# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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data_global


data_e:\120716a\work\mo_120716a_0m
#TrackingRef 'web_deposit_cif_file_0_Chun-JiangWang_1344175046.mo_120716a_0m.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl F3 N2 O3'
_chemical_formula_weight         428.83

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   10.1424(12)
_cell_length_b                   10.9573(13)
_cell_length_c                   19.058(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2118.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14383
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4170
_reflns_number_gt                3974
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.4721P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0322(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_number_reflns         4170
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2805(5) -0.2968(2) 0.49153(13) 0.1111(14) Uani 1 1 d . . .
H1A H 0.1952 -0.3268 0.4781 0.167 Uiso 1 1 calc R . .
H1B H 0.2904 -0.3031 0.5415 0.167 Uiso 1 1 calc R . .
H1C H 0.3476 -0.3444 0.4689 0.167 Uiso 1 1 calc R . .
C2 C 0.2973(2) -0.15001(17) 0.40040(9) 0.0475(4) Uani 1 1 d . . .
C3 C 0.26772(18) -0.23324(16) 0.34843(9) 0.0440(4) Uani 1 1 d . . .
H3 H 0.2445 -0.3126 0.3605 0.053 Uiso 1 1 calc R . .
C4 C 0.27225(16) -0.19960(15) 0.27827(9) 0.0383(3) Uani 1 1 d . . .
H4 H 0.2515 -0.2568 0.2440 0.046 Uiso 1 1 calc R . .
C5 C 0.30732(15) -0.08184(14) 0.25835(8) 0.0336(3) Uani 1 1 d . . .
C6 C 0.33768(17) 0.00128(15) 0.31160(9) 0.0397(3) Uani 1 1 d . . .
H6 H 0.3608 0.0809 0.3000 0.048 Uiso 1 1 calc R . .
C7 C 0.3338(2) -0.03318(17) 0.38124(9) 0.0478(4) Uani 1 1 d . . .
H7 H 0.3560 0.0231 0.4158 0.057 Uiso 1 1 calc R . .
C8 C 0.38182(15) 0.06807(13) 0.16776(8) 0.0334(3) Uani 1 1 d . . .
H8 H 0.4622 0.0737 0.1961 0.040 Uiso 1 1 calc R . .
C9 C 0.42582(17) -0.07920(15) 0.08251(8) 0.0378(3) Uani 1 1 d . . .
C10 C 0.31671(17) -0.13264(14) 0.13076(8) 0.0373(3) Uani 1 1 d . . .
H10 H 0.3459 -0.2115 0.1494 0.045 Uiso 1 1 calc R . .
C11 C 0.30242(15) 0.18432(14) 0.17723(8) 0.0338(3) Uani 1 1 d . . .
C12 C 0.36684(17) 0.29491(15) 0.17536(10) 0.0448(4) Uani 1 1 d . . .
H12 H 0.4582 0.2966 0.1712 0.054 Uiso 1 1 calc R . .
C13 C 0.29754(19) 0.40384(16) 0.17964(11) 0.0500(4) Uani 1 1 d . . .
H13 H 0.3415 0.4783 0.1780 0.060 Uiso 1 1 calc R . .
C14 C 0.16305(19) 0.39948(15) 0.18627(10) 0.0466(4) Uani 1 1 d . . .
C15 C 0.09633(18) 0.29102(18) 0.18996(12) 0.0545(5) Uani 1 1 d . . .
H15 H 0.0052 0.2898 0.1955 0.065 Uiso 1 1 calc R . .
C16 C 0.16717(17) 0.18277(16) 0.18535(11) 0.0493(4) Uani 1 1 d . . .
H16 H 0.1230 0.1085 0.1877 0.059 Uiso 1 1 calc R . .
C17 C 0.4219(2) -0.10818(19) 0.00395(9) 0.0535(5) Uani 1 1 d . . .
H17A H 0.3420 -0.0763 -0.0160 0.080 Uiso 1 1 calc R . .
H17B H 0.4247 -0.1950 -0.0027 0.080 Uiso 1 1 calc R . .
H17C H 0.4964 -0.0714 -0.0188 0.080 Uiso 1 1 calc R . .
C18 C 0.55748(19) -0.13189(16) 0.10969(9) 0.0441(4) Uani 1 1 d . . .
