# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_exp_138
_database_code_depnum_ccdc_archive 'CCDC 2332061'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;University of Toyama
Japan
;
_audit_update_record             
;
2024-02-09 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'carbonyl-bridged rhodol'
_chemical_name_systematic        1a
_chemical_formula_moiety         'C27 H17 N O3'
_chemical_formula_sum            'C27 H17 N O3'
_chemical_formula_weight         403.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.3843(2)
_cell_length_b                   20.0427(5)
_cell_length_c                   24.5666(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3635.89(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4641
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      67.6560
_cell_measurement_theta_min      3.6030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 14 0.0237
0 -6 -14 0.0250
-5 4 1 0.0939
0 -9 -12 0.0273
-3 -10 3 0.0620
2 11 -1 0.1036
0 -13 2 0.0101
0 7 14 0.0154
0 13 -1 0.0042
0 13 -4 0.0077

_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.4964 5.6007 14.2981 0.0783 0.3152 0.9458
-0.0522 -5.8630 -14.2342 -0.0570 -0.2265 -0.9723
-4.6001 3.5148 1.2671 -0.2127 -0.8883 0.4069
0.2033 -8.8482 -11.6687 0.2232 -0.1745 -0.9590
-2.6840 -10.3990 3.4770 0.7903 -0.6073 -0.0817
2.3766 11.2859 -0.6190 -0.7608 0.5853 0.2805
0.3432 -12.8162 2.4591 0.9314 -0.0258 -0.3631
0.0750 6.7463 13.6322 -0.0206 0.2329 0.9723
-0.0146 12.9974 -0.5707 -0.8828 0.1156 0.4553
-0.2325 12.5170 -4.2602 -0.9676 0.0252 0.2513

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12026
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.465
_diffrn_reflns_theta_min         3.598
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  30.00   0.50   40.00    --  -40.71  25.00  30.00  120
  2  ω    -14.00  11.00   0.50   40.00    --  -40.71  43.00 -84.00   50
  3  ω    -56.00 -30.00   0.50  110.00    --  -96.35  50.00  30.00   52
  4  ω    -56.00 -30.00   0.50  110.00    --  -96.35  50.00  60.00   52
  5  ω    -56.00 -31.00   0.50  110.00    --  -96.35  50.00  90.00   50
  6  ω    -57.00 -32.00   0.50  110.00    --  -96.35  50.00 150.00   50
  7  ω    -57.00 -17.00   0.50   40.00    --  -40.71  82.00  52.00   80
  8  ω    -72.00 -47.00   0.50   40.00    --  -40.71 110.00 136.00   50
  9  ω   -100.00 -75.00   0.50  110.00    --  -96.35  82.00  52.00   50
 10  ω    -57.00 -31.00   0.50  110.00    --  -96.35  50.00   0.00   52
 11  ω    -64.00 -24.00   0.50  110.00    --  -96.35  96.00-120.00   80
 12  ω    -69.00 -29.00   0.50  110.00    --  -96.35  59.00-180.00   80
 13  ω   -105.00 -76.00   0.50  110.00    --  -96.35  96.00-120.00   58
 14  ω    -70.00 -30.00   0.50   40.00    --  -40.71 -43.00 123.00   80
 15  ω   -105.00 -80.00   0.50   40.00    --  -40.71 -43.00 123.00   50
 16  ω   -136.00 -86.00   0.50  110.00    --  -96.35-110.00  41.00  100
 17  ω   -160.00 -79.00   0.50  110.00    --  -96.35 -43.00 123.00  162
 18  ω     38.00  63.00   0.50   40.00    --   40.40-110.00  41.00   50
 19  ω     56.00  81.00   0.50   40.00    --   40.40  43.00 -84.00   50
 20  ω    126.00 160.00   0.50  110.00    --   96.04  43.00 -84.00   68
 21  ω     78.00 122.00   0.50  110.00    --   96.04  82.00  52.00   88
 22  ω    107.00 132.00   0.50  110.00    --   96.04 110.00 136.00   50
 23  ω     31.00  56.00   0.50  110.00    --   96.04 -50.00  60.00   50
 24  ω     29.00  54.00   0.50  110.00    --   96.04 -50.00  90.00   50
 25  ω     33.00  59.00   0.50  110.00    --   96.04 -59.00 120.00   52
 26  ω     49.00  76.00   0.50  110.00    --   96.04-110.00  41.00   54
 27  ω     29.00  54.00   0.50  110.00    --   96.04 -50.00 -60.00   50
 28  ω     74.00  99.00   0.50  110.00    --   96.04 -82.00 -68.00   50
 29  ω     62.00  97.00   0.50   40.00    --   40.40-138.00 -30.00   70
 30  ω     25.00  55.00   0.50   40.00    --   40.40-138.00 -30.00   60
 31  ω      5.00  30.00   0.50   40.00    --   40.40 -43.00 123.00   50
 32  ω    -13.00  14.00   0.50   40.00    --   40.40 -25.00  90.00   54
 33  ω     24.00  51.00   0.50   40.00    --   40.40 -82.00 -68.00   54
 34  ω    -27.00  -2.00   0.50   40.00    --   40.40 -12.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0040461000
_diffrn_orient_matrix_UB_12      -0.0665400000
_diffrn_orient_matrix_UB_13      0.0313993000
_diffrn_orient_matrix_UB_21      0.2035461000
_diffrn_orient_matrix_UB_22      0.0096115000
_diffrn_orient_matrix_UB_23      0.0112105000
_diffrn_orient_matrix_UB_31      -0.0453278000
_diffrn_orient_matrix_UB_32      0.0373086000
_diffrn_orient_matrix_UB_33      0.0531084000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2655
_reflns_number_total             3292
_reflns_odcompleteness_completeness 99.46
_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 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0527
_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)+(0.0839P)²+2.3233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1520
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00T(H00T), C00V(H00V)
2.b Idealised Me refined as rotating group:
 C00U(H00A,H00B,H00C)
;
_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
O001 O 0.5337(2) 0.59705(7) 0.76777(5) 0.0289(4) Uani 1 1 d . . . . .
O002 O 0.3958(2) 0.37332(8) 0.61156(6) 0.0348(4) Uani 1 1 d . . . . .
O003 O 0.6319(3) 0.58958(9) 0.95519(6) 0.0442(5) Uani 1 1 d . . . . .
N004 N 0.6236(3) 0.60642(8) 0.57621(7) 0.0295(4) Uani 1 1 d . . . . .
C005 C 0.4013(3) 0.40021(10) 0.65651(8) 0.0243(5) Uani 1 1 d . . . . .
C006 C 0.4333(3) 0.46031(10) 0.76490(8) 0.0243(4) Uani 1 1 d . . . . .
C007 C 0.5232(3) 0.56493(10) 0.71847(8) 0.0244(5) Uani 1 1 d . . . . .
C008 C 0.5665(3) 0.57275(10) 0.62133(8) 0.0253(5) Uani 1 1 d . . . . .
C009 C 0.4843(3) 0.48972(10) 0.81395(8) 0.0245(5) Uani 1 1 d . . . . .
C00A C 0.4595(3) 0.47015(10) 0.66342(8) 0.0235(4) Uani 1 1 d . . . . .
C00B C 0.4663(3) 0.49789(10) 0.71600(8) 0.0238(5) Uani 1 1 d . . . . .
C00C C 0.3567(3) 0.39236(10) 0.75847(8) 0.0243(4) Uani 1 1 d . . . . .
C00D C 0.6384(3) 0.67784(10) 0.57432(8) 0.0280(5) Uani 1 1 d . . . . .
C00E C 0.5088(3) 0.50554(11) 0.61773(8) 0.0262(5) Uani 1 1 d . . . . .
H00E H 0.503947 0.484455 0.583125 0.031 Uiso 1 1 calc R U . . .
C00F C 0.3450(3) 0.36366(10) 0.70597(8) 0.0257(5) Uani 1 1 d . . . . .
C00G C 0.5326(3) 0.55984(11) 0.81498(8) 0.0275(5) Uani 1 1 d . . . . .
C00H C 0.2867(3) 0.35435(11) 0.80171(9) 0.0281(5) Uani 1 1 d . . . . .
H00H H 0.281103 0.373642 0.836989 0.034 Uiso 1 1 calc R U . . .
C00I C 0.5692(3) 0.60224(10) 0.67359(8) 0.0260(5) Uani 1 1 d . . . . .
H00I H 0.602715 0.647730 0.677688 0.031 Uiso 1 1 calc R U . . .
C00J C 0.5033(3) 0.45642(11) 0.86570(8) 0.0275(5) Uani 1 1 d . . . . .
H00J H 0.483658 0.409611 0.867259 0.033 Uiso 1 1 calc R U . . .
C00K C 0.5753(3) 0.59361(11) 0.86108(9) 0.0307(5) Uani 1 1 d . . . . .
H00K H 0.598915 0.640148 0.859221 0.037 Uiso 1 1 calc R U . . .
C00L C 0.2794(3) 0.29869(11) 0.69916(9) 0.0308(5) Uani 1 1 d . . . . .
H00L H 0.273382 0.280151 0.663615 0.037 Uiso 1 1 calc R U . . .
C00M C 0.8035(3) 0.70625(11) 0.56027(8) 0.0318(5) Uani 1 1 d . . . . .
H00M H 0.907679 0.678916 0.556065 0.038 Uiso 1 1 calc R U . . .
C00N C 0.2231(3) 0.26094(11) 0.74311(9) 0.0329(5) Uani 1 1 d . . . . .
H00N H 0.183393 0.216250 0.738280 0.039 Uiso 1 1 calc R U . . .
C00O C 0.5476(3) 0.48873(12) 0.91192(9) 0.0315(5) Uani 1 1 d . . . . .
H00O H 0.554340 0.464225 0.944965 0.038 Uiso 1 1 calc R U . . .
C00P C 0.2260(3) 0.28980(11) 0.79443(9) 0.0312(5) Uani 1 1 d . . . . .
H00P H 0.185567 0.264831 0.824974 0.037 Uiso 1 1 calc R U . . .
C00Q C 0.4867(3) 0.71759(11) 0.58117(8) 0.0331(5) Uani 1 1 d . . . . .
H00Q H 0.374282 0.698120 0.591262 0.040 Uiso 1 1 calc R U . . .
C00R C 0.4995(4) 0.78587(11) 0.57322(9) 0.0357(6) Uani 1 1 d . . . . .
H00R H 0.395638 0.813285 0.577778 0.043 Uiso 1 1 calc R U . . .
C00S C 0.5855(3) 0.55996(12) 0.91281(9) 0.0343(5) Uani 1 1 d . . . . .
C00T C 0.8159(4) 0.77451(12) 0.55240(9) 0.0370(6) Uani 1 1 d . . . . .
H00T H 0.928596 0.794060 0.542735 0.044 Uiso 1 1 calc R U . . .
C00U C 0.6237(4) 0.57372(11) 0.52310(8) 0.0355(5) Uani 1 1 d . . . . .
H00A H 0.690045 0.531478 0.525538 0.053 Uiso 1 1 calc R U . . .
H00B H 0.682406 0.602781 0.496310 0.053 Uiso 1 1 calc R U . . .
H00C H 0.498656 0.564941 0.511801 0.053 Uiso 1 1 calc R U . . .
C00V C 0.6640(4) 0.81426(11) 0.55861(8) 0.0384(6) Uani 1 1 d . . . . .
H00V H 0.672316 0.861038 0.552871 0.046 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
O001 C007 1.374(2) . ?
O001 C00G 1.379(2) . ?
O002 C005 1.229(2) . ?
O003 C00S 1.247(3) . ?
N004 C008 1.365(3) . ?
N004 C00D 1.436(3) . ?
N004 C00U 1.460(3) . ?
C005 C00A 1.476(3) . ?
C005 C00F 1.478(3) . ?
C006 C009 1.393(3) . ?
C006 C00B 1.439(3) . ?
