#------------------------------------------------------------------------------
#$Date: 2022-08-03 23:51:43 +0200 (Wed 03 de Aug de 2022) $
#$Revision: 277054 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/04/7130468.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_7130468
loop_
_publ_author_name
'Wang, Xinmou'
'Yu, Mo'
'Song, Hongjian'
'Liu, Yuxiu'
'Wang, Qingmin'
_publ_section_title
;
 Palladium metallaphotoredox-catalyzed 3-acylation of indole derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03658D
_journal_year                    2022
_chemical_formula_moiety         'C24 H30 N O2 P'
_chemical_formula_sum            'C24 H30 N O2 P'
_chemical_formula_weight         395.46
_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             2021-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-27 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.458(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6702(8)
_cell_length_b                   8.6322(3)
_cell_length_c                   16.6363(7)
_cell_measurement_reflns_used    15935
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.7050
_cell_measurement_theta_min      2.3920
_cell_volume                     2143.23(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0140228000
_diffrn_orient_matrix_UB_12      -0.0377900000
_diffrn_orient_matrix_UB_13      0.0419714000
_diffrn_orient_matrix_UB_21      -0.0389199000
_diffrn_orient_matrix_UB_22      -0.0470501000
_diffrn_orient_matrix_UB_23      -0.0184531000
_diffrn_orient_matrix_UB_31      0.0233594000
_diffrn_orient_matrix_UB_32      -0.0558016000
_diffrn_orient_matrix_UB_33      -0.0128412000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31479
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.836
_diffrn_reflns_theta_min         2.726
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         7447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0479
_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)+(0.0574P)²+0.5278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1296
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5814
_reflns_number_total             7447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03658d2.cif
_cod_data_source_block           r20210121d
_cod_database_code               7130468
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C19(H19), C20(H20), C22(H22), C23(H23)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C24(H24A,H24B,H24C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.971
_oxdiff_exptl_absorpt_empirical_full_min 0.590
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
P1 P 0.13452(2) 0.67056(4) 0.32126(2) 0.02131(8) Uani 1 1 d . . . . .
O1 O 0.05439(6) 0.67504(11) 0.23343(6) 0.0292(2) Uani 1 1 d . . . . .
O2 O 0.43123(7) 0.17041(11) 0.39507(7) 0.0363(2) Uani 1 1 d . . . . .
N1 N 0.20382(7) 0.52253(12) 0.31987(6) 0.0227(2) Uani 1 1 d . . . . .
C1 C 0.27977(8) 0.35627(13) 0.27185(8) 0.0231(2) Uani 1 1 d . . . . .
C2 C 0.29782(10) 0.27623(15) 0.20802(9) 0.0292(3) Uani 1 1 d . . . . .
H2 H 0.347647 0.208180 0.226202 0.035 Uiso 1 1 calc R . . . .
C3 C 0.24090(10) 0.29943(16) 0.11786(9) 0.0337(3) Uani 1 1 d . . . . .
H3 H 0.251928 0.246431 0.073728 0.040 Uiso 1 1 calc R . . . .
C4 C 0.16769(10) 0.39931(17) 0.09087(8) 0.0319(3) Uani 1 1 d . . . . .
H4 H 0.129313 0.411010 0.028579 0.038 Uiso 1 1 calc R . . . .
C5 C 0.14918(9) 0.48196(15) 0.15200(8) 0.0275(3) Uani 1 1 d . . . . .
H5 H 0.099959 0.551495 0.133120 0.033 Uiso 1 1 calc R . . . .
C6 C 0.20653(8) 0.45798(13) 0.24290(8) 0.0223(2) Uani 1 1 d . . . . .
C7 C 0.27442(8) 0.45978(14) 0.39378(8) 0.0226(2) Uani 1 1 d . . . . .
H7 H 0.287764 0.483401 0.454210 0.027 Uiso 1 1 calc R . . . .
