#------------------------------------------------------------------------------
#$Date: 2024-08-05 20:23:25 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293687 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/31/7133198.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_7133198
loop_
_publ_author_name
'Liu, Yong'
'Jia, Mengying'
'Wang, Guodong'
'Yang, Wenhui'
'Xu, Xianxiu'
_publ_section_title
;
 Silver-catalyzed P-centered anion nucleophilic addition to isocyanide:
 access to 2-phosphinoyl indoles/indol-3-ols.
;
_journal_issue                   56
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7196
_journal_page_last               7199
_journal_paper_doi               10.1039/d4cc01984a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C29 H24 N O3 P, 0.6(C H2 Cl2)'
_chemical_formula_sum            'C29.6 H25.2 Cl1.2 N O3 P'
_chemical_formula_weight         516.42
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-04-06
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2024-02-23 deposited with the CCDC.	2024-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                91.104(5)
_cell_angle_beta                 99.247(6)
_cell_angle_gamma                107.898(5)
_cell_formula_units_Z            2
_cell_length_a                   9.9338(7)
_cell_length_b                   11.4115(6)
_cell_length_c                   13.4261(9)
_cell_measurement_reflns_used    3414
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.5820
_cell_measurement_theta_min      6.6860
_cell_volume                     1425.68(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9759
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  12.00   1.00    1.00    --    0.00 104.00 -64.00   31
  2  ω     11.00  82.00   1.00    2.00    --   54.00-104.00-165.00   71
  3  ω     70.00  96.00   1.00    2.00    --  108.00-104.00-165.00   26
  4  ω    104.00 169.00   1.00    2.00    --  108.00 104.00 -64.00   65
  5  ω    -21.00   7.00   1.00    1.00    --    0.00 -77.00 150.00   28
  6  ω    -16.00  24.00   1.00    1.00    --    0.00 -77.00  90.00   40
  7  ω     -4.00  21.00   1.00    1.00    --    0.00 -77.00-180.00   25
  8  ω    -13.00  40.00   1.00    1.00    --    0.00  77.00  60.00   53
  9  ω     89.00 115.00   1.00    2.00    --   54.00  57.00-120.00   26
 10  ω    -16.00  57.00   1.00    2.00    --   54.00 -77.00-120.00   73
 11  ω     19.00  74.00   1.00    2.00    --   54.00 -57.00  90.00   55
 12  ω    -19.00  98.00   1.00    2.00    --   54.00 -19.00 -90.00  117
 13  ω     42.00 122.00   1.00    2.00    --   54.00  57.00  90.00   80
 14  ω     38.00 103.00   1.00    2.00    --   54.00-125.00  60.00   65
 15  ω     33.00  64.00   1.00    2.00    --   54.00-125.00   0.00   31
 16  ω     87.00 174.00   1.00    2.00    --  108.00  50.00 -90.00   87
 17  ω     36.00 109.00   1.00    2.00    --  108.00-111.00 150.00   73
 18  ω    105.00 177.00   1.00    2.00    --  108.00 111.00   0.00   72
 19  ω    107.00 134.00   1.00    2.00    --  108.00  77.00 -90.00   27
 20  ω    120.00 146.00   1.00    2.00    --  108.00 111.00 -30.00   26
 21  ω     54.00 125.00   1.00    2.00    --  108.00 -50.00 -30.00   71
 22  ω    108.00 174.00   1.00    2.00    --  108.00  77.00 -30.00   66
 23  ω    110.00 137.00   1.00    2.00    --  108.00 178.00-180.00   27
 24  ω     67.00  93.00   1.00    2.00    --  108.00 178.00-180.00   26
 25  ω     71.00 105.00   1.00    2.00    --  108.00-111.00 -60.00   34
 26  ω     77.00 123.00   1.00    2.00    --  108.00 -50.00-120.00   46
 27  ω     81.00 106.00   1.00    2.00    --  108.00-111.00 -30.00   25
