#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/03/2230317.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_2230317
loop_
_publ_author_name
'Nesterov, Volodymyr V.'
'Sarkisov, Sergey S.'
'Shulaev, Vladimir'
'Nesterov, Vladimir N.'
_publ_section_title
;
 1-Benzyl-3,5-bis(4-chlorobenzylidene)piperidin-4-one
;
_journal_coeditor_code           FL2348
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1505
_journal_page_last               o1506
_journal_paper_doi               10.1107/S1600536811018587
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C26 H21 Cl2 N O'
_chemical_formula_moiety         'C26 H21 Cl2 N O'
_chemical_formula_sum            'C26 H21 Cl2 N O'
_chemical_formula_weight         434.34
_chemical_name_systematic
;
1-Benzyl-3,5-bis(4-chlorobenzylidene)piperidin-4-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.736(3)
_cell_angle_beta                 111.676(2)
_cell_angle_gamma                104.066(3)
_cell_formula_units_Z            4
_cell_length_a                   12.504(2)
_cell_length_b                   13.414(4)
_cell_length_c                   14.763(2)
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.41
_cell_measurement_theta_min      2.44
_cell_volume                     2095.7(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       ω
_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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24542
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.9617
_exptl_absorpt_correction_T_min  0.9224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.475
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0386
_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)+(0.0570P)²+1.1100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                7049
_reflns_number_total             8251
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2348.cif
_cod_data_source_block           I
_cod_database_code               2230317
_cod_database_fobs_code          2230317
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 0.01606(5) 0.78507(4) 0.69670(4) 0.03870(13) Uani d . 1 1 . .
Cl Cl2A 0.65255(5) 0.12893(5) 0.08931(4) 0.03854(13) Uani d . 1 1 . .
O O1A 0.35806(13) 0.34345(11) 0.51320(10) 0.0336(3) Uani d . 1 1 . .
N N1A 0.24037(13) 0.45157(12) 0.27541(11) 0.0214(3) Uani d . 1 1 . .
C C1A 0.20424(16) 0.49694(15) 0.19088(13) 0.0235(4) Uani d . 1 1 . .
H H1AA 0.2213 0.4597 0.1348 0.028 Uiso calc R 1 1 . .
H H1AB 0.2548 0.5758 0.2178 0.028 Uiso calc R 1 1 . .
C C2A 0.24894(16) 0.52293(14) 0.37107(13) 0.0225(4) Uani d . 1 1 . .
H H2AA 0.1714 0.5376 0.3558 0.027 Uiso calc R 1 1 . .
H H2AB 0.3172 0.5937 0.3974 0.027 Uiso calc R 1 1 . .
C C3A 0.27142(16) 0.46956(14) 0.45281(13) 0.0225(4) Uani d . 1 1 . .
C C4A 0.33892(16) 0.39154(14) 0.44991(13) 0.0237(4) Uani d . 1 1 . .
C C5A 0.38468(15) 0.37528(14) 0.36967(13) 0.0226(4) Uani d . 1 1 . .
C C6A 0.35812(16) 0.43693(15) 0.29532(13) 0.0230(4) Uani d . 1 1 . .
H H6AA 0.4249 0.5093 0.3251 0.028 Uiso calc R 1 1 . .
H H6AB 0.3550 0.3959 0.2293 0.028 Uiso calc R 1 1 . .
C C7A 0.23584(16) 0.48474(15) 0.52962(13) 0.0243(4) Uani d . 1 1 . .
H H7AA 0.2517 0.4389 0.5698 0.029 Uiso calc R 1 1 . .
C C8A 0.17781(16) 0.55822(15) 0.56197(13) 0.0242(4) Uani d . 1 1 . .
C C9A 0.12682(16) 0.53599(16) 0.62905(13) 0.0273(4) Uani d . 1 1 . .
H H9AA 0.1272 0.4722 0.6470 0.033 Uiso calc R 1 1 . .
C C10A 0.07631(16) 0.60382(16) 0.66965(14) 0.0279(4) Uani d . 1 1 . .
H H10A 0.0426 0.5874 0.7150 0.033 Uiso calc R 1 1 . .
C C11A 0.07585(17) 0.69624(16) 0.64286(14) 0.0283(4) Uani d . 1 1 . .
C C12A 0.12458(17) 0.72161(15) 0.57642(14) 0.0287(4) Uani d . 1 1 . .
H H12A 0.1224 0.7849 0.5581 0.034 Uiso calc R 1 1 . .
