# 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_a22060802a0122
_database_code_depnum_ccdc_archive 'CCDC 2265350'
loop_
_audit_author_name
_audit_author_address
'Ning Wang'
;SUN YAT SEN UNIVERSITY
China
;
_audit_update_record             
;
2023-05-25 deposited with the CCDC.	2024-06-28 downloaded from the CCDC.
;
_vrf_PLAT420_a22060802a0122      
;
PROBLEM: PLAT420_ALERT_2_B D-H Bond Without Acceptor  O1       --H1       .     Please Check 
RESPONSE: There is no suitable acceptor close to the bridging OH
hydrogen atoms; on the other hand, the presence of the bridging OH groups
was unambiguously evidenced by H NMR; also, the H atoms of the two OH
groups gave corresponding peaks on the Fourier maps.
;
_audit_creation_date             2022-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     ID-4Me
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   7.41780(10)
_cell_length_b                   10.28570(10)
_cell_length_c                   18.5504(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.8160(10)
_cell_angle_gamma                90
_cell_volume                     1410.35(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13805
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.0430
_cell_measurement_theta_min      4.2430
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18322
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.204
_diffrn_reflns_theta_min         4.785
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -88.00   1.00    1.00    --  -41.14 -57.00-180.00   26
  2  ω   -105.00 -78.00   1.00    1.00    --  -41.14 -57.00 -90.00   27
  3  ω    -52.00 -13.00   1.00    1.00    --  -41.14 -57.00-180.00   39
  4  ω    -76.00 -17.00   1.00    1.00    --  -41.14 -38.00   0.00   59
  5  ω    -74.00  33.00   1.00    1.00    --  -41.14  77.00  30.00  107
  6  ω   -113.00 -80.00   1.00    1.00    --  -41.14 -38.00   0.00   33
  7  ω    -76.00 -13.00   1.00    1.00    --  -41.14 -57.00 -90.00   63
  8  ω     24.00  97.00   1.00    1.00    --   41.14-125.00-120.00   73
  9  ω      6.00  31.00   1.00    1.00    --   42.00  88.00  17.61   25
 10  ω     11.00  36.00   1.00    1.00    --   46.00  84.00 171.71   25
 11  ω     11.00  36.00   1.00    1.00    --   46.00  84.00 -92.05   25
 12  ω     11.00  36.00   1.00    1.00    --   46.00  84.00 113.89   25
 13  ω     19.00  45.00   1.00    1.00    --   50.00  80.00  28.48   26
 14  ω     88.00 138.00   1.00    1.00    --   62.00  76.00  93.47   50
 15  ω     33.00  64.00   1.00    1.00    --   62.00  74.00 -25.47   31
 16  ω     34.00  60.00   1.00    1.00    --   62.00  75.00  41.94   26
 17  ω     30.00  56.00   1.00    1.00    --   62.00  75.00-114.20   26
 18  ω     31.00  56.00   1.00    1.00    --   62.00  76.00-177.97   25
 19  ω     75.00 136.00   1.00    1.00    --   62.00  74.00 -25.47   61
 20  ω     94.00 136.00   1.00    1.00    --   62.00  75.00  41.94   42
 21  ω     31.00  63.00   1.00    1.00    --   62.00  77.00 -63.71   32
 22  ω     30.00  64.00   1.00    1.00    --   62.00  76.00  93.47   34
 23  ω     33.00  82.00   1.00    1.00    --   66.00  77.00-171.31   49
 24  ω     34.00  74.00   1.00    1.00    --   66.00  76.00 -87.57   40
 25  ω     35.00  70.00   1.00    1.00    --   66.00  76.00 129.67   35
 26  ω     38.00  71.00   1.00    1.00    --   70.00  77.00   7.76   33
 27  ω     61.00 162.00   1.00    4.00    --   90.00  68.00 -98.84  101
