#------------------------------------------------------------------------------
#$Date: 2022-03-04 03:42:16 +0200 (Fri, 04 Mar 2022) $
#$Revision: 273316 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158548.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_7158548
loop_
_publ_author_name
'Wang, Wei-Na'
'Liu, Ren-Ming'
'Zhang, Lei'
'Liu, Xiong-Li'
'Dai, Yi-Feng'
'Yu, Zhang-Biao'
'Peng, Li-Jun'
_publ_section_title
;
 Ring opening and skeletal reconstruction of 3-vinyl
 benzofuranone-chromone synthons: catalyst-free access to
 skeletally-diverse 2-pyridone and optically active imidazoline
 derivatives
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D1OB02432A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H30 N2 O3'
_chemical_formula_sum            'C35 H30 N2 O3'
_chemical_formula_weight         526.61
_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             2021-10-06
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-10-28 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.743(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5600(2)
_cell_length_b                   7.67541(19)
_cell_length_c                   16.0245(3)
_cell_measurement_reflns_used    13067
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.9210
_cell_measurement_theta_min      2.7970
_cell_volume                     1368.48(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00  -9.00   1.00    1.00    --  -41.80 -77.00-150.00  109
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00-120.00   99
  3  ω   -130.00  46.00   1.00    1.00    --  -41.80   0.00   0.00  176
  4  ω   -115.00 -14.00   1.00    1.00    --  -41.80 -57.00 120.00  101
  5  ω   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00 120.00   99
  6  ω     23.00  98.00   1.00    1.00    --   41.80-125.00 -30.00   75
  7  ω     82.00 178.00   1.00    1.00    --  107.51  45.00-150.00   96
  8  ω     75.00 178.00   1.00    1.00    --  107.51  77.00 150.00  103
  9  ω     82.00 178.00   1.00    1.00    --  107.51  45.00 -90.00   96
 10  ω     76.00 103.00   1.00    1.00    --  107.51  77.00-120.00   27
 11  ω     82.00 111.00   1.00    1.00    --  107.51  45.00-120.00   29
 12  ω     75.00 102.00   1.00    1.00    --  107.51  77.00-180.00   27
 13  ω     45.00 103.00   1.00    1.00    --  107.51 -95.00-120.00   58
 14  ω     78.00 105.00   1.00    1.00    --  107.51  61.00-120.00   27
 15  ω    139.00 174.00   1.00    1.00    --  107.51  45.00 -60.00   35
 16  ω     78.00 105.00   1.00    1.00    --  107.51  61.00-150.00   27
 17  ω    118.00 171.00   1.00    1.00    --  107.51  61.00 -90.00   53
 18  ω    137.00 170.00   1.00    1.00    --  107.51  61.00-120.00   33
 19  ω     80.00 107.00   1.00    1.00    --  107.51  61.00-180.00   27
 20  ω     75.00 102.00   1.00    1.00    --  107.51  77.00 120.00   27
 21  ω     85.00 112.00   1.00    1.00    --  107.51  45.00 -60.00   27
 22  ω     79.00 111.00   1.00    1.00    --  107.51  61.00 -90.00   32
 23  ω     80.00 106.00   1.00    1.00    --  107.51  61.00 120.00   26
 24  ω     83.00 178.00   1.00    1.00    --  107.51  45.00-180.00   95
 25  ω     78.00 108.00   1.00    1.00    --  107.51  61.00 150.00   30
 26  ω     75.00 101.00   1.00    1.00    --  107.51  77.00-150.00   26
 27  ω     84.00 111.00   1.00    1.00    --  107.51  45.00 150.00   27
 28  ω     85.00 112.00   1.00    1.00    --  107.51  30.00-180.00   27
 29  ω     32.00 135.00   1.00    1.00    --  107.51 -30.00 120.00  103
 30  ω    148.00 173.00   1.00    1.00    --  107.51  61.00 120.00   25
 31  ω     25.00 104.00   1.00    1.00    --  107.51 -95.00 -60.00   79
