# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_mo_210316_dap_0m
_database_code_depnum_ccdc_archive 'CCDC 2195841'
loop_
_audit_author_name
_audit_author_address
'wei yuefang'
;Zhejiang University
China
;
_audit_update_record             
;
2022-08-09 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;
_audit_creation_date             2021-03-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            DAP
_chemical_name_systematic        
20,21-dimethyl-20,21-dihydro-9H-dibenzo[a,i]benzo[4,5]indolo[3,2-c]benzo[4,5]indolo[2,3-g]carbazole
_chemical_formula_moiety         '2(C4 H8 O), C42 H27 N3'
_chemical_formula_sum            'C50 H43 N3 O2'
_chemical_formula_weight         717.87
_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      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                   10.8046(4)
_cell_length_b                   22.2850(7)
_cell_length_c                   15.2955(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.9480(10)
_cell_angle_gamma                90
_cell_volume                     3678.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1178 before and 0.0687 after correction.
The Ratio of minimum to maximum transmission is 0.9496.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            72290
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.119
_diffrn_reflns_theta_min         2.097
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6115
_reflns_number_total             8116
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.628
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         8116
_refine_ls_number_restraints     46
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      5.703
_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)+(0.0744P)²+2.9964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1678
_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
 C49-C50 \\sim C49-C50A
 with sigma of 0.02
 C50-O2 \\sim C50A-O2A
 with sigma of 0.02
 C47-O2 \\sim C47-O2A
 with sigma of 0.02
 C19-O2 \\sim C49-O2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C49 \\sim O2 \\sim C50 \\sim O2A \\sim C50A: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04
4. Others
 Sof(H47C)=Sof(H47D)=Sof(H49C)=Sof(H49D)=Sof(O2A)=Sof(C50A)=Sof(H50C)=
 Sof(H50D)=1-FVAR(1)
 Sof(H47A)=Sof(H47B)=Sof(H49A)=Sof(H49B)=Sof(O2)=Sof(C50)=Sof(H50A)=Sof(H50B)=
 FVAR(1)
 Fixed X: O2A(0.10253) C50A(0.157261)
 Fixed Y: O2A(0.926519) C50A(0.86261)
 Fixed Z: O2A(0.404929) C50A(0.39559)
5.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,
 H47B), C47(H47C,H47D), C48(H48A,H48B), C49(H49A,H49B), C49(H49C,H49D),
 C50(H50A,H50B), C50A(H50C,H50D)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C7(H7), C8(H8), C17(H17), C18(H18),
 C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34),
  C37(H37), C38(H38), C39(H39), C40(H40)
5.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_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 0.29373(14) 0.49314(7) 0.69472(10) 0.0352(3) Uani 1 1 d . . . . .
C43 C 0.3127(2) 0.53496(10) 0.76471(14) 0.0394(5) Uani 1 1 d . . . . .
H43A H 0.261887 0.571437 0.753892 0.047 Uiso 1 1 calc R . . . .
H43B H 0.400991 0.546766 0.771605 0.047 Uiso 1 1 calc R . . . .
C44 C 0.2729(2) 0.50215(13) 0.84531(15) 0.0461(6) Uani 1 1 d . . . . .
H44A H 0.239518 0.530358 0.888224 0.055 Uiso 1 1 calc R . . . .
H44B H 0.342761 0.479521 0.873760 0.055 Uiso 1 1 calc R . . . .
C45 C 0.1722(3) 0.45984(14) 0.80830(19) 0.0576(7) Uani 1 1 d . . . . .
H45A H 0.186412 0.418470 0.830156 0.069 Uiso 1 1 calc R . . . .
H45B H 0.089277 0.473320 0.824864 0.069 Uiso 1 1 calc R . . . .
C46 C 0.1822(3) 0.46253(15) 0.7108(2) 0.0635(8) Uani 1 1 d . . . . .
H46A H 0.183852 0.421502 0.686081 0.076 Uiso 1 1 calc R . . . .
H46B H 0.110363 0.484230 0.683316 0.076 Uiso 1 1 calc R . . . .
N1 N 0.37450(15) 0.68698(7) 0.64178(11) 0.0273(4) Uani 1 1 d . . . . .
N2 N 0.51869(15) 0.56966(7) 0.40754(10) 0.0267(4) Uani 1 1 d . . . . .
