) 0.69646(11) 0.08796(11) 0.0405(3) Uani 1 1 d . . . . .
H7 H -0.0352 0.6639 0.0202 0.049 Uiso 1 1 calc R U . . .
C22 C 0.51423(12) 0.53211(11) 0.21399(12) 0.0386(3) Uani 1 1 d . . . . .
H22 H 0.4875 0.4712 0.2816 0.046 Uiso 1 1 calc R U . . .
C15 C 0.18947(14) 0.88749(11) 0.21687(11) 0.0396(3) Uani 1 1 d . . . . .
C23 C 0.39088(15) 0.90134(12) 0.33541(13) 0.0445(3) Uani 1 1 d . . . . .
H23A H 0.3797 0.9871 0.2915 0.053 Uiso 1 1 calc R U . . .
H23B H 0.4918 0.8700 0.3216 0.053 Uiso 1 1 calc R U . . .
C21 C 0.61674(13) 0.50058(13) 0.12208(14) 0.0467(3) Uani 1 1 d . . . . .
H21 H 0.6557 0.4182 0.1275 0.056 Uiso 1 1 calc R U . . .
C5 C 0.20773(14) 0.28627(11) 0.30668(13) 0.0429(3) Uani 1 1 d . . . . .
H5 H 0.2644 0.2105 0.3218 0.051 Uiso 1 1 calc R U . . .
C18 C 0.49895(15) 0.74339(13) 0.10622(12) 0.0454(3) Uani 1 1 d . . . . .
H18 H 0.4602 0.8259 0.0998 0.054 Uiso 1 1 calc R U . . .
C20 C 0.66133(14) 0.58978(15) 0.02300(13) 0.0507(3) Uani 1 1 d . . . . .
H20 H 0.7297 0.5680 -0.0386 0.061 Uiso 1 1 calc R U . . .
C29 C 0.44366(16) 0.83195(13) 0.55834(14) 0.0504(3) Uani 1 1 d . . . . .
H29 H 0.5312 0.7915 0.5322 0.060 Uiso 1 1 calc R U . . .
C25 C 0.22209(15) 0.95705(12) 0.51312(14) 0.0479(3) Uani 1 1 d . . . . .
H25 H 0.1598 1.0014 0.4561 0.057 Uiso 1 1 calc R U . . .
C8 C -0.02828(17) 0.83888(12) 0.08917(13) 0.0489(3) Uani 1 1 d . . . . .
H8A H -0.0024 0.8930 0.0109 0.059 Uiso 1 1 calc R U . . .
H8B H -0.1222 0.8661 0.1270 0.059 Uiso 1 1 calc R U . . .
C19 C 0.60384(16) 0.71113(15) 0.01601(13) 0.0518(3) Uani 1 1 d . . . . .
H19 H 0.6353 0.7723 -0.0496 0.062 Uiso 1 1 calc R U . . .
C26 C 0.18446(18) 0.95118(15) 0.63764(16) 0.0592(4) Uani 1 1 d . . . . .
H26 H 0.0967 0.9909 0.6643 0.071 Uiso 1 1 calc R U . . .
C27 C 0.2766(2) 0.88653(16) 0.72317(15) 0.0645(4) Uani 1 1 d . . . . .
H27 H 0.2517 0.8836 0.8072 0.077 Uiso 1 1 calc R U . . .
C28 C 0.40571(19) 0.82644(16) 0.68324(16) 0.0616(4) Uani 1 1 d . . . . .
H28 H 0.4675 0.7820 0.7406 0.074 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 C15 1.2305(15) . ?
N2 C14 1.4895(14) . ?
N2 C15 1.3667(17) . ?
N2 C23 1.4754(15) . ?
N1 C1 1.3456(14) . ?
N1 C5 1.3350(16) . ?
C1 C13 1.5530(14) . ?
C1 C2 1.4125(16) . ?
C13 C12 1.5238(15) . ?
C13 C14 1.6237(15) . ?
C13 C16 1.5396(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.5110(16) . ?
C2 C6 1.5090(15) . ?
C2 C3 1.3905(16) . ?
C17 C14 1.5329(15) . ?
C17 C22 1.3909(17) . ?
C17 C18 1.3933(17) . ?
C6 H6 0.9800 . ?
C6 C11 1.5420(15) . ?
C6 C7 1.5534(16) . ?
C11 H11 0.9800 . ?
C11 C10 1.5543(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.3796(18) . ?
C10 C9 1.5632(16) . ?
C10 C15 1.4878(17) . ?
C10 C8 1.5574(18) . ?
C14 H14 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C7 1.5314(18) . ?
C24 C23 1.5072(18) . ?
C24 C29 1.385(2) . ?
C24 C25 1.3932(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.3739(19) . ?
C7 H7 0.9800 . ?
C7 C8 1.5598(18) . ?
C22 H22 0.9300 . ?
C22 C21 1.3871(18) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C21 H21 0.9300 . ?
C21 C20 1.376(2) . ?
C5 H5 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.3894(19) . ?
C20 H20 0.9300 . ?
C20 C19 1.372(2) . ?
C29 H29 0.9300 . ?
C29 C28 1.382(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C19 H19 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.382(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.378(3) . ?
C28 H28 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 N2 C14 128.06(9) . . ?
C15 N2 C23 118.09(10) . . ?
C23 N2 C14 113.68(10) . . ?
C5 N1 C1 119.03(10) . . ?
N1 C1 C13 115.73(9) . . ?
N1 C1 C2 120.84(10) . . ?
C2 C1 C13 122.60(9) . . ?
C1 C13 C14 121.82(8) . . ?
C12 C13 C1 105.17(9) . . ?
C12 C13 C14 108.84(9) . . ?
C12 C13 C16 107.94(9) . . ?
C16 C13 C1 107.31(9) . . ?
C16 C13 C14 105.16(9) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C11 C12 C13 111.82(9) . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C1 C2 C6 123.11(10) . . ?
C3 C2 C1 118.07(10) . . ?
C3 C2 C6 118.78(10) . . ?
C22 C17 C14 120.62(10) . . ?
C22 C17 C18 117.79(11) . . ?
C18 C17 C14 121.27(11) . . ?
C2 C6 H6 111.5 . . ?
C2 C6 C11 110.68(9) . . ?
C2 C6 C7 111.81(9) . . ?
C11 C6 H6 111.5 . . ?
C11 C6 C7 99.20(9) . . ?
C7 C6 H6 111.5 . . ?
C12 C11 C6 115.35(9) . . ?
C12 C11 H11 108.4 . . ?
C12 C11 C10 117.55(10) . . ?
C6 C11 H11 108.4 . . ?
C6 C11 C10 97.95(9) . . ?
C10 C11 H11 108.4 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.65(11) . . ?
C4 C3 H3 119.7 . . ?
C11 C10 C9 107.48(9) . . ?
C11 C10 C8 97.61(10) . . ?
C15 C10 C11 112.09(10) . . ?
C15 C10 C9 121.06(11) . . ?
C15 C10 C8 129.16(10) . . ?
C8 C10 C9 84.63(9) . . ?
N2 C14 C13 116.62(9) . . ?
N2 C14 C17 111.02(9) . . ?
N2 C14 H14 101.6 . . ?
C13 C14 H14 101.6 . . ?
C17 C14 C13 120.40(9) . . ?
C17 C14 H14 101.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C9 H9A 114.9 . . ?
C10 C9 H9B 114.9 . . ?
H9A C9 H9B 111.9 . . ?
C7 C9 C10 82.51(9) . . ?
C7 C9 H9A 114.9 . . ?
C7 C9 H9B 114.9 . . ?
C29 C24 C23 121.21(12) . . ?
C29 C24 C25 118.68(13) . . ?
C25 C24 C23 120.09(12) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.25(11) . . ?
C5 C4 H4 121.4 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 104.37(10) . . ?
C9 C7 C6 100.23(9) . . ?
C9 C7 H7 120.0 . . ?
C9 C7 C8 85.62(10) . . ?
C8 C7 H7 120.0 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.73(12) . . ?
C21 C22 H22 119.6 . . ?
O1 C15 N2 122.29(12) . . ?
O1 C15 C10 123.06(12) . . ?
N2 C15 C10 114.49(10) . . ?
N2 C23 C24 111.62(10) . . ?
N2 C23 H23A 109.3 . . ?
N2 C23 H23B 109.3 . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.72(13) . . ?
C20 C21 H21 119.6 . . ?
N1 C5 C4 124.13(11) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.90(13) . . ?
C19 C18 H18 119.6 . . ?
C21 C20 H20 120.4 . . ?
C19 C20 C21 119.29(12) . . ?
C19 C20 H20 120.4 . . ?
C24 C29 H29 119.7 . . ?
C28 C29 C24 120.63(14) . . ?
C28 C29 H29 119.7 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.55(14) . . ?
C26 C25 H25 119.7 . . ?
C10 C8 C7 81.80(9) . . ?
C10 C8 H8A 115.0 . . ?
C10 C8 H8B 115.0 . . ?
C7 C8 H8A 115.0 . . ?
C7 C8 H8B 115.0 . . ?
H8A C8 H8B 112.0 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.50(13) . . ?
C20 C19 H19 119.8 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.26(15) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.64(15) . . ?
C28 C27 H27 120.2 . . ?
C29 C28 H28 119.9 . . ?
C27 C28 C29 120.24(15) . . ?
C27 C28 H28 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C13 C12 -147.37(9) . . . . ?
N1 C1 C13 C14 88.44(12) . . . . ?
N1 C1 C13 C16 -32.61(12) . . . . ?
N1 C1 C2 C6 -176.88(10) . . . . ?
N1 C1 C2 C3 0.85(16) . . . . ?
C1 N1 C5 C4 -1.50(19) . . . . ?
C1 C13 C12 C11 -57.36(11) . . . . ?
C1 C13 C14 N2 120.43(11) . . . . ?
C1 C13 C14 C17 -18.97(15) . . . . ?
C1 C2 C6 C11 -14.31(14) . . . . ?
C1 C2 C6 C7 95.28(12) . . . . ?
C1 C2 C3 C4 -1.15(17) . . . . ?
C13 C1 C2 C6 14.04(16) . . . . ?
C13 C1 C2 C3 -168.23(10) . . . . ?
