# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_472
_database_code_depnum_ccdc_archive 'CCDC 2160123'
loop_
_audit_author_name
_audit_author_address
'Ryukichi Takagi'
;Hiroshima University
Japan
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
_audit_creation_date             2022-03-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
1,1,2,2-tetramethyl-cyclobuta-quinolin-3(1H)-one
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O'
_chemical_formula_sum            'C15 H19 N O'
_chemical_formula_weight         229.31
_chemical_absolute_configuration ad
_chemical_melting_point          135
_chemical_oxdiff_formula         C15H19N1O1
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.11510(10)
_cell_length_b                   8.44480(10)
_cell_length_c                   21.3264(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1281.41(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20763
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.2120
_cell_measurement_theta_min      4.0680
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.27a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0186
0 0 1 0.0130
1 1 -1 0.0305
-1 -1 1 0.0382
-1 0 -1 0.0341
1 0 1 0.0356
0 -1 1 0.0391
0 1 -1 0.0257
0 -2 -1 0.0334
2 -1 -2 0.0349
0 -1 -2 0.0224

_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
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
0.0002 0.0003 -0.9992 0.0001 0.0721 0.0028
-0.0002 -0.0003 0.9992 -0.0001 -0.0721 -0.0028
1.0003 1.0002 -0.9790 -0.0331 0.0600 0.2839
-1.0003 -1.0002 0.9790 0.0331 -0.0600 -0.2839
-0.9992 -0.0002 -1.0121 -0.1189 0.0800 -0.1778
0.9992 0.0002 1.0121 0.1189 -0.0800 0.1778
-0.0008 -0.9998 0.9919 0.1521 -0.0679 -0.1032
0.0008 0.9998 -0.9919 -0.1521 0.0679 0.1032
-0.0011 -1.9987 -1.0140 0.3044 0.0805 -0.1979
1.9986 -0.9980 -1.9800 0.3902 0.1327 0.2666
-0.0003 -0.9989 -2.0058 0.1523 0.1484 -0.0947

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35155
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.621
_diffrn_reflns_theta_min         4.146
_diffrn_ambient_temperature      100
_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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -64.00   0.50    0.50    --  -41.38-140.00  60.00   88
  2  ω    -86.00 -60.00   0.50    0.50    --  -41.38 140.00 119.00   52
  3  ω    -66.00 -17.00   0.50    0.50    --  -41.38 130.00 -54.00   98
  4  ω     28.00 103.00   0.50    0.50    --   41.38-140.00  60.00  150
  5  ω     28.00  97.00   0.50    0.50    --   41.38-130.00-125.00  138
  6  ω   -138.00-113.00   0.50    0.50    -- -104.00-130.00-125.00   50
  7  ω   -123.00 -97.00   0.50    0.50    -- -104.00-140.00  60.00   52
  8  ω   -100.00 -75.00   0.50    0.50    -- -104.00 140.00 119.00   50
  9  ω    -73.00 -33.00   0.50    0.50    -- -104.00 130.00 -54.00   80
 10  ω     75.00 171.00   0.50    0.50    --  108.75 130.00 -54.00  192
 11  ω     94.00 120.00   0.50    0.50    --  108.75-140.00  60.00   52
 12  ω     94.00 123.00   0.50    0.50    --  108.75 140.00 119.00   58
 13  ω     38.00  64.00   0.50    0.50    --  108.75-130.00-125.00   52
 14  ω    -34.00  35.00   0.50    0.50    --  -41.38  38.00 120.00  138
 15  ω    -64.00 -37.00   0.50    0.50    --  -41.38 -19.00   0.00   54