H2 H 0.572975 0.551111 0.376153 0.032 Uiso 1 1 calc R . . . .
N3 N 0.12335(15) 0.63791(7) 0.48598(10) 0.0256(3) Uani 1 1 d . . . . .
C1 C 0.5616(2) 0.69227(11) 0.98619(14) 0.0392(5) Uani 1 1 d . . . . .
H1 H 0.544388 0.724553 1.024278 0.047 Uiso 1 1 calc R . . . .
C2 C 0.6266(2) 0.64418(12) 1.01867(15) 0.0423(5) Uani 1 1 d . . . . .
H2A H 0.654744 0.643145 1.078519 0.051 Uiso 1 1 calc R . . . .
C3 C 0.6516(2) 0.59616(11) 0.96297(15) 0.0389(5) Uani 1 1 d . . . . .
H3 H 0.692833 0.561534 0.986042 0.047 Uiso 1 1 calc R . . . .
C4 C 0.61700(19) 0.59876(10) 0.87538(13) 0.0308(4) Uani 1 1 d . . . . .
H4 H 0.635529 0.565957 0.838600 0.037 Uiso 1 1 calc R . . . .
C5 C 0.55432(18) 0.64933(9) 0.83886(13) 0.0270(4) Uani 1 1 d . . . . .
C6 C 0.5190(2) 0.69553(10) 0.89743(14) 0.0320(4) Uani 1 1 d . . . . .
C7 C 0.4378(2) 0.74214(10) 0.86716(14) 0.0365(5) Uani 1 1 d . . . . .
H7 H 0.420434 0.774265 0.905476 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3841(2) 0.74186(10) 0.78457(14) 0.0346(5) Uani 1 1 d . . . . .
H8 H 0.324487 0.771263 0.766511 0.042 Uiso 1 1 calc R . . . .
C9 C 0.42004(18) 0.69651(9) 0.72678(13) 0.0279(4) Uani 1 1 d . . . . .
C10 C 0.51383(18) 0.65483(9) 0.74831(13) 0.0258(4) Uani 1 1 d . . . . .
C11 C 0.53583(17) 0.62303(8) 0.66803(12) 0.0243(4) Uani 1 1 d . . . . .
C12 C 0.44255(17) 0.64105(8) 0.60639(12) 0.0238(4) Uani 1 1 d . . . . .
C13 C 0.43067(17) 0.61459(8) 0.52130(12) 0.0239(4) Uani 1 1 d . . . . .
C14 C 0.53379(17) 0.58204(8) 0.49554(12) 0.0244(4) Uani 1 1 d . . . . .
C15 C 0.63736(17) 0.56597(8) 0.55258(12) 0.0242(4) Uani 1 1 d . . . . .
C16 C 0.63865(17) 0.58709(8) 0.64069(12) 0.0245(4) Uani 1 1 d . . . . .
C17 C 0.74782(19) 0.57704(9) 0.69335(13) 0.0299(4) Uani 1 1 d . . . . .
H17 H 0.755125 0.594131 0.750281 0.036 Uiso 1 1 calc R . . . .
C18 C 0.84387(19) 0.54317(10) 0.66438(14) 0.0321(4) Uani 1 1 d . . . . .
H18 H 0.915504 0.536497 0.701762 0.039 Uiso 1 1 calc R . . . .
C19 C 0.83676(18) 0.51847(9) 0.58022(14) 0.0297(4) Uani 1 1 d D . . . .
H19 H 0.901298 0.493281 0.561654 0.036 Uiso 1 1 calc R . . . .
C20 C 0.73641(18) 0.53071(9) 0.52458(13) 0.0273(4) Uani 1 1 d . . . . .
H20 H 0.733497 0.515320 0.466593 0.033 Uiso 1 1 calc R . . . .
C21 C 0.34310(17) 0.61530(8) 0.44629(12) 0.0242(4) Uani 1 1 d . . . . .
C22 C 0.21593(17) 0.62973(8) 0.42766(12) 0.0242(4) Uani 1 1 d . . . . .
C23 C 0.16591(17) 0.63515(8) 0.34153(12) 0.0250(4) Uani 1 1 d . . . . .
C24 C 0.23337(18) 0.61150(9) 0.27000(13) 0.0267(4) Uani 1 1 d . . . . .
