##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# 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  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
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data_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2008-06-25
_journal_date_accepted     2008-08-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      9
_journal_page_first     o1772
_journal_page_last     o1773
_journal_paper_category     QO
_journal_coeditor_code     FB2102
_publ_contact_author_name     'Ling-Ling Zhao'
_publ_contact_author_address
;
School of Chemistry and Chemical Engineering
Xuzhou Normal University
Xuzhou 221116
People's Republic of China
;
_publ_contact_author_email     zllcpu@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
10-(4-Chlorophenyl)-9-(4-fluorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-\
hexahydroacridine-1,8(2<i>H</i>,5<i>H</i>)-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Ling-Ling Zhao'
;
School of Chemistry and Chemical Engineering
Xuzhou Normal University
Xuzhou 221116
People's Republic of China
;
    'Da Teng'
;
School of Chemistry and Chemical Engineering
Xuzhou Normal University
Xuzhou 221116
People's Republic of China
;
data_I
_chemical_name_systematic
;
10-(4-Chlorophenyl)-9-(4-fluorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2<i>H</i>,5<i>H</i>)-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C29 H29 Cl F N O2'
_chemical_formula_sum     'C29 H29 Cl F N O2'
_chemical_formula_iupac     'C29 H29 Cl F N O2'
_chemical_formula_weight     477.98
_chemical_melting_point     ?
_chemical_melting_point_gt     583
_chemical_melting_point_lt     585
_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     12.0985(12)
_cell_length_b     10.9001(10)
_cell_length_c     19.4724(18)
_cell_angle_alpha     90.00
_cell_angle_beta     101.231(3)
_cell_angle_gamma     90.00
_cell_volume     2518.7(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8097
_cell_measurement_theta_min     1.7
_cell_measurement_theta_max     27.9
_cell_measurement_temperature     113(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.260
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1008
_exptl_absorpt_coefficient_mu     0.185
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrystalClear; Rigaku, 1999)'
_exptl_absorpt_correction_T_min     0.9431
_exptl_absorpt_correction_T_max     0.9674
_exptl_special_details
;
;
_diffrn_ambient_temperature     113(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_source     'rotating anode'
_diffrn_radiation_monochromator     confocal
_diffrn_measurement_device_type     'Rigaku Saturn'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     14.63
_diffrn_reflns_number     30908
_diffrn_reflns_av_R_equivalents     0.0400
_diffrn_reflns_av_sigmaI/netI     0.0336
_diffrn_reflns_theta_min     1.72
_diffrn_reflns_theta_max     27.89
_diffrn_reflns_theta_full     27.89
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     25
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     6016
_reflns_number_gt     5436
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0631
_refine_ls_R_factor_gt     0.0549
_refine_ls_wR_factor_gt     0.1314
_refine_ls_wR_factor_ref     0.1370
_refine_ls_goodness_of_fit_ref     1.102
_refine_ls_restrained_S_all     1.102
_refine_ls_number_reflns     6016
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_number_constraints     112
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[\s^2^(Fo^2^)+(0.0579P)^2^+1.0431P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     difmap
_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     0.423
_refine_diff_density_min     -0.447
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0058(9)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
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'
    'F' 'F' 0.0171 0.0103
                         '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     'CrystalClear (Rigaku, 1999)'
_computing_cell_refinement     'CrystalClear (Rigaku, 1999)'
_computing_data_reduction     'CrystalClear (Rigaku, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'CrystalStructure (Rigaku/MSC, 2003)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.86649(5) 1.04288(4) 0.25315(3) 0.04213(16) Uani d . 1 . .
    F F1 1.03322(14) 0.02721(16) 0.07820(8) 0.0761(5) Uani d . 1 . .
    O O1 0.56729(11) 0.16766(11) 0.17692(7) 0.0326(3) Uani d . 1 . .
    O O2 0.57270(11) 0.31474(12) -0.06509(7) 0.0330(3) Uani d . 1 . .
    N N1 0.70646(12) 0.56013(12) 0.13279(7) 0.0229(3) Uani d . 1 . .
