#------------------------------------------------------------------------------
#$Date: 2025-01-06 15:51:52 +0200 (Mon, 06 Jan 2025) $
#$Revision: 297133 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160186.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160186
loop_
_publ_author_name
'Amire, Niyaz'
'Almagambetova, Kamila M.'
'Turlykul, Assel'
'Taishybay, Aidyn'
'Nuroldayeva, Gulzat'
'Belyaev, Andrey'
'Peshkov, Anatoly A.'
'Utepbergenov, Darkhan'
'Peshkov, Vsevolod A.'
_publ_section_title
;
 Triflic acid-promoted post-Ugi condensation for the assembly of
 2,6-diarylmorpholin-3-ones.
;
_journal_issue                   48
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9379
_journal_page_last               9387
_journal_paper_doi               10.1039/d4ob01270d
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-05
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2024-07-23 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.234(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.39260(10)
_cell_length_b                   9.5816(2)
_cell_length_c                   16.9103(4)
_cell_measurement_reflns_used    9514
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      77.8820
_cell_measurement_theta_min      5.2800
_cell_volume                     873.74(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  69.00   0.50    0.10    --  102.07-125.00-150.00   52
  2  ω     65.00 105.00   0.50    0.10    --  102.07 -99.00 -30.00   80
  3  ω     65.00  91.00   0.50    0.10    --  102.07-114.00  59.00   52
  4  ω     81.00 106.00   0.50    0.10    --  102.07 -99.00  90.00   50
  5  ω     78.00 104.00   0.50    0.10    --  102.07 -99.00  60.00   52
  6  ω     35.00  65.00   0.50    0.10    --  102.07 -99.00  90.00   60
  7  ω     15.00  97.00   0.50    0.10    --   52.08-114.00  59.00  164
  8  ω     70.00  99.00   0.50    0.10    --  102.07 -99.00 -60.00   58
  9  ω     92.00 117.00   0.50    0.10    --  107.25 -84.00-145.81   50
 10  ω     43.00  77.00   0.50    0.10    --  107.25 -84.00-145.81   68
 11  ω     42.00  67.00   0.50    0.10    --  107.25 -82.00-171.70   50
 12  ω     42.00  67.00   0.50    0.10    --  107.25 -82.00 -56.58   50
 13  ω     45.00  71.00   0.50    0.10    --  107.25 -81.00 -68.56   52
 14  ω     87.00 112.00   0.50    0.10    --  107.25 -81.00 -68.56   50
 15  ω    106.00 136.00   0.50    0.10    --  107.25 -86.00  25.78   60
 16  ω     94.00 120.00   0.50    0.10    --  107.25 -85.00 156.28   52
 17  ω     54.00  82.00   0.50    0.10    --  107.25 -78.00 121.68   56
 18  ω     39.00  64.00   0.50    0.10    --  107.25 -74.00 106.40   50
 19  ω     96.00 121.00   0.50    0.10    --  107.25 -74.00 106.40   50
 20  ω     41.00  87.00   0.50    0.10    --  107.25 -72.00  77.44   92
 21  ω     41.00  67.00   0.50    0.10    --  107.25 -73.00  -3.73   52
 22  ω     67.00  93.00   0.50    0.10    --  107.25 -69.00-139.77   52
 23  ω     42.00  93.00   0.50    0.10    --  107.25 -71.00-122.77  102
 24  ω     45.00  74.00   0.50    0.10    --  102.07 -57.00 -90.00   58
 25  ω     43.00 120.00   0.50    0.10    --  107.25 -76.00 -36.25  154
 26  ω     92.00 117.00   0.50    0.10    --  107.25 -73.00  -3.73   50
 27  ω     42.00  89.00   0.50    0.10    --  107.25 -68.00 128.76   94
 28  ω     26.00  51.00   0.50    0.10    --  102.07 -38.00  90.00   50
 29  ω     37.00  71.00   0.50    0.10    --  102.07 -57.00  30.00   68
 30  ω    -20.00  13.00   0.50    0.10    --   52.08 -19.00 120.00   66
 31  ω     25.00  50.00   0.50    0.10    --  102.07 -38.00   0.00   50
 32  ω     26.00  51.00   0.50    0.10    --  102.07 -38.00 -60.00   50
 33  ω     28.00  53.00   0.50    0.10    --  102.07 -57.00-150.00   50
 34  ω     26.00  51.00   0.50    0.10    --  102.07 -38.00-180.00   50
 35  ω     46.00  96.00   0.50    0.10    --  107.25  13.00-163.63  100
 36  ω     68.00 114.00   0.50    0.10    --  107.25  19.00 -64.14   92
