#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
#
####################################################################### 

data_aq35m
_database_code_depnum_ccdc_archive 'CCDC 696932'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3-Iodo-6-methoxy-4-(p-methoxyphenyl)-2-trifluoromethyl)quinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 F3 I N O2'
_chemical_formula_sum            'C18 H13 F3 I N O2'
_chemical_formula_weight         459.19

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'
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_int_tables_number      2
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.995(2)
_cell_length_b                   10.147(2)
_cell_length_c                   11.016(3)
_cell_angle_alpha                107.100(4)
_cell_angle_beta                 95.726(4)
_cell_angle_gamma                110.042(3)
_cell_volume                     880.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6302
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7577
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2973
_reflns_number_gt                2691
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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^)+(0.0345P)^2^+0.2514P] 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         2973
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0672
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.003
_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 0.5892(3) 0.3631(3) 1.0641(2) 0.0440(5) Uani 1 1 d . . .
C2 C 0.7151(3) 0.2766(3) 0.9040(2) 0.0437(5) Uani 1 1 d . . .
C3 C 0.8593(3) 0.2933(3) 0.8563(3) 0.0560(7) Uani 1 1 d . . .
H3 H 0.9532 0.3788 0.8987 0.067 Uiso 1 1 calc R . .
C4 C 0.8608(3) 0.1844(3) 0.7485(3) 0.0618(7) Uani 1 1 d . . .
H4 H 0.9556 0.1965 0.7180 0.074 Uiso 1 1 calc R . .
C5 C 0.7180(3) 0.0528(3) 0.6827(2) 0.0522(6) Uani 1 1 d . . .
C6 C 0.5759(3) 0.0346(3) 0.7242(2) 0.0452(5) Uani 1 1 d . . .
H6 H 0.4827 -0.0507 0.6792 0.054 Uiso 1 1 calc R . .
C7 C 0.5710(3) 0.1458(3) 0.8358(2) 0.0403(5) Uani 1 1 d . . .
C8 C 0.4274(3) 0.1307(3) 0.8866(2) 0.0407(5) Uani 1 1 d . . .
C9 C 0.4370(3) 0.2378(3) 1.0017(2) 0.0428(5) Uani 1 1 d . . .
C10 C 0.2746(3) -0.0043(3) 0.8115(2) 0.0400(5) Uani 1 1 d . . .
C11 C 0.1843(3) -0.0089(3) 0.6991(3) 0.0559(7) Uani 1 1 d . . .
H11 H 0.2129 0.0753 0.6748 0.067 Uiso 1 1 calc R . .
C12 C 0.0516(3) -0.1387(4) 0.6226(3) 0.0635(8) Uani 1 1 d . . .
H12 H -0.0075 -0.1406 0.5474 0.076 Uiso 1 1 calc R . .
C13 C 0.0070(3) -0.2645(3) 0.6575(3) 0.0527(6) Uani 1 1 d . . .
C14 C 0.0943(3) -0.2613(3) 0.7698(3) 0.0534(6) Uani 1 1 d . . .
H14 H 0.0650 -0.3453 0.7943 0.064 Uiso 1 1 calc R . .
C15 C 0.2268(3) -0.1307(3) 0.8457(3) 0.0514(6) Uani 1 1 d . . .
H15 H 0.2847 -0.1285 0.9216 0.062 Uiso 1 1 calc R . .
C16 C 0.6125(3) 0.4838(3) 1.1941(3) 0.0543(6) Uani 1 1 d . . .
C17 C 0.6067(4) -0.1921(4) 0.5201(3) 0.0719(9) Uani 1 1 d . . .
H17A H 0.5768 -0.2350 0.5854 0.108 Uiso 1 1 calc R . .
H17B H 0.6395 -0.2572 0.4561 0.108 Uiso 1 1 calc R . .
H17C H 0.5155 -0.1801 0.4789 0.108 Uiso 1 1 calc R . .
C18 C -0.1678(5) -0.5228(4) 0.5992(4) 0.0886(11) Uani 1 1 d . . .
H18A H -0.0759 -0.5503 0.6040 0.133 Uiso 1 1 calc R . .
H18B H -0.2554 -0.6004 0.5303 0.133 Uiso 1 1 calc R . .
H18C H -0.2014 -0.5096 0.6804 0.133 Uiso 1 1 calc R . .
