data_1
_audit_creation_method             'SHELXL-2014/7'
_shelx_SHELXL_version_number       '2014/7'
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C19 H13 Cl N2 O'
_chemical_formula_sum              'C19 H13 Cl N2 O'
_chemical_formula_weight           320.76
_chemical_melting_point            ?
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'
 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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. 
;
_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'
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                     31.575(9)
_cell_length_b                     4.3839(12)
_cell_length_c                     25.202(7)
_cell_angle_alpha                  90
_cell_angle_beta                   110.474(5)
_cell_angle_gamma                  90
_cell_volume                       3268.2(16)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      2013
_cell_measurement_temperature      296(2)
_cell_measurement_theta_max        25.51
_cell_measurement_theta_min        3.24
_shelx_estimated_absorpt_T_max     0.963
_shelx_estimated_absorpt_T_min     0.940
_exptl_absorpt_coefficient_mu      0.239
_exptl_absorpt_correction_T_max    0.963
_exptl_absorpt_correction_T_min    0.940
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS; Bruker, 2008'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.304
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         block
_exptl_crystal_F_000               1328
_exptl_crystal_size_max            0.260
_exptl_crystal_size_mid            0.230
_exptl_crystal_size_min            0.160
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0332
_diffrn_reflns_av_unetI/netI       0.0401
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         30
_diffrn_reflns_limit_h_min         -36
_diffrn_reflns_limit_k_max         5
_diffrn_reflns_limit_k_min         -5
_diffrn_reflns_limit_l_max         28
_diffrn_reflns_limit_l_min         -29
_diffrn_reflns_number              7395
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          24.995
_diffrn_reflns_theta_max           24.995
_diffrn_reflns_theta_min           1.377
_diffrn_ambient_temperature        296(2)
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2004
_reflns_number_total               2864
_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. 
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SMART'
_computing_data_collection         'SMART (Bruker, 2008)'
_computing_data_reduction          'SAINT (Bruker, 2008)'
_computing_molecular_graphics      'SHELXTL (Bruker, 2008)'
_computing_publication_material    'SHELXTL (Bruker, 2008)'
_computing_structure_refinement    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution      'SHELXTL (Bruker, 2008)'
_refine_diff_density_max           0.511
_refine_diff_density_min           -0.321
_refine_diff_density_rms           0.127
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.070
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       208
_refine_ls_number_reflns           2864
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0981
_refine_ls_R_factor_gt             0.0630
_refine_ls_restrained_S_all        1.070
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.1460P)²+0.3432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1990
_refine_ls_wR_factor_ref           0.2276
_refine_special_details            ?
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
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 1.12975(10) 0.4642(7) 0.15364(13) 0.0440(8) Uani 1 1 d . . . . .
 C2 C 1.15071(12) 0.5581(9) 0.20886(16) 0.0665(11) Uani 1 1 d . . . . .
 H2 H 1.1404 0.4905 0.2371 0.080 Uiso 1 1 calc R U . . .
 C3 C 1.18775(16) 0.7566(11) 0.2219(2) 0.0965(18) Uani 1 1 d . . . . .
 H3 H 1.2023 0.8222 0.2589 0.116 Uiso 1 1 calc R U . . .
 C4 C 1.20247(15) 0.8539(12) 0.1789(4) 0.120(3) Uani 1 1 d . . . . .
 H4 H 1.2274 0.9829 0.1876 0.144 Uiso 1 1 calc R U . . .
 C5 C 1.18144(15) 0.7653(11) 0.1247(3) 0.0966(17) Uani 1 1 d . . . . .
 H5 H 1.1914 0.8358 0.0963 0.116 Uiso 1 1 calc R U . . .
 C6 C 1.14547(12) 0.5717(9) 0.11198(17) 0.0640(10) Uani 1 1 d . . . . .
 H6 H 1.1311 0.5102 0.0746 0.077 Uiso 1 1 calc R U . . .
 C7 C 1.09130(10) 0.2409(7) 0.13857(13) 0.0474(8) Uani 1 1 d . . . . .
 H7A H 1.0874 0.1533 0.1018 0.057 Uiso 1 1 calc R U . . .
 H7B H 1.0992 0.0765 0.1661 0.057 Uiso 1 1 calc R U . . .
 C8 C 1.02447(9) 0.5545(6) 0.09253(11) 0.0341(7) Uani 1 1 d . . . . .
 H8 H 1.0377 0.6078 0.0662 0.041 Uiso 1 1 calc R U . . .
 C9 C 0.98213(9) 0.6609(6) 0.08554(10) 0.0305(6) Uani 1 1 d . . . . .
 C10 C 0.96094(9) 0.5739(6) 0.12558(10) 0.0335(7) Uani 1 1 d . . . . .
