# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_Sugita_B2
_database_code_depnum_ccdc_archive 'CCDC 2207403'
loop_
_audit_author_name
_audit_author_address
'Yi Lu'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2022-09-15 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_audit_creation_date             2021-06-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H26 N O2'
_chemical_formula_sum            'C19 H26 N O2'
_chemical_formula_weight         300.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.46250(10)
_cell_length_b                   15.60580(10)
_cell_length_c                   17.06840(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.5240(10)
_cell_angle_gamma                90
_cell_volume                     3558.46(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    17469
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      75.2190
_cell_measurement_theta_min      4.3480
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.819
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
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    1.121
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 9 4 0.0696
-3 1 11 0.1632
6 6 1 0.0931
1 -3 -10 0.1619
-6 -6 -1 0.0875
-7 -6 2 0.0872
-7 -3 9 0.1584
6 6 3 0.0972
3 9 1 0.0793
0 -2 10 0.1686
4 -6 5 0.1267
3 -10 0 0.0950
-2 -3 -8 0.1565
-7 6 0 0.1053
4 -8 -6 0.0758
7 -7 -2 0.0725
7 -6 0 0.0759
-7 6 6 0.0711
8 -2 0 0.0838
6 -6 -7 0.0851
7 -3 -9 0.1120
0 10 1 0.0665
0 10 -3 0.1114
-5 8 6 0.0635
-7 5 8 0.0936
-8 -2 0 0.0882
-9 1 5 0.0851
4 8 -6 0.1228
-4 -8 -2 0.0846
-4 -9 0 0.0895
-4 -9 4 0.1283
8 -4 0 0.0763
6 7 1 0.0900
3 10 -3 0.0980
3 9 3 0.0816
3 9 3 0.0867
-6 6 7 0.0693
-8 2 -1 0.1052

_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.4930 9.1196 3.8657 -0.1961 -0.8184 0.5401
-3.2564 1.0371 11.0112 0.5874 -0.1408 0.7970
6.2280 6.3721 1.3429 -0.6321 0.1516 0.7599
1.2287 -2.6938 -10.3283 -0.3571 0.0855 -0.9302
-6.3445 -6.3784 -1.0650 0.6505 -0.1561 -0.7433
-7.3260 -6.1903 1.9198 0.8202 -0.1967 -0.5371
-7.1583 -3.4386 8.8738 0.9550 -0.2290 0.1887
5.6864 6.2997 2.5177 -0.5488 0.1317 0.8255
2.7280 9.4122 1.1091 -0.6473 -0.3517 0.6762
-0.2570 -2.4854 10.0356 0.6032 0.3277 0.7272
3.9132 -5.7953 5.4627 0.3889 0.8158 0.4282
2.9437 -9.5398 -0.1143 0.4141 0.8688 -0.2714
-2.3670 -2.7803 -8.4292 -0.0877 -0.1838 -0.9790
-6.8646 6.0921 -0.1863 -0.0257 -0.9905 -0.1352
4.3034 -8.1987 -5.6843 0.0205 0.7946 -0.6068
6.5364 -7.1401 -1.5965 0.0258 0.9962 -0.0827
6.8810 -5.9574 0.3845 0.0256 0.9869 0.1591
-7.0756 6.0264 6.0331 0.2631 -0.8872 0.3791
8.3032 -2.3456 0.3967 -0.2599 0.8766 0.4050
6.1118 -6.3839 -7.0754 -0.2394 0.8074 -0.5393
6.8984 -3.3822 -9.1506 -0.5488 0.6422 -0.5352
0.2621 10.0991 0.6018 -0.5868 -0.6188 0.5223
-0.4552 9.6128 -2.9826 -0.6799 -0.7169 0.1541
-5.3153 7.6466 5.7696 0.0668 -0.8448 0.5309
-6.6068 4.9618 8.2396 0.4001 -0.7363 0.5457
-8.4159 -1.9004 -0.3154 0.5214 -0.6104 -0.5963
-9.3571 0.5894 4.7973 0.6462 -0.7562 -0.1028
4.1635 8.2731 -5.6677 -0.9506 -0.2818 0.1304
-3.7999 -8.4481 -2.1256 0.5990 0.1776 -0.7808
