#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:55:26 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278420 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/55/7245545.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_7245545
loop_
_publ_author_name
'Chen, Shaomin'
'Chen, Zhiyan'
'Zhang, Tianjian'
'Zhao, Bo'
'You, Bo'
'Li, Minghao'
'Gu, Yanlong'
_publ_section_title
;
 Brønsted acid-catalyzed cascade cyclization: an efficient strategy for
 divergent synthesis of cyclohepta[b]indole derivatives
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              7376
_journal_page_last               7381
_journal_paper_doi               10.1039/D2GC02072F
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C23 H20 Cl N O2, C H Cl3'
_chemical_formula_sum            'C24 H21 Cl4 N O2'
_chemical_formula_weight         497.22
_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     dual
_audit_creation_date             2022-07-29
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-30 deposited with the CCDC.	2022-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.785(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8280(9)
_cell_length_b                   9.9575(4)
_cell_length_c                   16.1714(9)
_cell_measurement_reflns_used    2962
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.5910
_cell_measurement_theta_min      3.0770
_cell_volume                     2275.3(2)
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(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 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -66.00   1.00    1.00    --  -40.73 141.00   4.00   36
  2  ω   -114.00 -25.00   1.00    1.00    --  -40.73 -38.00-150.00   89
  3  ω   -110.00 -29.00   1.00    1.00    --  -40.73 -38.00 120.00   81
  4  ω    120.00 177.00   1.00    2.00    --  107.58 125.00   0.00   57
  5  ω     79.00 175.00   1.00    2.00    --  107.58  30.00 120.00   96
  6  ω     81.00 174.00   1.00    2.00    --  107.58  30.00  30.00   93
  7  ω     71.00 118.00   1.00    2.00    --  107.58 -45.00  60.00   47
  8  ω     46.00 119.00   1.00    2.00    --  107.58-125.00  60.00   73
  9  ω     25.00  96.00   1.00    2.00    --  107.58 -95.00 -60.00   71
;
_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      0.0843156000
_diffrn_orient_matrix_UB_12      -0.0127739000
_diffrn_orient_matrix_UB_13      0.0969264000
_diffrn_orient_matrix_UB_21      0.0679349000
_diffrn_orient_matrix_UB_22      -0.0123187000
_diffrn_orient_matrix_UB_23      -0.0442150000
_diffrn_orient_matrix_UB_31      0.0126615000
_diffrn_orient_matrix_UB_32      0.1537390000
_diffrn_orient_matrix_UB_33      0.0045695000
_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  0.0857
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7879
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         3.128
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26242
_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            'light yellow'
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0866
_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)+(0.1655P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2314
_refine_ls_wR_factor_ref         0.2709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2816
_reflns_number_total             4011
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc02072f2.cif
_cod_data_source_block           exp_4129
_cod_depositor_comments          'Adding full bibliography for 7245545.cif.'
_cod_database_code               7245545
_shelx_shelxl_version_number     2017/1
_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. 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:
 C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C9(H9), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_olex2_date_sample_data_collection 2022-07-29
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.663
_oxdiff_exptl_absorpt_empirical_full_min 0.479
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
Cl1 Cl 0.60225(10) -0.04920(12) 0.79618(7) 0.0435(4) Uani 1 1 d . . . . .
O1 O 0.1534(3) 0.5507(4) 0.4198(3) 0.0476(10) Uani 1 1 d . . . . .
O2 O 0.1737(2) 0.3635(4) 0.5034(2) 0.0403(8) Uani 1 1 d . . . . .
N1 N 0.5360(2) 0.2196(3) 0.4515(2) 0.0246(8) Uani 1 1 d . . . . .
C1 C 0.4971(3) 0.1755(4) 0.5672(3) 0.0255(9) Uani 1 1 d . . . . .
C2 C 0.5082(3) 0.1138(4) 0.6490(3) 0.0292(9) Uani 1 1 d . . . . .
