#------------------------------------------------------------------------------
#$Date: 2022-06-24 00:56:50 +0300 (Fri, 24 Jun 2022) $
#$Revision: 276196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/02/7130276.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_7130276
loop_
_publ_author_name
'Cristóbal, Christian'
'Gaviña, Daniel'
'Alonso, Inés'
'Ribagorda, María'
'Carretero, Juan C.'
'del Pozo, Carlos'
'Adrio, Javier'
_publ_section_title
;
 Catalytic enantioselective intramolecular 1,3-dipolar cycloaddition of
 azomethine ylides with fluorinated dipolarophiles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02902B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H12 Cl2 F3 N O3'
_chemical_formula_weight         370.15
_chemical_name_common            JASOdiCl
_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   geom
_audit_update_record
;
2022-05-18 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.35(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.577(7)
_cell_length_b                   11.122(7)
_cell_length_c                   12.605(8)
_cell_measurement_reflns_used    1507
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      17.8801
_cell_measurement_theta_min      2.5073
_cell_volume                     1531.3(17)
_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-2014/7 (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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0839
_diffrn_reflns_av_unetI/netI     0.1625
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13716
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         1.71
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.469
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.227
_refine_ls_abs_structure_details
;

Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         5403
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1828
_refine_ls_R_factor_gt           0.0534
_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)+(0.0197P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                2310
_reflns_number_total             5403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02902b2.cif
_cod_data_source_block           03196
_cod_original_cell_volume        1531.3(16)
_cod_database_code               7130276
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
C C1 0.6611(8) 0.5466(8) 0.5930(8) 0.050(2) Uani d . . . 1 . .
C C2 0.7575(9) 0.4999(8) 0.5653(8) 0.055(3) Uani d . . . 1 . .
H H2 0.7422 0.4424 0.5086 0.067 Uiso calc U . R 1 . .
C C3 0.8742(9) 0.5358(9) 0.6187(9) 0.063(3) Uani d . . . 1 . .
C C4 0.9006(9) 0.6205(9) 0.7039(9) 0.064(3) Uani d . . . 1 . .
H H4 0.9803 0.646 0.741 0.076 Uiso calc U . R 1 . .
C C5 0.8049(11) 0.6642(7) 0.7305(8) 0.055(3) Uani d . . . 1 . .
C C6 0.6856(9) 0.6286(7) 0.6792(8) 0.045(2) Uani d . . . 1 . .
C C7 0.5308(8) 0.5160(7) 0.5267(7) 0.053(3) Uani d . . . 1 . .
H H7 0.5186 0.5268 0.4465 0.064 Uiso calc U . R 1 . .
C C8 0.4390(7) 0.5929(7) 0.5576(8) 0.050(2) Uani d . . . 1 . .
H H8 0.425 0.6691 0.5162 0.06 Uiso calc U . R 1 . .
C C9 0.4836(8) 0.6145(8) 0.6827(8) 0.057(3) Uani d . . . 1 . .
H H9A 0.423 0.6602 0.7034 0.068 Uiso calc U . R 1 . .
H H9B 0.4954 0.5381 0.7221 0.068 Uiso calc U . R 1 . .
C C10 0.3207(7) 0.5146(7) 0.5226(7) 0.048(2) Uani d . . . 1 . .
H H10 0.2836 0.5181 0.582 0.058 Uiso calc U . R 1 . .
C C11 0.3656(8) 0.3858(8) 0.5150(8) 0.054(3) Uani d . . . 1 . .
H H11 0.3314 0.3589 0.4367 0.065 Uiso calc U . R 1 . .
C C12 0.3297(11) 0.2976(9) 0.5877(10) 0.065(3) Uani d . . . 1 . .
C C13 0.2284(10) 0.5549(11) 0.4138(9) 0.067(3) Uani d . . . 1 . .
C C14 0.1691(9) 0.2021(9) 0.6336(9) 0.088(4) Uani d . . . 1 . .
H H14A 0.2121 0.1269 0.6432 0.132 Uiso calc U . R 1 . .
H H14B 0.083 0.1882 0.5989 0.132 Uiso calc U . R 1 . .
H H14C 0.1839 0.2392 0.7057 0.132 Uiso calc U . R 1 . .
C C15 0.6438(8) 0.5263(8) 0.1092(8) 0.055(3) Uani d . . . 1 . .
