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#$Date: 2022-03-11 12:29:27 +0200 (Fri, 11 Mar 2022) $
#$Revision: 273660 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104749.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_8104749
loop_
_publ_author_name
'Li, Huixing'
'Han, Xinlong'
'Cao, Bin'
_publ_section_title
;
 Crystal structure of
 4-(2,2-difluoroethyl)-2,4,6-trimethylisoquinoline-1,3(2H,4H)-dione,
 C14H15F2NO2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              499
_journal_page_last               501
_journal_paper_doi               10.1515/ncrs-2020-0635
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C14 H15 F2 N O2'
_chemical_formula_sum            'C14 H15 F2 N O2'
_chemical_formula_weight         267.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 114.979(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5474(10)
_cell_length_b                   11.0737(7)
_cell_length_c                   11.4311(10)
_cell_measurement_reflns_used    1402
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      3.25
_cell_volume                     1325.0(2)
_computing_cell_refinement       'APEX2-2008 [1]'
_computing_data_collection       'APEX2-2008 [1]'
_computing_data_reduction        'SAINT- 2008 [1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7513
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.801
_diffrn_reflns_theta_min         3.576
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2008 [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0753P)²+0.9106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.2034
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1886
_reflns_number_total             2688
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0635_suppl.cif
_cod_data_source_block           1
_cod_database_code               8104749
_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   0.981
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C4A, C5A, C6A, C1A, C12A, O1A, C10A, C13A, C9A, F1A, F2A, C11A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C12, C1, C5, N1, O1, C4, C6, C2, C14, C3, C10, C13, O2, C7, C9, F1, F2, C8, C11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Others
 Sof(H8B)=Sof(C1A)=Sof(C5A)=Sof(O1A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C9A)=Sof(C10A)=Sof(H10A)=Sof(C4A)=Sof(C13A)=
 Sof(H13A)=Sof(F1A)=Sof(F2A)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(C1)=Sof(H8A)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C4)=Sof(C5)=Sof(C6)=Sof(H6A)=
 Sof(H6B)=Sof(H6C)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=
 Sof(H12B)=Sof(C13)=Sof(H13)=Sof(F1)=Sof(F2)=Sof(O1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C13(H13), C13A(H13A)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8A), C8(H8B), C10(H10), C10A(H10A)
4.d Fitted hexagon refined as free rotating group:
 C3(C7,C8,C9,C10,C4)
4.e Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C6A(H6AA,H6AB,
 H6AC), C11A(H11D,H11E,H11F)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.3381(4) 0.2220(3) 0.6764(4) 0.0424(9) Uani 0.788(4) 1 d . U P A 1
C1A C 0.309(2) 0.2344(18) 0.7149(18) 0.063(4) Uani 0.212(4) 1 d . U P A 2
C2 C 0.1206(3) 0.2426(3) 0.5044(3) 0.0499(7) Uani 1 1 d . U . . .
C3 C 0.14746(19) 0.36866(16) 0.48370(19) 0.0438(6) Uani 1 1 d . U . . .
C4 C 0.26464(17) 0.4227(2) 0.5567(2) 0.0374(9) Uani 0.788(4) 1 d G U P A 1
C4A C 0.2437(19) 0.4292(19) 0.5913(18) 0.063(5) Uani 0.212(4) 1 d . U P A 2
C5 C 0.3726(3) 0.3513(3) 0.6581(3) 0.0370(7) Uani 0.788(4) 1 d . U P A 1
C5A C 0.3353(17) 0.3682(15) 0.7129(15) 0.061(3) Uani 0.212(4) 1 d . U P A 2
C6 C 0.4896(7) 0.3449(8) 0.6261(6) 0.0507(12) Uani 0.788(4) 1 d . U P A 1
H6A H 0.556342 0.299340 0.691633 0.076 Uiso 0.788(4) 1 calc GR . P A 1
H6B H 0.519585 0.425103 0.622734 0.076 Uiso 0.788(4) 1 calc GR . P A 1
H6C H 0.465712 0.306211 0.543993 0.076 Uiso 0.788(4) 1 calc GR . P A 1
C6A C 0.329(3) 0.456(3) 0.823(4) 0.069(7) Uani 0.212(4) 1 d . U P A 2
H6AA H 0.251067 0.501618 0.788107 0.104 Uiso 0.212(4) 1 calc GR . P A 2
H6AB H 0.400531 0.510650 0.852032 0.104 Uiso 0.212(4) 1 calc GR . P A 2
H6AC H 0.332302 0.408580 0.894532 0.104 Uiso 0.212(4) 1 calc GR . P A 2
C7 C 0.05091(15) 0.43441(18) 0.38855(18) 0.0563(7) Uani 1 1 d G U . A .
