#------------------------------------------------------------------------------
#$Date: 2024-09-06 02:09:28 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294413 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/34/7133438.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_7133438
loop_
_publ_author_name
'Meena, Shivam A.'
'Thakur, Deepika'
'Nandy, Abhijit'
'Ranjan, Rahul'
'Rai, Anubhav'
'Banerjee, Shibdas'
'Verma, Akhilesh K.'
_publ_section_title
;
 Transition-metal free, radical oxidation of 1,6-enyne cyclopropanation:
 synthesis of aza-bicyclo[4.1.0]heptane derivatives.
;
_journal_issue                   69
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9230
_journal_page_last               9233
_journal_paper_doi               10.1039/d4cc02639j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-04 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                103.773(4)
_cell_angle_beta                 97.032(3)
_cell_angle_gamma                114.529(4)
_cell_formula_units_Z            4
_cell_length_a                   10.6199(4)
_cell_length_b                   10.8504(5)
_cell_length_c                   15.1555(6)
_cell_measurement_reflns_used    7219
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8660
_cell_measurement_theta_min      3.5090
_cell_volume                     1493.92(13)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_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 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  69.00   0.50    5.00    --    5.23  73.00  85.00  132
  2  ω    -64.00  25.00   0.50    5.00    --    5.23 -73.00 -43.00  178
  3  ω    -16.00  10.00   0.50    5.00    --   -4.91 -99.00 -60.00   52
  4  ω    -22.00  27.00   0.50    5.00    --   -4.91 -99.00 150.00   98
  5  ω    -23.00  28.00   0.50    5.00    --   -4.91 -99.00  30.00  102
  6  ω    -48.00  10.00   0.50    5.00    --    5.23 -57.00  30.00  116
  7  ω     12.00  38.00   0.50    5.00    --    5.23 -99.00-120.00   52
  8  ω     -1.00  47.00   0.50    5.00    --    5.23  38.00-120.00   96
  9  ω    -22.00   3.00   0.50    5.00    --    5.23 -99.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0322609000
_diffrn_orient_matrix_UB_12      -0.0131420000
_diffrn_orient_matrix_UB_13      0.0373303000
_diffrn_orient_matrix_UB_21      0.0094341000
_diffrn_orient_matrix_UB_22      0.0711006000
_diffrn_orient_matrix_UB_23      0.0143476000
_diffrn_orient_matrix_UB_31      -0.0679747000
_diffrn_orient_matrix_UB_32      -0.0228916000
_diffrn_orient_matrix_UB_33      -0.0296296000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21311
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.130
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6120
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0652
_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)+(0.1019P)²+0.2925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1858
_refine_ls_wR_factor_ref         0.2094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3685
_reflns_number_total             6120
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02639j2.cif
_cod_data_source_block           smt-317_auto
_cod_depositor_comments
'Adding full bibliography for 7133436--7133438.cif.'
_cod_original_cell_volume        1493.92(12)
_cod_database_code               7133438
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     14-09-2023
_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.
;
_olex2_refinement_description
;
1. Restrained distances
 C9-C10 \\sim C8-C7 \\sim C6-C5
 with sigma of 0.02
2. Restrained planarity
 C10, C9, C8, C7, C6, C5
 with sigma of 0.1
3. Rigid bond restraints
 C9, C10, C5, C4, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C3 \\sim C4 \\sim C5 \\sim C10 \\sim C9: within 1.4A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 1.4A
Uanis(C21) = Uanis(C22) = Uanis(C23)
Uanis(C9) = Uanis(C10)
5. Rigid body (RIGU) restrains
 C9, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C31(H31A,H31B)
6.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C21(H21), C9(H9), C25(H25), C22(H22), C2(H2), C26(H26), C28(H28),
 C27(H27), C6(H6), C4(H4), C8(H8), C3(H3), C7(H7)
6.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C36(H36A,H36B,H36C), C35(H35A,H35B,
 H35C)
;
_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 1.350
_oxdiff_exptl_absorpt_empirical_full_min 0.818
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O5 O -0.0622(2) 0.3848(2) 0.54590(14) 0.0668(5) Uani 1 1 d . . . . .
O4 O 0.17114(19) 0.5948(2) 0.67957(14) 0.0664(5) Uani 1 1 d . . . . .
O3 O 0.4022(2) 0.4379(2) 0.66718(14) 0.0713(6) Uani 1 1 d . . . . .
O6 O -0.0332(2) 0.8861(2) 0.68591(18) 0.0837(7) Uani 1 1 d . . . . .