 28  ω     75.00 101.00   1.00    4.00    --  107.79  77.00-180.00   26
 29  ω     75.00 102.00   1.00    4.00    --  107.79  77.00  60.00   27
 30  ω    104.00 177.00   1.00    4.00    --  107.79  77.00 150.00   73
 31  ω     54.00 102.00   1.00    4.00    --  107.79 -94.00-180.00   48
 32  ω     75.00 101.00   1.00    4.00    --  107.79  77.00 150.00   26
 33  ω     79.00 158.00   1.00    4.00    --  107.79  77.00  90.00   79
 34  ω     79.00 115.00   1.00    4.00    --  107.79  61.00  90.00   36
 35  ω     36.00 112.00   1.00    4.00    --  107.79-125.00-180.00   76
 36  ω     75.00 129.00   1.00    4.00    --  107.79  77.00  30.00   54
 37  ω     34.00  63.00   1.00    4.00    --  107.79 -77.00 -60.00   29
 38  ω     75.00 139.00   1.00    4.00    --  107.79  77.00-150.00   64
 39  ω     75.00 172.00   1.00    4.00    --  107.79  77.00 -60.00   97
 40  ω     78.00 141.00   1.00    4.00    --  107.79  77.00-120.00   63
 41  ω     79.00 171.00   1.00    4.00    --  107.79  61.00  60.00   92
 42  ω     75.00 175.00   1.00    4.00    --  107.79  77.00 -30.00  100
 43  ω     25.00 109.00   1.00    4.00    --  107.79 -94.00 -90.00   84
 44  ω     98.00 139.00   1.00    4.00    --  107.79 -77.00 -60.00   41
 45  ω     80.00  97.00   1.00    4.00    --  107.79  61.00-150.00   17
;
_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      -0.0849971000
_diffrn_orient_matrix_UB_12      0.1356562000
_diffrn_orient_matrix_UB_13      -0.0123594000
_diffrn_orient_matrix_UB_21      0.1881547000
_diffrn_orient_matrix_UB_22      0.0627234000
_diffrn_orient_matrix_UB_23      0.0144606000
_diffrn_orient_matrix_UB_31      0.0286018000
_diffrn_orient_matrix_UB_32      -0.0094766000
_diffrn_orient_matrix_UB_33      -0.0811452000
_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                2740
_reflns_number_total             2831
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0065(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.023
_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)+(0.0406P)²+0.6026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0885
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C9(H9), C12(H12), C16(H16), C15(H15), C14(H14), C13(H13), C6(H6),
 C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.87992(10) 0.37921(8) 0.10441(4) 0.0255(2) Uani 1 1 d . . . . .
H1 H 0.8120 0.3328 0.0785 0.038 Uiso 1 1 calc R U . . .
N1 N 0.80677(12) 0.74033(9) 0.33129(5) 0.0226(2) Uani 1 1 d . . . . .
H1A H 0.9032 0.7818 0.3466 0.027 Uiso 1 1 calc R U . . .
C1 C 0.60275(13) 0.63391(10) 0.25604(6) 0.0181(2) Uani 1 1 d . . . . .
C2 C 0.53371(14) 0.64281(10) 0.32642(6) 0.0179(2) Uani 1 1 d . . . . .
C3 C 0.66659(14) 0.70945(10) 0.37171(6) 0.0203(2) Uani 1 1 d . . . . .
C9 C 0.76782(14) 0.69414(10) 0.26230(6) 0.0208(2) Uani 1 1 d . . . . .
H9 H 0.8432 0.7026 0.2250 0.025 Uiso 1 1 calc R U . . .
C11 C 0.35869(13) 0.65429(10) 0.15237(5) 0.0177(2) Uani 1 1 d . . . . .
C10 C 0.51218(13) 0.57201(10) 0.18854(5) 0.0181(2) Uani 1 1 d . . . . .
H10 H 0.4578 0.4907 0.2036 0.022 Uiso 1 1 calc R U . . .
C7 C 0.37497(14) 0.59931(10) 0.35641(6) 0.0211(2) Uani 1 1 d . . . . .
C12 C 0.34813(14) 0.78805(10) 0.16127(6) 0.0213(2) Uani 1 1 d . . . . .
H12 H 0.4365 0.8306 0.1910 0.026 Uiso 1 1 calc R U . . .
C16 C 0.22426(14) 0.59317(11) 0.10745(6) 0.0217(2) Uani 1 1 d . . . . .
H16 H 0.2291 0.5037 0.1008 0.026 Uiso 1 1 calc R U . . .
C15 C 0.08354(14) 0.66356(11) 0.07250(6) 0.0234(2) Uani 1 1 d . . . . .