C25 C 0.35585(18) 0.58921(9) 0.28805(13) 0.0265(4) Uani 1 1 d . . . . .
C26 C 0.40521(18) 0.59090(9) 0.37636(13) 0.0259(4) Uani 1 1 d . . . . .
C27 C 0.4244(2) 0.56684(10) 0.21923(14) 0.0340(5) Uani 1 1 d . . . . .
H27 H 0.507697 0.554335 0.230968 0.041 Uiso 1 1 calc R . . . .
C28 C 0.3729(2) 0.56283(11) 0.13558(14) 0.0390(5) Uani 1 1 d . . . . .
H28 H 0.421073 0.549091 0.089334 0.047 Uiso 1 1 calc R . . . .
C29 C 0.2492(2) 0.57910(11) 0.11898(14) 0.0377(5) Uani 1 1 d . . . . .
H29 H 0.211652 0.573857 0.061967 0.045 Uiso 1 1 calc R . . . .
C30 C 0.1813(2) 0.60263(10) 0.18435(13) 0.0320(4) Uani 1 1 d . . . . .
H30 H 0.097107 0.613202 0.171603 0.038 Uiso 1 1 calc R . . . .
C31 C 0.03972(18) 0.65591(9) 0.34890(13) 0.0256(4) Uani 1 1 d . . . . .
C32 C 0.01538(18) 0.65214(9) 0.43782(13) 0.0265(4) Uani 1 1 d . . . . .
C33 C -0.10307(19) 0.66211(9) 0.47010(14) 0.0298(4) Uani 1 1 d . . . . .
H33 H -0.118492 0.655073 0.529823 0.036 Uiso 1 1 calc R . . . .
C34 C -0.1947(2) 0.68221(10) 0.41252(15) 0.0346(5) Uani 1 1 d . . . . .
H34 H -0.276216 0.687125 0.431876 0.042 Uiso 1 1 calc R . . . .
C35 C -0.1705(2) 0.69597(10) 0.32391(14) 0.0336(5) Uani 1 1 d . . . . .
C36 C -0.05199(19) 0.68395(9) 0.29083(13) 0.0284(4) Uani 1 1 d . . . . .
C37 C -0.0288(2) 0.70509(10) 0.20591(14) 0.0348(5) Uani 1 1 d . . . . .
H37 H 0.050935 0.699456 0.183843 0.042 Uiso 1 1 calc R . . . .
C38 C -0.1189(2) 0.73353(11) 0.15475(16) 0.0431(6) Uani 1 1 d . . . . .
H38 H -0.101077 0.747183 0.097929 0.052 Uiso 1 1 calc R . . . .
C39 C -0.2371(2) 0.74248(12) 0.18597(16) 0.0480(6) Uani 1 1 d . . . . .
H39 H -0.299666 0.761404 0.149813 0.058 Uiso 1 1 calc R . . . .
C40 C -0.2625(2) 0.72410(11) 0.26820(16) 0.0434(6) Uani 1 1 d . . . . .
H40 H -0.343082 0.730208 0.288591 0.052 Uiso 1 1 calc R . . . .
C41 C 0.29773(19) 0.73110(9) 0.59426(14) 0.0315(4) Uani 1 1 d . . . . .
H41A H 0.216333 0.733113 0.619567 0.047 Uiso 1 1 calc GR . . . .
H41B H 0.287491 0.719348 0.532571 0.047 Uiso 1 1 calc GR . . . .
H41C H 0.337721 0.770535 0.598658 0.047 Uiso 1 1 calc GR . . . .
C42 C 0.12450(19) 0.61424(10) 0.57477(13) 0.0309(4) Uani 1 1 d . . . . .
H42A H 0.069593 0.579290 0.576256 0.046 Uiso 1 1 calc GR . . . .
H42B H 0.095642 0.645224 0.614366 0.046 Uiso 1 1 calc GR . . . .
H42C H 0.209058 0.602266 0.593426 0.046 Uiso 1 1 calc GR . . . .
C47 C -0.0276(4) 0.9058(3) 0.4045(3) 0.122(2) Uani 1 1 d D . . . .
