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

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

data_1bHBr
_database_code_depnum_ccdc_archive 'CCDC 2208587'
loop_
_audit_author_name
_audit_author_address
'XRD service University of Bern'
;University of Bern
Switzerland
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_audit_creation_date             2022-01-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C12 H18 N'
_chemical_formula_sum            'C12 H18 Br N'
_chemical_formula_weight         256.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12NBrH19
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.16550(10)
_cell_length_b                   10.60420(10)
_cell_length_c                   14.47160(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.4950(10)
_cell_angle_gamma                90
_cell_volume                     1223.40(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19746
_cell_measurement_temperature    249.97(10)
_cell_measurement_theta_max      78.8490
_cell_measurement_theta_min      3.1110
_shelx_estimated_absorpt_T_max   0.546
_shelx_estimated_absorpt_T_min   0.441
_exptl_absorpt_coefficient_mu    4.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 -1 0.0958
-2 1 2 0.1097
1 1 1 0.1107
-1 1 2 0.1097
1 -1 -2 0.1004
0 0 1 0.0656
0 0 -1 0.1481
0 -2 1 0.0760
0 2 -1 0.0854
2 1 -2 0.1076
-5 -2 2 0.0760
0 -7 -3 0.0815
4 -5 -4 0.0865
0 5 6 0.0996
0 -5 -6 0.0824
-5 -2 0 0.0820
2 0 8 0.0627
-2 0 -8 0.1340
-3 -2 7 0.0718
1 -5 6 0.0616
2 -5 5 0.0702
-1 -4 7 0.0580
-5 -2 4 0.0662
-3 -3 -6 0.0992
1 2 8 0.0724

_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.161
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
-0.9999 -1.0028 -0.9981 0.2384 -0.0733 -0.1317
-2.0002 1.0018 1.9988 -0.0922 0.0384 -0.4143
0.9999 1.0028 0.9981 -0.2384 0.0733 0.1317
-1.0000 1.0026 1.9986 -0.1726 0.0333 -0.2386
1.0000 -1.0026 -1.9986 0.1726 -0.0333 0.2386
0.0004 0.0013 1.0002 -0.0950 -0.0502 -0.0189
-0.0004 -0.0013 -1.0002 0.0950 0.0502 0.0189
0.0017 -2.0001 1.0041 0.0311 -0.3073 0.0313
-0.0017 2.0001 -1.0041 -0.0311 0.3073 -0.0313
1.9989 0.9996 -2.0026 -0.0338 0.2187 0.3641
-5.0503 -2.0800 2.0931 0.3387 -0.3461 -0.8749
0.0521 -6.5804 -2.7103 0.6689 -0.7085 0.2249
3.6452 -4.6029 -3.9968 0.3772 -0.4086 0.8311
0.3243 5.2350 5.8020 -0.9073 0.3782 -0.1837
0.1295 -5.2390 -5.9925 0.8892 -0.3715 0.2671
-4.9258 -1.9797 -0.2254 0.5423 -0.2171 -0.8116
2.1361 -0.2135 7.5698 -0.8761 -0.4197 0.2372
-1.9941 0.1769 -7.7296 0.8822 0.4223 -0.2084
-3.4733 -2.3686 7.4964 -0.2822 -0.6634 -0.6930
0.8853 -4.6089 6.3018 -0.3775 -0.9136 0.1513
2.3988 -4.5523 4.5722 -0.3386 -0.8271 0.4486
-0.6993 -4.2226 7.4106 -0.3798 -0.9115 -0.1577
-4.7684 -2.2905 4.4126 0.1094 -0.4914 -0.8641
-2.8175 -2.9300 -5.6327 0.9459 -0.0778 -0.3151
0.6359 2.2816 8.3372 -0.9861 -0.1302 -0.1032

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0099
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23375
_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         69.122
_diffrn_reflns_theta_min         5.215
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      249.97(10)
_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    -61.00  -3.00   0.50    0.20    --  -23.00 112.00-105.00  116
  2  ω     41.00 108.00   0.50    0.66    --  111.50-112.00 161.00  134
  3  ω    -37.00  49.00   0.50    0.20    --  -23.00  61.00   0.00  172
  4  ω    -28.00  50.00   0.50    0.20    --  -23.00  15.00 150.00  156
  5  ω    -94.00 -10.00   0.50    0.20    --  -23.00 -57.00 150.00  168
  6  ω    -21.00  62.00   0.50    0.20    --   49.64 -57.00 120.00  166
  7  ω    -23.00  23.00   0.50    0.20    --   49.64 -19.00-120.00   92
  8  ω     25.00  88.00   0.50    0.20    --   49.64-112.00 161.00  126
  9  ω     42.00 121.00   0.50    0.20    --   49.64  38.00 -90.00  158
 10  ω    -23.00  23.00   0.50    0.20    --   49.64 -19.00 -30.00   92
 11  ω     41.00 105.00   0.50    0.66    --  111.50 -94.00   0.00  128
