#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:09:36 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298111 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/35/1573570.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_1573570
loop_
_publ_author_name
'Huang, Mao-Gui'
'Fu, Yue-Liu-Ting'
'Li, Jia-Wei'
'Liu, Yue-Jin'
_publ_section_title
;
 Ruthenium-catalyzed three-component tandem remote C-H functionalization
 of naphthalenes: modular and concise synthesis of multifunctional
 naphthalenes.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              1957
_journal_page_last               1965
_journal_paper_doi               10.1039/d4sc06846g
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C31 H29 F2 O4 P'
_chemical_formula_sum            'C31 H29 F2 O4 P'
_chemical_formula_weight         534.51
_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             2020-12-26
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-07-08 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                99.3100(10)
_cell_angle_beta                 98.0540(10)
_cell_angle_gamma                100.6190(10)
_cell_formula_units_Z            2
_cell_length_a                   9.62340(10)
_cell_length_b                   10.49270(10)
_cell_length_c                   14.0802(2)
_cell_measurement_reflns_used    17430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8670
_cell_measurement_theta_min      3.2010
_cell_volume                     1357.67(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00 -27.00   0.50    0.39    --  -43.30  42.00-103.00   58
  2  ω     -8.00  32.00   0.50    0.39    --  -43.30  42.00-103.00   80
  3  ω     94.00 120.00   0.50    0.39    --   43.30  42.00-103.00   52
  4  ω     85.00 111.00   0.50    0.39    --   43.30  57.00 -30.00   52
  5  ω     91.00 117.00   0.50    0.39    --   43.30  77.00 -30.00   52
  6  ω     64.00  90.00   0.50    0.39    --   43.30  77.00  60.00   52
  7  ω     28.00  65.00   0.50    0.39    --   43.30  77.00 -30.00   74
  8  ω     22.00  69.00   0.50    0.39    --   43.30  42.00-103.00   94
  9  ω     22.00  48.00   0.50    0.39    --   43.30  57.00 -30.00   52
 10  ω     14.00  51.00   0.50    0.39    --   43.30  77.00  60.00   74
 11  ω     88.00 174.00   0.50    1.56    --  109.88  61.00  90.00  172
 12  ω     94.00 170.00   0.50    1.56    --  109.88  61.00  30.00  152
 13  ω     90.00 168.00   0.50    1.56    --  109.88  42.00-103.00  156
 14  ω    113.00 176.00   0.50    1.56    --  109.88 125.00-120.00  126
 15  ω     93.00 174.00   0.50    1.56    --  109.88 125.00 -30.00  162
 16  ω     95.00 171.00   0.50    1.56    --  109.88 125.00  30.00  152
 17  ω     83.00 164.00   0.50    1.56    --  109.88  77.00 120.00  162
 18  ω     61.00 168.00   0.50    1.56    --  109.88  15.00   0.00  214
 19  ω     74.00 107.00   0.50    1.56    --  109.88 -94.00 120.00   66
 20  ω     44.00  79.00   0.50    0.39    --   43.30 -99.00   0.00   70
 21  ω     32.00  97.00   0.50    0.39    --   43.30-125.00 -30.00  130
 22  ω     34.00 101.00   0.50    1.56    --  109.88 -42.00 103.00  134
 23  ω     37.00 103.00   0.50    1.56    --  109.88 -94.00   0.00  132
 24  ω     93.00 120.00   0.50    1.56    --  109.88-125.00   0.00   54
 25  ω     53.00  94.00   0.50    1.56    --  109.88 -94.00-120.00   82
 26  ω     42.00  67.00   0.50    1.56    --  109.88-125.00   0.00   50