H47A H 0.007324 0.937679 0.443556 0.146 Uiso 0.788(5) 1 calc R . P A 1
H47B H -0.111156 0.918680 0.382388 0.146 Uiso 0.788(5) 1 calc R . P A 1
H47C H -0.079134 0.937041 0.430879 0.146 Uiso 0.212(5) 1 calc R . P A 2
H47D H -0.059483 0.899464 0.343350 0.146 Uiso 0.212(5) 1 calc R . P A 2
C48 C -0.0367(5) 0.8522(3) 0.4516(4) 0.131(2) Uani 1 1 d . . . . .
H48A H -0.112637 0.830016 0.432299 0.158 Uiso 1 1 calc R . . . .
H48B H -0.039354 0.860510 0.515082 0.158 Uiso 1 1 calc R . . . .
C49 C 0.0788(5) 0.81585(18) 0.4326(3) 0.1095(16) Uani 1 1 d D U . . .
H49A H 0.064063 0.772053 0.435013 0.131 Uiso 0.788(5) 1 calc R . P A 1
H49B H 0.150997 0.826669 0.471959 0.131 Uiso 0.788(5) 1 calc R . P A 1
H49C H 0.118143 0.798435 0.486720 0.131 Uiso 0.212(5) 1 calc R . P A 2
H49D H 0.059670 0.783380 0.389849 0.131 Uiso 0.212(5) 1 calc R . P A 2
O2 O 0.0499(3) 0.89767(18) 0.3327(2) 0.0907(13) Uani 0.788(5) 1 d D U P A 1
C50 C 0.0921(8) 0.8383(2) 0.3389(4) 0.124(2) Uani 0.788(5) 1 d D U P A 1
H50A H 0.180074 0.836321 0.323915 0.149 Uiso 0.788(5) 1 calc R . P A 1
H50B H 0.043000 0.812651 0.297305 0.149 Uiso 0.788(5) 1 calc R . P A 1
O2A O 0.102530 0.926519 0.404929 0.150(6) Uani 0.212(5) 1 d D U P A 2
C50A C 0.157261 0.862610 0.395590 0.117(5) Uani 0.212(5) 1 d D U P A 2
H50C H 0.166920 0.854004 0.332809 0.140 Uiso 0.212(5) 1 calc R . P A 2
H50D H 0.240566 0.861260 0.425667 0.140 Uiso 0.212(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
O1 C43 1.426(3) . ?
O1 C46 1.417(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.515(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C44 C45 1.526(4) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C45 C46 1.502(4) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
N1 C9 1.383(3) . ?
N1 C12 1.387(2) . ?
N1 C41 1.456(2) . ?
N2 H2 0.8800 . ?
N2 C14 1.375(2) . ?
N2 C26 1.377(2) . ?
N3 C22 1.386(2) . ?
N3 C32 1.384(2) . ?
N3 C42 1.456(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.361(3) . ?
C1 C6 1.413(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.403(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.415(3) . ?
C5 C6 1.429(3) . ?
C5 C10 1.436(3) . ?
C6 C7 1.422(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.362(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.410(3) . ?
C9 C10 1.401(3) . ?
C10 C11 1.448(3) . ?
C11 C12 1.403(3) . ?
C11 C16 1.449(3) . ?
C12 C13 1.429(3) . ?
C13 C14 1.403(3) . ?
C13 C21 1.449(3) . ?
C14 C15 1.429(3) . ?
C15 C16 1.427(3) . ?
C15 C20 1.412(3) . ?
C16 C17 1.412(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.398(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.371(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.426(3) . ?
C21 C26 1.401(3) . ?
C22 C23 1.403(3) . ?
C23 C24 1.445(3) . ?
C23 C31 1.450(3) . ?
C24 C25 1.427(3) . ?
C24 C30 1.413(3) . ?
C25 C26 1.427(3) . ?
C25 C27 1.409(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.372(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.395(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.375(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.401(3) . ?
C31 C36 1.439(3) . ?
C32 C33 1.413(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.366(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.427(3) . ?
C35 C36 1.426(3) . ?
C35 C40 1.421(3) . ?
C36 C37 1.416(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.372(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.400(4) . ?
C39 H39 0.9500 . ?
C39 C40 1.364(4) . ?
C40 H40 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 H47C 0.9900 . ?
C47 H47D 0.9900 . ?
C47 C48 1.402(6) . ?
C47 O2 1.426(5) . ?
C47 O2A 1.479(5) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.528(7) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 H49C 0.9900 . ?
C49 H49D 0.9900 . ?