 C11 C 0.98545(10) 0.4024(7) 0.17043(11) 0.0439(8) Uani 1 1 d . . . . .
 H11 H 0.9724 0.3504 0.1970 0.053 Uiso 1 1 calc R U . . .
 C12 C 1.03033(11) 0.2961(7) 0.17940(12) 0.0475(8) Uani 1 1 d . . . . .
 C13 C 0.96055(9) 0.8611(7) 0.03908(12) 0.0379(7) Uani 1 1 d . . . . .
 C14 C 0.91382(9) 0.6656(7) 0.11713(11) 0.0377(7) Uani 1 1 d . . . . .
 C15 C 0.90362(11) 0.8048(8) 0.16051(13) 0.0508(8) Uani 1 1 d . . . . .
 H15 H 0.9265 0.8401 0.1951 0.061 Uiso 1 1 calc R U . . .
 C16 C 0.85980(13) 0.8917(9) 0.15279(17) 0.0695(11) Uani 1 1 d . . . . .
 H16 H 0.8532 0.9911 0.1816 0.083 Uiso 1 1 calc R U . . .
 C17 C 0.82641(12) 0.8308(10) 0.10276(18) 0.0731(12) Uani 1 1 d . . . . .
 C18 C 0.83508(12) 0.6898(11) 0.05938(17) 0.0765(12) Uani 1 1 d . . . . .
 H18 H 0.8118 0.6490 0.0254 0.092 Uiso 1 1 calc R U . . .
 C19 C 0.87892(11) 0.6086(9) 0.06665(13) 0.0579(10) Uani 1 1 d . . . . .
 H19 H 0.8851 0.5141 0.0372 0.070 Uiso 1 1 calc R U . . .
 Cl1 Cl 0.77111(4) 0.9366(4) 0.09470(7) 0.1348(7) Uani 1 1 d . . . . .
 N1 N 1.04769(7) 0.3740(5) 0.13667(9) 0.0356(6) Uani 1 1 d . . . . .
 N2 N 0.94376(9) 1.0254(7) 0.00217(11) 0.0564(8) Uani 1 1 d . . . . .
 O1 O 1.05342(8) 0.1404(7) 0.21988(10) 0.0779(9) 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 C2 1.378(5) . ?
 C1 C6 1.391(5) . ?
 C1 C7 1.501(4) . ?
 C2 H2 0.9300 . ?
 C2 C3 1.402(7) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.387(8) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.349(8) . ?
 C5 H5 0.9300 . ?
 C5 C6 1.363(6) . ?
 C6 H6 0.9300 . ?
 C7 H7A 0.9700 . ?
 C7 H7B 0.9700 . ?
 C7 N1 1.481(4) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.368(4) . ?
 C8 N1 1.353(3) . ?
 C9 C10 1.443(4) . ?
 C9 C13 1.431(4) . ?
 C10 C11 1.353(4) . ?
 C10 C14 1.483(4) . ?
 C11 H11 0.9300 . ?
 C11 C12 1.432(4) . ?
 C12 N1 1.410(4) . ?
 C12 O1 1.232(4) . ?
 C13 N2 1.149(4) . ?
 C14 C15 1.385(4) . ?
 C14 C19 1.384(4) . ?
 C15 H15 0.9300 . ?
 C15 C16 1.382(5) . ?
 C16 H16 0.9300 . ?
 C16 C17 1.357(5) . ?
 C17 C18 1.364(6) . ?
 C17 Cl1 1.748(4) . ?
 C18 H18 0.9300 . ?
 C18 C19 1.378(5) . ?
 C19 H19 0.9300 . ?

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
 C2 C1 C6 119.3(4) . . ?
 C2 C1 C7 120.7(3) . . ?
 C6 C1 C7 120.0(3) . . ?
 C1 C2 H2 120.4 . . ?
 C1 C2 C3 119.2(4) . . ?
 C3 C2 H2 120.4 . . ?
 C2 C3 H3 120.4 . . ?
 C4 C3 C2 119.2(5) . . ?
 C4 C3 H3 120.4 . . ?
 C3 C4 H4 119.3 . . ?
 C5 C4 C3 121.4(5) . . ?
 C5 C4 H4 119.3 . . ?
 C4 C5 H5 120.3 . . ?
 C4 C5 C6 119.5(5) . . ?
 C6 C5 H5 120.3 . . ?
 C1 C6 H6 119.3 . . ?
 C5 C6 C1 121.4(4) . . ?
 C5 C6 H6 119.3 . . ?
 C1 C7 H7A 108.7 . . ?
 C1 C7 H7B 108.7 . . ?
 H7A C7 H7B 107.6 . . ?
 N1 C7 C1 114.3(2) . . ?
 N1 C7 H7A 108.7 . . ?