C19 C 0.7863(2) -0.1062(3) 0.11866(16) 0.0803(8) Uani 1 1 d . . .
H19A H 0.8449 -0.0400 0.1295 0.121 Uiso 1 1 calc R . .
H19B H 0.8202 -0.1511 0.0794 0.121 Uiso 1 1 calc R . .
H19C H 0.7793 -0.1593 0.1585 0.121 Uiso 1 1 calc R . .
C20 C 0.1830(2) -0.1476(2) 0.09645(10) 0.0534(5) Uani 1 1 d . . .
Cl1 Cl 0.07382(7) 0.53528(5) 0.19159(4) 0.0799(2) Uani 1 1 d . . .
F1 F 0.14028(12) -0.04826(14) 0.06301(7) 0.0728(4) Uani 1 1 d . . .
F2 F 0.18342(15) -0.23881(15) 0.04961(8) 0.0851(5) Uani 1 1 d . . .
F3 F 0.09011(12) -0.17574(13) 0.14353(7) 0.0667(3) Uani 1 1 d . . .
N1 N 0.30981(13) -0.04475(11) 0.18740(7) 0.0347(3) Uani 1 1 d . . .
N2 N 0.41856(14) 0.05183(12) 0.09437(7) 0.0388(3) Uani 1 1 d . . .
H2A H 0.3575 0.0856 0.0661 0.047 Uiso 1 1 d R . .
O1 O 0.2927(2) -0.17474(14) 0.47125(7) 0.0716(5) Uani 1 1 d . . .
O3 O 0.56801(19) -0.23240(16) 0.13174(13) 0.0932(6) Uani 1 1 d . . .
O4 O 0.65730(14) -0.05801(14) 0.10141(9) 0.0648(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.222(4) 0.0633(15) 0.0480(12) 0.0151(11) 0.0360(19) 0.035(2)
C2 0.0590(11) 0.0475(10) 0.0361(8) 0.0031(7) 0.0112(8) 0.0125(8)
C3 0.0480(9) 0.0372(8) 0.0467(9) 0.0080(7) 0.0083(8) 0.0006(7)
C4 0.0398(8) 0.0332(8) 0.0418(8) -0.0002(6) 0.0010(7) -0.0038(7)
C5 0.0299(7) 0.0335(7) 0.0375(8) 0.0011(6) 0.0021(6) 0.0022(6)
C6 0.0464(9) 0.0315(7) 0.0413(8) -0.0012(7) 0.0039(7) 0.0024(6)
C7 0.0596(11) 0.0448(9) 0.0389(9) -0.0073(7) 0.0070(8) 0.0032(8)
C8 0.0329(7) 0.0289(7) 0.0385(8) 0.0027(6) 0.0024(6) -0.0002(6)
C9 0.0407(8) 0.0357(8) 0.0371(8) 0.0006(6) -0.0019(7) 0.0068(7)
C10 0.0439(9) 0.0326(8) 0.0352(7) -0.0002(6) -0.0064(7) 0.0025(7)
C11 0.0335(7) 0.0309(7) 0.0370(7) 0.0006(6) 0.0017(6) 0.0020(6)
C12 0.0370(8) 0.0354(8) 0.0622(11) -0.0045(8) 0.0017(8) -0.0016(7)
C13 0.0484(10) 0.0308(8) 0.0706(12) -0.0041(8) 0.0011(9) -0.0018(7)
C14 0.0514(10) 0.0360(8) 0.0524(10) -0.0054(8) 0.0018(8) 0.0133(7)
C15 0.0336(8) 0.0499(10) 0.0801(13) -0.0039(10) 0.0079(9) 0.0067(8)
C16 0.0364(8) 0.0358(8) 0.0757(12) 0.0024(9) 0.0101(8) -0.0029(7)
C17 0.0596(12) 0.0625(12) 0.0383(9) -0.0039(8) -0.0009(8) 0.0144(10)
C18 0.0470(10) 0.0434(9) 0.0419(9) -0.0006(7) 0.0003(7) 0.0135(8)
C19 0.0432(12) 0.0919(19) 0.106(2) -0.0092(15) -0.0134(12) 0.0183(12)
C20 0.0501(11) 0.0628(12) 0.0474(10) 0.0021(9) -0.0083(9) -0.0100(9)
Cl1 0.0760(4) 0.0478(3) 0.1159(5) -0.0117(3) -0.0003(4) 0.0280(3)
F1 0.0547(7) 0.0939(10) 0.0697(8) 0.0306(7) -0.0209(6) -0.0008(7)
F2 0.0889(10) 0.0950(11) 0.0716(8) -0.0288(8) -0.0190(8) -0.0283(8)
F3 0.0466(6) 0.0799(8) 0.0735(8) 0.0142(7) -0.0074(6) -0.0155(6)
N1 0.0416(7) 0.0260(6) 0.0365(6) 0.0015(5) -0.0006(6) -0.0003(5)
N2 0.0436(7) 0.0335(6) 0.0392(7) 0.0054(5) 0.0056(6) 0.0095(6)
O1 0.1214(14) 0.0563(8) 0.0372(7) 0.0051(6) 0.0174(8) 0.0150(9)
O3 0.0652(10) 0.0614(10) 0.1530(18) 0.0426(11) -0.0096(11) 0.0190(8)
O4 0.0406(7) 0.0600(9) 0.0939(11) 0.0080(8) -0.0047(7) 0.0079(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.398(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.378(2) . ?
