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


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#
#                 Cambridge Crystallographic Data Centre
#                                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. 
# 
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#  fide research purposes only. It may contain copyright material 
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data_a
_database_code_depnum_ccdc_archive 'CCDC 923886'
#TrackingRef '17624_web_deposit_cif_file_0_ChaoChen_1360299383.chen5b.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 F3 N O'
_chemical_formula_sum            'C13 H16 F3 N O'
_chemical_formula_weight         259.27
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'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   5.8366(12)
_cell_length_b                   22.212(4)
_cell_length_c                   10.215(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.80(3)
_cell_angle_gamma                90.00
_cell_volume                     1274.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2887
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.5
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52025
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   DATABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      173(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  'Rigaku Saturn724+'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9053
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2913
_reflns_number_gt                2619
_reflns_threshold_expression     I>2sigma(I)
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_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^)+(0.0010P)^2^+1.2831P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2913
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_iucr_refine_instructions_details 
;
TITL a in P2(1)/c
CELL 0.71073 5.8366 22.2119 10.2151 90.000 105.797 90.000
ZERR 4.00 0.0012 0.0044 0.0020 0.000 0.030 0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O F
UNIT 52 64 4 4 12
EQIV $1 X, 0.5-Y, -0.5+Z
HTAB N1 O1_$1
L.S. 4
ACTA
BOND $H
FMAP 2
PLAN 10
WGHT 0.001000 1.283100
FVAR 0.91766
F1 5 0.445568 0.520454 0.772766 11.00000 0.06832 0.02760 =
0.05933 -0.00257 0.02051 0.00204
O1 4 0.203292 0.261198 0.778455 11.00000 0.06415 0.03574 =
0.02368 -0.00164 0.01138 -0.01243
F2 5 0.356431 0.448222 0.887156 11.00000 0.11613 0.04441 =
0.05920 -0.02075 0.05674 -0.02376
N1 3 0.225299 0.277197 0.563437 11.00000 0.04767 0.02944 =
0.02295 -0.00394 0.01032 -0.00407
H1 2 0.198930 0.261432 0.482289 11.00000 -1.20000
F3 5 0.723794 0.470023 0.909556 11.00000 0.07857 0.05534 =
0.04786 -0.01890 -0.00696 0.00358
C6 1 0.019587 0.186291 0.609895 11.00000 0.03493 0.02808 =
0.02846 -0.00275 0.00608 -0.00108
C7 1 0.155073 0.245004 0.659191 11.00000 0.03627 0.02826 =
0.02641 0.00025 0.00613 0.00161
C8 1 0.367285 0.370978 0.688265 11.00000 0.04127 0.02860 =
0.02659 0.00221 0.01234 0.00092
AFIX 43
H8 2 0.267980 0.364967 0.744492 11.00000 -1.20000
AFIX 0
C9 1 0.516553 0.340348 0.502703 11.00000 0.04758 0.03542 =
0.03028 -0.00352 0.01623 0.00229
AFIX 43
H9 2 0.518012 0.313403 0.433251 11.00000 -1.20000
AFIX 0
C10 1 0.664939 0.432583 0.623284 11.00000 0.03734 0.03374 =
0.03933 0.00222 0.01053 -0.00135
C11 1 0.370030 0.329538 0.586596 11.00000 0.03767 0.02714 =
0.02532 0.00148 0.00680 0.00080
C12 1 0.513972 0.421556 0.705555 11.00000 0.04001 0.02802 =
0.02664 0.00163 0.00716 0.00238
C13 1 0.660701 0.390878 0.521362 11.00000 0.04585 0.04343 =
0.04314 0.00268 0.02278 -0.00119
AFIX 43
H13 2 0.757662 0.397084 0.463885 11.00000 -1.20000
AFIX 0
C14 1 0.509453 0.464365 0.818042 11.00000 0.05639 0.03036 =
0.03764 -0.00207 0.01521 -0.00470
C15 1 0.825335 0.487164 0.638338 11.00000 0.05166 0.04674 =
0.06549 -0.00290 0.02404 -0.01244
AFIX 137
H15A 2 0.732218 0.521740 0.600222 11.00000 -1.50000
H15B 2 0.944659 0.480221 0.591322 11.00000 -1.50000
H15C 2 0.900849 0.494145 0.733017 11.00000 -1.50000
AFIX 0
C16 1 0.201902 0.139934 0.591854 11.00000 0.04828 0.03136 =
0.08826 -0.00995 0.01798 0.00187
AFIX 137
H16A 2 0.323511 0.135320 0.676046 11.00000 -1.50000
H16B 2 0.272603 0.153364 0.522426 11.00000 -1.50000
H16C 2 0.124170 0.101985 0.565751 11.00000 -1.50000
AFIX 0
C17 1 -0.097134 0.164300 0.717431 11.00000 0.07247 0.06051 =
0.04944 -0.01355 0.02576 -0.03472
AFIX 137
H17A 2 -0.207246 0.194145 0.731220 11.00000 -1.50000
H17B 2 0.022968 0.157479 0.801319 11.00000 -1.50000
H17C 2 -0.180740 0.127408 0.687577 11.00000 -1.50000
AFIX 0
C18 1 -0.172385 0.194094 0.476126 11.00000 0.06122 0.04191 =
0.04875 0.00362 -0.01188 -0.01116
AFIX 137
H18A 2 -0.255556 0.156725 0.451423 11.00000 -1.50000
H18B 2 -0.099985 0.205862 0.406191 11.00000 -1.50000
H18C 2 -0.282630 0.224615 0.486436 11.00000 -1.50000
HKLF 4
REM a in P2(1)/c
REM R1 = 0.0618 for 2619 Fo > 4sig(Fo) and 0.0690 for all 2913 data
REM 170 parameters refined using 0 restraints
END
;
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
F1 F 0.4456(3) 0.52045(5) 0.77277(14) 0.0511(4) Uani 1 1 d . . .
O1 O 0.2033(3) 0.26120(6) 0.77845(14) 0.0413(4) Uani 1 1 d . . .
F2 F 0.3564(3) 0.44822(6) 0.88716(15) 0.0668(5) Uani 1 1 d . . .
N1 N 0.2253(3) 0.27720(7) 0.56344(17) 0.0332(4) Uani 1 1 d . . .
H1 H 0.199(4) 0.2614(10) 0.482(2) 0.040 Uiso 1 1 d . . .
F3 F 0.7238(3) 0.47002(6) 0.90956(14) 0.0653(4) Uani 1 1 d . . .
C6 C 0.0196(3) 0.18629(8) 0.60989(19) 0.0310(4) Uani 1 1 d . . .
C7 C 0.1551(3) 0.24500(8) 0.65919(19) 0.0308(4) Uani 1 1 d . . .
C8 C 0.3673(4) 0.37098(8) 0.68827(19) 0.0315(4) Uani 1 1 d . . .
H8 H 0.2680 0.3650 0.7445 0.038 Uiso 1 1 calc R . .
C9 C 0.5166(4) 0.34035(9) 0.5027(2) 0.0367(5) Uani 1 1 d . . .
H9 H 0.5180 0.3134 0.4333 0.044 Uiso 1 1 calc R . .
C10 C 0.6649(4) 0.43258(9) 0.6233(2) 0.0368(5) Uani 1 1 d . . .
C11 C 0.3700(3) 0.32954(8) 0.58660(19) 0.0304(4) Uani 1 1 d . . .
C12 C 0.5140(4) 0.42156(8) 0.70556(19) 0.0319(4) Uani 1 1 d . . .
C13 C 0.6607(4) 0.39088(10) 0.5214(2) 0.0420(5) Uani 1 1 d . . .
H13 H 0.7577 0.3971 0.4639 0.050 Uiso 1 1 calc R . .
C14 C 0.5095(4) 0.46436(9) 0.8180(2) 0.0410(5) Uani 1 1 d . . .
C15 C 0.8253(4) 0.48716(11) 0.6383(3) 0.0530(6) Uani 1 1 d . . .
H15A H 0.7322 0.5217 0.6002 0.080 Uiso 1 1 calc R . .
H15B H 0.9447 0.4802 0.5913 0.080 Uiso 1 1 calc R . .
H15C H 0.9008 0.4941 0.7330 0.080 Uiso 1 1 calc R . .
C16 C 0.2019(4) 0.13993(10) 0.5919(3) 0.0561(7) Uani 1 1 d . . .
H16A H 0.3235 0.1353 0.6760 0.084 Uiso 1 1 calc R . .
H16B H 0.2726 0.1534 0.5224 0.084 Uiso 1 1 calc R . .
H16C H 0.1242 0.1020 0.5658 0.084 Uiso 1 1 calc R . .
C17 C -0.0971(5) 0.16430(12) 0.7174(3) 0.0590(7) Uani 1 1 d . . .
H17A H -0.2072 0.1941 0.7312 0.089 Uiso 1 1 calc R . .
H17B H 0.0230 0.1575 0.8013 0.089 Uiso 1 1 calc R . .
H17C H -0.1807 0.1274 0.6876 0.089 Uiso 1 1 calc R . .
C18 C -0.1724(5) 0.19409(11) 0.4761(2) 0.0559(7) Uani 1 1 d . . .
H18A H -0.2556 0.1567 0.4514 0.084 Uiso 1 1 calc R . .
H18B H -0.1000 0.2059 0.4062 0.084 Uiso 1 1 calc R . .
H18C H -0.2826 0.2246 0.4864 0.084 Uiso 1 1 calc R . .