C C13A 0.17646(17) 0.65334(15) 0.53720(13) 0.0265(4) Uani d . 1 1 . .
H H13A 0.2115 0.6712 0.4931 0.032 Uiso calc R 1 1 . .
C C14A 0.44035(15) 0.30143(15) 0.36640(13) 0.0238(4) Uani d . 1 1 . .
H H14A 0.4473 0.2674 0.4173 0.029 Uiso calc R 1 1 . .
C C15A 0.49216(15) 0.26528(15) 0.29595(13) 0.0235(4) Uani d . 1 1 . .
C C16A 0.49531(16) 0.15947(15) 0.27926(14) 0.0256(4) Uani d . 1 1 . .
H H16A 0.4647 0.1160 0.3133 0.031 Uiso calc R 1 1 . .
C C17A 0.54175(17) 0.11651(16) 0.21450(15) 0.0285(4) Uani d . 1 1 . .
H H17A 0.5406 0.0436 0.2023 0.034 Uiso calc R 1 1 . .
C C18A 0.59003(16) 0.18160(16) 0.16772(14) 0.0271(4) Uani d . 1 1 . .
C C19A 0.59069(16) 0.28780(15) 0.18407(14) 0.0269(4) Uani d . 1 1 . .
H H19A 0.6250 0.3321 0.1524 0.032 Uiso calc R 1 1 . .
C C20A 0.54096(16) 0.32860(15) 0.24702(13) 0.0250(4) Uani d . 1 1 . .
H H20A 0.5399 0.4007 0.2572 0.030 Uiso calc R 1 1 . .
C C21A 0.06923(16) 0.48300(14) 0.14668(12) 0.0212(3) Uani d . 1 1 . .
C C22A 0.03196(17) 0.57277(14) 0.14847(14) 0.0265(4) Uani d . 1 1 . .
H H22A 0.0921 0.6446 0.1806 0.032 Uiso calc R 1 1 . .
C C23A -0.09251(18) 0.55824(15) 0.10361(14) 0.0300(4) Uani d . 1 1 . .
H H23A -0.1169 0.6201 0.1046 0.036 Uiso calc R 1 1 . .
C C24A -0.18115(17) 0.45380(15) 0.05750(14) 0.0275(4) Uani d . 1 1 . .
H H24A -0.2662 0.4438 0.0266 0.033 Uiso calc R 1 1 . .
C C25A -0.14470(17) 0.36398(15) 0.05688(13) 0.0257(4) Uani d . 1 1 . .
H H25A -0.2051 0.2923 0.0263 0.031 Uiso calc R 1 1 . .
C C26A -0.02083(17) 0.37834(14) 0.10062(13) 0.0240(4) Uani d . 1 1 . .
H H26A 0.0032 0.3163 0.0993 0.029 Uiso calc R 1 1 . .
Cl Cl1B 0.95734(5) -0.23822(4) 0.32282(4) 0.03777(13) Uani d . 1 1 . .
Cl Cl2B 0.37099(5) 0.37742(4) 0.99889(4) 0.03390(13) Uani d . 1 1 . .
O O1B 0.56754(19) 0.16150(17) 0.50449(12) 0.0619(6) Uani d . 1 1 . .
N N1B 0.80808(13) 0.13829(11) 0.75624(11) 0.0214(3) Uani d . 1 1 . .
C C1B 0.90276(16) 0.13447(14) 0.85070(13) 0.0231(4) Uani d . 1 1 . .
H H1BA 0.9251 0.2006 0.9096 0.028 Uiso calc R 1 1 . .
H H1BB 0.9775 0.1383 0.8406 0.028 Uiso calc R 1 1 . .
C C2B 0.77495(16) 0.04704(14) 0.66319(13) 0.0218(3) Uani d . 1 1 . .
H H2BA 0.7250 -0.0217 0.6647 0.026 Uiso calc R 1 1 . .
H H2BB 0.8506 0.0382 0.6615 0.026 Uiso calc R 1 1 . .
C C3B 0.70258(17) 0.06941(14) 0.56795(13) 0.0244(4) Uani d . 1 1 . .
C C4B 0.62426(19) 0.13581(17) 0.57702(15) 0.0321(4) Uani d . 1 1 . .
C C5B 0.61373(16) 0.16622(14) 0.67621(13) 0.0236(4) Uani d . 1 1 . .
C C6B 0.69847(16) 0.14481(14) 0.76757(13) 0.0221(4) Uani d . 1 1 . .