C13 C12 C11 C6 61.34(13) . . . . ?
C13 C12 C11 C10 -53.48(13) . . . . ?
C12 C13 C14 N2 -2.06(13) . . . . ?
C12 C13 C14 C17 -141.45(10) . . . . ?
C12 C11 C10 C9 94.42(11) . . . . ?
C12 C11 C10 C15 -40.94(13) . . . . ?
C12 C11 C10 C8 -178.83(10) . . . . ?
C2 C1 C13 C12 22.23(13) . . . . ?
C2 C1 C13 C14 -101.96(12) . . . . ?
C2 C1 C13 C16 136.99(11) . . . . ?
C2 C6 C11 C12 -22.23(13) . . . . ?
C2 C6 C11 C10 103.43(10) . . . . ?
C2 C6 C7 C9 -60.70(11) . . . . ?
C2 C6 C7 C8 -148.76(10) . . . . ?
C2 C3 C4 C5 0.19(19) . . . . ?
C17 C22 C21 C20 1.99(19) . . . . ?
C17 C18 C19 C20 0.6(2) . . . . ?
C6 C2 C3 C4 176.68(11) . . . . ?
C6 C11 C10 C9 -29.67(11) . . . . ?
C6 C11 C10 C15 -165.03(9) . . . . ?
C6 C11 C10 C8 57.08(10) . . . . ?
C6 C7 C8 C10 62.34(10) . . . . ?
C11 C6 C7 C9 56.06(10) . . . . ?
C11 C6 C7 C8 -32.00(11) . . . . ?
C11 C10 C9 C7 59.31(10) . . . . ?
C11 C10 C15 O1 -109.61(13) . . . . ?
C11 C10 C15 N2 65.84(13) . . . . ?
C11 C10 C8 C7 -70.67(9) . . . . ?
C3 C2 C6 C11 167.98(10) . . . . ?
C3 C2 C6 C7 -82.44(13) . . . . ?
C3 C4 C5 N1 1.2(2) . . . . ?
C10 C9 C7 C6 -66.97(9) . . . . ?
C10 C9 C7 C8 36.87(8) . . . . ?
C14 N2 C15 O1 -175.28(11) . . . . ?
C14 N2 C15 C10 9.24(17) . . . . ?
C14 N2 C23 C24 -80.12(13) . . . . ?
C14 C13 C12 C11 74.69(11) . . . . ?
C14 C17 C22 C21 -176.59(11) . . . . ?
C14 C17 C18 C19 175.26(12) . . . . ?
C16 C13 C12 C11 -171.68(9) . . . . ?
C16 C13 C14 N2 -117.50(10) . . . . ?
C16 C13 C14 C17 103.10(11) . . . . ?
C9 C10 C15 O1 121.86(13) . . . . ?
C9 C10 C15 N2 -62.69(14) . . . . ?
C9 C10 C8 C7 36.29(9) . . . . ?
C9 C7 C8 C10 -37.11(9) . . . . ?
C24 C29 C28 C27 -0.3(2) . . . . ?
C24 C25 C26 C27 0.6(2) . . . . ?
C7 C6 C11 C12 -139.83(10) . . . . ?
C7 C6 C11 C10 -14.18(10) . . . . ?
C22 C17 C14 N2 176.41(10) . . . . ?
C22 C17 C14 C13 -42.14(15) . . . . ?
C22 C17 C18 C19 1.62(19) . . . . ?
C22 C21 C20 C19 0.3(2) . . . . ?
C15 N2 C14 C13 -58.60(15) . . . . ?
C15 N2 C14 C17 84.43(14) . . . . ?
C15 N2 C23 C24 104.28(13) . . . . ?
C15 C10 C9 C7 -170.15(11) . . . . ?
C15 C10 C8 C7 162.58(13) . . . . ?
C23 N2 C14 C13 126.33(10) . . . . ?
C23 N2 C14 C17 -90.64(11) . . . . ?
C23 N2 C15 O1 -0.40(18) . . . . ?
C23 N2 C15 C10 -175.89(10) . . . . ?
C23 C24 C29 C28 -178.46(12) . . . . ?
C23 C24 C25 C26 178.36(12) . . . . ?
C21 C20 C19 C18 -1.6(2) . . . . ?
C5 N1 C1 C13 170.22(10) . . . . ?
C5 N1 C1 C2 0.42(16) . . . . ?
C18 C17 C14 N2 2.96(15) . . . . ?
C18 C17 C14 C13 144.40(12) . . . . ?
C18 C17 C22 C21 -2.91(18) . . . . ?
C29 C24 C23 N2 108.23(13) . . . . ?
C29 C24 C25 C26 -0.10(19) . . . . ?
C25 C24 C23 N2 -70.19(15) . . . . ?
C25 C24 C29 C28 -0.02(19) . . . . ?
C25 C26 C27 C28 -0.9(2) . . . . ?
C8 C10 C9 C7 -37.00(9) . . . . ?
C8 C10 C15 O1 11.4(2) . . . . ?
C8 C10 C15 N2 -173.16(12) . . . . ?
C26 C27 C28 C29 0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.723
####################################################################### 
# 
# 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_620a_auto
_database_code_depnum_ccdc_archive 'CCDC 2382185'
loop_
_audit_author_name
_audit_author_address
'Qinhua Song'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;
_audit_creation_date             2024-08-02
_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         'C29 H36 N2 O'
_chemical_formula_sum            'C29 H36 N2 O'
_chemical_formula_weight         428.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20o2n2
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                   15.3885(3)
_cell_length_b                   9.63635(13)
_cell_length_c                   17.3679(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.5905(19)
_cell_angle_gamma                90
_cell_volume                     2410.94(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4884
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9300
_cell_measurement_theta_min      5.1990
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9147
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.952
_diffrn_reflns_theta_min         5.223
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00   9.00   1.00    2.00    --  -41.51  57.00-180.00   74
  2  ω   -115.00 -79.00   1.00    2.00    --  -41.51 -38.00  90.00   36
  3  ω     91.00 126.00   1.00    2.00    --   41.51-178.00-150.00   35
  4  ω    -30.00  62.00   1.00    2.00    --   41.51 -57.00 -60.00   92
  5  ω    132.00 176.00   1.00    6.00    --  105.74  77.00 -60.00   44
  6  ω     82.00 123.00   1.00    6.00    --  105.74  30.00  90.00   41
  7  ω     34.00 123.00   1.00    6.00    --  105.74 -61.00 -90.00   89
  8  ω     76.00 136.00   1.00    6.00    --  105.74 -77.00 -30.00   60
  9  ω     50.00  86.00   1.00    6.00    --  105.74-125.00 -90.00   36
 10  ω    127.00 177.00   1.00    6.00    --  105.74  77.00  30.00   50
 11  ω     81.00 177.00   1.00    6.00    --  105.74  45.00   0.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0022724000
_diffrn_orient_matrix_UB_12      0.1401202000
_diffrn_orient_matrix_UB_13      -0.0419787000
_diffrn_orient_matrix_UB_21      0.1010832000
_diffrn_orient_matrix_UB_22      -0.0280805000
_diffrn_orient_matrix_UB_23      0.0069666000
_diffrn_orient_matrix_UB_31      -0.0349746000
_diffrn_orient_matrix_UB_32      -0.0717213000
_diffrn_orient_matrix_UB_33      -0.0846222000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4010
_reflns_number_total             4667
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+0.5665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1299
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C14(H14), C13(H13), C12(H12), C11(H11), C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B)
1.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C29(H29), C27(H27), C3(H3), C26(H26), C5(H5), C28(H28), C4(H4)
1.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.00727(7) 0.34282(13) 0.35366(8) 0.0616(3) Uani 1 1 d . . . . .
N2 N 0.13906(7) 0.47472(12) 0.39283(7) 0.0385(3) Uani 1 1 d . . . . .
N1 N 0.40659(10) 0.11896(15) 0.63447(8) 0.0545(3) Uani 1 1 d . . . . .
C14 C 0.23972(9) 0.49712(14) 0.44179(8) 0.0378(3) Uani 1 1 d . . . . .
H14 H 0.2583 0.5587 0.4054 0.045 Uiso 1 1 calc R . . . .
C2 C 0.36804(9) 0.31104(16) 0.53890(8) 0.0422(3) Uani 1 1 d . . . . .
C13 C 0.31194(9) 0.37016(14) 0.45402(8) 0.0383(3) Uani 1 1 d . . . . .
H13 H 0.3590 0.4062 0.4332 0.046 Uiso 1 1 calc R . . . .
C12 C 0.26591(9) 0.25184(15) 0.39519(8) 0.0393(3) Uani 1 1 d . . . . .
H12 H 0.2196 0.2968 0.3478 0.047 Uiso 1 1 calc R . . . .
C11 C 0.21000(10) 0.16951(15) 0.43619(8) 0.0407(3) Uani 1 1 d . . . . .
H11 H 0.1770 0.0957 0.3984 0.049 Uiso 1 1 calc R . . . .
C15 C 0.08822(9) 0.36114(15) 0.39888(9) 0.0415(3) Uani 1 1 d . . . . .
C24 C 0.25347(10) 0.59086(14) 0.51581(9) 0.0413(3) Uani 1 1 d . . . . .
C1 C 0.34948(10) 0.18087(16) 0.56626(8) 0.0444(3) Uani 1 1 d . . . . .
C9 C 0.13728(9) 0.25448(15) 0.46065(9) 0.0422(3) Uani 1 1 d . . . . .
C20 C 0.09194(10) 0.58344(16) 0.32753(9) 0.0463(3) Uani 1 1 d . . . . .
C16 C 0.32863(11) 0.16642(18) 0.35862(9) 0.0511(4) Uani 1 1 d . . . . .
C25 C 0.18618(11) 0.61101(17) 0.55063(10) 0.0496(4) Uani 1 1 d . . . . .
H25 H 0.1310 0.5613 0.5306 0.060 Uiso 1 1 calc R . . . .
C6 C 0.26119(11) 0.10349(16) 0.52112(9) 0.0467(3) Uani 1 1 d . . . . .
H6 H 0.2724 0.0042 0.5167 0.056 Uiso 1 1 calc R . . . .
