# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_1_pp
_database_code_depnum_ccdc_archive 'CCDC 2394806'
loop_
_audit_author_name
_audit_author_address
'Takuya Kanetomo'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_audit_creation_date             2024-10-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
"10-benzyl-10'-methyl-9,9'(10H,10'H)spirobiacridine-2,7-diyl bis(tert-butyl nitroxide)"
_chemical_formula_moiety         'C40.879 H41.728 Br0.03 N3.97 O1.97'
_chemical_formula_sum            'C40.88 H41.73 Br0.03 N3.97 O1.97'
_chemical_formula_weight         622.55
_chemical_melting_point          445
_chemical_oxdiff_formula         C41H42N4O2
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.3776(5)
_cell_length_b                   13.0243(4)
_cell_length_c                   13.0653(3)
_cell_angle_alpha                96.956(2)
_cell_angle_beta                 103.047(3)
_cell_angle_gamma                113.442(3)
_cell_volume                     1829.35(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10568
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      28.9950
_cell_measurement_theta_min      2.6430
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
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            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             663
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -15 0 0.0676
17 -10 -1 0.1097
5 13 -1 0.0813
-16 11 -2 0.0289
-3 -2 18 0.0616
5 1 -18 0.0528

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
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
-2.8114 -14.9414 0.4992 0.9502 0.3084 -0.0448
17.0513 -10.1990 -1.3671 -0.0524 -0.0170 -0.9985
5.1058 13.3905 -0.6802 -0.9471 -0.3074 -0.0918
-16.2679 11.2795 -1.5381 0.0483 -0.1481 0.9878
-3.4284 -2.0555 18.4061 -0.3084 0.9500 0.0486
4.5090 1.3281 -18.3961 0.3067 -0.9450 -0.1134

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32489
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.733
_diffrn_reflns_theta_min         2.094
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00  58.00   0.50    5.60    --    4.20  37.00-180.00  282
  2  ω    -84.00 -18.00   0.50    5.60    --    4.20  18.00 -60.00  132
  3  ω      3.00  30.00   0.50    5.60    --    4.20  18.00 -60.00   54
  4  ω    -83.00  38.00   0.50    5.60    --    4.20  37.00  60.00  242
  5  ω     54.00  93.00   0.50    5.60    --    4.20  37.00  60.00   78
  6  ω    -29.00  14.00   0.50    5.60    --    4.20   9.00   0.00   86
  7  ω    -84.00  22.00   0.50    5.60    --    4.20  55.00 -30.00  212
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0397030000
_diffrn_orient_matrix_UB_12      -0.0571436000
_diffrn_orient_matrix_UB_13      -0.0305306000
_diffrn_orient_matrix_UB_21      -0.0076507000
_diffrn_orient_matrix_UB_22      -0.0175926000
_diffrn_orient_matrix_UB_23      0.0482250000
_diffrn_orient_matrix_UB_31      -0.0515221000
_diffrn_orient_matrix_UB_32      0.0125074000
_diffrn_orient_matrix_UB_33      -0.0055607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6619
_reflns_number_total             7722
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         7722
_refine_ls_number_restraints     762
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+1.8145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C18 \\sim O2 \\sim N3 \\sim C7 \\sim C8 \\sim C12 \\sim C19 \\sim C20 \\sim C21
\\sim C9 \\sim C11 \\sim C10 \\sim C13 \\sim N2 \\sim C3 \\sim C32 \\sim C38
\\sim C4 \\sim C22 \\sim C2 \\sim C33 \\sim C31 \\sim C39 \\sim C37 \\sim C5
\\sim C23 \\sim C1 \\sim N4 \\sim C34 \\sim C30 \\sim C40 \\sim C36 \\sim C6
\\sim C28 \\sim C24 \\sim N1 \\sim Br1 \\sim C29 \\sim C35 \\sim C41 \\sim C27
\\sim C25 \\sim O1 \\sim C14 \\sim C26 \\sim C17 \\sim C15 \\sim C16: within
2.2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2.2A
3. Rigid body (RIGU) restrains
 C18, O2, N3, C7, C8, C12, C19, C20, C21, C9, C11, C10, C13, N2, C3, C32, C38,
 C4, C22, C2, C33, C31, C39, C37, C5, C23, C1, N4, C34, C30, C40, C36, C6, C28,
 C24, N1, Br1, C29, C35, C41, C27, C25, O1, C14, C26, C17, C15, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Br1)=1-FVAR(1)
 Sof(O1)=Sof(N1)=Sof(C14)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C15)=
 Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C2(H2), C5(H5), C6(H6), C28(H28), C37(H37),
 C31(H31), C34(H34), C30(H30), C24(H24), C26(H26), C40(H40), C35(H35), C36(H36),
  C27(H27), C25(H25), C41(H41)
5.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C29(H29A,H29B,H29C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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
O2 O 0.42141(15) 0.41012(14) 0.10822(12) 0.0379(4) Uani 1 1 d . U . . .
N2 N 0.32808(14) 0.50344(13) 0.55236(12) 0.0232(3) Uani 1 1 d . U . . .
O1 O 0.20413(16) 0.90643(13) 0.70951(15) 0.0437(4) Uani 0.9698(16) 1 d . U P A
1
N4 N 0.42568(15) 0.84967(13) 0.32184(13) 0.0278(4) Uani 1 1 d . U . . .
N3 N 0.35566(14) 0.46155(13) 0.12761(13) 0.0256(3) Uani 1 1 d . U . . .
N1 N 0.1640(2) 0.80637(19) 0.72927(18) 0.0276(4) Uani 0.9698(16) 1 d . U P A 1
C3 C 0.27852(16) 0.66652(15) 0.54538(14) 0.0215(4) Uani 1 1 d . U . . .
C9 C 0.32962(16) 0.57945(15) 0.39174(14) 0.0211(4) Uani 1 1 d . U . . .
C10 C 0.33369(16) 0.49398(15) 0.44642(14) 0.0218(4) Uani 1 1 d . U . . .
C8 C 0.33424(16) 0.56656(15) 0.28580(14) 0.0216(4) Uani 1 1 d . U . . .
H8 H 0.331525 0.624087 0.248398 0.026 Uiso 1 1 calc R U . . .
C11 C 0.33936(16) 0.39744(15) 0.39236(15) 0.0231(4) Uani 1 1 d . U . . .
H11 H 0.339072 0.338318 0.428499 0.028 Uiso 1 1 calc R U . . .
C4 C 0.28641(16) 0.57855(15) 0.59491(14) 0.0232(4) Uani 1 1 d . U . . .
C7 C 0.34271(16) 0.47190(15) 0.23293(14) 0.0224(4) Uani 1 1 d . U . . .
C13 C 0.32665(16) 0.68903(15) 0.44793(14) 0.0210(4) Uani 1 1 d . U . . .
C32 C 0.45905(16) 0.78692(15) 0.48899(15) 0.0218(4) Uani 1 1 d . U . . .
C38 C 0.24562(17) 0.72277(15) 0.36559(14) 0.0218(4) Uani 1 1 d . U . . .
C1 C 0.20320(17) 0.72821(16) 0.68593(15) 0.0256(4) Uani 1 1 d . U . . .
C23 C 0.25753(17) 0.31910(15) 0.61657(14) 0.0225(4) Uani 1 1 d . U . . .
C12 C 0.34534(16) 0.38652(15) 0.28789(15) 0.0234(4) Uani 1 1 d . U . . .
H12 H 0.351233 0.321343 0.253168 0.028 Uiso 1 1 calc R U . . .
C2 C 0.23857(16) 0.74007(15) 0.59228(15) 0.0231(4) Uani 1 1 d . U . . .
H2 H 0.235079 0.800544 0.559766 0.028 Uiso 1 1 calc R U . . .
C5 C 0.25365(18) 0.56878(16) 0.69041(15) 0.0275(4) Uani 1 1 d . U . . .
H5 H 0.259522 0.510081 0.724667 0.033 Uiso 1 1 calc R U . . .
C6 C 0.21330(19) 0.64196(16) 0.73562(16) 0.0296(4) Uani 1 1 d . U . . .
H6 H 0.192217 0.633955 0.800727 0.035 Uiso 1 1 calc R U . . .
C39 C 0.29784(18) 0.79977(15) 0.30440(15) 0.0259(4) Uani 1 1 d . U . . .
C28 C 0.28410(19) 0.25395(17) 0.68623(16) 0.0295(4) Uani 1 1 d . U . . .
H28 H 0.365476 0.281108 0.733364 0.035 Uiso 1 1 calc R U . . .
C33 C 0.50397(17) 0.86052(15) 0.42268(15) 0.0247(4) Uani 1 1 d . U . . .
C22 C 0.36245(17) 0.43163(15) 0.61804(15) 0.0238(4) Uani 1 1 d . U . . .
H22A H 0.403088 0.477114 0.693819 0.029 Uiso 1 1 calc R U . . .
H22B H 0.424166 0.413833 0.592977 0.029 Uiso 1 1 calc R U . . .
C37 C 0.11790(18) 0.67043(17) 0.34389(15) 0.0281(4) Uani 1 1 d . U . . .
H37 H 0.082400 0.617895 0.384811 0.034 Uiso 1 1 calc R U . . .
C31 C 0.53815(18) 0.80148(16) 0.58988(16) 0.0269(4) Uani 1 1 d . U . . .
H31 H 0.507787 0.753189 0.635835 0.032 Uiso 1 1 calc R U . . .
C18 C 0.30073(18) 0.50522(18) 0.03979(15) 0.0289(4) Uani 1 1 d . U . . .
C34 C 0.62723(19) 0.94477(16) 0.45935(17) 0.0319(4) Uani 1 1 d . U . . .
H34 H 0.658244 0.995043 0.415081 0.038 Uiso 1 1 calc R U . . .
C30 C 0.65999(19) 0.88452(17) 0.62511(18) 0.0333(5) Uani 1 1 d . U . . .
H30 H 0.712730 0.892624 0.693908 0.040 Uiso 1 1 calc R U . . .
C24 C 0.13929(18) 0.27841(17) 0.54873(16) 0.0292(4) Uani 1 1 d . U . . .
H24 H 0.120119 0.322377 0.500906 0.035 Uiso 1 1 calc R U . . .
C26 C 0.07390(19) 0.10921(17) 0.61889(17) 0.0322(4) Uani 1 1 d . U . . .
H26 H 0.011214 0.037681 0.619884 0.039 Uiso 1 1 calc R U . . .
C40 C 0.2192(2) 0.82241(18) 0.22412(16) 0.0339(5) Uani 1 1 d . U . . .
H40 H 0.253355 0.874948 0.182707 0.041 Uiso 1 1 calc R U . . .
C35 C 0.70337(19) 0.95538(17) 0.55820(19) 0.0354(5) Uani 1 1 d . U . . .
H35 H 0.786883 1.012022 0.581083 0.042 Uiso 1 1 calc R U . . .
C36 C 0.0414(2) 0.6928(2) 0.26446(17) 0.0377(5) Uani 1 1 d . U . . .
H36 H -0.045587 0.656248 0.250987 0.045 Uiso 1 1 calc R U . . .
C27 C 0.1926(2) 0.14973(17) 0.68727(18) 0.0343(5) Uani 1 1 d . U . . .
H27 H 0.211458 0.105742 0.735234 0.041 Uiso 1 1 calc R U . . .
C25 C 0.04717(19) 0.17289(17) 0.54964(18) 0.0335(5) Uani 1 1 d . U . . .