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
F1 0.0683(9) 0.0276(6) 0.0593(9) -0.0026(6) 0.0205(7) 0.0020(6)
O1 0.0642(10) 0.0357(7) 0.0237(7) -0.0016(6) 0.0114(7) -0.0124(7)
F2 0.1161(14) 0.0444(7) 0.0592(9) -0.0208(7) 0.0567(9) -0.0238(8)
N1 0.0477(10) 0.0294(8) 0.0230(8) -0.0039(6) 0.0103(7) -0.0041(7)
F3 0.0786(11) 0.0553(9) 0.0479(8) -0.0189(7) -0.0070(8) 0.0036(8)
C6 0.0349(10) 0.0281(9) 0.0285(9) -0.0028(7) 0.0061(8) -0.0011(8)
C7 0.0363(10) 0.0283(9) 0.0264(9) 0.0003(7) 0.0061(8) 0.0016(8)
C8 0.0413(11) 0.0286(9) 0.0266(9) 0.0022(7) 0.0123(8) 0.0009(8)
C9 0.0476(12) 0.0354(10) 0.0303(10) -0.0035(8) 0.0162(9) 0.0023(9)
C10 0.0373(11) 0.0337(10) 0.0393(11) 0.0022(9) 0.0105(9) -0.0014(8)
C11 0.0377(10) 0.0271(9) 0.0253(9) 0.0015(7) 0.0068(8) 0.0008(8)
C12 0.0400(11) 0.0280(9) 0.0266(9) 0.0016(7) 0.0072(8) 0.0024(8)
C13 0.0459(12) 0.0434(11) 0.0431(12) 0.0027(10) 0.0228(10) -0.0012(10)
C14 0.0564(14) 0.0304(10) 0.0376(11) -0.0021(9) 0.0152(10) -0.0047(9)
C15 0.0517(14) 0.0467(13) 0.0655(17) -0.0029(12) 0.0240(13) -0.0124(11)
C16 0.0483(14) 0.0314(11) 0.088(2) -0.0099(12) 0.0180(14) 0.0019(10)
C17 0.0725(18) 0.0605(15) 0.0494(14) -0.0136(12) 0.0258(13) -0.0347(14)
C18 0.0612(16) 0.0419(12) 0.0488(14) 0.0036(11) -0.0119(12) -0.0112(11)
_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
F1 C14 1.346(2) . ?
O1 C7 1.227(2) . ?
F2 C14 1.330(3) . ?
N1 C7 1.362(2) . ?
N1 C11 1.419(2) . ?
N1 H1 0.87(2) . ?
F3 C14 1.348(3) . ?
C6 C17 1.522(3) . ?
C6 C18 1.523(3) . ?
C6 C16 1.528(3) . ?
C6 C7 1.537(3) . ?
C8 C11 1.391(3) . ?
C8 C12 1.394(3) . ?
C8 H8 0.9300 . ?
C9 C13 1.384(3) . ?
C9 C11 1.387(3) . ?
C9 H9 0.9300 . ?
C10 C13 1.389(3) . ?
C10 C12 1.395(3) . ?
C10 C15 1.514(3) . ?
C12 C14 1.497(3) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
C7 N1 C11 126.34(17) . . ?
C7 N1 H1 117.5(14) . . ?
C11 N1 H1 115.4(14) . . ?
C17 C6 C18 108.64(19) . . ?
C17 C6 C16 109.52(19) . . ?
C18 C6 C16 109.57(19) . . ?
C17 C6 C7 109.10(16) . . ?
C18 C6 C7 112.62(16) . . ?
C16 C6 C7 107.35(17) . . ?
O1 C7 N1 121.78(18) . . ?
O1 C7 C6 122.16(17) . . ?
N1 C7 C6 116.03(16) . . ?
C11 C8 C12 119.75(18) . . ?
C11 C8 H8 120.1 . . ?
C12 C8 H8 120.1 . . ?
C13 C9 C11 120.62(18) . . ?
C13 C9 H9 119.7 . . ?
C11 C9 H9 119.7 . . ?
C13 C10 C12 116.70(19) . . ?
C13 C10 C15 119.65(19) . . ?
C12 C10 C15 123.64(19) . . ?
C9 C11 C8 118.77(18) . . ?
C9 C11 N1 118.58(17) . . ?
C8 C11 N1 122.64(17) . . ?
C8 C12 C10 122.14(18) . . ?
C8 C12 C14 118.06(17) . . ?
C10 C12 C14 119.79(18) . . ?
C9 C13 C10 122.01(19) . . ?
C9 C13 H13 119.0 . . ?
C10 C13 H13 119.0 . . ?
F2 C14 F1 105.59(18) . . ?
F2 C14 F3 106.71(19) . . ?
F1 C14 F3 105.66(17) . . ?
F2 C14 C12 113.01(17) . . ?
F1 C14 C12 112.66(17) . . ?
F3 C14 C12 112.61(19) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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
N1 H1 O1 0.87(2) 2.15(2) 3.002(2) 165(2) 4_565
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.046


data_mx1683-c
_database_code_depnum_ccdc_archive 'CCDC 923887'
#TrackingRef '17625_web_deposit_cif_file_0_ChaoChen_1360299646.chen6.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Cu2 I4 O10, 2(C H4 O)'
_chemical_formula_sum            'C32 H32 Cu2 I4 O12'
_chemical_formula_weight         1243.26
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   9.136(3)
_cell_length_b                   10.351(4)
_cell_length_c                   11.044(4)
_cell_angle_alpha                87.89(3)
_cell_angle_beta                 73.90(2)
_cell_angle_gamma                78.59(2)
_cell_volume                     983.4(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2022
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.5
_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    2.099
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             590
_exptl_absorpt_coefficient_mu    4.277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3143
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      173(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  'Rigaku Saturn 724+'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8041
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4373
_reflns_number_gt                4205
_reflns_threshold_expression     I>2sigma(I)
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_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^)+(0.0400P)^2^+5.0000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4373
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_iucr_refine_instructions_details 
;
TITL mx1683-c in P-1
CELL 0.71073 9.1357 10.3510 11.0445 87.889 73.902 78.590
ZERR 1.00 0.0027 0.0043 0.0044 0.026 0.020 0.024
LATT 1
SFAC C H O Cu I
UNIT 32 32 12 2 4
OMIT -2 55
EQIV $1 2-X, 1-Y, 1-Z
HTAB O5 O6_$1
HTAB O6 O1
L.S. 8
DAMP 1500
ACTA
BOND $H
FMAP 2
PLAN 10
WGHT 0.040000 5.000000
FVAR 0.54480
I1 5 0.782583 0.090012 0.642351 11.00000 0.03435 0.02767 =
0.04490 0.00128 -0.01203 0.00037
I2 5 0.990635 0.249793 0.152862 11.00000 0.03322 0.03509 =
0.03565 -0.00420 0.00453 -0.01466
CU1 4 0.639393 0.527408 0.483019 11.00000 0.01529 0.01174 =
0.02005 -0.00046 -0.00508 -0.00412
O1 3 0.639795 0.427695 0.640804 11.00000 0.02402 0.02780 =
0.02396 0.00477 -0.00848 -0.00947
O2 3 0.402700 0.383611 0.668763 11.00000 0.02883 0.02711 =
0.03385 0.01401 -0.01398 -0.01537
O3 3 0.483941 0.317900 0.414781 11.00000 0.02167 0.01861 =
0.04524 -0.01116 -0.00555 -0.00196
O4 3 0.720712 0.360456 0.388838 11.00000 0.02453 0.01700 =
0.02732 -0.00392 -0.00495 -0.00631
O5 3 0.853597 0.584581 0.466267 11.00000 0.01864 0.02923 =
0.03425 -0.00338 -0.00416 -0.01055
AFIX 3
H5A 2 0.932236 0.568213 0.406968 11.00000 -1.20000
AFIX 0
O6 3 0.886002 0.469715 0.730204 11.00000 0.03452 0.06351 =
0.03233 0.00910 -0.01612 -0.02278
AFIX 147
H6 2 0.814540 0.454603 0.705017 11.00000 -1.50000
AFIX 0
C1 1 0.525885 0.376033 0.699122 11.00000 0.02462 0.01692 =
0.01916 -0.00018 -0.00597 -0.00580
C2 1 0.537957 0.300652 0.815388 11.00000 0.02703 0.02008 =
0.02375 0.00470 -0.00983 -0.00907
C3 1 0.639101 0.179934 0.813006 11.00000 0.02717 0.02621 =
0.03549 0.01051 -0.01376 -0.00958
C4 1 0.641688 0.113259 0.924782 11.00000 0.04586 0.03327 =
0.04616 0.02134 -0.02776 -0.01947
AFIX 43
H4 2 0.706200 0.031229 0.922758 11.00000 -1.20000
AFIX 0
C5 1 0.548505 0.169307 1.037894 11.00000 0.06623 0.05735 =
0.02879 0.02240 -0.02333 -0.03058
AFIX 43
H5B 2 0.553610 0.126889 1.112745 11.00000 -1.20000
AFIX 0
C6 1 0.447563 0.288041 1.040915 11.00000 0.07331 0.06130 =
0.02116 0.00431 -0.01251 -0.02548
AFIX 43
H6A 2 0.383774 0.324144 1.117916 11.00000 -1.20000
AFIX 0
C7 1 0.439718 0.354269 0.931201 11.00000 0.04759 0.03789 =
0.02436 0.00481 -0.00639 -0.01068
AFIX 43
H7 2 0.369982 0.433611 0.934135 11.00000 -1.20000
AFIX 0
C8 1 0.629290 0.289718 0.376629 11.00000 0.02498 0.01193 =
0.01694 0.00010 -0.00586 -0.00291
C9 1 0.695290 0.156166 0.313358 11.00000 0.02658 0.01480 =
0.01880 0.00013 -0.00820 -0.00567
C10 1 0.837303 0.121078 0.224021 11.00000 0.02424 0.01821 =
0.02616 -0.00214 -0.00541 -0.00684
C11 1 0.885955 -0.007643 0.173580 11.00000 0.02660 0.02714 =
0.03395 -0.01015 -0.00605 0.00034
AFIX 43
H11 2 0.981280 -0.031214 0.113577 11.00000 -1.20000
AFIX 0
C12 1 0.791698 -0.100119 0.213250 11.00000 0.04019 0.01952 =
0.04024 -0.01441 -0.01091 0.00051
AFIX 43
H12 2 0.823565 -0.184962 0.178516 11.00000 -1.20000
AFIX 0
C13 1 0.652691 -0.067127 0.302859 11.00000 0.03465 0.01600 =
0.03759 -0.00080 -0.00911 -0.00707
AFIX 43
H13 2 0.591738 -0.130141 0.330997 11.00000 -1.20000
AFIX 0
C14 1 0.602545 0.060584 0.351856 11.00000 0.02783 0.01495 =
0.02337 0.00067 -0.00451 -0.00199
AFIX 43
H14 2 0.506341 0.083275 0.410929 11.00000 -1.20000
AFIX 0
C15 1 0.871020 0.701890 0.520187 11.00000 0.03769 0.03008 =
0.05486 0.00353 -0.02263 -0.01863
AFIX 137
H15A 2 0.856749 0.774160 0.464882 11.00000 -1.50000
H15B 2 0.973189 0.689907 0.531699 11.00000 -1.50000
H15C 2 0.794843 0.720514 0.600250 11.00000 -1.50000
AFIX 0
C16 1 0.889746 0.400553 0.840784 11.00000 0.05229 0.04706 =
0.03642 0.00453 -0.01843 -0.00859
AFIX 137
H16A 2 0.975238 0.416231 0.868940 11.00000 -1.50000
H16B 2 0.902272 0.307961 0.824573 11.00000 -1.50000
H16C 2 0.794299 0.429972 0.904774 11.00000 -1.50000
HKLF 4
REM mx1683-c in P-1
REM R1 = 0.0488 for 4205 Fo > 4sig(Fo) and 0.0509 for all 4373 data
REM 229 parameters refined using 0 restraints
END
;
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
I1 I 0.78258(3) 0.09001(2) 0.64235(2) 0.03635(6) Uani 1 1 d . . .