F1 F 0.7631(2) 0.5885(2) 1.23531(19) 0.0917(7) Uani 1 1 d . . .
F2 F 0.5118(3) 0.5548(2) 1.19110(18) 0.0785(5) Uani 1 1 d . . .
F3 F 0.5858(2) 0.4266(2) 1.28936(15) 0.0752(5) Uani 1 1 d . . .
I1 I 0.22639(2) 0.21310(2) 1.078796(18) 0.06585(10) Uani 1 1 d . . .
N1 N 0.7207(2) 0.3829(2) 1.01714(19) 0.0455(5) Uani 1 1 d . . .
O1 O 0.7384(2) -0.0491(2) 0.5798(2) 0.0696(6) Uani 1 1 d . . .
O2 O -0.1244(3) -0.3872(3) 0.5740(2) 0.0764(6) 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 0.0447(13) 0.0378(12) 0.0408(12) 0.0077(10) 0.0071(10) 0.0115(10)
C2 0.0407(12) 0.0379(12) 0.0424(12) 0.0101(10) 0.0070(9) 0.0075(10)
C3 0.0391(12) 0.0467(15) 0.0597(15) 0.0069(12) 0.0127(11) 0.0001(11)
C4 0.0411(13) 0.0595(17) 0.0639(17) 0.0066(14) 0.0234(12) 0.0047(12)
C5 0.0460(13) 0.0500(15) 0.0477(14) 0.0057(11) 0.0144(11) 0.0122(11)
C6 0.0373(11) 0.0408(13) 0.0438(12) 0.0072(10) 0.0064(9) 0.0061(10)
C7 0.0357(11) 0.0395(12) 0.0389(11) 0.0115(10) 0.0061(9) 0.0092(9)
C8 0.0347(11) 0.0391(12) 0.0416(12) 0.0126(10) 0.0061(9) 0.0086(9)
C9 0.0372(11) 0.0438(13) 0.0420(12) 0.0121(10) 0.0117(9) 0.0114(10)
C10 0.0314(10) 0.0389(13) 0.0403(12) 0.0071(10) 0.0082(9) 0.0083(9)
C11 0.0488(14) 0.0516(16) 0.0576(15) 0.0220(13) 0.0012(12) 0.0090(12)
C12 0.0495(15) 0.068(2) 0.0559(16) 0.0187(15) -0.0081(12) 0.0113(14)
C13 0.0352(12) 0.0522(16) 0.0520(14) 0.0044(12) 0.0057(10) 0.0081(11)
C14 0.0427(13) 0.0444(14) 0.0618(16) 0.0168(12) 0.0086(11) 0.0063(11)
C15 0.0440(13) 0.0496(15) 0.0498(14) 0.0175(12) 0.0006(11) 0.0085(11)
C16 0.0518(14) 0.0451(14) 0.0496(14) 0.0055(12) 0.0106(11) 0.0092(12)
C17 0.0659(18) 0.0526(17) 0.0682(19) -0.0045(14) 0.0241(15) 0.0083(14)
C18 0.068(2) 0.055(2) 0.092(2) -0.0009(18) 0.0096(18) -0.0101(16)
F1 0.0718(12) 0.0675(12) 0.0721(11) -0.0196(9) 0.0204(9) -0.0114(10)
F2 0.0987(14) 0.0626(11) 0.0705(11) 0.0045(9) 0.0176(10) 0.0436(10)
F3 0.0938(13) 0.0737(12) 0.0434(8) 0.0131(8) 0.0137(8) 0.0222(10)
I1 0.04778(13) 0.06708(16) 0.06430(15) 0.00433(10) 0.02413(9) 0.01346(9)
N1 0.0421(10) 0.0372(11) 0.0443(11) 0.0090(9) 0.0068(8) 0.0058(9)
O1 0.0551(11) 0.0586(12) 0.0662(12) -0.0062(10) 0.0282(10) 0.0079(9)
O2 0.0516(11) 0.0612(14) 0.0721(14) 0.0025(11) -0.0092(10) -0.0060(10)

_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 N1 1.314(3) . ?
C1 C9 1.439(3) . ?
C1 C16 1.526(3) . ?
C2 N1 1.370(3) . ?
C2 C3 1.423(4) . ?
C2 C7 1.430(3) . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.424(4) . ?
C4 H4 0.9300 . ?
C5 O1 1.368(3) . ?
C5 C6 1.372(4) . ?
C6 C7 1.419(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.437(3) . ?
