#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/01/2230139.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_2230139
loop_
_publ_author_name
'Basiri, Alireza'
'Murugaiyah, Vikneswaran'
'Osman, Hasnah'
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 (3E,5E)-1-Acryloyl-3,5-bis(2-chlorobenzylidene)piperidin-4-one
;
_journal_coeditor_code           RZ2586
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1228
_journal_page_last               o1229
_journal_paper_doi               10.1107/S1600536811015042
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H17 Cl2 N O2'
_chemical_formula_moiety         'C22 H17 Cl2 N O2'
_chemical_formula_sum            'C22 H17 Cl2 N O2'
_chemical_formula_weight         398.27
_chemical_name_systematic
;
(3E,5E)-1-Acryloyl-3,5-bis(2-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                108.3480(10)
_cell_angle_beta                 102.6950(10)
_cell_angle_gamma                103.6490(10)
_cell_formula_units_Z            4
_cell_length_a                   9.1426(5)
_cell_length_b                   14.3459(8)
_cell_length_c                   16.6637(9)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.56
_cell_volume                     1910.71(18)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector
;
_diffrn_measurement_method       'φ and 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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30297
_diffrn_reflns_theta_full        30.15
_diffrn_reflns_theta_max         30.15
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.9468
_exptl_absorpt_correction_T_min  0.8582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.646
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         11008
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0456
_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)+(0.0638P)²+1.1810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1321
_reflns_number_gt                8952
_reflns_number_total             11008
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2586.cif
_cod_data_source_block           I
_cod_database_code               2230139
_cod_database_fobs_code          2230139
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 0.73359(6) 0.69893(3) 0.19867(3) 0.03298(11) Uani d . 1 1 . .
Cl Cl2A 1.26065(7) 1.12704(4) -0.00037(5) 0.04944(15) Uani d . 1 1 . .
O O1A 1.14934(15) 0.84607(9) 0.10213(8) 0.0263(3) Uani d . 1 1 . .
O O2A 0.62640(15) 0.62692(9) -0.19689(8) 0.0272(3) Uani d . 1 1 . .
N N1A 0.89407(16) 0.67110(11) -0.15374(9) 0.0223(3) Uani d . 1 1 . .
C C1A 0.71064(19) 0.57830(12) 0.11990(11) 0.0220(3) Uani d . 1 1 . .
C C2A 0.6011(2) 0.49154(14) 0.11782(12) 0.0272(3) Uani d . 1 1 . .
H H2AA 0.5427 0.4988 0.1573 0.033 Uiso calc R 1 1 . .
C C3A 0.5792(2) 0.39396(14) 0.05665(13) 0.0288(4) Uani d . 1 1 . .
H H3AA 0.5053 0.3355 0.0545 0.035 Uiso calc R 1 1 . .
C C4A 0.6682(2) 0.38369(13) -0.00161(12) 0.0269(3) Uani d . 1 1 . .
H H4AA 0.6551 0.3181 -0.0420 0.032 Uiso calc R 1 1 . .
C C5A 0.77649(19) 0.47130(12) 0.00057(11) 0.0220(3) Uani d . 1 1 . .
H H5AA 0.8349 0.4635 -0.0389 0.026 Uiso calc R 1 1 . .
C C6A 0.79983(18) 0.57133(12) 0.06093(10) 0.0191(3) Uani d . 1 1 . .
C C7A 0.91519(18) 0.66502(12) 0.06621(10) 0.0182(3) Uani d . 1 1 . .
H H7AA 0.9626 0.7183 0.1225 0.022 Uiso calc R 1 1 . .
C C8A 0.96124(18) 0.68365(11) -0.00029(10) 0.0184(3) Uani d . 1 1 . .
C C9A 0.8916(2) 0.61170(12) -0.09734(10) 0.0220(3) Uani d . 1 1 . .
H H9AA 0.9522 0.5651 -0.1110 0.026 Uiso calc R 1 1 . .
H H9AB 0.7830 0.5699 -0.1092 0.026 Uiso calc R 1 1 . .
C C10A 1.05515(19) 0.73114(13) -0.14312(10) 0.0231(3) Uani d . 1 1 . .
H H10A 1.0517 0.7655 -0.1848 0.028 Uiso calc R 1 1 . .
H H10B 1.1166 0.6849 -0.1560 0.028 Uiso calc R 1 1 . .