-4.1155 -8.8858 -0.1557 0.7278 0.2158 -0.6510
-4.3113 -8.8341 3.6949 0.9043 0.2681 -0.3322
8.0204 -3.7940 0.0626 -0.1744 0.9395 0.2949
6.1222 6.9395 0.5687 -0.6946 0.0912 0.7136
2.5529 9.5023 -3.3586 -0.8409 -0.4569 0.2899
2.6684 8.9821 2.5274 -0.5562 -0.3023 0.7741
2.6044 8.6228 3.3830 -0.4940 -0.2685 0.8270
-6.4565 6.2872 6.7532 0.2483 -0.8370 0.4877
-8.0389 1.6340 -1.3931 0.2450 -0.8266 -0.5067

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26464
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.350
_diffrn_reflns_theta_min         4.357
_diffrn_ambient_temperature      100.15
_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 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    103.00 138.00   0.50    0.17    --  108.48  77.00 150.00   70
  2  ω     86.00 178.00   0.50    0.17    --  108.48  45.00 -90.00  184
  3  ω     85.00 178.00   0.50    0.17    --  108.48  30.00-120.00  186
  4  ω    -42.00  34.00   0.50    0.05    --  -43.71  37.00-150.00  152
  5  ω    -28.00  37.00   0.50    0.05    --  -43.71  19.00   0.00  130
  6  ω    -42.00  34.00   0.50    0.05    --  -43.71  37.00  60.00  152
  7  ω    -28.00  37.00   0.50    0.05    --  -43.71  19.00 120.00  130
  8  ω    -19.00  76.00   0.50    0.05    --   43.71 -85.00 -11.00  190
  9  ω     36.00  97.00   0.50    0.05    --   43.71-125.00-150.00  122
 10  ω     36.00 105.00   0.50    0.17    --  108.48-125.00   0.00  138
 11  ω     35.00 101.00   0.50    0.17    --  108.48 -94.00 -90.00  132
 12  ω     81.00 108.00   0.50    0.17    --  108.48-125.00  90.00   54
 13  ω     44.00  75.00   0.50    0.17    --  108.48-125.00  90.00   62
 14  ω     36.00 108.00   0.50    0.17    --  108.48-125.00 120.00  144
 15  ω     35.00 103.00   0.50    0.17    --  108.48 -94.00 120.00  136
 16  ω     34.00 141.00   0.50    0.17    --  108.48 -85.00 -11.00  214
 17  ω     43.00 103.00   0.50    0.17    --  108.48 -77.00-180.00  120
 18  ω     37.00  70.00   0.50    0.17    --  108.48 -61.00-180.00   66
 19  ω     34.00  72.00   0.50    0.17    --  108.48 -61.00 -90.00   76
 20  ω     34.00  72.00   0.50    0.17    --  108.48 -61.00  30.00   76
 21  ω     34.00  72.00   0.50    0.17    --  108.48 -61.00 120.00   76
 22  ω    -36.00  29.00   0.50    0.05    --   43.71 -19.00-120.00  130
 23  ω     98.00 133.00   0.50    0.17    --  108.48 125.00 -60.00   70
 24  ω    143.00 169.00   0.50    0.17    --  108.48 125.00 -60.00   52
 25  ω    118.00 144.00   0.50    0.17    --  108.48  85.00 106.00   52
 26  ω    150.00 178.00   0.50    0.17    --  108.48  85.00 106.00   56
 27  ω   -128.00 -22.00   0.50    0.17    --  -96.00  85.00 106.00  212
 28  ω    -76.00  31.00   0.50    0.05    --  -43.71  85.00 106.00  214
 29  ω    -82.00 -15.00   0.50    0.05    --  -43.71 125.00-120.00  134
 30  ω    -83.00 -22.00   0.50    0.17    --  -96.00 125.00 -30.00  122
 31  ω    -50.00 -20.00   0.50    0.17    --  -96.00  45.00  60.00   60
 32  ω    -50.00 -20.00   0.50    0.17    --  -96.00  45.00  30.00   60
 33  ω    -50.00 -20.00   0.50    0.17    --  -96.00  45.00-150.00   60
