#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/91/1559112.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_1559112
loop_
_publ_author_name
'Sun, Xi-Shang'
'Wang, Xing-Heng'
'Tao, Hai-Yan'
'Wei, Liang'
'Wang, Chun-Jiang'
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Quaternary Trifluoromethyl α- to
 ϵ-Amino Acid Derivatives via Umpolung Allylation/2-aza-Cope
 Rearrangement
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04685J
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H25 F3 N2 O3'
_chemical_formula_weight         446.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2020-07-22 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.74(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.227(5)
_cell_length_b                   15.501(5)
_cell_length_c                   12.834(4)
_cell_measurement_reflns_used    3770
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      61.40
_cell_measurement_theta_min      3.68
_cell_volume                     2389.8(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14495
_diffrn_reflns_point_group_measured_fraction_full 0.831
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        63.259
_diffrn_reflns_theta_max         63.259
_diffrn_reflns_theta_min         3.505
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1400 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         6479
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0541
_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)+(0.0693P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1475
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.695
_reflns_Friedel_fraction_max     0.695
_reflns_number_gt                4356
_reflns_number_total             6479
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc04685j2.cif
_cod_data_source_block           x_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        2390.0(15)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1559112
_shelx_shelxl_version_number     2016/4
_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_min   0.960
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.9368(3) 0.5340(3) 0.2182(3) 0.0724(12) Uani 1 1 d . . . . .
F1 F 1.1828(4) 0.2750(3) 0.2236(3) 0.1272(18) Uani 1 1 d . . . . .
N1 N 1.0008(5) 0.4029(4) 0.3536(3) 0.0709(15) Uani 1 1 d . . . . .
H1 H 0.969(5) 0.458(4) 0.341(4) 0.072(19) Uiso 1 1 d . . . . .
C1 C 1.0541(5) 0.3733(4) 0.2773(4) 0.0584(15) Uani 1 1 d . . . . .
F2 F 1.0320(5) 0.2224(3) 0.2606(4) 0.1336(18) Uani 1 1 d . . . . .
N2 N 1.0888(4) 0.2804(3) 0.5911(3) 0.0610(13) Uani 1 1 d . . . . .
O2 O 1.0020(5) 0.5309(3) 0.0664(3) 0.1052(17) Uani 1 1 d . . . . .
C2 C 1.0564(5) 0.4191(4) 0.1863(4) 0.0644(16) Uani 1 1 d . . . . .
H2 H 1.099026 0.398518 0.138743 0.077 Uiso 1 1 calc R U . . .
N3 N 0.4722(6) 0.6506(4) 0.8341(4) 0.0857(19) Uani 1 1 d . . . . .
H3 H 0.464(5) 0.703(4) 0.825(5) 0.08(2) Uiso 1 1 d . . . . .
F3 F 1.1633(4) 0.2653(3) 0.3849(3) 0.1199(17) Uani 1 1 d . . . . .
O3 O 1.1764(4) 0.4080(3) 0.5576(4) 0.0863(13) Uani 1 1 d . . . . .
C3 C 0.9948(5) 0.4980(4) 0.1620(4) 0.0653(17) Uani 1 1 d . . . . .
C4 C 0.9228(8) 0.6060(6) 0.0247(6) 0.117(3) Uani 1 1 d D . . . .
H4A H 0.902236 0.604196 -0.052029 0.140 Uiso 1 1 calc R U . . .
H4AB H 0.855672 0.603785 0.054755 0.140 Uiso 1 1 calc R U . . .
O4 O 0.4573(4) 0.7946(3) 0.7102(3) 0.0778(12) Uani 1 1 d . . . . .
N4 N 0.5618(4) 0.5418(3) 1.0812(3) 0.0631(13) Uani 1 1 d . . . . .
F4 F 0.6227(5) 0.5044(3) 0.8715(3) 0.138(2) Uani 1 1 d . . . . .
C5 C 0.9871(10) 0.6827(8) 0.0593(10) 0.179(5) Uani 1 1 d D . . . .
H5A H 1.057828 0.679406 0.037276 0.268 Uiso 1 1 calc R U . . .