 32  ω     28.00  54.00   1.00    1.00    --   41.67  38.00 -30.00   26
 33  ω     82.00 108.00   1.00    1.00    --  107.51  45.00-180.00   26
 34  ω    153.00 178.00   1.00    1.00    --  107.51 125.00 -30.00   25
 35  ω    153.00 178.00   1.00    1.00    --  107.51  45.00   0.00   25
 36  ω    -66.00   9.00   1.00    1.00    --  -41.67  38.00 -90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0645306000
_diffrn_orient_matrix_UB_12      0.0360522000
_diffrn_orient_matrix_UB_13      0.0959326000
_diffrn_orient_matrix_UB_21      -0.1224124000
_diffrn_orient_matrix_UB_22      0.0283406000
_diffrn_orient_matrix_UB_23      0.0189314000
_diffrn_orient_matrix_UB_31      -0.0058603000
_diffrn_orient_matrix_UB_32      -0.1953298000
_diffrn_orient_matrix_UB_33      0.0204175000
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16343
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.091
_diffrn_reflns_theta_min         2.865
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2097 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(9)
_refine_ls_extinction_coef       0.0138(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5186
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0326
_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)+(0.0531P)²+0.1006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.859
_reflns_number_gt                5080
_reflns_number_total             5186
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02432a2.cif
_cod_data_source_block           g3
_cod_database_code               7158548
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H26 N26 O26 '
_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.
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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:
 C7(H7), C22(H22), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32),
  C33(H33), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_olex2_date_sample_data_collection 2021-10-06
_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.564
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
O1 O 0.23872(14) 0.6042(3) 0.37795(12) 0.0708(5) Uani 1 1 d . . . . .
H1 H 0.231945 0.631093 0.425921 0.106 Uiso 1 1 calc R U . . .
O2 O 0.30363(12) 0.7457(3) 0.52779(10) 0.0693(6) Uani 1 1 d . . . . .
O3 O 0.67603(14) 0.8681(3) 0.93944(11) 0.0684(5) Uani 1 1 d . . . . .
H3 H 0.703829 0.792928 0.914085 0.103 Uiso 1 1 calc R U . . .
N1 N 0.68554(12) 0.6267(2) 0.70204(9) 0.0338(3) Uani 1 1 d . . . . .
N2 N 0.73047(13) 0.6054(2) 0.84849(9) 0.0414(4) Uani 1 1 d . . . . .
C1 C 0.43845(15) 0.7182(3) 0.44280(12) 0.0388(4) Uani 1 1 d . . . . .
C2 C 0.34856(18) 0.6524(3) 0.37148(13) 0.0489(5) Uani 1 1 d . . . . .
C3 C 0.3721(2) 0.6364(4) 0.29196(14) 0.0590(6) Uani 1 1 d . . . . .
H3A H 0.313896 0.589842 0.245405 0.071 Uiso 1 1 calc R U . . .
C4 C 0.4807(2) 0.6883(3) 0.28066(14) 0.0575(6) Uani 1 1 d . . . . .
H4 H 0.494520 0.675675 0.226444 0.069 Uiso 1 1 calc R U . . .
C5 C 0.57080(19) 0.7596(3) 0.34839(13) 0.0464(5) Uani 1 1 d . . . . .
C6 C 0.54688(16) 0.7733(3) 0.42857(12) 0.0388(4) Uani 1 1 d . . . . .
H6 H 0.605298 0.821128 0.474629 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6928(2) 0.8161(3) 0.33930(16) 0.0585(6) Uani 1 1 d . . . . .
H7 H 0.704569 0.938339 0.357325 0.070 Uiso 1 1 calc R U . . .
C8 C 0.7043(4) 0.8040(6) 0.2471(2) 0.1044(13) Uani 1 1 d . . . . .
H8A H 0.703068 0.683845 0.230254 0.157 Uiso 1 1 calc R U . . .
H8B H 0.778637 0.856224 0.244388 0.157 Uiso 1 1 calc R U . . .
H8C H 0.638376 0.864291 0.208492 0.157 Uiso 1 1 calc R U . . .
