 
data_mo_d8v18867_0m 
  
_audit_creation_method            SHELXL-2013 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C15 H11 Cl2 N O' 
_chemical_formula_weight          292.15 
  
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' 
 'Cl'  'Cl'   0.1484   0.1585 
 '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' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/n' 
_space_group_name_Hall            '-P 2yn' 
  
_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+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    4.4481(2) 
_cell_length_b                    14.2679(6) 
_cell_length_c                    20.9740(12) 
_cell_angle_alpha                 90 
_cell_angle_beta                  92.061(2) 
_cell_angle_gamma                 90 
_cell_volume                      1330.25(11) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     3566 
_cell_measurement_theta_min       6.493 
_cell_measurement_theta_max       54.902 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.459 
_exptl_crystal_F_000              600 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.180 
_exptl_crystal_size_mid           0.150 
_exptl_crystal_size_min           0.120 
_exptl_absorpt_coefficient_mu     0.477 
_shelx_estimated_absorpt_T_min    0.919 
_shelx_estimated_absorpt_T_max    0.945 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6442 
_exptl_absorpt_correction_T_max   0.7456 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             6472 
_diffrn_reflns_av_unetI/netI      0.0269 
_diffrn_reflns_av_R_equivalents   0.0206 
_diffrn_reflns_limit_h_min        -5 
_diffrn_reflns_limit_h_max        5 
_diffrn_reflns_limit_k_min        -17 
_diffrn_reflns_limit_k_max        17 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        25 
_diffrn_reflns_theta_min          2.855 
_diffrn_reflns_theta_max          25.999 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.985 
_diffrn_measured_fraction_theta_full  0.984 
_diffrn_reflns_Laue_measured_fraction_max    0.985 
_diffrn_reflns_Laue_measured_fraction_full   0.984 
_diffrn_reflns_point_group_measured_fraction_max   0.985 
_diffrn_reflns_point_group_measured_fraction_full  0.984 
_reflns_number_total              2590 
_reflns_number_gt                 2167 
_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        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_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)+(0.0379P)²+0.4655P] 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      SHELXL 
_refine_ls_extinction_coef        0.015(6) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2590 
_refine_ls_number_parameters      173 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0466 
_refine_ls_R_factor_gt            0.0375 
_refine_ls_wR_factor_ref          0.0976 
_refine_ls_wR_factor_gt           0.0901 
_refine_ls_goodness_of_fit_ref    1.019 
_refine_ls_restrained_S_all       1.019 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_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 
Cl1 Cl 0.90055(13) 0.54463(4) 0.83031(3) 0.0755(2) Uani 1 1 d . . . . . 
Cl2 Cl 0.54655(16) 0.65622(4) 0.72144(3) 0.0819(3) Uani 1 1 d . . . . . 
O1 O 0.2593(3) 0.44755(9) 0.43416(6) 0.0654(4) Uani 1 1 d . . . . . 
N1 N 0.3692(3) 0.39168(10) 0.53515(7) 0.0467(4) Uani 1 1 d . . . . . 
H1 H 0.4801 0.4377 0.5482 0.056 Uiso 1 1 calc R U . . . 
C1 C 0.3406(4) 0.48878(12) 0.68117(8) 0.0464(4) Uani 1 1 d . . . . . 
H1A H 0.2343 0.5224 0.6497 0.056 Uiso 1 1 calc R U . . . 
C2 C 0.5217(4) 0.53561(13) 0.72553(9) 0.0492(4) Uani 1 1 d . . . . . 
C3 C 0.6774(4) 0.48696(14) 0.77326(8) 0.0502(4) Uani 1 1 d . . . . . 
C4 C 0.6538(4) 0.39080(14) 0.77575(9) 0.0563(5) Uani 1 1 d . . . . . 
H4 H 0.7577 0.3574 0.8076 0.068 Uiso 1 1 calc R U . . . 
C5 C 0.4764(4) 0.34432(13) 0.73106(9) 0.0528(5) Uani 1 1 d . . . . . 
H5 H 0.4632 0.2793 0.7329 0.063 Uiso 1 1 calc R U . . . 
C6 C 0.3164(4) 0.39219(12) 0.68324(8) 0.0429(4) Uani 1 1 d . . . . . 
C7 C 0.1282(4) 0.33962(12) 0.63416(8) 0.0469(4) Uani 1 1 d . . . . . 
H7A H -0.0418 0.3783 0.6207 0.056 Uiso 1 1 calc R U . . . 
H7B H 0.0498 0.2835 0.6536 0.056 Uiso 1 1 calc R U . . . 
C8 C 0.3016(4) 0.31165(11) 0.57518(8) 0.0427(4) Uani 1 1 d . . . . . 
H8 H 0.4882 0.2794 0.5883 0.051 Uiso 1 1 calc R U . . . 
C9 C 0.1202(4) 0.25127(11) 0.52950(8) 0.0438(4) Uani 1 1 d . . . . . 
C10 C -0.0030(5) 0.16320(13) 0.53816(10) 0.0579(5) Uani 1 1 d . . . . . 
H10 H 0.0216 0.1319 0.5769 0.069 Uiso 1 1 calc R U . . . 
C11 C -0.1636(5) 0.12342(15) 0.48739(12) 0.0694(6) Uani 1 1 d . . . . . 
H11 H -0.2496 0.0646 0.4923 0.083 Uiso 1 1 calc R U . . . 
C12 C -0.1989(5) 0.16903(15) 0.42974(12) 0.0724(6) Uani 1 1 d . . . . . 
H12 H -0.3070 0.1404 0.3963 0.087 Uiso 1 1 calc R U . . . 
C13 C -0.0763(5) 0.25649(14) 0.42086(10) 0.0625(5) Uani 1 1 d . . . . . 
H13 H -0.1004 0.2876 0.3820 0.075 Uiso 1 1 calc R U . . . 
C14 C 0.0839(4) 0.29656(12) 0.47156(8) 0.0465(4) Uani 1 1 d . . . . . 
C15 C 0.2433(4) 0.38755(12) 0.47594(8) 0.0476(4) 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 
Cl1 C3 1.7345(18) . ? 
Cl2 C2 1.7268(19) . ? 
O1 C15 1.229(2) . ? 
N1 C15 1.345(2) . ? 
N1 C8 1.455(2) . ? 
N1 H1 0.8600 . ? 
C1 C2 1.381(2) . ? 
C1 C6 1.383(2) . ? 
C1 H1A 0.9300 . ? 
C2 C3 1.383(3) . ? 
C3 C4 1.377(3) . ? 
C4 C5 1.374(3) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.388(2) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.504(2) . ? 
C7 C8 1.534(2) . ? 
C7 H7A 0.9700 . ? 
C7 H7B 0.9700 . ? 
C8 C9 1.502(2) . ? 
C8 H8 0.9800 . ? 
C9 C14 1.381(2) . ? 
C9 C10 1.385(2) . ? 
C10 C11 1.383(3) . ? 
C10 H10 0.9300 . ? 
C11 C12 1.377(3) . ? 
C11 H11 0.9300 . ? 
C12 C13 1.377(3) . ? 
C12 H12 0.9300 . ? 
C13 C14 1.382(2) . ? 
C13 H13 0.9300 . ? 
C14 C15 1.480(2) . ? 
  