C10 C 0.17943(11) 0.28817(17) 0.55472(9) 0.0474(3) Uani 1 1 d . . . . .
H10A H 0.2384 0.3368 0.5719 0.057 Uiso 1 1 calc R . . . .
H10B H 0.1364 0.3296 0.5776 0.057 Uiso 1 1 calc R . . . .
C29 C 0.33393(10) 0.67093(16) 0.54555(10) 0.0510(4) Uani 1 1 d . . . . .
H29 H 0.3794 0.6618 0.5220 0.061 Uiso 1 1 calc R . . . .
C8 C 0.09218(12) 0.12872(18) 0.48891(11) 0.0565(4) Uani 1 1 d . . . . .
H8A H 0.0387 0.1513 0.5038 0.068 Uiso 1 1 calc R . . . .
H8B H 0.0814 0.0477 0.4536 0.068 Uiso 1 1 calc R . . . .
C7 C 0.18690(12) 0.13008(18) 0.56157(10) 0.0539(4) Uani 1 1 d . . . . .
C27 C 0.28042(13) 0.77969(19) 0.64411(11) 0.0624(5) Uani 1 1 d . . . . .
H27 H 0.2898 0.8417 0.6873 0.075 Uiso 1 1 calc R . . . .
C3 C 0.45028(11) 0.37506(19) 0.58636(10) 0.0547(4) Uani 1 1 d . . . . .
H3 H 0.4664 0.4603 0.5702 0.066 Uiso 1 1 calc R . . . .
C26 C 0.19940(13) 0.70407(19) 0.61491(10) 0.0587(4) Uani 1 1 d . . . . .
H26 H 0.1538 0.7152 0.6381 0.070 Uiso 1 1 calc R . . . .
C5 C 0.48442(12) 0.1851(2) 0.67831(10) 0.0613(5) Uani 1 1 d . . . . .
H5 H 0.5245 0.1423 0.7254 0.074 Uiso 1 1 calc R . . . .
C28 C 0.34722(12) 0.76364(18) 0.60947(11) 0.0606(5) Uani 1 1 d . . . . .
H28 H 0.4017 0.8153 0.6290 0.073 Uiso 1 1 calc R . . . .
C4 C 0.50831(12) 0.3126(2) 0.65756(11) 0.0650(5) Uani 1 1 d . . . . .
H4 H 0.5624 0.3564 0.6906 0.078 Uiso 1 1 calc R . . . .
C23 C 0.15203(14) 0.7105(2) 0.33147(13) 0.0719(6) Uani 1 1 d . . . . .
H23A H 0.1726 0.7483 0.3861 0.108 Uiso 1 1 calc GR . . . .
H23B H 0.1165 0.7791 0.2932 0.108 Uiso 1 1 calc GR . . . .
H23C H 0.2049 0.6844 0.3176 0.108 Uiso 1 1 calc GR . . . .
C21 C 0.06917(19) 0.5197(2) 0.24266(11) 0.0830(7) Uani 1 1 d . . . . .
H21A H 0.1249 0.4837 0.2372 0.124 Uiso 1 1 calc GR . . . .
H21B H 0.0431 0.5894 0.2015 0.124 Uiso 1 1 calc GR . . . .
H21C H 0.0252 0.4458 0.2357 0.124 Uiso 1 1 calc GR . . . .
C22 C 0.00493(14) 0.6374(2) 0.34077(17) 0.0848(7) Uani 1 1 d . . . . .
H22A H -0.0344 0.5607 0.3420 0.127 Uiso 1 1 calc GR . . . .
H22B H -0.0280 0.6988 0.2966 0.127 Uiso 1 1 calc GR . . . .
H22C H 0.0224 0.6867 0.3920 0.127 Uiso 1 1 calc GR . . . .
C18 C 0.41159(16) 0.0948(3) 0.42054(13) 0.0882(8) Uani 1 1 d . . . . .
H18A H 0.4502 0.1625 0.4574 0.132 Uiso 1 1 calc GR . . . .
H18B H 0.4466 0.0482 0.3921 0.132 Uiso 1 1 calc GR . . . .
H18C H 0.3905 0.0283 0.4512 0.132 Uiso 1 1 calc GR . . . .
C19 C 0.26919(16) 0.0597(3) 0.29869(16) 0.0943(8) Uani 1 1 d . . . . .
H19A H 0.2537 -0.0141 0.3287 0.141 Uiso 1 1 calc GR . . . .
H19B H 0.3030 0.0226 0.2663 0.141 Uiso 1 1 calc GR . . . .
H19C H 0.2133 0.1030 0.2632 0.141 Uiso 1 1 calc GR . . . .
C17 C 0.36697(18) 0.2644(3) 0.30922(16) 0.0917(8) Uani 1 1 d . . . . .
H17A H 0.3166 0.3122 0.2690 0.138 Uiso 1 1 calc GR . . . .
H17B H 0.4007 0.2119 0.2820 0.138 Uiso 1 1 calc GR . . . .
H17C H 0.4077 0.3307 0.3456 0.138 Uiso 1 1 calc GR . . . .
H7 H 0.197(2) 0.081(3) 0.6143(19) 0.138 Uiso 1 1 d 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 C15 1.2295(17) . ?
N2 C14 1.4975(16) . ?
N2 C15 1.3707(18) . ?
N2 C20 1.5268(18) . ?
N1 C1 1.3415(19) . ?
N1 C5 1.334(2) . ?
C14 H14 0.9800 . ?
C14 C13 1.6159(19) . ?
C14 C24 1.5238(19) . ?
C2 C13 1.5323(19) . ?
C2 C1 1.406(2) . ?
C2 C3 1.388(2) . ?
C13 H13 0.9800 . ?
C13 C12 1.5287(19) . ?
C12 H12 0.9800 . ?
C12 C11 1.5191(19) . ?
C12 C16 1.5632(19) . ?
C11 H11 0.9800 . ?
C11 C9 1.5614(19) . ?
C11 C6 1.5439(19) . ?
C15 C9 1.486(2) . ?
C24 C25 1.384(2) . ?
C24 C29 1.395(2) . ?
C1 C6 1.506(2) . ?
C9 C10 1.565(2) . ?
C9 C8 1.559(2) . ?
C9 C7 2.037(2) . ?
C20 C23 1.522(2) . ?
C20 C21 1.520(2) . ?
C20 C22 1.527(2) . ?
C16 C18 1.516(2) . ?
C16 C19 1.520(3) . ?
C16 C17 1.527(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.390(2) . ?
C6 H6 0.9800 . ?
C6 C7 1.559(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C7 1.529(2) . ?
C29 H29 0.9300 . ?
C29 C28 1.383(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.557(2) . ?
C7 H7 1.00(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.378(3) . ?
C27 C28 1.370(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(2) . ?
C26 H26 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.367(3) . ?
C28 H28 0.9300 . ?
C4 H4 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C14 N2 C20 116.69(11) . . ?
C15 N2 C14 125.15(11) . . ?
C15 N2 C20 118.04(11) . . ?
C5 N1 C1 117.99(15) . . ?
N2 C14 H14 101.5 . . ?
N2 C14 C13 119.46(11) . . ?
N2 C14 C24 111.93(11) . . ?
C13 C14 H14 101.5 . . ?
C24 C14 H14 101.5 . . ?
C24 C14 C13 116.93(11) . . ?
C1 C2 C13 122.98(13) . . ?
C3 C2 C13 119.56(14) . . ?
C3 C2 C1 116.55(14) . . ?
C14 C13 H13 104.3 . . ?
C2 C13 C14 122.45(11) . . ?
C2 C13 H13 104.3 . . ?
C12 C13 C14 109.95(10) . . ?
C12 C13 C2 109.73(11) . . ?
C12 C13 H13 104.3 . . ?
C13 C12 H12 105.1 . . ?
C13 C12 C16 117.20(11) . . ?
C11 C12 C13 106.37(11) . . ?
C11 C12 H12 105.1 . . ?
C11 C12 C16 116.60(12) . . ?
C16 C12 H12 105.1 . . ?
C12 C11 H11 108.1 . . ?
C12 C11 C9 115.59(12) . . ?
C12 C11 C6 118.71(12) . . ?
C9 C11 H11 108.1 . . ?
C6 C11 H11 108.1 . . ?
C6 C11 C9 97.46(11) . . ?
O1 C15 N2 122.89(13) . . ?
O1 C15 C9 120.35(13) . . ?
N2 C15 C9 116.68(11) . . ?
C25 C24 C14 123.26(12) . . ?
C25 C24 C29 117.62(14) . . ?
C29 C24 C14 118.83(13) . . ?
N1 C1 C2 123.20(15) . . ?
N1 C1 C6 115.50(14) . . ?
C2 C1 C6 121.28(13) . . ?
C11 C9 C10 108.61(11) . . ?
C11 C9 C7 80.67(9) . . ?
C15 C9 C11 113.40(11) . . ?
C15 C9 C10 121.94(13) . . ?
C15 C9 C8 126.56(12) . . ?
C15 C9 C7 165.87(12) . . ?
C10 C9 C7 48.07(8) . . ?
C8 C9 C11 96.83(12) . . ?
C8 C9 C10 84.24(11) . . ?
C8 C9 C7 49.12(9) . . ?
N2 C20 C22 109.54(14) . . ?
C23 C20 N2 113.36(12) . . ?
C23 C20 C22 105.67(16) . . ?
C21 C20 N2 109.30(13) . . ?
C21 C20 C23 107.33(16) . . ?
C21 C20 C22 111.62(17) . . ?
C18 C16 C12 115.97(13) . . ?
C18 C16 C19 109.37(19) . . ?
C18 C16 C17 106.54(18) . . ?
C19 C16 C12 109.02(14) . . ?
C19 C16 C17 106.99(17) . . ?
C17 C16 C12 108.57(15) . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.38(15) . . ?
C26 C25 H25 119.3 . . ?
C11 C6 H6 111.9 . . ?
C11 C6 C7 98.87(12) . . ?
C1 C6 C11 110.93(12) . . ?
C1 C6 H6 111.9 . . ?
C1 C6 C7 110.75(13) . . ?
C7 C6 H6 111.9 . . ?
C9 C10 H10A 114.9 . . ?
C9 C10 H10B 114.9 . . ?
H10A C10 H10B 112.0 . . ?