C8 C 0.32284(8) 0.35908(13) 0.36898(8) 0.0221(2) Uani 1 1 d . . . . .
C9 C 0.20426(9) 0.84567(14) 0.34139(8) 0.0264(2) Uani 1 1 d . . . . .
C10 C 0.21071(11) 0.87411(17) 0.25297(10) 0.0361(3) Uani 1 1 d . . . . .
H10A H 0.238614 0.784263 0.239544 0.054 Uiso 1 1 calc GR . . . .
H10B H 0.247125 0.966552 0.259118 0.054 Uiso 1 1 calc GR . . . .
H10C H 0.150479 0.889605 0.204026 0.054 Uiso 1 1 calc GR . . . .
C11 C 0.15680(10) 0.98515(16) 0.35843(10) 0.0368(3) Uani 1 1 d . . . . .
H11A H 0.094216 0.987837 0.312713 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.186961 1.080857 0.355408 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.158922 0.975807 0.418055 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.29938(9) 0.82987(17) 0.41798(10) 0.0366(3) Uani 1 1 d . . . . .
H12A H 0.296107 0.809261 0.474375 0.055 Uiso 1 1 calc GR . . . .
H12B H 0.332523 0.926250 0.423540 0.055 Uiso 1 1 calc GR . . . .
H12C H 0.330240 0.744025 0.404936 0.055 Uiso 1 1 calc GR . . . .
C13 C 0.10333(8) 0.61945(16) 0.41170(8) 0.0270(2) Uani 1 1 d . . . . .
C14 C 0.07906(10) 0.44652(17) 0.40189(10) 0.0350(3) Uani 1 1 d . . . . .
H14A H 0.038258 0.423710 0.339060 0.053 Uiso 1 1 calc GR . . . .
H14B H 0.049742 0.420996 0.439819 0.053 Uiso 1 1 calc GR . . . .
H14C H 0.133697 0.384529 0.420527 0.053 Uiso 1 1 calc GR . . . .
C15 C 0.17149(10) 0.65501(18) 0.50860(9) 0.0334(3) Uani 1 1 d . . . . .
H15A H 0.227071 0.597988 0.522996 0.050 Uiso 1 1 calc GR . . . .
H15B H 0.146896 0.623336 0.549711 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.184061 0.766428 0.515026 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.01730(10) 0.7138(2) 0.39023(11) 0.0403(3) Uani 1 1 d . . . . .
H16A H 0.031515 0.824652 0.396198 0.060 Uiso 1 1 calc GR . . . .
H16B H -0.006761 0.684948 0.432212 0.060 Uiso 1 1 calc GR . . . .
H16C H -0.027378 0.691658 0.328671 0.060 Uiso 1 1 calc GR . . . .
C17 C 0.40093(8) 0.26835(13) 0.42785(8) 0.0241(2) Uani 1 1 d . . . . .
C18 C 0.44469(8) 0.29114(13) 0.52732(8) 0.0213(2) Uani 1 1 d . . . . .
C19 C 0.48251(8) 0.16078(14) 0.58072(8) 0.0244(2) Uani 1 1 d . . . . .
H19 H 0.474508 0.061614 0.553443 0.029 Uiso 1 1 calc R . . . .
C20 C 0.53139(8) 0.17450(14) 0.67269(8) 0.0253(2) Uani 1 1 d . . . . .
H20 H 0.555760 0.084163 0.707774 0.030 Uiso 1 1 calc R . . . .
C21 C 0.54571(8) 0.31850(14) 0.71517(8) 0.0240(2) Uani 1 1 d . . . . .
C22 C 0.50781(8) 0.44904(14) 0.66170(8) 0.0244(2) Uani 1 1 d . . . . .
H22 H 0.516699 0.548268 0.689038 0.029 Uiso 1 1 calc R . . . .
C23 C 0.45738(8) 0.43592(13) 0.56923(8) 0.0228(2) Uani 1 1 d . . . . .
