#------------------------------------------------------------------------------
#$Date: 2022-09-05 05:30:44 +0300 (Mon, 05 Sep 2022) $
#$Revision: 277619 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/06/7130653.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_7130653
loop_
_publ_author_name
'Debnath, Snehasish'
'Chatterjee, Pabitra B.'
_publ_section_title
;
 Enantiopure chiroptical probes for circular dichroism and absorbance
 based detection of nerve gas simulants.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9006
_journal_page_last               9009
_journal_paper_doi               10.1039/d2cc03392e
_journal_volume                  58
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C22 H28 N O4 V'
_chemical_formula_sum            'C22 H28 N O4 V'
_chemical_formula_weight         421.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-07-06 deposited with the CCDC.	2022-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.721(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.070(2)
_cell_length_b                   8.2000(8)
_cell_length_c                   15.4395(16)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.44
_cell_volume                     2113.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            45705
_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         27.250
_diffrn_reflns_theta_min         2.440
_diffrn_source                   'MICRO FOCUS TUBE'
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.6865
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4745
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0412P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3861
_reflns_number_total             4745
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03392e5.cif
_cod_data_source_block           snd394REPEAT_0ma_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7130653
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
V1 V 0.64513(3) 0.33234(7) 0.78758(3) 0.04316(15) Uani 1 1 d . . . . .
O1 O 0.55607(12) 0.3803(2) 0.66425(14) 0.0477(6) Uani 1 1 d . . . . .
O2 O 0.73799(12) 0.3584(3) 0.79733(16) 0.0498(6) Uani 1 1 d . . . . .
O3 O 0.64545(13) 0.3595(3) 0.90286(15) 0.0545(6) Uani 1 1 d . . . . .
O4 O 0.64198(16) 0.1374(3) 0.7844(2) 0.0653(8) Uani 1 1 d . . . . .
N1 N 0.65113(13) 0.6237(3) 0.80860(15) 0.0316(5) Uani 1 1 d . . . . .
C1 C 0.49994(18) 0.5011(4) 0.61633(19) 0.0392(7) Uani 1 1 d . . . . .
C9 C 0.78257(17) 0.6369(4) 0.8246(2) 0.0369(6) Uani 1 1 d . . . . .
C12 C 0.8801(2) 0.5544(5) 0.7571(2) 0.0530(9) Uani 1 1 d . . . . .
H12 H 0.912914 0.527366 0.734255 0.064 Uiso 1 1 calc R U . . .
C10 C 0.83181(19) 0.7519(4) 0.8221(2) 0.0460(7) Uani 1 1 d . . . . .
H10 H 0.831190 0.858377 0.842381 0.055 Uiso 1 1 calc R U . . .
C11 C 0.8822(2) 0.7121(5) 0.7901(3) 0.0521(9) Uani 1 1 d . . . . .
C15 C 0.61237(17) 0.6465(4) 0.86648(19) 0.0381(7) Uani 1 1 d . . . . .
H15 H 0.555076 0.625265 0.817109 0.046 Uiso 1 1 calc R U . . .
C14 C 0.78237(16) 0.4788(4) 0.7919(2) 0.0399(7) Uani 1 1 d . . . . .
C13 C 0.8311(2) 0.4349(5) 0.7565(2) 0.0453(8) Uani 1 1 d . . . . .
C16 C 0.6449(2) 0.5094(5) 0.9468(2) 0.0531(9) Uani 1 1 d . . . . .
H16A H 0.699030 0.535996 1.003850 0.064 Uiso 1 1 calc R U . . .
H16B H 0.612107 0.499652 0.974648 0.064 Uiso 1 1 calc R U . . .
C17 C 0.61950(18) 0.8146(5) 0.9129(2) 0.0495(8) Uani 1 1 d . . . . .
H17A H 0.604051 0.896554 0.859652 0.059 Uiso 1 1 calc R U . . .