 27  ω     42.00  89.00   0.50    1.56    --  109.88 -94.00 -30.00   94
 28  ω     36.00  98.00   0.50    1.56    --  109.88 -94.00  60.00  124
 29  ω     36.00  68.00   0.50    1.56    --  109.88 -94.00 120.00   64
 30  ω     -3.00  33.00   0.50    0.39    --   43.30 -99.00   0.00   72
 31  ω    -33.00  58.00   0.50    0.39    --   43.30 -42.00 103.00  182
 32  ω    -67.00 -16.00   0.50    0.39    --  -43.30 -77.00 120.00  102
 33  ω    -81.00 -16.00   0.50    0.39    --  -43.30 -77.00  60.00  130
 34  ω    -64.00 -15.00   0.50    0.39    --  -43.30 -77.00 -30.00   98
 35  ω    -65.00 -14.00   0.50    0.39    --  -43.30 -77.00-120.00  102
 36  ω    -52.00 -16.00   0.50    0.39    --  -43.30 -77.00-180.00   72
 37  ω    -83.00 -26.00   0.50    0.39    --  -43.30 -37.00-120.00  114
 38  ω    -91.00 -63.00   0.50    1.56    --  -90.25 -73.00 -18.94   56
 39  ω    -85.00 -59.00   0.50    1.56    --  -90.25 -83.00  27.10   52
 40  ω    -89.00 -61.00   0.50    1.56    --  -90.25 -77.00  60.00   56
 41  ω    -87.00 -61.00   0.50    1.56    --  -90.25 -77.00 114.21   52
 42  ω    -87.00 -61.00   0.50    1.56    --  -90.25 -77.00 150.00   52
 43  ω    -86.00 -61.00   0.50    1.56    --  -90.25 -78.00  86.79   50
 44  ω    -92.00 -59.00   0.50    1.56    --  -90.25 -81.00  58.60   66
 45  ω    -87.00 -61.00   0.50    1.56    --  -90.25 -77.00   0.00   52
 46  ω    -91.00 -61.00   0.50    1.56    --  -90.25 -77.00 -30.00   60
 47  ω    -86.00 -60.00   0.50    1.56    --  -90.25 -79.00 -77.28   52
 48  ω    -99.00 -60.00   0.50    1.56    --  -90.25 -82.00-131.20   78
 49  ω    -89.00 -64.00   0.50    1.56    --  -90.25 -77.00-150.00   50
 50  ω    -90.00 -61.00   0.50    1.56    --  -90.25 -77.00-180.00   58
 51  ω   -102.00 -63.00   0.50    1.56    --  -90.25 -72.00-167.87   78
 52  ω   -101.00 -63.00   0.50    1.56    --  -90.25 -73.00-121.56   76
 53  ω   -115.00 -68.00   0.50    0.39    --  -43.30 -77.00-120.00   94
 54  ω   -115.00 -62.00   0.50    1.56    --  -90.25 -76.00 -50.30  106
 55  ω   -115.00 -89.00   0.50    0.39    --  -43.30 -77.00  60.00   52
 56  ω   -103.00 -25.00   0.50    0.39    --  -43.30 -42.00 103.00  156
 57  ω    -92.00 -67.00   0.50    1.56    --  -90.25 -61.00 140.39   50
 58  ω   -103.00 -64.00   0.50    1.56    --  -90.25 -71.00 133.60   78
 59  ω   -108.00 -59.00   0.50    1.56    --  -90.25 -83.00  46.62   98
 60  ω    -96.00 -63.00   0.50    1.56    --  -90.25 -76.00  76.10   66
 61  ω   -101.00 -64.00   0.50    1.56    --  -90.25 -70.00  87.57   74
 62  ω   -110.00 -61.00   0.50    1.56    --  -90.25 -79.00  27.86   98
 63  ω   -109.00 -61.00   0.50    1.56    --  -90.25 -77.00 -60.00   96
 64  ω   -114.00 -63.00   0.50    1.56    --  -90.25 -77.00 -90.00  102
 65  ω   -116.00 -61.00   0.50    1.56    --  -90.25 -78.00-102.23  110
 66  ω   -129.00-103.00   0.50    1.56    --  -90.25 -73.00 -18.94   52
 67  ω   -142.00-117.00   0.50    1.56    --  -90.25 -83.00  27.10   50
 68  ω   -122.00 -96.00   0.50    1.56    --  -90.25 -42.00 103.00   52
 69  ω    -89.00 -64.00   0.50    1.56    --  -90.25 -69.00 116.02   50
 70  ω   -155.00-130.00   0.50    1.56    --  -90.25 -71.00 133.60   50
 71  ω   -160.00-135.00   0.50    1.56    --  -90.25 -78.00  86.79   50
 72  ω   -139.00-114.00   0.50    1.56    --  -90.25 -81.00  58.60   50
 73  ω   -163.00-124.00   0.50    1.56    --  -90.25 -79.00  27.86   78
