# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# 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_ta1_2_autored
_database_code_depnum_ccdc_archive 'CCDC 2249599'
loop_
_audit_author_name
_audit_author_address
'Takeshi Hata'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2021-11-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 Br N3'
_chemical_formula_sum            'C9 H6 Br N3'
_chemical_formula_weight         236.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H7Br2N3
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.1549(5)
_cell_length_b                   25.864(2)
_cell_length_c                   8.0655(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.904(11)
_cell_angle_gamma                90
_cell_volume                     848.11(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6423
_cell_measurement_temperature    90
_cell_measurement_theta_max      75.2320
_cell_measurement_theta_min      3.3930
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.439
_exptl_absorpt_coefficient_mu    6.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.019
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2096
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15988
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.537
_diffrn_reflns_theta_min         3.418
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00 -61.00   0.50    5.00    --  -46.45 134.00 148.00   60
  2  ω   -172.00 -98.00   0.50   10.00    -- -102.00  -1.00 135.00  148
  3  ω   -174.00 -81.00   0.50   10.00    -- -102.00-134.00  80.00  186
  4  ω   -168.00 -97.00   0.50   10.00    -- -102.00-132.00 -10.00  142
  5  ω    -16.00  11.00   0.50    5.00    --  -46.45  19.00 -90.00   54
  6  ω    -22.00  27.00   0.50    5.00    --  -46.45  19.00-180.00   98
  7  ω    -27.00  27.00   0.50    5.00    --   46.45 -19.00-180.00  108
  8  ω     38.00  70.00   0.50   10.00    --  104.61 -61.00 -60.00   64
  9  ω     37.00  72.00   0.50   10.00    --  104.61 -61.00  30.00   70
 10  ω     48.00  73.00   0.50   10.00    --  104.61 -61.00 120.00   50
 11  ω    -67.00 -39.00   0.50   10.00    -- -102.00  61.00-180.00   56
 12  ω    -54.00 -28.00   0.50    5.00    --  -46.45 -66.00  36.76   52
 13  ω   -103.00 -72.00   0.50    5.00    --  -46.45 -37.00 -30.00   62
 14  ω    -66.00 -34.00   0.50    5.00    --  -46.45 -37.00  90.00   64
 15  ω   -120.00 -35.00   0.50    5.00    --  -46.45 -37.00-180.00  170
 16  ω   -114.00 -35.00   0.50    5.00    --  -46.45 -37.00-120.00  158
 17  ω    -72.00 -26.00   0.50    5.00    --  -46.45 -72.00 -84.73   92
 18  ω    -93.00 -39.00   0.50    5.00    --  -46.45 125.00  30.00  108
 19  ω    -92.00 -17.00   0.50    5.00    --  -46.45 125.00 -60.00  150
 20  ω   -101.00 -75.00   0.50    5.00    --  -46.45 -67.00 -64.79   52
 21  ω    -52.00 -25.00   0.50    5.00    --  -46.45 -73.00-150.31   54
 22  ω    -67.00 -34.00   0.50    5.00    --  -46.45 -37.00 -30.00   66
 23  ω    -74.00 -36.00   0.50    5.00    --  -46.45 -37.00  30.00   76
 24  ω    -54.00 -28.00   0.50    5.00    --  -46.45 -67.00 -64.79   52
 25  ω    -54.00 -25.00   0.50    5.00    --  -46.45 -73.00  -8.24   58
 26  ω    -53.00 -27.00   0.50    5.00    --  -46.45 -68.00 158.37   52
 27  ω     34.00  61.00   0.50    5.00    --   46.45  57.00  60.00   54
 28  ω     32.00  68.00   0.50    5.00    --   46.45  57.00 150.00   72
 29  ω     32.00  74.00   0.50    5.00    --   46.45  57.00 -90.00   84
 30  ω     25.00  80.00   0.50    5.00    --   46.45  77.00   0.00  110
 31  ω     34.00  77.00   0.50    5.00    --   46.45  57.00-150.00   86
 32  ω     25.00  76.00   0.50    5.00    --   46.45  77.00 150.00  102
 33  ω     85.00 117.00   0.50    5.00    --   46.45  57.00  60.00   64
 34  ω     24.00  76.00   0.50    5.00    --   46.45  77.00 -30.00  104
 35  ω     32.00  70.00   0.50    5.00    --   46.45  57.00 -30.00   76
 36  ω     28.00  72.00   0.50    5.00    --   46.45  68.00  85.67   88
 37  ω   -105.00 -80.00   0.50   10.00    -- -102.00 -74.00  38.82   50
 38  ω   -156.00-130.00   0.50   10.00    -- -102.00 -74.00 -58.91   52
 39  ω   -104.00 -61.00   0.50   10.00    -- -102.00  77.00 120.00   86
 40  ω   -107.00 -80.00   0.50   10.00    -- -102.00 -74.00 -58.91   54
 41  ω   -114.00 -88.00   0.50   10.00    -- -102.00 -48.00 156.76   52
 42  ω   -107.00 -81.00   0.50   10.00    -- -102.00 -72.00 170.67   52
 43  ω   -163.00-137.00   0.50   10.00    -- -102.00 -74.00  38.82   52
 44  ω   -170.00-144.00   0.50   10.00    -- -102.00 -72.00 170.67   52
 45  ω   -108.00 -82.00   0.50   10.00    -- -102.00 -70.00 160.61   52
 46  ω   -136.00 -82.00   0.50   10.00    -- -102.00 -71.00-136.49  108
 47  ω   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00-103.00   52
 48  ω   -168.00-141.00   0.50   10.00    -- -102.00 -79.00-103.00   54
 49  ω   -106.00 -79.00   0.50   10.00    -- -102.00 -76.00  95.18   54
 50  ω   -174.00-127.00   0.50   10.00    -- -102.00 -77.00-120.00   94
 51  ω   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00 -47.87   52
 52  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00  53.90   52
 53  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00-176.21   52
 54  ω   -107.00 -81.00   0.50   10.00    -- -102.00 -72.00-131.36   52
 55  ω   -105.00 -80.00   0.50   10.00    -- -102.00 -74.00 130.64   50
 56  ω   -106.00 -80.00   0.50   10.00    -- -102.00 -75.00 -19.80   52
 57  ω   -114.00 -78.00   0.50   10.00    -- -102.00 -79.00-148.47   72
 58  ω   -127.00 -79.00   0.50   10.00    -- -102.00 -78.00 105.40   96
 59  ω   -140.00 -80.00   0.50   10.00    -- -102.00 -77.00  -5.64  120
 60  ω   -173.00 -78.00   0.50   10.00    -- -102.00 -79.00 -93.66  190
 61  ω   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00 -82.72   52
 62  ω   -107.00 -79.00   0.50   10.00    -- -102.00 -77.00 120.00   56
 63  ω   -175.00-147.00   0.50   10.00    -- -102.00 -74.00 130.64   56
 64  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  47.96   52
 65  ω   -108.00 -82.00   0.50   10.00    -- -102.00 -69.00  66.78   52
 66  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 -25.23   52
 67  ω   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00  29.99   52
 68  ω   -175.00 -82.00   0.50   10.00    -- -102.00 -69.00  -1.64  186
