#------------------------------------------------------------------------------
#$Date: 2019-11-17 12:34:39 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229901 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/62/7046231.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_7046231
loop_
_publ_author_name
'Wakatsuki, Ayana'
'Yukimoto, Mariko'
'Minoura, Mao'
'Fujii, Kaori'
'Kimura, Yoshifumi'
'Matano, Yoshihiro'
_publ_section_title
;
 Regioselective functionalization at the 7-position of
 1,2,3-triphenylbenzo[b]phosphole oxide via P[double bond, length as
 m-dash]O-directed lithiation.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7123
_journal_page_last               7127
_journal_paper_doi               10.1039/c8dt01503a
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         '(C70 H52 B F N2 O3 P2), 0.5(C4H10O), H2O'
_chemical_formula_sum            'C72 H59 B F N2 O4.5 P2'
_chemical_formula_weight         1115.96
_chemical_name_systematic        BODIPY_phosphole
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-29 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.421(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.9407(10)
_cell_length_b                   10.2627(4)
_cell_length_c                   32.0520(7)
_cell_measurement_reflns_used    39607
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      1.403
_cell_volume                     11787.2(6)
_computing_cell_refinement       'Rapid Auto'
_computing_data_collection       'Rapid Auto'
_computing_data_reduction        'Rapid Auto'
_computing_molecular_graphics
'Yadokari-XG 2011 (Wakita Nemoto et al. 2011)'
_computing_publication_material
'Yadokari-XG 2011 (Wakita Nemoto et al. 2011)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT-2013
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ω
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.78228
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            39607
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.403
_diffrn_source                   'SPring-8 BL40XU'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       plate
_exptl_crystal_F_000             4680
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and diethyl ether'
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     762
_refine_ls_number_reflns         7698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1041P)²+8.1075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6745
_reflns_number_total             7698
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8dt01503a2.cif
_cod_data_source_block           MM06MTN
_cod_depositor_comments
'Adding full bibliography for 7046230--7046231.cif.'
_cod_original_formula_sum        'C72 H59 B F N2 O4.50 P2'
_cod_database_code               7046231
_shelx_shelxl_version_number     2014/7
_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_min   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.26654(9) 0.1640(3) 0.14429(11) 0.0388(8) Uani 1 1 d . . . . .
O1 O 0.26712(5) 0.03140(18) 0.15548(7) 0.0461(5) Uani 1 1 d . . . . .
H1A H 0.2866 0.0154 0.1708 0.069 Uiso 1 1 calc R U . . .
F1 F 0.23941(4) 0.18731(16) 0.11122(5) 0.0457(4) Uani 1 1 d . . . . .
N1 N 0.30635(6) 0.2119(2) 0.13221(7) 0.0336(5) Uani 1 1 d . . . . .
C1 C 0.32736(7) 0.1598(3) 0.10316(9) 0.0354(7) Uani 1 1 d . . . . .
C2 C 0.36289(8) 0.2210(3) 0.10521(9) 0.0394(7) Uani 1 1 d . . . . .
H2A H 0.3825 0.2027 0.0878 0.047 Uiso 1 1 calc R U . . .
C3 C 0.36379(8) 0.3111(3) 0.13671(9) 0.0367(7) Uani 1 1 d . . . . .
H3A H 0.3840 0.3673 0.1452 0.044 Uiso 1 1 calc R U . . .
C4 C 0.32883(8) 0.3044(2) 0.15413(9) 0.0357(7) Uani 1 1 d . . . . .
C5 C 0.31699(8) 0.3692(3) 0.18920(9) 0.0373(7) Uani 1 1 d . . . . .
C6 C 0.28149(8) 0.3456(3) 0.20219(9) 0.0399(7) Uani 1 1 d . . . . .
C7 C 0.26215(9) 0.4068(3) 0.23347(9) 0.0467(8) Uani 1 1 d . . . . .
H7A H 0.2722 0.4697 0.2530 0.056 Uiso 1 1 calc R U . . .
C8 C 0.22641(8) 0.3597(3) 0.23079(9) 0.0445(7) Uani 1 1 d . . . . .
H8A H 0.2072 0.3844 0.2480 0.053 Uiso 1 1 calc R U . . .
C9 C 0.22322(8) 0.2680(3) 0.19800(9) 0.0368(7) Uani 1 1 d . . . . .
N2 N 0.25665(6) 0.2582(2) 0.18115(7) 0.0361(6) Uani 1 1 d . . . . .
C10 C 0.31440(7) 0.0535(2) 0.07462(9) 0.0345(7) Uani 1 1 d . . . . .
C11 C 0.33602(7) -0.0599(3) 0.07244(9) 0.0344(7) Uani 1 1 d . . . . .
C12 C 0.32447(7) -0.1624(2) 0.04501(9) 0.0334(6) Uani 1 1 d . . . . .
C13 C 0.29173(7) -0.1498(3) 0.01906(9) 0.0360(7) Uani 1 1 d . . . . .
H13A H 0.2842 -0.2173 -0.0001 0.043 Uiso 1 1 calc R U . . .
C14 C 0.27015(8) -0.0380(3) 0.02131(9) 0.0372(7) Uani 1 1 d . . . . .
H14A H 0.2476 -0.0302 0.0039 0.045 Uiso 1 1 calc R U . . .
