#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:46:32 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284201 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/16/7131643.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_7131643
loop_
_publ_author_name
'Miao, Yu-Hang'
'Hua, Yuan-Zhao'
'Jia, Shi-Kun'
'Xiao, Xiao'
'Wang, Min-Can'
'Mei, Guang-Jian'
_publ_section_title
;
 Zn-ProPhenol catalyzed asymmetric inverse-electron-demand Diels-Alder
 reaction.
;
_journal_issue                   45
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6929
_journal_page_last               6932
_journal_paper_doi               10.1039/d3cc01641b
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H28 F N O3'
_chemical_formula_sum            'C33 H28 F N O3'
_chemical_formula_weight         505.56
_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     direct
_audit_creation_date             2020-10-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-22 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.756(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5394(8)
_cell_length_b                   11.1681(9)
_cell_length_c                   12.3498(12)
_cell_measurement_reflns_used    3256
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9310
_cell_measurement_theta_min      3.6420
_cell_volume                     1288.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -15.00   1.00    1.00    --  -33.50 -57.00-150.00   73
  2  ω    -95.00 -33.00   1.00    1.00    --  -33.50 -19.00 -60.00   62
  3  ω    -48.00  36.00   1.00    1.00    --  -33.50  37.00  30.00   84
  4  ω    -22.00  25.00   1.00    1.00    --  -33.50  57.00  90.00   47
  5  ω    -28.00   1.00   1.00    1.00    --  -33.50 -19.00 -60.00   29
  6  ω     44.00  76.00   1.00    1.00    --   36.47 -99.00-150.00   32
  7  ω     61.00 110.00   1.00    1.00    --   36.47 178.00-150.00   49
  8  ω     46.00 106.00   1.00    1.00    --   36.47  19.00 150.00   60
  9  ω     44.00  77.00   1.00    1.00    --   36.47  57.00-180.00   33
 10  ω     26.00  70.00   1.00    1.00    --   36.47  57.00  90.00   44
 11  ω     57.00 109.00   1.00    1.00    --   36.47 178.00   0.00   52
 12  ω     -4.00  21.00   1.00    1.00    --   36.47 103.00 -22.43   25
 13  ω     20.00  60.00   1.00    1.00    --   36.47  57.00 150.00   40
 14  ω      9.00  41.00   1.00    1.00    --   36.47 -99.00-150.00   32
 15  ω     16.00  85.00   1.00    1.00    --   36.47  37.00   0.00   69
 16  ω     79.00 105.00   1.00    3.00    --  108.00  77.00 150.00   26
 17  ω     82.00 108.00   1.00    3.00    --  108.00  30.00 120.00   26
 18  ω    125.00 173.00   1.00    3.00    --  108.00  77.00  90.00   48
 19  ω     45.00 104.00   1.00    3.00    --  108.00 -94.00 -60.00   59
 20  ω     79.00 105.00   1.00    3.00    --  108.00  77.00  90.00   26
 21  ω    148.00 177.00   1.00    3.00    --  108.00  45.00 150.00   29
 22  ω     88.00 114.00   1.00    3.00    --  108.00  61.00 150.00   26
 23  ω     96.00 165.00   1.00    3.00    --  108.00  61.00-180.00   69
 24  ω    131.00 175.00   1.00    3.00    --  108.00  61.00  60.00   44
 25  ω     84.00 110.00   1.00    3.00    --  108.00  30.00 150.00   26
 26  ω     88.00 114.00   1.00    3.00    --  108.00  45.00  90.00   26
 27  ω     40.00 123.00   1.00    3.00    --  108.00 -61.00 120.00   83
 28  ω    139.00 165.00   1.00    3.00    --  108.00  30.00 120.00   26
 29  ω     93.00 119.00   1.00    3.00    --  108.00  45.00-180.00   26
 30  ω     38.00  71.00   1.00    3.00    --  108.00 -94.00  30.00   33
 31  ω    128.00 172.00   1.00    3.00    --  108.00  61.00 -90.00   44
 32  ω     40.00  77.00   1.00    3.00    --  108.00-111.00 -90.00   37
 33  ω     37.00 148.00   1.00    3.00    --  108.00 -15.00  90.00  111