C49 C50 1.531(7) . ?
C49 C50A 1.474(5) . ?
O2 C50 1.401(7) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
O2A C50A 1.55152(6) . ?
C50A H50C 0.9900 . ?
C50A H50D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C46 O1 C43 105.95(18) . . ?
O1 C43 H43A 110.7 . . ?
O1 C43 H43B 110.7 . . ?
O1 C43 C44 105.05(19) . . ?
H43A C43 H43B 108.8 . . ?
C44 C43 H43A 110.7 . . ?
C44 C43 H43B 110.7 . . ?
C43 C44 H44A 111.2 . . ?
C43 C44 H44B 111.2 . . ?
C43 C44 C45 102.9(2) . . ?
H44A C44 H44B 109.1 . . ?
C45 C44 H44A 111.2 . . ?
C45 C44 H44B 111.2 . . ?
C44 C45 H45A 110.8 . . ?
C44 C45 H45B 110.8 . . ?
H45A C45 H45B 108.8 . . ?
C46 C45 C44 104.9(2) . . ?
C46 C45 H45A 110.8 . . ?
C46 C45 H45B 110.8 . . ?
O1 C46 C45 107.3(2) . . ?
O1 C46 H46A 110.3 . . ?
O1 C46 H46B 110.3 . . ?
C45 C46 H46A 110.3 . . ?
C45 C46 H46B 110.3 . . ?
H46A C46 H46B 108.5 . . ?
C9 N1 C12 108.07(16) . . ?
C9 N1 C41 122.12(17) . . ?
C12 N1 C41 127.11(17) . . ?
C14 N2 H2 125.4 . . ?
C14 N2 C26 109.20(16) . . ?
C26 N2 H2 125.4 . . ?
C22 N3 C42 125.49(16) . . ?
C32 N3 C22 107.69(16) . . ?
C32 N3 C42 123.09(16) . . ?
C2 C1 H1 119.1 . . ?
C2 C1 C6 121.8(2) . . ?
C6 C1 H1 119.1 . . ?
C1 C2 H2A 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 117.65(18) . . ?
C4 C5 C10 124.37(18) . . ?
C6 C5 C10 117.72(18) . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 121.0(2) . . ?
C7 C6 C5 120.14(19) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.65(19) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C9 117.8(2) . . ?
C9 C8 H8 121.1 . . ?
N1 C9 C8 127.11(19) . . ?
N1 C9 C10 109.72(17) . . ?
C10 C9 C8 123.14(19) . . ?
C5 C10 C11 136.14(18) . . ?
C9 C10 C5 117.64(17) . . ?
C9 C10 C11 105.86(17) . . ?
C10 C11 C16 132.63(18) . . ?
C12 C11 C10 106.64(16) . . ?
C12 C11 C16 119.95(17) . . ?
N1 C12 C11 109.02(16) . . ?
N1 C12 C13 129.48(17) . . ?
C11 C12 C13 121.46(17) . . ?
C12 C13 C21 137.83(17) . . ?
C14 C13 C12 115.72(17) . . ?
C14 C13 C21 106.19(16) . . ?
N2 C14 C13 108.82(16) . . ?
N2 C14 C15 126.66(17) . . ?
C13 C14 C15 124.51(17) . . ?
C16 C15 C14 117.60(17) . . ?
C20 C15 C14 122.44(18) . . ?
C20 C15 C16 119.96(17) . . ?
C15 C16 C11 118.99(17) . . ?
C17 C16 C11 123.62(18) . . ?
C17 C16 C15 116.99(17) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.71(19) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.40(19) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.83(18) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.67(18) . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C13 138.07(18) . . ?
C26 C21 C13 106.34(16) . . ?
C26 C21 C22 115.43(17) . . ?
N3 C22 C21 128.39(17) . . ?
N3 C22 C23 109.70(16) . . ?
C23 C22 C21 121.86(17) . . ?
C22 C23 C24 119.64(17) . . ?
C22 C23 C31 105.84(16) . . ?
C24 C23 C31 133.49(18) . . ?
C25 C24 C23 118.63(17) . . ?
C30 C24 C23 124.11(18) . . ?
C30 C24 C25 116.87(18) . . ?
C26 C25 C24 118.14(17) . . ?
C27 C25 C24 119.78(18) . . ?