 74  ω   -162.00-136.00   0.50    1.56    --  -90.25 -77.00 114.21   52
 75  ω   -162.00 -99.00   0.50    1.56    --  -90.25 -77.00   0.00  126
 76  ω   -146.00-120.00   0.50    1.56    --  -90.25 -77.00 -90.00   52
 77  ω   -147.00-116.00   0.50    1.56    --  -90.25 -82.00-131.20   62
 78  ω   -151.00-125.00   0.50    1.56    --  -90.25 -77.00-150.00   52
 79  ω   -158.00-116.00   0.50    1.56    --  -90.25 -73.00-121.56   84
 80  ω   -155.00-107.00   0.50    1.56    --  -90.25 -77.00-180.00   96
 81  ω   -164.00-113.00   0.50    1.56    --  -90.25 -79.00 -77.28  102
 82  ω    -93.00 -68.00   0.50    1.56    --  -90.25  42.00-103.00   50
 83  ω     88.00 172.00   0.50    1.56    --  109.88  77.00-180.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1257805000
_diffrn_orient_matrix_UB_12      0.0333252000
_diffrn_orient_matrix_UB_13      -0.0649641000
_diffrn_orient_matrix_UB_21      0.0881692000
_diffrn_orient_matrix_UB_22      0.1408700000
_diffrn_orient_matrix_UB_23      0.0081777000
_diffrn_orient_matrix_UB_31      0.0614296000
_diffrn_orient_matrix_UB_32      -0.0471227000
_diffrn_orient_matrix_UB_33      -0.0916245000
_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  0.0332
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30872
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.090
_diffrn_reflns_theta_min         3.231
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0366
_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)+(0.0457P)²+0.2786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4840
_reflns_number_total             5457
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc06846g2.cif
_cod_data_source_block           fuyue-2-100
_cod_depositor_comments          'Adding full bibliography for 1573570.cif.'
_cod_database_code               1573570
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O P F'
_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   0.780
_shelx_estimated_absorpt_t_min   0.780
_reflns_odcompleteness_completeness 99.79
_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 Secondary CH2 refined with riding coordinates:
 C00L(H00B,H00C), C00Z(H00R,H00U)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K), C00M(H00M),
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00V(H00V),
 C00W(H00W), C00X(H00X), C010(H010), C011(H011)
2.c Idealised Me refined as rotating group:
 C00O(H00D,H00E,H00F), C00U(H00I,H00L,H00O), C012(H01A,H01B,H01C)
;
_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 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.848
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
P001 P 0.67255(4) 0.81681(3) 0.53204(2) 0.04266(12) Uani 1 1 d . . . . .
O002 O 0.79889(12) 0.44134(10) 0.11708(8) 0.0534(3) Uani 1 1 d . . . . .
O003 O 0.66071(14) 0.45327(12) -0.02026(9) 0.0691(3) Uani 1 1 d . . . . .
O004 O 0.56658(13) 0.89620(11) 0.13573(9) 0.0612(3) Uani 1 1 d . . . . .
F005 F 0.64399(17) 0.90029(15) -0.04175(10) 0.1032(5) Uani 1 1 d . . . . .
F006 F 0.86789(16) 0.92356(13) 0.02457(13) 0.1098(5) Uani 1 1 d . . . . .
C007 C 0.72388(14) 0.68852(13) 0.24539(9) 0.0379(3) Uani 1 1 d . . . . .
C008 C 0.75144(14) 0.74788(13) 0.34712(9) 0.0393(3) Uani 1 1 d . . . . .
C009 C 0.64056(14) 0.72604(13) 0.40485(9) 0.0392(3) Uani 1 1 d . . . . .
C00A C 0.58562(14) 0.60954(13) 0.20534(9) 0.0408(3) Uani 1 1 d . . . . .