C7 C10 C9 82.35(12) . . ?
C7 C10 H10A 114.9 . . ?
C7 C10 H10B 114.9 . . ?
C24 C29 H29 119.5 . . ?
C28 C29 C24 121.06(16) . . ?
C28 C29 H29 119.5 . . ?
C9 C8 H8A 115.0 . . ?
C9 C8 H8B 115.0 . . ?
H8A C8 H8B 112.1 . . ?
C7 C8 C9 81.67(11) . . ?
C7 C8 H8A 115.0 . . ?
C7 C8 H8B 115.0 . . ?
C9 C7 H7 164.4(18) . . ?
C6 C7 C9 79.71(9) . . ?
C6 C7 H7 115.8(18) . . ?
C10 C7 C9 49.59(8) . . ?
C10 C7 C6 100.11(12) . . ?
C10 C7 C8 85.53(13) . . ?
C10 C7 H7 122.2(19) . . ?
C8 C7 C9 49.22(8) . . ?
C8 C7 C6 105.02(13) . . ?
C8 C7 H7 122.6(18) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C28 C27 C26 120.02(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.31(17) . . ?
C4 C3 H3 119.8 . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.65(17) . . ?
C27 C26 H26 120.2 . . ?
N1 C5 H5 118.3 . . ?
N1 C5 C4 123.37(15) . . ?
C4 C5 H5 118.3 . . ?
C29 C28 H28 119.9 . . ?
C27 C28 C29 120.22(16) . . ?
C27 C28 H28 119.9 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.55(17) . . ?
C5 C4 H4 120.7 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C15 C9 C11 105.55(16) . . . . ?
O1 C15 C9 C10 -121.64(16) . . . . ?
O1 C15 C9 C8 -13.3(2) . . . . ?
O1 C15 C9 C7 -80.2(5) . . . . ?
N2 C14 C13 C2 -118.37(14) . . . . ?
N2 C14 C13 C12 12.67(16) . . . . ?
N2 C14 C24 C25 21.87(19) . . . . ?
N2 C14 C24 C29 -151.79(13) . . . . ?
N2 C15 C9 C11 -71.26(16) . . . . ?
N2 C15 C9 C10 61.55(18) . . . . ?
N2 C15 C9 C8 169.90(14) . . . . ?
N2 C15 C9 C7 103.0(5) . . . . ?
N1 C1 C6 C11 -169.49(12) . . . . ?
N1 C1 C6 C7 81.76(16) . . . . ?
N1 C5 C4 C3 -1.8(3) . . . . ?
C14 N2 C15 O1 -175.12(14) . . . . ?
C14 N2 C15 C9 1.6(2) . . . . ?
C14 N2 C20 C23 -8.83(19) . . . . ?
C14 N2 C20 C21 110.85(16) . . . . ?
C14 N2 C20 C22 -126.57(15) . . . . ?
C14 C13 C12 C11 -82.61(13) . . . . ?
C14 C13 C12 C16 144.87(12) . . . . ?
C14 C24 C25 C26 -175.95(14) . . . . ?
C14 C24 C29 C28 176.20(14) . . . . ?
C2 C13 C12 C11 54.84(14) . . . . ?
C2 C13 C12 C16 -77.68(15) . . . . ?
C2 C1 C6 C11 12.28(19) . . . . ?
C2 C1 C6 C7 -96.47(16) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C13 C14 C24 C25 -121.19(15) . . . . ?
C13 C14 C24 C29 65.15(17) . . . . ?
C13 C2 C1 N1 169.16(13) . . . . ?
C13 C2 C1 C6 -12.8(2) . . . . ?
C13 C2 C3 C4 -170.83(15) . . . . ?
C13 C12 C11 C9 55.77(14) . . . . ?
C13 C12 C11 C6 -59.47(16) . . . . ?
C13 C12 C16 C18 59.0(2) . . . . ?
C13 C12 C16 C19 -177.05(16) . . . . ?
C13 C12 C16 C17 -60.82(19) . . . . ?
C12 C11 C9 C15 38.96(16) . . . . ?
C12 C11 C9 C10 -99.97(13) . . . . ?
C12 C11 C9 C8 173.83(12) . . . . ?
C12 C11 C9 C7 -139.62(12) . . . . ?
C12 C11 C6 C1 25.06(18) . . . . ?
C12 C11 C6 C7 141.39(13) . . . . ?
C11 C12 C16 C18 -68.7(2) . . . . ?
C11 C12 C16 C19 55.2(2) . . . . ?
C11 C12 C16 C17 171.45(15) . . . . ?
C11 C9 C10 C7 -57.82(13) . . . . ?
C11 C9 C8 C7 71.35(12) . . . . ?
C11 C6 C7 C9 -12.87(10) . . . . ?
C11 C6 C7 C10 -58.31(14) . . . . ?
C11 C6 C7 C8 29.74(15) . . . . ?
C15 N2 C14 C13 43.89(18) . . . . ?
C15 N2 C14 C24 -98.13(15) . . . . ?
C15 N2 C20 C23 174.92(15) . . . . ?
C15 N2 C20 C21 -65.40(19) . . . . ?
C15 N2 C20 C22 57.18(18) . . . . ?
C15 C9 C10 C7 167.45(13) . . . . ?
C15 C9 C8 C7 -162.72(15) . . . . ?
C24 C14 C13 C2 21.82(18) . . . . ?
C24 C14 C13 C12 152.86(11) . . . . ?
C24 C25 C26 C27 1.0(3) . . . . ?
C24 C29 C28 C27 -0.9(3) . . . . ?
C1 N1 C5 C4 0.5(3) . . . . ?
C1 C2 C13 C14 107.75(16) . . . . ?
C1 C2 C13 C12 -23.38(18) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
C1 C6 C7 C9 103.60(12) . . . . ?
C1 C6 C7 C10 58.16(15) . . . . ?
C1 C6 C7 C8 146.20(13) . . . . ?
C9 C11 C6 C1 -99.58(13) . . . . ?
C9 C11 C6 C7 16.76(13) . . . . ?
C9 C10 C7 C6 67.04(12) . . . . ?
C9 C10 C7 C8 -37.45(10) . . . . ?
C9 C8 C7 C6 -61.59(13) . . . . ?
C9 C8 C7 C10 37.69(11) . . . . ?
C20 N2 C14 C13 -132.07(12) . . . . ?
C20 N2 C14 C24 85.91(14) . . . . ?
C20 N2 C15 O1 0.8(2) . . . . ?
C20 N2 C15 C9 177.51(12) . . . . ?
C16 C12 C11 C9 -171.39(12) . . . . ?
C16 C12 C11 C6 73.38(16) . . . . ?
C25 C24 C29 C28 2.2(2) . . . . ?
C6 C11 C9 C15 165.82(12) . . . . ?
C6 C11 C9 C10 26.89(14) . . . . ?
C6 C11 C9 C8 -59.31(13) . . . . ?
C6 C11 C9 C7 -12.76(10) . . . . ?
C10 C9 C8 C7 -36.77(11) . . . . ?
C29 C24 C25 C26 -2.2(2) . . . . ?
C8 C9 C10 C7 37.47(11) . . . . ?
C3 C2 C13 C14 -83.59(17) . . . . ?
C3 C2 C13 C12 145.29(13) . . . . ?
C3 C2 C1 N1 0.2(2) . . . . ?
C3 C2 C1 C6 178.26(14) . . . . ?
C26 C27 C28 C29 -0.4(3) . . . . ?
C5 N1 C1 C2 0.3(2) . . . . ?
C5 N1 C1 C6 -177.88(14) . . . . ?
C28 C27 C26 C25 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.142
_oxdiff_exptl_absorpt_empirical_full_min 0.865
####################################################################### 
# 
# 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_539-2b_auto
_database_code_depnum_ccdc_archive 'CCDC 2382180'
loop_
_audit_author_name
_audit_author_address
'Qinhua Song'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;
_audit_creation_date             2024-08-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
(5S,6aS,7R,9R,9aS,13R)-12-benzyl-13-phenyl-5,6,6a,8,9,9a-hexahydro-7,9-methano-5,7-(methanoiminomethano)cyclopenta[h]quinolin-11-one
_chemical_formula_moiety         'C28 H26 N2 O'
_chemical_formula_sum            'C28 H26 N2 O'
_chemical_formula_weight         406.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20o2n2
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                   11.3527(4)
_cell_length_b                   11.9601(4)
_cell_length_c                   16.1020(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.689(4)
_cell_angle_gamma                90
_cell_volume                     2104.86(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3285
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.6340
_cell_measurement_theta_min      4.0180
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8423
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.867
_diffrn_reflns_theta_min         4.045
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -17.00   1.00    5.00    --  -41.51 -38.00 150.00   98
  2  ω      6.00  33.00   1.00    5.00    --  -41.51  38.00 120.00   27
  3  ω    -66.00 -28.00   1.00    5.00    --  -41.51  38.00 120.00   38
  4  ω     62.00 126.00   1.00    5.00    --   41.51 178.00  90.00   64
  5  ω     76.00 125.00   1.00    5.00    --   41.51-178.00-120.00   49
  6  ω     49.00 109.00   1.00   10.00    --  105.74-125.00 -30.00   60
  7  ω     73.00 100.00   1.00   10.00    --  105.74-125.00  30.00   27
  8  ω    139.00 175.00   1.00   10.00    --  105.74  77.00 150.00   36
  9  ω    126.00 166.00   1.00   10.00    --  105.74  77.00-120.00   40
 10  ω    110.00 177.00   1.00   10.00    --  105.74 125.00 -30.00   67
 11  ω     62.00 102.00   1.00   10.00    --  105.74-125.00  90.00   40
 12  ω     77.00 165.00   1.00   10.00    --  105.74  30.00   0.00   88
 13  ω     33.00 113.00   1.00   10.00    --  105.74 -15.00-180.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1172845000
_diffrn_orient_matrix_UB_12      0.0570550000
_diffrn_orient_matrix_UB_13      0.0095870000
_diffrn_orient_matrix_UB_21      -0.0705218000
_diffrn_orient_matrix_UB_22      -0.1106787000
_diffrn_orient_matrix_UB_23      -0.0238123000
_diffrn_orient_matrix_UB_31      0.0340933000
_diffrn_orient_matrix_UB_32      -0.0337144000
_diffrn_orient_matrix_UB_33      0.0958692000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2887
_reflns_number_total             4079
_reflns_odcompleteness_completeness 99.85
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4079
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.020
_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)+(0.0612P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Restrained distances
 C28-H28A = C28-H28B = C13-H13
 0.95 with sigma of 0.01
2.a Ternary CH refined with riding coordinates:
 C12(H12), C10(H10), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C11(H11A,H11B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C16(H16), C23(H23), C20(H20), C27(H27), C4(H4), C19(H19), C5(H5),
 C24(H24), C17(H17), C18(H18), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.96481(12) 0.49706(12) 0.70967(10) 0.0635(4) Uani 1 1 d . . . . .