C C16 0.7320(9) 0.5574(8) 0.0646(8) 0.058(3) Uani d . . . 1 . .
H H16 0.7159 0.6129 0.0062 0.069 Uiso calc U . R 1 . .
C C17 0.8471(9) 0.5040(9) 0.1086(9) 0.056(3) Uani d . . . 1 . .
C C18 0.8730(8) 0.4202(8) 0.1909(9) 0.058(3) Uani d . . . 1 . .
H H18 0.9502 0.3852 0.2179 0.07 Uiso calc U . R 1 . .
C C19 0.7815(9) 0.3876(7) 0.2340(7) 0.048(3) Uani d . . . 1 . .
C C20 0.6685(8) 0.4408(8) 0.1931(8) 0.048(2) Uani d . . . 1 . .
C C21 0.5214(8) 0.5877(8) 0.0713(8) 0.057(3) Uani d . . . 1 . .
H H21 0.5342 0.6746 0.0689 0.068 Uiso calc U . R 1 . .
C C22 0.4464(7) 0.5628(7) 0.1481(7) 0.044(2) Uani d . . . 1 . .
H H22 0.472 0.6153 0.2143 0.053 Uiso calc U . R 1 . .
C C23 0.4608(7) 0.4347(8) 0.1815(8) 0.056(3) Uani d . . . 1 . .
H H23A 0.4094 0.4168 0.2266 0.067 Uiso calc U . R 1 . .
H H23B 0.4337 0.3848 0.1146 0.067 Uiso calc U . R 1 . .
C C24 0.3155(7) 0.5896(8) 0.0750(7) 0.052(2) Uani d . . . 1 . .
H H24 0.2598 0.5344 0.0948 0.062 Uiso calc U . R 1 . .
C C25 0.3153(8) 0.5600(9) -0.0478(8) 0.061(3) Uani d . . . 1 . .
H H25 0.2791 0.6275 -0.0976 0.073 Uiso calc U . R 1 . .
C C26 0.2445(10) 0.4490(12) -0.0923(8) 0.066(3) Uani d . . . 1 . .
C C27 0.2777(10) 0.7162(10) 0.0854(12) 0.073(3) Uani d . . . 1 . .
C C28 0.0509(9) 0.3562(9) -0.1407(9) 0.100(4) Uani d . . . 1 . .
H H28A -0.0031 0.366 -0.2166 0.15 Uiso calc U . R 1 . .
H H28B 0.0036 0.3468 -0.0915 0.15 Uiso calc U . R 1 . .
H H28C 0.1008 0.2862 -0.136 0.15 Uiso calc U . R 1 . .
Cl Cl1 0.9958(2) 0.4765(3) 0.5812(2) 0.0899(9) Uani d . . . 1 . .
Cl Cl2 0.8346(2) 0.7744(2) 0.8362(2) 0.0723(8) Uani d . . . 1 . .
Cl Cl3 0.9616(2) 0.5425(2) 0.0523(3) 0.0926(10) Uani d . . . 1 . .
Cl Cl4 0.8153(2) 0.2781(2) 0.3380(2) 0.0776(8) Uani d . . . 1 . .
F F1 0.1887(5) 0.6666(5) 0.4215(5) 0.091(2) Uani d . . . 1 . .
F F2 0.1296(5) 0.4854(6) 0.3834(4) 0.0836(18) Uani d . . . 1 . .
F F3 0.2758(5) 0.5535(5) 0.3306(5) 0.0832(17) Uani d . . . 1 . .
F F4 0.2756(6) 0.7445(5) 0.1846(6) 0.102(2) Uani d . . . 1 . .
F F5 0.1622(5) 0.7375(5) 0.0140(5) 0.097(2) Uani d . . . 1 . .
F F6 0.3488(5) 0.7959(5) 0.0583(5) 0.0890(19) Uani d . . . 1 . .
N N1 0.4993(7) 0.3916(6) 0.5453(7) 0.064(2) Uani d . . . 1 . .
H H1 0.5498 0.3331 0.5695 0.077 Uiso calc U . R 1 . .
N N2 0.4444(6) 0.5483(8) -0.0384(6) 0.072(2) Uani d . . . 1 . .
H H2A 0.4704 0.5219 -0.0905 0.086 Uiso calc U . R 1 . .
O O1 0.5977(6) 0.6798(5) 0.7146(5) 0.0581(18) Uani d . . . 1 . .