H25 H -0.034136 0.145201 0.502188 0.040 Uiso 1 1 calc R U . . .
C14 C 0.0709(2) 0.77802(18) 0.79131(17) 0.0318(5) Uani 0.9698(16) 1 d . U P A 1
C19 C 0.17374(19) 0.4934(2) 0.04305(17) 0.0346(5) Uani 1 1 d . U . . .
H19A H 0.120993 0.413368 0.041575 0.052 Uiso 1 1 calc R U . . .
H19B H 0.136043 0.515079 -0.019804 0.052 Uiso 1 1 calc R U . . .
H19C H 0.182749 0.544043 0.109483 0.052 Uiso 1 1 calc R U . . .
C41 C 0.0931(2) 0.7692(2) 0.20487(17) 0.0403(5) Uani 1 1 d . U . . .
H41 H 0.041171 0.785091 0.150089 0.048 Uiso 1 1 calc R U . . .
C29 C 0.4777(2) 0.92128(18) 0.25089(18) 0.0389(5) Uani 1 1 d . U . . .
H29A H 0.422210 0.888195 0.176668 0.058 Uiso 1 1 calc R U . . .
H29B H 0.558556 0.924194 0.253087 0.058 Uiso 1 1 calc R U . . .
H29C H 0.487144 0.999369 0.275439 0.058 Uiso 1 1 calc R U . . .
C20 C 0.2862(2) 0.4313(2) -0.06725(16) 0.0385(5) Uani 1 1 d . U . . .
H20A H 0.367886 0.444146 -0.073120 0.058 Uiso 1 1 calc R U . . .
H20B H 0.243113 0.452649 -0.127413 0.058 Uiso 1 1 calc R U . . .
H20C H 0.238223 0.349885 -0.069830 0.058 Uiso 1 1 calc R U . . .
C21 C 0.3903(2) 0.63077(18) 0.04969(18) 0.0355(5) Uani 1 1 d . U . . .
H21A H 0.399544 0.678789 0.117902 0.053 Uiso 1 1 calc R U . . .
H21B H 0.357533 0.658337 -0.010942 0.053 Uiso 1 1 calc R U . . .
H21C H 0.470888 0.635260 0.048416 0.053 Uiso 1 1 calc R U . . .
C17 C -0.0255(2) 0.6516(2) 0.7481(2) 0.0389(5) Uani 0.9698(16) 1 d . U P A 1
H17A H -0.052414 0.633094 0.668891 0.058 Uiso 0.9698(16) 1 calc R U P A 1
H17B H -0.096651 0.639493 0.774522 0.058 Uiso 0.9698(16) 1 calc R U P A 1
H17C H 0.011255 0.601539 0.773366 0.058 Uiso 0.9698(16) 1 calc R U P A 1
C15 C 0.0047(2) 0.8548(2) 0.7718(2) 0.0441(6) Uani 0.9698(16) 1 d . U P A 1
H15A H 0.064524 0.935800 0.800850 0.066 Uiso 0.9698(16) 1 calc R U P A 1
H15B H -0.059479 0.836124 0.808158 0.066 Uiso 0.9698(16) 1 calc R U P A 1
H15C H -0.033145 0.841400 0.694024 0.066 Uiso 0.9698(16) 1 calc R U P A 1
C16 C 0.1377(3) 0.8030(2) 0.91159(19) 0.0495(7) Uani 0.9698(16) 1 d . U P A 1
H16A H 0.174645 0.749720 0.923382 0.074 Uiso 0.9698(16) 1 calc R U P A 1
H16B H 0.078595 0.792814 0.952798 0.074 Uiso 0.9698(16) 1 calc R U P A 1
H16C H 0.202670 0.882357 0.935724 0.074 Uiso 0.9698(16) 1 calc R U P A 1
Br1 Br 0.1263(14) 0.8365(13) 0.7286(11) 0.066(5) Uani 0.0302(16) 1 d . U 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
O2 N3 1.289(2) . ?
N2 C10 1.395(2) . ?
N2 C4 1.390(2) . ?
N2 C22 1.462(2) . ?
O1 N1 1.279(3) . ?
N4 C39 1.400(3) . ?
N4 C33 1.402(3) . ?
N4 C29 1.464(2) . ?
N3 C7 1.417(2) . ?
N3 C18 1.489(2) . ?
N1 C1 1.404(3) . ?
N1 C14 1.509(3) . ?
C3 C4 1.408(2) . ?
C3 C13 1.535(2) . ?
C3 C2 1.382(3) . ?
C9 C10 1.405(2) . ?
C9 C8 1.391(2) . ?
C9 C13 1.542(3) . ?
C10 C11 1.401(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.392(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(3) . ?
C4 C5 1.401(3) . ?
C7 C12 1.402(2) . ?
C13 C32 1.541(2) . ?
C13 C38 1.528(2) . ?
C32 C33 1.405(2) . ?
C32 C31 1.393(3) . ?
C38 C39 1.405(2) . ?
C38 C37 1.392(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.397(3) . ?
C1 Br1 2.079(15) . ?
C23 C28 1.389(3) . ?
C23 C22 1.517(2) . ?
C23 C24 1.375(3) . ?
C12 H12 0.9500 . ?
C2 H2 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.372(3) . ?
C6 H6 0.9500 . ?
C39 C40 1.406(3) . ?
C28 H28 0.9500 . ?
C28 C27 1.383(3) . ?
C33 C34 1.404(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C37 H37 0.9500 . ?
C37 C36 1.381(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.387(3) . ?
C18 C19 1.528(3) . ?
C18 C20 1.529(3) . ?
C18 C21 1.537(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.371(3) . ?
C30 H30 0.9500 . ?
C30 C35 1.385(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.397(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.383(3) . ?
C26 C25 1.372(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.379(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C36 C41 1.382(3) . ?
C27 H27 0.9500 . ?
C25 H25 0.9500 . ?
C14 C17 1.536(3) . ?
C14 C15 1.534(3) . ?
C14 C16 1.528(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C41 H41 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N2 C22 120.04(15) . . ?
C4 N2 C10 120.23(15) . . ?
C4 N2 C22 119.70(15) . . ?
C39 N4 C33 119.20(15) . . ?
C39 N4 C29 119.36(17) . . ?
C33 N4 C29 118.62(17) . . ?
O2 N3 C7 116.04(15) . . ?
O2 N3 C18 118.40(15) . . ?
C7 N3 C18 125.56(16) . . ?
O1 N1 C1 117.9(2) . . ?
O1 N1 C14 117.5(2) . . ?
C1 N1 C14 124.50(18) . . ?
C4 C3 C13 120.61(16) . . ?
C2 C3 C4 119.02(16) . . ?
C2 C3 C13 120.05(16) . . ?
C10 C9 C13 121.70(15) . . ?
C8 C9 C10 118.62(17) . . ?
C8 C9 C13 119.61(15) . . ?
N2 C10 C9 120.23(16) . . ?
N2 C10 C11 120.36(16) . . ?
C11 C10 C9 119.38(16) . . ?
C9 C8 H8 119.0 . . ?
C9 C8 C7 121.97(16) . . ?
C7 C8 H8 119.0 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.32(17) . . ?
C12 C11 H11 119.3 . . ?
N2 C4 C3 121.47(16) . . ?
N2 C4 C5 119.77(16) . . ?
C5 C4 C3 118.75(17) . . ?
C8 C7 N3 122.45(16) . . ?
C8 C7 C12 118.91(16) . . ?
C12 C7 N3 118.55(17) . . ?
C3 C13 C9 109.43(14) . . ?
C3 C13 C32 108.50(14) . . ?
C32 C13 C9 108.86(14) . . ?
C38 C13 C3 111.94(15) . . ?
C38 C13 C9 108.67(14) . . ?
C38 C13 C32 109.38(14) . . ?
C33 C32 C13 120.13(16) . . ?
C31 C32 C13 121.17(15) . . ?
C31 C32 C33 118.65(17) . . ?
C39 C38 C13 120.47(16) . . ?
C37 C38 C13 120.31(16) . . ?
C37 C38 C39 119.01(17) . . ?
C2 C1 N1 118.87(18) . . ?
C2 C1 C6 118.62(18) . . ?
C2 C1 Br1 114.2(4) . . ?
C6 C1 N1 122.45(18) . . ?
C6 C1 Br1 127.0(4) . . ?
C28 C23 C22 117.71(17) . . ?
C24 C23 C28 119.09(17) . . ?
C24 C23 C22 123.19(16) . . ?
C11 C12 C7 119.77(17) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C3 C2 C1 121.99(17) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.58(18) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.00(17) . . ?
C5 C6 H6 120.0 . . ?
N4 C39 C38 119.93(17) . . ?
N4 C39 C40 121.27(17) . . ?
C38 C39 C40 118.77(18) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 C23 120.30(19) . . ?
C27 C28 H28 119.8 . . ?
N4 C33 C32 119.92(16) . . ?
N4 C33 C34 121.01(17) . . ?
C34 C33 C32 119.07(18) . . ?
N2 C22 C23 115.93(15) . . ?
N2 C22 H22A 108.3 . . ?
N2 C22 H22B 108.3 . . ?
C23 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
C38 C37 H37 119.1 . . ?
C36 C37 C38 121.78(19) . . ?
C36 C37 H37 119.1 . . ?
C32 C31 H31 119.1 . . ?
C30 C31 C32 121.84(18) . . ?
C30 C31 H31 119.1 . . ?
N3 C18 C19 111.15(15) . . ?
N3 C18 C20 106.91(17) . . ?
N3 C18 C21 109.00(16) . . ?
C19 C18 C20 108.90(17) . . ?
C19 C18 C21 111.73(18) . . ?
C20 C18 C21 109.01(17) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 C33 120.83(18) . . ?
C35 C34 H34 119.6 . . ?
C31 C30 H30 120.6 . . ?
C35 C30 C31 118.8(2) . . ?
C35 C30 H30 120.6 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.49(18) . . ?
C25 C24 H24 119.8 . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.62(18) . . ?
C39 C40 H40 119.7 . . ?
C41 C40 C39 120.69(19) . . ?
C41 C40 H40 119.7 . . ?
C34 C35 C30 120.78(19) . . ?
C34 C35 H35 119.6 . . ?
C30 C35 H35 119.6 . . ?
C37 C36 H36 120.5 . . ?
C37 C36 C41 119.1(2) . . ?
C41 C36 H36 120.5 . . ?
C28 C27 H27 119.8 . . ?
C26 C27 C28 120.37(19) . . ?
C26 C27 H27 119.8 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H25 119.9 . . ?
N1 C14 C17 110.24(18) . . ?
N1 C14 C15 107.09(18) . . ?
N1 C14 C16 109.4(2) . . ?
C15 C14 C17 108.40(19) . . ?
C16 C14 C17 111.18(18) . . ?
C16 C14 C15 110.4(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C40 C41 C36 120.7(2) . . ?
C40 C41 H41 119.7 . . ?
C36 C41 H41 119.7 . . ?
N4 C29 H29A 109.5 . . ?
N4 C29 H29B 109.5 . . ?
N4 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 C7 C8 146.17(17) . . . . ?
O2 N3 C7 C12 -30.3(2) . . . . ?
O2 N3 C18 C19 144.57(18) . . . . ?
O2 N3 C18 C20 25.9(2) . . . . ?
O2 N3 C18 C21 -91.8(2) . . . . ?
