#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:59:04 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160298.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_7160298
loop_
_publ_author_name
'Roy, Anik'
'Dutta, Ranjan'
'Halder, Dibakar'
'Mandal, Koushik'
'Kundu, Somenath'
'Hossain, Maidul'
'Saha, Indrajit'
'Lee, Chang-Hee'
_publ_section_title
;
 Submicromolar fluorescence 'turn-on' detection of fluoride anions using
 meso-(tetra-aryl) calix[4]pyrrole.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1209
_journal_page_last               1214
_journal_paper_doi               10.1039/d4ob01708k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C2 H6 O2, C48 H40 F4 N4'
_chemical_formula_sum            'C50 H46 F4 N4 O2'
_chemical_formula_weight         810.91
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-01-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-09-27 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.116(6)
_cell_length_b                   22.806(9)
_cell_length_c                   11.975(4)
_cell_measurement_reflns_used    9236
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.74
_cell_measurement_theta_min      2.17
_cell_volume                     4128(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            46133
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         2.170
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1099 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.9070.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0523
_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)+(0.0532P)²+1.8647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2677
_reflns_number_total             3877
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01708k2.cif
_cod_data_source_block           2648rkm_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7160298--7160301.cif.'
_cod_database_code               7160298
_shelx_shelxl_version_number     2016/6
_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   0.989
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H25A(0.5) H25B(0.5) H25C(0.5) H26A(0.5) H26B(0.5) H26C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C1(H1A), C18(H18), C12(H12), C13(H13), C24(H24),
 C10(H10), C6(H6), C20(H20), C9(H9), C7(H7), C21(H21), C23(H23)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
O1 O 0.59745(14) 0.750000 0.61943(18) 0.0456(6) Uani 1 2 d S T P . .
N1 N 0.65446(16) 0.750000 0.3468(2) 0.0337(6) Uani 1 2 d S T P . .
H1 H 0.613015 0.750000 0.297627 0.040 Uiso 1 2 calc R U P . .
F1 F 0.90662(11) 0.49678(7) 0.59560(16) 0.0875(6) Uani 1 1 d . . . . .
N2 N 0.53070(11) 0.64782(7) 0.47212(15) 0.0353(4) Uani 1 1 d . . . . .
H2 H 0.552176 0.674895 0.514128 0.042 Uiso 1 1 calc R U . . .
N3 N 0.40325(16) 0.750000 0.5808(2) 0.0373(6) Uani 1 2 d S T P . .
H3 H 0.458779 0.750001 0.596490 0.045 Uiso 1 2 calc R U P . .
F2 F 0.57730(12) 0.62035(10) 0.98952(15) 0.1009(7) Uani 1 1 d . . . . .
C2 C 0.69207(13) 0.70053(9) 0.39148(17) 0.0320(5) Uani 1 1 d . . . . .
C11 C 0.57292(14) 0.62419(9) 0.38124(17) 0.0356(5) Uani 1 1 d . . . . .
C1 C 0.75371(13) 0.71881(9) 0.46607(18) 0.0371(5) Uani 1 1 d . . . . .
H1A H 0.789626 0.694816 0.509516 0.044 Uiso 1 1 calc R U . . .
C3 C 0.66795(14) 0.63881(9) 0.35339(18) 0.0353(5) Uani 1 1 d . . . . .
C17 C 0.35306(13) 0.70021(10) 0.56670(18) 0.0374(5) Uani 1 1 d . . . . .
C14 C 0.44946(13) 0.62220(10) 0.48651(19) 0.0386(5) Uani 1 1 d . . . . .
C5 C 0.73064(14) 0.59642(9) 0.41439(19) 0.0383(5) Uani 1 1 d . . . . .
C15 C 0.38980(14) 0.63863(10) 0.58317(19) 0.0415(6) Uani 1 1 d . . . . .
C19 C 0.44042(14) 0.63394(10) 0.69440(19) 0.0422(6) Uani 1 1 d . . . . .
C18 C 0.27031(14) 0.71900(11) 0.54010(19) 0.0457(6) Uani 1 1 d . . . . .
H18 H 0.221958 0.695135 0.524565 0.055 Uiso 1 1 calc R U . . .
C12 C 0.51754(16) 0.58357(11) 0.3367(2) 0.0507(6) Uani 1 1 d . . . . .
H12 H 0.528553 0.560687 0.273964 0.061 Uiso 1 1 calc R U . . .
C13 C 0.44052(16) 0.58231(11) 0.4026(2) 0.0519(7) Uani 1 1 d . . . . .
H13 H 0.391689 0.558286 0.390777 0.062 Uiso 1 1 calc R U . . .