C C11A 1.13322(18) 0.81139(12) -0.04866(10) 0.0189(3) Uani d . 1 1 . .
C C12A 1.08627(18) 0.78603(11) 0.02452(10) 0.0189(3) Uani d . 1 1 . .
C C13A 1.23844(19) 0.90544(12) -0.02641(11) 0.0219(3) Uani d . 1 1 . .
H H13A 1.2719 0.9500 0.0333 0.026 Uiso calc R 1 1 . .
C C14A 1.3064(2) 0.94591(14) -0.08475(12) 0.0293(4) Uani d . 1 1 . .
C C15A 1.3639(2) 0.88519(18) -0.14667(13) 0.0379(5) Uani d . 1 1 . .
H H15A 1.3529 0.8170 -0.1525 0.045 Uiso calc R 1 1 . .
C C16A 1.4369(3) 0.9256(2) -0.19928(14) 0.0541(7) Uani d . 1 1 . .
H H16A 1.4726 0.8843 -0.2405 0.065 Uiso calc R 1 1 . .
C C17A 1.4558(3) 1.0263(2) -0.18998(16) 0.0568(8) Uani d . 1 1 . .
H H17A 1.5055 1.0532 -0.2247 0.068 Uiso calc R 1 1 . .
C C18A 1.4020(3) 1.0886(2) -0.12963(18) 0.0535(7) Uani d . 1 1 . .
H H18A 1.4154 1.1569 -0.1239 0.064 Uiso calc R 1 1 . .
C C19A 1.3276(2) 1.04845(16) -0.07725(15) 0.0384(5) Uani d . 1 1 . .
C C20A 0.7534(2) 0.67443(12) -0.20127(10) 0.0215(3) Uani d . 1 1 . .
C C21A 0.7581(2) 0.73289(14) -0.26091(11) 0.0273(3) Uani d . 1 1 . .
H H21A 0.8551 0.7700 -0.2623 0.033 Uiso calc R 1 1 . .
C C22A 0.6255(3) 0.73198(17) -0.31145(16) 0.0413(5) Uani d . 1 1 . .
Cl Cl1B 0.66752(5) 0.47648(3) 0.49413(3) 0.03091(10) Uani d . 1 1 . .
Cl Cl2B 0.27364(6) -0.25290(4) 0.23104(3) 0.03402(11) Uani d . 1 1 . .
O O1B 0.50001(14) 0.11375(9) 0.41521(8) 0.0239(2) Uani d . 1 1 . .
O O2B 1.06328(17) 0.17824(9) 0.37831(9) 0.0306(3) Uani d . 1 1 . .
N N1B 0.92667(16) 0.09419(10) 0.44623(9) 0.0206(3) Uani d . 1 1 . .
C C1B 0.8476(2) 0.48776(12) 0.56386(11) 0.0226(3) Uani d . 1 1 . .
C C2B 0.9637(2) 0.58533(13) 0.60446(12) 0.0279(4) Uani d . 1 1 . .
H H2BA 0.9435 0.6419 0.5943 0.034 Uiso calc R 1 1 . .
C C3B 1.1093(2) 0.59741(14) 0.66010(12) 0.0326(4) Uani d . 1 1 . .
H H3BA 1.1891 0.6618 0.6856 0.039 Uiso calc R 1 1 . .
C C4B 1.1371(2) 0.51401(15) 0.67801(12) 0.0342(4) Uani d . 1 1 . .
H H4BA 1.2339 0.5231 0.7172 0.041 Uiso calc R 1 1 . .
C C5B 1.0198(2) 0.41642(14) 0.63712(11) 0.0284(4) Uani d . 1 1 . .
H H5BA 1.0390 0.3612 0.6503 0.034 Uiso calc R 1 1 . .
C C6B 0.8727(2) 0.39952(12) 0.57631(10) 0.0213(3) Uani d . 1 1 . .
C C7B 0.75084(19) 0.29687(12) 0.52643(10) 0.0205(3) Uani d . 1 1 . .
H H7BA 0.6459 0.2955 0.5128 0.025 Uiso calc R 1 1 . .
C C8B 0.77430(18) 0.20415(12) 0.49812(10) 0.0186(3) Uani d . 1 1 . .
C C9B 0.93589(19) 0.19091(12) 0.51313(11) 0.0208(3) Uani d . 1 1 . .