O O2 0.4041(7) 0.2532(7) 0.6682(8) 0.119(3) Uani d . . . 1 . .
O O3 0.2130(7) 0.2822(6) 0.5614(5) 0.0666(18) Uani d . . . 1 . .
O O4 0.5870(5) 0.4056(5) 0.2452(5) 0.0576(17) Uani d . . . 1 . .
O O5 0.2887(7) 0.3587(8) -0.1097(8) 0.130(4) Uani d . . . 1 . .
O O6 0.1292(6) 0.4622(6) -0.1071(5) 0.075(2) 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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 . . 118.6(8) ?
C6 C1 C7 . . 119.8(9) ?
C2 C1 C7 . . 121.5(9) ?
C3 C2 C1 . . 121.4(9) ?
C3 C2 H2 . . 119.3 ?
C1 C2 H2 . . 119.3 ?
C2 C3 C4 . . 120.9(9) ?
C2 C3 Cl1 . . 120.8(9) ?
C4 C3 Cl1 . . 118.3(9) ?
C5 C4 C3 . . 116.7(9) ?
C5 C4 H4 . . 121.7 ?
C3 C4 H4 . . 121.7 ?
C4 C5 C6 . . 124.0(9) ?
C4 C5 Cl2 . . 118.0(9) ?
C6 C5 Cl2 . . 118.0(9) ?
O1 C6 C1 . . 123.7(9) ?
O1 C6 C5 . . 117.9(9) ?
C1 C6 C5 . . 118.3(9) ?
N1 C7 C1 . . 112.4(7) ?
N1 C7 C8 . . 104.9(7) ?
C1 C7 C8 . . 113.0(8) ?
N1 C7 H7 . . 108.8 ?
C1 C7 H7 . . 108.8 ?
C8 C7 H7 . . 108.8 ?
C9 C8 C7 . . 109.5(7) ?
C9 C8 C10 . . 110.4(7) ?
C7 C8 C10 . . 103.8(7) ?
C9 C8 H8 . . 111.0 ?
C7 C8 H8 . . 111.0 ?
C10 C8 H8 . . 111.0 ?
O1 C9 C8 . . 109.7(7) ?
O1 C9 H9A . . 109.7 ?
C8 C9 H9A . . 109.7 ?
O1 C9 H9B . . 109.7 ?
C8 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
C13 C10 C11 . . 112.0(7) ?
C13 C10 C8 . . 112.6(8) ?
C11 C10 C8 . . 104.7(6) ?
C13 C10 H10 . . 109.1 ?
C11 C10 H10 . . 109.1 ?
C8 C10 H10 . . 109.1 ?
N1 C11 C12 . . 110.7(8) ?
N1 C11 C10 . . 107.0(6) ?
C12 C11 C10 . . 113.9(8) ?
N1 C11 H11 . . 108.4 ?
C12 C11 H11 . . 108.4 ?
C10 C11 H11 . . 108.4 ?
O2 C12 O3 . . 124.0(11) ?
O2 C12 C11 . . 121.5(10) ?
O3 C12 C11 . . 114.2(9) ?
F2 C13 F3 . . 107.8(9) ?
F2 C13 F1 . . 106.1(8) ?
F3 C13 F1 . . 108.0(10) ?
F2 C13 C10 . . 112.0(9) ?
F3 C13 C10 . . 111.2(8) ?
F1 C13 C10 . . 111.6(8) ?
O3 C14 H14A . . 109.5 ?
O3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 C20 . . 119.8(9) ?
C16 C15 C21 . . 120.6(9) ?
C20 C15 C21 . . 119.5(9) ?
C15 C16 C17 . . 118.3(9) ?
C15 C16 H16 . . 120.8 ?
C17 C16 H16 . . 120.8 ?
C18 C17 C16 . . 122.6(9) ?
C18 C17 Cl3 . . 118.3(8) ?
C16 C17 Cl3 . . 119.1(8) ?
C17 C18 C19 . . 118.4(9) ?
C17 C18 H18 . . 120.8 ?
C19 C18 H18 . . 120.8 ?
C20 C19 C18 . . 119.8(9) ?
C20 C19 Cl4 . . 122.3(9) ?
C18 C19 Cl4 . . 117.9(8) ?
C19 C20 O4 . . 114.8(9) ?
