#------------------------------------------------------------------------------
#$Date: 2021-01-04 05:13:38 +0200 (Mon, 04 Jan 2021) $
#$Revision: 260428 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/54/4135418.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_4135418
loop_
_publ_author_name
'Chandrachud, Preeti P.'
'Wojtas, Lukasz'
'Lopchuk, Justin M.'
_publ_section_title
;
 Decarboxylative Amination: Diazirines as Single and Double Electrophilic
 Nitrogen Transfer Reagents.
;
_journal_issue                   52
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              21743
_journal_page_last               21750
_journal_paper_doi               10.1021/jacs.0c09403
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C12 H13 F3 N2 O'
_chemical_formula_sum            'C12 H13 F3 N2 O'
_chemical_formula_weight         258.24
_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   mixed
_audit_creation_date             2019-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0379(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3765(4)
_cell_length_b                   23.4519(9)
_cell_length_c                   10.6409(4)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.84
_cell_measurement_theta_min      3.77
_cell_volume                     2339.90(16)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.07
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            36778
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.156
_diffrn_reflns_theta_min         3.769
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.105
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1258 before and 0.0883 after correction.
The Ratio of minimum to maximum transmission is 0.8010.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0480
_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)+(0.0548P)²+2.0186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4354
_reflns_number_total             4895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c09403_si_006.cif
_cod_data_source_block           D
_cod_depositor_comments
'Adding full bibliography for 4135411--4135418.cif.'
_cod_database_code               4135418
_shelx_shelxl_version_number     2018/3
_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   0.949
_shelx_estimated_absorpt_t_min   0.875
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6404(17)
 0.3596(17)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C21(H21A,H21B), C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C34(H34), C35(H35),
 C36(H36), C37(H37), C38(H38)
3.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C25(H25A,H25B,H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.9020(3) 0.22496(11) 0.3491(3) 0.0280(5) Uani 1 1 d . . . . .
H1A H 0.890837 0.218579 0.440581 0.034 Uiso 1 1 calc R . . . .
H1B H 0.996663 0.211724 0.320088 0.034 Uiso 1 1 calc R . . . .
O2 O 0.8679(2) 0.28324(8) 0.30982(18) 0.0319(4) Uani 1 1 d . . . . .
C3 C 0.7287(3) 0.26411(11) 0.2660(2) 0.0277(5) Uani 1 1 d . . . . .
H3A H 0.705024 0.277450 0.180220 0.033 Uiso 1 1 calc R . . . .
H3B H 0.650302 0.272866 0.325179 0.033 Uiso 1 1 calc R . . . .
C4 C 0.7775(3) 0.20149(11) 0.2707(2) 0.0246(5) Uani 1 1 d . . . . .
C5 C 0.8215(3) 0.17849(12) 0.1432(3) 0.0302(6) Uani 1 1 d . . . . .
H5A H 0.885002 0.205868 0.101964 0.045 Uiso 1 1 calc GR . . . .
H5B H 0.736431 0.172631 0.091237 0.045 Uiso 1 1 calc GR . . . .
H5C H 0.871380 0.142109 0.154189 0.045 Uiso 1 1 calc GR . . . .
N6 N 0.6693(2) 0.16286(9) 0.32138(19) 0.0231(4) Uani 1 1 d . . . . .
N7 N 0.6513(2) 0.16895(9) 0.4616(2) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.7120(3) 0.11773(10) 0.4061(2) 0.0232(5) Uani 1 1 d . . . . .
C9 C 0.6163(3) 0.06581(11) 0.3948(3) 0.0274(5) Uani 1 1 d . . . . .
F10 F 0.47832(17) 0.07940(7) 0.38295(17) 0.0358(4) Uani 1 1 d . . . . .
F11 F 0.6501(2) 0.03353(7) 0.29547(16) 0.0367(4) Uani 1 1 d . . . . .
F12 F 0.62823(18) 0.03285(7) 0.49724(15) 0.0327(4) Uani 1 1 d . . . . .
C13 C 0.8636(3) 0.10307(10) 0.4418(2) 0.0234(5) Uani 1 1 d . . . . .
