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

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

data_4-brelepyrrolepro-1
_database_code_depnum_ccdc_archive 'CCDC 2383150'
loop_
_audit_author_name
_audit_author_address
'Shuichi Nakamura'
;Nagoya Institute of Technology
Japan
;
_audit_update_record             
;
2024-09-10 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 Br N3 O2'
_chemical_formula_sum            'C17 H18 Br N3 O2'
_chemical_formula_weight         376.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H18 Br1 N3 O2'
_chemical_oxdiff_usercomment     'MicroMount200, -150oC'
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'
Br Br -0.6763 1.2805 '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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   20.10730(10)
_cell_length_b                   17.86380(10)
_cell_length_c                   15.33700(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5508.94(5)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    44531
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.5640
_cell_measurement_theta_min      2.1700
_shelx_estimated_absorpt_T_max   0.667
_shelx_estimated_absorpt_T_min   0.557
_exptl_absorpt_coefficient_mu    3.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2304
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 12 0 0.0707
2 1 10 0.1008
-1 -11 3 0.1032
-2 -11 -3 0.1066
-2 -4 -9 0.1099
9 9 1 0.0544
9 -8 -3 0.1026
-6 -10 -2 0.0889
-9 -8 -1 0.0900
-8 8 3 0.0803
1 1 -10 0.0817
6 -2 -9 0.0871
-9 9 0 0.0562
-9 -8 -3 0.0904
7 2 8 0.0926
6 -6 7 0.1022
-9 -5 5 0.1362
8 -8 3 0.1004

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
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
1.1750 11.5434 -0.1640 -0.0365 -0.2513 0.9672
1.9055 0.8564 9.8173 0.1349 0.9374 0.3211
-0.6797 -11.1634 2.6267 0.0698 0.4831 -0.8728
-1.7197 -10.8916 -3.1487 -0.0118 -0.0841 -0.9964
-2.1214 -4.0403 -9.1873 -0.1167 -0.8112 -0.5730
8.5786 8.6333 1.1654 -0.5577 0.0807 0.8261
9.1734 -7.7132 -2.5280 -0.7804 0.1121 -0.6151
-6.1984 -10.0127 -1.6828 0.3620 -0.0525 -0.9307
-9.0205 -8.2917 -1.0503 0.5950 -0.0860 -0.7991
-8.4421 8.3161 2.5977 0.7314 -0.1051 0.6738
1.0151 1.0905 -9.8744 -0.3420 -0.9302 -0.1331
5.5648 -1.8533 -8.8579 -0.6622 -0.6816 -0.3112
-8.7353 8.6198 0.2274 0.6890 -0.3396 0.6403
-8.6432 -8.0274 -2.8600 0.5186 -0.2543 -0.8164
6.6070 2.2592 8.3656 -0.2441 0.8603 0.4476
5.9819 -5.7266 7.3574 -0.2637 0.9326 -0.2463
-9.3721 -5.3420 5.1863 0.8069 0.4256 -0.4097
8.0297 -8.3169 3.2711 -0.5392 0.6471 -0.5390

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            53680
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.917
_diffrn_reflns_theta_min         2.881
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -124.00  54.00   0.50    0.50    --  -35.00 -20.00  19.00  356
  2  ω    -46.00 133.00   0.50    0.50    --   43.60  20.00-173.00  358
  3  ω     20.00 199.00   0.50    0.50    --  109.30 -20.00  19.00  358
  4  ω     20.00 199.00   0.50    0.50    --  109.30  20.00-173.00  358
  5  ω    -79.00  39.00   0.50    0.50    --  -35.00  82.00-180.00  236
  6  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00   0.00   96
  7  ω    -39.00   9.00   0.50    0.50    --  -35.00 -82.00-180.00   96
  8  ω      2.00  46.00   0.50    0.50    --   43.60  77.00 -30.00   88
  9  ω      2.00  48.00   0.50    0.50    --   43.60  77.00 -90.00   92
 10  ω     75.00 132.00   0.50    0.50    --   43.60  77.00   0.00  114
 11  ω     19.00  44.00   0.50    0.50    --   43.60 -20.00  19.00   50
 12  ω     81.00 132.00   0.50    0.50    --   43.60  82.00 -90.00  102
 13  ω      5.00  48.00   0.50    0.50    --   43.60  77.00   0.00   86
 14  ω     26.00  52.00   0.50    0.50    --  109.30 -45.00  30.00   52
 15  ω     76.00 198.00   0.50    0.50    --  109.30  61.00-150.00  244
 16  ω     60.00 139.00   0.50    0.50    --  109.30 -77.00-150.00  158
 17  ω     20.00  55.00   0.50    0.50    --  109.30 -77.00-150.00   70
 18  ω    108.00 144.00   0.50    0.50    --  109.30 -61.00-120.00   72
 19  ω     44.00  70.00   0.50    0.50    --  109.30 -61.00-120.00   52
 20  ω     75.00 149.00   0.50    0.50    --  109.30 -45.00  30.00  148
 21  ω     20.00  85.00   0.50    0.50    --  109.30 -77.00  30.00  130
 22  ω     21.00 143.00   0.50    0.50    --  109.30 -61.00-150.00  244
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0735065000
_diffrn_orient_matrix_UB_12      0.0047133000
_diffrn_orient_matrix_UB_13      0.0275969000
_diffrn_orient_matrix_UB_21      0.0192145000
_diffrn_orient_matrix_UB_22      -0.0223985000
_diffrn_orient_matrix_UB_23      0.0937081000
_diffrn_orient_matrix_UB_31      0.0093878000
_diffrn_orient_matrix_UB_32      0.0831690000
_diffrn_orient_matrix_UB_33      0.0236286000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                11060
_reflns_number_total             11206
_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 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 40.35a 64-bit (release 18-12-2018))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 4809 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         11206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.018
_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)+(0.0301P)²+3.5764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0668
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N37(H37), N13(H13), N14(H14), N60(H60), N36(H36), N59(H59), C12(H12),
 C52(H52), C4(H4), C3(H3), C30(H30), C53(H53), C49(H49), C11(H11), C10(H10),
 C6(H6), C35(H35), C7(H7), C29(H29), C50(H50), C27(H27), C34(H34), C33(H33),
 C58(H58), C56(H56), C26(H26), C57(H57)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C42(H42A,H42B,H42C), C65(H65A,H65B,H65C), C44(H44A,H44B,
 H44C), C67(H67A,H67B,H67C), C21(H21A,H21B,H21C), C43(H43A,H43B,H43C), C66(H66A,
 H66B,H66C), C20(H20A,H20B,H20C)
;
_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
Br1 Br 0.54528(2) 0.59823(2) 0.27154(2) 0.03986(9) Uani 1 1 d . . . . .
Br24 Br 0.89599(2) 0.32486(2) 0.82373(3) 0.04779(11) Uani 1 1 d . . . . .
Br47 Br 0.60328(2) 0.85203(3) 0.79027(3) 0.04951(11) Uani 1 1 d . . . . .
O39 O 0.49712(10) 0.40190(12) 0.94376(14) 0.0276(4) Uani 1 1 d . . . . .
O16 O 0.76807(10) 0.49973(11) 0.57684(13) 0.0238(4) Uani 1 1 d . . . . .
O40 O 0.59570(10) 0.35064(11) 0.98539(13) 0.0241(4) Uani 1 1 d . . . . .
O63 O 0.80325(12) 0.62512(11) 0.40719(13) 0.0293(5) Uani 1 1 d . . . . .
O62 O 0.81703(11) 0.74545(11) 0.45534(14) 0.0259(4) Uani 1 1 d . . . . .
O17 O 0.80454(10) 0.37841(11) 0.57432(16) 0.0317(5) Uani 1 1 d . . . . .
N37 N 0.59134(11) 0.47171(12) 0.95251(15) 0.0202(5) Uani 1 1 d . . . . .
H37 H 0.574655 0.507836 0.920201 0.024 Uiso 1 1 calc R U . . .
N13 N 0.56215(12) 0.33963(13) 0.60656(16) 0.0250(5) Uani 1 1 d . . . . .
H13 H 0.576611 0.324714 0.555272 0.030 Uiso 1 1 calc R U . . .
N14 N 0.69909(11) 0.40160(12) 0.60394(15) 0.0212(5) Uani 1 1 d . . . . .
H14 H 0.695884 0.352893 0.611389 0.025 Uiso 1 1 calc R U . . .
N60 N 0.82705(13) 0.64513(13) 0.54506(16) 0.0249(5) Uani 1 1 d . . . . .
H60 H 0.825426 0.596047 0.549453 0.030 Uiso 1 1 calc R U . . .
N36 N 0.68076(13) 0.60374(14) 0.91705(16) 0.0267(5) Uani 1 1 d . . . . .
H36 H 0.680360 0.582832 0.865105 0.032 Uiso 1 1 calc R U . . .
N59 N 0.82390(13) 0.59674(14) 0.74241(17) 0.0293(5) Uani 1 1 d . . . . .
H59 H 0.780663 0.594302 0.733975 0.035 Uiso 1 1 calc R U . . .
N69 N 0.94332(14) 0.77694(16) 0.58069(18) 0.0324(6) Uani 1 1 d . . . . .
N23 N 0.66727(14) 0.55021(14) 0.73251(17) 0.0295(5) Uani 1 1 d . . . . .
N46 N 0.64921(14) 0.44364(16) 1.16010(17) 0.0336(6) Uani 1 1 d . . . . .
C68 C 0.89899(15) 0.74009(15) 0.59926(18) 0.0235(6) Uani 1 1 d . . . . .
C9 C 0.58468(13) 0.40095(15) 0.65092(17) 0.0207(5) Uani 1 1 d . . . . .
C38 C 0.55618(13) 0.40674(16) 0.96031(17) 0.0222(5) Uani 1 1 d . . . . .
C32 C 0.66973(14) 0.56727(16) 0.99392(18) 0.0210(5) Uani 1 1 d . . . . .
C12 C 0.51359(14) 0.30506(17) 0.6544(2) 0.0279(6) Uani 1 1 d . . . . .
H12 H 0.490456 0.260746 0.638478 0.033 Uiso 1 1 calc R U . . .
C52 C 0.79303(14) 0.79888(16) 0.70713(19) 0.0250(6) Uani 1 1 d . . . . .
H52 H 0.836740 0.817704 0.715599 0.030 Uiso 1 1 calc R U . . .
C15 C 0.75903(14) 0.43224(15) 0.58345(18) 0.0222(5) Uani 1 1 d . . . . .
C4 C 0.63412(14) 0.45452(16) 0.44832(19) 0.0244(6) Uani 1 1 d . . . . .
H4 H 0.660442 0.410404 0.446111 0.029 Uiso 1 1 calc R U . . .
C5 C 0.61840(13) 0.48631(15) 0.52854(17) 0.0198(5) Uani 1 1 d . . . . .
C61 C 0.81504(14) 0.67796(16) 0.46699(19) 0.0232(6) Uani 1 1 d . . . . .
C55 C 0.86735(14) 0.64003(15) 0.69494(18) 0.0230(6) Uani 1 1 d . . . . .
C45 C 0.65123(15) 0.46158(16) 1.08886(19) 0.0243(6) Uani 1 1 d . . . . .
C54 C 0.84266(14) 0.69002(15) 0.62214(18) 0.0214(5) Uani 1 1 d . . . . .
C22 C 0.65542(14) 0.50681(15) 0.67967(18) 0.0227(5) Uani 1 1 d . . . . .
C8 C 0.64019(14) 0.44823(15) 0.61372(18) 0.0205(5) Uani 1 1 d . . . . .
C51 C 0.78330(14) 0.73563(15) 0.65561(18) 0.0215(5) Uani 1 1 d . . . . .
C31 C 0.65559(13) 0.48429(15) 0.99535(17) 0.0200(5) Uani 1 1 d . . . . .
C3 C 0.61167(15) 0.48671(18) 0.37180(18) 0.0273(6) Uani 1 1 d . . . . .