H7 H -0.027483 0.398238 0.339692 0.068 Uiso 1 1 calc R . . . .
C8 C 0.0715(2) 0.55423(18) 0.3664(2) 0.0588(8) Uani 1 1 d G U . A .
H8A H 0.006941 0.598223 0.302756 0.071 Uiso 0.788(4) 1 calc R . P A 1
H8B H 0.019846 0.589992 0.287992 0.071 Uiso 0.212(4) 1 calc R . P A 2
C9 C 0.1887(3) 0.60829(18) 0.4394(3) 0.0490(15) Uani 0.788(4) 1 d G U P A 1
C9A C 0.1726(18) 0.6245(17) 0.464(2) 0.048(4) Uani 0.212(4) 1 d . U P A 2
C10 C 0.2853(2) 0.5425(2) 0.5346(3) 0.0471(11) Uani 0.788(4) 1 d G U P A 1
H10 H 0.363663 0.578714 0.583448 0.056 Uiso 0.788(4) 1 calc R . P A 1
C10A C 0.2533(17) 0.5515(18) 0.564(2) 0.063(5) Uani 0.212(4) 1 d . U P A 2
H10A H 0.325853 0.590211 0.623566 0.075 Uiso 0.212(4) 1 calc R . P A 2
C11 C 0.2099(8) 0.7392(6) 0.4190(10) 0.075(2) Uani 0.788(4) 1 d . U P A 1
H11A H 0.203857 0.750053 0.333255 0.113 Uiso 0.788(4) 1 calc GR . P A 1
H11B H 0.293119 0.763442 0.480688 0.113 Uiso 0.788(4) 1 calc GR . P A 1
H11C H 0.146102 0.787517 0.429835 0.113 Uiso 0.788(4) 1 calc GR . P A 1
C11A C 0.183(4) 0.760(3) 0.440(5) 0.090(10) Uani 0.212(4) 1 d . U P A 2
H11D H 0.259637 0.774047 0.428523 0.136 Uiso 0.212(4) 1 calc GR . P A 2
H11E H 0.185264 0.805206 0.511943 0.136 Uiso 0.212(4) 1 calc GR . P A 2
H11F H 0.110237 0.783817 0.363068 0.136 Uiso 0.212(4) 1 calc GR . P A 2
C12 C 0.4183(3) 0.4144(3) 0.7916(3) 0.0417(8) Uani 0.788(4) 1 d . U P A 1
H12A H 0.482532 0.364469 0.856423 0.050 Uiso 0.788(4) 1 calc R . P A 1
H12B H 0.457919 0.490891 0.788453 0.050 Uiso 0.788(4) 1 calc R . P A 1
C12A C 0.4682(18) 0.3829(15) 0.7371(19) 0.074(4) Uani 0.212(4) 1 d . U P A 2
H12C H 0.521538 0.332796 0.809461 0.088 Uiso 0.212(4) 1 calc R . P A 2
H12D H 0.493714 0.466403 0.758745 0.088 Uiso 0.212(4) 1 calc R . P A 2
C13 C 0.3088(9) 0.4373(9) 0.8314(9) 0.0568(12) Uani 0.788(4) 1 d . U P A 1
H13 H 0.247933 0.493367 0.769502 0.068 Uiso 0.788(4) 1 calc R . P A 1
C13A C 0.488(5) 0.342(5) 0.603(5) 0.107(6) Uani 0.212(4) 1 d . U P A 2
H13A H 0.438219 0.383208 0.520989 0.129 Uiso 0.212(4) 1 calc R . P A 2
C14 C 0.1886(4) 0.0518(3) 0.6244(4) 0.0773(11) Uani 1 1 d . U . . .