 34  ω    -50.00 -20.00   0.50    0.17    --  -96.00  45.00-180.00   60
 35  ω   -175.00 -72.00   0.50    0.17    --  -96.00 -30.00-120.00  206
 36  ω   -172.00 -74.00   0.50    0.17    --  -96.00 -45.00 -60.00  196
 37  ω   -170.00 -81.00   0.50    0.17    --  -96.00 -85.00 -11.00  178
 38  ω   -170.00 -85.00   0.50    0.17    --  -96.00 -94.00  60.00  170
 39  ω   -170.00 -81.00   0.50    0.17    --  -96.00 -77.00  60.00  178
;
_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      -0.0501938000
_diffrn_orient_matrix_UB_12      -0.0594255000
_diffrn_orient_matrix_UB_13      0.0440990000
_diffrn_orient_matrix_UB_21      0.0864143000
_diffrn_orient_matrix_UB_22      -0.0646363000
_diffrn_orient_matrix_UB_23      0.0188578000
_diffrn_orient_matrix_UB_31      0.0574650000
_diffrn_orient_matrix_UB_32      0.0451571000
_diffrn_orient_matrix_UB_33      0.0851180000
_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                3443
_reflns_number_total             3624
_reflns_odcompleteness_completeness 100.00
_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 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3624
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.035
_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)+(0.0449P)²+2.6683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0958
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C9(H9)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_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
O001 O 0.48667(5) 0.44972(5) 0.59409(4) 0.01856(17) Uani 1 1 d . . . . .
O002 O 0.58946(6) 0.41854(5) 0.72813(5) 0.02129(18) Uani 1 1 d . . . . .
N003 N 0.29458(7) 0.55637(6) 0.61404(6) 0.0238(2) Uani 1 1 d . . . . .
C6 C 0.54015(7) 0.62304(6) 0.67565(6) 0.0140(2) Uani 1 1 d . . . . .
C10 C 0.68814(7) 0.68164(6) 0.66108(6) 0.0155(2) Uani 1 1 d . . . . .
C8 C 0.53642(7) 0.76843(6) 0.62517(6) 0.0155(2) Uani 1 1 d . . . . .
C11 C 0.63853(7) 0.61405(6) 0.68245(6) 0.0151(2) Uani 1 1 d . . . . .
H11 H 0.672557 0.561388 0.701845 0.018 Uiso 1 1 calc R U . . .
C3 C 0.52759(7) 0.46271(6) 0.67699(6) 0.0148(2) Uani 1 1 d . . . . .
C2 C 0.37884(7) 0.55167(6) 0.65264(6) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.48849(7) 0.54732(6) 0.70059(6) 0.0140(2) Uani 1 1 d . . . . .
C7 C 0.48954(7) 0.70027(6) 0.64759(6) 0.0150(2) Uani 1 1 d . . . . .
H7 H 0.422584 0.706339 0.643775 0.018 Uiso 1 1 calc R U . . .
C9 C 0.63576(7) 0.75754(6) 0.63246(6) 0.0161(2) Uani 1 1 d . . . . .
H9 H 0.668357 0.803725 0.617270 0.019 Uiso 1 1 calc R U . . .
C12 C 0.48339(8) 0.85366(6) 0.59140(6) 0.0182(2) Uani 1 1 d . . . . .
C16 C 0.79777(7) 0.66994(7) 0.67227(7) 0.0197(2) Uani 1 1 d . . . . .
C5 C 0.62507(8) 0.38730(7) 0.56324(7) 0.0238(2) Uani 1 1 d . . . . .
H5A H 0.625971 0.439829 0.532076 0.036 Uiso 1 1 calc R U . . .
H5B H 0.643169 0.338359 0.536049 0.036 Uiso 1 1 calc R U . . .
H5C H 0.673304 0.392477 0.621898 0.036 Uiso 1 1 calc R U . . .
C4 C 0.52160(8) 0.37382(7) 0.56279(7) 0.0205(2) Uani 1 1 d . . . . .
H4A H 0.474512 0.360970 0.504283 0.025 Uiso 1 1 calc R U . . .
