 
data_260514_KK_DHL01
 
_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 H12 N2'
_chemical_formula_sum
 'C16 H12 N2' 
_chemical_formula_weight          232.28

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'
 
_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                    6.5221(3)
_cell_length_b                    12.6675(7)
_cell_length_c                    14.7843(8)
_cell_angle_alpha                 90
_cell_angle_beta                  100.902(2)
_cell_angle_gamma                 90
_cell_volume                      1199.41(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     7154
_cell_measurement_theta_min       2.81
_cell_measurement_theta_max       26.31
 
_exptl_crystal_description        'needle'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.286          
_exptl_crystal_F_000              488
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.150
_exptl_crystal_size_mid           0.070
_exptl_crystal_size_min           0.070
_exptl_absorpt_coefficient_mu     0.077
_shelx_estimated_absorpt_T_min    0.989
_shelx_estimated_absorpt_T_max    0.995
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.7094
_exptl_absorpt_correction_T_max   0.7454
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(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             28739
_diffrn_reflns_av_unetI/netI      0.0282
_diffrn_reflns_av_R_equivalents   0.0688
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.806
_diffrn_reflns_theta_max          26.401
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              2459
_reflns_number_gt                 2107
_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 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)+(0.0773P)²+0.1805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef        0.013(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2459
_refine_ls_number_parameters      164
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0420
_refine_ls_R_factor_gt            0.0357
_refine_ls_wR_factor_ref          0.1210
_refine_ls_wR_factor_gt           0.1117
_refine_ls_goodness_of_fit_ref    1.013
_refine_ls_restrained_S_all       1.013
_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
N1 N 0.21146(16) 0.57225(8) 0.44934(7) 0.0361(3) Uani 1 1 d . . . . .
C1 C 0.55959(17) 0.41239(8) 0.27415(7) 0.0271(3) Uani 1 1 d . . . . .
N2 N 0.32225(16) 0.62551(8) 0.39594(7) 0.0357(3) Uani 1 1 d . . . . .
C2 C 0.47847(19) 0.33185(9) 0.21356(8) 0.0319(3) Uani 1 1 d . . . . .
H2 H 0.343985 0.303921 0.215088 0.038 Uiso 1 1 calc R U . . .
C3 C 0.5930(2) 0.29225(10) 0.15104(9) 0.0377(3) Uani 1 1 d . . . . .
H3 H 0.535370 0.238325 0.109215 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7909(2) 0.33081(10) 0.14920(9) 0.0378(3) Uani 1 1 d . . . . .
H4 H 0.869959 0.302757 0.107041 0.045 Uiso 1 1 calc R U . . .
C5 C 0.87232(18) 0.41055(10) 0.20931(9) 0.0363(3) Uani 1 1 d . . . . .
H5 H 1.008074 0.437181 0.208393 0.044 Uiso 1 1 calc R U . . .
C6 C 0.75763(18) 0.45186(9) 0.27079(8) 0.0311(3) Uani 1 1 d . . . . .
H6 H 0.814221 0.507474 0.310972 0.037 Uiso 1 1 calc R U . . .
C7 C 0.43689(17) 0.46031(9) 0.33838(7) 0.0272(3) Uani 1 1 d . . . . .
C8 C 0.32213(16) 0.40553(9) 0.39344(7) 0.0274(3) Uani 1 1 d . . . . .
C9 C 0.21347(18) 0.46773(9) 0.44719(8) 0.0320(3) Uani 1 1 d . . . . .
H9 H 0.134417 0.431753 0.485379 0.038 Uiso 1 1 calc R U . . .
C10 C 0.42856(18) 0.57100(9) 0.34382(8) 0.0313(3) Uani 1 1 d . . . . .
H10 H 0.505962 0.610093 0.306886 0.038 Uiso 1 1 calc R U . . .
C11 C 0.30688(17) 0.28896(9) 0.39953(7) 0.0281(3) Uani 1 1 d . . . . .
C12 C 0.48507(19) 0.22589(9) 0.41430(8) 0.0323(3) Uani 1 1 d . . . . .
H12 H 0.619272 0.257340 0.420652 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4663(2) 0.11747(10) 0.41970(9) 0.0387(3) Uani 1 1 d . . . . .
H13 H 0.588004 0.074585 0.429423 0.046 Uiso 1 1 calc R U . . .
C14 C 0.2715(2) 0.07094(10) 0.41105(9) 0.0415(3) Uani 1 1 d . . . . .
H14 H 0.259612 -0.003686 0.413868 0.050 Uiso 1 1 calc R U . . .
C15 C 0.0953(2) 0.13284(10) 0.39838(9) 0.0406(3) Uani 1 1 d . . . . .
H15 H -0.038263 0.100988 0.393258 0.049 Uiso 1 1 calc R U . . .
C16 C 0.11212(19) 0.24185(10) 0.39306(8) 0.0349(3) Uani 1 1 d . . . . .
H16 H -0.009935 0.284393 0.384956 0.042 Uiso 1 1 calc R U . . .
 