 28  ω    150.00 175.00   1.00    2.00    --  108.00 111.00 -30.00   25
 29  ω     49.00 107.00   1.00    2.00    --  108.00 -91.00   0.00   58
 30  ω     44.00  69.00   1.00    2.00    --  108.00 -50.00-120.00   25
 31  ω     37.00  71.00   1.00    2.00    --  108.00-111.00 -30.00   34
 32  ω    124.00 163.00   1.00    2.00    --  108.00  50.00 120.00   39
 33  ω     36.00  62.00   1.00    2.00    --  108.00 -91.00 150.00   26
 34  ω     70.00  96.00   1.00    2.00    --  108.00 -50.00-180.00   26
 35  ω     75.00 151.00   1.00    2.00    --  108.00  25.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1593984000
_diffrn_orient_matrix_UB_12      0.0288603000
_diffrn_orient_matrix_UB_13      0.0478988000
_diffrn_orient_matrix_UB_21      -0.0325846000
_diffrn_orient_matrix_UB_22      0.0389986000
_diffrn_orient_matrix_UB_23      0.1016718000
_diffrn_orient_matrix_UB_31      -0.0304903000
_diffrn_orient_matrix_UB_32      -0.1337174000
_diffrn_orient_matrix_UB_33      0.0309258000
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10015
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         4.75
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             538
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5070
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1196P)²+1.4681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.2079
_reflns_number_gt                4118
_reflns_number_total             5070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4cc01984a2.cif
_cod_data_source_block           exp_1357
_cod_depositor_comments
'Adding full bibliography for 7133196--7133198.cif.'
_cod_original_cell_volume        1425.67(16)
_cod_original_formula_sum        'C29.60 H25.20 Cl1.20 N O3 P'
_cod_database_code               7133198
_diffrn_oxdiff_digest_frames
;
0192709b5a6f92c48f1d603c06eaebf1070002832b7
;
_diffrn_oxdiff_digest_hkl
;
01743002a3073f09793c1e19647de681d02887
;
_reflns_odcompleteness_completeness 99.94
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1'-C30' = Cl2'-C30'
 1.7 with sigma of 0.01
 Cl1-C30 = Cl2-C30
 1.7 with sigma of 0.01
 Cl1'-Cl2' \\sim Cl1-Cl2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C30') = Uanis(C30)
Uanis(Cl2') = Uanis(Cl1')
4. Others
 Fixed Sof: C30(0.5) H30A(0.5) H30B(0.5) Cl2(0.5) Cl1(0.5) Cl1'(0.1) Cl2'(0.1)
 C30'(0.1) H30C(0.1) H30D(0.1)
5.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C30'(H30C,H30D)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C22(H22), C10(H10), C9(H9), C18(H18), C24(H24), C20(H20), C19(H19),
 C12(H12), C21(H21), C16(H16), C2(H2), C5(H5), C15(H15), C25(H25), C13(H13),
 C28(H28), C26(H26), C3(H3), C4(H4), C27(H27)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.849
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.37764(8) 0.66027(6) 0.58360(5) 0.0210(2) Uani 1 1 d . . .
O1 O 0.3350(2) 0.53119(18) 0.53792(16) 0.0272(5) Uani 1 1 d . . .
O2 O 0.6050(2) 0.95407(19) 0.64160(18) 0.0333(5) Uani 1 1 d . . .
N1 N 0.6414(3) 0.6632(2) 0.58091(19) 0.0255(6) Uani 1 1 d . . .
H1 H 0.6144 0.5867 0.5592 0.031 Uiso 1 1 calc R . .
O3 O 0.6607(3) 0.9403(3) -0.00129(19) 0.0515(7) Uani 1 1 d . . .
C23 C 0.2470(3) 0.7348(3) 0.5346(2) 0.0224(6) Uani 1 1 d . . .
C7 C 0.5581(3) 0.7473(3) 0.5574(2) 0.0229(6) Uani 1 1 d . . .
C29 C 0.3944(3) 0.6634(3) 0.7196(2) 0.0252(6) Uani 1 1 d . . .
C22 C 0.1157(3) 0.6556(3) 0.4836(2) 0.0290(7) Uani 1 1 d . . .
H22 H 0.1023 0.5715 0.4747 0.035 Uiso 1 1 calc R . .
C11 C 0.6247(3) 0.7986(3) 0.2805(2) 0.0279(7) Uani 1 1 d . . .
C10 C 0.6170(3) 0.7535(3) 0.3816(2) 0.0253(6) Uani 1 1 d . . .