C15 C 0.28106(8) 0.0621(3) 0.04852(9) 0.0364(7) Uani 1 1 d . . . . .
H15A H 0.2659 0.1375 0.0496 0.044 Uiso 1 1 calc R U . . .
C16 C 0.34862(7) -0.2808(3) 0.05004(9) 0.0343(7) Uani 1 1 d . . . . .
C17 C 0.37675(8) -0.2726(3) 0.08090(9) 0.0343(7) Uani 1 1 d . . . . .
P1 P 0.37764(2) -0.10939(7) 0.10331(2) 0.0345(2) Uani 1 1 d . . . . .
O2 O 0.37873(5) -0.09525(18) 0.14914(6) 0.0419(5) Uani 1 1 d . . . . .
C18 C 0.33899(7) -0.3955(3) 0.02274(9) 0.0350(7) Uani 1 1 d . . . . .
C19 C 0.33700(8) -0.3812(3) -0.02058(9) 0.0415(7) Uani 1 1 d . . . . .
H19A H 0.3422 -0.2991 -0.0325 0.050 Uiso 1 1 calc R U . . .
C20 C 0.32742(9) -0.4860(3) -0.04650(10) 0.0469(8) Uani 1 1 d . . . . .
H20A H 0.3257 -0.4751 -0.0760 0.056 Uiso 1 1 calc R U . . .
C21 C 0.32034(8) -0.6062(3) -0.02947(11) 0.0486(8) Uani 1 1 d . . . . .
H21A H 0.3142 -0.6783 -0.0473 0.058 Uiso 1 1 calc R U . . .
C22 C 0.32219(8) -0.6217(3) 0.01298(11) 0.0473(8) Uani 1 1 d . . . . .
H22A H 0.3172 -0.7045 0.0246 0.057 Uiso 1 1 calc R U . . .
C23 C 0.33143(8) -0.5164(3) 0.03954(10) 0.0410(7) Uani 1 1 d . . . . .
H23A H 0.3325 -0.5276 0.0690 0.049 Uiso 1 1 calc R U . . .
C24 C 0.40568(8) -0.3702(3) 0.09542(9) 0.0351(7) Uani 1 1 d . . . . .
C25 C 0.41966(8) -0.4632(3) 0.06891(10) 0.0384(7) Uani 1 1 d . . . . .
H25A H 0.4107 -0.4662 0.0402 0.046 Uiso 1 1 calc R U . . .
C26 C 0.44669(8) -0.5516(3) 0.08451(10) 0.0441(8) Uani 1 1 d . . . . .
H26A H 0.4558 -0.6152 0.0663 0.053 Uiso 1 1 calc R U . . .
C27 C 0.46046(8) -0.5488(3) 0.12554(10) 0.0456(8) Uani 1 1 d . . . . .
H27A H 0.4789 -0.6098 0.1357 0.055 Uiso 1 1 calc R U . . .
C28 C 0.44720(8) -0.4559(3) 0.15203(10) 0.0457(8) Uani 1 1 d . . . . .
H28A H 0.4568 -0.4521 0.1805 0.055 Uiso 1 1 calc R U . . .
C29 C 0.41992(8) -0.3682(3) 0.13715(10) 0.0421(7) Uani 1 1 d . . . . .
H29A H 0.4108 -0.3058 0.1557 0.050 Uiso 1 1 calc R U . . .
C30 C 0.41765(8) -0.0316(2) 0.08253(10) 0.0372(7) Uani 1 1 d . . . . .
C31 C 0.44510(8) 0.0231(3) 0.11015(11) 0.0462(8) Uani 1 1 d . . . . .
H31A H 0.4432 0.0177 0.1395 0.055 Uiso 1 1 calc R U . . .
C32 C 0.47589(8) 0.0868(3) 0.09422(13) 0.0532(9) Uani 1 1 d . . . . .
H32A H 0.4949 0.1235 0.1129 0.064 Uiso 1 1 calc R U . . .
C33 C 0.47834(9) 0.0955(3) 0.05210(12) 0.0512(9) Uani 1 1 d . . . . .
H33A H 0.4990 0.1389 0.0415 0.061 Uiso 1 1 calc R U . . .
C34 C 0.45119(8) 0.0418(3) 0.02490(11) 0.0490(8) Uani 1 1 d . . . . .
H34A H 0.4532 0.0479 -0.0044 0.059 Uiso 1 1 calc R U . . .
C35 C 0.42060(8) -0.0219(3) 0.03992(10) 0.0406(7) Uani 1 1 d . . . . .
H35A H 0.4019 -0.0584 0.0209 0.049 Uiso 1 1 calc R U . . .
C36 C 0.34333(8) 0.4649(3) 0.21178(9) 0.0389(7) Uani 1 1 d . . . . .
C37 C 0.37295(9) 0.4168(3) 0.23858(10) 0.0458(8) Uani 1 1 d . . . . .
C38 C 0.39838(9) 0.5067(3) 0.25819(10) 0.0497(8) Uani 1 1 d . . . . .
H38A H 0.4186 0.4755 0.2762 0.060 Uiso 1 1 calc R U . . .
C39 C 0.39441(9) 0.6391(3) 0.25167(10) 0.0482(8) Uani 1 1 d . . . . .
C40 C 0.36481(9) 0.6834(3) 0.22584(10) 0.0498(8) Uani 1 1 d . . . . .
