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

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

data_nid_enantio
_database_code_depnum_ccdc_archive 'CCDC 2321027'
loop_
_audit_author_name
_audit_author_address
'Celine Besnard'
;university of Geneva
Switzerland
;
_audit_update_record             
;
2023-12-21 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_audit_creation_date             2023-11-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N2'
_chemical_formula_sum            'C17 H16 N2'
_chemical_formula_weight         248.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H16 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'
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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   25.8699(2)
_cell_length_b                   14.53966(15)
_cell_length_c                   7.44906(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2801.89(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    50782
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      73.5160
_cell_measurement_theta_min      3.3990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
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_primary    colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0356
0 0 1 0.0356
0 -1 0 0.0787
0 1 0 0.0787
-1 0 0 0.0155
1 0 0 0.0155

_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.031
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0017 -0.0002 -0.9997 0.2067 0.0009 0.0037
-0.0017 0.0002 0.9997 -0.2067 -0.0009 -0.0037
-0.0029 -0.9994 0.0001 -0.0019 0.0371 0.0992
0.0029 0.9994 -0.0001 0.0019 -0.0371 -0.0992
-0.9995 0.0002 -0.0001 -0.0001 -0.0557 0.0209
0.9995 -0.0002 0.0001 0.0001 0.0557 -0.0209

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            85307
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.875
_diffrn_reflns_theta_min         3.417
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00 -18.00   0.50    6.00    --  -52.73   0.00 -60.00   74
  2  ω    -88.00 -24.00   0.50    6.00    --  -52.73   0.00-150.00  128
  3  ω    -76.00 -47.00   0.50    6.00    --  -52.73 125.00  30.00   58
  4  ω    -82.00 -22.00   0.50    6.00    --  -52.73 -15.00  90.00  120
  5  ω    -70.00 -38.00   0.50    6.00    --  -52.73 125.00  60.00   64
  6  ω    -78.00 -37.00   0.50    6.00    --  -52.73 125.00-180.00   82
  7  ω    -62.00 -36.00   0.50    6.00    --  -52.73 125.00  90.00   52
  8  ω     34.00  74.00   0.50    6.00    --   66.46 -94.00 -90.00   80
  9  ω     34.00  63.00   0.50    6.00    --   66.46 -94.00 120.00   58
 10  ω     38.00  66.00   0.50    6.00    --   66.46-125.00   0.00   56
 11  ω     37.00  73.00   0.50    6.00    --   66.46 -94.00  60.00   72
 12  ω     34.00  60.00   0.50    6.00    --   66.46 -94.00-180.00   52
 13  ω     29.00  70.00   0.50    6.00    --   66.46 -94.00   0.00   82
 14  ω     77.00 111.00   0.50    6.00    --   66.46  15.00 -30.00   68
 15  ω     42.00  68.00   0.50    6.00    --   66.46  15.00 -30.00   52
 16  ω     75.00 113.00   0.50    6.00    --   66.46  26.00  -5.00   76
 17  ω     29.00  55.00   0.50    6.00    --   66.46 -94.00  30.00   52
 18  ω     31.00  69.00   0.50    6.00    --   66.46 -94.00-150.00   76
 19  ω     68.00  93.00   0.50    6.00    --   66.46-125.00  90.00   50
 20  ω     71.00  97.00   0.50    6.00    --   69.88-125.00 150.00   52
 21  ω     41.00  68.00   0.50    6.00    --   69.88 -94.00 150.00   54
 22  ω     49.00  96.00   0.50    6.00    --   69.88  15.00-150.00   94
 23  ω     42.00  96.00   0.50    6.00    --   69.88-125.00 120.00  108
