# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_Structure-5
_database_code_depnum_ccdc_archive 'CCDC 2128283'
loop_
_audit_author_name
_audit_author_address
'Darya V. Spiridonova'
;Research Park of St Petersburg State University
Russia
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2022-08-24 downloaded from the CCDC.
;
_audit_creation_date             2021-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C18 H23 N2'
_chemical_formula_sum            'C18 H23 Br N2'
_chemical_formula_weight         347.29
_chemical_absolute_configuration ?
_chemical_melting_point          '168-170 deg.C (decomp.)'
_chemical_oxdiff_formula         'C18 H27 N2 Br1'
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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   7.79650(10)
_cell_length_b                   18.2667(2)
_cell_length_c                   11.37140(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.6140(10)
_cell_angle_gamma                90
_cell_volume                     1618.83(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21438
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.9300
_cell_measurement_theta_min      3.7870
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.647
_exptl_absorpt_coefficient_mu    3.405
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22273
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.974
_diffrn_reflns_theta_min         4.842
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00 -26.00   0.50    0.15    --  -47.20  50.00-105.00   54
  2  ω    -82.00 -56.00   0.50    0.50    -- -106.00 125.00  30.00   52
  3  ω    -67.00 -37.00   0.50    0.50    -- -106.00 109.00  85.63   60
  4  ω    -71.00 -46.00   0.50    0.50    -- -106.00  61.00 -30.00   50
  5  ω    -60.00 -34.00   0.50    0.50    -- -106.00 111.00-121.06   52
  6  ω    -66.00 -33.00   0.50    0.50    -- -106.00 142.00 -83.60   66
  7  ω    -86.00 -33.00   0.50    0.50    -- -106.00  77.00-120.00  106
  8  ω   -108.00 -83.00   0.50    0.50    -- -106.00 111.00-121.06   50
  9  ω   -124.00 -89.00   0.50    0.50    -- -106.00 142.00 -83.60   70
 10  ω   -111.00 -85.00   0.50    0.50    -- -106.00 125.00  30.00   52
 11  ω   -108.00 -71.00   0.50    0.50    -- -106.00 109.00  85.63   74
 12  ω    -95.00 -55.00   0.50    0.50    -- -106.00 114.00  68.56   80
 13  ω   -103.00 -73.00   0.50    0.50    -- -106.00  77.00  60.00   60
 14  ω   -104.00 -34.00   0.50    0.50    -- -106.00  77.00  90.00  140
 15  ω   -111.00 -34.00   0.50    0.50    -- -106.00 125.00 120.00  154
 16  ω   -129.00 -97.00   0.50    0.50    -- -106.00 -15.00  30.00   64
 17  ω   -118.00 -86.00   0.50    0.50    -- -106.00 -77.00  60.00   64
 18  ω   -113.00 -35.00   0.50    0.15    --  -47.20 -50.00 107.00  156
 19  ω    -11.00  57.00   0.50    0.15    --   47.20 -50.00 107.00  136
 20  ω     64.00  94.00   0.50    0.15    --   47.20-125.00  90.00   60
 21  ω     34.00  92.00   0.50    0.15    --   47.20-125.00 -30.00  116
 22  ω     80.00 110.00   0.50    0.50    --  107.75-125.00  30.00   60
 23  ω     70.00 112.00   0.50    0.50    --  107.75-125.00  90.00   84
 24  ω     46.00  71.00   0.50    0.50    --  107.75 -61.00   0.00   50
 25  ω     38.00  71.00   0.50    0.50    --  107.75 -61.00 -60.00   66
 26  ω     55.00 105.00   0.50    0.50    --  107.75 -94.00 -90.00  100
 27  ω     70.00 112.00   0.50    0.50    --  107.75-125.00-150.00   84
 28  ω     75.00 105.00   0.50    0.50    --  107.75 -94.00-180.00   60
 29  ω     40.00 112.00   0.50    0.50    --  107.75-125.00-180.00  144
 30  ω     37.00  94.00   0.50    0.50    --  107.75 -77.00 -90.00  114
 31  ω     41.00  74.00   0.50    0.50    --  107.75-125.00  30.00   66
 32  ω     35.00 105.00   0.50    0.50    --  107.75 -94.00  90.00  140
 33  ω    148.00 177.00   0.50    0.50    --  107.75  15.00 120.00   58
 34  ω     96.00 174.00   0.50    0.50    --  107.75  61.00   0.00  156
 35  ω    105.00 176.00   0.50    0.50    --  107.75  45.00  30.00  142
 36  ω    100.00 178.00   0.50    0.50    --  107.75  50.00-105.00  156
 37  ω    101.00 150.00   0.50    0.50    --  107.75  77.00 -90.00   98
 38  ω     74.00  99.00   0.50    0.15    --   47.20 125.00 -90.00   50
 39  ω     40.00 119.00   0.50    0.15    --   47.20  50.00-105.00  158
 40  ω     35.00  61.00   0.50    0.50    --  107.75 -61.00-180.00   52
 41  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00-120.00  142
 42  ω     -6.00  26.00   0.50    0.15    --   47.20 -19.00   0.00   64
 43  ω    -24.00  25.00   0.50    0.15    --   47.20 -19.00 -30.00   98
 44  ω     97.00 134.00   0.50    0.50    --  107.75  15.00 120.00   74
 45  ω   -116.00 -91.00   0.50    0.15    --  -47.20-125.00  60.00   50
 46  ω   -164.00-122.00   0.50    0.50    -- -106.00 -50.00 107.00   84
 47  ω   -168.00-142.00   0.50    0.50    -- -106.00 -77.00  60.00   52
 48  ω   -169.00-144.00   0.50    0.50    -- -106.00 -15.00  30.00   50
 49  ω   -153.00 -88.00   0.50    0.50    -- -106.00 -77.00-150.00  130
 50  ω   -132.00 -94.00   0.50    0.50    -- -106.00 -94.00-180.00   76
 51  ω   -131.00 -92.00   0.50    0.50    -- -106.00 -61.00-180.00   78
 52  ω   -161.00-136.00   0.50    0.50    -- -106.00 -94.00-180.00   50
 53  ω    -22.00  17.00   0.50    0.15    --   47.20 -50.00 107.00   78
 54  ω     -9.00  21.00   0.50    0.15    --   14.00  85.00 141.33   60
 55  ω    -14.00  11.00   0.50    0.15    --   18.00  96.00  61.62   50
 56  ω     -1.00  24.00   0.50    0.15    --   30.00  95.00-129.19   50
 57  ω      8.00  33.00   0.50    0.15    --   38.00  93.00 -95.21   50
 58  ω     16.00  41.00   0.50    0.15    --   42.00  84.00  28.45   50
 59  ω     17.00  42.00   0.50    0.15    --   46.00  90.00-134.71   50
 60  ω     17.00  42.00   0.50    0.15    --   46.00  90.00 -65.36   50
 61  ω    -72.00 -35.00   0.50    0.15    --  -47.20 -37.00   0.00   74
 62  ω     26.00  61.00   0.50    0.15    --   47.20  77.00 120.00   70
 63  ω     33.00  58.00   0.50    0.15    --   54.00  72.00  76.33   50
 64  ω     31.00  66.00   0.50    0.15    --   54.00  78.00 145.30   70
 65  ω     32.00  58.00   0.50    0.15    --   54.00  78.00-103.81   52
 66  ω     33.00  58.00   0.50    0.15    --   54.00  72.00  -2.83   50
 67  ω     35.00  75.00   0.50    0.15    --   58.00  78.00 172.68   80
 68  ω     35.00  61.00   0.50    0.15    --   58.00  79.00 -58.78   52
 69  ω     39.00  65.00   0.50    0.15    --   62.00  77.00 -15.71   52
 70  ω     39.00  65.00   0.50    0.15    --   62.00  78.00  24.27   52
 71  ω     43.00  69.00   0.50    0.15    --   62.00  72.00-103.35   52
 72  ω     39.00  65.00   0.50    0.15    --   62.00  77.00   9.94   52
 73  ω     40.00  65.00   0.50    0.15    --   62.00  75.00 105.10   50
 74  ω     41.00  67.00   0.50    0.15    --   62.00  74.00 159.79   52
 75  ω     39.00  85.00   0.50    0.15    --   62.00  77.00  51.99   92
 76  ω     39.00  67.00   0.50    0.15    --   62.00  77.00-156.42   56
 77  ω    110.00 135.00   0.50    0.15    --   62.00  78.00  24.27   50
 78  ω     43.00  68.00   0.50    0.15    --   66.00  78.00 177.75   50
