#------------------------------------------------------------------------------
#$Date: 2025-07-06 17:22:54 +0300 (Sun, 06 Jul 2025) $
#$Revision: 300617 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/47/1574746.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_1574746
loop_
_publ_author_name
'Zhang, Fangqing'
'Xu, Chun'
'Zhang, Zichun'
'Yang, Zhuang'
'Peng, Tao'
'Shao, Wen'
'Feng, Xiaoming'
'Liu, Yangbin'
_publ_section_title
;
 Synthesis of polysubstituted cyclobutanes through a photoredox
 strain-release/[3,3]-rearrangement cascade
;
_journal_issue                   25
_journal_name_full               'Chemical Science'
_journal_page_first              11508
_journal_page_last               11518
_journal_paper_doi               10.1039/D5SC01431J
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C19 H24 N2 O2'
_chemical_formula_sum            'C19 H24 N2 O2'
_chemical_formula_weight         312.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-07-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-19 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.624(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7265(2)
_cell_length_b                   14.7461(2)
_cell_length_c                   12.5014(2)
_cell_measurement_reflns_used    8141
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.6770
_cell_measurement_theta_min      4.7720
_cell_volume                     1699.16(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     74.00 100.00   0.50    0.11    --  105.65 -94.00  90.00   52
  2  ω     36.00  62.00   0.50    0.11    --  105.65 -94.00  90.00   52
  3  ω    -21.00  28.00   0.50    0.05    --   46.79 -94.00-108.00   98
  4  ω     31.00  57.00   0.50    0.05    --   46.79 -94.00-108.00   52
  5  ω     33.00 104.00   0.50    0.11    --  105.65 -94.00-108.00  142
  6  ω     33.00  58.00   0.50    0.11    --  105.65 -61.00 -90.00   50
  7  ω     33.00  58.00   0.50    0.11    --  105.65 -61.00 -60.00   50
  8  ω    -27.00  -1.00   0.50    0.05    --   46.79 -19.00-180.00   52
  9  ω    -15.00  28.00   0.50    0.05    --   46.79 -19.00-120.00   86
 10  ω    118.00 144.00   0.50    0.11    --  105.65  94.00   3.00   52
 11  ω    131.00 157.00   0.50    0.11    --  105.65  61.00 -30.00   52
 12  ω    100.00 126.00   0.50    0.11    --  105.65  61.00 -30.00   52
 13  ω    -64.00 -33.00   0.50    0.11    -- -104.00  61.00-180.00   62
 14  ω    -57.00 -31.00   0.50    0.11    -- -104.00  61.00-150.00   52
 15  ω    -68.00 -36.00   0.50    0.11    -- -104.00  61.00 -30.00   64
 16  ω    -68.00 -34.00   0.50    0.11    -- -104.00  61.00 120.00   68
 17  ω    -65.00 -34.00   0.50    0.11    -- -104.00  61.00 150.00   62
 18  ω    -38.00  26.00   0.50    0.05    --  -46.79  37.00 120.00  128
 19  ω    -62.00  25.00   0.50    0.05    --  -46.79  94.00   3.00  174
 20  ω   -101.00 -37.00   0.50    0.11    -- -104.00  94.00   3.00  128
 21  ω   -174.00 -96.00   0.50    0.11    -- -104.00 -45.00 -90.00  156
 22  ω   -149.00-116.00   0.50    0.11    -- -104.00 -94.00-108.00   66
;
_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      0.1352807000
_diffrn_orient_matrix_UB_12      0.0585990000
_diffrn_orient_matrix_UB_13      0.0549517000
_diffrn_orient_matrix_UB_21      0.0658712000
_diffrn_orient_matrix_UB_22      -0.0770490000
_diffrn_orient_matrix_UB_23      0.0839784000
_diffrn_orient_matrix_UB_31      0.0727664000
_diffrn_orient_matrix_UB_32      -0.0392616000
_diffrn_orient_matrix_UB_33      -0.0827351000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10262
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.910
_diffrn_reflns_theta_min         4.788
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       cube
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0376
_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)+(0.0466P)²+0.5207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3100
_reflns_number_total             3388
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc01431j2.cif
_cod_data_source_block           zfq-2-20240708_auto
_cod_depositor_comments
'Adding full bibliography for 1574745--1574746.cif.'