    C C1 0.67413(13) 0.47215(14) 0.17771(8) 0.0219(3) Uani d . 1 . .
    C C2 0.64094(13) 0.35886(15) 0.15353(8) 0.0223(3) Uani d . 1 . .
    C C3 0.64825(14) 0.31701(14) 0.08070(9) 0.0231(3) Uani d . 1 . .
    H H3 0.5793 0.2681 0.0614 0.028 Uiso calc R 1 . .
    C C4 0.65130(13) 0.42790(15) 0.03444(9) 0.0231(3) Uani d . 1 . .
    C C5 0.68642(13) 0.53925(14) 0.06063(9) 0.0224(3) Uani d . 1 . .
    C C6 0.74535(14) 0.67913(14) 0.16009(8) 0.0228(3) Uani d . 1 . .
    C C7 0.85853(15) 0.69498(17) 0.18908(10) 0.0304(4) Uani d . 1 . .
    H H7 0.9099 0.6289 0.1895 0.036 Uiso calc R 1 . .
    C C8 0.89647(16) 0.80758(18) 0.21746(10) 0.0336(4) Uani d . 1 . .
    H H8 0.9738 0.8194 0.2376 0.040 Uiso calc R 1 . .
    C C9 0.82031(15) 0.90184(16) 0.21587(9) 0.0278(4) Uani d . 1 . .
    C C10 0.70815(15) 0.88861(15) 0.18595(9) 0.0269(4) Uani d . 1 . .
    H H10 0.6576 0.9557 0.1844 0.032 Uiso calc R 1 . .
    C C11 0.67004(14) 0.77543(15) 0.15803(9) 0.0244(3) Uani d . 1 . .
    H H11 0.5927 0.7642 0.1376 0.029 Uiso calc R 1 . .
    C C12 0.67473(15) 0.51183(15) 0.25200(9) 0.0263(4) Uani d . 1 . .
    H H12A 0.6074 0.5631 0.2527 0.032 Uiso calc R 1 . .
    H H12B 0.7422 0.5631 0.2686 0.032 Uiso calc R 1 . .
    C C13 0.67515(15) 0.40361(15) 0.30251(9) 0.0264(4) Uani d . 1 . .
    C C14 0.58278(15) 0.31382(16) 0.26947(9) 0.0274(4) Uani d . 1 . .
    H H14A 0.5842 0.2417 0.3006 0.033 Uiso calc R 1 . .
    H H14B 0.5085 0.3541 0.2656 0.033 Uiso calc R 1 . .
    C C15 0.59618(13) 0.27108(15) 0.19831(9) 0.0242(3) Uani d . 1 . .
    C C16 0.65091(19) 0.45153(17) 0.37181(10) 0.0365(4) Uani d . 1 . .
    H H16A 0.5787 0.4952 0.3632 0.055 Uiso calc R 1 . .
    H H16B 0.7111 0.5077 0.3931 0.055 Uiso calc R 1 . .
    H H16C 0.6474 0.3825 0.4035 0.055 Uiso calc R 1 . .
    C C17 0.78922(16) 0.33872(18) 0.31572(11) 0.0367(4) Uani d . 1 . .
    H H17A 0.8487 0.3977 0.3342 0.055 Uiso calc R 1 . .
    H H17B 0.8031 0.3043 0.2717 0.055 Uiso calc R 1 . .
    H H17C 0.7890 0.2725 0.3497 0.055 Uiso calc R 1 . .
    C C18 0.70364(15) 0.64547(15) 0.01412(9) 0.0263(4) Uani d . 1 . .
    H H18A 0.7669 0.6965 0.0386 0.032 Uiso calc R 1 . .
    H H18B 0.6350 0.6970 0.0056 0.032 Uiso calc R 1 . .
    C C19 0.72913(15) 0.60365(16) -0.05647(9) 0.0276(4) Uani d . 1 . .
    C C20 0.63778(15) 0.51338(17) -0.08888(9) 0.0293(4) Uani d . 1 . .