H17B H 0.674997 0.833952 0.968455 0.059 Uiso 1 1 calc R U . . .
C19 C 0.3992(2) 0.2769(5) 0.5221(3) 0.0682(12) Uani 1 1 d . . . . .
H19A H 0.342791 0.266794 0.470464 0.102 Uiso 1 1 calc R U . . .
H19B H 0.412375 0.221365 0.584454 0.102 Uiso 1 1 calc R U . . .
H19C H 0.428591 0.229273 0.496233 0.102 Uiso 1 1 calc R U . . .
C18 C 0.5674(2) 0.8332(7) 0.9560(2) 0.0695(10) Uani 1 1 d . . . . .
H18A H 0.570148 0.943730 0.978270 0.104 Uiso 1 1 calc R U . . .
H18B H 0.586407 0.761015 1.014163 0.104 Uiso 1 1 calc R U . . .
H18C H 0.512920 0.806551 0.902721 0.104 Uiso 1 1 calc R U . . .
C20 C 0.3176(2) 0.8688(5) 0.4654(3) 0.0721(13) Uani 1 1 d . . . . .
H20A H 0.327485 0.935567 0.422666 0.108 Uiso 1 1 calc R U . . .
H20B H 0.318468 0.935313 0.517226 0.108 Uiso 1 1 calc R U . . .
H20C H 0.266072 0.817695 0.422862 0.108 Uiso 1 1 calc R U . . .
C21 C 0.9378(3) 0.8388(7) 0.7918(4) 0.0863(13) Uani 1 1 d . . . . .
H21A H 0.957290 0.908744 0.851069 0.129 Uiso 1 1 calc R U . . .
H21B H 0.909214 0.902526 0.729215 0.129 Uiso 1 1 calc R U . . .
H21C H 0.982195 0.785323 0.796323 0.129 Uiso 1 1 calc R U . . .
C2 C 0.4209(2) 0.4547(4) 0.5458(2) 0.0449(8) Uani 1 1 d . . . . .
C3 C 0.3635(2) 0.5766(5) 0.4990(2) 0.0489(9) Uani 1 1 d . . . . .
H3 H 0.310251 0.546669 0.452422 0.059 Uiso 1 1 calc R U . . .
C4 C 0.38163(19) 0.7393(5) 0.5183(2) 0.0454(7) Uani 1 1 d . . . . .
C5 C 0.46196(18) 0.7820(4) 0.58765(19) 0.0394(7) Uani 1 1 d . . . . .
H5 H 0.475613 0.891795 0.600998 0.047 Uiso 1 1 calc R U . . .
C6 C 0.52182(17) 0.6657(4) 0.63714(18) 0.0344(6) Uani 1 1 d . . . . .
C7 C 0.60821(17) 0.7124(4) 0.70714(19) 0.0351(6) Uani 1 1 d . . . . .
H7A H 0.634769 0.690337 0.671660 0.042 Uiso 1 1 calc R U . . .
H7B H 0.611791 0.828686 0.720521 0.042 Uiso 1 1 calc R U . . .
C22 C 0.8323(2) 0.2628(5) 0.7262(3) 0.0624(11) Uani 1 1 d . . . . .
H22A H 0.779832 0.232755 0.668525 0.094 Uiso 1 1 calc R U . . .
H22B H 0.848011 0.192133 0.784136 0.094 Uiso 1 1 calc R U . . .
H22C H 0.869840 0.252645 0.706509 0.094 Uiso 1 1 calc R U . . .
C8 C 0.73546(16) 0.6790(4) 0.8707(2) 0.0388(7) Uani 1 1 d . . . . .
H8A H 0.761937 0.630967 0.939551 0.047 Uiso 1 1 calc R U . . .
H8B H 0.736268 0.796459 0.878814 0.047 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 0.0033 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'
V V 0.3005 0.5294 '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
O4 V1 O1 100.82(11) . . ?
