#------------------------------------------------------------------------------
#$Date: 2020-08-12 02:09:26 +0300 (Wed, 12 Aug 2020) $
#$Revision: 255240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038671.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_4038671
loop_
_publ_author_name
'Winters, Karen R.'
'Montchamp, Jean-Luc'
_publ_section_title
;
 Evaluation and Development of Methodologies for the Synthesis of
 Thiophosphinic Acids
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01151
_journal_year                    2020
_chemical_formula_moiety         '1(C26 H22 N O2 P)'
_chemical_formula_sum            'C26 H22 N O2 P'
_chemical_formula_weight         411.41
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-01
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                96.509(4)
_cell_angle_beta                 95.256(4)
_cell_angle_gamma                90.126(4)
_cell_formula_units_Z            2
_cell_length_a                   5.0456(4)
_cell_length_b                   10.0717(8)
_cell_length_c                   20.3776(17)
_cell_measurement_reflns_used    9789
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      44.956
_cell_measurement_theta_min      3.031
_cell_volume                     1024.46(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      99.98
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            44276
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         3.028
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0678 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.9137.
The λ/2 correction factor is Not present.
;
_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    1.334
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.379
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.856
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 4754 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     718
_refine_ls_number_reflns         10065
_refine_ls_number_restraints     305
_refine_ls_restrained_S_all      1.241
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0309P)²+1.9349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.992
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                9950
_reflns_number_total             10065
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01151_si_002.cif
_cod_data_source_block           ssphenyldopo
_cod_database_code               4038671
_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   0.991
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9918(11)
 0.0082(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C22-C26 \\sim C22A-C26A
 with sigma of 0.04
 C21-C20 \\sim C21-C22 \\sim C21-C26 \\sim C21-C22A \\sim C21-C26A
 with sigma of 0.02
 C52-C48 \\sim C52A-C48A
 with sigma of 0.04
 C47-C45 \\sim C47-C52 \\sim C47-C48 \\sim C47-C52A \\sim C47-C48A
 with sigma of 0.02
 C18-C14 \\sim C14A-C18A
 with sigma of 0.04
 C13-C11 \\sim C13-C18 \\sim C13-C14 \\sim C13-C14A \\sim C13-C18A
 with sigma of 0.02
 C31-C27 \\sim C31A-C27A
 with sigma of 0.04
 C32-C34 \\sim C32-C31 \\sim C32-C27 \\sim C32-C31A \\sim C32-C27A
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 C21, C24, C22, C26, C23, C25, C22A, C23A, C24A, C25A, C26A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13, C16, C18, C14, C17, C15, C14A, C15A, C16A, C17A, C18A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C47, C50, C51, C52, C49, C48, C50A, C51A, C52A, C48A, C49A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C32, C29, C31, C28, C30, C27, C30A, C31A, C27A, C28A, C29A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=
 Sof(H25A)=Sof(C26A)=Sof(H26A)=1-FVAR(1)
 Sof(C24)=Sof(H24)=Sof(C22)=Sof(H22)=Sof(C26)=Sof(H26)=Sof(C23)=Sof(H23)=
 Sof(C25)=Sof(H25)=FVAR(1)
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=1-FVAR(2)
 Sof(C16)=Sof(H16)=Sof(C18)=Sof(H18)=Sof(C14)=Sof(H14)=Sof(C17)=Sof(H17)=
 Sof(C15)=Sof(H15)=FVAR(2)
 Sof(C50A)=Sof(H50A)=Sof(C51A)=Sof(H51A)=Sof(C52A)=Sof(H52A)=Sof(C48A)=
 Sof(H48A)=Sof(C49A)=Sof(H49A)=1-FVAR(3)
 Sof(C50)=Sof(H50)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52)=Sof(C49)=Sof(H49)=
 Sof(C48)=Sof(H48)=FVAR(3)
 Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=
 Sof(H28A)=Sof(C29A)=Sof(H29A)=1-FVAR(4)
 Sof(C29)=Sof(H29)=Sof(C31)=Sof(H31)=Sof(C28)=Sof(H28)=Sof(C30)=Sof(H30)=
 Sof(C27)=Sof(H27)=FVAR(4)
6.a Riding coordinates:
 N1(H1), N2(H2)
6.b Ternary CH refined with riding coordinates:
 C20(H20), C34(H34)
6.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C43(H43), C42(H42), C1(H1A), C8(H8), C44(H44), C38(H38), C3(H3),
 C16(H16), C37(H37), C9(H9), C39(H39), C10(H10), C4(H4), C2(H2A), C24(H24),
 C50(H50), C29(H29), C18(H18), C51(H51), C52(H52), C31(H31), C28(H28), C22(H22),
  C30(H30), C27(H27), C26(H26), C49(H49), C48(H48), C14(H14), C17(H17),
 C23(H23), C15(H15), C25(H25), C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A),
 C26A(H26A), C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A),
 C50A(H50A), C51A(H51A), C52A(H52A), C48A(H48A), C49A(H49A), C30A(H30A),
 C31A(H31A), C27A(H27A), C28A(H28A), C29A(H29A)
6.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'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
P2 P 0.03418(18) 0.71845(10) 0.81238(6) 0.0105(2) Uani 1 1 d . . . . .