 79  ω     43.00  68.00   0.50    0.15    --   66.00  78.00  59.56   50
 80  ω    -73.00 -47.00   0.50    0.15    --  -70.00 -77.00 127.99   52
 81  ω    -74.00 -48.00   0.50    0.15    --  -70.00 -80.00 -79.79   52
 82  ω     47.00  73.00   0.50    0.15    --   70.00  77.00 112.93   52
 83  ω     49.00  75.00   0.50    0.15    --   70.00  76.00 -55.94   52
 84  ω     47.00  72.00   0.50    0.15    --   70.00  78.00 -98.28   50
 85  ω    105.00 137.00   0.50    0.15    --   70.00  78.00 -98.28   64
 86  ω     49.00  75.00   0.50    0.15    --   70.00  76.00  65.91   52
 87  ω     92.00 143.00   0.50    0.15    --   70.00  76.00  65.91  102
 88  ω    -90.00 -56.00   0.50    0.15    --  -74.00 -65.00  -0.44   68
 89  ω    -77.00 -51.00   0.50    0.15    --  -74.00 -77.00-153.77   52
 90  ω    -77.00 -51.00   0.50    0.15    --  -74.00 -76.00-179.25   52
 91  ω    -80.00 -54.00   0.50    0.15    --  -74.00 -69.00-157.56   52
 92  ω     51.00  77.00   0.50    0.15    --   74.00  77.00 -13.15   52
 93  ω    -88.00 -55.00   0.50    0.50    --  -78.00 -76.00  50.55   66
 94  ω    -82.00 -56.00   0.50    0.50    --  -78.00 -74.00 -18.06   52
 95  ω    -87.00 -62.00   0.50    0.50    --  -82.00 -73.00   6.93   50
 96  ω    -88.00 -62.00   0.50    0.50    --  -82.00 -73.00 172.35   52
 97  ω    -86.00 -60.00   0.50    0.50    --  -82.00 -74.00 157.31   52
 98  ω    -87.00 -61.00   0.50    0.50    --  -82.00 -74.00 -52.22   52
 99  ω    -86.00 -58.00   0.50    0.50    --  -82.00 -79.00  81.17   56
100  ω    -92.00 -66.00   0.50    0.50    --  -86.00 -73.00  50.67   52
101  ω    -90.00 -64.00   0.50    0.50    --  -86.00 -74.00 107.29   52
102  ω    -94.00 -68.00   0.50    0.50    --  -86.00 -65.00 -82.42   52
103  ω    -87.00 -62.00   0.50    0.50    --  -86.00 -79.00  44.89   50
104  ω    -89.00 -63.00   0.50    0.50    --  -86.00 -76.00-123.41   52
105  ω    -91.00 -65.00   0.50    0.50    --  -86.00 -72.00 -42.10   52
106  ω    -93.00 -68.00   0.50    0.50    --  -86.00 -65.00-108.21   50
107  ω    -93.00 -68.00   0.50    0.50    --  -86.00 -65.00 -36.86   50
108  ω   -128.00-102.00   0.50    0.50    --  -86.00 -65.00 -36.86   52
109  ω   -153.00-127.00   0.50    0.50    --  -90.00 -75.00 -49.66   52
110  ω    -97.00 -72.00   0.50    0.50    --  -90.00 -64.00 -23.32   50
111  ω    -94.00 -69.00   0.50    0.50    --  -90.00 -72.00 133.93   50
112  ω   -126.00-100.00   0.50    0.50    --  -90.00 -72.00 133.93   52
113  ω     73.00  99.00   0.50    0.50    --   90.00  65.00 -74.36   52
114  ω    -94.00 -69.00   0.50    0.50    --  -90.00 -72.00 122.05   50
115  ω    -97.00 -72.00   0.50    0.50    --  -90.00 -64.00-149.91   50
116  ω    -92.00 -67.00   0.50    0.50    --  -90.00 -76.00 162.62   50
117  ω    -96.00 -70.00   0.50    0.50    --  -90.00 -71.00  -0.14   52
118  ω    -93.00 -68.00   0.50    0.50    --  -90.00 -75.00 -49.66   50
119  ω   -134.00 -79.50   0.50    0.50    --  -94.00 -67.00 -74.46  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0519858000
_diffrn_orient_matrix_UB_12      -0.0803002000
_diffrn_orient_matrix_UB_13      0.0222579000
_diffrn_orient_matrix_UB_21      -0.0144917500
_diffrn_orient_matrix_UB_22      -0.0153293500
_diffrn_orient_matrix_UB_23      -0.1331056000
_diffrn_orient_matrix_UB_31      0.1901900500
_diffrn_orient_matrix_UB_32      0.0207218500
_diffrn_orient_matrix_UB_33      -0.0123269000
_diffrn_oxdiff_digest_frames     
;
01a0f70d4208699a307e68d303486e2bb8000488986
;
_diffrn_oxdiff_digest_hkl        
;
0166a51585206b56f341db87c6751e3a3e0745
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2960
_reflns_number_total             2966
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.060(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0139
_refine_ls_R_factor_gt           0.0139
_refine_ls_restrained_S_all      1.111
_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)+(0.0196P)²+0.5885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0359
_refine_ls_wR_factor_ref         0.0360
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.51509(2) 0.20354(2) 0.25146(2) 0.01746(7) Uani 1 1 d . . . . .
N1 N 0.5392(2) 0.33463(9) 0.55764(15) 0.0133(3) Uani 1 1 d . . . . .
N2 N 0.3215(2) 0.46040(10) 0.62216(16) 0.0148(4) Uani 1 1 d . . . . .
C1 C 0.6151(3) 0.39398(11) 0.48461(18) 0.0137(4) Uani 1 1 d . . . . .
C2 C 0.5861(3) 0.47064(11) 0.50725(18) 0.0139(4) Uani 1 1 d . . . . .
C3 C 0.4579(3) 0.50347(12) 0.57965(19) 0.0148(4) Uani 1 1 d . . . . .
C4 C 0.4693(3) 0.57698(12) 0.6061(2) 0.0193(4) Uani 1 1 d . . . . .
H4 H 0.391875 0.596749 0.658149 0.023 Uiso 1 1 calc R . . . .
C5 C 0.5924(3) 0.62322(12) 0.5580(2) 0.0218(5) Uani 1 1 d . . . . .
H5 H 0.600063 0.671949 0.581231 0.026 Uiso 1 1 calc R . . . .
C6 C 0.7009(3) 0.59604(12) 0.4766(2) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.777175 0.627162 0.439904 0.023 Uiso 1 1 calc R . . . .
C7 C 0.6978(3) 0.52027(12) 0.4478(2) 0.0160(4) Uani 1 1 d . . . . .
C8 C 0.8054(3) 0.49536(13) 0.3581(2) 0.0189(4) Uani 1 1 d . . . . .
H8 H 0.874316 0.528533 0.319200 0.023 Uiso 1 1 calc R . . . .
C9 C 0.8090(3) 0.42330(13) 0.32830(19) 0.0193(4) Uani 1 1 d . . . . .
H9 H 0.872021 0.407829 0.264658 0.023 Uiso 1 1 calc R . . . .
C10 C 0.7166(3) 0.37220(12) 0.39450(19) 0.0172(4) Uani 1 1 d . . . . .
H10 H 0.724626 0.322650 0.376668 0.021 Uiso 1 1 calc R . . . .
C11 C 0.3508(3) 0.31703(12) 0.52129(19) 0.0158(4) Uani 1 1 d . . . . .
H11A H 0.349620 0.273246 0.473004 0.019 Uiso 1 1 calc R . . . .
H11B H 0.288451 0.306034 0.591779 0.019 Uiso 1 1 calc R . . . .
C12 C 0.2559(3) 0.37711(12) 0.45437(19) 0.0167(4) Uani 1 1 d . . . . .
H12A H 0.159040 0.355795 0.411317 0.020 Uiso 1 1 calc R . . . .
H12B H 0.331936 0.398267 0.397465 0.020 Uiso 1 1 calc R . . . .
C13 C 0.1914(3) 0.43752(12) 0.53360(19) 0.0172(4) Uani 1 1 d . . . . .
H13A H 0.158265 0.479421 0.485738 0.021 Uiso 1 1 calc R . . . .
H13B H 0.090330 0.420428 0.573135 0.021 Uiso 1 1 calc R . . . .
C14 C 0.2446(3) 0.48576(13) 0.7304(2) 0.0216(5) Uani 1 1 d . . . . .
H14A H 0.333641 0.496702 0.787812 0.032 Uiso 1 1 calc GR . . . .
H14B H 0.171536 0.448211 0.760285 0.032 Uiso 1 1 calc GR . . . .
H14C H 0.178218 0.529061 0.714402 0.032 Uiso 1 1 calc GR . . . .
C15 C 0.5669(3) 0.34865(11) 0.69040(17) 0.0160(4) Uani 1 1 d . . . . .
H15A H 0.682737 0.365755 0.707488 0.019 Uiso 1 1 calc R . . . .
H15B H 0.486415 0.384908 0.717806 0.019 Uiso 1 1 calc R . . . .
C16 C 0.6388(3) 0.26201(12) 0.55000(19) 0.0171(4) Uani 1 1 d . . . . .
H16A H 0.613387 0.237327 0.476024 0.021 Uiso 1 1 calc R . . . .
H16B H 0.761548 0.270331 0.557390 0.021 Uiso 1 1 calc R . . . .
C17 C 0.5756(3) 0.21766(13) 0.6529(2) 0.0217(5) Uani 1 1 d . . . . .
H17A H 0.663078 0.183597 0.680891 0.026 Uiso 1 1 calc R . . . .
H17B H 0.473093 0.190376 0.630508 0.026 Uiso 1 1 calc R . . . .
C18 C 0.5364(4) 0.27491(11) 0.7486(3) 0.0197(5) Uani 1 1 d . . . . .
H18A H 0.418525 0.270707 0.772846 0.024 Uiso 1 1 calc R . . . .
H18B H 0.612190 0.268559 0.816905 0.024 Uiso 1 1 calc R . . . .


_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
N1 C1 1.497(3) . ?
N1 C11 1.548(3) . ?
N1 C15 1.540(2) . ?
N1 C16 1.541(3) . ?
N2 C3 1.419(3) . ?