O1 O 0.3211(2) 0.6637(2) 0.92874(15) 0.0820(7) Uani 1 1 d . . . . .
N1 N 0.3719(2) 0.5458(2) 0.80417(15) 0.0572(6) Uani 1 1 d . . . . .
N2 N 0.0671(2) 0.7406(2) 0.69346(15) 0.0547(6) Uani 1 1 d . . . . .
O2 O 0.0382(2) 0.4886(2) 0.84860(19) 0.0931(8) Uani 1 1 d . . . . .
C13 C -0.2079(2) 0.4916(3) 0.59220(17) 0.0480(6) Uani 1 1 d . . . . .
C12 C -0.0721(3) 0.4849(3) 0.59339(17) 0.0484(6) Uani 1 1 d . . . . .
C14 C -0.1954(2) 0.6403(3) 0.63350(17) 0.0495(6) Uani 1 1 d . . . . .
C23 C 0.7689(3) 0.7908(3) 0.8871(2) 0.0656(5) Uani 1 1 d . . . . .
C11 C 0.0666(3) 0.6108(3) 0.66007(18) 0.0505(6) Uani 1 1 d . . . . .
C15 C -0.0518(3) 0.7651(3) 0.67007(19) 0.0553(6) Uani 1 1 d . . . . .
C16 C -0.2295(3) 0.5384(3) 0.68920(18) 0.0564(7) Uani 1 1 d . . . . .
H16A H -0.325981 0.495928 0.697045 0.068 Uiso 1 1 calc R U . . .
H16B H -0.155347 0.558451 0.742650 0.068 Uiso 1 1 calc R U . . .
C33 C 0.3273(3) 0.4302(3) 0.72171(19) 0.0544(6) Uani 1 1 d . . . . .
C24 C 0.6340(3) 0.6710(3) 0.86925(18) 0.0580(7) Uani 1 1 d . . . . .
C32 C 0.1932(3) 0.2974(3) 0.70784(19) 0.0560(6) Uani 1 1 d . . . . .
C30 C 0.1240(3) 0.4504(3) 0.8249(2) 0.0604(7) Uani 1 1 d . . . . .
C10 C 0.2971(3) 0.9543(3) 0.7182(2) 0.0640(5) Uani 1 1 d D U . . .
C34 C 0.0863(3) 0.3060(3) 0.7657(2) 0.0584(7) Uani 1 1 d . . . . .
C18 C -0.3112(3) 0.6724(3) 0.5926(2) 0.0665(8) Uani 1 1 d . . . . .
H18A H -0.299051 0.686812 0.533500 0.100 Uiso 1 1 calc R U . . .
H18B H -0.304953 0.757174 0.635008 0.100 Uiso 1 1 calc R U . . .
H18C H -0.403183 0.593406 0.583295 0.100 Uiso 1 1 calc R U . . .
C1 C 0.1997(3) 0.8625(3) 0.7564(2) 0.0609(7) Uani 1 1 d . . . . .
C19 C 0.5125(3) 0.6713(3) 0.82281(19) 0.0584(7) Uani 1 1 d . . . . .
C20 C 0.5213(3) 0.7822(3) 0.7949(2) 0.0649(7) Uani 1 1 d . . . . .
H20 H 0.438038 0.778743 0.764169 0.078 Uiso 1 1 calc R U . . .
C29 C 0.2815(3) 0.5628(3) 0.85895(19) 0.0592(7) Uani 1 1 d . . . . .
C17 C -0.3326(3) 0.3815(3) 0.5109(2) 0.0674(8) Uani 1 1 d . . . . .
H17A H -0.325512 0.411668 0.456286 0.101 Uiso 1 1 calc R U . . .
H17B H -0.420481 0.371708 0.526517 0.101 Uiso 1 1 calc R U . . .
H17C H -0.331106 0.291188 0.498251 0.101 Uiso 1 1 calc R U . . .
C21 C 0.6521(3) 0.9033(3) 0.8106(2) 0.0656(5) Uani 1 1 d . . . . .
H21 H 0.655606 0.979009 0.790525 0.079 Uiso 1 1 calc R U . . .
C9 C 0.2784(3) 0.9337(3) 0.6205(2) 0.0640(5) Uani 1 1 d D U . . .
H9 H 0.196384 0.858371 0.577695 0.077 Uiso 1 1 calc R U . . .
C25 C 0.6300(3) 0.5527(3) 0.89911(19) 0.0668(8) Uani 1 1 d . . . . .