P1 P 0.96508(18) 0.30665(10) 0.18531(6) 0.0116(2) Uani 1 1 d . . . . .
O1 O 0.8679(6) 0.1880(3) 0.22390(16) 0.0139(6) Uani 1 1 d . . . . .
O3 O 0.1297(6) 0.5814(3) 0.77423(15) 0.0135(6) Uani 1 1 d . . . . .
O2 O 1.2422(6) 0.3480(3) 0.20690(17) 0.0193(7) Uani 1 1 d . . . . .
O4 O -0.2426(6) 0.7491(4) 0.79065(17) 0.0201(7) Uani 1 1 d . . . . .
N1 N 0.7584(8) 0.4292(4) 0.1964(2) 0.0166(8) Uani 1 1 d . . . . .
H1 H 0.623255 0.402233 0.216164 0.020 Uiso 1 1 d R . . . .
C46 C 0.3419(8) 0.5068(4) 0.7972(2) 0.0100(7) Uani 1 1 d . . . . .
C12 C 0.6570(8) 0.1011(4) 0.2015(2) 0.0108(7) Uani 1 1 d . . . . .
N2 N 0.2402(7) 0.8347(4) 0.80061(19) 0.0143(7) Uani 1 1 d . . . . .
H2 H 0.376429 0.798234 0.781637 0.017 Uiso 1 1 d R . . . .
C6 C 0.9172(8) 0.2306(4) 0.1016(2) 0.0130(8) Uani 1 1 d . . . . .
C5 C 0.7332(8) 0.1252(4) 0.0833(2) 0.0112(7) Uani 1 1 d . . . . .
C40 C 0.2654(8) 0.5865(4) 0.9154(2) 0.0106(7) Uani 1 1 d . . . . .
C7 C 0.5849(8) 0.0696(4) 0.1332(2) 0.0114(7) Uani 1 1 d . . . . .
C36 C -0.0713(9) 0.7521(5) 0.9426(2) 0.0154(9) Uani 1 1 d . . . . .
H36 H -0.196404 0.816178 0.928948 0.019 Uiso 1 1 calc R . . . .
C41 C 0.4146(8) 0.5067(4) 0.8654(2) 0.0108(7) Uani 1 1 d . . . . .
C35 C 0.0833(8) 0.6835(4) 0.8963(2) 0.0117(7) Uani 1 1 d . . . . .
C43 C 0.7615(8) 0.3497(4) 0.8372(2) 0.0148(8) Uani 1 1 d . . . . .
H43 H 0.907349 0.296499 0.850719 0.018 Uiso 1 1 calc R . . . .
C42 C 0.6296(8) 0.4267(4) 0.8842(2) 0.0132(8) Uani 1 1 d . . . . .
H42 H 0.685441 0.425417 0.929881 0.016 Uiso 1 1 calc R . . . .
C13 C 0.6043(9) 0.0847(4) 0.3221(2) 0.0141(8) Uani 1 1 d D U . . .
C1 C 1.0724(10) 0.2779(5) 0.0554(2) 0.0187(9) Uani 1 1 d . . . . .
H1A H 1.198263 0.348190 0.068909 0.022 Uiso 1 1 calc R . . . .