I2 I 0.99063(3) 0.24979(2) 0.15286(2) 0.03625(6) Uani 1 1 d . . .
Cu1 Cu 0.63939(4) 0.52741(3) 0.48302(3) 0.01542(7) Uani 1 1 d . . .
O1 O 0.6398(2) 0.4277(2) 0.6408(2) 0.0244(5) Uani 1 1 d . . .
O2 O 0.4027(3) 0.3836(2) 0.6688(2) 0.0278(5) Uani 1 1 d . . .
O3 O 0.4839(3) 0.3179(2) 0.4148(2) 0.0292(6) Uani 1 1 d . . .
O4 O 0.7207(2) 0.3605(2) 0.3888(2) 0.0230(5) Uani 1 1 d . . .
O5 O 0.8536(2) 0.5846(2) 0.4663(2) 0.0271(6) Uani 1 1 d . . .
H5A H 0.9322 0.5682 0.4070 0.032 Uiso 1 1 d R . .
O6 O 0.8860(3) 0.4697(3) 0.7302(2) 0.0404(7) Uani 1 1 d . . .
H6 H 0.8145 0.4546 0.7050 0.061 Uiso 1 1 calc R . .
C1 C 0.5259(3) 0.3760(3) 0.6991(3) 0.0200(6) Uani 1 1 d . . .
C2 C 0.5380(3) 0.3007(3) 0.8154(3) 0.0225(7) Uani 1 1 d . . .
C3 C 0.6391(4) 0.1799(3) 0.8130(3) 0.0282(8) Uani 1 1 d . . .
C4 C 0.6417(4) 0.1133(4) 0.9248(4) 0.0375(9) Uani 1 1 d . . .
H4 H 0.7062 0.0312 0.9228 0.045 Uiso 1 1 calc R . .
C5 C 0.5485(5) 0.1693(4) 1.0379(4) 0.0466(10) Uani 1 1 d . . .
H5B H 0.5536 0.1269 1.1127 0.056 Uiso 1 1 calc R . .
C6 C 0.4476(6) 0.2880(5) 1.0409(4) 0.0504(12) Uani 1 1 d . . .
H6A H 0.3838 0.3241 1.1179 0.060 Uiso 1 1 calc R . .
C7 C 0.4397(5) 0.3543(4) 0.9312(3) 0.0371(10) Uani 1 1 d . . .
H7 H 0.3700 0.4336 0.9341 0.045 Uiso 1 1 calc R . .
C8 C 0.6293(3) 0.2897(3) 0.3766(3) 0.0180(6) Uani 1 1 d . . .
C9 C 0.6953(3) 0.1562(3) 0.3134(3) 0.0194(6) Uani 1 1 d . . .
C10 C 0.8373(3) 0.1211(3) 0.2240(3) 0.0227(7) Uani 1 1 d . . .
C11 C 0.8860(4) -0.0076(3) 0.1736(3) 0.0302(8) Uani 1 1 d . . .
H11 H 0.9813 -0.0312 0.1136 0.036 Uiso 1 1 calc R . .
C12 C 0.7917(4) -0.1001(3) 0.2133(4) 0.0339(9) Uani 1 1 d . . .
H12 H 0.8236 -0.1850 0.1785 0.041 Uiso 1 1 calc R . .
C13 C 0.6527(4) -0.0671(3) 0.3029(3) 0.0292(8) Uani 1 1 d . . .
H13 H 0.5917 -0.1301 0.3310 0.035 Uiso 1 1 calc R . .
C14 C 0.6025(4) 0.0606(3) 0.3519(3) 0.0229(7) Uani 1 1 d . . .
H14 H 0.5063 0.0833 0.4109 0.027 Uiso 1 1 calc R . .
C15 C 0.8710(4) 0.7019(4) 0.5202(4) 0.0372(9) Uani 1 1 d . . .
H15A H 0.8567 0.7742 0.4649 0.056 Uiso 1 1 calc R . .
H15B H 0.9732 0.6899 0.5317 0.056 Uiso 1 1 calc R . .
H15C H 0.7948 0.7205 0.6002 0.056 Uiso 1 1 calc R . .
C16 C 0.8897(5) 0.4006(4) 0.8408(4) 0.0442(11) Uani 1 1 d . . .
H16A H 0.9752 0.4162 0.8689 0.066 Uiso 1 1 calc R . .
H16B H 0.9023 0.3080 0.8246 0.066 Uiso 1 1 calc R . .
H16C H 0.7943 0.4300 0.9048 0.066 Uiso 1 1 calc R . .
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
I1 0.03435(11) 0.02767(11) 0.04490(13) 0.00128(9) -0.01203(9) 0.00037(9)
I2 0.03322(10) 0.03509(11) 0.03565(12) -0.00420(9) 0.00453(9) -0.01466(9)
Cu1 0.01529(13) 0.01174(14) 0.02005(15) -0.00046(11) -0.00508(11) -0.00412(11)
O1 0.0240(9) 0.0278(10) 0.0240(10) 0.0048(8) -0.0085(8) -0.0095(8)
O2 0.0288(9) 0.0271(10) 0.0338(11) 0.0140(9) -0.0140(8) -0.0154(8)
O3 0.0217(9) 0.0186(10) 0.0452(13) -0.0112(9) -0.0055(9) -0.0020(8)
O4 0.0245(9) 0.0170(9) 0.0273(10) -0.0039(8) -0.0050(8) -0.0063(8)
O5 0.0186(9) 0.0292(10) 0.0343(12) -0.0034(9) -0.0042(8) -0.0106(8)
O6 0.0345(11) 0.0635(16) 0.0323(12) 0.0091(11) -0.0161(9) -0.0228(11)
C1 0.0246(12) 0.0169(12) 0.0192(12) -0.0002(10) -0.0060(10) -0.0058(10)
C2 0.0270(12) 0.0201(12) 0.0237(13) 0.0047(10) -0.0098(11) -0.0091(10)
C3 0.0272(13) 0.0262(14) 0.0355(16) 0.0105(12) -0.0138(12) -0.0096(11)
C4 0.0459(16) 0.0333(16) 0.0462(18) 0.0213(14) -0.0278(14) -0.0195(13)
C5 0.066(2) 0.057(2) 0.0288(16) 0.0224(15) -0.0233(15) -0.0306(18)
C6 0.073(3) 0.061(3) 0.0212(17) 0.0043(17) -0.0125(17) -0.025(2)
C7 0.0476(19) 0.0379(18) 0.0244(16) 0.0048(14) -0.0064(14) -0.0107(16)
C8 0.0250(12) 0.0119(11) 0.0169(12) 0.0001(9) -0.0059(10) -0.0029(10)
C9 0.0266(12) 0.0148(11) 0.0188(12) 0.0001(10) -0.0082(10) -0.0057(10)
C10 0.0242(12) 0.0182(12) 0.0262(14) -0.0021(11) -0.0054(11) -0.0068(10)
C11 0.0266(14) 0.0271(15) 0.0340(17) -0.0101(13) -0.0060(13) 0.0003(12)
C12 0.0402(17) 0.0195(14) 0.0402(18) -0.0144(13) -0.0109(14) 0.0005(13)
C13 0.0346(15) 0.0160(13) 0.0376(17) -0.0008(12) -0.0091(13) -0.0071(11)
C14 0.0278(13) 0.0150(12) 0.0234(14) 0.0007(11) -0.0045(11) -0.0020(11)
C15 0.0377(14) 0.0301(15) 0.055(2) 0.0035(14) -0.0226(14) -0.0186(12)
C16 0.052(2) 0.047(2) 0.0364(19) 0.0045(17) -0.0184(16) -0.0086(18)
_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
I1 C3 2.101(3) . ?