 69  ω   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00 113.61   52
 70  ω   -175.00-135.00   0.50   10.00    -- -102.00 -74.00 142.75   80
 71  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  90.00   52
 72  ω   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00 -32.34   52
 73  ω   -103.00 -78.00   0.50   10.00    -- -102.00  77.00-150.00   50
 74  ω   -105.00 -78.00   0.50   10.00    -- -102.00 -80.00   3.08   54
 75  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00 -58.88   52
 76  ω   -174.00 -80.00   0.50   10.00    -- -102.00 -74.00 -16.14  188
 77  ω   -130.00 -80.00   0.50   10.00    -- -102.00 -75.00 -42.04  100
 78  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  35.35   52
 79  ω   -160.00 -82.00   0.50   10.00    -- -102.00 -69.00  71.42  156
 80  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00  16.65   52
 81  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 154.17   52
 82  ω   -173.00-128.00   0.50   10.00    -- -102.00 -76.00 154.17   90
 83  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 137.95   52
 84  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 159.53   52
 85  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  22.08   52
 86  ω   -144.00-118.00   0.50   10.00    -- -102.00 -76.00  16.65   52
 87  ω   -173.00 -80.00   0.50   10.00    -- -102.00 -75.00 113.04  186
 88  ω   -170.00 -79.00   0.50   10.00    -- -102.00 -76.00 -71.68  182
 89  ω   -138.00 -88.00   0.50   10.00    -- -102.00 -53.00-102.91  100
 90  ω   -104.00 -78.00   0.50   10.00    -- -102.00 -79.00-110.93   52
 91  ω   -175.00 -81.00   0.50   10.00    -- -102.00 -72.00  61.09  188
 92  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00 -30.00   52
 93  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -77.00  60.00   52
 94  ω   -106.00 -79.00   0.50   10.00    -- -102.00 -77.00-120.00   54
 95  ω   -111.00 -79.00   0.50   10.00    -- -102.00 -77.00-138.93   64
 96  ω   -105.00 -79.00   0.50   10.00    -- -102.00 -76.00 125.40   52
 97  ω   -106.00 -80.00   0.50   10.00    -- -102.00 -74.00 142.75   52
 98  ω   -106.00 -80.00   0.50   10.00    -- -102.00 -74.00-162.47   52
 99  ω     41.00  89.00   0.50   10.00    --  104.61 -94.00-120.00   96
100  ω     34.00  86.00   0.50   10.00    --  104.61 -94.00 -30.00  104
101  ω     54.00 104.00   0.50   10.00    --  104.61 -94.00 -90.00  100
102  ω     62.00 105.00   0.50   10.00    --  104.61 -94.00-180.00   86
103  ω     33.00  58.00   0.50   10.00    --  104.61 -94.00-180.00   50
104  ω     32.00  94.00   0.50   10.00    --  104.61 -94.00   0.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0625900000
_diffrn_orient_matrix_UB_12      -0.0247426000
_diffrn_orient_matrix_UB_13      -0.1774847000
_diffrn_orient_matrix_UB_21      -0.0271802000
_diffrn_orient_matrix_UB_22      0.0542449000
_diffrn_orient_matrix_UB_23      -0.0806073000
_diffrn_orient_matrix_UB_31      0.3724234000
_diffrn_orient_matrix_UB_32      -0.0000557000
_diffrn_orient_matrix_UB_33      0.0043847000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1278
_reflns_number_total             1666
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         3.611
_refine_diff_density_min         -1.513
_refine_diff_density_rms         0.322
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.311
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1433
_refine_ls_R_factor_gt           0.1178
_refine_ls_restrained_S_all      1.311
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2942
_refine_ls_wR_factor_ref         0.3278
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00B), C00C(H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.5459(2) 0.44942(3) 0.15860(11) 0.0483(6) Uani 1 1 d . . . . .
N002 N 0.3720(18) 0.3143(3) 0.3577(9) 0.0460(17) Uani 1 1 d . . . . .
N003 N 0.5727(17) 0.3396(3) 0.1470(9) 0.052(2) Uani 1 1 d . . . . .
N4 N 0.5052(19) 0.2976(3) 0.2279(10) 0.0514(19) Uani 1 1 d . . . . .
C005 C 0.153(2) 0.3336(3) 0.5893(12) 0.048(2) Uani 1 1 d . . . . .
C006 C 0.3490(19) 0.3664(3) 0.3644(12) 0.0416(18) Uani 1 1 d . . . . .
C007 C 0.481(2) 0.3819(3) 0.2283(10) 0.0424(19) Uani 1 1 d . . . . .
C008 C 0.136(2) 0.4275(3) 0.5722(12) 0.046(2) Uani 1 1 d . . . . .
H008 H 0.174487 0.459054 0.519140 0.055 Uiso 1 1 calc R U . . .
C009 C 0.003(2) 0.4272(4) 0.7185(13) 0.048(2) Uani 1 1 d . . . . .
H009 H -0.052244 0.459215 0.763192 0.058 Uiso 1 1 calc R U . . .
C00A C 0.209(2) 0.3804(3) 0.5079(11) 0.045(2) Uani 1 1 d . . . . .
C00B C -0.050(2) 0.3827(4) 0.7989(13) 0.048(2) Uani 1 1 d . . . . .
H00B H -0.138668 0.384066 0.898443 0.058 Uiso 1 1 calc R U . . .
C00C C 0.026(2) 0.3344(4) 0.7343(12) 0.049(2) Uani 1 1 d . . . . .
H00C H -0.010074 0.303162 0.789754 0.058 Uiso 1 1 calc R U . . .
C00D C 0.254(2) 0.2872(3) 0.4942(11) 0.047(2) Uani 1 1 d . . . . .
H00A H 0.430500 0.266729 0.566154 0.057 Uiso 1 1 calc R U . . .
H00D H 0.064421 0.264407 0.449096 0.057 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
Br01 C007 1.872(9) . ?
N002 N4 1.353(10) . ?
N002 C006 1.352(10) . ?
N002 C00D 1.472(10) . ?
N003 N4 1.329(11) . ?
N003 C007 1.368(11) . ?
C005 C00A 1.420(12) . ?
C005 C00C 1.380(15) . ?
C005 C00D 1.529(12) . ?
C006 C007 1.383(12) . ?
C006 C00A 1.445(13) . ?
C008 H008 0.9500 . ?
C008 C009 1.402(14) . ?
C008 C00A 1.383(12) . ?
C009 H009 0.9500 . ?
C009 C00B 1.361(13) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.413(13) . ?
C00C H00C 0.9500 . ?
C00D H00A 0.9900 . ?
C00D H00D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 N002 C00D 132.7(7) . . ?
C006 N002 N4 113.2(7) . . ?
C006 N002 C00D 114.1(7) . . ?
N4 N003 C007 108.1(7) . . ?
N003 N4 N002 106.2(7) . . ?
C00A C005 C00D 110.5(8) . . ?
C00C C005 C00A 120.4(8) . . ?
C00C C005 C00D 129.1(8) . . ?
N002 C006 C007 102.3(7) . . ?
N002 C006 C00A 109.0(8) . . ?
C007 C006 C00A 148.7(8) . . ?
N003 C007 Br01 121.9(6) . . ?
N003 C007 C006 110.2(8) . . ?
C006 C007 Br01 127.8(6) . . ?
C009 C008 H008 121.1 . . ?
C00A C008 H008 121.1 . . ?
C00A C008 C009 117.7(8) . . ?
C008 C009 H009 118.8 . . ?
C00B C009 C008 122.5(9) . . ?
C00B C009 H009 118.8 . . ?
C005 C00A C006 106.7(8) . . ?
C008 C00A C005 120.6(9) . . ?
C008 C00A C006 132.6(9) . . ?
C009 C00B H00B 120.0 . . ?