C8 C 0.3704(8) -0.0199(4) 0.1153(2) 0.0142(8) Uani 1 1 d . . . . .
H8 H 0.314047 -0.043299 0.069704 0.017 Uiso 1 1 calc R . . . .
C47 C 0.3960(9) 0.4310(5) 0.6765(2) 0.0168(9) Uani 1 1 d D U . . .
C44 C 0.6800(9) 0.3503(5) 0.7698(2) 0.0164(8) Uani 1 1 d . . . . .
H44 H 0.769472 0.295614 0.737967 0.020 Uiso 1 1 calc R . . . .
C45 C 0.4715(8) 0.4290(4) 0.7485(2) 0.0136(8) Uani 1 1 d D . . . .
C38 C 0.1417(10) 0.6344(5) 1.0280(2) 0.0186(9) Uani 1 1 d . . . . .
H38 H 0.163726 0.618479 1.073228 0.022 Uiso 1 1 calc R . . . .
C11 C 0.5286(8) 0.0472(4) 0.2503(2) 0.0120(8) Uani 1 1 d D . . . .
C3 C 0.8567(10) 0.1191(5) -0.0295(2) 0.0204(9) Uani 1 1 d . . . . .
H3 H 0.833764 0.081824 -0.074647 0.024 Uiso 1 1 calc R . . . .
C16 C 0.726(6) 0.158(3) 0.4546(13) 0.026(5) Uani 0.492(7) 1 d . U P A 1
H16 H 0.756106 0.183906 0.500974 0.032 Uiso 0.492(7) 1 calc R . P A 1
C37 C -0.0416(10) 0.7265(5) 1.0080(2) 0.0188(9) Uani 1 1 d . . . . .
H37 H -0.147642 0.772374 1.039266 0.023 Uiso 1 1 calc R . . . .
C9 C 0.2392(9) -0.0748(5) 0.1627(2) 0.0174(9) Uani 1 1 d . . . . .
H9 H 0.093007 -0.134404 0.149384 0.021 Uiso 1 1 calc R . . . .
C39 C 0.2943(9) 0.5646(4) 0.9825(2) 0.0139(8) Uani 1 1 d . . . . .
H39 H 0.419694 0.501455 0.997001 0.017 Uiso 1 1 calc R . . . .
C10 C 0.3204(9) -0.0432(5) 0.2296(2) 0.0174(9) Uani 1 1 d . . . . .
H10 H 0.232701 -0.083719 0.261676 0.021 Uiso 1 1 calc R . . . .
C4 C 0.7054(9) 0.0705(4) 0.0160(2) 0.0159(8) Uani 1 1 d . . . . .
H4 H 0.581435 -0.000436 0.001846 0.019 Uiso 1 1 calc R . . . .
C21 C 0.8019(9) 0.5924(4) 0.2988(2) 0.0198(9) Uani 1 1 d D U . . .
C2 C 1.0418(10) 0.2216(5) -0.0100(2) 0.0206(9) Uani 1 1 d . . . . .
H2A H 1.146934 0.253003 -0.041590 0.025 Uiso 1 1 calc R . . . .
C20 C 0.8368(10) 0.5659(4) 0.2251(3) 0.0212(10) Uani 1 1 d D . . . .
H20 H 1.029610 0.578563 0.219352 0.025 Uiso 1 1 calc R . . . .
C24 C 0.738(4) 0.651(2) 0.4403(9) 0.014(4) Uiso 0.500(8) 1 d . U P B 1
H24 H 0.713661 0.673672 0.485894 0.017 Uiso 0.500(8) 1 calc R . P B 1
C32 C 0.2030(9) 0.9452(5) 0.6964(3) 0.0227(10) Uani 1 1 d D U . . .
C50 C 0.276(5) 0.4453(17) 0.5389(12) 0.014(3) Uani 0.490(8) 1 d . U P C 1
H50 H 0.237798 0.444764 0.492348 0.016 Uiso 0.490(8) 1 calc R . P C 1
C34 C 0.1622(10) 0.9570(5) 0.7698(3) 0.0243(11) Uani 1 1 d D . . . .