N2 C10 C11 C12 -179.80(17) . . . . ?
N2 C4 C5 C6 179.33(18) . . . . ?
O1 N1 C1 C2 -26.0(3) . . . . ?
O1 N1 C1 C6 151.1(2) . . . . ?
O1 N1 C14 C17 142.9(2) . . . . ?
O1 N1 C14 C15 25.1(3) . . . . ?
O1 N1 C14 C16 -94.6(2) . . . . ?
N4 C39 C40 C41 177.39(19) . . . . ?
N4 C33 C34 C35 179.75(19) . . . . ?
N3 C7 C12 C11 176.67(16) . . . . ?
N1 C1 C2 C3 179.80(18) . . . . ?
N1 C1 C6 C5 -179.18(19) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C13 C32 C33 -150.21(17) . . . . ?
C3 C13 C32 C31 32.5(2) . . . . ?
C3 C13 C38 C39 147.34(16) . . . . ?
C3 C13 C38 C37 -38.0(2) . . . . ?
C9 C10 C11 C12 2.3(3) . . . . ?
C9 C8 C7 N3 -175.74(16) . . . . ?
C9 C8 C7 C12 0.7(3) . . . . ?
C9 C13 C32 C33 90.77(19) . . . . ?
C9 C13 C32 C31 -86.5(2) . . . . ?
C9 C13 C38 C39 -91.68(19) . . . . ?
C9 C13 C38 C37 83.0(2) . . . . ?
C10 N2 C4 C3 -16.2(3) . . . . ?
C10 N2 C4 C5 165.13(17) . . . . ?
C10 N2 C22 C23 -93.3(2) . . . . ?
C10 C9 C8 C7 0.0(3) . . . . ?
C10 C9 C13 C3 -22.0(2) . . . . ?
C10 C9 C13 C32 96.39(18) . . . . ?
C10 C9 C13 C38 -144.55(16) . . . . ?
C10 C11 C12 C7 -1.6(3) . . . . ?
C8 C9 C10 N2 -179.39(16) . . . . ?
C8 C9 C10 C11 -1.5(3) . . . . ?
C8 C9 C13 C3 161.03(16) . . . . ?
C8 C9 C13 C32 -80.54(19) . . . . ?
C8 C9 C13 C38 38.5(2) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C4 N2 C10 C9 17.0(2) . . . . ?
C4 N2 C10 C11 -160.91(16) . . . . ?
C4 N2 C22 C23 84.8(2) . . . . ?
C4 C3 C13 C9 22.7(2) . . . . ?
C4 C3 C13 C32 -95.92(19) . . . . ?
C4 C3 C13 C38 143.28(16) . . . . ?
C4 C3 C2 C1 -1.4(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C7 N3 C18 C19 -35.8(3) . . . . ?
C7 N3 C18 C20 -154.48(17) . . . . ?
C7 N3 C18 C21 87.8(2) . . . . ?
C13 C3 C4 N2 -5.4(3) . . . . ?
C13 C3 C4 C5 173.27(16) . . . . ?
C13 C3 C2 C1 -174.90(16) . . . . ?
C13 C9 C10 N2 3.7(3) . . . . ?
C13 C9 C10 C11 -178.42(15) . . . . ?
C13 C9 C8 C7 177.03(16) . . . . ?
C13 C32 C33 N4 4.2(3) . . . . ?
C13 C32 C33 C34 -176.28(17) . . . . ?
C13 C32 C31 C30 175.83(18) . . . . ?
C13 C38 C39 N4 -2.6(3) . . . . ?
C13 C38 C39 C40 175.56(17) . . . . ?
C13 C38 C37 C36 -175.27(18) . . . . ?
C32 C13 C38 C39 27.1(2) . . . . ?
C32 C13 C38 C37 -158.24(16) . . . . ?
C32 C33 C34 C35 0.2(3) . . . . ?
C32 C31 C30 C35 0.6(3) . . . . ?
C38 C13 C32 C33 -27.8(2) . . . . ?
C38 C13 C32 C31 154.88(17) . . . . ?
C38 C39 C40 C41 -0.7(3) . . . . ?
C38 C37 C36 C41 0.1(3) . . . . ?
C1 N1 C14 C17 -32.8(3) . . . . ?
C1 N1 C14 C15 -150.5(2) . . . . ?
C1 N1 C14 C16 89.8(3) . . . . ?
C23 C28 C27 C26 0.1(3) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C2 C3 C4 N2 -178.83(16) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C2 C3 C13 C9 -163.91(16) . . . . ?
C2 C3 C13 C32 77.4(2) . . . . ?
C2 C3 C13 C38 -43.4(2) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C6 C1 C2 C3 2.5(3) . . . . ?
C39 N4 C33 C32 24.0(3) . . . . ?
C39 N4 C33 C34 -155.56(18) . . . . ?
C39 C38 C37 C36 -0.5(3) . . . . ?
C39 C40 C41 C36 0.3(3) . . . . ?
C28 C23 C22 N2 -173.61(17) . . . . ?
C28 C23 C24 C25 -0.1(3) . . . . ?
C33 N4 C39 C38 -24.9(3) . . . . ?
C33 N4 C39 C40 157.01(18) . . . . ?
C33 C32 C31 C30 -1.5(3) . . . . ?
C33 C34 C35 C30 -1.1(3) . . . . ?
C22 N2 C10 C9 -164.91(16) . . . . ?
C22 N2 C10 C11 17.2(2) . . . . ?
C22 N2 C4 C3 165.70(16) . . . . ?
C22 N2 C4 C5 -13.0(2) . . . . ?
C22 C23 C28 C27 -178.99(18) . . . . ?
C22 C23 C24 C25 178.67(19) . . . . ?
C37 C38 C39 N4 -177.34(17) . . . . ?
C37 C38 C39 C40 0.8(3) . . . . ?
C37 C36 C41 C40 0.0(3) . . . . ?
C31 C32 C33 N4 -178.50(17) . . . . ?
C31 C32 C33 C34 1.1(3) . . . . ?
C31 C30 C35 C34 0.7(3) . . . . ?
C18 N3 C7 C8 -33.5(3) . . . . ?
C18 N3 C7 C12 150.05(17) . . . . ?
C24 C23 C28 C27 -0.1(3) . . . . ?
C24 C23 C22 N2 7.6(3) . . . . ?
C27 C26 C25 C24 -0.4(3) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C14 N1 C1 C2 149.6(2) . . . . ?
C14 N1 C1 C6 -33.2(3) . . . . ?
C29 N4 C39 C38 174.37(17) . . . . ?
C29 N4 C39 C40 -3.7(3) . . . . ?
C29 N4 C33 C32 -175.13(18) . . . . ?
C29 N4 C33 C34 5.3(3) . . . . ?
Br1 C1 C2 C3 -172.7(5) . . . . ?
Br1 C1 C6 C5 172.5(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.283 0.000 0.000 306.4 72.5 ?
2 0.000 0.500 0.500 17.3 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 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 1.169
_oxdiff_exptl_absorpt_empirical_full_min 0.921
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, n-hexane'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_1_mp
_database_code_depnum_ccdc_archive 'CCDC 2394807'
loop_
_audit_author_name
_audit_author_address
'Takuya Kanetomo'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_audit_creation_date             2024-10-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
"10-benzyl-10'-methyl-9,9'(10H,10'H)spirobiacridine-2,6-diyl bis(tert-butyl nitroxide)"
_chemical_formula_moiety         'C41 H42 N4 O2'
_chemical_formula_sum            'C41 H42 N4 O2'
_chemical_formula_weight         622.78
_chemical_melting_point          407
_chemical_oxdiff_formula         C42H44N4O2Cl2
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                   17.4124(8)
_cell_length_b                   10.2091(4)
_cell_length_c                   20.8163(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.887(4)
_cell_angle_gamma                90
_cell_volume                     3607.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15538
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      29.2980
_cell_measurement_theta_min      2.5800
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
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            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 1 0.0942
-1 -2 1 0.1309
0 1 -2 0.1155
2 0 1 0.0656
-1 0 -2 0.1063
2 -1 0 0.0878
-2 -1 1 0.1411
-2 0 -1 0.0839
0 1 1 0.0868
-2 1 -1 0.0691
1 -1 2 0.1025
1 -2 -2 0.1229
1 0 -2 0.1263
-1 0 2 0.1201
0 -2 -1 0.1095
0 0 1 0.1029

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
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
1.9984 0.9996 0.9998 0.0895 -0.0743 -0.0284
-1.0007 -1.9985 1.0004 -0.1280 -0.0239 0.0682
0.0012 0.9990 -1.9993 0.0450 0.0628 -0.0609
1.9976 0.0002 1.0009 0.0235 -0.0930 -0.0173
-0.9985 -0.0004 -1.9991 -0.0274 0.0796 -0.0287
1.9971 -0.9993 0.0028 -0.0529 -0.0896 -0.0312
-1.9988 -0.9992 0.9985 -0.0685 0.0302 0.0782
-1.9976 -0.0002 -1.0009 -0.0235 0.0930 0.0173
0.0006 0.9995 0.9980 0.0764 -0.0034 0.0138
-1.9968 0.9991 -1.0020 0.0424 0.1117 0.0063
0.9977 -0.9989 2.0002 -0.0385 -0.0983 0.0398
0.9978 -1.9990 -1.9952 -0.1463 -0.0287 -0.0488
0.9993 -0.0003 -1.9974 -0.0144 0.0087 -0.0709
-0.9993 0.0003 1.9974 0.0144 -0.0087 0.0709
-0.0013 -1.9988 -0.9969 -0.1423 -0.0153 -0.0028
-0.0002 0.0002 0.9991 0.0105 -0.0221 0.0249

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45426
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.328
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00   2.00   0.50   10.30    --   -3.30  55.00 -60.00   76
  2  ω    -92.00 -67.00   0.50   10.30    --   -3.30  55.00 -60.00   50
  3  ω    -39.00 -10.00   0.50   10.30    --   -3.30  46.00 150.00   58
  4  ω     -4.00  86.00   0.50   10.30    --   -3.30  46.00 150.00  180
  5  ω     26.00  80.00   0.50   10.30    --   -3.30  55.00 -60.00  108
  6  ω     60.00  85.00   0.50   10.30    --   -3.30  28.00  90.00   50
  7  ω    -53.00  93.00   0.50   10.30    --    4.20  55.00  60.00  292
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065222000
_diffrn_orient_matrix_UB_12      0.0659952000
_diffrn_orient_matrix_UB_13      0.0104554000
_diffrn_orient_matrix_UB_21      -0.0354941000
_diffrn_orient_matrix_UB_22      0.0186914000
_diffrn_orient_matrix_UB_23      -0.0220955000
_diffrn_orient_matrix_UB_31      -0.0211651000
_diffrn_orient_matrix_UB_32      -0.0110295000
_diffrn_orient_matrix_UB_33      0.0249227000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6250
_reflns_number_total             7370
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         7370
_refine_ls_number_restraints     726
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+4.4158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1120
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
O1 \\sim N1 \\sim C6 \\sim C14 \\sim C5 \\sim C1 \\sim C16 \\sim C17 \\sim C15
\\sim C4 \\sim C2 \\sim N2 \\sim C3 \\sim C10 \\sim C22 \\sim C13 \\sim C9
\\sim C11 \\sim C23 \\sim C38 \\sim C32 \\sim C8 \\sim C12 \\sim C24 \\sim C28
\\sim C39 \\sim C37 \\sim C33 \\sim C31 \\sim C7 \\sim C25 \\sim C27 \\sim N4
\\sim C40 \\sim C36 \\sim C34 \\sim C30 \\sim N3 \\sim C26 \\sim C29 \\sim C41
\\sim C35 \\sim O2 \\sim C18 \\sim C21 \\sim C19 \\sim C20: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
3. Rigid body (RIGU) restrains
 O1, N1, C6, C14, C5, C1, C16, C17, C15, C4, C2, N2, C3, C10, C22, C13, C9,
 C11, C23, C38, C32, C8, C12, C24, C28, C39, C37, C33, C31, C7, C25, C27, N4,
 C40, C36, C34, C30, N3, C26, C29, C41, C35, O2, C18, C21, C19, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C12(H12), C1(H1), C31(H31), C11(H11), C2(H2), C37(H37),
 C35(H35), C30(H30), C34(H34), C24(H24), C36(H36), C28(H28), C41(H41), C40(H40),
  C27(H27), C26(H26), C25(H25)
4.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C29(H29A,H29B,H29C), C15(H15A,H15B,H15C)
;
_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 0.43955(8) 0.65492(14) 0.84045(6) 0.0302(3) Uani 1 1 d . U . . .