H40A H 0.3618 0.7747 0.2220 0.060 Uiso 1 1 calc R U . . .
C41 C 0.33881(9) 0.5989(3) 0.20482(9) 0.0436(8) Uani 1 1 d . . . . .
C42 C 0.37819(11) 0.2739(3) 0.24698(12) 0.0693(11) Uani 1 1 d . . . . .
H42A H 0.3572 0.2409 0.2617 0.104 Uiso 1 1 calc R U . . .
H42B H 0.4015 0.2600 0.2643 0.104 Uiso 1 1 calc R U . . .
H42C H 0.3792 0.2273 0.2204 0.104 Uiso 1 1 calc R U . . .
C43 C 0.42338(10) 0.7331(4) 0.27195(12) 0.0664(10) Uani 1 1 d . . . . .
H43A H 0.4337 0.6972 0.2987 0.100 Uiso 1 1 calc R U . . .
H43B H 0.4115 0.8173 0.2767 0.100 Uiso 1 1 calc R U . . .
H43C H 0.4435 0.7452 0.2534 0.100 Uiso 1 1 calc R U . . .
C44 C 0.30805(11) 0.6514(3) 0.17526(11) 0.0627(10) Uani 1 1 d . . . . .
H44A H 0.2840 0.6376 0.1871 0.094 Uiso 1 1 calc R U . . .
H44B H 0.3081 0.6062 0.1483 0.094 Uiso 1 1 calc R U . . .
H44C H 0.3119 0.7449 0.1711 0.094 Uiso 1 1 calc R U . . .
C45 C 0.18892(7) 0.2028(3) 0.17941(8) 0.0357(7) Uani 1 1 d . . . . .
C46 C 0.15885(7) 0.2798(3) 0.16381(9) 0.0353(7) Uani 1 1 d . . . . .
C47 C 0.12807(7) 0.2250(3) 0.14021(8) 0.0344(6) Uani 1 1 d . . . . .
C48 C 0.12470(8) 0.0903(3) 0.13680(9) 0.0361(7) Uani 1 1 d . . . . .
H48A H 0.1034 0.0519 0.1224 0.043 Uiso 1 1 calc R U . . .
C49 C 0.15359(8) 0.0128(3) 0.15515(9) 0.0386(7) Uani 1 1 d . . . . .
H49A H 0.1512 -0.0793 0.1540 0.046 Uiso 1 1 calc R U . . .
C50 C 0.18563(8) 0.0671(3) 0.17488(9) 0.0379(7) Uani 1 1 d . . . . .
H50A H 0.2055 0.0122 0.1854 0.045 Uiso 1 1 calc R U . . .
C51 C 0.10148(7) 0.3227(3) 0.12009(9) 0.0351(7) Uani 1 1 d . . . . .
C52 C 0.10992(8) 0.4479(3) 0.13143(9) 0.0376(7) Uani 1 1 d . . . . .
P2 P 0.15127(2) 0.45357(7) 0.16764(2) 0.0359(2) Uani 1 1 d . . . . .
O3 O 0.14444(5) 0.50767(18) 0.20911(6) 0.0404(5) Uani 1 1 d . . . . .
C53 C 0.06977(7) 0.2775(2) 0.09123(9) 0.0345(7) Uani 1 1 d . . . . .
C54 C 0.07670(8) 0.1989(3) 0.05699(9) 0.0410(7) Uani 1 1 d . . . . .
H54A H 0.1017 0.1783 0.0516 0.049 Uiso 1 1 calc R U . . .
C55 C 0.04743(8) 0.1512(3) 0.03098(9) 0.0430(7) Uani 1 1 d . . . . .
H55A H 0.0525 0.0988 0.0076 0.052 Uiso 1 1 calc R U . . .
C56 C 0.01064(8) 0.1790(3) 0.03846(10) 0.0440(7) Uani 1 1 d . . . . .
H56A H -0.0093 0.1446 0.0207 0.053 Uiso 1 1 calc R U . . .
C57 C 0.00348(8) 0.2566(3) 0.07186(10) 0.0460(8) Uani 1 1 d . . . . .
H57A H -0.0215 0.2766 0.0771 0.055 Uiso 1 1 calc R U . . .
C58 C 0.03284(8) 0.3059(3) 0.09799(10) 0.0409(7) Uani 1 1 d . . . . .
H58A H 0.0276 0.3600 0.1209 0.049 Uiso 1 1 calc R U . . .
C59 C 0.09161(8) 0.5707(3) 0.11613(9) 0.0373(7) Uani 1 1 d . . . . .
C60 C 0.08902(9) 0.6023(3) 0.07418(10) 0.0458(8) Uani 1 1 d . . . . .
H60A H 0.0973 0.5418 0.0545 0.055 Uiso 1 1 calc R U . . .
C61 C 0.07445(9) 0.7217(3) 0.06039(11) 0.0521(8) Uani 1 1 d . . . . .
H61A H 0.0730 0.7423 0.0314 0.062 Uiso 1 1 calc R U . . .
C62 C 0.06210(9) 0.8107(3) 0.08878(12) 0.0525(9) Uani 1 1 d . . . . .
H62A H 0.0521 0.8922 0.0794 0.063 Uiso 1 1 calc R U . . .
C63 C 0.06454(9) 0.7799(3) 0.13041(12) 0.0535(9) Uani 1 1 d . . . . .