 34  ω     83.00 108.00   1.00    3.00    --  108.00  30.00-180.00   25
 35  ω    118.00 176.00   1.00    3.00    --  108.00  77.00 120.00   58
 36  ω     88.00 114.00   1.00    3.00    --  108.00  61.00 120.00   26
 37  ω     79.00 105.00   1.00    3.00    --  108.00  77.00 120.00   26
 38  ω     94.00 120.00   1.00    3.00    --  108.00  61.00 -90.00   26
 39  ω     88.00 114.00   1.00    3.00    --  108.00  61.00  90.00   26
 40  ω     89.00 114.00   1.00    3.00    --  108.00  61.00  60.00   25
 41  ω     95.00 121.00   1.00    3.00    --  108.00  45.00 150.00   26
 42  ω     85.00 139.00   1.00    3.00    --  108.00  30.00-150.00   54
 43  ω     88.00 126.00   1.00    3.00    --  108.00  61.00 -30.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1365033000
_diffrn_orient_matrix_UB_12      -0.0687376000
_diffrn_orient_matrix_UB_13      -0.0537450000
_diffrn_orient_matrix_UB_21      -0.0809506000
_diffrn_orient_matrix_UB_22      0.0577192000
_diffrn_orient_matrix_UB_23      0.0825916000
_diffrn_orient_matrix_UB_31      -0.0449242000
_diffrn_orient_matrix_UB_32      0.1047422000
_diffrn_orient_matrix_UB_33      -0.0807993000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10480
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.675
_diffrn_reflns_theta_min         3.656
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.303
_exptl_crystal_description       prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1666 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4794
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0396
_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)+(0.0405P)²+0.0314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                4182
_reflns_number_total             4794
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc01641b2.cif
_cod_data_source_block           202010220
_cod_depositor_comments          'Adding full bibliography for 7131643.cif.'
_cod_database_code               7131643
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N3F1
_chemical_oxdiff_usercomment     r
_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   0.932
_shelx_estimated_absorpt_t_min   0.871
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.862
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 0.5296(3) 0.3533(3) 0.2579(2) 0.0405(6) Uani 1 1 d . . . . .
H1 H 0.4816 0.2840 0.2827 0.049 Uiso 1 1 calc R . . . .
C2 C 0.6251(3) 0.3089(3) 0.1806(2) 0.0391(6) Uani 1 1 d . . . . .
H2 H 0.6906 0.3737 0.1708 0.047 Uiso 1 1 calc R . . . .
C3 C 0.7150(3) 0.2049(3) 0.2432(2) 0.0400(6) Uani 1 1 d . . . . .
H3 H 0.6477 0.1425 0.2555 0.048 Uiso 1 1 calc R . . . .
C4 C 0.7873(3) 0.2521(3) 0.3556(2) 0.0442(7) Uani 1 1 d . . . . .
H4 H 0.8694 0.2142 0.3937 0.053 Uiso 1 1 calc R . . . .
C5 C 0.7371(3) 0.3461(3) 0.4014(2) 0.0448(7) Uani 1 1 d . . . . .
C6 C 0.8121(3) 0.4023(3) 0.5084(3) 0.0481(7) Uani 1 1 d . . . . .
C7 C 0.4167(3) 0.4461(3) 0.2115(3) 0.0457(7) Uani 1 1 d . . . . .
H7A H 0.4543 0.5255 0.2319 0.055 Uiso 1 1 calc R . . . .
H7B H 0.3954 0.4410 0.1315 0.055 Uiso 1 1 calc R . . . .
C8 C 0.2796(3) 0.4282(3) 0.2541(2) 0.0427(6) Uani 1 1 d . . . . .
C9 C 0.1827(3) 0.5327(3) 0.2552(2) 0.0429(6) Uani 1 1 d . . . . .
C10 C 0.1943(3) 0.6358(3) 0.1949(3) 0.0485(7) Uani 1 1 d . . . . .
H10 H 0.2640 0.6408 0.1524 0.058 Uiso 1 1 calc R . . . .
C11 C 0.1027(4) 0.7313(3) 0.1977(3) 0.0582(8) Uani 1 1 d . . . . .
H11 H 0.1095 0.7998 0.1563 0.070 Uiso 1 1 calc R . . . .
C12 C 0.0012(4) 0.7241(4) 0.2626(3) 0.0657(10) Uani 1 1 d . . . . .
H12 H -0.0597 0.7885 0.2657 0.079 Uiso 1 1 calc R . . . .
C13 C -0.0105(4) 0.6225(4) 0.3225(3) 0.0685(10) Uani 1 1 d . . . . .
H13 H -0.0792 0.6186 0.3660 0.082 Uiso 1 1 calc R . . . .
C14 C 0.0784(4) 0.5265(3) 0.3187(3) 0.0566(8) Uani 1 1 d . . . . .
H14 H 0.0687 0.4574 0.3587 0.068 Uiso 1 1 calc R . . . .