I2 C10 2.099(3) . ?
Cu1 O4 1.954(2) . ?
Cu1 O3 1.955(2) 2_666 ?
Cu1 O2 1.977(3) 2_666 ?
Cu1 O1 1.993(2) . ?
Cu1 O5 2.113(2) . ?
Cu1 Cu1 2.6412(10) 2_666 ?
O1 C1 1.268(4) . ?
O2 C1 1.248(4) . ?
O3 C8 1.254(4) . ?
O4 C8 1.250(4) . ?
O5 C15 1.427(4) . ?
O5 H5A 0.8203 . ?
O6 C16 1.398(5) . ?
O6 H6 0.8200 . ?
C1 C2 1.497(4) . ?
C2 C3 1.396(4) . ?
C2 C7 1.403(5) . ?
C3 C4 1.396(5) . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(7) . ?
C5 H5B 0.9300 . ?
C6 C7 1.382(6) . ?
C6 H6A 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.507(4) . ?
C9 C10 1.385(4) . ?
C9 C14 1.407(4) . ?
C10 C11 1.402(4) . ?
C11 C12 1.391(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
O4 Cu1 O3 167.86(10) . 2_666 ?
O4 Cu1 O2 90.44(10) . 2_666 ?
O3 Cu1 O2 89.53(11) 2_666 2_666 ?
O4 Cu1 O1 88.42(10) . . ?
O3 Cu1 O1 89.15(11) 2_666 . ?
O2 Cu1 O1 168.30(10) 2_666 . ?
O4 Cu1 O5 97.97(9) . . ?
O3 Cu1 O5 94.09(10) 2_666 . ?
O2 Cu1 O5 97.13(10) 2_666 . ?
O1 Cu1 O5 94.56(10) . . ?
O4 Cu1 Cu1 86.72(7) . 2_666 ?
O3 Cu1 Cu1 81.21(8) 2_666 2_666 ?
O2 Cu1 Cu1 83.42(7) 2_666 2_666 ?
O1 Cu1 Cu1 84.89(7) . 2_666 ?
O5 Cu1 Cu1 175.27(7) . 2_666 ?
C1 O1 Cu1 121.5(2) . . ?
C1 O2 Cu1 124.5(2) . 2_666 ?
C8 O3 Cu1 126.1(2) . 2_666 ?
C8 O4 Cu1 119.77(18) . . ?
C15 O5 Cu1 124.98(19) . . ?
C15 O5 H5A 102.7 . . ?
Cu1 O5 H5A 126.9 . . ?
C16 O6 H6 109.5 . . ?
O2 C1 O1 125.6(3) . . ?
O2 C1 C2 116.7(3) . . ?
O1 C1 C2 117.8(3) . . ?
C3 C2 C7 119.3(3) . . ?
C3 C2 C1 123.2(3) . . ?
C7 C2 C1 117.5(3) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 I1 118.4(2) . . ?
C2 C3 I1 121.3(2) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5B 119.8 . . ?
C6 C5 H5B 119.8 . . ?
C5 C6 C7 121.0(4) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C6 C7 C2 119.4(4) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
O4 C8 O3 126.0(3) . . ?
O4 C8 C9 118.8(3) . . ?
O3 C8 C9 115.1(3) . . ?
C10 C9 C14 118.8(3) . . ?
C10 C9 C8 125.7(3) . . ?
C14 C9 C8 115.5(2) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 I2 124.5(2) . . ?
C11 C10 I2 115.5(2) . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
O5 H5A O6 0.82 1.90 2.717(3) 180.0 2_766
O6 H6 O1 0.82 1.99 2.806(4) 177.0 .
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         1.037
_refine_diff_density_min         -1.624
_refine_diff_density_rms         0.182


data_try
_database_code_depnum_ccdc_archive 'CCDC 929074'
#TrackingRef '18536_web_deposit_cif_file_0_ShangjunCai_1363226207.csj-3c.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C13H16F3NO2
_chemical_formula_sum            'C13 H16 F3 N O2'
_chemical_formula_weight         275.27
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'
_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   12.572(3)
_cell_length_b                   13.249(3)
_cell_length_c                   18.106(4)
_cell_angle_alpha                81.11(3)
_cell_angle_beta                 75.27(3)
_cell_angle_gamma                73.23(3)
_cell_volume                     2782.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8416
_cell_measurement_theta_min      1.61
_cell_measurement_theta_max      27.48
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          .849
_exptl_crystal_size_mid          .232
_exptl_crystal_size_min          .215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  .9090
_exptl_absorpt_correction_T_max  .9758
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      173(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36225
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.48
_reflns_number_total             12721
_reflns_number_gt                10132
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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^)+(0.1347P)^2^+1.1033P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         12721
_refine_ls_number_parameters     685
_refine_ls_number_restraints     6
_refine_ls_R_factor_ref          0.1112
_refine_ls_R_factor_gt           0.0868
_refine_ls_wR_factor_ref         0.2775
_refine_ls_wR_factor_gt          0.2448
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0.000
_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
C8 C 0.8004(3) 0.7968(2) 1.00229(16) 0.0341(6) Uani 1 1 d . . .
C2 C 0.6671(3) 0.6237(2) 0.96431(17) 0.0390(7) Uani 1 1 d . . .
C1 C 0.7499(3) 0.6325(2) 0.99992(16) 0.0331(6) Uani 1 1 d . . .
C6 C 0.8415(3) 0.5461(2) 1.00540(17) 0.0383(7) Uani 1 1 d . . .
H6A H 0.8998 0.5521 1.0278 0.046 Uiso 1 1 calc R . .
C9 C 0.7665(3) 0.8992(2) 1.04181(17) 0.0360(6) Uani 1 1 d . . .
C4 C 0.7667(3) 0.4425(2) 0.94513(19) 0.0450(8) Uani 1 1 d . . .
C5 C 0.8499(3) 0.4511(2) 0.97887(19) 0.0448(8) Uani 1 1 d . . .
H5A H 0.9127 0.3921 0.9839 0.054 Uiso 1 1 calc R . .
C3 C 0.6762(3) 0.5286(3) 0.9371(2) 0.0475(8) Uani 1 1 d . . .
H3A H 0.6198 0.5227 0.9129 0.057 Uiso 1 1 calc R . .
C10 C 0.7656(3) 0.8772(3) 1.12725(19) 0.0469(8) Uani 1 1 d . . .
H10A H 0.7107 0.8361 1.1521 0.070 Uiso 1 1 calc R . .
H10B H 0.7439 0.9443 1.1505 0.070 Uiso 1 1 calc R . .
H10C H 0.8418 0.8370 1.1340 0.070 Uiso 1 1 calc R . .
C12 C 0.8509(5) 0.9646(3) 1.0037(2) 0.0744(14) Uani 1 1 d . . .
H12A H 0.9273 0.9251 1.0104 0.112 Uiso 1 1 calc R . .
H12B H 0.8282 1.0316 1.0274 0.112 Uiso 1 1 calc R . .
H12C H 0.8515 0.9792 0.9489 0.112 Uiso 1 1 calc R . .
C7 C 0.5656(3) 0.7152(3) 0.9575(2) 0.0514(8) Uani 1 1 d . . .
C34 C 0.5503(2) 0.6398(2) 0.23393(15) 0.0301(6) Uani 1 1 d . . .
C27 C 0.5038(3) 0.8015(2) 0.29453(16) 0.0327(6) Uani 1 1 d . . .
C30 C 0.5398(3) 0.9985(2) 0.29693(18) 0.0383(7) Uani 1 1 d . . .
C29 C 0.4603(3) 0.9906(2) 0.26013(19) 0.0389(7) Uani 1 1 d . . .
H29A H 0.4184 1.0519 0.2352 0.047 Uiso 1 1 calc R . .
C36 C 0.5886(3) 0.4829(3) 0.16082(19) 0.0461(8) Uani 1 1 d . . .
H36A H 0.5731 0.4142 0.1621 0.069 Uiso 1 1 calc R . .
H36B H 0.6707 0.4730 0.1543 0.069 Uiso 1 1 calc R . .
H36C H 0.5625 0.5298 0.1179 0.069 Uiso 1 1 calc R . .
C35 C 0.5258(2) 0.5321(2) 0.23570(16) 0.0329(6) Uani 1 1 d . . .
C28 C 0.4408(2) 0.8917(2) 0.25938(18) 0.0359(6) Uani 1 1 d . . .
C37 C 0.3977(3) 0.5470(3) 0.2448(2) 0.0455(8) Uani 1 1 d . . .
H37A H 0.3829 0.4781 0.2455 0.068 Uiso 1 1 calc R . .
H37B H 0.3722 0.5940 0.2018 0.068 Uiso 1 1 calc R . .
H37C H 0.3563 0.5783 0.2930 0.068 Uiso 1 1 calc R . .
C38 C 0.5679(3) 0.4600(2) 0.3023(2) 0.0468(8) Uani 1 1 d . . .
H38A H 0.5535 0.3907 0.3038 0.070 Uiso 1 1 calc R . .