H63A H 0.0560 0.8402 0.1500 0.064 Uiso 1 1 calc R U . . .
C64 C 0.07946(8) 0.6611(3) 0.14432(10) 0.0453(8) Uani 1 1 d . . . . .
H64A H 0.0814 0.6416 0.1734 0.054 Uiso 1 1 calc R U . . .
C65 C 0.18666(8) 0.5412(3) 0.14208(9) 0.0388(7) Uani 1 1 d . . . . .
C66 C 0.19437(8) 0.6700(3) 0.15328(11) 0.0484(8) Uani 1 1 d . . . . .
H66A H 0.1823 0.7089 0.1755 0.058 Uiso 1 1 calc R U . . .
C67 C 0.21968(9) 0.7416(3) 0.13216(12) 0.0578(9) Uani 1 1 d . . . . .
H67A H 0.2246 0.8301 0.1394 0.069 Uiso 1 1 calc R U . . .
C68 C 0.23748(9) 0.6848(4) 0.10094(12) 0.0603(10) Uani 1 1 d . . . . .
H68A H 0.2546 0.7341 0.0863 0.072 Uiso 1 1 calc R U . . .
C69 C 0.23082(10) 0.5557(4) 0.09032(11) 0.0583(9) Uani 1 1 d . . . . .
H69A H 0.2439 0.5164 0.0689 0.070 Uiso 1 1 calc R U . . .
C70 C 0.20512(9) 0.4835(3) 0.11084(10) 0.0496(8) Uani 1 1 d . . . . .
H70A H 0.2003 0.3952 0.1034 0.060 Uiso 1 1 calc R U . . .
O4W O 0.16731(6) 0.5084(2) 0.29438(7) 0.0508(6) Uani 1 1 d . . . . .
H4WA H 0.1465(15) 0.481(5) 0.3133(16) 0.124(18) Uiso 1 1 d . . . . .
H4WB H 0.1541 0.5138 0.2669 0.111(17) Uiso 1 1 d . . . . .
C76 C 0.5004(8) 1.3923(11) 0.2560(7) 0.059(4) Uiso 0.25 1 d . . P A -2
H76A H 0.5148 1.4246 0.2335 0.089 Uiso 0.25 1 d . U P B -2
H76B H 0.5037 1.4478 0.2804 0.089 Uiso 0.25 1 d . U P C -2
H76C H 0.4738 1.3878 0.2460 0.089 Uiso 0.25 1 d . U P D -2
C72 C 0.5020(4) 0.9712(14) 0.2863(4) 0.128(4) Uiso 0.5 1 d . . P . .
H72A H 0.4789 1.0217 0.2850 0.192 Uiso 0.25 1 d . U P E -2
H72B H 0.5085 0.9424 0.3151 0.192 Uiso 0.25 1 d . U P F -2
H72C H 0.4986 0.8946 0.2680 0.192 Uiso 0.25 1 d . U P G -2
H72D H 0.5058 1.0342 0.3094 0.153 Uiso 0.25 1 d . U P H -3
H72E H 0.4746 0.9590 0.2807 0.153 Uiso 0.25 1 d . U P I -3
O5 O 0.5155(6) 1.026(2) 0.2517(9) 0.167(8) Uiso 0.25 1 d . . P A -3
C73 C 0.5112(4) 1.2788(16) 0.2650(4) 0.145(5) Uiso 0.5 1 d . . P . .
H73A H 0.4921 1.2436 0.2823 0.174 Uiso 0.25 1 d . U P J -2
H73B H 0.5338 1.2906 0.2837 0.174 Uiso 0.25 1 d . U P K -2
H73C H 0.5029 1.2503 0.2928 0.218 Uiso 0.25 1 d . U P L -3
H73D H 0.5012 1.3621 0.2579 0.218 Uiso 0.25 1 d . U P M -3
H73E H 0.5385 1.2783 0.2670 0.218 Uiso 0.25 1 d . U P N -3
C74 C 0.4951(7) 1.163(2) 0.2282(7) 0.086(5) Uiso 0.25 1 d . . P A -3
H74A H 0.4672 1.1544 0.2248 0.103 Uiso 0.25 1 d . U P O -3
H74B H 0.5042 1.1785 0.1997 0.103 Uiso 0.25 1 d . U P P -3
C75 C 0.5376(10) 1.065(3) 0.2701(10) 0.152(11) Uiso 0.25 1 d . . P A -2
H75A H 0.5486 1.1103 0.2931 0.182 Uiso 0.25 1 d . U P Q -2
H75B H 0.5523 1.0116 0.2549 0.182 Uiso 0.25 1 d . U P R -2
C71 C 0.5171(6) 0.851(2) 0.3001(7) 0.111(7) Uiso 0.25 1 d . . P A -3
H71A H 0.5166 0.7905 0.2767 0.167 Uiso 0.25 1 d . U P S -3
H71B H 0.5022 0.8164 0.3220 0.167 Uiso 0.25 1 d . U P T -3
H71C H 0.5428 0.8649 0.3117 0.167 Uiso 0.25 1 d . U P U -3
O6 O 0.5200(7) 1.165(3) 0.2404(9) 0.179(9) Uiso 0.25 1 d . . P A -2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0045 0.0021 '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'
P P 0.1220 0.1167 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0084 0.0042 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0142 0.0077 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0020 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0220 0.0131 '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
F1 B1 O1 110.7(2) .
