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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_a210509c
_database_code_depnum_ccdc_archive 'CCDC 2129040'
loop_
_audit_author_name
_audit_author_address
'junsong zhao'
;Tianjin Normal University
China
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2021-09-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H27 N3 O'
_chemical_formula_sum            'C29 H27 N3 O'
_chemical_formula_weight         433.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.0837(10)
_cell_length_b                   11.1991(10)
_cell_length_c                   11.8993(11)
_cell_angle_alpha                105.919(8)
_cell_angle_beta                 108.497(9)
_cell_angle_gamma                96.764(8)
_cell_volume                     1194.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2514
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3340
_cell_measurement_theta_min      2.2490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8547
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         2.186
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00 -15.00   1.00   29.46    --  -10.77  77.00  60.00   26
  2  ω     -5.00  26.00   1.00   29.46    --  -10.77 -99.00-150.00   31
  3  ω     -8.00  53.00   1.00   29.46    --   11.63 -99.00   0.00   61
  4  ω      2.00  85.00   1.00   29.46    --   11.63  38.00-120.00   83
  5  ω    -68.00  41.00   1.00   29.46    --   11.63 -19.00  60.00  109
;
_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      0.0486236000
_diffrn_orient_matrix_UB_12      0.0434151000
_diffrn_orient_matrix_UB_13      0.0585119000
_diffrn_orient_matrix_UB_21      -0.0497719000
_diffrn_orient_matrix_UB_22      -0.0120345000
_diffrn_orient_matrix_UB_23      0.0285712000
_diffrn_orient_matrix_UB_31      0.0308583000
_diffrn_orient_matrix_UB_32      -0.0503826000
_diffrn_orient_matrix_UB_33      0.0140257000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2268
_reflns_number_total             4198
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4198
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.095
_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)+(0.0752P)²+0.0819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C20, C21, C19
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C20 \\sim C21 \\sim C19: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.005
Uanis(C7) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
4.a Ternary CH refined with riding coordinates:
 C12(H12), C19(H19)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C20(H20A,H20B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C24(H24), C25(H25), C27(H27), C28(H28)
4.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1755(2) 0.68943(19) 0.6248(2) 0.0966(7) Uani 1 1 d . . . . .
N1 N 0.6677(3) 0.9289(3) 0.8515(3) 0.1013(9) Uani 1 1 d . . . . .
N2 N 0.4121(3) 0.7714(2) 0.7377(2) 0.0714(7) Uani 1 1 d . . . . .
H2 H 0.493532 0.750185 0.756857 0.086 Uiso 1 1 calc R . . . .
N3 N 0.3362(3) -0.3731(3) 0.3019(3) 0.1107(10) Uani 1 1 d . . . . .
C1 C 0.4159(4) 0.9007(3) 0.7936(2) 0.0719(8) Uani 1 1 d . . . . .
C2 C 0.5543(4) 0.9812(3) 0.8544(3) 0.0770(8) Uani 1 1 d . . . . .
C3 C 0.7980(5) 1.0045(4) 0.9080(5) 0.1498(19) Uani 1 1 d . . . . .
H3 H 0.875941 0.968907 0.904252 0.180 Uiso 1 1 calc R . . . .
C4 C 0.8246(6) 1.1352(5) 0.9733(5) 0.165(2) Uani 1 1 d . . . . .
H4 H 0.917781 1.184477 1.013761 0.199 Uiso 1 1 calc R . . . .
C5 C 0.7107(6) 1.1875(4) 0.9756(4) 0.1286(15) Uani 1 1 d . . . . .
H5 H 0.725933 1.274049 1.017847 0.154 Uiso 1 1 calc R . . . .
C6 C 0.5719(5) 1.1143(3) 0.9163(3) 0.0928(10) Uani 1 1 d . . . . .
C7 C 0.4491(6) 1.1596(4) 0.9138(3) 0.1089(12) Uani 1 1 d . U . . .
H7 H 0.458092 1.245919 0.953061 0.131 Uiso 1 1 calc R . . . .
C8 C 0.3184(5) 1.0829(4) 0.8567(4) 0.1181(15) Uani 1 1 d . . . . .
H8 H 0.238358 1.116335 0.857179 0.142 Uiso 1 1 calc R . . . .
C9 C 0.3004(4) 0.9507(3) 0.7953(3) 0.0993(11) Uani 1 1 d . . . . .
H9 H 0.208759 0.898277 0.755978 0.119 Uiso 1 1 calc R . . . .
C10 C 0.2978(3) 0.6760(3) 0.6578(3) 0.0666(7) Uani 1 1 d . . . . .
C11 C 0.3360(3) 0.5503(2) 0.6083(3) 0.0673(7) Uani 1 1 d . . . . .
H11A H 0.428598 0.549438 0.665848 0.081 Uiso 1 1 calc R . . . .
H11B H 0.344717 0.543225 0.527929 0.081 Uiso 1 1 calc R . . . .
C12 C 0.2246(3) 0.4345(2) 0.5917(2) 0.0570(7) Uani 1 1 d . . . . .
H12 H 0.132566 0.436247 0.531988 0.068 Uiso 1 1 calc R . . . .
C13 C 0.2058(3) 0.4438(2) 0.7144(2) 0.0549(6) Uani 1 1 d . . . . .
C14 C 0.3151(3) 0.4385(3) 0.8167(3) 0.0794(9) Uani 1 1 d . . . . .