 37  ω     89.00 174.00   0.50    0.10    --  102.07  38.00 -60.00  170
 38  ω    142.00 174.00   0.50    0.10    --  107.25  17.00 -33.14   64
 39  ω    138.00 163.00   0.50    0.10    --  107.25  19.00 -64.14   50
 40  ω    100.00 126.00   0.50    0.10    --  107.25  17.00 -33.14   52
 41  ω    142.00 176.00   0.50    0.10    --  107.25  15.00  19.69   68
 42  ω     88.00 123.00   0.50    0.10    --  102.07  38.00  90.00   70
 43  ω     63.00  91.00   0.50    0.10    --  107.25  13.00  73.52   56
 44  ω     66.00  95.00   0.50    0.10    --  107.25  15.00  19.69   58
 45  ω    140.00 165.00   0.50    0.10    --  107.25  16.00 115.57   50
 46  ω    113.00 176.00   0.50    0.10    --  107.25  13.00  73.52  126
 47  ω    112.00 137.00   0.50    0.10    --  107.25  13.00-163.63   50
 48  ω     29.00 115.00   0.50    0.10    --   52.08  77.00 120.00  172
 49  ω     80.00 124.00   0.50    0.10    --  102.07 125.00 120.00   88
 50  ω     88.00 123.00   0.50    0.10    --  102.07 114.00 150.00   70
 51  ω    127.00 153.00   0.50    0.10    --  102.07 114.00 150.00   52
 52  ω     -1.00  24.00   0.50    0.10    --  -51.83  19.00 120.00   50
 53  ω     -3.00  25.00   0.50    0.10    --  -51.83  19.00  90.00   56
 54  ω     -2.00  25.00   0.50    0.10    --  -51.83  19.00  60.00   54
 55  ω    -52.00 -22.00   0.50    0.10    --  -87.67  57.00 -60.00   60
 56  ω    -48.00 -14.00   0.50    0.10    --  -87.67  57.00 -90.00   68
 57  ω     -1.00  25.00   0.50    0.10    --  -51.83  19.00 -90.00   52
 58  ω   -101.00 -62.00   0.50    0.10    --  -87.67 114.00 150.00   78
 59  ω    -75.00 -50.00   0.50    0.10    --  -51.83 114.00 150.00   50
 60  ω   -131.00 -81.00   0.50    0.10    --  -87.67-114.00  59.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2035890000
_diffrn_orient_matrix_UB_12      -0.1057027000
_diffrn_orient_matrix_UB_13      0.0226388000
_diffrn_orient_matrix_UB_21      0.0853678000
_diffrn_orient_matrix_UB_22      -0.0051162000
_diffrn_orient_matrix_UB_23      -0.0867803000
_diffrn_orient_matrix_UB_31      0.1812460000
_diffrn_orient_matrix_UB_32      0.1210424000
_diffrn_orient_matrix_UB_33      0.0161124000
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13716
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.255
_diffrn_reflns_theta_min         2.613
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1280 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0329
_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)+(0.0571P)²+0.0492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.824
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                3221
_reflns_number_total             3373
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01270d2.cif
_cod_data_source_block           vp_6a_2_auto
_cod_depositor_comments
'Adding full bibliography for 7160185--7160187.cif.'
_cod_database_code               7160186
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_chemical_oxdiff_usercomment     'colorless plates, etoac'
_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.
;
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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 2.323
_oxdiff_exptl_absorpt_empirical_full_min 0.530
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
C1 C 0.4452(3) 0.36369(19) 0.78274(11) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.301912 0.329706 0.750337 0.027 Uiso 1 1 calc R U . . .
C2 C 0.6716(3) 0.3759(2) 0.72830(11) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.4783(3) 0.5931(2) 0.69190(12) 0.0248(4) Uani 1 1 d . . . . .
H3 H 0.448588 0.658952 0.650964 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3435(3) 0.5983(2) 0.75742(11) 0.0222(4) Uani 1 1 d . . . . .
C5 C 0.1530(3) 0.7023(2) 0.77659(11) 0.0219(4) Uani 1 1 d . . . . .
C6 C 0.1363(3) 0.8264(2) 0.73294(12) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.252260 0.844239 0.692028 0.032 Uiso 1 1 calc R U . . .