H H9BA 1.0108 0.2488 0.5098 0.025 Uiso calc R 1 1 . .
H H9BB 0.9734 0.1904 0.5721 0.025 Uiso calc R 1 1 . .
C C10B 0.82372(19) 0.00428(12) 0.45274(12) 0.0226(3) Uani d . 1 1 . .
H H10C 0.8583 0.0066 0.5129 0.027 Uiso calc R 1 1 . .
H H10D 0.8298 -0.0591 0.4122 0.027 Uiso calc R 1 1 . .
C C11B 0.65483(18) 0.00467(11) 0.42949(10) 0.0179(3) Uani d . 1 1 . .
C C12B 0.63143(18) 0.10822(12) 0.44444(10) 0.0182(3) Uani d . 1 1 . .
C C13B 0.52661(18) -0.08136(12) 0.39480(10) 0.0184(3) Uani d . 1 1 . .
H H13B 0.4282 -0.0727 0.3785 0.022 Uiso calc R 1 1 . .
C C14B 0.52654(18) -0.18800(12) 0.38001(10) 0.0186(3) Uani d . 1 1 . .
C C15B 0.63354(18) -0.21000(12) 0.43978(11) 0.0208(3) Uani d . 1 1 . .
H H15B 0.7100 -0.1552 0.4892 0.025 Uiso calc R 1 1 . .
C C16B 0.62897(19) -0.31117(12) 0.42763(11) 0.0228(3) Uani d . 1 1 . .
H H16B 0.7017 -0.3234 0.4683 0.027 Uiso calc R 1 1 . .
C C17B 0.5149(2) -0.39402(12) 0.35426(11) 0.0244(3) Uani d . 1 1 . .
H H17B 0.5122 -0.4619 0.3451 0.029 Uiso calc R 1 1 . .
C C18B 0.4052(2) -0.37492(13) 0.29471(11) 0.0253(3) Uani d . 1 1 . .
H H18B 0.3277 -0.4301 0.2460 0.030 Uiso calc R 1 1 . .
C C19B 0.41142(19) -0.27359(13) 0.30805(10) 0.0222(3) Uani d . 1 1 . .
C C20B 0.98641(19) 0.09578(12) 0.37874(11) 0.0211(3) Uani d . 1 1 . .
C C21B 0.9646(2) -0.00569(14) 0.30854(12) 0.0308(4) Uani d . 1 1 . .
H H21B 0.8758 -0.0628 0.2943 0.037 Uiso calc R 1 1 . .
C C22B 1.0686(4) -0.0153(2) 0.26683(19) 0.0587(8) Uani d . 1 1 . .
H H22A 0.620(3) 0.769(2) -0.3504(17) 0.044(7) Uiso d . 1 1 . .
H H22C 1.055(4) -0.080(2) 0.223(2) 0.062(8) Uiso d . 1 1 . .
H H22B 0.525(4) 0.697(2) -0.3109(19) 0.058(8) Uiso d . 1 1 . .
H H22D 1.163(3) 0.042(2) 0.2836(19) 0.055(8) Uiso d . 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
C20A N1A C9A . . 119.33(13) ?
C20A N1A C10A . . 127.79(14) ?
C9A N1A C10A . . 112.45(13) ?
C2A C1A C6A . . 122.26(15) ?
C2A C1A Cl1A . . 117.47(13) ?
C6A C1A Cl1A . . 120.27(12) ?
C3A C2A C1A . . 119.58(16) ?
C3A C2A H2AA . . 120.2 ?
C1A C2A H2AA . . 120.2 ?
C2A C3A C4A . . 119.82(15) ?
C2A C3A H3AA . . 120.1 ?
C4A C3A H3AA . . 120.1 ?
C5A C4A C3A . . 120.05(16) ?
C5A C4A H4AA . . 120.0 ?
C3A C4A H4AA . . 120.0 ?
C4A C5A C6A . . 121.48(16) ?
C4A C5A H5AA . . 119.3 ?
C6A C5A H5AA . . 119.3 ?
C5A C6A C1A . . 116.79(14) ?
C5A C6A C7A . . 122.87(14) ?
C1A C6A C7A . . 120.29(14) ?
C8A C7A C6A . . 128.07(14) ?
C8A C7A H7AA . . 116.0 ?