 24  ω     85.00 110.00   0.50    6.00    --   69.88  15.00 150.00   50
 25  ω     68.00  95.00   0.50    6.00    --   69.88   0.00-120.00   54
 26  ω     74.00  99.00   0.50    6.00    --   69.88-132.00 145.00   50
 27  ω     71.00 111.00   0.50    6.00    --   69.88  15.00 120.00   80
 28  ω     40.00  65.00   0.50    6.00    --   69.88  15.00 120.00   50
 29  ω     51.00  76.00   0.50    6.00    --   69.88  15.00 150.00   50
 30  ω      9.00  34.00   0.50    6.00    --    4.00  30.00 145.61   50
 31  ω      4.00  30.00   0.50    6.00    --   -4.00  33.00-152.91   52
 32  ω     12.00  39.00   0.50    6.00    --    8.00  29.00-149.92   54
 33  ω      1.00  27.00   0.50    6.00    --   -8.00  35.00  66.01   52
 34  ω      1.00  26.00   0.50    6.00    --   -8.00  35.00-108.57   50
 35  ω     11.00  37.00   0.50    6.00    --    8.00  29.00 119.23   52
 36  ω     14.00  40.00   0.50    6.00    --   12.00  28.00 -86.04   52
 37  ω     14.00  40.00   0.50    6.00    --   12.00  28.00 -15.15   52
 38  ω     -2.00  25.00   0.50    6.00    --  -12.00  36.00 -50.62   54
 39  ω     20.00  48.00   0.50    6.00    --   20.00  26.00  22.21   56
 40  ω     21.00  48.00   0.50    6.00    --   20.00  26.00  65.56   54
 41  ω     25.00  51.00   0.50    6.00    --   20.00  25.00-136.04   52
 42  ω    -12.00  13.00   0.50    6.00    --  -24.00  44.00   2.51   50
 43  ω    -51.00 -26.00   0.50    6.00    --  -32.00 -25.00 -48.28   50
 44  ω    -51.00 -26.00   0.50    6.00    --  -32.00 -25.00  13.94   50
 45  ω    -29.00  -3.00   0.50    6.00    --  -40.00  67.00  65.87   52
 46  ω     32.00  60.00   0.50    6.00    --   40.00  23.00 -86.02   56
 47  ω     34.00  59.00   0.50    6.00    --   48.00  23.00   0.75   50
 48  ω    -62.00 -37.00   0.50    6.00    --  -48.00 -23.00 -59.25   50
 49  ω    -62.00 -36.00   0.50    6.00    --  -48.00 -23.00-134.31   52
 50  ω    -78.00 -15.00   0.50    6.00    --  -52.73   0.00   0.00  126
 51  ω    -90.00 -37.00   0.50    6.00    --  -52.73   0.00 -90.00  106
 52  ω     41.00  69.00   0.50    6.00    --   56.00  22.00 -68.76   56
 53  ω     43.00  71.00   0.50    6.00    --   56.00  22.00  54.40   56
 54  ω    -70.00 -45.00   0.50    6.00    --  -60.00 -22.00  60.62   50
 55  ω    -70.00 -45.00   0.50    6.00    --  -60.00 -22.00  76.43   50
 56  ω    -71.00 -45.00   0.50    6.00    --  -60.50 -22.00   5.65   52
 57  ω    -50.00 -19.00   0.50    6.00    --  -60.50  61.00 -26.59   62
 58  ω    -49.00 -23.00   0.50    6.00    --  -60.50  45.00  47.63   52
 59  ω    -48.00 -22.00   0.50    6.00    --  -60.50  62.00  -4.04   52
 60  ω    -71.00 -45.00   0.50    6.00    --  -60.50 -22.00 179.33   52
 61  ω    -71.00 -46.00   0.50    6.00    --  -60.50 -22.00  -9.88   50
 62  ω    -48.00 -23.00   0.50    6.00    --  -60.50  66.00  98.25   50
 63  ω    -39.00 -14.00   0.50    6.00    --  -60.50  37.00  74.04   50
 64  ω     35.00  60.00   0.50    6.00    --   66.46-125.00 -90.00   50
 65  ω     67.00  93.00   0.50    6.00    --   66.46-125.00 -90.00   52
 66  ω     35.00  91.00   0.50    6.00    --   66.46-125.00 -30.00  112
 67  ω     38.00  64.00   0.50    6.00    --   66.46-125.00 120.00   52
 68  ω     68.00  93.00   0.50    6.00    --   66.46-125.00 150.00   50
 69  ω     35.00  61.00   0.50    6.00    --   66.46-125.00 150.00   52
 70  ω     35.00  61.00   0.50    6.00    --   69.88-125.00   0.00   52
 71  ω     33.00  62.00   0.50    6.00    --   69.88   0.00 -60.00   58
 72  ω     40.00  95.00   0.50    6.00    --   69.88   0.00 150.00  110