H14 H 0.402755 0.428611 0.809815 0.095 Uiso 1 1 calc R . . . .
C15 C 0.2976(4) 0.4474(3) 0.9297(3) 0.0944(10) Uani 1 1 d . . . . .
H15 H 0.372695 0.443830 0.997635 0.113 Uiso 1 1 calc R . . . .
C16 C 0.1683(4) 0.4616(3) 0.9397(3) 0.0933(10) Uani 1 1 d . . . . .
H16 H 0.155098 0.467246 1.014683 0.112 Uiso 1 1 calc R . . . .
C17 C 0.0596(4) 0.4674(3) 0.8405(3) 0.0934(10) Uani 1 1 d . . . . .
H17 H -0.027761 0.477804 0.847964 0.112 Uiso 1 1 calc R . . . .
C18 C 0.0781(3) 0.4580(3) 0.7281(3) 0.0739(8) Uani 1 1 d . . . . .
H18 H 0.002274 0.461465 0.660659 0.089 Uiso 1 1 calc R . . . .
C19 C 0.2648(3) 0.3075(2) 0.5352(2) 0.0628(6) Uani 1 1 d . U . . .
H19 H 0.354366 0.305017 0.597631 0.075 Uiso 1 1 calc R . . . .
C20 C 0.2933(3) 0.2969(3) 0.4147(3) 0.0728(7) Uani 1 1 d . U . . .
H20A H 0.375466 0.363903 0.434050 0.087 Uiso 1 1 calc R . . . .
H20B H 0.319164 0.216114 0.387443 0.087 Uiso 1 1 calc R . . . .
C21 C 0.1705(4) 0.3057(3) 0.3065(3) 0.0973(10) Uani 1 1 d . U . . .
H21A H 0.196414 0.291345 0.233712 0.146 Uiso 1 1 calc GR . . . .
H21B H 0.150491 0.388877 0.328638 0.146 Uiso 1 1 calc GR . . . .
H21C H 0.086829 0.242441 0.288541 0.146 Uiso 1 1 calc GR . . . .
C22 C 0.1507(3) 0.1943(2) 0.5188(3) 0.0764(8) Uani 1 1 d . . . . .
H22A H 0.139813 0.203519 0.598638 0.092 Uiso 1 1 calc R . . . .
H22B H 0.059480 0.195606 0.459531 0.092 Uiso 1 1 calc R . . . .
C23 C 0.1870(3) 0.0667(3) 0.4724(3) 0.0694(8) Uani 1 1 d . . . . .
C24 C 0.1011(3) -0.0232(3) 0.3628(4) 0.0987(11) Uani 1 1 d . . . . .
H24 H 0.015970 -0.007005 0.316384 0.118 Uiso 1 1 calc R . . . .
C25 C 0.1347(4) -0.1387(3) 0.3169(4) 0.0989(11) Uani 1 1 d . . . . .
H25 H 0.073109 -0.198317 0.240885 0.119 Uiso 1 1 calc R . . . .
C26 C 0.2583(3) -0.1644(3) 0.3836(3) 0.0729(8) Uani 1 1 d . . . . .
C27 C 0.3433(4) -0.0776(3) 0.4975(3) 0.1030(12) Uani 1 1 d . . . . .
H27 H 0.425463 -0.095797 0.546318 0.124 Uiso 1 1 calc R . . . .
C28 C 0.3078(4) 0.0370(3) 0.5406(3) 0.1032(12) Uani 1 1 d . . . . .
H28 H 0.367540 0.095495 0.618051 0.124 Uiso 1 1 calc R . . . .
C29 C 0.3000(3) -0.2817(3) 0.3368(3) 0.0843(9) Uani 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 C10 1.211(3) . ?
N1 C2 1.350(4) . ?
N1 C3 1.327(5) . ?
N2 H2 0.8600 . ?
N2 C1 1.408(3) . ?
N2 C10 1.353(3) . ?
N3 C29 1.143(3) . ?
C1 C2 1.410(4) . ?
C1 C9 1.355(4) . ?
C2 C6 1.431(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.403(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.354(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C6 C7 1.388(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.334(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.420(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.515(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.535(4) . ?
C12 H12 0.9800 . ?
C12 C13 1.508(3) . ?
C12 C19 1.557(3) . ?
C13 C14 1.380(4) . ?
C13 C18 1.371(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.355(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9800 . ?
C19 C20 1.526(4) . ?
C19 C22 1.532(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.512(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.516(3) . ?
C23 C24 1.350(4) . ?
C23 C28 1.368(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.386(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.359(4) . ?
C26 C27 1.364(4) . ?
C26 C29 1.446(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(4) . ?
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
C3 N1 C2 118.2(3) . . ?
C1 N2 H2 115.6 . . ?
C10 N2 H2 115.6 . . ?
C10 N2 C1 128.8(2) . . ?
N2 C1 C2 115.1(3) . . ?
C9 C1 N2 125.7(3) . . ?
C9 C1 C2 119.2(3) . . ?
N1 C2 C1 118.0(3) . . ?
N1 C2 C6 121.7(3) . . ?
C1 C2 C6 120.2(3) . . ?
N1 C3 H3 118.2 . . ?
N1 C3 C4 123.6(5) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.1(5) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(4) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C2 117.3(4) . . ?
C5 C6 C7 125.0(4) . . ?