C9 C 0.7913(3) 0.7099(5) 0.4006(3) 0.0965(12) Uani 1 1 d . . . . .
H9A H 0.791566 0.733863 0.459442 0.145 Uiso 1 1 calc R U . . .
H9B H 0.867822 0.740698 0.392168 0.145 Uiso 1 1 calc R U . . .
H9C H 0.776586 0.588027 0.388811 0.145 Uiso 1 1 calc R U . . .
C10 C 0.41042(15) 0.7314(3) 0.52729(12) 0.0425(4) Uani 1 1 d . . . . .
C11 C 0.50113(15) 0.7175(3) 0.61040(11) 0.0363(4) Uani 1 1 d . . . . .
C12 C 0.46463(15) 0.7565(3) 0.68720(12) 0.0382(4) Uani 1 1 d . . . . .
H12 H 0.389175 0.806044 0.680219 0.046 Uiso 1 1 calc R U . . .
C13 C 0.53287(15) 0.7260(3) 0.76935(11) 0.0377(4) Uani 1 1 d . . . . .
C14 C 0.61431(14) 0.6509(2) 0.62162(11) 0.0343(4) Uani 1 1 d . . . . .
H14 H 0.641523 0.622622 0.573769 0.041 Uiso 1 1 calc R U . . .
C15 C 0.65059(15) 0.6510(3) 0.77855(11) 0.0356(4) Uani 1 1 d . . . . .
C16 C 0.48557(16) 0.7740(3) 0.84409(12) 0.0413(4) Uani 1 1 d . . . . .
C17 C 0.36115(18) 0.7605(3) 0.83359(14) 0.0500(5) Uani 1 1 d . . . . .
H17 H 0.313247 0.707617 0.783951 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3080(2) 0.8238(4) 0.89529(17) 0.0611(6) Uani 1 1 d . . . . .
H18 H 0.225617 0.811999 0.887181 0.073 Uiso 1 1 calc R U . . .
C19 C 0.3778(2) 0.9047(4) 0.96891(16) 0.0645(7) Uani 1 1 d . . . . .
H19 H 0.342159 0.952078 1.009289 0.077 Uiso 1 1 calc R U . . .
C20 C 0.5005(2) 0.9147(4) 0.98207(15) 0.0608(6) Uani 1 1 d . . . . .
H20 H 0.547615 0.966367 1.032344 0.073 Uiso 1 1 calc R U . . .
C21 C 0.55513(19) 0.8484(3) 0.92110(14) 0.0497(5) Uani 1 1 d . . . . .
C22 C 0.80526(14) 0.5426(3) 0.72427(11) 0.0345(4) Uani 1 1 d . . . . .
H22 H 0.795691 0.419252 0.707966 0.041 Uiso 1 1 calc R U . . .
C23 C 0.84158(15) 0.5575(3) 0.82514(11) 0.0383(4) Uani 1 1 d . . . . .
H23 H 0.898685 0.654059 0.841814 0.046 Uiso 1 1 calc R U . . .
C24 C 0.90312(16) 0.3936(3) 0.86570(11) 0.0407(4) Uani 1 1 d . . . . .
C25 C 0.84469(18) 0.2637(3) 0.89842(12) 0.0467(5) Uani 1 1 d . . . . .
H25 H 0.764924 0.278528 0.898629 0.056 Uiso 1 1 calc R U . . .
C26 C 0.9050(2) 0.1110(4) 0.93096(14) 0.0598(6) Uani 1 1 d . . . . .
H26 H 0.865755 0.024991 0.953725 0.072 Uiso 1 1 calc R U . . .
C27 C 1.0228(2) 0.0864(4) 0.92968(15) 0.0658(7) Uani 1 1 d . . . . .
H27 H 1.062183 -0.016878 0.950535 0.079 Uiso 1 1 calc R U . . .
C28 C 1.0818(2) 0.2149(4) 0.89749(15) 0.0653(7) Uani 1 1 d . . . . .
H28 H 1.161192 0.198597 0.896696 0.078 Uiso 1 1 calc R U . . .
