#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/49/2224925.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_2224925
loop_
_publ_author_name
'Kobkeatthawin, Thawanrat'
'Chantrapromma, Suchada'
'Fun, Hoong-Kun'
_publ_section_title
;
 (E)-1-(4-Chlorophenyl)-3-[4-(diethylamino)phenyl]prop-2-en-1-one
;
_journal_coeditor_code           CV2675
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o254
_journal_page_last               o255
_journal_paper_doi               10.1107/S1600536809054683
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H20 Cl N O'
_chemical_formula_moiety         'C19 H20 Cl N O'
_chemical_formula_sum            'C19 H20 Cl N O'
_chemical_formula_weight         313.81
_chemical_melting_point_gt       374
_chemical_melting_point_lt       375
_chemical_name_systematic
;
(E)-1-(4-Chlorophenyl)-3-[4-(diethylamino)phenyl]prop-2-en-1-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.2680(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.2073(2)
_cell_length_b                   11.94670(10)
_cell_length_c                   15.7996(2)
_cell_measurement_reflns_used    9400
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      1.91
_cell_volume                     3221.83(6)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0568
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            47596
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_correction_T_min  0.9252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         9400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0479
_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)+(0.0474P)²+0.7024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                6241
_reflns_number_total             9400
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2675.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_cell_volume        3221.84(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224925
_cod_database_fobs_code          2224925
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 Cl1A 1.33545(2) 0.22869(4) 0.37652(3) 0.02632(11) Uani d . 1 . .
O O1A 1.00783(6) -0.07143(9) 0.29241(7) 0.0250(3) Uani d . 1 . .
N N1A 0.62274(7) 0.22634(11) -0.01499(8) 0.0220(3) Uani d . 1 . .
C C1A 1.11964(9) 0.17759(13) 0.25803(10) 0.0203(3) Uani d . 1 . .
H H1AA 1.0859 0.2119 0.2151 0.024 Uiso calc R 1 . .
C C2A 1.19351(9) 0.22284(13) 0.28205(10) 0.0209(3) Uani d . 1 . .
H H2AA 1.2099 0.2857 0.2544 0.025 Uiso calc R 1 . .
C C3A 1.24235(9) 0.17306(13) 0.34767(10) 0.0193(3) Uani d . 1 . .
C C4A 1.21866(9) 0.07958(13) 0.38999(10) 0.0216(3) Uani d . 1 . .
H H4AA 1.2513 0.0484 0.4353 0.026 Uiso calc R 1 . .
C C5A 1.14600(9) 0.03364(13) 0.36369(10) 0.0208(3) Uani d . 1 . .
H H5AA 1.1305 -0.0304 0.3906 0.025 Uiso calc R 1 . .
C C6A 1.09523(9) 0.08156(13) 0.29733(10) 0.0186(3) Uani d . 1 . .
C C7A 1.01754(9) 0.02632(13) 0.27110(10) 0.0185(3) Uani d . 1 . .
C C8A 0.95504(9) 0.09153(13) 0.22182(10) 0.0197(3) Uani d . 1 . .
H H8AA 0.9640 0.1659 0.2086 0.024 Uiso calc R 1 . .
C C9A 0.88478(9) 0.04481(13) 0.19551(9) 0.0193(3) Uani d . 1 . .
H H9AA 0.8786 -0.0291 0.2118 0.023 Uiso calc R 1 . .
C C10A 0.81767(9) 0.09526(13) 0.14509(10) 0.0190(3) Uani d . 1 . .
C C11A 0.81717(9) 0.20500(13) 0.11330(10) 0.0208(3) Uani d . 1 . .
H H11A 0.8611 0.2498 0.1272 0.025 Uiso calc R 1 . .
C C12A 0.75375(9) 0.24823(13) 0.06228(10) 0.0215(4) Uani d . 1 . .
H H12A 0.7560 0.3214 0.0427 0.026 Uiso calc R 1 . .
C C13A 0.68503(9) 0.18439(13) 0.03865(10) 0.0194(3) Uani d . 1 . .
C C14A 0.68454(9) 0.07499(13) 0.07266(10) 0.0220(4) Uani d . 1 . .
H H14A 0.6400 0.0308 0.0606 0.026 Uiso calc R 1 . .