H34 H -0.031883 0.971024 0.774164 0.029 Uiso 1 1 calc R . . . .
C29 C 0.280(6) 0.946(2) 0.5648(11) 0.018(3) Uani 0.502(8) 1 d . U P D 1
H29 H 0.305486 0.943729 0.519078 0.021 Uiso 0.502(8) 1 calc R . P D 1
C33 C 0.3130(15) 1.0755(5) 0.8092(4) 0.0424(18) Uani 1 1 d . . . . .
H33A H 0.272489 1.081977 0.855566 0.064 Uiso 1 1 calc GR . . . .
H33B H 0.258915 1.157751 0.790449 0.064 Uiso 1 1 calc GR . . . .
H33C H 0.504617 1.063046 0.806933 0.064 Uiso 1 1 calc GR . . . .
C19 C 0.6781(14) 0.6628(5) 0.1843(3) 0.0359(15) Uani 1 1 d . . . . .
H19A H 0.712093 0.644168 0.137622 0.054 Uiso 1 1 calc GR . . . .
H19B H 0.733051 0.754807 0.200831 0.054 Uiso 1 1 calc GR . . . .
H19C H 0.487706 0.651262 0.188514 0.054 Uiso 1 1 calc GR . . . .
C18 C 0.6181(17) 0.2134(8) 0.3511(4) 0.0125(17) Uani 0.492(7) 1 d D U P A 1
H18 H 0.580638 0.283248 0.324080 0.015 Uiso 0.492(7) 1 calc R . P A 1
C51 C 0.0683(18) 0.4405(8) 0.5793(4) 0.0121(17) Uani 0.490(8) 1 d . U P C 1
H51 H -0.111351 0.438440 0.560599 0.014 Uiso 0.490(8) 1 calc R . P C 1
C52 C 0.1264(17) 0.4388(9) 0.6476(4) 0.0138(17) Uani 0.490(8) 1 d D U P C 1
H52 H -0.015035 0.442790 0.675424 0.017 Uiso 0.490(8) 1 calc R . P C 1
C31 C 0.2429(19) 0.8333(9) 0.6629(4) 0.0163(18) Uani 0.502(8) 1 d D U P D 1
H31 H 0.253132 0.753827 0.684029 0.020 Uiso 0.502(8) 1 calc R . P D 1
C28 C 0.249(2) 1.0659(10) 0.6033(5) 0.021(2) Uani 0.502(8) 1 d . U P D 1
H28 H 0.246353 1.146262 0.582977 0.026 Uiso 0.502(8) 1 calc R . P D 1
C22 C 0.5612(17) 0.5758(8) 0.3259(4) 0.0125(17) Uani 0.500(8) 1 d D U P B 1
H22 H 0.413027 0.541100 0.296816 0.015 Uiso 0.500(8) 1 calc R . P B 1
C30 C 0.272(2) 0.8276(10) 0.5949(5) 0.0182(19) Uani 0.502(8) 1 d . U P D 1
H30 H 0.285400 0.743608 0.569143 0.022 Uiso 0.502(8) 1 calc R . P D 1
C27 C 0.2225(18) 1.0729(8) 0.6715(5) 0.0161(18) Uani 0.502(8) 1 d D U P D 1
H27 H 0.217630 1.155269 0.699054 0.019 Uiso 0.502(8) 1 calc R . P D 1
C26 C 1.0231(18) 0.6335(9) 0.3504(5) 0.020(2) Uani 0.500(8) 1 d D U P B 1
H26 H 1.197878 0.641224 0.337288 0.024 Uiso 0.500(8) 1 calc R . P B 1
C49 C 0.537(2) 0.4507(10) 0.5664(5) 0.020(2) Uani 0.490(8) 1 d . U P C 1
H49 H 0.677171 0.455061 0.538576 0.024 Uiso 0.490(8) 1 calc R . P C 1
C48 C 0.5965(18) 0.4498(9) 0.6337(5) 0.0156(18) Uani 0.490(8) 1 d D U P C 1
H48 H 0.776111 0.462080 0.651950 0.019 Uiso 0.490(8) 1 calc R . P C 1