C15 C 0.5419(3) 0.2729(3) 0.0682(2) 0.0397(6) Uani 1 1 d . . . . .
C16 C 0.4308(3) 0.1905(3) 0.0544(3) 0.0541(8) Uani 1 1 d . . . . .
H16 H 0.4078 0.1541 0.1162 0.065 Uiso 1 1 calc R . . . .
C17 C 0.3534(4) 0.1614(4) -0.0501(3) 0.0604(9) Uani 1 1 d . . . . .
H17 H 0.2787 0.1066 -0.0577 0.072 Uiso 1 1 calc R . . . .
C18 C 0.3871(4) 0.2135(4) -0.1424(3) 0.0586(9) Uani 1 1 d . . . . .
H18 H 0.3353 0.1940 -0.2124 0.070 Uiso 1 1 calc R . . . .
C19 C 0.4973(4) 0.2942(3) -0.1309(3) 0.0563(8) Uani 1 1 d . . . . .
H19 H 0.5206 0.3292 -0.1932 0.068 Uiso 1 1 calc R . . . .
C20 C 0.5741(3) 0.3239(3) -0.0263(2) 0.0477(7) Uani 1 1 d . . . . .
H20 H 0.6486 0.3789 -0.0194 0.057 Uiso 1 1 calc R . . . .
C21 C 0.8161(3) 0.1486(3) 0.1779(2) 0.0396(6) Uani 1 1 d . . . . .
C22 C 0.7870(3) 0.0352(3) 0.1340(3) 0.0491(7) Uani 1 1 d . . . . .
H22 H 0.7068 -0.0056 0.1466 0.059 Uiso 1 1 calc R . . . .
C23 C 0.8750(4) -0.0189(3) 0.0716(3) 0.0532(8) Uani 1 1 d . . . . .
H23 H 0.8547 -0.0950 0.0420 0.064 Uiso 1 1 calc R . . . .
C24 C 0.9923(3) 0.0430(3) 0.0550(3) 0.0511(7) Uani 1 1 d . . . . .
C25 C 1.0255(3) 0.1550(3) 0.0966(3) 0.0519(8) Uani 1 1 d . . . . .
H25 H 1.1060 0.1949 0.0837 0.062 Uiso 1 1 calc R . . . .
C26 C 0.9360(3) 0.2082(3) 0.1589(3) 0.0464(7) Uani 1 1 d . . . . .
H26 H 0.9571 0.2844 0.1881 0.056 Uiso 1 1 calc R . . . .
C27 C 0.7938(4) 0.5212(4) 0.6696(3) 0.0673(10) Uani 1 1 d . . . . .
H27A H 0.7672 0.6028 0.6515 0.101 Uiso 1 1 calc GR . . . .
H27B H 0.8961 0.5137 0.6822 0.101 Uiso 1 1 calc GR . . . .
H27C H 0.7611 0.4983 0.7352 0.101 Uiso 1 1 calc GR . . . .
C28 C 0.5851(3) 0.4014(3) 0.5742(2) 0.0440(6) Uani 1 1 d . . . . .
C29 C 0.5547(3) 0.2798(3) 0.5705(2) 0.0482(7) Uani 1 1 d . . . . .
H29 H 0.6275 0.2241 0.5715 0.058 Uiso 1 1 calc R . . . .
C30 C 0.4150(4) 0.2419(3) 0.5654(3) 0.0578(9) Uani 1 1 d . . . . .
H30 H 0.3942 0.1605 0.5617 0.069 Uiso 1 1 calc R . . . .
C31 C 0.3067(4) 0.3234(4) 0.5657(3) 0.0619(9) Uani 1 1 d . . . . .
H31 H 0.2130 0.2974 0.5608 0.074 Uiso 1 1 calc R . . . .
C32 C 0.3383(4) 0.4434(4) 0.5734(3) 0.0613(9) Uani 1 1 d . . . . .
H32 H 0.2659 0.4986 0.5755 0.074 Uiso 1 1 calc R . . . .
C33 C 0.4764(4) 0.4830(3) 0.5781(3) 0.0536(8) Uani 1 1 d . . . . .
H33 H 0.4968 0.5645 0.5840 0.064 Uiso 1 1 calc R . . . .
F1 F 1.0800(3) -0.0107(2) -0.0043(2) 0.0784(7) Uani 1 1 d . . . . .
N1 N 0.7279(3) 0.4430(2) 0.5775(2) 0.0492(6) Uani 1 1 d . . . . .
O1 O 0.6177(2) 0.4095(2) 0.35402(17) 0.0490(5) Uani 1 1 d . . . . .
