 
data_a
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety     'C17 H11 Cl F N O2'
_chemical_formula_sum
 'C17 H11 Cl F N O2' 
_chemical_formula_weight          315.72

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    12.500(3)
_cell_length_b                    16.914(3)
_cell_length_c                    14.059(3)
_cell_angle_alpha                 90
_cell_angle_beta                  100.76(3)
_cell_angle_gamma                 90
_cell_volume                      2920.2(11)
_cell_formula_units_Z             8
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     546
_cell_measurement_theta_min       2.45
_cell_measurement_theta_max       26.75
 
_exptl_crystal_description        block
_exptl_crystal_colour             yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.436          
_exptl_crystal_F_000              1296
_exptl_transmission_factor_min    0.998
_exptl_transmission_factor_max    1.000
_exptl_crystal_size_max           0.230
_exptl_crystal_size_mid           0.120
_exptl_crystal_size_min           0.090
_exptl_absorpt_coefficient_mu     0.278
_shelx_estimated_absorpt_T_min    0.696
_shelx_estimated_absorpt_T_max    0.862
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details  'mulabs in platon'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed-tube'
_diffrn_measurement_device_type   'stoe ipds 2t'
_diffrn_measurement_method        'ω scan'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             17585
_diffrn_reflns_av_unetI/netI      0.0304
_diffrn_reflns_av_R_equivalents   0.0404
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -23
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          2.700
_diffrn_reflns_theta_max          29.288
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.991
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.991
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.991
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              3964
_reflns_number_gt                 2644
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'X-Area 1.43 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement        'X-Area 1.43 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction         'X-Area 1.43 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement   'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material   'SHELXTL, PLATON (Spek, 2009)'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0669P)²+0.1468P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3964
_refine_ls_number_parameters      200
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0630
_refine_ls_R_factor_gt            0.0414
_refine_ls_wR_factor_ref          0.1213
_refine_ls_wR_factor_gt           0.1135
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.85595(12) 0.74764(9) 0.36895(11) 0.0537(3) Uani 1 1 d . . . . .
H1A H 0.9281 0.7592 0.3664 0.064 Uiso 1 1 calc R U . . .
C2 C 0.82711(11) 0.66711(8) 0.37320(9) 0.0459(3) Uani 1 1 d . . . . .
C3 C 0.72000(10) 0.64761(8) 0.37560(9) 0.0428(3) Uani 1 1 d . . . . .
C4 C 0.64466(10) 0.71135(8) 0.37539(8) 0.0441(3) Uani 1 1 d . . . . .
C5 C 0.68336(12) 0.78980(8) 0.37185(9) 0.0484(3) Uani 1 1 d . . . . .
C6 C 0.61071(14) 0.85373(9) 0.37272(11) 0.0598(4) Uani 1 1 d . . . . .
H6A H 0.6359 0.9053 0.3699 0.072 Uiso 1 1 calc R U . . .
C7 C 0.50402(13) 0.84084(10) 0.37761(11) 0.0612(4) Uani 1 1 d . . . . .
H7A H 0.4567 0.8831 0.3785 0.073 Uiso 1 1 calc R U . . .
C8 C 0.46707(12) 0.76277(9) 0.38120(10) 0.0547(3) Uani 1 1 d . . . . .
C9 C 0.53324(11) 0.69916(9) 0.37888(9) 0.0490(3) Uani 1 1 d . . . . .
H9A H 0.5056 0.6482 0.3796 0.059 Uiso 1 1 calc R U . . .
C10 C 0.91488(11) 0.60589(9) 0.37943(10) 0.0512(3) Uani 1 1 d . . . . .
C11 C 1.10356(13) 0.58602(14) 0.39357(18) 0.0890(6) Uani 1 1 d . . . . .
H11A H 1.1695 0.6162 0.4001 0.133 Uiso 1 1 calc R U . . .
H11B H 1.0969 0.5526 0.3376 0.133 Uiso 1 1 calc R U . . .
H11C H 1.1055 0.5540 0.4503 0.133 Uiso 1 1 calc R U . . .
C12 C 0.68186(10) 0.56451(8) 0.38041(9) 0.0432(3) Uani 1 1 d . . . . .
C13 C 0.65545(11) 0.53346(8) 0.46510(11) 0.0511(3) Uani 1 1 d . . . . .
H13A H 0.6590 0.5658 0.5191 0.061 Uiso 1 1 calc R U . . .
C14 C 0.62423(13) 0.45574(10) 0.46971(12) 0.0608(4) Uani 1 1 d . . . . .
H14A H 0.6072 0.4359 0.5268 0.073 Uiso 1 1 calc R U . . .
C15 C 0.61809(13) 0.40717(10) 0.39028(14) 0.0679(4) Uani 1 1 d . . . . .
H15A H 0.5983 0.3544 0.3943 0.081 Uiso 1 1 calc R U . . .
C16 C 0.64122(14) 0.43643(10) 0.30452(13) 0.0673(4) Uani 1 1 d . . . . .
H16A H 0.6364 0.4042 0.2503 0.081 Uiso 1 1 calc R U . . .
C17 C 0.67156(12) 0.51434(9) 0.30163(11) 0.0540(3) Uani 1 1 d . . . . .
N1 N 0.78912(10) 0.80723(7) 0.36831(9) 0.0561(3) Uani 1 1 d . . . . .
O1 O 0.90329(9) 0.53619(8) 0.38394(12) 0.0857(4) Uani 1 1 d . . . . .
O2 O 1.01147(9) 0.63902(7) 0.38266(10) 0.0746(4) Uani 1 1 d . . . . .
F1 F 0.69565(10) 0.54350(7) 0.21790(7) 0.0854(3) Uani 1 1 d . . . . .
Cl1 Cl 0.33111(3) 0.74778(3) 0.38848(4) 0.07734(17) Uani 1 1 d . . . . .
 