C19 C20 C15 . . 121.0(9) ?
O4 C20 C15 . . 124.1(8) ?
N2 C21 C15 . . 112.7(8) ?
N2 C21 C22 . . 104.7(7) ?
C15 C21 C22 . . 113.0(8) ?
N2 C21 H21 . . 108.8 ?
C15 C21 H21 . . 108.8 ?
C22 C21 H21 . . 108.8 ?
C23 C22 C24 . . 110.9(7) ?
C23 C22 C21 . . 108.7(8) ?
C24 C22 C21 . . 104.0(7) ?
C23 C22 H22 . . 111.0 ?
C24 C22 H22 . . 111.0 ?
C21 C22 H22 . . 111.0 ?
O4 C23 C22 . . 111.7(7) ?
O4 C23 H23A . . 109.3 ?
C22 C23 H23A . . 109.3 ?
O4 C23 H23B . . 109.3 ?
C22 C23 H23B . . 109.3 ?
H23A C23 H23B . . 107.9 ?
C27 C24 C22 . . 113.2(8) ?
C27 C24 C25 . . 112.2(8) ?
C22 C24 C25 . . 103.3(7) ?
C27 C24 H24 . . 109.3 ?
C22 C24 H24 . . 109.3 ?
C25 C24 H24 . . 109.3 ?
N2 C25 C26 . . 112.2(8) ?
N2 C25 C24 . . 105.6(7) ?
C26 C25 C24 . . 111.4(8) ?
N2 C25 H25 . . 109.2 ?
C26 C25 H25 . . 109.2 ?
C24 C25 H25 . . 109.2 ?
O5 C26 O6 . . 124.1(11) ?
O5 C26 C25 . . 123.9(10) ?
O6 C26 C25 . . 112.0(10) ?
F4 C27 F6 . . 107.3(11) ?
F4 C27 F5 . . 105.5(9) ?
F6 C27 F5 . . 105.7(9) ?
F4 C27 C24 . . 114.4(10) ?
F6 C27 C24 . . 112.4(9) ?
F5 C27 C24 . . 111.0(9) ?
O6 C28 H28A . . 109.5 ?
O6 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
O6 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C11 N1 C7 . . 107.2(6) ?
C11 N1 H1 . . 126.4 ?
C7 N1 H1 . . 126.4 ?
C21 N2 C25 . . 109.9(7) ?
C21 N2 H2A . . 125.1 ?
C25 N2 H2A . . 125.1 ?
C6 O1 C9 . . 114.3(7) ?
C12 O3 C14 . . 117.8(8) ?
C20 O4 C23 . . 113.4(7) ?
C26 O6 C28 . . 117.5(8) ?
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
C1 C6 . 1.374(11) ?
C1 C2 . 1.377(11) ?
C1 C7 . 1.501(11) ?
C2 C3 . 1.355(11) ?
C2 H2 . 0.93 ?
C3 C4 . 1.384(12) ?
C3 Cl1 . 1.754(9) ?
C4 C5 . 1.350(12) ?
C4 H4 . 0.93 ?
C5 C6 . 1.375(11) ?
C5 Cl2 . 1.759(9) ?
C6 O1 . 1.364(10) ?
C7 N1 . 1.469(10) ?
C7 C8 . 1.513(11) ?
C7 H7 . 0.98 ?
C8 C9 . 1.507(11) ?
C8 C10 . 1.558(10) ?
C8 H8 . 0.98 ?
C9 O1 . 1.443(9) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 C13 . 1.501(12) ?
C10 C11 . 1.537(11) ?
C10 H10 . 0.98 ?
C11 N1 . 1.468(10) ?
C11 C12 . 1.493(13) ?
C11 H11 . 0.98 ?
C12 O2 . 1.198(10) ?
C12 O3 . 1.292(11) ?
C13 F2 . 1.328(10) ?
C13 F3 . 1.333(11) ?
C13 F1 . 1.340(11) ?
C14 O3 . 1.479(10) ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 C16 . 1.365(11) ?
C15 C20 . 1.379(11) ?
C15 C21 . 1.501(11) ?
C16 C17 . 1.395(12) ?
C16 H16 . 0.93 ?
C17 C18 . 1.352(11) ?
C17 Cl3 . 1.751(9) ?
C18 C19 . 1.389(12) ?
C18 H18 . 0.93 ?
C19 C20 . 1.371(11) ?