H23 H 0.431370 0.525721 0.534274 0.027 Uiso 1 1 calc R . . . .
C24 C 0.60119(10) 0.33307(16) 0.81521(9) 0.0328(3) Uani 1 1 d . . . . .
H24A H 0.561514 0.340466 0.844272 0.049 Uiso 1 1 calc GR . . . .
H24B H 0.638389 0.426411 0.828504 0.049 Uiso 1 1 calc GR . . . .
H24C H 0.639771 0.241812 0.837921 0.049 Uiso 1 1 calc GR . . . .
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'
P P 0.1023 0.0942 '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
O1 P1 N1 108.74(5) . . ?
O1 P1 C9 112.16(6) . . ?
O1 P1 C13 110.64(6) . . ?
N1 P1 C9 103.72(6) . . ?
N1 P1 C13 105.43(5) . . ?
C9 P1 C13 115.49(6) . . ?
C6 N1 P1 126.41(8) . . ?
C7 N1 P1 126.02(8) . . ?
C7 N1 C6 107.07(10) . . ?
C2 C1 C8 133.20(12) . . ?
C6 C1 C2 119.60(11) . . ?
C6 C1 C8 107.20(10) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.17(13) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.10(12) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 122.08(12) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.69(12) . . ?
C6 C5 H5 121.7 . . ?
C1 C6 N1 108.02(10) . . ?
C5 C6 N1 129.64(11) . . ?
C5 C6 C1 122.34(11) . . ?
N1 C7 H7 124.3 . . ?
C8 C7 N1 111.36(10) . . ?
C8 C7 H7 124.3 . . ?
C1 C8 C17 126.20(11) . . ?
C7 C8 C1 106.35(10) . . ?
C7 C8 C17 127.43(11) . . ?
C10 C9 P1 105.28(9) . . ?
C11 C9 P1 109.96(9) . . ?
C11 C9 C10 108.19(11) . . ?
C11 C9 C12 110.07(11) . . ?
C12 C9 P1 114.35(9) . . ?
C12 C9 C10 108.72(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 P1 107.54(9) . . ?
C14 C13 C16 108.31(12) . . ?
C15 C13 P1 117.51(9) . . ?
C15 C13 C14 110.05(11) . . ?
C15 C13 C16 108.29(11) . . ?
C16 C13 P1 104.73(9) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 C8 119.41(11) . . ?
O2 C17 C18 119.15(11) . . ?
C8 C17 C18 121.44(10) . . ?
C19 C18 C17 117.20(10) . . ?
C19 C18 C23 118.47(11) . . ?
C23 C18 C17 124.03(10) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.75(11) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.34(11) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C22 117.89(11) . . ?
C20 C21 C24 121.04(11) . . ?
C22 C21 C24 121.07(11) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.11(11) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.41(11) . . ?
C22 C23 H23 119.8 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
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
P1 O1 1.4771(9) . ?
P1 N1 1.7296(10) . ?
P1 C9 1.8444(13) . ?
P1 C13 1.8510(13) . ?
O2 C17 1.2300(15) . ?
N1 C6 1.4155(15) . ?
N1 C7 1.3788(14) . ?
C1 C2 1.4073(17) . ?
C1 C6 1.4034(17) . ?
C1 C8 1.4469(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3863(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3850(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.3983(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3689(16) . ?
C8 C17 1.4598(16) . ?
C9 C10 1.5416(18) . ?
C9 C11 1.5349(18) . ?
C9 C12 1.5350(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.536(2) . ?
C13 C15 1.5336(18) . ?
C13 C16 1.5465(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.4946(17) . ?
C18 C19 1.3977(16) . ?
C18 C23 1.4005(16) . ?
C19 H19 0.9500 . ?
C19 C20 1.3814(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.3968(17) . ?
C21 C22 1.3998(17) . ?
C21 C24 1.5064(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.3905(16) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
P1 N1 C6 C1 172.14(8) . . . . ?
P1 N1 C6 C5 -8.73(18) . . . . ?