H38B H 0.5274 0.4916 0.3505 0.070 Uiso 1 1 calc R . .
H38C H 0.6498 0.4513 0.2953 0.070 Uiso 1 1 calc R . .
C31 C 0.6005(3) 0.9094(3) 0.3339(2) 0.0448(8) Uani 1 1 d . . .
H31A H 0.6539 0.9153 0.3609 0.054 Uiso 1 1 calc R . .
C32 C 0.5829(3) 0.8127(2) 0.33125(18) 0.0426(7) Uani 1 1 d . . .
H32A H 0.6265 0.7516 0.3554 0.051 Uiso 1 1 calc R . .
C33 C 0.3520(3) 0.8854(3) 0.2204(2) 0.0516(9) Uani 1 1 d . . .
C14 C 0.2737(2) 0.7783(2) 0.51569(15) 0.0295(5) Uani 1 1 d . . .
C15 C 0.2043(2) 0.8618(2) 0.48018(17) 0.0328(6) Uani 1 1 d . . .
C16 C 0.2287(3) 0.9602(2) 0.46257(18) 0.0350(6) Uani 1 1 d . . .
H16A H 0.1804 1.0175 0.4385 0.042 Uiso 1 1 calc R . .
C19 C 0.3688(2) 0.7934(2) 0.53307(17) 0.0352(6) Uani 1 1 d . . .
H19A H 0.4177 0.7362 0.5569 0.042 Uiso 1 1 calc R . .
C21 C 0.2863(3) 0.6014(2) 0.48899(16) 0.0354(6) Uani 1 1 d . . .
C17 C 0.3243(2) 0.9733(2) 0.48058(17) 0.0319(6) Uani 1 1 d . . .
C18 C 0.3935(2) 0.8905(2) 0.51610(18) 0.0366(6) Uani 1 1 d . . .
H18A H 0.4584 0.9001 0.5290 0.044 Uiso 1 1 calc R . .
C22 C 0.2469(3) 0.4995(2) 0.51418(18) 0.0423(7) Uani 1 1 d . . .
C20 C 0.0979(3) 0.8494(3) 0.4631(2) 0.0472(8) Uani 1 1 d . . .
C23 C 0.1855(5) 0.4905(4) 0.5964(3) 0.0883(17) Uani 1 1 d U . .
H23A H 0.1159 0.5485 0.6051 0.132 Uiso 1 1 calc R . .
H23B H 0.2348 0.4945 0.6293 0.132 Uiso 1 1 calc R . .
H23C H 0.1656 0.4226 0.6086 0.132 Uiso 1 1 calc R . .
C25 C 0.3551(4) 0.4062(3) 0.5017(3) 0.0693(12) Uani 1 1 d . . .
H25A H 0.3336 0.3392 0.5171 0.104 Uiso 1 1 calc R . .
H25B H 0.4064 0.4118 0.5326 0.104 Uiso 1 1 calc R . .
H25C H 0.3937 0.4083 0.4473 0.104 Uiso 1 1 calc R . .
C41 C 0.0735(2) 0.4205(2) 0.23778(16) 0.0311(6) Uani 1 1 d . . .
C40 C -0.0121(2) 0.4045(2) 0.20949(15) 0.0309(6) Uani 1 1 d . . .
C42 C 0.0752(3) 0.5228(2) 0.24710(18) 0.0379(6) Uani 1 1 d . . .
H42A H 0.1354 0.5338 0.2650 0.045 Uiso 1 1 calc R . .
C47 C -0.0864(2) 0.2507(2) 0.25092(15) 0.0298(5) Uani 1 1 d . . .
C44 C -0.0991(3) 0.5920(2) 0.20318(19) 0.0411(7) Uani 1 1 d . . .
H44A H -0.1591 0.6506 0.1921 0.049 Uiso 1 1 calc R . .
C45 C -0.0984(3) 0.4906(2) 0.19262(18) 0.0394(7) Uani 1 1 d . . .
H45A H -0.1578 0.4799 0.1736 0.047 Uiso 1 1 calc R . .
C48 C -0.0843(3) 0.1401(2) 0.23409(17) 0.0355(6) Uani 1 1 d . . .
C43 C -0.0117(3) 0.6077(2) 0.23001(18) 0.0395(7) Uani 1 1 d . . .
C51 C 0.0368(3) 0.0696(3) 0.2234(2) 0.0524(9) Uani 1 1 d . . .
H51A H 0.0635 0.0623 0.2708 0.079 Uiso 1 1 calc R . .
H51B H 0.0867 0.1013 0.1814 0.079 Uiso 1 1 calc R . .
H51C H 0.0381 -0.0004 0.2112 0.079 Uiso 1 1 calc R . .
C46 C 0.1620(3) 0.3284(2) 0.2617(2) 0.0432(7) Uani 1 1 d . . .
C49 C -0.1613(3) 0.0919(3) 0.3009(2) 0.0519(9) Uani 1 1 d . . .
H49A H -0.1324 0.0839 0.3475 0.078 Uiso 1 1 calc R . .
H49B H -0.1621 0.0224 0.2892 0.078 Uiso 1 1 calc R . .
H49C H -0.2388 0.1384 0.3089 0.078 Uiso 1 1 calc R . .
C50 C -0.1275(4) 0.1518(3) 0.1602(2) 0.0546(9) Uani 1 1 d . . .
H50A H -0.0773 0.1825 0.1177 0.082 Uiso 1 1 calc R . .
H50B H -0.2051 0.1981 0.1673 0.082 Uiso 1 1 calc R . .
H50C H -0.1276 0.0820 0.1485 0.082 Uiso 1 1 calc R . .
N4 N -0.0155(2) 0.30016(19) 0.19957(14) 0.0347(5) Uani 1 1 d . . .
H4A H 0.0293 0.2681 0.1595 0.042 Uiso 1 1 calc R . .
N3 N 0.2469(2) 0.67913(18) 0.53618(13) 0.0324(5) Uani 1 1 d . . .
H3B H 0.2029 0.6684 0.5814 0.039 Uiso 1 1 calc R . .
N2 N 0.4888(2) 0.69963(18) 0.29171(14) 0.0353(5) Uani 1 1 d . . .
H2A H 0.4388 0.6755 0.3282 0.042 Uiso 1 1 calc R . .
N1 N 0.7371(2) 0.72750(18) 1.03267(14) 0.0339(5) Uani 1 1 d . . .
H1A H 0.6850 0.7418 1.0752 0.041 Uiso 1 1 calc R . .
O5 O 0.62234(19) 0.66967(17) 0.18246(12) 0.0409(5) Uani 1 1 d . . .
O7 O -0.15032(19) 0.29326(17) 0.30741(12) 0.0414(5) Uani 1 1 d . . .
O3 O 0.3506(2) 0.61179(17) 0.42619(13) 0.0490(6) Uani 1 1 d . . .
O1 O 0.8783(2) 0.77883(19) 0.94594(14) 0.0594(7) Uani 1 1 d . . .
F3 F 0.5948(2) 0.80190(16) 0.91923(13) 0.0638(6) Uani 1 1 d . . .
F1 F 0.50146(19) 0.7440(2) 1.02564(14) 0.0667(6) Uani 1 1 d . . .
F2 F 0.4954(2) 0.6939(2) 0.92058(18) 0.0848(9) Uani 1 1 d . . .
F7 F 0.3898(2) 0.82174(19) 0.16516(15) 0.0682(7) Uani 1 1 d . . .
F9 F 0.26814(19) 0.8506(2) 0.27019(18) 0.0816(8) Uani 1 1 d . . .
F8 F 0.3020(2) 0.98033(19) 0.18878(19) 0.0810(9) Uani 1 1 d . . .
F6 F 0.0429(2) 0.93593(17) 0.42653(15) 0.0665(7) Uani 1 1 d . . .
F4 F 0.1192(2) 0.77061(18) 0.41907(15) 0.0687(7) Uani 1 1 d . . .
F5 F 0.02336(17) 0.82827(18) 0.52681(15) 0.0650(6) Uani 1 1 d . . .
F11 F 0.11643(19) 0.26763(17) 0.32071(14) 0.0600(6) Uani 1 1 d . . .
F10 F 0.21943(19) 0.26474(17) 0.20747(15) 0.0657(6) Uani 1 1 d . . .
F12 F 0.24029(19) 0.35758(17) 0.28652(17) 0.0716(7) Uani 1 1 d . . .
C24 C 0.1770(4) 0.4931(3) 0.4594(3) 0.0750(14) Uani 1 1 d . . .
H24A H 0.1073 0.5511 0.4658 0.113 Uiso 1 1 calc R . .
H24B H 0.1571 0.4253 0.4702 0.113 Uiso 1 1 calc R . .
H24C H 0.2214 0.4988 0.4067 0.113 Uiso 1 1 calc R . .
C11 C 0.6475(4) 0.9613(3) 1.0325(3) 0.0804(15) Uani 1 1 d . . .
H11A H 0.5934 0.9190 1.0566 0.121 Uiso 1 1 calc R . .
H11B H 0.6473 0.9775 0.9779 0.121 Uiso 1 1 calc R . .
H11C H 0.6251 1.0274 1.0572 0.121 Uiso 1 1 calc R . .
O4 O 0.35486(19) 1.06720(16) 0.46736(14) 0.0433(5) Uani 1 1 d . . .
O6 O 0.5643(2) 1.09132(17) 0.30073(15) 0.0512(6) Uani 1 1 d . . .
O8 O -0.0206(2) 0.71056(17) 0.23886(16) 0.0545(7) Uani 1 1 d . . .