 12  ω     41.00 102.00   0.50    0.66    --  111.50 -77.00 150.00  122
 13  ω     41.00 105.00   0.50    0.66    --  111.50 -94.00 -90.00  128
 14  ω     41.00  68.00   0.50    0.66    --  111.50 -61.00  60.00   54
 15  ω    102.00 177.00   0.50    0.66    --  111.50  45.00   0.00  150
 16  ω     97.00 177.00   0.50    0.66    --  111.50  61.00-120.00  160
 17  ω     41.00 160.00   0.50    0.66    --  111.50   0.00-120.00  238
 18  ω     41.00 102.00   0.50    0.66    --  111.50 -77.00  30.00  122
 19  ω     41.00  68.00   0.50    0.66    --  111.50 -61.00-150.00   54
 20  ω    104.00 177.00   0.50    0.66    --  111.50  15.00 -60.00  146
 21  ω     41.00  68.00   0.50    0.66    --  111.50 -61.00  90.00   54
 22  ω     41.00  68.00   0.50    0.66    --  111.50 -61.00 150.00   54
 23  ω     41.00 105.00   0.50    0.66    --  111.50 -94.00 150.00  128
 24  ω     41.00  68.00   0.50    0.66    --  111.50 -61.00 -30.00   54
 25  ω     41.00 105.00   0.50    0.66    --  111.50 -94.00-120.00  128
 26  ω     41.00 105.00   0.50    0.66    --  111.50 -94.00 -30.00  128
 27  ω     41.00 102.00   0.50    0.66    --  111.50 -77.00  60.00  122
 28  ω    104.00 177.00   0.50    0.66    --  111.50  15.00 120.00  146
 29  ω     41.00 107.00   0.50    0.66    --  111.50-104.00 -17.64  132
 30  ω     41.00  68.00   0.50    0.66    --  111.50 -61.00-180.00   54
 31  ω     41.00 105.00   0.50    0.66    --  111.50 -94.00-180.00  128
 32  ω    104.00 177.00   0.50    0.66    --  111.50  15.00  90.00  146
 33  ω     41.00  68.00   0.50    0.66    --  111.50 -61.00   0.00   54
 34  ω    102.00 177.00   0.50    0.66    --  111.50  45.00 -90.00  150
 35  ω     97.00 177.00   0.50    0.66    --  111.50  61.00 -30.00  160
 36  ω     41.00 105.00   0.50    0.66    --  111.50 -94.00  30.00  128
 37  ω     91.00 177.00   0.50    0.66    --  111.50  77.00-180.00  172
 38  ω     91.00 177.00   0.50    0.66    --  111.50  77.00  30.00  172
 39  ω     41.00 102.00   0.50    0.66    --  111.50 -77.00  90.00  122
 40  ω     29.00 122.00   0.50    0.20    --   49.64  77.00 -60.00  186
 41  ω     29.00 122.00   0.50    0.20    --   49.64  77.00 120.00  186
 42  ω     29.00 122.00   0.50    0.20    --   49.64  77.00-180.00  186
 43  ω     29.00 122.00   0.50    0.20    --   49.64  77.00   0.00  186
 44  ω     29.00 122.00   0.50    0.20    --   49.64  77.00-120.00  186
 45  ω     29.00 122.00   0.50    0.20    --   49.64  77.00  30.00  186
;
_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      -0.0803472000
_diffrn_orient_matrix_UB_12      -0.0632178000
_diffrn_orient_matrix_UB_13      -0.0948486000
_diffrn_orient_matrix_UB_21      -0.0052106000
_diffrn_orient_matrix_UB_22      0.1283713000
_diffrn_orient_matrix_UB_23      -0.0503515000
_diffrn_orient_matrix_UB_31      0.1756817000
_diffrn_orient_matrix_UB_32      -0.0249878000
_diffrn_orient_matrix_UB_33      -0.0189397000
_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                2264
_reflns_number_total             2285
_reflns_odcompleteness_completeness 99.81
_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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         1.168
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2285
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.116
_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)+(0.0493P)²+1.6441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.2
Uanis(C2) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.009 and sigma for
terminal atoms of 0.01
Uanis(C8) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.005
Uanis(C8) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.003
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C9(H9A,H9B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C4(H4), C3(H3), C2(H2)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.70166(5) 0.41864(4) 0.38472(2) 0.06248(18) Uani 1 1 d . . . . .