C14 C 0.6634(19) -0.0198(8) 0.3656(5) 0.0152(18) Uani 0.492(7) 1 d D U P A 1
H14 H 0.653477 -0.111255 0.347854 0.018 Uiso 0.492(7) 1 calc R . P A 1
C17 C 0.685(2) 0.2466(9) 0.4189(5) 0.0184(19) Uani 0.492(7) 1 d . U P A 1
H17 H 0.698947 0.337671 0.437227 0.022 Uiso 0.492(7) 1 calc R . P A 1
C23 C 0.524(2) 0.6071(10) 0.3936(5) 0.020(2) Uani 0.500(8) 1 d . U P B 1
H23 H 0.352052 0.598219 0.408011 0.023 Uiso 0.500(8) 1 calc R . P B 1
C15 C 0.734(2) 0.0147(10) 0.4327(5) 0.0182(19) Uani 0.492(7) 1 d . U P A 1
H15 H 0.782893 -0.049610 0.462138 0.022 Uiso 0.492(7) 1 calc R . P A 1
C25 C 0.983(2) 0.6613(10) 0.4174(5) 0.022(2) Uani 0.500(8) 1 d . U P B 1
H25 H 1.131352 0.688008 0.448286 0.026 Uiso 0.500(8) 1 calc R . P B 1
C22A C 0.7479(19) 0.4896(9) 0.3324(5) 0.0173(18) Uani 0.500(8) 1 d D U P B 2
H22A H 0.723658 0.401211 0.310753 0.021 Uiso 0.500(8) 1 calc R . P B 2
C23A C 0.729(2) 0.5180(10) 0.4000(5) 0.022(2) Uani 0.500(8) 1 d . U P B 2
H23A H 0.701976 0.447974 0.426360 0.026 Uiso 0.500(8) 1 calc R . P B 2
C24A C 0.750(5) 0.648(2) 0.4284(9) 0.026(5) Uani 0.500(8) 1 d . U P B 2
H24A H 0.741084 0.666014 0.474958 0.032 Uiso 0.500(8) 1 calc R . P B 2
C25A C 0.783(2) 0.7532(10) 0.3930(5) 0.022(2) Uani 0.500(8) 1 d . U P B 2
H25A H 0.788930 0.842580 0.413814 0.026 Uiso 0.500(8) 1 calc R . P B 2
C26A C 0.8067(19) 0.7250(9) 0.3244(4) 0.0179(19) Uani 0.500(8) 1 d D U P B 2
H26A H 0.825427 0.794267 0.297173 0.022 Uiso 0.500(8) 1 calc R . P B 2
C14A C 0.4011(17) 0.1203(9) 0.3630(5) 0.0173(18) Uani 0.508(7) 1 d D U P A 2
H14A H 0.221529 0.121755 0.344473 0.021 Uiso 0.508(7) 1 calc R . P A 2
C15A C 0.4633(19) 0.1535(9) 0.4311(5) 0.0178(19) Uani 0.508(7) 1 d . U P A 2
H15A H 0.324504 0.178436 0.458379 0.021 Uiso 0.508(7) 1 calc R . P A 2
C16A C 0.743(4) 0.151(2) 0.4622(11) 0.009(4) Uiso 0.508(7) 1 d . U P A 2
H16A H 0.787112 0.159793 0.508843 0.010 Uiso 0.508(7) 1 calc R . P A 2
C17A C 0.9321(18) 0.1334(9) 0.4170(4) 0.0149(18) Uani 0.508(7) 1 d . U P A 2
H17A H 1.114137 0.145400 0.433198 0.018 Uiso 0.508(7) 1 calc R . P A 2
C18A C 0.8707(17) 0.0992(9) 0.3483(4) 0.0161(18) Uani 0.508(7) 1 d D U P A 2
H18A H 1.009561 0.086014 0.319880 0.019 Uiso 0.508(7) 1 calc R . P A 2
C50A C 0.264(6) 0.4109(19) 0.5411(13) 0.018(3) Uani 0.510(8) 1 d . U P C 2
H50A H 0.217702 0.407067 0.494727 0.021 Uiso 0.510(8) 1 calc R . P C 2
C51A C 0.302(2) 0.5350(9) 0.5794(4) 0.0183(19) Uani 0.510(8) 1 d . U P C 2
