# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_h
_audit_block_doi                 10.5517/ccdc.csd.cc2bcyl8
_database_code_depnum_ccdc_archive 'CCDC 2156440'
loop_
_audit_author_name
_audit_author_address
'Qun-Liang Zhang'
;Wuhan University of Technology
China
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-03-20 downloaded from the CCDC.
;
_audit_creation_date             2022-02-22
_audit_creation_method           
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 N'
_chemical_formula_sum            'C19 H13 N'
_chemical_formula_weight         255.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3350(2)
_cell_length_b                   8.0285(2)
_cell_length_c                   12.0544(2)
_cell_angle_alpha                96.504(2)
_cell_angle_beta                 95.479(2)
_cell_angle_gamma                111.870(2)
_cell_volume                     647.21(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6028
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.5590
_cell_measurement_theta_min      3.7130
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12073
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.859
_diffrn_reflns_theta_min         3.732
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.961
_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 -24.00   0.50    0.20    --  -43.18 -37.00 -90.00   58
  2  ω    -56.00 -21.00   0.50    0.20    --  -43.18 -57.00-150.00   70
  3  ω    -72.00 -14.00   0.50    0.20    --  -43.18 -77.00-180.00  116
  4  ω    -83.00 -16.00   0.50    0.20    --  -43.18 -77.00 -90.00  134
  5  ω    -68.00 -15.00   0.50    0.20    --  -43.18 -77.00  30.00  106
  6  ω    -43.00 -14.00   0.50    0.20    --  -43.18 -77.00  90.00   58
  7  ω    -66.00 -21.00   0.50    0.20    --  -43.18 -57.00  90.00   90
  8  ω    -91.00 -17.00   0.50    0.20    --  -43.18 -77.00 -30.00  148
  9  ω    -87.00 -61.00   0.50    1.00    --  -90.25 -77.00  60.00   52
 10  ω    -90.00 -62.00   0.50    1.00    --  -90.25 -77.00 120.00   56
 11  ω    -92.00 -64.00   0.50    1.00    --  -90.25 -71.00 153.94   56
 12  ω    -88.00 -62.00   0.50    1.00    --  -90.25 -74.00  94.80   52
 13  ω    -95.00 -69.00   0.50    1.00    --  -90.25 -61.00  30.00   52
 14  ω    -87.00 -61.00   0.50    1.00    --  -90.25 -77.00  30.00   52
 15  ω    -90.00 -62.00   0.50    1.00    --  -90.25 -77.00 -30.00   56
 16  ω    -86.00 -61.00   0.50    1.00    --  -90.25 -77.00 -60.00   50
 17  ω    -90.00 -61.00   0.50    1.00    --  -90.25 -77.00-120.00   58
 18  ω   -101.00 -62.00   0.50    1.00    --  -90.25 -74.00-172.16   78
 19  ω    -99.00 -60.00   0.50    1.00    --  -90.25 -79.00-138.58   78
 20  ω    -94.00 -60.00   0.50    1.00    --  -90.25 -82.00 -78.70   68
 21  ω    -99.00 -62.00   0.50    1.00    --  -90.25 -80.00 -39.90   74
 22  ω    -96.00 -61.00   0.50    1.00    --  -90.25 -77.00 -67.13   70
 23  ω    -95.00 -61.00   0.50    1.00    --  -90.25 -78.00 -98.79   68
 24  ω   -113.00 -63.00   0.50    0.20    --  -43.18 -57.00-150.00  100
 25  ω   -117.00 -77.00   0.50    0.20    --  -43.18 -77.00-180.00   80
 26  ω   -123.00 -62.00   0.50    1.00    --  -90.25 -77.00-180.00  122
 27  ω   -142.00-116.00   0.50    1.00    --  -90.25 -77.00 -60.00   52
 28  ω    -99.00 -62.00   0.50    1.00    --  -90.25 -81.00  -5.57   74
 29  ω   -103.00 -67.00   0.50    1.00    --  -90.25 -61.00  60.00   72
 30  ω    -98.00 -70.00   0.50    1.00    --  -90.25 -51.00  97.11   56
 31  ω   -111.00 -65.00   0.50    1.00    --  -90.25 -77.00 150.00   92
 32  ω    -92.00 -46.00   0.50    0.20    --  -43.18 -77.00  90.00   92
 33  ω   -117.00 -74.00   0.50    0.20    --  -43.18 -77.00  30.00   86