O2 O 0.7649(3) 0.35255(19) 0.91712(16) 0.0647(8) Uani 1 1 d . . .
C26 C 0.2882(3) 1.1536(3) 0.4285(3) 0.0572(10) Uani 1 1 d . . .
H26A H 0.3183 1.2154 0.4231 0.086 Uiso 1 1 calc R . .
H26B H 0.2092 1.1701 0.4579 0.086 Uiso 1 1 calc R . .
H26C H 0.2910 1.1350 0.3776 0.086 Uiso 1 1 calc R . .
C52 C 0.0632(5) 0.7294(3) 0.2713(3) 0.0757(15) Uani 1 1 d . . .
H52A H 0.0482 0.8055 0.2747 0.114 Uiso 1 1 calc R . .
H52B H 0.1389 0.7034 0.2387 0.114 Uiso 1 1 calc R . .
H52C H 0.0601 0.6923 0.3226 0.114 Uiso 1 1 calc R . .
C39 C 0.5271(4) 1.1786(3) 0.2483(3) 0.0648(11) Uani 1 1 d . . .
H39A H 0.5501 1.2398 0.2567 0.097 Uiso 1 1 calc R . .
H39B H 0.4440 1.1963 0.2564 0.097 Uiso 1 1 calc R . .
H39C H 0.5618 1.1597 0.1956 0.097 Uiso 1 1 calc R . .
C13 C 0.8413(5) 0.2571(3) 0.9362(3) 0.0858(17) Uani 1 1 d . . .
H13A H 0.8317 0.1996 0.9125 0.129 Uiso 1 1 calc R . .
H13B H 0.8259 0.2416 0.9921 0.129 Uiso 1 1 calc R . .
H13C H 0.9195 0.2636 0.9175 0.129 Uiso 1 1 calc R . .
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
C8 0.0414(16) 0.0340(13) 0.0245(14) -0.0057(11) 0.0029(12) -0.0132(12)
C2 0.0527(18) 0.0423(15) 0.0266(15) -0.0045(12) -0.0066(13) -0.0207(14)
C1 0.0423(16) 0.0368(13) 0.0210(13) -0.0049(11) 0.0024(11) -0.0183(12)
C6 0.0447(17) 0.0432(15) 0.0290(15) -0.0063(12) -0.0009(13) -0.0191(13)
C9 0.0482(17) 0.0327(13) 0.0259(14) -0.0046(11) 0.0001(12) -0.0151(12)
C4 0.072(2) 0.0380(15) 0.0301(16) -0.0058(12) -0.0046(15) -0.0270(15)
C5 0.060(2) 0.0356(14) 0.0355(17) -0.0047(13) -0.0027(15) -0.0127(14)
C3 0.065(2) 0.0494(17) 0.0361(18) -0.0084(14) -0.0144(16) -0.0229(16)
C10 0.073(2) 0.0405(15) 0.0310(16) -0.0083(13) -0.0044(15) -0.0241(16)
C12 0.125(4) 0.054(2) 0.046(2) -0.0148(17) 0.023(2) -0.058(2)
C7 0.059(2) 0.0561(19) 0.047(2) -0.0090(16) -0.0224(17) -0.0141(17)
C34 0.0314(13) 0.0393(13) 0.0212(13) -0.0014(11) -0.0011(10) -0.0166(11)
C27 0.0422(16) 0.0342(13) 0.0214(13) -0.0082(10) 0.0053(11) -0.0171(12)
C30 0.0468(17) 0.0348(13) 0.0334(16) -0.0048(12) -0.0007(13) -0.0172(12)
C29 0.0350(15) 0.0335(13) 0.0441(18) -0.0088(12) -0.0022(13) -0.0054(11)
C36 0.0518(19) 0.0560(18) 0.0370(17) -0.0203(15) 0.0072(14) -0.0306(16)
C35 0.0387(15) 0.0396(14) 0.0245(14) -0.0081(11) 0.0002(11) -0.0200(12)
C28 0.0296(14) 0.0415(15) 0.0348(16) -0.0126(12) 0.0020(12) -0.0100(12)
C37 0.0442(18) 0.0565(18) 0.0455(19) -0.0133(15) -0.0026(15) -0.0297(15)
C38 0.063(2) 0.0358(14) 0.0399(18) -0.0042(13) -0.0109(16) -0.0107(14)
C31 0.059(2) 0.0473(16) 0.0390(18) 0.0008(14) -0.0203(16) -0.0253(15)
C32 0.064(2) 0.0391(15) 0.0306(16) 0.0057(12) -0.0175(15) -0.0204(14)
C33 0.0358(17) 0.0473(17) 0.072(3) -0.0147(17) -0.0132(17) -0.0045(14)
C14 0.0319(14) 0.0312(12) 0.0227(13) -0.0067(10) 0.0017(10) -0.0083(10)
C15 0.0359(15) 0.0363(13) 0.0300(15) -0.0073(11) -0.0081(12) -0.0124(11)
C16 0.0375(15) 0.0328(13) 0.0365(16) -0.0030(12) -0.0129(13) -0.0081(11)
C19 0.0322(14) 0.0374(14) 0.0336(15) -0.0018(12) -0.0072(12) -0.0063(11)
C21 0.0435(16) 0.0365(13) 0.0228(14) -0.0058(11) 0.0059(12) -0.0152(12)
C17 0.0347(14) 0.0337(13) 0.0298(14) -0.0056(11) -0.0043(11) -0.0138(11)
C18 0.0312(14) 0.0405(14) 0.0405(17) -0.0002(12) -0.0101(12) -0.0132(12)
C22 0.060(2) 0.0382(14) 0.0277(15) -0.0076(12) 0.0082(14) -0.0244(14)
C20 0.055(2) 0.0434(16) 0.053(2) 0.0003(15) -0.0265(17) -0.0181(15)
C23 0.142(4) 0.068(2) 0.054(2) -0.021(2) 0.040(3) -0.071(3)
C25 0.082(3) 0.0419(18) 0.079(3) 0.0100(19) -0.016(2) -0.0181(19)
C41 0.0305(14) 0.0366(13) 0.0258(14) -0.0029(11) -0.0023(11) -0.0115(11)
C40 0.0358(14) 0.0388(13) 0.0188(12) -0.0026(10) 0.0007(10) -0.0170(11)
C42 0.0442(17) 0.0412(15) 0.0332(16) 0.0002(12) -0.0095(13) -0.0197(13)
C47 0.0290(13) 0.0383(13) 0.0223(13) -0.0043(11) -0.0026(10) -0.0111(11)
C44 0.0418(17) 0.0386(14) 0.0401(17) 0.0059(13) -0.0096(14) -0.0105(13)
C45 0.0410(16) 0.0434(15) 0.0356(16) 0.0055(13) -0.0109(13) -0.0163(13)
C48 0.0397(16) 0.0410(14) 0.0270(14) -0.0098(12) 0.0033(12) -0.0181(12)
C43 0.0536(19) 0.0330(13) 0.0329(16) -0.0001(12) -0.0087(14) -0.0153(13)
C51 0.051(2) 0.0398(16) 0.054(2) -0.0034(15) 0.0080(16) -0.0090(14)
C46 0.0371(16) 0.0429(15) 0.053(2) -0.0051(14) -0.0128(15) -0.0128(13)
C49 0.059(2) 0.0504(18) 0.045(2) -0.0080(15) 0.0105(16) -0.0296(16)
C50 0.070(2) 0.069(2) 0.0399(19) -0.0135(17) -0.0123(18) -0.0367(19)
N4 0.0402(13) 0.0403(12) 0.0241(12) -0.0105(10) 0.0053(10) -0.0182(10)
N3 0.0395(13) 0.0346(11) 0.0210(11) -0.0041(9) 0.0047(10) -0.0155(10)
N2 0.0449(14) 0.0358(12) 0.0252(12) -0.0049(9) 0.0066(10) -0.0220(11)
N1 0.0414(13) 0.0355(11) 0.0237(12) -0.0103(9) 0.0057(10) -0.0154(10)
O5 0.0466(12) 0.0469(11) 0.0309(11) -0.0079(9) 0.0063(9) -0.0255(10)
O7 0.0473(12) 0.0452(11) 0.0265(11) -0.0098(9) 0.0106(9) -0.0171(10)
O3 0.0664(15) 0.0433(11) 0.0307(12) -0.0103(9) 0.0184(11) -0.0257(11)
O1 0.0772(18) 0.0546(14) 0.0419(14) -0.0230(11) 0.0310(12) -0.0391(13)
F3 0.0836(16) 0.0464(11) 0.0542(14) 0.0007(10) -0.0191(12) -0.0053(11)
F1 0.0513(13) 0.0864(16) 0.0545(14) -0.0129(12) -0.0066(11) -0.0069(11)
F2 0.0924(19) 0.0801(16) 0.102(2) -0.0143(15) -0.0651(18) -0.0129(14)
F7 0.0700(15) 0.0748(15) 0.0707(16) -0.0271(13) -0.0348(13) -0.0081(12)
F9 0.0451(13) 0.106(2) 0.105(2) -0.0265(17) -0.0030(13) -0.0406(13)
F8 0.0635(15) 0.0628(14) 0.130(3) -0.0102(15) -0.0585(17) -0.0029(11)
F6 0.0660(14) 0.0602(12) 0.0909(18) 0.0134(12) -0.0528(14) -0.0232(11)
F4 0.0947(18) 0.0626(13) 0.0760(17) -0.0108(12) -0.0501(15) -0.0327(12)
F5 0.0404(11) 0.0727(14) 0.0862(18) 0.0079(12) -0.0158(11) -0.0279(10)
F11 0.0580(13) 0.0584(12) 0.0613(14) 0.0212(10) -0.0230(11) -0.0169(10)
F10 0.0497(12) 0.0540(12) 0.0795(17) -0.0177(11) -0.0018(11) 0.0029(10)
F12 0.0552(13) 0.0535(12) 0.121(2) 0.0003(13) -0.0490(14) -0.0159(10)
C24 0.098(3) 0.065(2) 0.085(3) 0.017(2) -0.043(3) -0.049(2)
C11 0.093(3) 0.052(2) 0.097(4) -0.021(2) -0.046(3) 0.010(2)
O4 0.0463(12) 0.0351(10) 0.0556(15) 0.0009(10) -0.0171(11) -0.0188(9)
O6 0.0724(17) 0.0382(11) 0.0544(15) -0.0025(10) -0.0198(13) -0.0276(11)
O8 0.0745(17) 0.0351(11) 0.0618(17) -0.0007(11) -0.0276(14) -0.0174(11)
O2 0.112(2) 0.0417(12) 0.0525(16) -0.0096(11) -0.0229(16) -0.0311(14)
C26 0.062(2) 0.0351(15) 0.079(3) 0.0054(17) -0.028(2) -0.0147(15)
C52 0.120(4) 0.0434(18) 0.089(3) 0.001(2) -0.063(3) -0.029(2)
C39 0.076(3) 0.0309(15) 0.090(3) 0.0019(18) -0.026(2) -0.0149(16)
C13 0.167(5) 0.0350(17) 0.058(3) -0.0036(18) -0.035(3) -0.022(2)
_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
C8 O1 1.220(4) . ?
