#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/04/2220445.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220445
loop_
_publ_author_name
'Thenmozhi, M.'
'Ponnuswamy, S.'
'Mohanraj, V.'
'Vijayalakshmi, R.'
'Ponnuswamy, M. N.'
_publ_section_title
1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-c-3,t-3-dimethylpiperidin-4-one
_journal_coeditor_code           CI2726
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o11
_journal_paper_doi               10.1107/S1600536808040063
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C23 H25 Cl2 N O4'
_chemical_formula_moiety         'C23 H25 Cl2 N O4'
_chemical_formula_sum            'C23 H25 Cl2 N O4'
_chemical_formula_weight         450.34
_chemical_melting_point_gt       377
_chemical_melting_point_lt       379
_chemical_name_systematic
;
1-Dichloroacetyl-r-2,c-6-bis(4-methoxyphenyl)-c-3,t-3-dimethylpiperidin-4-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.7340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.6295(9)
_cell_length_b                   10.3999(4)
_cell_length_c                   19.2617(9)
_cell_measurement_reflns_used    6905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.2
_cell_volume                     4508.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXS97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29354
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.631
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         6905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0869P)²+2.9239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1836
_reflns_number_gt                4138
_reflns_number_total             6905
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2726.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2220445
_cod_database_fobs_code          2220445
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.18029(3) 0.52254(7) 0.14172(4) 0.0790(2) Uani d . 1 . .
Cl Cl2 0.26274(4) 0.62339(11) 0.07261(4) 0.1127(4) Uani d . 1 . .
O O1 0.26407(7) 0.74756(16) 0.21261(9) 0.0635(4) Uani d . 1 . .
O O2 0.56012(6) 0.89254(16) 0.36906(9) 0.0604(4) Uani d . 1 . .
O O3 0.37036(9) 0.4204(2) 0.48165(10) 0.0798(6) Uani d . 1 . .
O O4 0.48349(7) 0.30777(15) 0.10880(9) 0.0592(4) Uani d . 1 . .
N N1 0.31916(6) 0.58476(15) 0.27717(8) 0.0402(3) Uani d . 1 . .
C C2 0.33601(8) 0.66580(19) 0.34377(10) 0.0407(4) Uani d . 1 . .
H H2 0.3092 0.7400 0.3325 0.049 Uiso calc R 1 . .
C C3 0.32172(8) 0.5947(2) 0.40675(11) 0.0481(5) Uani d . 1 . .
C C4 0.35641(9) 0.4707(2) 0.42265(12) 0.0530(5) Uani d . 1 . .
C C5 0.37393(9) 0.4121(2) 0.36076(12) 0.0521(5) Uani d . 1 . .
H H5A 0.3721 0.3194 0.3651 0.063 Uiso calc R 1 . .
H H5B 0.4151 0.4343 0.3676 0.063 Uiso calc R 1 . .
C C6 0.33818(8) 0.44832(19) 0.28249(11) 0.0435(4) Uani d . 1 . .
H H6 0.3023 0.3950 0.2685 0.052 Uiso calc R 1 . .
C C7 0.28061(8) 0.6362(2) 0.21725(11) 0.0460(4) Uani d . 1 . .
C C8 0.25568(9) 0.5486(2) 0.15090(12) 0.0550(5) Uani d . 1 . .
H H8 0.2771 0.4665 0.1587 0.066 Uiso calc R 1 . .
C C9 0.39837(8) 0.72041(18) 0.35651(10) 0.0402(4) Uani d . 1 . .
C C10 0.40476(8) 0.81147(19) 0.30699(10) 0.0431(4) Uani d . 1 . .
H H10 0.3716 0.8357 0.2689 0.052 Uiso calc R 1 . .
C C11 0.45865(9) 0.8669(2) 0.31249(11) 0.0476(5) Uani d . 1 . .
H H11 0.4616 0.9282 0.2786 0.057 Uiso calc R 1 . .
C C12 0.50864(8) 0.83169(19) 0.36834(11) 0.0453(4) Uani d . 1 . .
C C13 0.50374(8) 0.7419(2) 0.41826(11) 0.0475(5) Uani d . 1 . .
H H13 0.5371 0.7176 0.4560 0.057 Uiso calc R 1 . .