H H6BA 0.7233 0.2045 0.8326 0.026 Uiso calc R 1 1 . .
H H6BB 0.6544 0.0753 0.7718 0.026 Uiso calc R 1 1 . .
C C7B 0.70371(17) 0.03605(15) 0.47530(14) 0.0259(4) Uani d . 1 1 . .
H H7BA 0.6560 0.0600 0.4238 0.031 Uiso calc R 1 1 . .
C C8B 0.76759(16) -0.03161(14) 0.44228(13) 0.0242(4) Uani d . 1 1 . .
C C9B 0.79157(17) -0.02325(15) 0.35788(14) 0.0260(4) Uani d . 1 1 . .
H H9BA 0.7661 0.0258 0.3247 0.031 Uiso calc R 1 1 . .
C C10B 0.85128(18) -0.08460(15) 0.32190(14) 0.0288(4) Uani d . 1 1 . .
H H10B 0.8684 -0.0767 0.2658 0.035 Uiso calc R 1 1 . .
C C11B 0.88558(17) -0.15780(15) 0.36921(14) 0.0274(4) Uani d . 1 1 . .
C C12B 0.86061(17) -0.17053(15) 0.45097(14) 0.0273(4) Uani d . 1 1 . .
H H12B 0.8835 -0.2218 0.4820 0.033 Uiso calc R 1 1 . .
C C13B 0.80220(17) -0.10792(14) 0.48681(13) 0.0254(4) Uani d . 1 1 . .
H H13B 0.7851 -0.1167 0.5427 0.030 Uiso calc R 1 1 . .
C C14B 0.52956(16) 0.21299(14) 0.67633(13) 0.0241(4) Uani d . 1 1 . .
H H14B 0.4869 0.2238 0.6133 0.029 Uiso calc R 1 1 . .
C C15B 0.49337(15) 0.24968(14) 0.75771(13) 0.0216(3) Uani d . 1 1 . .
C C16B 0.43215(16) 0.32462(14) 0.74851(14) 0.0235(4) Uani d . 1 1 . .
H H16B 0.4161 0.3487 0.6906 0.028 Uiso calc R 1 1 . .
C C17B 0.39458(16) 0.36416(15) 0.82178(14) 0.0256(4) Uani d . 1 1 . .
H H17B 0.3554 0.4164 0.8154 0.031 Uiso calc R 1 1 . .
C C18B 0.41504(16) 0.32627(15) 0.90467(13) 0.0235(4) Uani d . 1 1 . .
C C19B 0.47058(16) 0.24907(15) 0.91413(13) 0.0245(4) Uani d . 1 1 . .
H H19B 0.4811 0.2217 0.9697 0.029 Uiso calc R 1 1 . .
C C20B 0.51062(16) 0.21212(14) 0.84192(13) 0.0234(4) Uani d . 1 1 . .
H H20B 0.5505 0.1604 0.8494 0.028 Uiso calc R 1 1 . .
C C21B 0.86682(15) 0.03449(14) 0.88084(13) 0.0223(4) Uani d . 1 1 . .
C C22B 0.88113(16) -0.06166(15) 0.83723(14) 0.0265(4) Uani d . 1 1 . .
H H22B 0.9155 -0.0639 0.7895 0.032 Uiso calc R 1 1 . .
C C23B 0.84610(18) -0.15432(16) 0.86226(15) 0.0324(4) Uani d . 1 1 . .
H H23B 0.8552 -0.2196 0.8310 0.039 Uiso calc R 1 1 . .
C C24B 0.79766(18) -0.15083(17) 0.93324(16) 0.0360(5) Uani d . 1 1 . .
H H24B 0.7741 -0.2137 0.9511 0.043 Uiso calc R 1 1 . .
C C25B 0.78367(18) -0.05629(18) 0.97777(16) 0.0344(4) Uani d . 1 1 . .
H H25B 0.7504 -0.0542 1.0262 0.041 Uiso calc R 1 1 . .
C C26B 0.81808(17) 0.03602(16) 0.95213(14) 0.0278(4) Uani d . 1 1 . .
H H26B 0.8083 0.1009 0.9835 0.033 Uiso calc R 1 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
C6A N1A C2A . . 109.92(13) ?
C6A N1A C1A . . 110.49(13) ?
C2A N1A C1A . . 111.03(13) ?
N1A C1A C21A . . 112.10(14) ?
N1A C1A H1AA . . 109.2 ?