H25 H 0.543487 0.472643 0.889702 0.080 Uiso 1 1 calc R U . . .
C22 C 0.7749(3) 0.9081(3) 0.8562(2) 0.0656(5) Uani 1 1 d . . . . .
H22 H 0.862389 0.987718 0.867100 0.079 Uiso 1 1 calc R U . . .
C5 C 0.4212(3) 1.0724(3) 0.7815(2) 0.0738(9) Uani 1 1 d D U . . .
C36 C 0.1370(3) 0.1956(3) 0.6093(2) 0.0742(9) Uani 1 1 d . . . . .
H36A H 0.105469 0.237627 0.568041 0.111 Uiso 1 1 calc R U . . .
H36B H 0.058143 0.108022 0.606919 0.111 Uiso 1 1 calc R U . . .
H36C H 0.211451 0.176208 0.589931 0.111 Uiso 1 1 calc R U . . .
C31 C 0.1835(3) 0.2439(3) 0.7908(2) 0.0668(8) Uani 1 1 d . . . . .
H31A H 0.261525 0.299784 0.846882 0.080 Uiso 1 1 calc R U . . .
H31B H 0.140886 0.141316 0.778507 0.080 Uiso 1 1 calc R U . . .
C2 C 0.2221(3) 0.8817(4) 0.8490(2) 0.0732(9) Uani 1 1 d . . . . .
H2 H 0.156089 0.816733 0.871347 0.088 Uiso 1 1 calc R U . . .
C26 C 0.7544(4) 0.5606(4) 0.9410(2) 0.0748(9) Uani 1 1 d . . . . .
H26 H 0.752281 0.484192 0.959650 0.090 Uiso 1 1 calc R U . . .
C28 C 0.8930(3) 0.7932(4) 0.9321(2) 0.0753(9) Uani 1 1 d . . . . .
H28 H 0.980645 0.873350 0.944777 0.090 Uiso 1 1 calc R U . . .
C35 C -0.0719(3) 0.2092(3) 0.7251(3) 0.0827(10) Uani 1 1 d . . . . .
H35A H -0.108361 0.243772 0.680620 0.124 Uiso 1 1 calc R U . . .
H35B H -0.120297 0.208192 0.774566 0.124 Uiso 1 1 calc R U . . .
H35C H -0.087526 0.114021 0.694121 0.124 Uiso 1 1 calc R U . . .
C27 C 0.8869(4) 0.6807(4) 0.9572(2) 0.0843(10) Uani 1 1 d . . . . .
H27 H 0.970528 0.682201 0.985493 0.101 Uiso 1 1 calc R U . . .
C6 C 0.5230(4) 1.1635(4) 0.7426(4) 0.0986(13) Uani 1 1 d D . . . .
H6 H 0.604621 1.242593 0.783062 0.118 Uiso 1 1 calc R U . . .
C4 C 0.4441(4) 1.0952(4) 0.8779(3) 0.0963(12) Uani 1 1 d . U . . .
H4 H 0.525264 1.174045 0.918877 0.116 Uiso 1 1 calc R U . . .
C8 C 0.3825(4) 1.0261(4) 0.5904(3) 0.0966(11) Uani 1 1 d D . . . .
H8 H 0.370382 1.012230 0.526385 0.116 Uiso 1 1 calc R U . . .
C3 C 0.3458(4) 1.0003(5) 0.9127(2) 0.1008(13) Uani 1 1 d . U . . .
H3 H 0.360908 1.014373 0.976842 0.121 Uiso 1 1 calc R U . . .
C7 C 0.5056(5) 1.1396(4) 0.6516(4) 0.1135(15) Uani 1 1 d D . . . .
H7 H 0.575811 1.198939 0.628595 0.136 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C33 N1 C19 118.4(2) . . ?
C29 N1 C33 123.5(2) . . ?
C29 N1 C19 116.7(2) . . ?
C11 N2 C15 124.0(2) . . ?
C11 N2 C1 118.3(2) . . ?
C15 N2 C1 117.6(2) . . ?
C12 C13 C14 115.9(2) . . ?
C12 C13 C16 113.5(2) . . ?
C12 C13 C17 115.7(2) . . ?
C16 C13 C14 59.12(17) . . ?
C17 C13 C14 119.8(2) . . ?
C17 C13 C16 120.9(2) . . ?
O5 C12 C13 124.0(2) . . ?
O5 C12 C11 117.0(2) . . ?