C14 C 0.9521(3) 0.07301(11) 0.3602(2) 0.0285(5) Uani 1 1 d . . . . .
H14 H 0.918334 0.062317 0.279414 0.034 Uiso 1 1 calc R . . . .
C15 C 1.0893(3) 0.05866(12) 0.3968(3) 0.0320(6) Uani 1 1 d . . . . .
H15 H 1.149414 0.038334 0.340580 0.038 Uiso 1 1 calc R . . . .
C16 C 1.1398(3) 0.07375(12) 0.5149(3) 0.0314(6) Uani 1 1 d . . . . .
H16 H 1.234249 0.064128 0.539163 0.038 Uiso 1 1 calc R . . . .
C17 C 1.0516(3) 0.10290(11) 0.5970(3) 0.0284(5) Uani 1 1 d . . . . .
H17 H 1.085336 0.112891 0.678238 0.034 Uiso 1 1 calc R . . . .
C18 C 0.9135(3) 0.11765(11) 0.5609(2) 0.0256(5) Uani 1 1 d . . . . .
H18 H 0.853412 0.137660 0.617640 0.031 Uiso 1 1 calc R . . . .
C21 C 0.2288(3) 0.23336(11) 0.5944(3) 0.0283(5) Uani 1 1 d . . . . .
H21A H 0.201303 0.219117 0.678545 0.034 Uiso 1 1 calc R . . . .
H21B H 0.153212 0.225095 0.531951 0.034 Uiso 1 1 calc R . . . .
O22 O 0.3701(2) 0.21490(8) 0.55481(18) 0.0314(4) Uani 1 1 d . . . . .
C23 C 0.4058(3) 0.27339(11) 0.5189(3) 0.0283(5) Uani 1 1 d . . . . .
H23A H 0.398520 0.280560 0.427474 0.034 Uiso 1 1 calc R . . . .
H23B H 0.499037 0.286446 0.551874 0.034 Uiso 1 1 calc R . . . .
C24 C 0.2770(3) 0.29597(11) 0.5945(2) 0.0239(5) Uani 1 1 d . . . . .
C25 C 0.3165(3) 0.31821(12) 0.7244(2) 0.0299(6) Uani 1 1 d . . . . .
H25A H 0.229594 0.323803 0.774057 0.045 Uiso 1 1 calc GR . . . .
H25B H 0.366900 0.354616 0.716102 0.045 Uiso 1 1 calc GR . . . .
H25C H 0.378352 0.290520 0.766716 0.045 Uiso 1 1 calc GR . . . .
N26 N 0.1709(2) 0.33497(9) 0.54128(19) 0.0229(4) Uani 1 1 d . . . . .
N27 N 0.1537(2) 0.32928(9) 0.40090(19) 0.0242(4) Uani 1 1 d . . . . .
C28 C 0.2161(3) 0.38018(10) 0.4573(2) 0.0231(5) Uani 1 1 d . . . . .
C29 C 0.1214(3) 0.43237(11) 0.4714(2) 0.0258(5) Uani 1 1 d . . . . .
F30 F -0.01752(16) 0.41955(7) 0.47607(16) 0.0335(4) Uani 1 1 d . . . . .
F31 F 0.15276(19) 0.46155(7) 0.57604(15) 0.0333(4) Uani 1 1 d . . . . .
F32 F 0.13827(18) 0.46847(6) 0.37429(15) 0.0321(3) Uani 1 1 d . . . . .
C33 C 0.3675(3) 0.39404(10) 0.4240(2) 0.0238(5) Uani 1 1 d . . . . .
C34 C 0.4586(3) 0.42047(11) 0.5103(2) 0.0276(5) Uani 1 1 d . . . . .
H34 H 0.425300 0.429371 0.592291 0.033 Uiso 1 1 calc R . . . .
C35 C 0.5980(3) 0.43375(12) 0.4764(3) 0.0300(6) Uani 1 1 d . . . . .
H35 H 0.660139 0.451277 0.535442 0.036 Uiso 1 1 calc R . . . .