C009 C00B C00C 120.1(9) . . ?
C00C C00B H00B 120.0 . . ?
C005 C00C C00B 118.7(8) . . ?
C005 C00C H00C 120.6 . . ?
C00B C00C H00C 120.6 . . ?
N002 C00D C005 99.7(6) . . ?
N002 C00D H00A 111.8 . . ?
N002 C00D H00D 111.8 . . ?
C005 C00D H00A 111.8 . . ?
C005 C00D H00D 111.8 . . ?
H00A C00D H00D 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
N002 C006 C007 Br01 -177.9(6) . . . . ?
N002 C006 C007 N003 0.5(9) . . . . ?
N002 C006 C00A C005 0.9(9) . . . . ?
N002 C006 C00A C008 179.4(9) . . . . ?
N4 N002 C006 C007 -0.4(9) . . . . ?
N4 N002 C006 C00A -179.2(7) . . . . ?
N4 N002 C00D C005 178.3(8) . . . . ?
N4 N003 C007 Br01 178.1(5) . . . . ?
N4 N003 C007 C006 -0.4(10) . . . . ?
C006 N002 N4 N003 0.2(9) . . . . ?
C006 N002 C00D C005 -0.3(9) . . . . ?
C007 N003 N4 N002 0.2(9) . . . . ?
C007 C006 C00A C005 -176.9(13) . . . . ?
C007 C006 C00A C008 2(2) . . . . ?
C008 C009 C00B C00C -0.7(15) . . . . ?
C009 C008 C00A C005 -0.7(14) . . . . ?
C009 C008 C00A C006 -179.0(9) . . . . ?
C009 C00B C00C C005 -0.2(14) . . . . ?
C00A C005 C00C C00B 0.6(14) . . . . ?
C00A C005 C00D N002 0.9(9) . . . . ?
C00A C006 C007 Br01 0.0(19) . . . . ?
C00A C006 C007 N003 178.4(12) . . . . ?
C00A C008 C009 C00B 1.1(15) . . . . ?
C00C C005 C00A C006 178.6(8) . . . . ?
C00C C005 C00A C008 -0.1(14) . . . . ?
C00C C005 C00D N002 -178.8(9) . . . . ?
C00D N002 N4 N003 -178.5(8) . . . . ?
C00D N002 C006 C007 178.5(7) . . . . ?
C00D N002 C006 C00A -0.3(9) . . . . ?
C00D C005 C00A C006 -1.2(10) . . . . ?
C00D C005 C00A C008 -179.8(7) . . . . ?
C00D C005 C00C C00B -179.8(8) . . . . ?

_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 8.566
_oxdiff_exptl_absorpt_empirical_full_min 0.160
####################################################################### 
# 
# 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_kk-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2249600'
loop_
_audit_author_name
_audit_author_address
'Takeshi Hata'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-01-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N3 O'
_chemical_formula_sum            'C13 H11 N3 O'
_chemical_formula_weight         225.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0182(5)
_cell_length_b                   13.7411(4)
_cell_length_c                   9.4416(5)
_cell_angle_alpha                90
_cell_angle_beta                 118.495(7)
_cell_angle_gamma                90
_cell_volume                     1028.27(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2695
_cell_measurement_temperature    90
_cell_measurement_theta_max      74.9020
_cell_measurement_theta_min      6.2220
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4567
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.398
_diffrn_reflns_theta_min         5.585
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    124.00 166.00   0.50   30.00    --  105.67 105.00 -48.00   84
  2  ω     85.00 178.00   0.50   30.00    --  105.67  39.00  96.00  186
  3  ω     39.00 104.00   0.50   30.00    --  105.67 -89.00 106.00  130
  4  ω     94.00 121.00   0.50   30.00    --  105.67 105.00 -48.00   54
  5  ω    -28.00  22.00   0.50   40.00    --  -41.39  37.00-150.00  100
  6  ω    -10.00  16.00   0.50   40.00    --  -41.39  19.00 -30.00   52
  7  ω      5.00  31.00   0.50   40.00    --  -41.39  19.00  30.00   52
  8  ω    -23.00  72.00   0.50   40.00    --   41.39 -89.00 106.00  190
  9  ω    -56.00 -31.00   0.50   30.00    -- -102.00  61.00 150.00   50
 10  ω    -60.00 -31.00   0.50   30.00    -- -102.00  61.00  90.00   58
 11  ω    -85.00 -43.00   0.50   30.00    -- -102.00  77.00 -30.00   84
 12  ω   -124.00 -86.00   0.50   30.00    -- -102.00 -94.00-180.00   76
 13  ω     46.00  72.00   0.50   30.00    --  105.67 -61.00 -30.00   52
 14  ω     40.00  77.00   0.50   30.00    --  105.67 -61.00 150.00   74
 15  ω     35.00  62.00   0.50   30.00    --  105.67 -45.00 150.00   54
 16  ω     31.00  62.00   0.50   30.00    --  105.67 -45.00 -60.00   62
 17  ω    131.00 178.00   0.50   30.00    --  105.67  61.00 -90.00   94
 18  ω     82.00 124.00   0.50   30.00    --  105.67  61.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1045350000
_diffrn_orient_matrix_UB_12      0.0171590000
_diffrn_orient_matrix_UB_13      -0.0876376000
_diffrn_orient_matrix_UB_21      -0.0587924000
_diffrn_orient_matrix_UB_22      0.1068652000
_diffrn_orient_matrix_UB_23      -0.0299920000
_diffrn_orient_matrix_UB_31      0.1527913000
_diffrn_orient_matrix_UB_32      0.0292973000
_diffrn_orient_matrix_UB_33      0.1609786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1673
_reflns_number_total             1928
_reflns_odcompleteness_completeness 95.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.054
_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)+(0.0720P)²+0.2346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1159
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C15(H15)
;
_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
O17 O 0.77556(13) 0.64744(7) 0.43806(13) 0.0317(3) Uani 1 1 d . . . . .
N1 N 0.06928(16) 0.61435(8) 0.12846(16) 0.0307(3) Uani 1 1 d . . . . .
N13 N -0.00492(18) 0.61051(9) -0.03235(16) 0.0383(4) Uani 1 1 d . . . . .
N12 N 0.11808(19) 0.61216(9) -0.07174(15) 0.0385(4) Uani 1 1 d . . . . .
C5 C 0.34505(17) 0.62181(9) 0.37019(17) 0.0226(3) Uani 1 1 d . . . . .
C14 C 0.61020(18) 0.63552(9) 0.61668(17) 0.0252(3) Uani 1 1 d . . . . .
H14 H 0.728628 0.646183 0.670097 0.030 Uiso 1 1 calc R U . . .
C6 C 0.52050(17) 0.63972(9) 0.44843(17) 0.0227(3) Uani 1 1 d . . . . .
C4 C 0.26420(18) 0.59918(9) 0.46220(18) 0.0251(3) Uani 1 1 d . . . . .
C11 C 0.24029(18) 0.61932(9) 0.19542(18) 0.0251(3) Uani 1 1 d . . . . .
C16 C 0.35686(19) 0.59811(10) 0.62930(18) 0.0280(3) Uani 1 1 d . . . . .
H16 H 0.301650 0.584934 0.691366 0.034 Uiso 1 1 calc R U . . .
C7 C 0.62324(17) 0.66135(9) 0.36466(17) 0.0250(3) Uani 1 1 d . . . . .
C15 C 0.52946(19) 0.61609(10) 0.70673(17) 0.0280(3) Uani 1 1 d . . . . .