H51A H 0.281211 0.615031 0.559017 0.022 Uiso 0.510(8) 1 calc R . P C 2
C52A C 0.3712(19) 0.5407(9) 0.6468(4) 0.0164(18) Uani 0.510(8) 1 d D U P C 2
H52A H 0.401311 0.625285 0.672281 0.020 Uiso 0.510(8) 1 calc R . P C 2
C48A C 0.3620(17) 0.2990(8) 0.6381(4) 0.0150(17) Uani 0.510(8) 1 d D U P C 2
H48A H 0.386087 0.219555 0.658838 0.018 Uiso 0.510(8) 1 calc R . P C 2
C49A C 0.2933(18) 0.2941(9) 0.5702(5) 0.0159(18) Uani 0.510(8) 1 d . U P C 2
H49A H 0.266495 0.210249 0.543882 0.019 Uiso 0.510(8) 1 calc R . P C 2
C30A C 0.487(2) 0.9078(10) 0.6020(5) 0.020(2) Uani 0.498(8) 1 d . U P D 2
H30A H 0.661519 0.897728 0.588334 0.024 Uiso 0.498(8) 1 calc R . P D 2
C31A C 0.4445(18) 0.9180(10) 0.6691(5) 0.0156(19) Uani 0.498(8) 1 d D U P D 2
H31A H 0.594744 0.905273 0.699302 0.019 Uiso 0.498(8) 1 calc R . P D 2
C27A C -0.0221(18) 0.9382(10) 0.6422(5) 0.020(2) Uani 0.498(8) 1 d D U P D 2
H27A H -0.199143 0.940974 0.654605 0.024 Uiso 0.498(8) 1 calc R . P D 2
C28A C 0.014(2) 0.9276(10) 0.5744(5) 0.020(2) Uani 0.498(8) 1 d . U P D 2
H28A H -0.134151 0.930992 0.542404 0.024 Uiso 0.498(8) 1 calc R . P D 2
C29A C 0.265(6) 0.9126(17) 0.5548(12) 0.018(4) Uani 0.498(8) 1 d . U P D 2
H29A H 0.290300 0.905233 0.508958 0.022 Uiso 0.498(8) 1 calc R . P D 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
O3 P2 N2 107.44(19) . . ?
O3 P2 C35 100.98(18) . . ?
O4 P2 O3 112.0(2) . . ?
O4 P2 N2 112.3(2) . . ?
O4 P2 C35 113.9(2) . . ?
N2 P2 C35 109.5(2) . . ?
O1 P1 N1 107.44(19) . . ?
O1 P1 C6 100.73(19) . . ?
O2 P1 O1 112.2(2) . . ?
O2 P1 N1 112.3(2) . . ?
O2 P1 C6 113.8(2) . . ?
N1 P1 C6 109.7(2) . . ?
C12 O1 P1 125.1(3) . . ?
C46 O3 P2 124.4(3) . . ?
C20 N1 P1 124.4(3) . . ?
O3 C46 C41 121.2(4) . . ?
O3 C46 C45 116.1(4) . . ?
C45 C46 C41 122.7(4) . . ?
O1 C12 C7 120.7(4) . . ?
O1 C12 C11 116.0(4) . . ?
C11 C12 C7 123.3(4) . . ?
C34 N2 P2 124.3(3) . . ?
C5 C6 P1 120.7(3) . . ?
C1 C6 P1 117.8(3) . . ?
C1 C6 C5 121.5(4) . . ?
C6 C5 C7 121.1(4) . . ?
C6 C5 C4 117.4(4) . . ?
C4 C5 C7 121.4(4) . . ?
C35 C40 C41 120.6(4) . . ?
C39 C40 C41 121.4(4) . . ?
C39 C40 C35 117.9(4) . . ?
C12 C7 C5 121.3(4) . . ?
C8 C7 C12 116.6(4) . . ?
C8 C7 C5 122.1(4) . . ?
C37 C36 C35 120.0(4) . . ?
C46 C41 C40 121.0(4) . . ?
C42 C41 C46 117.3(4) . . ?
C42 C41 C40 121.7(4) . . ?
C40 C35 P2 121.1(3) . . ?
C36 C35 P2 118.2(3) . . ?