 16  ω   -105.00 -78.00   0.50    0.50    --  -41.38 -77.00 150.00   54
 17  ω   -121.00 -82.00   0.50    0.50    --  -41.38 -19.00   0.00   78
 18  ω    -43.00 -13.00   0.50    0.50    --  -41.38 -77.00 150.00   60
 19  ω     18.00  70.00   0.50    0.50    --   41.38  77.00 -90.00  104
 20  ω     27.00  79.00   0.50    0.50    --   41.38  57.00 120.00  104
 21  ω     70.00 117.00   0.50    0.50    --   41.38  38.00 120.00   94
 22  ω     13.00  87.00   0.50    0.50    --   41.38  77.00-120.00  148
 23  ω     22.00  54.00   0.50    0.50    --   41.38  38.00 120.00   64
 24  ω     13.00  71.00   0.50    0.50    --   41.38  77.00 -30.00  116
 25  ω     20.00  98.00   0.50    0.50    --   41.38  57.00-150.00  156
 26  ω     76.00 109.00   0.50    0.50    --   41.38  77.00 -30.00   66
 27  ω     49.00  75.00   0.50    0.50    --   41.38  77.00   0.00   52
 28  ω     14.00  75.00   0.50    0.50    --   41.38  77.00 150.00  122
 29  ω     14.00  43.00   0.50    0.50    --   41.38  77.00   0.00   58
 30  ω     13.00  62.00   0.50    0.50    --   41.38  77.00  60.00   98
 31  ω     91.00 116.00   0.50    0.50    --   41.38  77.00 -90.00   50
 32  ω   -110.00 -75.00   0.50    0.50    -- -104.00 -77.00  27.76   70
 33  ω   -173.00-127.00   0.50    0.50    -- -104.00 -72.00 -16.70   92
 34  ω   -170.00-144.00   0.50    0.50    -- -104.00 -64.00  86.97   52
 35  ω   -132.00 -80.00   0.50    0.50    -- -104.00 -61.00-180.00  104
 36  ω   -101.00 -75.00   0.50    0.50    -- -104.00 -77.00   0.00   52
 37  ω   -171.00-126.00   0.50    0.50    -- -104.00 -77.00 120.00   90
 38  ω   -102.00 -76.00   0.50    0.50    -- -104.00 -77.00-180.00   52
 39  ω   -106.00 -80.00   0.50    0.50    -- -104.00 -61.00  60.00   52
 40  ω   -102.00 -77.00   0.50    0.50    -- -104.00 -72.00 -16.70   50
 41  ω   -134.00 -79.00   0.50    0.50    -- -104.00 -67.00 156.92  110
 42  ω   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00  90.00   50
 43  ω   -146.00-120.00   0.50    0.50    -- -104.00 -58.00 -10.34   52
 44  ω   -118.00 -75.00   0.50    0.50    -- -104.00 -77.00 146.11   86
 45  ω   -166.00-137.00   0.50    0.50    -- -104.00 -77.00-180.00   58
 46  ω   -106.00 -80.00   0.50    0.50    -- -104.00 -61.00 -90.00   52
 47  ω   -113.00 -77.00   0.50    0.50    -- -104.00 -71.00 -88.44   72
 48  ω   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00  60.00   50
 49  ω   -163.00-138.00   0.50    0.50    -- -104.00 -60.00-134.63   50
 50  ω   -105.00 -80.00   0.50    0.50    -- -104.00 -61.00  30.00   50
 51  ω   -105.00 -78.00   0.50    0.50    -- -104.00 -70.00  99.86   54
 52  ω   -103.00 -77.00   0.50    0.50    -- -104.00 -77.00 120.00   52
 53  ω   -103.00 -77.00   0.50    0.50    -- -104.00 -76.00-129.93   52
 54  ω   -109.00 -81.00   0.50    0.50    -- -104.00 -60.00-134.63   56
 55  ω   -102.00 -77.00   0.50    0.50    -- -104.00 -73.00 131.81   50
 56  ω   -104.00 -78.00   0.50    0.50    -- -104.00 -70.00 -59.62   52
 57  ω   -108.00 -83.00   0.50    0.50    -- -104.00 -54.00 -21.05   50
 58  ω   -174.00-143.00   0.50    0.50    -- -104.00 -77.00   0.00   62
 59  ω   -107.00 -82.00   0.50    0.50    -- -104.00 -58.00 -10.34   50
 60  ω   -166.00-139.00   0.50    0.50    -- -104.00 -77.00 146.11   54