H15 H -0.0049 0.6212 0.0427 0.028 Uiso 1 1 calc R U . . .
C17 C 0.64624(14) 0.53559(11) 0.13275(6) 0.0212(2) Uani 1 1 d . . . . .
H17A H 0.5791 0.5030 0.0894 0.025 Uiso 1 1 calc R U . . .
H17B H 0.7105 0.6131 0.1197 0.025 Uiso 1 1 calc R U . . .
C14 C 0.07444(15) 0.79711(11) 0.08198(6) 0.0247(2) Uani 1 1 d . . . . .
H14 H -0.0200 0.8446 0.0587 0.030 Uiso 1 1 calc R U . . .
C13 C 0.20712(15) 0.85917(11) 0.12636(6) 0.0257(3) Uani 1 1 d . . . . .
H13 H 0.2019 0.9487 0.1328 0.031 Uiso 1 1 calc R U . . .
C18 C 0.78290(15) 0.43336(11) 0.16091(6) 0.0242(2) Uani 1 1 d . . . . .
H18A H 0.8682 0.4724 0.1971 0.029 Uiso 1 1 calc R U . . .
H18B H 0.7202 0.3642 0.1841 0.029 Uiso 1 1 calc R U . . .
C6 C 0.36111(17) 0.62222(11) 0.42939(6) 0.0274(3) Uani 1 1 d . . . . .
H6 H 0.2591 0.5925 0.4503 0.033 Uiso 1 1 calc R U . . .
C8 C 0.22374(15) 0.53156(12) 0.31224(7) 0.0281(3) Uani 1 1 d . . . . .
H8A H 0.1874 0.5828 0.2703 0.042 Uiso 1 1 calc R U . . .
H8B H 0.1228 0.5207 0.3409 0.042 Uiso 1 1 calc R U . . .
H8C H 0.2645 0.4479 0.2974 0.042 Uiso 1 1 calc R U . . .
C5 C 0.49474(18) 0.68849(12) 0.47304(6) 0.0310(3) Uani 1 1 d . . . . .
H5 H 0.4792 0.7019 0.5217 0.037 Uiso 1 1 calc R U . . .
C4 C 0.64853(17) 0.73390(11) 0.44483(6) 0.0270(3) Uani 1 1 d . . . . .
H4 H 0.7368 0.7790 0.4733 0.032 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
O1 H1 0.8200 . ?
O1 C18 1.4329(13) . ?
N1 H1A 0.8600 . ?
N1 C3 1.3694(14) . ?
N1 C9 1.3728(14) . ?
C1 C2 1.4449(15) . ?
C1 C9 1.3684(15) . ?
C1 C10 1.5110(14) . ?
C2 C3 1.4171(14) . ?
C2 C7 1.4164(15) . ?
C3 C4 1.3969(16) . ?
C9 H9 0.9300 . ?
C11 C10 1.5278(14) . ?
C11 C12 1.3887(15) . ?
C11 C16 1.3944(14) . ?
C10 H10 0.9800 . ?
C10 C17 1.5405(14) . ?
C7 C6 1.3866(16) . ?
C7 C8 1.5036(15) . ?
C12 H12 0.9300 . ?
C12 C13 1.3910(15) . ?
C16 H16 0.9300 . ?
C16 C15 1.3858(15) . ?
C15 H15 0.9300 . ?
C15 C14 1.3872(16) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.5223(14) . ?
C14 H14 0.9300 . ?
C14 C13 1.3849(16) . ?
C13 H13 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.4029(18) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.3761(18) . ?
C4 H4 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
C18 O1 H1 109.5 . . ?
C3 N1 H1A 125.7 . . ?
C3 N1 C9 108.67(9) . . ?
C9 N1 H1A 125.7 . . ?
C2 C1 C10 127.50(9) . . ?
C9 C1 C2 106.08(9) . . ?
C9 C1 C10 126.41(10) . . ?
C3 C2 C1 106.54(9) . . ?
C7 C2 C1 134.77(10) . . ?
C7 C2 C3 118.68(10) . . ?
N1 C3 C2 108.05(9) . . ?
N1 C3 C4 128.98(10) . . ?
C4 C3 C2 122.96(10) . . ?
N1 C9 H9 124.7 . . ?
C1 C9 N1 110.65(10) . . ?
