#------------------------------------------------------------------------------
#$Date: 2020-11-06 13:30:32 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/83/1558314.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_1558314
loop_
_publ_author_name
'Labella, Jorge'
'Durán-Sampedro, Gonzalo'
'Martínez-Díaz, M. Victoria'
'Torres, Tomás'
_publ_section_title
;
 Annulative π-extension of BODIPYs made easy via gold(i)-catalyzed
 cycloisomerization
;
_journal_issue                   39
_journal_name_full               'Chemical Science'
_journal_page_first              10778
_journal_page_last               10785
_journal_paper_doi               10.1039/D0SC01054E
_journal_volume                  11
_journal_year                    2020
_chemical_formula_sum            'C48 H37 B F2 N2 O2'
_chemical_formula_weight         722.60
_chemical_name_common            JL363-68_200K
_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
_audit_update_record
;
2020-02-20 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                111.599(3)
_cell_angle_beta                 95.542(3)
_cell_angle_gamma                94.737(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4833(5)
_cell_length_b                   14.4445(10)
_cell_length_c                   19.1563(10)
_cell_measurement_reflns_used    3919
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      20.7423
_cell_measurement_theta_min      2.8300
_cell_volume                     1900.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31803
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.15
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'intense purple'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.351
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     589
_refine_ls_number_reflns         6928
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0528
_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)+(0.1022P)²+0.0087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1859
_reflns_number_gt                4056
_reflns_number_total             6928
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc01054e2.cif
_cod_data_source_block           02878JorgeLabella
_cod_depositor_comments
'Adding full bibliography for 1558304--1558314.cif.'
_cod_database_code               1558314
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.2703(4) 0.5017(2) 0.08471(16) 0.0370(7) Uani d . . . 1.0 . .
C C1 -0.0220(3) 0.3801(2) 0.06528(14) 0.0372(6) Uani d . . . 1.0 . .
H H1 -0.0722 0.3823 0.0185 0.045 Uiso calc U . R 1.0 . .
C C2 -0.1023(3) 0.3221(2) 0.10151(14) 0.0364(6) Uani d . . . 1.0 . .
C C3 0.0124(3) 0.3417(2) 0.16763(14) 0.0394(6) Uani d . . . 1.0 . .
H H3 -0.0055 0.3134 0.2044 0.047 Uiso calc U . R 1.0 . .
C C4 0.1593(3) 0.4104(2) 0.17109(13) 0.0346(6) Uani d . . . 1.0 . .
C C5 0.3020(3) 0.46029(19) 0.22837(13) 0.0327(6) Uani d . . . 1.0 . .
C C6 0.4322(3) 0.52730(19) 0.21936(13) 0.0316(6) Uani d . . . 1.0 . .
C C7 0.5835(3) 0.58793(18) 0.26830(14) 0.0344(6) Uani d . . . 1.0 . .
H H7 0.6177 0.594 0.319 0.041 Uiso calc U . R 1.0 . .
C C8 0.6745(3) 0.63750(19) 0.23014(14) 0.0350(6) Uani d . . . 1.0 . .
C C9 0.5744(3) 0.60632(19) 0.15810(14) 0.0374(6) Uani d . . . 1.0 . .
H H9 0.6058 0.6284 0.1194 0.045 Uiso calc U . R 1.0 . .
C C10 -0.2808(3) 0.2608(2) 0.07646(13) 0.0386(6) Uani d . . . 1.0 . .
C C11 -0.4252(3) 0.2964(2) 0.04770(14) 0.0436(7) Uani d . . . 1.0 . .
H H11 -0.4065 0.3585 0.0414 0.052 Uiso calc U . R 1.0 . .
C C12 -0.5965(4) 0.2423(2) 0.02799(17) 0.0543(8) Uani d . . . 1.0 . .
H H12 -0.6937 0.2671 0.0076 0.065 Uiso calc U . R 1.0 . .
C C13 -0.6263(4) 0.1532(2) 0.03774(17) 0.0590(9) Uani d . . . 1.0 . .
H H13 -0.7448 0.1177 0.0259 0.071 Uiso calc U . R 1.0 . .
C C14 -0.4844(4) 0.1155(2) 0.06466(16) 0.0534(8) Uani d . . . 1.0 . .
H H14 -0.5053 0.053 0.0704 0.064 Uiso calc U . R 1.0 . .
C C15 -0.3110(3) 0.1673(2) 0.08359(14) 0.0414(7) Uani d . . . 1.0 . .
C C16 -0.1656(4) 0.1222(2) 0.10726(15) 0.0490(7) Uani d . . . 1.0 . .
C C17 -0.0450(4) 0.0809(2) 0.12361(16) 0.0529(8) Uani d . . D 1.0 . .