F1 B1 N2 106.0(2) .
O1 B1 N2 113.5(3) .
F1 B1 N1 110.5(2) .
O1 B1 N1 111.4(2) .
N2 B1 N1 104.5(2) .
C1 N1 C4 106.4(2) .
C1 N1 B1 127.3(2) .
C4 N1 B1 125.7(2) .
N1 C1 C2 109.9(2) .
N1 C1 C10 123.6(2) .
C2 C1 C10 126.5(2) .
C3 C2 C1 107.7(2) .
C2 C3 C4 106.7(2) .
C5 C4 N1 121.7(2) .
C5 C4 C3 128.9(3) .
N1 C4 C3 109.3(2) .
C6 C5 C4 119.9(3) .
C6 C5 C36 121.7(3) .
C4 C5 C36 118.4(2) .
C5 C6 N2 122.1(3) .
C5 C6 C7 130.3(3) .
N2 C6 C7 107.3(2) .
C8 C7 C6 108.0(3) .
C7 C8 C9 107.7(3) .
N2 C9 C8 108.8(2) .
N2 C9 C45 122.6(2) .
C8 C9 C45 128.1(2) .
C9 N2 C6 108.1(2) .
C9 N2 B1 126.6(2) .
C6 N2 B1 125.2(2) .
C11 C10 C15 118.0(2) .
C11 C10 C1 119.6(3) .
C15 C10 C1 122.4(2) .
C10 C11 C12 120.7(3) .
C10 C11 P1 130.2(2) .
C12 C11 P1 108.87(19) .
C13 C12 C11 119.8(2) .
C13 C12 C16 126.6(2) .
C11 C12 C16 113.4(2) .
C14 C13 C12 119.6(3) .
C15 C14 C13 120.9(3) .
C14 C15 C10 120.9(3) .
C17 C16 C18 126.9(2) .
C17 C16 C12 114.9(2) .
C18 C16 C12 118.1(2) .
C16 C17 C24 130.2(2) .
C16 C17 P1 109.4(2) .
C24 C17 P1 120.3(2) .
O2 P1 C11 118.47(12) .
O2 P1 C30 111.19(13) .
C11 P1 C30 108.78(13) .
O2 P1 C17 118.81(12) .
C11 P1 C17 93.10(13) .
C30 P1 C17 104.48(12) .
C23 C18 C19 118.9(3) .
C23 C18 C16 121.4(3) .
C19 C18 C16 119.6(2) .
C20 C19 C18 120.5(3) .
C21 C20 C19 120.1(3) .
C22 C21 C20 120.1(3) .
C21 C22 C23 120.4(3) .
C18 C23 C22 119.9(3) .
C29 C24 C25 118.1(3) .
C29 C24 C17 119.0(2) .
C25 C24 C17 122.9(3) .
C26 C25 C24 120.0(3) .
C27 C26 C25 121.4(3) .
C26 C27 C28 119.2(3) .
C27 C28 C29 120.2(3) .
C28 C29 C24 121.2(3) .
C35 C30 C31 119.7(3) .
C35 C30 P1 121.2(2) .
C31 C30 P1 119.1(2) .
C30 C31 C32 119.5(3) .
C33 C32 C31 120.0(3) .
C32 C33 C34 120.4(3) .
C33 C34 C35 120.6(3) .
C30 C35 C34 119.8(3) .
C41 C36 C37 121.0(3) .
C41 C36 C5 120.1(3) .
C37 C36 C5 118.9(3) .
C36 C37 C38 118.5(3) .
C36 C37 C42 122.1(3) .
C38 C37 C42 119.4(3) .
C39 C38 C37 121.4(3) .
C40 C39 C38 118.9(3) .
C40 C39 C43 121.2(3) .
C38 C39 C43 119.9(3) .
C39 C40 C41 122.6(3) .
C36 C41 C40 117.7(3) .
C36 C41 C44 121.6(3) .
C40 C41 C44 120.7(3) .
C46 C45 C50 117.8(3) .
C46 C45 C9 118.9(2) .
C50 C45 C9 123.2(3) .
C45 C46 C47 121.3(3) .
C45 C46 P2 130.4(2) .
C47 C46 P2 108.3(2) .
C48 C47 C46 119.9(3) .
C48 C47 C51 125.7(3) .
C46 C47 C51 114.4(2) .
C47 C48 C49 118.3(3) .
C50 C49 C48 121.7(3) .
C49 C50 C45 120.4(3) .
C52 C51 C53 127.2(2) .
C52 C51 C47 113.3(2) .
C53 C51 C47 119.5(2) .
C51 C52 C59 128.8(3) .
C51 C52 P2 110.8(2) .
C59 C52 P2 120.2(2) .
O3 P2 C65 113.11(12) .
O3 P2 C46 117.87(12) .
C65 P2 C46 110.21(12) .
O3 P2 C52 113.73(12) .
C65 P2 C52 107.24(13) .
C46 P2 C52 92.60(13) .
C58 C53 C54 118.2(3) .
C58 C53 C51 122.2(2) .
C54 C53 C51 119.6(2) .
C55 C54 C53 120.3(3) .
C54 C55 C56 120.9(3) .
C57 C56 C55 119.4(3) .
C56 C57 C58 120.1(3) .
C53 C58 C57 121.2(3) .
C60 C59 C64 118.4(3) .