C13 C12 C11 119.0(2) . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 C16 115.0(2) . . ?
C15 C14 C18 114.4(2) . . ?
C16 C14 C13 60.02(16) . . ?
C16 C14 C18 119.2(2) . . ?
C18 C14 C13 118.6(2) . . ?
C24 C23 C22 118.4(3) . . ?
C28 C23 C24 120.5(3) . . ?
C28 C23 C22 121.0(3) . . ?
O4 C11 N2 122.2(2) . . ?
O4 C11 C12 120.0(2) . . ?
N2 C11 C12 117.7(2) . . ?
O6 C15 N2 118.9(2) . . ?
O6 C15 C14 122.7(2) . . ?
N2 C15 C14 118.2(2) . . ?
C13 C16 H16A 117.7 . . ?
C13 C16 H16B 117.7 . . ?
C14 C16 C13 60.86(16) . . ?
C14 C16 H16A 117.7 . . ?
C14 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
O3 C33 N1 119.4(2) . . ?
O3 C33 C32 122.0(2) . . ?
N1 C33 C32 118.4(2) . . ?
C23 C24 C25 117.8(3) . . ?
C19 C24 C23 119.0(3) . . ?
C19 C24 C25 123.2(3) . . ?
C33 C32 C34 118.8(2) . . ?
C33 C32 C36 113.7(2) . . ?
C33 C32 C31 114.6(2) . . ?
C36 C32 C34 118.8(2) . . ?
C36 C32 C31 121.2(2) . . ?
C31 C32 C34 59.43(18) . . ?
O2 C30 C34 124.1(3) . . ?
O2 C30 C29 116.7(2) . . ?
C34 C30 C29 119.2(2) . . ?
C1 C10 C9 123.6(3) . . ?
C1 C10 C5 117.3(3) . . ?
C5 C10 C9 119.0(3) . . ?
C30 C34 C32 114.6(2) . . ?
C30 C34 C31 116.6(3) . . ?
C30 C34 C35 115.1(2) . . ?
C31 C34 C32 59.20(18) . . ?
C31 C34 C35 119.7(2) . . ?
C35 C34 C32 120.2(3) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C1 N2 119.2(3) . . ?
C2 C1 N2 118.3(3) . . ?
C2 C1 C10 122.5(3) . . ?
C24 C19 N1 118.8(2) . . ?
C20 C19 N1 120.0(3) . . ?
C20 C19 C24 121.2(3) . . ?
C19 C20 H20 118.9 . . ?
C19 C20 C21 122.2(3) . . ?
C21 C20 H20 118.9 . . ?
O1 C29 N1 122.6(3) . . ?
O1 C29 C30 120.2(2) . . ?
N1 C29 C30 117.2(2) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 H21 120.6 . . ?
C10 C9 H9 120.6 . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H9 120.6 . . ?
C24 C25 H25 120.6 . . ?
C26 C25 C24 118.8(3) . . ?
C26 C25 H25 120.6 . . ?
C23 C22 H22 119.8 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C10 C5 C6 117.5(3) . . ?
C4 C5 C10 120.7(3) . . ?
C4 C5 C6 121.8(3) . . ?
C32 C36 H36A 109.5 . . ?
C32 C36 H36B 109.5 . . ?
C32 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C32 C31 C34 61.37(18) . . ?
C32 C31 H31A 117.6 . . ?
C32 C31 H31B 117.6 . . ?
C34 C31 H31A 117.6 . . ?
C34 C31 H31B 117.6 . . ?
H31A C31 H31B 114.7 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
C25 C26 H26 119.0 . . ?
C25 C26 C27 122.1(3) . . ?
C27 C26 H26 119.0 . . ?
C23 C28 H28 119.7 . . ?
C27 C28 C23 120.5(3) . . ?
C27 C28 H28 119.7 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.3(4) . . ?
C7 C6 H6 118.8 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C9 C8 H8 118.8 . . ?
C9 C8 C7 122.4(4) . . ?
C7 C8 H8 118.8 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
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
O5 C12 1.203(3) . ?
O4 C11 1.206(3) . ?
O3 C33 1.209(3) . ?
O6 C15 1.201(3) . ?
O1 C29 1.205(3) . ?
N1 C33 1.405(3) . ?
N1 C19 1.479(3) . ?
N1 C29 1.384(3) . ?
N2 C11 1.376(3) . ?
N2 C15 1.416(3) . ?
N2 C1 1.472(3) . ?
O2 C30 1.206(3) . ?