H10 H 0.6626 0.6950 0.3993 0.030 Uiso 1 1 calc R . .
C9 C 0.5515(3) 0.7876(3) 0.4505(2) 0.0250(6) Uani 1 1 d . . .
H9 H 0.4978 0.8400 0.4316 0.030 Uiso 1 1 calc R . .
C6 C 0.7686(3) 0.7236(3) 0.6425(2) 0.0261(6) Uani 1 1 d . . .
C1 C 0.7784(3) 0.8439(3) 0.6721(2) 0.0285(7) Uani 1 1 d . . .
C8 C 0.6444(3) 0.8649(3) 0.6293(2) 0.0253(6) Uani 1 1 d . . .
C18 C 0.2670(3) 0.8612(3) 0.5467(2) 0.0287(7) Uani 1 1 d . . .
H18 H 0.3540 0.9149 0.5803 0.034 Uiso 1 1 calc R . .
C24 C 0.3689(3) 0.7542(3) 0.7772(2) 0.0297(7) Uani 1 1 d . . .
H24 H 0.3482 0.8203 0.7463 0.036 Uiso 1 1 calc R . .
C20 C 0.0254(4) 0.8270(3) 0.4585(3) 0.0369(8) Uani 1 1 d . . .
H20 H -0.0486 0.8582 0.4336 0.044 Uiso 1 1 calc R . .
C19 C 0.1557(4) 0.9057(3) 0.5080(3) 0.0350(8) Uani 1 1 d . . .
H19 H 0.1690 0.9899 0.5154 0.042 Uiso 1 1 calc R . .
C12 C 0.5453(4) 0.8744(3) 0.2385(2) 0.0346(7) Uani 1 1 d . . .
H12 H 0.4831 0.8957 0.2750 0.041 Uiso 1 1 calc R . .
C14 C 0.6531(4) 0.8881(3) 0.0892(2) 0.0366(8) Uani 1 1 d . . .
C21 C 0.0053(4) 0.7017(3) 0.4461(3) 0.0372(8) Uani 1 1 d . . .
H21 H -0.0822 0.6485 0.4127 0.045 Uiso 1 1 calc R . .
C16 C 0.7154(4) 0.7681(3) 0.2229(3) 0.0334(7) Uani 1 1 d . . .
H16 H 0.7675 0.7168 0.2484 0.040 Uiso 1 1 calc R . .
C2 C 0.9033(4) 0.9225(3) 0.7333(3) 0.0397(8) Uani 1 1 d . . .
H2 H 0.9105 1.0034 0.7520 0.048 Uiso 1 1 calc R . .
C5 C 0.8810(3) 0.6758(3) 0.6758(3) 0.0351(7) Uani 1 1 d . . .
H5 H 0.8746 0.5949 0.6578 0.042 Uiso 1 1 calc R . .
C15 C 0.7301(4) 0.8124(3) 0.1280(3) 0.0388(8) Uani 1 1 d . . .
H15 H 0.7917 0.7909 0.0910 0.047 Uiso 1 1 calc R . .
C25 C 0.3743(4) 0.7467(3) 0.8808(3) 0.0368(8) Uani 1 1 d . . .
H25 H 0.3560 0.8072 0.9189 0.044 Uiso 1 1 calc R . .
C13 C 0.5582(4) 0.9173(3) 0.1445(3) 0.0380(8) Uani 1 1 d . . .
H13 H 0.5036 0.9661 0.1175 0.046 Uiso 1 1 calc R . .
C28 C 0.4279(5) 0.5660(3) 0.7663(3) 0.0445(9) Uani 1 1 d . . .
H28 H 0.4462 0.5054 0.7283 0.053 Uiso 1 1 calc R . .
C26 C 0.4071(5) 0.6490(4) 0.9275(3) 0.0486(10) Uani 1 1 d . . .
H26 H 0.4108 0.6440 0.9969 0.058 Uiso 1 1 calc R . .
C3 C 1.0141(4) 0.8765(4) 0.7646(3) 0.0504(10) Uani 1 1 d . . .
H3 H 1.0981 0.9268 0.8046 0.061 Uiso 1 1 calc R . .