C C14 0.44863(8) 0.6872(2) 0.41224(11) 0.0474(5) Uani d . 1 . .
H H14 0.4456 0.6268 0.4466 0.057 Uiso calc R 1 . .
C C15 0.61272(11) 0.8573(4) 0.4232(2) 0.1002(11) Uani d . 1 . .
H H15A 0.6096 0.8793 0.4703 0.150 Uiso calc R 1 . .
H H15B 0.6457 0.9022 0.4154 0.150 Uiso calc R 1 . .
H H15C 0.6188 0.7663 0.4210 0.150 Uiso calc R 1 . .
C C16 0.25568(9) 0.5548(3) 0.38209(14) 0.0630(6) Uani d . 1 . .
H H16A 0.2487 0.4941 0.3428 0.095 Uiso calc R 1 . .
H H16B 0.2313 0.6293 0.3659 0.095 Uiso calc R 1 . .
H H16C 0.2459 0.5160 0.4222 0.095 Uiso calc R 1 . .
C C17 0.33296(11) 0.6809(3) 0.47360(12) 0.0646(6) Uani d . 1 . .
H H17A 0.3258 0.6332 0.5128 0.097 Uiso calc R 1 . .
H H17B 0.3067 0.7536 0.4621 0.097 Uiso calc R 1 . .
H H17C 0.3734 0.7101 0.4881 0.097 Uiso calc R 1 . .
C C18 0.37492(8) 0.41315(18) 0.23272(11) 0.0416(4) Uani d . 1 . .
C C19 0.37935(9) 0.2855(2) 0.21607(12) 0.0498(5) Uani d . 1 . .
H H19 0.3576 0.2247 0.2326 0.060 Uiso calc R 1 . .
C C20 0.41538(9) 0.2454(2) 0.17531(12) 0.0507(5) Uani d . 1 . .
H H20 0.4180 0.1587 0.1650 0.061 Uiso calc R 1 . .
C C21 0.44721(8) 0.3353(2) 0.15026(11) 0.0458(4) Uani d . 1 . .
C C22 0.44278(9) 0.4630(2) 0.16603(13) 0.0533(5) Uani d . 1 . .
H H22 0.4640 0.5240 0.1488 0.064 Uiso calc R 1 . .
C C23 0.40738(9) 0.5018(2) 0.20705(13) 0.0508(5) Uani d . 1 . .
H H23 0.4052 0.5885 0.2177 0.061 Uiso calc R 1 . .
C C24 0.49748(14) 0.1779(2) 0.10196(17) 0.0750(7) Uani d . 1 . .
H H24A 0.5128 0.1402 0.1495 0.113 Uiso calc R 1 . .
H H24B 0.5269 0.1721 0.0770 0.113 Uiso calc R 1 . .
H H24C 0.4623 0.1326 0.0747 0.113 Uiso calc R 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'
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
C12 O2 C15 . . 117.99(19) ?
C21 O4 C24 . . 117.58(18) ?
C7 N1 C6 . . 123.51(16) ?
C7 N1 C2 . . 116.70(15) ?
C6 N1 C2 . . 119.19(15) ?
N1 C2 C9 . . 109.97(14) ?
N1 C2 C3 . . 109.99(16) ?
C9 C2 C3 . . 118.89(16) ?
N1 C2 H2 . . 105.7 ?
C9 C2 H2 . . 105.7 ?
C3 C2 H2 . . 105.7 ?
C4 C3 C17 . . 112.76(18) ?
C4 C3 C16 . . 105.59(19) ?
C17 C3 C16 . . 108.54(17) ?
C4 C3 C2 . . 109.49(15) ?
C17 C3 C2 . . 111.01(18) ?
C16 C3 C2 . . 109.25(17) ?
O3 C4 C5 . . 120.7(2) ?
O3 C4 C3 . . 122.7(2) ?
C5 C4 C3 . . 116.68(17) ?
C4 C5 C6 . . 118.50(17) ?
C4 C5 H5A . . 107.7 ?
C6 C5 H5A . . 107.7 ?
C4 C5 H5B . . 107.7 ?
C6 C5 H5B . . 107.7 ?
H5A C5 H5B . . 107.1 ?
N1 C6 C18 . . 113.94(15) ?
N1 C6 C5 . . 111.57(16) ?