_cod_database_code               1574746
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_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   0.884
_shelx_estimated_absorpt_t_min   0.884
_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, All O(H) groups
2. Rigid bond restraints
 C19, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C19 \\sim C22 \\sim C23 \\sim C22A \\sim C23A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
{C19, C22A, C23A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{C19, C22, C23}
5. Others
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23A)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23)=FVAR(1)
 Sof(H18)=1-FVAR(2)
 Sof(H17)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C12(H12)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C23(H23), C23A(H23A)
6.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B), C22A(H22C,H22D)
6.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
6.f Idealised tetrahedral OH refined as rotating group:
 O17(H17), O18(H18)
;
_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 1.071
_oxdiff_exptl_absorpt_empirical_full_min 0.922
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'
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 0.85115(11) 0.80327(7) 0.49428(9) 0.0219(2) Uani 1 1 d . . . . .
C2 C 0.91087(11) 0.79815(8) 0.61308(9) 0.0233(2) Uani 1 1 d . . . . .
H2 H 0.9261 0.8522 0.6567 0.028 Uiso 1 1 calc R U . . .
C3 C 0.94734(11) 0.71544(8) 0.66631(9) 0.0238(2) Uani 1 1 d . . . . .
H3 H 0.9874 0.7134 0.7462 0.029 Uiso 1 1 calc R U . . .
C4 C 0.92633(11) 0.63474(8) 0.60472(9) 0.0229(2) Uani 1 1 d . . . . .
C5 C 0.87163(11) 0.63916(7) 0.48688(9) 0.0226(2) Uani 1 1 d . . . . .
H5 H 0.8595 0.5850 0.4437 0.027 Uiso 1 1 calc R U . . .
C6 C 0.83528(12) 0.72129(8) 0.43303(9) 0.0232(2) Uani 1 1 d . . . . .
H6 H 0.7987 0.7229 0.3529 0.028 Uiso 1 1 calc R U . . .
C8 C 0.81638(15) 0.96652(8) 0.50802(12) 0.0356(3) Uani 1 1 d . . . . .
H8A H 0.7492 0.9597 0.5515 0.053 Uiso 1 1 calc R U . . .
H8B H 0.7880 1.0192 0.4581 0.053 Uiso 1 1 calc R U . . .
H8C H 0.9151 0.9753 0.5598 0.053 Uiso 1 1 calc R U . . .
C9 C 0.71714(13) 0.88791(8) 0.32295(10) 0.0273(3) Uani 1 1 d . . . . .
H9A H 0.7549 0.8454 0.2776 0.033 Uiso 1 1 calc R U . . .
H9B H 0.7188 0.9497 0.2924 0.033 Uiso 1 1 calc R U . . .
C10 C 0.95484(13) 0.54842(8) 0.66021(10) 0.0289(3) Uani 1 1 d . . . . .
C12 C 0.56134(12) 0.86239(8) 0.31144(9) 0.0240(2) Uani 1 1 d . . . . .
H12 H 0.5630 0.8059 0.3560 0.029 Uiso 1 1 calc R U . . .
C13 C 0.43848(12) 0.85248(8) 0.19400(9) 0.0239(2) Uani 1 1 d . . . . .
C14 C 0.33261(13) 0.89491(8) 0.25060(10) 0.0268(3) Uani 1 1 d . . . . .
H14A H 0.2684 0.9422 0.2044 0.032 Uiso 1 1 calc R U . . .