 34  ω   -142.00-116.00   0.50    1.00    --  -90.25 -71.00 153.94   52
 35  ω   -155.00-129.00   0.50    1.00    --  -90.25-109.00  41.00   52
 36  ω   -160.00 -61.00   0.50    1.00    --  -90.25 -77.00   0.00  198
 37  ω   -150.00-124.00   0.50    1.00    --  -90.25 -77.00-180.00   52
 38  ω   -153.00-127.00   0.50    1.00    --  -90.25 -77.00-120.00   52
 39  ω   -155.00-123.00   0.50    1.00    --  -90.25 -78.00 -98.79   64
 40  ω   -163.00-125.00   0.50    1.00    --  -90.25 -77.00 -30.00   76
 41  ω   -164.00-110.00   0.50    1.00    --  -90.25 -77.00  60.00  108
 42  ω   -164.00-118.00   0.50    1.00    --  -90.25 -77.00 150.00   92
 43  ω    -86.00 -12.00   0.50    0.20    --  -43.18 109.00 138.00  148
 44  ω     19.00  61.00   0.50    0.20    --   43.18-109.00  41.00   84
 45  ω     34.00  94.00   0.50    0.20    --   43.18-125.00 -60.00  120
 46  ω     74.00 114.00   0.50    1.00    --  109.88-109.00  41.00   80
 47  ω     73.00 108.00   0.50    1.00    --  109.88 -94.00  60.00   70
 48  ω     92.00 123.00   0.50    1.00    --  109.88 -45.00 -60.00   62
 49  ω     86.00 178.00   0.50    1.00    --  109.88  30.00  60.00  184
 50  ω    149.00 177.00   0.50    1.00    --  109.88 125.00 -30.00   56
 51  ω    143.00 171.00   0.50    1.00    --  109.88  77.00 -60.00   56
 52  ω    112.00 138.00   0.50    1.00    --  109.88  61.00 -30.00   52
 53  ω     97.00 144.00   0.50    1.00    --  109.88 125.00 -30.00   94
 54  ω     88.00 178.00   0.50    1.00    --  109.88  61.00 -90.00  180
 55  ω     93.00 139.00   0.50    1.00    --  109.88 125.00-180.00   92
 56  ω     95.00 178.00   0.50    1.00    --  109.88  77.00-150.00  166
 57  ω     92.00 117.00   0.50    1.00    --  109.88  77.00 -60.00   50
 58  ω     89.00 177.00   0.50    1.00    --  109.88  61.00  90.00  176
 59  ω    102.00 167.00   0.50    1.00    --  109.88 109.00 138.00  130
 60  ω     90.00 139.00   0.50    1.00    --  109.88  61.00 150.00   98
 61  ω     94.00 120.00   0.50    1.00    --  109.88  61.00 120.00   52
 62  ω     38.00  70.00   0.50    1.00    --  109.88 -45.00 -60.00   64
 63  ω     44.00  84.00   0.50    1.00    --  109.88 -94.00   0.00   80
 64  ω     36.00 107.00   0.50    1.00    --  109.88 -94.00 -90.00  142
 65  ω     36.00 102.00   0.50    1.00    --  109.88 -94.00-120.00  132
 66  ω      7.00  42.00   0.50    0.20    --   43.18 -57.00-150.00   70
 67  ω    -75.00 -50.00   0.50    1.00    --  -90.25 109.00 138.00   50
 68  ω     36.00 101.00   0.50    1.00    --  109.88 -94.00 120.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0252039000
_diffrn_orient_matrix_UB_12      -0.1992835000
_diffrn_orient_matrix_UB_13      -0.0000700000
_diffrn_orient_matrix_UB_21      -0.0171086000
_diffrn_orient_matrix_UB_22      0.0204234000
_diffrn_orient_matrix_UB_23      0.1267785000
_diffrn_orient_matrix_UB_31      -0.2268455000
_diffrn_orient_matrix_UB_32      -0.0613263000
_diffrn_orient_matrix_UB_33      -0.0291515000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2253
_reflns_number_total             2580
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.081
_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)+(0.0741P)²+0.0765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1259
_refine_special_details          ?
_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:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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
N1 N 0.68252(15) 0.84323(14) 0.56899(8) 0.0417(3) Uani 1 1 d . . . . .
C1 C -0.05439(16) 0.43538(15) 0.53272(9) 0.0363(3) Uani 1 1 d . . . . .
C2 C 0.05531(17) 0.38268(17) 0.61617(9) 0.0405(3) Uani 1 1 d . . . . .