C13 C12 1.472(3) . ?
C13 C14 1.528(3) . ?
C13 C16 1.515(3) . ?
C13 C17 1.512(3) . ?
C12 C11 1.538(3) . ?
C14 C15 1.479(3) . ?
C14 C16 1.501(4) . ?
C14 C18 1.513(4) . ?
C23 C24 1.417(4) . ?
C23 C22 1.438(4) . ?
C23 C28 1.394(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C33 C32 1.492(4) . ?
C24 C19 1.394(4) . ?
C24 C25 1.446(4) . ?
C32 C34 1.536(4) . ?
C32 C36 1.502(4) . ?
C32 C31 1.503(4) . ?
C30 C34 1.463(4) . ?
C30 C29 1.531(4) . ?
C10 C1 1.401(4) . ?
C10 C9 1.420(4) . ?
C10 C5 1.415(4) . ?
C34 C31 1.507(4) . ?
C34 C35 1.509(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C1 C2 1.343(4) . ?
C19 C20 1.339(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.403(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C22 1.373(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.363(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.353(4) . ?
C22 H22 0.9300 . ?
C5 C6 1.429(5) . ?
C5 C4 1.395(5) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C3 1.417(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.407(5) . ?
C28 H28 0.9300 . ?
C28 C27 1.341(5) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C27 H27 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.315(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.389(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.381(6) . ?
C3 H3 0.9300 . ?
C7 H7 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
O5 C12 C11 O4 -17.1(4) . . . . ?
O5 C12 C11 N2 161.1(2) . . . . ?
O3 C33 C32 C34 -165.7(3) . . . . ?
O3 C33 C32 C36 -18.3(4) . . . . ?
O3 C33 C32 C31 127.1(3) . . . . ?
N1 C33 C32 C34 18.8(4) . . . . ?
N1 C33 C32 C36 166.2(2) . . . . ?
N1 C33 C32 C31 -48.4(3) . . . . ?
N1 C19 C20 C21 -179.7(2) . . . . ?
N2 C1 C2 C3 -177.9(3) . . . . ?
O2 C30 C34 C32 152.7(3) . . . . ?
O2 C30 C34 C31 -140.9(3) . . . . ?
O2 C30 C34 C35 7.1(5) . . . . ?
O2 C30 C29 O1 24.5(4) . . . . ?
O2 C30 C29 N1 -152.8(3) . . . . ?
C13 C12 C11 O4 161.8(2) . . . . ?
C13 C12 C11 N2 -20.0(3) . . . . ?
C13 C14 C15 O6 164.7(3) . . . . ?
C13 C14 C15 N2 -20.0(4) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 C16 -103.0(2) . . . . ?
C12 C13 C14 C18 147.9(2) . . . . ?
C12 C13 C16 C14 107.2(2) . . . . ?
C14 C13 C12 O5 -162.4(3) . . . . ?
C14 C13 C12 C11 18.7(3) . . . . ?
C23 C24 C19 N1 179.8(2) . . . . ?
C23 C24 C19 C20 0.0(4) . . . . ?
C23 C24 C25 C26 -1.0(4) . . . . ?
C23 C28 C27 C26 -1.9(5) . . . . ?
C11 N2 C15 O6 -164.4(3) . . . . ?
C11 N2 C15 C14 20.1(4) . . . . ?
C11 N2 C1 C10 92.8(3) . . . . ?
C11 N2 C1 C2 -87.5(3) . . . . ?
C15 N2 C11 O4 178.0(2) . . . . ?
C15 N2 C11 C12 -0.1(4) . . . . ?
C15 N2 C1 C10 -86.4(3) . . . . ?
C15 N2 C1 C2 93.3(3) . . . . ?
C15 C14 C16 C13 -110.5(2) . . . . ?
C16 C13 C12 O5 131.8(3) . . . . ?
C16 C13 C12 C11 -47.0(3) . . . . ?
C16 C13 C14 C15 103.7(3) . . . . ?
C16 C13 C14 C18 -109.1(3) . . . . ?
C16 C14 C15 O6 -127.2(3) . . . . ?
C16 C14 C15 N2 48.2(3) . . . . ?
C33 N1 C19 C24 -87.0(3) . . . . ?
C33 N1 C19 C20 92.8(3) . . . . ?
C33 N1 C29 O1 -178.9(3) . . . . ?
C33 N1 C29 C30 -1.7(4) . . . . ?
C33 C32 C34 C30 4.4(4) . . . . ?
