#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:31:10 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268946 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158171.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_7158171
loop_
_publ_author_name
'Fan, Tao'
'Liu, Yan'
'Jiang, Caina'
'Xu, Yanli'
'Chen, Yanyan'
_publ_section_title
;
 A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy
 phenylacetylenes to synthesize diphosphonyl xanthene derivatives.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6609
_journal_page_last               6612
_journal_paper_doi               10.1039/d1ob01045j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C39 H32 O3 P2'
_chemical_formula_sum            'C39 H32 O3 P2'
_chemical_formula_weight         610.58
_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             2020-09-01
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-04-21 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                95.672(7)
_cell_angle_beta                 91.026(7)
_cell_angle_gamma                113.558(8)
_cell_formula_units_Z            2
_cell_length_a                   10.8036(9)
_cell_length_b                   11.4967(9)
_cell_length_c                   15.6103(14)
_cell_measurement_reflns_used    4094
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      26.2840
_cell_measurement_theta_min      2.3680
_cell_volume                     1765.1(3)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  59.00   1.00    5.00    --  -11.27  57.00  30.00   98
  2  ω     59.00  86.00   1.00    5.00    --   11.90 178.00-120.00   27
  3  ω    -81.00  14.00   1.00    5.00    --  -11.27 -57.00-120.00   95
  4  ω    -77.00  20.00   1.00    5.00    --  -11.27 -77.00 120.00   97
;
_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      -0.0489421000
_diffrn_orient_matrix_UB_12      -0.0349591000
_diffrn_orient_matrix_UB_13      0.0278559000
_diffrn_orient_matrix_UB_21      -0.0523150000
_diffrn_orient_matrix_UB_22      -0.0000750000
_diffrn_orient_matrix_UB_23      -0.0281444000
_diffrn_orient_matrix_UB_31      -0.0042589000
_diffrn_orient_matrix_UB_32      -0.0580455000
_diffrn_orient_matrix_UB_33      -0.0229173000
_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  0.0477
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12566
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.945
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45077
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.046
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6213
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0787
_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)+(0.1008P)²+1.4600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1988
_refine_ls_wR_factor_ref         0.2200
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4305
_reflns_number_total             6213
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01045j2.cif
_cod_data_source_block           f-214
_cod_depositor_comments          'Adding full bibliography for 7158171.cif.'
_cod_database_code               7158171
_shelx_shelxl_version_number     2018/3
_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   0.988
_shelx_estimated_absorpt_t_min   0.980
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Rigid bond restraints
 C11, C12
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C11 \\sim C12: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34),
 C35(H35), C36(H36), C37(H37), C38(H38)
4.c Idealised Me refined as rotating group:
 C01C(H01A,H01B,H01C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.626
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
P1 P 0.53746(11) 0.43521(10) 0.66280(6) 0.0344(3) Uani 1 1 d . . . . .
P2 P 0.32495(11) 0.70073(10) 0.68564(6) 0.0344(3) Uani 1 1 d . . . . .
O1 O 0.6175(3) 0.4967(3) 0.59123(16) 0.0405(7) Uani 1 1 d . . . . .
O2 O 0.2724(3) 0.6860(3) 0.77244(17) 0.0439(7) Uani 1 1 d . . . . .
O3 O 0.4848(6) 0.5907(5) 0.9065(2) 0.0969(17) Uani 1 1 d . . . . .
C1 C 0.3489(6) 0.4637(5) 0.7770(3) 0.0486(12) Uani 1 1 d . . . . .
C01C C 0.0168(9) 0.1959(9) 0.7719(6) 0.137(3) Uani 1 1 d . . . . .
H01A H -0.019172 0.216290 0.721576 0.206 Uiso 1 1 calc R U . . .
H01B H -0.046457 0.182409 0.816192 0.206 Uiso 1 1 calc R U . . .
H01C H 0.031992 0.119751 0.757665 0.206 Uiso 1 1 calc R U . . .
C2 C 0.2277(6) 0.3652(5) 0.7462(3) 0.0574(14) Uani 1 1 d . . . . .
H2 H 0.208077 0.346800 0.686898 0.069 Uiso 1 1 calc R U . . .