C18 C6 C5 . . 108.14(15) ?
N1 C6 H6 . . 107.6 ?
C18 C6 H6 . . 107.6 ?
C5 C6 H6 . . 107.6 ?
O1 C7 N1 . . 124.06(19) ?
O1 C7 C8 . . 118.08(18) ?
N1 C7 C8 . . 117.85(18) ?
C7 C8 Cl2 . . 109.96(16) ?
C7 C8 Cl1 . . 107.21(15) ?
Cl2 C8 Cl1 . . 110.00(12) ?
C7 C8 H8 . . 109.9 ?
Cl2 C8 H8 . . 109.9 ?
Cl1 C8 H8 . . 109.9 ?
C14 C9 C10 . . 117.29(17) ?
C14 C9 C2 . . 126.23(17) ?
C10 C9 C2 . . 116.48(16) ?
C11 C10 C9 . . 121.84(18) ?
C11 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
C10 C11 C12 . . 120.10(19) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
O2 C12 C13 . . 124.98(18) ?
O2 C12 C11 . . 115.57(18) ?
C13 C12 C11 . . 119.45(18) ?
C12 C13 C14 . . 119.78(18) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
C9 C14 C13 . . 121.55(19) ?
C9 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
O2 C15 H15A . . 109.5 ?
O2 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O2 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C3 C16 H16A . . 109.5 ?
C3 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C3 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C3 C17 H17A . . 109.5 ?
C3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C19 C18 C23 . . 117.99(18) ?
C19 C18 C6 . . 118.50(17) ?
C23 C18 C6 . . 123.37(18) ?
C18 C19 C20 . . 121.69(18) ?
C18 C19 H19 . . 119.2 ?
C20 C19 H19 . . 119.2 ?
C21 C20 C19 . . 119.30(19) ?
C21 C20 H20 . . 120.3 ?
C19 C20 H20 . . 120.3 ?
O4 C21 C22 . . 115.80(18) ?
O4 C21 C20 . . 124.66(19) ?
C22 C21 C20 . . 119.54(18) ?
C21 C22 C23 . . 120.75(19) ?
C21 C22 H22 . . 119.6 ?
C23 C22 H22 . . 119.6 ?
C22 C23 C18 . . 120.72(19) ?
C22 C23 H23 . . 119.6 ?
C18 C23 H23 . . 119.6 ?
O4 C24 H24A . . 109.5 ?
O4 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
O4 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
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
Cl1 C8 . 1.757(2) ?
Cl2 C8 . 1.749(2) ?
O1 C7 . 1.217(2) ?
O2 C12 . 1.368(2) ?
O2 C15 . 1.406(3) ?
O3 C4 . 1.202(3) ?
O4 C21 . 1.368(2) ?
O4 C24 . 1.406(3) ?
N1 C7 . 1.344(2) ?
N1 C6 . 1.483(2) ?
N1 C2 . 1.484(2) ?
C2 C9 . 1.528(2) ?
C2 C3 . 1.544(3) ?
C2 H2 . 0.98 ?
C3 C4 . 1.508(3) ?
C3 C17 . 1.524(3) ?
C3 C16 . 1.543(3) ?
C4 C5 . 1.505(3) ?
C5 C6 . 1.534(3) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 C18 . 1.521(3) ?
C6 H6 . 0.98 ?
C7 C8 . 1.533(3) ?
C8 H8 . 0.98 ?
C9 C14 . 1.380(3) ?
C9 C10 . 1.385(3) ?
C10 C11 . 1.372(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.383(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.370(3) ?
C13 C14 . 1.393(3) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C18 C19 . 1.377(3) ?
C18 C23 . 1.383(3) ?
C19 C20 . 1.387(3) ?
C19 H19 . 0.93 ?
C20 C21 . 1.376(3) ?
C20 H20 . 0.93 ?
C21 C22 . 1.373(3) ?
C22 C23 . 1.374(3) ?
C22 H22 . 0.93 ?
C23 H23 . 0.93 ?
C24 H24A . 0.96 ?
C24 H24B . 0.96 ?
C24 H24C . 0.96 ?
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
C6 H6 O1 4_545 0.98 2.30 3.216(2) 155
C13 H13 O3 5_666 0.93 2.58 3.453(3) 155
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
C7 N1 C2 C9 . . . . -104.12(18) ?