H00A H 0.564791 0.570960 0.139299 0.049 Uiso 1 1 calc R U . . .
C00B C 0.83525(14) 0.71234(14) 0.18816(10) 0.0422(3) Uani 1 1 d . . . . .
O00C O 0.78447(17) 1.02738(15) 0.18472(15) 0.0991(5) Uani 1 1 d . . . . .
C00D C 0.49443(15) 0.77742(13) 0.56542(10) 0.0432(3) Uani 1 1 d . . . . .
C00E C 0.77150(15) 0.71765(15) 0.60070(10) 0.0468(3) Uani 1 1 d . . . . .
C00F C 0.74532(16) 0.50692(15) 0.05247(10) 0.0471(3) Uani 1 1 d . . . . .
C00G C 0.88865(16) 0.82740(16) 0.38873(11) 0.0510(4) Uani 1 1 d . . . . .
H00G H 0.908242 0.865640 0.454833 0.061 Uiso 1 1 calc R U . . .
C00H C 0.48270(15) 0.58904(14) 0.26161(10) 0.0448(3) Uani 1 1 d . . . . .
H00H H 0.393237 0.535765 0.233692 0.054 Uiso 1 1 calc R U . . .
C00I C 0.81006(15) 0.65556(15) 0.07765(10) 0.0447(3) Uani 1 1 d . . . . .
C00J C 0.50977(15) 0.64721(14) 0.36121(10) 0.0447(3) Uani 1 1 d . . . . .
H00J H 0.437789 0.632041 0.398268 0.054 Uiso 1 1 calc R U . . .
C00K C 0.45692(18) 0.68944(15) 0.62635(11) 0.0511(3) Uani 1 1 d . . . . .
H00K H 0.523400 0.643189 0.650242 0.061 Uiso 1 1 calc R U . . .
C00L C 0.70606(18) 0.72021(16) 0.01628(11) 0.0520(4) Uani 1 1 d . . . . .
H00B H 0.706971 0.688116 -0.052178 0.062 Uiso 1 1 calc R U . . .
H00C H 0.609890 0.688090 0.027768 0.062 Uiso 1 1 calc R U . . .
C00M C 0.39169(17) 0.84491(16) 0.53157(12) 0.0544(4) Uani 1 1 d . . . . .
H00M H 0.413889 0.903732 0.490375 0.065 Uiso 1 1 calc R U . . .
C00N C 0.96511(16) 0.79047(17) 0.23355(11) 0.0553(4) Uani 1 1 d . . . . .
H00N H 1.037927 0.805600 0.197150 0.066 Uiso 1 1 calc R U . . .
C00O C 0.95298(18) 0.66596(18) 0.03739(12) 0.0580(4) Uani 1 1 d . . . . .
H00D H 0.996171 0.757303 0.041895 0.087 Uiso 1 1 calc R U . . .
H00E H 0.933974 0.621481 -0.029720 0.087 Uiso 1 1 calc R U . . .
H00F H 1.017208 0.625513 0.075098 0.087 Uiso 1 1 calc R U . . .
C00P C 0.78990(18) 0.59326(16) 0.56251(13) 0.0569(4) Uani 1 1 d . . . . .
H00P H 0.754061 0.556340 0.497044 0.068 Uiso 1 1 calc R U . . .
C00Q C 0.99218(17) 0.84850(19) 0.33309(12) 0.0615(4) Uani 1 1 d . . . . .
H00Q H 1.081541 0.901786 0.361240 0.074 Uiso 1 1 calc R U . . .
C00R C 0.7001(2) 0.94155(16) 0.12812(15) 0.0635(4) Uani 1 1 d . . . . .
C00S C 0.82992(19) 0.7724(2) 0.69835(12) 0.0644(4) Uani 1 1 d . . . . .
H00S H 0.821894 0.857477 0.724431 0.077 Uiso 1 1 calc R U . . .
C00T C 0.3220(2) 0.67005(18) 0.65175(13) 0.0622(4) Uani 1 1 d . . . . .
H00T H 0.298376 0.610185 0.691942 0.075 Uiso 1 1 calc R U . . .