H15 H 0.591770 0.615050 0.821063 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2691(2) 0.61800(10) 0.06446(17) 0.0297(3) Uani 1 1 d . . . . .
C3 C 0.08130(18) 0.56786(10) 0.37884(19) 0.0302(3) Uani 1 1 d . . . . .
H3A H 0.031956 0.581588 0.450583 0.036 Uiso 1 1 calc R U . . .
H3B H 0.075666 0.496696 0.360589 0.036 Uiso 1 1 calc R U . . .
C8 C 0.54644(18) 0.70195(10) 0.19584(17) 0.0275(3) Uani 1 1 d . . . . .
H8A H 0.638462 0.722765 0.173671 0.033 Uiso 1 1 calc R U . . .
H8B H 0.479423 0.760398 0.189698 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4325(2) 0.62986(11) 0.06466(18) 0.0328(4) Uani 1 1 d . . . . .
H9A H 0.412201 0.653849 -0.041998 0.039 Uiso 1 1 calc R U . . .
H9B H 0.489818 0.565996 0.084015 0.039 Uiso 1 1 calc R U . . .
C2 C -0.02343(19) 0.61852(11) 0.2189(2) 0.0346(4) Uani 1 1 d . . . . .
H2A H -0.133905 0.585652 0.158186 0.042 Uiso 1 1 calc R U . . .
H2B H -0.043710 0.687087 0.236953 0.042 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
O17 C7 1.2229(16) . ?
N1 N13 1.3366(19) . ?
N1 C11 1.3610(19) . ?
N1 C2 1.453(2) . ?
N13 N12 1.328(2) . ?
N12 C10 1.358(2) . ?
C5 C6 1.4123(19) . ?
C5 C4 1.4097(19) . ?
C5 C11 1.459(2) . ?
C14 C6 1.398(2) . ?
C14 C15 1.384(2) . ?
C6 C7 1.5071(19) . ?
C4 C16 1.389(2) . ?
C4 C3 1.512(2) . ?
C11 C10 1.379(2) . ?
C16 C15 1.390(2) . ?
C7 C8 1.509(2) . ?
C10 C9 1.482(2) . ?
C3 C2 1.515(2) . ?
C8 C9 1.535(2) . ?

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
N13 N1 C11 111.83(13) . . ?
N13 N1 C2 123.53(13) . . ?
C11 N1 C2 124.55(13) . . ?
N12 N13 N1 106.57(12) . . ?
N13 N12 C10 109.28(13) . . ?
C6 C5 C11 123.71(13) . . ?
C4 C5 C6 119.73(13) . . ?
C4 C5 C11 116.46(13) . . ?
C15 C14 C6 121.14(13) . . ?
C5 C6 C7 125.15(13) . . ?
C14 C6 C5 118.92(13) . . ?
C14 C6 C7 115.92(12) . . ?
C5 C4 C3 119.90(13) . . ?
C16 C4 C5 119.64(13) . . ?
C16 C4 C3 120.26(13) . . ?
N1 C11 C5 120.35(13) . . ?
N1 C11 C10 103.83(13) . . ?
C10 C11 C5 135.79(14) . . ?
C4 C16 C15 120.75(13) . . ?
O17 C7 C6 118.52(13) . . ?
O17 C7 C8 118.79(12) . . ?
C6 C7 C8 122.67(12) . . ?
C14 C15 C16 119.77(13) . . ?
N12 C10 C11 108.49(14) . . ?
N12 C10 C9 123.72(14) . . ?
C11 C10 C9 127.57(14) . . ?
C4 C3 C2 113.23(12) . . ?
C7 C8 C9 114.00(11) . . ?
C10 C9 C8 110.74(12) . . ?
N1 C2 C3 107.91(12) . . ?

_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 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.822
####################################################################### 
# 
# 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_kk-x_auto
_database_code_depnum_ccdc_archive 'CCDC 2249601'
loop_
_audit_author_name
_audit_author_address
'Takeshi Hata'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-04-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 N4'
_chemical_formula_sum            'C16 H12 N4'
_chemical_formula_weight         260.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

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

_cell_length_a                   9.3536(3)
_cell_length_b                   10.4366(3)
_cell_length_c                   13.3657(4)
_cell_angle_alpha                78.907(2)
_cell_angle_beta                 79.540(3)
_cell_angle_gamma                76.410(3)
_cell_volume                     1231.75(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11432
_cell_measurement_temperature    90
_cell_measurement_theta_max      73.6710
_cell_measurement_theta_min      4.8670
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.414
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.017
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32072
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.363
_diffrn_reflns_theta_min         3.405
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -61.00   0.50    1.01    --  -41.30 -65.00  93.00   96
  2  ω     20.00  47.00   0.50    1.01    --   41.30  65.00-131.00   54
  3  ω     75.00 100.00   0.50    1.01    --   41.30  65.00-131.00   50
  4  ω   -131.00-100.00   0.50    4.04    -- -104.00 -65.00  93.00   62
  5  ω   -160.00-134.00   0.50    4.04    -- -104.00 -65.00  93.00   52
  6  ω    -63.00 -32.00   0.50    4.04    -- -104.00  65.00-131.00   62
  7  ω    136.00 163.00   0.50    4.04    --  104.88  65.00-131.00   54
  8  ω    102.00 128.00   0.50    4.04    --  104.88  65.00-131.00   52
  9  ω   -113.00 -72.00   0.50    1.01    --  -41.30 -37.00 -90.00   82
 10  ω    -64.00 -21.00   0.50    1.01    --  -41.30 -37.00 -90.00   86
 11  ω   -114.00 -71.00   0.50    1.01    --  -41.30 -57.00-180.00   86
 12  ω    -78.00 -18.00   0.50    1.01    --  -41.30 -37.00  30.00  120
 13  ω    -65.00   7.00   0.50    1.01    --  -41.30  65.00-131.00  144
 14  ω   -119.00 -80.00   0.50    1.01    --  -41.30 -37.00  30.00   78
 15  ω    -55.00 -26.00   0.50    1.01    --  -41.30 -65.00  93.00   58
 16  ω    -67.00 -18.00   0.50    1.01    --  -41.30 -57.00-180.00   98
 17  ω    -95.00 -18.00   0.50    1.01    --  -41.30 125.00   0.00  154
 18  ω    -31.00  29.00   0.50    1.01    --   41.30 -65.00  93.00  120
 19  ω     35.00  61.00   0.50    1.01    --   41.30 -65.00  93.00   52
 20  ω    -37.00 -11.00   0.50    1.01    --  -44.00 -86.00-157.69   52
 21  ω     16.00  41.00   0.50    1.01    --   44.00  81.00 114.05   50
 22  ω     18.00  54.00   0.50    1.01    --   44.00  71.00 -47.14   72
 23  ω     14.00  41.00   0.50    1.01    --   44.00  85.00  -3.50   54
 24  ω     15.00  42.00   0.50    1.01    --   48.00  87.00 128.13   54
 25  ω     13.00  38.00   0.50    1.01    --   48.00  91.00 -53.18   50
 26  ω     13.00  40.00   0.50    1.01    --   48.00  92.00-165.22   54
 27  ω     12.00  37.00   0.50    1.01    --   48.00  92.00  24.04   50
 28  ω     16.00  41.00   0.50    1.01    --   48.00  84.00 173.83   50
 29  ω    106.00 132.00   0.50    1.01    --   60.00  73.00 -21.67   52
 30  ω     33.00  59.00   0.50    1.01    --   60.00  73.00 -21.67   52
 31  ω     34.00  60.00   0.50    1.01    --   60.00  76.00 167.63   52
 32  ω     34.00  60.00   0.50    1.01    --   60.00  75.00-164.30   52
 33  ω     32.00  71.00   0.50    1.01    --   60.00  77.00  26.83   78
 34  ω    107.00 133.00   0.50    1.01    --   60.00  77.00  26.83   52
 35  ω     32.00  60.00   0.50    1.01    --   60.00  76.00 -61.06   56
 36  ω     35.00  60.00   0.50    1.01    --   64.00  77.00-112.52   50
 37  ω    -68.00 -42.00   0.50    1.01    --  -68.00 -73.00  78.36   52
 38  ω     39.00  65.00   0.50    1.01    --   68.00  77.00  54.90   52