C6 N1 C2 C9 . . . . 84.47(19) ?
C7 N1 C2 C3 . . . . 123.10(17) ?
C6 N1 C2 C3 . . . . -48.31(19) ?
N1 C2 C3 C4 . . . . 60.4(2) ?
C9 C2 C3 C4 . . . . -67.6(2) ?
N1 C2 C3 C17 . . . . -174.47(15) ?
C9 C2 C3 C17 . . . . 57.5(2) ?
N1 C2 C3 C16 . . . . -54.8(2) ?
C9 C2 C3 C16 . . . . 177.18(18) ?
C17 C3 C4 O3 . . . . 29.1(3) ?
C16 C3 C4 O3 . . . . -89.2(3) ?
C2 C3 C4 O3 . . . . 153.3(2) ?
C17 C3 C4 C5 . . . . -150.11(19) ?
C16 C3 C4 C5 . . . . 91.5(2) ?
C2 C3 C4 C5 . . . . -26.0(2) ?
O3 C4 C5 C6 . . . . 158.4(2) ?
C3 C4 C5 C6 . . . . -22.3(3) ?
C7 N1 C6 C18 . . . . 66.7(2) ?
C2 N1 C6 C18 . . . . -122.54(17) ?
C7 N1 C6 C5 . . . . -170.53(17) ?
C2 N1 C6 C5 . . . . 0.3(2) ?
C4 C5 C6 N1 . . . . 36.3(2) ?
C4 C5 C6 C18 . . . . 162.32(18) ?
C6 N1 C7 O1 . . . . 178.95(18) ?
C2 N1 C7 O1 . . . . 7.9(3) ?
C6 N1 C7 C8 . . . . -0.6(3) ?
C2 N1 C7 C8 . . . . -171.63(16) ?
O1 C7 C8 Cl2 . . . . 49.9(2) ?
N1 C7 C8 Cl2 . . . . -130.51(17) ?
O1 C7 C8 Cl1 . . . . -69.7(2) ?
N1 C7 C8 Cl1 . . . . 109.92(18) ?
N1 C2 C9 C14 . . . . -110.8(2) ?
C3 C2 C9 C14 . . . . 17.3(3) ?
N1 C2 C9 C10 . . . . 68.9(2) ?
C3 C2 C9 C10 . . . . -163.05(18) ?
C14 C9 C10 C11 . . . . 0.1(3) ?
C2 C9 C10 C11 . . . . -179.62(18) ?
C9 C10 C11 C12 . . . . 0.4(3) ?
C15 O2 C12 C13 . . . . 2.6(3) ?
C15 O2 C12 C11 . . . . -177.9(3) ?
C10 C11 C12 O2 . . . . -179.95(18) ?
C10 C11 C12 C13 . . . . -0.5(3) ?
O2 C12 C13 C14 . . . . 179.43(19) ?
C11 C12 C13 C14 . . . . 0.0(3) ?
C10 C9 C14 C13 . . . . -0.6(3) ?
C2 C9 C14 C13 . . . . 179.11(18) ?
C12 C13 C14 C9 . . . . 0.5(3) ?
N1 C6 C18 C19 . . . . -160.22(17) ?
C5 C6 C18 C19 . . . . 75.1(2) ?
N1 C6 C18 C23 . . . . 24.2(3) ?
C5 C6 C18 C23 . . . . -100.5(2) ?
C23 C18 C19 C20 . . . . 0.4(3) ?
C6 C18 C19 C20 . . . . -175.39(19) ?
C18 C19 C20 C21 . . . . -0.5(3) ?
C24 O4 C21 C22 . . . . 169.2(2) ?
C24 O4 C21 C20 . . . . -11.7(3) ?
C19 C20 C21 O4 . . . . -179.0(2) ?
C19 C20 C21 C22 . . . . 0.0(3) ?
O4 C21 C22 C23 . . . . 179.7(2) ?
C20 C21 C22 C23 . . . . 0.6(3) ?
C21 C22 C23 C18 . . . . -0.7(4) ?
C19 C18 C23 C22 . . . . 0.2(3) ?
C6 C18 C23 C22 . . . . 175.8(2) ?