N2 C13 1.470(3) . ?
N2 C14 1.460(3) . ?
C1 C2 1.443(3) . ?
C1 C10 1.371(3) . ?
C2 C3 1.443(3) . ?
C2 C7 1.439(3) . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.422(3) . ?
C7 C8 1.414(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.360(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.410(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.516(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.519(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C18 1.522(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.517(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.545(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 112.90(16) . . ?
C1 N1 C15 112.11(15) . . ?
C1 N1 C16 112.59(16) . . ?
C15 N1 C11 113.71(16) . . ?
C15 N1 C16 98.12(15) . . ?
C16 N1 C11 106.39(16) . . ?
C3 N2 C13 115.71(18) . . ?
C3 N2 C14 116.15(17) . . ?
C14 N2 C13 112.12(17) . . ?
C2 C1 N1 122.50(18) . . ?
C10 C1 N1 116.73(18) . . ?
C10 C1 C2 120.77(19) . . ?
C1 C2 C3 128.29(19) . . ?
C7 C2 C1 115.32(19) . . ?
C7 C2 C3 116.37(19) . . ?
N2 C3 C2 120.12(18) . . ?
C4 C3 N2 120.66(19) . . ?
C4 C3 C2 119.2(2) . . ?
C3 C4 H4 118.6 . . ?
C3 C4 C5 122.8(2) . . ?
C5 C4 H4 118.6 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.8(2) . . ?
C8 C7 C2 121.0(2) . . ?
C8 C7 C6 118.2(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C1 C10 C9 121.4(2) . . ?
C1 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
N1 C11 H11A 108.4 . . ?
N1 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 N1 115.42(17) . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C11 C12 C13 113.14(18) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
N2 C13 C12 112.30(17) . . ?
N2 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 110.7 . . ?
N1 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C18 C15 N1 105.03(18) . . ?
C18 C15 H15A 110.7 . . ?
C18 C15 H15B 110.7 . . ?
N1 C16 H16A 111.0 . . ?
N1 C16 H16B 111.0 . . ?
H16A C16 H16B 109.0 . . ?
C17 C16 N1 103.94(17) . . ?
C17 C16 H16A 111.0 . . ?
C17 C16 H16B 111.0 . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
C16 C17 C18 104.86(19) . . ?
H17A C17 H17B 108.8 . . ?
C18 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C15 C18 C17 104.9(2) . . ?
C15 C18 H18A 110.8 . . ?
C15 C18 H18B 110.8 . . ?
C17 C18 H18A 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.8 . . ?

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
N1 C1 C2 C3 -15.0(3) . . . . ?
N1 C1 C2 C7 166.29(18) . . . . ?
N1 C1 C10 C9 -173.16(19) . . . . ?
N1 C11 C12 C13 -79.6(2) . . . . ?
N1 C15 C18 C17 25.4(2) . . . . ?
N1 C16 C17 C18 -32.2(2) . . . . ?
N2 C3 C4 C5 -174.2(2) . . . . ?
C1 N1 C11 C12 -21.4(2) . . . . ?
C1 N1 C15 C18 -162.40(18) . . . . ?
C1 N1 C16 C17 164.58(17) . . . . ?
C1 C2 C3 N2 -11.4(3) . . . . ?
C1 C2 C3 C4 169.1(2) . . . . ?
C1 C2 C7 C6 -170.05(19) . . . . ?
C1 C2 C7 C8 10.9(3) . . . . ?
C2 C1 C10 C9 6.2(3) . . . . ?
C2 C3 C4 C5 5.4(3) . . . . ?
C2 C7 C8 C9 -1.8(3) . . . . ?
C3 N2 C13 C12 74.2(2) . . . . ?
C3 C2 C7 C6 11.1(3) . . . . ?
C3 C2 C7 C8 -167.9(2) . . . . ?
C3 C4 C5 C6 3.5(4) . . . . ?
C4 C5 C6 C7 -4.8(3) . . . . ?
C5 C6 C7 C2 -2.7(3) . . . . ?
C5 C6 C7 C8 176.4(2) . . . . ?
C6 C7 C8 C9 179.1(2) . . . . ?
C7 C2 C3 N2 167.30(18) . . . . ?
C7 C2 C3 C4 -12.3(3) . . . . ?
C7 C8 C9 C10 -5.8(3) . . . . ?
C8 C9 C10 C1 3.7(3) . . . . ?
C10 C1 C2 C3 165.7(2) . . . . ?
C10 C1 C2 C7 -13.0(3) . . . . ?
C11 N1 C1 C2 81.7(2) . . . . ?
C11 N1 C1 C10 -99.0(2) . . . . ?
C11 N1 C15 C18 68.0(2) . . . . ?
C11 N1 C16 C17 -71.2(2) . . . . ?
C11 C12 C13 N2 44.7(2) . . . . ?
C13 N2 C3 C2 -71.2(2) . . . . ?
C13 N2 C3 C4 108.4(2) . . . . ?
C14 N2 C3 C2 154.2(2) . . . . ?
C14 N2 C3 C4 -26.2(3) . . . . ?
C14 N2 C13 C12 -149.48(19) . . . . ?
C15 N1 C1 C2 -48.3(2) . . . . ?
C15 N1 C1 C10 131.04(19) . . . . ?
C15 N1 C11 C12 107.7(2) . . . . ?
C15 N1 C16 C17 46.48(19) . . . . ?
C16 N1 C1 C2 -157.80(18) . . . . ?
C16 N1 C1 C10 21.5(2) . . . . ?
C16 N1 C11 C12 -145.40(17) . . . . ?
C16 N1 C15 C18 -43.9(2) . . . . ?
C16 C17 C18 C15 4.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.832
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether/dichloromethane'
####################################################################### 
# 
# 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_Structure-14
_database_code_depnum_ccdc_archive 'CCDC 2128284'
loop_
_audit_author_name
_audit_author_address
'Darya V. Spiridonova'
;Research Park of St Petersburg State University
Russia
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2022-08-24 downloaded from the CCDC.
;
_audit_creation_date             2021-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H23 N2, I'
_chemical_formula_sum            'C17 H23 I N2'
_chemical_formula_weight         382.27
_chemical_melting_point          '134-136 deg.C (decomp.)'
_chemical_oxdiff_formula         'C17 H23 N2 I1'
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'
I I -0.3257 6.8362 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.96030(10)
_cell_length_b                   9.88890(10)
_cell_length_c                   27.9480(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.0630(10)
_cell_angle_gamma                90
_cell_volume                     3300.81(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15276
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2900
_cell_measurement_theta_min      3.1540
_shelx_estimated_absorpt_T_max   0.377
_shelx_estimated_absorpt_T_min   0.263
_exptl_absorpt_coefficient_mu    15.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            24250
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.993
_diffrn_reflns_theta_min         3.167
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -74.00   0.50    0.30    --  -38.82 154.00 141.00   52
  2  ω    -80.00 -54.00   0.50    0.30    --  -38.82 120.00 -16.00   52
  3  ω     44.00  74.00   0.50    0.30    --   38.82-154.00 101.00   60
  4  ω     17.00  51.00   0.50    0.30    --   38.82-120.00-100.00   68
  5  ω     33.00  98.00   0.50    1.20    --  100.00-120.00-100.00  130
  6  ω     84.00 109.00   0.50    1.20    --  100.00 154.00 141.00   50
  7  ω     67.00 126.00   0.50    1.20    --  100.00-154.00 101.00  118
  8  ω     91.00 119.00   0.50    1.20    --  100.00 120.00 -16.00   56
  9  ω   -104.00 -70.00   0.50    0.30    --  -38.82 -65.00  90.00   68
 10  ω    -73.00 -10.00   0.50    0.30    --  -38.82 104.00-180.00  126
 11  ω    -57.00  28.00   0.50    0.30    --  -38.82  77.00  30.00  170
 12  ω    -65.00 -20.00   0.50    0.30    --  -38.82 -65.00  90.00   90
 13  ω   -111.00 -21.00   0.50    0.30    --  -38.82 -21.00-150.00  180
 14  ω    -74.00 -22.00   0.50    0.30    --  -38.82 -43.00  30.00  104
 15  ω     38.00  71.00   0.50    0.30    --   38.82 -11.00  90.00   66
 16  ω     -4.00  66.00   0.50    0.30    --   38.82 -77.00 -90.00  140
 17  ω    -25.00   2.00   0.50    0.30    --   38.82 -11.00  90.00   54
 18  ω    -19.00   9.00   0.50    0.30    --   38.82 -54.00  90.00   56
 19  ω     23.00  49.00   0.50    0.30    --   38.82 -54.00  90.00   52