C4 C 1.0018(4) 0.7547(4) 0.7367(3) 0.0482(10) Uani 1 1 d . . .
H4 H 1.0779 0.7254 0.7600 0.058 Uiso 1 1 calc R . .
C27 C 0.4338(6) 0.5596(4) 0.8710(3) 0.0587(12) Uani 1 1 d . . .
H27 H 0.4561 0.4944 0.9025 0.070 Uiso 1 1 calc R . .
C17 C 0.7442(6) 0.9032(5) -0.0657(3) 0.0662(13) Uani 1 1 d . . .
H17A H 0.8438 0.9320 -0.0348 0.099 Uiso 1 1 calc R . .
H17B H 0.7322 0.9380 -0.1298 0.099 Uiso 1 1 calc R . .
H17C H 0.7127 0.8148 -0.0758 0.099 Uiso 1 1 calc R . .
C30 C 0.1280(13) 0.6906(12) 0.2070(9) 0.121(5) Uani 0.50 1 d PDU A 1
H30A H 0.1432 0.7436 0.2678 0.145 Uiso 0.50 1 calc PR A 1
H30B H 0.2060 0.6554 0.2129 0.145 Uiso 0.50 1 calc PR A 1
Cl2 Cl 0.1359(4) 0.7796(3) 0.1049(3) 0.1078(11) Uani 0.50 1 d PDU A 1
Cl1 Cl -0.0333(4) 0.5709(3) 0.2008(3) 0.0889(9) Uani 0.50 1 d PDU A 1
Cl1' Cl 0.229(3) 0.611(2) 0.1988(19) 0.154(7) Uani 0.10 1 d PD B 2
Cl2' Cl -0.004(2) 0.638(2) 0.0458(19) 0.154(7) Uani 0.10 1 d PD B 2
C30' C 0.157(5) 0.704(2) 0.124(5) 0.121(5) Uani 0.10 1 d PD B 2
H30C H 0.2265 0.7445 0.0826 0.145 Uiso 0.10 1 calc PR B 2
H30D H 0.1463 0.7676 0.1682 0.145 Uiso 0.10 1 calc PR B 2
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'
P P 0.2955 0.4335 '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 C23 110.82(13) . . ?
O1 P1 C7 109.21(12) . . ?
O1 P1 C29 111.14(13) . . ?
C23 P1 C7 110.77(13) . . ?
C29 P1 C23 108.69(14) . . ?
C29 P1 C7 106.12(13) . . ?
C7 N1 H1 125.0 . . ?
C6 N1 H1 125.0 . . ?
C6 N1 C7 110.0(2) . . ?
C14 O3 C17 117.1(3) . . ?
C22 C23 P1 115.2(2) . . ?
C18 C23 P1 125.2(2) . . ?
C18 C23 C22 119.5(3) . . ?
N1 C7 P1 103.67(19) . . ?
N1 C7 C9 114.7(2) . . ?
N1 C7 C8 103.3(2) . . ?
C9 C7 P1 112.0(2) . . ?
C9 C7 C8 106.7(2) . . ?
C8 C7 P1 116.35(19) . . ?
C24 C29 P1 123.2(2) . . ?
C28 C29 P1 117.0(2) . . ?
C28 C29 C24 119.7(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C12 C11 C10 122.7(3) . . ?
C16 C11 C10 119.7(3) . . ?
C16 C11 C12 117.6(3) . . ?
C11 C10 H10 116.7 . . ?
C9 C10 C11 126.7(3) . . ?
C9 C10 H10 116.7 . . ?
C7 C9 H9 117.7 . . ?
C10 C9 C7 124.6(3) . . ?
C10 C9 H9 117.7 . . ?
N1 C6 C1 112.4(3) . . ?
N1 C6 C5 126.7(3) . . ?
C1 C6 C5 120.9(3) . . ?
C6 C1 C8 108.3(3) . . ?
C6 C1 C2 121.0(3) . . ?
C2 C1 C8 130.7(3) . . ?
O2 C8 C7 125.3(3) . . ?
O2 C8 C1 129.6(3) . . ?
C1 C8 C7 105.0(2) . . ?
C23 C18 H18 120.4 . . ?
C19 C18 C23 119.3(3) . . ?