H14A H 0.239775 -0.001354 0.599200 0.116 Uiso 1 1 calc GR . . . .
H14B H 0.099829 0.034741 0.573610 0.116 Uiso 1 1 calc GR . . . .
H14C H 0.208731 0.039699 0.714090 0.116 Uiso 1 1 calc GR . . . .
F1 F 0.2497(3) 0.3426(3) 0.8359(3) 0.0807(9) Uani 0.788(4) 1 d . U P A 1
F1A F 0.6286(14) 0.3575(16) 0.6669(19) 0.155(7) Uani 0.212(4) 1 d . U P A 2
F2 F 0.3601(3) 0.4912(3) 0.9509(3) 0.0985(11) Uani 0.788(4) 1 d . U P A 1
F2A F 0.4822(15) 0.2247(13) 0.6108(16) 0.126(5) Uani 0.212(4) 1 d . U P A 2
N1 N 0.2156(2) 0.1779(2) 0.6035(2) 0.0538(6) Uani 1 1 d . U . . .
O1 O 0.4173(4) 0.1580(4) 0.7576(4) 0.0680(11) Uani 0.788(4) 1 d . U P A 1
O1A O 0.379(2) 0.1726(18) 0.8021(18) 0.112(8) Uani 0.212(4) 1 d . U P A 2
O2 O 0.0203(2) 0.1934(2) 0.4379(2) 0.0784(8) Uani 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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'
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
N1 C1 C5 120.4(3) . .
O1 C1 C5 119.7(4) . .
O1 C1 N1 119.9(4) . .
N1 C2 C3 118.1(2) . .
O2 C2 C3 122.4(3) . .
O2 C2 N1 119.6(3) . .
C7 C3 C2 117.98(17) . .
C7 C3 C4 120.0 . .
C7 C3 C4A 120.2(9) . .
C4 C3 C2 122.02(17) . .
C4A C3 C2 116.5(8) . .
C3 C7 H7 120.0 . .
C8 C7 C3 120.0 . .
C8 C7 H7 120.0 . .
C7 C8 H8A 120.0 . .
C7 C8 H8B 119.5 . .
C7 C8 C9 120.0 . .
C7 C8 C9A 121.0(8) . .
C9 C8 H8A 120.0 . .
C9A C8 H8B 119.5 . .
C8 C9 C10 120.0 . .
C8 C9 C11 120.2(4) . .
C10 C9 C11 119.8(4) . .
C9 C10 H10 120.0 . .
C9 C10 C4 120.0 . .
C4 C10 H10 120.0 . .
C3 C4 C5 120.77(19) . .
C10 C4 C3 120.0 . .
C10 C4 C5 119.20(19) . .
C1 C5 C6 107.2(4) . .
C1 C5 C12 106.8(3) . .
C4 C5 C1 114.6(3) . .
C4 C5 C6 111.2(4) . .
C4 C5 C12 110.1(3) . .
C6 C5 C12 106.6(4) . .
C5 C6 H6A 109.5 . .
C5 C6 H6B 109.5 . .
C5 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C5 C12 H12A 109.1 . .
C5 C12 H12B 109.1 . .
H12A C12 H12B 107.8 . .
C13 C12 C5 112.6(4) . .
C13 C12 H12A 109.1 . .
C13 C12 H12B 109.1 . .
C12 C13 H13 108.6 . .
F1 C13 C12 113.7(7) . .
F1 C13 H13 108.6 . .
F1 C13 F2 109.5(6) . .
F2 C13 C12 107.6(6) . .
F2 C13 H13 108.6 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
N1 C14 H14A 109.5 . .
N1 C14 H14B 109.5 . .
N1 C14 H14C 109.5 . .
C1 N1 C2 123.9(3) . .
C1 N1 C14 117.8(3) . .
C2 N1 C14 118.1(3) . .
C2 N1 C1A 122.8(9) . .