 20  ω     36.00 108.00   0.50    1.20    --  100.00-111.00 -90.00  144
 21  ω     87.00 113.00   0.50    1.20    --  100.00  30.00 150.00   52
 22  ω     81.00 109.00   0.50    1.20    --  100.00  22.00  60.00   56
 23  ω     36.00 120.00   0.50    1.20    --  100.00 -53.00-120.00  168
 24  ω     83.00 127.00   0.50    1.20    --  100.00 -77.00   0.00   88
 25  ω     45.00  71.00   0.50    1.20    --  100.00 -77.00   0.00   52
 26  ω    122.00 157.00   0.50    1.20    --  100.00  22.00  90.00   70
 27  ω     85.00 118.00   0.50    1.20    --  100.00-133.00  30.00   66
 28  ω     49.00  75.00   0.50    1.20    --  100.00-133.00  30.00   52
 29  ω    114.00 156.00   0.50    1.20    --  100.00  77.00 -60.00   84
 30  ω     81.00 129.00   0.50    1.20    --  100.00  22.00 -60.00   96
 31  ω     80.00 105.00   0.50    1.20    --  100.00 -93.00  30.00   50
 32  ω     42.00  68.00   0.50    1.20    --  100.00-111.00-180.00   52
 33  ω     52.00  78.00   0.50    1.20    --  100.00 -93.00 -90.00   52
 34  ω    126.00 156.00   0.50    1.20    --  100.00  45.00  30.00   60
 35  ω     59.00 115.00   0.50    1.20    --  100.00 -22.00-150.00  112
 36  ω     53.00 113.00   0.50    1.20    --  100.00 -86.00-120.00  120
 37  ω     52.00  96.00   0.50    1.20    --  100.00-111.00  60.00   88
 38  ω    129.00 155.00   0.50    1.20    --  100.00  22.00  60.00   52
 39  ω     83.00 109.00   0.50    1.20    --  100.00  45.00  30.00   52
 40  ω     50.00 104.00   0.50    1.20    --  100.00 -77.00-120.00  108
 41  ω     37.00  90.00   0.50    1.20    --  100.00 -15.00  30.00  106
 42  ω    107.00 132.00   0.50    1.20    --  100.00  30.00-120.00   50
 43  ω     97.00 157.00   0.50    1.20    --  100.00  77.00 -30.00  120
 44  ω    102.00 128.00   0.50    1.20    --  100.00 -86.00  60.00   52
 45  ω     86.00 111.00   0.50    1.20    --  100.00 -45.00 150.00   50
 46  ω     57.00 110.00   0.50    1.20    --  100.00 -30.00-150.00  106
 47  ω     65.00  91.00   0.50    0.30    --   38.82  65.00 -90.00   52
 48  ω    -62.00 -33.00   0.50    0.30    --  -38.82 -32.00 150.00   58
 49  ω    -78.00 -52.00   0.50    0.30    --  -38.82 -43.00 -30.00   52
 50  ω   -107.00 -19.00   0.50    0.30    --  -38.82 -21.00 120.00  176
 51  ω    -50.00 -24.00   0.50    0.30    --  -38.82 -43.00 -30.00   52
 52  ω    -18.00  38.00   0.50    0.30    --   38.82 -77.00  90.00  112
 53  ω     41.00  65.50   0.50    0.30    --   38.82-138.00 150.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0899471000
_diffrn_orient_matrix_UB_12      0.0814494000
_diffrn_orient_matrix_UB_13      -0.0249884000
_diffrn_orient_matrix_UB_21      0.0646385000
_diffrn_orient_matrix_UB_22      -0.1315467000
_diffrn_orient_matrix_UB_23      -0.0088347000
_diffrn_orient_matrix_UB_31      -0.0660912000
_diffrn_orient_matrix_UB_32      -0.0180350000
_diffrn_orient_matrix_UB_33      -0.0484341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5881
_reflns_number_total             6246
_reflns_odcompleteness_completeness 98.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.230
_refine_diff_density_min         -1.789
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.068
_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)+(0.0445P)²+14.3800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0993
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C1'(H1'A,H1'B), C2'(H2'A,
 H2'B), C3'(H3'A,H3'B), C4'(H4'A,H4'B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C9'(H9'),
 C10'(H10'), C11'(H11'), C13'(H13'), C14'(H14'), C15'(H15')
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C5'(H5'A,H5'B,H5'C),
 C6'(H6'A,H6'B,H6'C), C7'(H7'A,H7'B,H7'C)
;
_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
I1' I 0.72054(2) 0.13684(3) 0.21209(2) 0.01988(9) Uani 1 1 d . . . . .
I1 I 0.21349(2) 0.34811(3) 0.55718(2) 0.02341(9) Uani 1 1 d . . . . .
N1 N 0.0799(3) 0.3915(3) 0.39631(11) 0.0137(6) Uani 1 1 d . . . . .
N2 N 0.1065(3) 0.2087(3) 0.30876(11) 0.0156(7) Uani 1 1 d . . . . .
C1 C 0.0896(3) 0.4888(4) 0.43954(14) 0.0189(8) Uani 1 1 d . . . . .
H1A H 0.026223 0.550127 0.439177 0.023 Uiso 1 1 calc R . . . .
H1B H 0.092971 0.438908 0.469462 0.023 Uiso 1 1 calc R . . . .
C2 C 0.1971(3) 0.5652(4) 0.43339(16) 0.0220(9) Uani 1 1 d . . . . .
H2A H 0.223017 0.609574 0.462885 0.026 Uiso 1 1 calc R . . . .
H2B H 0.188437 0.631936 0.408029 0.026 Uiso 1 1 calc R . . . .
C3 C 0.2760(3) 0.4525(4) 0.42014(15) 0.0201(8) Uani 1 1 d . . . . .
H3A H 0.302896 0.402610 0.448349 0.024 Uiso 1 1 calc R . . . .
H3B H 0.339752 0.488271 0.404184 0.024 Uiso 1 1 calc R . . . .
C4 C 0.2039(3) 0.3623(4) 0.38622(15) 0.0152(8) Uani 1 1 d . . . . .
H4A H 0.221339 0.267759 0.392081 0.018 Uiso 1 1 calc R . . . .
H4B H 0.217773 0.383032 0.353132 0.018 Uiso 1 1 calc R . . . .
C5 C 0.0210(3) 0.4679(4) 0.35547(14) 0.0171(8) Uani 1 1 d . . . . .
H5A H 0.010596 0.409310 0.328200 0.026 Uiso 1 1 calc GR . . . .
H5B H 0.065482 0.544327 0.347174 0.026 Uiso 1 1 calc GR . . . .
H5C H -0.050613 0.498548 0.365078 0.026 Uiso 1 1 calc GR . . . .
C6 C 0.0150(4) 0.2157(5) 0.27162(16) 0.0293(10) Uani 1 1 d . . . . .
H6A H 0.014002 0.134269 0.252898 0.044 Uiso 1 1 calc GR . . . .
H6B H 0.026422 0.291987 0.251202 0.044 Uiso 1 1 calc GR . . . .
H6C H -0.055041 0.225396 0.286478 0.044 Uiso 1 1 calc GR . . . .
C7 C 0.2149(4) 0.1971(5) 0.28673(17) 0.0269(10) Uani 1 1 d . . . . .
H7A H 0.272017 0.175001 0.310919 0.040 Uiso 1 1 calc GR . . . .
H7B H 0.232809 0.281554 0.272019 0.040 Uiso 1 1 calc GR . . . .
H7C H 0.210796 0.127190 0.262874 0.040 Uiso 1 1 calc GR . . . .
C8 C 0.0855(3) 0.1039(4) 0.34229(14) 0.0135(7) Uani 1 1 d . . . . .
C9 C 0.1075(3) -0.0287(4) 0.33114(15) 0.0188(8) Uani 1 1 d . . . . .
H9 H 0.146745 -0.046849 0.304015 0.023 Uiso 1 1 calc R . . . .
C10 C 0.0737(4) -0.1361(4) 0.35871(17) 0.0226(9) Uani 1 1 d . . . . .
H10 H 0.093487 -0.224191 0.351092 0.027 Uiso 1 1 calc R . . . .
C11 C 0.0108(3) -0.1113(4) 0.39728(16) 0.0206(8) Uani 1 1 d . . . . .
H11 H -0.015871 -0.183455 0.414729 0.025 Uiso 1 1 calc R . . . .
C12 C -0.0140(3) 0.0221(4) 0.41088(14) 0.0160(8) Uani 1 1 d . . . . .
C13 C -0.0875(3) 0.0427(4) 0.44857(15) 0.0201(8) Uani 1 1 d . . . . .
H13 H -0.116405 -0.031512 0.464190 0.024 Uiso 1 1 calc R . . . .
C14 C -0.1156(4) 0.1686(5) 0.46188(15) 0.0214(9) Uani 1 1 d . . . . .
H14 H -0.170277 0.181226 0.483880 0.026 Uiso 1 1 calc R . . . .
C15 C -0.0619(3) 0.2810(4) 0.44242(14) 0.0188(8) Uani 1 1 d . . . . .
H15 H -0.078452 0.367254 0.453247 0.023 Uiso 1 1 calc R . . . .
C16 C 0.0145(3) 0.2660(4) 0.40773(13) 0.0136(7) Uani 1 1 d . . . . .
C17 C 0.0312(3) 0.1354(4) 0.38610(14) 0.0125(7) Uani 1 1 d . . . . .
N1' N 0.4532(3) 0.4468(3) 0.14998(11) 0.0143(6) Uani 1 1 d . . . . .
N2' N 0.3963(3) 0.7559(3) 0.14589(12) 0.0180(7) Uani 1 1 d . . . . .
C1' C 0.4563(3) 0.2913(4) 0.14978(15) 0.0196(8) Uani 1 1 d . . . . .
H1'A H 0.449818 0.256756 0.117269 0.024 Uiso 1 1 calc R . . . .
H1'B H 0.525493 0.258340 0.165283 0.024 Uiso 1 1 calc R . . . .
C2' C 0.3561(4) 0.2488(4) 0.17758(16) 0.0232(9) Uani 1 1 d . . . . .