H3 H 0.621509 0.464533 0.316996 0.033 Uiso 1 1 calc R U . . .
C2 C 0.57446(15) 0.55210(18) 0.3766(2) 0.0274(6) Uani 1 1 d . . . . .
C30 C 0.76285(15) 0.37647(16) 0.83083(19) 0.0251(6) Uani 1 1 d . . . . .
H30 H 0.759257 0.356370 0.773677 0.030 Uiso 1 1 calc R U . . .
C53 C 0.73980(16) 0.83452(17) 0.7460(2) 0.0302(6) Uani 1 1 d . . . . .
H53 H 0.746304 0.878254 0.780228 0.036 Uiso 1 1 calc R U . . .
C49 C 0.66569(15) 0.74293(19) 0.6834(2) 0.0324(7) Uani 1 1 d . . . . .
H49 H 0.621963 0.723783 0.676068 0.039 Uiso 1 1 calc R U . . .
C48 C 0.67670(15) 0.80510(18) 0.7341(2) 0.0309(7) Uani 1 1 d . . . . .
C25 C 0.82161(15) 0.37177(17) 0.8760(2) 0.0293(6) Uani 1 1 d . . . . .
C11 C 0.50422(15) 0.34555(17) 0.7291(2) 0.0288(6) Uani 1 1 d . . . . .
H11 H 0.473150 0.334860 0.774084 0.035 Uiso 1 1 calc R U . . .
C10 C 0.54939(14) 0.40629(16) 0.72703(18) 0.0256(5) Uani 1 1 d . . . . .
H10 H 0.554306 0.443837 0.770417 0.031 Uiso 1 1 calc R U . . .
C6 C 0.57967(15) 0.55082(16) 0.53173(19) 0.0258(6) Uani 1 1 d . . . . .
H6 H 0.568034 0.571918 0.586506 0.031 Uiso 1 1 calc R U . . .
C35 C 0.69250(17) 0.67768(18) 0.9333(2) 0.0340(7) Uani 1 1 d . . . . .
H35 H 0.701044 0.715199 0.890860 0.041 Uiso 1 1 calc R U . . .
C7 C 0.55801(15) 0.58440(18) 0.4555(2) 0.0287(6) Uani 1 1 d . . . . .
H7 H 0.532236 0.628947 0.457397 0.034 Uiso 1 1 calc R U . . .
C28 C 0.71373(13) 0.44108(15) 0.95294(18) 0.0203(5) Uani 1 1 d . . . . .
C29 C 0.70887(14) 0.41097(16) 0.86992(18) 0.0231(5) Uani 1 1 d . . . . .
H29 H 0.667871 0.414051 0.839350 0.028 Uiso 1 1 calc R U . . .
C18 C 0.87225(15) 0.39402(18) 0.5421(2) 0.0282(6) Uani 1 1 d . . . . .
C50 C 0.71925(15) 0.70854(17) 0.6431(2) 0.0272(6) Uani 1 1 d . . . . .
H50 H 0.712139 0.666243 0.606727 0.033 Uiso 1 1 calc R U . . .
C27 C 0.77378(15) 0.43530(19) 0.9973(2) 0.0294(7) Uani 1 1 d . . . . .
H27 H 0.777686 0.455933 1.054134 0.035 Uiso 1 1 calc R U . . .
C34 C 0.6898(2) 0.68810(19) 1.0211(2) 0.0405(8) Uani 1 1 d . . . . .
H34 H 0.696707 0.734044 1.050927 0.049 Uiso 1 1 calc R U . . .
C41 C 0.56832(16) 0.28010(18) 1.0209(2) 0.0332(7) Uani 1 1 d . . . . .
C64 C 0.78586(17) 0.64479(18) 0.3160(2) 0.0316(7) Uani 1 1 d . . . . .
C33 C 0.67481(17) 0.61814(18) 1.0601(2) 0.0336(7) Uani 1 1 d . . . . .
H33 H 0.669364 0.608502 1.120615 0.040 Uiso 1 1 calc R U . . .
C58 C 0.85820(18) 0.55822(17) 0.8045(2) 0.0334(7) Uani 1 1 d . . . . .
H58 H 0.839741 0.524615 0.846003 0.040 Uiso 1 1 calc R U . . .
C56 C 0.93001(15) 0.62806(17) 0.7274(2) 0.0301(6) Uani 1 1 d . . . . .
H56 H 0.969987 0.650362 0.707049 0.036 Uiso 1 1 calc R U . . .
C19 C 0.90891(16) 0.44391(18) 0.6056(2) 0.0338(7) Uani 1 1 d . . . . .
H19A H 0.903396 0.424402 0.664909 0.051 Uiso 1 1 calc R U . . .
H19B H 0.890806 0.494768 0.602474 0.051 Uiso 1 1 calc R U . . .
H19C H 0.956293 0.444870 0.590679 0.051 Uiso 1 1 calc R U . . .
C26 C 0.82772(15) 0.4001(2) 0.9601(2) 0.0336(7) Uani 1 1 d . . . . .
H26 H 0.868329 0.395340 0.991248 0.040 Uiso 1 1 calc R U . . .
C57 C 0.92416(18) 0.57665(18) 0.7965(2) 0.0358(7) Uani 1 1 d . . . . .
H57 H 0.959547 0.558030 0.831315 0.043 Uiso 1 1 calc R U . . .
C42 C 0.5274(2) 0.23955(19) 0.9525(3) 0.0454(9) Uani 1 1 d . . . . .
H42A H 0.517765 0.188606 0.972546 0.068 Uiso 1 1 calc R U . . .
H42B H 0.552446 0.237349 0.897732 0.068 Uiso 1 1 calc R U . . .
H42C H 0.485579 0.266512 0.942996 0.068 Uiso 1 1 calc R U . . .
C65 C 0.8421(2) 0.6876(2) 0.2735(2) 0.0470(9) Uani 1 1 d . . . . .
H65A H 0.883579 0.659346 0.279822 0.070 Uiso 1 1 calc R U . . .
H65B H 0.846799 0.736541 0.301692 0.070 Uiso 1 1 calc R U . . .
H65C H 0.832288 0.694645 0.211445 0.070 Uiso 1 1 calc R U . . .
C44 C 0.5292(2) 0.2977(2) 1.1020(3) 0.0472(9) Uani 1 1 d . . . . .
H44A H 0.487351 0.322249 1.085902 0.071 Uiso 1 1 calc R U . . .
H44B H 0.555157 0.331091 1.139562 0.071 Uiso 1 1 calc R U . . .
H44C H 0.519477 0.251183 1.133466 0.071 Uiso 1 1 calc R U . . .
C67 C 0.7778(2) 0.5679(2) 0.2754(3) 0.0446(9) Uani 1 1 d . . . . .
H67A H 0.764738 0.573262 0.214134 0.067 Uiso 1 1 calc R U . . .
H67B H 0.743376 0.539998 0.306883 0.067 Uiso 1 1 calc R U . . .
H67C H 0.820044 0.540702 0.278881 0.067 Uiso 1 1 calc R U . . .
C21 C 0.90282(18) 0.3165(2) 0.5401(3) 0.0432(8) Uani 1 1 d . . . . .
H21A H 0.948614 0.319760 0.518527 0.065 Uiso 1 1 calc R U . . .
H21B H 0.876756 0.284181 0.501345 0.065 Uiso 1 1 calc R U . . .
H21C H 0.902862 0.295383 0.599049 0.065 Uiso 1 1 calc R U . . .
C43 C 0.6317(2) 0.2374(2) 1.0431(3) 0.0480(10) Uani 1 1 d . . . . .
H43A H 0.620161 0.188216 1.066985 0.072 Uiso 1 1 calc R U . . .
H43B H 0.657374 0.265643 1.086342 0.072 Uiso 1 1 calc R U . . .
H43C H 0.658448 0.230883 0.990182 0.072 Uiso 1 1 calc R U . . .
C66 C 0.72081(19) 0.6877(2) 0.3154(3) 0.0468(9) Uani 1 1 d . . . . .
H66A H 0.727150 0.736315 0.343770 0.070 Uiso 1 1 calc R U . . .
H66B H 0.686937 0.659057 0.347042 0.070 Uiso 1 1 calc R U . . .
H66C H 0.706296 0.695359 0.255087 0.070 Uiso 1 1 calc R U . . .
C20 C 0.8673(3) 0.4273(3) 0.4513(3) 0.0598(13) Uani 1 1 d . . . . .
H20A H 0.850306 0.478613 0.455197 0.090 Uiso 1 1 calc R U . . .
H20B H 0.836915 0.397015 0.415867 0.090 Uiso 1 1 calc R U . . .
H20C H 0.911403 0.427761 0.424153 0.090 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
Br1 C2 1.903(3) . ?
Br24 C25 1.892(3) . ?
Br47 C48 1.904(3) . ?
O39 C38 1.217(3) . ?
O16 C15 1.223(3) . ?
O40 C38 1.336(3) . ?
O40 C41 1.479(3) . ?
O63 C61 1.337(4) . ?
O63 C64 1.484(4) . ?
O62 C61 1.219(4) . ?
O17 C15 1.335(3) . ?
O17 C18 1.475(4) . ?
N37 H37 0.8800 . ?
N37 C38 1.364(4) . ?
N37 C31 1.467(3) . ?
N13 H13 0.8800 . ?
N13 C9 1.367(3) . ?
N13 C12 1.368(4) . ?
N14 H14 0.8800 . ?
N14 C15 1.361(4) . ?
N14 C8 1.456(3) . ?
N60 H60 0.8800 . ?
N60 C61 1.355(4) . ?
N60 C54 1.463(4) . ?
N36 H36 0.8800 . ?
N36 C32 1.365(4) . ?
N36 C35 1.365(4) . ?
N59 H59 0.8800 . ?
N59 C55 1.375(4) . ?
N59 C58 1.363(4) . ?
N69 C68 1.144(4) . ?
N23 C22 1.147(4) . ?
N46 C45 1.139(4) . ?
C68 C54 1.485(4) . ?
C9 C8 1.511(4) . ?
C9 C10 1.369(4) . ?
C32 C31 1.509(4) . ?
C32 C33 1.366(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.368(4) . ?
C52 H52 0.9500 . ?
C52 C51 1.392(4) . ?
C52 C53 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(4) . ?
C4 C3 1.383(4) . ?
C5 C8 1.537(4) . ?
C5 C6 1.392(4) . ?
C55 C54 1.513(4) . ?
C55 C56 1.372(4) . ?
C45 C31 1.493(4) . ?
C54 C51 1.534(4) . ?
C22 C8 1.487(4) . ?
C51 C50 1.389(4) . ?
C31 C28 1.545(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.389(4) . ?
C2 C7 1.380(4) . ?
C30 H30 0.9500 . ?
C30 C25 1.372(4) . ?
C30 C29 1.385(4) . ?
C53 H53 0.9500 . ?
C53 C48 1.386(4) . ?
C49 H49 0.9500 . ?
C49 C48 1.374(5) . ?
C49 C50 1.385(5) . ?
C25 C26 1.391(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.415(4) . ?
C10 H10 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.385(4) . ?
C35 H35 0.9500 . ?
C35 C34 1.360(5) . ?
C7 H7 0.9500 . ?
C28 C29 1.386(4) . ?
C28 C27 1.390(4) . ?
C29 H29 0.9500 . ?
C18 C19 1.513(4) . ?
C18 C21 1.516(4) . ?
C18 C20 1.517(5) . ?
C50 H50 0.9500 . ?
C27 H27 0.9500 . ?
C27 C26 1.377(4) . ?
C34 H34 0.9500 . ?
C34 C33 1.418(5) . ?
C41 C42 1.518(5) . ?
C41 C44 1.505(5) . ?
C41 C43 1.524(5) . ?
C64 C65 1.512(5) . ?
C64 C67 1.517(5) . ?
C64 C66 1.516(5) . ?
C33 H33 0.9500 . ?
C58 H58 0.9500 . ?