H5B H 0.998578 0.686752 0.135224 0.268 Uiso 1 1 calc R U . . .
H5C H 0.947546 0.732740 0.028424 0.268 Uiso 1 1 calc R U . . .
O5 O 0.5437(5) 0.7845(3) 0.5702(3) 0.1021(16) Uani 1 1 d . . . . .
F5 F 0.6395(5) 0.5060(3) 0.7092(4) 0.165(3) Uani 1 1 d . . . . .
C6 C 1.1105(6) 0.2860(5) 0.2867(5) 0.084(2) Uani 1 1 d . . . . .
O6 O 0.6499(4) 0.6645(3) 1.0366(4) 0.0963(15) Uani 1 1 d . . . . .
F6 F 0.4826(6) 0.4703(3) 0.7487(4) 0.160(3) Uani 1 1 d . . . . .
C7 C 0.9860(5) 0.3694(4) 0.4572(3) 0.0541(14) Uani 1 1 d . . . . .
C8 C 0.9285(5) 0.2823(4) 0.4584(4) 0.0572(15) Uani 1 1 d . . . . .
C9 C 0.8306(5) 0.2486(4) 0.3990(4) 0.0708(17) Uani 1 1 d . . . . .
H9 H 0.790268 0.279767 0.342794 0.085 Uiso 1 1 calc R U . . .
C11 C 0.8517(7) 0.1223(5) 0.5109(6) 0.086(2) Uani 1 1 d . . . . .
H11 H 0.824567 0.069422 0.529038 0.103 Uiso 1 1 calc R U . . .
C10 C 0.7938(6) 0.1672(5) 0.4253(6) 0.090(2) Uani 1 1 d . . . . .
H10 H 0.730066 0.143271 0.384762 0.108 Uiso 1 1 calc R U . . .
C12 C 0.9524(6) 0.1553(4) 0.5723(5) 0.0743(18) Uani 1 1 d . . . . .
H12 H 0.991560 0.124492 0.629497 0.089 Uiso 1 1 calc R U . . .
C13 C 0.9908(5) 0.2361(4) 0.5437(4) 0.0602(15) Uani 1 1 d . . . . .
C14 C 1.1731(6) 0.2516(5) 0.6838(5) 0.096(2) Uani 1 1 d . . . . .
H14A H 1.202571 0.196578 0.668530 0.143 Uiso 1 1 calc R U . . .
H14B H 1.138613 0.246531 0.744900 0.143 Uiso 1 1 calc R U . . .
H14C H 1.232310 0.293040 0.697718 0.143 Uiso 1 1 calc R U . . .
C15 C 1.0977(5) 0.3567(4) 0.5385(4) 0.0602(15) Uani 1 1 d . . . . .
C16 C 0.9206(5) 0.4443(4) 0.5049(4) 0.0547(15) Uani 1 1 d . . . . .
H16 H 0.964732 0.496857 0.502877 0.066 Uiso 1 1 calc R U . . .
C17 C 0.8024(5) 0.4643(4) 0.4383(4) 0.0719(18) Uani 1 1 d . . . . .
H17A H 0.808578 0.473652 0.364893 0.086 Uiso 1 1 calc R U . . .
H17B H 0.754415 0.414754 0.440698 0.086 Uiso 1 1 calc R U . . .
C18 C 0.7489(5) 0.5439(4) 0.4792(5) 0.084(2) Uani 1 1 d . . . . .
H18A H 0.679252 0.556075 0.433309 0.127 Uiso 1 1 calc R U . . .
H18B H 0.797764 0.592550 0.480310 0.127 Uiso 1 1 calc R U . . .
H18C H 0.736376 0.532981 0.549672 0.127 Uiso 1 1 calc R U . . .
C19 C 0.9176(5) 0.4280(4) 0.6217(4) 0.0527(14) Uani 1 1 d . . . . .
C20 C 0.9869(5) 0.4780(4) 0.7000(4) 0.0680(17) Uani 1 1 d . . . . .
H20 H 1.035157 0.518441 0.679878 0.082 Uiso 1 1 calc R U . . .