C C18A 0.1037(5) 0.0479(4) 0.1486(3) 0.047(2) Uani d . P DG 0.533(6) A 1
C C19A 0.1480(6) -0.0451(4) 0.1037(2) 0.0483(19) Uani d . P G 0.533(6) A 1
H H19A 0.0756 -0.0837 0.0566 0.058 Uiso calc U P R 0.533(6) A 1
C C20A 0.2984(8) -0.0817(4) 0.1276(2) 0.0486(19) Uani d . P G 0.533(6) A 1
H H20A 0.3286 -0.1453 0.0969 0.058 Uiso calc U P R 0.533(6) A 1
C C21A 0.4043(6) -0.0253(4) 0.1965(3) 0.050(2) Uani d . P DG 0.533(6) A 1
C C22A 0.3600(6) 0.0676(4) 0.2414(3) 0.0632(19) Uani d . P G 0.533(6) A 1
H H22A 0.4324 0.1062 0.2884 0.076 Uiso calc U P R 0.533(6) A 1
C C23A 0.2097(7) 0.1042(3) 0.2174(3) 0.0558(18) Uani d . P G 0.533(6) A 1
H H23A 0.1794 0.1678 0.2481 0.067 Uiso calc U P R 0.533(6) A 1
O O1A 0.5501(6) -0.0547(4) 0.2250(3) 0.0783(19) Uani d . P D 0.533(6) A 1
C C24A 0.6291(18) -0.1333(10) 0.1748(8) 0.086(5) Uani d . P D 0.533(6) A 1
H H24A 0.5489 -0.1965 0.1601 0.128 Uiso calc U P R 0.533(6) A 1
H H24B 0.746 -0.139 0.1997 0.128 Uiso calc U P R 0.533(6) A 1
H H24C 0.6474 -0.1193 0.1295 0.128 Uiso calc U P R 0.533(6) A 1
C C18B 0.1012(6) 0.0167(5) 0.1362(4) 0.051(3) Uani d . P DG 0.467(6) A 2
C C19B 0.0823(7) -0.0874(5) 0.1024(3) 0.053(2) Uani d . P G 0.467(6) A 2
H H19B -0.0281 -0.1234 0.0722 0.064 Uiso calc U P R 0.467(6) A 2
C C20B 0.2251(8) -0.1389(4) 0.1127(3) 0.059(2) Uani d . P G 0.467(6) A 2
H H20B 0.2122 -0.2101 0.0896 0.071 Uiso calc U P R 0.467(6) A 2
C C21B 0.3866(6) -0.0863(5) 0.1568(4) 0.049(2) Uani d . P DG 0.467(6) A 2
C C22B 0.4055(5) 0.0178(5) 0.1906(4) 0.053(3) Uani d . P G 0.467(6) A 2
H H22B 0.5159 0.0538 0.2208 0.064 Uiso calc U P R 0.467(6) A 2
C C23B 0.2628(7) 0.0694(4) 0.1803(4) 0.058(2) Uani d . P G 0.467(6) A 2
H H23B 0.2757 0.1405 0.2034 0.07 Uiso calc U P R 0.467(6) A 2
C C24B 0.7011(16) -0.0937(12) 0.1909(11) 0.076(4) Uani d . P D 0.467(6) A 2
H H24D 0.7425 -0.0668 0.1543 0.113 Uiso calc U P R 0.467(6) A 2
H H24E 0.7806 -0.1418 0.1965 0.113 Uiso calc U P R 0.467(6) A 2
H H24F 0.7044 -0.0386 0.24 0.113 Uiso calc U P R 0.467(6) A 2
O O1B 0.5208(9) -0.1427(6) 0.1645(4) 0.066(2) Uani d . P D 0.467(6) A 2
C C25 0.3071(3) 0.44351(19) 0.30081(13) 0.0337(6) Uani d . . . 1.0 . .
C C26 0.1874(3) 0.4878(2) 0.35118(14) 0.0396(6) Uani d . . . 1.0 . .
C C27 0.1895(4) 0.4702(2) 0.41761(15) 0.0470(7) Uani d . . . 1.0 . .
H H27 0.1094 0.501 0.4523 0.056 Uiso calc U . R 1.0 . .
C C28 0.3040(4) 0.4095(2) 0.43502(15) 0.0461(7) Uani d . . . 1.0 . .
C C29 0.4211(4) 0.3657(2) 0.38390(15) 0.0452(7) Uani d . . . 1.0 . .
H H29 0.5002 0.3233 0.395 0.054 Uiso calc U . R 1.0 . .
C C30 0.4262(3) 0.3821(2) 0.31699(14) 0.0374(6) Uani d . . . 1.0 . .
C C31 0.0568(4) 0.5531(3) 0.33427(16) 0.0566(8) Uani d . . . 1.0 . .
H H31A -0.0416 0.511 0.295 0.085 Uiso calc U . R 1.0 . .
H H31B 0.1203 0.6004 0.3164 0.085 Uiso calc U . R 1.0 . .
H H31C 0.0066 0.5905 0.3804 0.085 Uiso calc U . R 1.0 . .
C C32 0.3025(5) 0.3922(3) 0.50832(17) 0.0663(10) Uani d . . . 1.0 . .