C58 C57 1.372(5) . ?
C56 H56 0.9500 . ?
C56 C57 1.407(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C26 H26 0.9500 . ?
C57 H57 0.9500 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C38 O40 C41 121.6(2) . . ?
C61 O63 C64 121.4(2) . . ?
C15 O17 C18 122.1(2) . . ?
C38 N37 H37 118.4 . . ?
C38 N37 C31 123.2(2) . . ?
C31 N37 H37 118.4 . . ?
C9 N13 H13 125.3 . . ?
C9 N13 C12 109.4(2) . . ?
C12 N13 H13 125.3 . . ?
C15 N14 H14 119.5 . . ?
C15 N14 C8 121.0(2) . . ?
C8 N14 H14 119.5 . . ?
C61 N60 H60 119.5 . . ?
C61 N60 C54 121.0(2) . . ?
C54 N60 H60 119.5 . . ?
C32 N36 H36 125.3 . . ?
C35 N36 H36 125.3 . . ?
C35 N36 C32 109.4(3) . . ?
C55 N59 H59 125.3 . . ?
C58 N59 H59 125.3 . . ?
C58 N59 C55 109.4(3) . . ?
N69 C68 C54 178.1(3) . . ?
N13 C9 C8 120.3(2) . . ?
N13 C9 C10 108.0(2) . . ?
C10 C9 C8 131.7(2) . . ?
O39 C38 O40 126.0(3) . . ?
O39 C38 N37 123.2(3) . . ?
O40 C38 N37 110.8(2) . . ?
N36 C32 C31 120.8(2) . . ?
N36 C32 C33 108.2(3) . . ?
C33 C32 C31 131.0(3) . . ?
N13 C12 H12 126.0 . . ?
N13 C12 C11 108.0(3) . . ?
C11 C12 H12 126.0 . . ?
C51 C52 H52 119.7 . . ?
C53 C52 H52 119.7 . . ?
C53 C52 C51 120.7(3) . . ?
O16 C15 O17 126.8(3) . . ?
O16 C15 N14 123.2(3) . . ?
O17 C15 N14 110.0(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C4 C5 C8 120.4(2) . . ?
C4 C5 C6 119.7(3) . . ?
C6 C5 C8 119.7(2) . . ?
O63 C61 N60 109.4(2) . . ?
O62 C61 O63 127.1(3) . . ?
O62 C61 N60 123.5(3) . . ?
N59 C55 C54 120.9(2) . . ?
C56 C55 N59 107.7(2) . . ?
C56 C55 C54 131.4(3) . . ?
N46 C45 C31 178.6(3) . . ?
N60 C54 C68 107.6(2) . . ?
N60 C54 C55 110.1(2) . . ?
N60 C54 C51 113.3(2) . . ?
C68 C54 C55 106.2(2) . . ?
C68 C54 C51 110.6(2) . . ?
C55 C54 C51 108.8(2) . . ?
N23 C22 C8 177.8(3) . . ?
N14 C8 C9 108.7(2) . . ?
N14 C8 C5 113.4(2) . . ?
N14 C8 C22 107.8(2) . . ?
C9 C8 C5 111.0(2) . . ?
C22 C8 C9 106.8(2) . . ?
C22 C8 C5 109.0(2) . . ?
C52 C51 C54 120.8(2) . . ?
C50 C51 C52 119.4(3) . . ?
C50 C51 C54 119.4(2) . . ?
N37 C31 C32 108.1(2) . . ?
N37 C31 C45 109.7(2) . . ?
N37 C31 C28 113.7(2) . . ?
C32 C31 C28 110.0(2) . . ?
C45 C31 C32 107.0(2) . . ?
C45 C31 C28 108.2(2) . . ?
C4 C3 H3 120.6 . . ?
C4 C3 C2 118.7(3) . . ?
C2 C3 H3 120.6 . . ?
C3 C2 Br1 119.0(2) . . ?
C7 C2 Br1 119.2(2) . . ?
C7 C2 C3 121.8(3) . . ?
C25 C30 H30 120.5 . . ?
C25 C30 C29 118.9(3) . . ?
C29 C30 H30 120.5 . . ?
C52 C53 H53 120.7 . . ?
C52 C53 C48 118.5(3) . . ?
C48 C53 H53 120.7 . . ?
C48 C49 H49 120.5 . . ?
C48 C49 C50 119.1(3) . . ?
C50 C49 H49 120.5 . . ?
C53 C48 Br47 118.9(2) . . ?
C49 C48 Br47 119.2(2) . . ?
C49 C48 C53 122.0(3) . . ?
C30 C25 Br24 119.6(2) . . ?
C30 C25 C26 121.4(3) . . ?
C26 C25 Br24 118.9(2) . . ?
C12 C11 H11 126.3 . . ?
C12 C11 C10 107.3(3) . . ?
C10 C11 H11 126.3 . . ?
C9 C10 C11 107.4(3) . . ?
C9 C10 H10 126.3 . . ?
C11 C10 H10 126.3 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
N36 C35 H35 126.1 . . ?
C34 C35 N36 107.8(3) . . ?
C34 C35 H35 126.1 . . ?
C2 C7 C6 118.9(3) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C29 C28 C31 121.8(2) . . ?
C29 C28 C27 118.8(3) . . ?
C27 C28 C31 119.3(3) . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
O17 C18 C19 110.2(2) . . ?
O17 C18 C21 102.0(3) . . ?
O17 C18 C20 108.7(3) . . ?
C19 C18 C21 110.7(3) . . ?
C19 C18 C20 113.1(3) . . ?
C21 C18 C20 111.5(3) . . ?
C51 C50 H50 119.8 . . ?
C49 C50 C51 120.3(3) . . ?
C49 C50 H50 119.8 . . ?
C28 C27 H27 119.5 . . ?
C26 C27 C28 121.0(3) . . ?
C26 C27 H27 119.5 . . ?
C35 C34 H34 126.1 . . ?
C35 C34 C33 107.8(3) . . ?
C33 C34 H34 126.1 . . ?
O40 C41 C42 110.7(3) . . ?
O40 C41 C44 108.7(3) . . ?
O40 C41 C43 101.4(2) . . ?
C42 C41 C43 111.6(3) . . ?
C44 C41 C42 112.8(3) . . ?
C44 C41 C43 111.0(3) . . ?
O63 C64 C65 110.5(3) . . ?
O63 C64 C67 101.4(2) . . ?
O63 C64 C66 109.2(3) . . ?
C65 C64 C67 111.2(3) . . ?
C65 C64 C66 112.8(3) . . ?
C66 C64 C67 111.3(3) . . ?
C32 C33 C34 106.8(3) . . ?
C32 C33 H33 126.6 . . ?
C34 C33 H33 126.6 . . ?
N59 C58 H58 126.1 . . ?
N59 C58 C57 107.8(3) . . ?
C57 C58 H58 126.1 . . ?
C55 C56 H56 126.3 . . ?
C55 C56 C57 107.4(3) . . ?
C57 C56 H56 126.3 . . ?
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 . . ?
C25 C26 H26 120.6 . . ?
C27 C26 C25 118.7(3) . . ?
C27 C26 H26 120.6 . . ?
C58 C57 C56 107.8(3) . . ?
C58 C57 H57 126.1 . . ?
C56 C57 H57 126.1 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C64 C65 H65A 109.5 . . ?
C64 C65 H65B 109.5 . . ?
C64 C65 H65C 109.5 . . ?
H65A C65 H65B 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C64 C67 H67A 109.5 . . ?
C64 C67 H67B 109.5 . . ?
C64 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 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 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C64 C66 H66A 109.5 . . ?
C64 C66 H66B 109.5 . . ?
C64 C66 H66C 109.5 . . ?
H66A C66 H66B 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 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 . . ?

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
Br1 C2 C7 C6 -179.7(2) . . . . ?
Br24 C25 C26 C27 179.0(3) . . . . ?
N37 C31 C28 C29 16.7(4) . . . . ?
N37 C31 C28 C27 -166.5(3) . . . . ?
N13 C9 C8 N14 -60.6(3) . . . . ?
N13 C9 C8 C5 64.8(3) . . . . ?
N13 C9 C8 C22 -176.6(2) . . . . ?
N13 C9 C10 C11 0.5(3) . . . . ?
N13 C12 C11 C10 -0.8(3) . . . . ?
N60 C54 C51 C52 -157.9(2) . . . . ?
N60 C54 C51 C50 29.8(3) . . . . ?
N36 C32 C31 N37 -66.2(3) . . . . ?
N36 C32 C31 C45 175.7(3) . . . . ?
N36 C32 C31 C28 58.4(3) . . . . ?
N36 C32 C33 C34 -0.2(4) . . . . ?
N36 C35 C34 C33 -0.9(4) . . . . ?
N59 C55 C54 N60 -76.1(3) . . . . ?
N59 C55 C54 C68 167.6(3) . . . . ?
N59 C55 C54 C51 48.5(3) . . . . ?
N59 C55 C56 C57 -0.3(4) . . . . ?
N59 C58 C57 C56 0.1(4) . . . . ?
C68 C54 C51 C52 -37.0(3) . . . . ?
C68 C54 C51 C50 150.7(3) . . . . ?
C9 N13 C12 C11 1.1(3) . . . . ?
C38 O40 C41 C42 64.0(4) . . . . ?
C38 O40 C41 C44 -60.4(4) . . . . ?
C38 O40 C41 C43 -177.4(3) . . . . ?
C38 N37 C31 C32 -164.0(2) . . . . ?
C38 N37 C31 C45 -47.7(3) . . . . ?
C38 N37 C31 C28 73.6(3) . . . . ?
C32 N36 C35 C34 0.8(4) . . . . ?
C32 C31 C28 C29 -104.6(3) . . . . ?
C32 C31 C28 C27 72.2(3) . . . . ?
C12 N13 C9 C8 178.2(2) . . . . ?
C12 N13 C9 C10 -1.0(3) . . . . ?
C12 C11 C10 C9 0.2(3) . . . . ?
C52 C51 C50 C49 -1.7(4) . . . . ?
C52 C53 C48 Br47 178.1(2) . . . . ?
C52 C53 C48 C49 -1.5(5) . . . . ?
C15 O17 C18 C19 64.6(4) . . . . ?
C15 O17 C18 C21 -177.8(3) . . . . ?
C15 O17 C18 C20 -59.9(4) . . . . ?
C15 N14 C8 C9 -170.6(2) . . . . ?
C15 N14 C8 C5 65.5(3) . . . . ?
C15 N14 C8 C22 -55.3(3) . . . . ?
C4 C5 C8 N14 26.1(3) . . . . ?
C4 C5 C8 C9 -96.6(3) . . . . ?
C4 C5 C8 C22 146.1(3) . . . . ?
C4 C5 C6 C7 -1.5(4) . . . . ?
C4 C3 C2 Br1 178.4(2) . . . . ?
C4 C3 C2 C7 -1.7(5) . . . . ?
C5 C4 C3 C2 1.4(4) . . . . ?
C5 C6 C7 C2 1.1(5) . . . . ?
C61 O63 C64 C65 61.9(4) . . . . ?
C61 O63 C64 C67 179.9(3) . . . . ?
C61 O63 C64 C66 -62.6(4) . . . . ?
C61 N60 C54 C68 -53.2(3) . . . . ?
C61 N60 C54 C55 -168.5(3) . . . . ?
C61 N60 C54 C51 69.5(3) . . . . ?
C55 N59 C58 C57 -0.3(4) . . . . ?
C55 C54 C51 C52 79.3(3) . . . . ?
C55 C54 C51 C50 -93.0(3) . . . . ?
C55 C56 C57 C58 0.2(4) . . . . ?
C45 C31 C28 C29 138.9(3) . . . . ?
C45 C31 C28 C27 -44.4(3) . . . . ?
C54 N60 C61 O63 178.9(2) . . . . ?
C54 N60 C61 O62 0.8(4) . . . . ?
C54 C55 C56 C57 178.9(3) . . . . ?