C21 C 0.9830(6) 0.4671(5) 0.8061(5) 0.082(2) Uani 1 1 d . . . . .
H21 H 1.027963 0.500851 0.856765 0.099 Uiso 1 1 calc R U . . .
C22 C 0.9134(6) 0.4068(5) 0.8374(4) 0.0777(19) Uani 1 1 d . . . . .
H22 H 0.912680 0.398950 0.909110 0.093 Uiso 1 1 calc R U . . .
C23 C 0.8437(6) 0.3572(4) 0.7621(4) 0.0762(19) Uani 1 1 d . . . . .
H23 H 0.796136 0.316828 0.783435 0.091 Uiso 1 1 calc R U . . .
C24 C 0.8455(5) 0.3683(4) 0.6547(4) 0.0582(15) Uani 1 1 d . . . . .
H24 H 0.798342 0.335721 0.604514 0.070 Uiso 1 1 calc R U . . .
C26 C 0.5322(6) 0.6184(4) 0.7634(4) 0.0747(19) Uani 1 1 d . . . . .
C25 C 0.4575(5) 0.6224(4) 0.9396(4) 0.0597(15) Uani 1 1 d . . . . .
C27 C 0.5496(6) 0.6650(5) 0.6782(4) 0.0758(19) Uani 1 1 d . . . . .
H27 H 0.587258 0.638516 0.630283 0.091 Uiso 1 1 calc R U . . .
C28 C 0.5134(6) 0.7525(4) 0.6578(4) 0.0716(18) Uani 1 1 d . . . . .
C29 C 0.5065(9) 0.8732(6) 0.5381(7) 0.132(3) Uani 1 1 d D U . . .
H29A H 0.486176 0.876451 0.461467 0.159 Uiso 1 1 calc R U . . .
H29B H 0.441377 0.887645 0.567753 0.159 Uiso 1 1 calc R U . . .
C30 C 0.5951(10) 0.9339(8) 0.5756(12) 0.200(5) Uani 1 1 d D U . . .
H30A H 0.600700 0.974620 0.520500 0.300 Uiso 1 1 calc R U . . .
H30B H 0.664257 0.903370 0.594837 0.300 Uiso 1 1 calc R U . . .
H30C H 0.579210 0.964006 0.636478 0.300 Uiso 1 1 calc R U . . .
C31 C 0.5744(9) 0.5272(6) 0.7753(6) 0.111(3) Uani 1 1 d . . . . .
C32 C 0.4029(5) 0.5371(4) 0.9484(4) 0.0596(15) Uani 1 1 d . . . . .
C33 C 0.3057(6) 0.4971(5) 0.8904(5) 0.087(2) Uani 1 1 d . . . . .
H33 H 0.264601 0.523606 0.830677 0.104 Uiso 1 1 calc R U . . .
C34 C 0.2733(8) 0.4181(6) 0.9243(8) 0.110(3) Uani 1 1 d . . . . .
H34 H 0.210176 0.391356 0.886290 0.132 Uiso 1 1 calc R U . . .
C35 C 0.3323(8) 0.3779(5) 1.0129(8) 0.110(3) Uani 1 1 d . . . . .
H35 H 0.307748 0.325142 1.034248 0.132 Uiso 1 1 calc R U . . .
C36 C 0.4295(7) 0.4157(5) 1.0719(5) 0.084(2) Uani 1 1 d . . . . .
H36 H 0.468940 0.388833 1.132157 0.101 Uiso 1 1 calc R U . . .
C37 C 0.4644(5) 0.4944(4) 1.0371(4) 0.0604(15) Uani 1 1 d . . . . .
C38 C 0.6407(6) 0.5196(5) 1.1794(5) 0.096(2) Uani 1 1 d . . . . .
H38A H 0.681185 0.468548 1.167885 0.144 Uiso 1 1 calc R U . . .
H38B H 0.600314 0.509496 1.235647 0.144 Uiso 1 1 calc R U . . .
H38C H 0.691859 0.566478 1.198600 0.144 Uiso 1 1 calc R U . . .
C39 C 0.5713(5) 0.6139(4) 1.0224(4) 0.0634(16) Uani 1 1 d . . . . .