C6 C 0.7923(4) 0.7051(3) 0.6158(2) 0.0464(7) Uani 1 1 d . . . . .
N1 N 0.6903(3) 0.4821(2) 0.60499(17) 0.0416(5) Uani 1 1 d . . . . .
H1A H 0.702658 0.463556 0.546193 0.050 Uiso 1 1 calc R U . . .
H1B H 0.588181 0.516353 0.601075 0.050 Uiso 1 1 calc R U . . .
C7 C 0.8252(4) 0.5718(3) 0.6526(3) 0.0531(8) Uani 1 1 d . . . . .
H7 H 0.932263 0.543552 0.637863 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8725(4) 0.7446(3) 0.5466(2) 0.0531(8) Uani 1 1 d . . . . .
H5 H 0.943419 0.688698 0.523375 0.064 Uiso 1 1 calc R U . . .
C1 C 0.6881(6) 0.7892(4) 0.6466(3) 0.0785(13) Uani 1 1 d . . . . .
H1 H 0.629996 0.764046 0.692954 0.094 Uiso 1 1 calc R U . . .
C4 C 0.8499(5) 0.8660(4) 0.5108(3) 0.0624(9) Uani 1 1 d . . . . .
H4 H 0.905645 0.891855 0.463516 0.075 Uiso 1 1 calc R U . . .
C3 C 0.7478(6) 0.9480(4) 0.5434(3) 0.0700(11) Uani 1 1 d . . . . .
H3 H 0.733107 1.030583 0.519445 0.084 Uiso 1 1 calc R U . . .
C2 C 0.6674(7) 0.9091(4) 0.6111(4) 0.0887(14) Uani 1 1 d . U . . .
H2 H 0.596424 0.965321 0.633952 0.106 Uiso 1 1 calc R U . . .
C10 C 0.7106(4) 0.3643(3) 0.6662(2) 0.0490(7) Uani 1 1 d . . . . .
C9 C 0.7380(6) 0.4250(4) 0.7636(3) 0.0673(10) Uani 1 1 d . . . . .
H9A H 0.630225 0.443438 0.780108 0.081 Uiso 1 1 calc R U . . .
H9B H 0.802325 0.368619 0.811806 0.081 Uiso 1 1 calc R U . . .
C12 C 0.5537(5) 0.2844(4) 0.6393(3) 0.0638(9) Uani 1 1 d . . . . .
H12A H 0.539945 0.256570 0.574244 0.096 Uiso 1 1 calc R U . . .
H12B H 0.456977 0.333907 0.645848 0.096 Uiso 1 1 calc R U . . .
H12C H 0.563768 0.211503 0.680679 0.096 Uiso 1 1 calc R U . . .
C8 C 0.8341(6) 0.5452(4) 0.7577(3) 0.0740(11) Uani 1 1 d . U . . .
H8A H 0.951096 0.535515 0.791506 0.089 Uiso 1 1 calc R U . . .