C6A C7A H7AA . . 116.0 ?
C7A C8A C12A . . 116.92(13) ?
C7A C8A C9A . . 124.88(14) ?
C12A C8A C9A . . 118.15(13) ?
N1A C9A C8A . . 110.41(12) ?
N1A C9A H9AA . . 109.6 ?
C8A C9A H9AA . . 109.6 ?
N1A C9A H9AB . . 109.6 ?
C8A C9A H9AB . . 109.6 ?
H9AA C9A H9AB . . 108.1 ?
N1A C10A C11A . . 109.79(12) ?
N1A C10A H10A . . 109.7 ?
C11A C10A H10A . . 109.7 ?
N1A C10A H10B . . 109.7 ?
C11A C10A H10B . . 109.7 ?
H10A C10A H10B . . 108.2 ?
C13A C11A C12A . . 117.63(14) ?
C13A C11A C10A . . 124.21(14) ?
C12A C11A C10A . . 118.12(13) ?
O1A C12A C11A . . 120.96(14) ?
O1A C12A C8A . . 120.93(14) ?
C11A C12A C8A . . 118.10(13) ?
C11A C13A C14A . . 127.59(15) ?
C11A C13A H13A . . 116.2 ?
C14A C13A H13A . . 116.2 ?
C19A C14A C15A . . 117.47(18) ?
C19A C14A C13A . . 121.45(18) ?
C15A C14A C13A . . 120.93(17) ?
C16A C15A C14A . . 121.1(2) ?
C16A C15A H15A . . 119.5 ?
C14A C15A H15A . . 119.5 ?
C17A C16A C15A . . 119.8(3) ?
C17A C16A H16A . . 120.1 ?
C15A C16A H16A . . 120.1 ?
C16A C17A C18A . . 120.9(2) ?
C16A C17A H17A . . 119.6 ?
C18A C17A H17A . . 119.6 ?
C17A C18A C19A . . 119.7(2) ?
C17A C18A H18A . . 120.2 ?
C19A C18A H18A . . 120.2 ?
C18A C19A C14A . . 121.1(2) ?
C18A C19A Cl2A . . 119.90(19) ?
C14A C19A Cl2A . . 119.04(16) ?
O2A C20A N1A . . 120.45(15) ?
O2A C20A C21A . . 120.99(16) ?
N1A C20A C21A . . 118.50(14) ?
C22A C21A C20A . . 119.99(17) ?
C22A C21A H21A . . 120.0 ?
C20A C21A H21A . . 120.0 ?
C21A C22A H22A . . 124.2(16) ?
C21A C22A H22B . . 122.6(18) ?
H22A C22A H22B . . 113(2) ?
C20B N1B C9B . . 120.01(13) ?
C20B N1B C10B . . 127.25(14) ?
C9B N1B C10B . . 111.67(13) ?
C2B C1B C6B . . 122.55(16) ?
C2B C1B Cl1B . . 117.54(13) ?
C6B C1B Cl1B . . 119.91(13) ?
C3B C2B C1B . . 119.30(17) ?
C3B C2B H2BA . . 120.3 ?
C1B C2B H2BA . . 120.3 ?
C2B C3B C4B . . 120.32(17) ?
C2B C3B H3BA . . 119.8 ?
C4B C3B H3BA . . 119.8 ?
C3B C4B C5B . . 119.92(18) ?
C3B C4B H4BA . . 120.0 ?
C5B C4B H4BA . . 120.0 ?
C4B C5B C6B . . 121.53(17) ?
C4B C5B H5BA . . 119.2 ?
C6B C5B H5BA . . 119.2 ?
C1B C6B C5B . . 116.21(15) ?
C1B C6B C7B . . 120.32(15) ?
C5B C6B C7B . . 123.47(15) ?
C8B C7B C6B . . 127.12(15) ?
C8B C7B H7BA . . 116.4 ?
C6B C7B H7BA . . 116.4 ?
C7B C8B C12B . . 118.21(14) ?
C7B C8B C9B . . 124.09(14) ?
C12B C8B C9B . . 117.63(13) ?
N1B C9B C8B . . 109.99(13) ?
N1B C9B H9BA . . 109.7 ?
C8B C9B H9BA . . 109.7 ?
N1B C9B H9BB . . 109.7 ?
C8B C9B H9BB . . 109.7 ?