C006 C00C 1.483(3) . ?
C007 C00B 1.409(3) . ?
C007 C00I 1.375(3) . ?
C008 C00E 1.416(3) . ?
C008 C00I 1.413(3) . ?
C009 C00G 1.450(3) . ?
C009 C00J 1.443(3) . ?
C00A C00B 1.407(3) . ?
C00A C00E 1.377(3) . ?
C00C C00F 1.415(3) . ?
C00C C00H 1.405(3) . ?
C00D C00M 1.389(3) . ?
C00D C00Q 1.385(3) . ?
C00E H00E 0.9500 . ?
C00F C00L 1.399(3) . ?
C00G C00K 1.356(3) . ?
C00H H00H 0.9500 . ?
C00H C00P 1.381(3) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C00O 1.348(3) . ?
C00K H00K 0.9500 . ?
C00K C00S 1.441(3) . ?
C00L H00L 0.9500 . ?
C00L C00N 1.382(3) . ?
C00M H00M 0.9500 . ?
C00M C00T 1.385(3) . ?
C00N H00N 0.9500 . ?
C00N C00P 1.387(3) . ?
C00O H00O 0.9500 . ?
C00O C00S 1.455(3) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00Q C00R 1.386(3) . ?
C00R H00R 0.9500 . ?
C00R C00V 1.389(4) . ?
C00T H00T 0.9500 . ?
C00T C00V 1.384(4) . ?
C00U H00A 0.9800 . ?
C00U H00B 0.9800 . ?
C00U H00C 0.9800 . ?
C00V H00V 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 O001 C00G 119.20(16) . . ?
C008 N004 C00D 122.85(17) . . ?
C008 N004 C00U 120.27(17) . . ?
C00D N004 C00U 114.74(17) . . ?
O002 C005 C00A 121.95(18) . . ?
O002 C005 C00F 120.78(18) . . ?
C00A C005 C00F 117.25(17) . . ?
C009 C006 C00B 117.05(19) . . ?
C009 C006 C00C 125.71(18) . . ?
C00B C006 C00C 117.16(18) . . ?
O001 C007 C00B 120.10(17) . . ?
O001 C007 C00I 115.99(18) . . ?
C00I C007 C00B 123.90(18) . . ?
N004 C008 C00E 120.85(18) . . ?
N004 C008 C00I 121.79(18) . . ?
C00I C008 C00E 117.32(18) . . ?
C006 C009 C00G 119.45(18) . . ?
C006 C009 C00J 126.34(19) . . ?
C00J C009 C00G 114.15(18) . . ?
C00B C00A C005 119.42(18) . . ?
C00E C00A C005 118.19(18) . . ?
C00E C00A C00B 122.38(19) . . ?
C007 C00B C006 120.92(18) . . ?
C00A C00B C006 123.61(19) . . ?
C00A C00B C007 115.27(18) . . ?
C00F C00C C006 119.58(18) . . ?
C00H C00C C006 123.88(18) . . ?
C00H C00C C00F 116.50(18) . . ?
C00M C00D N004 118.9(2) . . ?
C00Q C00D N004 120.5(2) . . ?
C00Q C00D C00M 120.3(2) . . ?
C008 C00E H00E 119.4 . . ?
C00A C00E C008 121.25(19) . . ?
C00A C00E H00E 119.4 . . ?
C00C C00F C005 122.05(18) . . ?
C00L C00F C005 117.40(18) . . ?
C00L C00F C00C 120.56(19) . . ?
O001 C00G C009 120.72(18) . . ?
C00K C00G O001 115.54(19) . . ?
C00K C00G C009 123.73(19) . . ?
C00C C00H H00H 119.0 . . ?
C00P C00H C00C 122.0(2) . . ?
C00P C00H H00H 119.0 . . ?
C007 C00I C008 119.83(19) . . ?
C007 C00I H00I 120.1 . . ?
C008 C00I H00I 120.1 . . ?
C009 C00J H00J 118.5 . . ?
C00O C00J C009 122.9(2) . . ?
C00O C00J H00J 118.5 . . ?
C00G C00K H00K 119.5 . . ?
C00G C00K C00S 121.0(2) . . ?
C00S C00K H00K 119.5 . . ?
C00F C00L H00L 119.3 . . ?
C00N C00L C00F 121.3(2) . . ?
C00N C00L H00L 119.3 . . ?
C00D C00M H00M 120.1 . . ?
C00T C00M C00D 119.8(2) . . ?
C00T C00M H00M 120.1 . . ?
C00L C00N H00N 120.8 . . ?
C00L C00N C00P 118.5(2) . . ?
C00P C00N H00N 120.8 . . ?
C00J C00O H00O 119.0 . . ?
C00J C00O C00S 122.1(2) . . ?
C00S C00O H00O 119.0 . . ?
C00H C00P C00N 120.9(2) . . ?
C00H C00P H00P 119.6 . . ?
C00N C00P H00P 119.6 . . ?
C00D C00Q H00Q 120.1 . . ?
C00D C00Q C00R 119.7(2) . . ?
C00R C00Q H00Q 120.1 . . ?
C00Q C00R H00R 120.0 . . ?
C00Q C00R C00V 120.1(2) . . ?
C00V C00R H00R 120.0 . . ?
O003 C00S C00K 121.9(2) . . ?
O003 C00S C00O 122.2(2) . . ?
C00K C00S C00O 115.85(19) . . ?
C00M C00T H00T 120.0 . . ?
C00V C00T C00M 120.0(2) . . ?
C00V C00T H00T 120.0 . . ?
N004 C00U H00A 109.5 . . ?
N004 C00U H00B 109.5 . . ?
N004 C00U H00C 109.5 . . ?
H00A C00U H00B 109.5 . . ?
H00A C00U H00C 109.5 . . ?
H00B C00U H00C 109.5 . . ?
C00R C00V H00V 120.0 . . ?
C00T C00V C00R 120.1(2) . . ?
C00T C00V H00V 120.0 . . ?

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
O001 C007 C00B C006 -5.4(3) . . . . ?
O001 C007 C00B C00A 179.64(18) . . . . ?
O001 C007 C00I C008 178.47(19) . . . . ?
O001 C00G C00K C00S -177.7(2) . . . . ?
O002 C005 C00A C00B -178.8(2) . . . . ?
O002 C005 C00A C00E 0.0(3) . . . . ?
O002 C005 C00F C00C 177.4(2) . . . . ?
O002 C005 C00F C00L -2.4(3) . . . . ?
N004 C008 C00E C00A 176.7(2) . . . . ?
N004 C008 C00I C007 -175.2(2) . . . . ?
N004 C00D C00M C00T 172.96(19) . . . . ?
N004 C00D C00Q C00R -172.82(19) . . . . ?
C005 C00A C00B C006 5.2(3) . . . . ?
C005 C00A C00B C007 -179.90(18) . . . . ?
C005 C00A C00E C008 -179.84(19) . . . . ?
C005 C00F C00L C00N -179.8(2) . . . . ?
C006 C009 C00G O001 -1.9(3) . . . . ?
C006 C009 C00G C00K 176.6(2) . . . . ?
C006 C009 C00J C00O -177.7(2) . . . . ?
C006 C00C C00F C005 -2.1(3) . . . . ?
C006 C00C C00F C00L 177.64(19) . . . . ?
C006 C00C C00H C00P -176.29(19) . . . . ?
C007 O001 C00G C009 -12.5(3) . . . . ?
C007 O001 C00G C00K 168.81(19) . . . . ?
C008 N004 C00D C00M 124.2(2) . . . . ?
C008 N004 C00D C00Q -62.0(3) . . . . ?
C009 C006 C00B C007 -8.9(3) . . . . ?
C009 C006 C00B C00A 165.7(2) . . . . ?
C009 C006 C00C C00F -167.2(2) . . . . ?
C009 C006 C00C C00H 15.3(3) . . . . ?
C009 C00G C00K C00S 3.6(4) . . . . ?
C009 C00J C00O C00S -1.9(3) . . . . ?
C00A C005 C00F C00C -4.0(3) . . . . ?
C00A C005 C00F C00L 176.26(19) . . . . ?
C00B C006 C009 C00G 12.2(3) . . . . ?
C00B C006 C009 C00J -164.7(2) . . . . ?
C00B C006 C00C C00F 9.4(3) . . . . ?
C00B C006 C00C C00H -168.03(19) . . . . ?
C00B C007 C00I C008 -2.1(3) . . . . ?
C00B C00A C00E C008 -1.1(3) . . . . ?
C00C C006 C009 C00G -171.13(19) . . . . ?
C00C C006 C009 C00J 11.9(3) . . . . ?
C00C C006 C00B C007 174.18(19) . . . . ?
C00C C006 C00B C00A -11.2(3) . . . . ?
C00C C00F C00L C00N 0.5(3) . . . . ?
C00C C00H C00P C00N -3.3(3) . . . . ?
C00D N004 C008 C00E 163.4(2) . . . . ?
C00D N004 C008 C00I -19.2(3) . . . . ?
C00D C00M C00T C00V 0.1(3) . . . . ?
C00D C00Q C00R C00V -0.2(3) . . . . ?
C00E C008 C00I C007 2.3(3) . . . . ?
C00E C00A C00B C006 -173.5(2) . . . . ?
C00E C00A C00B C007 1.3(3) . . . . ?
C00F C005 C00A C00B 2.6(3) . . . . ?
C00F C005 C00A C00E -178.63(19) . . . . ?
C00F C00C C00H C00P 6.2(3) . . . . ?
C00F C00L C00N C00P 2.6(3) . . . . ?
C00G O001 C007 C00B 16.0(3) . . . . ?
C00G O001 C007 C00I -164.56(19) . . . . ?
C00G C009 C00J C00O 5.2(3) . . . . ?
C00G C00K C00S O003 176.9(2) . . . . ?
C00G C00K C00S C00O 0.1(3) . . . . ?
C00H C00C C00F C005 175.52(19) . . . . ?
C00H C00C C00F C00L -4.7(3) . . . . ?
C00I C007 C00B C006 175.3(2) . . . . ?
C00I C007 C00B C00A 0.3(3) . . . . ?
C00I C008 C00E C00A -0.8(3) . . . . ?
C00J C009 C00G O001 175.36(18) . . . . ?
C00J C009 C00G C00K -6.1(3) . . . . ?
C00J C00O C00S O003 -177.8(2) . . . . ?
C00J C00O C00S C00K -0.9(3) . . . . ?
C00L C00N C00P C00H -1.2(3) . . . . ?
C00M C00D C00Q C00R 0.9(3) . . . . ?
C00M C00T C00V C00R 0.6(3) . . . . ?
C00Q C00D C00M C00T -0.8(3) . . . . ?
C00Q C00R C00V C00T -0.5(3) . . . . ?
C00U N004 C008 C00E 0.8(3) . . . . ?
C00U N004 C008 C00I 178.3(2) . . . . ?
C00U N004 C00D C00M -72.4(3) . . . . ?