C60 C59 C52 121.0(3) .
C64 C59 C52 120.3(3) .
C59 C60 C61 120.8(3) .
C62 C61 C60 120.2(3) .
C63 C62 C61 119.3(3) .
C62 C63 C64 120.6(3) .
C59 C64 C63 120.6(3) .
C70 C65 C66 119.9(3) .
C70 C65 P2 120.8(2) .
C66 C65 P2 119.3(2) .
C67 C66 C65 120.2(3) .
C68 C67 C66 119.7(3) .
C67 C68 C69 120.6(3) .
C68 C69 C70 120.2(3) .
C65 C70 C69 119.4(3) .
O5 C72 C71 117.6(16) .
C72 O5 C74 121.6(17) .
C73 C73 C76 69.0(13) 2_655
C73 C73 O6 74.2(14) 2_655
C76 C73 O6 134(2) .
C73 C73 C74 45.0(8) 2_655
O5 C74 C73 98.6(14) .
O6 C75 C72 107(2) .
C73 O6 C75 108(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.404(4) .
B1 O1 1.407(4) .
B1 N2 1.587(4) .
B1 N1 1.589(4) .
N1 C1 1.353(3) .
N1 C4 1.400(3) .
C1 C2 1.421(4) .
C1 C10 1.475(4) .
C2 C3 1.368(4) .
C3 C4 1.415(4) .
C4 C5 1.400(4) .
C5 C6 1.394(4) .
C5 C36 1.509(4) .
C6 N2 1.401(4) .
C6 C7 1.411(4) .
C7 C8 1.369(4) .
C8 C9 1.409(4) .
C9 N2 1.359(4) .
C9 C45 1.486(4) .
C10 C11 1.404(4) .
C10 C15 1.410(4) .
C11 C12 1.413(4) .
C11 P1 1.802(3) .
C12 C13 1.394(4) .
C12 C16 1.494(4) .
C13 C14 1.390(4) .
C14 C15 1.385(4) .
C16 C17 1.362(4) .
C16 C18 1.491(4) .
C17 C24 1.492(4) .
C17 P1 1.821(3) .
P1 O2 1.474(2) .
P1 C30 1.816(3) .
C18 C23 1.388(4) .
C18 C19 1.393(4) .
C19 C20 1.386(4) .
C20 C21 1.381(5) .
C21 C22 1.366(5) .
C22 C23 1.400(4) .
C24 C29 1.395(4) .
C24 C25 1.397(4) .
C25 C26 1.393(4) .
C26 C27 1.369(4) .
C27 C28 1.386(4) .
C28 C29 1.388(4) .
C30 C35 1.382(4) .
C30 C31 1.392(4) .
C31 C32 1.414(5) .
C32 C33 1.363(5) .
C33 C34 1.373(5) .
C34 C35 1.396(4) .
C36 C41 1.401(4) .
C36 C37 1.405(4) .
C37 C38 1.412(4) .
C37 C42 1.501(5) .
C38 C39 1.380(5) .
C39 C40 1.374(5) .
C39 C43 1.527(4) .
C40 C41 1.408(4) .
C41 C44 1.500(5) .
C45 C46 1.400(4) .
C45 C50 1.405(4) .
C46 C47 1.408(4) .
C46 P2 1.809(3) .
C47 C48 1.391(4) .
C47 C51 1.497(4) .
C48 C49 1.401(4) .
C49 C50 1.387(4) .
C51 C52 1.363(4) .
C51 C53 1.486(4) .
C52 C59 1.487(4) .
C52 P2 1.815(3) .
P2 O3 1.478(2) .
P2 C65 1.805(3) .
C53 C58 1.392(4) .
C53 C54 1.400(4) .
C54 C55 1.381(4) .
C55 C56 1.391(4) .
C56 C57 1.375(4) .
C57 C58 1.391(4) .
C59 C60 1.379(4) .
C59 C64 1.389(4) .
C60 C61 1.391(4) .
C61 C62 1.386(5) .
C62 C63 1.367(5) .
C63 C64 1.392(4) .
C65 C70 1.377(4) .
C65 C66 1.392(4) .
C66 C67 1.386(4) .
C67 C68 1.360(5) .
C68 C69 1.384(5) .
C69 C70 1.389(5) .
C76 C73 1.254(19) .
C72 O5 1.37(3) .
C72 C71 1.41(3) .
C72 C75 1.71(4) .
O5 C74 1.73(3) .
C73 C73 1.20(2) 2_655
C73 O6 1.46(3) .
C73 C74 1.74(2) .
C75 O6 1.51(4) .
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
F1 B1 N1 C1 -68.6(3) .
O1 B1 N1 C1 54.8(4) .
N2 B1 N1 C1 177.8(2) .
F1 B1 N1 C4 121.7(3) .
O1 B1 N1 C4 -114.9(3) .
N2 B1 N1 C4 8.1(4) .
C4 N1 C1 C2 -1.9(3) .
B1 N1 C1 C2 -173.2(3) .
C4 N1 C1 C10 177.2(2) .
B1 N1 C1 C10 5.9(4) .
N1 C1 C2 C3 1.0(3) .
C10 C1 C2 C3 -178.1(3) .
C1 C2 C3 C4 0.3(3) .
C1 N1 C4 C5 -174.1(2) .
B1 N1 C4 C5 -2.7(4) .