O2 O 0.12922(9) 0.42125(14) 0.32914(6) 0.0313(3) Uani 1 1 d . U . . .
N2 N 0.34651(8) 0.75244(15) 0.55065(7) 0.0187(3) Uani 1 1 d . U . . .
N1 N 0.44120(9) 0.72707(15) 0.79036(7) 0.0194(3) Uani 1 1 d . U . . .
N4 N 0.08377(9) 0.45325(16) 0.59873(7) 0.0218(3) Uani 1 1 d . U . . .
N3 N 0.16703(9) 0.52454(15) 0.31853(7) 0.0213(3) Uani 1 1 d . U . . .
C3 C 0.27785(10) 0.61821(17) 0.61685(8) 0.0161(3) Uani 1 1 d . U . . .
C38 C 0.20507(10) 0.42443(17) 0.56087(8) 0.0176(3) Uani 1 1 d . U . . .
C6 C 0.38573(10) 0.69715(17) 0.73121(8) 0.0171(3) Uani 1 1 d . U . . .
C5 C 0.39284(10) 0.74290(17) 0.66968(8) 0.0176(3) Uani 1 1 d . U . . .
H5 H 0.434845 0.800239 0.666627 0.021 Uiso 1 1 calc R U . . .
C4 C 0.33857(10) 0.70506(17) 0.61227(8) 0.0164(3) Uani 1 1 d . U . . .
C10 C 0.30468(10) 0.69389(17) 0.49236(8) 0.0166(3) Uani 1 1 d . U . . .
C33 C 0.07656(10) 0.58277(18) 0.57622(8) 0.0189(4) Uani 1 1 d . U . . .
C32 C 0.13879(10) 0.64401(17) 0.55516(8) 0.0168(3) Uani 1 1 d . U . . .
C7 C 0.21570(10) 0.58451(17) 0.37432(8) 0.0185(3) Uani 1 1 d . U . . .
C8 C 0.20088(10) 0.55291(17) 0.43547(8) 0.0179(3) Uani 1 1 d . U . . .
H8 H 0.159931 0.492502 0.437333 0.021 Uiso 1 1 calc R U . . .
C12 C 0.27802(11) 0.67023(18) 0.37300(9) 0.0198(4) Uani 1 1 d . U . . .
H12 H 0.290167 0.692813 0.332118 0.024 Uiso 1 1 calc R U . . .
C9 C 0.24346(10) 0.60607(16) 0.49347(8) 0.0157(3) Uani 1 1 d . U . . .
C1 C 0.32407(10) 0.61257(17) 0.73586(8) 0.0178(3) Uani 1 1 d . U . . .
H1 H 0.318342 0.581490 0.777556 0.021 Uiso 1 1 calc R U . . .
C13 C 0.21658(10) 0.57266(17) 0.55649(8) 0.0162(3) Uani 1 1 d . U . . .
C39 C 0.14088(10) 0.37123(18) 0.58213(8) 0.0195(4) Uani 1 1 d . U . . .
C31 C 0.13080(11) 0.77368(18) 0.53416(9) 0.0205(4) Uani 1 1 d . U . . .
H31 H 0.173282 0.814764 0.520254 0.025 Uiso 1 1 calc R U . . .
C11 C 0.32205(10) 0.72227(18) 0.43101(9) 0.0197(4) Uani 1 1 d . U . . .
H11 H 0.365029 0.778517 0.429356 0.024 Uiso 1 1 calc R U . . .
C23 C 0.48847(11) 0.80824(18) 0.55888(8) 0.0200(4) Uani 1 1 d . U . . .
C2 C 0.27179(10) 0.57509(17) 0.67903(8) 0.0176(3) Uani 1 1 d . U . . .
H2 H 0.229954 0.517570 0.682329 0.021 Uiso 1 1 calc R U . . .
C22 C 0.40382(10) 0.85526(17) 0.54855(9) 0.0195(4) Uani 1 1 d . U . . .
H22A H 0.400740 0.920909 0.582893 0.023 Uiso 1 1 calc R U . . .
H22B H 0.389161 0.899754 0.505289 0.023 Uiso 1 1 calc R U . . .
C37 C 0.26137(11) 0.34078(18) 0.54541(9) 0.0216(4) Uani 1 1 d . U . . .
H37 H 0.304953 0.377328 0.531214 0.026 Uiso 1 1 calc R U . . .
C35 C 0.00090(11) 0.7835(2) 0.55299(9) 0.0243(4) Uani 1 1 d . U . . .
H35 H -0.046357 0.830565 0.552210 0.029 Uiso 1 1 calc R U . . .
C18 C 0.14904(11) 0.5798(2) 0.24957(9) 0.0246(4) Uani 1 1 d . U . . .
C30 C 0.06266(11) 0.84458(19) 0.53295(9) 0.0242(4) Uani 1 1 d . U . . .
H30 H 0.058366 0.933199 0.518681 0.029 Uiso 1 1 calc R U . . .
C34 C 0.00728(11) 0.6549(2) 0.57409(9) 0.0232(4) Uani 1 1 d . U . . .
H34 H -0.035834 0.614541 0.587383 0.028 Uiso 1 1 calc R U . . .
C14 C 0.50089(11) 0.83668(19) 0.80003(9) 0.0237(4) Uani 1 1 d . U . . .
C24 C 0.50743(11) 0.67755(19) 0.55345(9) 0.0251(4) Uani 1 1 d . U . . .
H24 H 0.466637 0.614766 0.540501 0.030 Uiso 1 1 calc R U . . .
C36 C 0.25593(12) 0.20619(19) 0.55003(9) 0.0262(4) Uani 1 1 d . U . . .
H36 H 0.295134 0.150868 0.539317 0.031 Uiso 1 1 calc R U . . .
C28 C 0.54898(11) 0.8991(2) 0.57694(9) 0.0261(4) Uani 1 1 d . U . . .
H28 H 0.536685 0.989189 0.580140 0.031 Uiso 1 1 calc R U . . .
C41 C 0.19209(12) 0.15372(19) 0.57060(9) 0.0274(4) Uani 1 1 d . U . . .
H41 H 0.187359 0.061403 0.573960 0.033 Uiso 1 1 calc R U . . .
C40 C 0.13528(12) 0.23424(19) 0.58628(9) 0.0254(4) Uani 1 1 d . U . . .
H40 H 0.091743 0.196545 0.600085 0.030 Uiso 1 1 calc R U . . .
C27 C 0.62706(12) 0.8594(2) 0.59029(11) 0.0327(5) Uani 1 1 d . U . . .
H27 H 0.667944 0.922215 0.602532 0.039 Uiso 1 1 calc R U . . .
C26 C 0.64564(12) 0.7282(2) 0.58584(10) 0.0320(5) Uani 1 1 d . U . . .
H26 H 0.699105 0.700676 0.595791 0.038 Uiso 1 1 calc R U . . .
C21 C 0.07717(13) 0.5065(2) 0.21057(9) 0.0319(5) Uani 1 1 d . U . . .
H21A H 0.089349 0.412848 0.209610 0.048 Uiso 1 1 calc R U . . .
H21B H 0.063356 0.540401 0.165419 0.048 Uiso 1 1 calc R U . . .
H21C H 0.032697 0.519063 0.231642 0.048 Uiso 1 1 calc R U . . .
C19 C 0.21883(13) 0.5554(2) 0.21774(10) 0.0317(5) Uani 1 1 d . U . . .
H19A H 0.265347 0.601351 0.242877 0.048 Uiso 1 1 calc R U . . .
H19B H 0.206179 0.588117 0.172336 0.048 Uiso 1 1 calc R U . . .
H19C H 0.229712 0.461272 0.217618 0.048 Uiso 1 1 calc R U . . .
C20 C 0.12947(13) 0.7256(2) 0.25206(10) 0.0309(4) Uani 1 1 d . U . . .
H20A H 0.085645 0.736930 0.274018 0.046 Uiso 1 1 calc R U . . .
H20B H 0.114483 0.760288 0.207106 0.046 Uiso 1 1 calc R U . . .
H20C H 0.175756 0.772845 0.276642 0.046 Uiso 1 1 calc R U . . .
C25 C 0.58584(12) 0.6375(2) 0.56682(10) 0.0298(4) Uani 1 1 d . U . . .
H25 H 0.598298 0.547711 0.562877 0.036 Uiso 1 1 calc R U . . .
C16 C 0.46061(13) 0.96408(19) 0.77209(10) 0.0303(4) Uani 1 1 d . U . . .
H16A H 0.448233 0.960266 0.723833 0.045 Uiso 1 1 calc R U . . .
H16B H 0.495932 1.038106 0.786956 0.045 Uiso 1 1 calc R U . . .
H16C H 0.411845 0.975481 0.787573 0.045 Uiso 1 1 calc R U . . .
C17 C 0.53142(12) 0.8533(2) 0.87429(10) 0.0321(5) Uani 1 1 d . U . . .
H17A H 0.487504 0.875842 0.894588 0.048 Uiso 1 1 calc R U . . .
H17B H 0.570779 0.923512 0.882683 0.048 Uiso 1 1 calc R U . . .
H17C H 0.555574 0.771235 0.893232 0.048 Uiso 1 1 calc R U . . .
C29 C 0.02092(12) 0.3955(2) 0.62565(11) 0.0314(5) Uani 1 1 d . U . . .
H29A H -0.002419 0.462962 0.648826 0.047 Uiso 1 1 calc R U . . .
H29B H 0.042691 0.325321 0.656509 0.047 Uiso 1 1 calc R U . . .
H29C H -0.019668 0.359311 0.589676 0.047 Uiso 1 1 calc R U . . .
C15 C 0.57015(12) 0.7989(2) 0.76941(11) 0.0319(5) Uani 1 1 d . U . . .
H15A H 0.593663 0.717036 0.789194 0.048 Uiso 1 1 calc R U . . .
H15B H 0.609828 0.868596 0.777666 0.048 Uiso 1 1 calc R U . . .
H15C H 0.551204 0.786887 0.721791 0.048 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.2822(19) . ?
O2 N3 1.288(2) . ?
N2 C4 1.406(2) . ?
N2 C10 1.402(2) . ?
N2 C22 1.456(2) . ?