H2 H -0.009774 0.281768 0.649274 0.049 Uiso 1 1 calc R U . . .
C3 C 0.25318(17) 0.47770(17) 0.64790(9) 0.0409(3) Uani 1 1 d . . . . .
H3 H 0.318701 0.449202 0.708224 0.049 Uiso 1 1 calc R U . . .
C4 C 0.36253(17) 0.61980(16) 0.59100(9) 0.0374(3) Uani 1 1 d . . . . .
C5 C 0.26909(16) 0.64454(15) 0.49057(9) 0.0358(3) Uani 1 1 d . . . . .
C6 C 0.39811(17) 0.74516(15) 0.41646(9) 0.0369(3) Uani 1 1 d . . . . .
C7 C 0.34064(18) 0.73901(17) 0.30035(10) 0.0421(3) Uani 1 1 d . . . . .
H7 H 0.210212 0.668847 0.267521 0.050 Uiso 1 1 calc R U . . .
C8 C 0.4731(2) 0.83424(19) 0.23518(11) 0.0493(3) Uani 1 1 d . . . . .
H8 H 0.431522 0.827732 0.158893 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6693(2) 0.94074(19) 0.28183(11) 0.0509(3) Uani 1 1 d . . . . .
H9 H 0.756600 1.009074 0.237620 0.061 Uiso 1 1 calc R U . . .
C10 C 0.73329(19) 0.94468(17) 0.39264(11) 0.0454(3) Uani 1 1 d . . . . .
H10 H 0.864789 1.014948 0.423382 0.055 Uiso 1 1 calc R U . . .
C11 C 0.60184(17) 0.84320(16) 0.46085(10) 0.0384(3) Uani 1 1 d . . . . .
C12 C 0.57048(17) 0.73289(16) 0.62944(9) 0.0393(3) Uani 1 1 d . . . . .
C13 C 0.66643(18) 0.73295(17) 0.74415(10) 0.0413(3) Uani 1 1 d . . . . .
C14 C 0.85481(18) 0.73028(17) 0.75830(10) 0.0447(3) Uani 1 1 d . . . . .
H14 H 0.920389 0.729047 0.696073 0.054 Uiso 1 1 calc R U . . .
C15 C 0.9469(2) 0.72941(19) 0.86391(11) 0.0517(3) Uani 1 1 d . . . . .
H15 H 1.072849 0.726225 0.871282 0.062 Uiso 1 1 calc R U . . .
C16 C 0.8544(2) 0.7332(2) 0.95924(11) 0.0556(4) Uani 1 1 d . . . . .
C17 C 0.9558(3) 0.7335(3) 1.07465(14) 0.0808(5) Uani 1 1 d . . . . .
H17A H 1.028680 0.656199 1.067713 0.121 Uiso 1 1 calc R U . . .
H17B H 0.857563 0.689198 1.123021 0.121 Uiso 1 1 calc R U . . .
H17C H 1.045364 0.855102 1.106440 0.121 Uiso 1 1 calc R U . . .
C18 C 0.6682(2) 0.7391(3) 0.94475(12) 0.0649(4) Uani 1 1 d . . . . .
H18 H 0.604100 0.743791 1.007270 0.078 Uiso 1 1 calc R U . . .
C19 C 0.5746(2) 0.7382(2) 0.83930(11) 0.0565(4) Uani 1 1 d . . . . .
H19 H 0.448531 0.741238 0.832046 0.068 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.3791(15) . ?
N1 C12 1.3073(16) . ?
C1 C1 1.423(2) 2_566 ?
C1 C2 1.4262(16) . ?
C1 C5 1.4466(16) 2_566 ?
C2 H2 0.9300 . ?
C2 C3 1.3557(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.4198(16) . ?
C4 C5 1.4044(15) . ?
C4 C12 1.4504(16) . ?
C5 C6 1.4498(15) . ?
C6 C7 1.4125(15) . ?
C6 C11 1.4194(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.3689(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.3922(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3658(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.4097(16) . ?
C12 C13 1.4904(15) . ?
C13 C14 1.3845(18) . ?
C13 C19 1.3888(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.3850(17) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(2) . ?
C16 C17 1.5129(18) . ?
C16 C18 1.380(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18 0.9300 . ?
C18 C19 1.3838(19) . ?
C19 H19 0.9300 . ?

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
C12 N1 C11 118.15(10) . . ?