 73  ω     40.00  99.00   0.50    6.00    --   69.88   0.00  90.00  118
 74  ω     72.00  97.00   0.50    6.00    --   69.88-125.00   0.00   50
 75  ω     36.00  92.00   0.50    6.00    --   69.88   0.00  30.00  112
 76  ω     56.00  98.00   0.50    6.00    --   69.88   0.00 -30.00   84
 77  ω     39.00 100.00   0.50    6.00    --   69.88   0.00-150.00  122
 78  ω     72.00  97.00   0.50    6.00    --   69.88-125.00 -60.00   50
 79  ω     36.00  62.00   0.50    6.00    --   69.88-125.00 -60.00   52
 80  ω     69.00  95.00   0.50    6.00    --   69.88-125.00-150.00   52
 81  ω     35.00  61.00   0.50    6.00    --   69.88-125.00-150.00   52
 82  ω     65.00  90.00   0.50    6.00    --   69.88   0.00 -60.00   50
 83  ω     64.00 100.00   0.50    6.00    --   75.27-120.00  56.72   72
 84  ω     36.00  61.00   0.50    6.00    --   75.27-120.00  56.72   50
 85  ω     70.00 105.00   0.50    6.00    --   75.27-131.00-168.92   70
 86  ω     42.00  68.00   0.50    6.00    --   75.27-131.00-168.92   52
 87  ω     59.00 112.00   0.50    6.00    --   75.27  21.00  74.82  106
 88  ω     76.00 106.00   0.50    6.00    --   75.27-131.00  95.96   60
 89  ω     39.00  64.00   0.50    6.00    --   75.27-131.00  95.96   50
 90  ω     94.00 119.00   0.50    6.00    --   75.27  21.00 113.72   50
 91  ω     57.00  83.00   0.50    6.00    --   75.27  21.00 113.72   52
 92  ω     58.00 111.00   0.50    6.00    --   75.27  21.00-126.54  106
 93  ω     89.00 120.00   0.50    6.00    --   75.27  20.00-153.78   62
 94  ω     54.00  83.00   0.50    6.00    --   75.27  20.00-153.78   58
 95  ω     58.00  83.00   0.50    6.00    --   75.27  21.00  57.80   50
 96  ω     69.00 101.00   0.50    6.00    --   75.27  21.00  27.83   64
 97  ω     70.00  96.00   0.50    6.00    --   75.27-114.00 -89.35   52
 98  ω     37.00  98.00   0.50    6.00    --   75.27-118.00 -17.85  122
 99  ω     36.00  63.00   0.50    6.00    --   75.27-114.00 -89.35   54
100  ω     65.00  96.00   0.50    6.00    --   75.27  21.00 -40.79   62
101  ω     86.00 120.00   0.50    6.00    --   75.27  21.00-114.62   68
102  ω     57.00  83.00   0.50    6.00    --   75.27  20.00 178.08   52
103  ω     76.00 101.00   0.50    6.00    --   75.27-123.00-140.91   50
104  ω     60.00  85.00   0.50    6.00    --   75.27  21.00-114.62   50
105  ω     57.00  95.00   0.50    6.00    --   75.27  21.00   2.58   76
106  ω     50.00 101.00   0.50    6.00    --   75.27  19.00 -60.70  102
107  ω     34.00  60.00   0.50    6.00    --   75.27-123.00-140.91   52
108  ω     94.00 120.00   0.50    6.00    --   75.27  21.00 130.01   52
109  ω     54.00 104.00   0.50    6.00    --   75.27  20.00 -53.29  100
110  ω     60.00  85.00   0.50    6.00    --   75.27  21.00 130.01   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001445000
_diffrn_orient_matrix_UB_12      0.0018664000
_diffrn_orient_matrix_UB_13      -0.2067417000
_diffrn_orient_matrix_UB_21      0.0557637000
_diffrn_orient_matrix_UB_22      -0.0372640000
_diffrn_orient_matrix_UB_23      -0.0008131000
_diffrn_orient_matrix_UB_31      -0.0209133000
_diffrn_orient_matrix_UB_32      -0.0991780000
_diffrn_orient_matrix_UB_33      -0.0036780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                5436
_reflns_number_total             5555
_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 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 2246 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The resonant scattering is weak for this sample (Friedif 12) 
 as reflected by the large error of the refined Flack parameter (-0.1(4)). 