C40 C 0.3934(5) 0.7005(4) 0.9826(4) 0.0597(15) Uani 1 1 d . . . . .
H40 H 0.437130 0.752535 0.975806 0.072 Uiso 1 1 calc R U . . .
C41 C 0.2751(6) 0.7167(5) 0.9148(4) 0.085(2) Uani 1 1 d . . . . .
H41A H 0.279097 0.714522 0.840029 0.102 Uiso 1 1 calc R U . . .
H41B H 0.224834 0.671565 0.928834 0.102 Uiso 1 1 calc R U . . .
C42 C 0.2297(7) 0.8042(6) 0.9405(6) 0.114(3) Uani 1 1 d . . . . .
H42A H 0.171036 0.821452 0.883748 0.171 Uiso 1 1 calc R U . . .
H42B H 0.288370 0.846249 0.948865 0.171 Uiso 1 1 calc R U . . .
H42C H 0.201138 0.800100 1.005114 0.171 Uiso 1 1 calc R U . . .
C43 C 0.3912(5) 0.6906(4) 1.1013(4) 0.0606(16) Uani 1 1 d . . . . .
C44 C 0.4659(6) 0.7376(5) 1.1766(5) 0.082(2) Uani 1 1 d . . . . .
H44 H 0.515914 0.775583 1.154495 0.098 Uiso 1 1 calc R U . . .
C45 C 0.4654(8) 0.7276(6) 1.2855(5) 0.113(3) Uani 1 1 d . . . . .
H45 H 0.516988 0.757069 1.335263 0.135 Uiso 1 1 calc R U . . .
C46 C 0.3896(8) 0.6749(6) 1.3182(5) 0.107(3) Uani 1 1 d . . . . .
H46 H 0.387468 0.670290 1.390089 0.128 Uiso 1 1 calc R U . . .
C47 C 0.3151(6) 0.6276(5) 1.2443(5) 0.098(2) Uani 1 1 d . . . . .
H47 H 0.264728 0.590829 1.267814 0.117 Uiso 1 1 calc R U . . .
C48 C 0.3146(5) 0.6344(4) 1.1363(4) 0.0698(17) Uani 1 1 d . . . . .
H48 H 0.264513 0.602476 1.087850 0.084 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
F F 0.0727 0.0534 '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
C1 N1 C7 133.8(6) . . ?
C1 N1 H1 115(3) . . ?
C7 N1 H1 111(3) . . ?
N1 C1 C2 122.0(6) . . ?
N1 C1 C6 121.2(5) . . ?
C2 C1 C6 116.8(5) . . ?
C15 N2 C13 110.1(5) . . ?
C15 N2 C14 122.9(6) . . ?
C13 N2 C14 127.0(5) . . ?
C3 O2 C4 117.3(5) . . ?
C1 C2 C3 122.1(5) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C26 N3 C25 132.8(6) . . ?
C26 N3 H3 109(4) . . ?
C25 N3 H3 113(4) . . ?
O1 C3 O2 120.2(6) . . ?
O1 C3 C2 126.3(5) . . ?
O2 C3 C2 113.5(5) . . ?
C5 C4 O2 104.0(8) . . ?
C5 C4 H4A 111.0 . . ?
O2 C4 H4A 111.0 . . ?
C5 C4 H4AB 111.0 . . ?
O2 C4 H4AB 111.0 . . ?
H4A C4 H4AB 109.0 . . ?
C39 N4 C37 110.7(5) . . ?
C39 N4 C38 123.5(6) . . ?
C37 N4 C38 125.7(5) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C28 O5 C29 117.2(6) . . ?
F1 C6 F3 106.6(6) . . ?
F1 C6 F2 106.0(6) . . ?
F3 C6 F2 104.4(6) . . ?
F1 C6 C1 114.5(6) . . ?
F3 C6 C1 114.9(5) . . ?
F2 C6 C1 109.6(6) . . ?
N1 C7 C8 117.2(4) . . ?
N1 C7 C15 114.1(5) . . ?
C8 C7 C15 103.2(4) . . ?