C4 C 0.67943(17) 0.63492(11) 0.22538(19) 0.0508(6) Uani 1 1 d . . . . .
H4A H 0.636678 0.659732 0.189591 0.076 Uiso 1 1 calc R U . . .
H4B H 0.670795 0.595126 0.201599 0.076 Uiso 1 1 calc R U . . .
H4C H 0.737951 0.647470 0.205420 0.076 Uiso 1 1 calc R U . . .
C24 C 0.41883(16) 0.66812(12) 0.7858(2) 0.0524(7) Uani 1 1 d . . . . .
H24 H 0.372566 0.694822 0.779942 0.063 Uiso 1 1 calc R U . . .
C10 C 0.70774(16) 0.57136(11) 0.5153(2) 0.0540(7) Uani 1 1 d . . . . .
H10 H 0.650980 0.577373 0.543004 0.065 Uiso 1 1 calc R U . . .
C6 C 0.81488(16) 0.58611(11) 0.3764(2) 0.0542(7) Uani 1 1 d . . . . .
H6 H 0.832653 0.602276 0.308767 0.065 Uiso 1 1 calc R U . . .
C8 C 0.84818(17) 0.52906(10) 0.5353(3) 0.0564(7) Uani 1 1 d . . . . .
C20 C 0.50697(16) 0.59264(12) 0.7074(2) 0.0556(7) Uani 1 1 d . . . . .
H20 H 0.520874 0.567821 0.648284 0.067 Uiso 1 1 calc R U . . .
C16 C 0.31248(16) 0.59467(12) 0.5885(2) 0.0588(7) Uani 1 1 d . . . . .
H16A H 0.274121 0.604780 0.649441 0.088 Uiso 1 1 calc R U . . .
H16B H 0.335315 0.555825 0.599653 0.088 Uiso 1 1 calc R U . . .
H16C H 0.279840 0.596012 0.519799 0.088 Uiso 1 1 calc R U . . .
C9 C 0.76612(17) 0.53770(12) 0.5766(2) 0.0608(7) Uani 1 1 d . . . . .
H9 H 0.749327 0.521388 0.644512 0.073 Uiso 1 1 calc R U . . .
C7 C 0.87402(18) 0.55217(12) 0.4366(3) 0.0638(8) Uani 1 1 d . . . . .
H7 H 0.930751 0.545363 0.409510 0.077 Uiso 1 1 calc R U . . .
C21 C 0.55302(18) 0.58777(14) 0.8068(3) 0.0680(9) Uani 1 1 d . . . . .
H21 H 0.597971 0.560253 0.814934 0.082 Uiso 1 1 calc R U . . .
C23 C 0.46406(19) 0.66365(14) 0.8853(2) 0.0642(8) Uani 1 1 d . . . . .
H23 H 0.449055 0.687103 0.945966 0.077 Uiso 1 1 calc R U . . .
C22 C 0.53095(19) 0.62426(15) 0.8927(2) 0.0665(8) Uani 1 1 d . . . . .
C25 C 0.6357(3) 0.750000 0.7279(3) 0.0753(13) Uani 1 2 d S T P . .
H25A H 0.653511 0.789118 0.747085 0.113 Uiso 0.5 1 calc R U P A -1
H25B H 0.686370 0.724645 0.728626 0.113 Uiso 0.5 1 calc R U P A -1
H25C H 0.592976 0.736236 0.781091 0.113 Uiso 0.5 1 calc R U P A -1
C26 C 0.4186(4) 0.750000 0.2650(5) 0.111(2) Uani 1 2 d S T P . .
H26A H 0.375294 0.732878 0.216200 0.166 Uiso 0.5 1 calc R U P B -1
H26B H 0.401748 0.789568 0.282282 0.166 Uiso 0.5 1 calc R U P B -1
H26C H 0.421929 0.727555 0.332691 0.166 Uiso 0.5 1 calc R U P B -1
O2 O 0.4910(3) 0.750000 0.2188(4) 0.223(4) Uani 1 2 d S T P . .
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
_geom_angle_publ_flag
C2 N1 H1 124.7 7_575 . ?
C2 N1 H1 124.7 . . ?
C2 N1 C2 110.7(2) 7_575 . ?
C11 N2 H2 124.8 . . ?
C14 N2 H2 124.8 . . ?
C14 N2 C11 110.42(18) . . ?
C17 N3 H3 124.4 . . ?
C17 N3 H3 124.4 7_575 . ?
C17 N3 C17 111.2(2) . 7_575 ?
N1 C2 C3 122.94(18) . . ?
C1 C2 N1 106.77(19) . . ?