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 
C15 N1 C8 114.23(13) . . ? 
C15 N1 H1 122.9 . . ? 
C8 N1 H1 122.9 . . ? 
C2 C1 C6 120.33(16) . . ? 
C2 C1 H1A 119.8 . . ? 
C6 C1 H1A 119.8 . . ? 
C1 C2 C3 120.64(17) . . ? 
C1 C2 Cl2 119.04(14) . . ? 
C3 C2 Cl2 120.31(14) . . ? 
C4 C3 C2 119.37(17) . . ? 
C4 C3 Cl1 119.27(15) . . ? 
C2 C3 Cl1 121.36(15) . . ? 
C5 C4 C3 119.85(17) . . ? 
C5 C4 H4 120.1 . . ? 
C3 C4 H4 120.1 . . ? 
C4 C5 C6 121.48(17) . . ? 
C4 C5 H5 119.3 . . ? 
C6 C5 H5 119.3 . . ? 
C1 C6 C5 118.33(16) . . ? 
C1 C6 C7 121.16(15) . . ? 
C5 C6 C7 120.49(16) . . ? 
C6 C7 C8 113.48(13) . . ? 
C6 C7 H7A 108.9 . . ? 
C8 C7 H7A 108.9 . . ? 
C6 C7 H7B 108.9 . . ? 
C8 C7 H7B 108.9 . . ? 
H7A C7 H7B 107.7 . . ? 
N1 C8 C9 101.50(13) . . ? 
N1 C8 C7 112.42(14) . . ? 
C9 C8 C7 112.94(13) . . ? 
N1 C8 H8 109.9 . . ? 
C9 C8 H8 109.9 . . ? 
C7 C8 H8 109.9 . . ? 
C14 C9 C10 120.38(17) . . ? 
C14 C9 C8 109.64(14) . . ? 
C10 C9 C8 129.98(17) . . ? 
C11 C10 C9 117.85(19) . . ? 
C11 C10 H10 121.1 . . ? 
C9 C10 H10 121.1 . . ? 
C12 C11 C10 121.44(19) . . ? 
C12 C11 H11 119.3 . . ? 
C10 C11 H11 119.3 . . ? 
C13 C12 C11 120.9(2) . . ? 
C13 C12 H12 119.5 . . ? 
C11 C12 H12 119.5 . . ? 
C12 C13 C14 117.8(2) . . ? 
C12 C13 H13 121.1 . . ? 
C14 C13 H13 121.1 . . ? 
C9 C14 C13 121.61(17) . . ? 
C9 C14 C15 108.38(15) . . ? 
C13 C14 C15 130.01(17) . . ? 
O1 C15 N1 126.50(16) . . ? 
O1 C15 C14 127.34(16) . . ? 
N1 C15 C14 106.16(15) . . ? 
  