C21A C1A H1AA . . 109.2 ?
N1A C1A H1AB . . 109.2 ?
C21A C1A H1AB . . 109.2 ?
H1AA C1A H1AB . . 107.9 ?
N1A C2A C3A . . 110.47(14) ?
N1A C2A H2AA . . 109.6 ?
C3A C2A H2AA . . 109.6 ?
N1A C2A H2AB . . 109.6 ?
C3A C2A H2AB . . 109.6 ?
H2AA C2A H2AB . . 108.1 ?
C7A C3A C4A . . 115.94(16) ?
C7A C3A C2A . . 126.30(16) ?
C4A C3A C2A . . 117.76(15) ?
O1A C4A C5A 1 . 120.82(16) ?
O1A C4A C5A . . 120.82(16) ?
O1A C4A C3A 1 . 120.99(16) ?
O1A C4A C3A . . 120.99(16) ?
C5A C4A C3A . . 118.17(15) ?
C14A C5A C4A . . 116.67(16) ?
C14A C5A C6A . . 125.41(16) ?
C4A C5A C6A . . 117.80(15) ?
N1A C6A C5A . . 110.04(14) ?
N1A C6A H6AA . . 109.7 ?
C5A C6A H6AA . . 109.7 ?
N1A C6A H6AB . . 109.7 ?
C5A C6A H6AB . . 109.7 ?
H6AA C6A H6AB . . 108.2 ?
C3A C7A C8A . . 131.99(17) ?
C3A C7A H7AA . . 114.0 ?
C8A C7A H7AA . . 114.0 ?
C13A C8A C9A . . 117.67(17) ?
C13A C8A C7A . . 125.01(16) ?
C9A C8A C7A . . 117.16(17) ?
C10A C9A C8A . . 122.13(18) ?
C10A C9A H9AA . . 118.9 ?
C8A C9A H9AA . . 118.9 ?
C9A C10A C11A . . 118.51(17) ?
C9A C10A H10A . . 120.7 ?
C11A C10A H10A . . 120.7 ?
C10A C11A C12A . . 121.59(17) ?
C10A C11A Cl1A . . 118.99(14) ?
C12A C11A Cl1A . . 119.40(15) ?
C13A C12A C11A . . 119.25(18) ?
C13A C12A H12A . . 120.4 ?
C11A C12A H12A . . 120.4 ?
C12A C13A C8A . . 120.83(17) ?
C12A C13A H13A . . 119.6 ?
C8A C13A H13A . . 119.6 ?
C5A C14A C15A . . 129.81(16) ?
C5A C14A H14A . . 115.1 ?
C15A C14A H14A . . 115.1 ?
C16A C15A C20A . . 117.86(17) ?
C16A C15A C14A . . 116.56(16) ?
C20A C15A C14A . . 125.56(17) ?
C17A C16A C15A . . 121.75(17) ?
C17A C16A H16A . . 119.1 ?
C15A C16A H16A . . 119.1 ?
C16A C17A C18A . . 118.90(18) ?
C16A C17A H17A . . 120.5 ?
C18A C17A H17A . . 120.5 ?
C17A C18A C19A . . 120.95(17) ?
C17A C18A Cl2A . . 118.89(15) ?
C19A C18A Cl2A . . 120.16(14) ?
C20A C19A C18A . . 119.41(16) ?
C20A C19A H19A . . 120.3 ?
C18A C19A H19A . . 120.3 ?
C19A C20A C15A . . 121.08(17) ?
C19A C20A H20A . . 119.5 ?
C15A C20A H20A . . 119.5 ?
C22A C21A C26A . . 118.64(16) ?
C22A C21A C1A . . 121.36(16) ?
C26A C21A C1A . . 119.98(15) ?
C23A C22A C21A . . 120.60(17) ?
C23A C22A H22A . . 119.7 ?
C21A C22A H22A . . 119.7 ?
C24A C23A C22A . . 120.22(17) ?
C24A C23A H23A . . 119.9 ?
C22A C23A H23A . . 119.9 ?
C23A C24A C25A . . 119.49(17) ?
C23A C24A H24A . . 120.3 ?
C25A C24A H24A . . 120.3 ?
C26A C25A C24A . . 120.30(17) ?
C26A C25A H25A . . 119.9 ?
C24A C25A H25A . . 119.8 ?
C25A C26A C21A . . 120.73(16) ?
C25A C26A H26A . . 119.6 ?
C21A C26A H26A . . 119.6 ?