C54 C51 C50 C49 170.7(3) . . . . ?
C8 N14 C15 O16 4.1(4) . . . . ?
C8 N14 C15 O17 -177.3(2) . . . . ?
C8 C9 C10 C11 -178.6(3) . . . . ?
C8 C5 C6 C7 -178.0(3) . . . . ?
C51 C52 C53 C48 1.3(4) . . . . ?
C31 N37 C38 O39 161.4(3) . . . . ?
C31 N37 C38 O40 -20.5(3) . . . . ?
C31 C32 C33 C34 179.1(3) . . . . ?
C31 C28 C29 C30 175.9(3) . . . . ?
C31 C28 C27 C26 -177.1(3) . . . . ?
C3 C4 C5 C8 176.7(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C3 C2 C7 C6 0.5(5) . . . . ?
C30 C25 C26 C27 -1.7(5) . . . . ?
C53 C52 C51 C54 -172.0(3) . . . . ?
C53 C52 C51 C50 0.3(4) . . . . ?
C48 C49 C50 C51 1.5(5) . . . . ?
C25 C30 C29 C28 0.6(4) . . . . ?
C10 C9 C8 N14 118.4(3) . . . . ?
C10 C9 C8 C5 -116.2(3) . . . . ?
C10 C9 C8 C22 2.4(4) . . . . ?
C6 C5 C8 N14 -157.4(3) . . . . ?
C6 C5 C8 C9 80.0(3) . . . . ?
C6 C5 C8 C22 -37.3(3) . . . . ?
C35 N36 C32 C31 -179.8(3) . . . . ?
C35 N36 C32 C33 -0.3(4) . . . . ?
C35 C34 C33 C32 0.7(4) . . . . ?
C28 C27 C26 C25 1.5(5) . . . . ?
C29 C30 C25 Br24 -180.0(2) . . . . ?
C29 C30 C25 C26 0.7(4) . . . . ?
C29 C28 C27 C26 -0.2(5) . . . . ?
C18 O17 C15 O16 -8.8(5) . . . . ?
C18 O17 C15 N14 172.7(2) . . . . ?
C50 C49 C48 Br47 -179.5(2) . . . . ?
C50 C49 C48 C53 0.1(5) . . . . ?
C27 C28 C29 C30 -0.8(4) . . . . ?
C41 O40 C38 O39 -18.4(4) . . . . ?
C41 O40 C38 N37 163.6(2) . . . . ?
C64 O63 C61 O62 -4.4(5) . . . . ?
C64 O63 C61 N60 177.6(3) . . . . ?
C33 C32 C31 N37 114.5(3) . . . . ?
C33 C32 C31 C45 -3.6(4) . . . . ?
C33 C32 C31 C28 -120.9(3) . . . . ?
C58 N59 C55 C54 -179.0(3) . . . . ?
C58 N59 C55 C56 0.4(4) . . . . ?
C56 C55 C54 N60 104.7(4) . . . . ?
C56 C55 C54 C68 -11.6(4) . . . . ?
C56 C55 C54 C51 -130.7(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 0.000 0.000 0.893 11.5 0.0 ?
2 0.000 0.500 0.195 254.2 54.0 ?
3 0.500 0.000 0.805 254.2 53.9 ?
4 0.500 0.500 0.107 11.5 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 1.323
_oxdiff_exptl_absorpt_empirical_full_min 0.734
####################################################################### 
# 
# 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_20241031-1
_database_code_depnum_ccdc_archive 'CCDC 2395238'
loop_
_audit_author_name
_audit_author_address
'Shuichi Nakamura'
;Nagoya Institute of Technology
Japan
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2024-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 Br N3 O2'
_chemical_formula_sum            'C22 H22 Br N3 O2'
_chemical_formula_weight         440.33
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H22 Br1 N3 O2'
_chemical_oxdiff_usercomment     -170oC
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.35120(10)
_cell_length_b                   11.21500(10)
_cell_length_c                   19.5965(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2055.16(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19905
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      75.5630
_cell_measurement_theta_min      3.9240
_shelx_estimated_absorpt_T_max   0.801
_shelx_estimated_absorpt_T_min   0.654
_exptl_absorpt_coefficient_mu    2.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 3 5 0.0599
-1 7 -5 0.0565
-5 -3 -5 0.0710
0 -7 5 0.0652
5 4 -3 0.0620
4 -1 -9 0.0485
0 -6 -8 0.0522
-4 -5 0 0.0764
0 0 -13 0.0541
-2 7 5 0.0360
6 0 -5 0.0534
-5 3 7 0.0614
0 4 11 0.0226
0 -2 12 0.0601
5 -5 -1 0.0740

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
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
4.9942 2.7772 5.3509 0.5341 -0.0766 0.8420
-0.6265 6.5375 -5.4245 -0.7889 0.1139 0.6039
-4.9499 -3.0261 -5.1145 -0.5006 0.0717 -0.8627
0.4349 -6.6186 5.2016 0.7657 -0.1105 -0.6336
4.7242 4.2041 -3.1260 0.0619 0.4316 0.8999
4.1324 -0.6756 -9.2544 0.1376 0.9559 0.2595
-0.1327 -5.6014 -8.1247 0.1034 0.7164 -0.6900
-4.0827 -5.3832 0.0807 -0.0199 -0.1405 -0.9899
0.3308 0.0484 -12.7049 -0.4654 0.8825 -0.0676
-1.5228 6.5471 4.5617 -0.4957 -0.6288 0.5991
5.5351 0.3141 -5.2057 0.3709 0.7556 0.5399
-4.5426 2.7980 6.8933 -0.4396 -0.8938 -0.0889
-0.4395 3.9871 10.6104 0.0576 -0.8763 0.4783
-0.1169 -2.1982 12.1240 0.6331 -0.7594 -0.1499
4.5690 -4.7651 -0.9362 0.8287 0.5549 -0.0729

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23219
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.754
_diffrn_reflns_theta_min         4.513
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  54.00   0.50    0.50    --  -35.00  50.00  95.00  246
  2  ω    -72.00  54.00   0.50    0.50    --  -35.00  71.00 -80.00  252
  3  ω      6.00 133.00   0.50    0.50    --   43.60  71.00 -80.00  254
  4  ω      9.00 133.00   0.50    0.50    --   43.60  50.00  95.00  248
  5  ω     75.00 199.00   0.50    0.50    --  109.30  50.00  95.00  248
  6  ω     20.00 145.00   0.50    0.50    --  109.30 -50.00 -51.00  250
  7  ω     72.00 199.00   0.50    0.50    --  109.30  71.00 -80.00  254
  8  ω     20.00 148.00   0.50    0.50    --  109.30 -71.00 149.00  256
  9  ω   -124.00 -76.00   0.50    0.50    --  -35.00 -77.00-180.00   96
 10  ω      2.00  48.00   0.50    0.50    --   43.60  77.00-150.00   92
 11  ω      2.00  48.00   0.50    0.50    --   43.60  77.00  60.00   92
 12  ω      2.00  48.00   0.50    0.50    --   43.60  77.00 150.00   92
 13  ω     20.00 149.00   0.50    0.50    --  109.30 -45.00 150.00  258
 14  ω     76.00 199.00   0.50    0.50    --  109.30  61.00-180.00  246
 15  ω     82.00 199.00   0.50    0.50    --  109.30  82.00 120.00  234
 16  ω     82.00 199.00   0.50    0.50    --  109.30  82.00 -90.00  234
 17  ω     76.00 199.00   0.50    0.50    --  109.30  61.00   0.00  246
 18  ω     75.00 133.00   0.50    0.50    --   43.60  77.00 -30.00  116
 19  ω      0.00 133.00   0.50    0.50    --   43.60  38.00 -90.00  266
 20  ω    -46.00  -1.00   0.50    0.50    --   43.60 -57.00 150.00   90
 21  ω      2.00  48.00   0.50    0.50    --   43.60  77.00   0.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1082533000
_diffrn_orient_matrix_UB_12      -0.0778097000
_diffrn_orient_matrix_UB_13      0.0391531000
_diffrn_orient_matrix_UB_21      0.0746843000
_diffrn_orient_matrix_UB_22      -0.0315490000
_diffrn_orient_matrix_UB_23      -0.0676390000
_diffrn_orient_matrix_UB_31      0.0991911000
_diffrn_orient_matrix_UB_32      0.1087796000
_diffrn_orient_matrix_UB_33      0.0083142000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                4114
_reflns_number_total             4135
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 40.35a 64-bit (release 18-12-2018))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0217
_refine_ls_restrained_S_all      1.066
_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)+(0.0243P)²+1.0171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0547
_refine_ls_wR_factor_ref         0.0547
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10), N21(H21), C12(H12), C3(H3), C4(H4), C7(H7), C6(H6), C13(H13),
 C15(H15), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C27(H27A,H27B,
 H27C)
;
_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
Br1 Br 0.85498(3) 1.08967(2) 0.63039(2) 0.03408(8) Uani 1 1 d . . . . .
O23 O 0.90315(17) 0.64464(16) 0.41185(8) 0.0232(3) Uani 1 1 d . . . . .
O24 O 0.73993(18) 0.5865(2) 0.33272(8) 0.0318(4) Uani 1 1 d . . . . .
N10 N 0.4834(2) 0.60708(18) 0.58760(9) 0.0198(4) Uani 1 1 d . . . . .
H10 H 0.491302 0.684483 0.593950 0.024 Uiso 1 1 calc R U . . .
N21 N 0.67824(19) 0.5893(2) 0.44167(9) 0.0207(4) Uani 1 1 d . . . . .
H21 H 0.590859 0.576108 0.426808 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5764(2) 0.5369(2) 0.55029(11) 0.0186(4) Uani 1 1 d . . . . .
N20 N 0.9232(3) 0.4459(2) 0.54117(12) 0.0344(5) Uani 1 1 d . . . . .
C22 C 0.7857(2) 0.6094(2) 0.39577(11) 0.0194(5) Uani 1 1 d . . . . .
C8 C 0.7064(2) 0.5893(2) 0.51530(10) 0.0191(4) Uani 1 1 d . . . . .
C2 C 0.8049(3) 0.9360(2) 0.59585(12) 0.0237(5) Uani 1 1 d . . . . .
C17 C 0.5324(3) 0.4199(2) 0.55183(12) 0.0241(5) Uani 1 1 d . . . . .
C5 C 0.7432(2) 0.7140(2) 0.54297(11) 0.0184(4) Uani 1 1 d . . . . .
C12 C 0.2573(3) 0.5650(3) 0.65279(12) 0.0330(6) Uani 1 1 d . . . . .
H12 H 0.237685 0.644987 0.665803 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7199(2) 0.9285(2) 0.53825(12) 0.0236(5) Uani 1 1 d . . . . .
H3 H 0.683724 0.998240 0.516887 0.028 Uiso 1 1 calc R U . . .
C19 C 0.8303(3) 0.5085(2) 0.52978(11) 0.0236(5) Uani 1 1 d . . . . .
C4 C 0.6891(2) 0.8159(2) 0.51251(11) 0.0215(5) Uani 1 1 d . . . . .
H4 H 0.629815 0.808765 0.473344 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3765(3) 0.5357(2) 0.61314(10) 0.0232(5) Uani 1 1 d . . . . .
C7 C 0.8581(3) 0.8362(2) 0.62839(12) 0.0266(5) Uani 1 1 d . . . . .
H7 H 0.914514 0.843585 0.668491 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4047(3) 0.4179(2) 0.59227(11) 0.0256(5) Uani 1 1 d . . . . .
C6 C 0.8273(3) 0.7250(2) 0.60114(12) 0.0237(5) Uani 1 1 d . . . . .
H6 H 0.864084 0.655446 0.622497 0.028 Uiso 1 1 calc R U . . .
C25 C 0.8456(3) 0.5681(2) 0.27634(11) 0.0284(5) Uani 1 1 d . . . . .
C13 C 0.1692(3) 0.4717(3) 0.67213(14) 0.0421(8) Uani 1 1 d . . . . .