N1 C7 C16 104.2(4) . . ?
C8 C7 C16 112.1(4) . . ?
C15 C7 C16 105.8(4) . . ?
C9 C8 C13 121.3(6) . . ?
C9 C8 C7 132.6(5) . . ?
C13 C8 C7 105.9(5) . . ?
C8 C9 C10 119.1(6) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C10 C11 C12 121.4(7) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C10 C9 120.4(7) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C13 C12 C11 118.0(6) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C8 C13 C12 119.7(6) . . ?
C8 C13 N2 112.3(5) . . ?
C12 C13 N2 127.9(6) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 N2 125.8(6) . . ?
O3 C15 C7 126.9(5) . . ?
N2 C15 C7 107.2(5) . . ?
C19 C16 C17 112.3(4) . . ?
C19 C16 C7 111.2(4) . . ?
C17 C16 C7 114.4(4) . . ?
C19 C16 H16 106.1 . . ?
C17 C16 H16 106.1 . . ?
C7 C16 H16 106.1 . . ?
C18 C17 C16 112.4(5) . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
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 . . ?
C24 C19 C20 118.3(5) . . ?
C24 C19 C16 122.7(5) . . ?
C20 C19 C16 119.0(5) . . ?
C21 C20 C19 120.4(6) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.5(6) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.3(5) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 119.8(6) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C19 120.6(5) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C27 C26 N3 121.6(6) . . ?
C27 C26 C31 118.6(5) . . ?
N3 C26 C31 119.6(6) . . ?
N3 C25 C32 117.9(5) . . ?
N3 C25 C39 113.5(5) . . ?
C32 C25 C39 102.9(5) . . ?
N3 C25 C40 104.2(4) . . ?
C32 C25 C40 113.0(4) . . ?
C39 C25 C40 104.9(4) . . ?
C26 C27 C28 124.0(5) . . ?
C26 C27 H27 118.0 . . ?
C28 C27 H27 118.0 . . ?
O4 C28 O5 122.0(6) . . ?
O4 C28 C27 125.8(5) . . ?
O5 C28 C27 112.2(5) . . ?
C30 C29 O5 109.8(9) . . ?
C30 C29 H29A 109.7 . . ?
O5 C29 H29A 109.7 . . ?
C30 C29 H29B 109.7 . . ?
O5 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
F5 C31 F4 108.7(7) . . ?
F5 C31 F6 103.7(8) . . ?
F4 C31 F6 104.9(7) . . ?
F5 C31 C26 114.1(7) . . ?
F4 C31 C26 115.7(7) . . ?
F6 C31 C26 108.6(7) . . ?
C37 C32 C33 119.1(6) . . ?
C37 C32 C25 107.4(5) . . ?
C33 C32 C25 133.4(6) . . ?
C34 C33 C32 118.8(7) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C35 C34 C33 121.6(8) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C34 C35 C36 121.0(8) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C37 C36 C35 118.0(7) . . ?
C37 C36 H36 121.0 . . ?
C35 C36 H36 121.0 . . ?
C36 C37 C32 121.4(6) . . ?
C36 C37 N4 127.4(6) . . ?
C32 C37 N4 111.1(5) . . ?
N4 C38 H38A 109.5 . . ?
N4 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N4 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O6 C39 N4 125.9(6) . . ?
O6 C39 C25 127.5(6) . . ?
N4 C39 C25 106.5(6) . . ?
C43 C40 C41 112.5(5) . . ?
C43 C40 C25 111.5(4) . . ?
C41 C40 C25 113.1(5) . . ?
C43 C40 H40 106.4 . . ?
C41 C40 H40 106.4 . . ?
C25 C40 H40 106.4 . . ?
C42 C41 C40 111.0(6) . . ?
C42 C41 H41A 109.4 . . ?
C40 C41 H41A 109.4 . . ?
C42 C41 H41B 109.4 . . ?
C40 C41 H41B 109.4 . . ?
H41A C41 H41B 108.0 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C48 119.1(5) . . ?
C44 C43 C40 120.1(6) . . ?
C48 C43 C40 120.9(5) . . ?