C6B N1B C2B . . 110.96(13) ?
C6B N1B C1B . . 112.52(13) ?
C2B N1B C1B . . 112.25(13) ?
N1B C1B C21B . . 116.12(14) ?
N1B C1B H1BA . . 108.3 ?
C21B C1B H1BA . . 108.3 ?
N1B C1B H1BB . . 108.3 ?
C21B C1B H1BB . . 108.3 ?
H1BA C1B H1BB . . 107.4 ?
N1B C2B C3B . . 109.53(14) ?
N1B C2B H2BA . . 109.8 ?
C3B C2B H2BA . . 109.8 ?
N1B C2B H2BB . . 109.8 ?
C3B C2B H2BB . . 109.8 ?
H2BA C2B H2BB . . 108.2 ?
C7B C3B C4B . . 117.08(16) ?
C7B C3B C2B . . 125.51(16) ?
C4B C3B C2B . . 117.40(15) ?
O1B C4B C5B 1 . 120.89(18) ?
O1B C4B C5B . . 120.89(18) ?
O1B C4B C3B 1 . 121.05(17) ?
O1B C4B C3B . . 121.05(17) ?
C5B C4B C3B . . 118.02(16) ?
C14B C5B C4B . . 116.11(16) ?
C14B C5B C6B . . 125.67(16) ?
C4B C5B C6B . . 118.20(15) ?
N1B C6B C5B . . 110.34(14) ?
N1B C6B H6BA . . 109.6 ?
C5B C6B H6BA . . 109.6 ?
N1B C6B H6BB . . 109.6 ?
C5B C6B H6BB . . 109.6 ?
H6BA C6B H6BB . . 108.1 ?
C3B C7B C8B . . 129.59(17) ?
C3B C7B H7BA . . 115.2 ?
C8B C7B H7BA . . 115.2 ?
C13B C8B C9B . . 117.56(16) ?
C13B C8B C7B . . 124.16(16) ?
C9B C8B C7B . . 118.23(16) ?
C10B C9B C8B . . 121.70(17) ?
C10B C9B H9BA . . 119.1 ?
C8B C9B H9BA . . 119.1 ?
C9B C10B C11B . . 118.80(17) ?
C9B C10B H10B . . 120.6 ?
C11B C10B H10B . . 120.6 ?
C10B C11B C12B . . 121.21(17) ?
C10B C11B Cl1B . . 119.43(14) ?
C12B C11B Cl1B . . 119.33(15) ?
C13B C12B C11B . . 119.37(17) ?
C13B C12B H12B . . 120.3 ?
C11B C12B H12B . . 120.3 ?
C12B C13B C8B . . 121.32(17) ?
C12B C13B H13B . . 119.3 ?
C8B C13B H13B . . 119.3 ?
C5B C14B C15B . . 130.51(16) ?
C5B C14B H14B . . 114.7 ?
C15B C14B H14B . . 114.7 ?
C16B C15B C20B . . 117.61(16) ?
C16B C15B C14B . . 117.40(15) ?
C20B C15B C14B . . 124.93(16) ?
C17B C16B C15B . . 121.57(16) ?
C17B C16B H16B . . 119.2 ?
C15B C16B H16B . . 119.2 ?
C16B C17B C18B . . 118.99(16) ?
C16B C17B H17B . . 120.5 ?
C18B C17B H17B . . 120.5 ?
C19B C18B C17B . . 121.11(16) ?
C19B C18B Cl2B . . 119.42(14) ?
C17B C18B Cl2B . . 119.47(14) ?
C20B C19B C18B . . 119.43(16) ?
C20B C19B H19B . . 120.3 ?
C18B C19B H19B . . 120.3 ?
C19B C20B C15B . . 121.20(16) ?
C19B C20B H20B . . 119.4 ?
C15B C20B H20B . . 119.4 ?
C22B C21B C26B . . 118.14(17) ?
C22B C21B C1B . . 120.62(16) ?
C26B C21B C1B . . 121.24(16) ?
C23B C22B C21B . . 121.22(18) ?
C23B C22B H22B . . 119.4 ?
C21B C22B H22B . . 119.4 ?
C24B C23B C22B . . 119.57(18) ?
C24B C23B H23B . . 120.2 ?
C22B C23B H23B . . 120.2 ?
C25B C24B C23B . . 120.06(18) ?
C25B C24B H24B . . 120.0 ?
C23B C24B H24B . . 120.0 ?
C24B C25B C26B . . 120.25(19) ?