H2 H 0.464980 0.127918 0.672407 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5855(3) 0.0312(4) 0.6939(3) 0.0312(10) Uani 1 1 d . . . . .
C4 C 0.6522(3) 0.0080(4) 0.6613(3) 0.0305(10) Uani 1 1 d . . . . .
H4 H 0.703548 -0.047975 0.694134 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6419(3) 0.0680(4) 0.5801(3) 0.0308(10) Uani 1 1 d . . . . .
H5 H 0.685843 0.053465 0.557566 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5638(3) 0.1508(4) 0.5333(3) 0.0247(9) Uani 1 1 d . . . . .
C7 C 0.4277(3) 0.2662(4) 0.5029(3) 0.0260(9) Uani 1 1 d . . . . .
C8 C 0.4546(3) 0.2905(4) 0.4321(3) 0.0245(9) Uani 1 1 d . . . . .
C9 C 0.4031(3) 0.3613(4) 0.3464(3) 0.0259(9) Uani 1 1 d . . . . .
H9 H 0.412943 0.336470 0.296030 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3413(3) 0.4618(4) 0.3345(3) 0.0258(9) Uani 1 1 d . . . . .
C11 C 0.3331(3) 0.5196(5) 0.4167(3) 0.0299(10) Uani 1 1 d . . . . .
H11A H 0.292955 0.598613 0.397508 0.036 Uiso 1 1 calc R U . . .
H11B H 0.395243 0.547030 0.463240 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2920(3) 0.4182(4) 0.4581(3) 0.0264(9) Uani 1 1 d . . . . .
C13 C 0.3405(3) 0.3070(4) 0.5021(2) 0.0235(9) Uani 1 1 d . . . . .
H13 H 0.315950 0.254080 0.533445 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2866(3) 0.5223(5) 0.2406(3) 0.0280(9) Uani 1 1 d . . . . .
C15 C 0.2652(3) 0.6600(5) 0.2314(3) 0.0321(10) Uani 1 1 d . . . . .
H15 H 0.284387 0.713576 0.283822 0.038 Uiso 1 1 calc R U . . .
C16 C 0.2156(4) 0.7161(5) 0.1442(3) 0.0376(11) Uani 1 1 d . . . . .
H16 H 0.203252 0.807805 0.138600 0.045 Uiso 1 1 calc R U . . .
C17 C 0.1842(4) 0.6376(6) 0.0654(3) 0.0403(12) Uani 1 1 d . . . . .
H17 H 0.150194 0.675700 0.007126 0.048 Uiso 1 1 calc R U . . .
C18 C 0.2042(3) 0.5011(5) 0.0745(3) 0.0361(11) Uani 1 1 d . . . . .
H18 H 0.182862 0.447473 0.021881 0.043 Uiso 1 1 calc R U . . .
C19 C 0.2552(3) 0.4440(5) 0.1606(3) 0.0321(10) Uani 1 1 d . . . . .
H19 H 0.268743 0.352577 0.165482 0.039 Uiso 1 1 calc R U . . .
C20 C 0.1999(3) 0.4511(5) 0.4571(3) 0.0325(10) Uani 1 1 d . . . . .
C21 C 0.0861(4) 0.3957(8) 0.5064(5) 0.0588(17) Uani 1 1 d . . . . .
H21A H 0.089279 0.486581 0.529215 0.071 Uiso 1 1 calc R U . . .
H21B H 0.034179 0.391259 0.444329 0.071 Uiso 1 1 calc R U . . .
C22 C 0.0694(6) 0.3039(8) 0.5654(6) 0.078(2) Uani 1 1 d . . . . .
H22A H 0.063086 0.214599 0.540892 0.117 Uiso 1 1 calc R U . . .
H22B H 0.012305 0.328595 0.568513 0.117 Uiso 1 1 calc R U . . .
H22C H 0.121637 0.306830 0.626343 0.117 Uiso 1 1 calc R U . . .
C24 C 0.5916(3) 0.2246(5) 0.4004(3) 0.0321(10) Uani 1 1 d . . . . .