 
_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
N1 C9 1.3244(15) . ?
N1 N2 1.3477(14) . ?
C1 C2 1.3942(16) . ?
C1 C6 1.3947(15) . ?
C1 C7 1.4825(15) . ?
N2 C10 1.3242(15) . ?
C2 C3 1.3877(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3847(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3833(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3845(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3909(15) . ?
C7 C10 1.4062(16) . ?
C8 C9 1.4027(16) . ?
C8 C11 1.4839(16) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.3903(16) . ?
C11 C12 1.3931(16) . ?
C12 C13 1.3825(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3845(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3745(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3886(17) . ?
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
C9 N1 N2 118.53(10) . . ?
C2 C1 C6 118.74(10) . . ?
C2 C1 C7 121.73(10) . . ?
C6 C1 C7 119.46(10) . . ?
C10 N2 N1 118.52(10) . . ?
C3 C2 C1 120.38(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.44(12) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.41(11) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.55(11) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.46(11) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C10 115.66(10) . . ?
C8 C7 C1 125.87(10) . . ?
C10 C7 C1 118.45(10) . . ?
C7 C8 C9 115.90(11) . . ?
C7 C8 C11 125.56(10) . . ?
C9 C8 C11 118.54(10) . . ?
N1 C9 C8 125.69(11) . . ?
N1 C9 H9 117.2 . . ?
C8 C9 H9 117.2 . . ?
N2 C10 C7 125.69(11) . . ?
N2 C10 H10 117.2 . . ?
C7 C10 H10 117.2 . . ?
C16 C11 C12 119.27(11) . . ?
C16 C11 C8 119.60(10) . . ?
C12 C11 C8 121.11(10) . . ?
C13 C12 C11 119.90(11) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.48(12) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.91(12) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.14(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.26(11) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
 
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
C9 N1 N2 C10 -0.14(16) . . . . ?
C6 C1 C2 C3 -0.20(17) . . . . ?
C7 C1 C2 C3 176.73(11) . . . . ?
C1 C2 C3 C4 1.22(19) . . . . ?
C2 C3 C4 C5 -1.06(19) . . . . ?
C3 C4 C5 C6 -0.11(18) . . . . ?
C4 C5 C6 C1 1.13(18) . . . . ?
C2 C1 C6 C5 -0.96(17) . . . . ?
C7 C1 C6 C5 -177.96(10) . . . . ?
C2 C1 C7 C8 46.09(16) . . . . ?
C6 C1 C7 C8 -137.00(12) . . . . ?
C2 C1 C7 C10 -132.15(11) . . . . ?
C6 C1 C7 C10 44.76(15) . . . . ?
C10 C7 C8 C9 -0.07(14) . . . . ?
C1 C7 C8 C9 -178.36(10) . . . . ?
C10 C7 C8 C11 -179.93(10) . . . . ?
C1 C7 C8 C11 1.78(17) . . . . ?
N2 N1 C9 C8 -0.04(18) . . . . ?
C7 C8 C9 N1 0.15(17) . . . . ?
C11 C8 C9 N1 -179.98(11) . . . . ?
N1 N2 C10 C7 0.21(17) . . . . ?
C8 C7 C10 N2 -0.10(17) . . . . ?
C1 C7 C10 N2 178.32(11) . . . . ?
C7 C8 C11 C16 -131.90(12) . . . . ?
C9 C8 C11 C16 48.25(15) . . . . ?
C7 C8 C11 C12 49.96(16) . . . . ?
C9 C8 C11 C12 -129.89(11) . . . . ?
C16 C11 C12 C13 1.84(16) . . . . ?
C8 C11 C12 C13 179.99(10) . . . . ?
C11 C12 C13 C14 -0.36(17) . . . . ?
C12 C13 C14 C15 -0.99(18) . . . . ?
C13 C14 C15 C16 0.83(19) . . . . ?
C14 C15 C16 C11 0.67(18) . . . . ?
C12 C11 C16 C15 -2.00(17) . . . . ?
C8 C11 C16 C15 179.82(11) . . . . ?
 
_refine_diff_density_max    0.184
_refine_diff_density_min   -0.159
_refine_diff_density_rms    0.034