N1 C6 1.418(2) . ?
N1 C14 1.510(2) . ?
N4 C33 1.399(2) . ?
N4 C39 1.401(2) . ?
N4 C29 1.461(2) . ?
N3 C7 1.415(2) . ?
N3 C18 1.509(2) . ?
C3 C4 1.399(2) . ?
C3 C13 1.528(2) . ?
C3 C2 1.393(2) . ?
C38 C13 1.532(2) . ?
C38 C39 1.400(2) . ?
C38 C37 1.391(3) . ?
C6 C5 1.394(2) . ?
C6 C1 1.398(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.402(2) . ?
C10 C9 1.397(2) . ?
C10 C11 1.407(2) . ?
C33 C32 1.403(2) . ?
C33 C34 1.406(3) . ?
C32 C13 1.533(2) . ?
C32 C31 1.391(3) . ?
C7 C8 1.392(2) . ?
C7 C12 1.399(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.384(3) . ?
C9 C13 1.527(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.376(2) . ?
C39 C40 1.406(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.385(3) . ?
C11 H11 0.9500 . ?
C23 C22 1.519(3) . ?
C23 C24 1.385(3) . ?
C23 C28 1.391(3) . ?
C2 H2 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C37 H37 0.9500 . ?
C37 C36 1.382(3) . ?
C35 H35 0.9500 . ?
C35 C30 1.386(3) . ?
C35 C34 1.381(3) . ?
C18 C21 1.527(3) . ?
C18 C19 1.528(3) . ?
C18 C20 1.531(3) . ?
C30 H30 0.9500 . ?
C34 H34 0.9500 . ?
C14 C16 1.530(3) . ?
C14 C17 1.528(3) . ?
C14 C15 1.534(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.392(3) . ?
C36 H36 0.9500 . ?
C36 C41 1.385(3) . ?
C28 H28 0.9500 . ?
C28 C27 1.386(3) . ?
C41 H41 0.9500 . ?
C41 C40 1.380(3) . ?
C40 H40 0.9500 . ?
C27 H27 0.9500 . ?
C27 C26 1.386(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.383(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C25 H25 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N2 C22 118.87(14) . . ?
C10 N2 C4 120.33(14) . . ?
C10 N2 C22 120.58(14) . . ?
O1 N1 C6 116.60(14) . . ?
O1 N1 C14 117.19(14) . . ?
C6 N1 C14 126.20(14) . . ?
C33 N4 C39 119.86(15) . . ?
C33 N4 C29 119.43(16) . . ?
C39 N4 C29 119.14(16) . . ?
O2 N3 C7 116.67(14) . . ?
O2 N3 C18 117.61(14) . . ?
C7 N3 C18 125.34(15) . . ?
C4 C3 C13 122.44(15) . . ?
C2 C3 C4 118.58(15) . . ?
C2 C3 C13 118.95(15) . . ?
C39 C38 C13 121.75(16) . . ?
C37 C38 C13 118.98(16) . . ?
C37 C38 C39 119.24(17) . . ?
C5 C6 N1 122.85(16) . . ?
C5 C6 C1 119.83(16) . . ?
C1 C6 N1 117.24(15) . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.63(16) . . ?
C4 C5 H5 119.7 . . ?
C3 C4 N2 120.63(15) . . ?
C3 C4 C5 119.49(15) . . ?
C5 C4 N2 119.87(15) . . ?
N2 C10 C11 121.50(15) . . ?
C9 C10 N2 120.68(15) . . ?
C9 C10 C11 117.81(16) . . ?
N4 C33 C32 120.52(16) . . ?
N4 C33 C34 121.19(16) . . ?
C32 C33 C34 118.29(17) . . ?
C33 C32 C13 121.56(16) . . ?
C31 C32 C33 119.47(16) . . ?
C31 C32 C13 118.94(15) . . ?
C8 C7 N3 116.80(16) . . ?
C8 C7 C12 117.75(16) . . ?
C12 C7 N3 125.43(16) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 C7 122.42(16) . . ?
C9 C8 H8 118.8 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.28(16) . . ?
C11 C12 H12 119.9 . . ?
C10 C9 C13 122.61(15) . . ?
C8 C9 C10 120.08(16) . . ?
C8 C9 C13 117.15(15) . . ?
C6 C1 H1 120.6 . . ?
C2 C1 C6 118.89(16) . . ?
C2 C1 H1 120.6 . . ?
C3 C13 C38 109.17(14) . . ?
C3 C13 C32 108.81(13) . . ?
C38 C13 C32 110.11(14) . . ?
C9 C13 C3 110.30(14) . . ?
C9 C13 C38 109.94(14) . . ?
C9 C13 C32 108.50(14) . . ?
N4 C39 C40 121.11(17) . . ?
C38 C39 N4 120.44(16) . . ?
C38 C39 C40 118.45(17) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 C32 121.88(17) . . ?
C30 C31 H31 119.1 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.58(16) . . ?
C12 C11 H11 119.2 . . ?
C24 C23 C22 122.29(16) . . ?
C24 C23 C28 118.98(18) . . ?
C28 C23 C22 118.68(17) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 C3 122.55(16) . . ?
C1 C2 H2 118.7 . . ?
N2 C22 C23 114.70(15) . . ?
N2 C22 H22A 108.6 . . ?
N2 C22 H22B 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C38 C37 H37 118.9 . . ?
C36 C37 C38 122.11(18) . . ?
C36 C37 H37 118.9 . . ?
C30 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C34 C35 C30 120.73(17) . . ?
N3 C18 C21 107.12(15) . . ?
N3 C18 C19 109.59(16) . . ?
N3 C18 C20 109.37(15) . . ?
C21 C18 C19 109.06(16) . . ?
C21 C18 C20 109.41(17) . . ?
C19 C18 C20 112.16(17) . . ?
C31 C30 C35 118.58(18) . . ?
C31 C30 H30 120.7 . . ?
C35 C30 H30 120.7 . . ?
C33 C34 H34 119.5 . . ?
C35 C34 C33 121.04(17) . . ?
C35 C34 H34 119.5 . . ?
N1 C14 C16 109.63(15) . . ?
N1 C14 C17 106.93(15) . . ?
N1 C14 C15 109.86(15) . . ?
C16 C14 C15 113.09(17) . . ?
C17 C14 C16 108.47(16) . . ?
C17 C14 C15 108.66(16) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.48(18) . . ?
C25 C24 H24 119.8 . . ?
C37 C36 H36 120.7 . . ?
C37 C36 C41 118.56(18) . . ?
C41 C36 H36 120.7 . . ?
C23 C28 H28 119.7 . . ?
C27 C28 C23 120.58(19) . . ?
C27 C28 H28 119.7 . . ?
C36 C41 H41 119.7 . . ?
C40 C41 C36 120.65(18) . . ?
C40 C41 H41 119.7 . . ?
C39 C40 H40 119.5 . . ?
C41 C40 C39 120.98(18) . . ?
C41 C40 H40 119.5 . . ?
C28 C27 H27 119.9 . . ?
C26 C27 C28 120.17(19) . . ?
C26 C27 H27 119.9 . . ?
C27 C26 H26 120.2 . . ?
C25 C26 C27 119.59(19) . . ?
C25 C26 H26 120.2 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.18(19) . . ?
C26 C25 H25 119.9 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C29 H29A 109.5 . . ?
N4 C29 H29B 109.5 . . ?
N4 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C6 C5 -163.20(16) . . . . ?
O1 N1 C6 C1 13.5(2) . . . . ?
O1 N1 C14 C16 -131.27(17) . . . . ?
O1 N1 C14 C17 -13.9(2) . . . . ?
O1 N1 C14 C15 103.87(19) . . . . ?
O2 N3 C7 C8 -18.8(2) . . . . ?
O2 N3 C7 C12 159.85(17) . . . . ?
O2 N3 C18 C21 9.2(2) . . . . ?
O2 N3 C18 C19 -109.03(18) . . . . ?
O2 N3 C18 C20 127.64(18) . . . . ?
N2 C10 C9 C8 177.60(16) . . . . ?
N2 C10 C9 C13 2.3(3) . . . . ?
N2 C10 C11 C12 -176.36(16) . . . . ?
N1 C6 C5 C4 176.72(16) . . . . ?
N1 C6 C1 C2 -176.16(16) . . . . ?
N4 C33 C32 C13 -0.5(2) . . . . ?
N4 C33 C32 C31 -178.79(15) . . . . ?
N4 C33 C34 C35 178.80(16) . . . . ?
N4 C39 C40 C41 -179.27(17) . . . . ?
N3 C7 C8 C9 -179.13(16) . . . . ?
N3 C7 C12 C11 -179.52(17) . . . . ?
C38 C39 C40 C41 0.8(3) . . . . ?
C38 C37 C36 C41 0.2(3) . . . . ?
C6 N1 C14 C16 47.7(2) . . . . ?
C6 N1 C14 C17 165.14(17) . . . . ?
C6 N1 C14 C15 -77.1(2) . . . . ?
C6 C5 C4 N2 179.82(16) . . . . ?
C6 C5 C4 C3 -1.5(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C5 C6 C1 C2 0.6(3) . . . . ?
C4 N2 C10 C9 12.7(2) . . . . ?
C4 N2 C10 C11 -168.03(16) . . . . ?
C4 N2 C22 C23 79.1(2) . . . . ?
C4 C3 C13 C38 135.11(16) . . . . ?
C4 C3 C13 C32 -104.71(18) . . . . ?
C4 C3 C13 C9 14.2(2) . . . . ?
C4 C3 C2 C1 -1.3(3) . . . . ?
C10 N2 C4 C3 -13.2(2) . . . . ?
C10 N2 C4 C5 165.51(16) . . . . ?
C10 N2 C22 C23 -95.54(19) . . . . ?
C10 C9 C13 C3 -14.7(2) . . . . ?
C10 C9 C13 C38 -135.16(16) . . . . ?
C10 C9 C13 C32 104.37(18) . . . . ?
C33 N4 C39 C38 19.1(2) . . . . ?
C33 N4 C39 C40 -160.79(17) . . . . ?
C33 C32 C13 C3 -101.16(18) . . . . ?
C33 C32 C13 C38 18.4(2) . . . . ?
C33 C32 C13 C9 138.81(16) . . . . ?
C33 C32 C31 C30 -0.4(3) . . . . ?
C32 C33 C34 C35 -1.2(3) . . . . ?
C32 C31 C30 C35 -0.3(3) . . . . ?
C7 N3 C18 C21 -163.57(17) . . . . ?
C7 N3 C18 C19 78.2(2) . . . . ?
C7 N3 C18 C20 -45.1(2) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C7 C8 C9 C13 174.73(16) . . . . ?
C7 C12 C11 C10 -1.6(3) . . . . ?
C8 C7 C12 C11 -0.9(3) . . . . ?
C8 C9 C13 C3 169.85(15) . . . . ?
C8 C9 C13 C38 49.4(2) . . . . ?
C8 C9 C13 C32 -71.05(19) . . . . ?
C12 C7 C8 C9 2.1(3) . . . . ?
C9 C10 C11 C12 2.9(3) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C13 C3 C4 N2 -1.3(3) . . . . ?
C13 C3 C4 C5 179.98(15) . . . . ?
C13 C3 C2 C1 -179.34(16) . . . . ?
C13 C38 C39 N4 1.5(2) . . . . ?
C13 C38 C39 C40 -178.57(16) . . . . ?
