##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
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# of the IUCr Commission on Journals.                                        #
#                                                                            #
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# are given in the paper "The Crystallographic Information File (CIF):       #
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# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-12-05
_journal_date_accepted     2009-12-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o254
_journal_page_last     o255
_journal_paper_category     QO
_journal_coeditor_code     CV2675
_publ_contact_author_name     'Assoc.Prof. Dr. Suchada Chantrapromma'
_publ_contact_author_address
;
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      THAILAND
;
_publ_contact_author_email     'suchada.c@psu.ac.th'
_publ_contact_author_fax     '66 74 212918'
_publ_contact_author_phone     '66 74 288447'
_publ_section_title
;
(E)-1-(4-Chlorophenyl)-3-[4-(diethylamino)phenyl]prop-2-en-1-one
;
_publ_section_title_footnote
;
 This paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand
(King Rama IX) on the occasion of his 82th Birthday Anniversary which fell on
December 5th, 2009.
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Thawanrat Kobkeatthawin' ?
;     Crystal Materials Research Unit
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Suchada Chantrapromma'
;
      Thomson Reuters ResearcherID: A-5085-2009.
;
;     Crystal Materials Research Unit
      Department of Chemistry
      Faculty of Science
      Prince of Songkla University
      Hat-Yai, Songkhla 90112
      Thailand
;
    'Hoong-Kun Fun'
;
      Additional correspondence author, e-mail: hkfun@usm.my.
      Thomson Reuters ResearcherID: A-3561-2009.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-1-(4-Chlorophenyl)-3-[4-(diethylamino)phenyl]prop-2-en-1-one
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C19 H20 Cl N O'
_chemical_formula_sum     'C19 H20 Cl N O'
_chemical_formula_iupac     'C19 H20 Cl N O'
_chemical_formula_weight     313.81
_chemical_melting_point     ?
_chemical_melting_point_gt     374
_chemical_melting_point_lt     375
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     17.2073(2)
_cell_length_b     11.94670(10)
_cell_length_c     15.7996(2)
_cell_angle_alpha     90.00
_cell_angle_beta     97.2680(10)
_cell_angle_gamma     90.00
_cell_volume     3221.84(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9400
_cell_measurement_theta_min     1.91
_cell_measurement_theta_max     30.00
_cell_measurement_temperature     100
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.294
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1328
_exptl_absorpt_coefficient_mu     0.239
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.9252
_exptl_absorpt_correction_T_max     0.9765
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1) K.
;
_diffrn_ambient_temperature     100
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     47596
_diffrn_reflns_av_R_equivalents     0.0407
_diffrn_reflns_av_sigmaI/netI     0.0568
_diffrn_reflns_theta_min     1.19
_diffrn_reflns_theta_max     30.00
_diffrn_reflns_theta_full     30.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     9400
_reflns_number_gt     6241
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0834
_refine_ls_R_factor_gt     0.0479
_refine_ls_wR_factor_gt     0.1021
_refine_ls_wR_factor_ref     0.1220
_refine_ls_goodness_of_fit_ref     1.098
_refine_ls_restrained_S_all     1.098
_refine_ls_number_reflns     9400
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0474P)²+0.7024P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.318
_refine_diff_density_min     -0.346
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) ?
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