C C15A 0.74903(9) 0.03261(13) 0.12349(10) 0.0207(3) Uani d . 1 . .
H H15A 0.7469 -0.0401 0.1441 0.025 Uiso calc R 1 . .
C C16A 0.62152(9) 0.34250(13) -0.04343(10) 0.0236(4) Uani d . 1 . .
H H16A 0.5841 0.3495 -0.0945 0.028 Uiso calc R 1 . .
H H16B 0.6728 0.3615 -0.0586 0.028 Uiso calc R 1 . .
C C17A 0.60016(10) 0.42641(14) 0.02253(11) 0.0268(4) Uani d . 1 . .
H H17A 0.6049 0.5011 0.0013 0.040 Uiso calc R 1 . .
H H17B 0.6349 0.4173 0.0746 0.040 Uiso calc R 1 . .
H H17C 0.5472 0.4137 0.0333 0.040 Uiso calc R 1 . .
C C18A 0.55139(9) 0.16108(14) -0.03719(10) 0.0231(4) Uani d . 1 . .
H H18A 0.5658 0.0839 -0.0462 0.028 Uiso calc R 1 . .
H H18B 0.5244 0.1890 -0.0906 0.028 Uiso calc R 1 . .
C C19A 0.49514(10) 0.16418(15) 0.02990(11) 0.0290(4) Uani d . 1 . .
H H19A 0.4499 0.1194 0.0112 0.043 Uiso calc R 1 . .
H H19B 0.4792 0.2400 0.0380 0.043 Uiso calc R 1 . .
H H19C 0.5209 0.1351 0.0828 0.043 Uiso calc R 1 . .
Cl Cl1B 0.16956(2) 0.81186(4) 0.18284(3) 0.03390(13) Uani d . 1 . .
O O1B 0.51160(6) 1.07982(9) 0.24066(8) 0.0283(3) Uani d . 1 . .
N N1B 0.90996(7) 0.73741(11) 0.47926(8) 0.0193(3) Uani d . 1 . .
C C1B 0.40036(9) 0.82319(13) 0.25395(10) 0.0209(3) Uani d . 1 . .
H H1BA 0.4401 0.7729 0.2726 0.025 Uiso calc R 1 . .
C C2B 0.32374(9) 0.78546(14) 0.23590(10) 0.0227(4) Uani d . 1 . .
H H2BA 0.3121 0.7102 0.2425 0.027 Uiso calc R 1 . .
C C3B 0.26505(9) 0.86039(14) 0.20805(10) 0.0221(4) Uani d . 1 . .
C C4B 0.28072(9) 0.97338(14) 0.19930(10) 0.0250(4) Uani d . 1 . .
H H4BA 0.2405 1.0234 0.1816 0.030 Uiso calc R 1 . .
C C5B 0.35717(9) 1.01030(13) 0.21739(10) 0.0217(3) Uani d . 1 . .
H H5BA 0.3682 1.0859 0.2115 0.026 Uiso calc R 1 . .
C C6B 0.41803(9) 0.93639(13) 0.24428(9) 0.0176(3) Uani d . 1 . .
C C7B 0.49926(9) 0.98249(13) 0.26100(10) 0.0189(3) Uani d . 1 . .
C C8B 0.56250(9) 0.91209(13) 0.30276(10) 0.0207(3) Uani d . 1 . .
H H8BA 0.5512 0.8404 0.3206 0.025 Uiso calc R 1 . .
C C9B 0.63645(9) 0.94976(13) 0.31555(9) 0.0187(3) Uani d . 1 . .
H H9BA 0.6447 1.0201 0.2932 0.022 Uiso calc R 1 . .
C C10B 0.70517(9) 0.89533(13) 0.35960(10) 0.0180(3) Uani d . 1 . .
C C11B 0.70277(9) 0.79079(13) 0.39960(10) 0.0200(3) Uani d . 1 . .
H H11B 0.6547 0.7551 0.3992 0.024 Uiso calc R 1 . .
C C12B 0.76888(9) 0.73904(13) 0.43942(10) 0.0196(3) Uani d . 1 . .
H H12B 0.7645 0.6699 0.4655 0.023 Uiso calc R 1 . .
C C13B 0.84368(9) 0.78947(13) 0.44136(9) 0.0173(3) Uani d . 1 . .