C1 C9 H9 124.7 . . ?
C12 C11 C10 122.95(9) . . ?
C12 C11 C16 118.23(9) . . ?
C16 C11 C10 118.81(9) . . ?
C1 C10 C11 113.18(8) . . ?
C1 C10 H10 106.8 . . ?
C1 C10 C17 113.07(8) . . ?
C11 C10 H10 106.8 . . ?
C11 C10 C17 109.81(8) . . ?
C17 C10 H10 106.8 . . ?
C2 C7 C8 122.64(10) . . ?
C6 C7 C2 117.51(10) . . ?
C6 C7 C8 119.85(10) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.89(10) . . ?
C13 C12 H12 119.6 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.12(10) . . ?
C15 C16 H16 119.4 . . ?
C16 C15 H15 120.0 . . ?
C16 C15 C14 120.05(10) . . ?
C14 C15 H15 120.0 . . ?
C10 C17 H17A 109.0 . . ?
C10 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C10 112.72(9) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C15 C14 H14 120.3 . . ?
C13 C14 C15 119.48(10) . . ?
C13 C14 H14 120.3 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.23(10) . . ?
C14 C13 H13 119.9 . . ?
O1 C18 C17 112.23(9) . . ?
O1 C18 H18A 109.2 . . ?
O1 C18 H18B 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C7 C6 H6 118.7 . . ?
C7 C6 C5 122.65(11) . . ?
C5 C6 H6 118.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 120.90(11) . . ?
C4 C5 H5 119.5 . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.28(11) . . ?
C5 C4 H4 121.4 . . ?

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 C3 C4 C5 -177.98(11) . . . . ?
C1 C2 C3 N1 0.58(11) . . . . ?
C1 C2 C3 C4 -178.58(10) . . . . ?
C1 C2 C7 C6 176.94(11) . . . . ?
C1 C2 C7 C8 -3.60(18) . . . . ?
C1 C10 C17 C18 63.28(12) . . . . ?
C2 C1 C9 N1 -0.18(12) . . . . ?
C2 C1 C10 C11 75.27(13) . . . . ?
C2 C1 C10 C17 -159.06(10) . . . . ?
C2 C3 C4 C5 0.99(17) . . . . ?
C2 C7 C6 C5 1.53(16) . . . . ?
C3 N1 C9 C1 0.56(12) . . . . ?
C3 C2 C7 C6 -1.46(15) . . . . ?
C3 C2 C7 C8 178.01(10) . . . . ?
C9 N1 C3 C2 -0.70(12) . . . . ?
C9 N1 C3 C4 178.39(11) . . . . ?
C9 C1 C2 C3 -0.24(11) . . . . ?
C9 C1 C2 C7 -178.78(11) . . . . ?
C9 C1 C10 C11 -104.19(12) . . . . ?
C9 C1 C10 C17 21.48(15) . . . . ?
C11 C10 C17 C18 -169.26(9) . . . . ?
C11 C12 C13 C14 0.03(17) . . . . ?
C11 C16 C15 C14 -0.12(17) . . . . ?
C10 C1 C2 C3 -179.79(9) . . . . ?
C10 C1 C2 C7 1.68(19) . . . . ?
C10 C1 C9 N1 179.37(9) . . . . ?
C10 C11 C12 C13 179.04(10) . . . . ?
C10 C11 C16 C15 -179.03(10) . . . . ?
C10 C17 C18 O1 167.00(9) . . . . ?
C7 C2 C3 N1 179.39(9) . . . . ?
C7 C2 C3 C4 0.23(15) . . . . ?
C7 C6 C5 C4 -0.31(18) . . . . ?
C12 C11 C10 C1 24.04(14) . . . . ?
C12 C11 C10 C17 -103.36(11) . . . . ?
C12 C11 C16 C15 -0.01(16) . . . . ?
C16 C11 C10 C1 -156.98(9) . . . . ?
C16 C11 C10 C17 75.62(12) . . . . ?
C16 C11 C12 C13 0.05(16) . . . . ?
C16 C15 C14 C13 0.20(17) . . . . ?
C15 C14 C13 C12 -0.15(17) . . . . ?
C6 C5 C4 C3 -0.96(17) . . . . ?
C8 C7 C6 C5 -177.95(11) . . . . ?

_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 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.689
