 
data_A25054O_019
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C10 H10 N2'
_chemical_formula_sum
 'C10 H10 N2' 
_chemical_formula_weight          158.20

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       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    5.8167(4)
_cell_length_b                    7.6196(6)
_cell_length_c                    19.0009(16)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      842.14(11)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     4058
_cell_measurement_theta_min       3.43
_cell_measurement_theta_max       27.90
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.248          
_exptl_crystal_F_000              336
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.089
_exptl_crystal_size_mid           0.056
_exptl_crystal_size_min           0.022
_exptl_absorpt_coefficient_mu     0.076
_shelx_estimated_absorpt_T_min    0.993
_shelx_estimated_absorpt_T_max    0.998
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.6787
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(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             12298
_diffrn_reflns_av_unetI/netI      0.0473
_diffrn_reflns_av_R_equivalents   0.0599
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          2.880
_diffrn_reflns_theta_max          28.063
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.993
_diffrn_measured_fraction_theta_full  0.991
_diffrn_reflns_Laue_measured_fraction_max    0.993
_diffrn_reflns_Laue_measured_fraction_full   0.991
_diffrn_reflns_point_group_measured_fraction_max   0.992
_diffrn_reflns_point_group_measured_fraction_full  0.992
_reflns_number_total              2027
_reflns_number_gt                 1298
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.677
_reflns_Friedel_fraction_max      0.992
_reflns_Friedel_fraction_full     0.993
 
_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 APEX5 software' 
_computing_cell_refinement        'Bruker APEX5 software' 
_computing_data_reduction         'Bruker APEX5 software' 
_computing_structure_solution     'SHELXS-2013/1 (Sheldrick, 2013)'
_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)+(0.0341P)²+0.0996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_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_abs_structure_details
;
 Flack x determined using 396 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -1.1(10)
_chemical_absolute_configuration  .
_refine_ls_number_reflns          2027
_refine_ls_number_parameters      115
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1012
_refine_ls_R_factor_gt            0.0531
_refine_ls_wR_factor_ref          0.1113
_refine_ls_wR_factor_gt           0.0930
_refine_ls_goodness_of_fit_ref    1.102
_refine_ls_restrained_S_all       1.102
_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
C1 C -0.0024(5) 0.7675(4) 0.68878(17) 0.0645(8) Uani 1 1 d . . . . .
H1 H -0.086527 0.827076 0.722872 0.077 Uiso 1 1 calc R U . . .
C2 C -0.0833(6) 0.7609(4) 0.6208(2) 0.0784(10) Uani 1 1 d . . . . .
H2 H -0.220599 0.816850 0.609556 0.094 Uiso 1 1 calc R U . . .
C3 C 0.0342(6) 0.6740(5) 0.56987(19) 0.0801(10) Uani 1 1 d . . . . .
H3 H -0.023039 0.668908 0.524213 0.096 Uiso 1 1 calc R U . . .
C4 C 0.2378(6) 0.5938(4) 0.58637(16) 0.0706(9) Uani 1 1 d . . . . .
H4 H 0.320039 0.535644 0.551489 0.085 Uiso 1 1 calc R U . . .
C5 C 0.3222(5) 0.5985(3) 0.65411(15) 0.0585(7) Uani 1 1 d . . . . .
H5 H 0.459922 0.542171 0.664473 0.070 Uiso 1 1 calc R U . . .
C6 C 0.2039(4) 0.6864(3) 0.70739(14) 0.0519(7) Uani 1 1 d . . . . .
C7 C 0.4894(5) 0.6138(3) 0.80405(14) 0.0547(7) Uani 1 1 d . . . . .
H7 H 0.593967 0.550915 0.776931 0.066 Uiso 1 1 calc R U . . .
C8 C 0.2917(5) 0.6908(3) 0.77994(13) 0.0503(6) Uani 1 1 d . . . . .
C9 C 0.1883(5) 0.7724(3) 0.83883(16) 0.0615(7) Uani 1 1 d . . . . .
H9 H 0.051715 0.835880 0.838393 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3224(6) 0.7422(4) 0.89628(16) 0.0664(8) Uani 1 1 d . . . . .
H10 H 0.293998 0.780590 0.941917 0.080 Uiso 1 1 calc R U . . .
N11 N 0.5070(4) 0.6447(3) 0.87448(12) 0.0603(6) Uani 1 1 d . . . . .
N12 N 0.6864(6) 0.5914(4) 0.91981(15) 0.0803(8) Uani 1 1 d . . . . .
H12A H 0.687(7) 0.465(6) 0.914(2) 0.121 Uiso 1 1 d . U . . .
H12B H 0.841(7) 0.649(6) 0.9039(18) 0.121 Uiso 1 1 d . 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
C1 C2 1.376(4) . ?
C1 C6 1.395(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.357(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(4) . ?
C5 H5 0.9300 . ?
C6 C8 1.471(4) . ?
C7 N11 1.363(3) . ?
C7 C8 1.370(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.414(4) . ?
C9 C10 1.362(4) . ?
C9 H9 0.9300 . ?
C10 N11 1.369(4) . ?
C10 H10 0.9300 . ?
N11 N12 1.413(4) . ?
N12 H12A 0.97(4) . ?
N12 H12B 1.05(4) . ?
 
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 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 116.9(3) . . ?
C5 C6 C8 121.3(2) . . ?
C1 C6 C8 121.7(2) . . ?
N11 C7 C8 108.5(2) . . ?
N11 C7 H7 125.8 . . ?
C8 C7 H7 125.8 . . ?
C7 C8 C9 106.3(2) . . ?
C7 C8 C6 126.5(2) . . ?
C9 C8 C6 127.2(2) . . ?
C10 C9 C8 108.4(2) . . ?
C10 C9 H9 125.8 . . ?
C8 C9 H9 125.8 . . ?
C9 C10 N11 107.4(2) . . ?
C9 C10 H10 126.3 . . ?
N11 C10 H10 126.3 . . ?
C7 N11 C10 109.4(2) . . ?
C7 N11 N12 127.2(3) . . ?
C10 N11 N12 123.4(3) . . ?
N11 N12 H12A 102(2) . . ?
N11 N12 H12B 110(2) . . ?
H12A N12 H12B 112(4) . . ?
 
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 0.5(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 C8 179.5(2) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C1 C6 C8 -179.4(3) . . . . ?
N11 C7 C8 C9 0.4(3) . . . . ?
N11 C7 C8 C6 -178.6(2) . . . . ?
C5 C6 C8 C7 -0.2(4) . . . . ?
C1 C6 C8 C7 179.0(2) . . . . ?
C5 C6 C8 C9 -179.0(3) . . . . ?
C1 C6 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C6 C8 C9 C10 178.6(2) . . . . ?
C8 C9 C10 N11 0.3(3) . . . . ?
C8 C7 N11 C10 -0.3(3) . . . . ?
C8 C7 N11 N12 -178.8(3) . . . . ?
C9 C10 N11 C7 0.0(3) . . . . ?
C9 C10 N11 N12 178.6(3) . . . . ?
 
_refine_diff_density_max    0.106
_refine_diff_density_min   -0.135
_refine_diff_density_rms    0.029