C1A N1 C14 113.9(8) . .
N1 C1A C5A 119.8(14) . .
O1A C1A N1 119.1(19) . .
O1A C1A C5A 120.2(19) . .
C1A C5A C6A 120.2(18) . .
C12A C5A C1A 107.9(15) . .
C12A C5A C6A 100.0(17) . .
C12A C5A C4A 113.7(16) . .
C4A C5A C1A 112.7(15) . .
C4A C5A C6A 102(2) . .
C5A C6A H6AA 109.5 . .
C5A C6A H6AB 109.5 . .
C5A C6A H6AC 109.5 . .
H6AA C6A H6AB 109.5 . .
H6AA C6A H6AC 109.5 . .
H6AB C6A H6AC 109.5 . .
C5A C12A H12C 109.8 . .
C5A C12A H12D 109.8 . .
C5A C12A C13A 109(2) . .
H12C C12A H12D 108.2 . .
C13A C12A H12C 109.8 . .
C13A C12A H12D 109.8 . .
C8 C9A C11A 119(2) . .
C10A C9A C8 111.3(15) . .
C10A C9A C11A 130(3) . .
C9A C10A H10A 114.6 . .
C9A C10A C4A 130.8(18) . .
C4A C10A H10A 114.6 . .
C3 C4A C5A 124.9(16) . .
C10A C4A C3 111.6(15) . .
C10A C4A C5A 123.0(17) . .
C12A C13A H13A 119.7 . .
F1A C13A C12A 94(3) . .
F1A C13A H13A 119.7 . .
F2A C13A C12A 100(3) . .
F2A C13A H13A 119.7 . .
F2A C13A F1A 99(4) . .
C9A C11A H11D 109.5 . .
C9A C11A H11E 109.5 . .
C9A C11A H11F 109.5 . .
H11D C11A H11E 109.5 . .
H11D C11A H11F 109.5 . .
H11E C11A H11F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C5 1.525(5) .
C1 N1 1.392(5) .
C1 O1 1.218(5) .
C2 C3 1.471(3) .
C2 N1 1.396(4) .
C2 O2 1.213(3) .
C3 C7 1.3900 .
C3 C4 1.3900 .
C3 C4A 1.43(2) .
C7 H7 0.9300 .
C7 C8 1.3900 .
C8 H8A 0.9300 .
C8 H8B 0.9300 .
C8 C9 1.3900 .
C8 C9A 1.45(2) .
C9 C10 1.3900 .
C9 C11 1.504(6) .
C10 H10 0.9300 .
C10 C4 1.3900 .
C4 C5 1.518(4) .
C5 C6 1.543(7) .
C5 C12 1.554(5) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 C13 1.536(8) .
C13 H13 0.9800 .
C13 F1 1.264(10) .
C13 F2 1.374(10) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C14 N1 1.472(4) .
N1 C1A 1.42(2) .
C1A C5A 1.51(2) .
C1A O1A 1.20(2) .
C5A C6A 1.62(4) .
C5A C12A 1.45(3) .
C5A C4A 1.50(2) .
C6A H6AA 0.9600 .
C6A H6AB 0.9600 .
C6A H6AC 0.9600 .
C12A H12C 0.9700 .
C12A H12D 0.9700 .
C12A C13A 1.70(5) .
C9A C10A 1.39(2) .
C9A C11A 1.54(3) .
C10A H10A 0.9300 .
C10A C4A 1.40(2) .
C13A H13A 0.9800 .
C13A F1A 1.48(6) .
C13A F2A 1.31(6) .
C11A H11D 0.9600 .
C11A H11E 0.9600 .
C11A H11F 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 C5 C12 C13 -70.7(5) . . . .
C2 C3 C7 C8 179.3(2) . . . .
C2 C3 C4 C10 -179.3(2) . . . .
C2 C3 C4 C5 2.6(3) . . . .
C2 C3 C4A C5A 13(2) . . . .
C2 C3 C4A C10A -174.7(12) . . . .
C2 N1 C1A C5A -19(2) . . . .
C2 N1 C1A O1A 172.2(17) . . . .