C00U N004 C00D C00Q 101.4(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 1.845
_oxdiff_exptl_absorpt_empirical_full_min 0.624
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/Et2O'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_140
_database_code_depnum_ccdc_archive 'CCDC 2332063'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;University of Toyama
Japan
;
_audit_update_record             
;
2024-02-09 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2021-05-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'carbonyl-bridged rhodol'
_chemical_name_systematic        1c
_chemical_formula_moiety         '2(C28 H16 F3 N O3)'
_chemical_formula_sum            'C56 H32 F6 N2 O6'
_chemical_formula_weight         942.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
F F 0.0727 0.0534 '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                   10.9940(3)
_cell_length_b                   11.0404(3)
_cell_length_c                   17.6631(4)
_cell_angle_alpha                83.512(2)
_cell_angle_beta                 80.770(2)
_cell_angle_gamma                72.972(3)
_cell_volume                     2018.43(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8954
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      67.9470
_cell_measurement_theta_min      2.5260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.384
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 1 0.1633
-1 -2 10 0.1275
4 -4 2 0.1296
2 1 -10 0.1022
-1 6 6 0.0995
6 -2 3 0.1380
-7 -3 -1 0.1591
-3 -7 -1 0.1256
0 7 1 0.1113
6 6 1 0.0976
2 -6 0 0.1264
0 5 -7 0.1268
3 3 -8 0.0995
-5 -2 7 0.1600
-2 -4 8 0.1399
-2 -2 -11 0.1086
-5 1 -9 0.1342
1 -4 -8 0.1311
3 2 11 0.1125
-2 4 7 0.1060
-6 -5 -6 0.1075
1 -6 -3 0.1153
7 1 5 0.1272
5 5 6 0.1105
0 7 4 0.0914
5 5 -3 0.0920

_exptl_crystal_size_max          0.313
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.216
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.5755 3.8468 0.7917 0.0206 0.0750 0.9970
-1.2395 -2.3154 10.0980 0.2332 0.9701 -0.0677
4.1202 -4.3198 1.8066 0.0395 0.1746 -0.9839
2.1460 1.4755 -10.0258 -0.2321 -0.9629 -0.1377
-0.7627 5.5235 6.4941 -0.4810 0.4595 0.7467
5.5233 -2.4702 3.3164 -0.2512 0.2354 -0.9389
-6.9436 -3.4281 -0.6944 0.8754 0.1629 0.4552
-3.0044 -7.0824 -0.7423 0.8836 0.1622 -0.4392
0.4820 6.9754 0.5798 -0.6682 -0.1217 0.7339
5.8825 5.5449 0.7966 -0.9797 -0.1813 -0.0856
1.5899 -6.2126 -0.3932 0.4305 0.0773 -0.8993
0.4278 5.2135 -6.8338 -0.4512 -0.7331 0.5090
3.4879 3.3125 -7.9367 -0.5209 -0.8495 -0.0842
-4.6952 -1.6428 7.2506 0.4743 0.7750 0.4175
-2.1457 -4.4181 7.7842 0.5122 0.8339 -0.2054
-2.3181 -2.3031 -11.1222 0.4766 -0.8787 -0.0262
-4.7020 0.8689 -8.5907 0.3671 -0.6801 0.6346
1.4144 -4.4131 -7.8840 0.3390 -0.6215 -0.7063
2.6154 2.0302 11.1159 -0.4762 0.8784 -0.0410
-1.7039 4.4839 7.3986 -0.3182 0.5830 0.7475
-5.6348 -4.8246 -6.3740 0.9363 -0.3324 0.1129
1.0506 -6.2364 -3.3839 0.4985 -0.1746 -0.8491
6.8161 1.2361 4.7628 -0.6988 0.2496 -0.6704
5.2004 5.2825 6.4143 -0.9424 0.3343 -0.0079
0.1483 6.5573 4.2880 -0.6312 0.2219 0.7432
5.3243 5.1960 -2.7621 -0.8768 -0.4753 -0.0724

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19341
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.495
_diffrn_reflns_theta_min         2.541
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_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  99.00   0.50    0.20    --   40.40  37.00-150.00   54
  2  ω     72.00 162.00   0.50    0.36    --   96.04  68.00-150.00  180
  3  ω     79.00 162.00   0.50    0.36    --   96.04  59.00 -60.00  166
  4  ω    126.00 152.00   0.50    0.36    --   96.04  68.00  90.00   52
  5  ω     72.00 112.00   0.50    0.36    --   96.04  68.00  90.00   80
  6  ω    -26.00  30.00   0.50    0.20    --   40.40 -25.00 120.00  112
  7  ω     -8.00  22.00   0.50    0.20    --   40.40 -37.00  90.00   60
  8  ω    -14.00  28.00   0.50    0.20    --   40.40 -50.00  60.00   84
  9  ω     25.00  51.00   0.50    0.20    --   40.40-141.00  66.00   52
 10  ω      2.00  79.00   0.50    0.20    --   40.40-104.00 -30.00  154
 11  ω     11.00  38.00   0.50    0.20    --   40.40-128.00-122.00   54
 12  ω     57.00  90.00   0.50    0.20    --   40.40-128.00-122.00   66
 13  ω     94.00 129.00   0.50    0.36    --   96.04-144.00  30.00   70
 14  ω     88.00 113.00   0.50    0.36    --   96.04-117.00 120.00   50
 15  ω     29.00 112.00   0.50    0.36    --   96.04-117.00  90.00  166
 16  ω     30.00  59.00   0.50    0.36    --   96.04-117.00 120.00   58
 17  ω     38.00  74.00   0.50    0.36    --   96.04-144.00  30.00   72
 18  ω     74.00 107.00   0.50    0.36    --   96.04-128.00-122.00   66
 19  ω     52.00  83.00   0.50    0.36    --   96.04 -68.00-120.00   62
 20  ω     28.00  54.00   0.50    0.36    --   96.04 -59.00-120.00   52
 21  ω     29.00  54.00   0.50    0.36    --   96.04 -50.00   0.00   50
 22  ω     32.00  68.00   0.50    0.36    --   96.04 -59.00 120.00   72
 23  ω     91.00 132.00   0.50    0.36    --   96.04 128.00 -47.00   82
 24  ω     62.00  88.00   0.50    0.20    --   40.40 141.00 123.00   52
 25  ω     94.00 159.00   0.50    0.36    --   96.04 141.00 123.00  130
 26  ω     59.00  88.00   0.50    0.36    --   96.04 141.00 123.00   58
 27  ω    -78.00   5.00   0.50    0.20    --  -40.71 104.00 120.00  166
 28  ω    -84.00 -49.00   0.50    0.20    --  -40.71 141.00 123.00   70
 29  ω   -103.00 -78.00   0.50    0.36    --  -96.35 141.00 123.00   50
 30  ω    -75.00 -50.00   0.50    0.20    --  -40.71 128.00 -47.00   50
 31  ω   -119.00 -94.00   0.50    0.36    --  -96.35 128.00 -47.00   50
 32  ω   -108.00 -46.00   0.50    0.36    --  -96.35  96.00 -60.00  124
 33  ω   -109.00 -44.00   0.50    0.36    --  -96.35  96.00-150.00  130
 34  ω   -105.00 -35.00   0.50    0.36    --  -96.35  77.00-180.00  140
 35  ω    -53.00 -28.00   0.50    0.36    --  -96.35  59.00-180.00   50
 36  ω    -76.00 -42.00   0.50    0.36    --  -96.35  77.00 -90.00   68
 37  ω    -57.00 -31.00   0.50    0.36    --  -96.35  50.00-180.00   52
 38  ω   -104.00 -79.00   0.50    0.36    --  -96.35  77.00 -90.00   50
 39  ω    -56.00 -30.00   0.50    0.36    --  -96.35  50.00 -90.00   52
 40  ω    -57.00 -30.00   0.50    0.36    --  -96.35  50.00 -30.00   54
 41  ω    -16.00  28.00   0.50    0.20    --  -40.71  12.00   0.00   88
 42  ω    -33.00  12.00   0.50    0.20    --  -40.71  37.00 120.00   90
 43  ω    -76.00 -43.00   0.50    0.36    --  -96.35  68.00 120.00   66
 44  ω    -69.00 -44.00   0.50    0.36    --  -96.35  59.00 150.00   50
 45  ω   -165.00-127.00   0.50    0.36    --  -96.35 -25.00  90.00   76
 46  ω   -163.00 -74.00   0.50    0.36    --  -96.35 -68.00 120.00  178
 47  ω   -108.00 -83.00   0.50    0.36    --  -96.35 -33.00-120.00   50
 48  ω   -109.00 -84.00   0.50    0.36    --  -96.35 -33.00-150.00   50
 49  ω   -163.00-125.00   0.50    0.36    --  -96.35 -33.00-150.00   76
 50  ω   -158.00-132.00   0.50    0.36    --  -96.35 -33.00-120.00   52
 51  ω   -107.00 -82.00   0.50    0.36    --  -96.35 -25.00  90.00   50
 52  ω    -95.00 -55.00   0.50    0.20    --  -40.71 -50.00  90.00   80
 53  ω   -100.00 -71.00   0.50    0.20    --  -40.71 -63.00-120.00   58
 54  ω    -65.00 -26.00   0.50    0.20    --  -40.71 -63.00-120.00   78
 55  ω    -53.00 -26.00   0.50    0.20    --  -40.71 -63.00-150.00   54
 56  ω    -91.00 -65.00   0.50    0.20    --  -40.71 -63.00-150.00   52
 57  ω    -86.00 -61.00   0.50    0.20    --  -40.71-138.00-180.00   50
 58  ω   -108.00 -68.00   0.50    0.20    --  -40.71-138.00 -90.00   80
 59  ω   -107.00 -81.00   0.50    0.20    --  -40.71-141.00  66.00   52
 60  ω    -86.00 -61.00   0.50    0.20    --  -40.71-138.00 120.00   50
 61  ω   -162.00 -57.00   0.50    0.36    --  -96.35-144.00 -90.00  210
 62  ω   -163.00 -75.00   0.50    0.36    --  -96.35-117.00-150.00  176
 63  ω   -125.00 -99.00   0.50    0.36    --  -96.35-128.00-122.00   52
 64  ω   -136.00-111.00   0.50    0.36    --  -96.35-141.00  66.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0811032000
_diffrn_orient_matrix_UB_12      -0.0895816000
_diffrn_orient_matrix_UB_13      -0.0073979000
_diffrn_orient_matrix_UB_21      -0.0207570000
_diffrn_orient_matrix_UB_22      -0.0233368000
_diffrn_orient_matrix_UB_23      0.0881657000
_diffrn_orient_matrix_UB_31      -0.1219084000
_diffrn_orient_matrix_UB_32      0.1132806000
_diffrn_orient_matrix_UB_33      0.0043087000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6165
_reflns_number_total             7344
_reflns_odcompleteness_completeness 99.99
_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 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.065
_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     631
_refine_ls_number_reflns         7344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.022
_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)+(0.1017P)²+0.1633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1534
_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 Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C54(H54A,H54B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C52(H52), C5(H5), C50(H50), C12(H12), C17(H17), C2(H2), C35(H35),
 C4(H4), C19(H19), C20(H20), C69(H69), C70(H70), C68(H68), C18(H18), C62(H62),
 C66(H66), C59(H59), C39(H39), C67(H67), C34(H34), C60(H60), C42(H42), C61(H61),
  C33(H33), C41(H41), C31(H31), C32(H32)
;
_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
F5 F 0.50389(12) 1.12566(10) 0.32576(7) 0.0444(3) Uani 1 1 d . . . . .
F6 F 0.59692(12) 0.97177(11) 0.40171(7) 0.0478(3) Uani 1 1 d . . . . .
F4 F 0.39132(12) 1.02268(11) 0.40304(7) 0.0502(3) Uani 1 1 d . . . . .
O14 O 0.83900(12) 0.52790(11) 0.39880(7) 0.0317(3) Uani 1 1 d . . . . .
O65 O 0.35406(12) 0.57550(12) 0.37812(7) 0.0333(3) Uani 1 1 d . . . . .
F2 F 0.06096(14) 1.16872(11) 0.29684(7) 0.0548(4) Uani 1 1 d . . . . .
F3 F 0.14041(13) 1.01262(12) 0.37531(8) 0.0545(3) Uani 1 1 d . . . . .
F1 F -0.06398(13) 1.08947(12) 0.38007(8) 0.0576(4) Uani 1 1 d . . . . .
O22 O 1.08927(13) 0.73294(12) 0.10671(8) 0.0389(3) Uani 1 1 d . . . . .
O63 O 0.54983(13) 0.69059(13) 0.05267(7) 0.0405(3) Uani 1 1 d . . . . .
O64 O 0.52697(13) 0.25558(13) 0.55700(8) 0.0415(4) Uani 1 1 d . . . . .