H H32A 0.2434 0.4444 0.5437 0.099 Uiso calc U . R 1.0 . .
H H32B 0.4271 0.3949 0.5307 0.099 Uiso calc U . R 1.0 . .
H H32C 0.2359 0.3262 0.4979 0.099 Uiso calc U . R 1.0 . .
C C33 0.5557(4) 0.3330(2) 0.26350(17) 0.0527(8) Uani d . . . 1.0 . .
H H33A 0.6151 0.286 0.2811 0.079 Uiso calc U . R 1.0 . .
H H33B 0.6473 0.3845 0.2619 0.079 Uiso calc U . R 1.0 . .
H H33C 0.4891 0.2964 0.2126 0.079 Uiso calc U . R 1.0 . .
C C34 0.8452(4) 0.7067(2) 0.25673(16) 0.0454(7) Uani d . . . 1.0 . .
C C35 0.9753(4) 0.6967(2) 0.20923(19) 0.0557(8) Uani d . . . 1.0 . .
H H35 0.9517 0.6463 0.1596 0.067 Uiso calc U . R 1.0 . .
C C36 1.1386(5) 0.7574(3) 0.2317(2) 0.0837(12) Uani d . . . 1.0 . .
H H36 1.2258 0.7488 0.1976 0.1 Uiso calc U . R 1.0 . .
C C37 1.1748(6) 0.8294(4) 0.3020(3) 0.1148(17) Uani d . . . 1.0 . .
H H37 1.288 0.871 0.3178 0.138 Uiso calc U . R 1.0 . .
C C38 1.0476(6) 0.8423(3) 0.3509(2) 0.1006(15) Uani d . . . 1.0 . .
H H38 1.0741 0.8931 0.4003 0.121 Uiso calc U . R 1.0 . .
C C39 0.8803(5) 0.7823(2) 0.32952(18) 0.0608(9) Uani d . . . 1.0 . .
C C40 0.7492(5) 0.7991(2) 0.38168(19) 0.0654(9) Uani d . . . 1.0 . .
C C41 0.6438(5) 0.8167(2) 0.42673(19) 0.0675(10) Uani d . . D 1.0 . .
C C42A 0.5390(11) 0.8362(6) 0.4791(3) 0.067(3) Uani d . P DG 0.518(5) B 1
C C43A 0.5938(10) 0.9049(6) 0.5527(4) 0.115(4) Uani d . P G 0.518(5) B 1
H H43A 0.7147 0.9376 0.5672 0.138 Uiso calc U P R 0.518(5) B 1
C C44A 0.4719(12) 0.9258(6) 0.6052(3) 0.136(5) Uani d . P G 0.518(5) B 1
H H44A 0.5094 0.9727 0.6555 0.163 Uiso calc U P R 0.518(5) B 1
C C45A 0.2951(10) 0.8779(6) 0.5840(4) 0.097(4) Uani d . P DG 0.518(5) B 1
C C46A 0.2402(9) 0.8092(6) 0.5104(4) 0.098(4) Uani d . P G 0.518(5) B 1
H H46A 0.1193 0.7765 0.4959 0.118 Uiso calc U P R 0.518(5) B 1
C C47A 0.3622(11) 0.7884(5) 0.4580(3) 0.081(4) Uani d . P G 0.518(5) B 1
H H47A 0.3247 0.7414 0.4077 0.098 Uiso calc U P R 0.518(5) B 1
O O2A 0.1704(10) 0.9052(6) 0.6332(3) 0.138(2) Uani d . P D 0.518(5) B 1
C C48A 0.001(2) 0.8537(18) 0.6200(11) 0.244(8) Uani d . P D 0.518(5) B 1
H H48A -0.0726 0.865 0.5794 0.366 Uiso calc U P R 0.518(5) B 1
H H48B -0.0564 0.8773 0.6663 0.366 Uiso calc U P R 0.518(5) B 1
H H48C 0.0097 0.7818 0.6049 0.366 Uiso calc U P R 0.518(5) B 1
C C42B 0.4911(9) 0.8277(5) 0.4772(3) 0.054(3) Uani d . P DG 0.482(5) B 2
C C43B 0.4808(8) 0.9190(4) 0.5351(3) 0.068(2) Uani d . P G 0.482(5) B 2
H H43B 0.5669 0.9755 0.5435 0.082 Uiso calc U P R 0.482(5) B 2
C C44B 0.3444(10) 0.9278(5) 0.5806(3) 0.086(4) Uani d . P G 0.482(5) B 2
H H44B 0.3373 0.9903 0.6202 0.103 Uiso calc U P R 0.482(5) B 2
C C45B 0.2183(9) 0.8453(6) 0.5684(4) 0.084(4) Uani d . P DG 0.482(5) B 2
C C46B 0.2286(9) 0.7539(5) 0.5105(4) 0.078(3) Uani d . P G 0.482(5) B 2
H H46B 0.1425 0.6975 0.5021 0.094 Uiso calc U P R 0.482(5) B 2
C C47B 0.3650(11) 0.7451(4) 0.4649(3) 0.067(3) Uani d . P G 0.482(5) B 2
H H47B 0.372 0.6827 0.4254 0.08 Uiso calc U P R 0.482(5) B 2
O O2B 0.0657(13) 0.8408(7) 0.6070(5) 0.138(2) Uani d . P D 0.482(5) B 2
C C48B 0.064(2) 0.9198(15) 0.6762(8) 0.244(8) Uani d . P D 0.482(5) B 2
H H48D 0.1881 0.9414 0.7031 0.366 Uiso calc U P R 0.482(5) B 2
H H48E -0.0123 0.8974 0.7071 0.366 Uiso calc U P R 0.482(5) B 2
H H48F 0.0168 0.9761 0.6671 0.366 Uiso calc U P R 0.482(5) B 2
F F1 0.1890(2) 0.58134(12) 0.07839(9) 0.0571(5) Uani d . . . 1.0 . .