 61  ω   -105.00 -80.00   0.50    0.50    -- -104.00 -65.00 143.19   50
 62  ω   -103.00 -78.00   0.50    0.50    -- -104.00 -70.00-173.22   50
 63  ω   -148.00 -77.00   0.50    0.50    -- -104.00 -72.00-107.05  142
 64  ω   -168.00-142.00   0.50    0.50    -- -104.00 -77.00-150.00   52
 65  ω   -104.00 -76.00   0.50    0.50    -- -104.00 -77.00-150.00   56
 66  ω   -104.00 -79.00   0.50    0.50    -- -104.00 -66.00 117.05   50
 67  ω   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00 -60.00   50
 68  ω   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00 -92.69   50
 69  ω   -175.00-140.00   0.50    0.50    -- -104.00 -77.00 -92.69   70
 70  ω   -102.00 -77.00   0.50    0.50    -- -104.00 -71.00 -49.22   50
 71  ω   -163.00-137.00   0.50    0.50    -- -104.00 -77.00 -60.00   52
 72  ω   -126.00 -82.00   0.50    0.50    -- -104.00 -64.00  86.97   88
 73  ω   -106.00 -81.00   0.50    0.50    -- -104.00 -65.00 148.70   50
 74  ω   -103.00 -78.00   0.50    0.50    -- -104.00 -70.00 -26.31   50
 75  ω   -100.00 -75.00   0.50    0.50    -- -104.00 -77.00 -30.00   50
 76  ω     80.00 112.00   0.50    0.50    --  108.75-125.00 -90.00   64
 77  ω     77.00 112.00   0.50    0.50    --  108.75-125.00 150.00   70
 78  ω     44.00  72.00   0.50    0.50    --  108.75-125.00 -90.00   56
 79  ω     53.00  97.00   0.50    0.50    --  108.75-125.00-150.00   88
 80  ω     39.00  72.00   0.50    0.50    --  108.75-125.00 150.00   66
 81  ω     36.00  67.00   0.50    0.50    --  108.75 -61.00  60.00   62
 82  ω     38.00  73.00   0.50    0.50    --  108.75 -61.00-180.00   70
 83  ω     40.00  70.00   0.50    0.50    --  108.75 -77.00-120.00   60
 84  ω    152.00 177.00   0.50    0.50    --  108.75  77.00  90.00   50
 85  ω     81.00 146.00   0.50    0.50    --  108.75  77.00  90.00  130
 86  ω     37.00  71.00   0.50    0.50    --  108.75 -61.00 120.00   68
 87  ω     53.00 105.00   0.50    0.50    --  108.75 -95.00   0.00  104
 88  ω     59.00  85.00   0.50    0.50    --  108.75 -95.00-150.00   52
 89  ω    113.00 147.00   0.50    0.50    --  108.75  77.00 -90.00   68
 90  ω     85.00 110.00   0.50    0.50    --  108.75  77.00 -90.00   50
 91  ω    120.00 174.00   0.50    0.50    --  108.75  30.00  60.00  108
 92  ω     85.00 145.00   0.50    0.50    --  108.75  61.00 -30.00  120
 93  ω     89.00 114.00   0.50    0.50    --  108.75  30.00  60.00   50
 94  ω     95.00 165.00   0.50    0.50    --  108.75  61.00-150.00  140
 95  ω     80.00 178.00   0.50    0.50    --  108.75  77.00 150.00  196
 96  ω     69.00 107.00   0.50    0.50    --  108.75-125.00   0.00   76
 97  ω    126.00 175.00   0.50    0.50    --  108.75  45.00  90.00   98
 98  ω     85.00 135.00   0.50    0.50    --  108.75  61.00-120.00  100
 99  ω     38.00  64.00   0.50    0.50    --  108.75-125.00   0.00   52
100  ω     89.00 115.00   0.50    0.50    --  108.75  45.00  90.00   52
101  ω     40.00 106.00   0.50    0.50    --  108.75 -77.00  60.00  132
102  ω    142.00 178.00   0.50    0.50    --  108.75  77.00  30.00   72
103  ω    141.00 175.00   0.50    0.50    --  108.75  45.00   0.00   68
104  ω     80.00 105.00   0.50    0.50    --  108.75 -95.00 -60.00   50
105  ω     90.00 122.00   0.50    0.50    --  108.75  45.00   0.00   64