 However, all indicators confirm the absolute structure (Hooft -0.05(6) 
 with P3(true)=1 and the post refinement Parsons-Flack 
 x determined using 2246 quotients is -0.03(7)  
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_coef       0.00139(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+0.4160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0759
_refine_special_details          
;
 
 The resonant scattering is weak for this sample (Friedif 12) 
 as reflected by the large error of the refined Flack parameter (-0.1(4)). 
 However, all indicators confirm the absolute structure (Hooft -0.05(6) 
 with P3(true)=1 and the post refinement Parsons-Flack 
 x determined using 2246 quotients is -0.03(7)  
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C13(H13), C18(H18), C5B(H5B), C16(H16), C17(H17), C4B(H4B),
 C18B(H18B), C12B(H12B), C15(H15), C13B(H13B), C15B(H15B), C12(H12), C17B(H17B),
  C16B(H16B)
2.b Idealised Me refined as rotating group:
 C11(H11D,H11E,H11F), C7B(H7BA,H7BB,H7BC), C7(H7A,H7B,H7C), C11B(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
N1B N 0.69827(5) 0.38325(9) 0.86516(19) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.79450(5) 0.23301(9) 0.67366(19) 0.0282(3) Uani 1 1 d . . . . .
N3B N 0.76941(6) 0.43572(11) 0.7117(2) 0.0358(3) Uani 1 1 d . . . . .
C10 C 0.90664(6) 0.33335(11) 0.6930(2) 0.0278(3) Uani 1 1 d . . . . .
N3 N 0.71694(6) 0.18123(12) 0.7843(3) 0.0478(5) Uani 1 1 d . . . . .
C9 C 0.87183(6) 0.30297(11) 0.5662(2) 0.0253(3) Uani 1 1 d . . . . .
C9B C 0.62496(6) 0.31416(11) 1.0096(2) 0.0279(3) Uani 1 1 d . . . . .
C4 C 0.77610(6) 0.07182(11) 0.6512(2) 0.0295(4) Uani 1 1 d . . . . .
H4 H 0.753247 0.021802 0.672103 0.035 Uiso 1 1 calc R U . . .
C8B C 0.65417(6) 0.39920(11) 0.9572(2) 0.0269(3) Uani 1 1 d . . . . .
C2B C 0.72639(6) 0.45548(11) 0.8090(2) 0.0280(3) Uani 1 1 d . . . . .
C5 C 0.82288(7) 0.05790(11) 0.5704(2) 0.0293(4) Uani 1 1 d . . . . .
H5 H 0.832324 -0.002440 0.534096 0.035 Uiso 1 1 calc R U . . .
C8 C 0.84052(6) 0.21693(10) 0.5948(2) 0.0251(3) Uani 1 1 d . . . . .
C19 C 0.86196(6) 0.35511(11) 0.4075(2) 0.0262(3) Uani 1 1 d . . . . .
C6 C 0.85724(6) 0.13093(11) 0.5398(2) 0.0277(3) Uani 1 1 d . . . . .
C14 C 0.88793(6) 0.44061(11) 0.3818(2) 0.0279(3) Uani 1 1 d . . . . .
C2 C 0.76245(6) 0.16168(11) 0.7030(2) 0.0301(3) Uani 1 1 d . . . . .
C13 C 0.92273(6) 0.47138(11) 0.5160(2) 0.0307(4) Uani 1 1 d . . . . .
H13 H 0.939941 0.528647 0.501951 0.037 Uiso 1 1 calc R U . . .
C10B C 0.63562(6) 0.26851(12) 1.1673(2) 0.0316(4) Uani 1 1 d . . . . .
C18 C 0.82702(6) 0.32487(11) 0.2731(2) 0.0300(4) Uani 1 1 d . . . . .
H18 H 0.809149 0.268383 0.289111 0.036 Uiso 1 1 calc R U . . .
C19B C 0.58629(6) 0.28127(11) 0.8888(2) 0.0294(4) Uani 1 1 d . . . . .
C6B C 0.63555(6) 0.48621(12) 0.9967(2) 0.0310(4) Uani 1 1 d . . . . .
C5B C 0.66658(7) 0.56014(12) 0.9427(2) 0.0348(4) Uani 1 1 d . . . . .
H5B H 0.656115 0.621161 0.970160 0.042 Uiso 1 1 calc R U . . .