N2 N 0.84008(12) 0.34455(12) 0.67464(9) 0.0393(3) Uani 1 1 d . . . . .
N1 N 0.35701(15) 0.50507(15) 0.65517(11) 0.0599(4) Uani 1 1 d . . . . .
C15 C 0.71474(14) 0.17345(14) 0.61568(10) 0.0382(4) Uani 1 1 d . . . . .
C2 C 0.50309(15) 0.35489(14) 0.66746(10) 0.0402(4) Uani 1 1 d . . . . .
C22 C 0.96506(14) 0.25739(14) 0.58548(11) 0.0405(4) Uani 1 1 d . . . . .
C12 C 0.63062(14) 0.30688(14) 0.70671(10) 0.0383(4) Uani 1 1 d . . . . .
H12 H 0.6190 0.2309 0.7259 0.046 Uiso 1 1 calc R U . . .
C13 C 0.71380(14) 0.29602(13) 0.64198(10) 0.0349(3) Uani 1 1 d D . . . .
C21 C 0.94757(15) 0.27664(15) 0.67397(11) 0.0435(4) Uani 1 1 d . . . . .
H21A H 0.9403 0.2047 0.6999 0.052 Uiso 1 1 calc R U . . .
H21B H 1.0200 0.3132 0.7096 0.052 Uiso 1 1 calc R U . . .
C9 C 0.75094(16) 0.52504(14) 0.69011(12) 0.0447(4) Uani 1 1 d . . . . .
C14 C 0.86128(16) 0.45685(15) 0.69166(11) 0.0439(4) Uani 1 1 d . . . . .
C10 C 0.69171(16) 0.49501(15) 0.76370(11) 0.0454(4) Uani 1 1 d . . . . .
H10 H 0.7348 0.5362 0.8156 0.054 Uiso 1 1 calc R U . . .
C11 C 0.68923(16) 0.37325(15) 0.78663(10) 0.0459(4) Uani 1 1 d . . . . .
H11A H 0.6432 0.3635 0.8289 0.055 Uiso 1 1 calc R U . . .
H11B H 0.7720 0.3468 0.8117 0.055 Uiso 1 1 calc R U . . .
C1 C 0.47215(16) 0.46546(16) 0.68235(11) 0.0467(4) Uani 1 1 d . . . . .
C3 C 0.41018(16) 0.28680(16) 0.62052(11) 0.0462(4) Uani 1 1 d . . . . .
H3 H 0.4274 0.2139 0.6074 0.055 Uiso 1 1 calc R U . . .
C16 C 0.67094(17) 0.14442(16) 0.53011(11) 0.0487(4) Uani 1 1 d . . . . .
H16 H 0.6493 0.2001 0.4884 0.058 Uiso 1 1 calc R U . . .
C28 C 0.64709(19) 0.54112(16) 0.60463(13) 0.0503(5) Uani 1 1 d D . . . .
C23 C 1.01160(16) 0.15595(16) 0.56718(13) 0.0511(5) Uani 1 1 d . . . . .
H23 H 1.0271 0.0993 0.6083 0.061 Uiso 1 1 calc R U . . .
C20 C 0.74768(18) 0.08884(15) 0.67619(11) 0.0512(5) Uani 1 1 d . . . . .
H20 H 0.7773 0.1068 0.7343 0.061 Uiso 1 1 calc R U . . .
C6 C 0.56725(17) 0.55096(16) 0.72551(12) 0.0519(5) Uani 1 1 d . . . . .
H6 H 0.5410 0.5941 0.7691 0.062 Uiso 1 1 calc R U . . .
C27 C 0.94244(18) 0.33963(18) 0.52290(12) 0.0546(5) Uani 1 1 d . . . . .
H27 H 0.9110 0.4082 0.5339 0.065 Uiso 1 1 calc R U . . .
C4 C 0.29209(17) 0.32687(19) 0.59319(13) 0.0567(5) Uani 1 1 d . . . . .
H4 H 0.2288 0.2816 0.5622 0.068 Uiso 1 1 calc R U . . .
C19 C 0.7370(2) -0.02231(16) 0.65097(14) 0.0607(5) Uani 1 1 d . . . . .
H19 H 0.7609 -0.0784 0.6921 0.073 Uiso 1 1 calc R U . . .
C7 C 0.6031(2) 0.62845(16) 0.65877(15) 0.0609(5) Uani 1 1 d . . . . .
C5 C 0.27048(18) 0.4349(2) 0.61289(13) 0.0618(5) Uani 1 1 d . . . . .
H5 H 0.1903 0.4609 0.5957 0.074 Uiso 1 1 calc R U . . .
C24 C 1.03511(19) 0.13839(19) 0.48830(15) 0.0644(6) Uani 1 1 d . . . . .
H24 H 1.0668 0.0701 0.4770 0.077 Uiso 1 1 calc R U . . .
C17 C 0.6587(2) 0.03297(18) 0.50544(13) 0.0621(6) Uani 1 1 d . . . . .
H17 H 0.6281 0.0144 0.4475 0.074 Uiso 1 1 calc R U . . .
C18 C 0.6915(2) -0.04993(17) 0.56611(14) 0.0622(6) Uani 1 1 d . . . . .
H18 H 0.6828 -0.1246 0.5495 0.075 Uiso 1 1 calc R U . . .
C8 C 0.74190(19) 0.65458(16) 0.69784(16) 0.0656(6) Uani 1 1 d . . . . .
H8A H 0.7797 0.6972 0.6607 0.079 Uiso 1 1 calc R U . . .
H8B H 0.7634 0.6832 0.7564 0.079 Uiso 1 1 calc R U . . .
C25 C 1.0123(2) 0.2202(2) 0.42684(14) 0.0670(6) Uani 1 1 d . . . . .
H25 H 1.0280 0.2076 0.3738 0.080 Uiso 1 1 calc R U . . .
C26 C 0.9659(2) 0.3214(2) 0.44399(13) 0.0664(6) Uani 1 1 d . . . . .
H26 H 0.9503 0.3775 0.4025 0.080 Uiso 1 1 calc R U . . .
H7 H 0.547(2) 0.687(2) 0.6332(14) 0.080 Uiso 1 1 d . U . . .
H13 H 0.6750(13) 0.3374(12) 0.5902(7) 0.038(4) Uiso 1 1 d D . . . .
H28A H 0.5927(14) 0.4811(12) 0.5784(11) 0.047(5) Uiso 1 1 d D . . . .
H28B H 0.6803(17) 0.5732(16) 0.5614(10) 0.060(6) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.230(2) . ?
N2 C13 1.504(2) . ?
N2 C21 1.468(2) . ?
N2 C14 1.379(2) . ?
N1 C1 1.347(2) . ?
N1 C5 1.331(3) . ?
C15 C13 1.527(2) . ?
C15 C16 1.377(2) . ?
C15 C20 1.384(2) . ?
C2 C12 1.527(2) . ?
C2 C1 1.405(2) . ?
C2 C3 1.384(2) . ?
C22 C21 1.508(2) . ?
C22 C23 1.386(2) . ?
C22 C27 1.382(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.590(2) . ?
C12 C11 1.505(2) . ?
C13 H13 0.967(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C9 C14 1.489(2) . ?
C9 C10 1.554(2) . ?
C9 C28 1.563(3) . ?
C9 C7 2.036(3) . ?
C9 C8 1.560(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.504(3) . ?
C10 C6 1.534(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C1 C6 1.513(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(3) . ?
C28 C7 1.528(3) . ?
C28 H28A 0.967(9) . ?
C28 H28B 0.957(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.386(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.554(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.384(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.364(3) . ?
C7 C8 1.562(3) . ?
C7 H7 0.96(2) . ?
C5 H5 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.365(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.371(3) . ?
C18 H18 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C25 H25 0.9300 . ?
C25 C26 1.377(3) . ?
C26 H26 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
C21 N2 C13 119.97(13) . . ?
C14 N2 C13 122.96(13) . . ?
C14 N2 C21 116.08(13) . . ?
C5 N1 C1 117.48(18) . . ?
C16 C15 C13 119.47(15) . . ?
C16 C15 C20 118.40(16) . . ?
C20 C15 C13 121.84(15) . . ?
C1 C2 C12 122.42(16) . . ?
C3 C2 C12 120.14(15) . . ?
C3 C2 C1 117.27(16) . . ?
C23 C22 C21 119.30(16) . . ?
C27 C22 C21 122.29(16) . . ?
C27 C22 C23 118.31(16) . . ?
C2 C12 H12 106.6 . . ?
C2 C12 C13 115.11(13) . . ?
C13 C12 H12 106.6 . . ?
C11 C12 C2 107.82(13) . . ?
C11 C12 H12 106.6 . . ?
C11 C12 C13 113.58(13) . . ?
N2 C13 C15 112.96(13) . . ?
N2 C13 C12 114.73(12) . . ?
N2 C13 H13 105.8(10) . . ?
C15 C13 C12 108.07(12) . . ?
C15 C13 H13 106.7(10) . . ?
C12 C13 H13 108.1(10) . . ?
N2 C21 C22 114.42(14) . . ?
N2 C21 H21A 108.7 . . ?
N2 C21 H21B 108.7 . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C14 C9 C10 113.33(15) . . ?
C14 C9 C28 120.85(15) . . ?
C14 C9 C7 166.00(15) . . ?
C14 C9 C8 128.01(16) . . ?
C10 C9 C28 108.72(14) . . ?
C10 C9 C7 80.31(11) . . ?