H24A H 0.553758 0.260966 0.339784 0.048 Uiso 1 1 calc R U . . .
H24B H 0.611713 0.135513 0.394777 0.048 Uiso 1 1 calc R U . . .
H24C H 0.646130 0.280487 0.432863 0.048 Uiso 1 1 calc R U . . .
Cl2 Cl 0.02656(12) 0.5182(2) 0.16193(13) 0.0752(6) Uani 1 1 d . . . . .
Cl3 Cl -0.12566(11) 0.65581(15) 0.17654(10) 0.0545(4) Uani 1 1 d . . . . .
Cl4 Cl -0.08963(13) 0.3791(2) 0.22951(19) 0.0923(8) Uani 1 1 d . . . . .
C23 C -0.0375(4) 0.5325(7) 0.2252(4) 0.0479(14) Uani 1 1 d . . . . .
H23 H 0.005852 0.559451 0.288629 0.058 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'
Cl Cl 0.3639 0.7018 '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
C20 O2 C21 114.8(4) . . ?
C6 N1 C8 109.7(3) . . ?
C6 N1 C24 123.4(4) . . ?
C8 N1 C24 126.7(4) . . ?
C2 C1 C6 119.6(4) . . ?
C2 C1 C7 133.5(4) . . ?
C6 C1 C7 106.9(4) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.7(4) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 Cl1 119.5(4) . . ?
C2 C3 C4 122.9(4) . . ?
C4 C3 Cl1 117.6(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.8(4) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C1 108.3(4) . . ?
N1 C6 C5 129.8(4) . . ?
C5 C6 C1 121.9(4) . . ?
C8 C7 C1 106.4(4) . . ?
C8 C7 C13 125.8(4) . . ?
C13 C7 C1 127.2(4) . . ?
N1 C8 C7 108.7(4) . . ?
N1 C8 C9 122.6(4) . . ?
C7 C8 C9 128.3(4) . . ?
C8 C9 H9 117.9 . . ?
C10 C9 C8 124.1(4) . . ?
C10 C9 H9 117.9 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 C14 119.6(4) . . ?
C14 C10 C11 120.1(4) . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C10 C11 C12 111.1(4) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 C20 120.6(4) . . ?
C20 C12 C11 117.6(4) . . ?
C7 C13 H13 118.1 . . ?
C12 C13 C7 123.7(4) . . ?
C12 C13 H13 118.1 . . ?
C15 C14 C10 120.3(4) . . ?
C19 C14 C10 121.1(4) . . ?
C19 C14 C15 118.6(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.1(4) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.9(4) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.5(4) . . ?
C18 C19 H19 119.8 . . ?
O1 C20 O2 122.7(5) . . ?
O1 C20 C12 123.6(4) . . ?
O2 C20 C12 113.6(4) . . ?
O2 C21 H21A 109.6 . . ?
O2 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C22 C21 O2 110.4(5) . . ?
C22 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Cl2 C23 Cl3 110.4(3) . . ?
Cl2 C23 Cl4 111.2(4) . . ?
Cl2 C23 H23 108.5 . . ?
Cl3 C23 H23 108.5 . . ?
Cl4 C23 Cl3 109.5(3) . . ?
Cl4 C23 H23 108.5 . . ?
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
Cl1 C3 1.747(4) . ?
O1 C20 1.220(6) . ?
O2 C20 1.332(6) . ?
O2 C21 1.444(6) . ?
N1 C6 1.374(5) . ?
N1 C8 1.376(6) . ?
N1 C24 1.456(5) . ?
C1 C2 1.396(6) . ?
C1 C6 1.413(6) . ?
C1 C7 1.440(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(6) . ?
C3 C4 1.395(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(6) . ?
C7 C8 1.411(6) . ?
C7 C13 1.432(6) . ?
C8 C9 1.436(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.351(6) . ?
C10 C11 1.506(6) . ?
C10 C14 1.494(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.513(6) . ?