    H H20A 0.5663 0.5589 -0.1036 0.035 Uiso calc R 1 . .
    H H20B 0.6584 0.4777 -0.1314 0.035 Uiso calc R 1 . .
    C C21 0.61825(14) 0.41026(16) -0.04108(9) 0.0264(4) Uani d . 1 . .
    C C22 0.84573(16) 0.54320(18) -0.04596(10) 0.0338(4) Uani d . 1 . .
    H H22A 0.8465 0.4697 -0.0168 0.051 Uiso calc R 1 . .
    H H22B 0.9029 0.6011 -0.0228 0.051 Uiso calc R 1 . .
    H H22C 0.8622 0.5201 -0.0916 0.051 Uiso calc R 1 . .
    C C23 0.72650(17) 0.71613(17) -0.10400(10) 0.0347(4) Uani d . 1 . .
    H H23A 0.7434 0.6909 -0.1491 0.052 Uiso calc R 1 . .
    H H23B 0.7829 0.7758 -0.0818 0.052 Uiso calc R 1 . .
    H H23C 0.6515 0.7537 -0.1114 0.052 Uiso calc R 1 . .
    C C24 0.75157(15) 0.23635(15) 0.08100(9) 0.0262(4) Uani d . 1 . .
    C C25 0.85885(16) 0.28331(19) 0.10536(10) 0.0350(4) Uani d . 1 . .
    H H25 0.8671 0.3649 0.1227 0.042 Uiso calc R 1 . .
    C C26 0.95412(18) 0.2128(2) 0.10467(11) 0.0443(5) Uani d . 1 . .
    H H26 1.0274 0.2449 0.1214 0.053 Uiso calc R 1 . .
    C C27 0.9395(2) 0.0961(2) 0.07926(11) 0.0480(6) Uani d . 1 . .
    C C28 0.8360(2) 0.0456(2) 0.05529(11) 0.0479(6) Uani d . 1 . .
    H H28 0.8289 -0.0363 0.0382 0.057 Uiso calc R 1 . .
    C C29 0.74091(18) 0.11699(17) 0.05649(10) 0.0357(4) Uani d . 1 . .
    H H29 0.6680 0.0834 0.0403 0.043 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl1 0.0539(3) 0.0306(3) 0.0401(3) -0.0193(2) 0.0050(2) -0.00797(19)
    F1 0.0758(10) 0.1001(13) 0.0550(9) 0.0666(10) 0.0195(8) 0.0108(8)
    O1 0.0356(7) 0.0234(6) 0.0404(7) -0.0077(5) 0.0110(6) -0.0044(5)
    O2 0.0345(7) 0.0322(7) 0.0303(7) -0.0003(5) 0.0012(5) -0.0087(5)
    N1 0.0274(7) 0.0189(6) 0.0234(7) -0.0022(5) 0.0071(5) -0.0024(5)
    C1 0.0220(8) 0.0207(8) 0.0236(8) 0.0005(6) 0.0060(6) -0.0010(6)
    C2 0.0210(8) 0.0212(8) 0.0255(8) 0.0014(6) 0.0062(6) -0.0019(6)
    C3 0.0240(8) 0.0199(8) 0.0255(8) -0.0012(6) 0.0051(6) -0.0040(6)
    C4 0.0214(8) 0.0228(8) 0.0249(8) 0.0013(6) 0.0042(6) -0.0019(6)
    C5 0.0215(8) 0.0215(8) 0.0248(8) 0.0021(6) 0.0058(6) -0.0007(6)
    C6 0.0272(8) 0.0195(8) 0.0225(8) -0.0033(6) 0.0069(6) -0.0011(6)
    C7 0.0247(9) 0.0297(9) 0.0361(10) 0.0017(7) 0.0042(7) 0.0027(7)
    C8 0.0251(9) 0.0359(10) 0.0374(10) -0.0087(7) 0.0000(7) 0.0017(8)
    C9 0.0338(9) 0.0255(8) 0.0242(8) -0.0101(7) 0.0058(7) -0.0005(7)
    C10 0.0297(9) 0.0215(8) 0.0310(9) -0.0012(7) 0.0093(7) -0.0027(7)