C36 C35 C40 120.6(4) . . ?
C42 C43 C44 119.9(4) . . ?
C43 C42 C41 121.1(4) . . ?
C18 C13 C11 123.3(5) . . ?
C18 C13 C14 116.9(6) . . ?
C14 C13 C11 119.8(5) . . ?
C14A C13 C11 118.0(5) . . ?
C18A C13 C11 122.1(5) . . ?
C18A C13 C14A 119.5(6) . . ?
C2 C1 C6 119.7(5) . . ?
C9 C8 C7 121.4(4) . . ?
C52 C47 C45 124.1(5) . . ?
C48 C47 C45 119.5(5) . . ?
C48 C47 C52 115.5(6) . . ?
C52A C47 C45 124.4(5) . . ?
C52A C47 C48A 120.6(6) . . ?
C48A C47 C45 114.9(5) . . ?
C45 C44 C43 121.4(4) . . ?
C46 C45 C47 122.3(4) . . ?
C44 C45 C46 117.6(4) . . ?
C44 C45 C47 120.1(4) . . ?
C37 C38 C39 120.5(4) . . ?
C12 C11 C13 122.2(4) . . ?
C10 C11 C12 117.6(4) . . ?
C10 C11 C13 120.2(4) . . ?
C4 C3 C2 120.9(4) . . ?
C17 C16 C15 126(2) . . ?
C38 C37 C36 120.1(4) . . ?
C8 C9 C10 120.2(4) . . ?
C38 C39 C40 120.8(4) . . ?
C9 C10 C11 120.9(4) . . ?
C3 C4 C5 120.7(4) . . ?
C22 C21 C20 123.9(5) . . ?
C22 C21 C26 112.4(6) . . ?
C26 C21 C20 123.7(5) . . ?
C22A C21 C20 119.4(5) . . ?
C22A C21 C26A 125.0(6) . . ?
C26A C21 C20 115.4(5) . . ?
C1 C2 C3 119.8(4) . . ?
N1 C20 C21 113.1(4) . . ?
N1 C20 C19 107.6(4) . . ?
C21 C20 C19 112.4(4) . . ?
C25 C24 C23 117.3(14) . . ?
C31 C32 C34 122.4(5) . . ?
C31 C32 C27 124.1(7) . . ?
C27 C32 C34 113.2(5) . . ?
C31A C32 C34 125.7(5) . . ?
C31A C32 C27A 110.0(6) . . ?
C27A C32 C34 123.6(5) . . ?
C49 C50 C51 120.2(19) . . ?
N2 C34 C32 112.7(4) . . ?
N2 C34 C33 108.4(5) . . ?
C32 C34 C33 112.5(4) . . ?
C28 C29 C30 118.3(16) . . ?
C13 C18 C17 122.5(8) . . ?
C50 C51 C52 119.5(13) . . ?
C51 C52 C47 121.3(7) . . ?
C32 C31 C30 120.0(8) . . ?
C29 C28 C27 122.1(12) . . ?
C21 C22 C23 124.1(8) . . ?
C31 C30 C29 120.0(11) . . ?
C28 C27 C32 114.8(8) . . ?
C25 C26 C21 122.3(8) . . ?
C48 C49 C50 120.8(13) . . ?
C49 C48 C47 121.7(8) . . ?
C15 C14 C13 120.0(7) . . ?
C16 C17 C18 119.5(16) . . ?
C24 C23 C22 121.2(11) . . ?
C14 C15 C16 114.8(12) . . ?
C24 C25 C26 122.4(11) . . ?
C21 C22A C23A 117.2(8) . . ?
C24A C23A C22A 119.3(11) . . ?
C25A C24A C23A 123.1(14) . . ?
C24A C25A C26A 117.9(11) . . ?
C21 C26A C25A 117.0(8) . . ?
C15A C14A C13 119.8(8) . . ?
C14A C15A C16A 121.6(12) . . ?
C17A C16A C15A 114.0(16) . . ?
C16A C17A C18A 123.9(13) . . ?
C13 C18A C17A 119.9(7) . . ?
C49A C50A C51A 121(2) . . ?
C52A C51A C50A 119.8(12) . . ?
C47 C52A C51A 121.2(8) . . ?