C27 C25 C26 122.08(18) . . ?
N2 C26 C21 108.78(17) . . ?
N2 C26 C25 126.99(18) . . ?
C21 C26 C25 124.23(18) . . ?
C25 C27 H27 119.5 . . ?
C28 C27 C25 121.1(2) . . ?
C28 C27 H27 119.5 . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.5(2) . . ?
C29 C28 H28 120.3 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.6(2) . . ?
C30 C29 H29 119.7 . . ?
C24 C30 H30 119.1 . . ?
C29 C30 C24 121.7(2) . . ?
C29 C30 H30 119.1 . . ?
C32 C31 C23 106.29(16) . . ?
C32 C31 C36 117.88(18) . . ?
C36 C31 C23 135.33(18) . . ?
N3 C32 C31 109.60(17) . . ?
N3 C32 C33 127.14(18) . . ?
C31 C32 C33 123.26(18) . . ?
C32 C33 H33 121.1 . . ?
C34 C33 C32 117.75(19) . . ?
C34 C33 H33 121.1 . . ?
C33 C34 H34 119.3 . . ?
C33 C34 C35 121.4(2) . . ?
C35 C34 H34 119.3 . . ?
C36 C35 C34 120.56(19) . . ?
C40 C35 C34 120.5(2) . . ?
C40 C35 C36 118.9(2) . . ?
C35 C36 C31 117.70(18) . . ?
C37 C36 C31 124.20(19) . . ?
C37 C36 C35 117.86(19) . . ?
C36 C37 H37 119.2 . . ?
C38 C37 C36 121.5(2) . . ?
C38 C37 H37 119.2 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.3(2) . . ?
C39 C38 H38 119.9 . . ?
C38 C39 H39 119.9 . . ?
C40 C39 C38 120.1(2) . . ?
C40 C39 H39 119.9 . . ?
C35 C40 H40 119.4 . . ?
C39 C40 C35 121.2(2) . . ?
C39 C40 H40 119.4 . . ?
N1 C41 H41A 109.5 . . ?
N1 C41 H41B 109.5 . . ?
N1 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N3 C42 H42A 109.5 . . ?
N3 C42 H42B 109.5 . . ?
N3 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
H47A C47 H47B 108.1 . . ?
H47C C47 H47D 108.1 . . ?
C48 C47 H47A 109.6 . . ?
C48 C47 H47B 109.6 . . ?
C48 C47 H47C 109.5 . . ?
C48 C47 H47D 109.5 . . ?
C48 C47 O2 110.3(5) . . ?
C48 C47 O2A 110.8(4) . . ?
O2 C47 H47A 109.6 . . ?
O2 C47 H47B 109.6 . . ?
O2A C47 H47C 109.5 . . ?
O2A C47 H47D 109.5 . . ?
C47 C48 H48A 110.6 . . ?
C47 C48 H48B 110.6 . . ?
C47 C48 C49 105.9(4) . . ?
H48A C48 H48B 108.7 . . ?
C49 C48 H48A 110.6 . . ?
C49 C48 H48B 110.6 . . ?
C48 C49 H49A 112.4 . . ?
C48 C49 H49B 112.4 . . ?
C48 C49 H49C 111.6 . . ?
C48 C49 H49D 111.6 . . ?
C48 C49 C50 97.0(4) . . ?
H49A C49 H49B 109.9 . . ?
H49C C49 H49D 109.4 . . ?
C50 C49 H49A 112.4 . . ?
C50 C49 H49B 112.4 . . ?
C50A C49 C48 100.9(3) . . ?
C50A C49 H49C 111.6 . . ?
C50A C49 H49D 111.6 . . ?
C50 O2 C47 105.7(4) . . ?
C49 C50 H50A 109.9 . . ?
C49 C50 H50B 109.9 . . ?
O2 C50 C49 109.1(4) . . ?
O2 C50 H50A 109.9 . . ?
O2 C50 H50B 109.9 . . ?
H50A C50 H50B 108.3 . . ?
C47 O2A C50A 94.6(2) . . ?
C49 C50A O2A 112.6(2) . . ?
C49 C50A H50C 109.1 . . ?
C49 C50A H50D 109.1 . . ?
O2A C50A H50C 109.1 . . ?
O2A C50A H50D 109.1 . . ?
H50C C50A H50D 107.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