C19 C18 H18 120.4 . . ?
C29 C24 H24 119.9 . . ?
C25 C24 C29 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 119.4 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
O3 C14 C15 125.5(3) . . ?
O3 C14 C13 114.8(3) . . ?
C15 C14 C13 119.7(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 119.9(3) . . ?
C20 C21 H21 120.0 . . ?
C11 C16 H16 119.1 . . ?
C11 C16 C15 121.7(3) . . ?
C15 C16 H16 119.1 . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2 121.0 . . ?
C6 C5 H5 121.6 . . ?
C4 C5 C6 116.8(3) . . ?
C4 C5 H5 121.6 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25 120.0 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C29 C28 H28 120.3 . . ?
C29 C28 C27 119.5(3) . . ?
C27 C28 H28 120.3 . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.9(3) . . ?
C27 C26 H26 120.1 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 122.7(3) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C28 C27 H27 119.7 . . ?
C26 C27 C28 120.5(3) . . ?
C26 C27 H27 119.7 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H30A C30 H30B 107.6 . . ?
Cl2 C30 H30A 108.6 . . ?
Cl2 C30 H30B 108.6 . . ?
Cl2 C30 Cl1 114.7(6) . . ?
Cl1 C30 H30A 108.6 . . ?
Cl1 C30 H30B 108.6 . . ?
Cl1' C30' Cl2' 118.4(11) . . ?
Cl1' C30' H30C 107.7 . . ?
Cl1' C30' H30D 107.7 . . ?
Cl2' C30' H30C 107.7 . . ?
Cl2' C30' H30D 107.7 . . ?
H30C C30' H30D 107.1 . . ?
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
P1 O1 1.491(2) . ?
P1 C23 1.807(3) . ?
P1 C7 1.856(3) . ?
P1 C29 1.806(3) . ?
O2 C8 1.214(4) . ?
N1 H1 0.8600 . ?
N1 C7 1.456(4) . ?
N1 C6 1.365(4) . ?
O3 C14 1.367(4) . ?
O3 C17 1.431(5) . ?
C23 C22 1.397(4) . ?
C23 C18 1.397(4) . ?
C7 C9 1.513(4) . ?
C7 C8 1.564(4) . ?
C29 C24 1.389(4) . ?
C29 C28 1.388(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.385(4) . ?
C11 C10 1.466(4) . ?
C11 C12 1.409(4) . ?
C11 C16 1.392(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.328(4) . ?
C9 H9 0.9300 . ?
C6 C1 1.392(4) . ?
C6 C5 1.402(4) . ?
C1 C8 1.455(4) . ?
C1 C2 1.407(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.388(5) . ?
C20 H20 0.9300 . ?
C20 C19 1.382(5) . ?
C20 C21 1.385(5) . ?
C19 H19 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.374(5) . ?
C14 C15 1.378(5) . ?
C14 C13 1.400(5) . ?
C21 H21 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.392(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(5) . ?
C15 H15 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.388(5) . ?
C13 H13 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.402(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.374(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(6) . ?
C4 H4 0.9300 . ?
C27 H27 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 Cl2 1.719(9) . ?
C30 Cl1 1.745(9) . ?
Cl1' C30' 1.707(10) . ?
Cl2' C30' 1.710(10) . ?
C30' H30C 0.9700 . ?
C30' H30D 0.9700 . ?
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 C23 C22 C21 177.5(3) . . . . ?
P1 C23 C18 C19 -177.9(2) . . . . ?
P1 C7 C9 C10 -119.1(3) . . . . ?
P1 C7 C8 O2 -59.5(4) . . . . ?
P1 C7 C8 C1 122.6(2) . . . . ?
P1 C29 C24 C25 175.7(3) . . . . ?
P1 C29 C28 C27 -176.2(3) . . . . ?
O1 P1 C23 C22 14.6(3) . . . . ?
O1 P1 C23 C18 -167.3(2) . . . . ?
O1 P1 C7 N1 -45.8(2) . . . . ?
O1 P1 C7 C9 78.4(2) . . . . ?
O1 P1 C7 C8 -158.5(2) . . . . ?
O1 P1 C29 C24 -150.2(3) . . . . ?