C3 C2 N1 C1 -5.8(4) . . . .
C3 C2 N1 C14 179.9(3) . . . .
C3 C2 N1 C1A 27.2(11) . . . .
C3 C7 C8 C9 0.0 . . . .
C3 C7 C8 C9A -20.2(10) . . . .
C3 C4 C5 C1 -3.4(4) . . . .
C3 C4 C5 C6 118.3(4) . . . .
C3 C4 C5 C12 -123.8(3) . . . .
C7 C3 C4 C10 0.0 . . . .
C7 C3 C4 C5 -178.1(3) . . . .
C7 C3 C4A C5A 166.3(14) . . . .
C7 C3 C4A C10A -20.9(19) . . . .
C7 C8 C9 C10 0.0 . . . .
C7 C8 C9 C11 -177.9(5) . . . .
C7 C8 C9A C10A 10.5(19) . . . .
C7 C8 C9A C11A -174.2(14) . . . .
C8 C9 C10 C4 0.0 . . . .
C8 C9A C10A C4A -8(3) . . . .
C9 C10 C4 C3 0.0 . . . .
C9 C10 C4 C5 178.1(2) . . . .
C10 C4 C5 C1 178.5(2) . . . .
C10 C4 C5 C6 -59.7(4) . . . .
C10 C4 C5 C12 58.2(3) . . . .
C4 C3 C7 C8 0.0 . . . .
C4 C5 C12 C13 54.3(5) . . . .
C5 C1 N1 C2 4.9(5) . . . .
C5 C1 N1 C14 179.2(3) . . . .
C5 C12 C13 F1 57.6(8) . . . .
C5 C12 C13 F2 179.0(5) . . . .
C6 C5 C12 C13 175.0(6) . . . .
C11 C9 C10 C4 177.9(4) . . . .
C14 N1 C1A C5A -172.5(13) . . . .
C14 N1 C1A O1A 18(2) . . . .
N1 C1 C5 C4 -0.2(5) . . . .
N1 C1 C5 C6 -124.1(4) . . . .
N1 C1 C5 C12 122.0(4) . . . .
N1 C2 C3 C7 -177.4(2) . . . .
N1 C2 C3 C4 1.9(3) . . . .
N1 C2 C3 C4A -23.1(10) . . . .
N1 C1A C5A C6A 126(2) . . . .
N1 C1A C5A C12A -119.9(18) . . . .
N1 C1A C5A C4A 6(2) . . . .
O1 C1 C5 C4 -178.4(4) . . . .
O1 C1 C5 C6 57.7(5) . . . .
O1 C1 C5 C12 -56.2(5) . . . .
O1 C1 N1 C2 -176.9(3) . . . .
O1 C1 N1 C14 -2.6(5) . . . .
O2 C2 C3 C7 3.5(4) . . . .
O2 C2 C3 C4 -177.1(3) . . . .
O2 C2 C3 C4A 157.9(10) . . . .
O2 C2 N1 C1 173.3(3) . . . .
O2 C2 N1 C14 -1.1(4) . . . .
O2 C2 N1 C1A -153.8(10) . . . .
C1A C5A C12A C13A 74(3) . . . .
C1A C5A C4A C3 -4(3) . . . .
C1A C5A C4A C10A -176.3(18) . . . .
C5A C12A C13A F1A -175(2) . . . .
C5A C12A C13A F2A -75(4) . . . .
O1A C1A C5A C6A -65(3) . . . .
O1A C1A C5A C12A 49(3) . . . .
O1A C1A C5A C4A 175(2) . . . .
C6A C5A C12A C13A -159(3) . . . .
C6A C5A C4A C3 -134.5(19) . . . .
C6A C5A C4A C10A 54(2) . . . .
C12A C5A C4A C3 118.9(19) . . . .
C12A C5A C4A C10A -53(3) . . . .
C9A C10A C4A C3 13(3) . . . .
C9A C10A C4A C5A -174(2) . . . .
C4A C3 C7 C8 26.0(10) . . . .
C4A C5A C12A C13A -52(3) . . . .
C11A C9A C10A C4A 177(2) . . . .
