#------------------------------------------------------------------------------
#$Date: 2020-11-06 13:30:32 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/83/1558308.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_1558308
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            'C36 H29 B F2 N2'
_chemical_formula_weight         538.42
_chemical_name_common            JL376-11
_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                105.446(3)
_cell_angle_beta                 103.611(3)
_cell_angle_gamma                94.765(3)
_cell_formula_units_Z            2
_cell_length_a                   10.1937(6)
_cell_length_b                   11.0010(6)
_cell_length_c                   14.2800(7)
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      20.3272
_cell_measurement_theta_min      2.8115
_cell_volume                     1481.92(14)
_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      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0840
_diffrn_reflns_av_unetI/netI     0.0957
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21050
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.487
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1582
_refine_ls_R_factor_gt           0.0561
_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)+(0.1180P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.2279
_reflns_number_gt                2660
_reflns_number_total             5433
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc01054e2.cif
_cod_data_source_block           02815JorgeLabella
_cod_depositor_comments
'Adding full bibliography for 1558304--1558314.cif.'
_cod_database_code               1558308
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 0.3264(4) 0.7310(4) 0.2789(3) 0.0434(10) Uani d . . . 1 . .
C C1 0.4357(3) 0.9688(3) 0.3286(3) 0.0465(9) Uani d . . . 1 . .
C C2 0.5595(4) 1.0436(4) 0.3895(3) 0.0599(11) Uani d . . . 1 . .
H H2 0.5809 1.1317 0.4045 0.072 Uiso calc U . R 1 . .
C C3 0.6433(4) 0.9652(4) 0.4229(3) 0.0538(10) Uani d . . . 1 . .
H H3 0.7315 0.9901 0.4654 0.065 Uiso calc U . R 1 . .
C C4 0.5722(3) 0.8398(3) 0.3814(2) 0.0417(9) Uani d . . . 1 . .
C C5 0.6154(3) 0.7230(3) 0.3790(2) 0.0379(8) Uani d . . . 1 . .
C C6 0.5297(3) 0.6100(3) 0.3198(2) 0.0390(8) Uani d . . . 1 . .
C C7 0.5582(4) 0.4852(3) 0.2905(3) 0.0464(9) Uani d . . . 1 . .
H H7 0.6407 0.4582 0.3132 0.056 Uiso calc U . R 1 . .
C C8 0.4435(3) 0.4100(3) 0.2227(3) 0.0469(9) Uani d . . . 1 . .
H H8 0.4346 0.3232 0.1902 0.056 Uiso calc U . R 1 . .
C C9 0.3420(3) 0.4869(3) 0.2112(2) 0.0385(8) Uani d . . . 1 . .
C C10 0.3158(4) 1.0097(3) 0.2704(3) 0.0487(9) Uani d . . . 1 . .
C C11 0.1899(4) 0.9997(4) 0.2914(3) 0.0637(11) Uani d . . . 1 . .
H H11 0.18 0.9665 0.3432 0.076 Uiso calc U . R 1 . .
C C12 0.0799(4) 1.0379(4) 0.2373(4) 0.0722(13) Uani d . . . 1 . .
H H12 -0.0033 1.0324 0.2534 0.087 Uiso calc U . R 1 . .
C C13 0.0930(5) 1.0842(4) 0.1593(4) 0.0727(13) Uani d . . . 1 . .
H H13 0.0182 1.1096 0.122 0.087 Uiso calc U . R 1 . .
C C14 0.2154(4) 1.0934(4) 0.1361(3) 0.0659(12) Uani d . . . 1 . .
H H14 0.2227 1.1243 0.0826 0.079 Uiso calc U . R 1 . .
C C15 0.3288(4) 1.0574(3) 0.1909(3) 0.0519(10) Uani d . . . 1 . .
C C16 0.4564(5) 1.0663(4) 0.1651(3) 0.0605(11) Uani d . . . 1 . .
C C17 0.5599(5) 1.0747(5) 0.1430(3) 0.0750(13) Uani d . . . 1 . .
C C18 0.6910(5) 1.0819(7) 0.1155(4) 0.130(2) Uani d . . . 1 . .
H H18A 0.7472 1.1622 0.1544 0.195 Uiso calc U . R 1 . .
H H18B 0.6735 1.0747 0.045 0.195 Uiso calc U . R 1 . .
H H18C 0.7372 1.0135 0.1292 0.195 Uiso calc U . R 1 . .