C8 C9 1.378(3) . ?
C8 C10 1.505(3) . ?
C9 I1 2.119(2) . ?
C10 C15 1.382(4) . ?
C10 C11 1.392(4) . ?
C11 C12 1.392(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9300 . ?
C13 O2 1.376(3) . ?
C13 C14 1.383(4) . ?
C14 C15 1.394(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 F1 1.333(3) . ?
C16 F2 1.340(3) . ?
C16 F3 1.345(3) . ?
C17 O1 1.431(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O2 1.414(5) . ?
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
N1 C1 C9 123.8(2) . . ?
N1 C1 C16 113.9(2) . . ?
C9 C1 C16 122.2(2) . . ?
N1 C2 C3 118.9(2) . . ?
N1 C2 C7 122.1(2) . . ?
C3 C2 C7 118.9(2) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O1 C5 C6 125.1(2) . . ?
O1 C5 C4 114.2(2) . . ?
C6 C5 C4 120.7(2) . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 119.5(2) . . ?
C6 C7 C8 122.6(2) . . ?
C2 C7 C8 117.8(2) . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 C10 123.6(2) . . ?
C7 C8 C10 117.6(2) . . ?
C8 C9 C1 118.6(2) . . ?
C8 C9 I1 118.85(16) . . ?
C1 C9 I1 122.52(17) . . ?
C15 C10 C11 118.1(2) . . ?
C15 C10 C8 121.5(2) . . ?
C11 C10 C8 120.2(2) . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O2 C13 C12 115.8(2) . . ?
O2 C13 C14 124.5(3) . . ?
C12 C13 C14 119.7(2) . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C10 C15 C14 122.0(2) . . ?
C10 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
F1 C16 F2 107.0(2) . . ?
F1 C16 F3 105.9(2) . . ?
F2 C16 F3 105.7(2) . . ?
F1 C16 C1 112.5(2) . . ?
F2 C16 C1 113.4(2) . . ?
F3 C16 C1 111.8(2) . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C2 118.6(2) . . ?
C5 O1 C17 117.2(2) . . ?
C13 O2 C18 118.2(3) . . ?

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
N1 C2 C3 C4 175.7(3) . . . . ?
C7 C2 C3 C4 -1.3(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 O1 -177.5(3) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
O1 C5 C6 C7 177.5(3) . . . . ?
C4 C5 C6 C7 -1.6(4) . . . . ?
C5 C6 C7 C2 0.1(4) . . . . ?
C5 C6 C7 C8 -177.8(2) . . . . ?
N1 C2 C7 C6 -175.6(2) . . . . ?
C3 C2 C7 C6 1.3(4) . . . . ?
N1 C2 C7 C8 2.4(4) . . . . ?
C3 C2 C7 C8 179.3(2) . . . . ?
C6 C7 C8 C9 174.4(2) . . . . ?
C2 C7 C8 C9 -3.5(3) . . . . ?
C6 C7 C8 C10 -4.3(3) . . . . ?
C2 C7 C8 C10 177.7(2) . . . . ?
C7 C8 C9 C1 2.1(3) . . . . ?
C10 C8 C9 C1 -179.2(2) . . . . ?
C7 C8 C9 I1 -178.73(17) . . . . ?
C10 C8 C9 I1 0.0(3) . . . . ?
N1 C1 C9 C8 0.7(4) . . . . ?
C16 C1 C9 C8 -177.7(2) . . . . ?
N1 C1 C9 I1 -178.52(19) . . . . ?
C16 C1 C9 I1 3.1(3) . . . . ?
C9 C8 C10 C15 -81.3(3) . . . . ?
C7 C8 C10 C15 97.4(3) . . . . ?
C9 C8 C10 C11 103.7(3) . . . . ?
C7 C8 C10 C11 -77.6(3) . . . . ?
C15 C10 C11 C12 -1.2(4) . . . . ?
C8 C10 C11 C12 174.0(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 O2 -179.1(3) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
O2 C13 C14 C15 179.1(3) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C11 C10 C15 C14 1.3(4) . . . . ?
C8 C10 C15 C14 -173.8(2) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
N1 C1 C16 F1 0.6(3) . . . . ?
C9 C1 C16 F1 179.1(3) . . . . ?
N1 C1 C16 F2 122.2(3) . . . . ?
C9 C1 C16 F2 -59.3(3) . . . . ?