H14B H 0.2761 0.8496 0.2775 0.032 Uiso 1 1 calc R U . . .
C15 C 0.46412(13) 0.93297(8) 0.34442(9) 0.0268(3) Uani 1 1 d . . . . .
H15A H 0.4583 0.9245 0.4214 0.032 Uiso 1 1 calc R U . . .
H15B H 0.4877 0.9966 0.3320 0.032 Uiso 1 1 calc R U . . .
C16 C 0.46368(12) 0.91759(8) 0.10759(9) 0.0247(2) Uani 1 1 d . . . . .
C19 C 0.40255(14) 0.75518(8) 0.14120(9) 0.0291(3) Uani 1 1 d D U . . .
C22 C 0.4085(3) 0.63655(13) 0.28991(16) 0.0323(6) Uani 0.645(4) 1 d D U P A 1
H22A H 0.5085 0.6264 0.3007 0.039 Uiso 0.645(4) 1 calc R U P A 1
H22B H 0.3609 0.6032 0.3328 0.039 Uiso 0.645(4) 1 calc R U P A 1
C23 C 0.3359(3) 0.69701(14) 0.21551(17) 0.0264(5) Uani 0.645(4) 1 d D U P A 1
H23 H 0.2361 0.7055 0.2069 0.032 Uiso 0.645(4) 1 calc R U P A 1
C20 C 0.27199(14) 0.76040(10) 0.03308(12) 0.0396(3) Uani 1 1 d . U . . .
H20A H 0.1914 0.7910 0.0492 0.059 Uiso 1 1 calc R U . . .
H20B H 0.2422 0.6990 0.0054 0.059 Uiso 1 1 calc R U . . .
H20C H 0.2989 0.7945 -0.0245 0.059 Uiso 1 1 calc R U . . .
C21 C 0.53108(15) 0.71412(10) 0.11389(12) 0.0399(3) Uani 1 1 d . . . . .
H21A H 0.5510 0.7497 0.0543 0.060 Uiso 1 1 calc R U . . .
H21B H 0.5083 0.6515 0.0881 0.060 Uiso 1 1 calc R U . . .
H21C H 0.6166 0.7147 0.1817 0.060 Uiso 1 1 calc R U . . .
N7 N 0.81177(11) 0.88530(7) 0.44064(8) 0.0277(2) Uani 1 1 d . . . . .
N11 N 0.97631(14) 0.47915(8) 0.70442(10) 0.0418(3) Uani 1 1 d . . . . .
O17 O 0.58092(10) 0.91035(7) 0.08429(8) 0.0405(3) Uani 1 1 d . . . . .
H17 H 0.5792 0.9461 0.0315 0.061 Uiso 0.56(3) 1 calc R U P B 1
O18 O 0.36733(10) 0.97502(6) 0.06085(7) 0.0351(2) Uani 1 1 d . . . . .
H18 H 0.3933 1.0049 0.0134 0.053 Uiso 0.44(3) 1 calc R U P B 2
C22A C 0.3025(4) 0.6465(2) 0.2497(3) 0.0298(10) Uani 0.355(4) 1 d D U P A 2
H22C H 0.2095 0.6563 0.1959 0.036 Uiso 0.355(4) 1 calc R U P A 2
H22D H 0.3132 0.6060 0.3110 0.036 Uiso 0.355(4) 1 calc R U P A 2
C23A C 0.4160(5) 0.6890(2) 0.2395(3) 0.0237(9) Uani 0.355(4) 1 d D U P A 2
H23A H 0.5085 0.6788 0.2938 0.028 Uiso 0.355(4) 1 calc R U P A 2
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
C6 C1 C2 117.44(10) . . ?
N7 C1 C2 121.05(10) . . ?
N7 C1 C6 121.51(10) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.65(10) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.15(10) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.71(10) . . ?
C3 C4 C10 121.21(10) . . ?
C5 C4 C10 120.04(10) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.54(10) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.44(10) . . ?