C7 C6 C2 117.7(4) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.8(4) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.7(4) . . ?
C9 C8 H8 119.7 . . ?
C1 C9 C8 120.4(4) . . ?
C1 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
O1 C10 N2 123.7(2) . . ?
O1 C10 C11 122.2(3) . . ?
N2 C10 C11 114.1(2) . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C10 C11 C12 113.0(2) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C11 C12 H12 107.6 . . ?
C11 C12 C19 111.22(19) . . ?
C13 C12 C11 110.5(2) . . ?
C13 C12 H12 107.6 . . ?
C13 C12 C19 112.07(19) . . ?
C19 C12 H12 107.6 . . ?
C14 C13 C12 121.9(2) . . ?
C18 C13 C12 120.8(2) . . ?
C18 C13 C14 117.4(3) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.8(3) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 121.4(3) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C12 C19 H19 106.8 . . ?
C20 C19 C12 114.0(2) . . ?
C20 C19 H19 106.8 . . ?
C20 C19 C22 112.2(2) . . ?
C22 C19 C12 109.79(19) . . ?
C22 C19 H19 106.8 . . ?
C19 C20 H20A 108.3 . . ?
C19 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C21 C20 C19 116.0(2) . . ?
C21 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
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 . . ?
C19 C22 H22A 109.0 . . ?
C19 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 C19 113.1(2) . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C24 C23 C22 121.7(3) . . ?
C24 C23 C28 116.9(3) . . ?
C28 C23 C22 121.4(3) . . ?
C23 C24 H24 118.8 . . ?
C23 C24 C25 122.5(3) . . ?
C25 C24 H24 118.8 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.7(3) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C27 118.8(3) . . ?
C25 C26 C29 121.4(3) . . ?
C27 C26 C29 119.8(3) . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 C27 121.7(3) . . ?
C23 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
N3 C29 C26 178.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C11 C12 -38.3(4) . . . . ?
N1 C2 C6 C5 -1.2(5) . . . . ?
N1 C2 C6 C7 179.6(3) . . . . ?
N1 C3 C4 C5 -1.8(9) . . . . ?
N2 C1 C2 N1 1.3(4) . . . . ?
N2 C1 C2 C6 -179.0(2) . . . . ?
N2 C1 C9 C8 179.0(3) . . . . ?
N2 C10 C11 C12 144.0(2) . . . . ?
C1 N2 C10 O1 -2.4(5) . . . . ?
C1 N2 C10 C11 175.3(2) . . . . ?
C1 C2 C6 C5 179.1(3) . . . . ?
C1 C2 C6 C7 0.0(4) . . . . ?
C2 N1 C3 C4 1.6(7) . . . . ?
C2 C1 C9 C8 0.5(5) . . . . ?
C2 C6 C7 C8 0.4(5) . . . . ?
C3 N1 C2 C1 179.7(3) . . . . ?
C3 N1 C2 C6 0.0(5) . . . . ?
C3 C4 C5 C6 0.5(8) . . . . ?
C4 C5 C6 C2 0.9(6) . . . . ?
C4 C5 C6 C7 -180.0(4) . . . . ?
C5 C6 C7 C8 -178.7(4) . . . . ?
C6 C7 C8 C9 -0.3(6) . . . . ?
C7 C8 C9 C1 -0.1(6) . . . . ?
C9 C1 C2 N1 179.9(3) . . . . ?
C9 C1 C2 C6 -0.4(4) . . . . ?
C10 N2 C1 C2 -169.0(3) . . . . ?
C10 N2 C1 C9 12.5(5) . . . . ?
C10 C11 C12 C13 -57.4(3) . . . . ?
C10 C11 C12 C19 177.5(2) . . . . ?
C11 C12 C13 C14 -65.5(3) . . . . ?
C11 C12 C13 C18 114.4(3) . . . . ?
C11 C12 C19 C20 -52.5(3) . . . . ?
C11 C12 C19 C22 -179.4(2) . . . . ?
C12 C13 C14 C15 179.8(3) . . . . ?
C12 C13 C18 C17 -179.6(3) . . . . ?
C12 C19 C20 C21 -59.2(3) . . . . ?
C12 C19 C22 C23 -176.1(2) . . . . ?
C13 C12 C19 C20 -176.7(2) . . . . ?
C13 C12 C19 C22 56.4(3) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C13 C18 C17 0.4(4) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
C16 C17 C18 C13 -0.6(5) . . . . ?
C18 C13 C14 C15 -0.2(4) . . . . ?
C19 C12 C13 C14 59.1(3) . . . . ?
C19 C12 C13 C18 -121.0(3) . . . . ?
C19 C22 C23 C24 -119.6(3) . . . . ?
C19 C22 C23 C28 61.2(4) . . . . ?
C20 C19 C22 C23 56.0(3) . . . . ?
C22 C19 C20 C21 66.4(3) . . . . ?
C22 C23 C24 C25 177.9(3) . . . . ?
C22 C23 C28 C27 -178.4(3) . . . . ?
C23 C24 C25 C26 0.2(6) . . . . ?
C24 C23 C28 C27 2.4(5) . . . . ?
C24 C25 C26 C27 3.0(5) . . . . ?
C24 C25 C26 C29 -177.7(3) . . . . ?
C25 C26 C27 C28 -3.5(5) . . . . ?
C26 C27 C28 C23 0.8(6) . . . . ?