C3 C 0.1342(7) 0.2929(6) 0.8004(4) 0.0783(18) Uani 1 1 d . . . . .
C4 C 0.1636(11) 0.3223(9) 0.8892(5) 0.111(3) Uani 1 1 d . . . . .
H4 H 0.103967 0.273418 0.926841 0.133 Uiso 1 1 calc R U . . .
C5 C 0.2790(11) 0.4222(8) 0.9209(4) 0.107(3) Uani 1 1 d . . . . .
H5 H 0.295752 0.443474 0.980242 0.128 Uiso 1 1 calc R U . . .
C6 C 0.3717(8) 0.4924(6) 0.8668(3) 0.0709(18) Uani 1 1 d . . . . .
C7 C 0.5770(8) 0.6691(6) 0.8557(4) 0.0760(19) Uani 1 1 d . . . . .
C8 C 0.5718(6) 0.6524(5) 0.7678(3) 0.0541(14) Uani 1 1 d . . . . .
C9 C 0.4534(5) 0.5361(4) 0.7173(2) 0.0379(10) Uani 1 1 d . . . . .
C10 C 0.6744(6) 0.7366(5) 0.7248(4) 0.0618(15) Uani 1 1 d . . . . .
H10 H 0.669910 0.724309 0.664869 0.074 Uiso 1 1 calc R U . . .
C11 C 0.7869(8) 0.8418(6) 0.7688(5) 0.110(2) Uani 1 1 d . U . . .
H11 H 0.856839 0.897716 0.740072 0.132 Uiso 1 1 calc R U . . .
C12 C 0.7829(9) 0.8535(8) 0.8582(6) 0.114(2) Uani 1 1 d . U . . .
H12 H 0.853163 0.921518 0.889633 0.137 Uiso 1 1 calc R U . . .
C13 C 0.6857(10) 0.7743(7) 0.9023(4) 0.102(3) Uani 1 1 d . . . . .
H13 H 0.689096 0.787570 0.962215 0.123 Uiso 1 1 calc R U . . .
C14 C 0.3882(4) 0.5811(4) 0.6445(2) 0.0354(9) Uani 1 1 d . . . . .
H14A H 0.313934 0.507730 0.614671 0.042 Uiso 1 1 calc R U . . .
H14B H 0.454972 0.616969 0.603054 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4596(4) 0.8583(4) 0.6832(3) 0.0371(10) Uani 1 1 d . . . . .
C16 C 0.5119(5) 0.9062(4) 0.6068(3) 0.0470(11) Uani 1 1 d . . . . .
H16 H 0.477882 0.856289 0.554290 0.056 Uiso 1 1 calc R U . . .
C17 C 0.6131(5) 1.0265(4) 0.6084(3) 0.0517(12) Uani 1 1 d . . . . .
H17 H 0.647177 1.058356 0.557385 0.062 Uiso 1 1 calc R U . . .
C18 C 0.6638(5) 1.0997(4) 0.6872(4) 0.0570(13) Uani 1 1 d . . . . .
H18 H 0.731815 1.181289 0.688781 0.068 Uiso 1 1 calc R U . . .
C19 C 0.6153(5) 1.0537(5) 0.7624(3) 0.0569(13) Uani 1 1 d . . . . .
H19 H 0.651144 1.103406 0.814773 0.068 Uiso 1 1 calc R U . . .
C20 C 0.5116(5) 0.9318(4) 0.7611(3) 0.0428(10) Uani 1 1 d . . . . .
H20 H 0.477949 0.900638 0.812354 0.051 Uiso 1 1 calc R U . . .
C21 C 0.1951(4) 0.6864(4) 0.6053(2) 0.0345(9) Uani 1 1 d . . . . .
C22 C 0.2030(4) 0.6622(4) 0.5168(2) 0.0398(10) Uani 1 1 d . . . . .
H22 H 0.277004 0.649228 0.495585 0.048 Uiso 1 1 calc R U . . .
C23 C 0.0998(5) 0.6574(4) 0.4603(3) 0.0432(11) Uani 1 1 d . . . . .
H23 H 0.106588 0.645064 0.401034 0.052 Uiso 1 1 calc R U . . .