C C14B 0.84647(9) 0.89580(13) 0.40271(10) 0.0186(3) Uani d . 1 . .
H H14B 0.8943 0.9322 0.4034 0.022 Uiso calc R 1 . .
C C15B 0.77899(9) 0.94644(13) 0.36396(10) 0.0189(3) Uani d . 1 . .
H H15B 0.7826 1.0170 0.3399 0.023 Uiso calc R 1 . .
C C16B 0.98874(9) 0.77527(13) 0.46801(10) 0.0198(3) Uani d . 1 . .
H H16C 0.9861 0.8185 0.4157 0.024 Uiso calc R 1 . .
H H16D 1.0215 0.7104 0.4619 0.024 Uiso calc R 1 . .
C C17B 1.02667(9) 0.84630(14) 0.54171(11) 0.0251(4) Uani d . 1 . .
H H17D 1.0795 0.8637 0.5329 0.038 Uiso calc R 1 . .
H H17E 1.0269 0.8056 0.5941 0.038 Uiso calc R 1 . .
H H17F 0.9975 0.9144 0.5446 0.038 Uiso calc R 1 . .
C C18B 0.90602(9) 0.63347(13) 0.52717(10) 0.0209(3) Uani d . 1 . .
H H18C 0.8606 0.6359 0.5578 0.025 Uiso calc R 1 . .
H H18D 0.9523 0.6276 0.5689 0.025 Uiso calc R 1 . .
C C19B 0.90064(10) 0.53012(14) 0.47043(11) 0.0259(4) Uani d . 1 . .
H H19D 0.9030 0.4641 0.5053 0.039 Uiso calc R 1 . .
H H19E 0.9435 0.5298 0.4370 0.039 Uiso calc R 1 . .
H H19F 0.8520 0.5312 0.4332 0.039 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
C13A N1A C16A . . 121.13(13) ?
C13A N1A C18A . . 121.34(13) ?
C16A N1A C18A . . 117.10(12) ?
C2A C1A C6A . . 121.02(14) ?
C2A C1A H1AA . . 119.5 ?
C6A C1A H1AA . . 119.5 ?
C3A C2A C1A . . 119.04(15) ?
C3A C2A H2AA . . 120.5 ?
C1A C2A H2AA . . 120.5 ?
C2A C3A C4A . . 121.26(14) ?
C2A C3A Cl1A . . 118.93(12) ?
C4A C3A Cl1A . . 119.81(12) ?
C5A C4A C3A . . 118.98(15) ?
C5A C4A H4AA . . 120.5 ?
C3A C4A H4AA . . 120.5 ?
C4A C5A C6A . . 121.24(15) ?
C4A C5A H5AA . . 119.4 ?
C6A C5A H5AA . . 119.4 ?
C1A C6A C5A . . 118.40(14) ?
C1A C6A C7A . . 123.13(14) ?
C5A C6A C7A . . 118.47(14) ?
O1A C7A C8A . . 122.12(14) ?
O1A C7A C6A . . 119.20(14) ?
C8A C7A C6A . . 118.68(14) ?
C9A C8A C7A . . 120.77(15) ?
C9A C8A H8AA . . 119.6 ?
C7A C8A H8AA . . 119.6 ?
C8A C9A C10A . . 128.20(15) ?
C8A C9A H9AA . . 115.9 ?
C10A C9A H9AA . . 115.9 ?
C15A C10A C11A . . 116.37(14) ?
C15A C10A C9A . . 119.98(14) ?
C11A C10A C9A . . 123.63(14) ?
C12A C11A C10A . . 122.00(14) ?
C12A C11A H11A . . 119.0 ?
C10A C11A H11A . . 119.0 ?
C11A C12A C13A . . 121.81(15) ?
C11A C12A H12A . . 119.1 ?
C13A C12A H12A . . 119.1 ?
N1A C13A C14A . . 122.01(14) ?
N1A C13A C12A . . 121.73(14) ?
C14A C13A C12A . . 116.25(14) ?
C15A C14A C13A . . 121.14(14) ?
C15A C14A H14A . . 119.4 ?
C13A C14A H14A . . 119.4 ?
C14A C15A C10A . . 122.38(15) ?
C14A C15A H15A . . 118.8 ?
C10A C15A H15A . . 118.8 ?