C36 C 0.6463(3) 0.42136(11) 0.3560(3) 0.0306(6) Uani 1 1 d . . . . .
H36 H 0.741373 0.430394 0.332628 0.037 Uiso 1 1 calc R . . . .
C37 C 0.5549(3) 0.39570(11) 0.2699(3) 0.0292(5) Uani 1 1 d . . . . .
H37 H 0.587962 0.387554 0.187494 0.035 Uiso 1 1 calc R . . . .
C38 C 0.4163(3) 0.38187(11) 0.3031(2) 0.0267(5) Uani 1 1 d . . . . .
H38 H 0.354766 0.364185 0.243808 0.032 Uiso 1 1 calc R . . . .
H7 H 0.555(4) 0.1659(14) 0.473(3) 0.039(9) Uiso 1 1 d . . . . .
H27 H 0.056(4) 0.3356(14) 0.387(3) 0.041(9) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
H1A C1 H1B 110.8 . . ?
O2 C1 H1A 113.5 . . ?
O2 C1 H1B 113.5 . . ?
O2 C1 C4 90.78(19) . . ?
C4 C1 H1A 113.5 . . ?
C4 C1 H1B 113.5 . . ?
C3 O2 C1 89.95(18) . . ?
O2 C3 H3A 113.5 . . ?
O2 C3 H3B 113.5 . . ?
O2 C3 C4 91.0(2) . . ?
H3A C3 H3B 110.8 . . ?
C4 C3 H3A 113.5 . . ?
C4 C3 H3B 113.5 . . ?
C1 C4 C3 84.35(19) . . ?
C5 C4 C1 114.0(2) . . ?
C5 C4 C3 113.0(2) . . ?
N6 C4 C1 123.3(2) . . ?
N6 C4 C3 113.4(2) . . ?
N6 C4 C5 107.3(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 N6 N7 112.57(19) . . ?
C8 N6 C4 119.4(2) . . ?
C8 N6 N7 58.94(14) . . ?
N6 N7 H7 104(2) . . ?
C8 N7 N6 58.41(15) . . ?
C8 N7 H7 112(2) . . ?
N6 C8 N7 62.65(15) . . ?
N6 C8 C9 112.0(2) . . ?
N6 C8 C13 125.7(2) . . ?
N7 C8 C9 117.6(2) . . ?
N7 C8 C13 117.0(2) . . ?
C13 C8 C9 113.2(2) . . ?
F10 C9 C8 112.8(2) . . ?
F10 C9 F11 106.8(2) . . ?
F10 C9 F12 107.1(2) . . ?
F11 C9 C8 112.1(2) . . ?
F11 C9 F12 107.2(2) . . ?
F12 C9 C8 110.5(2) . . ?
C14 C13 C8 121.3(2) . . ?
C14 C13 C18 119.4(2) . . ?
C18 C13 C8 119.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
H21A C21 H21B 110.8 . . ?
O22 C21 H21A 113.5 . . ?
O22 C21 H21B 113.5 . . ?
O22 C21 C24 90.94(19) . . ?
C24 C21 H21A 113.5 . . ?
C24 C21 H21B 113.5 . . ?
C21 O22 C23 90.31(17) . . ?
O22 C23 H23A 113.6 . . ?
O22 C23 H23B 113.6 . . ?
O22 C23 C24 90.35(18) . . ?
H23A C23 H23B 110.9 . . ?
C24 C23 H23A 113.6 . . ?
C24 C23 H23B 113.6 . . ?
C21 C24 C23 84.39(19) . . ?
C25 C24 C21 113.6(2) . . ?
C25 C24 C23 113.6(2) . . ?
N26 C24 C21 113.3(2) . . ?
N26 C24 C23 122.9(2) . . ?
N26 C24 C25 107.6(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 N26 N27 113.58(19) . . ?
C28 N26 C24 119.8(2) . . ?
C28 N26 N27 59.03(15) . . ?
N26 N27 H27 104(2) . . ?
C28 N27 N26 58.49(15) . . ?
C28 N27 H27 109(2) . . ?