 39  ω    -71.00 -45.00   0.50    1.01    --  -72.00 -71.00 116.47   52
 40  ω    -72.00 -46.00   0.50    1.01    --  -72.00 -71.00  97.64   52
 41  ω    -76.00 -50.00   0.50    4.04    --  -76.00 -74.00 -94.31   52
 42  ω    -75.00 -50.00   0.50    4.04    --  -76.00 -69.00 -31.26   50
 43  ω    -73.00 -48.00   0.50    4.04    --  -76.00 -75.00 -59.48   50
 44  ω   -146.00-120.00   0.50    4.04    --  -76.00 -75.00 -59.48   52
 45  ω    -79.00 -53.00   0.50    4.04    --  -80.00 -74.00-131.69   52
 46  ω    -79.00 -53.00   0.50    4.04    --  -80.00 -74.00 173.41   52
 47  ω    -81.00 -56.00   0.50    4.04    --  -80.00 -67.00  37.23   50
 48  ω    -81.00 -55.00   0.50    4.04    --  -80.00 -69.00  87.84   52
 49  ω    -78.00 -53.00   0.50    4.04    --  -80.00 -72.00   7.13   50
 50  ω   -141.00-115.00   0.50    4.04    --  -80.00 -72.00   7.13   52
 51  ω    -85.00 -56.00   0.50    4.04    --  -80.00 -67.00 132.23   58
 52  ω    -83.00 -53.00   0.50    4.04    --  -80.00 -73.00  60.33   60
 53  ω    -83.00 -57.00   0.50    4.04    --  -84.00 -74.00-144.26   52
 54  ω   -158.00-121.00   0.50    4.04    --  -84.00 -72.00 125.27   74
 55  ω    -83.00 -57.00   0.50    4.04    --  -84.00 -72.00 125.27   52
 56  ω    -82.00 -55.00   0.50    4.04    --  -84.00 -76.00-158.83   54
 57  ω    -82.00 -57.00   0.50    4.04    --  -84.00 -72.00-119.15   50
 58  ω    -89.00 -61.00   0.50    4.04    --  -88.00 -73.00  86.54   56
 59  ω     62.00  88.00   0.50    4.04    --   88.00  74.00 129.62   52
 60  ω    -89.00 -63.00   0.50    4.04    --  -92.00 -76.00  -1.76   52
 61  ω    -94.00 -68.00   0.50    4.04    --  -92.00 -65.00 -76.16   52
 62  ω    -91.00 -65.00   0.50    4.04    --  -92.00 -72.00 136.33   52
 63  ω    -94.00 -67.00   0.50    4.04    --  -92.00 -67.00   3.22   54
 64  ω   -149.00-123.00   0.50    4.04    --  -92.00 -67.00   3.22   52
 65  ω   -124.00 -68.00   0.50    4.04    --  -92.00 -65.00  32.73  112
 66  ω   -161.00-134.00   0.50    4.04    --  -92.00 -65.00  32.73   54
 67  ω    -95.00 -69.00   0.50    4.04    --  -92.00 -62.00 -42.88   52
 68  ω   -166.00 -67.00   0.50    4.04    --  -92.00 -68.00 168.09  198
 69  ω   -168.00 -68.00   0.50    4.04    --  -96.00 -74.00  29.57  200
 70  ω   -163.00-120.00   0.50    4.04    --  -96.00 -76.00 -70.23   86
 71  ω   -103.00 -71.00   0.50    4.04    --  -96.00 -66.00 146.78   64
 72  ω   -166.00-139.00   0.50    4.04    --  -96.00 -57.00  55.39   54
 73  ω   -158.00-108.00   0.50    4.04    --  -96.00 -66.00 146.78  100
 74  ω   -151.00 -72.00   0.50    4.04    --  -96.00 -64.00 -97.92  158
 75  ω   -113.00 -67.00   0.50    4.04    --  -96.00 -76.00 -70.23   92
 76  ω   -103.00 -73.00   0.50    4.04    --  -96.00 -57.00  55.39   60
 77  ω    -96.00 -71.00   0.50    4.04    -- -100.00 -77.00 172.83   50
 78  ω   -152.00-126.00   0.50    4.04    -- -100.00 -77.00 172.83   52
 79  ω   -171.00 -72.00   0.50    4.04    -- -100.00 -77.00-134.77  198
 80  ω   -100.00 -73.00   0.50    4.04    -- -100.00 -74.00 135.97   54
 81  ω   -171.00-116.00   0.50    4.04    -- -100.00 -74.00 135.97  110
 82  ω   -131.00 -74.00   0.50    4.04    -- -100.00 -69.00-161.51  114
 83  ω   -138.00 -71.00   0.50    4.04    -- -100.00 -77.00  -0.60  134
 84  ω   -109.00 -30.00   0.50    4.04    -- -104.00 125.00   0.00  158
 85  ω   -100.00 -75.00   0.50    4.04    -- -104.00 -76.00-160.72   50
 86  ω   -155.00-129.00   0.50    4.04    -- -104.00 -76.00-160.72   52
 87  ω    -59.00 -32.00   0.50    4.04    -- -104.00  77.00  30.00   54
 88  ω    -96.00 -62.00   0.50    4.04    -- -104.00  77.00  30.00   68
 89  ω   -170.00 -80.00   0.50    4.04    -- -104.00 -66.00  67.63  180
 90  ω   -171.00 -75.00   0.50    4.04    -- -104.00 -76.00 -20.05  192
 91  ω   -101.00 -76.00   0.50    4.04    -- -104.00 -74.00-102.33   50
 92  ω   -175.00 -76.00   0.50    4.04    -- -104.00 -74.00 -32.49  198
 93  ω   -134.00 -80.00   0.50    4.04    -- -104.00 -72.00-115.83  108
 94  ω   -123.00 -81.00   0.50    4.04    -- -104.00 -67.00 101.97   84
 95  ω   -174.00-128.00   0.50    4.04    -- -104.00 -67.00 101.97   92
 96  ω     35.00  72.00   0.50    4.04    --  104.88 -61.00 120.00   74
 97  ω     50.00  88.00   0.50    4.04    --  104.88 -77.00-120.00   76
 98  ω     59.00 103.00   0.50    4.04    --  104.88 -94.00 120.00   88
 99  ω     72.00  98.00   0.50    4.04    --  104.88 -94.00 -30.00   52
100  ω     32.00  69.00   0.50    4.04    --  104.88 -94.00 -30.00   74
101  ω     69.00 102.00   0.50    4.04    --  104.88 -94.00-120.00   66
102  ω     73.00 111.00   0.50    4.04    --  104.88-125.00-150.00   76
103  ω     41.00 103.00   0.50    4.04    --  104.88 -77.00-180.00  124
104  ω    127.00 173.00   0.50    4.04    --  104.88  77.00 120.00   92
105  ω     78.00 123.00   0.50    4.04    --  104.88  77.00 120.00   90
106  ω     40.00  66.00   0.50    4.04    --  104.88 -94.00-120.00   52
107  ω     31.00 107.00   0.50    4.04    --  104.88-106.00  90.11  152
108  ω     30.00  55.00   0.50    4.04    --  104.88 -45.00 -30.00   50
109  ω     32.00  80.00   0.50    4.04    --  104.88 -65.00  93.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0129440000
_diffrn_orient_matrix_UB_12      0.1234849000
_diffrn_orient_matrix_UB_13      -0.0847479000
_diffrn_orient_matrix_UB_21      0.1362591000
_diffrn_orient_matrix_UB_22      0.0354477000
_diffrn_orient_matrix_UB_23      0.0293101000
_diffrn_orient_matrix_UB_31      0.1028424000
_diffrn_orient_matrix_UB_32      -0.0844796000
_diffrn_orient_matrix_UB_33      -0.0777341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4163
_reflns_number_total             4815
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     528
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.078
_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)+(0.0556P)²+0.8636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1434
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.002 within 2A
C26 \\sim C27 \\sim C9 \\sim C10: within 2A with sigma of 0.001 and sigma for
terminal atoms of 0.002 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C27(H27A,H27B), C10(H10A,H10B), C26(H26A,H26B)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C40(H40), C4(H4), C32(H32), C29(H29), C7(H7), C31(H31), C5(H5),
 C15(H15), C30(H30), C39(H39), C6(H6), C17(H17), C37(H37), C16(H16), C38(H38)
;
_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
N28 N 0.6544(2) 0.57739(17) 0.84224(13) 0.0319(4) Uani 1 1 d . U . . .