C28 C23 C24 C25 -2.9(5) . . . . ?
C29 C26 C27 C28 177.2(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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.718
####################################################################### 
# 
# 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_a210802a
_database_code_depnum_ccdc_archive 'CCDC 2129080'
loop_
_audit_author_name
_audit_author_address
'junsong zhao'
;Tianjin Normal University
China
;
_audit_update_record             
;
2021-12-16 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_audit_creation_date             2021-08-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H27 N3 O'
_chemical_formula_sum            'C29 H27 N3 O'
_chemical_formula_weight         433.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.2156(16)
_cell_length_b                   10.6541(17)
_cell_length_c                   12.2607(19)
_cell_angle_alpha                75.489(14)
_cell_angle_beta                 86.653(13)
_cell_angle_gamma                68.487(15)
_cell_volume                     1201.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1674
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6000
_cell_measurement_theta_min      2.1720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.1461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8555
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         2.376
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  35.00   1.00   24.68    --   11.47 -70.00  81.00   91
  2  ω    -17.00  77.00   1.00   24.68    --   11.47  70.00-146.00   94
  3  ω      5.00  30.00   1.00   24.68    --  -10.61 -99.00-150.00   25
  4  ω    -42.00  21.00   1.00   24.68    --  -10.61  77.00 -30.00   63
  5  ω    -17.00  17.00   1.00   24.68    --  -10.61  77.00   0.00   34
;
_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      0.0048135000
_diffrn_orient_matrix_UB_12      0.0593831000
_diffrn_orient_matrix_UB_13      -0.0394208000
_diffrn_orient_matrix_UB_21      0.0659145000
_diffrn_orient_matrix_UB_22      -0.0126374000
_diffrn_orient_matrix_UB_23      0.0250898000
_diffrn_orient_matrix_UB_31      0.0347823000
_diffrn_orient_matrix_UB_32      -0.0420333000
_diffrn_orient_matrix_UB_33      -0.0373156000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1341
_reflns_number_total             4223
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4223
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.2430
_refine_ls_R_factor_gt           0.0759
_refine_ls_restrained_S_all      0.994
_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)+(0.0655P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.2299
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C11 = C13-C12 = C16-C13 = C16-C13' = C13'-C12' = C12'-C11 = C14-C13 =
 C14'-C13' = C15-C14 = C15'-C14'
 1.52 with sigma of 0.01
 C16'-C13' = C16-C13
 1.52 with sigma of 0.01
 C17-C16' = C17-C16 = C23-C16' = C23-C16
 1.48 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C12') \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C13') \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C14') \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C15') \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C13) = Uanis(C13')
Uanis(C15) = Uanis(C15')
Uanis(C14) = Uanis(C14')
Uanis(C12) = Uanis(C12')
Uanis(C16) = Uanis(C16')
4. Others
 Sof(H11C)=Sof(H11D)=Sof(C14')=Sof(H14A)=Sof(H14B)=Sof(C15')=Sof(H15A)=
 Sof(H15B)=Sof(H15C)=Sof(C13')=Sof(H13')=Sof(C12')=Sof(H12C)=Sof(H12D)=
 Sof(C16')=Sof(H16')=1-FVAR(1)
 Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C16)=Sof(H16)=Sof(C13)=
 Sof(H13)=Sof(C14)=Sof(H14C)=Sof(H14D)=Sof(C15)=Sof(H15D)=Sof(H15E)=Sof(H15F)=
 FVAR(1)
5.a Riding coordinates:
 C12'(H12C,H12D)
5.b Ternary CH refined with riding coordinates:
 C16(H16), C13'(H13'), C13(H13), C16'(H16')
5.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11(H11C,H11D), C12(H12A,H12B), C14'(H14A,H14B), C14(H14C,H14D)
5.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C20(H20), C27(H27), C21(H21), C28(H28), C18(H18), C22(H22), C7(H7),
 C19(H19), C25(H25), C24(H24), C1(H1A), C5(H5), C2(H2), C6(H6), C3(H3)
5.e Idealised Me refined as rotating group:
 C15'(H15A,H15B,H15C), C15(H15D,H15E,H15F)
;
_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
N1 N 0.1161(4) 0.5653(4) 0.3134(3) 0.0763(13) Uani 1 1 d . . . . .
H1 H 0.056780 0.623857 0.346336 0.092 Uiso 1 1 calc R . . . .
O1 O 0.3057(4) 0.3640(4) 0.3462(3) 0.1094(16) Uani 1 1 d . . . . .
N3 N -0.0595(5) 0.8186(5) 0.2081(4) 0.0959(15) Uani 1 1 d . . . . .
C17 C 0.4730(6) 0.2825(5) 0.8629(3) 0.0726(16) Uani 1 1 d D . . . .
C8 C 0.0969(5) 0.5955(5) 0.1950(4) 0.0732(15) Uani 1 1 d . . . . .
C10 C 0.2161(5) 0.4557(6) 0.3817(4) 0.0789(16) Uani 1 1 d . . . . .
C23 C 0.5621(7) 0.1919(6) 0.6957(4) 0.0869(19) Uani 1 1 d D . . . .
C20 C 0.4948(6) 0.2357(6) 1.0960(4) 0.0842(18) Uani 1 1 d . . . . .
H20 H 0.500036 0.220707 1.173912 0.101 Uiso 1 1 calc R . . . .