O29 O 1.01849(13) 0.21701(13) 0.58245(8) 0.0412(3) Uani 1 1 d . . . . .
N53 N 0.15662(14) 0.93581(14) 0.22106(9) 0.0307(3) Uani 1 1 d . . . . .
N23 N 0.64018(14) 0.89672(14) 0.24728(9) 0.0317(3) Uani 1 1 d . . . . .
C9 C 0.96604(17) 0.67529(16) 0.21980(10) 0.0286(4) Uani 1 1 d . . . . .
C51 C 0.25637(17) 0.82740(16) 0.23191(10) 0.0293(4) Uani 1 1 d . . . . .
C10 C 0.85932(17) 0.77478(16) 0.20797(10) 0.0302(4) Uani 1 1 d . . . . .
H10 H 0.862553 0.830951 0.163271 0.036 Uiso 1 1 calc R U . . .
C13 C 0.85115(17) 0.61015(16) 0.33553(10) 0.0287(4) Uani 1 1 d . . . . .
C1 C 0.94608(17) 0.44037(16) 0.42187(11) 0.0292(4) Uani 1 1 d . . . . .
C49 C 0.46988(17) 0.61111(16) 0.25439(10) 0.0291(4) Uani 1 1 d . . . . .
C48 C 0.46112(17) 0.68460(16) 0.18352(10) 0.0289(4) Uani 1 1 d . . . . .
C8 C 0.96646(17) 0.58899(16) 0.28532(10) 0.0283(4) Uani 1 1 d . . . . .
C21 C 1.18803(17) 0.45833(16) 0.24141(10) 0.0282(4) Uani 1 1 d . . . . .
C16 C 1.19252(17) 0.54536(16) 0.17609(10) 0.0291(4) Uani 1 1 d . . . . .
C6 C 1.06983(17) 0.42309(16) 0.37483(10) 0.0291(4) Uani 1 1 d . . . . .
C44 C 0.57818(17) 0.50444(16) 0.26930(10) 0.0289(4) Uani 1 1 d . . . . .
C52 C 0.25901(18) 0.75067(17) 0.30148(11) 0.0306(4) Uani 1 1 d . . . . .
H52 H 0.190285 0.771260 0.342223 0.037 Uiso 1 1 calc R U . . .
C7 C 1.07673(17) 0.48689(16) 0.30239(10) 0.0282(4) Uani 1 1 d . . . . .
C36 C 0.36197(17) 0.64584(16) 0.30976(10) 0.0296(4) Uani 1 1 d . . . . .
C30 C 0.65104(17) 0.98856(16) 0.18333(11) 0.0305(4) Uani 1 1 d . . . . .
C46 C 0.67904(18) 0.54157(16) 0.13487(11) 0.0306(4) Uani 1 1 d . . . . .
C38 C 0.45259(17) 0.47091(16) 0.39382(10) 0.0301(4) Uani 1 1 d . . . . .
C45 C 0.69282(18) 0.48255(16) 0.21008(10) 0.0299(4) Uani 1 1 d . . . . .
C5 C 1.17646(17) 0.33914(16) 0.41062(11) 0.0309(4) Uani 1 1 d . . . . .
H5 H 1.261257 0.330974 0.385390 0.037 Uiso 1 1 calc R U . . .
C50 C 0.35829(17) 0.78831(16) 0.17222(10) 0.0303(4) Uani 1 1 d . . . . .
H50 H 0.355792 0.834427 0.123447 0.036 Uiso 1 1 calc R U . . .
C12 C 0.74290(17) 0.70863(16) 0.32540(10) 0.0301(4) Uani 1 1 d . . . . .
H12 H 0.667480 0.718048 0.361649 0.036 Uiso 1 1 calc R U . . .
C11 C 0.74555(17) 0.79536(16) 0.26045(11) 0.0300(4) Uani 1 1 d . . . . .
C43 C 0.56580(17) 0.43063(17) 0.33804(10) 0.0293(4) Uani 1 1 d . . . . .
C65 C 0.15903(17) 1.01881(16) 0.15200(10) 0.0291(4) Uani 1 1 d . . . . .
C24 C 0.51792(17) 0.91750(17) 0.29678(10) 0.0314(4) Uani 1 1 d . . . . .
H24A H 0.509811 0.835082 0.322213 0.038 Uiso 1 1 calc R U . . .
H24B H 0.447549 0.951407 0.264820 0.038 Uiso 1 1 calc R U . . .
C15 C 1.08362(18) 0.65866(16) 0.16340(10) 0.0304(4) Uani 1 1 d . . . . .
C17 C 1.29825(18) 0.52158(17) 0.11879(10) 0.0311(4) Uani 1 1 d . . . . .
H17 H 1.300861 0.581390 0.075872 0.037 Uiso 1 1 calc R U . . .
C2 C 0.92651(18) 0.37033(17) 0.48818(11) 0.0322(4) Uani 1 1 d . . . . .
H2 H 0.841664 0.380697 0.513863 0.039 Uiso 1 1 calc R U . . .
C35 C 0.59673(17) 0.98659(16) 0.11810(11) 0.0326(4) Uani 1 1 d . . . . .
H35 H 0.552050 0.925705 0.115563 0.039 Uiso 1 1 calc R U . . .
C4 C 1.16003(17) 0.27241(17) 0.47810(11) 0.0323(4) Uani 1 1 d . . . . .
H4 H 1.233412 0.218674 0.498839 0.039 Uiso 1 1 calc R U . . .
C19 C 1.39217(18) 0.32319(17) 0.18499(11) 0.0334(4) Uani 1 1 d . . . . .
H19 H 1.459881 0.246842 0.187975 0.040 Uiso 1 1 calc R U . . .
C20 C 1.28774(17) 0.34478(16) 0.24160(10) 0.0310(4) Uani 1 1 d . . . . .
H20 H 1.283145 0.280930 0.281918 0.037 Uiso 1 1 calc R U . . .
C69 C 0.24756(18) 1.17034(17) 0.07011(11) 0.0343(4) Uani 1 1 d . . . . .
H69 H 0.309145 1.217069 0.058702 0.041 Uiso 1 1 calc R U . . .
C70 C 0.24686(17) 1.08943(16) 0.13664(11) 0.0321(4) Uani 1 1 d . . . . .
H70 H 0.306472 1.082669 0.171411 0.038 Uiso 1 1 calc R U . . .
C68 C 0.15815(18) 1.18237(16) 0.02071(11) 0.0339(4) Uani 1 1 d . . . . .
H68 H 0.158077 1.238067 -0.024417 0.041 Uiso 1 1 calc R U . . .
C18 C 1.39888(18) 0.41297(17) 0.12331(11) 0.0335(4) Uani 1 1 d . . . . .
H18 H 1.471835 0.399381 0.084976 0.040 Uiso 1 1 calc R U . . .
C47 C 0.56172(18) 0.64193(17) 0.11776(11) 0.0317(4) Uani 1 1 d . . . . .
C3 C 1.03267(18) 0.27994(17) 0.52059(11) 0.0328(4) Uani 1 1 d . . . . .
C62 C 0.78175(18) 0.51404(17) 0.07571(11) 0.0346(4) Uani 1 1 d . . . . .
H62 H 0.770033 0.550818 0.025180 0.042 Uiso 1 1 calc R U . . .
C66 C 0.07029(18) 1.03038(17) 0.10215(11) 0.0329(4) Uani 1 1 d . . . . .
H66 H 0.010463 0.981613 0.112542 0.040 Uiso 1 1 calc R U . . .
C54 C 0.04130(17) 0.96731(17) 0.27665(11) 0.0331(4) Uani 1 1 d . . . . .
H54A H 0.029699 0.888324 0.305482 0.040 Uiso 1 1 calc R U . . .
H54B H -0.033867 1.005279 0.248873 0.040 Uiso 1 1 calc R U . . .
C59 C 0.81629(17) 0.41006(16) 0.22314(11) 0.0325(4) Uani 1 1 d . . . . .
H59 H 0.831000 0.376924 0.273931 0.039 Uiso 1 1 calc R U . . .
C40 C 0.53406(18) 0.30443(17) 0.48998(11) 0.0334(4) Uani 1 1 d . . . . .
C39 C 0.43665(18) 0.41281(17) 0.46476(11) 0.0332(4) Uani 1 1 d . . . . .
H39 H 0.359763 0.444201 0.498453 0.040 Uiso 1 1 calc R U . . .
C67 C 0.06917(18) 1.11390(17) 0.03667(11) 0.0343(4) Uani 1 1 d . . . . .
H67 H 0.007120 1.123654 0.003028 0.041 Uiso 1 1 calc R U . . .
C34 C 0.60815(19) 1.07460(17) 0.05625(11) 0.0362(4) Uani 1 1 d . . . . .
H34 H 0.568960 1.075372 0.011947 0.043 Uiso 1 1 calc R U . . .
C60 C 0.91756(18) 0.38534(17) 0.16408(11) 0.0341(4) Uani 1 1 d . . . . .
H60 H 0.999908 0.334397 0.174595 0.041 Uiso 1 1 calc R U . . .
C42 C 0.65555(18) 0.31235(17) 0.36121(11) 0.0332(4) Uani 1 1 d . . . . .
H42 H 0.726602 0.274624 0.324977 0.040 Uiso 1 1 calc R U . . .
C61 C 0.89937(18) 0.43473(17) 0.08935(11) 0.0355(4) Uani 1 1 d . . . . .
H61 H 0.967482 0.413837 0.048287 0.043 Uiso 1 1 calc R U . . .
C33 C 0.67583(18) 1.16019(17) 0.05911(11) 0.0367(4) Uani 1 1 d . . . . .
H33 H 0.685640 1.218162 0.016111 0.044 Uiso 1 1 calc R U . . .
C41 C 0.64258(18) 0.25367(17) 0.43184(11) 0.0358(4) Uani 1 1 d . . . . .
H41 H 0.705515 0.177319 0.444229 0.043 Uiso 1 1 calc R U . . .
C31 C 0.71615(17) 1.07711(17) 0.18734(12) 0.0355(4) Uani 1 1 d . . . . .
H31 H 0.751184 1.079584 0.232749 0.043 Uiso 1 1 calc R U . . .
C25 C 0.50320(18) 1.00826(17) 0.35739(11) 0.0364(4) Uani 1 1 d . . . . .
C55 C 0.04569(19) 1.05838(18) 0.33266(12) 0.0392(5) Uani 1 1 d . . . . .
C32 C 0.73004(18) 1.16247(18) 0.12457(12) 0.0381(4) Uani 1 1 d . . . . .
H32 H 0.776450 1.222129 0.126459 0.046 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
F5 C25 1.354(2) . ?
F6 C25 1.335(2) . ?
F4 C25 1.336(2) . ?
O14 C13 1.373(2) . ?
O14 C1 1.373(2) . ?
O65 C36 1.365(2) . ?
O65 C38 1.369(2) . ?
F2 C55 1.351(2) . ?
F3 C55 1.328(2) . ?
F1 C55 1.331(2) . ?
O22 C15 1.226(2) . ?
O63 C47 1.223(2) . ?
O64 C40 1.245(2) . ?
O29 C3 1.240(2) . ?
N53 C51 1.385(2) . ?
N53 C65 1.442(2) . ?
N53 C54 1.453(2) . ?
N23 C30 1.445(2) . ?
N23 C11 1.385(2) . ?
N23 C24 1.453(2) . ?
C9 C10 1.378(2) . ?
C9 C8 1.413(2) . ?
C9 C15 1.479(2) . ?
C51 C52 1.411(2) . ?
C51 C50 1.412(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.409(3) . ?
C13 C8 1.400(2) . ?
C13 C12 1.377(2) . ?
C1 C6 1.449(2) . ?
C1 C2 1.352(2) . ?
C49 C48 1.413(2) . ?
C49 C44 1.443(2) . ?
C49 C36 1.399(2) . ?
C48 C50 1.375(2) . ?