F F2 0.3285(2) 0.44903(13) 0.01694(8) 0.0546(5) Uani d . . . 1.0 . .
N N1 0.1355(3) 0.43204(16) 0.10580(11) 0.0342(5) Uani d . . . 1.0 . .
N N2 0.4286(3) 0.54148(15) 0.15074(10) 0.0328(5) Uani d . . . 1.0 . .
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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 B1 F1 . . 109.0(2) ?
F2 B1 N2 . . 111.7(2) ?
F1 B1 N2 . . 109.6(2) ?
F2 B1 N1 . . 110.2(2) ?
F1 B1 N1 . . 110.5(2) ?
N2 B1 N1 . . 105.86(19) ?
N1 C1 C2 . . 110.7(2) ?
N1 C1 H1 . . 124.7 ?
C2 C1 H1 . . 124.7 ?
C3 C2 C1 . . 106.0(2) ?
C3 C2 C10 . . 127.8(2) ?
C1 C2 C10 . . 126.0(2) ?
C2 C3 C4 . . 108.2(2) ?
C2 C3 H3 . . 125.9 ?
C4 C3 H3 . . 125.9 ?
C5 C4 N1 . . 121.1(2) ?
C5 C4 C3 . . 130.7(2) ?
N1 C4 C3 . . 107.9(2) ?
C6 C5 C4 . . 120.5(2) ?
C6 C5 C25 . . 120.9(2) ?
C4 C5 C25 . . 118.6(2) ?
C5 C6 C7 . . 131.4(2) ?
C5 C6 N2 . . 120.7(2) ?
C7 C6 N2 . . 107.88(19) ?
C8 C7 C6 . . 108.2(2) ?
C8 C7 H7 . . 125.9 ?
C6 C7 H7 . . 125.9 ?
C7 C8 C9 . . 105.8(2) ?
C7 C8 C34 . . 128.6(2) ?
C9 C8 C34 . . 125.6(2) ?
N2 C9 C8 . . 111.3(2) ?
N2 C9 H9 . . 124.3 ?
C8 C9 H9 . . 124.3 ?
C11 C10 C15 . . 118.6(2) ?
C11 C10 C2 . . 120.0(2) ?
C15 C10 C2 . . 121.4(2) ?
C12 C11 C10 . . 120.7(3) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C13 C12 C11 . . 120.4(3) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 119.9(3) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
C13 C14 C15 . . 120.8(3) ?
C13 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C14 C15 C10 . . 119.5(3) ?
C14 C15 C16 . . 118.8(3) ?
C10 C15 C16 . . 121.7(2) ?
C17 C16 C15 . . 176.9(3) ?
C16 C17 C18A . . 171.6(4) ?
C16 C17 C18B . . 173.2(4) ?
C17 C18A C19A . . 118.4(4) ?
C17 C18A C23A . . 121.6(4) ?
C19A C18A C23A . . 120.0 ?
C20A C19A C18A . . 120.0 ?
C20A C19A H19A . . 120.0 ?
C18A C19A H19A . . 120.0 ?
C21A C20A C19A . . 120.0 ?
C21A C20A H20A . . 120.0 ?
C19A C20A H20A . . 120.0 ?
O1A C21A C20A . . 124.5(4) ?
O1A C21A C22A . . 115.5(4) ?
C20A C21A C22A . . 120.0 ?
C21A C22A C23A . . 120.0 ?
C21A C22A H22A . . 120.0 ?
C23A C22A H22A . . 120.0 ?
C22A C23A C18A . . 120.0 ?
C22A C23A H23A . . 120.0 ?
C18A C23A H23A . . 120.0 ?
C21A O1A C24A . . 117.5(7) ?
O1A C24A H24A . . 109.5 ?
O1A C24A H24B . . 109.5 ?
H24A C24A H24B . . 109.5 ?
O1A C24A H24C . . 109.5 ?
H24A C24A H24C . . 109.5 ?
H24B C24A H24C . . 109.5 ?
C19B C18B C23B . . 120.0 ?
C19B C18B C17 . . 123.7(4) ?
C23B C18B C17 . . 116.2(4) ?