N1 C1 C16 F3 -118.4(3) . . . . ?
C9 C1 C16 F3 60.2(3) . . . . ?
C9 C1 N1 C2 -1.8(4) . . . . ?
C16 C1 N1 C2 176.7(2) . . . . ?
C3 C2 N1 C1 -176.7(2) . . . . ?
C7 C2 N1 C1 0.2(4) . . . . ?
C6 C5 O1 C17 -7.3(4) . . . . ?
C4 C5 O1 C17 171.8(3) . . . . ?
C12 C13 O2 C18 175.1(3) . . . . ?
C14 C13 O2 C18 -4.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.053


data_ad61m
_database_code_depnum_ccdc_archive 'CCDC 696933'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3-Iodo-4-phenyl-2-trifluoromethyl-1-aza-spiro[4.5]deca-1,3,6,9-tetraen-8-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 F3 I N O'
_chemical_formula_sum            'C16 H9 F3 I N O'
_chemical_formula_weight         415.14

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_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                   5.5479(6)
_cell_length_b                   18.4740(19)
_cell_length_c                   14.5807(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.871(2)
_cell_angle_gamma                90.00
_cell_volume                     1472.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6659
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    2.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'


_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13503
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2584
_reflns_number_gt                2502
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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^)+(0.0214P)^2^+1.3746P] 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         2584
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0549
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.002
_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 0.2627(4) 0.65241(14) 0.69973(17) 0.0324(5) Uani 1 1 d . . .
C2 C 0.4533(5) 0.74357(14) 0.78006(17) 0.0343(5) Uani 1 1 d . . .
C3 C 0.3490(4) 0.70025(14) 0.84783(16) 0.0321(5) Uani 1 1 d . . .
C4 C 0.2266(4) 0.64528(13) 0.80118(16) 0.0310(5) Uani 1 1 d . . .
C5 C 0.0251(5) 0.65919(15) 0.63332(17) 0.0360(6) Uani 1 1 d . . .
H5 H -0.0956 0.6894 0.6490 0.043 Uiso 1 1 calc R . .
C6 C -0.0190(5) 0.62395(16) 0.55347(18) 0.0413(6) Uani 1 1 d . . .
H6 H -0.1709 0.6292 0.5156 0.050 Uiso 1 1 calc R . .
C7 C 0.1634(5) 0.57692(16) 0.52283(18) 0.0427(6) Uani 1 1 d . . .
C8 C 0.3820(5) 0.56073(16) 0.59098(19) 0.0432(6) Uani 1 1 d . . .
H8 H 0.4917 0.5261 0.5769 0.052 Uiso 1 1 calc R . .
C9 C 0.4271(5) 0.59416(15) 0.67190(18) 0.0382(6) Uani 1 1 d . . .
H9 H 0.5664 0.5813 0.7138 0.046 Uiso 1 1 calc R . .
C10 C 0.0714(4) 0.58807(14) 0.83116(17) 0.0334(5) Uani 1 1 d . . .
C11 C -0.0759(5) 0.60204(16) 0.89703(19) 0.0405(6) Uani 1 1 d . . .
H11 H -0.0708 0.6474 0.9250 0.049 Uiso 1 1 calc R . .
C12 C -0.2301(6) 0.54937(18) 0.9217(2) 0.0510(7) Uani 1 1 d . . .
H12 H -0.3271 0.5595 0.9662 0.061 Uiso 1 1 calc R . .
C13 C -0.2407(6) 0.48216(18) 0.8807(2) 0.0549(8) Uani 1 1 d . . .
H13 H -0.3440 0.4467 0.8975 0.066 Uiso 1 1 calc R . .
C14 C -0.0974(6) 0.46766(18) 0.8145(3) 0.0597(9) Uani 1 1 d . . .
H14 H -0.1040 0.4223 0.7865 0.072 Uiso 1 1 calc R . .
C15 C 0.0559(5) 0.52019(16) 0.7895(2) 0.0481(7) Uani 1 1 d . . .
H15 H 0.1502 0.5100 0.7442 0.058 Uiso 1 1 calc R . .
C16 C 0.6126(6) 0.80978(16) 0.8003(2) 0.0453(7) Uani 1 1 d . . .
F1 F 0.6621(5) 0.83952(12) 0.72367(14) 0.0831(7) Uani 1 1 d . . .