C27 C 0.6256(6) -0.0175(5) 0.6271(4) 0.0796(16) Uani 1 1 d . . . . .
H27 H 0.599172 -0.085516 0.610273 0.096 Uiso 1 1 calc R . . . .
C26 C 0.7620(6) -0.0208(6) 0.6129(4) 0.0805(16) Uani 1 1 d . . . . .
C21 C 0.5569(6) 0.3194(6) 1.0288(4) 0.0851(18) Uani 1 1 d . . . . .
H21 H 0.606072 0.360526 1.060559 0.102 Uiso 1 1 calc R . . . .
C9 C 0.0049(5) 0.7324(6) 0.1396(5) 0.0821(16) Uani 1 1 d . . . . .
C28 C 0.5289(6) 0.0906(6) 0.6675(4) 0.0858(17) Uani 1 1 d . . . . .
H28 H 0.436668 0.094033 0.675654 0.103 Uiso 1 1 calc R . . . .
C18 C 0.4146(6) 0.1990(6) 0.9345(4) 0.0920(19) Uani 1 1 d . . . . .
H18 H 0.365080 0.156976 0.904326 0.110 Uiso 1 1 calc R . . . .
C4 C -0.0148(6) 0.7657(7) 0.0201(5) 0.0899(17) Uani 1 1 d . . . . .
C22 C 0.5460(5) 0.3429(5) 0.9115(4) 0.0837(17) Uani 1 1 d . . . . .
H22 H 0.588325 0.399824 0.865498 0.100 Uiso 1 1 calc R . . . .
C11 C 0.2109(5) 0.4546(5) 0.5046(4) 0.0830(16) Uani 1 1 d D U . . .
H11A H 0.155696 0.547014 0.513668 0.100 Uiso 0.507(5) 1 calc R . P A 1
H11B H 0.165909 0.391318 0.544643 0.100 Uiso 0.507(5) 1 calc R . P A 1
H11C H 0.200403 0.369506 0.548321 0.100 Uiso 0.493(5) 1 calc R . P A 2
H11D H 0.130076 0.532669 0.516850 0.100 Uiso 0.493(5) 1 calc R . P A 2
C7 C 0.1625(5) 0.5029(6) 0.1325(4) 0.0855(17) Uani 1 1 d . . . . .
H7 H 0.222510 0.413503 0.167613 0.103 Uiso 1 1 calc R . . . .
C19 C 0.4258(6) 0.1747(6) 1.0490(5) 0.0954(18) Uani 1 1 d . . . . .
H19 H 0.385638 0.115716 1.094864 0.114 Uiso 1 1 calc R . . . .
C25 C 0.8007(7) 0.0765(7) 0.6418(4) 0.0990(19) Uani 1 1 d . . . . .
H25 H 0.893267 0.072242 0.634037 0.119 Uiso 1 1 calc R . . . .
C12 C 0.3556(9) 0.4097(13) 0.5524(7) 0.070(2) Uani 0.507(5) 1 d D U P A 1
H12A H 0.393186 0.483107 0.527340 0.084 Uiso 0.507(5) 1 calc R . P A 1
H12B H 0.417568 0.327384 0.529791 0.084 Uiso 0.507(5) 1 calc R . P A 1
C29 C 0.8629(6) -0.1294(7) 0.5651(5) 0.105(2) Uani 1 1 d . . . . .
C24 C 0.7021(9) 0.1820(6) 0.6830(4) 0.106(2) Uani 1 1 d . . . . .
H24 H 0.729780 0.247721 0.702519 0.127 Uiso 1 1 calc R . . . .
C1 C -0.1475(6) 0.9489(7) 0.1537(7) 0.115(2) Uani 1 1 d . . . . .
H1A H -0.192936 1.013009 0.195741 0.138 Uiso 1 1 calc R . . . .
C5 C 0.0560(7) 0.6663(8) -0.0383(5) 0.103(2) Uani 1 1 d . . . . .
H5 H 0.044038 0.687887 -0.116324 0.123 Uiso 1 1 calc R . . . .
C2 C -0.1711(7) 0.9881(7) 0.0382(7) 0.121(2) Uani 1 1 d . . . . .
H2 H -0.232326 1.077614 0.004862 0.145 Uiso 1 1 calc R . . . .
N2 N 0.9418(6) -0.2093(7) 0.5243(5) 0.145(2) Uani 1 1 d . . . . .
C6 C 0.1403(7) 0.5413(7) 0.0158(5) 0.108(2) Uani 1 1 d . . . . .
H6 H 0.186550 0.476404 -0.025468 0.130 Uiso 1 1 calc R . . . .
C16 C 0.4877(9) 0.3204(9) 0.7362(6) 0.067(3) Uani 0.507(5) 1 d D U P A 1
H16 H 0.534956 0.387547 0.713741 0.081 Uiso 0.507(5) 1 calc R . P A 1
C3 C -0.1079(6) 0.9002(8) -0.0273(6) 0.117(2) Uani 1 1 d . . . . .
H3 H -0.126509 0.929463 -0.104797 0.140 Uiso 1 1 calc R . . . .