O4 V1 O3 97.66(13) . . ?
O1 V1 O3 118.76(11) . . ?
O4 V1 O2 98.21(13) . . ?
O1 V1 O2 116.12(10) . . ?
O3 V1 O2 118.08(10) . . ?
O4 V1 N1 174.34(11) . . ?
O1 V1 N1 82.57(8) . . ?
O3 V1 N1 76.71(10) . . ?
O2 V1 N1 84.18(10) . . ?
C1 O1 V1 140.48(18) . . ?
C14 O2 V1 139.8(2) . . ?
C16 O3 V1 126.2(2) . . ?
C8 N1 C15 111.4(2) . . ?
C8 N1 C7 108.5(2) . . ?
C15 N1 C7 112.3(2) . . ?
C8 N1 V1 110.22(19) . . ?
C15 N1 V1 101.66(17) . . ?
C7 N1 V1 112.70(17) . . ?
O1 C1 C2 117.7(3) . . ?
O1 C1 C6 121.0(3) . . ?
C2 C1 C6 121.3(3) . . ?
C10 C9 C14 119.0(3) . . ?
C10 C9 C8 120.2(3) . . ?
C14 C9 C8 120.6(3) . . ?
C11 C12 C13 122.8(3) . . ?
C11 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C9 C10 C11 121.6(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 118.1(3) . . ?
C12 C11 C21 121.4(4) . . ?
C10 C11 C21 120.5(4) . . ?
N1 C15 C17 116.9(3) . . ?
N1 C15 C16 105.3(3) . . ?
C17 C15 C16 113.5(2) . . ?
N1 C15 H15 106.8 . . ?
C17 C15 H15 106.8 . . ?
C16 C15 H15 106.8 . . ?
O2 C14 C9 121.6(3) . . ?
O2 C14 C13 117.2(3) . . ?
C9 C14 C13 121.1(3) . . ?
C12 C13 C14 117.5(3) . . ?
C12 C13 C22 122.5(3) . . ?
C14 C13 C22 120.0(3) . . ?
O3 C16 C15 111.5(2) . . ?
O3 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
O3 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C15 C17 C18 112.8(3) . . ?
C15 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C15 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C2 C19 H19A 109.5 . . ?
C2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 C2 C1 117.9(3) . . ?
C3 C2 C19 121.7(3) . . ?
C1 C2 C19 120.3(3) . . ?
C4 C3 C2 122.9(3) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C20 121.5(3) . . ?
C5 C4 C20 120.8(3) . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 118.1(3) . . ?
C5 C6 C7 121.7(3) . . ?
C1 C6 C7 120.1(3) . . ?
N1 C7 C6 113.3(2) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C13 C22 H22A 109.5 . . ?
C13 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C13 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C8 C9 114.6(2) . . ?
N1 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
N1 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
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
V1 O4 1.599(3) . ?
V1 O1 1.788(2) . ?
V1 O3 1.790(2) . ?
V1 O2 1.797(2) . ?
V1 N1 2.405(3) . ?
O1 C1 1.368(4) . ?
O2 C14 1.363(4) . ?
O3 C16 1.406(5) . ?
N1 C8 1.479(4) . ?
N1 C15 1.487(3) . ?
N1 C7 1.492(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.401(4) . ?
C9 C10 1.382(4) . ?
C9 C14 1.390(5) . ?
C9 C8 1.505(4) . ?
C12 C11 1.382(6) . ?
C12 C13 1.384(5) . ?
C12 H12 0.9300 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9300 . ?
C11 C21 1.513(6) . ?
C15 C17 1.523(5) . ?
C15 C16 1.526(4) . ?
C15 H15 0.9800 . ?
C14 C13 1.407(4) . ?
C13 C22 1.491(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.527(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C2 1.508(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 C4 1.510(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C2 C3 1.387(5) . ?
C3 C4 1.371(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
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
O4 V1 O1 C1 152.7(3) . . . . ?