O2 O 0.9414(3) 0.4164(3) 0.5276(2) 0.0696(7) Uani 1 1 d . . . . .
O3 O 0.2483(3) 0.3307(2) 0.2839(3) 0.0685(7) 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'
F F 0.0727 0.0534 '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 108.4 . . ?
C7 C1 H1 108.4 . . ?
C7 C1 C2 116.9(2) . . ?
O1 C1 H1 108.4 . . ?
O1 C1 C2 109.4(2) . . ?
O1 C1 C7 105.1(2) . . ?
C1 C2 H2 108.2 . . ?
C1 C2 C3 105.7(2) . . ?
C3 C2 H2 108.2 . . ?
C15 C2 C1 113.1(2) . . ?
C15 C2 H2 108.2 . . ?
C15 C2 C3 113.2(2) . . ?
C2 C3 H3 107.2 . . ?
C4 C3 C2 107.4(2) . . ?
C4 C3 H3 107.2 . . ?
C4 C3 C21 114.3(2) . . ?
C21 C3 C2 113.1(2) . . ?
C21 C3 H3 107.2 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 123.8(3) . . ?
C4 C5 O1 124.7(3) . . ?
O1 C5 C6 111.4(3) . . ?
N1 C6 C5 117.0(3) . . ?
O2 C6 C5 120.4(3) . . ?
O2 C6 N1 122.5(3) . . ?
C1 C7 H7A 109.2 . . ?
C1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C1 112.0(3) . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C9 C8 C7 118.7(3) . . ?
O3 C8 C7 120.6(3) . . ?
O3 C8 C9 120.8(3) . . ?
C10 C9 C8 121.8(3) . . ?
C10 C9 C14 119.3(3) . . ?
C14 C9 C8 118.9(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.9(4) . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C2 122.4(3) . . ?
C20 C15 C2 120.0(3) . . ?
C20 C15 C16 117.6(3) . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.1(3) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 121.2(3) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C3 119.3(3) . . ?
C22 C21 C26 118.8(3) . . ?
C26 C21 C3 121.9(3) . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.3(3) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 121.0 . . ?
C24 C23 C22 118.1(3) . . ?
C24 C23 H23 121.0 . . ?
C25 C24 C23 122.7(3) . . ?
F1 C24 C23 118.2(3) . . ?
F1 C24 C25 119.1(3) . . ?
C24 C25 H25 120.7 . . ?
C24 C25 C26 118.6(3) . . ?
C26 C25 H25 120.7 . . ?
C21 C26 C25 120.6(3) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
C29 C28 C33 119.4(3) . . ?
C29 C28 N1 120.6(3) . . ?
C33 C28 N1 119.9(3) . . ?
C28 C29 H29 120.3 . . ?
C28 C29 C30 119.5(3) . . ?
C30 C29 H29 120.3 . . ?
C29 C30 H30 119.6 . . ?
C31 C30 C29 120.8(3) . . ?
C31 C30 H30 119.6 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.4(3) . . ?
C32 C31 H31 120.3 . . ?
C31 C32 H32 119.7 . . ?
C31 C32 C33 120.7(3) . . ?
C33 C32 H32 119.7 . . ?
C28 C33 H33 120.0 . . ?
C32 C33 C28 120.1(3) . . ?
C32 C33 H33 120.0 . . ?
C6 N1 C27 118.0(3) . . ?
C6 N1 C28 123.5(3) . . ?
C28 N1 C27 118.0(3) . . ?
C5 O1 C1 114.8(2) . . ?
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 0.9800 . ?
C1 C2 1.530(4) . ?
C1 C7 1.520(4) . ?
C1 O1 1.450(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.553(4) . ?
C2 C15 1.507(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.513(4) . ?
C3 C21 1.515(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.327(4) . ?
C5 C6 1.506(4) . ?
C5 O1 1.368(4) . ?
C6 N1 1.363(4) . ?
C6 O2 1.219(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.518(4) . ?
C8 C9 1.491(4) . ?
C8 O3 1.206(4) . ?
C9 C10 1.388(4) . ?
C9 C14 1.389(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(4) . ?
C15 C20 1.387(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(4) . ?
C21 C26 1.384(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.388(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.366(5) . ?
C24 C25 1.365(5) . ?
C24 F1 1.358(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.393(4) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C27 N1 1.470(4) . ?
C28 C29 1.387(5) . ?
C28 C33 1.389(5) . ?
C28 N1 1.432(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.387(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.378(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.373(6) . ?
C32 H32 0.9300 . ?
C32 C33 1.380(5) . ?