C43 C44 C45 120.2(7) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C46 C45 C44 120.2(8) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C45 C46 C47 120.1(7) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C48 C47 C46 121.4(7) . . ?
C48 C47 H47 119.3 . . ?
C46 C47 H47 119.3 . . ?
C47 C48 C43 119.0(6) . . ?
C47 C48 H48 120.5 . . ?
C43 C48 H48 120.5 . . ?
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 C3 1.235(6) . ?
F1 C6 1.317(7) . ?
N1 C1 1.354(7) . ?
N1 C7 1.470(6) . ?
N1 H1 0.93(6) . ?
C1 C2 1.371(7) . ?
C1 C6 1.512(9) . ?
F2 C6 1.374(9) . ?
N2 C15 1.376(7) . ?
N2 C13 1.416(7) . ?
N2 C14 1.490(7) . ?
O2 C3 1.347(6) . ?
O2 C4 1.545(9) . ?
C2 C3 1.439(8) . ?
C2 H2 0.9300 . ?
N3 C26 1.363(7) . ?
N3 C25 1.466(6) . ?
N3 H3 0.83(7) . ?
F3 C6 1.344(7) . ?
O3 C15 1.237(7) . ?
C4 C5 1.449(11) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
O4 C28 1.233(7) . ?
N4 C39 1.366(8) . ?
N4 C37 1.423(7) . ?
N4 C38 1.478(7) . ?
F4 C31 1.314(9) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
O5 C28 1.342(6) . ?
O5 C29 1.483(10) . ?
F5 C31 1.309(8) . ?
O6 C39 1.228(7) . ?
F6 C31 1.418(11) . ?
C7 C8 1.524(8) . ?
C7 C15 1.568(8) . ?
C7 C16 1.595(7) . ?
C8 C9 1.395(8) . ?
C8 C13 1.407(7) . ?
C9 C10 1.402(9) . ?
C9 H9 0.9300 . ?
C11 C10 1.379(10) . ?
C11 C12 1.428(9) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C12 C13 1.410(8) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C19 1.527(6) . ?
C16 C17 1.568(8) . ?
C16 H16 0.9800 . ?
C17 C18 1.534(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.396(7) . ?
C19 C20 1.419(8) . ?
C20 C21 1.381(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.394(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.393(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C26 C27 1.360(8) . ?
C26 C31 1.503(10) . ?
C25 C32 1.494(8) . ?
C25 C39 1.591(8) . ?
C25 C40 1.596(7) . ?
C27 C28 1.436(9) . ?
C27 H27 0.9300 . ?
C29 C30 1.449(12) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C32 C37 1.407(8) . ?
C32 C33 1.423(9) . ?
C33 C34 1.382(11) . ?
C33 H33 0.9300 . ?
C34 C35 1.377(11) . ?
C34 H34 0.9300 . ?
C35 C36 1.411(10) . ?
C35 H35 0.9300 . ?
C36 C37 1.394(9) . ?
C36 H36 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C40 C43 1.536(7) . ?
C40 C41 1.564(8) . ?
C40 H40 0.9800 . ?
C41 C42 1.525(10) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.405(8) . ?
C43 C48 1.413(8) . ?
C44 C45 1.408(9) . ?
C44 H44 0.9300 . ?
C45 C46 1.359(12) . ?
C45 H45 0.9300 . ?
C46 C47 1.394(11) . ?
C46 H46 0.9300 . ?
C47 C48 1.389(7) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
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
C7 N1 C1 C2 -179.0(6) . . . . ?
C7 N1 C1 C6 3.4(11) . . . . ?
N1 C1 C2 C3 -5.2(9) . . . . ?
C6 C1 C2 C3 172.5(6) . . . . ?
C4 O2 C3 O1 -8.7(9) . . . . ?
C4 O2 C3 C2 169.4(6) . . . . ?
C1 C2 C3 O1 1.7(10) . . . . ?
C1 C2 C3 O2 -176.3(6) . . . . ?
C3 O2 C4 C5 93.0(9) . . . . ?
N1 C1 C6 F1 -162.7(6) . . . . ?