C00U C 0.7426(2) 0.29989(17) 0.09643(15) 0.0658(4) Uani 1 1 d . . . . .
H00I H 0.756977 0.262963 0.032495 0.099 Uiso 1 1 calc R U . . .
H00L H 0.641795 0.282626 0.098896 0.099 Uiso 1 1 calc R U . . .
H00O H 0.791708 0.260379 0.144235 0.099 Uiso 1 1 calc R U . . .
C00V C 0.22261(19) 0.73811(19) 0.61834(14) 0.0665(5) Uani 1 1 d . . . . .
H00V H 0.132319 0.725171 0.636144 0.080 Uiso 1 1 calc R U . . .
C00W C 0.25792(18) 0.82624(19) 0.55788(14) 0.0642(4) Uani 1 1 d . . . . .
H00W H 0.191222 0.872933 0.534979 0.077 Uiso 1 1 calc R U . . .
C00X C 0.8617(2) 0.5229(2) 0.62138(16) 0.0712(5) Uani 1 1 d . . . . .
H00X H 0.874059 0.439325 0.595293 0.085 Uiso 1 1 calc R U . . .
C00Y C 0.7323(2) 0.8687(2) 0.03276(15) 0.0691(5) Uani 1 1 d . . . . .
C00Z C 0.5178(2) 0.9540(2) 0.22336(15) 0.0718(5) Uani 1 1 d . . . . .
H00R H 0.534302 1.049358 0.230104 0.086 Uiso 1 1 calc R U . . .
H00U H 0.570157 0.933488 0.280987 0.086 Uiso 1 1 calc R U . . .
C010 C 0.91452(19) 0.5775(2) 0.71867(16) 0.0757(6) Uani 1 1 d . . . . .
H010 H 0.960474 0.529700 0.758480 0.091 Uiso 1 1 calc R U . . .
C011 C 0.8995(2) 0.7014(3) 0.75659(14) 0.0758(6) Uani 1 1 d . . . . .
H011 H 0.936391 0.738096 0.821963 0.091 Uiso 1 1 calc R U . . .
C012 C 0.3624(2) 0.8976(2) 0.21305(18) 0.0826(6) Uani 1 1 d . . . . .
H01A H 0.310889 0.923733 0.158543 0.124 Uiso 1 1 calc R U . . .
H01B H 0.328944 0.929509 0.271652 0.124 Uiso 1 1 calc R U . . .
H01C H 0.346667 0.802945 0.202262 0.124 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'
F F 0.0727 0.0534 '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
C00D P001 C009 102.00(6) . . ?
C00E P001 C009 103.66(7) . . ?
C00E P001 C00D 101.88(6) . . ?
C00F O002 C00U 115.37(12) . . ?
C00R O004 C00Z 116.76(15) . . ?
C008 C007 C00B 119.39(12) . . ?
C00A C007 C008 117.79(12) . . ?
C00A C007 C00B 122.82(12) . . ?
C007 C008 C009 119.93(11) . . ?
C00G C008 C007 118.82(12) . . ?
C00G C008 C009 121.25(12) . . ?
C008 C009 P001 118.99(10) . . ?
C00J C009 P001 121.79(10) . . ?
C00J C009 C008 118.97(12) . . ?
C007 C00A H00A 119.4 . . ?
C00H C00A C007 121.30(12) . . ?
C00H C00A H00A 119.4 . . ?
C007 C00B C00I 121.71(12) . . ?
C00N C00B C007 118.40(13) . . ?
C00N C00B C00I 119.86(12) . . ?
C00K C00D P001 124.41(12) . . ?
C00K C00D C00M 117.69(14) . . ?
C00M C00D P001 117.82(11) . . ?
C00P C00E P001 124.43(11) . . ?
C00P C00E C00S 118.67(15) . . ?
C00S C00E P001 116.89(13) . . ?
O002 C00F C00I 112.93(12) . . ?
O003 C00F O002 122.92(14) . . ?
O003 C00F C00I 124.05(13) . . ?
C008 C00G H00G 119.7 . . ?
C00Q C00G C008 120.69(14) . . ?
C00Q C00G H00G 119.7 . . ?