C13 C38 C37 C36 178.17(17) . . . . ?
C13 C32 C31 C30 -178.75(16) . . . . ?
C39 N4 C33 C32 -19.6(2) . . . . ?
C39 N4 C33 C34 160.41(16) . . . . ?
C39 C38 C13 C3 100.44(18) . . . . ?
C39 C38 C13 C32 -18.9(2) . . . . ?
C39 C38 C13 C9 -138.44(16) . . . . ?
C39 C38 C37 C36 0.3(3) . . . . ?
C31 C32 C13 C3 77.11(19) . . . . ?
C31 C32 C13 C38 -163.28(15) . . . . ?
C31 C32 C13 C9 -42.9(2) . . . . ?
C11 C10 C9 C8 -1.7(2) . . . . ?
C11 C10 C9 C13 -176.99(15) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C23 C28 C27 C26 -0.1(3) . . . . ?
C2 C3 C4 N2 -179.27(16) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C2 C3 C13 C38 -46.9(2) . . . . ?
C2 C3 C13 C32 73.25(19) . . . . ?
C2 C3 C13 C9 -167.84(15) . . . . ?
C22 N2 C4 C3 172.11(16) . . . . ?
C22 N2 C4 C5 -9.2(2) . . . . ?
C22 N2 C10 C9 -172.69(16) . . . . ?
C22 N2 C10 C11 6.6(2) . . . . ?
C22 C23 C24 C25 -176.47(17) . . . . ?
C22 C23 C28 C27 176.53(17) . . . . ?
C37 C38 C13 C3 -77.37(19) . . . . ?
C37 C38 C13 C32 163.24(15) . . . . ?
C37 C38 C13 C9 43.8(2) . . . . ?
C37 C38 C39 N4 179.29(16) . . . . ?
C37 C38 C39 C40 -0.8(2) . . . . ?
C37 C36 C41 C40 -0.1(3) . . . . ?
C18 N3 C7 C8 154.00(17) . . . . ?
C18 N3 C7 C12 -27.4(3) . . . . ?
C30 C35 C34 C33 0.4(3) . . . . ?
C34 C33 C32 C13 179.44(15) . . . . ?
C34 C33 C32 C31 1.2(2) . . . . ?
C34 C35 C30 C31 0.4(3) . . . . ?
C14 N1 C6 C5 17.8(3) . . . . ?
C14 N1 C6 C1 -165.53(16) . . . . ?
C24 C23 C22 N2 16.1(2) . . . . ?
C24 C23 C28 C27 -1.0(3) . . . . ?
C36 C41 C40 C39 -0.3(3) . . . . ?
C28 C23 C22 N2 -161.35(16) . . . . ?
C28 C23 C24 C25 1.0(3) . . . . ?
C28 C27 C26 C25 1.2(3) . . . . ?
C27 C26 C25 C24 -1.2(3) . . . . ?
C29 N4 C33 C32 174.77(17) . . . . ?
C29 N4 C33 C34 -5.2(3) . . . . ?
C29 N4 C39 C38 -175.22(16) . . . . ?
C29 N4 C39 C40 4.8(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.163 0.070 0.335 132.8 42.3 ?
2 -0.163 -0.070 0.665 132.8 42.3 ?
3 0.163 0.430 0.835 132.8 42.3 ?
4 -0.163 0.570 0.165 132.8 42.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 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 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.854
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, n-hexane'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_1_mm
_database_code_depnum_ccdc_archive 'CCDC 2394808'
loop_
_audit_author_name
_audit_author_address
'Takuya Kanetomo'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2025-03-03 downloaded from the CCDC.
;
_audit_creation_date             2024-10-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
"10-benzyl-10'-methyl-9,9'(10H,10'H)spirobiacridine-3,6-diyl bis(tert-butyl nitroxide)"
_chemical_formula_moiety         'C41 H42 N4 O2'
_chemical_formula_sum            'C41 H42 N4 O2'
_chemical_formula_weight         622.78
_chemical_melting_point          464
_chemical_oxdiff_formula         'C42H44N4O2Cl2 '
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                   21.4155(5)
_cell_length_b                   13.3956(3)
_cell_length_c                   11.9815(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.165(2)
_cell_angle_gamma                90
_cell_volume                     3410.33(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15657
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      29.4230
_cell_measurement_theta_min      2.4200
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
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            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 0 0.0570
-1 -1 0 0.0990
-1 0 0 0.0630
1 0 0 0.0390
1 0 -2 0.2775
0 0 1 0.0895
1 2 0 0.0735
-2 1 0 0.0676
1 -2 0 0.0975
-1 2 0 0.0705

_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
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
2.0000 0.9994 -0.0003 0.0851 -0.0019 -0.0028
-1.0000 -0.9994 0.0001 -0.0594 -0.0194 0.0015
-0.9999 0.0001 0.0001 -0.0257 0.0213 0.0013
0.9999 -0.0001 -0.0001 0.0257 -0.0213 -0.0013
0.9994 -0.0001 -1.9994 0.0104 -0.0095 -0.1190
0.0003 0.0000 0.9996 0.0076 -0.0059 0.0589
1.0001 1.9990 -0.0001 0.0932 0.0602 -0.0018
-1.9998 0.9996 0.0003 -0.0175 0.0833 0.0022
0.9998 -1.9990 -0.0001 -0.0419 -0.1028 -0.0007
-0.9998 1.9990 0.0001 0.0419 0.1028 0.0007

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41220
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.291
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  -4.00   0.50    5.27    --   -3.30  37.00 -60.00   60
  2  ω    -61.00 -14.00   0.50    5.27    --    4.30  46.00-150.00   94
  3  ω     44.00  94.00   0.50    5.27    --    4.30  46.00-150.00  100
  4  ω    -85.00  94.00   0.50    5.27    --    4.30  37.00 -30.00  358
  5  ω     -5.00  20.00   0.50    5.27    --    4.30  18.00  60.00   50
  6  ω    -47.00  -7.00   0.50    5.27    --    4.30  18.00  60.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0256648000
_diffrn_orient_matrix_UB_12      0.0338014000
_diffrn_orient_matrix_UB_13      0.0076144000
_diffrn_orient_matrix_UB_21      -0.0213088000
_diffrn_orient_matrix_UB_22      0.0407511000
_diffrn_orient_matrix_UB_23      -0.0059229000
_diffrn_orient_matrix_UB_31      -0.0012511000
_diffrn_orient_matrix_UB_32      -0.0002737000
_diffrn_orient_matrix_UB_33      0.0588848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6606
_reflns_number_total             7459
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     431
_refine_ls_number_reflns         7459
_refine_ls_number_restraints     726
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      0.995
_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)+(0.0464P)²+2.0583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C7 \\sim O2 \\sim N3 \\sim C12 \\sim C18 \\sim C11 \\sim C20 \\sim C19 \\sim
C21 \\sim C10 \\sim C8 \\sim N2 \\sim C9 \\sim C4 \\sim C22 \\sim C13 \\sim C3
\\sim C5 \\sim C23 \\sim C38 \\sim C32 \\sim C2 \\sim C6 \\sim C24 \\sim C28
\\sim C39 \\sim C37 \\sim C33 \\sim C31 \\sim C1 \\sim N1 \\sim C25 \\sim C27
\\sim N4 \\sim C40 \\sim C36 \\sim C34 \\sim C30 \\sim O1 \\sim C14 \\sim C26
\\sim C29 \\sim C41 \\sim C35 \\sim C16 \\sim C17 \\sim C15: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
3. Rigid body (RIGU) restrains
 C7, O2, N3, C12, C18, C11, C20, C19, C21, C10, C8, N2, C9, C4, C22, C13, C3,
 C5, C23, C38, C32, C2, C6, C24, C28, C39, C37, C33, C31, C1, N1, C25, C27, N4,
 C40, C36, C34, C30, O1, C14, C26, C29, C41, C35, C16, C17, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
4.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C24(H24), C31(H31), C37(H37), C28(H28), C2(H2), C8(H8),
 C30(H30), C1(H1), C7(H7), C41(H41), C36(H36), C40(H40), C34(H34), C25(H25),
 C35(H35), C26(H26), C27(H27)
4.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C20(H20A,H20B,H20C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C15(H15A,H15B,H15C)
;
_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
O2 O 0.90253(5) 0.49042(8) 0.00474(8) 0.0267(2) Uani 1 1 d . U . . .
N2 N 0.71905(5) 0.41104(8) 0.20876(8) 0.0160(2) Uani 1 1 d . U . . .
N3 N 0.90234(5) 0.56193(9) 0.07587(9) 0.0193(2) Uani 1 1 d . U . . .
N4 N 0.78290(5) 0.49647(9) 0.68232(9) 0.0200(2) Uani 1 1 d . U . . .
O1 O 0.49846(6) 0.30828(13) 0.18885(9) 0.0514(4) Uani 1 1 d . U . . .
N1 N 0.51340(5) 0.31337(10) 0.29547(9) 0.0250(3) Uani 1 1 d . U . . .
C10 C 0.77313(6) 0.47048(9) 0.22930(10) 0.0143(2) Uani 1 1 d . U . . .
C4 C 0.67527(6) 0.40775(9) 0.28711(10) 0.0153(2) Uani 1 1 d . U . . .
C39 C 0.76312(6) 0.58301(10) 0.62317(11) 0.0174(3) Uani 1 1 d . U . . .
C23 C 0.67795(6) 0.39644(9) 0.00247(10) 0.0156(2) Uani 1 1 d . U . . .
C3 C 0.69170(6) 0.44140(9) 0.39789(10) 0.0158(2) Uani 1 1 d . U . . .
C9 C 0.79023(6) 0.51190(9) 0.33609(10) 0.0149(2) Uani 1 1 d . U . . .
C11 C 0.81093(6) 0.48904(9) 0.14363(10) 0.0161(2) Uani 1 1 d . U . . .
H11 H 0.800049 0.460254 0.071356 0.019 Uiso 1 1 calc R U . . .
C6 C 0.57278(6) 0.35585(10) 0.33438(11) 0.0198(3) Uani 1 1 d . U . . .
C5 C 0.61488(6) 0.36936(10) 0.25538(10) 0.0174(2) Uani 1 1 d . U . . .
H5 H 0.602296 0.352208 0.178950 0.021 Uiso 1 1 calc R U . . .
C38 C 0.74881(6) 0.58081(10) 0.50571(10) 0.0164(2) Uani 1 1 d . U . . .
C22 C 0.71017(6) 0.34791(9) 0.10872(10) 0.0154(2) Uani 1 1 d . U . . .
H22A H 0.685183 0.288851 0.125623 0.019 Uiso 1 1 calc R U . . .
H22B H 0.751939 0.323611 0.093513 0.019 Uiso 1 1 calc R U . . .
C12 C 0.86421(6) 0.54930(9) 0.16379(11) 0.0170(2) Uani 1 1 d . U . . .
C13 C 0.75636(6) 0.48593(9) 0.43731(10) 0.0148(2) Uani 1 1 d . U . . .
C33 C 0.80799(6) 0.41714(10) 0.62672(11) 0.0175(3) Uani 1 1 d . U . . .
C32 C 0.79640(6) 0.40869(9) 0.50905(10) 0.0159(2) Uani 1 1 d . U . . .
C24 C 0.64934(6) 0.48955(10) 0.00265(11) 0.0188(3) Uani 1 1 d . U . . .
H24 H 0.650095 0.525507 0.071148 0.023 Uiso 1 1 calc R U . . .