C12 C13 1.352(6) . ?
C12 C20 1.487(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.403(7) . ?
C14 C19 1.397(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(6) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.430(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
Cl2 C23 1.742(6) . ?
Cl3 C23 1.756(6) . ?
Cl4 C23 1.752(6) . ?
C23 H23 0.9800 . ?
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
Cl1 C3 C4 C5 179.3(3) . . . . ?
N1 C8 C9 C10 -159.7(4) . . . . ?
C1 C2 C3 Cl1 -179.6(3) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C1 C7 C8 N1 -0.2(4) . . . . ?
C1 C7 C8 C9 172.1(4) . . . . ?
C1 C7 C13 C12 160.6(4) . . . . ?
C2 C1 C6 N1 178.4(4) . . . . ?
C2 C1 C6 C5 -1.2(6) . . . . ?
C2 C1 C7 C8 -178.8(4) . . . . ?
C2 C1 C7 C13 -7.9(7) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 N1 -178.6(4) . . . . ?
C4 C5 C6 C1 0.9(6) . . . . ?
C6 N1 C8 C7 -0.6(4) . . . . ?
C6 N1 C8 C9 -173.5(4) . . . . ?
C6 C1 C2 C3 0.6(6) . . . . ?
C6 C1 C7 C8 0.9(4) . . . . ?
C6 C1 C7 C13 171.8(4) . . . . ?
C7 C1 C2 C3 -179.7(4) . . . . ?
C7 C1 C6 N1 -1.3(4) . . . . ?
C7 C1 C6 C5 179.0(4) . . . . ?
C7 C8 C9 C10 29.0(7) . . . . ?
C8 N1 C6 C1 1.2(4) . . . . ?
C8 N1 C6 C5 -179.2(4) . . . . ?
C8 C7 C13 C12 -30.2(6) . . . . ?
C8 C9 C10 C11 8.9(6) . . . . ?
C8 C9 C10 C14 -175.9(4) . . . . ?
C9 C10 C11 C12 -67.4(5) . . . . ?
C9 C10 C14 C15 -144.8(5) . . . . ?
C9 C10 C14 C19 35.7(6) . . . . ?
C10 C11 C12 C13 68.4(5) . . . . ?
C10 C11 C12 C20 -117.4(4) . . . . ?
C10 C14 C15 C16 179.2(4) . . . . ?
C10 C14 C19 C18 179.5(4) . . . . ?
C11 C10 C14 C15 30.4(6) . . . . ?
C11 C10 C14 C19 -149.1(4) . . . . ?
C11 C12 C13 C7 -8.4(6) . . . . ?
C11 C12 C20 O1 4.7(6) . . . . ?
C11 C12 C20 O2 -173.3(4) . . . . ?
C13 C7 C8 N1 -171.2(4) . . . . ?
C13 C7 C8 C9 1.0(7) . . . . ?
C13 C12 C20 O1 179.0(4) . . . . ?
C13 C12 C20 O2 0.9(6) . . . . ?
C14 C10 C11 C12 117.4(4) . . . . ?
C14 C15 C16 C17 1.8(8) . . . . ?
C15 C14 C19 C18 0.0(7) . . . . ?
C15 C16 C17 C18 -0.9(8) . . . . ?
C16 C17 C18 C19 -0.5(8) . . . . ?
C17 C18 C19 C14 0.9(8) . . . . ?
C19 C14 C15 C16 -1.3(7) . . . . ?
C20 O2 C21 C22 -173.9(6) . . . . ?
C20 C12 C13 C7 177.5(4) . . . . ?
C21 O2 C20 O1 -0.2(7) . . . . ?
C21 O2 C20 C12 177.9(4) . . . . ?
C24 N1 C6 C1 175.7(4) . . . . ?
C24 N1 C6 C5 -4.7(7) . . . . ?
C24 N1 C8 C7 -174.8(4) . . . . ?
C24 N1 C8 C9 12.4(6) . . . . ?