O1 P1 C29 C28 26.7(3) . . . . ?
N1 C7 C9 C10 -1.3(4) . . . . ?
N1 C7 C8 O2 -172.4(3) . . . . ?
N1 C7 C8 C1 9.7(3) . . . . ?
N1 C6 C1 C8 1.9(4) . . . . ?
N1 C6 C1 C2 -178.0(3) . . . . ?
N1 C6 C5 C4 178.8(3) . . . . ?
O3 C14 C15 C16 178.1(3) . . . . ?
O3 C14 C13 C12 -177.4(3) . . . . ?
C23 P1 C7 N1 -168.15(18) . . . . ?
C23 P1 C7 C9 -44.0(2) . . . . ?
C23 P1 C7 C8 79.2(2) . . . . ?
C23 P1 C29 C24 -28.0(3) . . . . ?
C23 P1 C29 C28 148.9(3) . . . . ?
C23 C22 C21 C20 0.5(5) . . . . ?
C23 C18 C19 C20 0.5(5) . . . . ?
C7 P1 C23 C22 135.9(2) . . . . ?
C7 P1 C23 C18 -45.9(3) . . . . ?
C7 P1 C29 C24 91.2(3) . . . . ?
C7 P1 C29 C28 -91.9(3) . . . . ?
C7 N1 C6 C1 4.9(3) . . . . ?
C7 N1 C6 C5 -175.5(3) . . . . ?
C29 P1 C23 C22 -107.8(2) . . . . ?
C29 P1 C23 C18 70.3(3) . . . . ?
C29 P1 C7 N1 74.0(2) . . . . ?
C29 P1 C7 C9 -161.8(2) . . . . ?
C29 P1 C7 C8 -38.6(2) . . . . ?
C29 C24 C25 C26 0.8(5) . . . . ?
C29 C28 C27 C26 -0.1(7) . . . . ?
C22 C23 C18 C19 0.2(5) . . . . ?
C11 C10 C9 C7 -174.0(3) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C11 C16 C15 C14 -0.2(5) . . . . ?
C10 C11 C12 C13 178.4(3) . . . . ?
C10 C11 C16 C15 -177.7(3) . . . . ?
C9 C7 C8 O2 66.3(4) . . . . ?
C9 C7 C8 C1 -111.6(3) . . . . ?
C6 N1 C7 P1 -130.8(2) . . . . ?
C6 N1 C7 C9 106.8(3) . . . . ?
C6 N1 C7 C8 -9.0(3) . . . . ?
C6 C1 C8 O2 174.9(3) . . . . ?
C6 C1 C8 C7 -7.3(3) . . . . ?
C6 C1 C2 C3 -1.2(5) . . . . ?
C6 C5 C4 C3 -0.1(6) . . . . ?
C1 C6 C5 C4 -1.6(5) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C8 C7 C9 C10 112.5(3) . . . . ?
C8 C1 C2 C3 178.8(3) . . . . ?
C18 C23 C22 C21 -0.7(5) . . . . ?
C24 C29 C28 C27 0.8(6) . . . . ?
C24 C25 C26 C27 -0.1(6) . . . . ?
C19 C20 C21 C22 0.2(6) . . . . ?
C12 C11 C10 C9 -8.6(5) . . . . ?
C12 C11 C16 C15 1.3(5) . . . . ?
C21 C20 C19 C18 -0.7(5) . . . . ?
C16 C11 C10 C9 170.3(3) . . . . ?
C16 C11 C12 C13 -0.6(5) . . . . ?
C2 C1 C8 O2 -5.1(6) . . . . ?
C2 C1 C8 C7 172.7(3) . . . . ?
C2 C3 C4 C5 1.2(7) . . . . ?
C5 C6 C1 C8 -177.7(3) . . . . ?
C5 C6 C1 C2 2.3(5) . . . . ?
C15 C14 C13 C12 2.2(5) . . . . ?
C25 C26 C27 C28 -0.2(7) . . . . ?
C13 C14 C15 C16 -1.6(5) . . . . ?
C28 C29 C24 C25 -1.1(5) . . . . ?
C17 O3 C14 C15 6.8(5) . . . . ?
C17 O3 C14 C13 -173.5(4) . . . . ?