C19 Cl4 . 1.737(9) ?
C20 O4 . 1.374(10) ?
C21 N2 . 1.443(10) ?
C21 C22 . 1.525(11) ?
C21 H21 . 0.98 ?
C22 C23 . 1.480(10) ?
C22 C24 . 1.520(10) ?
C22 H22 . 0.98 ?
C23 O4 . 1.451(9) ?
C23 H23A . 0.97 ?
C23 H23B . 0.97 ?
C24 C27 . 1.493(13) ?
C24 C25 . 1.581(11) ?
C24 H24 . 0.98 ?
C25 N2 . 1.465(9) ?
C25 C26 . 1.486(13) ?
C25 H25 . 0.98 ?
C26 O5 . 1.180(12) ?
C26 O6 . 1.293(11) ?
C27 F4 . 1.297(12) ?
C27 F6 . 1.329(11) ?
C27 F5 . 1.363(11) ?
C28 O6 . 1.462(10) ?
C28 H28A . 0.96 ?
C28 H28B . 0.96 ?
C28 H28C . 0.96 ?
N1 H1 . 0.86 ?
N2 H2A . 0.86 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C9 H9A Cl4 2_656 0.97 2.94 3.841(9) 154.9 ?
C14 H14C O5 1_556 0.96 2.60 3.528(14) 161.6 ?
C21 H21 F6 . 0.98 2.50 3.027(10) 113.4 ?
C22 H22 O2 2_656 0.98 2.28 3.191(12) 154.3 ?
C28 H28A Cl1 1_454 0.96 2.83 3.606(11) 139.0 ?
C28 H28B Cl3 1_455 0.96 2.97 3.598(12) 123.9 ?
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
C6 C1 C2 C3 . . . . -2.0(13) ?
C7 C1 C2 C3 . . . . 174.0(8) ?
C1 C2 C3 C4 . . . . 0.5(14) ?
C1 C2 C3 Cl1 . . . . -179.3(7) ?
C2 C3 C4 C5 . . . . 0.2(14) ?
Cl1 C3 C4 C5 . . . . -180.0(7) ?
C3 C4 C5 C6 . . . . 0.7(14) ?
C3 C4 C5 Cl2 . . . . -178.6(7) ?
C2 C1 C6 O1 . . . . -179.3(8) ?
C7 C1 C6 O1 . . . . 4.7(13) ?
C2 C1 C6 C5 . . . . 2.7(12) ?
C7 C1 C6 C5 . . . . -173.3(7) ?
C4 C5 C6 O1 . . . . 179.7(8) ?
Cl2 C5 C6 O1 . . . . -1.0(10) ?
C4 C5 C6 C1 . . . . -2.2(13) ?
Cl2 C5 C6 C1 . . . . 177.1(7) ?
C6 C1 C7 N1 . . . . -112.5(9) ?
C2 C1 C7 N1 . . . . 71.6(11) ?
C6 C1 C7 C8 . . . . 6.1(12) ?
C2 C1 C7 C8 . . . . -169.8(8) ?
N1 C7 C8 C9 . . . . 84.6(8) ?
C1 C7 C8 C9 . . . . -38.2(10) ?
N1 C7 C8 C10 . . . . -33.3(8) ?
C1 C7 C8 C10 . . . . -156.2(7) ?
C7 C8 C9 O1 . . . . 62.3(9) ?
C10 C8 C9 O1 . . . . 176.0(6) ?
C9 C8 C10 C13 . . . . 140.6(8) ?
C7 C8 C10 C13 . . . . -102.2(8) ?
C9 C8 C10 C11 . . . . -97.5(8) ?
C7 C8 C10 C11 . . . . 19.7(9) ?
C13 C10 C11 N1 . . . . 123.2(9) ?
C8 C10 C11 N1 . . . . 0.9(10) ?
C13 C10 C11 C12 . . . . -114.2(10) ?
C8 C10 C11 C12 . . . . 123.5(8) ?
N1 C11 C12 O2 . . . . 9.4(13) ?
C10 C11 C12 O2 . . . . -111.2(11) ?
N1 C11 C12 O3 . . . . -176.0(7) ?
C10 C11 C12 O3 . . . . 63.4(11) ?
C11 C10 C13 F2 . . . . 60.5(11) ?
C8 C10 C13 F2 . . . . 178.3(8) ?