F2 F 0.8240(3) 0.79280(11) 0.85403(16) 0.0666(5) Uani 1 1 d . . .
F3 F 0.5098(4) 0.86003(10) 0.84548(15) 0.0667(5) Uani 1 1 d . . .
I1 I 0.40186(3) 0.723446(10) 0.990063(11) 0.04059(8) Uani 1 1 d . . .
N1 N 0.4061(4) 0.72014(12) 0.69659(16) 0.0368(5) Uani 1 1 d . . .
O1 O 0.1368(5) 0.55275(13) 0.44337(14) 0.0618(6) 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 0.0352(12) 0.0383(13) 0.0243(12) -0.0055(10) 0.0066(10) -0.0034(10)
C2 0.0384(13) 0.0375(13) 0.0266(13) -0.0026(11) 0.0043(10) -0.0012(11)
C3 0.0365(13) 0.0379(13) 0.0223(12) -0.0023(10) 0.0060(10) 0.0036(10)
C4 0.0321(12) 0.0370(13) 0.0239(12) -0.0005(10) 0.0051(9) 0.0043(10)
C5 0.0346(13) 0.0440(15) 0.0299(13) 0.0022(11) 0.0067(10) 0.0012(11)
C6 0.0393(14) 0.0544(17) 0.0285(13) 0.0036(12) 0.0008(11) -0.0076(12)
C7 0.0550(16) 0.0452(16) 0.0295(14) -0.0060(11) 0.0124(12) -0.0155(13)
C8 0.0461(15) 0.0476(16) 0.0393(15) -0.0081(12) 0.0173(12) -0.0001(12)
C9 0.0320(13) 0.0502(16) 0.0331(14) -0.0033(12) 0.0076(10) 0.0015(11)
C10 0.0335(12) 0.0391(14) 0.0273(12) 0.0039(10) 0.0038(10) 0.0023(10)
C11 0.0412(14) 0.0451(15) 0.0361(14) 0.0012(12) 0.0091(11) 0.0013(12)
C12 0.0473(16) 0.065(2) 0.0441(17) 0.0087(15) 0.0177(13) -0.0024(14)
C13 0.0508(17) 0.0523(19) 0.063(2) 0.0153(16) 0.0123(15) -0.0085(14)
C14 0.063(2) 0.0413(17) 0.078(2) -0.0039(16) 0.0194(18) -0.0081(14)
C15 0.0508(16) 0.0442(16) 0.0529(18) -0.0061(14) 0.0196(14) -0.0030(13)
C16 0.0553(17) 0.0439(16) 0.0358(15) -0.0028(12) 0.0059(13) -0.0083(13)
F1 0.1225(19) 0.0775(14) 0.0512(12) 0.0007(10) 0.0202(12) -0.0536(14)
F2 0.0483(10) 0.0641(12) 0.0804(15) -0.0084(10) -0.0084(10) -0.0104(9)
F3 0.0832(13) 0.0407(10) 0.0750(14) -0.0153(9) 0.0109(11) -0.0004(9)
I1 0.05103(13) 0.04722(13) 0.02308(11) -0.00571(6) 0.00511(8) -0.00086(7)
N1 0.0401(12) 0.0425(13) 0.0283(11) -0.0010(9) 0.0073(9) -0.0051(9)
O1 0.0854(16) 0.0706(15) 0.0302(11) -0.0174(10) 0.0123(10) -0.0150(12)

_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 N1 1.488(3) . ?
C1 C5 1.501(3) . ?
C1 C9 1.510(4) . ?
C1 C4 1.532(3) . ?
C2 N1 1.276(3) . ?
C2 C3 1.466(4) . ?
C2 C16 1.508(4) . ?
C3 C4 1.341(4) . ?
C3 I1 2.088(2) . ?
C4 C10 1.476(4) . ?
C5 C6 1.320(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.461(4) . ?
C6 H6 0.9300 . ?
C7 O1 1.227(3) . ?
C7 C8 1.461(4) . ?
C8 C9 1.317(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.388(4) . ?
C10 C15 1.389(4) . ?
C11 C12 1.384(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 F1 1.316(3) . ?
C16 F3 1.322(4) . ?
C16 F2 1.332(4) . ?

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
N1 C1 C5 109.0(2) . . ?
N1 C1 C9 103.9(2) . . ?
C5 C1 C9 113.0(2) . . ?
N1 C1 C4 105.14(19) . . ?