C29 C 1.02309(17) 0.3681(4) 0.86637(13) 0.0536(5) Uani 1 1 d . . . . .
H29 H 1.063841 0.455317 0.845643 0.064 Uiso 1 1 calc R U . . .
C30 C 0.89274(14) 0.6255(3) 0.68127(11) 0.0382(4) Uani 1 1 d . . . . .
C31 C 0.94132(18) 0.5270(3) 0.62631(14) 0.0503(5) Uani 1 1 d . . . . .
H31 H 0.917191 0.412087 0.613927 0.060 Uiso 1 1 calc R U . . .
C32 C 1.0264(2) 0.6011(4) 0.58978(16) 0.0612(6) Uani 1 1 d . . . . .
H32 H 1.058417 0.535423 0.552622 0.073 Uiso 1 1 calc R U . . .
C33 C 1.06309(19) 0.7692(4) 0.60814(17) 0.0622(6) Uani 1 1 d . . . . .
H33 H 1.120207 0.817391 0.583776 0.075 Uiso 1 1 calc R U . . .
C34 C 1.0154(2) 0.8681(4) 0.6630(2) 0.0679(7) Uani 1 1 d . . . . .
H34 H 1.040202 0.982693 0.675488 0.081 Uiso 1 1 calc R U . . .
C35 C 0.93038(19) 0.7956(3) 0.69921(16) 0.0540(5) Uani 1 1 d . . . . .
H35 H 0.898332 0.862216 0.736010 0.065 Uiso 1 1 calc R U . . .
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 O1 H1 109.5 . . ?
C21 O3 H3 109.5 . . ?
C14 N1 C15 125.02(14) . . ?
C14 N1 C22 125.59(14) . . ?
C15 N1 C22 108.65(13) . . ?
C15 N2 C23 108.26(14) . . ?
C2 C1 C10 118.00(17) . . ?
C6 C1 C2 118.11(17) . . ?
C6 C1 C10 123.84(16) . . ?
O1 C2 C1 122.35(19) . . ?
O1 C2 C3 118.12(19) . . ?
C3 C2 C1 119.5(2) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C7 123.59(19) . . ?
C6 C5 C4 117.1(2) . . ?
C6 C5 C7 119.3(2) . . ?
C1 C6 H6 118.7 . . ?
C5 C6 C1 122.65(18) . . ?
C5 C6 H6 118.7 . . ?
C5 C7 H7 107.6 . . ?
C5 C7 C8 113.8(3) . . ?
C5 C7 C9 109.63(19) . . ?
C8 C7 H7 107.6 . . ?
C8 C7 C9 110.3(3) . . ?
C9 C7 H7 107.6 . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C1 118.51(16) . . ?
O2 C10 C11 118.06(16) . . ?
C11 C10 C1 123.31(15) . . ?
C12 C11 C10 117.48(15) . . ?
C14 C11 C10 124.86(16) . . ?
C14 C11 C12 117.21(15) . . ?
C11 C12 H12 117.8 . . ?
C13 C12 C11 124.45(16) . . ?
C13 C12 H12 117.8 . . ?
C12 C13 C15 116.72(15) . . ?
C12 C13 C16 119.50(16) . . ?
C15 C13 C16 123.76(16) . . ?
N1 C14 C11 119.56(15) . . ?
N1 C14 H14 120.2 . . ?
C11 C14 H14 120.2 . . ?
N1 C15 C13 116.71(15) . . ?
N2 C15 N1 114.47(15) . . ?
N2 C15 C13 128.81(15) . . ?
C17 C16 C13 118.15(17) . . ?
C21 C16 C13 124.12(16) . . ?
C21 C16 C17 117.40(17) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.7(2) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
O3 C21 C16 123.27(17) . . ?
O3 C21 C20 116.3(2) . . ?
C20 C21 C16 120.4(2) . . ?
N1 C22 H22 109.1 . . ?
N1 C22 C23 100.86(13) . . ?
N1 C22 C30 113.85(15) . . ?
C23 C22 H22 109.1 . . ?
C30 C22 H22 109.1 . . ?