C16 C 0.84472(7) 0.46022(12) 0.0958(3) 0.0349(4) Uani 1 1 d . . . . .
H16 H 0.838982 0.495212 -0.010063 0.042 Uiso 1 1 calc R U . . .
C17 C 0.81851(7) 0.37543(12) 0.1208(3) 0.0342(4) Uani 1 1 d . . . . .
H17 H 0.795106 0.353786 0.032093 0.041 Uiso 1 1 calc R U . . .
C4B C 0.71176(7) 0.54597(11) 0.8509(2) 0.0317(4) Uani 1 1 d . . . . .
H4B H 0.732820 0.596453 0.816153 0.038 Uiso 1 1 calc R U . . .
C18B C 0.57650(7) 0.32379(12) 0.7211(3) 0.0345(4) Uani 1 1 d . . . . .
H18B H 0.595700 0.376791 0.687713 0.041 Uiso 1 1 calc R U . . .
C12B C 0.60613(7) 0.18883(12) 1.2112(3) 0.0376(4) Uani 1 1 d . . . . .
H12B H 0.613061 0.156980 1.319898 0.045 Uiso 1 1 calc R U . . .
C14B C 0.55716(6) 0.20147(12) 0.9356(3) 0.0341(4) Uani 1 1 d . . . . .
C15 C 0.87809(6) 0.49147(11) 0.2234(2) 0.0330(4) Uani 1 1 d . . . . .
H15 H 0.895131 0.548629 0.205670 0.040 Uiso 1 1 calc R U . . .
C13B C 0.56824(7) 0.15751(12) 1.1003(3) 0.0389(4) Uani 1 1 d . . . . .
H13B H 0.548794 0.104896 1.134330 0.047 Uiso 1 1 calc R U . . .
C15B C 0.51928(7) 0.16880(13) 0.8145(3) 0.0413(5) Uani 1 1 d . . . . .
H15B H 0.499442 0.116123 0.845205 0.050 Uiso 1 1 calc R U . . .
C12 C 0.93167(6) 0.41933(11) 0.6652(2) 0.0303(4) Uani 1 1 d . . . . .
H12 H 0.955286 0.441129 0.753057 0.036 Uiso 1 1 calc R U . . .
C11 C 0.91976(7) 0.27870(12) 0.8578(2) 0.0350(4) Uani 1 1 d . . . . .
H11D H 0.894057 0.229938 0.874510 0.052 Uiso 1 1 calc R U . . .
H11E H 0.919698 0.319313 0.962786 0.052 Uiso 1 1 calc R U . . .
H11F H 0.954103 0.251169 0.843678 0.052 Uiso 1 1 calc R U . . .
C7B C 0.58455(7) 0.50004(14) 1.0914(3) 0.0440(5) Uani 1 1 d . . . . .
H7BA H 0.556634 0.474069 1.018311 0.066 Uiso 1 1 calc R U . . .
H7BB H 0.578479 0.565954 1.109054 0.066 Uiso 1 1 calc R U . . .
H7BC H 0.585437 0.469095 1.208193 0.066 Uiso 1 1 calc R U . . .
C7 C 0.90881(7) 0.11658(12) 0.4495(3) 0.0367(4) Uani 1 1 d . . . . .
H7A H 0.936623 0.126730 0.536635 0.055 Uiso 1 1 calc R U . . .
H7B H 0.912458 0.160131 0.349923 0.055 Uiso 1 1 calc R U . . .
H7C H 0.910855 0.053566 0.403397 0.055 Uiso 1 1 calc R U . . .
C17B C 0.54000(7) 0.28996(14) 0.6068(3) 0.0422(4) Uani 1 1 d . . . . .
H17B H 0.534161 0.319166 0.494563 0.051 Uiso 1 1 calc R U . . .
C11B C 0.67748(7) 0.29890(13) 1.2955(3) 0.0399(4) Uani 1 1 d . . . . .
H11A H 0.704705 0.252095 1.299809 0.060 Uiso 1 1 calc R U . . .
H11B H 0.662726 0.307024 1.415588 0.060 Uiso 1 1 calc R U . . .
H11C H 0.692168 0.357307 1.254136 0.060 Uiso 1 1 calc R U . . .
C16B C 0.51077(7) 0.21141(14) 0.6550(3) 0.0452(5) Uani 1 1 d . . . . .