 
_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 1.308(2) . ?
C1 C2 1.413(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.3855(18) . ?
C2 C10 1.499(2) . ?
C3 C4 1.4312(18) . ?
C3 C12 1.4897(18) . ?
C4 C5 1.416(2) . ?
C4 C9 1.4179(19) . ?
C5 N1 1.3646(19) . ?
C5 C6 1.414(2) . ?
C6 C7 1.366(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.403(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.361(2) . ?
C8 Cl1 1.7402(17) . ?
C9 H9A 0.9300 . ?
C10 O1 1.191(2) . ?
C10 O2 1.3242(17) . ?
C11 O2 1.444(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.3821(19) . ?
C12 C13 1.3960(19) . ?
C13 C14 1.376(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.377(2) . ?
C14 H14A 0.9300 . ?
C15 C16 1.383(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.374(2) . ?
C16 H16A 0.9300 . ?
C17 F1 1.3610(18) . ?
 
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 C2 125.13(14) . . ?
N1 C1 H1A 117.4 . . ?
C2 C1 H1A 117.4 . . ?
C3 C2 C1 119.07(13) . . ?
C3 C2 C10 122.29(12) . . ?
C1 C2 C10 118.59(12) . . ?
C2 C3 C4 117.33(12) . . ?
C2 C3 C12 123.00(12) . . ?
C4 C3 C12 119.65(11) . . ?
C5 C4 C9 118.79(13) . . ?
C5 C4 C3 118.48(12) . . ?
C9 C4 C3 122.73(13) . . ?
N1 C5 C6 117.61(13) . . ?
N1 C5 C4 122.91(13) . . ?
C6 C5 C4 119.48(13) . . ?
C7 C6 C5 120.88(15) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C8 118.90(14) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 H7A 120.5 . . ?
C9 C8 C7 122.51(15) . . ?
C9 C8 Cl1 119.39(13) . . ?
C7 C8 Cl1 118.10(12) . . ?
C8 C9 C4 119.41(14) . . ?
C8 C9 H9A 120.3 . . ?
C4 C9 H9A 120.3 . . ?
O1 C10 O2 122.43(14) . . ?
O1 C10 C2 126.29(13) . . ?
O2 C10 C2 111.25(13) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 116.81(13) . . ?
C17 C12 C3 121.71(12) . . ?
C13 C12 C3 121.48(12) . . ?
C14 C13 C12 120.92(14) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 120.33(15) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C14 C15 C16 120.30(15) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C17 C16 C15 118.21(15) . . ?
C17 C16 H16A 120.9 . . ?
C15 C16 H16A 120.9 . . ?
F1 C17 C16 118.69(14) . . ?
F1 C17 C12 117.91(13) . . ?
C16 C17 C12 123.37(14) . . ?
C1 N1 C5 117.07(12) . . ?
C10 O2 C11 116.40(14) . . ?
 
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 C1 C2 C3 1.0(2) . . . . ?
N1 C1 C2 C10 -176.34(13) . . . . ?
C1 C2 C3 C4 -1.12(19) . . . . ?
C10 C2 C3 C4 176.08(12) . . . . ?
C1 C2 C3 C12 -179.80(12) . . . . ?
C10 C2 C3 C12 -2.6(2) . . . . ?
C2 C3 C4 C5 0.58(17) . . . . ?
C12 C3 C4 C5 179.31(11) . . . . ?
C2 C3 C4 C9 -179.22(12) . . . . ?
C12 C3 C4 C9 -0.49(18) . . . . ?
C9 C4 C5 N1 -179.97(12) . . . . ?
C3 C4 C5 N1 0.23(19) . . . . ?
C9 C4 C5 C6 0.55(19) . . . . ?
C3 C4 C5 C6 -179.26(12) . . . . ?
N1 C5 C6 C7 -179.05(13) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 -0.8(2) . . . . ?
C6 C7 C8 Cl1 179.44(12) . . . . ?
C7 C8 C9 C4 1.8(2) . . . . ?
Cl1 C8 C9 C4 -178.43(10) . . . . ?
C5 C4 C9 C8 -1.64(19) . . . . ?
C3 C4 C9 C8 178.15(12) . . . . ?
C3 C2 C10 O1 2.4(2) . . . . ?
C1 C2 C10 O1 179.61(16) . . . . ?
C3 C2 C10 O2 -175.50(12) . . . . ?
C1 C2 C10 O2 1.71(19) . . . . ?
C2 C3 C12 C17 -72.56(18) . . . . ?
C4 C3 C12 C17 108.78(15) . . . . ?
C2 C3 C12 C13 107.02(15) . . . . ?
C4 C3 C12 C13 -71.63(16) . . . . ?
C17 C12 C13 C14 2.1(2) . . . . ?
C3 C12 C13 C14 -177.54(13) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
C15 C16 C17 F1 179.29(14) . . . . ?
C15 C16 C17 C12 1.1(2) . . . . ?
C13 C12 C17 F1 179.28(13) . . . . ?
C3 C12 C17 F1 -1.1(2) . . . . ?
C13 C12 C17 C16 -2.5(2) . . . . ?
C3 C12 C17 C16 177.08(15) . . . . ?
C2 C1 N1 C5 -0.1(2) . . . . ?
C6 C5 N1 C1 179.04(13) . . . . ?
C4 C5 N1 C1 -0.5(2) . . . . ?
O1 C10 O2 C11 -0.9(3) . . . . ?
C2 C10 O2 C11 177.05(15) . . . . ?
 
_refine_diff_density_max    0.180
_refine_diff_density_min   -0.349
_refine_diff_density_rms    0.039