    C11 0.0231(8) 0.0227(8) 0.0281(8) -0.0023(6) 0.0065(6) -0.0025(6)
    C12 0.0355(9) 0.0201(8) 0.0248(8) -0.0015(7) 0.0097(7) -0.0032(6)
    C13 0.0335(9) 0.0199(8) 0.0253(8) -0.0007(7) 0.0046(7) -0.0001(6)
    C14 0.0311(9) 0.0244(8) 0.0282(9) -0.0023(7) 0.0091(7) 0.0014(7)
    C15 0.0203(8) 0.0207(8) 0.0314(9) 0.0002(6) 0.0044(6) -0.0022(6)
    C16 0.0572(13) 0.0263(9) 0.0267(9) -0.0019(8) 0.0100(8) 0.0006(7)
    C17 0.0349(10) 0.0314(10) 0.0394(11) 0.0016(8) -0.0038(8) -0.0039(8)
    C18 0.0303(9) 0.0230(8) 0.0268(9) 0.0019(7) 0.0084(7) 0.0003(7)
    C19 0.0307(9) 0.0282(9) 0.0249(8) 0.0044(7) 0.0081(7) 0.0028(7)
    C20 0.0307(9) 0.0318(9) 0.0243(8) 0.0053(7) 0.0028(7) 0.0005(7)
    C21 0.0217(8) 0.0286(9) 0.0283(9) 0.0059(7) 0.0039(6) -0.0034(7)
    C22 0.0292(9) 0.0388(10) 0.0356(10) 0.0058(8) 0.0121(8) 0.0053(8)
    C23 0.0415(11) 0.0330(10) 0.0309(10) 0.0053(8) 0.0106(8) 0.0067(8)
    C24 0.0332(9) 0.0248(8) 0.0221(8) 0.0069(7) 0.0096(7) 0.0026(6)
    C25 0.0299(10) 0.0371(10) 0.0395(11) 0.0063(8) 0.0107(8) 0.0043(8)
    C26 0.0334(11) 0.0602(14) 0.0423(12) 0.0169(10) 0.0146(9) 0.0142(10)
    C27 0.0546(14) 0.0618(15) 0.0310(10) 0.0382(12) 0.0168(9) 0.0116(10)
    C28 0.0770(17) 0.0372(11) 0.0303(11) 0.0299(11) 0.0124(10) -0.0012(8)
    C29 0.0515(12) 0.0278(9) 0.0273(9) 0.0104(8) 0.0058(8) -0.0018(7)
_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
    Cl1 C9 . 1.7449(18) ?
    F1 C27 . 1.364(2) ?
    O1 C15 . 1.229(2) ?
    O2 C21 . 1.227(2) ?
    N1 C5 . 1.397(2) ?
    N1 C1 . 1.404(2) ?
    N1 C6 . 1.445(2) ?
    C1 C2 . 1.354(2) ?
    C1 C12 . 1.509(2) ?
    C2 C15 . 1.467(2) ?
    C2 C3 . 1.509(2) ?
    C3 C4 . 1.512(2) ?
    C3 C24 . 1.527(2) ?
    C3 H3 . 1.0000 ?
    C4 C5 . 1.353(2) ?
    C4 C21 . 1.460(2) ?
    C5 C18 . 1.509(2) ?
    C6 C11 . 1.385(2) ?
    C6 C7 . 1.387(2) ?
    C7 C8 . 1.387(3) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.376(3) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.376(2) ?
    C10 C11 . 1.390(2) ?
    C10 H10 . 0.9500 ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.535(2) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C17 . 1.527(2) ?
    C13 C16 . 1.528(2) ?
    C13 C14 . 1.530(2) ?
    C14 C15 . 1.500(2) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 C19 . 1.535(2) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 C20 . 1.522(3) ?
    C19 C23 . 1.533(2) ?
    C19 C22 . 1.534(2) ?