C1 C2 C3 130.20(19) . . ?
N2 C11 C3 122.02(18) . . ?
C12 C11 N2 107.02(19) . . ?
C12 C11 C3 130.5(2) . . ?
C2 C1 C1 107.91(12) . 7_575 ?
C2 C1 H1A 126.0 . . ?
C1 C1 H1A 126.0 7_575 . ?
C2 C3 C5 106.91(17) . . ?
C2 C3 C4 108.86(18) . . ?
C11 C3 C2 111.41(17) . . ?
C11 C3 C5 109.99(17) . . ?
C11 C3 C4 108.23(18) . . ?
C5 C3 C4 111.45(18) . . ?
N3 C17 C15 122.95(18) . . ?
C18 C17 N3 106.0(2) . . ?
C18 C17 C15 131.0(2) . . ?
N2 C14 C15 121.61(19) . . ?
C13 C14 N2 106.3(2) . . ?
C13 C14 C15 132.1(2) . . ?
C10 C5 C3 121.4(2) . . ?
C6 C5 C3 121.5(2) . . ?
C6 C5 C10 116.8(2) . . ?
C17 C15 C19 110.93(18) . . ?
C17 C15 C16 109.19(18) . . ?
C14 C15 C17 110.26(18) . . ?
C14 C15 C19 110.38(18) . . ?
C14 C15 C16 108.81(19) . . ?
C19 C15 C16 107.20(19) . . ?
C24 C19 C15 121.9(2) . . ?
C24 C19 C20 117.7(2) . . ?
C20 C19 C15 120.3(2) . . ?
C17 C18 C18 108.37(14) . 7_575 ?
C17 C18 H18 125.8 . . ?
C18 C18 H18 125.8 7_575 . ?
C11 C12 H12 126.1 . . ?
C11 C12 C13 107.7(2) . . ?
C13 C12 H12 126.1 . . ?
C14 C13 C12 108.5(2) . . ?
C14 C13 H13 125.7 . . ?
C12 C13 H13 125.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C19 C24 H24 119.1 . . ?
C23 C24 C19 121.7(3) . . ?
C23 C24 H24 119.1 . . ?
C5 C10 H10 118.8 . . ?
C9 C10 C5 122.3(2) . . ?
C9 C10 H10 118.8 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.5(3) . . ?
C7 C6 H6 119.3 . . ?
C9 C8 F1 118.9(3) . . ?
C9 C8 C7 121.9(2) . . ?
C7 C8 F1 119.2(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C9 H9 120.8 . . ?
C8 C9 C10 118.3(3) . . ?
C8 C9 H9 120.8 . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 H7 120.4 . . ?
C20 C21 H21 120.8 . . ?
C22 C21 C20 118.5(3) . . ?
C22 C21 H21 120.8 . . ?
C24 C23 H23 120.8 . . ?
C22 C23 C24 118.4(3) . . ?
C22 C23 H23 120.8 . . ?
F2 C22 C21 118.5(3) . . ?
C23 C22 F2 119.0(3) . . ?
C23 C22 C21 122.5(3) . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C25 1.421(4) . ?
N1 H1 0.8600 . ?
N1 C2 1.372(2) 7_575 ?
N1 C2 1.372(2) . ?
F1 C8 1.358(3) . ?
N2 H2 0.8600 . ?
N2 C11 1.372(3) . ?
N2 C14 1.371(3) . ?
N3 H3 0.8600 . ?
N3 C17 1.376(2) 7_575 ?
N3 C17 1.376(2) . ?
F2 C22 1.357(3) . ?
C2 C1 1.356(3) . ?
C2 C3 1.524(3) . ?
C11 C3 1.512(3) . ?
C11 C12 1.358(3) . ?
C1 C1 1.423(4) 7_575 ?
C1 H1A 0.9300 . ?
C3 C5 1.538(3) . ?
C3 C4 1.545(3) . ?
C17 C15 1.523(3) . ?
C17 C18 1.360(3) . ?
C14 C15 1.514(3) . ?
C14 C13 1.363(3) . ?
C5 C10 1.381(3) . ?
C5 C6 1.372(3) . ?
C15 C19 1.540(3) . ?
C15 C16 1.541(3) . ?
C19 C24 1.383(3) . ?
C19 C20 1.387(3) . ?
C18 C18 1.414(5) 7_575 ?
C18 H18 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.406(3) . ?
C13 H13 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C24 H24 0.9300 . ?
C24 C23 1.378(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.381(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(4) . ?
C8 C9 1.350(4) . ?
C8 C7 1.352(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C9 H9 0.9300 . ?