C C19 0.1981(3) 0.4454(3) 0.1516(3) 0.0414(9) Uani d . . . 1 . .
C C20 0.0924(4) 0.4725(3) 0.1954(3) 0.0505(10) Uani d . . . 1 . .
H H20 0.1122 0.5213 0.2625 0.061 Uiso calc U . R 1 . .
C C21 -0.0421(4) 0.4282(4) 0.1409(4) 0.0638(11) Uani d . . . 1 . .
H H21 -0.1122 0.4475 0.1713 0.077 Uiso calc U . R 1 . .
C C22 -0.0722(4) 0.3554(4) 0.0415(3) 0.0662(12) Uani d . . . 1 . .
H H22 -0.1627 0.3251 0.005 0.079 Uiso calc U . R 1 . .
C C23 0.0300(4) 0.3274(4) -0.0038(3) 0.0597(11) Uani d . . . 1 . .
H H23 0.0084 0.2786 -0.071 0.072 Uiso calc U . R 1 . .
C C24 0.1666(4) 0.3712(3) 0.0498(3) 0.0462(9) Uani d . . . 1 . .
C C25 0.2734(4) 0.3438(4) 0.0015(3) 0.0543(10) Uani d . . . 1 . .
C C26 0.3647(5) 0.3236(4) -0.0354(3) 0.0661(12) Uani d . . . 1 . .
C C27 0.4811(5) 0.3001(6) -0.0780(4) 0.1040(18) Uani d . . . 1 . .
H H27A 0.5144 0.3752 -0.0927 0.156 Uiso calc U . R 1 . .
H H27B 0.4526 0.2301 -0.1389 0.156 Uiso calc U . R 1 . .
H H27C 0.5526 0.2797 -0.0302 0.156 Uiso calc U . R 1 . .
C C28 0.7561(3) 0.7158(3) 0.4352(2) 0.0399(8) Uani d . . . 1 . .
C C29 0.8676(4) 0.7368(4) 0.3977(3) 0.0530(10) Uani d . . . 1 . .
C C30 0.9955(4) 0.7237(4) 0.4514(3) 0.0647(12) Uani d . . . 1 . .
H H30 1.0703 0.7377 0.4268 0.078 Uiso calc U . R 1 . .
C C31 1.0159(4) 0.6908(4) 0.5397(3) 0.0556(10) Uani d . . . 1 . .
C C32 0.9044(4) 0.6708(4) 0.5745(3) 0.0535(10) Uani d . . . 1 . .
H H32 0.9168 0.6489 0.6342 0.064 Uiso calc U . R 1 . .
C C33 0.7740(3) 0.6818(3) 0.5248(2) 0.0427(9) Uani d . . . 1 . .
C C34 0.8517(5) 0.7686(5) 0.2992(3) 0.0894(16) Uani d . . . 1 . .
H H34A 0.9384 0.7734 0.2837 0.134 Uiso calc U . R 1 . .
H H34B 0.8199 0.8494 0.3052 0.134 Uiso calc U . R 1 . .
H H34C 0.7869 0.7034 0.2461 0.134 Uiso calc U . R 1 . .
C C35 1.1564(4) 0.6747(5) 0.5940(4) 0.0974(17) Uani d . . . 1 . .
H H35A 1.2 0.7531 0.6451 0.146 Uiso calc U . R 1 . .
H H35B 1.21 0.653 0.5467 0.146 Uiso calc U . R 1 . .
H H35C 1.1486 0.6077 0.6248 0.146 Uiso calc U . R 1 . .
C C36 0.6569(4) 0.6563(4) 0.5675(3) 0.0633(11) Uani d . . . 1 . .
H H36A 0.6192 0.5673 0.5412 0.095 Uiso calc U . R 1 . .
H H36B 0.5878 0.7062 0.5489 0.095 Uiso calc U . R 1 . .
H H36C 0.6889 0.6792 0.6397 0.095 Uiso calc U . R 1 . .
F F1 0.2514(2) 0.7314(2) 0.18584(17) 0.0702(7) Uani d . . . 1 . .
F F2 0.2453(2) 0.7371(2) 0.34451(19) 0.0771(7) Uani d . . . 1 . .
N N1 0.4429(2) 0.8456(3) 0.32453(19) 0.0393(7) Uani d . . . 1 . .
N N2 0.3936(2) 0.6085(3) 0.26926(19) 0.0359(7) Uani d . . . 1 . .
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'
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
F1 B1 F2 . . 110.9(3) ?