H9BA C9B H9BB . . 108.2 ?
N1B C10B C11B . . 109.53(13) ?
N1B C10B H10C . . 109.8 ?
C11B C10B H10C . . 109.8 ?
N1B C10B H10D . . 109.8 ?
C11B C10B H10D . . 109.8 ?
H10C C10B H10D . . 108.2 ?
C13B C11B C12B . . 118.89(14) ?
C13B C11B C10B . . 124.03(14) ?
C12B C11B C10B . . 117.06(13) ?
O1B C12B C11B . . 120.86(14) ?
O1B C12B C8B . . 121.61(14) ?
C11B C12B C8B . . 117.52(13) ?
C11B C13B C14B . . 126.35(14) ?
C11B C13B H13B . . 116.8 ?
C14B C13B H13B . . 116.8 ?
C19B C14B C15B . . 116.55(14) ?
C19B C14B C13B . . 121.11(14) ?
C15B C14B C13B . . 122.19(14) ?
C16B C15B C14B . . 122.09(15) ?
C16B C15B H15B . . 119.0 ?
C14B C15B H15B . . 119.0 ?
C15B C16B C17B . . 119.62(15) ?
C15B C16B H16B . . 120.2 ?
C17B C16B H16B . . 120.2 ?
C18B C17B C16B . . 119.69(15) ?
C18B C17B H17B . . 120.2 ?
C16B C17B H17B . . 120.2 ?
C19B C18B C17B . . 119.85(15) ?
C19B C18B H18B . . 120.1 ?
C17B C18B H18B . . 120.1 ?
C18B C19B C14B . . 122.17(15) ?
C18B C19B Cl2B . . 118.41(13) ?
C14B C19B Cl2B . . 119.40(13) ?
O2B C20B N1B . . 120.88(14) ?
O2B C20B C21B . . 121.09(15) ?
N1B C20B C21B . . 117.92(14) ?
C22B C21B C20B . . 120.63(19) ?
C22B C21B H21B . . 119.7 ?
C20B C21B H21B . . 119.7 ?
C21B C22B H22C . . 120.4(18) ?
C21B C22B H22D . . 119.8(17) ?
H22C C22B H22D . . 120(2) ?
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 C1A . 1.7434(17) ?
Cl2A C19A . 1.746(3) ?
O1A C12A . 1.2180(19) ?
O2A C20A . 1.230(2) ?
N1A C20A . 1.374(2) ?
N1A C9A . 1.454(2) ?
N1A C10A . 1.460(2) ?
C1A C2A . 1.387(2) ?
C1A C6A . 1.403(2) ?
C2A C3A . 1.385(3) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.393(3) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.389(2) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.403(2) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.464(2) ?
C7A C8A . 1.347(2) ?
C7A H7AA . 0.9300 ?
C8A C12A . 1.501(2) ?
C8A C9A . 1.508(2) ?
C9A H9AA . 0.9700 ?
C9A H9AB . 0.9700 ?
C10A C11A . 1.513(2) ?
C10A H10A . 0.9700 ?
C10A H10B . 0.9700 ?
C11A C13A . 1.341(2) ?
C11A C12A . 1.497(2) ?
C13A C14A . 1.456(2) ?
C13A H13A . 0.9300 ?
C14A C19A . 1.399(3) ?
C14A C15A . 1.410(3) ?
C15A C16A . 1.395(3) ?
C15A H15A . 0.9300 ?
C16A C17A . 1.367(4) ?
C16A H16A . 0.9300 ?
C17A C18A . 1.382(4) ?
C17A H17A . 0.9300 ?
C18A C19A . 1.396(3) ?
C18A H18A . 0.9300 ?
C20A C21A . 1.490(2) ?
C21A C22A . 1.310(3) ?
C21A H21A . 0.9300 ?
C22A H22A . 0.96(3) ?
C22A H22B . 0.94(3) ?
Cl1B C1B . 1.7328(18) ?
Cl2B C19B . 1.7399(17) ?
O1B C12B . 1.2244(19) ?
O2B C20B . 1.2283(19) ?
N1B C20B . 1.358(2) ?
N1B C9B . 1.4508(19) ?
N1B C10B . 1.4565(19) ?
C1B C2B . 1.389(2) ?
C1B C6B . 1.407(2) ?