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 
C6 C1 C2 C3 -1.1(3) . . . . ? 
C6 C1 C2 Cl2 179.96(13) . . . . ? 
C1 C2 C3 C4 0.9(3) . . . . ? 
Cl2 C2 C3 C4 179.83(15) . . . . ? 
C1 C2 C3 Cl1 -178.80(14) . . . . ? 
Cl2 C2 C3 Cl1 0.1(2) . . . . ? 
C2 C3 C4 C5 -0.1(3) . . . . ? 
Cl1 C3 C4 C5 179.63(15) . . . . ? 
C3 C4 C5 C6 -0.6(3) . . . . ? 
C2 C1 C6 C5 0.5(3) . . . . ? 
C2 C1 C6 C7 -178.04(15) . . . . ? 
C4 C5 C6 C1 0.4(3) . . . . ? 
C4 C5 C6 C7 178.87(17) . . . . ? 
C1 C6 C7 C8 88.97(19) . . . . ? 
C5 C6 C7 C8 -89.49(19) . . . . ? 
C15 N1 C8 C9 3.02(18) . . . . ? 
C15 N1 C8 C7 -117.92(16) . . . . ? 
C6 C7 C8 N1 -71.44(18) . . . . ? 
C6 C7 C8 C9 174.43(14) . . . . ? 
N1 C8 C9 C14 -2.31(18) . . . . ? 
C7 C8 C9 C14 118.28(16) . . . . ? 
N1 C8 C9 C10 177.54(18) . . . . ? 
C7 C8 C9 C10 -61.9(2) . . . . ? 
C14 C9 C10 C11 -0.6(3) . . . . ? 
C8 C9 C10 C11 179.60(18) . . . . ? 
C9 C10 C11 C12 0.5(3) . . . . ? 
C10 C11 C12 C13 -0.4(4) . . . . ? 
C11 C12 C13 C14 0.3(3) . . . . ? 
C10 C9 C14 C13 0.5(3) . . . . ? 
C8 C9 C14 C13 -179.68(16) . . . . ? 
C10 C9 C14 C15 -178.87(16) . . . . ? 
C8 C9 C14 C15 1.0(2) . . . . ? 
C12 C13 C14 C9 -0.3(3) . . . . ? 
C12 C13 C14 C15 178.9(2) . . . . ? 
C8 N1 C15 O1 177.65(18) . . . . ? 
C8 N1 C15 C14 -2.5(2) . . . . ? 
C9 C14 C15 O1 -179.31(19) . . . . ? 
C13 C14 C15 O1 1.4(3) . . . . ? 
C9 C14 C15 N1 0.9(2) . . . . ? 
C13 C14 C15 N1 -178.37(19) . . . . ? 
  
_refine_diff_density_max    0.189 
_refine_diff_density_min   -0.290 
_refine_diff_density_rms    0.032 
  
_shelxl_version_number 2013-4 
  
  
  