C18B C19B C20B . . 120.0 ?
C18B C19B H19B . . 120.0 ?
C20B C19B H19B . . 120.0 ?
C21B C20B C19B . . 120.0 ?
C21B C20B H20B . . 120.0 ?
C19B C20B H20B . . 120.0 ?
O1B C21B C22B . . 123.6(5) ?
O1B C21B C20B . . 116.4(5) ?
C22B C21B C20B . . 120.0 ?
C23B C22B C21B . . 120.0 ?
C23B C22B H22B . . 120.0 ?
C21B C22B H22B . . 120.0 ?
C22B C23B C18B . . 120.0 ?
C22B C23B H23B . . 120.0 ?
C18B C23B H23B . . 120.0 ?
O1B C24B H24D . . 109.5 ?
O1B C24B H24E . . 109.5 ?
H24D C24B H24E . . 109.5 ?
O1B C24B H24F . . 109.5 ?
H24D C24B H24F . . 109.5 ?
H24E C24B H24F . . 109.5 ?
C21B O1B C24B . . 118.3(10) ?
C26 C25 C30 . . 120.6(2) ?
C26 C25 C5 . . 118.8(2) ?
C30 C25 C5 . . 120.6(2) ?
C27 C26 C25 . . 118.7(2) ?
C27 C26 C31 . . 120.0(2) ?
C25 C26 C31 . . 121.3(2) ?
C28 C27 C26 . . 122.2(2) ?
C28 C27 H27 . . 118.9 ?
C26 C27 H27 . . 118.9 ?
C27 C28 C29 . . 118.1(2) ?
C27 C28 C32 . . 120.6(3) ?
C29 C28 C32 . . 121.3(3) ?
C28 C29 C30 . . 122.0(3) ?
C28 C29 H29 . . 119.0 ?
C30 C29 H29 . . 119.0 ?
C29 C30 C25 . . 118.4(2) ?
C29 C30 C33 . . 119.9(2) ?
C25 C30 C33 . . 121.7(2) ?
C26 C31 H31A . . 109.5 ?
C26 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C26 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C28 C32 H32A . . 109.5 ?
C28 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C28 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C30 C33 H33A . . 109.5 ?
C30 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C30 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C35 C34 C39 . . 118.6(3) ?
C35 C34 C8 . . 119.4(3) ?
C39 C34 C8 . . 122.0(3) ?
C36 C35 C34 . . 121.9(3) ?
C36 C35 H35 . . 119.1 ?
C34 C35 H35 . . 119.1 ?
C37 C36 C35 . . 120.0(4) ?
C37 C36 H36 . . 120.0 ?
C35 C36 H36 . . 120.0 ?
C36 C37 C38 . . 119.8(4) ?
C36 C37 H37 . . 120.1 ?
C38 C37 H37 . . 120.1 ?
C37 C38 C39 . . 121.4(4) ?
C37 C38 H38 . . 119.3 ?
C39 C38 H38 . . 119.3 ?
C38 C39 C34 . . 118.3(3) ?
C38 C39 C40 . . 119.9(3) ?
C34 C39 C40 . . 121.8(3) ?
C41 C40 C39 . . 177.4(3) ?
C40 C41 C42A . . 176.0(5) ?
C40 C41 C42B . . 172.5(4) ?
C41 C42A C43A . . 123.0(6) ?
C41 C42A C47A . . 116.9(6) ?
C43A C42A C47A . . 120.0 ?
C44A C43A C42A . . 120.0 ?
C44A C43A H43A . . 120.0 ?
C42A C43A H43A . . 120.0 ?
C43A C44A C45A . . 120.0 ?
C43A C44A H44A . . 120.0 ?
C45A C44A H44A . . 120.0 ?
O2A C45A C44A . . 120.0(6) ?
O2A C45A C46A . . 119.7(6) ?
C44A C45A C46A . . 120.0 ?
C47A C46A C45A . . 120.0 ?
C47A C46A H46A . . 120.0 ?
C45A C46A H46A . . 120.0 ?
C46A C47A C42A . . 120.0 ?
C46A C47A H47A . . 120.0 ?
C42A C47A H47A . . 120.0 ?
C45A O2A C48A . . 123.2(9) ?
O2A C48A H48A . . 109.5 ?
O2A C48A H48B . . 109.5 ?
H48A C48A H48B . . 109.5 ?
O2A C48A H48C . . 109.5 ?
H48A C48A H48C . . 109.5 ?
H48B C48A H48C . . 109.5 ?
C43B C42B C47B . . 120.0 ?
C43B C42B C41 . . 120.4(4) ?
C47B C42B C41 . . 119.6(4) ?
C42B C43B C44B . . 120.0 ?
C42B C43B H43B . . 120.0 ?
C44B C43B H43B . . 120.0 ?
C45B C44B C43B . . 120.0 ?
C45B C44B H44B . . 120.0 ?
C43B C44B H44B . . 120.0 ?
C46B C45B C44B . . 120.0 ?