C14' C 0.2804(13) 0.5611(10) 0.7159(10) 0.073(2) Uani 0.493(5) 1 d D U P A 2
H14A H 0.188428 0.557595 0.705939 0.087 Uiso 0.493(5) 1 calc R . P A 2
H14B H 0.299684 0.540982 0.796282 0.087 Uiso 0.493(5) 1 calc R . P A 2
C15' C 0.2756(19) 0.7078(12) 0.6616(13) 0.111(4) Uani 0.493(5) 1 d D U P A 2
H15A H 0.241296 0.734784 0.584743 0.167 Uiso 0.493(5) 1 calc GR . P A 2
H15B H 0.368561 0.710056 0.663401 0.167 Uiso 0.493(5) 1 calc GR . P A 2
H15C H 0.213995 0.771250 0.702226 0.167 Uiso 0.493(5) 1 calc GR . P A 2
C13' C 0.3909(10) 0.4475(8) 0.6685(6) 0.0587(19) Uani 0.493(5) 1 d D U P A 2
H13' H 0.476716 0.469071 0.664141 0.070 Uiso 0.493(5) 1 calc R . P A 2
C13 C 0.3407(8) 0.3775(10) 0.6818(6) 0.0587(19) Uani 0.507(5) 1 d D U P A 1
H13 H 0.298803 0.305958 0.704225 0.070 Uiso 0.507(5) 1 calc R . P A 1
C14 C 0.2477(11) 0.5069(10) 0.7217(10) 0.073(2) Uani 0.507(5) 1 d D U P A 1
H14C H 0.152011 0.533341 0.693792 0.087 Uiso 0.507(5) 1 calc R . P A 1
H14D H 0.247306 0.481099 0.803359 0.087 Uiso 0.507(5) 1 calc R . P A 1
C12' C 0.3484(10) 0.4642(13) 0.5446(8) 0.070(2) Uani 0.493(5) 1 d D U P A 2
H12C H 0.372810 0.544114 0.509423 0.084 Uiso 0.493(5) 1 d R . P A 2
H12D H 0.382630 0.395214 0.500593 0.084 Uiso 0.493(5) 1 d R . P A 2
C15 C 0.2901(19) 0.6349(15) 0.6858(14) 0.111(4) Uani 0.507(5) 1 d D U P A 1
H15D H 0.291458 0.661901 0.605079 0.167 Uiso 0.507(5) 1 calc GR . P A 1
H15E H 0.382123 0.612670 0.717321 0.167 Uiso 0.507(5) 1 calc GR . P A 1
H15F H 0.223389 0.710199 0.712628 0.167 Uiso 0.507(5) 1 calc GR . P A 1
C16' C 0.4331(10) 0.2977(9) 0.7404(6) 0.067(3) Uani 0.493(5) 1 d D . P A 2
H16' H 0.352624 0.268388 0.740706 0.081 Uiso 0.493(5) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.8600 . ?
N1 C8 1.415(5) . ?
N1 C10 1.358(5) . ?
O1 C10 1.222(5) . ?
N3 C9 1.364(6) . ?
N3 C1 1.367(7) . ?
C17 C18 1.361(7) . ?
C17 C22 1.387(7) . ?
C17 C16 1.517(8) . ?
C17 C16' 1.532(8) . ?
C8 C9 1.430(7) . ?
C8 C7 1.359(6) . ?
C10 C11 1.501(5) . ?
C23 C28 1.367(7) . ?
C23 C24 1.397(8) . ?
C23 C16 1.494(8) . ?
C23 C16' 1.564(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.365(8) . ?
C20 C19 1.350(7) . ?
C27 H27 0.9300 . ?
C27 C26 1.383(7) . ?
C27 C28 1.393(6) . ?
C26 C25 1.364(7) . ?
C26 C29 1.462(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.400(6) . ?
C9 C4 1.427(7) . ?
C28 H28 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.365(6) . ?
C4 C5 1.384(7) . ?
C4 C3 1.394(8) . ?
C22 H22 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C11 C12 1.483(8) . ?
C11 C12' 1.561(8) . ?
C7 H7 0.9300 . ?
C7 C6 1.394(6) . ?
C19 H19 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.388(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.547(8) . ?
C29 N2 1.134(6) . ?
C24 H24 0.9300 . ?
C1 H1A 0.9300 . ?
C1 C2 1.380(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.318(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.346(8) . ?
C6 H6 0.9300 . ?
C16 H16 0.9800 . ?
C16 C13 1.521(6) . ?
C3 H3 0.9300 . ?
C14' H14A 0.9700 . ?
C14' H14B 0.9700 . ?
C14' C15' 1.522(9) . ?
C14' C13' 1.533(8) . ?
C15' H15A 0.9600 . ?
C15' H15B 0.9600 . ?
C15' H15C 0.9600 . ?
C13' H13' 0.9800 . ?
C13' C12' 1.554(8) . ?
C13' C16' 1.531(8) . ?
C13 H13 0.9800 . ?
C13 C14 1.537(8) . ?
C14 H14C 0.9700 . ?
C14 H14D 0.9700 . ?
C14 C15 1.534(9) . ?
C12' H12C 0.9657 . ?
C12' H12D 0.9706 . ?
C15 H15D 0.9600 . ?
C15 H15E 0.9600 . ?
C15 H15F 0.9600 . ?
C16' H16' 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 H1 115.8 . . ?
C10 N1 H1 115.8 . . ?
C10 N1 C8 128.3(4) . . ?
C9 N3 C1 115.0(5) . . ?
C18 C17 C22 116.8(4) . . ?
C18 C17 C16 134.7(6) . . ?
C18 C17 C16' 110.2(6) . . ?