H16B H 0.485125 0.188446 0.575426 0.054 Uiso 1 1 calc R U . . .
H3BA H 0.7765(8) 0.3758(17) 0.690(3) 0.047(6) Uiso 1 1 d . . . . .
H3BB H 0.7874(9) 0.4807(17) 0.657(3) 0.052(6) Uiso 1 1 d . . . . .
H3A H 0.7092(8) 0.2393(17) 0.808(3) 0.047(6) Uiso 1 1 d . . . . .
H3B H 0.6935(9) 0.1360(17) 0.807(3) 0.052(6) Uiso 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
N1B C8B 1.351(2) . ?
N1B C2B 1.344(2) . ?
N1 C8 1.348(2) . ?
N1 C2 1.346(2) . ?
N3B C2B 1.359(2) . ?
N3B H3BA 0.91(2) . ?
N3B H3BB 0.90(2) . ?
C10 C9 1.378(2) . ?
C10 C12 1.423(2) . ?
C10 C11 1.501(2) . ?
N3 C2 1.354(2) . ?
N3 H3A 0.89(2) . ?
N3 H3B 0.91(2) . ?
C9 C8 1.505(2) . ?
C9 C19 1.427(2) . ?
C9B C8B 1.501(2) . ?
C9B C10B 1.377(2) . ?
C9B C19B 1.428(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.367(2) . ?
C4 C2 1.407(2) . ?
C8B C6B 1.385(2) . ?
C2B C4B 1.404(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.403(2) . ?
C8 C6 1.385(2) . ?
C19 C14 1.426(2) . ?
C19 C18 1.419(2) . ?
C6 C7 1.508(2) . ?
C14 C13 1.418(2) . ?
C14 C15 1.416(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.364(2) . ?
C10B C12B 1.425(2) . ?
C10B C11B 1.509(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.370(2) . ?
C19B C18B 1.417(3) . ?
C19B C14B 1.427(2) . ?
C6B C5B 1.401(2) . ?
C6B C7B 1.509(2) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.370(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.419(2) . ?
C16 C15 1.362(3) . ?
C17 H17 0.9500 . ?
C4B H4B 0.9500 . ?
C18B H18B 0.9500 . ?
C18B C17B 1.363(3) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.360(3) . ?
C14B C13B 1.412(3) . ?
C14B C15B 1.415(3) . ?
C15 H15 0.9500 . ?
C13B H13B 0.9500 . ?
C15B H15B 0.9500 . ?
C15B C16B 1.358(3) . ?
C12 H12 0.9500 . ?
C11 H11D 0.9800 . ?
C11 H11E 0.9800 . ?
C11 H11F 0.9800 . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C17B H17B 0.9500 . ?
C17B C16B 1.416(3) . ?
C11B H11A 0.9800 . ?
C11B H11B 0.9800 . ?
C11B H11C 0.9800 . ?
C16B H16B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2B N1B C8B 118.73(14) . . ?
C2 N1 C8 118.77(14) . . ?
C2B N3B H3BA 117.7(14) . . ?
C2B N3B H3BB 120.7(15) . . ?
H3BA N3B H3BB 121(2) . . ?
C9 C10 C12 118.64(15) . . ?
C9 C10 C11 122.59(14) . . ?
C12 C10 C11 118.76(15) . . ?
C2 N3 H3A 119.1(14) . . ?
C2 N3 H3B 120.7(15) . . ?
H3A N3 H3B 120(2) . . ?
C10 C9 C8 121.42(14) . . ?
C10 C9 C19 120.95(14) . . ?
C19 C9 C8 117.53(14) . . ?
C10B C9B C8B 121.21(15) . . ?
C10B C9B C19B 121.09(15) . . ?
C19B C9B C8B 117.69(15) . . ?
C5 C4 H4 120.6 . . ?
C5 C4 C2 118.70(15) . . ?
C2 C4 H4 120.6 . . ?
N1B C8B C9B 114.58(14) . . ?
N1B C8B C6B 123.93(15) . . ?
C6B C8B C9B 121.46(15) . . ?
N1B C2B N3B 116.36(15) . . ?
N1B C2B C4B 121.15(15) . . ?
N3B C2B C4B 122.50(15) . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.36(15) . . ?
C6 C5 H5 119.3 . . ?
N1 C8 C9 113.12(13) . . ?
N1 C8 C6 124.14(14) . . ?
