 
data_260312_KK_DSM01_sq
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C16 H13 N3 O'
_chemical_formula_sum
 'C17 H0 Cl3 N3 O' 
_chemical_formula_weight          368.55

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                    9.7927(6)
_cell_length_b                    9.7276(7)
_cell_length_c                    19.7920(14)
_cell_angle_alpha                 90
_cell_angle_beta                  103.471(2)
_cell_angle_gamma                 90
_cell_volume                      1833.5(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     198(2)
_cell_measurement_reflns_used     5959
_cell_measurement_theta_min       2.35
_cell_measurement_theta_max       25.78
 
_exptl_crystal_description        'needle'
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.335          
_exptl_crystal_F_000              728
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.120
_exptl_crystal_size_min           0.090
_exptl_absorpt_coefficient_mu     0.506
_shelx_estimated_absorpt_T_min    0.906
_shelx_estimated_absorpt_T_max    0.956
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.5730
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       198(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Ius 3.0 microfocus source'
_diffrn_measurement_device_type   'PHOTON II CPAD detector'
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             44124
_diffrn_reflns_av_unetI/netI      0.0577
_diffrn_reflns_av_R_equivalents   0.1043
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          2.116
_diffrn_reflns_theta_max          26.438
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3779
_reflns_number_gt                 2735
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX4 software' 
_computing_cell_refinement        'Bruker APEX4 software' 
_computing_data_reduction         'Bruker APEX4 software' 
_computing_structure_solution     'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement   'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
_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)+(0.1885P)²+0.5443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3779
_refine_ls_number_parameters      184
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0926
_refine_ls_R_factor_gt            0.0714
_refine_ls_wR_factor_ref          0.2760
_refine_ls_wR_factor_gt           0.2372
_refine_ls_goodness_of_fit_ref    1.042
_refine_ls_restrained_S_all       1.042
_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
O1 O 0.4546(3) 0.46086(19) 0.74784(11) 0.0568(5) Uani 1 1 d . . . . .
N1 N 0.1742(3) 0.6585(3) 0.52498(14) 0.0621(7) Uani 1 1 d . . . . .
C1 C 0.7205(3) 0.6436(3) 0.93110(14) 0.0420(5) Uani 1 1 d . . . . .
C2 C 0.3161(3) 0.7449(3) 0.63181(16) 0.0487(6) Uani 1 1 d . . . . .
H1AA H 0.372(4) 0.825(4) 0.659(2) 0.073 Uiso 1 1 d . U . . .
N2 N 0.5185(3) 0.6821(2) 0.75830(12) 0.0507(6) Uani 1 1 d . . . . .
H2 H 0.504476 0.766019 0.741568 0.061 Uiso 1 1 calc R U . . .
N3 N 0.6191(3) 0.6575(2) 0.81924(12) 0.0470(5) Uani 1 1 d . . . . .
C3 C 0.2323(3) 0.7612(3) 0.56578(17) 0.0576(7) Uani 1 1 d . . . . .
H3 H 0.215047 0.852111 0.548383 0.069 Uiso 1 1 calc R U . . .
C4 C 0.1979(4) 0.5329(3) 0.55085(18) 0.0649(9) Uani 1 1 d . . . . .
H4 H 0.154352 0.457770 0.523479 0.078 Uiso 1 1 calc R U . . .
C5 C 0.2828(4) 0.5056(3) 0.61562(16) 0.0571(7) Uani 1 1 d . . . . .
H5 H 0.298373 0.413377 0.631367 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4428(3) 0.5771(3) 0.72517(13) 0.0427(6) Uani 1 1 d . . . . .
C7 C 0.7585(3) 0.6457(3) 0.82319(16) 0.0538(7) Uani 1 1 d . . . . .
H7 H 0.802425 0.644018 0.785168 0.065 Uiso 1 1 calc R U . . .
C8 C 0.8238(3) 0.6366(3) 0.89139(15) 0.0516(7) Uani 1 1 d . . . . .
H8 H 0.922063 0.627219 0.909559 0.062 Uiso 1 1 calc R U . . .
C10 C 0.5924(3) 0.6574(3) 0.88441(14) 0.0437(6) Uani 1 1 d . . . . .
H10 H 0.503162 0.665320 0.895205 0.052 Uiso 1 1 calc R U . . .
C11 C 0.7435(3) 0.6379(3) 1.00708(14) 0.0417(5) Uani 1 1 d . . . . .
C12 C 0.8768(3) 0.6353(4) 1.04854(17) 0.0669(9) Uani 1 1 d . . . . .
H12 H 0.954769 0.637387 1.027591 0.080 Uiso 1 1 calc R U . . .
C13 C 0.9004(4) 0.6297(5) 1.11993(19) 0.0795(12) Uani 1 1 d . . . . .
H13 H 0.993915 0.629352 1.147393 0.095 Uiso 1 1 calc R U . . .
C14 C 0.7899(4) 0.6247(4) 1.15174(17) 0.0637(8) Uani 1 1 d . . . . .
H14 H 0.805950 0.619901 1.200910 0.076 Uiso 1 1 calc R U . . .
C15 C 0.6571(4) 0.6267(5) 1.11138(19) 0.0765(11) Uani 1 1 d . . . . .
H15 H 0.579739 0.623677 1.132750 0.092 Uiso 1 1 calc R U . . .
C16 C 0.6324(4) 0.6330(5) 1.03967(18) 0.0699(10) Uani 1 1 d . . . . .
H16 H 0.538635 0.634104 1.012508 0.084 Uiso 1 1 calc R U . . .
C19 C 0.3445(3) 0.6119(3) 0.65703(13) 0.0409(5) 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
O1 C6 1.212(3) . ?
N1 C4 1.324(4) . ?
N1 C3 1.327(4) . ?
C1 C10 1.380(4) . ?
C1 C8 1.420(4) . ?
C1 C11 1.469(4) . ?
C2 C3 1.381(4) . ?
C2 C19 1.392(4) . ?
C2 H1AA 1.03(4) . ?
N2 C6 1.340(4) . ?
N2 N3 1.389(3) . ?
N2 H2 0.8800 . ?
N3 C7 1.353(4) . ?
N3 C10 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9500 . ?
C5 C19 1.370(4) . ?
C5 H5 0.9500 . ?
C6 C19 1.502(4) . ?
C7 C8 1.355(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.371(4) . ?
C11 C16 1.389(4) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.358(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
 