C46B C45B O2B . . 111.9(6) ?
C44B C45B O2B . . 128.0(6) ?
C45B C46B C47B . . 120.0 ?
C45B C46B H46B . . 120.0 ?
C47B C46B H46B . . 120.0 ?
C46B C47B C42B . . 120.0 ?
C46B C47B H47B . . 120.0 ?
C42B C47B H47B . . 120.0 ?
C48B O2B C45B . . 116.6(10) ?
O2B C48B H48D . . 109.5 ?
O2B C48B H48E . . 109.5 ?
H48D C48B H48E . . 109.5 ?
O2B C48B H48F . . 109.5 ?
H48D C48B H48F . . 109.5 ?
H48E C48B H48F . . 109.5 ?
C1 N1 C4 . . 107.21(19) ?
C1 N1 B1 . . 127.4(2) ?
C4 N1 B1 . . 125.4(2) ?
C9 N2 C6 . . 106.8(2) ?
C9 N2 B1 . . 127.1(2) ?
C6 N2 B1 . . 125.49(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F2 . 1.375(3) ?
B1 F1 . 1.383(3) ?
B1 N2 . 1.548(3) ?
B1 N1 . 1.550(3) ?
C1 N1 . 1.343(3) ?
C1 C2 . 1.404(3) ?
C1 H1 . 0.95 ?
C2 C3 . 1.381(3) ?
C2 C10 . 1.472(3) ?
C3 C4 . 1.399(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.388(3) ?
C4 N1 . 1.395(3) ?
C5 C6 . 1.384(3) ?
C5 C25 . 1.492(3) ?
C6 C7 . 1.398(3) ?
C6 N2 . 1.401(3) ?
C7 C8 . 1.383(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.399(3) ?
C8 C34 . 1.476(4) ?
C9 N2 . 1.338(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.386(4) ?
C10 C15 . 1.408(4) ?
C11 C12 . 1.385(4) ?
C11 H11 . 0.95 ?
C12 C13 . 1.370(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.374(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.387(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.434(4) ?
C16 C17 . 1.200(4) ?
C17 C18A . 1.360(4) ?
C17 C18B . 1.548(5) ?
C18A C19A . 1.39 ?
C18A C23A . 1.39 ?
C19A C20A . 1.39 ?
C19A H19A . 0.95 ?
C20A C21A . 1.39 ?
C20A H20A . 0.95 ?
C21A O1A . 1.342(5) ?
C21A C22A . 1.39 ?
C22A C23A . 1.39 ?
C22A H22A . 0.95 ?
C23A H23A . 0.95 ?
O1A C24A . 1.408(12) ?
C24A H24A . 0.98 ?
C24A H24B . 0.98 ?
C24A H24C . 0.98 ?
C18B C19B . 1.39 ?
C18B C23B . 1.39 ?
C19B C20B . 1.39 ?
C19B H19B . 0.95 ?
C20B C21B . 1.39 ?
C20B H20B . 0.95 ?
C21B O1B . 1.374(7) ?
C21B C22B . 1.39 ?
C22B C23B . 1.39 ?
C22B H22B . 0.95 ?
C23B H23B . 0.95 ?
C24B O1B . 1.423(12) ?
C24B H24D . 0.98 ?
C24B H24E . 0.98 ?
C24B H24F . 0.98 ?
C25 C26 . 1.397(3) ?
C25 C30 . 1.398(3) ?
C26 C27 . 1.386(3) ?
C26 C31 . 1.505(4) ?
C27 C28 . 1.378(4) ?
C27 H27 . 0.95 ?
C28 C29 . 1.388(4) ?
C28 C32 . 1.515(4) ?
C29 C30 . 1.390(3) ?
C29 H29 . 0.95 ?
C30 C33 . 1.505(4) ?
C31 H31A . 0.98 ?
C31 H31B . 0.98 ?
C31 H31C . 0.98 ?
C32 H32A . 0.98 ?
C32 H32B . 0.98 ?
C32 H32C . 0.98 ?
C33 H33A . 0.98 ?
C33 H33B . 0.98 ?
C33 H33C . 0.98 ?
C34 C35 . 1.376(4) ?
C34 C39 . 1.402(4) ?
C35 C36 . 1.376(4) ?
C35 H35 . 0.95 ?
C36 C37 . 1.350(6) ?
C36 H36 . 0.95 ?
C37 C38 . 1.375(6) ?
C37 H37 . 0.95 ?
C38 C39 . 1.394(5) ?
C38 H38 . 0.95 ?
C39 C40 . 1.439(5) ?
C40 C41 . 1.197(5) ?
C41 C42A . 1.297(6) ?
C41 C42B . 1.548(6) ?
C42A C43A . 1.39 ?
C42A C47A . 1.39 ?
C43A C44A . 1.39 ?
C43A H43A . 0.95 ?
C44A C45A . 1.39 ?
C44A H44A . 0.95 ?
C45A O2A . 1.368(7) ?
C45A C46A . 1.39 ?