C2 C1 C6 F1 19.6(9) . . . . ?
N1 C1 C6 F3 -38.9(10) . . . . ?
C2 C1 C6 F3 143.5(6) . . . . ?
N1 C1 C6 F2 78.3(7) . . . . ?
C2 C1 C6 F2 -99.3(6) . . . . ?
C1 N1 C7 C8 -59.8(9) . . . . ?
C1 N1 C7 C15 61.0(9) . . . . ?
C1 N1 C7 C16 175.8(6) . . . . ?
N1 C7 C8 C9 -48.5(8) . . . . ?
C15 C7 C8 C9 -174.8(5) . . . . ?
C16 C7 C8 C9 71.8(7) . . . . ?
N1 C7 C8 C13 136.2(5) . . . . ?
C15 C7 C8 C13 10.0(5) . . . . ?
C16 C7 C8 C13 -103.4(5) . . . . ?
C13 C8 C9 C10 0.1(8) . . . . ?
C7 C8 C9 C10 -174.5(5) . . . . ?
C12 C11 C10 C9 -2.6(10) . . . . ?
C8 C9 C10 C11 2.2(9) . . . . ?
C10 C11 C12 C13 0.7(9) . . . . ?
C9 C8 C13 C12 -2.0(8) . . . . ?
C7 C8 C13 C12 173.9(4) . . . . ?
C9 C8 C13 N2 178.1(4) . . . . ?
C7 C8 C13 N2 -6.0(6) . . . . ?
C11 C12 C13 C8 1.6(8) . . . . ?
C11 C12 C13 N2 -178.6(5) . . . . ?
C15 N2 C13 C8 -1.4(6) . . . . ?
C14 N2 C13 C8 178.9(5) . . . . ?
C15 N2 C13 C12 178.8(5) . . . . ?
C14 N2 C13 C12 -1.0(9) . . . . ?
C13 N2 C15 O3 -176.5(5) . . . . ?
C14 N2 C15 O3 3.3(9) . . . . ?
C13 N2 C15 C7 7.9(6) . . . . ?
C14 N2 C15 C7 -172.4(5) . . . . ?
N1 C7 C15 O3 45.2(8) . . . . ?
C8 C7 C15 O3 173.4(5) . . . . ?
C16 C7 C15 O3 -68.7(7) . . . . ?
N1 C7 C15 N2 -139.2(5) . . . . ?
C8 C7 C15 N2 -11.0(5) . . . . ?
C16 C7 C15 N2 106.9(5) . . . . ?
N1 C7 C16 C19 -169.0(5) . . . . ?
C8 C7 C16 C19 63.3(6) . . . . ?
C15 C7 C16 C19 -48.5(6) . . . . ?
N1 C7 C16 C17 62.5(6) . . . . ?
C8 C7 C16 C17 -65.1(5) . . . . ?
C15 C7 C16 C17 -176.9(5) . . . . ?
C19 C16 C17 C18 59.3(6) . . . . ?
C7 C16 C17 C18 -172.8(4) . . . . ?
C17 C16 C19 C24 52.2(7) . . . . ?
C7 C16 C19 C24 -77.4(7) . . . . ?
C17 C16 C19 C20 -124.9(6) . . . . ?
C7 C16 C19 C20 105.5(6) . . . . ?
C24 C19 C20 C21 0.4(9) . . . . ?
C16 C19 C20 C21 177.6(6) . . . . ?
C19 C20 C21 C22 1.0(10) . . . . ?
C20 C21 C22 C23 -1.5(10) . . . . ?
C21 C22 C23 C24 0.6(10) . . . . ?
C22 C23 C24 C19 0.8(9) . . . . ?
C20 C19 C24 C23 -1.3(8) . . . . ?
C16 C19 C24 C23 -178.4(5) . . . . ?
C25 N3 C26 C27 -167.3(7) . . . . ?
C25 N3 C26 C31 16.7(13) . . . . ?
C26 N3 C25 C32 -63.7(11) . . . . ?
C26 N3 C25 C39 56.7(10) . . . . ?
C26 N3 C25 C40 170.2(8) . . . . ?
