data_2203266
loop_
_publ_author_name
'Seshadri, Tarimala'
'Fl\"orke, Ulrich'
'Henkel, Gerald'
_publ_section_title
;
N-(8-Quinolyl)-o-phenylenediamine
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o399
_journal_page_last             o400
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C15 H13 N3'
_chemical_formula_moiety       'C15 H13 N3'
_chemical_formula_sum          'C15 H13 N3'
_chemical_formula_weight       235.28
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
N-(8-Quinolyl)-o-phenylenediamine
;
_symmetry_cell_setting         Orthorhombic
_symmetry_space_group_name_H-M 'P c a 21'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_audit_creation_method         SHELXL-97
_cell_angle_alpha              90.00
_cell_angle_beta               90.00
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 10.7227(13)
_cell_length_b                 11.0789(13)
_cell_length_c                 10.1268(12)
_cell_measurement_reflns_used  1682
_cell_measurement_temperature  120(2)
_cell_measurement_theta_max    23.16
_cell_measurement_theta_min    2.64
_cell_volume                   1203.0(2)
_computing_cell_refinement     SMART
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_data_reduction      'SAINT (Bruker, 2002)'
_computing_molecular_graphics  SHELXTL
_computing_publication_material SHELXTL
_computing_structure_refinement SHELXTL
_computing_structure_solution  'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature    120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Bruker SMART CCD area-detector'
_diffrn_measurement_method     '\f and \w'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source       'sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.0593
_diffrn_reflns_av_sigmaI/netI  0.0381
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_l_max     13
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_number          7244
_diffrn_reflns_theta_full      28.30
_diffrn_reflns_theta_max       28.30
_diffrn_reflns_theta_min       1.84
_diffrn_standards_decay_%      <1
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time 480
_diffrn_standards_number       1687
_exptl_absorpt_coefficient_mu  0.080
_exptl_absorpt_correction_T_max 0.989
_exptl_absorpt_correction_T_min 0.941
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2002)'
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  1.299
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     plate
_exptl_crystal_F_000           496
_exptl_crystal_size_max        0.50
_exptl_crystal_size_mid        0.45
_exptl_crystal_size_min        0.02
_refine_diff_density_max       0.284
_refine_diff_density_min       -0.203
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.105
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   174
_refine_ls_number_reflns       1584
_refine_ls_number_restraints   1
_refine_ls_restrained_S_all    1.104
_refine_ls_R_factor_all        0.0496
_refine_ls_R_factor_gt         0.0427
_refine_ls_shift/su_max        0.000
_refine_ls_shift/su_mean       0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0655P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1033
_refine_ls_wR_factor_ref       0.1073
_reflns_number_gt              1409
_reflns_number_total           1584
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 -0.0321(2) 0.4222(2) 0.5373(3) 0.0371(5) Uani d . 1 . . N
H1A -0.002(3) 0.472(3) 0.480(4) 0.042(6) Uiso d . 1 . . H
H1B -0.073(3) 0.354(2) 0.495(3) 0.042(6) Uiso d . 1 . . H
N2 0.16621(17) 0.57715(15) 0.6004(2) 0.0251(4) Uani d . 1 . . N