C1 N1 C4 C3 2.2(3) .
B1 N1 C4 C3 173.6(2) .
C2 C3 C4 C5 174.4(3) .
C2 C3 C4 N1 -1.6(3) .
N1 C4 C5 C6 -2.3(4) .
C3 C4 C5 C6 -177.8(3) .
N1 C4 C5 C36 178.3(2) .
C3 C4 C5 C36 2.9(4) .
C4 C5 C6 N2 -0.1(4) .
C36 C5 C6 N2 179.2(2) .
C4 C5 C6 C7 -173.2(3) .
C36 C5 C6 C7 6.2(5) .
C5 C6 C7 C8 172.6(3) .
N2 C6 C7 C8 -1.3(3) .
C6 C7 C8 C9 0.4(4) .
C7 C8 C9 N2 0.6(3) .
C7 C8 C9 C45 -171.5(3) .
C8 C9 N2 C6 -1.4(3) .
C45 C9 N2 C6 171.2(2) .
C8 C9 N2 B1 178.2(3) .
C45 C9 N2 B1 -9.2(4) .
C5 C6 N2 C9 -172.8(3) .
C7 C6 N2 C9 1.6(3) .
C5 C6 N2 B1 7.6(4) .
C7 C6 N2 B1 -178.0(3) .
F1 B1 N2 C9 53.3(4) .
O1 B1 N2 C9 -68.4(4) .
N1 B1 N2 C9 170.0(2) .
F1 B1 N2 C6 -127.2(3) .
O1 B1 N2 C6 111.1(3) .
N1 B1 N2 C6 -10.5(4) .
N1 C1 C10 C11 -126.3(3) .
C2 C1 C10 C11 52.6(4) .
N1 C1 C10 C15 54.8(4) .
C2 C1 C10 C15 -126.2(3) .
C15 C10 C11 C12 -0.3(4) .
C1 C10 C11 C12 -179.3(2) .
C15 C10 C11 P1 -174.8(2) .
C1 C10 C11 P1 6.3(4) .
C10 C11 C12 C13 1.6(4) .
P1 C11 C12 C13 177.1(2) .
C10 C11 C12 C16 -173.9(2) .
P1 C11 C12 C16 1.6(3) .
C11 C12 C13 C14 -1.9(4) .
C16 C12 C13 C14 172.9(3) .
C12 C13 C14 C15 1.1(4) .
C13 C14 C15 C10 0.2(4) .
C11 C10 C15 C14 -0.5(4) .
C1 C10 C15 C14 178.4(3) .
C13 C12 C16 C17 -172.9(3) .
C11 C12 C16 C17 2.2(3) .
C13 C12 C16 C18 4.8(4) .
C11 C12 C16 C18 179.8(2) .
C18 C16 C17 C24 1.5(5) .
C12 C16 C17 C24 178.9(2) .
C18 C16 C17 P1 177.8(2) .
C12 C16 C17 P1 -4.9(3) .
C10 C11 P1 O2 46.0(3) .
C12 C11 P1 O2 -128.98(18) .
C10 C11 P1 C30 -82.3(3) .
C12 C11 P1 C30 102.8(2) .
C10 C11 P1 C17 171.3(3) .
C12 C11 P1 C17 -3.6(2) .
C16 C17 P1 O2 129.99(19) .
C24 C17 P1 O2 -53.3(2) .
C16 C17 P1 C11 4.9(2) .
C24 C17 P1 C11 -178.4(2) .
C16 C17 P1 C30 -105.4(2) .
C24 C17 P1 C30 71.3(2) .
C17 C16 C18 C23 55.8(4) .
C12 C16 C18 C23 -121.5(3) .
C17 C16 C18 C19 -125.1(3) .
C12 C16 C18 C19 57.6(3) .
C23 C18 C19 C20 0.4(4) .
C16 C18 C19 C20 -178.8(3) .
C18 C19 C20 C21 -1.0(4) .
C19 C20 C21 C22 1.0(4) .
C20 C21 C22 C23 -0.3(4) .
C19 C18 C23 C22 0.3(4) .
C16 C18 C23 C22 179.5(3) .
C21 C22 C23 C18 -0.4(4) .
C16 C17 C24 C29 -150.6(3) .
P1 C17 C24 C29 33.6(3) .
C16 C17 C24 C25 30.3(4) .
P1 C17 C24 C25 -145.6(2) .
C29 C24 C25 C26 0.8(4) .
C17 C24 C25 C26 180.0(3) .
C24 C25 C26 C27 -0.8(4) .
C25 C26 C27 C28 0.0(4) .
C26 C27 C28 C29 0.9(4) .
C27 C28 C29 C24 -0.9(4) .
C25 C24 C29 C28 0.0(4) .
C17 C24 C29 C28 -179.1(3) .
O2 P1 C30 C35 -173.8(2) .
C11 P1 C30 C35 -41.6(3) .
C17 P1 C30 C35 56.9(2) .
O2 P1 C30 C31 3.9(3) .
C11 P1 C30 C31 136.2(2) .
C17 P1 C30 C31 -125.4(2) .
C35 C30 C31 C32 -0.7(4) .
P1 C30 C31 C32 -178.4(2) .
C30 C31 C32 C33 0.7(4) .
C31 C32 C33 C34 -0.5(4) .
C32 C33 C34 C35 0.4(4) .
C31 C30 C35 C34 0.5(4) .