C30 C22 C23 114.60(14) . . ?
N2 C23 C22 105.81(13) . . ?
N2 C23 H23 108.1 . . ?
N2 C23 C24 116.13(15) . . ?
C22 C23 H23 108.1 . . ?
C24 C23 C22 110.42(15) . . ?
C24 C23 H23 108.1 . . ?
C25 C24 C23 122.96(17) . . ?
C25 C24 C29 118.8(2) . . ?
C29 C24 C23 118.18(18) . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.1(2) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.1 . . ?
C28 C27 C26 119.9(2) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.0(2) . . ?
C29 C28 H28 120.0 . . ?
C24 C29 H29 119.6 . . ?
C28 C29 C24 120.7(2) . . ?
C28 C29 H29 119.6 . . ?
C31 C30 C22 119.71(19) . . ?
C35 C30 C22 121.03(17) . . ?
C35 C30 C31 119.17(18) . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C32 119.8(2) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.5(2) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 120.1(2) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.7(3) . . ?
C35 C34 H34 120.1 . . ?
C30 C35 C34 120.7(2) . . ?
C30 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
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 C2 1.353(3) . ?
O2 C10 1.242(2) . ?
O3 H3 0.8200 . ?
O3 C21 1.356(3) . ?
N1 C14 1.341(2) . ?
N1 C15 1.404(2) . ?
N1 C22 1.480(2) . ?
N2 C15 1.292(2) . ?
N2 C23 1.478(2) . ?
C1 C2 1.413(3) . ?
C1 C6 1.399(3) . ?
C1 C10 1.479(3) . ?
C2 C3 1.379(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(3) . ?
C5 C6 1.390(3) . ?
C5 C7 1.520(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.522(3) . ?
C7 C9 1.523(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.458(2) . ?
C11 C12 1.437(2) . ?
C11 C14 1.370(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(3) . ?
C13 C15 1.448(2) . ?
C13 C16 1.491(2) . ?
C14 H14 0.9300 . ?
C16 C17 1.406(2) . ?
C16 C21 1.399(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.395(3) . ?
C22 H22 0.9800 . ?
C22 C23 1.560(2) . ?
C22 C30 1.510(2) . ?
C23 H23 0.9800 . ?
C23 C24 1.504(3) . ?
C24 C25 1.385(3) . ?
C24 C29 1.398(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.390(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.380(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.377(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.381(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.390(3) . ?
C30 C35 1.382(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.395(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.365(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.384(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.386(3) . ?
C35 H35 0.9300 . ?
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
O1 C2 C3 C4 177.9(2) . . . . ?
O2 C10 C11 C12 -12.4(3) . . . . ?
O2 C10 C11 C14 159.6(2) . . . . ?
N1 C22 C23 N2 13.57(18) . . . . ?
N1 C22 C23 C24 139.99(15) . . . . ?
N1 C22 C30 C31 -119.95(19) . . . . ?
N1 C22 C30 C35 63.5(2) . . . . ?
N2 C23 C24 C25 21.1(3) . . . . ?
N2 C23 C24 C29 -162.13(17) . . . . ?
C1 C2 C3 C4 -1.9(4) . . . . ?
C1 C10 C11 C12 171.63(18) . . . . ?
C1 C10 C11 C14 -16.3(3) . . . . ?
C2 C1 C6 C5 -2.5(3) . . . . ?
C2 C1 C10 O2 -25.3(3) . . . . ?
C2 C1 C10 C11 150.7(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C7 179.0(2) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C7 C8 5.4(3) . . . . ?
C4 C5 C7 C9 -118.6(3) . . . . ?
C6 C1 C2 O1 -176.6(2) . . . . ?
C6 C1 C2 C3 3.2(3) . . . . ?
C6 C1 C10 O2 152.1(2) . . . . ?
C6 C1 C10 C11 -32.0(3) . . . . ?
C6 C5 C7 C8 -176.6(3) . . . . ?
C6 C5 C7 C9 59.4(3) . . . . ?
C7 C5 C6 C1 -177.62(19) . . . . ?