    C20 C21 . 1.507(3) ?
    C20 H20A . 0.9900 ?
    C20 H20B . 0.9900 ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    C24 C29 . 1.383(2) ?
    C24 C25 . 1.390(3) ?
    C25 C26 . 1.388(3) ?
    C25 H25 . 0.9500 ?
    C26 C27 . 1.364(3) ?
    C26 H26 . 0.9500 ?
    C27 C28 . 1.364(4) ?
    C28 C29 . 1.393(3) ?
    C28 H28 . 0.9500 ?
    C29 H29 . 0.9500 ?
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
    C5 N1 C1 . . 120.03(13) ?
    C5 N1 C6 . . 119.75(13) ?
    C1 N1 C6 . . 119.62(13) ?
    C2 C1 N1 . . 120.39(15) ?
    C2 C1 C12 . . 122.73(15) ?
    N1 C1 C12 . . 116.85(13) ?
    C1 C2 C15 . . 120.44(15) ?
    C1 C2 C3 . . 122.33(15) ?
    C15 C2 C3 . . 117.23(14) ?
    C2 C3 C4 . . 109.33(13) ?
    C2 C3 C24 . . 111.60(13) ?
    C4 C3 C24 . . 110.34(13) ?
    C2 C3 H3 . . 108.5 ?
    C4 C3 H3 . . 108.5 ?
    C24 C3 H3 . . 108.5 ?
    C5 C4 C21 . . 120.15(15) ?
    C5 C4 C3 . . 122.35(15) ?
    C21 C4 C3 . . 117.47(14) ?
    C4 C5 N1 . . 120.36(15) ?
    C4 C5 C18 . . 122.15(15) ?
    N1 C5 C18 . . 117.48(14) ?
    C11 C6 C7 . . 120.61(15) ?
    C11 C6 N1 . . 120.28(14) ?
    C7 C6 N1 . . 119.11(15) ?
    C6 C7 C8 . . 119.77(17) ?
    C6 C7 H7 . . 120.1 ?
    C8 C7 H7 . . 120.1 ?
    C9 C8 C7 . . 118.91(16) ?
    C9 C8 H8 . . 120.5 ?
    C7 C8 H8 . . 120.5 ?
    C10 C9 C8 . . 122.13(16) ?
    C10 C9 Cl1 . . 118.55(14) ?
    C8 C9 Cl1 . . 119.32(14) ?
    C9 C10 C11 . . 118.90(16) ?
    C9 C10 H10 . . 120.6 ?
    C11 C10 H10 . . 120.6 ?
    C6 C11 C10 . . 119.66(15) ?
    C6 C11 H11 . . 120.2 ?
    C10 C11 H11 . . 120.2 ?
    C1 C12 C13 . . 113.13(13) ?
    C1 C12 H12A . . 109.0 ?
    C13 C12 H12A . . 109.0 ?
    C1 C12 H12B . . 109.0 ?
    C13 C12 H12B . . 109.0 ?
    H12A C12 H12B . . 107.8 ?
    C17 C13 C16 . . 109.41(15) ?
    C17 C13 C14 . . 109.67(14) ?
    C16 C13 C14 . . 109.88(15) ?
    C17 C13 C12 . . 110.72(15) ?
    C16 C13 C12 . . 109.02(14) ?
    C14 C13 C12 . . 108.12(14) ?
    C15 C14 C13 . . 112.68(14) ?
    C15 C14 H14A . . 109.1 ?
    C13 C14 H14A . . 109.1 ?
    C15 C14 H14B . . 109.1 ?
    C13 C14 H14B . . 109.1 ?
    H14A C14 H14B . . 107.8 ?
    O1 C15 C2 . . 120.69(16) ?
    O1 C15 C14 . . 121.55(15) ?
    C2 C15 C14 . . 117.72(14) ?
    C13 C16 H16A . . 109.5 ?
    C13 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C13 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    C13 C17 H17A . . 109.5 ?
    C13 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C13 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C5 C18 C19 . . 112.63(14) ?
