 
data_1 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C13 H10 Cl N5 O' 
_chemical_formula_weight          287.71 
  
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' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
  
_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+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    8.5083(11) 
_cell_length_b                    14.3480(17) 
_cell_length_c                    10.4672(13) 
_cell_angle_alpha                 90 
_cell_angle_beta                  105.064(2) 
_cell_angle_gamma                 90 
_cell_volume                      1233.9(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     3408 
_cell_measurement_theta_min       2.46 
_cell_measurement_theta_max       27.37 
  
_exptl_crystal_description        BLOCK 
_exptl_crystal_colour             COLORLESS
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.549 
_exptl_crystal_F_000              592 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.260 
_exptl_crystal_size_mid           0.250 
_exptl_crystal_size_min           0.240 
_exptl_absorpt_coefficient_mu     0.313 
_shelx_estimated_absorpt_T_min    0.923 
_shelx_estimated_absorpt_T_max    0.929 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             6173 
_diffrn_reflns_av_unetI/netI      0.0208 
_diffrn_reflns_av_R_equivalents   0.0235 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        17 
_diffrn_reflns_limit_l_min        -11 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.857 
_diffrn_reflns_theta_max          24.993 
_diffrn_reflns_theta_full         24.993 
_diffrn_measured_fraction_theta_max   0.997 
_diffrn_measured_fraction_theta_full  0.997 
_diffrn_reflns_Laue_measured_fraction_max    0.997 
_diffrn_reflns_Laue_measured_fraction_full   0.997 
_diffrn_reflns_point_group_measured_fraction_max   0.997 
_diffrn_reflns_point_group_measured_fraction_full  0.997 
_reflns_number_total              2159 
_reflns_number_gt                 1864 
_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 SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'Bruker SHELXTL' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_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+0.3754P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014' 
_refine_ls_extinction_coef        0.030(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2159 
_refine_ls_number_parameters      190 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0382 
_refine_ls_R_factor_gt            0.0316 
_refine_ls_wR_factor_ref          0.0829 
_refine_ls_wR_factor_gt           0.0795 
_refine_ls_goodness_of_fit_ref    1.086 
_refine_ls_restrained_S_all       1.086 
_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 
Cl1 Cl 0.23625(6) 0.59671(3) 0.24509(5) 0.05404(18) Uani 1 1 d . . . . . 
N5 N 0.44502(15) 0.18455(9) 0.52273(13) 0.0346(3) Uani 1 1 d . . . . . 
N4 N 0.14358(15) 0.14295(9) 0.55012(13) 0.0360(3) Uani 1 1 d . . . . . 
O1 O 0.42445(17) 0.07142(10) 0.36815(14) 0.0626(4) Uani 1 1 d . . . . . 
N1 N 0.13631(16) 0.24573(10) 0.69883(13) 0.0426(4) Uani 1 1 d . . . . . 
N2 N 0.00795(18) 0.18592(11) 0.68209(15) 0.0496(4) Uani 1 1 d . . . . . 
N3 N 0.01102(17) 0.12342(11) 0.59345(15) 0.0472(4) Uani 1 1 d . . . . . 
C3 C 0.36878(17) 0.25496(10) 0.58885(14) 0.0308(3) Uani 1 1 d . . . . . 
H3 H 0.4448 0.2696 0.6742 0.037 Uiso 1 1 calc R U . . . 
C13 C 0.34091(17) 0.34356(10) 0.50588(14) 0.0294(3) Uani 1 1 d . . . . . 
C8 C 0.44535(17) 0.36528(10) 0.42606(14) 0.0300(3) Uani 1 1 d . . . . . 
C4 C 0.21767(17) 0.21667(10) 0.61482(14) 0.0318(3) Uani 1 1 d . . . . . 
C9 C 0.41173(18) 0.44402(11) 0.34502(14) 0.0343(4) Uani 1 1 d . . . . . 
H9 H 0.4782 0.4591 0.2902 0.041 Uiso 1 1 calc R U . . . 
C6 C 0.58905(18) 0.30527(11) 0.42920(15) 0.0350(4) Uani 1 1 d . . . . . 
C10 C 0.28015(19) 0.49912(11) 0.34655(15) 0.0360(4) Uani 1 1 d . . . . . 
C2 C 0.3652(2) 0.11528(11) 0.44384(16) 0.0389(4) Uani 1 1 d . . . . . 
C12 C 0.2117(2) 0.40200(11) 0.50745(17) 0.0400(4) Uani 1 1 d . . . . . 
H12 H 0.1455 0.3884 0.5630 0.048 Uiso 1 1 calc R U . . . 
C11 C 0.1800(2) 0.48001(12) 0.42789(17) 0.0433(4) Uani 1 1 d . . . . . 
H11 H 0.0929 0.5189 0.4290 0.052 Uiso 1 1 calc R U . . . 
C5 C 0.60279(18) 0.21591(12) 0.50851(17) 0.0414(4) Uani 1 1 d . . . . . 
H5A H 0.6496 0.1676 0.4649 0.050 Uiso 1 1 calc R U . . . 
H5B H 0.6755 0.2259 0.5956 0.050 Uiso 1 1 calc R U . . . 
C7 C 0.7054(2) 0.32788(15) 0.3716(2) 0.0490(5) Uani 1 1 d . . . . . 
C1 C 0.1970(2) 0.08920(12) 0.45154(18) 0.0465(4) Uani 1 1 d . . . . . 
H1A H 0.1213 0.0989 0.3657 0.056 Uiso 1 1 calc R U . . . 
H1B H 0.1952 0.0235 0.4728 0.056 Uiso 1 1 calc R U . . . 
H7A H 0.705(2) 0.3889(15) 0.3246(19) 0.057(6) Uiso 1 1 d . . . . . 
H7B H 0.800(3) 0.2849(14) 0.3782(19) 0.062(6) Uiso 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 C10 1.7384(16) . ? 
N5 C2 1.356(2) . ? 
N5 C5 1.460(2) . ? 
N5 C3 1.4676(19) . ? 
N4 C4 1.324(2) . ? 
N4 N3 1.3498(18) . ? 
N4 C1 1.453(2) . ? 
O1 C2 1.219(2) . ? 
N1 C4 1.320(2) . ? 
N1 N2 1.364(2) . ? 
N2 N3 1.295(2) . ? 
C3 C4 1.487(2) . ? 
C3 C13 1.523(2) . ? 
C3 H3 0.9800 . ? 
C13 C12 1.386(2) . ? 
C13 C8 1.404(2) . ? 
C8 C9 1.397(2) . ? 
C8 C6 1.489(2) . ? 
C9 C10 1.374(2) . ? 
C9 H9 0.9300 . ? 
C6 C7 1.326(2) . ? 
C6 C5 1.515(2) . ? 
C10 C11 1.380(2) . ? 
C2 C1 1.501(2) . ? 
C12 C11 1.379(2) . ? 
C12 H12 0.9300 . ? 
C11 H11 0.9300 . ? 
C5 H5A 0.9700 . ? 
C5 H5B 0.9700 . ? 
C7 H7A 1.00(2) . ? 
C7 H7B 1.00(2) . ? 
C1 H1A 0.9700 . ? 
C1 H1B 0.9700 . ? 
  