H13 H 0.087880 0.488041 0.699609 0.050 Uiso 1 1 calc R U . . .
C18 C 0.6000(3) 0.3131(2) 0.51924(17) 0.0393(7) Uani 1 1 d . . . . .
H18A H 0.653549 0.337969 0.478688 0.059 Uiso 1 1 calc R U . . .
H18B H 0.525403 0.256241 0.505930 0.059 Uiso 1 1 calc R U . . .
H18C H 0.665224 0.275048 0.551772 0.059 Uiso 1 1 calc R U . . .
C15 C 0.3126(3) 0.3264(3) 0.61279(14) 0.0370(7) Uani 1 1 d . . . . .
H15 H 0.330193 0.246241 0.599461 0.044 Uiso 1 1 calc R U . . .
C14 C 0.1965(3) 0.3542(3) 0.65247(15) 0.0426(8) Uani 1 1 d . . . . .
H14 H 0.133543 0.292619 0.666804 0.051 Uiso 1 1 calc R U . . .
C26 C 0.9205(4) 0.6820(3) 0.25906(15) 0.0431(8) Uani 1 1 d . . . . .
H26A H 0.849533 0.743903 0.249028 0.065 Uiso 1 1 calc R U . . .
H26B H 0.981458 0.669671 0.219009 0.065 Uiso 1 1 calc R U . . .
H26C H 0.979490 0.707094 0.297809 0.065 Uiso 1 1 calc R U . . .
C28 C 0.9470(5) 0.4708(3) 0.29557(17) 0.0597(11) Uani 1 1 d . . . . .
H28A H 0.998383 0.493225 0.337209 0.090 Uiso 1 1 calc R U . . .
H28B H 1.015603 0.458222 0.258467 0.090 Uiso 1 1 calc R U . . .
H28C H 0.893398 0.397000 0.303642 0.090 Uiso 1 1 calc R U . . .
C27 C 0.7494(4) 0.5319(5) 0.21815(16) 0.0815(18) Uani 1 1 d . . . . .
H27A H 0.691452 0.463193 0.231934 0.122 Uiso 1 1 calc R U . . .
H27B H 0.807830 0.510405 0.178502 0.122 Uiso 1 1 calc R U . . .
H27C H 0.686429 0.598560 0.206210 0.122 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
Br1 C2 1.910(2) . ?
O23 C22 1.209(3) . ?
O24 C22 1.333(3) . ?
O24 C25 1.496(3) . ?
N10 H10 0.8800 . ?
N10 C9 1.382(3) . ?
N10 C11 1.376(3) . ?
N21 H21 0.8800 . ?
N21 C22 1.367(3) . ?
N21 C8 1.467(3) . ?
C9 C8 1.515(3) . ?
C9 C17 1.375(3) . ?
N20 C19 1.140(3) . ?
C8 C5 1.539(3) . ?
C8 C19 1.497(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.380(3) . ?
C17 C16 1.433(3) . ?
C17 C18 1.498(4) . ?
C5 C4 1.385(3) . ?
C5 C6 1.390(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.398(3) . ?
C12 C13 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C11 C16 1.407(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.387(3) . ?
C16 C15 1.399(4) . ?
C6 H6 0.9500 . ?
C25 C26 1.495(4) . ?
C25 C28 1.494(4) . ?
C25 C27 1.508(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C15 H15 0.9500 . ?
C15 C14 1.372(5) . ?
C14 H14 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C22 O24 C25 119.93(18) . . ?
C9 N10 H10 125.7 . . ?
C11 N10 H10 125.7 . . ?
C11 N10 C9 108.54(19) . . ?
C22 N21 H21 119.5 . . ?
C22 N21 C8 120.99(18) . . ?
C8 N21 H21 119.5 . . ?
N10 C9 C8 121.5(2) . . ?
C17 C9 N10 110.1(2) . . ?
C17 C9 C8 128.4(2) . . ?
O23 C22 O24 126.6(2) . . ?
O23 C22 N21 123.4(2) . . ?
O24 C22 N21 109.99(18) . . ?
N21 C8 C9 107.51(17) . . ?
N21 C8 C5 112.8(2) . . ?
N21 C8 C19 108.98(18) . . ?
C9 C8 C5 111.89(18) . . ?
C19 C8 C9 107.4(2) . . ?
C19 C8 C5 108.08(18) . . ?
C3 C2 Br1 119.02(18) . . ?
C7 C2 Br1 118.63(18) . . ?
C7 C2 C3 122.3(2) . . ?
C9 C17 C16 106.1(2) . . ?
C9 C17 C18 128.9(2) . . ?
C16 C17 C18 125.1(2) . . ?
C4 C5 C8 121.1(2) . . ?
C4 C5 C6 119.1(2) . . ?
C6 C5 C8 119.7(2) . . ?
C11 C12 H12 121.7 . . ?
C13 C12 H12 121.7 . . ?
C13 C12 C11 116.6(3) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.1(2) . . ?
C4 C3 H3 120.9 . . ?
N20 C19 C8 179.0(3) . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
N10 C11 C12 130.1(2) . . ?
N10 C11 C16 107.7(2) . . ?
C12 C11 C16 122.2(2) . . ?
C2 C7 H7 120.8 . . ?
C2 C7 C6 118.4(2) . . ?
C6 C7 H7 120.8 . . ?
C11 C16 C17 107.6(2) . . ?
C15 C16 C17 133.1(3) . . ?
C15 C16 C11 119.3(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.6 . . ?
O24 C25 C27 101.6(2) . . ?
C26 C25 O24 111.1(2) . . ?
C26 C25 C27 109.8(3) . . ?
C28 C25 O24 109.5(2) . . ?
C28 C25 C26 112.6(3) . . ?
C28 C25 C27 111.8(3) . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.0(3) . . ?
C14 C13 H13 119.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C15 H15 120.6 . . ?
C14 C15 C16 118.9(3) . . ?
C14 C15 H15 120.6 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(3) . . ?
C15 C14 H14 119.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
Br1 C2 C3 C4 177.69(17) . . . . ?
Br1 C2 C7 C6 -176.85(18) . . . . ?
N10 C9 C8 N21 -107.9(2) . . . . ?
N10 C9 C8 C5 16.4(3) . . . . ?
N10 C9 C8 C19 134.9(2) . . . . ?
N10 C9 C17 C16 0.2(3) . . . . ?
N10 C9 C17 C18 -179.6(2) . . . . ?
N10 C11 C16 C17 -0.9(2) . . . . ?
N10 C11 C16 C15 178.8(2) . . . . ?
N21 C8 C5 C4 29.2(3) . . . . ?
N21 C8 C5 C6 -153.5(2) . . . . ?
C9 N10 C11 C12 -178.9(2) . . . . ?
C9 N10 C11 C16 1.0(2) . . . . ?
C9 C8 C5 C4 -92.1(2) . . . . ?
C9 C8 C5 C6 85.2(3) . . . . ?
C9 C17 C16 C11 0.5(3) . . . . ?
C9 C17 C16 C15 -179.1(2) . . . . ?
C22 O24 C25 C26 -69.4(3) . . . . ?
C22 O24 C25 C28 55.5(4) . . . . ?
C22 O24 C25 C27 173.9(3) . . . . ?
C22 N21 C8 C9 -167.1(2) . . . . ?
C22 N21 C8 C5 69.1(3) . . . . ?
C22 N21 C8 C19 -50.9(3) . . . . ?
C8 N21 C22 O23 -10.8(4) . . . . ?
C8 N21 C22 O24 170.2(2) . . . . ?
C8 C9 C17 C16 179.4(2) . . . . ?
C8 C9 C17 C18 -0.4(4) . . . . ?
C8 C5 C4 C3 178.7(2) . . . . ?
C8 C5 C6 C7 -177.9(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C7 C6 C5 -0.8(4) . . . . ?
C17 C9 C8 N21 72.9(3) . . . . ?
C17 C9 C8 C5 -162.7(2) . . . . ?
C17 C9 C8 C19 -44.2(3) . . . . ?
C17 C16 C15 C14 180.0(2) . . . . ?
C12 C11 C16 C17 179.0(2) . . . . ?
C12 C11 C16 C15 -1.3(3) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C3 C2 C7 C6 1.4(4) . . . . ?
C19 C8 C5 C4 149.8(2) . . . . ?
C19 C8 C5 C6 -32.9(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C11 N10 C9 C8 179.99(19) . . . . ?
C11 N10 C9 C17 -0.7(3) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C11 C16 C15 C14 0.4(4) . . . . ?
C7 C2 C3 C4 -0.6(3) . . . . ?
C16 C15 C14 C13 0.3(4) . . . . ?
C6 C5 C4 C3 1.4(3) . . . . ?
C25 O24 C22 O23 18.3(4) . . . . ?
C25 O24 C22 N21 -162.7(2) . . . . ?
C13 C12 C11 N10 -178.6(2) . . . . ?
C13 C12 C11 C16 1.5(4) . . . . ?
C18 C17 C16 C11 -179.8(2) . . . . ?
C18 C17 C16 C15 0.6(4) . . . . ?

_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 1.117
_oxdiff_exptl_absorpt_empirical_full_min 0.940
####################################################################### 
# 
# 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_6-clindolepro-3
_database_code_depnum_ccdc_archive 'CCDC 2383151'
loop_
_audit_author_name
_audit_author_address
'Shuichi Nakamura'
;Nagoya Institute of Technology
Japan
;
_audit_update_record             
;
2024-09-10 deposited with the CCDC.	2025-02-11 downloaded from the CCDC.