N26 C28 N27 62.48(15) . . ?
N26 C28 C29 110.9(2) . . ?
N26 C28 C33 125.5(2) . . ?
N27 C28 C29 117.8(2) . . ?
N27 C28 C33 117.4(2) . . ?
C33 C28 C29 113.7(2) . . ?
F30 C29 C28 113.1(2) . . ?
F30 C29 F31 107.3(2) . . ?
F30 C29 F32 106.6(2) . . ?
F31 C29 C28 111.4(2) . . ?
F31 C29 F32 106.9(2) . . ?
F32 C29 C28 111.2(2) . . ?
C34 C33 C28 121.3(2) . . ?
C38 C33 C28 119.0(2) . . ?
C38 C33 C34 119.7(2) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.2(2) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 119.9(3) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 120.1 . . ?
C35 C36 C37 119.8(3) . . ?
C37 C36 H36 120.1 . . ?
C36 C37 H37 119.6 . . ?
C38 C37 C36 120.7(3) . . ?
C38 C37 H37 119.6 . . ?
C33 C38 H38 120.2 . . ?
C37 C38 C33 119.7(3) . . ?
C37 C38 H38 120.2 . . ?
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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 O2 1.465(3) . ?
C1 C4 1.537(4) . ?
O2 C3 1.457(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.539(3) . ?
C4 C5 1.517(3) . ?
C4 N6 1.464(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N6 N7 1.509(3) . ?
N6 C8 1.447(3) . ?
N7 C8 1.455(3) . ?
N7 H7 0.91(4) . ?
C8 C9 1.517(4) . ?
C8 C13 1.511(3) . ?
C9 F10 1.339(3) . ?
C9 F11 1.339(3) . ?
C9 F12 1.341(3) . ?
C13 C14 1.393(3) . ?
C13 C18 1.394(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(4) . ?
C18 H18 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 O22 1.456(3) . ?
C21 C24 1.536(3) . ?
O22 C23 1.463(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.545(3) . ?
C24 C25 1.523(3) . ?
C24 N26 1.465(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N26 N27 1.508(3) . ?
N26 C28 1.450(3) . ?
N27 C28 1.458(3) . ?
N27 H27 0.94(4) . ?
C28 C29 1.520(3) . ?
C28 C33 1.499(3) . ?
C29 F30 1.337(3) . ?
C29 F31 1.340(3) . ?
C29 F32 1.345(3) . ?
C33 C34 1.399(4) . ?
C33 C38 1.396(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.392(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.389(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.391(4) . ?
C37 H37 0.9500 . ?
C37 C38 1.386(4) . ?
C38 H38 0.9500 . ?
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
C1 O2 C3 C4 -15.27(18) . . . . ?
C1 C4 N6 N7 25.6(3) . . . . ?
C1 C4 N6 C8 -40.4(3) . . . . ?
O2 C1 C4 C3 -14.53(17) . . . . ?
O2 C1 C4 C5 98.2(2) . . . . ?
O2 C1 C4 N6 -128.8(2) . . . . ?
O2 C3 C4 C1 14.61(17) . . . . ?
O2 C3 C4 C5 -99.1(2) . . . . ?
O2 C3 C4 N6 138.5(2) . . . . ?
C3 C4 N6 N7 -73.3(3) . . . . ?
C3 C4 N6 C8 -139.3(2) . . . . ?
C4 C1 O2 C3 15.29(18) . . . . ?
C4 N6 N7 C8 -111.7(2) . . . . ?
C4 N6 C8 N7 100.1(2) . . . . ?
C4 N6 C8 C9 -149.2(2) . . . . ?
C4 N6 C8 C13 -4.9(3) . . . . ?
C5 C4 N6 N7 161.2(2) . . . . ?
C5 C4 N6 C8 95.2(3) . . . . ?
N6 N7 C8 C9 -101.9(2) . . . . ?
N6 N7 C8 C13 118.3(2) . . . . ?
N6 C8 C9 F10 -40.9(3) . . . . ?
N6 C8 C9 F11 79.7(3) . . . . ?