C00A C00H H00H 119.6 . . ?
C00A C00H C00J 120.87(12) . . ?
C00J C00H H00H 119.6 . . ?
C00B C00I C00L 113.24(12) . . ?
C00B C00I C00O 111.92(12) . . ?
C00F C00I C00B 112.91(11) . . ?
C00F C00I C00L 105.68(12) . . ?
C00F C00I C00O 103.03(12) . . ?
C00L C00I C00O 109.41(12) . . ?
C009 C00J C00H 121.13(13) . . ?
C009 C00J H00J 119.4 . . ?
C00H C00J H00J 119.4 . . ?
C00D C00K H00K 119.6 . . ?
C00T C00K C00D 120.76(15) . . ?
C00T C00K H00K 119.6 . . ?
C00I C00L H00B 107.7 . . ?
C00I C00L H00C 107.7 . . ?
H00B C00L H00C 107.1 . . ?
C00Y C00L C00I 118.51(14) . . ?
C00Y C00L H00B 107.7 . . ?
C00Y C00L H00C 107.7 . . ?
C00D C00M H00M 119.3 . . ?
C00W C00M C00D 121.32(15) . . ?
C00W C00M H00M 119.3 . . ?
C00B C00N H00N 118.9 . . ?
C00B C00N C00Q 122.24(14) . . ?
C00Q C00N H00N 118.9 . . ?
C00I C00O H00D 109.5 . . ?
C00I C00O H00E 109.5 . . ?
C00I C00O H00F 109.5 . . ?
H00D C00O H00E 109.5 . . ?
H00D C00O H00F 109.5 . . ?
H00E C00O H00F 109.5 . . ?
C00E C00P H00P 119.8 . . ?
C00E C00P C00X 120.41(17) . . ?
C00X C00P H00P 119.8 . . ?
C00G C00Q C00N 120.45(14) . . ?
C00G C00Q H00Q 119.8 . . ?
C00N C00Q H00Q 119.8 . . ?
O004 C00R C00Y 109.40(16) . . ?
O00C C00R O004 126.3(2) . . ?
O00C C00R C00Y 124.31(19) . . ?
C00E C00S H00S 119.7 . . ?
C011 C00S C00E 120.54(19) . . ?
C011 C00S H00S 119.7 . . ?
C00K C00T H00T 119.6 . . ?
C00V C00T C00K 120.73(16) . . ?
C00V C00T H00T 119.6 . . ?
O002 C00U H00I 109.5 . . ?
O002 C00U H00L 109.5 . . ?
O002 C00U H00O 109.5 . . ?
H00I C00U H00L 109.5 . . ?
H00I C00U H00O 109.5 . . ?
H00L C00U H00O 109.5 . . ?
C00T C00V H00V 120.3 . . ?
C00T C00V C00W 119.39(16) . . ?
C00W C00V H00V 120.3 . . ?
C00M C00W C00V 120.09(17) . . ?
C00M C00W H00W 120.0 . . ?
C00V C00W H00W 120.0 . . ?
C00P C00X H00X 120.1 . . ?
C010 C00X C00P 119.8(2) . . ?
C010 C00X H00X 120.1 . . ?
F005 C00Y C00L 106.93(17) . . ?
F005 C00Y C00R 105.93(15) . . ?
F006 C00Y F005 105.67(14) . . ?
F006 C00Y C00L 112.13(15) . . ?
F006 C00Y C00R 107.67(18) . . ?
C00L C00Y C00R 117.69(13) . . ?
O004 C00Z H00R 110.2 . . ?
O004 C00Z H00U 110.2 . . ?
O004 C00Z C012 107.77(17) . . ?
H00R C00Z H00U 108.5 . . ?
C012 C00Z H00R 110.2 . . ?
C012 C00Z H00U 110.2 . . ?
C00X C010 H010 119.9 . . ?
C011 C010 C00X 120.23(17) . . ?
C011 C010 H010 119.9 . . ?
C00S C011 H011 119.9 . . ?
C010 C011 C00S 120.28(18) . . ?
C010 C011 H011 119.9 . . ?