106  ω     38.00  74.00   0.50    0.50    --  108.75 -95.00 -60.00   72
107  ω    108.00 171.00   0.50    0.50    --  108.75  77.00-180.00  126
108  ω    143.00 173.00   0.50    0.50    --  108.75  45.00-120.00   60
109  ω     45.00  91.00   0.50    0.50    --  108.75 -77.00  30.00   92
110  ω    127.00 153.00   0.50    0.50    --  108.75  77.00 -60.00   52
111  ω     83.00 115.00   0.50    0.50    --  108.75  77.00 -60.00   64
112  ω     96.00 121.00   0.50    0.50    --  108.75  45.00-120.00   50
113  ω    135.00 161.00   0.50    0.50    --  108.75  77.00  60.00   52
114  ω     95.00 175.00   0.50    0.50    --  108.75  77.00 120.00  160
115  ω     80.00 106.00   0.50    0.50    --  108.75  77.00  60.00   52
116  ω     93.00 167.00   0.50    0.50    --  108.75  45.00 -90.00  148
117  ω     67.00 102.00   0.50    0.50    --  108.75 -95.00-120.00   70
118  ω     84.00 137.00   0.50    0.50    --  108.75  77.00  30.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1191121000
_diffrn_orient_matrix_UB_12      -0.1523191000
_diffrn_orient_matrix_UB_13      -0.0000904000
_diffrn_orient_matrix_UB_21      -0.0069407000
_diffrn_orient_matrix_UB_22      -0.0036612000
_diffrn_orient_matrix_UB_23      -0.0721654000
_diffrn_orient_matrix_UB_31      0.1807540000
_diffrn_orient_matrix_UB_32      0.1003112000
_diffrn_orient_matrix_UB_33      -0.0027811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2604
_reflns_number_total             2676
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.90
_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 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.020
_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)+(0.0473P)²+0.2464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0773
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_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 0.40626(15) 0.21011(13) 0.51946(5) 0.0231(2) Uani 1 1 d . . . . .
N1 N 0.58134(17) 0.42731(14) 0.53678(6) 0.0183(3) Uani 1 1 d . . . . .
H1 H 0.675529 0.380496 0.517507 0.022 Uiso 1 1 calc R U . . .
C1 C 0.2909(2) 0.47601(18) 0.67549(6) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.1896(2) 0.33907(17) 0.63810(7) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.2559(2) 0.41985(17) 0.57542(6) 0.0174(3) Uani 1 1 d . . . . .
H3 H 0.147907 0.435925 0.546078 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2993(2) 0.57281(17) 0.61254(6) 0.0177(3) Uani 1 1 d . . . . .
H4 H 0.190069 0.647081 0.610060 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4767(2) 0.65805(17) 0.59605(7) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.5133(2) 0.81153(18) 0.61694(7) 0.0222(3) Uani 1 1 d . . . . .
H6 H 0.422407 0.864546 0.641911 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6802(2) 0.88848(19) 0.60199(7) 0.0246(3) Uani 1 1 d . . . . .
H7 H 0.703181 0.992712 0.616883 0.030 Uiso 1 1 calc R U . . .
C8 C 0.8129(2) 0.81188(19) 0.56512(7) 0.0235(3) Uani 1 1 d . . . . .
H8 H 0.927231 0.863841 0.554868 0.028 Uiso 1 1 calc R U . . .
C9 C 0.7792(2) 0.65961(18) 0.54315(7) 0.0208(3) Uani 1 1 d . . . . .
H9 H 0.869418 0.608069 0.517423 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6124(2) 0.58280(17) 0.55903(6) 0.0177(3) Uani 1 1 d . . . . .