C10 C9 C8 96.74(14) . . ?
C28 C9 C7 48.09(11) . . ?
C8 C9 C28 84.14(15) . . ?
C8 C9 C7 49.36(11) . . ?
O1 C14 N2 122.14(16) . . ?
O1 C14 C9 122.39(16) . . ?
N2 C14 C9 115.42(14) . . ?
C9 C10 H10 108.4 . . ?
C11 C10 C9 116.83(13) . . ?
C11 C10 H10 108.4 . . ?
C11 C10 C6 116.39(15) . . ?
C6 C10 C9 97.76(14) . . ?
C6 C10 H10 108.4 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C10 C11 C12 109.51(14) . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
N1 C1 C2 122.73(18) . . ?
N1 C1 C6 114.87(17) . . ?
C2 C1 C6 122.29(16) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.09(18) . . ?
C4 C3 H3 120.0 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.66(18) . . ?
C17 C16 H16 119.7 . . ?
C9 C28 H28A 122.2(11) . . ?
C9 C28 H28B 109.7(12) . . ?
C7 C28 C9 82.35(15) . . ?
C7 C28 H28A 119.2(11) . . ?
C7 C28 H28B 113.2(12) . . ?
H28A C28 H28B 108.2(16) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.50(19) . . ?
C24 C23 H23 119.7 . . ?
C15 C20 H20 119.7 . . ?
C15 C20 C19 120.63(17) . . ?
C19 C20 H20 119.7 . . ?
C10 C6 H6 111.6 . . ?
C10 C6 C7 98.77(15) . . ?
C1 C6 C10 110.78(15) . . ?
C1 C6 H6 111.6 . . ?
C1 C6 C7 111.90(16) . . ?
C7 C6 H6 111.6 . . ?
C22 C27 H27 119.6 . . ?
C22 C27 C26 120.87(19) . . ?
C26 C27 H27 119.6 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.29(19) . . ?
C5 C4 H4 120.9 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.34(19) . . ?
C18 C19 H19 119.8 . . ?
C9 C7 H7 162.6(14) . . ?
C28 C7 C9 49.56(11) . . ?
C28 C7 C6 100.02(15) . . ?
C28 C7 C8 85.22(16) . . ?
C28 C7 H7 122.3(13) . . ?
C6 C7 C9 79.56(12) . . ?
C6 C7 C8 105.36(18) . . ?
C6 C7 H7 117.9(14) . . ?
C8 C7 C9 49.25(10) . . ?
C8 C7 H7 120.2(14) . . ?
N1 C5 C4 124.07(18) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.7(2) . . ?
C25 C24 H24 119.6 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.27(18) . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 119.67(19) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C9 C8 C7 81.38(14) . . ?
C9 C8 H8A 115.1 . . ?
C9 C8 H8B 115.1 . . ?
C7 C8 H8A 115.1 . . ?
C7 C8 H8B 115.1 . . ?
H8A C8 H8B 112.1 . . ?
C24 C25 H25 120.3 . . ?
C24 C25 C26 119.47(19) . . ?
C26 C25 H25 120.3 . . ?
C27 C26 H26 119.9 . . ?
C25 C26 C27 120.1(2) . . ?
C25 C26 H26 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C6 C10 173.10(15) . . . . ?
N1 C1 C6 C7 -77.73(19) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C15 C20 C19 C18 -1.3(3) . . . . ?
C2 C12 C13 N2 130.12(15) . . . . ?
C2 C12 C13 C15 -102.87(16) . . . . ?
C2 C12 C11 C10 -56.96(17) . . . . ?
C2 C1 C6 C10 -10.4(2) . . . . ?
C2 C1 C6 C7 98.8(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
C22 C27 C26 C25 0.1(3) . . . . ?
C12 C2 C1 N1 -173.18(16) . . . . ?
C12 C2 C1 C6 10.6(2) . . . . ?
C12 C2 C3 C4 172.86(15) . . . . ?
C13 N2 C21 C22 72.34(19) . . . . ?
C13 N2 C14 O1 -172.26(15) . . . . ?
C13 N2 C14 C9 10.0(2) . . . . ?
C13 C15 C16 C17 -173.18(17) . . . . ?
C13 C15 C20 C19 174.02(17) . . . . ?
C13 C12 C11 C10 71.84(18) . . . . ?
C21 N2 C13 C15 3.42(19) . . . . ?
C21 N2 C13 C12 127.89(14) . . . . ?
C21 N2 C14 O1 -3.7(2) . . . . ?
C21 N2 C14 C9 178.65(14) . . . . ?
C21 C22 C23 C24 -176.30(17) . . . . ?
C21 C22 C27 C26 176.35(18) . . . . ?
C9 C10 C11 C12 -53.7(2) . . . . ?
C9 C10 C6 C1 99.95(16) . . . . ?
C9 C10 C6 C7 -17.58(16) . . . . ?
C9 C28 C7 C6 -66.90(16) . . . . ?
C9 C28 C7 C8 37.88(14) . . . . ?
C14 N2 C13 C15 171.59(14) . . . . ?
C14 N2 C13 C12 -63.94(19) . . . . ?
C14 N2 C21 C22 -96.62(18) . . . . ?
C14 C9 C10 C11 -38.5(2) . . . . ?
C14 C9 C10 C6 -163.34(15) . . . . ?
C14 C9 C28 C7 -169.31(16) . . . . ?
C14 C9 C8 C7 162.20(19) . . . . ?
C10 C9 C14 O1 -111.27(19) . . . . ?
C10 C9 C14 N2 66.41(19) . . . . ?
C10 C9 C28 C7 57.11(16) . . . . ?
C10 C9 C8 C7 -71.05(15) . . . . ?
C10 C6 C7 C9 13.44(12) . . . . ?
C10 C6 C7 C28 58.82(18) . . . . ?
C10 C6 C7 C8 -28.92(18) . . . . ?
C11 C12 C13 N2 5.14(19) . . . . ?
C11 C12 C13 C15 132.16(15) . . . . ?
C11 C10 C6 C1 -25.2(2) . . . . ?
C11 C10 C6 C7 -142.76(15) . . . . ?
C1 N1 C5 C4 -2.2(3) . . . . ?
C1 C2 C12 C13 -103.72(17) . . . . ?
C1 C2 C12 C11 24.2(2) . . . . ?
C1 C2 C3 C4 -2.4(2) . . . . ?
C1 C6 C7 C9 -103.24(15) . . . . ?
C1 C6 C7 C28 -57.9(2) . . . . ?
C1 C6 C7 C8 -145.60(16) . . . . ?
C3 C2 C12 C13 81.25(19) . . . . ?
C3 C2 C12 C11 -150.82(15) . . . . ?
C3 C2 C1 N1 2.0(3) . . . . ?
C3 C2 C1 C6 -174.25(15) . . . . ?
C3 C4 C5 N1 1.7(3) . . . . ?
C16 C15 C13 N2 -112.56(17) . . . . ?
C16 C15 C13 C12 119.40(16) . . . . ?
C16 C15 C20 C19 0.1(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C28 C9 C14 O1 117.08(19) . . . . ?
C28 C9 C14 N2 -65.2(2) . . . . ?
C28 C9 C10 C11 98.89(17) . . . . ?
C28 C9 C10 C6 -25.97(17) . . . . ?
C28 C9 C8 C7 37.17(14) . . . . ?
C28 C7 C8 C9 -38.09(14) . . . . ?
C23 C22 C21 N2 -144.77(16) . . . . ?
C23 C22 C27 C26 -0.1(3) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C20 C15 C13 N2 73.63(19) . . . . ?
C20 C15 C13 C12 -54.4(2) . . . . ?
C20 C15 C16 C17 0.8(3) . . . . ?
C20 C19 C18 C17 1.4(3) . . . . ?
C6 C10 C11 C12 61.15(18) . . . . ?
C6 C7 C8 C9 61.00(16) . . . . ?
C27 C22 C21 N2 38.8(2) . . . . ?
C27 C22 C23 C24 0.3(3) . . . . ?
C7 C9 C14 O1 82.3(6) . . . . ?
C7 C9 C14 N2 -100.0(6) . . . . ?
C7 C9 C10 C11 138.23(16) . . . . ?
C7 C9 C10 C6 13.37(12) . . . . ?
C5 N1 C1 C2 0.2(3) . . . . ?
C5 N1 C1 C6 176.74(17) . . . . ?
C24 C25 C26 C27 -0.1(3) . . . . ?
C8 C9 C14 O1 8.7(3) . . . . ?
C8 C9 C14 N2 -173.64(18) . . . . ?
C8 C9 C10 C11 -175.04(16) . . . . ?
C8 C9 C10 C6 60.10(16) . . . . ?
C8 C9 C28 C7 -38.04(14) . . . . ?