C2 C3 1.379(3) . ?
C2 C7 1.382(3) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(2) . ?
C5 N1 1.412(2) . ?
C6 C7 1.380(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N2 1.458(2) . ?
C8 N1 1.4839(19) . ?
C8 C11 1.518(2) . ?
C8 H8 0.9800 . ?
C9 N2 1.455(2) . ?
C9 C17 1.531(2) . ?
C9 C18 1.544(2) . ?
C9 C10 1.553(2) . ?
C10 N1 1.448(2) . ?
C10 C20 1.515(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.377(2) . ?
C11 C16 1.381(2) . ?
C12 C13 1.388(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(3) . ?
C14 Cl1 1.7445(17) . ?
C15 C16 1.390(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O3 1.184(2) . ?
C18 O4 1.306(3) . ?
C19 O4 1.449(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 F1 1.333(2) . ?
C20 F3 1.337(2) . ?
C20 F2 1.340(2) . ?
N2 H2A 0.9000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.48(17) . . ?
O1 C2 C7 116.77(17) . . ?
C3 C2 C7 118.76(16) . . ?
C2 C3 C4 120.59(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 121.18(15) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 117.55(15) . . ?
C4 C5 N1 122.20(14) . . ?
C6 C5 N1 120.24(14) . . ?
C7 C6 C5 120.89(16) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 121.02(17) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
N2 C8 N1 105.42(12) . . ?
N2 C8 C11 110.61(12) . . ?
N1 C8 C11 114.08(12) . . ?
N2 C8 H8 108.9 . . ?
N1 C8 H8 108.9 . . ?
C11 C8 H8 108.9 . . ?
N2 C9 C17 110.80(14) . . ?
N2 C9 C18 111.13(14) . . ?
C17 C9 C18 105.85(14) . . ?
N2 C9 C10 104.12(13) . . ?
C17 C9 C10 118.82(15) . . ?
C18 C9 C10 106.06(13) . . ?
N1 C10 C20 110.51(14) . . ?
N1 C10 C9 103.00(12) . . ?
C20 C10 C9 115.04(14) . . ?
N1 C10 H10 109.4 . . ?
C20 C10 H10 109.4 . . ?
C9 C10 H10 109.4 . . ?
C12 C11 C16 119.02(15) . . ?
C12 C11 C8 118.92(13) . . ?
C16 C11 C8 122.02(14) . . ?
C11 C12 C13 121.00(16) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.65(16) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 121.78(16) . . ?
C15 C14 Cl1 118.74(14) . . ?
C13 C14 Cl1 119.47(14) . . ?
C14 C15 C16 118.82(16) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C11 C16 C15 120.68(16) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 O4 123.35(19) . . ?
O3 C18 C9 123.02(19) . . ?
O4 C18 C9 113.46(15) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
F1 C20 F3 106.29(18) . . ?
F1 C20 F2 106.94(16) . . ?
F3 C20 F2 106.10(17) . . ?
F1 C20 C10 114.13(16) . . ?