H2'A H 0.377323 0.238307 0.211363 0.028 Uiso 1 1 calc R . . . .
H2'B H 0.325355 0.163975 0.165427 0.028 Uiso 1 1 calc R . . . .
C3' C 0.2701(3) 0.3649(4) 0.16971(16) 0.0197(8) Uani 1 1 d . . . . .
H3'A H 0.202079 0.332059 0.153170 0.024 Uiso 1 1 calc R . . . .
H3'B H 0.251280 0.403832 0.200103 0.024 Uiso 1 1 calc R . . . .
C4' C 0.3277(3) 0.4690(4) 0.13931(14) 0.0179(8) Uani 1 1 d . . . . .
H4'A H 0.306284 0.559989 0.148022 0.021 Uiso 1 1 calc R . . . .
H4'B H 0.308040 0.455105 0.105542 0.021 Uiso 1 1 calc R . . . .
C5' C 0.4910(3) 0.4953(5) 0.19955(14) 0.0204(8) Uani 1 1 d . . . . .
H5'A H 0.566293 0.465573 0.207007 0.031 Uiso 1 1 calc GR . . . .
H5'B H 0.442429 0.458733 0.222579 0.031 Uiso 1 1 calc GR . . . .
H5'C H 0.488128 0.592234 0.200523 0.031 Uiso 1 1 calc GR . . . .
C6' C 0.4822(4) 0.8394(5) 0.17159(17) 0.0273(10) Uani 1 1 d . . . . .
H6'A H 0.554869 0.801275 0.167463 0.041 Uiso 1 1 calc GR . . . .
H6'B H 0.468100 0.841560 0.205080 0.041 Uiso 1 1 calc GR . . . .
H6'C H 0.479563 0.929704 0.158977 0.041 Uiso 1 1 calc GR . . . .
C7' C 0.2851(4) 0.8141(5) 0.15194(17) 0.0265(9) Uani 1 1 d . . . . .
H7'A H 0.283169 0.905312 0.140124 0.040 Uiso 1 1 calc GR . . . .
H7'B H 0.269668 0.813997 0.185303 0.040 Uiso 1 1 calc GR . . . .
H7'C H 0.229560 0.761179 0.134353 0.040 Uiso 1 1 calc GR . . . .
C8' C 0.4254(3) 0.7364(4) 0.09718(14) 0.0161(8) Uani 1 1 d . . . . .
C9' C 0.3942(4) 0.8308(4) 0.06259(17) 0.0230(9) Uani 1 1 d . . . . .
H9' H 0.342141 0.897000 0.069468 0.028 Uiso 1 1 calc R . . . .
C10' C 0.4397(4) 0.8290(5) 0.01695(16) 0.0252(9) Uani 1 1 d . . . . .
H10' H 0.412933 0.887922 -0.006927 0.030 Uiso 1 1 calc R . . . .
C11' C 0.5227(3) 0.7406(5) 0.00833(15) 0.0228(9) Uani 1 1 d . . . . .
H11' H 0.558213 0.745909 -0.020409 0.027 Uiso 1 1 calc R . . . .
C12' C 0.5563(3) 0.6408(4) 0.04209(15) 0.0180(8) Uani 1 1 d . . . . .
C13' C 0.6502(4) 0.5587(5) 0.03364(15) 0.0226(9) Uani 1 1 d . . . . .
H13' H 0.687520 0.570175 0.005570 0.027 Uiso 1 1 calc R . . . .
C14' C 0.6867(4) 0.4634(5) 0.06580(15) 0.0220(9) Uani 1 1 d . . . . .
H14' H 0.754228 0.418788 0.062194 0.026 Uiso 1 1 calc R . . . .
C15' C 0.6209(3) 0.4331(4) 0.10468(15) 0.0192(8) Uani 1 1 d . . . . .
H15' H 0.641772 0.362102 0.125076 0.023 Uiso 1 1 calc R . . . .
C16' C 0.5265(3) 0.5064(4) 0.11303(13) 0.0151(8) Uani 1 1 d . . . . .
C17' C 0.4989(3) 0.6265(4) 0.08588(14) 0.0145(8) Uani 1 1 d . . . . .


_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
N1 C1 1.544(5) . ?
N1 C4 1.552(5) . ?
N1 C5 1.511(5) . ?
N1 C16 1.511(5) . ?
N2 C6 1.468(5) . ?
N2 C7 1.470(5) . ?
N2 C8 1.429(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.510(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.519(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.533(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.376(6) . ?
C8 C17 1.450(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.409(6) . ?
C12 C13 1.422(6) . ?
C12 C17 1.438(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.347(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.407(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(6) . ?
C16 C17 1.444(5) . ?
N1' C1' 1.538(5) . ?
N1' C4' 1.530(5) . ?
N1' C5' 1.512(5) . ?
N1' C16' 1.510(5) . ?
N2' C6' 1.474(5) . ?
N2' C7' 1.468(5) . ?
N2' C8' 1.436(5) . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C1' C2' 1.522(6) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C2' C3' 1.549(6) . ?
C3' H3'A 0.9700 . ?
C3' H3'B 0.9700 . ?
C3' C4' 1.523(5) . ?
C4' H4'A 0.9700 . ?
C4' H4'B 0.9700 . ?
C5' H5'A 0.9600 . ?
C5' H5'B 0.9600 . ?
C5' H5'C 0.9600 . ?
C6' H6'A 0.9600 . ?
C6' H6'B 0.9600 . ?
C6' H6'C 0.9600 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8' C9' 1.381(6) . ?
C8' C17' 1.443(5) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.414(7) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.353(7) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.409(6) . ?
C12' C13' 1.416(6) . ?
C12' C17' 1.442(6) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.358(6) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.408(6) . ?
C15' H15' 0.9300 . ?
C15' C16' 1.373(6) . ?
C16' C17' 1.438(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 103.1(3) . . ?
C5 N1 C1 107.0(3) . . ?
C5 N1 C4 111.6(3) . . ?
C16 N1 C1 111.4(3) . . ?
C16 N1 C4 113.3(3) . . ?
C16 N1 C5 110.1(3) . . ?
C6 N2 C7 110.4(4) . . ?
C8 N2 C6 110.3(3) . . ?
C8 N2 C7 114.1(3) . . ?
N1 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 N1 104.5(3) . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
C1 C2 H2A 111.4 . . ?
C1 C2 H2B 111.4 . . ?
C1 C2 C3 101.8(3) . . ?
H2A C2 H2B 109.3 . . ?
C3 C2 H2A 111.4 . . ?
C3 C2 H2B 111.4 . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C2 C3 C4 103.9(3) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
N1 C4 H4A 110.3 . . ?
N1 C4 H4B 110.3 . . ?
C3 C4 N1 106.9(3) . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C17 120.0(3) . . ?
C9 C8 N2 120.0(4) . . ?
C9 C8 C17 119.7(4) . . ?
C8 C9 H9 118.7 . . ?
C8 C9 C10 122.6(4) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 118.8(4) . . ?
C11 C12 C17 120.7(4) . . ?
C13 C12 C17 120.5(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 N1 115.5(3) . . ?
C15 C16 C17 120.2(4) . . ?
C17 C16 N1 124.2(3) . . ?
C12 C17 C8 115.8(3) . . ?
C12 C17 C16 115.6(3) . . ?
C16 C17 C8 128.6(3) . . ?
C4' N1' C1' 99.6(3) . . ?
C5' N1' C1' 108.3(3) . . ?
C5' N1' C4' 112.0(3) . . ?
C16' N1' C1' 111.9(3) . . ?
C16' N1' C4' 114.2(3) . . ?
C16' N1' C5' 110.3(3) . . ?
C7' N2' C6' 109.7(3) . . ?
C8' N2' C6' 109.9(3) . . ?
C8' N2' C7' 115.4(3) . . ?
N1' C1' H1'A 110.8 . . ?
N1' C1' H1'B 110.8 . . ?
H1'A C1' H1'B 108.9 . . ?
C2' C1' N1' 104.7(3) . . ?
C2' C1' H1'A 110.8 . . ?
C2' C1' H1'B 110.8 . . ?
C1' C2' H2'A 110.8 . . ?
C1' C2' H2'B 110.8 . . ?
C1' C2' C3' 104.9(3) . . ?
H2'A C2' H2'B 108.8 . . ?
C3' C2' H2'A 110.8 . . ?
C3' C2' H2'B 110.8 . . ?
C2' C3' H3'A 110.7 . . ?
C2' C3' H3'B 110.7 . . ?
H3'A C3' H3'B 108.8 . . ?
C4' C3' C2' 105.3(3) . . ?
C4' C3' H3'A 110.7 . . ?
C4' C3' H3'B 110.7 . . ?
N1' C4' H4'A 110.7 . . ?
N1' C4' H4'B 110.7 . . ?
C3' C4' N1' 105.2(3) . . ?
C3' C4' H4'A 110.7 . . ?
C3' C4' H4'B 110.7 . . ?
H4'A C4' H4'B 108.8 . . ?
N1' C5' H5'A 109.5 . . ?
N1' C5' H5'B 109.5 . . ?
N1' C5' H5'C 109.5 . . ?
H5'A C5' H5'B 109.5 . . ?
H5'A C5' H5'C 109.5 . . ?
H5'B C5' H5'C 109.5 . . ?
N2' C6' H6'A 109.5 . . ?
N2' C6' H6'B 109.5 . . ?
N2' C6' H6'C 109.5 . . ?