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 N5 C5 119.47(13) . . ? 
C2 N5 C3 125.37(13) . . ? 
C5 N5 C3 111.52(12) . . ? 
C4 N4 N3 108.80(13) . . ? 
C4 N4 C1 126.31(13) . . ? 
N3 N4 C1 124.86(14) . . ? 
C4 N1 N2 104.87(14) . . ? 
N3 N2 N1 111.28(13) . . ? 
N2 N3 N4 105.73(13) . . ? 
N5 C3 C4 109.94(12) . . ? 
N5 C3 C13 109.15(12) . . ? 
C4 C3 C13 113.51(12) . . ? 
N5 C3 H3 108.0 . . ? 
C4 C3 H3 108.0 . . ? 
C13 C3 H3 108.0 . . ? 
C12 C13 C8 119.95(14) . . ? 
C12 C13 C3 120.31(13) . . ? 
C8 C13 C3 119.73(13) . . ? 
C9 C8 C13 118.66(14) . . ? 
C9 C8 C6 121.23(14) . . ? 
C13 C8 C6 120.11(14) . . ? 
N1 C4 N4 109.31(14) . . ? 
N1 C4 C3 129.28(14) . . ? 
N4 C4 C3 121.41(13) . . ? 
C10 C9 C8 119.81(14) . . ? 
C10 C9 H9 120.1 . . ? 
C8 C9 H9 120.1 . . ? 
C7 C6 C8 123.66(17) . . ? 
C7 C6 C5 119.71(16) . . ? 
C8 C6 C5 116.58(13) . . ? 
C9 C10 C11 121.92(15) . . ? 
C9 C10 Cl1 120.18(12) . . ? 
C11 C10 Cl1 117.90(13) . . ? 
O1 C2 N5 123.22(16) . . ? 
O1 C2 C1 117.85(15) . . ? 
N5 C2 C1 118.91(14) . . ? 
C11 C12 C13 121.03(15) . . ? 
C11 C12 H12 119.5 . . ? 
C13 C12 H12 119.5 . . ? 
C12 C11 C10 118.57(15) . . ? 
C12 C11 H11 120.7 . . ? 
C10 C11 H11 120.7 . . ? 
N5 C5 C6 112.00(13) . . ? 
N5 C5 H5A 109.2 . . ? 
C6 C5 H5A 109.2 . . ? 
N5 C5 H5B 109.2 . . ? 
C6 C5 H5B 109.2 . . ? 
H5A C5 H5B 107.9 . . ? 
C6 C7 H7A 122.1(12) . . ? 
C6 C7 H7B 120.0(12) . . ? 
H7A C7 H7B 117.8(17) . . ? 
N4 C1 C2 112.61(13) . . ? 
N4 C1 H1A 109.1 . . ? 
C2 C1 H1A 109.1 . . ? 
N4 C1 H1B 109.1 . . ? 
C2 C1 H1B 109.1 . . ? 
H1A C1 H1B 107.8 . . ? 
  