N3 C26 C27 C28 3.9(12) . . . . ?
C31 C26 C27 C28 179.9(8) . . . . ?
C29 O5 C28 O4 -0.3(11) . . . . ?
C29 O5 C28 C27 177.3(7) . . . . ?
C26 C27 C28 O4 -4.3(12) . . . . ?
C26 C27 C28 O5 178.2(7) . . . . ?
C28 O5 C29 C30 97.8(10) . . . . ?
C27 C26 C31 F5 9.9(13) . . . . ?
N3 C26 C31 F5 -173.9(8) . . . . ?
C27 C26 C31 F4 137.2(8) . . . . ?
N3 C26 C31 F4 -46.7(12) . . . . ?
C27 C26 C31 F6 -105.2(8) . . . . ?
N3 C26 C31 F6 70.9(9) . . . . ?
N3 C25 C32 C37 136.2(5) . . . . ?
C39 C25 C32 C37 10.5(5) . . . . ?
C40 C25 C32 C37 -102.1(5) . . . . ?
N3 C25 C32 C33 -46.7(9) . . . . ?
C39 C25 C32 C33 -172.4(6) . . . . ?
C40 C25 C32 C33 75.1(7) . . . . ?
C37 C32 C33 C34 1.3(9) . . . . ?
C25 C32 C33 C34 -175.6(6) . . . . ?
C32 C33 C34 C35 0.5(12) . . . . ?
C33 C34 C35 C36 -0.9(13) . . . . ?
C34 C35 C36 C37 -0.6(12) . . . . ?
C35 C36 C37 C32 2.5(9) . . . . ?
C35 C36 C37 N4 -177.0(6) . . . . ?
C33 C32 C37 C36 -2.8(8) . . . . ?
C25 C32 C37 C36 174.8(5) . . . . ?
C33 C32 C37 N4 176.7(5) . . . . ?
C25 C32 C37 N4 -5.7(6) . . . . ?
C39 N4 C37 C36 176.8(6) . . . . ?
C38 N4 C37 C36 -5.6(9) . . . . ?
C39 N4 C37 C32 -2.7(6) . . . . ?
C38 N4 C37 C32 174.9(5) . . . . ?
C37 N4 C39 O6 -175.1(5) . . . . ?
C38 N4 C39 O6 7.2(9) . . . . ?
C37 N4 C39 C25 9.3(6) . . . . ?
C38 N4 C39 C25 -168.4(5) . . . . ?
N3 C25 C39 O6 43.9(8) . . . . ?
C32 C25 C39 O6 172.4(5) . . . . ?
C40 C25 C39 O6 -69.2(7) . . . . ?
N3 C25 C39 N4 -140.6(5) . . . . ?
C32 C25 C39 N4 -12.1(5) . . . . ?
C40 C25 C39 N4 106.2(5) . . . . ?
N3 C25 C40 C43 -168.6(5) . . . . ?
C32 C25 C40 C43 62.3(6) . . . . ?
C39 C25 C40 C43 -49.0(6) . . . . ?
N3 C25 C40 C41 63.4(7) . . . . ?
C32 C25 C40 C41 -65.7(6) . . . . ?
C39 C25 C40 C41 -177.0(5) . . . . ?
C43 C40 C41 C42 67.0(7) . . . . ?
C25 C40 C41 C42 -165.5(5) . . . . ?
C41 C40 C43 C44 -131.0(6) . . . . ?
C25 C40 C43 C44 100.8(6) . . . . ?
C41 C40 C43 C48 49.0(7) . . . . ?
C25 C40 C43 C48 -79.3(7) . . . . ?
C48 C43 C44 C45 1.1(9) . . . . ?
C40 C43 C44 C45 -178.9(6) . . . . ?
C43 C44 C45 C46 -2.6(12) . . . . ?
C44 C45 C46 C47 2.7(13) . . . . ?
C45 C46 C47 C48 -1.4(12) . . . . ?
C46 C47 C48 C43 -0.1(10) . . . . ?
C44 C43 C48 C47 0.2(9) . . . . ?
C40 C43 C48 C47 -179.7(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306759