C7 H7 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.365(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.355(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 O2 1.228(6) . ?
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
_geom_torsion_publ_flag
N1 C2 C1 C1 -0.32(18) . . . 7_575 ?
N1 C2 C3 C11 -65.4(3) . . . . ?
N1 C2 C3 C5 174.4(2) . . . . ?
N1 C2 C3 C4 53.8(3) . . . . ?
F1 C8 C9 C10 179.0(2) . . . . ?
F1 C8 C7 C6 -178.6(2) . . . . ?
N2 C11 C3 C2 -30.1(3) . . . . ?
N2 C11 C3 C5 88.2(2) . . . . ?
N2 C11 C3 C4 -149.8(2) . . . . ?
N2 C11 C12 C13 -0.4(3) . . . . ?
N2 C14 C15 C17 70.7(3) . . . . ?
N2 C14 C15 C19 -52.2(3) . . . . ?
N2 C14 C15 C16 -169.6(2) . . . . ?
N2 C14 C13 C12 0.3(3) . . . . ?
N3 C17 C15 C14 -73.9(3) . . . . ?
N3 C17 C15 C19 48.7(3) . . . . ?
N3 C17 C15 C16 166.6(2) . . . . ?
N3 C17 C18 C18 -1.00(19) . . . 7_575 ?
C2 N1 C2 C1 0.5(3) 7_575 . . . ?
C2 N1 C2 C3 -176.30(13) 7_575 . . . ?
C2 C3 C5 C10 92.0(2) . . . . ?
C2 C3 C5 C6 -81.8(3) . . . . ?
C11 N2 C14 C15 177.95(19) . . . . ?
C11 N2 C14 C13 -0.6(3) . . . . ?
C11 C3 C5 C10 -29.1(3) . . . . ?
C11 C3 C5 C6 157.1(2) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C1 C2 C3 C11 118.5(2) . . . . ?
C1 C2 C3 C5 -1.7(3) . . . . ?
C1 C2 C3 C4 -122.2(2) . . . . ?
C3 C2 C1 C1 176.21(18) . . . 7_575 ?
C3 C11 C12 C13 172.0(2) . . . . ?
C3 C5 C10 C9 -173.7(2) . . . . ?
C3 C5 C6 C7 174.1(2) . . . . ?
C17 N3 C17 C15 -176.80(14) 7_575 . . . ?
C17 N3 C17 C18 1.7(3) 7_575 . . . ?
C17 C15 C19 C24 29.2(3) . . . . ?
C17 C15 C19 C20 -154.0(2) . . . . ?
C14 N2 C11 C3 -172.56(19) . . . . ?
C14 N2 C11 C12 0.6(3) . . . . ?
C14 C15 C19 C24 151.7(2) . . . . ?
C14 C15 C19 C20 -31.5(3) . . . . ?
C5 C10 C9 C8 -0.3(4) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C15 C17 C18 C18 177.3(2) . . . 7_575 ?
C15 C14 C13 C12 -178.0(2) . . . . ?
C15 C19 C24 C23 179.8(2) . . . . ?
C15 C19 C20 C21 -179.9(2) . . . . ?
C19 C24 C23 C22 -0.4(4) . . . . ?
C19 C20 C21 C22 0.6(4) . . . . ?
C18 C17 C15 C14 108.1(3) . . . . ?
C18 C17 C15 C19 -129.4(2) . . . . ?
C18 C17 C15 C16 -11.4(3) . . . . ?
C12 C11 C3 C2 158.4(2) . . . . ?
C12 C11 C3 C5 -83.2(3) . . . . ?
C12 C11 C3 C4 38.8(3) . . . . ?
C13 C14 C15 C17 -111.2(3) . . . . ?
C13 C14 C15 C19 125.9(3) . . . . ?
C13 C14 C15 C16 8.5(4) . . . . ?
C4 C3 C5 C10 -149.1(2) . . . . ?
C4 C3 C5 C6 37.0(3) . . . . ?
C24 C19 C20 C21 -3.0(4) . . . . ?
C24 C23 C22 F2 178.6(2) . . . . ?
C24 C23 C22 C21 -2.2(4) . . . . ?
C10 C5 C6 C7 0.0(4) . . . . ?
C6 C5 C10 C9 0.4(4) . . . . ?
C20 C19 C24 C23 2.9(4) . . . . ?
C20 C21 C22 F2 -178.7(2) . . . . ?
C20 C21 C22 C23 2.1(4) . . . . ?
C16 C15 C19 C24 -89.9(3) . . . . ?
C16 C15 C19 C20 86.8(3) . . . . ?
C9 C8 C7 C6 0.6(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