O3 V1 O1 C1 47.6(4) . . . . ?
O2 V1 O1 C1 -102.5(3) . . . . ?
N1 V1 O1 C1 -22.7(3) . . . . ?
O4 V1 O2 C14 169.8(3) . . . . ?
O1 V1 O2 C14 63.4(3) . . . . ?
O3 V1 O2 C14 -87.0(3) . . . . ?
N1 V1 O2 C14 -15.4(3) . . . . ?
O4 V1 O3 C16 -177.6(3) . . . . ?
O1 V1 O3 C16 -70.7(3) . . . . ?
O2 V1 O3 C16 78.8(3) . . . . ?
N1 V1 O3 C16 3.0(2) . . . . ?
V1 O1 C1 C2 -142.6(3) . . . . ?
V1 O1 C1 C6 38.0(5) . . . . ?
C14 C9 C10 C11 -1.5(4) . . . . ?
C8 C9 C10 C11 173.3(3) . . . . ?
C13 C12 C11 C10 -1.2(5) . . . . ?
C13 C12 C11 C21 178.7(3) . . . . ?
C9 C10 C11 C12 2.2(5) . . . . ?
C9 C10 C11 C21 -177.8(3) . . . . ?
C8 N1 C15 C17 51.1(3) . . . . ?
C7 N1 C15 C17 -70.9(3) . . . . ?
V1 N1 C15 C17 168.4(2) . . . . ?
C8 N1 C15 C16 -76.0(3) . . . . ?
C7 N1 C15 C16 162.1(2) . . . . ?
V1 N1 C15 C16 41.3(2) . . . . ?
V1 O2 C14 C9 32.4(4) . . . . ?
V1 O2 C14 C13 -150.5(2) . . . . ?
C10 C9 C14 O2 176.8(2) . . . . ?
C8 C9 C14 O2 2.1(4) . . . . ?
C10 C9 C14 C13 -0.1(4) . . . . ?
C8 C9 C14 C13 -174.9(3) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C11 C12 C13 C22 -176.6(3) . . . . ?
O2 C14 C13 C12 -176.0(3) . . . . ?
C9 C14 C13 C12 1.0(4) . . . . ?
O2 C14 C13 C22 0.3(4) . . . . ?
C9 C14 C13 C22 177.4(3) . . . . ?
V1 O3 C16 C15 21.9(4) . . . . ?
N1 C15 C16 O3 -44.2(3) . . . . ?
C17 C15 C16 O3 -173.4(3) . . . . ?
N1 C15 C17 C18 171.2(2) . . . . ?
C16 C15 C17 C18 -65.8(4) . . . . ?
O1 C1 C2 C3 178.4(3) . . . . ?
C6 C1 C2 C3 -2.2(4) . . . . ?
O1 C1 C2 C19 -1.4(5) . . . . ?
C6 C1 C2 C19 178.0(3) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C19 C2 C3 C4 -179.2(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 C20 179.7(3) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C20 C4 C5 C6 180.0(3) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 176.8(3) . . . . ?
O1 C1 C6 C5 -178.7(2) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
O1 C1 C6 C7 4.1(4) . . . . ?
C2 C1 C6 C7 -175.3(3) . . . . ?
C8 N1 C7 C6 179.8(3) . . . . ?
C15 N1 C7 C6 -56.6(3) . . . . ?
V1 N1 C7 C6 57.5(3) . . . . ?
C5 C6 C7 N1 132.2(3) . . . . ?
C1 C6 C7 N1 -50.7(4) . . . . ?
C15 N1 C8 C9 171.1(3) . . . . ?
C7 N1 C8 C9 -64.7(3) . . . . ?
V1 N1 C8 C9 59.1(3) . . . . ?
C10 C9 C8 N1 135.5(3) . . . . ?
C14 C9 C8 N1 -49.8(4) . . . . ?