C48 C47 1.483(2) . ?
C8 C7 1.439(2) . ?
C21 C16 1.420(2) . ?
C21 C7 1.478(2) . ?
C21 C20 1.403(2) . ?
C16 C15 1.481(2) . ?
C16 C17 1.396(2) . ?
C6 C7 1.391(2) . ?
C6 C5 1.450(2) . ?
C44 C45 1.482(2) . ?
C44 C43 1.395(2) . ?
C52 H52 0.9500 . ?
C52 C36 1.375(3) . ?
C30 C35 1.385(3) . ?
C30 C31 1.384(3) . ?
C46 C45 1.422(2) . ?
C46 C47 1.482(2) . ?
C46 C62 1.397(3) . ?
C38 C43 1.449(2) . ?
C38 C39 1.351(2) . ?
C45 C59 1.400(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.344(3) . ?
C50 H50 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.411(2) . ?
C43 C42 1.449(2) . ?
C65 C70 1.387(3) . ?
C65 C66 1.386(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.506(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.445(3) . ?
C35 H35 0.9500 . ?
C35 C34 1.393(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.463(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(3) . ?
C19 C18 1.396(2) . ?
C20 H20 0.9500 . ?
C69 H69 0.9500 . ?
C69 C70 1.394(2) . ?
C69 C68 1.385(3) . ?
C70 H70 0.9500 . ?
C68 H68 0.9500 . ?
C68 C67 1.380(3) . ?
C18 H18 0.9500 . ?
C62 H62 0.9500 . ?
C62 C61 1.373(3) . ?
C66 H66 0.9500 . ?
C66 C67 1.395(2) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C54 C55 1.503(3) . ?
C59 H59 0.9500 . ?
C59 C60 1.384(3) . ?
C40 C39 1.435(3) . ?
C40 C41 1.462(3) . ?
C39 H39 0.9500 . ?
C67 H67 0.9500 . ?
C34 H34 0.9500 . ?
C34 C33 1.373(3) . ?
C60 H60 0.9500 . ?
C60 C61 1.392(3) . ?
C42 H42 0.9500 . ?
C42 C41 1.346(3) . ?
C61 H61 0.9500 . ?
C33 H33 0.9500 . ?
C33 C32 1.389(3) . ?
C41 H41 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.391(3) . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O14 C13 119.88(14) . . ?
C36 O65 C38 120.35(13) . . ?
C51 N53 C65 121.56(14) . . ?
C51 N53 C54 121.57(14) . . ?
C65 N53 C54 116.78(13) . . ?
C30 N23 C24 117.69(13) . . ?
C11 N23 C30 119.68(14) . . ?
C11 N23 C24 122.61(14) . . ?
C10 C9 C8 121.48(16) . . ?
C10 C9 C15 119.60(15) . . ?
C8 C9 C15 118.92(15) . . ?
N53 C51 C52 121.86(15) . . ?
N53 C51 C50 120.55(15) . . ?
C52 C51 C50 117.57(15) . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.70(16) . . ?
C11 C10 H10 119.1 . . ?
O14 C13 C8 120.25(15) . . ?
O14 C13 C12 115.30(15) . . ?
C12 C13 C8 124.43(16) . . ?
O14 C1 C6 120.54(15) . . ?
C2 C1 O14 115.85(16) . . ?
C2 C1 C6 123.56(16) . . ?
C48 C49 C44 123.84(16) . . ?
C36 C49 C48 114.92(15) . . ?
C36 C49 C44 121.19(16) . . ?
C49 C48 C47 118.40(15) . . ?
C50 C48 C49 122.22(16) . . ?
C50 C48 C47 119.21(16) . . ?
C9 C8 C7 123.90(16) . . ?
C13 C8 C9 115.51(15) . . ?
C13 C8 C7 120.58(16) . . ?
C16 C21 C7 119.36(15) . . ?
C20 C21 C16 116.96(16) . . ?
C20 C21 C7 123.55(15) . . ?
C21 C16 C15 122.02(15) . . ?
C17 C16 C21 120.21(15) . . ?
C17 C16 C15 117.65(15) . . ?
C1 C6 C5 114.37(15) . . ?
C7 C6 C1 119.10(15) . . ?
C7 C6 C5 126.52(16) . . ?
C49 C44 C45 117.16(15) . . ?
C43 C44 C49 117.22(16) . . ?
C43 C44 C45 125.63(15) . . ?
C51 C52 H52 120.3 . . ?
C36 C52 C51 119.38(16) . . ?
C36 C52 H52 120.3 . . ?
C8 C7 C21 117.26(15) . . ?
C6 C7 C8 117.39(15) . . ?
C6 C7 C21 125.35(15) . . ?
O65 C36 C49 120.52(15) . . ?
O65 C36 C52 115.09(15) . . ?
C52 C36 C49 124.39(16) . . ?
C35 C30 N23 119.55(17) . . ?
C31 C30 N23 119.96(17) . . ?
C31 C30 C35 120.49(17) . . ?
C45 C46 C47 122.01(16) . . ?
C62 C46 C45 120.26(16) . . ?
C62 C46 C47 117.49(16) . . ?
O65 C38 C43 121.13(15) . . ?
C39 C38 O65 114.94(15) . . ?
C39 C38 C43 123.91(16) . . ?
C46 C45 C44 118.57(16) . . ?
C59 C45 C44 124.63(17) . . ?
C59 C45 C46 116.77(16) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 C6 122.57(17) . . ?
C4 C5 H5 118.7 . . ?
C51 C50 H50 119.4 . . ?
C48 C50 C51 121.11(16) . . ?
C48 C50 H50 119.4 . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 119.09(16) . . ?
C11 C12 H12 120.5 . . ?
N23 C11 C10 120.38(15) . . ?
N23 C11 C12 121.86(16) . . ?
C10 C11 C12 117.76(15) . . ?
C44 C43 C38 119.30(15) . . ?
C44 C43 C42 126.76(16) . . ?
C38 C43 C42 113.93(16) . . ?
C70 C65 N53 120.36(17) . . ?
C66 C65 N53 119.46(16) . . ?
C66 C65 C70 120.16(16) . . ?
N23 C24 H24A 109.0 . . ?
N23 C24 H24B 109.0 . . ?
N23 C24 C25 112.90(16) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
O22 C15 C9 121.43(15) . . ?
O22 C15 C16 121.13(16) . . ?
C9 C15 C16 117.39(15) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.23(16) . . ?
C18 C17 H17 119.4 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.02(17) . . ?
C3 C2 H2 119.5 . . ?
C30 C35 H35 120.3 . . ?
C30 C35 C34 119.48(18) . . ?
C34 C35 H35 120.3 . . ?
C5 C4 H4 119.0 . . ?
C5 C4 C3 122.05(16) . . ?
C3 C4 H4 119.0 . . ?
C20 C19 H19 119.8 . . ?
C20 C19 C18 120.31(16) . . ?
C18 C19 H19 119.8 . . ?
C21 C20 H20 119.0 . . ?
C19 C20 C21 121.91(16) . . ?
C19 C20 H20 119.0 . . ?
C70 C69 H69 120.1 . . ?
C68 C69 H69 120.1 . . ?
C68 C69 C70 119.76(18) . . ?
C65 C70 C69 119.92(18) . . ?
C65 C70 H70 120.0 . . ?
C69 C70 H70 120.0 . . ?
C69 C68 H68 119.8 . . ?
C67 C68 C69 120.36(17) . . ?
C67 C68 H68 119.8 . . ?
C17 C18 C19 119.08(16) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
O63 C47 C48 121.25(16) . . ?
O63 C47 C46 121.55(16) . . ?
C46 C47 C48 117.16(16) . . ?
O29 C3 C2 122.66(17) . . ?
O29 C3 C4 121.53(16) . . ?
C2 C3 C4 115.71(16) . . ?
C46 C62 H62 119.4 . . ?
C61 C62 C46 121.14(18) . . ?
C61 C62 H62 119.4 . . ?
C65 C66 H66 120.1 . . ?
C65 C66 C67 119.73(18) . . ?
C67 C66 H66 120.1 . . ?
N53 C54 H54A 109.0 . . ?
N53 C54 H54B 109.0 . . ?
N53 C54 C55 112.85(16) . . ?
H54A C54 H54B 107.8 . . ?
C55 C54 H54A 109.0 . . ?
C55 C54 H54B 109.0 . . ?
C45 C59 H59 119.1 . . ?
C60 C59 C45 121.80(18) . . ?
C60 C59 H59 119.1 . . ?
O64 C40 C39 122.44(17) . . ?
O64 C40 C41 121.66(16) . . ?
C39 C40 C41 115.90(16) . . ?
C38 C39 C40 121.02(17) . . ?
C38 C39 H39 119.5 . . ?
C40 C39 H39 119.5 . . ?
C68 C67 C66 120.04(18) . . ?
C68 C67 H67 120.0 . . ?
C66 C67 H67 120.0 . . ?
C35 C34 H34 119.9 . . ?
C33 C34 C35 120.21(19) . . ?
C33 C34 H34 119.9 . . ?
C59 C60 H60 119.8 . . ?
C59 C60 C61 120.34(17) . . ?
C61 C60 H60 119.8 . . ?
C43 C42 H42 118.6 . . ?
C41 C42 C43 122.82(17) . . ?
C41 C42 H42 118.6 . . ?
C62 C61 C60 119.19(17) . . ?
C62 C61 H61 120.4 . . ?
C60 C61 H61 120.4 . . ?
C34 C33 H33 119.8 . . ?
C34 C33 C32 120.33(17) . . ?
C32 C33 H33 119.8 . . ?
C40 C41 H41 119.2 . . ?
C42 C41 C40 121.67(16) . . ?
C42 C41 H41 119.2 . . ?
C30 C31 H31 120.2 . . ?
C30 C31 C32 119.67(19) . . ?
C32 C31 H31 120.2 . . ?
F5 C25 C24 111.57(16) . . ?
F6 C25 F5 106.48(17) . . ?
F6 C25 F4 108.00(16) . . ?
F6 C25 C24 113.01(14) . . ?
F4 C25 F5 106.07(14) . . ?
F4 C25 C24 111.33(17) . . ?
F2 C55 C54 111.97(16) . . ?
F3 C55 F2 106.72(18) . . ?
F3 C55 F1 107.76(16) . . ?
F3 C55 C54 113.21(15) . . ?
F1 C55 F2 105.87(14) . . ?
F1 C55 C54 110.91(18) . . ?
C33 C32 C31 119.77(19) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 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
O14 C13 C8 C9 176.52(16) . . . . ?
O14 C13 C8 C7 -4.9(3) . . . . ?
O14 C13 C12 C11 -177.96(16) . . . . ?
O14 C1 C6 C7 -6.5(3) . . . . ?
O14 C1 C6 C5 172.80(16) . . . . ?
O14 C1 C2 C3 -176.61(17) . . . . ?
O65 C38 C43 C44 4.2(3) . . . . ?
O65 C38 C43 C42 -174.98(17) . . . . ?
O65 C38 C39 C40 -178.00(17) . . . . ?
O64 C40 C39 C38 173.77(19) . . . . ?
O64 C40 C41 C42 -174.5(2) . . . . ?
N53 C51 C52 C36 -178.41(17) . . . . ?
N53 C51 C50 C48 176.64(17) . . . . ?
N53 C65 C70 C69 -179.36(15) . . . . ?
N53 C65 C66 C67 177.72(15) . . . . ?
N53 C54 C55 F2 58.9(2) . . . . ?
N53 C54 C55 F3 -61.8(2) . . . . ?
N53 C54 C55 F1 176.97(14) . . . . ?
N23 C30 C35 C34 -179.51(15) . . . . ?
N23 C30 C31 C32 177.81(15) . . . . ?
N23 C24 C25 F5 63.30(19) . . . . ?
N23 C24 C25 F6 -56.7(2) . . . . ?