C33 H33 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
C1 C2 C3 C4 -53.4(3) . . . . ?
C1 C2 C3 C21 179.5(2) . . . . ?
C1 C2 C15 C16 -54.1(4) . . . . ?
C1 C2 C15 C20 125.0(3) . . . . ?
C1 C7 C8 C9 156.1(3) . . . . ?
C1 C7 C8 O3 -25.7(4) . . . . ?
C2 C1 C7 C8 143.9(3) . . . . ?
C2 C1 O1 C5 -46.4(3) . . . . ?
C2 C3 C4 C5 22.5(4) . . . . ?
C2 C3 C21 C22 -108.3(3) . . . . ?
C2 C3 C21 C26 70.6(3) . . . . ?
C2 C15 C16 C17 178.3(3) . . . . ?
C2 C15 C20 C19 -178.7(3) . . . . ?
C3 C2 C15 C16 66.0(4) . . . . ?
C3 C2 C15 C20 -114.8(3) . . . . ?
C3 C4 C5 C6 -174.7(3) . . . . ?
C3 C4 C5 O1 0.0(5) . . . . ?
C3 C21 C22 C23 178.6(3) . . . . ?
C3 C21 C26 C25 -178.7(3) . . . . ?
C4 C3 C21 C22 128.5(3) . . . . ?
C4 C3 C21 C26 -52.7(4) . . . . ?
C4 C5 C6 N1 -142.5(3) . . . . ?
C4 C5 C6 O2 41.7(5) . . . . ?
C4 C5 O1 C1 12.0(4) . . . . ?
C5 C6 N1 C27 -166.7(3) . . . . ?
C5 C6 N1 C28 21.8(5) . . . . ?
C6 C5 O1 C1 -172.7(2) . . . . ?
C7 C1 C2 C3 -172.9(3) . . . . ?
C7 C1 C2 C15 -48.6(4) . . . . ?
C7 C1 O1 C5 -172.8(2) . . . . ?
C7 C8 C9 C10 16.2(4) . . . . ?
C7 C8 C9 C14 -163.6(3) . . . . ?
C8 C9 C10 C11 -180.0(3) . . . . ?
C8 C9 C14 C13 178.9(3) . . . . ?
C9 C10 C11 C12 1.1(5) . . . . ?
C10 C9 C14 C13 -0.9(5) . . . . ?
C10 C11 C12 C13 -1.0(6) . . . . ?
C11 C12 C13 C14 -0.1(7) . . . . ?
C12 C13 C14 C9 1.1(6) . . . . ?
C14 C9 C10 C11 -0.2(5) . . . . ?
C15 C2 C3 C4 -177.7(2) . . . . ?
C15 C2 C3 C21 55.2(3) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
C16 C15 C20 C19 0.5(5) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C15 0.1(5) . . . . ?
C20 C15 C16 C17 -0.9(5) . . . . ?
C21 C3 C4 C5 148.8(3) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C21 C26 C25 0.1(5) . . . . ?
C22 C23 C24 C25 -0.3(5) . . . . ?
C22 C23 C24 F1 178.8(3) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
C24 C25 C26 C21 -0.1(5) . . . . ?
C26 C21 C22 C23 -0.2(5) . . . . ?
C28 C29 C30 C31 -1.1(5) . . . . ?
C29 C28 C33 C32 -2.9(5) . . . . ?
C29 C28 N1 C6 47.8(4) . . . . ?
C29 C28 N1 C27 -123.7(4) . . . . ?
C29 C30 C31 C32 -1.3(6) . . . . ?
C30 C31 C32 C33 1.5(6) . . . . ?
C31 C32 C33 C28 0.6(6) . . . . ?
C33 C28 C29 C30 3.1(5) . . . . ?
C33 C28 N1 C6 -134.3(3) . . . . ?
C33 C28 N1 C27 54.3(4) . . . . ?
F1 C24 C25 C26 -178.9(3) . . . . ?
N1 C28 C29 C30 -178.9(3) . . . . ?
N1 C28 C33 C32 179.1(3) . . . . ?
O1 C1 C2 C3 67.8(3) . . . . ?
O1 C1 C2 C15 -167.8(2) . . . . ?
O1 C1 C7 C8 -94.6(3) . . . . ?
O1 C5 C6 N1 42.1(4) . . . . ?
O1 C5 C6 O2 -133.6(3) . . . . ?
O2 C6 N1 C27 9.0(5) . . . . ?
O2 C6 N1 C28 -162.5(3) . . . . ?
O3 C8 C9 C10 -162.0(3) . . . . ?
O3 C8 C9 C14 18.2(5) . . . . ?