C8 N1 1.349(4) . ?
C8 C9 1.531(4) . ?
C2 C3 1.386(4) . ?
C2 C1 1.395(4) . ?
C2 C7 1.502(5) . ?
C1 C6 1.382(4) . ?
C1 N1 1.424(3) . ?
C6 C5 1.382(4) . ?
C6 H6A 0.9500 . ?
C9 C11 1.523(5) . ?
C9 C12 1.525(5) . ?
C9 C10 1.527(4) . ?
C4 O2 1.373(4) . ?
C4 C5 1.376(5) . ?
C4 C3 1.379(5) . ?
C5 H5A 0.9500 . ?
C3 H3A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C7 F1 1.334(4) . ?
C7 F3 1.343(4) . ?
C7 F2 1.345(4) . ?
C34 O5 1.229(3) . ?
C34 N2 1.346(4) . ?
C34 C35 1.538(4) . ?
C27 C32 1.381(4) . ?
C27 C28 1.391(4) . ?
C27 N2 1.426(3) . ?
C30 O6 1.366(3) . ?
C30 C29 1.370(4) . ?
C30 C31 1.385(4) . ?
C29 C28 1.404(4) . ?
C29 H29A 0.9500 . ?
C36 C35 1.523(4) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C35 C38 1.524(4) . ?
C35 C37 1.533(4) . ?
C28 C33 1.491(5) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C31 C32 1.372(4) . ?
C31 H31A 0.9500 . ?
C32 H32A 0.9500 . ?
C33 F7 1.314(4) . ?
C33 F9 1.344(5) . ?
C33 F8 1.345(4) . ?
C14 C15 1.381(4) . ?
C14 C19 1.385(4) . ?
C14 N3 1.422(3) . ?
C15 C16 1.396(4) . ?
C15 C20 1.505(4) . ?
C16 C17 1.384(4) . ?
C16 H16A 0.9500 . ?
C19 C18 1.380(4) . ?
C19 H19A 0.9500 . ?
C21 O3 1.230(4) . ?
C21 N3 1.341(4) . ?
C21 C22 1.535(4) . ?
C17 O4 1.374(3) . ?
C17 C18 1.375(4) . ?
C18 H18A 0.9500 . ?
C22 C23 1.496(5) . ?
C22 C24 1.508(5) . ?
C22 C25 1.546(5) . ?
C20 F6 1.331(4) . ?
C20 F4 1.335(4) . ?
C20 F5 1.338(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C41 C40 1.382(4) . ?
C41 C42 1.398(4) . ?
C41 C46 1.488(4) . ?
C40 C45 1.385(4) . ?
C40 N4 1.435(3) . ?
C42 C43 1.382(4) . ?
C42 H42A 0.9500 . ?
C47 O7 1.228(3) . ?
C47 N4 1.348(4) . ?
C47 C48 1.533(4) . ?
C44 C45 1.383(4) . ?
C44 C43 1.385(4) . ?
C44 H44A 0.9500 . ?
C45 H45A 0.9500 . ?
C48 C51 1.521(5) . ?
C48 C49 1.527(4) . ?
C48 C50 1.538(5) . ?
C43 O8 1.367(3) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C46 F10 1.319(4) . ?
C46 F11 1.344(4) . ?
C46 F12 1.349(4) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
N4 H4A 0.8800 . ?
N3 H3B 0.8800 . ?
N2 H2A 0.8800 . ?
N1 H1A 0.8800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O4 C26 1.416(4) . ?
O6 C39 1.426(4) . ?
O8 C52 1.423(5) . ?
O2 C13 1.405(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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 C8 N1 121.4(3) . . ?
O1 C8 C9 122.7(3) . . ?
N1 C8 C9 115.9(2) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 C7 119.4(3) . . ?
C1 C2 C7 120.6(3) . . ?
C6 C1 C2 118.7(3) . . ?
C6 C1 N1 120.9(3) . . ?
C2 C1 N1 120.3(3) . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6A 119.4 . . ?
C1 C6 H6A 119.4 . . ?
C11 C9 C12 109.5(3) . . ?
C11 C9 C10 108.7(3) . . ?
C12 C9 C10 109.2(3) . . ?
C11 C9 C8 108.7(3) . . ?
C12 C9 C8 109.0(3) . . ?
C10 C9 C8 111.8(2) . . ?
O2 C4 C5 125.2(3) . . ?
O2 C4 C3 114.7(3) . . ?
C5 C4 C3 120.1(3) . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F1 C7 F3 106.3(3) . . ?
F1 C7 F2 105.7(3) . . ?
F3 C7 F2 106.1(3) . . ?
F1 C7 C2 112.5(3) . . ?
F3 C7 C2 112.6(3) . . ?
F2 C7 C2 112.9(3) . . ?
O5 C34 N2 121.7(2) . . ?
O5 C34 C35 121.7(2) . . ?
N2 C34 C35 116.6(2) . . ?
C32 C27 C28 118.4(3) . . ?
C32 C27 N2 120.6(3) . . ?
C28 C27 N2 121.1(3) . . ?
O6 C30 C29 123.9(3) . . ?
O6 C30 C31 115.8(3) . . ?
C29 C30 C31 120.3(3) . . ?
C30 C29 C28 119.8(3) . . ?
C30 C29 H29A 120.1 . . ?
C28 C29 H29A 120.1 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C36 C35 C38 109.4(3) . . ?
C36 C35 C37 108.6(2) . . ?
C38 C35 C37 110.7(3) . . ?
C36 C35 C34 109.6(2) . . ?
C38 C35 C34 108.5(2) . . ?
C37 C35 C34 110.0(2) . . ?
C27 C28 C29 120.1(3) . . ?
C27 C28 C33 121.0(3) . . ?
C29 C28 C33 118.9(3) . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C32 C31 C30 119.4(3) . . ?
C32 C31 H31A 120.3 . . ?
C30 C31 H31A 120.3 . . ?
C31 C32 C27 121.9(3) . . ?
C31 C32 H32A 119.0 . . ?
C27 C32 H32A 119.0 . . ?
F7 C33 F9 106.1(3) . . ?
F7 C33 F8 106.1(3) . . ?
F9 C33 F8 106.3(3) . . ?
F7 C33 C28 114.4(3) . . ?
F9 C33 C28 111.2(3) . . ?
F8 C33 C28 112.2(3) . . ?
C15 C14 C19 119.0(2) . . ?
C15 C14 N3 120.9(3) . . ?
C19 C14 N3 120.1(3) . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 C20 120.3(3) . . ?
C16 C15 C20 118.9(3) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16A 120.4 . . ?
C15 C16 H16A 120.4 . . ?
C18 C19 C14 120.7(3) . . ?
C18 C19 H19A 119.6 . . ?
C14 C19 H19A 119.6 . . ?
O3 C21 N3 121.2(3) . . ?
O3 C21 C22 120.4(3) . . ?
N3 C21 C22 118.4(2) . . ?
O4 C17 C18 115.7(2) . . ?
O4 C17 C16 124.0(3) . . ?
C18 C17 C16 120.2(3) . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C23 C22 C24 112.9(4) . . ?
C23 C22 C21 114.3(3) . . ?
C24 C22 C21 107.0(3) . . ?
C23 C22 C25 108.4(4) . . ?
C24 C22 C25 107.1(3) . . ?
C21 C22 C25 106.8(3) . . ?
F6 C20 F4 106.2(3) . . ?
F6 C20 F5 106.4(3) . . ?
F4 C20 F5 106.3(3) . . ?
F6 C20 C15 112.7(3) . . ?
F4 C20 C15 112.5(3) . . ?
F5 C20 C15 112.2(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C40 C41 C42 120.5(3) . . ?
C40 C41 C46 120.1(2) . . ?
C42 C41 C46 119.4(3) . . ?
C41 C40 C45 119.3(3) . . ?
C41 C40 N4 121.4(3) . . ?
C45 C40 N4 119.3(3) . . ?
C43 C42 C41 119.3(3) . . ?
C43 C42 H42A 120.4 . . ?