N23 C24 C25 F4 -178.41(14) . . . . ?
C9 C10 C11 N23 179.52(17) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C9 C8 C7 C21 -10.7(3) . . . . ?
C9 C8 C7 C6 169.42(17) . . . . ?
C51 N53 C65 C70 -68.0(2) . . . . ?
C51 N53 C65 C66 113.91(19) . . . . ?
C51 N53 C54 C55 95.9(2) . . . . ?
C51 C52 C36 O65 -178.13(16) . . . . ?
C51 C52 C36 C49 2.9(3) . . . . ?
C10 C9 C8 C13 1.4(3) . . . . ?
C10 C9 C8 C7 -177.12(17) . . . . ?
C10 C9 C15 O22 1.3(3) . . . . ?
C10 C9 C15 C16 -175.97(17) . . . . ?
C13 O14 C1 C6 -7.7(3) . . . . ?
C13 O14 C1 C2 174.81(16) . . . . ?
C13 C8 C7 C21 170.87(16) . . . . ?
C13 C8 C7 C6 -9.1(3) . . . . ?
C13 C12 C11 N23 -179.60(17) . . . . ?
C13 C12 C11 C10 1.3(3) . . . . ?
C1 O14 C13 C8 13.3(3) . . . . ?
C1 O14 C13 C12 -168.52(16) . . . . ?
C1 C6 C7 C8 14.3(3) . . . . ?
C1 C6 C7 C21 -165.56(17) . . . . ?
C1 C6 C5 C4 6.9(3) . . . . ?
C1 C2 C3 O29 177.77(19) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C49 C48 C50 C51 0.8(3) . . . . ?
C49 C48 C47 O63 169.42(18) . . . . ?
C49 C48 C47 C46 -12.9(3) . . . . ?
C49 C44 C45 C46 -17.5(2) . . . . ?
C49 C44 C45 C59 160.63(18) . . . . ?
C49 C44 C43 C38 -6.2(3) . . . . ?
C49 C44 C43 C42 172.90(18) . . . . ?
C48 C49 C44 C45 8.3(3) . . . . ?
C48 C49 C44 C43 -171.50(17) . . . . ?
C48 C49 C36 O65 174.38(16) . . . . ?
C48 C49 C36 C52 -6.7(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C8 C9 C15 O22 -178.01(18) . . . . ?
C8 C9 C15 C16 4.7(3) . . . . ?
C8 C13 C12 C11 0.1(3) . . . . ?
C21 C16 C15 O22 179.87(18) . . . . ?
C21 C16 C15 C9 -2.8(3) . . . . ?
C21 C16 C17 C18 1.2(3) . . . . ?
C16 C21 C7 C8 12.2(3) . . . . ?
C16 C21 C7 C6 -167.92(18) . . . . ?
C16 C21 C20 C19 6.2(3) . . . . ?
C16 C17 C18 C19 2.5(3) . . . . ?
C6 C1 C2 C3 6.0(3) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C44 C49 C48 C50 -177.74(17) . . . . ?
C44 C49 C48 C47 7.0(3) . . . . ?
C44 C49 C36 O65 -3.2(3) . . . . ?
C44 C49 C36 C52 175.76(18) . . . . ?
C44 C45 C59 C60 175.08(17) . . . . ?
C44 C43 C42 C41 173.10(19) . . . . ?
C52 C51 C50 C48 -4.8(3) . . . . ?
C7 C21 C16 C15 -5.7(3) . . . . ?
C7 C21 C16 C17 178.45(17) . . . . ?
C7 C21 C20 C19 -177.84(18) . . . . ?
C7 C6 C5 C4 -173.93(18) . . . . ?
C36 O65 C38 C43 -1.4(3) . . . . ?
C36 O65 C38 C39 176.76(17) . . . . ?
C36 C49 C48 C50 4.8(3) . . . . ?
C36 C49 C48 C47 -170.49(17) . . . . ?
C36 C49 C44 C45 -174.35(17) . . . . ?
C36 C49 C44 C43 5.9(3) . . . . ?
C30 N23 C11 C10 -5.9(3) . . . . ?
C30 N23 C11 C12 175.04(17) . . . . ?
C30 N23 C24 C25 -83.1(2) . . . . ?
C30 C35 C34 C33 1.9(3) . . . . ?
C30 C31 C32 C33 1.6(3) . . . . ?
C46 C45 C59 C60 -6.8(3) . . . . ?
C46 C62 C61 C60 -2.7(3) . . . . ?
C38 O65 C36 C49 0.9(3) . . . . ?
C38 O65 C36 C52 -178.14(16) . . . . ?
C38 C43 C42 C41 -7.7(3) . . . . ?
C45 C44 C43 C38 174.01(17) . . . . ?
C45 C44 C43 C42 -6.9(3) . . . . ?
C45 C46 C47 O63 -178.72(18) . . . . ?
C45 C46 C47 C48 3.6(3) . . . . ?
C45 C46 C62 C61 -3.1(3) . . . . ?
C45 C59 C60 C61 1.2(3) . . . . ?
C5 C6 C7 C8 -164.81(17) . . . . ?
C5 C6 C7 C21 15.3(3) . . . . ?
C5 C4 C3 O29 179.29(19) . . . . ?
C5 C4 C3 C2 -4.2(3) . . . . ?
C50 C51 C52 C36 3.0(3) . . . . ?
C50 C48 C47 O63 -6.0(3) . . . . ?
C50 C48 C47 C46 171.73(17) . . . . ?
C12 C13 C8 C9 -1.5(3) . . . . ?
C12 C13 C8 C7 177.10(18) . . . . ?
C11 N23 C30 C35 104.8(2) . . . . ?
C11 N23 C30 C31 -74.8(2) . . . . ?
C11 N23 C24 C25 95.2(2) . . . . ?
C43 C44 C45 C46 162.31(18) . . . . ?
C43 C44 C45 C59 -19.6(3) . . . . ?
C43 C38 C39 C40 0.1(3) . . . . ?
C43 C42 C41 C40 1.5(3) . . . . ?
C65 N53 C51 C52 175.40(17) . . . . ?
C65 N53 C51 C50 -6.1(3) . . . . ?
C65 N53 C54 C55 -87.6(2) . . . . ?
C65 C66 C67 C68 1.6(3) . . . . ?
C24 N23 C30 C35 -76.9(2) . . . . ?
C24 N23 C30 C31 103.6(2) . . . . ?
C24 N23 C11 C10 175.85(17) . . . . ?
C24 N23 C11 C12 -3.2(3) . . . . ?
C15 C9 C10 C11 -179.33(17) . . . . ?
C15 C9 C8 C13 -179.28(17) . . . . ?
C15 C9 C8 C7 2.2(3) . . . . ?
C15 C16 C17 C18 -174.78(18) . . . . ?
C17 C16 C15 O22 -4.2(3) . . . . ?
C17 C16 C15 C9 173.10(17) . . . . ?
C2 C1 C6 C7 170.81(18) . . . . ?
C2 C1 C6 C5 -9.9(3) . . . . ?
C35 C30 C31 C32 -1.7(3) . . . . ?
C35 C34 C33 C32 -2.0(3) . . . . ?
C20 C21 C16 C15 170.39(17) . . . . ?
C20 C21 C16 C17 -5.5(3) . . . . ?
C20 C21 C7 C8 -163.66(18) . . . . ?
C20 C21 C7 C6 16.3(3) . . . . ?
C20 C19 C18 C17 -1.8(3) . . . . ?
C69 C68 C67 C66 -1.1(3) . . . . ?
C70 C65 C66 C67 -0.4(3) . . . . ?
C70 C69 C68 C67 -0.6(3) . . . . ?
C68 C69 C70 C65 1.7(3) . . . . ?
C18 C19 C20 C21 -2.7(3) . . . . ?
C47 C48 C50 C51 175.98(17) . . . . ?
C47 C46 C45 C44 11.7(3) . . . . ?
C47 C46 C45 C59 -166.55(17) . . . . ?
C47 C46 C62 C61 171.37(18) . . . . ?
C62 C46 C45 C44 -174.08(17) . . . . ?
C62 C46 C45 C59 7.7(3) . . . . ?
C62 C46 C47 O63 6.9(3) . . . . ?
C62 C46 C47 C48 -170.80(17) . . . . ?
C66 C65 C70 C69 -1.3(3) . . . . ?
C54 N53 C51 C52 -8.3(3) . . . . ?
C54 N53 C51 C50 170.24(17) . . . . ?
C54 N53 C65 C70 115.51(19) . . . . ?
C54 N53 C65 C66 -62.6(2) . . . . ?
C59 C60 C61 C62 3.6(3) . . . . ?
C39 C38 C43 C44 -173.77(19) . . . . ?
C39 C38 C43 C42 7.0(3) . . . . ?
C39 C40 C41 C42 5.9(3) . . . . ?
C34 C33 C32 C31 0.3(3) . . . . ?
C41 C40 C39 C38 -6.7(3) . . . . ?
C31 C30 C35 C34 0.0(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 1.569
_oxdiff_exptl_absorpt_empirical_full_min 0.659
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/Et2O'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_141
_database_code_depnum_ccdc_archive 'CCDC 2332062'
loop_
_audit_author_name
_audit_author_address
'Masaru Tanioka'
;University of Toyama
Japan
;
_audit_update_record             
;
2024-02-09 deposited with the CCDC.	2024-05-27 downloaded from the CCDC.