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
C4 N1 C3 116.6(3) . . ?
C10 C1 C8 106.7(2) . . ?
C10 C1 C11 126.0(3) . . ?
C8 C1 C11 127.3(3) . . ?
C3 C2 C19 118.1(3) . . ?
C3 C2 H1AA 123(2) . . ?
C19 C2 H1AA 118(2) . . ?
C6 N2 N3 119.6(2) . . ?
C6 N2 H2 120.2 . . ?
N3 N2 H2 120.2 . . ?
C7 N3 C10 110.8(2) . . ?
C7 N3 N2 124.5(2) . . ?
C10 N3 N2 124.3(3) . . ?
N1 C3 C2 124.5(3) . . ?
N1 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
N1 C4 C5 123.4(3) . . ?
N1 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C19 C5 C4 119.7(3) . . ?
C19 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
O1 C6 N2 122.4(3) . . ?
O1 C6 C19 121.9(2) . . ?
N2 C6 C19 115.7(2) . . ?
N3 C7 C8 107.4(3) . . ?
N3 C7 H7 126.3 . . ?
C8 C7 H7 126.3 . . ?
C7 C8 C1 108.4(3) . . ?
C7 C8 H8 125.8 . . ?
C1 C8 H8 125.8 . . ?
N3 C10 C1 106.6(2) . . ?
N3 C10 H10 126.7 . . ?
C1 C10 H10 126.7 . . ?
C12 C11 C16 117.5(3) . . ?
C12 C11 C1 120.7(3) . . ?
C16 C11 C1 121.8(3) . . ?
C11 C12 C13 121.5(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C5 C19 C2 117.7(3) . . ?
C5 C19 C6 117.9(2) . . ?
C2 C19 C6 124.4(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
C6 N2 N3 C7 99.6(3) . . . . ?
C6 N2 N3 C10 -88.1(3) . . . . ?
C4 N1 C3 C2 1.1(5) . . . . ?
C19 C2 C3 N1 1.5(5) . . . . ?
C3 N1 C4 C5 -2.6(6) . . . . ?
N1 C4 C5 C19 1.6(6) . . . . ?
N3 N2 C6 O1 3.0(4) . . . . ?
N3 N2 C6 C19 -175.5(2) . . . . ?
C10 N3 C7 C8 0.5(3) . . . . ?
N2 N3 C7 C8 173.7(3) . . . . ?
N3 C7 C8 C1 -0.2(3) . . . . ?
C10 C1 C8 C7 -0.2(3) . . . . ?
C11 C1 C8 C7 -180.0(3) . . . . ?
C7 N3 C10 C1 -0.6(3) . . . . ?
N2 N3 C10 C1 -173.8(2) . . . . ?
C8 C1 C10 N3 0.5(3) . . . . ?
C11 C1 C10 N3 -179.7(2) . . . . ?
C10 C1 C11 C12 -174.6(3) . . . . ?
C8 C1 C11 C12 5.2(4) . . . . ?
C10 C1 C11 C16 6.3(4) . . . . ?
C8 C1 C11 C16 -174.0(3) . . . . ?
C16 C11 C12 C13 -0.7(6) . . . . ?
C1 C11 C12 C13 -179.9(4) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 C11 -0.2(7) . . . . ?
C12 C11 C16 C15 0.4(6) . . . . ?
C1 C11 C16 C15 179.5(3) . . . . ?
C4 C5 C19 C2 1.1(5) . . . . ?
C4 C5 C19 C6 -176.4(3) . . . . ?
C3 C2 C19 C5 -2.5(4) . . . . ?
C3 C2 C19 C6 174.8(3) . . . . ?
O1 C6 C19 C5 -9.4(4) . . . . ?
N2 C6 C19 C5 169.1(3) . . . . ?
O1 C6 C19 C2 173.2(3) . . . . ?
N2 C6 C19 C2 -8.2(4) . . . . ?
 
_refine_diff_density_max    0.531
_refine_diff_density_min   -0.483
_refine_diff_density_rms    0.120