H8B H 0.784193 0.615076 0.786375 0.089 Uiso 1 1 calc R U . . .
C11 C 0.8620(5) 0.2903(4) 0.6511(4) 0.0779(12) Uani 1 1 d . . . . .
H11A H 0.962209 0.341339 0.670127 0.117 Uiso 1 1 calc R U . . .
H11B H 0.846948 0.268322 0.584738 0.117 Uiso 1 1 calc R U . . .
H11C H 0.873552 0.213887 0.688856 0.117 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
C6 C7 1.514(5) . ?
C6 C5 1.375(4) . ?
C6 C1 1.373(5) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 C7 1.504(4) . ?
N1 C10 1.520(4) . ?
C7 H7 0.9900 . ?
C7 C8 1.533(5) . ?
C5 H5 0.9400 . ?
C5 C4 1.385(5) . ?
C1 H1 0.9400 . ?
C1 C2 1.368(6) . ?
C4 H4 0.9400 . ?
C4 C3 1.358(6) . ?
C3 H3 0.9400 . ?
C3 C2 1.356(7) . ?
C2 H2 0.9400 . ?
C10 C9 1.522(5) . ?
C10 C12 1.515(5) . ?
C10 C11 1.520(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 C8 1.509(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 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
C5 C6 C7 117.7(3) . . ?
C1 C6 C7 124.6(3) . . ?
C1 C6 C5 117.7(3) . . ?
H1A N1 H1B 108.7 . . ?
C7 N1 H1A 110.5 . . ?
C7 N1 H1B 110.5 . . ?
C7 N1 C10 106.0(2) . . ?
C10 N1 H1A 110.5 . . ?
C10 N1 H1B 110.5 . . ?
C6 C7 H7 107.7 . . ?
C6 C7 C8 119.2(3) . . ?
N1 C7 C6 111.9(3) . . ?
N1 C7 H7 107.7 . . ?
N1 C7 C8 102.2(3) . . ?
C8 C7 H7 107.7 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C1 H1 119.4 . . ?
C2 C1 C6 121.1(4) . . ?
C2 C1 H1 119.4 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3 120.4 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
N1 C10 C9 99.7(3) . . ?
C12 C10 N1 109.3(3) . . ?
C12 C10 C9 114.9(3) . . ?
C12 C10 C11 110.1(3) . . ?
C11 C10 N1 109.3(3) . . ?
C11 C10 C9 113.0(3) . . ?
C10 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C8 C9 C10 106.2(3) . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
C9 C8 C7 107.3(3) . . ?
C9 C8 H8A 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C7 C8 C9 136.9(4) . . . . ?
C6 C5 C4 C3 -0.1(6) . . . . ?
C6 C1 C2 C3 0.8(9) . . . . ?
N1 C7 C8 C9 13.1(4) . . . . ?
N1 C10 C9 C8 -34.3(4) . . . . ?
C7 C6 C5 C4 -179.1(3) . . . . ?
C7 C6 C1 C2 178.7(4) . . . . ?
C7 N1 C10 C9 43.8(3) . . . . ?
C7 N1 C10 C12 164.6(3) . . . . ?
C7 N1 C10 C11 -74.9(4) . . . . ?
C5 C6 C7 N1 -97.2(4) . . . . ?
C5 C6 C7 C8 143.8(3) . . . . ?
C5 C6 C1 C2 -1.3(7) . . . . ?
C5 C4 C3 C2 -0.5(7) . . . . ?
C1 C6 C7 N1 82.8(5) . . . . ?
C1 C6 C7 C8 -36.2(5) . . . . ?
C1 C6 C5 C4 0.9(5) . . . . ?
C4 C3 C2 C1 0.1(8) . . . . ?
C10 N1 C7 C6 -164.3(3) . . . . ?
C10 N1 C7 C8 -35.7(3) . . . . ?
C10 C9 C8 C7 13.7(5) . . . . ?
C12 C10 C9 C8 -151.0(3) . . . . ?
C11 C10 C9 C8 81.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.630
_oxdiff_exptl_absorpt_empirical_full_min 0.816