;
_audit_creation_date             2021-05-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'carbonyl-bridged rhodol'
_chemical_name_systematic        1b
_chemical_formula_moiety         'C32 H19 N O3'
_chemical_formula_sum            'C32 H19 N O3'
_chemical_formula_weight         465.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.75825(12)
_cell_length_b                   18.8157(4)
_cell_length_c                   31.7145(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4629.59(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14013
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      68.1400
_cell_measurement_theta_min      2.7860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.531
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1936
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -10 -12 0.1062
0 10 12 0.0826
5 -1 2 0.3965
0 1 -21 0.1693
-5 1 6 0.4456
0 -1 21 0.1327
0 -12 -2 0.0376
1 12 0 0.1362
0 12 -2 0.0356
0 -12 2 0.0468
0 12 0 0.0263
0 -12 0 0.0339
0 -12 0 0.0337

_exptl_crystal_size_max          0.939
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0053 -9.7560 -12.3736 0.2278 0.9442 0.2380
0.0969 9.7858 12.3005 -0.2289 -0.9488 -0.2178
4.9868 -1.2887 1.8961 0.2866 -0.2691 0.9195
0.0128 0.9890 -20.5177 -0.6909 0.6573 0.3011
-4.7890 0.8489 6.2163 -0.0044 0.0007 -1.0000
0.1310 -1.0230 20.5060 0.6969 -0.6629 -0.2736
0.0372 -12.1323 -2.3443 0.6845 0.7209 0.1084
1.4823 11.6716 0.2936 -0.6736 -0.7083 0.2111
0.2052 12.1143 -2.4852 -0.8244 -0.5660 0.0090
-0.0137 -12.1414 2.2349 0.8241 0.5656 0.0310
0.0259 12.2128 0.0063 -0.7594 -0.6477 -0.0623
0.2479 -12.1958 -0.3753 0.7551 0.6446 0.1193
-0.0163 -12.2128 -0.0257 0.7591 0.6478 0.0644

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            37485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.443
_diffrn_reflns_theta_min         2.787
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  31.00   0.50    0.44    --   40.40 -37.00  30.00   96
  2  ω     12.00  60.00   0.50    0.44    --   40.40 -63.00 -30.00   96
  3  ω    -12.00  24.00   0.50    0.44    --   40.40 -12.00 -30.00   72
  4  ω    -21.00   7.00   0.50    0.44    --   40.40 -63.00 -30.00   56
  5  ω     10.00  40.00   0.50    0.44    --   40.40-104.00   0.00   60
  6  ω     11.00  70.00   0.50    0.44    --   40.40-104.00 -30.00  118
  7  ω     28.00  78.00   0.50    0.44    --   40.40-104.00-150.00  100
  8  ω     29.00  57.00   0.50    1.77    --   96.04 -50.00 -60.00   56
  9  ω     35.00  67.00   0.50    1.77    --   96.04 -59.00 -90.00   64
 10  ω     29.00  56.00   0.50    1.77    --   96.04 -50.00 -30.00   54
 11  ω     40.00  75.00   0.50    1.77    --   96.04 -68.00  30.00   70
 12  ω     59.00 105.00   0.50    1.77    --   96.04-117.00  30.00   92
 13  ω     74.00  99.00   0.50    0.44    --   40.40-138.00 120.00   50
 14  ω     45.00  71.00   0.50    0.44    --   40.40-138.00 120.00   52
 15  ω     29.00  55.00   0.50    1.77    --   96.04 -50.00  30.00   52
 16  ω     26.00  52.00   0.50    1.77    --   96.04   0.00  30.00   52
 17  ω     84.00 163.00   0.50    1.77    --   96.04  50.00  60.00  158
 18  ω    137.00 163.00   0.50    1.77    --   96.04  68.00  30.00   52
 19  ω    138.00 163.00   0.50    1.77    --   96.04 117.00  90.00   50
 20  ω     80.00 106.00   0.50    1.77    --   96.04 117.00  90.00   52
 21  ω     72.00  98.00   0.50    1.77    --   96.04  68.00  30.00   52
 22  ω     76.00 164.00   0.50    1.77    --   96.04  68.00  90.00  176
 23  ω     89.00 139.00   0.50    1.77    --   96.04   0.00  30.00  100
 24  ω     74.00 126.00   0.50    1.77    --   96.04  68.00 150.00  104
 25  ω     26.00 100.00   0.50    0.44    --   40.40  50.00  30.00  148
 26  ω     79.00 154.00   0.50    1.77    --   96.04  42.00-150.00  150
 27  ω     29.00  97.00   0.50    0.44    --   40.40  50.00-180.00  136
 28  ω    -11.00  28.00   0.50    0.44    --  -40.71  63.00-180.00   78
 29  ω    -33.00  10.00   0.50    0.44    --   40.40 -12.00 -90.00   86
 30  ω     -7.00  40.00   0.50    0.44    --   40.40 -63.00-150.00   94
 31  ω     29.00 108.00   0.50    1.77    --   96.04-117.00 -30.00  158
 32  ω     -4.00  77.00   0.50    0.44    --   40.40-104.00 120.00  162
 33  ω      2.00  27.00   0.50    0.44    --   40.40 -37.00 150.00   50
 34  ω    -24.00  19.00   0.50    0.44    --   40.40 -37.00  90.00   86
 35  ω    -32.00   8.00   0.50    0.44    --   40.40 -12.00  30.00   80
 36  ω    -60.00 -29.00   0.50    0.44    --  -40.71 -37.00  60.00   62
 37  ω    -24.00  26.00   0.50    0.44    --  -40.71  12.00   0.00  100
 38  ω    -42.00 -17.00   0.50    0.44    --  -40.71  37.00   0.00   50
 39  ω    -57.00 -30.00   0.50    1.77    --  -96.35  50.00-120.00   54
 40  ω    -57.00 -30.00   0.50    1.77    --  -96.35  50.00-150.00   54
 41  ω    -57.00 -30.00   0.50    1.77    --  -96.35  50.00-180.00   54
 42  ω    -69.00 -44.00   0.50    1.77    --  -96.35  59.00 -90.00   50
 43  ω    -83.00 -57.00   0.50    1.77    --  -96.35  77.00-150.00   52
 44  ω    -76.00 -31.00   0.50    1.77    --  -96.35  68.00-120.00   90
 45  ω    -40.00 -15.00   0.50    0.44    --  -40.71  63.00-180.00   50
 46  ω    -23.00  33.00   0.50    0.44    --   40.40 -37.00-150.00  112
 47  ω    -82.00 -28.00   0.50    1.77    --  -96.35  77.00  60.00  108
 48  ω    -68.00 -38.00   0.50    1.77    --  -96.35  59.00 120.00   60
 49  ω   -100.00 -23.00   0.50    1.77    --  -96.35  96.00  90.00  154
 50  ω   -102.00 -49.00   0.50    1.77    --  -96.35  96.00 120.00  106
 51  ω   -110.00 -55.00   0.50    1.77    --  -96.35 117.00 120.00  110
 52  ω   -105.00 -80.00   0.50    0.44    --  -40.71 -37.00  60.00   50
 53  ω   -115.00 -89.00   0.50    1.77    --  -96.35-117.00  60.00   52
 54  ω   -163.00 -91.00   0.50    1.77    --  -96.35 -33.00   0.00  144
 55  ω   -162.00 -80.00   0.50    1.77    --  -96.35 -42.00 -30.00  164
 56  ω   -164.00-100.00   0.50    1.77    --  -96.35 -68.00  90.00  128
 57  ω   -104.00 -26.00   0.50    1.77    --  -96.35  96.00-120.00  156
 58  ω   -104.00 -67.00   0.50    1.77    --  -96.35 117.00-120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0297173000
_diffrn_orient_matrix_UB_12      -0.0622570000
_diffrn_orient_matrix_UB_13      0.0306887000
_diffrn_orient_matrix_UB_21      -0.0544671000
_diffrn_orient_matrix_UB_22      -0.0528995000
_diffrn_orient_matrix_UB_23      -0.0346204000
_diffrn_orient_matrix_UB_31      0.1885985000
_diffrn_orient_matrix_UB_32      -0.0054907000
_diffrn_orient_matrix_UB_33      -0.0148214000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3827
_reflns_number_total             4249
_reflns_odcompleteness_completeness 99.98
_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 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00031(5)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.027
_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)+(0.0596P)²+1.3197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C9(H9), C4(H4), C2(H2), C29(H29), C10(H10), C32(H32), C30(H30),
 C21(H21), C17(H17), C31(H31), C20(H20), C19(H19), C23(H23), C18(H18), C27(H27),
  C26(H26), C25(H25), C24(H24)
;
_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
O14 O 0.45588(12) 0.74636(4) 0.24719(3) 0.0277(2) Uani 1 1 d . . . . .
O36 O 0.37597(11) 0.75166(5) 0.10136(3) 0.0314(2) Uani 1 1 d . . . . .
O35 O 0.60946(12) 0.49934(5) 0.35992(3) 0.0321(2) Uani 1 1 d . . . . .
N15 N 0.39803(15) 0.74681(6) 0.39630(3) 0.0301(3) Uani 1 1 d . . . . .
C6 C 0.52902(15) 0.63878(6) 0.28396(4) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.47233(16) 0.70955(7) 0.28428(4) 0.0253(3) Uani 1 1 d . . . . .
C13 C 0.45824(15) 0.71036(7) 0.20948(4) 0.0257(3) Uani 1 1 d . . . . .
C8 C 0.50439(15) 0.63587(6) 0.20798(4) 0.0247(3) Uani 1 1 d . . . . .
C5 C 0.53999(15) 0.60562(6) 0.32382(4) 0.0256(3) Uani 1 1 d . . . . .
C7 C 0.55937(15) 0.60229(6) 0.24479(4) 0.0247(3) Uani 1 1 d . . . . .
C12 C 0.42021(16) 0.74954(7) 0.17488(4) 0.0278(3) Uani 1 1 d . . . . .
H12 H 0.400145 0.799112 0.177728 0.033 Uiso 1 1 calc R U . . .
C34 C 0.60263(15) 0.53147(7) 0.32630(4) 0.0265(3) Uani 1 1 d . . . . .
C28 C 0.64290(15) 0.53177(6) 0.24695(4) 0.0255(3) Uani 1 1 d . . . . .
C3 C 0.44168(16) 0.71225(7) 0.35986(4) 0.0271(3) Uani 1 1 d . . . . .
C11 C 0.40979(15) 0.71710(7) 0.13388(4) 0.0278(3) Uani 1 1 d . . . . .
C9 C 0.48113(15) 0.60301(7) 0.16725(4) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.498721 0.553236 0.164671 0.032 Uiso 1 1 calc R U . . .
C33 C 0.66246(16) 0.49801(6) 0.28646(4) 0.0260(3) Uani 1 1 d . . . . .
C16 C 0.38586(17) 0.82332(7) 0.39824(4) 0.0279(3) Uani 1 1 d . . . . .
C4 C 0.49358(16) 0.64017(7) 0.36043(4) 0.0275(3) Uani 1 1 d . . . . .
H4 H 0.496484 0.615184 0.386452 0.033 Uiso 1 1 calc R U . . .
C2 C 0.43361(16) 0.74680(7) 0.32045(4) 0.0270(3) Uani 1 1 d . . . . .
H2 H 0.401657 0.795464 0.318860 0.032 Uiso 1 1 calc R U . . .
C29 C 0.71348(15) 0.49721(7) 0.21158(4) 0.0275(3) Uani 1 1 d . . . . .
H29 H 0.710746 0.520156 0.184911 0.033 Uiso 1 1 calc R U . . .
C10 C 0.43542(16) 0.64029(7) 0.13280(4) 0.0282(3) Uani 1 1 d . . . . .
H10 H 0.419305 0.615773 0.106911 0.034 Uiso 1 1 calc R U . . .
C32 C 0.74196(16) 0.43179(7) 0.28947(4) 0.0300(3) Uani 1 1 d . . . . .
H32 H 0.756091 0.410320 0.316363 0.036 Uiso 1 1 calc R U . . .
C22 C 0.39447(17) 0.70933(7) 0.43625(4) 0.0295(3) Uani 1 1 d . . . . .
C30 C 0.78688(16) 0.43030(7) 0.21496(4) 0.0305(3) Uani 1 1 d . . . . .
H30 H 0.828300 0.407037 0.190386 0.037 Uiso 1 1 calc R U . . .
C21 C 0.22609(17) 0.85562(7) 0.40204(4) 0.0302(3) Uani 1 1 d . . . . .
H21 H 0.123803 0.827883 0.401439 0.036 Uiso 1 1 calc R U . . .
C17 C 0.53600(17) 0.86367(7) 0.39828(4) 0.0320(3) Uani 1 1 d . . . . .
H17 H 0.645028 0.841269 0.395233 0.038 Uiso 1 1 calc R U . . .
C31 C 0.80061(17) 0.39688(7) 0.25385(4) 0.0317(3) Uani 1 1 d . . . . .
H31 H 0.849526 0.350730 0.255970 0.038 Uiso 1 1 calc R U . . .
C20 C 0.21685(18) 0.92919(7) 0.40673(4) 0.0331(3) Uani 1 1 d . . . . .
H20 H 0.107874 0.951722 0.409554 0.040 Uiso 1 1 calc R U . . .
C19 C 0.36585(19) 0.96940(7) 0.40730(4) 0.0343(3) Uani 1 1 d . . . . .
H19 H 0.359033 1.019473 0.410775 0.041 Uiso 1 1 calc R U . . .
C23 C 0.54758(19) 0.69531(7) 0.45729(4) 0.0356(3) Uani 1 1 d . . . . .
H23 H 0.654523 0.710589 0.445854 0.043 Uiso 1 1 calc R U . . .
C18 C 0.52540(18) 0.93695(7) 0.40280(4) 0.0350(3) Uani 1 1 d . . . . .
H18 H 0.627425 0.964876 0.402821 0.042 Uiso 1 1 calc R U . . .
C27 C 0.23784(19) 0.68852(7) 0.45304(4) 0.0358(3) Uani 1 1 d . . . . .
H27 H 0.133522 0.698889 0.438613 0.043 Uiso 1 1 calc R U . . .
C26 C 0.2346(2) 0.65227(8) 0.49126(5) 0.0405(3) Uani 1 1 d . . . . .
H26 H 0.127585 0.637822 0.503049 0.049 Uiso 1 1 calc R U . . .