;
_audit_creation_date             2024-04-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 Cl N3 O2'
_chemical_formula_sum            'C21 H20 Cl N3 O2'
_chemical_formula_weight         381.85
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H20 Cl1 N3 O2'
_chemical_oxdiff_usercomment     'Micormount, -120oC'
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'
Cl Cl 0.3639 0.7018 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   9.7777(3)
_cell_length_b                   10.8697(2)
_cell_length_c                   11.3717(3)
_cell_angle_alpha                62.837(2)
_cell_angle_beta                 64.591(3)
_cell_angle_gamma                74.964(2)
_cell_volume                     968.24(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15147
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      75.2490
_cell_measurement_theta_min      4.5750
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    1.914
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 4 -2 0.0318
0 -6 0 0.0181
-4 2 4 0.0332
0 6 0 0.0234
0 -2 -7 0.0490
6 2 3 0.0346
2 3 7 0.0332
-6 -1 -1 0.0220
-5 -3 -6 0.0414
4 0 -3 0.0378
-4 4 -2 0.0211
2 1 -5 0.0378
4 2 -2 0.0298
0 -5 -6 0.0446
-3 -7 -5 0.0418
4 3 7 0.0258
-5 2 -1 0.0170
-3 2 -4 0.0344
3 7 5 0.0235
0 5 6 0.0293

_exptl_crystal_size_max          0.084
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.044
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
2.0304 4.1937 -2.4005 0.7115 -0.1797 0.6794
0.1190 -6.1813 0.1594 -0.9645 0.2439 -0.1010
-3.5209 1.9597 3.7317 0.2116 -0.0539 -0.9759
-0.4698 6.2735 0.2173 0.9695 -0.2452 0.0015
-0.2682 -2.3544 -6.7809 -0.1444 -0.5698 0.8090
6.3044 2.0972 2.5936 0.1914 0.7573 0.6244
1.7232 2.8011 7.2696 0.1863 0.7358 -0.6511
-5.8924 -1.3218 -0.5445 -0.1405 -0.5564 -0.8190
-5.4189 -3.1409 -6.1703 -0.2450 -0.9686 -0.0430
3.7492 -0.4541 -3.4677 0.0115 0.0466 0.9988
-4.0576 3.8250 -1.5122 0.6741 -0.6554 -0.3406
1.8634 1.0957 -4.6858 0.3061 -0.2977 0.9043
4.3219 2.3758 -1.7737 0.3911 0.1573 0.9068
-0.2189 -5.1877 -6.1238 -0.6053 -0.4044 0.6856
-3.1229 -6.5780 -5.3024 -0.8242 -0.5517 0.1280
4.4266 3.2282 6.9871 0.2401 0.9481 -0.2087
-5.1442 2.4803 -1.4506 0.4723 -0.7042 -0.5302
-3.4949 2.4637 -4.4487 0.5532 -0.8265 0.1045
2.8982 6.8103 4.6832 0.8819 0.4651 -0.0766
-0.4333 5.0305 5.7621 0.5977 0.3153 -0.7371

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            73028
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.525
_diffrn_reflns_theta_min         4.587
_diffrn_ambient_temperature      153(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -124.00 -76.00   0.50    1.99    --  -35.00 -77.00 120.00   96
  2  ω    -78.00  54.00   0.50    1.99    --  -35.00  38.00-180.00  264
  3  ω   -124.00 -76.00   0.50    1.99    --  -35.00 -77.00-180.00   96
  4  ω    -78.00  54.00   0.50    1.99    --  -35.00  38.00-180.00  264
  5  ω    -46.00  77.00   0.50    1.99    --   43.60 -57.00 -60.00  246
  6  ω      2.00  48.00   0.50    1.99    --   43.60  77.00  90.00   92
  7  ω     81.00 133.00   0.50    1.99    --   43.60  82.00 -60.00  104
  8  ω      2.00  48.00   0.50    1.99    --   43.60  77.00  30.00   92
  9  ω      3.00  42.00   0.50    1.99    --   46.00  80.00 164.64   78
 10  ω      6.00  41.00   0.50    1.99    --   50.00  81.00-176.90   70
 11  ω      6.00  41.00   0.50    1.99    --   50.00  81.00 -81.50   70
 12  ω     11.00  43.00   0.50    1.99    --   54.00  79.00 145.93   64
 13  ω     10.00  41.00   0.50    1.99    --   54.00  81.00-127.35   62
 14  ω     14.00  41.00   0.50    1.99    --   58.00  81.00 -33.78   54
 15  ω     14.00  41.00   0.50    1.99    --   58.00  81.00-101.65   54
 16  ω     15.00  43.00   0.50    1.99    --   58.00  79.00 113.16   56
 17  ω     27.00  61.00   0.50    1.99    --   66.00  74.00-162.51   68
 18  ω     30.00  56.00   0.50    1.99    --   70.00  75.00  38.75   52
 19  ω     30.00  56.00   0.50    1.99    --   70.00  75.00 -11.82   52
 20  ω     35.00  61.00   0.50    1.99    --   74.00  74.00 -54.41   52
 21  ω     40.00 163.00   0.50    1.99    --   74.00  64.00 166.98  246
 22  ω     35.00  61.00   0.50    1.99    --   74.00  74.00   1.07   52
 23  ω     35.00 163.00   0.50    1.99    --   74.00  73.00-109.25  256
 24  ω     42.00 167.00   0.50    7.98    --   78.00  69.00 110.35  250
 25  ω     39.00 167.00   0.50    7.98    --   78.00  73.00 -85.89  256
 26  ω     40.00 167.00   0.50    7.98    --   78.00  72.00  19.50  254
 27  ω     43.00 171.00   0.50    7.98    --   82.00  73.00-169.26  256
 28  ω     51.00 175.00   0.50    7.98    --   86.00  67.00 173.26  248
 29  ω     47.00 175.00   0.50    7.98    --   86.00  73.00  51.24  256
 30  ω     51.00 179.00   0.50    7.98    --   90.00  73.00  75.49  256
 31  ω     51.00 179.00   0.50    7.98    --   90.00  73.00 -57.22  256
 32  ω     61.00 183.00   0.50    7.98    --   94.00  55.00-102.14  244
 33  ω     61.00 183.00   0.50    7.98    --   94.00  53.00 -81.68  244
 34  ω     60.00 187.00   0.50    7.98    --   98.00  72.00 113.32  254
 35  ω     64.00 191.00   0.50    7.98    --  102.00  72.00 -40.78  254
 36  ω     76.00 199.00   0.50    7.98    --  109.30  61.00-180.00  246
 37  ω     76.00 199.00   0.50    7.98    --  109.30  77.00 -90.00  246
 38  ω     76.00 199.00   0.50    7.98    --  109.30  77.00 -30.00  246
 39  ω     76.00 199.00   0.50    7.98    --  109.30  61.00 150.00  246
 40  ω     72.00 199.00   0.50    7.98    --  109.30  70.00  11.08  254
 41  ω     72.00 199.00   0.50    7.98    --  109.30  70.00  31.87  254
 42  ω     74.00 199.00   0.50    7.98    --  109.30  67.00  57.91  250
 43  ω     20.00 154.00   0.50    7.98    --  109.30 -82.00  30.00  268
 44  ω     76.00 199.00   0.50    7.98    --  109.30  61.00-150.00  246
 45  ω     70.00 199.00   0.50    7.98    --  109.30  45.00 120.00  258
 46  ω     20.00 154.00   0.50    7.98    --  109.30 -82.00-120.00  268
 47  ω     20.00 154.00   0.50    7.98    --  109.30 -82.00 -60.00  268
 48  ω     20.00 154.00   0.50    7.98    --  109.30 -82.00 120.00  268
 49  ω    -39.00   9.00   0.50    1.99    --  -35.00 -82.00  30.00   96
 50  ω    -79.00  39.00   0.50    1.99    --  -35.00  82.00 -90.00  236
 51  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00 -30.00  358
 52  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00  60.00  358
 53  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00 -60.00  358
 54  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00-120.00  358
 55  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00   0.00  358
 56  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00-150.00  358
 57  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00 -90.00  358
 58  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00  90.00  358
 59  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00 150.00  358
 60  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00  30.00  358
 61  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00-180.00  358
 62  ω    -46.00 133.00   0.50    1.99    --   43.60  19.00 120.00  358
 63  ω     15.00  42.00   0.50    1.99    --   58.00  80.00  57.22   54
 64  ω     35.00 159.00   0.50    1.99    --   70.00  67.00  92.69  248
 65  ω     35.00  61.00   0.50    1.99    --   74.00  74.00 -98.89   52
 66  ω     44.00 171.00   0.50    7.98    --   82.00  72.00  80.15  254
 67  ω     46.00 171.00   0.50    7.98    --   82.00  68.00  43.33  250
 68  ω     20.00 154.00   0.50    7.98    --  109.30 -82.00 -90.00  268
 69  ω     20.00 151.00   0.50    7.98    --  109.30 -77.00-180.00  262
 70  ω     76.00 199.00   0.50    7.98    --  109.30  77.00-120.00  246
 71  ω     76.00 199.00   0.50    7.98    --  109.30  77.00-150.00  246
 72  ω     20.00 199.00   0.50    7.98    --  109.30  15.00   0.00  358
 73  ω     20.00 199.00   0.50    7.98    --  109.30  15.00 -30.00  358
 74  ω     76.00 199.00   0.50    7.98    --  109.30  77.00 150.00  246
 75  ω     76.00 199.00   0.50    7.98    --  109.30  77.00 -60.00  246
 76  ω     20.00 199.00   0.50    7.98    --  109.30  15.00-150.00  358
 77  ω     82.00 199.00   0.50    7.98    --  109.30  82.00-120.00  234
 78  ω     20.00 199.00   0.50    7.98    --  109.30   0.00-180.00  358
 79  ω     76.00 199.00   0.50    7.98    --  109.30  77.00-180.00  246
 80  ω     20.00 199.00   0.50    7.98    --  109.30   0.00 120.00  358
 81  ω     20.00 199.00   0.50    7.98    --  109.30   0.00  90.00  358
 82  ω     82.00 199.00   0.50    7.98    --  109.30  82.00 -30.00  234
 83  ω     20.00 199.00   0.50    7.98    --  109.30   0.00  60.00  358
 84  ω     20.00 199.00   0.50    7.98    --  109.30   0.00  30.00  358
 85  ω     76.00 199.00   0.50    7.98    --  109.30  61.00  90.00  246
 86  ω     20.00 199.00   0.50    7.98    --  109.30   0.00   0.00  358
 87  ω     20.00 199.00   0.50    7.98    --  109.30   0.00 -30.00  358
 88  ω     82.00 199.00   0.50    7.98    --  109.30  82.00-150.00  234
 89  ω     20.00 199.00   0.50    7.98    --  109.30   0.00 150.00  358
 90  ω     20.00 199.00   0.50    7.98    --  109.30  15.00-180.00  358
 91  ω     20.00 199.00   0.50    7.98    --  109.30   0.00 -60.00  358
 92  ω     20.00 199.00   0.50    7.98    --  109.30  15.00-120.00  358
 93  ω     20.00 199.00   0.50    7.98    --  109.30  15.00 -90.00  358
 94  ω     20.00 199.00   0.50    7.98    --  109.30  15.00 -60.00  358
 95  ω     20.00 199.00   0.50    7.98    --  109.30   0.00 -90.00  358
 96  ω     20.00 199.00   0.50    7.98    --  109.30   0.00-120.00  358
 97  ω     20.00 199.00   0.50    7.98    --  109.30  15.00  30.00  358
 98  ω     20.00 199.00   0.50    7.98    --  109.30  15.00  60.00  358
 99  ω     20.00 199.00   0.50    7.98    --  109.30   0.00-150.00  358
100  ω    -46.00 133.00   0.50    1.99    --   43.60   0.00-150.00  358
101  ω    -46.00  56.00   0.50    1.99    --   43.60   0.00-120.00  204
102  ω    -46.00 133.00   0.50    1.99    --   43.60   0.00-180.00  358
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0079618000
_diffrn_orient_matrix_UB_12      0.1550536000
_diffrn_orient_matrix_UB_13      -0.0322315000
_diffrn_orient_matrix_UB_21      0.0937788000
_diffrn_orient_matrix_UB_22      -0.0352713000
_diffrn_orient_matrix_UB_23      0.0925696000
_diffrn_orient_matrix_UB_31      0.1475137000
_diffrn_orient_matrix_UB_32      0.0158052000
_diffrn_orient_matrix_UB_33      -0.1306259000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.911
_reflns_number_gt                6950
_reflns_number_total             7705
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 40.35a 64-bit (release 18-12-2018))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 3043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         7705
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.083
_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)+(0.0790P)²+0.3680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1448
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), N3(H3), N6(H6), N1(H1), C8(H8), C23(H23), C29(H29), C26(H26),
 C12(H12), C13(H13), C5(H5), C14(H14), C35(H35), C33(H33), C2(H2), C16(H16),
 C15(H15), C36(H36), C37(H37), C25(H25), C34(H34), C4(H4A)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C40(H40A,H40B,H40C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 1.02974(15) 0.32116(14) -0.46013(16) 0.0617(4) Uani 1 1 d . . . . .
Cl1 Cl 0.96516(16) 0.69042(14) 0.45447(17) 0.0651(4) Uani 1 1 d . . . . .
O2 O 0.7328(4) 0.2660(3) 0.1284(3) 0.0450(8) Uani 1 1 d . . . . .
O1 O 0.5326(4) 0.3240(3) 0.2998(3) 0.0424(7) Uani 1 1 d . . . . .
O3 O 0.2307(4) 0.6756(3) -0.3057(3) 0.0436(7) Uani 1 1 d . . . . .
O4 O 0.2599(4) 0.7431(3) -0.1565(3) 0.0460(8) Uani 1 1 d . . . . .
N4 N 0.4815(5) 0.3370(4) -0.4347(4) 0.0400(8) Uani 1 1 d . . . . .
H4 H 0.498402 0.322704 -0.510128 0.048 Uiso 1 1 calc R U . . .
N3 N 0.6699(5) 0.4862(3) 0.0919(4) 0.0393(8) Uani 1 1 d . . . . .
H3 H 0.757067 0.500278 0.019946 0.047 Uiso 1 1 calc R U . . .
N6 N 0.2561(5) 0.5193(4) -0.0967(4) 0.0411(8) Uani 1 1 d . . . . .