C22 C17 C16 108.3(6) . . ?
C22 C17 C16' 132.8(7) . . ?
N1 C8 C9 117.2(4) . . ?
C7 C8 N1 123.6(5) . . ?
C7 C8 C9 119.2(5) . . ?
N1 C10 C11 115.7(4) . . ?
O1 C10 N1 122.6(4) . . ?
O1 C10 C11 121.7(5) . . ?
C28 C23 C24 116.3(5) . . ?
C28 C23 C16 137.6(7) . . ?
C28 C23 C16' 112.2(7) . . ?
C24 C23 C16 106.1(7) . . ?
C24 C23 C16' 131.5(7) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.8(5) . . ?
C26 C27 H27 121.0 . . ?
C26 C27 C28 118.0(5) . . ?
C28 C27 H27 121.0 . . ?
C27 C26 C29 118.7(6) . . ?
C25 C26 C27 120.4(5) . . ?
C25 C26 C29 120.9(6) . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(6) . . ?
C22 C21 H21 120.3 . . ?
N3 C9 C8 115.9(5) . . ?
N3 C9 C4 125.9(5) . . ?
C4 C9 C8 118.2(5) . . ?
C23 C28 C27 123.6(6) . . ?
C23 C28 H28 118.2 . . ?
C27 C28 H28 118.2 . . ?
C17 C18 H18 118.7 . . ?
C17 C18 C19 122.6(5) . . ?
C19 C18 H18 118.7 . . ?
C5 C4 C9 119.5(5) . . ?
C5 C4 C3 125.7(6) . . ?
C3 C4 C9 114.7(6) . . ?
C17 C22 C21 120.9(5) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C10 C11 H11C 109.6 . . ?
C10 C11 H11D 109.6 . . ?
C10 C11 C12' 110.3(5) . . ?
H11A C11 H11B 108.2 . . ?
H11C C11 H11D 108.1 . . ?
C12 C11 C10 109.9(5) . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C12' C11 H11C 109.6 . . ?
C12' C11 H11D 109.6 . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.2(5) . . ?
C6 C7 H7 119.9 . . ?
C20 C19 C18 120.4(6) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C26 C25 H25 120.0 . . ?
C26 C25 C24 120.0(6) . . ?
C24 C25 H25 120.0 . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C11 C12 C13 105.2(7) . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
N2 C29 C26 177.0(8) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.6(6) . . ?
C25 C24 H24 119.2 . . ?
N3 C1 H1A 119.0 . . ?
N3 C1 C2 122.1(6) . . ?
C2 C1 H1A 119.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(6) . . ?
C6 C5 H5 119.8 . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(6) . . ?
C3 C2 H2 119.1 . . ?
C7 C6 H6 118.8 . . ?
C5 C6 C7 122.4(6) . . ?
C5 C6 H6 118.8 . . ?
C17 C16 H16 111.6 . . ?
C17 C16 C13 107.5(7) . . ?
C23 C16 C17 110.1(6) . . ?
C23 C16 H16 111.6 . . ?
C23 C16 C13 104.1(6) . . ?
C13 C16 H16 111.6 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.5(7) . . ?
C2 C3 H3 119.8 . . ?
H14A C14' H14B 107.6 . . ?
C15' C14' H14A 108.7 . . ?
C15' C14' H14B 108.7 . . ?
C15' C14' C13' 114.3(10) . . ?
C13' C14' H14A 108.7 . . ?
C13' C14' H14B 108.7 . . ?
C14' C15' H15A 109.5 . . ?
C14' C15' H15B 109.5 . . ?
C14' C15' H15C 109.5 . . ?
H15A C15' H15B 109.5 . . ?
H15A C15' H15C 109.5 . . ?
H15B C15' H15C 109.5 . . ?
C14' C13' H13' 105.4 . . ?
C14' C13' C12' 109.4(8) . . ?
C12' C13' H13' 105.4 . . ?
C16' C13' C14' 116.9(7) . . ?
C16' C13' H13' 105.4 . . ?
C16' C13' C12' 113.3(8) . . ?
C12 C13 H13 108.8 . . ?
C16 C13 C12 107.7(6) . . ?
C16 C13 H13 108.8 . . ?
C16 C13 C14 110.2(7) . . ?
C14 C13 C12 112.3(8) . . ?
C14 C13 H13 108.8 . . ?
C13 C14 H14C 108.2 . . ?
C13 C14 H14D 108.2 . . ?
H14C C14 H14D 107.3 . . ?
C15 C14 C13 116.4(10) . . ?
C15 C14 H14C 108.2 . . ?
C15 C14 H14D 108.2 . . ?
C11 C12' H12C 119.4 . . ?
C11 C12' H12D 76.5 . . ?
C13' C12' C11 125.7(8) . . ?
C13' C12' H12C 98.6 . . ?
C13' C12' H12D 127.4 . . ?
H12C C12' H12D 109.7 . . ?
C14 C15 H15D 109.5 . . ?
C14 C15 H15E 109.5 . . ?
C14 C15 H15F 109.5 . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
C17 C16' C23 105.8(5) . . ?
C17 C16' H16' 108.1 . . ?
C23 C16' H16' 108.1 . . ?
C13' C16' C17 113.0(7) . . ?
C13' C16' C23 113.6(7) . . ?
C13' C16' H16' 108.1 . . ?

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
N1 C8 C9 N3 -2.4(7) . . . . ?