C1 C1 C2 117.85(13) 2_566 . ?
C1 C1 C5 119.80(13) 2_566 2_566 ?
C2 C1 C5 122.27(10) . 2_566 ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.89(11) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.41(10) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C12 122.19(10) . . ?
C5 C4 C3 118.74(10) . . ?
C5 C4 C12 118.96(10) . . ?
C1 C5 C6 125.10(10) 2_566 . ?
C4 C5 C1 118.28(10) . 2_566 ?
C4 C5 C6 116.60(10) . . ?
C7 C6 C5 124.83(11) . . ?
C7 C6 C11 117.24(10) . . ?
C11 C6 C5 117.64(10) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.33(11) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.73(11) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.88(11) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.60(11) . . ?
C11 C10 H10 119.7 . . ?
N1 C11 C6 123.35(10) . . ?
N1 C11 C10 116.73(10) . . ?
C10 C11 C6 119.91(11) . . ?
N1 C12 C4 123.16(10) . . ?
N1 C12 C13 116.17(10) . . ?
C4 C12 C13 120.63(10) . . ?
C14 C13 C12 119.72(11) . . ?
C14 C13 C19 117.97(11) . . ?
C19 C13 C12 122.30(11) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.86(12) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.26(13) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 121.17(14) . . ?
C18 C16 C15 117.52(12) . . ?
C18 C16 C17 121.30(14) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18 119.2 . . ?
C16 C18 C19 121.50(13) . . ?
C19 C18 H18 119.2 . . ?
C13 C19 H19 119.6 . . ?
C18 C19 C13 120.87(13) . . ?
C18 C19 H19 119.6 . . ?

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 C12 C13 C14 -44.71(16) . . . . ?
N1 C12 C13 C19 134.35(14) . . . . ?
C1 C1 C2 C3 13.0(2) 2_566 . . . ?
C1 C2 C3 C4 -7.11(19) . . . . ?
C1 C5 C6 C7 -18.05(19) 2_566 . . . ?
C1 C5 C6 C11 168.37(11) 2_566 . . . ?
C2 C3 C4 C5 -9.01(18) . . . . ?
C2 C3 C4 C12 174.75(11) . . . . ?
C3 C4 C5 C1 18.42(16) . . . 2_566 ?
C3 C4 C5 C6 -159.88(11) . . . . ?
C3 C4 C12 N1 168.21(11) . . . . ?
C3 C4 C12 C13 -13.92(17) . . . . ?
C4 C5 C6 C7 160.12(11) . . . . ?
C4 C5 C6 C11 -13.46(16) . . . . ?
C4 C12 C13 C14 137.28(12) . . . . ?
C4 C12 C13 C19 -43.66(18) . . . . ?
C5 C1 C2 C3 -170.19(11) 2_566 . . . ?
C5 C4 C12 N1 -8.02(18) . . . . ?
C5 C4 C12 C13 169.85(10) . . . . ?
C5 C6 C7 C8 -178.11(12) . . . . ?
C5 C6 C11 N1 1.71(17) . . . . ?
C5 C6 C11 C10 -179.40(10) . . . . ?
C6 C7 C8 C9 -0.1(2) . . . . ?
C7 C6 C11 N1 -172.36(11) . . . . ?
C7 C6 C11 C10 6.52(17) . . . . ?
C7 C8 C9 C10 2.8(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 N1 174.87(12) . . . . ?
C9 C10 C11 C6 -4.08(19) . . . . ?
C11 N1 C12 C4 -4.19(18) . . . . ?
C11 N1 C12 C13 177.85(10) . . . . ?
C11 C6 C7 C8 -4.51(18) . . . . ?
C12 N1 C11 C6 7.31(17) . . . . ?
C12 N1 C11 C10 -171.61(11) . . . . ?
C12 C4 C5 C1 -165.23(10) . . . 2_566 ?
C12 C4 C5 C6 16.47(16) . . . . ?
C12 C13 C14 C15 -179.70(11) . . . . ?
C12 C13 C19 C18 -179.65(14) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C13 C19 C18 -0.6(2) . . . . ?
C14 C15 C16 C17 -179.61(14) . . . . ?
C14 C15 C16 C18 -0.4(2) . . . . ?
C15 C16 C18 C19 1.1(3) . . . . ?
C16 C18 C19 C13 -0.6(3) . . . . ?
C17 C16 C18 C19 -179.75(16) . . . . ?
C19 C13 C14 C15 1.2(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.821