F3 C20 C10 111.47(15) . . ?
F2 C20 C10 111.42(18) . . ?
C5 N1 C10 121.54(12) . . ?
C5 N1 C8 119.35(12) . . ?
C10 N1 C8 110.02(12) . . ?
C9 N2 C8 106.40(12) . . ?
C9 N2 H2A 110.4 . . ?
C8 N2 H2A 110.3 . . ?
C2 O1 C1 117.53(17) . . ?
C18 O4 C19 116.55(18) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 178.59(18) . . . . ?
C7 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C3 C4 C5 N1 -178.58(15) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
N1 C5 C6 C7 179.03(16) . . . . ?
C5 C6 C7 C2 -1.3(3) . . . . ?
O1 C2 C7 C6 -178.18(19) . . . . ?
C3 C2 C7 C6 1.6(3) . . . . ?
N2 C9 C10 N1 -28.67(15) . . . . ?
C17 C9 C10 N1 -152.47(15) . . . . ?
C18 C9 C10 N1 88.66(14) . . . . ?
N2 C9 C10 C20 91.64(17) . . . . ?
C17 C9 C10 C20 -32.2(2) . . . . ?
C18 C9 C10 C20 -151.03(15) . . . . ?
N2 C8 C11 C12 -75.23(18) . . . . ?
N1 C8 C11 C12 166.13(15) . . . . ?
N2 C8 C11 C16 102.60(19) . . . . ?
N1 C8 C11 C16 -16.0(2) . . . . ?
C16 C11 C12 C13 -1.7(3) . . . . ?
C8 C11 C12 C13 176.18(17) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 1.1(3) . . . . ?
C12 C13 C14 Cl1 -179.90(15) . . . . ?
C13 C14 C15 C16 -1.4(3) . . . . ?
Cl1 C14 C15 C16 179.65(17) . . . . ?
C12 C11 C16 C15 1.5(3) . . . . ?
C8 C11 C16 C15 -176.36(17) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
N2 C9 C18 O3 149.1(2) . . . . ?
C17 C9 C18 O3 -90.5(2) . . . . ?
C10 C9 C18 O3 36.5(3) . . . . ?
N2 C9 C18 O4 -35.4(2) . . . . ?
C17 C9 C18 O4 84.92(19) . . . . ?
C10 C9 C18 O4 -147.98(15) . . . . ?
N1 C10 C20 F1 66.2(2) . . . . ?
C9 C10 C20 F1 -49.9(2) . . . . ?
N1 C10 C20 F3 -54.3(2) . . . . ?
C9 C10 C20 F3 -170.35(15) . . . . ?
N1 C10 C20 F2 -172.59(15) . . . . ?
C9 C10 C20 F2 71.3(2) . . . . ?
C4 C5 N1 C10 -19.5(2) . . . . ?
C6 C5 N1 C10 161.98(15) . . . . ?
C4 C5 N1 C8 -163.22(14) . . . . ?
C6 C5 N1 C8 18.3(2) . . . . ?
C20 C10 N1 C5 103.25(17) . . . . ?
C9 C10 N1 C5 -133.38(14) . . . . ?
C20 C10 N1 C8 -110.08(15) . . . . ?
C9 C10 N1 C8 13.30(15) . . . . ?
N2 C8 N1 C5 154.34(13) . . . . ?
C11 C8 N1 C5 -84.10(16) . . . . ?
N2 C8 N1 C10 6.83(16) . . . . ?
C11 C8 N1 C10 128.39(14) . . . . ?
C17 C9 N2 C8 162.71(14) . . . . ?
C18 C9 N2 C8 -79.90(16) . . . . ?
C10 C9 N2 C8 33.86(16) . . . . ?
N1 C8 N2 C9 -25.75(16) . . . . ?
C11 C8 N2 C9 -149.53(13) . . . . ?
C3 C2 O1 C1 12.0(4) . . . . ?
C7 C2 O1 C1 -168.3(3) . . . . ?
O3 C18 O4 C19 1.9(3) . . . . ?
C9 C18 O4 C19 -173.53(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.90 2.56 3.451(2) 171.6 4_554
C6 H6 O3 0.93 2.53 3.255(2) 135.0 3_655

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.033
_database_code_depnum_ccdc_archive 'CCDC 894876'