P1 N1 C7 C8 -172.00(9) . . . . ?
O1 P1 N1 C6 24.06(11) . . . . ?
O1 P1 N1 C7 -165.06(10) . . . . ?
O1 P1 C9 C10 -45.09(11) . . . . ?
O1 P1 C9 C11 71.24(10) . . . . ?
O1 P1 C9 C12 -164.36(10) . . . . ?
O1 P1 C13 C14 72.71(10) . . . . ?
O1 P1 C13 C15 -162.54(10) . . . . ?
O1 P1 C13 C16 -42.35(11) . . . . ?
O2 C17 C18 C19 -32.88(17) . . . . ?
O2 C17 C18 C23 140.78(13) . . . . ?
N1 P1 C9 C10 72.07(10) . . . . ?
N1 P1 C9 C11 -171.61(9) . . . . ?
N1 P1 C9 C12 -47.20(11) . . . . ?
N1 P1 C13 C14 -44.68(10) . . . . ?
N1 P1 C13 C15 80.07(11) . . . . ?
N1 P1 C13 C16 -159.74(9) . . . . ?
N1 C7 C8 C1 -0.36(14) . . . . ?
N1 C7 C8 C17 -178.77(11) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C8 C17 O2 -5.87(19) . . . . ?
C1 C8 C17 C18 174.49(11) . . . . ?
C2 C1 C6 N1 -179.90(10) . . . . ?
C2 C1 C6 C5 0.89(18) . . . . ?
C2 C1 C8 C7 -179.94(13) . . . . ?
C2 C1 C8 C17 -1.5(2) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C3 C4 C5 C6 -1.39(19) . . . . ?
C4 C5 C6 N1 -178.70(12) . . . . ?
C4 C5 C6 C1 0.33(18) . . . . ?
C6 N1 C7 C8 0.33(14) . . . . ?
C6 C1 C2 C3 -1.05(18) . . . . ?
C6 C1 C8 C7 0.25(13) . . . . ?
C6 C1 C8 C17 178.68(11) . . . . ?
C7 N1 C6 C1 -0.16(13) . . . . ?
C7 N1 C6 C5 178.98(12) . . . . ?
C7 C8 C17 O2 172.23(13) . . . . ?
C7 C8 C17 C18 -7.41(19) . . . . ?
C8 C1 C2 C3 179.16(13) . . . . ?
C8 C1 C6 N1 -0.06(13) . . . . ?
C8 C1 C6 C5 -179.27(11) . . . . ?
C8 C17 C18 C19 146.77(12) . . . . ?
C8 C17 C18 C23 -39.57(17) . . . . ?
C9 P1 N1 C6 -95.47(11) . . . . ?
C9 P1 N1 C7 75.41(11) . . . . ?
C9 P1 C13 C14 -158.52(9) . . . . ?
C9 P1 C13 C15 -33.76(12) . . . . ?
C9 P1 C13 C16 86.42(11) . . . . ?
C13 P1 N1 C6 142.73(10) . . . . ?
C13 P1 N1 C7 -46.39(11) . . . . ?
C13 P1 C9 C10 -173.11(9) . . . . ?
C13 P1 C9 C11 -56.78(11) . . . . ?
C13 P1 C9 C12 67.62(12) . . . . ?
C17 C18 C19 C20 173.93(11) . . . . ?
C17 C18 C23 C22 -172.51(11) . . . . ?
C18 C19 C20 C21 -0.90(19) . . . . ?
C19 C18 C23 C22 1.07(17) . . . . ?
C19 C20 C21 C22 0.89(18) . . . . ?
C19 C20 C21 C24 -178.32(12) . . . . ?
C20 C21 C22 C23 0.10(18) . . . . ?
C21 C22 C23 C18 -1.09(18) . . . . ?
C23 C18 C19 C20 -0.09(18) . . . . ?
C24 C21 C22 C23 179.31(12) . . . . ?