H2 0.237(3) 0.588(2) 0.577(4) 0.049(9) Uiso d . 1 . . H
N3 0.26133(17) 0.77620(15) 0.4798(2) 0.0269(4) Uani d . 1 . . N
C1 0.0414(2) 0.39785(17) 0.6461(2) 0.0264(5) Uani d . 1 . . C
C2 0.0178(2) 0.2981(2) 0.7281(3) 0.0339(6) Uani d . 1 . . C
H2A -0.0485 0.2446 0.7071 0.041 Uiso calc R 1 . . H
C3 0.0897(2) 0.2768(2) 0.8384(3) 0.0372(6) Uani d . 1 . . C
H3A 0.0725 0.2084 0.8919 0.045 Uiso calc R 1 . . H
C4 0.1867(2) 0.3534(2) 0.8727(3) 0.0380(6) Uani d . 1 . . C
H4A 0.2363 0.3379 0.9486 0.046 Uiso calc R 1 . . H
C5 0.2094(2) 0.4526(2) 0.7940(2) 0.0301(5) Uani d . 1 . . C
H5A 0.2750 0.5062 0.8171 0.036 Uiso calc R 1 . . H
C6 0.13889(19) 0.47598(17) 0.6822(2) 0.0232(4) Uani d . 1 . . C
C7 0.10372(19) 0.68568(17) 0.6152(2) 0.0230(4) Uani d . 1 . . C
C8 -0.0067(2) 0.69593(19) 0.6842(2) 0.0261(5) Uani d . 1 . . C
H8A -0.0411 0.6269 0.7262 0.031 Uiso calc R 1 . . H
C9 -0.0691(2) 0.80762(19) 0.6931(2) 0.0297(5) Uani d . 1 . . C
H9A -0.1456 0.8122 0.7400 0.036 Uiso calc R 1 . . H
C10 -0.0220(2) 0.90953(19) 0.6356(2) 0.0296(5) Uani d . 1 . . C
H10A -0.0639 0.9846 0.6450 0.036 Uiso calc R 1 . . H
C11 0.0899(2) 0.90214(18) 0.5619(2) 0.0268(5) Uani d . 1 . . C
C12 0.1412(2) 1.00072(19) 0.4920(3) 0.0330(6) Uani d . 1 . . C
H12A 0.1033 1.0781 0.4975 0.040 Uiso calc R 1 . . H
C13 0.2452(3) 0.98452(19) 0.4167(3) 0.0362(6) Uani d . 1 . . C
H13A 0.2784 1.0495 0.3666 0.043 Uiso calc R 1 . . H
C14 0.3026(2) 0.8707(2) 0.4141(3) 0.0323(5) Uani d . 1 . . C
H14A 0.3756 0.8612 0.3618 0.039 Uiso calc R 1 . . H
C15 0.15355(19) 0.79004(17) 0.5516(2) 0.0227(4) Uani d . 1 . . C
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0339(11) 0.0359(10) 0.0415(12) -0.0089(9) -0.0070(10) 0.0051(10)
N2 0.0204(9) 0.0202(8) 0.0349(11) 0.0004(7) 0.0074(8) 0.0036(7)
N3 0.0225(9) 0.0251(8) 0.0332(11) -0.0031(7) -0.0002(8) 0.0038(8)
C1 0.0214(10) 0.0218(9) 0.0361(12) 0.0041(8) 0.0045(9) 0.0003(9)
C2 0.0270(12) 0.0244(10) 0.0504(16) -0.0003(8) 0.0125(11) 0.0048(11)
C3 0.0396(14) 0.0299(11) 0.0420(14) 0.0148(10) 0.0169(12) 0.0141(11)
C4 0.0389(14) 0.0429(13) 0.0321(14) 0.0161(11) 0.0056(11) 0.0079(11)
C5 0.0274(11) 0.0322(11) 0.0307(12) 0.0055(9) 0.0025(10) -0.0022(10)
C6 0.0220(10) 0.0194(8) 0.0282(11) 0.0052(7) 0.0076(9) 0.0026(9)
C7 0.0230(10) 0.0213(9) 0.0247(11) -0.0007(8) -0.0015(8) -0.0011(8)
C8 0.0252(11) 0.0253(9) 0.0277(11) 0.0003(8) 0.0031(9) 0.0004(9)
C9 0.0264(11) 0.0330(11) 0.0296(11) 0.0054(8) 0.0024(9) -0.0034(10)
C10 0.0309(12) 0.0241(10) 0.0338(13) 0.0080(8) -0.0041(10) -0.0038(9)
C11 0.0268(11) 0.0234(9) 0.0302(12) 0.0002(8) -0.0080(9) -0.0009(9)
C12 0.0330(12) 0.0228(10) 0.0433(15) -0.0013(9) -0.0112(11) 0.0045(10)
C13 0.0340(12) 0.0289(10) 0.0456(16) -0.0095(10) -0.0076(12) 0.0146(11)
C14 0.0256(11) 0.0337(12) 0.0376(13) -0.0051(9) 0.0003(10) 0.0075(10)
C15 0.0216(10) 0.0220(9) 0.0245(10) -0.0020(8) -0.0040(8) 0.0019(8)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 H1A . . 116(2) ?
C1 N1 H1B . . 116.7(17) ?
H1A N1 H1B . . 112(3) ?
C7 N2 C6 . . 121.40(18) ?
C7 N2 H2 . . 111.2(19) ?
C6 N2 H2 . . 119(2) ?
C14 N3 C15 . . 117.49(18) ?
N1 C1 C6 . . 120.7(2) ?
N1 C1 C2 . . 121.5(2) ?
C6 C1 C2 . . 117.7(2) ?
C3 C2 C1 . . 120.9(2) ?
C3 C2 H2A . . 119.5 ?
C1 C2 H2A . . 119.5 ?
C2 C3 C4 . . 121.2(2) ?
C2 C3 H3A . . 119.4 ?
C4 C3 H3A . . 119.4 ?
C5 C4 C3 . . 118.4(2) ?
C5 C4 H4A . . 120.8 ?
C3 C4 H4A . . 120.8 ?
C4 C5 C6 . . 121.7(2) ?
C4 C5 H5A . . 119.2 ?
C6 C5 H5A . . 119.2 ?
C5 C6 C1 . . 120.2(2) ?
C5 C6 N2 . . 120.7(2) ?
C1 C6 N2 . . 119.1(2) ?
C8 C7 N2 . . 122.81(18) ?