C24B C25B H25B . . 119.9 ?
C26B C25B H25B . . 119.9 ?
C25B C26B C21B . . 120.76(18) ?
C25B C26B H26B . . 119.6 ?
C21B C26B H26B . . 119.6 ?
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
Cl1A C11A . 1.7507(19) ?
Cl2A C18A . 1.7398(18) ?
O1A C4A . 1.234(2) ?
N1A C6A . 1.462(2) ?
N1A C2A . 1.471(2) ?
N1A C1A . 1.478(2) ?
C1A C21A . 1.513(2) ?
C1A H1AA . 0.9900 ?
C1A H1AB . 0.9900 ?
C2A C3A . 1.509(2) ?
C2A H2AA . 0.9900 ?
C2A H2AB . 0.9900 ?
C3A C7A . 1.357(2) ?
C3A C4A . 1.499(2) ?
C4A O1A 1 1.234(2) ?
C4A C5A . 1.492(2) ?
C5A C14A . 1.344(3) ?
C5A C6A . 1.505(2) ?
C6A H6AA . 0.9900 ?
C6A H6AB . 0.9900 ?
C7A C8A . 1.457(3) ?
C7A H7AA . 0.9500 ?
C8A C13A . 1.405(3) ?
C8A C9A . 1.407(3) ?
C9A C10A . 1.380(3) ?
C9A H9AA . 0.9500 ?
C10A C11A . 1.382(3) ?
C10A H10A . 0.9500 ?
C11A C12A . 1.392(3) ?
C12A C13A . 1.388(3) ?
C12A H12A . 0.9500 ?
C13A H13A . 0.9500 ?
C14A C15A . 1.471(2) ?
C14A H14A . 0.9500 ?
C15A C16A . 1.399(3) ?
C15A C20A . 1.400(3) ?
C16A C17A . 1.383(3) ?
C16A H16A . 0.9500 ?
C17A C18A . 1.386(3) ?
C17A H17A . 0.9500 ?
C18A C19A . 1.389(3) ?
C19A C20A . 1.385(3) ?
C19A H19A . 0.9500 ?
C20A H20A . 0.9500 ?
C21A C22A . 1.391(2) ?
C21A C26A . 1.395(2) ?
C22A C23A . 1.390(3) ?
C22A H22A . 0.9500 ?
C23A C24A . 1.386(3) ?
C23A H23A . 0.9500 ?
C24A C25A . 1.387(3) ?
C24A H24A . 0.9500 ?
C25A C26A . 1.384(3) ?
C25A H25A . 0.9500 ?
C26A H26A . 0.9500 ?
Cl1B C11B . 1.7427(19) ?
Cl2B C18B . 1.7430(18) ?
O1B C4B . 1.220(2) ?
N1B C6B . 1.461(2) ?
N1B C2B . 1.466(2) ?
N1B C1B . 1.480(2) ?
C1B C21B . 1.522(2) ?
C1B H1BA . 0.9900 ?
C1B H1BB . 0.9900 ?
C2B C3B . 1.505(2) ?
C2B H2BA . 0.9900 ?
C2B H2BB . 0.9900 ?
C3B C7B . 1.349(2) ?
C3B C4B . 1.496(3) ?
C4B O1B 1 1.220(2) ?
C4B C5B . 1.494(2) ?
C5B C14B . 1.350(2) ?
C5B C6B . 1.512(2) ?
C6B H6BA . 0.9900 ?
C6B H6BB . 0.9900 ?
C7B C8B . 1.464(3) ?
C7B H7BA . 0.9500 ?
C8B C13B . 1.403(3) ?
C8B C9B . 1.406(2) ?
C9B C10B . 1.384(3) ?
C9B H9BA . 0.9500 ?
C10B C11B . 1.386(3) ?
C10B H10B . 0.9500 ?
C11B C12B . 1.388(3) ?
C12B C13B . 1.381(3) ?
C12B H12B . 0.9500 ?
C13B H13B . 0.9500 ?
C14B C15B . 1.463(2) ?
C14B H14B . 0.9500 ?
C15B C16B . 1.404(2) ?
C15B C20B . 1.406(2) ?
C16B C17B . 1.384(2) ?
C16B H16B . 0.9500 ?
C17B C18B . 1.388(2) ?
C17B H17B . 0.9500 ?
C18B C19B . 1.384(3) ?
C19B C20B . 1.384(2) ?
C19B H19B . 0.9500 ?
C20B H20B . 0.9500 ?