C25 C 0.3864(2) 0.63729(8) 0.51205(5) 0.0401(3) Uani 1 1 d . . . . .
H25 H 0.383767 0.612167 0.538020 0.048 Uiso 1 1 calc R U . . .
C24 C 0.5425(2) 0.65871(8) 0.49522(5) 0.0414(4) Uani 1 1 d . . . . .
H24 H 0.646626 0.648298 0.509720 0.050 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
O14 C1 1.3711(14) . ?
O14 C13 1.3747(14) . ?
O36 C11 1.2472(15) . ?
O35 C34 1.2271(15) . ?
N15 C3 1.3684(16) . ?
N15 C16 1.4441(16) . ?
N15 C22 1.4502(16) . ?
C6 C1 1.4023(17) . ?
C6 C5 1.4123(17) . ?
C6 C7 1.4388(17) . ?
C1 C2 1.3775(17) . ?
C13 C8 1.4475(17) . ?
C13 C12 1.3543(18) . ?
C8 C7 1.3943(17) . ?
C8 C9 1.4432(17) . ?
C5 C34 1.4794(17) . ?
C5 C4 1.3786(18) . ?
C7 C28 1.4783(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.4389(17) . ?
C34 C33 1.4860(17) . ?
C28 C33 1.4129(17) . ?
C28 C29 1.4074(17) . ?
C3 C4 1.4150(18) . ?
C3 C2 1.4101(17) . ?
C11 C10 1.4592(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3461(18) . ?
C33 C32 1.3935(18) . ?
C16 C21 1.3857(19) . ?
C16 C17 1.3903(19) . ?
C4 H4 0.9500 . ?
C2 H2 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.3858(18) . ?
C10 H10 0.9500 . ?
C32 H32 0.9500 . ?
C32 C31 1.3839(19) . ?
C22 C23 1.3879(19) . ?
C22 C27 1.383(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.3885(19) . ?
C21 H21 0.9500 . ?
C21 C20 1.3941(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3888(19) . ?
C31 H31 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.382(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.388(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.3868(19) . ?
C18 H18 0.9500 . ?
C27 H27 0.9500 . ?
C27 C26 1.3909(19) . ?
C26 H26 0.9500 . ?
C26 C25 1.379(2) . ?
C25 H25 0.9500 . ?
C25 C24 1.383(2) . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O14 C13 119.75(10) . . ?
C3 N15 C16 121.74(10) . . ?
C3 N15 C22 120.75(10) . . ?
C16 N15 C22 116.49(10) . . ?
C1 C6 C5 115.59(11) . . ?
C1 C6 C7 120.71(11) . . ?
C5 C6 C7 123.51(11) . . ?
O14 C1 C6 120.18(11) . . ?
O14 C1 C2 115.92(11) . . ?
C2 C1 C6 123.89(11) . . ?
O14 C13 C8 120.60(11) . . ?
C12 C13 O14 115.71(11) . . ?
C12 C13 C8 123.66(11) . . ?
C7 C8 C13 119.14(11) . . ?
C7 C8 C9 126.40(11) . . ?
C9 C8 C13 114.41(11) . . ?
C6 C5 C34 118.95(11) . . ?
C4 C5 C6 121.99(11) . . ?
C4 C5 C34 119.06(11) . . ?
C6 C7 C28 117.39(11) . . ?
C8 C7 C6 117.17(11) . . ?
C8 C7 C28 125.43(11) . . ?
C13 C12 H12 119.5 . . ?
C13 C12 C11 120.90(12) . . ?
C11 C12 H12 119.5 . . ?
O35 C34 C5 121.67(11) . . ?
O35 C34 C33 121.12(11) . . ?
C5 C34 C33 117.19(11) . . ?
C33 C28 C7 119.45(11) . . ?
C29 C28 C7 123.25(11) . . ?
C29 C28 C33 117.21(11) . . ?
N15 C3 C4 121.01(11) . . ?
N15 C3 C2 121.22(11) . . ?
C2 C3 C4 117.76(11) . . ?
O36 C11 C12 122.55(12) . . ?
O36 C11 C10 121.72(12) . . ?
C12 C11 C10 115.70(11) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.43(11) . . ?
C10 C9 H9 118.8 . . ?
C28 C33 C34 122.01(11) . . ?
C32 C33 C34 117.30(11) . . ?
C32 C33 C28 120.68(11) . . ?
C21 C16 N15 119.96(12) . . ?
C21 C16 C17 120.66(12) . . ?
C17 C16 N15 119.31(12) . . ?
C5 C4 C3 121.04(11) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C1 C2 C3 119.60(11) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.19(12) . . ?
C30 C29 H29 119.4 . . ?
C11 C10 H10 118.9 . . ?
C9 C10 C11 122.20(11) . . ?
C9 C10 H10 118.9 . . ?
C33 C32 H32 119.5 . . ?
C31 C32 C33 120.93(12) . . ?
C31 C32 H32 119.5 . . ?
C23 C22 N15 119.75(12) . . ?
C27 C22 N15 119.39(12) . . ?
C27 C22 C23 120.85(12) . . ?
C29 C30 H30 119.6 . . ?
C29 C30 C31 120.78(12) . . ?
C31 C30 H30 119.6 . . ?
C16 C21 H21 120.3 . . ?
C16 C21 C20 119.39(12) . . ?
C20 C21 H21 120.3 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.51(13) . . ?
C18 C17 H17 120.2 . . ?
C32 C31 C30 119.00(12) . . ?
C32 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.14(13) . . ?
C19 C20 H20 119.9 . . ?
C20 C19 H19 119.9 . . ?
C20 C19 C18 120.27(12) . . ?
C18 C19 H19 119.9 . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.15(13) . . ?
C24 C23 H23 120.4 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.02(13) . . ?
C19 C18 H18 120.0 . . ?
C22 C27 H27 120.3 . . ?
C22 C27 C26 119.37(13) . . ?
C26 C27 H27 120.3 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 C27 120.08(14) . . ?
C25 C26 H26 120.0 . . ?
C26 C25 H25 119.9 . . ?
C26 C25 C24 120.26(13) . . ?
C24 C25 H25 119.9 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.28(14) . . ?
C25 C24 H24 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
O14 C1 C2 C3 177.93(10) . . . . ?
O14 C13 C8 C7 -4.90(17) . . . . ?
O14 C13 C8 C9 172.83(10) . . . . ?
O14 C13 C12 C11 -176.77(10) . . . . ?
O36 C11 C10 C9 176.32(12) . . . . ?
O35 C34 C33 C28 174.76(11) . . . . ?
O35 C34 C33 C32 -6.20(17) . . . . ?
N15 C3 C4 C5 -179.04(12) . . . . ?
N15 C3 C2 C1 -177.58(12) . . . . ?
N15 C16 C21 C20 175.72(11) . . . . ?
N15 C16 C17 C18 -176.00(12) . . . . ?
N15 C22 C23 C24 -179.26(12) . . . . ?
N15 C22 C27 C26 179.69(12) . . . . ?
C6 C1 C2 C3 -3.39(19) . . . . ?
C6 C5 C34 O35 -177.61(11) . . . . ?
C6 C5 C34 C33 4.28(16) . . . . ?
C6 C5 C4 C3 -3.60(19) . . . . ?
C6 C7 C28 C33 10.67(16) . . . . ?
C6 C7 C28 C29 -165.86(11) . . . . ?
C1 O14 C13 C8 -9.64(16) . . . . ?
C1 O14 C13 C12 172.22(11) . . . . ?
C1 C6 C5 C34 -178.59(10) . . . . ?
C1 C6 C5 C4 1.63(17) . . . . ?
C1 C6 C7 C8 -9.96(17) . . . . ?
C1 C6 C7 C28 171.25(11) . . . . ?
C13 O14 C1 C6 14.12(16) . . . . ?
C13 O14 C1 C2 -167.15(11) . . . . ?
C13 C8 C7 C6 14.19(17) . . . . ?
C13 C8 C7 C28 -167.13(11) . . . . ?
C13 C8 C9 C10 5.77(17) . . . . ?
C13 C12 C11 O36 -179.62(12) . . . . ?
C13 C12 C11 C10 2.46(17) . . . . ?
C8 C13 C12 C11 5.15(19) . . . . ?
C8 C7 C28 C33 -168.00(12) . . . . ?
C8 C7 C28 C29 15.47(19) . . . . ?
C8 C9 C10 C11 1.43(19) . . . . ?
C5 C6 C1 O14 -179.48(10) . . . . ?
C5 C6 C1 C2 1.90(18) . . . . ?
C5 C6 C7 C8 164.85(11) . . . . ?
C5 C6 C7 C28 -13.94(17) . . . . ?
C5 C34 C33 C28 -7.11(17) . . . . ?
C5 C34 C33 C32 171.93(11) . . . . ?
C7 C6 C1 O14 -4.27(18) . . . . ?
C7 C6 C1 C2 177.10(11) . . . . ?
C7 C6 C5 C34 6.36(17) . . . . ?
C7 C6 C5 C4 -173.43(11) . . . . ?
C7 C8 C9 C10 -176.70(12) . . . . ?
C7 C28 C33 C34 -0.47(17) . . . . ?
C7 C28 C33 C32 -179.47(11) . . . . ?
C7 C28 C29 C30 -178.43(11) . . . . ?
C12 C13 C8 C7 173.09(12) . . . . ?
C12 C13 C8 C9 -9.18(17) . . . . ?
C12 C11 C10 C9 -5.74(18) . . . . ?
C34 C5 C4 C3 176.62(11) . . . . ?
C34 C33 C32 C31 179.68(11) . . . . ?
C28 C33 C32 C31 -1.27(19) . . . . ?
C28 C29 C30 C31 -3.24(18) . . . . ?
C3 N15 C16 C21 109.04(14) . . . . ?
C3 N15 C16 C17 -73.97(16) . . . . ?
C3 N15 C22 C23 78.41(16) . . . . ?
C3 N15 C22 C27 -102.11(15) . . . . ?
C9 C8 C7 C6 -163.24(11) . . . . ?
C9 C8 C7 C28 15.4(2) . . . . ?
C33 C28 C29 C30 4.97(18) . . . . ?
C33 C32 C31 C30 3.13(19) . . . . ?
C16 N15 C3 C4 164.59(12) . . . . ?
C16 N15 C3 C2 -16.54(19) . . . . ?
C16 N15 C22 C23 -90.26(15) . . . . ?
C16 N15 C22 C27 89.22(15) . . . . ?
C16 C21 C20 C19 0.45(19) . . . . ?
C16 C17 C18 C19 0.1(2) . . . . ?
C4 C5 C34 O35 2.18(18) . . . . ?
C4 C5 C34 C33 -175.94(11) . . . . ?
C4 C3 C2 C1 1.33(18) . . . . ?
C2 C3 C4 C5 2.05(18) . . . . ?
C29 C28 C33 C34 176.27(11) . . . . ?
C29 C28 C33 C32 -2.74(18) . . . . ?
C29 C30 C31 C32 -0.90(19) . . . . ?
C22 N15 C3 C4 -3.48(19) . . . . ?
C22 N15 C3 C2 175.39(11) . . . . ?
C22 N15 C16 C21 -82.41(15) . . . . ?
C22 N15 C16 C17 94.58(14) . . . . ?
C22 C23 C24 C25 -0.8(2) . . . . ?
C22 C27 C26 C25 -0.1(2) . . . . ?
C21 C16 C17 C18 0.97(19) . . . . ?
C21 C20 C19 C18 0.6(2) . . . . ?
C17 C16 C21 C20 -1.23(18) . . . . ?
C20 C19 C18 C17 -0.9(2) . . . . ?
C23 C22 C27 C26 -0.8(2) . . . . ?
C27 C22 C23 C24 1.3(2) . . . . ?
C27 C26 C25 C24 0.5(2) . . . . ?
C26 C25 C24 C23 -0.1(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 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.736
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/Et2O'