C7 C -0.0474(4) 0.9231(2) 0.74881(13) 0.0295(4) Uani 1 1 d . . . . .
H7 H -0.058762 1.005806 0.718038 0.035 Uiso 1 1 calc R U . . .
C8 C -0.2146(4) 0.9000(2) 0.80928(13) 0.0293(4) Uani 1 1 d . . . . .
H8 H -0.339532 0.967035 0.820358 0.035 Uiso 1 1 calc R U . . .
C9 C -0.1990(3) 0.7786(2) 0.85357(12) 0.0292(4) Uani 1 1 d . . . . .
H9 H -0.312686 0.762734 0.895378 0.035 Uiso 1 1 calc R U . . .
C10 C -0.0171(3) 0.6800(2) 0.83698(12) 0.0251(4) Uani 1 1 d . . . . .
H10 H -0.008932 0.596478 0.867169 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4800(3) 0.2655(2) 0.85079(11) 0.0237(4) Uani 1 1 d . . . . .
C12 C 0.6827(3) 0.2786(2) 0.90165(12) 0.0281(4) Uani 1 1 d . . . . .
H12 H 0.805063 0.347707 0.891743 0.034 Uiso 1 1 calc R U . . .
C13 C 0.7064(4) 0.1916(2) 0.96647(12) 0.0332(5) Uani 1 1 d . . . . .
H13 H 0.844843 0.201339 1.000955 0.040 Uiso 1 1 calc R U . . .
C14 C 0.5296(4) 0.0902(3) 0.98141(13) 0.0353(5) Uani 1 1 d . . . . .
H14 H 0.546431 0.030530 1.025976 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3283(4) 0.0763(2) 0.93108(14) 0.0349(5) Uani 1 1 d . . . . .
H15 H 0.207438 0.006343 0.940847 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3021(3) 0.1642(2) 0.86642(13) 0.0288(4) Uani 1 1 d . . . . .
H16 H 0.161962 0.155122 0.832610 0.035 Uiso 1 1 calc R U . . .
C17 C 0.8533(3) 0.5155(2) 0.62106(11) 0.0284(4) Uani 1 1 d . . . . .
H17A H 0.970274 0.435913 0.620879 0.034 Uiso 1 1 calc R U . . .
H17B H 0.948552 0.600539 0.634806 0.034 Uiso 1 1 calc R U . . .
C18 C 0.7451(3) 0.5326(2) 0.53906(11) 0.0258(4) Uani 1 1 d . . . . .
C19 C 0.8572(4) 0.6237(2) 0.48615(12) 0.0289(4) Uani 1 1 d . . . . .
H19 H 0.998017 0.676192 0.502321 0.035 Uiso 1 1 calc R U . . .
C20 C 0.7650(4) 0.6385(2) 0.40986(13) 0.0345(5) Uani 1 1 d . . . . .
H20 H 0.845518 0.699183 0.373720 0.041 Uiso 1 1 calc R U . . .
C21 C 0.5567(4) 0.5653(2) 0.38618(13) 0.0346(5) Uani 1 1 d . . . . .
H21 H 0.491052 0.577544 0.334423 0.042 Uiso 1 1 calc R U . . .
C22 C 0.4439(4) 0.4737(3) 0.43848(13) 0.0344(5) Uani 1 1 d . . . . .
H22 H 0.301538 0.422558 0.422352 0.041 Uiso 1 1 calc R U . . .
C23 C 0.5385(4) 0.4568(2) 0.51412(12) 0.0311(4) Uani 1 1 d . . . . .
H23 H 0.461869 0.392853 0.549350 0.037 Uiso 1 1 calc R U . . .
N1 N 0.6647(3) 0.49150(18) 0.68202(9) 0.0249(3) Uani 1 1 d . . . . .
O1 O 0.3804(2) 0.49826(14) 0.81513(8) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.8354(2) 0.28768(16) 0.72513(8) 0.0300(3) Uani 1 1 d . . . . .
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'
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
C2 C1 H1 108.1 . . ?
C11 C1 H1 108.1 . . ?
C11 C1 C2 114.26(15) . . ?
O1 C1 H1 108.1 . . ?
O1 C1 C2 110.70(15) . . ?
O1 C1 C11 107.40(15) . . ?
N1 C2 C1 112.80(15) . . ?
O2 C2 C1 123.30(18) . . ?
O2 C2 N1 123.84(18) . . ?
C4 C3 H3 119.4 . . ?
C4 C3 N1 121.20(17) . . ?