N11 N 0.7551(2) 0.70672(17) 0.89103(14) 0.0338(4) Uani 1 1 d . U . . .
N20 N 0.5875(2) 0.51351(18) 0.79169(14) 0.0355(4) Uani 1 1 d . U . . .
N25 N 0.3167(2) 0.78814(17) 0.59945(14) 0.0349(4) Uani 1 1 d . U . . .
N26 N 0.1246(2) 0.91551(17) 0.65253(13) 0.0339(4) Uani 1 1 d . U . . .
N22 N 0.0004(2) 0.97757(19) 0.70619(14) 0.0385(4) Uani 1 1 d . U . . .
N12 N 0.6870(2) 0.69789(18) 0.81210(14) 0.0375(4) Uani 1 1 d . U . . .
N27 N 0.2055(2) 0.79420(19) 0.67985(14) 0.0398(4) Uani 1 1 d . U . . .
C33 C 0.4233(2) 0.9025(2) 0.43740(15) 0.0291(4) Uani 1 1 d . U . . .
C3 C 0.8348(2) 0.59775(19) 1.05520(15) 0.0282(4) Uani 1 1 d . U . . .
C2 C 0.7646(2) 0.59942(19) 0.96657(15) 0.0286(4) Uani 1 1 d . U . . .
C34 C 0.3074(2) 0.8973(2) 0.52564(16) 0.0302(4) Uani 1 1 d . U . . .
C1 C 0.6976(2) 0.51081(19) 0.93461(15) 0.0278(4) Uani 1 1 d . U . . .
C36 C 0.0749(2) 1.1091(2) 0.55058(15) 0.0290(4) Uani 1 1 d . U . . .
C35 C 0.1778(2) 0.9843(2) 0.56025(15) 0.0293(4) Uani 1 1 d . U . . .
C19 C 0.6552(2) 0.3862(2) 0.94738(15) 0.0278(4) Uani 1 1 d . U . . .
C14 C 0.5882(2) 0.3956(2) 0.85742(15) 0.0311(4) Uani 1 1 d . U . . .
C18 C 0.6692(2) 0.2690(2) 1.01937(16) 0.0317(4) Uani 1 1 d . U . . .
H18 H 0.712691 0.262439 1.079584 0.038 Uiso 1 1 calc R U . . .
C28 C 0.5511(2) 0.7994(2) 0.43800(17) 0.0330(5) Uani 1 1 d . U . . .
C40 C 0.0593(2) 1.2276(2) 0.47946(16) 0.0330(5) Uani 1 1 d . U . . .
H40 H 0.127659 1.236068 0.417810 0.040 Uiso 1 1 calc R U . . .
C21 C -0.0294(2) 1.0971(2) 0.64243(16) 0.0336(5) Uani 1 1 d . U . . .
C8 C 0.9096(2) 0.7013(2) 1.05273(17) 0.0327(5) Uani 1 1 d . U . . .
C4 C 0.8323(2) 0.4965(2) 1.13938(16) 0.0325(5) Uani 1 1 d . U . . .
H4 H 0.779685 0.428338 1.141089 0.039 Uiso 1 1 calc R U . . .
C32 C 0.4131(2) 1.0079(2) 0.35560(16) 0.0327(5) Uani 1 1 d . U . . .
H32 H 0.325842 1.076307 0.354803 0.039 Uiso 1 1 calc R U . . .
C29 C 0.6647(2) 0.8050(2) 0.35479(18) 0.0373(5) Uani 1 1 d . U . . .
H29 H 0.750008 0.734535 0.352864 0.045 Uiso 1 1 calc R U . . .
C7 C 0.9795(2) 0.6993(2) 1.13716(18) 0.0356(5) Uani 1 1 d . U . . .
H7 H 1.027748 0.769553 1.137961 0.043 Uiso 1 1 calc R U . . .
C31 C 0.5287(2) 1.0137(2) 0.27595(16) 0.0353(5) Uani 1 1 d . U . . .
H31 H 0.522480 1.087363 0.221549 0.042 Uiso 1 1 calc R U . . .
C5 C 0.9059(2) 0.4943(2) 1.22077(17) 0.0351(5) Uani 1 1 d . U . . .
H5 H 0.906528 0.423476 1.277315 0.042 Uiso 1 1 calc R U . . .
C15 C 0.5327(2) 0.2874(2) 0.84209(17) 0.0359(5) Uani 1 1 d . U . . .
H15 H 0.484529 0.293501 0.784090 0.043 Uiso 1 1 calc R U . . .
C30 C 0.6549(3) 0.9112(2) 0.27518(17) 0.0368(5) Uani 1 1 d . U . . .
H30 H 0.734265 0.914602 0.219815 0.044 Uiso 1 1 calc R U . . .
C39 C -0.0577(3) 1.3318(2) 0.50109(18) 0.0382(5) Uani 1 1 d . U . . .
H39 H -0.069055 1.413323 0.454324 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9792(2) 0.5966(2) 1.21937(17) 0.0366(5) Uani 1 1 d . U . . .
H6 H 1.029346 0.595578 1.275373 0.044 Uiso 1 1 calc R U . . .
C17 C 0.6184(3) 0.1632(2) 1.00088(17) 0.0372(5) Uani 1 1 d . U . . .
H17 H 0.629551 0.081972 1.047986 0.045 Uiso 1 1 calc R U . . .
C37 C -0.1489(3) 1.2039(2) 0.66180(18) 0.0389(5) Uani 1 1 d . U . . .
H37 H -0.219812 1.196454 0.722152 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5501(3) 0.1739(2) 0.91288(17) 0.0387(5) Uani 1 1 d . U . . .