C6 C8 C9 122.71(14) . . ?
C14 C19 C9 119.35(15) . . ?
C18 C19 C9 122.26(14) . . ?
C18 C19 C14 118.40(15) . . ?
C5 C6 C7 121.86(15) . . ?
C8 C6 C5 115.93(14) . . ?
C8 C6 C7 122.20(14) . . ?
C13 C14 C19 118.65(15) . . ?
C15 C14 C19 118.86(16) . . ?
C15 C14 C13 122.49(15) . . ?
N1 C2 N3 116.52(15) . . ?
N1 C2 C4 121.10(15) . . ?
N3 C2 C4 122.38(15) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.46(15) . . ?
C12 C13 H13 119.8 . . ?
C9B C10B C12B 118.68(16) . . ?
C9B C10B C11B 122.82(15) . . ?
C12B C10B C11B 118.50(16) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 C19 121.36(15) . . ?
C17 C18 H18 119.3 . . ?
C18B C19B C9B 122.32(15) . . ?
C18B C19B C14B 118.41(16) . . ?
C14B C19B C9B 119.24(16) . . ?
C8B C6B C5B 116.13(15) . . ?
C8B C6B C7B 121.67(15) . . ?
C5B C6B C7B 122.20(16) . . ?
C6B C5B H5B 119.4 . . ?
C4B C5B C6B 121.14(16) . . ?
C4B C5B H5B 119.4 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.06(16) . . ?
C18 C17 C16 119.89(17) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C2B C4B H4B 120.6 . . ?
C5B C4B C2B 118.80(15) . . ?
C5B C4B H4B 120.6 . . ?
C19B C18B H18B 119.4 . . ?
C17B C18B C19B 121.14(17) . . ?
C17B C18B H18B 119.4 . . ?
C10B C12B H12B 119.4 . . ?
C13B C12B C10B 121.25(18) . . ?
C13B C12B H12B 119.4 . . ?
C13B C14B C19B 118.23(16) . . ?
C13B C14B C15B 122.86(17) . . ?
C15B C14B C19B 118.89(18) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.42(15) . . ?
C16 C15 H15 119.3 . . ?
C12B C13B C14B 121.46(17) . . ?
C12B C13B H13B 119.3 . . ?
C14B C13B H13B 119.3 . . ?
C14B C15B H15B 119.4 . . ?
C16B C15B C14B 121.16(18) . . ?
C16B C15B H15B 119.4 . . ?
C10 C12 H12 119.0 . . ?
C13 C12 C10 121.93(16) . . ?
C13 C12 H12 119.0 . . ?
C10 C11 H11D 109.5 . . ?
C10 C11 H11E 109.5 . . ?
C10 C11 H11F 109.5 . . ?
H11D C11 H11E 109.5 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
C6B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C18B C17B H17B 119.9 . . ?
C18B C17B C16B 120.2(2) . . ?
C16B C17B H17B 119.9 . . ?
C10B C11B H11A 109.5 . . ?
C10B C11B H11B 109.5 . . ?
C10B C11B H11C 109.5 . . ?
H11A C11B H11B 109.5 . . ?
H11A C11B H11C 109.5 . . ?
H11B C11B H11C 109.5 . . ?
C15B C16B C17B 120.19(17) . . ?
C15B C16B H16B 119.9 . . ?
C17B C16B H16B 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1B C8B C6B C5B -2.9(2) . . . . ?
N1B C8B C6B C7B 176.67(16) . . . . ?
N1B C2B C4B C5B -3.4(3) . . . . ?
N1 C8 C6 C5 0.1(2) . . . . ?
N1 C8 C6 C7 179.07(16) . . . . ?
N3B C2B C4B C5B 177.07(16) . . . . ?
C10 C9 C8 N1 91.34(18) . . . . ?
C10 C9 C8 C6 -90.5(2) . . . . ?
C10 C9 C19 C14 -1.1(2) . . . . ?
C10 C9 C19 C18 178.89(15) . . . . ?
C9 C10 C12 C13 -1.0(2) . . . . ?
C9 C8 C6 C5 -177.83(15) . . . . ?
C9 C8 C6 C7 1.1(2) . . . . ?
C9 C19 C14 C13 -0.3(2) . . . . ?
C9 C19 C14 C15 179.62(14) . . . . ?
C9 C19 C18 C17 -179.27(15) . . . . ?