N6 C8 C9 F12 -160.8(2) . . . . ?
N6 C8 C13 C14 -77.0(3) . . . . ?
N6 C8 C13 C18 106.0(3) . . . . ?
N7 N6 C8 C9 110.7(2) . . . . ?
N7 N6 C8 C13 -105.0(3) . . . . ?
N7 C8 C9 F10 28.7(3) . . . . ?
N7 C8 C9 F11 149.3(2) . . . . ?
N7 C8 C9 F12 -91.1(3) . . . . ?
N7 C8 C13 C14 -151.4(2) . . . . ?
N7 C8 C13 C18 31.6(3) . . . . ?
C8 C13 C14 C15 -178.1(2) . . . . ?
C8 C13 C18 C17 178.0(2) . . . . ?
C9 C8 C13 C14 67.0(3) . . . . ?
C9 C8 C13 C18 -110.0(3) . . . . ?
C13 C8 C9 F10 170.1(2) . . . . ?
C13 C8 C9 F11 -69.3(3) . . . . ?
C13 C8 C9 F12 50.2(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C13 C18 C17 0.9(4) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C18 C13 C14 C15 -1.1(4) . . . . ?
C21 O22 C23 C24 15.4(2) . . . . ?
C21 C24 N26 N27 -70.9(3) . . . . ?
C21 C24 N26 C28 -137.5(2) . . . . ?
O22 C21 C24 C23 14.72(18) . . . . ?
O22 C21 C24 C25 -98.6(2) . . . . ?
O22 C21 C24 N26 138.2(2) . . . . ?
O22 C23 C24 C21 -14.65(19) . . . . ?
O22 C23 C24 C25 98.6(2) . . . . ?
O22 C23 C24 N26 -128.9(2) . . . . ?
C23 C24 N26 N27 27.9(3) . . . . ?
C23 C24 N26 C28 -38.7(3) . . . . ?
C24 C21 O22 C23 -15.50(19) . . . . ?
C24 N26 N27 C28 -111.7(2) . . . . ?
C24 N26 C28 N27 101.2(2) . . . . ?
C24 N26 C28 C29 -147.5(2) . . . . ?
C24 N26 C28 C33 -4.2(4) . . . . ?
C25 C24 N26 N27 162.72(19) . . . . ?
C25 C24 N26 C28 96.1(2) . . . . ?
N26 N27 C28 C29 -100.5(2) . . . . ?
N26 N27 C28 C33 117.9(2) . . . . ?
N26 C28 C29 F30 -44.6(3) . . . . ?
N26 C28 C29 F31 76.3(3) . . . . ?
N26 C28 C29 F32 -164.5(2) . . . . ?
N26 C28 C33 C34 -73.0(3) . . . . ?
N26 C28 C33 C38 109.1(3) . . . . ?
N27 N26 C28 C29 111.3(2) . . . . ?
N27 N26 C28 C33 -105.4(3) . . . . ?
N27 C28 C29 F30 24.5(3) . . . . ?
N27 C28 C29 F31 145.4(2) . . . . ?
N27 C28 C29 F32 -95.4(3) . . . . ?
N27 C28 C33 C34 -147.3(2) . . . . ?
N27 C28 C33 C38 34.8(3) . . . . ?
C28 C33 C34 C35 -178.9(2) . . . . ?
C28 C33 C38 C37 178.4(2) . . . . ?
C29 C28 C33 C34 69.5(3) . . . . ?
C29 C28 C33 C38 -108.4(3) . . . . ?
C33 C28 C29 F30 167.5(2) . . . . ?
C33 C28 C29 F31 -71.6(3) . . . . ?
C33 C28 C29 F32 47.6(3) . . . . ?
C33 C34 C35 C36 0.8(4) . . . . ?
C34 C33 C38 C37 0.5(4) . . . . ?
C34 C35 C36 C37 0.0(4) . . . . ?
C35 C36 C37 C38 -0.5(4) . . . . ?
C36 C37 C38 C33 0.3(4) . . . . ?
C38 C33 C34 C35 -1.0(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6404(17)
2 0.3596(17)