H16 H 0.515225 0.099600 0.902639 0.046 Uiso 1 1 calc R U . . .
C38 C -0.1605(3) 1.3184(2) 0.59195(18) 0.0404(5) Uani 1 1 d . U . . .
H38 H -0.240236 1.391382 0.604796 0.048 Uiso 1 1 calc R U . . .
C9 C 0.9180(3) 0.8046(2) 0.9578(2) 0.0436(5) Uani 1 1 d . U . . .
H9A H 0.923172 0.889347 0.978433 0.052 Uiso 1 1 calc R U . . .
H9B H 1.011575 0.775765 0.912256 0.052 Uiso 1 1 calc R U . . .
C27 C 0.5647(3) 0.6929(2) 0.5310(2) 0.0448(5) Uani 1 1 d . U . . .
H27A H 0.625433 0.609454 0.508301 0.054 Uiso 1 1 calc R U . . .
H27B H 0.619465 0.719692 0.577639 0.054 Uiso 1 1 calc R U . . .
C10 C 0.7932(3) 0.8308(2) 0.8979(2) 0.0448(5) Uani 1 1 d . U . . .
H10A H 0.705948 0.889158 0.931717 0.054 Uiso 1 1 calc R U . . .
H10B H 0.821651 0.877484 0.827854 0.054 Uiso 1 1 calc R U . . .
C26 C 0.4234(3) 0.6642(2) 0.5902(2) 0.0482(5) Uani 1 1 d . U . . .
H26A H 0.384289 0.607559 0.554726 0.058 Uiso 1 1 calc R U . . .
H26B H 0.440468 0.615055 0.659532 0.058 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
N28 N20 1.347(2) . ?
N28 N12 1.333(2) . ?
N28 C1 1.375(3) . ?
N11 N12 1.355(3) . ?
N11 C2 1.353(3) . ?
N11 C10 1.445(3) . ?
N20 C14 1.367(3) . ?
N25 N27 1.353(3) . ?
N25 C34 1.353(3) . ?
N25 C26 1.448(3) . ?
N26 N22 1.344(3) . ?
N26 N27 1.334(3) . ?
N26 C35 1.374(3) . ?
N22 C21 1.369(3) . ?
C33 C34 1.452(3) . ?
C33 C28 1.408(3) . ?
C33 C32 1.393(3) . ?
C3 C2 1.451(3) . ?
C3 C8 1.411(3) . ?
C3 C4 1.388(3) . ?
C2 C1 1.397(3) . ?
C34 C35 1.396(3) . ?
C1 C19 1.417(3) . ?
C36 C35 1.425(3) . ?
C36 C40 1.403(3) . ?
C36 C21 1.428(3) . ?
C19 C14 1.431(3) . ?
C19 C18 1.399(3) . ?
C14 C15 1.410(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.378(3) . ?
C28 C29 1.394(3) . ?
C28 C27 1.502(3) . ?
C40 H40 0.9500 . ?
C40 C39 1.383(3) . ?
C21 C37 1.407(3) . ?
C8 C7 1.397(3) . ?
C8 C9 1.502(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C32 H32 0.9500 . ?
C32 C31 1.376(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.380(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.380(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.394(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.364(3) . ?
C30 H30 0.9500 . ?
C39 H39 0.9500 . ?
C39 C38 1.412(3) . ?
C6 H6 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.412(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.363(3) . ?
C16 H16 0.9500 . ?
C38 H38 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.477(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C26 1.476(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N20 N28 C1 117.07(17) . . ?
N12 N28 N20 127.49(17) . . ?
N12 N28 C1 115.42(17) . . ?
N12 N11 C10 120.33(18) . . ?
C2 N11 N12 115.08(17) . . ?
C2 N11 C10 123.99(19) . . ?
N28 N20 C14 100.94(16) . . ?
N27 N25 C34 115.38(18) . . ?
N27 N25 C26 119.80(18) . . ?
C34 N25 C26 124.3(2) . . ?
N22 N26 C35 117.32(17) . . ?
N27 N26 N22 127.18(18) . . ?
N27 N26 C35 115.49(19) . . ?
N26 N22 C21 100.87(17) . . ?
N28 N12 N11 100.85(15) . . ?
N26 N27 N25 100.61(16) . . ?
C28 C33 C34 118.00(19) . . ?
C32 C33 C34 121.89(19) . . ?
C32 C33 C28 120.1(2) . . ?
C8 C3 C2 117.92(18) . . ?
C4 C3 C2 121.65(18) . . ?
C4 C3 C8 120.41(19) . . ?
N11 C2 C3 120.00(18) . . ?
N11 C2 C1 104.85(17) . . ?
C1 C2 C3 135.15(18) . . ?
N25 C34 C33 119.76(19) . . ?
N25 C34 C35 104.71(19) . . ?
C35 C34 C33 135.50(19) . . ?
N28 C1 C2 103.80(17) . . ?
N28 C1 C19 104.47(17) . . ?
C2 C1 C19 151.69(19) . . ?
C35 C36 C21 103.25(18) . . ?
C40 C36 C35 136.5(2) . . ?
C40 C36 C21 120.21(19) . . ?
N26 C35 C34 103.82(17) . . ?
N26 C35 C36 104.27(18) . . ?
C34 C35 C36 151.9(2) . . ?
C1 C19 C14 103.38(17) . . ?
C18 C19 C1 136.18(19) . . ?
C18 C19 C14 120.39(18) . . ?
N20 C14 C19 114.13(18) . . ?
N20 C14 C15 125.85(19) . . ?
C15 C14 C19 120.00(19) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 C19 118.44(19) . . ?
C17 C18 H18 120.8 . . ?
C33 C28 C27 119.0(2) . . ?
C29 C28 C33 118.5(2) . . ?
C29 C28 C27 122.4(2) . . ?
C36 C40 H40 120.7 . . ?
C39 C40 C36 118.5(2) . . ?
C39 C40 H40 120.7 . . ?
N22 C21 C36 114.30(19) . . ?
N22 C21 C37 125.6(2) . . ?
C37 C21 C36 120.1(2) . . ?
C3 C8 C9 119.0(2) . . ?
C7 C8 C3 118.3(2) . . ?
C7 C8 C9 122.69(19) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.34(19) . . ?
C5 C4 H4 119.8 . . ?
C33 C32 H32 119.8 . . ?
C31 C32 C33 120.4(2) . . ?
C31 C32 H32 119.8 . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 121.0(2) . . ?
C30 C29 H29 119.5 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.87(19) . . ?
C6 C7 H7 119.6 . . ?
C32 C31 H31 120.0 . . ?
C32 C31 C30 119.9(2) . . ?
C30 C31 H31 120.0 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C14 C15 H15 120.9 . . ?
C16 C15 C14 118.1(2) . . ?
C16 C15 H15 120.9 . . ?
C29 C30 C31 120.0(2) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C40 C39 H39 119.7 . . ?
C40 C39 C38 120.7(2) . . ?
C38 C39 H39 119.7 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C18 C17 H17 119.6 . . ?
C18 C17 C16 120.9(2) . . ?
C16 C17 H17 119.6 . . ?
C21 C37 H37 120.8 . . ?
C38 C37 C21 118.4(2) . . ?
C38 C37 H37 120.8 . . ?
C15 C16 C17 122.1(2) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C39 C38 H38 119.0 . . ?
C37 C38 C39 122.0(2) . . ?
C37 C38 H38 119.0 . . ?
C8 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 C8 115.4(2) . . ?