_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.549
####################################################################### 
# 
# 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_589-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2382183'
loop_
_audit_author_name
_audit_author_address
'Qinhua Song'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;
_audit_creation_date             2024-08-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H28 N2 O2'
_chemical_formula_sum            'C29 H28 N2 O2'
_chemical_formula_weight         436.53
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c20h20n2o2
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                   10.85402(11)
_cell_length_b                   11.58396(11)
_cell_length_c                   18.06561(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2271.43(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11353
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8870
_cell_measurement_theta_min      4.5080
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16813
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.932
_diffrn_reflns_theta_min         4.534
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  -1.00   1.00    2.00    --  -41.76 -19.00-180.00  119
  2  ω      6.00  32.00   1.00    2.00    --   41.76 -99.00   0.00   26
  3  ω     46.00  87.00   1.00    2.00    --   41.76-125.00 -60.00   41
  4  ω     17.00  53.00   1.00    2.00    --   41.76 -99.00  30.00   36
  5  ω     54.00  93.00   1.00    8.00    --  105.74-125.00  60.00   39
  6  ω     32.00 105.00   1.00    8.00    --  105.74 -94.00  60.00   73
  7  ω     46.00 102.00   1.00    8.00    --  105.74 -94.00-150.00   56
  8  ω     87.00 112.00   1.00    8.00    --  105.74-125.00 -30.00   25
  9  ω    116.00 174.00   1.00    8.00    --  105.74  77.00 150.00   58
 10  ω    104.00 172.00   1.00    8.00    --  105.74  77.00 -60.00   68
 11  ω    103.00 178.00   1.00    8.00    --  105.74  77.00-150.00   75
 12  ω     68.00 114.00   1.00    8.00    --  105.74 -45.00  30.00   46
 13  ω     45.00  73.00   1.00    2.00    --   41.76-124.00-136.00   28
 14  ω    124.00 172.00   1.00    8.00    --  105.74  77.00 120.00   48
 15  ω     76.00 102.00   1.00    8.00    --  105.74 -77.00 -90.00   26
 16  ω    153.00 178.00   1.00    8.00    --  105.74  77.00   0.00   25
 17  ω   -115.00 -14.00   1.00    2.00    --  -41.76 -57.00  30.00  101
 18  ω   -115.00 -14.00   1.00    2.00    --  -41.76 -57.00 -60.00  101
 19  ω    -70.00  31.00   1.00    2.00    --  -41.76  57.00-120.00  101
 20  ω   -116.00 -17.00   1.00    2.00    --  -41.76 -38.00  90.00   99
 21  ω     77.00 162.00   1.00    8.00    --  105.74  30.00  90.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1304459000
_diffrn_orient_matrix_UB_12      0.0499681000
_diffrn_orient_matrix_UB_13      -0.0102005000
_diffrn_orient_matrix_UB_21      -0.0111797000
_diffrn_orient_matrix_UB_22      -0.0162777000
_diffrn_orient_matrix_UB_23      -0.0843545000
_diffrn_orient_matrix_UB_31      -0.0548493000
_diffrn_orient_matrix_UB_32      0.1221778000
_diffrn_orient_matrix_UB_33      -0.0070494000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                4240
_reflns_number_total             4452
_reflns_odcompleteness_completeness 99.96
_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 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0307
_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)+(0.0517P)²+0.1283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C14(H14), C13(H13), C6(H6), C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C12(H12A,H12B), C8(H8A,H8B), C10(H10A,H10B)
1.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C22(H22), C3(H3), C4(H4), C5(H5), C29(H29), C19(H19), C20(H20),
 C25(H25), C21(H21), C28(H28), C26(H26), C27(H27)
1.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.53794(15) 0.57637(12) 0.46748(8) 0.0552(4) Uani 1 1 d . . . . .
N2 N 0.61779(13) 0.44153(11) 0.54610(7) 0.0349(3) Uani 1 1 d . . . . .
O1 O 0.88783(16) 0.64814(15) 0.46031(8) 0.0632(4) Uani 1 1 d . . . . .
N1 N 0.90636(15) 0.45278(14) 0.73686(9) 0.0456(4) Uani 1 1 d . . . . .
C1 C 0.89114(15) 0.50652(14) 0.67166(9) 0.0364(3) Uani 1 1 d . . . . .
C14 C 0.69021(14) 0.41022(13) 0.61470(8) 0.0319(3) Uani 1 1 d . . . . .
H14 H 0.6579 0.4568 0.6556 0.038 Uiso 1 1 calc R U . . .
C17 C 0.67185(15) 0.28404(14) 0.63495(9) 0.0345(3) Uani 1 1 d . . . . .
C13 C 0.83442(15) 0.43273(14) 0.61030(9) 0.0342(3) Uani 1 1 d . . . . .
H13 H 0.8731 0.3566 0.6149 0.041 Uiso 1 1 calc R U . . .
C15 C 0.61314(17) 0.55083(15) 0.51570(9) 0.0393(4) Uani 1 1 d . . . . .
C2 C 0.93462(15) 0.61861(15) 0.65824(11) 0.0394(4) Uani 1 1 d . . . . .
C23 C 0.51775(16) 0.36419(14) 0.52184(9) 0.0380(4) Uani 1 1 d . . . . .
H23A H 0.5501 0.2864 0.5177 0.046 Uiso 1 1 calc R U . . .
H23B H 0.4908 0.3879 0.4730 0.046 Uiso 1 1 calc R U . . .
C18 C 0.71088(18) 0.19496(15) 0.58880(11) 0.0434(4) Uani 1 1 d . . . . .
H18 H 0.7478 0.2124 0.5437 0.052 Uiso 1 1 calc R U . . .
C6 C 0.89957(17) 0.68523(15) 0.58940(11) 0.0443(4) Uani 1 1 d . . . . .
H6 H 0.9693 0.7294 0.5699 0.053 Uiso 1 1 calc R U . . .
C24 C 0.40750(16) 0.36237(15) 0.57285(10) 0.0407(4) Uani 1 1 d . . . . .
C22 C 0.6198(2) 0.25524(18) 0.70252(11) 0.0494(4) Uani 1 1 d . . . . .
H22 H 0.5932 0.3132 0.7344 0.059 Uiso 1 1 calc R U . . .
C9 C 0.70503(17) 0.63525(14) 0.54444(10) 0.0403(4) Uani 1 1 d . . . . .
C11 C 0.84379(17) 0.60563(16) 0.53033(10) 0.0424(4) Uani 1 1 d . . . . .
C12 C 0.87690(17) 0.47993(15) 0.53691(10) 0.0418(4) Uani 1 1 d . . . . .
H12A H 0.9655 0.4709 0.5326 0.050 Uiso 1 1 calc R U . . .
H12B H 0.8384 0.4370 0.4971 0.050 Uiso 1 1 calc R U . . .
C3 C 1.00294(18) 0.67139(16) 0.71404(12) 0.0489(5) Uani 1 1 d . . . . .
H3 H 1.0361 0.7445 0.7066 0.059 Uiso 1 1 calc R U . . .
C8 C 0.69144(17) 0.67322(14) 0.62755(11) 0.0415(4) Uani 1 1 d . . . . .
H8A H 0.6110 0.7034 0.6408 0.050 Uiso 1 1 calc R U . . .
H8B H 0.7210 0.6174 0.6634 0.050 Uiso 1 1 calc R U . . .
C4 C 1.0212(2) 0.61521(19) 0.78012(12) 0.0556(5) Uani 1 1 d . . . . .
H4 H 1.0681 0.6489 0.8174 0.067 Uiso 1 1 calc R U . . .
C5 C 0.9688(2) 0.50809(19) 0.79014(12) 0.0535(5) Uani 1 1 d . . . . .
H5 H 0.9771 0.4725 0.8360 0.064 Uiso 1 1 calc R U . . .
C29 C 0.36807(19) 0.25986(19) 0.60439(12) 0.0524(5) Uani 1 1 d . . . . .
H29 H 0.4126 0.1925 0.5960 0.063 Uiso 1 1 calc R U . . .
C7 C 0.78563(19) 0.76436(15) 0.60463(12) 0.0500(5) Uani 1 1 d . . . . .
H7 H 0.7953 0.8347 0.6342 0.060 Uiso 1 1 calc R U . . .
C19 C 0.6954(2) 0.08104(17) 0.60926(14) 0.0582(5) Uani 1 1 d . . . . .
H19 H 0.7201 0.0226 0.5773 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7127(2) 0.76851(16) 0.53045(13) 0.0564(5) Uani 1 1 d . . . . .
H10A H 0.7608 0.7910 0.4876 0.068 Uiso 1 1 calc R U . . .
H10B H 0.6346 0.8089 0.5328 0.068 Uiso 1 1 calc R U . . .
C20 C 0.6439(2) 0.05323(19) 0.67628(16) 0.0672(6) Uani 1 1 d . . . . .
H20 H 0.6341 -0.0236 0.6900 0.081 Uiso 1 1 calc R U . . .
C25 C 0.3407(2) 0.4621(2) 0.58696(15) 0.0613(6) Uani 1 1 d . . . . .
H25 H 0.3660 0.5320 0.5668 0.074 Uiso 1 1 calc R U . . .
C21 C 0.6070(3) 0.1402(2) 0.72293(13) 0.0671(6) Uani 1 1 d . . . . .
H21 H 0.5731 0.1218 0.7687 0.081 Uiso 1 1 calc R U . . .
C28 C 0.2635(2) 0.2560(3) 0.64814(16) 0.0744(7) Uani 1 1 d . . . . .
H28 H 0.2379 0.1864 0.6686 0.089 Uiso 1 1 calc R U . . .
C26 C 0.2366(3) 0.4577(3) 0.63101(19) 0.0857(9) Uani 1 1 d . . . . .
H26 H 0.1922 0.5248 0.6403 0.103 Uiso 1 1 calc R U . . .
C27 C 0.1981(3) 0.3545(3) 0.66120(19) 0.0877(9) Uani 1 1 d . . . . .
H27 H 0.1276 0.3520 0.6904 0.105 Uiso 1 1 calc R U . . .
C16 C 0.8259(3) 0.6073(3) 0.39611(13) 0.0842(9) Uani 1 1 d . . . . .
H16A H 0.8719 0.6287 0.3528 0.126 Uiso 1 1 calc R U . . .
H16B H 0.7452 0.6408 0.3937 0.126 Uiso 1 1 calc R U . . .
H16C H 0.8189 0.5247 0.3984 0.126 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
O2 C15 1.230(2) . ?
N2 C14 1.512(2) . ?
N2 C15 1.381(2) . ?
N2 C23 1.474(2) . ?
O1 C11 1.439(2) . ?
O1 C16 1.422(3) . ?
N1 C1 1.342(2) . ?
N1 C5 1.340(3) . ?
C1 C13 1.529(2) . ?
C1 C2 1.403(2) . ?
C14 H14 0.9800 . ?
C14 C17 1.520(2) . ?
C14 C13 1.589(2) . ?
C17 C18 1.393(3) . ?
C17 C22 1.386(2) . ?
C13 H13 0.9800 . ?
C13 C12 1.506(2) . ?
C15 C9 1.490(3) . ?
C2 C6 1.512(3) . ?
C2 C3 1.393(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.510(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C6 H6 0.9800 . ?
C6 C11 1.535(3) . ?
C6 C7 1.564(3) . ?
C24 C29 1.385(3) . ?
C24 C25 1.387(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.390(3) . ?
C9 C11 1.566(3) . ?
C9 C8 1.572(3) . ?
C9 C10 1.566(2) . ?
C11 C12 1.504(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.374(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.527(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(3) . ?
C5 H5 0.9300 . ?
C29 H29 0.9300 . ?
C29 C28 1.384(3) . ?