C46A C47A . 1.39 ?
C46A H46A . 0.95 ?
C47A H47A . 0.95 ?
O2A C48A . 1.369(15) ?
C48A H48A . 0.98 ?
C48A H48B . 0.98 ?
C48A H48C . 0.98 ?
C42B C43B . 1.39 ?
C42B C47B . 1.39 ?
C43B C44B . 1.39 ?
C43B H43B . 0.95 ?
C44B C45B . 1.39 ?
C44B H44B . 0.95 ?
C45B C46B . 1.39 ?
C45B O2B . 1.429(9) ?
C46B C47B . 1.39 ?
C46B H46B . 0.95 ?
C47B H47B . 0.95 ?
O2B C48B . 1.397(14) ?
C48B H48D . 0.98 ?
C48B H48E . 0.98 ?
C48B H48F . 0.98 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 F1 2_565 0.95 2.23 3.166(3) 169.1 ?
C9 H9 F2 2_665 0.95 2.55 3.317(3) 138.1 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 0.9(3) ?
N1 C1 C2 C10 . . . . 175.8(2) ?
C1 C2 C3 C4 . . . . 0.0(3) ?
C10 C2 C3 C4 . . . . -174.8(2) ?
C2 C3 C4 C5 . . . . 173.7(3) ?
C2 C3 C4 N1 . . . . -0.8(3) ?
N1 C4 C5 C6 . . . . -5.0(4) ?
C3 C4 C5 C6 . . . . -178.9(3) ?
N1 C4 C5 C25 . . . . 172.3(2) ?
C3 C4 C5 C25 . . . . -1.5(4) ?
C4 C5 C6 C7 . . . . 178.0(2) ?
C25 C5 C6 C7 . . . . 0.7(4) ?
C4 C5 C6 N2 . . . . -3.9(4) ?
C25 C5 C6 N2 . . . . 178.9(2) ?
C5 C6 C7 C8 . . . . 177.1(3) ?
N2 C6 C7 C8 . . . . -1.2(3) ?
C6 C7 C8 C9 . . . . 0.6(3) ?
C6 C7 C8 C34 . . . . -177.5(2) ?
C7 C8 C9 N2 . . . . 0.2(3) ?
C34 C8 C9 N2 . . . . 178.4(2) ?
C3 C2 C10 C11 . . . . 133.9(3) ?
C1 C2 C10 C11 . . . . -39.8(4) ?
C3 C2 C10 C15 . . . . -43.7(4) ?
C1 C2 C10 C15 . . . . 142.6(3) ?
C15 C10 C11 C12 . . . . 1.4(4) ?
C2 C10 C11 C12 . . . . -176.2(2) ?
C10 C11 C12 C13 . . . . 1.0(4) ?
C11 C12 C13 C14 . . . . -2.4(4) ?
C12 C13 C14 C15 . . . . 1.3(4) ?
C13 C14 C15 C10 . . . . 1.2(4) ?
C13 C14 C15 C16 . . . . -176.4(3) ?
C11 C10 C15 C14 . . . . -2.5(4) ?
C2 C10 C15 C14 . . . . 175.1(2) ?
C11 C10 C15 C16 . . . . 175.1(2) ?
C2 C10 C15 C16 . . . . -7.3(4) ?
C17 C18A C19A C20A . . . . -179.5(4) ?
C23A C18A C19A C20A . . . . 0 ?
C18A C19A C20A C21A . . . . 0 ?
C19A C20A C21A O1A . . . . 178.9(5) ?
C19A C20A C21A C22A . . . . 0 ?
O1A C21A C22A C23A . . . . -179.0(5) ?
C20A C21A C22A C23A . . . . 0 ?
C21A C22A C23A C18A . . . . 0 ?
C17 C18A C23A C22A . . . . 179.5(4) ?
C19A C18A C23A C22A . . . . 0 ?
C20A C21A O1A C24A . . . . 17.6(9) ?
C22A C21A O1A C24A . . . . -163.4(8) ?
C23B C18B C19B C20B . . . . 0 ?
C17 C18B C19B C20B . . . . 175.7(5) ?
C18B C19B C20B C21B . . . . 0 ?
C19B C20B C21B O1B . . . . 179.7(6) ?
C19B C20B C21B C22B . . . . 0 ?
O1B C21B C22B C23B . . . . -179.7(6) ?
C20B C21B C22B C23B . . . . 0 ?
C21B C22B C23B C18B . . . . 0 ?
C19B C18B C23B C22B . . . . 0 ?
C17 C18B C23B C22B . . . . -176.0(5) ?
C22B C21B O1B C24B . . . . -17.0(14) ?
C20B C21B O1B C24B . . . . 163.3(11) ?
C6 C5 C25 C26 . . . . 103.1(3) ?
C4 C5 C25 C26 . . . . -74.2(3) ?
C6 C5 C25 C30 . . . . -78.7(3) ?
C4 C5 C25 C30 . . . . 104.0(3) ?
C30 C25 C26 C27 . . . . 0.4(4) ?