P1 C30 C35 C34 178.2(2) .
C33 C34 C35 C30 -0.3(4) .
C6 C5 C36 C41 -78.9(4) .
C4 C5 C36 C41 100.5(3) .
C6 C5 C36 C37 103.3(3) .
C4 C5 C36 C37 -77.4(3) .
C41 C36 C37 C38 -0.5(4) .
C5 C36 C37 C38 177.4(3) .
C41 C36 C37 C42 179.3(3) .
C5 C36 C37 C42 -2.9(4) .
C36 C37 C38 C39 0.4(5) .
C42 C37 C38 C39 -179.4(3) .
C37 C38 C39 C40 0.7(5) .
C37 C38 C39 C43 -177.4(3) .
C38 C39 C40 C41 -1.7(5) .
C43 C39 C40 C41 176.3(3) .
C37 C36 C41 C40 -0.4(4) .
C5 C36 C41 C40 -178.3(3) .
C37 C36 C41 C44 178.0(3) .
C5 C36 C41 C44 0.2(4) .
C39 C40 C41 C36 1.6(4) .
C39 C40 C41 C44 -176.9(3) .
N2 C9 C45 C46 -115.8(3) .
C8 C9 C45 C46 55.3(4) .
N2 C9 C45 C50 61.1(4) .
C8 C9 C45 C50 -127.8(3) .
C50 C45 C46 C47 -7.0(4) .
C9 C45 C46 C47 170.1(2) .
C50 C45 C46 P2 174.2(2) .
C9 C45 C46 P2 -8.6(4) .
C45 C46 C47 C48 8.7(4) .
P2 C46 C47 C48 -172.2(2) .
C45 C46 C47 C51 -170.5(2) .
P2 C46 C47 C51 8.5(3) .
C46 C47 C48 C49 -3.8(4) .
C51 C47 C48 C49 175.3(2) .
C47 C48 C49 C50 -2.6(4) .
C48 C49 C50 C45 4.2(4) .
C46 C45 C50 C49 0.6(4) .
C9 C45 C50 C49 -176.4(3) .
C48 C47 C51 C52 175.0(3) .
C46 C47 C51 C52 -5.9(3) .
C48 C47 C51 C53 -4.7(4) .
C46 C47 C51 C53 174.4(2) .
C53 C51 C52 C59 -4.5(5) .
C47 C51 C52 C59 175.9(3) .
C53 C51 C52 P2 179.7(2) .
C47 C51 C52 P2 0.1(3) .
C45 C46 P2 O3 -69.6(3) .
C47 C46 P2 O3 111.5(2) .
C45 C46 P2 C65 62.3(3) .
C47 C46 P2 C65 -116.6(2) .
C45 C46 P2 C52 171.8(3) .
C47 C46 P2 C52 -7.1(2) .
C51 C52 P2 O3 -118.0(2) .
C59 C52 P2 O3 65.8(2) .
C51 C52 P2 C65 116.2(2) .
C59 C52 P2 C65 -60.1(2) .
C51 C52 P2 C46 4.1(2) .
C59 C52 P2 C46 -172.1(2) .
C52 C51 C53 C58 -57.2(4) .
C47 C51 C53 C58 122.5(3) .
C52 C51 C53 C54 125.7(3) .
C47 C51 C53 C54 -54.6(3) .
C58 C53 C54 C55 -0.2(4) .
C51 C53 C54 C55 177.1(3) .
C53 C54 C55 C56 -0.7(4) .
C54 C55 C56 C57 1.0(4) .
C55 C56 C57 C58 -0.5(4) .
C54 C53 C58 C57 0.8(4) .
C51 C53 C58 C57 -176.4(3) .
C56 C57 C58 C53 -0.4(4) .
C51 C52 C59 C60 -57.5(4) .
P2 C52 C59 C60 117.9(3) .
C51 C52 C59 C64 127.8(3) .
P2 C52 C59 C64 -56.8(3) .
C64 C59 C60 C61 -0.2(4) .
C52 C59 C60 C61 -175.0(3) .
C59 C60 C61 C62 -0.3(5) .
C60 C61 C62 C63 0.2(5) .
C61 C62 C63 C64 0.4(5) .
C60 C59 C64 C63 0.9(4) .
C52 C59 C64 C63 175.7(3) .
C62 C63 C64 C59 -1.0(5) .
O3 P2 C65 C70 158.9(2) .
C46 P2 C65 C70 24.6(3) .
C52 P2 C65 C70 -74.9(3) .
O3 P2 C65 C66 -23.2(3) .
C46 P2 C65 C66 -157.5(2) .
C52 P2 C65 C66 103.0(3) .
C70 C65 C66 C67 2.1(5) .
P2 C65 C66 C67 -175.8(2) .
C65 C66 C67 C68 -1.3(5) .
C66 C67 C68 C69 -0.6(5) .
C67 C68 C69 C70 1.5(5) .
C66 C65 C70 C69 -1.2(5) .
P2 C65 C70 C69 176.7(3) .
C68 C69 C70 C65 -0.6(5) .
C71 C72 O5 C74 171.8(18) .
C72 O5 C74 C73 74(2) .
C73 C73 C74 O5 -170(2) 2_655
C73 C73 O6 C75 -152(2) 2_655
C76 C73 O6 C75 171(3) .
C72 C75 O6 C73 90(2) .