C49A C48A C47 117.7(7) . . ?
C50A C49A C48A 119.9(14) . . ?
C31A C30A C29A 118.6(14) . . ?
C30A C31A C32 126.6(8) . . ?
C28A C27A C32 123.8(8) . . ?
C29A C28A C27A 119.3(14) . . ?
C28A C29A C30A 120.8(19) . . ?
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
P2 O3 1.603(3) . ?
P2 O4 1.470(3) . ?
P2 N2 1.617(4) . ?
P2 C35 1.780(4) . ?
P1 O1 1.603(3) . ?
P1 O2 1.471(3) . ?
P1 N1 1.627(4) . ?
P1 C6 1.785(4) . ?
O1 C12 1.386(5) . ?
O3 C46 1.386(5) . ?
N1 C20 1.472(6) . ?
C46 C41 1.406(5) . ?
C46 C45 1.403(6) . ?
C12 C7 1.405(6) . ?
C12 C11 1.394(6) . ?
N2 C34 1.483(6) . ?
C6 C5 1.403(6) . ?
C6 C1 1.400(7) . ?
C5 C7 1.475(6) . ?
C5 C4 1.414(6) . ?
C40 C41 1.486(6) . ?
C40 C35 1.406(6) . ?
C40 C39 1.404(6) . ?
C7 C8 1.402(6) . ?
C36 C35 1.402(6) . ?
C36 C37 1.381(7) . ?
C41 C42 1.404(6) . ?
C43 C42 1.382(6) . ?
C43 C44 1.397(6) . ?
C13 C11 1.482(6) . ?
C13 C18 1.361(9) . ?
C13 C14 1.467(9) . ?
C13 C14A 1.402(9) . ?
C13 C18A 1.401(9) . ?
C1 C2 1.383(7) . ?
C8 C9 1.383(7) . ?
C47 C45 1.485(6) . ?
C47 C52 1.438(9) . ?
C47 C48 1.420(9) . ?
C47 C52A 1.320(9) . ?
C47 C48A 1.466(9) . ?
C44 C45 1.386(6) . ?
C38 C37 1.379(7) . ?
C38 C39 1.389(6) . ?
C11 C10 1.392(6) . ?
C3 C4 1.383(7) . ?
C3 C2 1.390(7) . ?
C16 C17 1.22(3) . ?
C16 C15 1.46(3) . ?
C9 C10 1.388(6) . ?
C21 C20 1.523(7) . ?
C21 C22 1.396(9) . ?
C21 C26 1.485(10) . ?
C21 C22A 1.345(9) . ?
C21 C26A 1.377(9) . ?
C20 C19 1.532(8) . ?
C24 C23 1.41(2) . ?
C24 C25 1.37(2) . ?
C32 C34 1.519(7) . ?
C32 C31 1.277(10) . ?
C32 C27 1.442(9) . ?
C32 C31A 1.401(10) . ?
C32 C27A 1.507(10) . ?
C50 C51 1.39(3) . ?
C50 C49 1.38(3) . ?
C34 C33 1.521(9) . ?
C29 C28 1.38(2) . ?
C29 C30 1.40(2) . ?
C18 C17 1.395(13) . ?
C51 C52 1.396(11) . ?
C31 C30 1.401(12) . ?
C28 C27 1.401(13) . ?
C22 C23 1.410(12) . ?
C26 C25 1.397(14) . ?
C49 C48 1.378(13) . ?
C14 C15 1.384(13) . ?
C22A C23A 1.387(13) . ?
C23A C24A 1.37(2) . ?
C24A C25A 1.37(2) . ?
C25A C26A 1.409(12) . ?
C14A C15A 1.397(13) . ?
C15A C16A 1.49(2) . ?
C16A C17A 1.38(2) . ?
C17A C18A 1.408(12) . ?
C50A C51A 1.40(2) . ?
C50A C49A 1.38(2) . ?
C51A C52A 1.380(12) . ?
C48A C49A 1.390(12) . ?
C30A C31A 1.396(13) . ?
C30A C29A 1.41(3) . ?
C27A C28A 1.402(13) . ?
C28A C29A 1.36(3) . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9918(11)
2 0.0082(11)