C11 C10 C13 F3 . . . . -60.1(11) ?
C8 C10 C13 F3 . . . . 57.6(11) ?
C11 C10 C13 F1 . . . . 179.3(8) ?
C8 C10 C13 F1 . . . . -63.0(11) ?
C20 C15 C16 C17 . . . . -2.2(13) ?
C21 C15 C16 C17 . . . . 175.4(8) ?
C15 C16 C17 C18 . . . . 2.1(13) ?
C15 C16 C17 Cl3 . . . . 179.9(7) ?
C16 C17 C18 C19 . . . . -0.9(13) ?
Cl3 C17 C18 C19 . . . . -178.7(7) ?
C17 C18 C19 C20 . . . . -0.3(13) ?
C17 C18 C19 Cl4 . . . . 179.0(6) ?
C18 C19 C20 O4 . . . . -177.3(8) ?
Cl4 C19 C20 O4 . . . . 3.5(10) ?
C18 C19 C20 C15 . . . . 0.2(12) ?
Cl4 C19 C20 C15 . . . . -179.0(7) ?
C16 C15 C20 C19 . . . . 1.1(13) ?
C21 C15 C20 C19 . . . . -176.5(8) ?
C16 C15 C20 O4 . . . . 178.3(8) ?
C21 C15 C20 O4 . . . . 0.7(13) ?
C16 C15 C21 N2 . . . . 75.0(11) ?
C20 C15 C21 N2 . . . . -107.4(9) ?
C16 C15 C21 C22 . . . . -166.7(8) ?
C20 C15 C21 C22 . . . . 10.9(12) ?
N2 C21 C22 C23 . . . . 82.1(8) ?
C15 C21 C22 C23 . . . . -40.9(10) ?
N2 C21 C22 C24 . . . . -36.1(9) ?
C15 C21 C22 C24 . . . . -159.0(7) ?
C24 C22 C23 O4 . . . . 176.3(7) ?
C21 C22 C23 O4 . . . . 62.5(9) ?
C23 C22 C24 C27 . . . . 151.1(9) ?
C21 C22 C24 C27 . . . . -92.2(10) ?
C23 C22 C24 C25 . . . . -87.4(9) ?
C21 C22 C24 C25 . . . . 29.3(8) ?
C27 C24 C25 N2 . . . . 109.4(9) ?
C22 C24 C25 N2 . . . . -12.8(9) ?
C27 C24 C25 C26 . . . . -128.6(9) ?
C22 C24 C25 C26 . . . . 109.2(8) ?
N2 C25 C26 O5 . . . . 5.6(15) ?
C24 C25 C26 O5 . . . . -112.5(12) ?
N2 C25 C26 O6 . . . . -175.9(7) ?
C24 C25 C26 O6 . . . . 65.9(10) ?
C22 C24 C27 F4 . . . . -64.0(12) ?
C25 C24 C27 F4 . . . . 179.6(9) ?
C22 C24 C27 F6 . . . . 58.7(13) ?
C25 C24 C27 F6 . . . . -57.7(12) ?
C22 C24 C27 F5 . . . . 176.8(8) ?
C25 C24 C27 F5 . . . . 60.4(11) ?
C12 C11 N1 C7 . . . . -146.7(7) ?
C10 C11 N1 C7 . . . . -22.1(9) ?
C1 C7 N1 C11 . . . . 158.3(8) ?
C8 C7 N1 C11 . . . . 35.1(9) ?
C15 C21 N2 C25 . . . . 151.8(8) ?
C22 C21 N2 C25 . . . . 28.7(9) ?
C26 C25 N2 C21 . . . . -131.3(8) ?
C24 C25 N2 C21 . . . . -9.8(9) ?
C1 C6 O1 C9 . . . . 19.7(11) ?
C5 C6 O1 C9 . . . . -162.3(7) ?
C8 C9 O1 C6 . . . . -53.2(9) ?
O2 C12 O3 C14 . . . . -1.8(14) ?
C11 C12 O3 C14 . . . . -176.2(8) ?
C19 C20 O4 C23 . . . . -163.2(7) ?
C15 C20 O4 C23 . . . . 19.4(11) ?
C22 C23 O4 C20 . . . . -51.9(10) ?
O5 C26 O6 C28 . . . . 4.0(16) ?
C25 C26 O6 C28 . . . . -174.4(8) ?