C21B C22B . 1.393(3) ?
C21B C26B . 1.396(2) ?
C22B C23B . 1.390(3) ?
C22B H22B . 0.9500 ?
C23B C24B . 1.389(3) ?
C23B H23B . 0.9500 ?
C24B C25B . 1.377(3) ?
C24B H24B . 0.9500 ?
C25B C26B . 1.389(3) ?
C25B H25B . 0.9500 ?
C26B H26B . 0.9500 ?
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
C16B H16B O1A 1 0.95 2.42 3.334(2) 160
C14A H14A O1B 1 0.95 2.52 3.309(2) 141
C16A H16A O1B 1 0.95 2.48 3.099(2) 122
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
C6A N1A C1A C21A . . . . 163.42(14) ?
C2A N1A C1A C21A . . . . -74.36(18) ?
C6A N1A C2A C3A . . . . -63.95(17) ?
C1A N1A C2A C3A . . . . 173.49(14) ?
N1A C2A C3A C7A . . . . -151.02(17) ?
N1A C2A C3A C4A . . . . 28.7(2) ?
O1A O1A C4A C5A 1 . . . 0.0(3) ?
O1A O1A C4A C3A 1 . . . 0.0(3) ?
C7A C3A C4A O1A . . . 1 1.2(3) ?
C2A C3A C4A O1A . . . 1 -178.50(16) ?
C7A C3A C4A O1A . . . . 1.2(3) ?
C2A C3A C4A O1A . . . . -178.50(16) ?
C7A C3A C4A C5A . . . . -177.55(15) ?
C2A C3A C4A C5A . . . . 2.7(2) ?
O1A C4A C5A C14A 1 . . . 3.9(3) ?
O1A C4A C5A C14A . . . . 3.9(3) ?
C3A C4A C5A C14A . . . . -177.34(15) ?
O1A C4A C5A C6A 1 . . . -179.84(16) ?
O1A C4A C5A C6A . . . . -179.84(16) ?
C3A C4A C5A C6A . . . . -1.1(2) ?
C2A N1A C6A C5A . . . . 65.66(18) ?
C1A N1A C6A C5A . . . . -171.47(14) ?
C14A C5A C6A N1A . . . . 143.83(17) ?
C4A C5A C6A N1A . . . . -32.1(2) ?
C4A C3A C7A C8A . . . . 174.85(17) ?
C2A C3A C7A C8A . . . . -5.5(3) ?
C3A C7A C8A C13A . . . . -19.2(3) ?
C3A C7A C8A C9A . . . . 165.48(18) ?
C13A C8A C9A C10A . . . . 0.3(3) ?
C7A C8A C9A C10A . . . . 175.98(16) ?
C8A C9A C10A C11A . . . . 0.2(3) ?
C9A C10A C11A C12A . . . . 0.1(3) ?
C9A C10A C11A Cl1A . . . . -178.20(14) ?
C10A C11A C12A C13A . . . . -0.9(3) ?
Cl1A C11A C12A C13A . . . . 177.40(14) ?
C11A C12A C13A C8A . . . . 1.4(3) ?
C9A C8A C13A C12A . . . . -1.1(3) ?
C7A C8A C13A C12A . . . . -176.41(17) ?
C4A C5A C14A C15A . . . . 178.45(16) ?
C6A C5A C14A C15A . . . . 2.5(3) ?
C5A C14A C15A C16A . . . . -153.04(19) ?
C5A C14A C15A C20A . . . . 28.7(3) ?
C20A C15A C16A C17A . . . . -1.7(3) ?
C14A C15A C16A C17A . . . . 179.90(16) ?
C15A C16A C17A C18A . . . . 2.1(3) ?
C16A C17A C18A C19A . . . . -0.8(3) ?
C16A C17A C18A Cl2A . . . . 178.13(14) ?
C17A C18A C19A C20A . . . . -0.8(3) ?
Cl2A C18A C19A C20A . . . . -179.76(13) ?
C18A C19A C20A C15A . . . . 1.2(3) ?
C16A C15A C20A C19A . . . . 0.0(3) ?
C14A C15A C20A C19A . . . . 178.24(16) ?
N1A C1A C21A C22A . . . . 120.53(17) ?
N1A C1A C21A C26A . . . . -61.1(2) ?
C26A C21A C22A C23A . . . . -1.1(3) ?
C1A C21A C22A C23A . . . . 177.27(16) ?
C21A C22A C23A C24A . . . . 0.7(3) ?