C24 C -0.0128(5) 0.6710(4) 0.4920(3) 0.0512(12) Uani 1 1 d . . . . .
H24 H -0.082112 0.666671 0.453839 0.061 Uiso 1 1 calc R U . . .
C25 C -0.0235(5) 0.6910(4) 0.5798(3) 0.0506(12) Uani 1 1 d . . . . .
H25 H -0.100630 0.697936 0.600768 0.061 Uiso 1 1 calc R U . . .
C26 C 0.0811(4) 0.7006(4) 0.6363(3) 0.0409(10) Uani 1 1 d . . . . .
H26 H 0.075375 0.716720 0.695290 0.049 Uiso 1 1 calc R U . . .
C27 C 0.4069(4) 0.2812(4) 0.6230(2) 0.0355(9) Uani 1 1 d . . . . .
C28 C 0.3404(4) 0.2731(4) 0.5438(2) 0.0389(10) Uani 1 1 d . . . . .
H28 H 0.366534 0.343549 0.513058 0.047 Uiso 1 1 calc R U . . .
C29 C 0.2346(5) 0.1587(4) 0.5110(3) 0.0489(12) Uani 1 1 d . . . . .
H29 H 0.189122 0.153656 0.458671 0.059 Uiso 1 1 calc R U . . .
C30 C 0.1964(5) 0.0526(4) 0.5554(3) 0.0537(12) Uani 1 1 d . . . . .
H30 H 0.125142 -0.022927 0.533069 0.064 Uiso 1 1 calc R U . . .
C31 C 0.2643(5) 0.0587(4) 0.6332(3) 0.0534(12) Uani 1 1 d . . . . .
H31 H 0.239499 -0.012639 0.663004 0.064 Uiso 1 1 calc R U . . .
C32 C 0.3696(5) 0.1724(4) 0.6659(3) 0.0442(11) Uani 1 1 d . . . . .
H32 H 0.416345 0.176215 0.717405 0.053 Uiso 1 1 calc R U . . .
C33 C 0.6420(5) 0.4174(4) 0.7487(2) 0.0396(10) Uani 1 1 d . . . . .
C34 C 0.7795(5) 0.4649(4) 0.7363(3) 0.0488(12) Uani 1 1 d . . . . .
H34 H 0.812071 0.500778 0.686125 0.059 Uiso 1 1 calc R U . . .
C35 C 0.8682(6) 0.4584(5) 0.7996(4) 0.0667(15) Uani 1 1 d . . . . .
H35 H 0.960157 0.488767 0.790815 0.080 Uiso 1 1 calc R U . . .
C36 C 0.8233(7) 0.4089(6) 0.8735(4) 0.0722(18) Uani 1 1 d . . . . .
H36 H 0.884287 0.406681 0.915441 0.087 Uiso 1 1 calc R U . . .
C37 C 0.6888(7) 0.3621(5) 0.8866(3) 0.0655(17) Uani 1 1 d . . . . .
H37 H 0.658882 0.327680 0.937680 0.079 Uiso 1 1 calc R U . . .
C38 C 0.5935(6) 0.3646(4) 0.8242(3) 0.0503(12) Uani 1 1 d . . . . .
H38 H 0.501547 0.332082 0.833241 0.060 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'
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 C9 111.42(17) . . ?
O1 P1 C27 110.51(17) . . ?
O1 P1 C33 112.5(2) . . ?
C27 P1 C9 108.05(19) . . ?
C27 P1 C33 109.80(19) . . ?
C33 P1 C9 104.35(17) . . ?
O2 P2 C14 114.89(18) . . ?
O2 P2 C15 110.80(18) . . ?
O2 P2 C21 111.60(18) . . ?
C15 P2 C14 108.2(2) . . ?
C21 P2 C14 104.58(17) . . ?
C21 P2 C15 106.28(18) . . ?
C6 O3 C7 118.3(4) . . ?
C2 C1 C6 116.9(5) . . ?
C2 C1 C9 121.9(4) . . ?
C6 C1 C9 121.2(5) . . ?
H01A C01C H01B 109.5 . . ?
H01A C01C H01C 109.5 . . ?
H01B C01C H01C 109.5 . . ?