H6'A C6' H6'B 109.5 . . ?
H6'A C6' H6'C 109.5 . . ?
H6'B C6' H6'C 109.5 . . ?
N2' C7' H7'A 109.5 . . ?
N2' C7' H7'B 109.5 . . ?
N2' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
N2' C8' C17' 119.3(3) . . ?
C9' C8' N2' 120.1(4) . . ?
C9' C8' C17' 120.1(4) . . ?
C8' C9' H9' 119.3 . . ?
C8' C9' C10' 121.3(4) . . ?
C10' C9' H9' 119.3 . . ?
C9' C10' H10' 120.3 . . ?
C11' C10' C9' 119.4(4) . . ?
C11' C10' H10' 120.3 . . ?
C10' C11' H11' 119.4 . . ?
C10' C11' C12' 121.3(4) . . ?
C12' C11' H11' 119.4 . . ?
C11' C12' C13' 119.4(4) . . ?
C11' C12' C17' 120.3(4) . . ?
C13' C12' C17' 120.2(4) . . ?
C12' C13' H13' 119.4 . . ?
C14' C13' C12' 121.2(4) . . ?
C14' C13' H13' 119.4 . . ?
C13' C14' H14' 120.5 . . ?
C13' C14' C15' 119.0(4) . . ?
C15' C14' H14' 120.5 . . ?
C14' C15' H15' 119.4 . . ?
C16' C15' C14' 121.2(4) . . ?
C16' C15' H15' 119.4 . . ?
C15' C16' N1' 115.0(3) . . ?
C15' C16' C17' 120.9(4) . . ?
C17' C16' N1' 123.9(3) . . ?
C12' C17' C8' 115.8(3) . . ?
C16' C17' C8' 129.2(4) . . ?
C16' C17' C12' 115.0(4) . . ?

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
N1 C1 C2 C3 -44.3(4) . . . . ?
N1 C16 C17 C8 -18.7(6) . . . . ?
N1 C16 C17 C12 162.6(3) . . . . ?
N2 C8 C9 C10 -170.1(4) . . . . ?
N2 C8 C17 C12 163.5(3) . . . . ?
N2 C8 C17 C16 -15.2(6) . . . . ?
C1 N1 C4 C3 -5.2(4) . . . . ?
C1 N1 C16 C15 26.6(4) . . . . ?
C1 N1 C16 C17 -151.0(3) . . . . ?
C1 C2 C3 C4 40.3(4) . . . . ?
C2 C3 C4 N1 -21.6(4) . . . . ?
C4 N1 C1 C2 30.4(4) . . . . ?
C4 N1 C16 C15 142.3(3) . . . . ?
C4 N1 C16 C17 -35.3(5) . . . . ?
C5 N1 C1 C2 -87.3(4) . . . . ?
C5 N1 C4 C3 109.3(4) . . . . ?
C5 N1 C16 C15 -92.0(4) . . . . ?
C5 N1 C16 C17 90.5(4) . . . . ?
C6 N2 C8 C9 79.8(4) . . . . ?
C6 N2 C8 C17 -94.4(4) . . . . ?
C7 N2 C8 C9 -45.2(5) . . . . ?
C7 N2 C8 C17 140.7(4) . . . . ?
C8 C9 C10 C11 3.4(7) . . . . ?
C9 C8 C17 C12 -10.7(5) . . . . ?
C9 C8 C17 C16 170.6(4) . . . . ?
C9 C10 C11 C12 -3.8(6) . . . . ?
C10 C11 C12 C13 174.7(4) . . . . ?
C10 C11 C12 C17 -3.4(6) . . . . ?
C11 C12 C13 C14 -178.4(4) . . . . ?
C11 C12 C17 C8 10.4(5) . . . . ?
C11 C12 C17 C16 -170.8(4) . . . . ?
C12 C13 C14 C15 -7.6(6) . . . . ?
C13 C12 C17 C8 -167.6(3) . . . . ?
C13 C12 C17 C16 11.3(5) . . . . ?
C13 C14 C15 C16 3.9(6) . . . . ?
C14 C15 C16 N1 -169.9(4) . . . . ?
C14 C15 C16 C17 7.8(6) . . . . ?
C15 C16 C17 C8 163.8(4) . . . . ?
C15 C16 C17 C12 -14.8(5) . . . . ?
C16 N1 C1 C2 152.3(3) . . . . ?
C16 N1 C4 C3 -125.7(3) . . . . ?
C17 C8 C9 C10 4.1(6) . . . . ?
C17 C12 C13 C14 -0.3(6) . . . . ?
N1' C1' C2' C3' 28.4(4) . . . . ?
N1' C16' C17' C8' 23.2(6) . . . . ?
N1' C16' C17' C12' -159.3(3) . . . . ?
N2' C8' C9' C10' 167.3(4) . . . . ?
N2' C8' C17' C12' -158.2(3) . . . . ?
N2' C8' C17' C16' 19.3(6) . . . . ?
C1' N1' C4' C3' 42.1(4) . . . . ?
C1' N1' C16' C15' -32.8(4) . . . . ?
C1' N1' C16' C17' 143.7(4) . . . . ?
C1' C2' C3' C4' -1.9(4) . . . . ?
C2' C3' C4' N1' -25.5(4) . . . . ?
C4' N1' C1' C2' -43.3(4) . . . . ?
C4' N1' C16' C15' -144.9(4) . . . . ?
C4' N1' C16' C17' 31.6(5) . . . . ?
C5' N1' C1' C2' 73.9(4) . . . . ?
C5' N1' C4' C3' -72.2(4) . . . . ?
C5' N1' C16' C15' 87.8(4) . . . . ?
C5' N1' C16' C17' -95.7(4) . . . . ?
C6' N2' C8' C9' -86.3(4) . . . . ?
C6' N2' C8' C17' 86.1(4) . . . . ?
C7' N2' C8' C9' 38.3(5) . . . . ?
C7' N2' C8' C17' -149.3(4) . . . . ?
C8' C9' C10' C11' -5.9(7) . . . . ?
C9' C8' C17' C12' 14.2(5) . . . . ?
C9' C8' C17' C16' -168.3(4) . . . . ?
C9' C10' C11' C12' 6.9(6) . . . . ?
C10' C11' C12' C13' -174.1(4) . . . . ?
C10' C11' C12' C17' 3.0(6) . . . . ?
C11' C12' C13' C14' 178.5(4) . . . . ?
C11' C12' C17' C8' -13.3(5) . . . . ?
C11' C12' C17' C16' 168.9(4) . . . . ?
C12' C13' C14' C15' 9.0(6) . . . . ?
C13' C12' C17' C8' 163.8(4) . . . . ?
C13' C12' C17' C16' -14.0(5) . . . . ?
C13' C14' C15' C16' -6.1(6) . . . . ?
C14' C15' C16' N1' 169.1(4) . . . . ?
C14' C15' C16' C17' -7.5(6) . . . . ?
C15' C16' C17' C8' -160.5(4) . . . . ?
C15' C16' C17' C12' 17.1(5) . . . . ?
C16' N1' C1' C2' -164.4(3) . . . . ?
C16' N1' C4' C3' 161.5(3) . . . . ?
C17' C8' C9' C10' -5.1(6) . . . . ?
C17' C12' C13' C14' 1.4(6) . . . . ?

_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 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.794
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether/dichloromethane'
####################################################################### 
# 
# 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_Structure-18b
_database_code_depnum_ccdc_archive 'CCDC 2168929'
loop_
_audit_author_name
_audit_author_address
'Oleg P. Demidov'
;Center for collective use of scientific equipment of the North Caucasus Federal University
Russia
;
_audit_update_record             
;
2022-04-26 deposited with the CCDC.	2022-08-24 downloaded from the CCDC.