C5 C25 C26 C27 . . . . 178.5(2) ?
C30 C25 C26 C31 . . . . -179.3(2) ?
C5 C25 C26 C31 . . . . -1.1(4) ?
C25 C26 C27 C28 . . . . -0.9(4) ?
C31 C26 C27 C28 . . . . 178.8(3) ?
C26 C27 C28 C29 . . . . 0.5(4) ?
C26 C27 C28 C32 . . . . 179.9(3) ?
C27 C28 C29 C30 . . . . 0.5(4) ?
C32 C28 C29 C30 . . . . -179.0(3) ?
C28 C29 C30 C25 . . . . -0.9(4) ?
C28 C29 C30 C33 . . . . 179.9(3) ?
C26 C25 C30 C29 . . . . 0.5(4) ?
C5 C25 C30 C29 . . . . -177.6(2) ?
C26 C25 C30 C33 . . . . 179.6(2) ?
C5 C25 C30 C33 . . . . 1.5(4) ?
C7 C8 C34 C35 . . . . 135.4(3) ?
C9 C8 C34 C35 . . . . -42.4(4) ?
C7 C8 C34 C39 . . . . -44.0(4) ?
C9 C8 C34 C39 . . . . 138.2(3) ?
C39 C34 C35 C36 . . . . 1.0(5) ?
C8 C34 C35 C36 . . . . -178.4(3) ?
C34 C35 C36 C37 . . . . 0.1(6) ?
C35 C36 C37 C38 . . . . -0.6(7) ?
C36 C37 C38 C39 . . . . 0.1(8) ?
C37 C38 C39 C34 . . . . 0.9(6) ?
C37 C38 C39 C40 . . . . -178.9(4) ?
C35 C34 C39 C38 . . . . -1.4(5) ?
C8 C34 C39 C38 . . . . 177.9(3) ?
C35 C34 C39 C40 . . . . 178.4(3) ?
C8 C34 C39 C40 . . . . -2.3(4) ?
C41 C42A C43A C44A . . . . 176.9(8) ?
C47A C42A C43A C44A . . . . 0 ?
C42A C43A C44A C45A . . . . 0 ?
C43A C44A C45A O2A . . . . -173.8(10) ?
C43A C44A C45A C46A . . . . 0 ?
O2A C45A C46A C47A . . . . 173.8(9) ?
C44A C45A C46A C47A . . . . 0 ?
C45A C46A C47A C42A . . . . 0 ?
C41 C42A C47A C46A . . . . -177.1(7) ?
C43A C42A C47A C46A . . . . 0 ?
C44A C45A O2A C48A . . . . -171.8(17) ?
C46A C45A O2A C48A . . . . 14.(2) ?
C47B C42B C43B C44B . . . . 0 ?
C41 C42B C43B C44B . . . . -179.2(6) ?
C42B C43B C44B C45B . . . . 0 ?
C43B C44B C45B C46B . . . . 0 ?
C43B C44B C45B O2B . . . . -177.3(9) ?
C44B C45B C46B C47B . . . . 0 ?
O2B C45B C46B C47B . . . . 177.7(8) ?
C45B C46B C47B C42B . . . . 0 ?
C43B C42B C47B C46B . . . . 0 ?
C41 C42B C47B C46B . . . . 179.2(6) ?
C46B C45B O2B C48B . . . . 165.8(13) ?
C44B C45B O2B C48B . . . . -16.7(17) ?
C2 C1 N1 C4 . . . . -1.4(3) ?
C2 C1 N1 B1 . . . . 177.4(2) ?
C5 C4 N1 C1 . . . . -173.8(2) ?
C3 C4 N1 C1 . . . . 1.4(3) ?
C5 C4 N1 B1 . . . . 7.4(4) ?
C3 C4 N1 B1 . . . . -177.5(2) ?
F2 B1 N1 C1 . . . . -58.7(3) ?
F1 B1 N1 C1 . . . . 61.8(3) ?
N2 B1 N1 C1 . . . . -179.6(2) ?
F2 B1 N1 C4 . . . . 119.9(3) ?
F1 B1 N1 C4 . . . . -119.6(2) ?
N2 B1 N1 C4 . . . . -1.0(3) ?
C8 C9 N2 C6 . . . . -1.0(3) ?
C8 C9 N2 B1 . . . . 170.5(2) ?
C5 C6 N2 C9 . . . . -177.2(2) ?
C7 C6 N2 C9 . . . . 1.3(3) ?
C5 C6 N2 B1 . . . . 11.1(4) ?
C7 C6 N2 B1 . . . . -170.4(2) ?
F2 B1 N2 C9 . . . . 61.9(3) ?
F1 B1 N2 C9 . . . . -58.9(3) ?
N1 B1 N2 C9 . . . . -178.1(2) ?
F2 B1 N2 C6 . . . . -128.1(2) ?
F1 B1 N2 C6 . . . . 111.1(3) ?
N1 B1 N2 C6 . . . . -8.1(3) ?