F1 B1 N1 . . 110.9(3) ?
F2 B1 N1 . . 108.3(3) ?
F1 B1 N2 . . 109.8(3) ?
F2 B1 N2 . . 109.7(3) ?
N1 B1 N2 . . 107.0(3) ?
N1 C1 C2 . . 108.8(3) ?
N1 C1 C10 . . 122.9(3) ?
C2 C1 C10 . . 128.2(3) ?
C3 C2 C1 . . 108.2(3) ?
C3 C2 H2 . . 125.9 ?
C1 C2 H2 . . 125.9 ?
C2 C3 C4 . . 107.5(3) ?
C2 C3 H3 . . 126.3 ?
C4 C3 H3 . . 126.3 ?
C5 C4 N1 . . 120.6(3) ?
C5 C4 C3 . . 131.3(3) ?
N1 C4 C3 . . 107.5(3) ?
C4 C5 C6 . . 120.3(3) ?
C4 C5 C28 . . 121.0(3) ?
C6 C5 C28 . . 118.6(3) ?
C5 C6 C7 . . 130.3(3) ?
C5 C6 N2 . . 121.9(3) ?
C7 C6 N2 . . 107.4(3) ?
C8 C7 C6 . . 108.1(3) ?
C8 C7 H7 . . 126.0 ?
C6 C7 H7 . . 126.0 ?
C7 C8 C9 . . 107.7(3) ?
C7 C8 H8 . . 126.1 ?
C9 C8 H8 . . 126.1 ?
N2 C9 C8 . . 109.2(3) ?
N2 C9 C19 . . 123.6(3) ?
C8 C9 C19 . . 127.1(3) ?
C11 C10 C15 . . 118.9(3) ?
C11 C10 C1 . . 121.8(3) ?
C15 C10 C1 . . 119.3(3) ?
C12 C11 C10 . . 121.3(4) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 C13 . . 119.6(4) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C14 C13 C12 . . 120.3(4) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 121.1(4) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
C14 C15 C10 . . 118.8(4) ?
C14 C15 C16 . . 120.6(4) ?
C10 C15 C16 . . 120.6(3) ?
C17 C16 C15 . . 178.9(4) ?
C16 C17 C18 . . 178.4(5) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C20 C19 C24 . . 118.9(3) ?
C20 C19 C9 . . 121.0(3) ?
C24 C19 C9 . . 120.0(3) ?
C21 C20 C19 . . 121.0(4) ?
C21 C20 H20 . . 119.5 ?
C19 C20 H20 . . 119.5 ?
C22 C21 C20 . . 119.8(4) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C23 C22 C21 . . 120.5(4) ?
C23 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
C22 C23 C24 . . 120.6(4) ?
C22 C23 H23 . . 119.7 ?
C24 C23 H23 . . 119.7 ?
C23 C24 C19 . . 119.2(4) ?
C23 C24 C25 . . 120.5(3) ?
C19 C24 C25 . . 120.3(3) ?
C26 C25 C24 . . 177.7(4) ?
C25 C26 C27 . . 178.2(5) ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C29 C28 C33 . . 120.2(3) ?
C29 C28 C5 . . 121.0(3) ?
C33 C28 C5 . . 118.7(3) ?
C30 C29 C28 . . 118.3(3) ?
C30 C29 C34 . . 119.8(4) ?
C28 C29 C34 . . 121.8(3) ?
C31 C30 C29 . . 122.6(4) ?
C31 C30 H30 . . 118.7 ?
C29 C30 H30 . . 118.7 ?
C32 C31 C30 . . 117.7(3) ?
C32 C31 C35 . . 121.7(4) ?
C30 C31 C35 . . 120.6(4) ?
C31 C32 C33 . . 122.9(3) ?
C31 C32 H32 . . 118.6 ?
C33 C32 H32 . . 118.6 ?
C32 C33 C28 . . 118.3(3) ?
C32 C33 C36 . . 119.4(3) ?
C28 C33 C36 . . 122.3(3) ?
C29 C34 H34A . . 109.5 ?
C29 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C29 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C31 C35 H35A . . 109.5 ?
C31 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C31 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C33 C36 H36A . . 109.5 ?
C33 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C33 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C1 N1 C4 . . 108.1(3) ?
C1 N1 B1 . . 127.8(3) ?
C4 N1 B1 . . 123.7(3) ?
C9 N2 C6 . . 107.6(3) ?
C9 N2 B1 . . 129.7(3) ?