N1 C8 C9 C4 179.3(4) . . . . ?
N1 C8 C7 C6 -178.8(5) . . . . ?
N1 C10 C11 C12 -138.9(7) . . . . ?
N1 C10 C11 C12' -117.3(7) . . . . ?
O1 C10 C11 C12 40.5(9) . . . . ?
O1 C10 C11 C12' 62.2(8) . . . . ?
N3 C9 C4 C5 -178.8(6) . . . . ?
N3 C9 C4 C3 0.8(8) . . . . ?
N3 C1 C2 C3 -0.4(11) . . . . ?
C17 C18 C19 C20 1.1(8) . . . . ?
C17 C16 C13 C12 -177.3(7) . . . . ?
C17 C16 C13 C14 59.9(10) . . . . ?
C8 N1 C10 O1 -0.9(9) . . . . ?
C8 N1 C10 C11 178.5(5) . . . . ?
C8 C9 C4 C5 -0.7(8) . . . . ?
C8 C9 C4 C3 178.9(5) . . . . ?
C8 C7 C6 C5 -0.3(10) . . . . ?
C10 N1 C8 C9 -166.0(5) . . . . ?
C10 N1 C8 C7 12.9(8) . . . . ?
C10 C11 C12 C13 -166.5(6) . . . . ?
C10 C11 C12' C13' -171.9(8) . . . . ?
C23 C16 C13 C12 -60.5(10) . . . . ?
C23 C16 C13 C14 176.7(7) . . . . ?
C20 C21 C22 C17 0.1(7) . . . . ?
C27 C26 C25 C24 -1.8(8) . . . . ?
C26 C27 C28 C23 -1.3(8) . . . . ?
C26 C25 C24 C23 -0.1(9) . . . . ?
C21 C20 C19 C18 -1.7(8) . . . . ?
C9 N3 C1 C2 1.3(9) . . . . ?
C9 C8 C7 C6 0.1(8) . . . . ?
C9 C4 C5 C6 0.5(10) . . . . ?
C9 C4 C3 C2 0.3(9) . . . . ?
C28 C23 C24 C25 1.2(8) . . . . ?
C28 C23 C16 C17 82.4(9) . . . . ?
C28 C23 C16 C13 -32.5(11) . . . . ?
C28 C23 C16' C17 116.7(7) . . . . ?
C28 C23 C16' C13' -118.8(8) . . . . ?
C28 C27 C26 C25 2.5(8) . . . . ?
C28 C27 C26 C29 -176.9(5) . . . . ?
C18 C17 C22 C21 -0.7(7) . . . . ?
C18 C17 C16 C23 -57.1(10) . . . . ?
C18 C17 C16 C13 55.6(10) . . . . ?
C18 C17 C16' C23 -98.6(7) . . . . ?
C18 C17 C16' C13' 136.5(8) . . . . ?
C4 C5 C6 C7 -0.1(11) . . . . ?
C22 C17 C18 C19 0.1(8) . . . . ?
C22 C17 C16 C23 117.8(6) . . . . ?
C22 C17 C16 C13 -129.4(7) . . . . ?
C22 C17 C16' C23 86.3(8) . . . . ?
C22 C17 C16' C13' -38.5(11) . . . . ?
C11 C12 C13 C16 175.9(9) . . . . ?
C11 C12 C13 C14 -62.6(10) . . . . ?
C7 C8 C9 N3 178.7(5) . . . . ?
C7 C8 C9 C4 0.3(7) . . . . ?
C19 C20 C21 C22 1.1(8) . . . . ?
C12 C13 C14 C15 -54.6(13) . . . . ?
C29 C26 C25 C24 177.5(5) . . . . ?
C24 C23 C28 C27 -0.5(8) . . . . ?
C24 C23 C16 C17 -99.4(7) . . . . ?
C24 C23 C16 C13 145.7(7) . . . . ?
C24 C23 C16' C17 -61.4(9) . . . . ?
C24 C23 C16' C13' 63.0(10) . . . . ?
C1 N3 C9 C8 -179.7(5) . . . . ?
C1 N3 C9 C4 -1.6(8) . . . . ?
C1 C2 C3 C4 -0.5(11) . . . . ?
C5 C4 C3 C2 179.9(6) . . . . ?
C16 C17 C18 C19 174.7(6) . . . . ?
C16 C17 C22 C21 -176.6(5) . . . . ?
C16 C23 C28 C27 177.5(6) . . . . ?
C16 C23 C24 C25 -177.4(5) . . . . ?
C16 C13 C14 C15 65.5(14) . . . . ?
C3 C4 C5 C6 -179.0(7) . . . . ?
C14' C13' C12' C11 -61.2(13) . . . . ?
C14' C13' C16' C17 -50.5(12) . . . . ?
C14' C13' C16' C23 -171.0(9) . . . . ?
C15' C14' C13' C12' -67.4(14) . . . . ?
C15' C14' C13' C16' 162.0(12) . . . . ?
C12' C13' C16' C17 -179.2(7) . . . . ?
C12' C13' C16' C23 60.3(11) . . . . ?
C16' C17 C18 C19 -175.8(5) . . . . ?
C16' C17 C22 C21 174.1(6) . . . . ?
C16' C23 C28 C27 -178.9(5) . . . . ?
C16' C23 C24 C25 179.3(6) . . . . ?
C16' C13' C12' C11 71.2(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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.818