C3 C01C H01A 109.5 . . ?
C3 C01C H01B 109.5 . . ?
C3 C01C H01C 109.5 . . ?
C1 C2 H2 118.7 . . ?
C3 C2 C1 122.5(6) . . ?
C3 C2 H2 118.7 . . ?
C01C C3 C2 123.5(8) . . ?
C01C C3 C4 118.1(7) . . ?
C2 C3 C4 118.4(7) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(7) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(7) . . ?
C6 C5 H5 119.4 . . ?
O3 C6 C1 123.4(6) . . ?
O3 C6 C5 115.7(6) . . ?
C5 C6 C1 120.9(7) . . ?
O3 C7 C13 114.5(6) . . ?
C8 C7 O3 125.5(6) . . ?
C8 C7 C13 120.0(8) . . ?
C7 C8 C9 119.7(6) . . ?
C7 C8 C10 119.3(5) . . ?
C10 C8 C9 120.9(4) . . ?
C1 C9 P1 112.1(3) . . ?
C1 C9 C8 111.4(4) . . ?
C1 C9 C14 111.1(4) . . ?
C8 C9 P1 104.6(3) . . ?
C14 C9 P1 107.1(2) . . ?
C14 C9 C8 110.3(3) . . ?
C8 C10 H10 118.7 . . ?
C8 C10 C11 122.7(6) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 H11 122.9 . . ?
C12 C11 C10 114.3(8) . . ?
C12 C11 H11 122.9 . . ?
C11 C12 H12 117.5 . . ?
C13 C12 C11 125.0(7) . . ?
C13 C12 H12 117.5 . . ?
C7 C13 H13 120.7 . . ?
C12 C13 C7 118.7(7) . . ?
C12 C13 H13 120.7 . . ?
P2 C14 H14A 109.0 . . ?
P2 C14 H14B 109.0 . . ?
C9 C14 P2 112.8(2) . . ?
C9 C14 H14A 109.0 . . ?
C9 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 P2 123.0(3) . . ?
C20 C15 P2 117.5(3) . . ?
C20 C15 C16 119.5(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.1(5) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.9(5) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 119.6(4) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 P2 124.2(3) . . ?
C26 C21 P2 116.3(3) . . ?
C26 C21 C22 119.5(4) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.1(4) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(4) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 120.2 . . ?
C24 C25 C26 119.6(4) . . ?
C26 C25 H25 120.2 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.5(4) . . ?
C25 C26 H26 119.7 . . ?
C28 C27 P1 116.5(3) . . ?
C28 C27 C32 118.9(4) . . ?
C32 C27 P1 124.6(3) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.6(4) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.7(4) . . ?
C30 C29 H29 119.6 . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.2(4) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 120.4 . . ?
C32 C31 C30 119.2(4) . . ?
C32 C31 H31 120.4 . . ?
C27 C32 H32 119.3 . . ?
C31 C32 C27 121.4(4) . . ?
C31 C32 H32 119.3 . . ?
C34 C33 P1 115.2(3) . . ?
C34 C33 C38 120.2(4) . . ?
C38 C33 P1 124.6(4) . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.4(5) . . ?
C35 C34 H34 120.3 . . ?
C34 C35 H35 119.4 . . ?
C36 C35 C34 121.2(6) . . ?
C36 C35 H35 119.4 . . ?
C35 C36 H36 120.0 . . ?
C35 C36 C37 120.0(5) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 H37 119.3 . . ?
C36 C37 C38 121.3(5) . . ?
C38 C37 H37 119.3 . . ?
C33 C38 C37 117.8(5) . . ?
C33 C38 H38 121.1 . . ?
C37 C38 H38 121.1 . . ?
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 1.483(3) . ?
P1 C9 1.889(4) . ?
P1 C27 1.807(4) . ?
P1 C33 1.817(4) . ?
P2 O2 1.477(3) . ?
P2 C14 1.834(4) . ?
P2 C15 1.819(4) . ?
P2 C21 1.810(4) . ?
O3 C6 1.373(8) . ?
O3 C7 1.373(8) . ?
C1 C2 1.383(7) . ?
C1 C6 1.402(7) . ?
C1 C9 1.509(6) . ?