H6 H 0.275283 0.507246 -0.023142 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6730(5) 0.6416(4) 0.2629(5) 0.0368(9) Uani 1 1 d . . . . .
N1 N 0.4516(5) 0.6711(4) 0.4311(4) 0.0403(8) Uani 1 1 d . . . . .
H1 H 0.384493 0.687530 0.505204 0.048 Uiso 1 1 calc R U . . .
C22 C 0.5921(6) 0.3405(4) -0.3918(5) 0.0377(9) Uani 1 1 d . . . . .
C1 C 0.6073(5) 0.6665(4) 0.3889(5) 0.0372(9) Uani 1 1 d . . . . .
C30 C 0.2337(5) 0.3992(4) -0.1095(5) 0.0383(9) Uani 1 1 d . . . . .
C9 C 0.5651(5) 0.6059(4) 0.1079(4) 0.0364(9) Uani 1 1 d . . . . .
C7 C 0.5496(5) 0.6282(4) 0.2349(4) 0.0369(9) Uani 1 1 d . . . . .
C27 C 0.5177(5) 0.3622(4) -0.2642(4) 0.0367(9) Uani 1 1 d . . . . .
C28 C 0.3581(5) 0.3750(4) -0.2353(5) 0.0378(9) Uani 1 1 d . . . . .
C8 C 0.4184(5) 0.6460(4) 0.3389(5) 0.0383(9) Uani 1 1 d . . . . .
H8 H 0.319054 0.641684 0.346272 0.046 Uiso 1 1 calc R U . . .
C38 C 0.2479(5) 0.6499(4) -0.1963(5) 0.0388(9) Uani 1 1 d . . . . .
N5 N -0.0310(5) 0.4525(5) -0.1394(5) 0.0506(10) Uani 1 1 d . . . . .
C23 C 0.7500(6) 0.3271(4) -0.4549(5) 0.0433(10) Uani 1 1 d . . . . .
H23 H 0.798554 0.314004 -0.541230 0.052 Uiso 1 1 calc R U . . .
C17 C 0.6373(5) 0.3549(4) 0.1838(5) 0.0384(9) Uani 1 1 d . . . . .
C11 C 0.6186(5) 0.7350(4) -0.0323(5) 0.0378(9) Uani 1 1 d . . . . .
C10 C 0.4144(5) 0.5796(4) 0.1254(5) 0.0390(9) Uani 1 1 d . . . . .
C29 C 0.3412(6) 0.3592(4) -0.3414(5) 0.0393(9) Uani 1 1 d . . . . .
H29 H 0.246964 0.362947 -0.348928 0.047 Uiso 1 1 calc R U . . .
N2 N 0.3002(5) 0.5559(5) 0.1355(5) 0.0519(10) Uani 1 1 d . . . . .
C26 C 0.6063(6) 0.3680(5) -0.1973(5) 0.0440(10) Uani 1 1 d . . . . .
H26 H 0.558902 0.381845 -0.111335 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6194(6) 0.8619(4) -0.0319(5) 0.0417(10) Uani 1 1 d . . . . .
H12 H 0.588954 0.870326 0.055570 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6643(6) 0.9772(4) -0.1588(5) 0.0462(11) Uani 1 1 d . . . . .
H13 H 0.663909 1.064148 -0.157608 0.055 Uiso 1 1 calc R U . . .
C32 C 0.2187(5) 0.2703(5) 0.0318(5) 0.0406(9) Uani 1 1 d . . . . .
C5 C 0.8320(6) 0.6346(5) 0.1965(5) 0.0435(10) Uani 1 1 d . . . . .
H5 H 0.878775 0.619231 0.111327 0.052 Uiso 1 1 calc R U . . .
C18 C 0.7200(6) 0.1154(4) 0.2024(5) 0.0435(10) Uani 1 1 d . . . . .
C31 C 0.0851(6) 0.4277(5) -0.1281(5) 0.0402(9) Uani 1 1 d . . . . .
C14 C 0.7091(7) 0.9654(5) -0.2858(5) 0.0489(11) Uani 1 1 d . . . . .
H14 H 0.741332 1.043709 -0.372599 0.059 Uiso 1 1 calc R U . . .
C35 C 0.1798(7) 0.0339(5) 0.2838(6) 0.0517(12) Uani 1 1 d . . . . .
H35 H 0.166888 -0.046560 0.369302 0.062 Uiso 1 1 calc R U . . .
C33 C 0.2769(6) 0.1406(5) 0.0293(5) 0.0467(11) Uani 1 1 d . . . . .
H33 H 0.331634 0.132273 -0.059188 0.056 Uiso 1 1 calc R U . . .
C2 C 0.6951(6) 0.6816(4) 0.4507(5) 0.0432(10) Uani 1 1 d . . . . .
H2 H 0.649884 0.696509 0.536100 0.052 Uiso 1 1 calc R U . . .
C39 C 0.2224(6) 0.8926(5) -0.2303(6) 0.0466(11) Uani 1 1 d . . . . .
C16 C 0.6617(6) 0.7252(5) -0.1620(5) 0.0464(11) Uani 1 1 d . . . . .
H16 H 0.659697 0.639484 -0.164386 0.056 Uiso 1 1 calc R U . . .
C24 C 0.8316(6) 0.3340(5) -0.3853(6) 0.0472(11) Uani 1 1 d . . . . .
C15 C 0.7071(7) 0.8403(5) -0.2865(5) 0.0521(12) Uani 1 1 d . . . . .
H15 H 0.737628 0.832691 -0.374466 0.063 Uiso 1 1 calc R U . . .
C36 C 0.1225(7) 0.1624(5) 0.2877(5) 0.0535(12) Uani 1 1 d . . . . .
H36 H 0.071034 0.170707 0.376398 0.064 Uiso 1 1 calc R U . . .
C37 C 0.1399(6) 0.2808(5) 0.1618(5) 0.0472(11) Uani 1 1 d . . . . .
H37 H 0.097431 0.368724 0.165350 0.057 Uiso 1 1 calc R U . . .
C20 C 0.7386(7) 0.0624(5) 0.3437(6) 0.0508(12) Uani 1 1 d . . . . .
H20A H 0.830054 0.096651 0.329724 0.076 Uiso 1 1 calc R U . . .
H20B H 0.748068 -0.039256 0.384237 0.076 Uiso 1 1 calc R U . . .
H20C H 0.649596 0.095558 0.408617 0.076 Uiso 1 1 calc R U . . .
C25 C 0.7629(6) 0.3533(5) -0.2572(6) 0.0483(11) Uani 1 1 d . . . . .
H25 H 0.823797 0.356129 -0.212240 0.058 Uiso 1 1 calc R U . . .
C34 C 0.2564(7) 0.0230(5) 0.1537(6) 0.0535(12) Uani 1 1 d . . . . .
H34 H 0.294955 -0.065430 0.150048 0.064 Uiso 1 1 calc R U . . .
C4 C 0.9192(6) 0.6502(5) 0.2565(6) 0.0495(11) Uani 1 1 d . . . . .
H4A H 1.026756 0.645176 0.212719 0.059 Uiso 1 1 calc R U . . .
C3 C 0.8497(6) 0.6737(5) 0.3822(6) 0.0485(11) Uani 1 1 d . . . . .
C40 C 0.3327(8) 0.9478(6) -0.3816(6) 0.0613(14) Uani 1 1 d . . . . .
H40A H 0.436898 0.919688 -0.383094 0.092 Uiso 1 1 calc R U . . .
H40B H 0.317900 1.049220 -0.422884 0.092 Uiso 1 1 calc R U . . .
H40C H 0.314771 0.910114 -0.436912 0.092 Uiso 1 1 calc R U . . .
C19 C 0.5696(7) 0.0828(5) 0.2177(6) 0.0541(13) Uani 1 1 d . . . . .
H19A H 0.485725 0.127906 0.274823 0.081 Uiso 1 1 calc R U . . .
H19B H 0.562170 -0.017799 0.264496 0.081 Uiso 1 1 calc R U . . .
H19C H 0.564071 0.117200 0.123676 0.081 Uiso 1 1 calc R U . . .
C21 C 0.8523(8) 0.0610(5) 0.1019(6) 0.0621(15) Uani 1 1 d . . . . .
H21A H 0.845505 0.106499 0.007495 0.093 Uiso 1 1 calc R U . . .
H21B H 0.849501 -0.039410 0.136464 0.093 Uiso 1 1 calc R U . . .
H21C H 0.947661 0.080539 0.096459 0.093 Uiso 1 1 calc R U . . .
C41 C 0.0591(7) 0.9141(6) -0.2188(7) 0.0617(14) Uani 1 1 d . . . . .
H41A H 0.047470 0.868751 -0.270912 0.093 Uiso 1 1 calc R U . . .
H41B H 0.030107 1.013587 -0.259051 0.093 Uiso 1 1 calc R U . . .
H41C H -0.006441 0.873743 -0.118807 0.093 Uiso 1 1 calc R U . . .
C42 C 0.2424(8) 0.9542(6) -0.1430(7) 0.0603(14) Uani 1 1 d . . . . .
H42A H 0.178572 0.909109 -0.043211 0.090 Uiso 1 1 calc R U . . .
H42B H 0.212396 1.053955 -0.177455 0.090 Uiso 1 1 calc R U . . .
H42C H 0.349072 0.939297 -0.152045 0.090 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
Cl2 C24 1.747(6) . ?
Cl1 C3 1.739(5) . ?
O2 C17 1.336(5) . ?
O2 C18 1.471(5) . ?
O1 C17 1.231(6) . ?
O3 C38 1.222(5) . ?
O4 C38 1.330(5) . ?
O4 C39 1.480(5) . ?
N4 H4 0.8800 . ?
N4 C22 1.377(6) . ?
N4 C29 1.371(6) . ?
N3 H3 0.8800 . ?
N3 C9 1.463(5) . ?
N3 C17 1.348(5) . ?
N6 H6 0.8800 . ?
N6 C30 1.458(6) . ?
N6 C38 1.361(5) . ?
C6 C1 1.419(6) . ?
C6 C7 1.428(6) . ?
C6 C5 1.406(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.381(6) . ?
N1 C8 1.371(6) . ?
C22 C27 1.418(6) . ?
C22 C23 1.396(7) . ?
C1 C2 1.397(7) . ?
C30 C28 1.509(6) . ?
C30 C32 1.555(6) . ?
C30 C31 1.491(7) . ?
C9 C7 1.511(6) . ?
C9 C11 1.551(6) . ?
C9 C10 1.486(7) . ?
C7 C8 1.364(7) . ?
C27 C28 1.433(7) . ?
C27 C26 1.403(6) . ?
C28 C29 1.375(6) . ?
C8 H8 0.9500 . ?
N5 C31 1.145(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(7) . ?
C11 C12 1.383(6) . ?
C11 C16 1.397(6) . ?
C10 N2 1.156(6) . ?
C29 H29 0.9500 . ?
C26 H26 0.9500 . ?
C26 C25 1.383(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(7) . ?
C32 C33 1.385(6) . ?
C32 C37 1.386(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.379(7) . ?
C18 C20 1.516(7) . ?
C18 C19 1.521(8) . ?
C18 C21 1.510(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.369(7) . ?
C35 H35 0.9500 . ?
C35 C36 1.377(8) . ?
C35 C34 1.388(8) . ?
C33 H33 0.9500 . ?
C33 C34 1.383(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(8) . ?
C39 C40 1.511(8) . ?
C39 C41 1.508(8) . ?
C39 C42 1.522(7) . ?
C16 H16 0.9500 . ?
C16 C15 1.378(7) . ?
C24 C25 1.408(8) . ?
C15 H15 0.9500 . ?
C36 H36 0.9500 . ?
C36 C37 1.399(7) . ?
C37 H37 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C25 H25 0.9500 . ?
C34 H34 0.9500 . ?
C4 H4A 0.9500 . ?