C22A C23A C24A C25A . . . . 0.3(3) ?
C23A C24A C25A C26A . . . . -0.9(3) ?
C24A C25A C26A C21A . . . . 0.5(3) ?
C22A C21A C26A C25A . . . . 0.5(2) ?
C1A C21A C26A C25A . . . . -177.93(16) ?
C6B N1B C1B C21B . . . . 64.13(19) ?
C2B N1B C1B C21B . . . . -61.88(19) ?
C6B N1B C2B C3B . . . . 66.43(17) ?
C1B N1B C2B C3B . . . . -166.71(14) ?
N1B C2B C3B C7B . . . . 148.23(18) ?
N1B C2B C3B C4B . . . . -30.7(2) ?
O1B O1B C4B C5B 1 . . . 0.0(2) ?
O1B O1B C4B C3B 1 . . . 0.0(3) ?
C7B C3B C4B O1B . . . 1 -2.5(3) ?
C2B C3B C4B O1B . . . 1 176.6(2) ?
C7B C3B C4B O1B . . . . -2.5(3) ?
C2B C3B C4B O1B . . . . 176.6(2) ?
C7B C3B C4B C5B . . . . 175.28(17) ?
C2B C3B C4B C5B . . . . -5.7(3) ?
O1B C4B C5B C14B 1 . . . 6.4(3) ?
O1B C4B C5B C14B . . . . 6.4(3) ?
C3B C4B C5B C14B . . . . -171.31(17) ?
O1B C4B C5B C6B 1 . . . -172.3(2) ?
O1B C4B C5B C6B . . . . -172.3(2) ?
C3B C4B C5B C6B . . . . 9.9(3) ?
C2B N1B C6B C5B . . . . -62.09(18) ?
C1B N1B C6B C5B . . . . 171.20(14) ?
C14B C5B C6B N1B . . . . -155.89(17) ?
C4B C5B C6B N1B . . . . 22.7(2) ?
C4B C3B C7B C8B . . . . -178.06(18) ?
C2B C3B C7B C8B . . . . 3.0(3) ?
C3B C7B C8B C13B . . . . 25.4(3) ?
C3B C7B C8B C9B . . . . -157.34(19) ?
C13B C8B C9B C10B . . . . -2.4(3) ?
C7B C8B C9B C10B . . . . -179.87(17) ?
C8B C9B C10B C11B . . . . 1.5(3) ?
C9B C10B C11B C12B . . . . 0.3(3) ?
C9B C10B C11B Cl1B . . . . 178.39(14) ?
C10B C11B C12B C13B . . . . -1.0(3) ?
Cl1B C11B C12B C13B . . . . -179.10(14) ?
C11B C12B C13B C8B . . . . 0.0(3) ?
C9B C8B C13B C12B . . . . 1.7(3) ?
C7B C8B C13B C12B . . . . 178.97(17) ?
C4B C5B C14B C15B . . . . 178.23(18) ?
C6B C5B C14B C15B . . . . -3.1(3) ?
C5B C14B C15B C16B . . . . 160.85(19) ?
C5B C14B C15B C20B . . . . -22.0(3) ?
C20B C15B C16B C17B . . . . 2.8(3) ?
C14B C15B C16B C17B . . . . -179.86(16) ?
C15B C16B C17B C18B . . . . -1.8(3) ?
C16B C17B C18B C19B . . . . -0.8(3) ?
C16B C17B C18B Cl2B . . . . 178.72(14) ?
C17B C18B C19B C20B . . . . 2.5(3) ?
Cl2B C18B C19B C20B . . . . -177.08(14) ?
C18B C19B C20B C15B . . . . -1.5(3) ?
C16B C15B C20B C19B . . . . -1.1(3) ?
C14B C15B C20B C19B . . . . -178.24(17) ?
N1B C1B C21B C22B . . . . 85.3(2) ?
N1B C1B C21B C26B . . . . -94.30(19) ?
C26B C21B C22B C23B . . . . 1.1(3) ?
C1B C21B C22B C23B . . . . -178.52(16) ?
C21B C22B C23B C24B . . . . -1.0(3) ?
C22B C23B C24B C25B . . . . 0.5(3) ?
C23B C24B C25B C26B . . . . -0.1(3) ?
C24B C25B C26B C21B . . . . 0.2(3) ?
C22B C21B C26B C25B . . . . -0.7(3) ?
C1B C21B C26B C25B . . . . 178.92(17) ?