C01C H01A 0.9600 . ?
C01C H01B 0.9600 . ?
C01C H01C 0.9600 . ?
C01C C3 1.342(10) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(7) . ?
C3 C4 1.395(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.356(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(10) . ?
C7 C8 1.364(7) . ?
C7 C13 1.425(10) . ?
C8 C9 1.560(6) . ?
C8 C10 1.383(8) . ?
C9 C14 1.560(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.429(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.339(12) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.395(6) . ?
C15 C20 1.379(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.362(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.399(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(5) . ?
C21 C26 1.394(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.389(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.383(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.395(5) . ?
C27 C32 1.396(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.394(6) . ?
C29 H29 0.9300 . ?
C29 C30 1.383(7) . ?
C30 H30 0.9300 . ?
C30 C31 1.389(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.386(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.387(6) . ?
C33 C38 1.393(6) . ?
C34 H34 0.9300 . ?
C34 C35 1.393(7) . ?
C35 H35 0.9300 . ?
C35 C36 1.348(8) . ?
C36 H36 0.9300 . ?
C36 C37 1.360(8) . ?
C37 H37 0.9300 . ?
C37 C38 1.417(7) . ?
C38 H38 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
P1 C9 C14 P2 -171.0(2) . . . . ?
P1 C27 C28 C29 -177.2(3) . . . . ?
P1 C27 C32 C31 177.2(3) . . . . ?
P1 C33 C34 C35 178.5(3) . . . . ?
P1 C33 C38 C37 -177.6(3) . . . . ?
P2 C15 C16 C17 179.5(4) . . . . ?
P2 C15 C20 C19 -180.0(3) . . . . ?
P2 C21 C22 C23 -177.7(3) . . . . ?
P2 C21 C26 C25 -179.9(3) . . . . ?
O1 P1 C9 C1 167.9(3) . . . . ?
O1 P1 C9 C8 -71.3(3) . . . . ?
O1 P1 C9 C14 45.8(3) . . . . ?
O1 P1 C27 C28 -39.7(4) . . . . ?
O1 P1 C27 C32 140.2(3) . . . . ?
O1 P1 C33 C34 1.0(4) . . . . ?
O1 P1 C33 C38 179.0(3) . . . . ?
O2 P2 C14 C9 -33.0(4) . . . . ?
O2 P2 C15 C16 -168.9(3) . . . . ?
O2 P2 C15 C20 11.6(4) . . . . ?
O2 P2 C21 C22 -162.2(3) . . . . ?
O2 P2 C21 C26 17.6(4) . . . . ?
O3 C7 C8 C9 0.0(8) . . . . ?
O3 C7 C8 C10 -177.8(5) . . . . ?
O3 C7 C13 C12 177.8(6) . . . . ?
C1 C2 C3 C01C -179.1(7) . . . . ?
C1 C2 C3 C4 0.9(8) . . . . ?
C1 C9 C14 P2 66.3(4) . . . . ?
C01C C3 C4 C5 -177.9(8) . . . . ?
C2 C1 C6 O3 -177.3(5) . . . . ?
C2 C1 C6 C5 2.2(7) . . . . ?
C2 C1 C9 P1 -70.3(5) . . . . ?
C2 C1 C9 C8 172.9(4) . . . . ?
C2 C1 C9 C14 49.5(5) . . . . ?
C2 C3 C4 C5 2.2(10) . . . . ?
C3 C4 C5 C6 -2.9(11) . . . . ?
C4 C5 C6 O3 -179.7(6) . . . . ?
C4 C5 C6 C1 0.7(10) . . . . ?
C6 O3 C7 C8 -5.4(8) . . . . ?
C6 O3 C7 C13 175.4(5) . . . . ?
C6 C1 C2 C3 -3.0(7) . . . . ?
C6 C1 C9 P1 108.7(4) . . . . ?
C6 C1 C9 C8 -8.1(6) . . . . ?
C6 C1 C9 C14 -131.5(4) . . . . ?
C7 O3 C6 C1 3.5(8) . . . . ?
C7 O3 C6 C5 -176.0(5) . . . . ?
C7 C8 C9 P1 -114.8(4) . . . . ?
C7 C8 C9 C1 6.4(6) . . . . ?