C6 N2 B1 . . 122.6(3) ?
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 F1 . 1.370(4) ?
B1 F2 . 1.380(4) ?
B1 N1 . 1.542(5) ?
B1 N2 . 1.551(5) ?
C1 N1 . 1.349(4) ?
C1 C2 . 1.399(5) ?
C1 C10 . 1.483(5) ?
C2 C3 . 1.360(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.406(5) ?
C3 H3 . 0.93 ?
C4 C5 . 1.387(5) ?
C4 N1 . 1.392(4) ?
C5 C6 . 1.391(5) ?
C5 C28 . 1.489(4) ?
C6 C7 . 1.400(5) ?
C6 N2 . 1.402(4) ?
C7 C8 . 1.367(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.397(4) ?
C8 H8 . 0.93 ?
C9 N2 . 1.357(4) ?
C9 C19 . 1.476(5) ?
C10 C11 . 1.387(5) ?
C10 C15 . 1.400(5) ?
C11 C12 . 1.369(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.371(6) ?
C12 H12 . 0.93 ?
C13 C14 . 1.367(6) ?
C13 H13 . 0.93 ?
C14 C15 . 1.386(5) ?
C14 H14 . 0.93 ?
C15 C16 . 1.435(6) ?
C16 C17 . 1.175(5) ?
C17 C18 . 1.480(7) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 C20 . 1.382(5) ?
C19 C24 . 1.410(5) ?
C20 C21 . 1.381(5) ?
C20 H20 . 0.93 ?
C21 C22 . 1.378(6) ?
C21 H21 . 0.93 ?
C22 C23 . 1.365(5) ?
C22 H22 . 0.93 ?
C23 C24 . 1.395(5) ?
C23 H23 . 0.93 ?
C24 C25 . 1.432(5) ?
C25 C26 . 1.181(5) ?
C26 C27 . 1.467(6) ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?
C28 C29 . 1.393(5) ?
C28 C33 . 1.403(4) ?
C29 C30 . 1.389(5) ?
C29 C34 . 1.514(5) ?
C30 C31 . 1.377(5) ?
C30 H30 . 0.93 ?
C31 C32 . 1.367(5) ?
C31 C35 . 1.509(5) ?
C32 C33 . 1.383(5) ?
C32 H32 . 0.93 ?
C33 C36 . 1.501(5) ?
C34 H34A . 0.96 ?
C34 H34B . 0.96 ?
C34 H34C . 0.96 ?
C35 H35A . 0.96 ?
C35 H35B . 0.96 ?
C35 H35C . 0.96 ?
C36 H36A . 0.96 ?
C36 H36B . 0.96 ?
C36 H36C . 0.96 ?
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 . . . . 0.0(4) ?
C10 C1 C2 C3 . . . . -176.1(4) ?
C1 C2 C3 C4 . . . . 0.9(4) ?
C2 C3 C4 C5 . . . . 169.5(4) ?
C2 C3 C4 N1 . . . . -1.4(4) ?
N1 C4 C5 C6 . . . . -0.3(5) ?
C3 C4 C5 C6 . . . . -170.3(4) ?
N1 C4 C5 C28 . . . . 176.7(3) ?
C3 C4 C5 C28 . . . . 6.7(6) ?
C4 C5 C6 C7 . . . . 166.5(3) ?
C28 C5 C6 C7 . . . . -10.5(5) ?
C4 C5 C6 N2 . . . . -6.6(5) ?
C28 C5 C6 N2 . . . . 176.4(3) ?
C5 C6 C7 C8 . . . . -172.9(3) ?
N2 C6 C7 C8 . . . . 0.9(4) ?
C6 C7 C8 C9 . . . . -1.3(4) ?
C7 C8 C9 N2 . . . . 1.2(4) ?
C7 C8 C9 C19 . . . . -175.0(3) ?
N1 C1 C10 C11 . . . . 67.4(5) ?
C2 C1 C10 C11 . . . . -116.9(5) ?
N1 C1 C10 C15 . . . . -111.2(4) ?
C2 C1 C10 C15 . . . . 64.5(5) ?
C15 C10 C11 C12 . . . . -1.3(6) ?
C1 C10 C11 C12 . . . . 180.0(4) ?
C10 C11 C12 C13 . . . . 1.5(7) ?
C11 C12 C13 C14 . . . . -0.6(7) ?
C12 C13 C14 C15 . . . . -0.6(7) ?
C13 C14 C15 C10 . . . . 0.7(6) ?