N1A C16A C17A . . 114.24(13) ?
N1A C16A H16A . . 108.7 ?
C17A C16A H16A . . 108.7 ?
N1A C16A H16B . . 108.7 ?
C17A C16A H16B . . 108.7 ?
H16A C16A H16B . . 107.6 ?
C16A C17A H17A . . 109.5 ?
C16A C17A H17B . . 109.5 ?
H17A C17A H17B . . 109.5 ?
C16A C17A H17C . . 109.5 ?
H17A C17A H17C . . 109.5 ?
H17B C17A H17C . . 109.5 ?
N1A C18A C19A . . 114.14(13) ?
N1A C18A H18A . . 108.7 ?
C19A C18A H18A . . 108.7 ?
N1A C18A H18B . . 108.7 ?
C19A C18A H18B . . 108.7 ?
H18A C18A H18B . . 107.6 ?
C18A C19A H19A . . 109.5 ?
C18A C19A H19B . . 109.5 ?
H19A C19A H19B . . 109.5 ?
C18A C19A H19C . . 109.5 ?
H19A C19A H19C . . 109.5 ?
H19B C19A H19C . . 109.5 ?
C13B N1B C18B . . 121.49(12) ?
C13B N1B C16B . . 122.73(13) ?
C18B N1B C16B . . 115.52(12) ?
C2B C1B C6B . . 120.35(14) ?
C2B C1B H1BA . . 119.8 ?
C6B C1B H1BA . . 119.8 ?
C3B C2B C1B . . 119.53(15) ?
C3B C2B H2BA . . 120.2 ?
C1B C2B H2BA . . 120.2 ?
C2B C3B C4B . . 121.31(15) ?
C2B C3B Cl1B . . 119.26(13) ?
C4B C3B Cl1B . . 119.42(12) ?
C5B C4B C3B . . 118.81(15) ?
C5B C4B H4BA . . 120.6 ?
C3B C4B H4BA . . 120.6 ?
C4B C5B C6B . . 121.27(15) ?
C4B C5B H5BA . . 119.4 ?
C6B C5B H5BA . . 119.4 ?
C5B C6B C1B . . 118.71(14) ?
C5B C6B C7B . . 118.04(14) ?
C1B C6B C7B . . 123.26(14) ?
O1B C7B C8B . . 121.12(14) ?
O1B C7B C6B . . 119.33(14) ?
C8B C7B C6B . . 119.54(14) ?
C9B C8B C7B . . 120.80(15) ?
C9B C8B H8BA . . 119.6 ?
C7B C8B H8BA . . 119.6 ?
C8B C9B C10B . . 128.56(15) ?
C8B C9B H9BA . . 115.7 ?
C10B C9B H9BA . . 115.7 ?
C11B C10B C15B . . 116.32(14) ?
C11B C10B C9B . . 123.19(14) ?
C15B C10B C9B . . 120.48(14) ?
C12B C11B C10B . . 122.45(14) ?
C12B C11B H11B . . 118.8 ?
C10B C11B H11B . . 118.8 ?
C11B C12B C13B . . 121.00(14) ?
C11B C12B H12B . . 119.5 ?
C13B C12B H12B . . 119.5 ?
N1B C13B C14B . . 121.71(14) ?
N1B C13B C12B . . 121.35(14) ?
C14B C13B C12B . . 116.93(14) ?
C15B C14B C13B . . 120.84(14) ?
C15B C14B H14B . . 119.6 ?
C13B C14B H14B . . 119.6 ?
C14B C15B C10B . . 122.41(14) ?
C14B C15B H15B . . 118.8 ?
C10B C15B H15B . . 118.8 ?
N1B C16B C17B . . 113.25(13) ?
N1B C16B H16C . . 108.9 ?
C17B C16B H16C . . 108.9 ?
N1B C16B H16D . . 108.9 ?
C17B C16B H16D . . 108.9 ?
H16C C16B H16D . . 107.7 ?
C16B C17B H17D . . 109.5 ?
C16B C17B H17E . . 109.5 ?
H17D C17B H17E . . 109.5 ?
C16B C17B H17F . . 109.5 ?
H17D C17B H17F . . 109.5 ?
H17E C17B H17F . . 109.5 ?
N1B C18B C19B . . 112.83(13) ?