H4B H 0.522425 0.323976 0.598925 0.025 Uiso 1 1 calc R U . . .
C15 C 0.54411(9) 0.92796(7) 0.64639(7) 0.0240(2) Uani 1 1 d . . . . .
H15A H 0.550955 0.919452 0.705249 0.036 Uiso 1 1 calc R U . . .
H15B H 0.509419 0.982196 0.625112 0.036 Uiso 1 1 calc R U . . .
H15C H 0.610650 0.929581 0.643865 0.036 Uiso 1 1 calc R U . . .
C14 C 0.37734(8) 0.85570(7) 0.59112(7) 0.0236(2) Uani 1 1 d . . . . .
H14A H 0.337243 0.809937 0.554418 0.035 Uiso 1 1 calc R U . . .
H14B H 0.346405 0.911284 0.569772 0.035 Uiso 1 1 calc R U . . .
H14C H 0.380534 0.847185 0.648987 0.035 Uiso 1 1 calc R U . . .
C17 C 0.83757(8) 0.74555(7) 0.63724(7) 0.0237(2) Uani 1 1 d . . . . .
H17A H 0.796495 0.752815 0.576797 0.036 Uiso 1 1 calc R U . . .
H17B H 0.907070 0.734343 0.644554 0.036 Uiso 1 1 calc R U . . .
H17C H 0.834602 0.797877 0.667930 0.036 Uiso 1 1 calc R U . . .
C13 C 0.47536(9) 0.86641(7) 0.49958(7) 0.0265(3) Uani 1 1 d . . . . .
H13A H 0.542637 0.868576 0.498616 0.040 Uiso 1 1 calc R U . . .
H13B H 0.440260 0.920232 0.477203 0.040 Uiso 1 1 calc R U . . .
H13C H 0.438068 0.818549 0.464464 0.040 Uiso 1 1 calc R U . . .
C18 C 0.86028(9) 0.66284(10) 0.76813(8) 0.0352(3) Uani 1 1 d . . . . .
H18A H 0.854702 0.716252 0.796197 0.053 Uiso 1 1 calc R U . . .
H18B H 0.930566 0.652680 0.777384 0.053 Uiso 1 1 calc R U . . .
H18C H 0.835329 0.615075 0.791775 0.053 Uiso 1 1 calc R U . . .
C19 C 0.80945(10) 0.58836(8) 0.62730(10) 0.0375(3) Uani 1 1 d . . . . .
H19A H 0.789814 0.538631 0.652440 0.056 Uiso 1 1 calc R U . . .
H19B H 0.879422 0.582204 0.633725 0.056 Uiso 1 1 calc R U . . .
H19C H 0.766585 0.591960 0.566907 0.056 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
O001 C3 1.3237(12) . ?
O001 C4 1.4665(12) . ?
O002 C3 1.1997(12) . ?
N003 C2 1.1443(14) . ?
C6 C11 1.3896(13) . ?
C6 C1 1.5425(13) . ?
C6 C7 1.3961(14) . ?
C10 C11 1.4003(14) . ?
C10 C9 1.3900(14) . ?
C10 C16 1.5336(13) . ?
C8 C7 1.3915(14) . ?
C8 C9 1.4042(14) . ?
C8 C12 1.5334(13) . ?
C11 H11 0.9500 . ?
C3 C1 1.5492(13) . ?
C2 C1 1.4815(13) . ?
C1 C1 1.5893(18) 2_656 ?
C7 H7 0.9500 . ?
C9 H9 0.9500 . ?
C12 C15 1.5379(15) . ?
C12 C14 1.5323(14) . ?
C12 C13 1.5394(14) . ?
C16 C17 1.5312(14) . ?
C16 C18 1.5405(16) . ?
C16 C19 1.5291(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 C4 1.5082(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C3 O001 C4 115.96(8) . . ?
C11 C6 C1 119.23(8) . . ?
C11 C6 C7 120.09(9) . . ?
C7 C6 C1 120.68(8) . . ?
C11 C10 C16 119.11(9) . . ?
C9 C10 C11 117.96(9) . . ?
C9 C10 C16 122.92(9) . . ?