C13 C14 C15 C16 . . . . 179.4(4) ?
C11 C10 C15 C14 . . . . 0.2(6) ?
C1 C10 C15 C14 . . . . 178.9(4) ?
C11 C10 C15 C16 . . . . -178.4(4) ?
C1 C10 C15 C16 . . . . 0.3(5) ?
N2 C9 C19 C20 . . . . -51.3(4) ?
C8 C9 C19 C20 . . . . 124.4(4) ?
N2 C9 C19 C24 . . . . 132.1(3) ?
C8 C9 C19 C24 . . . . -52.2(5) ?
C24 C19 C20 C21 . . . . -0.1(5) ?
C9 C19 C20 C21 . . . . -176.7(3) ?
C19 C20 C21 C22 . . . . 0.3(6) ?
C20 C21 C22 C23 . . . . -0.5(6) ?
C21 C22 C23 C24 . . . . 0.4(6) ?
C22 C23 C24 C19 . . . . -0.2(5) ?
C22 C23 C24 C25 . . . . -178.8(3) ?
C20 C19 C24 C23 . . . . 0.0(5) ?
C9 C19 C24 C23 . . . . 176.7(3) ?
C20 C19 C24 C25 . . . . 178.6(3) ?
C9 C19 C24 C25 . . . . -4.7(5) ?
C4 C5 C28 C29 . . . . -78.1(4) ?
C6 C5 C28 C29 . . . . 98.9(4) ?
C4 C5 C28 C33 . . . . 104.7(4) ?
C6 C5 C28 C33 . . . . -78.3(4) ?
C33 C28 C29 C30 . . . . -0.3(6) ?
C5 C28 C29 C30 . . . . -177.4(4) ?
C33 C28 C29 C34 . . . . 177.6(4) ?
C5 C28 C29 C34 . . . . 0.5(6) ?
C28 C29 C30 C31 . . . . 0.1(6) ?
C34 C29 C30 C31 . . . . -177.8(4) ?
C29 C30 C31 C32 . . . . -0.1(6) ?
C29 C30 C31 C35 . . . . 178.5(4) ?
C30 C31 C32 C33 . . . . 0.3(6) ?
C35 C31 C32 C33 . . . . -178.4(4) ?
C31 C32 C33 C28 . . . . -0.5(6) ?
C31 C32 C33 C36 . . . . 179.1(4) ?
C29 C28 C33 C32 . . . . 0.4(5) ?
C5 C28 C33 C32 . . . . 177.7(3) ?
C29 C28 C33 C36 . . . . -179.1(4) ?
C5 C28 C33 C36 . . . . -1.8(5) ?
C2 C1 N1 C4 . . . . -0.9(4) ?
C10 C1 N1 C4 . . . . 175.5(3) ?
C2 C1 N1 B1 . . . . 171.1(3) ?
C10 C1 N1 B1 . . . . -12.4(5) ?
C5 C4 N1 C1 . . . . -170.7(3) ?
C3 C4 N1 C1 . . . . 1.5(4) ?
C5 C4 N1 B1 . . . . 16.9(5) ?
C3 C4 N1 B1 . . . . -171.0(3) ?
F1 B1 N1 C1 . . . . 46.3(5) ?
F2 B1 N1 C1 . . . . -75.6(4) ?
N2 B1 N1 C1 . . . . 166.1(3) ?
F1 B1 N1 C4 . . . . -142.7(3) ?
F2 B1 N1 C4 . . . . 95.3(4) ?
N2 B1 N1 C4 . . . . -23.0(4) ?
C8 C9 N2 C6 . . . . -0.6(3) ?
C19 C9 N2 C6 . . . . 175.8(3) ?
C8 C9 N2 B1 . . . . 176.2(3) ?
C19 C9 N2 B1 . . . . -7.4(5) ?
C5 C6 N2 C9 . . . . 174.3(3) ?
C7 C6 N2 C9 . . . . -0.2(3) ?
C5 C6 N2 B1 . . . . -2.8(5) ?
C7 C6 N2 B1 . . . . -177.3(3) ?
F1 B1 N2 C9 . . . . -40.1(5) ?
F2 B1 N2 C9 . . . . 82.1(4) ?
N1 B1 N2 C9 . . . . -160.5(3) ?
F1 B1 N2 C6 . . . . 136.3(3) ?
F2 B1 N2 C6 . . . . -101.5(3) ?
N1 B1 N2 C6 . . . . 15.8(4) ?