C10 C1 C2 O1 0.9(3) . . . . ?
C10 C1 C2 C3 -179.3(2) . . . . ?
C10 C1 C6 C5 -179.89(19) . . . . ?
C10 C11 C12 C13 170.17(19) . . . . ?
C10 C11 C14 N1 -172.65(18) . . . . ?
C11 C12 C13 C15 0.8(3) . . . . ?
C11 C12 C13 C16 179.37(18) . . . . ?
C12 C11 C14 N1 -0.6(3) . . . . ?
C12 C13 C15 N1 3.6(3) . . . . ?
C12 C13 C15 N2 -177.8(2) . . . . ?
C12 C13 C16 C17 33.3(3) . . . . ?
C12 C13 C16 C21 -139.9(2) . . . . ?
C13 C16 C17 C18 -171.3(2) . . . . ?
C13 C16 C21 O3 -7.1(4) . . . . ?
C13 C16 C21 C20 169.8(2) . . . . ?
C14 N1 C15 N2 174.17(19) . . . . ?
C14 N1 C15 C13 -7.1(3) . . . . ?
C14 N1 C22 C23 178.91(17) . . . . ?
C14 N1 C22 C30 55.7(2) . . . . ?
C14 C11 C12 C13 -2.5(3) . . . . ?
C15 N1 C14 C11 5.5(3) . . . . ?
C15 N1 C22 C23 -10.58(18) . . . . ?
C15 N1 C22 C30 -133.83(16) . . . . ?
C15 N2 C23 C22 -12.5(2) . . . . ?
C15 N2 C23 C24 -135.35(18) . . . . ?
C15 C13 C16 C17 -148.3(2) . . . . ?
C15 C13 C16 C21 38.5(3) . . . . ?
C16 C13 C15 N1 -174.87(18) . . . . ?
C16 C13 C15 N2 3.7(3) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C17 C16 C21 O3 179.6(2) . . . . ?
C17 C16 C21 C20 -3.5(3) . . . . ?
C17 C18 C19 C20 -2.9(4) . . . . ?
C18 C19 C20 C21 1.7(4) . . . . ?
C19 C20 C21 O3 178.6(3) . . . . ?
C19 C20 C21 C16 1.6(4) . . . . ?
C21 C16 C17 C18 2.3(4) . . . . ?
C22 N1 C14 C11 174.53(17) . . . . ?
C22 N1 C15 N2 3.6(2) . . . . ?
C22 N1 C15 C13 -177.64(16) . . . . ?
C22 C23 C24 C25 -99.3(2) . . . . ?
C22 C23 C24 C29 77.5(2) . . . . ?
C22 C30 C31 C32 -176.98(19) . . . . ?
C22 C30 C35 C34 176.6(2) . . . . ?
C23 N2 C15 N1 5.9(2) . . . . ?
C23 N2 C15 C13 -172.65(19) . . . . ?
C23 C22 C30 C31 124.65(19) . . . . ?
C23 C22 C30 C35 -51.9(2) . . . . ?
C23 C24 C25 C26 176.59(19) . . . . ?
C23 C24 C29 C28 -175.7(2) . . . . ?
C24 C25 C26 C27 -1.0(3) . . . . ?
C25 C24 C29 C28 1.3(3) . . . . ?
C25 C26 C27 C28 1.2(4) . . . . ?
C26 C27 C28 C29 -0.1(4) . . . . ?
C27 C28 C29 C24 -1.1(4) . . . . ?
C29 C24 C25 C26 -0.2(3) . . . . ?
C30 C22 C23 N2 136.30(17) . . . . ?
C30 C22 C23 C24 -97.27(19) . . . . ?
C30 C31 C32 C33 0.5(4) . . . . ?
C31 C30 C35 C34 0.1(3) . . . . ?
C31 C32 C33 C34 -0.4(4) . . . . ?
C32 C33 C34 C35 0.1(4) . . . . ?
C33 C34 C35 C30 0.1(4) . . . . ?
C35 C30 C31 C32 -0.4(3) . . . . ?