C31 C 0.82124(6) 0.32737(10) 0.45645(11) 0.0191(3) Uani 1 1 d . U . . .
H31 H 0.813314 0.321688 0.376906 0.023 Uiso 1 1 calc R U . . .
C37 C 0.72697(6) 0.66763(10) 0.44942(11) 0.0208(3) Uani 1 1 d . U . . .
H37 H 0.715629 0.665424 0.370236 0.025 Uiso 1 1 calc R U . . .
C28 C 0.67625(6) 0.34449(10) -0.09864(11) 0.0207(3) Uani 1 1 d . U . . .
H28 H 0.695454 0.280626 -0.099651 0.025 Uiso 1 1 calc R U . . .
C2 C 0.64831(6) 0.42923(10) 0.47437(11) 0.0203(3) Uani 1 1 d . U . . .
H2 H 0.659210 0.452073 0.549328 0.024 Uiso 1 1 calc R U . . .
C8 C 0.84330(6) 0.57254(10) 0.35300(11) 0.0198(3) Uani 1 1 d . U . . .
H8 H 0.854539 0.601285 0.425190 0.024 Uiso 1 1 calc R U . . .
C30 C 0.85718(6) 0.25455(10) 0.51690(12) 0.0228(3) Uani 1 1 d . U . . .
H30 H 0.872769 0.198977 0.479617 0.027 Uiso 1 1 calc R U . . .
C1 C 0.59012(6) 0.38536(11) 0.44586(11) 0.0227(3) Uani 1 1 d . U . . .
H1 H 0.562433 0.375435 0.500940 0.027 Uiso 1 1 calc R U . . .
C7 C 0.88031(6) 0.59270(10) 0.26932(11) 0.0201(3) Uani 1 1 d . U . . .
H7 H 0.915956 0.635170 0.283255 0.024 Uiso 1 1 calc R U . . .
C41 C 0.73742(6) 0.75944(10) 0.62129(12) 0.0240(3) Uani 1 1 d . U . . .
H41 H 0.734626 0.820507 0.660682 0.029 Uiso 1 1 calc R U . . .
C36 C 0.72134(7) 0.75682(10) 0.50554(13) 0.0243(3) Uani 1 1 d . U . . .
H36 H 0.706721 0.815215 0.465514 0.029 Uiso 1 1 calc R U . . .
C14 C 0.47093(6) 0.25979(11) 0.36791(11) 0.0230(3) Uani 1 1 d . U . . .
C40 C 0.75745(6) 0.67418(11) 0.67975(12) 0.0223(3) Uani 1 1 d . U . . .
H40 H 0.767553 0.676967 0.759178 0.027 Uiso 1 1 calc R U . . .
C34 C 0.84618(6) 0.34458(11) 0.68686(12) 0.0233(3) Uani 1 1 d . U . . .
H34 H 0.855835 0.350775 0.766121 0.028 Uiso 1 1 calc R U . . .
C25 C 0.61958(7) 0.53051(10) -0.09678(12) 0.0238(3) Uani 1 1 d . U . . .
H25 H 0.600044 0.594124 -0.095954 0.029 Uiso 1 1 calc R U . . .
C35 C 0.86985(6) 0.26452(11) 0.63260(13) 0.0250(3) Uani 1 1 d . U . . .
H35 H 0.894998 0.215974 0.674984 0.030 Uiso 1 1 calc R U . . .
C26 C 0.61846(7) 0.47849(11) -0.19699(12) 0.0278(3) Uani 1 1 d . U . . .
H26 H 0.598370 0.506519 -0.264994 0.033 Uiso 1 1 calc R U . . .
C18 C 0.93965(6) 0.65510(11) 0.05761(13) 0.0257(3) Uani 1 1 d . U . . .
C27 C 0.64676(8) 0.38533(11) -0.19771(12) 0.0277(3) Uani 1 1 d . U . . .
H27 H 0.645913 0.349465 -0.266282 0.033 Uiso 1 1 calc R U . . .
C29 C 0.79062(8) 0.49831(12) 0.80494(11) 0.0288(3) Uani 1 1 d . U . . .
H29A H 0.831948 0.526188 0.832769 0.043 Uiso 1 1 calc R U . . .
H29B H 0.787510 0.430212 0.833610 0.043 Uiso 1 1 calc R U . . .
H29C H 0.757580 0.539785 0.830851 0.043 Uiso 1 1 calc R U . . .
C20 C 1.00288(7) 0.65380(12) 0.13237(13) 0.0280(3) Uani 1 1 d . U . . .
H20A H 0.995731 0.655620 0.211553 0.042 Uiso 1 1 calc R U . . .
H20B H 1.027658 0.712170 0.115536 0.042 Uiso 1 1 calc R U . . .
H20C H 1.025810 0.592766 0.117977 0.042 Uiso 1 1 calc R U . . .
C16 C 0.50890(8) 0.17897(13) 0.43528(14) 0.0346(4) Uani 1 1 d . U . . .
H16A H 0.527481 0.134167 0.383788 0.052 Uiso 1 1 calc R U . . .
H16B H 0.481187 0.140731 0.478568 0.052 Uiso 1 1 calc R U . . .
H16C H 0.542464 0.210024 0.486835 0.052 Uiso 1 1 calc R U . . .
C17 C 0.44135(8) 0.33359(13) 0.44400(14) 0.0358(4) Uani 1 1 d . U . . .
H17A H 0.473342 0.355803 0.504564 0.054 Uiso 1 1 calc R U . . .
H17B H 0.406927 0.300728 0.476486 0.054 Uiso 1 1 calc R U . . .
H17C H 0.424895 0.391389 0.399554 0.054 Uiso 1 1 calc R U . . .
C19 C 0.95250(8) 0.65511(15) -0.06484(14) 0.0407(4) Uani 1 1 d . U . . .
H19A H 0.976568 0.595304 -0.079429 0.061 Uiso 1 1 calc R U . . .
H19B H 0.976717 0.714771 -0.079340 0.061 Uiso 1 1 calc R U . . .
H19C H 0.912469 0.655247 -0.114384 0.061 Uiso 1 1 calc R U . . .
C21 C 0.90091(8) 0.74709(13) 0.08056(19) 0.0450(5) Uani 1 1 d . U . . .
H21A H 0.860540 0.745430 0.032064 0.068 Uiso 1 1 calc R U . . .
H21B H 0.924006 0.807581 0.064760 0.068 Uiso 1 1 calc R U . . .
H21C H 0.893373 0.747198 0.159574 0.068 Uiso 1 1 calc R U . . .
C15 C 0.41862(8) 0.21093(16) 0.28855(14) 0.0425(4) Uani 1 1 d . U . . .
H15A H 0.395738 0.262230 0.241564 0.064 Uiso 1 1 calc R U . . .
H15B H 0.389544 0.176506 0.332562 0.064 Uiso 1 1 calc R U . . .
H15C H 0.436932 0.162639 0.240474 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N3 1.2825(15) . ?
N2 C10 1.4016(16) . ?
N2 C4 1.4077(15) . ?
N2 C22 1.4599(15) . ?
N3 C12 1.4211(16) . ?
N3 C18 1.5125(17) . ?
N4 C39 1.3967(17) . ?
N4 C33 1.3967(17) . ?
N4 C29 1.4580(16) . ?
O1 N1 1.2794(15) . ?
N1 C6 1.4181(17) . ?
N1 C14 1.5140(17) . ?
C10 C9 1.4008(17) . ?
C10 C11 1.4065(17) . ?
C4 C3 1.4045(17) . ?
C4 C5 1.3996(17) . ?
C39 C38 1.4027(17) . ?
C39 C40 1.4094(19) . ?
C23 C22 1.5166(17) . ?
C23 C24 1.3897(18) . ?
C23 C28 1.3937(18) . ?
C3 C13 1.5275(17) . ?
C3 C2 1.3936(18) . ?
C9 C13 1.5288(16) . ?
C9 C8 1.3910(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3939(18) . ?
C6 C5 1.3979(18) . ?
C6 C1 1.3981(19) . ?
C5 H5 0.9500 . ?
C38 C13 1.5318(17) . ?
C38 C37 1.3955(18) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C12 C7 1.3953(18) . ?
C13 C32 1.5364(17) . ?
C33 C32 1.4052(17) . ?
C33 C34 1.4093(19) . ?
C32 C31 1.3966(18) . ?
C24 H24 0.9500 . ?
C24 C25 1.3917(19) . ?
C31 H31 0.9500 . ?
C31 C30 1.3891(19) . ?
C37 H37 0.9500 . ?
C37 C36 1.3836(19) . ?
C28 H28 0.9500 . ?
C28 C27 1.3856(19) . ?
C2 H2 0.9500 . ?
C2 C1 1.3815(19) . ?
C8 H8 0.9500 . ?
C8 C7 1.3801(19) . ?
C30 H30 0.9500 . ?
C30 C35 1.385(2) . ?
C1 H1 0.9500 . ?
C7 H7 0.9500 . ?
C41 H41 0.9500 . ?
C41 C36 1.387(2) . ?
C41 C40 1.380(2) . ?
C36 H36 0.9500 . ?
C14 C16 1.524(2) . ?
C14 C17 1.534(2) . ?
C14 C15 1.524(2) . ?
C40 H40 0.9500 . ?
C34 H34 0.9500 . ?
C34 C35 1.383(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(2) . ?
C35 H35 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.388(2) . ?
C18 C20 1.528(2) . ?
C18 C19 1.526(2) . ?
C18 C21 1.529(2) . ?
C27 H27 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N2 C4 120.34(10) . . ?
C10 N2 C22 119.57(10) . . ?
C4 N2 C22 119.99(10) . . ?
O2 N3 C12 116.96(11) . . ?
O2 N3 C18 118.34(11) . . ?
C12 N3 C18 124.63(11) . . ?
C39 N4 C33 119.99(11) . . ?
C39 N4 C29 119.10(12) . . ?
C33 N4 C29 119.44(12) . . ?
O1 N1 C6 116.86(11) . . ?
O1 N1 C14 117.00(11) . . ?
C6 N1 C14 125.45(11) . . ?
N2 C10 C11 120.70(11) . . ?
C9 C10 N2 120.11(11) . . ?
C9 C10 C11 119.20(11) . . ?
C3 C4 N2 120.73(11) . . ?
C5 C4 N2 120.01(11) . . ?
C5 C4 C3 119.25(11) . . ?
N4 C39 C38 120.41(11) . . ?
N4 C39 C40 120.93(12) . . ?
C38 C39 C40 118.66(12) . . ?
C24 C23 C22 122.54(11) . . ?
C24 C23 C28 119.06(12) . . ?
C28 C23 C22 118.39(11) . . ?
C4 C3 C13 121.88(11) . . ?
C2 C3 C4 118.35(11) . . ?
C2 C3 C13 119.71(11) . . ?
C10 C9 C13 122.58(11) . . ?
C8 C9 C10 118.70(11) . . ?
C8 C9 C13 118.50(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.61(12) . . ?
C12 C11 H11 119.7 . . ?
C5 C6 N1 117.20(12) . . ?
C5 C6 C1 119.57(12) . . ?
C1 C6 N1 123.23(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.05(12) . . ?
C6 C5 H5 119.5 . . ?
C39 C38 C13 121.99(11) . . ?
C37 C38 C39 119.05(12) . . ?
C37 C38 C13 118.96(11) . . ?
N2 C22 C23 116.10(10) . . ?