C00Z C012 H01A 109.5 . . ?
C00Z C012 H01B 109.5 . . ?
C00Z C012 H01C 109.5 . . ?
H01A C012 H01B 109.5 . . ?
H01A C012 H01C 109.5 . . ?
H01B C012 H01C 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
P001 C009 1.8424(13) . ?
P001 C00D 1.8324(15) . ?
P001 C00E 1.8321(15) . ?
O002 C00F 1.3300(17) . ?
O002 C00U 1.449(2) . ?
O003 C00F 1.1997(18) . ?
O004 C00R 1.311(2) . ?
O004 C00Z 1.461(2) . ?
F005 C00Y 1.378(2) . ?
F006 C00Y 1.354(2) . ?
C007 C008 1.4331(18) . ?
C007 C00A 1.4168(18) . ?
C007 C00B 1.4384(18) . ?
C008 C009 1.4370(18) . ?
C008 C00G 1.4150(19) . ?
C009 C00J 1.3715(19) . ?
C00A H00A 0.9300 . ?
C00A C00H 1.3606(19) . ?
C00B C00I 1.5415(19) . ?
C00B C00N 1.368(2) . ?
O00C C00R 1.193(2) . ?
C00D C00K 1.392(2) . ?
C00D C00M 1.393(2) . ?
C00E C00P 1.382(2) . ?
C00E C00S 1.395(2) . ?
C00F C00I 1.532(2) . ?
C00G H00G 0.9300 . ?
C00G C00Q 1.360(2) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.403(2) . ?
C00I C00L 1.551(2) . ?
C00I C00O 1.552(2) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00T 1.383(2) . ?
C00L H00B 0.9700 . ?
C00L H00C 0.9700 . ?
C00L C00Y 1.505(3) . ?
C00M H00M 0.9300 . ?
C00M C00W 1.377(2) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.402(2) . ?
C00O H00D 0.9600 . ?
C00O H00E 0.9600 . ?
C00O H00F 0.9600 . ?
C00P H00P 0.9300 . ?
C00P C00X 1.391(2) . ?
C00Q H00Q 0.9300 . ?
C00R C00Y 1.535(3) . ?
C00S H00S 0.9300 . ?
C00S C011 1.380(3) . ?
C00T H00T 0.9300 . ?
C00T C00V 1.371(3) . ?
C00U H00I 0.9600 . ?
C00U H00L 0.9600 . ?
C00U H00O 0.9600 . ?
C00V H00V 0.9300 . ?
C00V C00W 1.384(3) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00X C010 1.381(3) . ?
C00Z H00R 0.9700 . ?
C00Z H00U 0.9700 . ?
C00Z C012 1.481(3) . ?
C010 H010 0.9300 . ?
C010 C011 1.364(3) . ?
C011 H011 0.9300 . ?
C012 H01A 0.9600 . ?
C012 H01B 0.9600 . ?
C012 H01C 0.9600 . ?
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
P001 C009 C00J C00H 173.69(11) . . . . ?
P001 C00D C00K C00T 176.83(12) . . . . ?
P001 C00D C00M C00W -176.39(13) . . . . ?
P001 C00E C00P C00X -177.30(13) . . . . ?
P001 C00E C00S C011 176.59(14) . . . . ?
O002 C00F C00I C00B -38.67(16) . . . . ?
O002 C00F C00I C00L -162.97(12) . . . . ?
O002 C00F C00I C00O 82.24(14) . . . . ?
O003 C00F C00I C00B 144.98(15) . . . . ?
O003 C00F C00I C00L 20.7(2) . . . . ?
O003 C00F C00I C00O -94.11(18) . . . . ?
O004 C00R C00Y F005 63.63(18) . . . . ?
O004 C00R C00Y F006 176.32(13) . . . . ?
O004 C00R C00Y C00L -55.8(2) . . . . ?
C007 C008 C009 P001 -173.85(10) . . . . ?
C007 C008 C009 C00J 0.54(19) . . . . ?
C007 C008 C00G C00Q 0.7(2) . . . . ?
C007 C00A C00H C00J 0.9(2) . . . . ?