    C5 C18 H18A . . 109.1 ?
    C19 C18 H18A . . 109.1 ?
    C5 C18 H18B . . 109.1 ?
    C19 C18 H18B . . 109.1 ?
    H18A C18 H18B . . 107.8 ?
    C20 C19 C23 . . 109.80(15) ?
    C20 C19 C22 . . 110.63(15) ?
    C23 C19 C22 . . 109.55(15) ?
    C20 C19 C18 . . 107.87(14) ?
    C23 C19 C18 . . 108.60(14) ?
    C22 C19 C18 . . 110.36(14) ?
    C21 C20 C19 . . 114.50(14) ?
    C21 C20 H20A . . 108.6 ?
    C19 C20 H20A . . 108.6 ?
    C21 C20 H20B . . 108.6 ?
    C19 C20 H20B . . 108.6 ?
    H20A C20 H20B . . 107.6 ?
    O2 C21 C4 . . 120.67(16) ?
    O2 C21 C20 . . 120.69(16) ?
    C4 C21 C20 . . 118.61(15) ?
    C19 C22 H22A . . 109.5 ?
    C19 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C19 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C19 C23 H23A . . 109.5 ?
    C19 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C19 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C29 C24 C25 . . 118.83(17) ?
    C29 C24 C3 . . 121.26(16) ?
    C25 C24 C3 . . 119.90(15) ?
    C26 C25 C24 . . 121.0(2) ?
    C26 C25 H25 . . 119.5 ?
    C24 C25 H25 . . 119.5 ?
    C27 C26 C25 . . 118.1(2) ?
    C27 C26 H26 . . 121.0 ?
    C25 C26 H26 . . 121.0 ?
    F1 C27 C26 . . 118.0(2) ?
    F1 C27 C28 . . 118.9(2) ?
    C26 C27 C28 . . 123.11(19) ?
    C27 C28 C29 . . 118.3(2) ?
    C27 C28 H28 . . 120.8 ?
    C29 C28 H28 . . 120.8 ?
    C24 C29 C28 . . 120.6(2) ?
    C24 C29 H29 . . 119.7 ?
    C28 C29 H29 . . 119.7 ?
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
    C5 N1 C1 C2 . . . . 11.0(2) ?
    C6 N1 C1 C2 . . . . -177.87(14) ?
    C5 N1 C1 C12 . . . . -166.96(14) ?
    C6 N1 C1 C12 . . . . 4.1(2) ?
    N1 C1 C2 C15 . . . . -173.71(14) ?
    C12 C1 C2 C15 . . . . 4.2(2) ?
    N1 C1 C2 C3 . . . . 6.5(2) ?
    C12 C1 C2 C3 . . . . -175.64(15) ?
    C1 C2 C3 C4 . . . . -22.1(2) ?
    C15 C2 C3 C4 . . . . 158.08(14) ?
    C1 C2 C3 C24 . . . . 100.24(18) ?
    C15 C2 C3 C24 . . . . -79.58(18) ?
    C2 C3 C4 C5 . . . . 23.5(2) ?
    C24 C3 C4 C5 . . . . -99.62(18) ?
    C2 C3 C4 C21 . . . . -158.60(14) ?
    C24 C3 C4 C21 . . . . 78.30(18) ?
    C21 C4 C5 N1 . . . . 173.05(14) ?
    C3 C4 C5 N1 . . . . -9.1(2) ?
    C21 C4 C5 C18 . . . . -5.9(2) ?
    C3 C4 C5 C18 . . . . 171.93(15) ?
    C1 N1 C5 C4 . . . . -9.7(2) ?
    C6 N1 C5 C4 . . . . 179.21(15) ?
    C1 N1 C5 C18 . . . . 169.32(14) ?
    C6 N1 C5 C18 . . . . -1.8(2) ?
    C5 N1 C6 C11 . . . . 79.2(2) ?
    C1 N1 C6 C11 . . . . -91.90(19) ?
    C5 N1 C6 C7 . . . . -101.61(19) ?