C11 C 0.4196(2) 0.34382(17) 0.54247(6) 0.0177(3) Uani 1 1 d . . . . .
C12 C 0.1828(3) 0.5542(2) 0.72864(8) 0.0304(4) Uani 1 1 d . . . . .
H12A H 0.061908 0.592956 0.712877 0.046 Uiso 1 1 calc R U . . .
H12B H 0.255943 0.643196 0.745196 0.046 Uiso 1 1 calc R U . . .
H12C H 0.160995 0.476787 0.762092 0.046 Uiso 1 1 calc R U . . .
C13 C 0.4858(2) 0.4292(2) 0.69915(7) 0.0256(3) Uani 1 1 d . . . . .
H13A H 0.473030 0.354143 0.733940 0.038 Uiso 1 1 calc R U . . .
H13B H 0.552563 0.523846 0.713660 0.038 Uiso 1 1 calc R U . . .
H13C H 0.556789 0.379567 0.665029 0.038 Uiso 1 1 calc R U . . .
C14 C -0.0243(2) 0.3475(2) 0.64251(8) 0.0248(3) Uani 1 1 d . . . . .
H14A H -0.063984 0.320189 0.685171 0.037 Uiso 1 1 calc R U . . .
H14B H -0.080042 0.272566 0.612737 0.037 Uiso 1 1 calc R U . . .
H14C H -0.066292 0.455044 0.632456 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2511(2) 0.16957(19) 0.65147(8) 0.0264(4) Uani 1 1 d . . . . .
H15A H 0.387568 0.160898 0.646213 0.040 Uiso 1 1 calc R U . . .
H15B H 0.188192 0.097455 0.622228 0.040 Uiso 1 1 calc R U . . .
H15C H 0.217186 0.141344 0.694584 0.040 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 C11 1.2348(18) . ?
N1 C10 1.4136(19) . ?
N1 C11 1.3553(19) . ?
C1 C2 1.579(2) . ?
C1 C4 1.5729(19) . ?
C1 C12 1.520(2) . ?
C1 C13 1.528(2) . ?
C2 C3 1.5730(19) . ?
C2 C14 1.527(2) . ?
C2 C15 1.524(2) . ?
C3 C4 1.5462(19) . ?
C3 C11 1.5042(19) . ?
C4 C5 1.495(2) . ?
C5 C6 1.395(2) . ?
C5 C10 1.400(2) . ?
C6 C7 1.390(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.394(2) . ?

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
C11 N1 C10 125.89(12) . . ?
C4 C1 C2 88.11(10) . . ?
C12 C1 C2 117.64(13) . . ?
C12 C1 C4 115.46(13) . . ?
C12 C1 C13 108.97(13) . . ?
C13 C1 C2 113.05(13) . . ?
C13 C1 C4 112.45(12) . . ?
C3 C2 C1 88.55(11) . . ?
C14 C2 C1 112.95(13) . . ?
C14 C2 C3 109.33(12) . . ?
C15 C2 C1 117.54(13) . . ?
C15 C2 C3 118.71(12) . . ?
C15 C2 C14 108.57(13) . . ?
C4 C3 C2 89.26(10) . . ?
C11 C3 C2 116.36(12) . . ?
C11 C3 C4 116.17(12) . . ?
C3 C4 C1 89.73(10) . . ?
C5 C4 C1 118.89(12) . . ?
C5 C4 C3 116.77(12) . . ?
C6 C5 C4 121.99(14) . . ?
C6 C5 C10 118.23(15) . . ?
C10 C5 C4 119.77(13) . . ?
C7 C6 C5 121.36(15) . . ?
C8 C7 C6 119.52(15) . . ?
C7 C8 C9 120.32(15) . . ?
C8 C9 C10 119.70(14) . . ?
C5 C10 N1 120.19(13) . . ?
C9 C10 N1 118.94(13) . . ?
C9 C10 C5 120.86(14) . . ?
O1 C11 N1 120.35(13) . . ?
O1 C11 C3 121.11(13) . . ?
N1 C11 C3 118.51(12) . . ?

_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 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.810