N1B C18B H18C . . 109.0 ?
C19B C18B H18C . . 109.0 ?
N1B C18B H18D . . 109.0 ?
C19B C18B H18D . . 109.0 ?
H18C C18B H18D . . 107.8 ?
C18B C19B H19D . . 109.5 ?
C18B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
C18B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 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
Cl1A C3A . 1.7411(15) ?
O1A C7A . 1.2326(18) ?
N1A C13A . 1.3741(19) ?
N1A C16A . 1.458(2) ?
N1A C18A . 1.459(2) ?
C1A C2A . 1.389(2) ?
C1A C6A . 1.394(2) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.384(2) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.389(2) ?
C4A C5A . 1.381(2) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.399(2) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.501(2) ?
C7A C8A . 1.469(2) ?
C8A C9A . 1.349(2) ?
C8A H8AA . 0.9300 ?
C9A C10A . 1.449(2) ?
C9A H9AA . 0.9300 ?
C10A C15A . 1.404(2) ?
C10A C11A . 1.404(2) ?
C11A C12A . 1.373(2) ?
C11A H11A . 0.9300 ?
C12A C13A . 1.417(2) ?
C12A H12A . 0.9300 ?
C13A C14A . 1.414(2) ?
C14A C15A . 1.381(2) ?
C14A H14A . 0.9300 ?
C15A H15A . 0.9300 ?
C16A C17A . 1.524(2) ?
C16A H16A . 0.9700 ?
C16A H16B . 0.9700 ?
C17A H17A . 0.9600 ?
C17A H17B . 0.9600 ?
C17A H17C . 0.9600 ?
C18A C19A . 1.524(2) ?
C18A H18A . 0.9700 ?
C18A H18B . 0.9700 ?
C19A H19A . 0.9600 ?
C19A H19B . 0.9600 ?
C19A H19C . 0.9600 ?
Cl1B C3B . 1.7405(16) ?
O1B C7B . 1.2320(18) ?
N1B C13B . 1.3687(19) ?
N1B C18B . 1.460(2) ?
N1B C16B . 1.4610(19) ?
C1B C2B . 1.388(2) ?
C1B C6B . 1.399(2) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.379(2) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.387(2) ?
C4B C5B . 1.383(2) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.394(2) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.495(2) ?
C7B C8B . 1.465(2) ?
C8B C9B . 1.341(2) ?
C8B H8BA . 0.9300 ?
C9B C10B . 1.448(2) ?
C9B H9BA . 0.9300 ?
C10B C11B . 1.403(2) ?
C10B C15B . 1.403(2) ?
C11B C12B . 1.375(2) ?
C11B H11B . 0.9300 ?
C12B C13B . 1.418(2) ?
C12B H12B . 0.9300 ?
C13B C14B . 1.413(2) ?
C14B C15B . 1.382(2) ?
C14B H14B . 0.9300 ?
C15B H15B . 0.9300 ?
C16B C17B . 1.520(2) ?
C16B H16C . 0.9700 ?
C16B H16D . 0.9700 ?
C17B H17D . 0.9600 ?
C17B H17E . 0.9600 ?
C17B H17F . 0.9600 ?
C18B C19B . 1.522(2) ?
C18B H18C . 0.9700 ?
C18B H18D . 0.9700 ?
C19B H19D . 0.9600 ?
C19B H19E . 0.9600 ?
C19B H19F . 0.9600 ?
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
C1B H1BA O1B 2_645 0.93 2.47 3.2746(19) 145 y
C16B H16C O1A 1_565 0.97 2.42 3.3749(19) 168 y
C2A H2AA Cg1 2_745 0.93 2.60 3.3377(17) 137 y
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 . . . . -1.8(2) ?
C1A C2A C3A C4A . . . . -0.4(2) ?
C1A C2A C3A Cl1A . . . . 179.03(12) ?
C2A C3A C4A C5A . . . . 2.3(2) ?
Cl1A C3A C4A C5A . . . . -177.11(12) ?
C3A C4A C5A C6A . . . . -2.0(2) ?
C2A C1A C6A C5A . . . . 2.1(2) ?
C2A C1A C6A C7A . . . . -177.12(14) ?
C4A C5A C6A C1A . . . . -0.1(2) ?