C5 C6 H6 119.3 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N7 C8 H8A 109.5 . . ?
N7 C8 H8B 109.5 . . ?
N7 C8 H8C 109.5 . . ?
H9A C9 H9B 107.9 . . ?
C12 C9 H9A 109.2 . . ?
C12 C9 H9B 109.2 . . ?
N7 C9 H9A 109.2 . . ?
N7 C9 H9B 109.2 . . ?
N7 C9 C12 112.04(9) . . ?
N11 C10 C4 179.36(13) . . ?
C9 C12 H12 108.3 . . ?
C9 C12 C13 123.12(9) . . ?
C9 C12 C15 118.86(10) . . ?
C13 C12 H12 108.3 . . ?
C15 C12 H12 108.3 . . ?
C15 C12 C13 87.96(8) . . ?
C14 C13 C12 87.37(8) . . ?
C14 C13 C19 117.89(10) . . ?
C16 C13 C12 110.88(9) . . ?
C16 C13 C14 110.43(9) . . ?
C16 C13 C19 110.02(9) . . ?
C19 C13 C12 118.47(9) . . ?
C13 C14 H14A 113.8 . . ?
C13 C14 H14B 113.8 . . ?
H14A C14 H14B 111.0 . . ?
C15 C14 C13 89.06(8) . . ?
C15 C14 H14A 113.8 . . ?
C15 C14 H14B 113.8 . . ?
C12 C15 H15A 113.8 . . ?
C12 C15 H15B 113.8 . . ?
C14 C15 C12 88.94(9) . . ?
C14 C15 H15A 113.8 . . ?
C14 C15 H15B 113.8 . . ?
H15A C15 H15B 111.0 . . ?
O17 C16 C13 118.04(10) . . ?
O18 C16 C13 119.24(10) . . ?
O18 C16 O17 122.70(10) . . ?
C23 C19 C13 109.45(10) . . ?
C20 C19 C13 109.58(10) . . ?
C20 C19 C23 99.72(14) . . ?
C20 C19 C23A 124.8(2) . . ?
C21 C19 C13 111.65(10) . . ?
C21 C19 C23 116.41(13) . . ?
C21 C19 C20 109.31(10) . . ?
C21 C19 C23A 93.44(18) . . ?
C23A C19 C13 107.00(15) . . ?
H22A C22 H22B 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C23 C22 H22B 120.0 . . ?
C19 C23 H23 117.8 . . ?
C22 C23 C19 124.3(2) . . ?
C22 C23 H23 117.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N7 C8 119.23(10) . . ?
C1 N7 C9 119.99(9) . . ?
C8 N7 C9 116.89(9) . . ?
C16 O17 H17 109.5 . . ?
C16 O18 H18 109.5 . . ?
H22C C22A H22D 120.0 . . ?
C23A C22A H22C 120.0 . . ?
C23A C22A H22D 120.0 . . ?
C19 C23A H23A 119.3 . . ?
C22A C23A C19 121.4(4) . . ?
C22A C23A H23A 119.3 . . ?
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 C2 1.4135(15) . ?
C1 C6 1.4127(15) . ?
C1 N7 1.3768(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3803(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3966(16) . ?
C4 C5 1.3990(15) . ?
C4 C10 1.4336(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3759(15) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 N7 1.4567(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C12 1.5230(17) . ?
C9 N7 1.4658(15) . ?
C10 N11 1.1485(17) . ?
C12 H12 1.0000 . ?
C12 C13 1.5762(15) . ?
C12 C15 1.5481(15) . ?
C13 C14 1.5549(15) . ?
C13 C16 1.5226(15) . ?
C13 C19 1.5713(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5390(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O17 1.2684(14) . ?
C16 O18 1.2597(14) . ?
C19 C23 1.551(2) . ?
C19 C20 1.5327(18) . ?
C19 C21 1.5227(18) . ?