C33 C32 C34 C31 -103.1(3) . . . . ?
C33 C32 C34 C35 148.2(3) . . . . ?
C33 C32 C31 C34 110.1(2) . . . . ?
C24 C23 C22 C21 0.1(4) . . . . ?
C24 C23 C28 C27 1.6(5) . . . . ?
C24 C19 C20 C21 0.0(4) . . . . ?
C24 C25 C26 C27 0.7(4) . . . . ?
C30 C34 C31 C32 -104.1(3) . . . . ?
C10 C1 C2 C3 1.9(5) . . . . ?
C10 C9 C8 C7 -0.3(5) . . . . ?
C10 C5 C6 C7 -1.0(6) . . . . ?
C10 C5 C4 C3 1.0(5) . . . . ?
C34 C30 C29 O1 -156.4(3) . . . . ?
C34 C30 C29 N1 26.4(4) . . . . ?
C18 C14 C15 O6 16.2(4) . . . . ?
C18 C14 C15 N2 -168.5(2) . . . . ?
C18 C14 C16 C13 108.0(3) . . . . ?
C1 N2 C11 O4 -1.1(4) . . . . ?
C1 N2 C11 C12 -179.3(2) . . . . ?
C1 N2 C15 O6 14.8(4) . . . . ?
C1 N2 C15 C14 -160.8(2) . . . . ?
C1 C10 C9 C8 -177.3(3) . . . . ?
C1 C10 C5 C6 178.0(3) . . . . ?
C1 C10 C5 C4 0.0(4) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C19 N1 C33 O3 -2.2(4) . . . . ?
C19 N1 C33 C32 173.5(2) . . . . ?
C19 N1 C29 O1 -12.6(4) . . . . ?
C19 N1 C29 C30 164.5(2) . . . . ?
C19 C24 C25 C26 177.8(3) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C29 N1 C33 O3 163.9(3) . . . . ?
C29 N1 C33 C32 -20.5(4) . . . . ?
C29 N1 C19 C24 106.0(3) . . . . ?
C29 N1 C19 C20 -74.2(3) . . . . ?
C29 C30 C34 C32 -26.4(4) . . . . ?
C29 C30 C34 C31 40.0(4) . . . . ?
C29 C30 C34 C35 -172.0(3) . . . . ?
C17 C13 C12 O5 -14.4(4) . . . . ?
C17 C13 C12 C11 166.8(2) . . . . ?
C17 C13 C14 C15 -145.9(3) . . . . ?
C17 C13 C14 C16 110.4(3) . . . . ?
C17 C13 C14 C18 1.2(4) . . . . ?
C17 C13 C16 C14 -108.5(3) . . . . ?
C9 C10 C1 N2 -2.5(4) . . . . ?
C9 C10 C1 C2 177.7(3) . . . . ?
C9 C10 C5 C6 -1.2(4) . . . . ?
C9 C10 C5 C4 -179.2(3) . . . . ?
C9 C8 C7 C6 -1.9(7) . . . . ?
C25 C24 C19 N1 1.0(4) . . . . ?
C25 C24 C19 C20 -178.8(3) . . . . ?
C25 C26 C27 C28 0.8(5) . . . . ?
C22 C23 C24 C19 -0.1(4) . . . . ?
C22 C23 C24 C25 178.8(3) . . . . ?
C22 C23 C28 C27 -177.3(3) . . . . ?
C5 C10 C1 N2 178.3(2) . . . . ?
C5 C10 C1 C2 -1.4(4) . . . . ?
C5 C10 C9 C8 1.8(4) . . . . ?
C5 C6 C7 C8 2.6(7) . . . . ?
C5 C4 C3 C2 -0.6(5) . . . . ?
C36 C32 C34 C30 -141.3(3) . . . . ?
C36 C32 C34 C31 111.2(3) . . . . ?
C36 C32 C34 C35 2.5(4) . . . . ?
C36 C32 C31 C34 -107.3(3) . . . . ?
C31 C32 C34 C30 107.5(3) . . . . ?
C31 C32 C34 C35 -108.7(3) . . . . ?
C28 C23 C24 C19 -179.0(3) . . . . ?
C28 C23 C24 C25 -0.1(4) . . . . ?
C28 C23 C22 C21 179.0(3) . . . . ?
C35 C34 C31 C32 109.5(3) . . . . ?
C6 C5 C4 C3 -176.9(3) . . . . ?
C4 C5 C6 C7 177.0(4) . . . . ?