N2 C22 H22A 108.3 . . ?
N2 C22 H22B 108.3 . . ?
C23 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
C11 C12 N3 118.30(11) . . ?
C11 C12 C7 120.18(12) . . ?
C7 C12 N3 121.48(11) . . ?
C3 C13 C9 110.19(10) . . ?
C3 C13 C38 109.71(10) . . ?
C3 C13 C32 109.34(10) . . ?
C9 C13 C38 109.13(10) . . ?
C9 C13 C32 108.07(10) . . ?
C38 C13 C32 110.38(10) . . ?
N4 C33 C32 120.63(11) . . ?
N4 C33 C34 120.94(12) . . ?
C32 C33 C34 118.43(12) . . ?
C33 C32 C13 121.57(11) . . ?
C31 C32 C13 119.35(11) . . ?
C31 C32 C33 119.08(12) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.49(12) . . ?
C25 C24 H24 119.8 . . ?
C32 C31 H31 119.0 . . ?
C30 C31 C32 122.00(12) . . ?
C30 C31 H31 119.0 . . ?
C38 C37 H37 119.0 . . ?
C36 C37 C38 121.94(13) . . ?
C36 C37 H37 119.0 . . ?
C23 C28 H28 119.8 . . ?
C27 C28 C23 120.48(13) . . ?
C27 C28 H28 119.8 . . ?
C3 C2 H2 118.6 . . ?
C1 C2 C3 122.82(12) . . ?
C1 C2 H2 118.6 . . ?
C9 C8 H8 118.6 . . ?
C7 C8 C9 122.77(12) . . ?
C7 C8 H8 118.6 . . ?
C31 C30 H30 120.6 . . ?
C35 C30 C31 118.74(13) . . ?
C35 C30 H30 120.6 . . ?
C6 C1 H1 120.6 . . ?
C2 C1 C6 118.71(12) . . ?
C2 C1 H1 120.6 . . ?
C12 C7 H7 120.7 . . ?
C8 C7 C12 118.51(12) . . ?
C8 C7 H7 120.7 . . ?
C36 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C40 C41 C36 120.61(13) . . ?
C37 C36 C41 118.81(13) . . ?
C37 C36 H36 120.6 . . ?
C41 C36 H36 120.6 . . ?
N1 C14 C16 108.76(11) . . ?
N1 C14 C17 110.93(12) . . ?
N1 C14 C15 107.06(11) . . ?
C16 C14 C17 112.07(12) . . ?
C16 C14 C15 109.13(14) . . ?
C15 C14 C17 108.76(13) . . ?
C39 C40 H40 119.6 . . ?
C41 C40 C39 120.87(13) . . ?
C41 C40 H40 119.6 . . ?
C33 C34 H34 119.4 . . ?
C35 C34 C33 121.20(13) . . ?
C35 C34 H34 119.4 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.01(13) . . ?
C26 C25 H25 120.0 . . ?
C30 C35 H35 119.7 . . ?
C34 C35 C30 120.51(13) . . ?
C34 C35 H35 119.7 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.80(13) . . ?
C27 C26 H26 120.1 . . ?
N3 C18 C20 110.57(11) . . ?
N3 C18 C19 107.52(12) . . ?
N3 C18 C21 109.30(11) . . ?
C20 C18 C21 111.39(14) . . ?
C19 C18 C20 108.11(12) . . ?
C19 C18 C21 109.86(14) . . ?
C28 C27 C26 120.16(13) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
N4 C29 H29A 109.5 . . ?
N4 C29 H29B 109.5 . . ?
N4 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 C12 C11 -28.11(17) . . . . ?
O2 N3 C12 C7 149.62(12) . . . . ?
O2 N3 C18 C20 -99.67(14) . . . . ?
O2 N3 C18 C19 18.15(16) . . . . ?
O2 N3 C18 C21 137.36(14) . . . . ?
N2 C10 C9 C13 7.03(18) . . . . ?
N2 C10 C9 C8 -178.45(11) . . . . ?
N2 C10 C11 C12 179.11(11) . . . . ?
N2 C4 C3 C13 2.06(18) . . . . ?
N2 C4 C3 C2 -175.02(12) . . . . ?
N2 C4 C5 C6 173.41(12) . . . . ?
N3 C12 C7 C8 -176.13(12) . . . . ?
N4 C39 C38 C13 -2.25(18) . . . . ?
N4 C39 C38 C37 177.68(12) . . . . ?
N4 C39 C40 C41 -179.48(12) . . . . ?
N4 C33 C32 C13 0.37(18) . . . . ?
N4 C33 C32 C31 -178.79(11) . . . . ?
N4 C33 C34 C35 178.36(12) . . . . ?
O1 N1 C6 C5 -12.8(2) . . . . ?
O1 N1 C6 C1 166.28(15) . . . . ?
O1 N1 C14 C16 117.96(16) . . . . ?
O1 N1 C14 C17 -118.35(16) . . . . ?
O1 N1 C14 C15 0.17(19) . . . . ?
N1 C6 C5 C4 -177.90(12) . . . . ?
N1 C6 C1 C2 -177.75(13) . . . . ?
C10 N2 C4 C3 -16.71(18) . . . . ?
C10 N2 C4 C5 164.17(11) . . . . ?
C10 N2 C22 C23 -87.52(14) . . . . ?
C10 C9 C13 C3 -19.26(16) . . . . ?
C10 C9 C13 C38 -139.78(12) . . . . ?
C10 C9 C13 C32 100.16(13) . . . . ?
C10 C9 C8 C7 -0.8(2) . . . . ?
C10 C11 C12 N3 177.17(11) . . . . ?
C10 C11 C12 C7 -0.58(19) . . . . ?
C4 N2 C10 C9 12.11(17) . . . . ?
C4 N2 C10 C11 -168.11(11) . . . . ?
C4 N2 C22 C23 96.06(13) . . . . ?
C4 C3 C13 C9 14.61(16) . . . . ?
C4 C3 C13 C38 134.79(12) . . . . ?
C4 C3 C13 C32 -104.03(13) . . . . ?
C4 C3 C2 C1 0.2(2) . . . . ?
C39 N4 C33 C32 -19.79(18) . . . . ?
C39 N4 C33 C34 159.31(12) . . . . ?
C39 C38 C13 C3 105.69(13) . . . . ?
C39 C38 C13 C9 -133.49(12) . . . . ?
C39 C38 C13 C32 -14.86(16) . . . . ?
C39 C38 C37 C36 2.57(19) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
C23 C28 C27 C26 -0.1(2) . . . . ?
C3 C4 C5 C6 -5.72(19) . . . . ?
C3 C13 C32 C33 -105.01(13) . . . . ?
C3 C13 C32 C31 74.15(14) . . . . ?
C3 C2 C1 C6 -2.9(2) . . . . ?
C9 C10 C11 C12 -1.10(18) . . . . ?
C9 C13 C32 C33 135.04(12) . . . . ?
C9 C13 C32 C31 -45.81(15) . . . . ?
C9 C8 C7 C12 -0.9(2) . . . . ?
C11 C10 C9 C13 -172.76(11) . . . . ?
C11 C10 C9 C8 1.76(18) . . . . ?
C11 C12 C7 C8 1.55(19) . . . . ?
C6 N1 C14 C16 -52.17(19) . . . . ?
C6 N1 C14 C17 71.51(17) . . . . ?
C6 N1 C14 C15 -169.96(15) . . . . ?
C5 C4 C3 C13 -178.82(11) . . . . ?
C5 C4 C3 C2 4.10(18) . . . . ?
C5 C6 C1 C2 1.3(2) . . . . ?
C38 C39 C40 C41 0.87(19) . . . . ?
C38 C13 C32 C33 15.76(16) . . . . ?
C38 C13 C32 C31 -165.08(11) . . . . ?
C38 C37 C36 C41 -0.6(2) . . . . ?
C22 N2 C10 C9 -164.30(11) . . . . ?
C22 N2 C10 C11 15.49(17) . . . . ?
C22 N2 C4 C3 159.68(11) . . . . ?
C22 N2 C4 C5 -19.44(17) . . . . ?
C22 C23 C24 C25 -179.11(12) . . . . ?
C22 C23 C28 C27 179.31(12) . . . . ?
C12 N3 C18 C20 83.56(15) . . . . ?
C12 N3 C18 C19 -158.63(13) . . . . ?
C12 N3 C18 C21 -39.42(18) . . . . ?
C13 C3 C2 C1 -176.97(13) . . . . ?
C13 C9 C8 C7 173.94(12) . . . . ?
C13 C38 C37 C36 -177.49(12) . . . . ?
C13 C32 C31 C30 -179.27(12) . . . . ?
C33 N4 C39 C38 20.75(18) . . . . ?
C33 N4 C39 C40 -158.89(12) . . . . ?
C33 C32 C31 C30 -0.09(19) . . . . ?
C33 C34 C35 C30 0.9(2) . . . . ?
C32 C33 C34 C35 -2.52(19) . . . . ?
C32 C31 C30 C35 -1.5(2) . . . . ?
C24 C23 C22 N2 -10.04(17) . . . . ?
C24 C23 C28 C27 0.4(2) . . . . ?
C24 C25 C26 C27 0.4(2) . . . . ?
C31 C30 C35 C34 1.1(2) . . . . ?
C37 C38 C13 C3 -74.25(14) . . . . ?
C37 C38 C13 C9 46.58(15) . . . . ?
C37 C38 C13 C32 165.21(11) . . . . ?
C28 C23 C22 N2 171.05(11) . . . . ?
C28 C23 C24 C25 -0.20(19) . . . . ?
C2 C3 C13 C9 -168.35(11) . . . . ?
C2 C3 C13 C38 -48.17(15) . . . . ?
C2 C3 C13 C32 73.01(14) . . . . ?
C8 C9 C13 C3 166.22(11) . . . . ?
C8 C9 C13 C38 45.69(15) . . . . ?
C8 C9 C13 C32 -74.37(14) . . . . ?
C1 C6 C5 C4 3.0(2) . . . . ?
C36 C41 C40 C39 1.2(2) . . . . ?
C14 N1 C6 C5 157.33(13) . . . . ?
C14 N1 C6 C1 -23.6(2) . . . . ?
C40 C39 C38 C13 177.40(11) . . . . ?
C40 C39 C38 C37 -2.67(18) . . . . ?
C40 C41 C36 C37 -1.3(2) . . . . ?
C34 C33 C32 C13 -178.76(11) . . . . ?
C34 C33 C32 C31 2.09(18) . . . . ?
C25 C26 C27 C28 -0.2(2) . . . . ?
C18 N3 C12 C11 148.71(12) . . . . ?
C18 N3 C12 C7 -33.56(18) . . . . ?
C29 N4 C39 C38 -173.17(12) . . . . ?
C29 N4 C39 C40 7.19(18) . . . . ?
C29 N4 C33 C32 174.18(12) . . . . ?
C29 N4 C33 C34 -6.72(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 141.9 41.6 ?
2 0.000 0.500 0.500 141.9 41.6 ?
3 0.500 0.042 0.156 7.3 0.0 ?
4 0.500 0.458 0.656 7.3 0.0 ?
5 0.500 0.542 0.344 7.3 0.0 ?
6 0.500 0.958 0.844 7.3 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 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 1.254
_oxdiff_exptl_absorpt_empirical_full_min 0.830
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, n-hexane'
_exptl_crystal_preparation       'Magnetic properties'