C7 C8 C9 C14 130.3(4) . . . . ?
C7 C8 C10 C11 -0.1(7) . . . . ?
C8 C7 C13 C12 -1.5(9) . . . . ?
C8 C9 C14 P2 -57.7(4) . . . . ?
C8 C10 C11 C12 -1.2(8) . . . . ?
C9 P1 C27 C28 82.5(3) . . . . ?
C9 P1 C27 C32 -97.7(4) . . . . ?
C9 P1 C33 C34 -119.9(3) . . . . ?
C9 P1 C33 C38 58.1(4) . . . . ?
C9 C1 C2 C3 176.1(4) . . . . ?
C9 C1 C6 O3 3.6(7) . . . . ?
C9 C1 C6 C5 -176.8(5) . . . . ?
C9 C8 C10 C11 -177.8(4) . . . . ?
C10 C8 C9 P1 62.9(5) . . . . ?
C10 C8 C9 C1 -175.8(4) . . . . ?
C10 C8 C9 C14 -52.0(5) . . . . ?
C10 C11 C12 C13 1.2(10) . . . . ?
C11 C12 C13 C7 0.1(11) . . . . ?
C13 C7 C8 C9 179.2(5) . . . . ?
C13 C7 C8 C10 1.5(8) . . . . ?
C14 P2 C15 C16 64.4(4) . . . . ?
C14 P2 C15 C20 -115.2(3) . . . . ?
C14 P2 C21 C22 -37.4(4) . . . . ?
C14 P2 C21 C26 142.4(3) . . . . ?
C15 P2 C14 C9 91.3(3) . . . . ?
C15 P2 C21 C22 76.9(4) . . . . ?
C15 P2 C21 C26 -103.3(3) . . . . ?
C15 C16 C17 C18 0.5(7) . . . . ?
C16 C15 C20 C19 0.4(6) . . . . ?
C16 C17 C18 C19 0.4(7) . . . . ?
C17 C18 C19 C20 -0.9(8) . . . . ?
C18 C19 C20 C15 0.5(7) . . . . ?
C20 C15 C16 C17 -0.9(7) . . . . ?
C21 P2 C14 C9 -155.7(3) . . . . ?
C21 P2 C15 C16 -47.4(4) . . . . ?
C21 P2 C15 C20 133.0(3) . . . . ?
C21 C22 C23 C24 -2.9(6) . . . . ?
C22 C21 C26 C25 -0.1(6) . . . . ?
C22 C23 C24 C25 0.8(7) . . . . ?
C23 C24 C25 C26 1.6(7) . . . . ?
C24 C25 C26 C21 -2.0(7) . . . . ?
C26 C21 C22 C23 2.5(6) . . . . ?
C27 P1 C9 C1 46.3(3) . . . . ?
C27 P1 C9 C8 167.1(3) . . . . ?
C27 P1 C9 C14 -75.8(3) . . . . ?
C27 P1 C33 C34 124.5(3) . . . . ?
C27 P1 C33 C38 -57.5(4) . . . . ?
C27 C28 C29 C30 -1.2(7) . . . . ?
C28 C27 C32 C31 -2.9(6) . . . . ?
C28 C29 C30 C31 -0.6(7) . . . . ?
C29 C30 C31 C32 0.5(7) . . . . ?
C30 C31 C32 C27 1.2(7) . . . . ?
C32 C27 C28 C29 2.9(6) . . . . ?
C33 P1 C9 C1 -70.5(4) . . . . ?
C33 P1 C9 C8 50.3(3) . . . . ?
C33 P1 C9 C14 167.4(3) . . . . ?
C33 P1 C27 C28 -164.3(3) . . . . ?
C33 P1 C27 C32 15.6(4) . . . . ?
C33 C34 C35 C36 -1.2(7) . . . . ?
C34 C33 C38 C37 0.3(6) . . . . ?
C34 C35 C36 C37 1.1(8) . . . . ?
C35 C36 C37 C38 -0.3(8) . . . . ?
C36 C37 C38 C33 -0.4(7) . . . . ?
C38 C33 C34 C35 0.5(6) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.426 0.000 0.000 339.1 124.6 ?