C2B C3B . 1.382(3) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.385(3) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.394(3) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.409(2) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.466(2) ?
C7B C8B . 1.350(2) ?
C7B H7BA . 0.9300 ?
C8B C12B . 1.504(2) ?
C8B C9B . 1.510(2) ?
C9B H9BA . 0.9700 ?
C9B H9BB . 0.9700 ?
C10B C11B . 1.509(2) ?
C10B H10C . 0.9700 ?
C10B H10D . 0.9700 ?
C11B C13B . 1.342(2) ?
C11B C12B . 1.502(2) ?
C13B C14B . 1.471(2) ?
C13B H13B . 0.9300 ?
C14B C19B . 1.401(2) ?
C14B C15B . 1.401(2) ?
C15B C16B . 1.390(2) ?
C15B H15B . 0.9300 ?
C16B C17B . 1.391(2) ?
C16B H16B . 0.9300 ?
C17B C18B . 1.389(2) ?
C17B H17B . 0.9300 ?
C18B C19B . 1.385(2) ?
C18B H18B . 0.9300 ?
C20B C21B . 1.488(2) ?
C21B C22B . 1.303(3) ?
C21B H21B . 0.9300 ?
C22B H22C . 0.95(3) ?
C22B H22D . 0.95(3) ?
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
C2A H2AA O2A 2_665 0.9300 2.4400 3.146(2) 133.00 yes
C2B H2BA O2B 2_766 0.9300 2.4900 3.385(2) 161.00 yes
C21A H21A O2B 2_765 0.9300 2.4700 3.180(2) 133.00 yes
C22A H22A O1B 2_665 0.96(3) 2.59(3) 3.455(3) 151(2) yes
C22B H22C O1A 1_545 0.94(3) 2.40(3) 3.191(3) 141(3) yes
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 C1A C2A C3A . . . . 0.9(3) ?
Cl1A C1A C2A C3A . . . . -179.72(14) ?
C1A C2A C3A C4A . . . . 0.6(3) ?
C2A C3A C4A C5A . . . . -1.2(3) ?
C3A C4A C5A C6A . . . . 0.3(3) ?
C4A C5A C6A C1A . . . . 1.1(2) ?
C4A C5A C6A C7A . . . . 178.74(15) ?
C2A C1A C6A C5A . . . . -1.7(2) ?
Cl1A C1A C6A C5A . . . . 178.93(12) ?
C2A C1A C6A C7A . . . . -179.43(15) ?
Cl1A C1A C6A C7A . . . . 1.2(2) ?
C5A C6A C7A C8A . . . . 32.4(3) ?
C1A C6A C7A C8A . . . . -150.03(17) ?
C6A C7A C8A C12A . . . . -178.17(14) ?
C6A C7A C8A C9A . . . . 4.7(3) ?
C20A N1A C9A C8A . . . . -110.40(16) ?
C10A N1A C9A C8A . . . . 62.70(18) ?
C7A C8A C9A N1A . . . . 147.54(16) ?
C12A C8A C9A N1A . . . . -29.6(2) ?
C20A N1A C10A C11A . . . . 109.04(17) ?
C9A N1A C10A C11A . . . . -63.35(18) ?
N1A C10A C11A C13A . . . . -146.70(16) ?
N1A C10A C11A C12A . . . . 31.1(2) ?
C13A C11A C12A O1A . . . . -4.7(2) ?
C10A C11A C12A O1A . . . . 177.33(16) ?
C13A C11A C12A C8A . . . . 176.31(15) ?
C10A C11A C12A C8A . . . . -1.6(2) ?
C7A C8A C12A O1A . . . . 4.4(2) ?
C9A C8A C12A O1A . . . . -178.23(15) ?
C7A C8A C12A C11A . . . . -176.63(14) ?
C9A C8A C12A C11A . . . . 0.7(2) ?
C12A C11A C13A C14A . . . . 177.29(17) ?
C10A C11A C13A C14A . . . . -4.9(3) ?
C11A C13A C14A C19A . . . . 139.06(19) ?
C11A C13A C14A C15A . . . . -45.5(3) ?
C19A C14A C15A C16A . . . . -0.9(3) ?
C13A C14A C15A C16A . . . . -176.49(18) ?
C14A C15A C16A C17A . . . . 1.1(3) ?
C15A C16A C17A C18A . . . . -0.6(4) ?