C7 H7 0.9800 . ?
C7 C10 1.557(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C21 1.373(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.383(4) . ?
C21 H21 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.364(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.379(5) . ?
C27 H27 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 N2 C14 124.40(14) . . ?
C15 N2 C23 114.33(14) . . ?
C23 N2 C14 118.74(13) . . ?
C16 O1 C11 116.50(17) . . ?
C5 N1 C1 118.08(17) . . ?
N1 C1 C13 115.24(15) . . ?
N1 C1 C2 122.65(16) . . ?
C2 C1 C13 121.85(15) . . ?
N2 C14 H14 107.5 . . ?
N2 C14 C17 111.10(12) . . ?
N2 C14 C13 115.59(13) . . ?
C17 C14 H14 107.5 . . ?
C17 C14 C13 107.40(12) . . ?
C13 C14 H14 107.5 . . ?
C18 C17 C14 121.90(15) . . ?
C22 C17 C14 119.81(16) . . ?
C22 C17 C18 118.23(17) . . ?
C1 C13 C14 116.88(13) . . ?
C1 C13 H13 105.6 . . ?
C14 C13 H13 105.6 . . ?
C12 C13 C1 108.17(14) . . ?
C12 C13 C14 113.90(14) . . ?
C12 C13 H13 105.6 . . ?
O2 C15 N2 121.77(17) . . ?
O2 C15 C9 122.22(16) . . ?
N2 C15 C9 116.02(14) . . ?
C1 C2 C6 121.99(16) . . ?
C3 C2 C1 117.42(17) . . ?
C3 C2 C6 120.34(16) . . ?
N2 C23 H23A 108.7 . . ?
N2 C23 H23B 108.7 . . ?
N2 C23 C24 114.25(13) . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.72(19) . . ?
C19 C18 H18 119.6 . . ?
C2 C6 H6 111.6 . . ?
C2 C6 C11 111.37(14) . . ?
C2 C6 C7 110.70(15) . . ?
C11 C6 H6 111.6 . . ?
C11 C6 C7 99.35(15) . . ?
C7 C6 H6 111.6 . . ?
C29 C24 C23 120.52(17) . . ?
C29 C24 C25 118.47(19) . . ?
C25 C24 C23 120.96(18) . . ?
C17 C22 H22 119.8 . . ?
C17 C22 C21 120.3(2) . . ?
C21 C22 H22 119.8 . . ?
C15 C9 C11 116.32(15) . . ?
C15 C9 C8 116.99(15) . . ?
C15 C9 C10 128.76(16) . . ?
C11 C9 C8 107.89(14) . . ?
C11 C9 C10 97.96(15) . . ?
C10 C9 C8 83.30(14) . . ?
O1 C11 C6 105.94(14) . . ?
O1 C11 C9 112.81(16) . . ?
O1 C11 C12 108.74(16) . . ?
C6 C11 C9 97.73(14) . . ?
C12 C11 C6 115.61(16) . . ?
C12 C11 C9 115.41(14) . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 C13 110.35(14) . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.85(18) . . ?
C4 C3 H3 120.1 . . ?
C9 C8 H8A 114.9 . . ?
C9 C8 H8B 114.9 . . ?
H8A C8 H8B 111.9 . . ?
C7 C8 C9 82.62(14) . . ?
C7 C8 H8A 114.9 . . ?
C7 C8 H8B 114.9 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.77(19) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.0(2) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C24 C29 H29 119.5 . . ?
C28 C29 C24 121.1(2) . . ?
C28 C29 H29 119.5 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 99.90(13) . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C10 85.09(15) . . ?
C10 C7 C6 105.58(17) . . ?
C10 C7 H7 119.9 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C9 C10 H10A 115.0 . . ?
C9 C10 H10B 115.0 . . ?
C7 C10 C9 81.83(14) . . ?
C7 C10 H10A 115.0 . . ?
C7 C10 H10B 115.0 . . ?
H10A C10 H10B 112.0 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.23(19) . . ?
C21 C20 H20 120.4 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H25 119.9 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 C29 119.9(3) . . ?
C27 C28 H28 120.0 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.5(3) . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 119.9(2) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C15 C9 C11 -116.6(2) . . . . ?
O2 C15 C9 C8 113.9(2) . . . . ?
O2 C15 C9 C10 9.9(3) . . . . ?
N2 C14 C17 C18 64.2(2) . . . . ?
N2 C14 C17 C22 -118.71(17) . . . . ?
N2 C14 C13 C1 126.12(15) . . . . ?
N2 C14 C13 C12 -1.25(19) . . . . ?
N2 C15 C9 C11 63.0(2) . . . . ?
N2 C15 C9 C8 -66.5(2) . . . . ?
N2 C15 C9 C10 -170.48(19) . . . . ?
N2 C23 C24 C29 -122.13(18) . . . . ?
N2 C23 C24 C25 60.3(2) . . . . ?
O1 C11 C12 C13 178.90(14) . . . . ?
N1 C1 C13 C14 76.27(19) . . . . ?
N1 C1 C13 C12 -153.61(15) . . . . ?
N1 C1 C2 C6 -170.02(17) . . . . ?
N1 C1 C2 C3 4.3(3) . . . . ?
C1 N1 C5 C4 -2.3(3) . . . . ?
C1 C13 C12 C11 -56.17(18) . . . . ?
C1 C2 C6 C11 -15.3(2) . . . . ?
C1 C2 C6 C7 94.25(19) . . . . ?
C1 C2 C3 C4 -2.5(3) . . . . ?
C14 N2 C15 O2 -167.94(16) . . . . ?
C14 N2 C15 C9 12.5(2) . . . . ?
C14 N2 C23 C24 68.81(18) . . . . ?
C14 C17 C18 C19 178.61(18) . . . . ?
C14 C17 C22 C21 -177.4(2) . . . . ?
C14 C13 C12 C11 75.58(18) . . . . ?
C17 C14 C13 C1 -109.25(15) . . . . ?
C17 C14 C13 C12 123.38(14) . . . . ?
C17 C18 C19 C20 -1.6(3) . . . . ?
C17 C22 C21 C20 -1.0(4) . . . . ?
C13 C1 C2 C6 16.2(2) . . . . ?
C13 C1 C2 C3 -169.50(16) . . . . ?
C13 C14 C17 C18 -63.14(19) . . . . ?
C13 C14 C17 C22 113.98(17) . . . . ?
C15 N2 C14 C17 177.86(15) . . . . ?
C15 N2 C14 C13 -59.4(2) . . . . ?
C15 N2 C23 C24 -93.95(18) . . . . ?
C15 C9 C11 O1 87.83(19) . . . . ?
C15 C9 C11 C6 -161.21(14) . . . . ?
C15 C9 C11 C12 -38.0(2) . . . . ?
C15 C9 C8 C7 -168.39(16) . . . . ?
C15 C9 C10 C7 156.7(2) . . . . ?
C2 C1 C13 C14 -109.54(18) . . . . ?
C2 C1 C13 C12 20.6(2) . . . . ?
C2 C6 C11 O1 -142.86(16) . . . . ?
C2 C6 C11 C9 100.68(16) . . . . ?
C2 C6 C11 C12 -22.4(2) . . . . ?
C2 C6 C7 C8 -59.46(19) . . . . ?
C2 C6 C7 C10 -147.08(15) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C23 N2 C14 C17 16.96(19) . . . . ?
C23 N2 C14 C13 139.66(14) . . . . ?
C23 N2 C15 O2 -6.3(3) . . . . ?
C23 N2 C15 C9 174.12(15) . . . . ?
C23 C24 C29 C28 -176.6(2) . . . . ?
C23 C24 C25 C26 176.9(2) . . . . ?
C18 C17 C22 C21 -0.2(3) . . . . ?
C18 C19 C20 C21 0.4(4) . . . . ?
C6 C2 C3 C4 171.90(18) . . . . ?
C6 C11 C12 C13 59.9(2) . . . . ?
C6 C7 C10 C9 60.54(16) . . . . ?
C24 C29 C28 C27 -0.5(4) . . . . ?
C24 C25 C26 C27 -0.1(5) . . . . ?
C22 C17 C18 C19 1.5(3) . . . . ?
C9 C11 C12 C13 -53.2(2) . . . . ?
C9 C8 C7 C6 -66.84(15) . . . . ?
C9 C8 C7 C10 38.16(13) . . . . ?
C11 C6 C7 C8 57.74(17) . . . . ?
C11 C6 C7 C10 -29.88(17) . . . . ?
C11 C9 C8 C7 58.20(15) . . . . ?
C11 C9 C10 C7 -69.96(16) . . . . ?
C3 C2 C6 C11 170.60(16) . . . . ?
C3 C2 C6 C7 -79.9(2) . . . . ?
C3 C4 C5 N1 3.9(3) . . . . ?
C8 C9 C11 O1 -138.41(15) . . . . ?
C8 C9 C11 C6 -27.45(16) . . . . ?
C8 C9 C11 C12 95.74(17) . . . . ?
C8 C9 C10 C7 37.25(14) . . . . ?
C8 C7 C10 C9 -38.39(14) . . . . ?
C5 N1 C1 C13 172.21(16) . . . . ?
C5 N1 C1 C2 -1.9(3) . . . . ?
C29 C24 C25 C26 -0.7(3) . . . . ?
C29 C28 C27 C26 -0.3(5) . . . . ?
C7 C6 C11 O1 100.45(16) . . . . ?
C7 C6 C11 C9 -16.02(15) . . . . ?
C7 C6 C11 C12 -139.06(15) . . . . ?
C19 C20 C21 C22 0.9(4) . . . . ?
C10 C9 C11 O1 -52.92(19) . . . . ?
C10 C9 C11 C6 58.04(16) . . . . ?
C10 C9 C11 C12 -178.77(16) . . . . ?
C10 C9 C8 C7 -38.03(14) . . . . ?
C25 C24 C29 C28 0.9(3) . . . . ?
C25 C26 C27 C28 0.5(5) . . . . ?
C16 O1 C11 C6 -165.0(2) . . . . ?
C16 O1 C11 C9 -59.2(3) . . . . ?
C16 O1 C11 C12 70.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.138
_oxdiff_exptl_absorpt_empirical_full_min 0.901