;
_audit_creation_date             2022-04-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
"1,1'-(2-Methylnaphthalene-1,8-diyl)dipyrrolidine hydrogen tetrafluoroborate"
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 N2, B F4'
_chemical_formula_sum            'C19 H25 B F4 N2'
_chemical_formula_weight         368.22
_chemical_melting_point          '214-216 deg.C'
_chemical_oxdiff_formula         'C19 H25 B F4 N2'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.78120(10)
_cell_length_b                   10.34370(10)
_cell_length_c                   17.7597(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.1060(10)
_cell_angle_gamma                90
_cell_volume                     1789.69(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11644
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9480
_cell_measurement_theta_min      4.5840
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -5 3 0.0783
3 -6 4 0.0738
2 -6 4 0.0738
1 -6 3 0.0760
1 -6 2 0.0760
2 -6 0 0.0839
-3 6 -2 0.0665
3 -6 -1 0.0839
3 -6 0 0.0857
-5 -4 1 0.1130
6 2 -1 0.1075
0 -1 -11 0.0762
2 -5 7 0.0680
-5 -1 -6 0.0847
4 3 6 0.1463
-2 0 11 0.0874
5 -1 6 0.0855
-6 1 -2 0.0920

_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.147
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
3.6775 -5.0406 3.0474 0.0878 -0.2166 0.9723
2.5921 -5.5809 3.9086 0.1913 -0.0478 0.9804
2.2501 -5.7721 3.8544 0.1967 0.0136 0.9804
1.4790 -6.3125 2.6048 0.1144 0.1832 0.9764
1.4543 -6.4186 1.8556 0.0522 0.2096 0.9764
2.0490 -6.3528 -0.2262 -0.1400 0.1667 0.9760
-2.7495 5.9054 -1.8061 -0.0088 0.0030 -1.0000
2.8002 -6.0204 -0.8138 -0.2112 0.0526 0.9760
3.4913 -5.6054 -0.4070 -0.1972 -0.0797 0.9771
-4.7080 -4.4968 1.2288 0.2229 0.9346 0.2771
6.0423 2.0483 -0.5335 -0.2302 -0.9614 0.1504
0.3516 -0.5935 -11.4781 -0.9691 0.2319 -0.0838
2.2243 -4.8320 6.5218 0.4266 -0.1039 0.8984
-4.9253 -0.9387 -6.2736 -0.3629 0.8723 -0.3278
4.2369 3.1012 6.0274 0.3835 -0.9235 -0.0091
-1.7213 0.3762 11.3129 0.9996 -0.0253 0.0126
5.0580 -1.0544 5.8875 0.3100 -0.7434 0.5927
-5.9704 1.2671 -2.2889 0.0210 0.7789 -0.6268

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.282
_diffrn_reflns_theta_min         4.953
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    1.00    --  -41.60  37.00  -5.00   99
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.60 -37.00-161.00   99
  3  ω    -33.00  66.00   1.00    1.00    --   41.60 -37.00-161.00   99
  4  ω     17.00 116.00   1.00    1.00    --   41.60  37.00  -5.00   99
  5  ω     38.00 136.00   1.00    2.30    --  112.00 -37.00-161.00   98
  6  ω     88.00 178.00   1.00    2.30    --  112.00  37.00  -5.00   90
  7  ω     23.00  98.00   1.00    1.00    --   41.60-125.00  30.00   75
  8  ω     23.00  98.00   1.00    1.00    --   41.60-125.00-150.00   75
  9  ω     36.00 113.00   1.00    2.30    --  112.00-111.00  30.00   77
 10  ω     36.00 113.00   1.00    2.30    --  112.00-111.00-150.00   77
 11  ω     57.00 150.00   1.00    2.30    --  112.00 178.00-150.00   93
 12  ω     59.00 178.00   1.00    2.30    --  112.00  15.00 -30.00  119
 13  ω     59.00 178.00   1.00    2.30    --  112.00  15.00  90.00  119
 14  ω    100.00 178.00   1.00    2.30    --  112.00 111.00 -30.00   78
 15  ω    100.00 178.00   1.00    2.30    --  112.00 111.00   0.00   78
 16  ω     30.00 110.00   1.00    2.30    --  112.00 -95.00 120.00   80
 17  ω     79.00 140.00   1.00    2.30    --  112.00  77.00  30.00   61
 18  ω     38.00 102.00   1.00    2.30    --  112.00-111.00   0.00   64
 19  ω     78.00 104.00   1.00    2.30    --  112.00-111.00  90.00   26
 20  ω    135.00 161.00   1.00    2.30    --  112.00 111.00  30.00   26
 21  ω     36.00  63.00   1.00    2.30    --  112.00-111.00 -60.00   27
 22  ω     81.00 106.00   1.00    2.30    --  112.00-111.00  60.00   25
 23  ω     58.00 110.00   1.00    2.30    --  112.00 -95.00-120.00   52
 24  ω    137.00 163.00   1.00    2.30    --  112.00 111.00 150.00   26
 25  ω     46.00  87.00   1.00    2.30    --  112.00-111.00-180.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0335733000
_diffrn_orient_matrix_UB_12      0.0082489000
_diffrn_orient_matrix_UB_13      0.0829765000
_diffrn_orient_matrix_UB_21      -0.1373002000
_diffrn_orient_matrix_UB_22      -0.0697789000
_diffrn_orient_matrix_UB_23      -0.0208037000
_diffrn_orient_matrix_UB_31      0.0708617000
_diffrn_orient_matrix_UB_32      -0.1313613000
_diffrn_orient_matrix_UB_33      0.0162666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3472
_reflns_number_total             3735
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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         0.352
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.046
_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)+(0.0511P)²+0.8206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F4) = Uanis(F4A)
Uanis(F1) = Uanis(F1A)
Uanis(F3A) = Uanis(F3)
3. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=1-FVAR(1)
 Sof(F3)=Sof(F4)=Sof(F1)=Sof(F2)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C12(H12A,H12B), C19(H19A,H19B), C13(H13A,
 H13B), C17(H17A,H17B), C18(H18A,H18B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C2(H2), C6(H6), C3(H3)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.17094(10) 0.63684(10) 0.58408(6) 0.0190(2) Uani 1 1 d . . . . .
N2 N 0.22300(10) 0.70489(10) 0.45120(6) 0.0189(2) Uani 1 1 d . . . . .
C10 C 0.28372(11) 0.48687(12) 0.50032(7) 0.0198(2) Uani 1 1 d . . . . .
C9 C 0.28457(12) 0.57774(12) 0.43924(7) 0.0200(2) Uani 1 1 d . . . . .
C5 C 0.33567(12) 0.35942(12) 0.48919(7) 0.0226(3) Uani 1 1 d . . . . .
C4 C 0.33338(12) 0.26537(12) 0.54668(8) 0.0248(3) Uani 1 1 d . . . . .
H4 H 0.365906 0.182607 0.538248 0.030 Uiso 1 1 calc R U . . .
C1 C 0.23145(12) 0.51072(12) 0.57156(7) 0.0203(2) Uani 1 1 d . . . . .
C7 C 0.38771(13) 0.41812(14) 0.36317(7) 0.0264(3) Uani 1 1 d . . . . .
H7 H 0.423201 0.395509 0.318118 0.032 Uiso 1 1 calc R U . . .
C8 C 0.33614(12) 0.54561(13) 0.37163(7) 0.0235(3) Uani 1 1 d . . . . .
C15 C 0.23842(13) 0.71442(13) 0.64811(7) 0.0230(3) Uani 1 1 d . . . . .
H15A H 0.323622 0.752243 0.634588 0.028 Uiso 1 1 calc R U . . .
H15B H 0.257327 0.661398 0.692878 0.028 Uiso 1 1 calc R U . . .
C2 C 0.23286(13) 0.41812(13) 0.62709(7) 0.0245(3) Uani 1 1 d . . . . .
H2 H 0.199702 0.437827 0.673207 0.029 Uiso 1 1 calc R U . . .
C16 C 0.31456(13) 0.82181(12) 0.45286(7) 0.0228(3) Uani 1 1 d . . . . .
H16A H 0.374692 0.819166 0.412306 0.027 Uiso 1 1 calc R U . . .
H16B H 0.369711 0.828941 0.500850 0.027 Uiso 1 1 calc R U . . .
C12 C 0.02284(12) 0.63371(13) 0.59848(8) 0.0247(3) Uani 1 1 d . . . . .
H12A H 0.007059 0.575186 0.639494 0.030 Uiso 1 1 calc R U . . .
H12B H -0.034498 0.608222 0.553555 0.030 Uiso 1 1 calc R U . . .
C6 C 0.38648(13) 0.32862(13) 0.41915(8) 0.0268(3) Uani 1 1 d . . . . .
H6 H 0.419536 0.245845 0.411336 0.032 Uiso 1 1 calc R U . . .
C19 C 0.09297(13) 0.73547(13) 0.40197(7) 0.0247(3) Uani 1 1 d . . . . .
H19A H 0.012754 0.719998 0.429108 0.030 Uiso 1 1 calc R U . . .
H19B H 0.086299 0.682873 0.356573 0.030 Uiso 1 1 calc R U . . .
C3 C 0.28424(13) 0.29358(13) 0.61454(8) 0.0273(3) Uani 1 1 d . . . . .
H3 H 0.284776 0.230914 0.652116 0.033 Uiso 1 1 calc R U . . .
C13 C -0.00368(14) 0.77343(15) 0.61979(8) 0.0311(3) Uani 1 1 d . . . . .
H13A H -0.077556 0.778716 0.652660 0.037 Uiso 1 1 calc R U . . .
H13B H -0.027556 0.825333 0.575059 0.037 Uiso 1 1 calc R U . . .
C11 C 0.34102(14) 0.63540(15) 0.30534(7) 0.0293(3) Uani 1 1 d . . . . .
H11A H 0.279314 0.706378 0.310523 0.044 Uiso 1 1 calc R U . . .
H11B H 0.314157 0.589421 0.259445 0.044 Uiso 1 1 calc R U . . .
H11C H 0.432712 0.667745 0.303742 0.044 Uiso 1 1 calc R U . . .
C17 C 0.21271(14) 0.93211(14) 0.44203(8) 0.0303(3) Uani 1 1 d . . . . .
H17A H 0.255767 1.009318 0.424057 0.036 Uiso 1 1 calc R U . . .
H17B H 0.172605 0.951924 0.488707 0.036 Uiso 1 1 calc R U . . .
B1 B 0.48807(14) 0.97947(12) 0.69117(7) 0.0169(3) Uani 1 1 d . . . . .
C18 C 0.10475(16) 0.87866(15) 0.38228(9) 0.0349(3) Uani 1 1 d . . . . .
H18A H 0.017474 0.922269 0.384798 0.042 Uiso 1 1 calc R U . . .
H18B H 0.134103 0.889312 0.331903 0.042 Uiso 1 1 calc R U . . .
C14 C 0.13273(15) 0.81928(16) 0.66117(9) 0.0363(3) Uani 1 1 d . . . . .