C4 C3 1.407(8) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 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 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
C17 O2 C18 122.0(4) . . ?
C38 O4 C39 120.9(4) . . ?
C22 N4 H4 125.3 . . ?
C29 N4 H4 125.3 . . ?
C29 N4 C22 109.4(4) . . ?
C9 N3 H3 118.9 . . ?
C17 N3 H3 118.9 . . ?
C17 N3 C9 122.2(4) . . ?
C30 N6 H6 119.3 . . ?
C38 N6 H6 119.3 . . ?
C38 N6 C30 121.4(3) . . ?
C1 C6 C7 106.4(4) . . ?
C5 C6 C1 118.7(4) . . ?
C5 C6 C7 134.9(4) . . ?
C1 N1 H1 125.5 . . ?
C8 N1 H1 125.5 . . ?
C8 N1 C1 109.0(4) . . ?
N4 C22 C27 107.6(4) . . ?
N4 C22 C23 129.9(4) . . ?
C23 C22 C27 122.5(4) . . ?
N1 C1 C6 107.4(4) . . ?
N1 C1 C2 130.2(4) . . ?
C2 C1 C6 122.4(4) . . ?
N6 C30 C28 111.8(4) . . ?
N6 C30 C32 109.3(3) . . ?
N6 C30 C31 107.0(4) . . ?
C28 C30 C32 112.3(4) . . ?
C31 C30 C28 109.4(4) . . ?
C31 C30 C32 106.8(4) . . ?
N3 C9 C7 112.6(3) . . ?
N3 C9 C11 108.4(4) . . ?
N3 C9 C10 107.3(4) . . ?
C7 C9 C11 112.2(3) . . ?
C10 C9 C7 109.0(4) . . ?
C10 C9 C11 107.1(3) . . ?
C6 C7 C9 125.1(4) . . ?
C8 C7 C6 107.6(4) . . ?
C8 C7 C9 127.3(4) . . ?
C22 C27 C28 106.4(4) . . ?
C26 C27 C22 118.7(4) . . ?
C26 C27 C28 134.8(4) . . ?
C27 C28 C30 125.5(4) . . ?
C29 C28 C30 127.2(4) . . ?
C29 C28 C27 107.3(4) . . ?
N1 C8 H8 125.2 . . ?
C7 C8 N1 109.7(4) . . ?
C7 C8 H8 125.2 . . ?
O3 C38 O4 125.7(4) . . ?
O3 C38 N6 123.8(4) . . ?
O4 C38 N6 110.6(4) . . ?
C22 C23 H23 121.8 . . ?
C24 C23 C22 116.4(5) . . ?
C24 C23 H23 121.8 . . ?
O2 C17 N3 109.8(4) . . ?
O1 C17 O2 126.0(4) . . ?
O1 C17 N3 124.1(4) . . ?
C12 C11 C9 121.4(4) . . ?
C12 C11 C16 118.8(4) . . ?
C16 C11 C9 119.7(4) . . ?
N2 C10 C9 177.1(5) . . ?
N4 C29 C28 109.4(4) . . ?
N4 C29 H29 125.3 . . ?
C28 C29 H29 125.3 . . ?
C27 C26 H26 120.2 . . ?
C25 C26 C27 119.6(5) . . ?
C25 C26 H26 120.2 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(4) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C33 C32 C30 119.8(4) . . ?
C33 C32 C37 118.8(4) . . ?
C37 C32 C30 121.3(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.2(5) . . ?
C4 C5 H5 120.4 . . ?
O2 C18 C20 110.2(4) . . ?
O2 C18 C19 109.3(4) . . ?
O2 C18 C21 102.2(4) . . ?
C20 C18 C19 112.6(4) . . ?
C21 C18 C20 110.8(5) . . ?
C21 C18 C19 111.2(5) . . ?
N5 C31 C30 177.4(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 H14 120.2 . . ?
C36 C35 H35 120.3 . . ?
C36 C35 C34 119.4(5) . . ?
C34 C35 H35 120.3 . . ?
C32 C33 H33 119.5 . . ?
C34 C33 C32 121.0(5) . . ?
C34 C33 H33 119.5 . . ?
C1 C2 H2 121.6 . . ?
C3 C2 C1 116.7(5) . . ?
C3 C2 H2 121.6 . . ?
O4 C39 C40 110.9(4) . . ?
O4 C39 C41 108.9(4) . . ?
O4 C39 C42 101.7(4) . . ?
C40 C39 C42 110.8(5) . . ?
C41 C39 C40 113.2(5) . . ?
C41 C39 C42 110.8(5) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 C11 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C23 C24 Cl2 118.8(4) . . ?
C23 C24 C25 123.1(5) . . ?
C25 C24 Cl2 118.1(4) . . ?
C14 C15 C16 121.2(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C35 C36 H36 119.8 . . ?
C35 C36 C37 120.3(5) . . ?
C37 C36 H36 119.8 . . ?
C32 C37 C36 120.3(5) . . ?
C32 C37 H37 119.9 . . ?
C36 C37 H37 119.9 . . ?
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 . . ?
C26 C25 C24 119.6(5) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C35 C34 H34 119.9 . . ?
C33 C34 C35 120.2(5) . . ?
C33 C34 H34 119.9 . . ?
C5 C4 H4A 119.8 . . ?
C5 C4 C3 120.3(5) . . ?
C3 C4 H4A 119.8 . . ?
C2 C3 Cl1 118.9(4) . . ?
C2 C3 C4 122.6(5) . . ?
C4 C3 Cl1 118.4(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
Cl2 C24 C25 C26 178.1(4) . . . . ?
N4 C22 C27 C28 -1.5(4) . . . . ?
N4 C22 C27 C26 179.1(4) . . . . ?
N4 C22 C23 C24 -179.4(4) . . . . ?
N3 C9 C7 C6 54.0(5) . . . . ?
N3 C9 C7 C8 -129.4(4) . . . . ?
N3 C9 C11 C12 -137.5(4) . . . . ?
N3 C9 C11 C16 45.0(6) . . . . ?
N6 C30 C28 C27 53.3(5) . . . . ?
N6 C30 C28 C29 -127.8(5) . . . . ?
N6 C30 C32 C33 -145.0(4) . . . . ?
N6 C30 C32 C37 39.0(6) . . . . ?
C6 C1 C2 C3 1.2(6) . . . . ?
C6 C7 C8 N1 0.5(5) . . . . ?
C6 C5 C4 C3 -0.3(7) . . . . ?
N1 C1 C2 C3 -179.1(4) . . . . ?
C22 N4 C29 C28 -1.0(5) . . . . ?
C22 C27 C28 C30 180.0(4) . . . . ?
C22 C27 C28 C29 0.9(4) . . . . ?
C22 C27 C26 C25 0.4(6) . . . . ?
C22 C23 C24 Cl2 -178.9(3) . . . . ?
C22 C23 C24 C25 0.1(6) . . . . ?
C1 C6 C7 C9 177.7(4) . . . . ?
C1 C6 C7 C8 0.6(4) . . . . ?
C1 C6 C5 C4 0.8(6) . . . . ?
C1 N1 C8 C7 -1.4(5) . . . . ?
C1 C2 C3 Cl1 -179.6(3) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C30 N6 C38 O3 -4.5(7) . . . . ?
C30 N6 C38 O4 175.0(4) . . . . ?
C30 C28 C29 N4 -179.0(4) . . . . ?
C30 C32 C33 C34 -175.7(5) . . . . ?
C30 C32 C37 C36 177.4(5) . . . . ?
C9 N3 C17 O2 165.6(4) . . . . ?
C9 N3 C17 O1 -13.0(7) . . . . ?
C9 C7 C8 N1 -176.6(4) . . . . ?
C9 C11 C12 C13 -178.4(4) . . . . ?
C9 C11 C16 C15 179.0(5) . . . . ?
C7 C6 C1 N1 -1.4(4) . . . . ?
C7 C6 C1 C2 178.3(4) . . . . ?
C7 C6 C5 C4 -178.7(4) . . . . ?
C7 C9 C11 C12 -12.5(6) . . . . ?
C7 C9 C11 C16 170.0(4) . . . . ?
C27 C22 C23 C24 1.0(6) . . . . ?
C27 C28 C29 N4 0.1(5) . . . . ?
C27 C26 C25 C24 0.6(7) . . . . ?
C28 C30 C32 C33 -20.4(6) . . . . ?
C28 C30 C32 C37 163.6(4) . . . . ?
C28 C27 C26 C25 -178.8(4) . . . . ?
C8 N1 C1 C6 1.8(5) . . . . ?
C8 N1 C1 C2 -178.0(4) . . . . ?
C38 O4 C39 C40 -65.9(6) . . . . ?
C38 O4 C39 C41 59.3(6) . . . . ?
C38 O4 C39 C42 176.3(5) . . . . ?
C38 N6 C30 C28 65.9(6) . . . . ?
C38 N6 C30 C32 -169.2(4) . . . . ?
C38 N6 C30 C31 -53.8(6) . . . . ?
C23 C22 C27 C28 178.2(4) . . . . ?
C23 C22 C27 C26 -1.2(6) . . . . ?
C23 C24 C25 C26 -0.8(7) . . . . ?
C17 O2 C18 C20 -60.6(6) . . . . ?
C17 O2 C18 C19 63.7(5) . . . . ?
C17 O2 C18 C21 -178.4(5) . . . . ?
C17 N3 C9 C7 68.9(6) . . . . ?
C17 N3 C9 C11 -166.4(4) . . . . ?
C17 N3 C9 C10 -51.1(5) . . . . ?
C11 C9 C7 C6 -68.6(5) . . . . ?
C11 C9 C7 C8 108.0(5) . . . . ?
C11 C12 C13 C14 -0.3(8) . . . . ?
C11 C16 C15 C14 -0.9(9) . . . . ?
C10 C9 C7 C6 173.0(4) . . . . ?
C10 C9 C7 C8 -10.5(6) . . . . ?
C10 C9 C11 C12 107.1(5) . . . . ?
C10 C9 C11 C16 -70.4(5) . . . . ?
C29 N4 C22 C27 1.6(5) . . . . ?
C29 N4 C22 C23 -178.1(4) . . . . ?
C26 C27 C28 C30 -0.8(7) . . . . ?
C26 C27 C28 C29 -179.9(5) . . . . ?
C12 C11 C16 C15 1.5(8) . . . . ?
C12 C13 C14 C15 1.0(8) . . . . ?
C13 C14 C15 C16 -0.4(9) . . . . ?
C32 C30 C28 C27 -70.0(5) . . . . ?
C32 C30 C28 C29 108.9(5) . . . . ?
C32 C33 C34 C35 -1.5(8) . . . . ?
C5 C6 C1 N1 178.9(4) . . . . ?
C5 C6 C1 C2 -1.3(6) . . . . ?
C5 C6 C7 C9 -2.7(7) . . . . ?
C5 C6 C7 C8 -179.8(5) . . . . ?
C5 C4 C3 Cl1 179.2(4) . . . . ?
C5 C4 C3 C2 0.3(7) . . . . ?
C18 O2 C17 O1 1.3(7) . . . . ?
C18 O2 C17 N3 -177.2(4) . . . . ?
C31 C30 C28 C27 171.6(4) . . . . ?
C31 C30 C28 C29 -9.5(6) . . . . ?
C31 C30 C32 C33 99.5(5) . . . . ?
C31 C30 C32 C37 -76.5(5) . . . . ?
C35 C36 C37 C32 -1.9(8) . . . . ?
C33 C32 C37 C36 1.3(8) . . . . ?
C39 O4 C38 O3 12.5(7) . . . . ?
C39 O4 C38 N6 -167.0(4) . . . . ?
C16 C11 C12 C13 -0.9(7) . . . . ?
C36 C35 C34 C33 0.9(9) . . . . ?
C37 C32 C33 C34 0.4(8) . . . . ?
C34 C35 C36 C37 0.8(9) . . . . ?

_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 1.575
_oxdiff_exptl_absorpt_empirical_full_min 0.561