C16A C17A C18A C19A . . . . 0.1(4) ?
C17A C18A C19A C14A . . . . 0.0(3) ?
C17A C18A C19A Cl2A . . . . 179.58(17) ?
C15A C14A C19A C18A . . . . 0.4(3) ?
C13A C14A C19A C18A . . . . 175.93(18) ?
C15A C14A C19A Cl2A . . . . -179.19(15) ?
C13A C14A C19A Cl2A . . . . -3.6(3) ?
C9A N1A C20A O2A . . . . -0.7(2) ?
C10A N1A C20A O2A . . . . -172.58(15) ?
C9A N1A C20A C21A . . . . -178.06(14) ?
C10A N1A C20A C21A . . . . 10.0(2) ?
O2A C20A C21A C22A . . . . -1.8(3) ?
N1A C20A C21A C22A . . . . 175.60(19) ?
C6B C1B C2B C3B . . . . -0.7(3) ?
Cl1B C1B C2B C3B . . . . -179.57(13) ?
C1B C2B C3B C4B . . . . -2.6(3) ?
C2B C3B C4B C5B . . . . 2.4(3) ?
C3B C4B C5B C6B . . . . 1.0(3) ?
C2B C1B C6B C5B . . . . 3.8(2) ?
Cl1B C1B C6B C5B . . . . -177.27(12) ?
C2B C1B C6B C7B . . . . -175.17(15) ?
Cl1B C1B C6B C7B . . . . 3.7(2) ?
C4B C5B C6B C1B . . . . -4.0(2) ?
C4B C5B C6B C7B . . . . 175.01(16) ?
C1B C6B C7B C8B . . . . 147.74(16) ?
C5B C6B C7B C8B . . . . -31.2(3) ?
C6B C7B C8B C12B . . . . -177.54(14) ?
C6B C7B C8B C9B . . . . -0.6(3) ?
C20B N1B C9B C8B . . . . 105.76(16) ?
C10B N1B C9B C8B . . . . -63.28(17) ?
C7B C8B C9B N1B . . . . -156.07(14) ?
C12B C8B C9B N1B . . . . 20.90(18) ?
C20B N1B C10B C11B . . . . -101.86(18) ?
C9B N1B C10B C11B . . . . 66.19(17) ?
N1B C10B C11B C13B . . . . 152.27(15) ?
N1B C10B C11B C12B . . . . -26.11(19) ?
C13B C11B C12B O1B . . . . -9.4(2) ?
C10B C11B C12B O1B . . . . 169.05(14) ?
C13B C11B C12B C8B . . . . 169.27(13) ?
C10B C11B C12B C8B . . . . -12.25(19) ?
C7B C8B C12B O1B . . . . 10.9(2) ?
C9B C8B C12B O1B . . . . -166.22(14) ?
C7B C8B C12B C11B . . . . -167.75(13) ?
C9B C8B C12B C11B . . . . 15.10(19) ?
C12B C11B C13B C14B . . . . -176.59(14) ?
C10B C11B C13B C14B . . . . 5.0(2) ?
C11B C13B C14B C19B . . . . -147.10(16) ?
C11B C13B C14B C15B . . . . 37.4(2) ?
C19B C14B C15B C16B . . . . 1.5(2) ?
C13B C14B C15B C16B . . . . 177.25(14) ?
C14B C15B C16B C17B . . . . -0.2(2) ?
C15B C16B C17B C18B . . . . -1.1(2) ?
C16B C17B C18B C19B . . . . 0.9(2) ?
C17B C18B C19B C14B . . . . 0.5(3) ?
C17B C18B C19B Cl2B . . . . 179.08(13) ?
C15B C14B C19B C18B . . . . -1.7(2) ?
C13B C14B C19B C18B . . . . -177.44(15) ?
C15B C14B C19B Cl2B . . . . 179.76(12) ?
C13B C14B C19B Cl2B . . . . 4.0(2) ?
C9B N1B C20B O2B . . . . 7.7(2) ?
C10B N1B C20B O2B . . . . 174.88(16) ?
C9B N1B C20B C21B . . . . -176.05(15) ?
C10B N1B C20B C21B . . . . -8.9(2) ?
O2B C20B C21B C22B . . . . 26.4(3) ?
N1B C20B C21B C22B . . . . -149.8(2) ?