    C1 N1 C6 C7 . . . . 87.3(2) ?
    C11 C6 C7 C8 . . . . 1.2(3) ?
    N1 C6 C7 C8 . . . . -177.99(16) ?
    C6 C7 C8 C9 . . . . -0.3(3) ?
    C7 C8 C9 C10 . . . . -1.2(3) ?
    C7 C8 C9 Cl1 . . . . 178.58(14) ?
    C8 C9 C10 C11 . . . . 1.7(3) ?
    Cl1 C9 C10 C11 . . . . -178.07(13) ?
    C7 C6 C11 C10 . . . . -0.7(3) ?
    N1 C6 C11 C10 . . . . 178.50(15) ?
    C9 C10 C11 C6 . . . . -0.7(3) ?
    C2 C1 C12 C13 . . . . 20.1(2) ?
    N1 C1 C12 C13 . . . . -161.93(14) ?
    C1 C12 C13 C17 . . . . 71.36(18) ?
    C1 C12 C13 C16 . . . . -168.23(15) ?
    C1 C12 C13 C14 . . . . -48.81(19) ?
    C17 C13 C14 C15 . . . . -64.45(19) ?
    C16 C13 C14 C15 . . . . 175.25(14) ?
    C12 C13 C14 C15 . . . . 56.38(19) ?
    C1 C2 C15 O1 . . . . -179.08(15) ?
    C3 C2 C15 O1 . . . . 0.7(2) ?
    C1 C2 C15 C14 . . . . 3.3(2) ?
    C3 C2 C15 C14 . . . . -176.84(14) ?
    C13 C14 C15 O1 . . . . 147.61(16) ?
    C13 C14 C15 C2 . . . . -34.8(2) ?
    C4 C5 C18 C19 . . . . -25.5(2) ?
    N1 C5 C18 C19 . . . . 155.53(14) ?
    C5 C18 C19 C20 . . . . 52.13(18) ?
    C5 C18 C19 C23 . . . . 171.08(15) ?
    C5 C18 C19 C22 . . . . -68.83(19) ?
    C23 C19 C20 C21 . . . . -169.46(14) ?
    C22 C19 C20 C21 . . . . 69.51(19) ?
    C18 C19 C20 C21 . . . . -51.28(19) ?
    C5 C4 C21 O2 . . . . -170.52(16) ?
    C3 C4 C21 O2 . . . . 11.5(2) ?
    C5 C4 C21 C20 . . . . 7.5(2) ?
    C3 C4 C21 C20 . . . . -170.44(14) ?
    C19 C20 C21 O2 . . . . -159.05(16) ?
    C19 C20 C21 C4 . . . . 22.9(2) ?
    C2 C3 C24 C29 . . . . 120.14(17) ?
    C4 C3 C24 C29 . . . . -118.09(17) ?
    C2 C3 C24 C25 . . . . -60.7(2) ?
    C4 C3 C24 C25 . . . . 61.0(2) ?
    C29 C24 C25 C26 . . . . 0.6(3) ?
    C3 C24 C25 C26 . . . . -178.51(17) ?
    C24 C25 C26 C27 . . . . 0.1(3) ?
    C25 C26 C27 F1 . . . . 179.58(18) ?
    C25 C26 C27 C28 . . . . -0.7(3) ?
    F1 C27 C28 C29 . . . . -179.85(18) ?
    C26 C27 C28 C29 . . . . 0.4(3) ?
    C25 C24 C29 C28 . . . . -0.9(3) ?
    C3 C24 C29 C28 . . . . 178.23(16) ?
    C27 C28 C29 C24 . . . . 0.4(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
    C16 H16C O2 4_566 0.98 2.45 3.359(2) 153.3
    C11 H11 O2 3_665 0.95 2.37 3.286(2) 160.4
    C10 H10 O1 1_565 0.95 2.55 3.474(2) 165.1
    C16 H16A O1 2_655 0.98 2.59 3.528(2) 159.3
    C17 H17A F1 2_755 0.98 2.45 3.373(2) 157.1