C5 C1 C4 112.6(2) . . ?
C9 C1 C4 112.5(2) . . ?
N1 C2 C3 114.7(2) . . ?
N1 C2 C16 118.7(2) . . ?
C3 C2 C16 126.6(2) . . ?
C4 C3 C2 107.2(2) . . ?
C4 C3 I1 129.19(19) . . ?
C2 C3 I1 123.57(18) . . ?
C3 C4 C10 131.5(2) . . ?
C3 C4 C1 106.6(2) . . ?
C10 C4 C1 121.8(2) . . ?
C6 C5 C1 122.5(2) . . ?
C6 C5 H5 118.7 . . ?
C1 C5 H5 118.7 . . ?
C5 C6 C7 122.0(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
O1 C7 C6 121.9(3) . . ?
O1 C7 C8 121.3(3) . . ?
C6 C7 C8 116.9(2) . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C1 123.0(3) . . ?
C8 C9 H9 118.5 . . ?
C1 C9 H9 118.5 . . ?
C11 C10 C15 118.1(3) . . ?
C11 C10 C4 121.0(2) . . ?
C15 C10 C4 120.8(2) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
F1 C16 F3 107.5(3) . . ?
F1 C16 F2 107.8(3) . . ?
F3 C16 F2 106.5(2) . . ?
F1 C16 C2 111.9(2) . . ?
F3 C16 C2 112.3(2) . . ?
F2 C16 C2 110.6(2) . . ?
C2 N1 C1 106.2(2) . . ?

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
N1 C2 C3 C4 -0.1(3) . . . . ?
C16 C2 C3 C4 -178.1(3) . . . . ?
N1 C2 C3 I1 178.42(19) . . . . ?
C16 C2 C3 I1 0.4(4) . . . . ?
C2 C3 C4 C10 -174.9(2) . . . . ?
I1 C3 C4 C10 6.7(4) . . . . ?
C2 C3 C4 C1 2.2(3) . . . . ?
I1 C3 C4 C1 -176.22(18) . . . . ?
N1 C1 C4 C3 -3.3(3) . . . . ?
C5 C1 C4 C3 -121.8(2) . . . . ?
C9 C1 C4 C3 109.1(2) . . . . ?
N1 C1 C4 C10 174.1(2) . . . . ?
C5 C1 C4 C10 55.5(3) . . . . ?
C9 C1 C4 C10 -73.5(3) . . . . ?
N1 C1 C5 C6 106.9(3) . . . . ?
C9 C1 C5 C6 -8.0(4) . . . . ?
C4 C1 C5 C6 -136.8(3) . . . . ?
C1 C5 C6 C7 -1.5(4) . . . . ?
C5 C6 C7 O1 -169.0(3) . . . . ?
C5 C6 C7 C8 10.1(4) . . . . ?
O1 C7 C8 C9 170.7(3) . . . . ?
C6 C7 C8 C9 -8.4(4) . . . . ?
C7 C8 C9 C1 -1.5(4) . . . . ?
N1 C1 C9 C8 -108.3(3) . . . . ?
C5 C1 C9 C8 9.6(4) . . . . ?
C4 C1 C9 C8 138.5(3) . . . . ?
C3 C4 C10 C11 35.1(4) . . . . ?
C1 C4 C10 C11 -141.6(2) . . . . ?
C3 C4 C10 C15 -149.4(3) . . . . ?
C1 C4 C10 C15 33.9(4) . . . . ?
C15 C10 C11 C12 1.2(4) . . . . ?
C4 C10 C11 C12 176.8(3) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C10 0.9(5) . . . . ?
C11 C10 C15 C14 -1.4(4) . . . . ?
C4 C10 C15 C14 -177.1(3) . . . . ?
N1 C2 C16 F1 6.7(4) . . . . ?
C3 C2 C16 F1 -175.4(3) . . . . ?
N1 C2 C16 F3 127.6(3) . . . . ?
C3 C2 C16 F3 -54.5(4) . . . . ?
N1 C2 C16 F2 -113.6(3) . . . . ?
C3 C2 C16 F2 64.4(4) . . . . ?
C3 C2 N1 C1 -2.1(3) . . . . ?
C16 C2 N1 C1 176.1(2) . . . . ?
C5 C1 N1 C2 124.2(2) . . . . ?
C9 C1 N1 C2 -115.2(2) . . . . ?
C4 C1 N1 C2 3.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.086