C7 C8 C9 118.23(9) . . ?
C7 C8 C12 122.70(9) . . ?
C9 C8 C12 119.06(9) . . ?
C6 C11 C10 120.84(9) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
O001 C3 C1 110.50(8) . . ?
O002 C3 O001 126.39(9) . . ?
O002 C3 C1 123.05(9) . . ?
N003 C2 C1 178.18(11) . . ?
C6 C1 C3 108.52(7) . . ?
C6 C1 C1 111.48(7) . 2_656 ?
C3 C1 C1 109.08(6) . 2_656 ?
C2 C1 C6 109.97(8) . . ?
C2 C1 C3 108.39(8) . . ?
C2 C1 C1 109.33(9) . 2_656 ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.50(9) . . ?
C8 C7 H7 119.8 . . ?
C10 C9 C8 122.38(9) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C8 C12 C15 109.76(8) . . ?
C8 C12 C13 109.06(8) . . ?
C15 C12 C13 109.07(9) . . ?
C14 C12 C8 112.03(8) . . ?
C14 C12 C15 108.85(9) . . ?
C14 C12 C13 108.00(9) . . ?
C10 C16 C18 107.39(9) . . ?
C17 C16 C10 112.64(8) . . ?
C17 C16 C18 108.35(9) . . ?
C19 C16 C10 110.14(9) . . ?
C19 C16 C17 108.37(9) . . ?
C19 C16 C18 109.91(11) . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
O001 C4 C5 111.41(8) . . ?
O001 C4 H4A 109.3 . . ?
O001 C4 H4B 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O001 C3 C1 C6 -75.43(9) . . . . ?
O001 C3 C1 C2 43.97(10) . . . . ?
O001 C3 C1 C1 162.93(9) . . . 2_656 ?
O002 C3 C1 C6 101.81(10) . . . . ?
O002 C3 C1 C2 -138.78(10) . . . . ?
O002 C3 C1 C1 -19.83(14) . . . 2_656 ?
C11 C6 C1 C3 -34.32(11) . . . . ?
C11 C6 C1 C2 -152.73(9) . . . . ?
C11 C6 C1 C1 85.83(11) . . . 2_656 ?
C11 C6 C7 C8 0.84(14) . . . . ?
C11 C10 C9 C8 0.55(14) . . . . ?
C11 C10 C16 C17 173.76(9) . . . . ?
C11 C10 C16 C18 -67.02(12) . . . . ?
C11 C10 C16 C19 52.64(13) . . . . ?
C3 O001 C4 C5 -74.53(11) . . . . ?
C1 C6 C11 C10 -179.45(8) . . . . ?
C1 C6 C7 C8 179.99(8) . . . . ?
C7 C6 C11 C10 -0.29(14) . . . . ?
C7 C6 C1 C3 146.52(9) . . . . ?
C7 C6 C1 C2 28.11(12) . . . . ?
C7 C6 C1 C1 -93.32(11) . . . 2_656 ?
C7 C8 C9 C10 -0.02(14) . . . . ?
C7 C8 C12 C15 124.65(10) . . . . ?
C7 C8 C12 C14 3.60(13) . . . . ?
C7 C8 C12 C13 -115.92(10) . . . . ?
C9 C10 C11 C6 -0.39(14) . . . . ?
C9 C10 C16 C17 -7.90(14) . . . . ?
C9 C10 C16 C18 111.32(11) . . . . ?
C9 C10 C16 C19 -129.01(11) . . . . ?
C9 C8 C7 C6 -0.68(14) . . . . ?
C9 C8 C12 C15 -56.61(12) . . . . ?
C9 C8 C12 C14 -177.66(9) . . . . ?
C9 C8 C12 C13 62.83(12) . . . . ?
C12 C8 C7 C6 178.08(9) . . . . ?
C12 C8 C9 C10 -178.83(9) . . . . ?
C16 C10 C11 C6 178.04(9) . . . . ?
C16 C10 C9 C8 -177.81(9) . . . . ?
C4 O001 C3 O002 -0.29(14) . . . . ?
C4 O001 C3 C1 176.83(8) . . . . ?

_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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.719
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: heptane/ethyl acetate'