C10 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C28 C27 H27A 108.3 . . ?
C28 C27 H27B 108.3 . . ?
H27A C27 H27B 107.4 . . ?
C26 C27 C28 115.8(2) . . ?
C26 C27 H27A 108.3 . . ?
C26 C27 H27B 108.3 . . ?
N11 C10 C9 110.12(19) . . ?
N11 C10 H10A 109.6 . . ?
N11 C10 H10B 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N25 C26 C27 109.5(2) . . ?
N25 C26 H26A 109.8 . . ?
N25 C26 H26B 109.8 . . ?
C27 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?

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
N28 N20 C14 C19 -0.3(2) . . . . ?
N28 N20 C14 C15 -179.0(2) . . . . ?
N28 C1 C19 C14 -0.5(2) . . . . ?
N28 C1 C19 C18 176.8(2) . . . . ?
N11 C2 C1 N28 -0.4(2) . . . . ?
N11 C2 C1 C19 176.5(4) . . . . ?
N20 N28 N12 N11 -178.42(19) . . . . ?
N20 N28 C1 C2 178.83(17) . . . . ?
N20 N28 C1 C19 0.4(2) . . . . ?
N20 C14 C15 C16 176.2(2) . . . . ?
N25 C34 C35 N26 0.2(2) . . . . ?
N25 C34 C35 C36 176.8(3) . . . . ?
N26 N22 C21 C36 -0.1(2) . . . . ?
N26 N22 C21 C37 -178.98(19) . . . . ?
N22 N26 N27 N25 -177.88(19) . . . . ?
N22 N26 C35 C34 178.06(17) . . . . ?
N22 N26 C35 C36 -0.3(2) . . . . ?
N22 C21 C37 C38 177.9(2) . . . . ?
N12 N28 N20 C14 178.4(2) . . . . ?
N12 N28 C1 C2 0.2(2) . . . . ?
N12 N28 C1 C19 -178.25(17) . . . . ?
N12 N11 C2 C3 -179.79(18) . . . . ?
N12 N11 C2 C1 0.4(2) . . . . ?
N12 N11 C10 C9 -155.3(2) . . . . ?
N27 N25 C34 C33 178.30(17) . . . . ?
N27 N25 C34 C35 0.1(2) . . . . ?
N27 N25 C26 C27 -154.1(2) . . . . ?
N27 N26 N22 C21 178.57(19) . . . . ?
N27 N26 C35 C34 -0.5(2) . . . . ?
N27 N26 C35 C36 -178.82(17) . . . . ?
C33 C34 C35 N26 -177.6(2) . . . . ?
C33 C34 C35 C36 -1.0(5) . . . . ?
C33 C28 C29 C30 2.3(3) . . . . ?
C33 C28 C27 C26 28.9(3) . . . . ?
C33 C32 C31 C30 2.1(3) . . . . ?
C3 C2 C1 N28 179.9(2) . . . . ?
C3 C2 C1 C19 -3.2(6) . . . . ?
C3 C8 C7 C6 2.0(3) . . . . ?
C3 C8 C9 C10 28.9(3) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
C2 N11 N12 N28 -0.3(2) . . . . ?
C2 N11 C10 C9 33.9(3) . . . . ?
C2 C3 C8 C7 -179.05(18) . . . . ?
C2 C3 C8 C9 -2.3(3) . . . . ?
C2 C3 C4 C5 177.1(2) . . . . ?
C2 C1 C19 C14 -177.3(4) . . . . ?
C2 C1 C19 C18 -0.1(6) . . . . ?
C34 N25 N27 N26 -0.3(2) . . . . ?
C34 N25 C26 C27 34.8(3) . . . . ?
C34 C33 C28 C29 -178.56(18) . . . . ?
C34 C33 C28 C27 -2.6(3) . . . . ?
C34 C33 C32 C31 176.27(18) . . . . ?
C1 N28 N20 C14 -0.1(2) . . . . ?
C1 N28 N12 N11 0.0(2) . . . . ?
C1 C19 C14 N20 0.5(2) . . . . ?
C1 C19 C14 C15 179.28(19) . . . . ?
C1 C19 C18 C17 -176.3(2) . . . . ?
C36 C40 C39 C38 -1.0(3) . . . . ?
C36 C21 C37 C38 -1.0(3) . . . . ?
C35 N26 N22 C21 0.2(2) . . . . ?
C35 N26 N27 N25 0.5(2) . . . . ?
C35 C36 C40 C39 -177.3(2) . . . . ?
C35 C36 C21 N22 -0.1(2) . . . . ?
C35 C36 C21 C37 178.89(18) . . . . ?
C19 C14 C15 C16 -2.4(3) . . . . ?
C19 C18 C17 C16 -1.7(3) . . . . ?
C14 C19 C18 C17 0.6(3) . . . . ?
C14 C15 C16 C17 1.4(3) . . . . ?
C18 C19 C14 N20 -177.33(19) . . . . ?
C18 C19 C14 C15 1.5(3) . . . . ?
C18 C17 C16 C15 0.7(4) . . . . ?
C28 C33 C34 N25 -7.4(3) . . . . ?
C28 C33 C34 C35 170.1(2) . . . . ?
C28 C33 C32 C31 -1.3(3) . . . . ?
C28 C29 C30 C31 -1.5(3) . . . . ?
C28 C27 C26 N25 -42.1(3) . . . . ?
C40 C36 C35 N26 178.4(2) . . . . ?
C40 C36 C35 C34 1.8(5) . . . . ?
C40 C36 C21 N22 -178.66(18) . . . . ?
C40 C36 C21 C37 0.3(3) . . . . ?
C40 C39 C38 C37 0.3(3) . . . . ?
C21 C36 C35 N26 0.2(2) . . . . ?
C21 C36 C35 C34 -176.4(3) . . . . ?
C21 C36 C40 C39 0.7(3) . . . . ?
C21 C37 C38 C39 0.7(3) . . . . ?
C8 C3 C2 N11 -8.6(3) . . . . ?
C8 C3 C2 C1 171.1(2) . . . . ?
C8 C3 C4 C5 -1.5(3) . . . . ?
C8 C7 C6 C5 -1.6(3) . . . . ?
C8 C9 C10 N11 -42.2(3) . . . . ?
C4 C3 C2 N11 172.78(19) . . . . ?
C4 C3 C2 C1 -7.5(4) . . . . ?
C4 C3 C8 C7 -0.4(3) . . . . ?
C4 C3 C8 C9 176.3(2) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C32 C33 C34 N25 174.93(18) . . . . ?
C32 C33 C34 C35 -7.5(3) . . . . ?
C32 C33 C28 C29 -0.9(3) . . . . ?
C32 C33 C28 C27 175.07(19) . . . . ?
C32 C31 C30 C29 -0.7(3) . . . . ?
C29 C28 C27 C26 -155.4(2) . . . . ?
C7 C8 C9 C10 -154.5(2) . . . . ?
C9 C8 C7 C6 -174.7(2) . . . . ?
C27 C28 C29 C30 -173.5(2) . . . . ?
C10 N11 N12 N28 -171.83(19) . . . . ?
C10 N11 C2 C3 -8.6(3) . . . . ?
C10 N11 C2 C1 171.6(2) . . . . ?
C26 N25 N27 N26 -172.25(19) . . . . ?
C26 N25 C34 C33 -10.2(3) . . . . ?
C26 N25 C34 C35 171.6(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 1.603
_oxdiff_exptl_absorpt_empirical_full_min 0.680