C9B C8B C6B C5B 179.29(16) . . . . ?
C9B C8B C6B C7B -1.1(3) . . . . ?
C9B C10B C12B C13B 0.3(3) . . . . ?
C9B C19B C18B C17B 178.77(16) . . . . ?
C9B C19B C14B C13B -0.6(2) . . . . ?
C9B C19B C14B C15B -179.39(15) . . . . ?
C4 C5 C6 C8 -0.6(2) . . . . ?
C4 C5 C6 C7 -179.56(17) . . . . ?
C8B N1B C2B N3B -177.75(15) . . . . ?
C8B N1B C2B C4B 2.6(2) . . . . ?
C8B C9B C10B C12B 179.17(15) . . . . ?
C8B C9B C10B C11B -1.2(2) . . . . ?
C8B C9B C19B C18B 2.6(2) . . . . ?
C8B C9B C19B C14B -178.99(14) . . . . ?
C8B C6B C5B C4B 2.1(3) . . . . ?
C2B N1B C8B C9B 178.51(14) . . . . ?
C2B N1B C8B C6B 0.6(2) . . . . ?
C5 C4 C2 N1 0.2(3) . . . . ?
C5 C4 C2 N3 -179.78(18) . . . . ?
C8 N1 C2 N3 179.31(17) . . . . ?
C8 N1 C2 C4 -0.6(2) . . . . ?
C8 C9 C19 C14 175.30(13) . . . . ?
C8 C9 C19 C18 -4.7(2) . . . . ?
C19 C9 C8 N1 -85.04(17) . . . . ?
C19 C9 C8 C6 93.13(19) . . . . ?
C19 C14 C13 C12 1.0(2) . . . . ?
C19 C14 C15 C16 -0.3(2) . . . . ?
C19 C18 C17 C16 -0.4(3) . . . . ?
C14 C19 C18 C17 0.7(2) . . . . ?
C14 C13 C12 C10 -0.4(2) . . . . ?
C2 N1 C8 C9 178.63(14) . . . . ?
C2 N1 C8 C6 0.5(2) . . . . ?
C2 C4 C5 C6 0.5(2) . . . . ?
C13 C14 C15 C16 179.60(16) . . . . ?
C10B C9B C8B N1B 87.45(19) . . . . ?
C10B C9B C8B C6B -94.6(2) . . . . ?
C10B C9B C19B C18B -176.37(15) . . . . ?
C10B C9B C19B C14B 2.1(2) . . . . ?
C10B C12B C13B C14B 1.2(3) . . . . ?
C18 C19 C14 C13 179.72(14) . . . . ?
C18 C19 C14 C15 -0.4(2) . . . . ?
C19B C9B C8B N1B -91.51(17) . . . . ?
C19B C9B C8B C6B 86.48(19) . . . . ?
C19B C9B C10B C12B -1.9(2) . . . . ?
C19B C9B C10B C11B 177.70(15) . . . . ?
C19B C18B C17B C16B 0.4(3) . . . . ?
C19B C14B C13B C12B -1.0(2) . . . . ?
C19B C14B C15B C16B 0.7(2) . . . . ?
C6B C5B C4B C2B 0.9(3) . . . . ?
C17 C16 C15 C14 0.7(3) . . . . ?
C18B C19B C14B C13B 177.93(15) . . . . ?
C18B C19B C14B C15B -0.9(2) . . . . ?
C18B C17B C16B C15B -0.6(3) . . . . ?
C14B C19B C18B C17B 0.3(2) . . . . ?
C14B C15B C16B C17B 0.1(3) . . . . ?
C15 C14 C13 C12 -178.91(15) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C13B C14B C15B C16B -178.05(16) . . . . ?
C15B C14B C13B C12B 177.73(17) . . . . ?
C12 C10 C9 C8 -174.52(14) . . . . ?
C12 C10 C9 C19 1.7(2) . . . . ?
C11 C10 C9 C8 6.4(2) . . . . ?
C11 C10 C9 C19 -177.37(15) . . . . ?
C11 C10 C12 C13 178.11(15) . . . . ?
C7B C6B C5B C4B -177.48(17) . . . . ?
C11B C10B C12B C13B -179.34(16) . . . . ?

_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 2.015
_oxdiff_exptl_absorpt_empirical_full_min 0.497