 N1 C7 H7B 108.7 . . ?
 C9 C8 H8 119.0 . . ?
 N1 C8 H8 119.0 . . ?
 N1 C8 C9 122.0(2) . . ?
 C8 C9 C10 119.4(2) . . ?
 C8 C9 C13 118.6(2) . . ?
 C13 C9 C10 122.0(2) . . ?
 C9 C10 C14 121.0(2) . . ?
 C11 C10 C9 117.5(3) . . ?
 C11 C10 C14 121.5(2) . . ?
 C10 C11 H11 118.0 . . ?
 C10 C11 C12 123.9(3) . . ?
 C12 C11 H11 118.0 . . ?
 N1 C12 C11 115.3(2) . . ?
 O1 C12 C11 125.2(3) . . ?
 O1 C12 N1 119.4(3) . . ?
 N2 C13 C9 178.9(3) . . ?
 C15 C14 C10 120.3(2) . . ?
 C19 C14 C10 121.3(2) . . ?
 C19 C14 C15 118.4(3) . . ?
 C14 C15 H15 119.7 . . ?
 C16 C15 C14 120.6(3) . . ?
 C16 C15 H15 119.7 . . ?
 C15 C16 H16 120.3 . . ?
 C17 C16 C15 119.4(3) . . ?
 C17 C16 H16 120.3 . . ?
 C16 C17 C18 121.7(3) . . ?
 C16 C17 Cl1 118.4(3) . . ?
 C18 C17 Cl1 119.9(3) . . ?
 C17 C18 H18 120.5 . . ?
 C17 C18 C19 119.0(3) . . ?
 C19 C18 H18 120.5 . . ?
 C14 C19 H19 119.5 . . ?
 C18 C19 C14 121.0(3) . . ?
 C18 C19 H19 119.5 . . ?
 C8 N1 C7 119.2(2) . . ?
 C8 N1 C12 121.7(2) . . ?
 C12 N1 C7 119.0(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
 C1 C2 C3 C4 0.0(6) . . . . ?
 C1 C7 N1 C8 74.2(3) . . . . ?
 C1 C7 N1 C12 -109.1(3) . . . . ?
 C2 C1 C6 C5 0.7(5) . . . . ?
 C2 C1 C7 N1 76.5(3) . . . . ?
 C2 C3 C4 C5 1.0(7) . . . . ?
 C3 C4 C5 C6 -1.2(7) . . . . ?
 C4 C5 C6 C1 0.3(6) . . . . ?
 C6 C1 C2 C3 -0.8(5) . . . . ?
 C6 C1 C7 N1 -105.4(3) . . . . ?
 C7 C1 C2 C3 177.3(3) . . . . ?
 C7 C1 C6 C5 -177.4(3) . . . . ?
 C8 C9 C10 C11 3.6(4) . . . . ?
 C8 C9 C10 C14 -175.4(2) . . . . ?
 C9 C8 N1 C7 173.8(2) . . . . ?
 C9 C8 N1 C12 -2.8(4) . . . . ?
 C9 C10 C11 C12 -1.9(4) . . . . ?
 C9 C10 C14 C15 -129.2(3) . . . . ?
 C9 C10 C14 C19 52.3(4) . . . . ?
 C10 C11 C12 N1 -2.0(5) . . . . ?
 C10 C11 C12 O1 179.8(3) . . . . ?
 C10 C14 C15 C16 179.8(3) . . . . ?
 C10 C14 C19 C18 178.9(3) . . . . ?
 C11 C10 C14 C15 51.8(4) . . . . ?
 C11 C10 C14 C19 -126.7(3) . . . . ?
 C11 C12 N1 C7 -172.2(3) . . . . ?
 C11 C12 N1 C8 4.4(4) . . . . ?
 C13 C9 C10 C11 -175.1(2) . . . . ?
 C13 C9 C10 C14 5.9(4) . . . . ?
 C14 C10 C11 C12 177.2(3) . . . . ?
 C14 C15 C16 C17 2.1(6) . . . . ?
 C15 C14 C19 C18 0.4(5) . . . . ?
 C15 C16 C17 C18 -1.1(7) . . . . ?
 C15 C16 C17 Cl1 178.7(3) . . . . ?
 C16 C17 C18 C19 -0.3(7) . . . . ?
 C17 C18 C19 C14 0.6(7) . . . . ?
 C19 C14 C15 C16 -1.7(5) . . . . ?
 Cl1 C17 C18 C19 179.9(3) . . . . ?
 N1 C8 C9 C10 -1.3(4) . . . . ?
 N1 C8 C9 C13 177.4(2) . . . . ?
 O1 C12 N1 C7 6.1(4) . . . . ?
 O1 C12 N1 C8 -177.3(3) . . . . ?