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 
C4 N1 N2 N3 0.36(18) . . . . ? 
N1 N2 N3 N4 -0.48(18) . . . . ? 
C4 N4 N3 N2 0.41(17) . . . . ? 
C1 N4 N3 N2 178.63(15) . . . . ? 
C2 N5 C3 C4 28.0(2) . . . . ? 
C5 N5 C3 C4 -173.80(12) . . . . ? 
C2 N5 C3 C13 -97.12(17) . . . . ? 
C5 N5 C3 C13 61.09(15) . . . . ? 
N5 C3 C13 C12 149.91(14) . . . . ? 
C4 C3 C13 C12 26.91(19) . . . . ? 
N5 C3 C13 C8 -29.18(17) . . . . ? 
C4 C3 C13 C8 -152.19(13) . . . . ? 
C12 C13 C8 C9 -2.8(2) . . . . ? 
C3 C13 C8 C9 176.31(12) . . . . ? 
C12 C13 C8 C6 176.92(14) . . . . ? 
C3 C13 C8 C6 -4.0(2) . . . . ? 
N2 N1 C4 N4 -0.09(17) . . . . ? 
N2 N1 C4 C3 179.91(14) . . . . ? 
N3 N4 C4 N1 -0.20(17) . . . . ? 
C1 N4 C4 N1 -178.38(15) . . . . ? 
N3 N4 C4 C3 179.80(13) . . . . ? 
C1 N4 C4 C3 1.6(2) . . . . ? 
N5 C3 C4 N1 161.06(15) . . . . ? 
C13 C3 C4 N1 -76.4(2) . . . . ? 
N5 C3 C4 N4 -18.95(19) . . . . ? 
C13 C3 C4 N4 103.63(16) . . . . ? 
C13 C8 C9 C10 1.1(2) . . . . ? 
C6 C8 C9 C10 -178.58(13) . . . . ? 
C9 C8 C6 C7 9.5(2) . . . . ? 
C13 C8 C6 C7 -170.20(15) . . . . ? 
C9 C8 C6 C5 -173.22(13) . . . . ? 
C13 C8 C6 C5 7.1(2) . . . . ? 
C8 C9 C10 C11 1.0(2) . . . . ? 
C8 C9 C10 Cl1 -179.47(11) . . . . ? 
C5 N5 C2 O1 6.6(2) . . . . ? 
C3 N5 C2 O1 163.20(16) . . . . ? 
C5 N5 C2 C1 -174.92(15) . . . . ? 
C3 N5 C2 C1 -18.3(2) . . . . ? 
C8 C13 C12 C11 2.4(2) . . . . ? 
C3 C13 C12 C11 -176.71(15) . . . . ? 
C13 C12 C11 C10 -0.3(3) . . . . ? 
C9 C10 C11 C12 -1.5(3) . . . . ? 
Cl1 C10 C11 C12 179.01(13) . . . . ? 
C2 N5 C5 C6 100.50(16) . . . . ? 
C3 N5 C5 C6 -59.16(17) . . . . ? 
C7 C6 C5 N5 -158.85(15) . . . . ? 
C8 C6 C5 N5 23.76(19) . . . . ? 
C4 N4 C1 C2 9.8(2) . . . . ? 
N3 N4 C1 C2 -168.12(14) . . . . ? 
O1 C2 C1 N4 176.86(16) . . . . ? 
N5 C2 C1 N4 -1.7(2) . . . . ? 
  
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 
C9 H9 O1  0.93 2.60 3.447(2) 152.2 2_655 
C5 H5A Cl1  0.97 2.81 3.7062(18) 153.2 2_645 
C1 H1A Cl1  0.97 2.96 3.7273(19) 136.7 2_545 
  
_refine_diff_density_max    0.229 
_refine_diff_density_min   -0.286 
_refine_diff_density_rms    0.041 
  
  
  