C41 C42 H42A 120.4 . . ?
O7 C47 N4 121.3(2) . . ?
O7 C47 C48 122.2(2) . . ?
N4 C47 C48 116.5(2) . . ?
C45 C44 C43 119.6(3) . . ?
C45 C44 H44A 120.2 . . ?
C43 C44 H44A 120.2 . . ?
C44 C45 C40 120.7(3) . . ?
C44 C45 H45A 119.6 . . ?
C40 C45 H45A 119.6 . . ?
C51 C48 C49 109.3(3) . . ?
C51 C48 C47 109.7(2) . . ?
C49 C48 C47 109.6(2) . . ?
C51 C48 C50 110.0(3) . . ?
C49 C48 C50 110.2(3) . . ?
C47 C48 C50 107.9(3) . . ?
O8 C43 C42 124.4(3) . . ?
O8 C43 C44 115.1(3) . . ?
C42 C43 C44 120.5(3) . . ?
C48 C51 H51A 109.5 . . ?
C48 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C48 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
F10 C46 F11 106.1(3) . . ?
F10 C46 F12 106.2(3) . . ?
F11 C46 F12 105.3(3) . . ?
F10 C46 C41 114.5(3) . . ?
F11 C46 C41 111.5(3) . . ?
F12 C46 C41 112.6(3) . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C47 N4 C40 120.8(2) . . ?
C47 N4 H4A 119.6 . . ?
C40 N4 H4A 119.6 . . ?
C21 N3 C14 122.2(2) . . ?
C21 N3 H3B 118.9 . . ?
C14 N3 H3B 118.9 . . ?
C34 N2 C27 120.9(2) . . ?
C34 N2 H2A 119.6 . . ?
C27 N2 H2A 119.6 . . ?
C8 N1 C1 123.8(2) . . ?
C8 N1 H1A 118.1 . . ?
C1 N1 H1A 118.1 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 O4 C26 117.6(2) . . ?
C30 O6 C39 117.5(3) . . ?
C43 O8 C52 116.9(3) . . ?
C4 O2 C13 117.7(3) . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O8 C52 H52A 109.5 . . ?
O8 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O8 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
O6 C39 H39A 109.5 . . ?
O6 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O6 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C2 C1 C6 1.8(4) . . . . ?
C7 C2 C1 C6 179.5(3) . . . . ?
C3 C2 C1 N1 -175.6(3) . . . . ?
C7 C2 C1 N1 2.1(4) . . . . ?
C2 C1 C6 C5 -2.4(4) . . . . ?
N1 C1 C6 C5 175.0(3) . . . . ?
O1 C8 C9 C11 114.3(4) . . . . ?
N1 C8 C9 C11 -64.4(4) . . . . ?
O1 C8 C9 C12 -4.9(5) . . . . ?
N1 C8 C9 C12 176.3(3) . . . . ?
O1 C8 C9 C10 -125.7(4) . . . . ?
N1 C8 C9 C10 55.5(4) . . . . ?
O2 C4 C5 C6 -179.5(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C1 C6 C5 C4 1.1(5) . . . . ?
O2 C4 C3 C2 178.9(3) . . . . ?
C5 C4 C3 C2 -1.3(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C7 C2 C3 C4 -177.8(3) . . . . ?
C3 C2 C7 F1 116.3(3) . . . . ?
C1 C2 C7 F1 -61.5(4) . . . . ?
C3 C2 C7 F3 -123.5(3) . . . . ?
C1 C2 C7 F3 58.7(4) . . . . ?
C3 C2 C7 F2 -3.3(5) . . . . ?
C1 C2 C7 F2 178.9(3) . . . . ?
O6 C30 C29 C28 -179.9(3) . . . . ?
C31 C30 C29 C28 -0.5(5) . . . . ?
O5 C34 C35 C36 -8.7(4) . . . . ?
N2 C34 C35 C36 171.4(3) . . . . ?
O5 C34 C35 C38 110.7(3) . . . . ?
N2 C34 C35 C38 -69.2(3) . . . . ?
O5 C34 C35 C37 -128.0(3) . . . . ?
N2 C34 C35 C37 52.0(3) . . . . ?
C32 C27 C28 C29 1.5(4) . . . . ?
N2 C27 C28 C29 -177.3(3) . . . . ?
C32 C27 C28 C33 -178.5(3) . . . . ?
N2 C27 C28 C33 2.6(4) . . . . ?
C30 C29 C28 C27 -1.3(4) . . . . ?
C30 C29 C28 C33 178.7(3) . . . . ?
O6 C30 C31 C32 -178.5(3) . . . . ?
C29 C30 C31 C32 2.1(5) . . . . ?
C30 C31 C32 C27 -1.9(5) . . . . ?
C28 C27 C32 C31 0.1(5) . . . . ?
N2 C27 C32 C31 179.0(3) . . . . ?
C27 C28 C33 F7 -57.9(5) . . . . ?
C29 C28 C33 F7 122.1(3) . . . . ?
C27 C28 C33 F9 62.2(4) . . . . ?
C29 C28 C33 F9 -117.8(3) . . . . ?
C27 C28 C33 F8 -178.9(3) . . . . ?
C29 C28 C33 F8 1.1(5) . . . . ?
C19 C14 C15 C16 -0.5(4) . . . . ?
N3 C14 C15 C16 177.7(3) . . . . ?
C19 C14 C15 C20 -177.8(3) . . . . ?
N3 C14 C15 C20 0.5(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C20 C15 C16 C17 177.8(3) . . . . ?
C15 C14 C19 C18 0.8(4) . . . . ?
N3 C14 C19 C18 -177.5(3) . . . . ?
C15 C16 C17 O4 -178.5(3) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
O4 C17 C18 C19 178.9(3) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C14 C19 C18 C17 -0.9(5) . . . . ?
O3 C21 C22 C23 170.2(4) . . . . ?
N3 C21 C22 C23 -11.3(5) . . . . ?
O3 C21 C22 C24 -64.1(4) . . . . ?
N3 C21 C22 C24 114.4(4) . . . . ?
O3 C21 C22 C25 50.3(4) . . . . ?
N3 C21 C22 C25 -131.2(3) . . . . ?
C14 C15 C20 F6 -177.9(3) . . . . ?
C16 C15 C20 F6 4.8(5) . . . . ?
C14 C15 C20 F4 -57.8(4) . . . . ?
C16 C15 C20 F4 124.9(3) . . . . ?
C14 C15 C20 F5 62.1(4) . . . . ?
C16 C15 C20 F5 -115.2(3) . . . . ?
C42 C41 C40 C45 -2.0(4) . . . . ?
C46 C41 C40 C45 175.4(3) . . . . ?
C42 C41 C40 N4 -179.9(3) . . . . ?
C46 C41 C40 N4 -2.5(4) . . . . ?
C40 C41 C42 C43 2.0(4) . . . . ?
C46 C41 C42 C43 -175.4(3) . . . . ?
C43 C44 C45 C40 0.8(5) . . . . ?
C41 C40 C45 C44 0.5(4) . . . . ?
N4 C40 C45 C44 178.5(3) . . . . ?
O7 C47 C48 C51 -126.1(3) . . . . ?
N4 C47 C48 C51 55.0(4) . . . . ?
O7 C47 C48 C49 -6.0(4) . . . . ?
N4 C47 C48 C49 175.1(3) . . . . ?
O7 C47 C48 C50 114.0(3) . . . . ?
N4 C47 C48 C50 -64.9(3) . . . . ?
C41 C42 C43 O8 178.1(3) . . . . ?
C41 C42 C43 C44 -0.7(5) . . . . ?
C45 C44 C43 O8 -179.7(3) . . . . ?
C45 C44 C43 C42 -0.8(5) . . . . ?
C40 C41 C46 F10 57.4(4) . . . . ?
C42 C41 C46 F10 -125.2(3) . . . . ?
C40 C41 C46 F11 -63.0(4) . . . . ?
C42 C41 C46 F11 114.4(3) . . . . ?
C40 C41 C46 F12 178.8(3) . . . . ?
C42 C41 C46 F12 -3.7(4) . . . . ?
O7 C47 N4 C40 0.2(4) . . . . ?
C48 C47 N4 C40 179.1(2) . . . . ?
C41 C40 N4 C47 101.3(3) . . . . ?
C45 C40 N4 C47 -76.7(4) . . . . ?
O3 C21 N3 C14 2.1(5) . . . . ?
C22 C21 N3 C14 -176.4(3) . . . . ?
C15 C14 N3 C21 91.4(4) . . . . ?
C19 C14 N3 C21 -90.3(4) . . . . ?
O5 C34 N2 C27 1.2(4) . . . . ?
C35 C34 N2 C27 -178.9(3) . . . . ?
C32 C27 N2 C34 -89.7(4) . . . . ?
C28 C27 N2 C34 89.1(4) . . . . ?
O1 C8 N1 C1 -4.2(5) . . . . ?
C9 C8 N1 C1 174.6(3) . . . . ?
C6 C1 N1 C8 74.5(4) . . . . ?
C2 C1 N1 C8 -108.2(3) . . . . ?
C18 C17 O4 C26 177.8(3) . . . . ?
C16 C17 O4 C26 -4.2(5) . . . . ?
C29 C30 O6 C39 -16.4(5) . . . . ?
C31 C30 O6 C39 164.2(3) . . . . ?
C42 C43 O8 C52 -3.0(5) . . . . ?
C44 C43 O8 C52 175.8(4) . . . . ?
C5 C4 O2 C13 12.2(6) . . . . ?
C3 C4 O2 C13 -168.0(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.100