C19 C23A 1.542(3) . ?
C22 H22A 0.9500 . ?
C22 H22B 0.9500 . ?
C22 C23 1.319(3) . ?
C23 H23 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O17 H17 0.8400 . ?
O18 H18 0.8400 . ?
C22A H22C 0.9500 . ?
C22A H22D 0.9500 . ?
C22A C23A 1.310(5) . ?
C23A H23A 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 C3 C4 -0.06(16) . . . . ?
C2 C1 C6 C5 2.25(16) . . . . ?
C2 C1 N7 C8 -7.05(16) . . . . ?
C2 C1 N7 C9 -164.18(10) . . . . ?
C2 C3 C4 C5 2.07(16) . . . . ?
C2 C3 C4 C10 -175.70(10) . . . . ?
C3 C4 C5 C6 -1.90(16) . . . . ?
C4 C5 C6 C1 -0.28(16) . . . . ?
C6 C1 C2 C3 -2.07(15) . . . . ?
C6 C1 N7 C8 173.75(11) . . . . ?
C6 C1 N7 C9 16.62(15) . . . . ?
C9 C12 C13 C14 -142.77(11) . . . . ?
C9 C12 C13 C16 -31.89(14) . . . . ?
C9 C12 C13 C19 96.71(12) . . . . ?
C9 C12 C15 C14 146.56(10) . . . . ?
C10 C4 C5 C6 175.90(10) . . . . ?
C12 C9 N7 C1 72.23(13) . . . . ?
C12 C9 N7 C8 -85.42(13) . . . . ?
C12 C13 C14 C15 19.27(8) . . . . ?
C12 C13 C16 O17 59.73(14) . . . . ?
C12 C13 C16 O18 -121.50(12) . . . . ?
C12 C13 C19 C23 66.71(16) . . . . ?
C12 C13 C19 C20 175.11(10) . . . . ?
C12 C13 C19 C21 -63.64(12) . . . . ?
C12 C13 C19 C23A 37.2(2) . . . . ?
C13 C12 C15 C14 19.35(8) . . . . ?
C13 C14 C15 C12 -19.62(8) . . . . ?
C13 C19 C23 C22 -100.1(2) . . . . ?
C13 C19 C23A C22A 113.4(3) . . . . ?
C14 C13 C16 O17 154.88(11) . . . . ?
C14 C13 C16 O18 -26.35(15) . . . . ?
C14 C13 C19 C23 -36.47(16) . . . . ?
C14 C13 C19 C20 71.93(12) . . . . ?
C14 C13 C19 C21 -166.82(10) . . . . ?
C14 C13 C19 C23A -65.9(2) . . . . ?
C15 C12 C13 C14 -19.16(8) . . . . ?
C15 C12 C13 C16 91.72(10) . . . . ?
C15 C12 C13 C19 -139.68(10) . . . . ?
C16 C13 C14 C15 -92.06(10) . . . . ?
C16 C13 C19 C23 -164.29(14) . . . . ?
C16 C13 C19 C20 -55.90(12) . . . . ?
C16 C13 C19 C21 65.35(12) . . . . ?
C16 C13 C19 C23A 166.2(2) . . . . ?
C19 C13 C14 C15 140.31(10) . . . . ?
C19 C13 C16 O17 -73.28(14) . . . . ?
C19 C13 C16 O18 105.49(12) . . . . ?
C20 C19 C23 C22 145.04(19) . . . . ?
C20 C19 C23A C22A -16.3(4) . . . . ?
C21 C19 C23 C22 27.7(2) . . . . ?
C21 C19 C23A C22A -132.7(3) . . . . ?
N7 C1 C2 C3 178.69(10) . . . . ?
N7 C1 C6 C5 -178.52(10) . . . . ?
N7 C9 C12 C13 -175.38(9) . . . . ?
N7 C9 C12 C15 76.49(12) . . . . ?