N1 C3 H3 119.4 . . ?
C3 C4 C5 126.56(17) . . ?
C3 C4 O1 119.00(16) . . ?
O1 C4 C5 114.45(15) . . ?
C6 C5 C4 120.19(17) . . ?
C10 C5 C4 121.40(18) . . ?
C10 C5 C6 118.39(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.69(18) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.37(19) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.68(18) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.16(18) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.70(19) . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C1 120.87(18) . . ?
C16 C11 C1 120.02(16) . . ?
C16 C11 C12 119.03(18) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.39(19) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.39(18) . . ?
C15 C16 H16 119.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
N1 C17 H17A 108.9 . . ?
N1 C17 H17B 108.9 . . ?
N1 C17 C18 113.26(15) . . ?
C19 C18 C17 119.43(17) . . ?
C19 C18 C23 118.80(18) . . ?
C23 C18 C17 121.75(18) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.48(19) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(2) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C2 N1 C3 120.90(16) . . ?
C2 N1 C17 121.00(16) . . ?
C3 N1 C17 118.09(16) . . ?
C4 O1 C1 112.71(14) . . ?
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
C1 H1 1.0000 . ?
C1 C2 1.537(3) . ?
C1 C11 1.497(3) . ?
C1 O1 1.444(2) . ?
C2 N1 1.357(3) . ?
C2 O2 1.224(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.329(3) . ?
C3 N1 1.409(2) . ?
C4 C5 1.468(2) . ?
C4 O1 1.382(2) . ?
C5 C6 1.402(3) . ?
C5 C10 1.392(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 C16 1.391(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.511(3) . ?
C17 N1 1.469(2) . ?
C18 C19 1.390(3) . ?
C18 C23 1.394(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 H23 0.9500 . ?
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
C1 C2 N1 C3 6.4(2) . . . . ?
C1 C2 N1 C17 -174.63(15) . . . . ?
C1 C11 C12 C13 176.90(18) . . . . ?
C1 C11 C16 C15 -177.56(19) . . . . ?
C2 C1 C11 C12 53.0(2) . . . . ?
C2 C1 C11 C16 -130.40(18) . . . . ?
C2 C1 O1 C4 54.60(18) . . . . ?
C3 C4 C5 C6 -14.5(3) . . . . ?
C3 C4 C5 C10 164.29(19) . . . . ?
C3 C4 O1 C1 -33.7(2) . . . . ?
C4 C3 N1 C2 17.0(3) . . . . ?
C4 C3 N1 C17 -162.06(17) . . . . ?
C4 C5 C6 C7 177.90(17) . . . . ?
C4 C5 C10 C9 -178.96(17) . . . . ?
C5 C4 O1 C1 146.54(15) . . . . ?
C5 C6 C7 C8 1.3(3) . . . . ?
C6 C5 C10 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C5 0.8(3) . . . . ?
C10 C5 C6 C7 -1.0(3) . . . . ?
C11 C1 C2 N1 -162.15(15) . . . . ?
C11 C1 C2 O2 20.5(3) . . . . ?
C11 C1 O1 C4 179.97(14) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C11 1.1(3) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
C17 C18 C19 C20 178.34(19) . . . . ?
C17 C18 C23 C22 -179.6(2) . . . . ?
C18 C17 N1 C2 122.58(19) . . . . ?
C18 C17 N1 C3 -58.4(2) . . . . ?
C18 C19 C20 C21 1.6(3) . . . . ?
C19 C18 C23 C22 -1.2(3) . . . . ?
C19 C20 C21 C22 -1.8(3) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C18 1.0(3) . . . . ?
C23 C18 C19 C20 -0.1(3) . . . . ?
N1 C3 C4 C5 176.87(17) . . . . ?
N1 C3 C4 O1 -2.9(3) . . . . ?
N1 C17 C18 C19 145.61(19) . . . . ?
N1 C17 C18 C23 -36.0(3) . . . . ?
O1 C1 C2 N1 -40.8(2) . . . . ?
O1 C1 C2 O2 141.87(18) . . . . ?
O1 C1 C11 C12 -70.2(2) . . . . ?
O1 C1 C11 C16 106.40(19) . . . . ?
O1 C4 C5 C6 165.21(16) . . . . ?
O1 C4 C5 C10 -16.0(2) . . . . ?
O2 C2 N1 C3 -176.28(17) . . . . ?
O2 C2 N1 C17 2.7(3) . . . . ?