H14A H 0.160306 0.901380 0.640904 0.044 Uiso 1 1 calc R U . . .
H14B H 0.123517 0.829674 0.714768 0.044 Uiso 1 1 calc R U . . .
H1 H 0.190(2) 0.690(2) 0.5178(13) 0.059(6) Uiso 1 1 d . . . . .
F3 F 0.5003(2) 0.85583(18) 0.72588(11) 0.0293(3) Uani 0.910(7) 1 d . . P A 1
F4 F 0.4717(2) 0.9651(3) 0.61243(14) 0.0284(4) Uani 0.910(7) 1 d . . P A 1
F1 F 0.3714(3) 1.03932(18) 0.71506(7) 0.0416(5) Uani 0.910(7) 1 d . . P A 1
F2 F 0.6025(3) 1.0528(2) 0.71203(14) 0.0425(5) Uani 0.910(7) 1 d . . P A 1
F1A F 0.428(2) 1.0718(18) 0.7216(8) 0.0416(5) Uani 0.090(7) 1 d . . P A 2
F2A F 0.634(2) 1.017(3) 0.6943(13) 0.042(5) Uani 0.090(7) 1 d . . P A 2
F3A F 0.500(3) 0.883(2) 0.7183(14) 0.0293(3) Uani 0.090(7) 1 d . . P A 2
F4A F 0.445(3) 0.961(3) 0.6172(18) 0.0284(4) Uani 0.090(7) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.4578(16) . ?
N1 C15 1.4964(15) . ?
N1 C12 1.4936(15) . ?
N1 H1 1.33(2) . ?
N2 C9 1.4698(15) . ?
N2 C16 1.5036(15) . ?
N2 C19 1.5113(15) . ?
N2 H1 1.26(2) . ?
C10 C9 1.4358(18) . ?
C10 C5 1.4329(17) . ?
C10 C1 1.4277(17) . ?
C9 C8 1.3837(17) . ?
C5 C4 1.4119(19) . ?
C5 C6 1.4162(18) . ?
C4 H4 0.9300 . ?
C4 C3 1.368(2) . ?
C1 C2 1.3739(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.4246(19) . ?
C7 C6 1.359(2) . ?
C8 C11 1.5036(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.5302(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.4078(19) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5156(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5222(19) . ?
C6 H6 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.5285(19) . ?
C3 H3 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.540(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.532(2) . ?
B1 F3 1.420(2) . ?
B1 F4 1.401(3) . ?
B1 F1 1.397(2) . ?
B1 F2 1.375(3) . ?
B1 F1A 1.269(13) . ?
B1 F2A 1.476(18) . ?
B1 F3A 1.11(2) . ?
B1 F4A 1.36(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C15 115.99(10) . . ?
C1 N1 C12 114.82(10) . . ?
C1 N1 H1 98.3(10) . . ?
C15 N1 H1 111.5(10) . . ?
C12 N1 C15 104.51(9) . . ?
C12 N1 H1 112.0(10) . . ?
C9 N2 C16 118.14(9) . . ?
C9 N2 C19 115.99(9) . . ?
C9 N2 H1 99.7(10) . . ?
C16 N2 C19 108.19(10) . . ?
C16 N2 H1 106.4(10) . . ?
C19 N2 H1 107.1(10) . . ?
C5 C10 C9 118.17(11) . . ?
C1 C10 C9 125.66(11) . . ?
C1 C10 C5 116.14(11) . . ?
C10 C9 N2 116.53(10) . . ?
C8 C9 N2 121.73(11) . . ?
C8 C9 C10 121.70(12) . . ?
C4 C5 C10 120.37(12) . . ?
C4 C5 C6 120.63(12) . . ?
C6 C5 C10 118.99(12) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.30(12) . . ?
C3 C4 H4 119.4 . . ?
C10 C1 N1 118.17(11) . . ?
C2 C1 N1 119.52(11) . . ?
C2 C1 C10 122.29(12) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.81(12) . . ?
C9 C8 C7 118.27(12) . . ?
C9 C8 C11 124.78(12) . . ?
C7 C8 C11 116.94(11) . . ?
N1 C15 H15A 111.0 . . ?
N1 C15 H15B 111.0 . . ?
N1 C15 C14 103.71(10) . . ?
H15A C15 H15B 109.0 . . ?
C14 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.35(12) . . ?
C3 C2 H2 119.8 . . ?
N2 C16 H16A 111.2 . . ?
N2 C16 H16B 111.2 . . ?
N2 C16 C17 102.67(10) . . ?
H16A C16 H16B 109.1 . . ?
C17 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
N1 C12 H12A 111.3 . . ?
N1 C12 H12B 111.3 . . ?
N1 C12 C13 102.20(10) . . ?
H12A C12 H12B 109.2 . . ?
C13 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.05(12) . . ?
C7 C6 H6 119.5 . . ?
N2 C19 H19A 110.8 . . ?
N2 C19 H19B 110.8 . . ?
N2 C19 C18 104.98(10) . . ?
H19A C19 H19B 108.8 . . ?
C18 C19 H19A 110.8 . . ?
C18 C19 H19B 110.8 . . ?
C4 C3 C2 119.54(12) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C12 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
C12 C13 C14 104.57(11) . . ?
H13A C13 H13B 108.9 . . ?
C14 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
C16 C17 C18 102.77(11) . . ?
H17A C17 H17B 109.1 . . ?
C18 C17 H17A 111.2 . . ?
C18 C17 H17B 111.2 . . ?
F4 B1 F3 109.58(17) . . ?
F1 B1 F3 107.86(15) . . ?
F1 B1 F4 109.06(13) . . ?
F2 B1 F3 110.16(16) . . ?
F2 B1 F4 110.20(14) . . ?
F2 B1 F1 109.95(13) . . ?
F1A B1 F2A 105.9(10) . . ?
F1A B1 F4A 113.4(15) . . ?
F3A B1 F1A 121.8(16) . . ?
F3A B1 F2A 98.9(18) . . ?
F3A B1 F4A 108(2) . . ?
F4A B1 F2A 106.9(13) . . ?
C19 C18 C17 104.63(11) . . ?
C19 C18 H18A 110.8 . . ?
C19 C18 H18B 110.8 . . ?
C17 C18 H18A 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
C15 C14 C13 106.13(11) . . ?
C15 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
C13 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?

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
N1 C1 C2 C3 176.64(11) . . . . ?
N1 C15 C14 C13 15.66(15) . . . . ?
N1 C12 C13 C14 -33.31(14) . . . . ?
N2 C9 C8 C7 -176.82(10) . . . . ?
N2 C9 C8 C11 2.65(19) . . . . ?
N2 C16 C17 C18 -40.37(13) . . . . ?
N2 C19 C18 C17 -19.13(14) . . . . ?
C10 C9 C8 C7 0.77(18) . . . . ?
C10 C9 C8 C11 -179.76(11) . . . . ?
C10 C5 C4 C3 -1.18(18) . . . . ?
C10 C5 C6 C7 0.63(19) . . . . ?
C10 C1 C2 C3 -1.39(19) . . . . ?
C9 N2 C16 C17 163.52(10) . . . . ?
C9 N2 C19 C18 -141.61(11) . . . . ?
C9 C10 C5 C4 -178.14(11) . . . . ?
C9 C10 C5 C6 0.52(17) . . . . ?
C9 C10 C1 N1 1.20(17) . . . . ?
C9 C10 C1 C2 179.26(11) . . . . ?
C5 C10 C9 N2 176.49(10) . . . . ?
C5 C10 C9 C8 -1.22(17) . . . . ?
C5 C10 C1 N1 -176.87(10) . . . . ?
C5 C10 C1 C2 1.19(17) . . . . ?
C5 C4 C3 C2 1.02(19) . . . . ?
C4 C5 C6 C7 179.27(12) . . . . ?
C1 N1 C15 C14 -164.74(11) . . . . ?
C1 N1 C12 C13 172.46(10) . . . . ?
C1 C10 C9 N2 -1.55(17) . . . . ?
C1 C10 C9 C8 -179.25(11) . . . . ?
C1 C10 C5 C4 0.08(17) . . . . ?
C1 C10 C5 C6 178.74(11) . . . . ?
C1 C2 C3 C4 0.26(19) . . . . ?
C8 C7 C6 C5 -1.1(2) . . . . ?
C15 N1 C1 C10 -119.54(11) . . . . ?
C15 N1 C1 C2 62.34(14) . . . . ?
C15 N1 C12 C13 44.26(12) . . . . ?
C16 N2 C9 C10 115.89(11) . . . . ?
C16 N2 C9 C8 -66.41(15) . . . . ?
C16 N2 C19 C18 -6.18(13) . . . . ?
C16 C17 C18 C19 37.14(14) . . . . ?
C12 N1 C1 C10 118.28(12) . . . . ?
C12 N1 C1 C2 -59.83(15) . . . . ?
C12 N1 C15 C14 -37.26(13) . . . . ?
C12 C13 C14 C15 10.91(16) . . . . ?
C6 C5 C4 C3 -179.81(12) . . . . ?
C6 C7 C8 C9 0.42(19) . . . . ?
C6 C7 C8 C11 -179.10(12) . . . . ?
C19 N2 C9 C10 -113.22(12) . . . . ?
C19 N2 C9 C8 64.48(15) . . . . ?
C19 N2 C16 C17 29.18(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 1.534
_oxdiff_exptl_absorpt_empirical_full_min 0.770
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_preparation       Luminescent