C8 C7 C15 . . 118.90(18) ?
N2 C7 C15 . . 118.24(18) ?
C7 C8 C9 . . 120.8(2) ?
C7 C8 H8A . . 119.6 ?
C9 C8 H8A . . 119.6 ?
C10 C9 C8 . . 121.5(2) ?
C10 C9 H9A . . 119.3 ?
C8 C9 H9A . . 119.3 ?
C9 C10 C11 . . 119.35(19) ?
C9 C10 H10A . . 120.3 ?
C11 C10 H10A . . 120.3 ?
C12 C11 C10 . . 123.3(2) ?
C12 C11 C15 . . 116.9(2) ?
C10 C11 C15 . . 119.76(19) ?
C13 C12 C11 . . 119.8(2) ?
C13 C12 H12A . . 120.1 ?
C11 C12 H12A . . 120.1 ?
C12 C13 C14 . . 119.2(2) ?
C12 C13 H13A . . 120.4 ?
C14 C13 H13A . . 120.4 ?
N3 C14 C13 . . 123.8(2) ?
N3 C14 H14A . . 118.1 ?
C13 C14 H14A . . 118.1 ?
N3 C15 C11 . . 122.70(18) ?
N3 C15 C7 . . 117.61(17) ?
C11 C15 C7 . . 119.68(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.381(3) ?
N1 H1A . 0.86(3) ?
N1 H1B . 0.97(3) ?
N2 C7 . 1.385(2) ?
N2 C6 . 1.424(3) ?
N2 H2 . 0.81(4) ?
N3 C14 . 1.317(3) ?
N3 C15 . 1.374(3) ?
C1 C6 . 1.406(3) ?
C1 C2 . 1.405(3) ?
C2 C3 . 1.377(4) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.387(4) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.379(3) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.387(3) ?
C5 H5A . 0.9500 ?
C7 C8 . 1.379(3) ?
C7 C15 . 1.427(3) ?
C8 C9 . 1.410(3) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.367(3) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.415(3) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.413(3) ?
C11 C15 . 1.421(3) ?
C12 C13 . 1.363(4) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.404(3) ?
C13 H13A . 0.9500 ?
C14 H14A . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A N2 . 0.86(3) 2.47(3) 2.806(3) 104(3)
N2 H2 N3 . 0.81(4) 2.32(3) 2.719(2) 111(2)
N1 H1B N3 3_465 0.97(3) 2.29(3) 3.175(3) 150(2)
N2 H2 N1 3_565 0.81(4) 2.51(4) 3.298(3) 166(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -178.2(2) ?
C6 C1 C2 C3 . . . . -1.2(3) ?
C1 C2 C3 C4 . . . . 0.5(4) ?
C2 C3 C4 C5 . . . . 0.5(3) ?
C3 C4 C5 C6 . . . . -0.7(3) ?
C4 C5 C6 C1 . . . . 0.0(3) ?
C4 C5 C6 N2 . . . . -178.3(2) ?
N1 C1 C6 C5 . . . . 177.9(2) ?
C2 C1 C6 C5 . . . . 1.0(3) ?
N1 C1 C6 N2 . . . . -3.8(3) ?
C2 C1 C6 N2 . . . . 179.25(19) ?
C7 N2 C6 C5 . . . . -95.6(2) ?
C7 N2 C6 C1 . . . . 86.1(3) ?
C6 N2 C7 C8 . . . . -16.3(3) ?
C6 N2 C7 C15 . . . . 166.3(2) ?
N2 C7 C8 C9 . . . . -177.9(2) ?
C15 C7 C8 C9 . . . . -0.6(3) ?
C7 C8 C9 C10 . . . . -0.9(4) ?
C8 C9 C10 C11 . . . . 2.1(4) ?
C9 C10 C11 C12 . . . . 175.7(2) ?
C9 C10 C11 C15 . . . . -1.7(3) ?
C10 C11 C12 C13 . . . . -176.0(2) ?
C15 C11 C12 C13 . . . . 1.6(3) ?
C11 C12 C13 C14 . . . . -2.5(4) ?
C15 N3 C14 C13 . . . . 2.0(4) ?
C12 C13 C14 N3 . . . . 0.7(4) ?
C14 N3 C15 C11 . . . . -3.0(3) ?
C14 N3 C15 C7 . . . . 175.6(2) ?
C12 C11 C15 N3 . . . . 1.2(3) ?
C10 C11 C15 N3 . . . . 178.9(2) ?
C12 C11 C15 C7 . . . . -177.4(2) ?
C10 C11 C15 C7 . . . . 0.3(3) ?
C8 C7 C15 N3 . . . . -177.8(2) ?
N2 C7 C15 N3 . . . . -0.3(3) ?
C8 C7 C15 C11 . . . . 0.9(3) ?
N2 C7 C15 C11 . . . . 178.3(2) ?