C007 C00B C00I C00F -50.78(17) . . . . ?
C007 C00B C00I C00L 69.27(17) . . . . ?
C007 C00B C00I C00O -166.49(13) . . . . ?
C007 C00B C00N C00Q -0.6(2) . . . . ?
C008 C007 C00A C00H -0.9(2) . . . . ?
C008 C007 C00B C00I -177.63(12) . . . . ?
C008 C007 C00B C00N 0.6(2) . . . . ?
C008 C009 C00J C00H -0.5(2) . . . . ?
C008 C00G C00Q C00N -0.7(3) . . . . ?
C009 P001 C00D C00K 105.39(13) . . . . ?
C009 P001 C00D C00M -77.98(13) . . . . ?
C009 P001 C00E C00P -10.07(15) . . . . ?
C009 P001 C00E C00S 170.76(12) . . . . ?
C009 C008 C00G C00Q -179.27(15) . . . . ?
C00A C007 C008 C009 0.14(19) . . . . ?
C00A C007 C008 C00G -179.88(12) . . . . ?
C00A C007 C00B C00I 1.5(2) . . . . ?
C00A C007 C00B C00N 179.77(14) . . . . ?
C00A C00H C00J C009 -0.2(2) . . . . ?
C00B C007 C008 C009 179.31(12) . . . . ?
C00B C007 C008 C00G -0.70(19) . . . . ?
C00B C007 C00A C00H 180.00(13) . . . . ?
C00B C00I C00L C00Y 49.66(18) . . . . ?
C00B C00N C00Q C00G 0.7(3) . . . . ?
O00C C00R C00Y F005 -115.3(2) . . . . ?
O00C C00R C00Y F006 -2.6(3) . . . . ?
O00C C00R C00Y C00L 125.3(2) . . . . ?
C00D P001 C009 C008 170.83(10) . . . . ?
C00D P001 C009 C00J -3.40(13) . . . . ?
C00D P001 C00E C00P 95.57(14) . . . . ?
C00D P001 C00E C00S -83.60(13) . . . . ?
C00D C00K C00T C00V -0.7(3) . . . . ?
C00D C00M C00W C00V -0.6(3) . . . . ?
C00E P001 C009 C008 -83.62(11) . . . . ?
C00E P001 C009 C00J 102.16(12) . . . . ?
C00E P001 C00D C00K -1.56(14) . . . . ?
C00E P001 C00D C00M 175.07(12) . . . . ?
C00E C00P C00X C010 0.2(3) . . . . ?
C00E C00S C011 C010 1.3(3) . . . . ?
C00F C00I C00L C00Y 173.75(13) . . . . ?
C00G C008 C009 P001 6.16(18) . . . . ?
C00G C008 C009 C00J -179.44(14) . . . . ?
C00I C00B C00N C00Q 177.68(16) . . . . ?
C00I C00L C00Y F005 168.97(13) . . . . ?
C00I C00L C00Y F006 53.6(2) . . . . ?
C00I C00L C00Y C00R -72.1(2) . . . . ?
C00K C00D C00M C00W 0.5(2) . . . . ?
C00K C00T C00V C00W 0.5(3) . . . . ?
C00M C00D C00K C00T 0.2(2) . . . . ?
C00N C00B C00I C00F 130.98(15) . . . . ?
C00N C00B C00I C00L -108.97(16) . . . . ?
C00N C00B C00I C00O 15.3(2) . . . . ?
C00O C00I C00L C00Y -75.93(17) . . . . ?
C00P C00E C00S C011 -2.6(3) . . . . ?
C00P C00X C010 C011 -1.6(3) . . . . ?
C00R O004 C00Z C012 175.20(15) . . . . ?
C00S C00E C00P C00X 1.9(2) . . . . ?
C00T C00V C00W C00M 0.1(3) . . . . ?
C00U O002 C00F O003 -3.0(2) . . . . ?
C00U O002 C00F C00I -179.39(13) . . . . ?
C00X C010 C011 C00S 0.8(3) . . . . ?
C00Z O004 C00R O00C -1.8(3) . . . . ?
C00Z O004 C00R C00Y 179.36(14) . . . . ?