C4A C5A C6A C7A . . . . 179.12(14) ?
C1A C6A C7A O1A . . . . 161.56(15) ?
C5A C6A C7A O1A . . . . -17.6(2) ?
C1A C6A C7A C8A . . . . -19.4(2) ?
C5A C6A C7A C8A . . . . 161.42(14) ?
O1A C7A C8A C9A . . . . -2.2(2) ?
C6A C7A C8A C9A . . . . 178.77(14) ?
C7A C8A C9A C10A . . . . -178.39(14) ?
C8A C9A C10A C15A . . . . 179.71(15) ?
C8A C9A C10A C11A . . . . 1.6(3) ?
C15A C10A C11A C12A . . . . -1.4(2) ?
C9A C10A C11A C12A . . . . 176.80(15) ?
C10A C11A C12A C13A . . . . -0.1(2) ?
C16A N1A C13A C14A . . . . 174.59(14) ?
C18A N1A C13A C14A . . . . 2.3(2) ?
C16A N1A C13A C12A . . . . -6.0(2) ?
C18A N1A C13A C12A . . . . -178.37(14) ?
C11A C12A C13A N1A . . . . -177.54(14) ?
C11A C12A C13A C14A . . . . 1.9(2) ?
N1A C13A C14A C15A . . . . 177.16(15) ?
C12A C13A C14A C15A . . . . -2.2(2) ?
C13A C14A C15A C10A . . . . 0.8(2) ?
C11A C10A C15A C14A . . . . 1.0(2) ?
C9A C10A C15A C14A . . . . -177.26(14) ?
C13A N1A C16A C17A . . . . -78.38(18) ?
C18A N1A C16A C17A . . . . 94.27(16) ?
C13A N1A C18A C19A . . . . 81.27(18) ?
C16A N1A C18A C19A . . . . -91.36(17) ?
C6B C1B C2B C3B . . . . 0.2(2) ?
C1B C2B C3B C4B . . . . -1.3(2) ?
C1B C2B C3B Cl1B . . . . 178.31(12) ?
C2B C3B C4B C5B . . . . 1.3(2) ?
Cl1B C3B C4B C5B . . . . -178.31(12) ?
C3B C4B C5B C6B . . . . -0.2(2) ?
C4B C5B C6B C1B . . . . -0.9(2) ?
C4B C5B C6B C7B . . . . 178.88(14) ?
C2B C1B C6B C5B . . . . 0.9(2) ?
C2B C1B C6B C7B . . . . -178.86(14) ?
C5B C6B C7B O1B . . . . -9.0(2) ?
C1B C6B C7B O1B . . . . 170.70(15) ?
C5B C6B C7B C8B . . . . 169.77(14) ?
C1B C6B C7B C8B . . . . -10.5(2) ?
O1B C7B C8B C9B . . . . -3.8(2) ?
C6B C7B C8B C9B . . . . 177.38(14) ?
C7B C8B C9B C10B . . . . 176.11(14) ?
C8B C9B C10B C11B . . . . -2.2(3) ?
C8B C9B C10B C15B . . . . 177.64(15) ?
C15B C10B C11B C12B . . . . -1.5(2) ?
C9B C10B C11B C12B . . . . 178.41(14) ?
C10B C11B C12B C13B . . . . -0.4(2) ?
C18B N1B C13B C14B . . . . 173.21(14) ?
C16B N1B C13B C14B . . . . -12.8(2) ?
C18B N1B C13B C12B . . . . -6.6(2) ?
C16B N1B C13B C12B . . . . 167.43(14) ?
C11B C12B C13B N1B . . . . -178.57(14) ?
C11B C12B C13B C14B . . . . 1.6(2) ?
N1B C13B C14B C15B . . . . 179.29(14) ?
C12B C13B C14B C15B . . . . -0.9(2) ?
C13B C14B C15B C10B . . . . -1.0(2) ?
C11B C10B C15B C14B . . . . 2.2(2) ?
C9B C10B C15B C14B . . . . -177.68(14) ?
C13B N1B C16B C17B . . . . 99.04(17) ?
C18B N1B C16B C17B . . . . -86.63(16) ?
C13B N1B C18B C19B . . . . 84.38(17) ?
C16B N1B C18B C19B . . . . -90.03(16) ?
