#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/53/2235329.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2235329
loop_
_publ_author_name
'Li, Yanfeng'
'Zhou, Hongbo'
'Shen, Xiaoping'
_publ_section_title
;
 N-(Quinolin-8-yl)quinoline-2-carboxamide
;
_journal_coeditor_code           ZL2476
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1688
_journal_paper_doi               10.1107/S1600536812020144
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C19 H13 N3 O'
_chemical_formula_moiety         'C19 H13 N3 O'
_chemical_formula_sum            'C19 H13 N3 O'
_chemical_formula_weight         299.32
_chemical_name_systematic
;
N-(Quinolin-8-yl)quinoline-2-carboxamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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                   6.3651(13)
_cell_length_b                   11.475(2)
_cell_length_c                   19.861(4)
_cell_measurement_reflns_used    6054
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.0137
_cell_measurement_theta_min      3.3611
_cell_volume                     1450.6(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2008)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn 724 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6769
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0351
_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/[σ²(Fo²)+(0.0494P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                1442
_reflns_number_total             1553
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2476.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     P2ac2ab
_cod_database_code               2235329
_cod_database_fobs_code          2235329
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
O O1 -0.0149(2) 0.41328(13) 0.73413(7) 0.0458(4) Uani d . 1 1
N N1 -0.1752(2) 0.46907(14) 0.56729(8) 0.0328(4) Uani d . 1 1
C C1 -0.3327(3) 0.44137(16) 0.52317(10) 0.0309(4) Uani d . 1 1
N N2 0.1160(2) 0.54135(14) 0.65635(8) 0.0336(4) Uani d . 1 1
H H2A 0.0898 0.5707 0.6163 0.040 Uiso calc R 1 1
C C2 -0.3099(3) 0.47410(18) 0.45477(10) 0.0367(5) Uani d . 1 1
H H2 -0.1874 0.5146 0.4407 0.044 Uiso calc R 1 1
N N3 0.3570(3) 0.69181(14) 0.58750(8) 0.0385(4) Uani d . 1 1
C C3 -0.4630(3) 0.44780(19) 0.40896(10) 0.0405(5) Uani d . 1 1
H H3 -0.4453 0.4691 0.3631 0.049 Uiso calc R 1 1
C C4 -0.6456(3) 0.38961(18) 0.42926(11) 0.0416(5) Uani d . 1 1
H H4 -0.7514 0.3724 0.3970 0.050 Uiso calc R 1 1
C C5 -0.6737(3) 0.35718(18) 0.49498(10) 0.0390(5) Uani d . 1 1
H H5 -0.7993 0.3187 0.5082 0.047 Uiso calc R 1 1
C C6 -0.5164(3) 0.38082(16) 0.54318(10) 0.0324(5) Uani d . 1 1
C C7 -0.5302(3) 0.34377(17) 0.61049(10) 0.0364(5) Uani d . 1 1
H H7 -0.6505 0.3024 0.6257 0.044 Uiso calc R 1 1
C C8 -0.3693(3) 0.36763(17) 0.65394(10) 0.0358(5) Uani d . 1 1
H H8 -0.3739 0.3413 0.6993 0.043 Uiso calc R 1 1
C C9 -0.1960(3) 0.43222(16) 0.62995(10) 0.0317(5) Uani d . 1 1
C C10 -0.0232(3) 0.46113(17) 0.67895(10) 0.0329(4) Uani d . 1 1
C C11 0.2965(3) 0.58357(17) 0.68860(10) 0.0322(5) Uani d . 1 1
C C12 0.3571(3) 0.55062(19) 0.75238(9) 0.0362(5) Uani d . 1 1
H H12 0.2716 0.4994 0.7781 0.043 Uiso calc R 1 1
C C13 0.5465(3) 0.59343(19) 0.77909(10) 0.0409(6) Uani d . 1 1
H H13 0.5880 0.5697 0.8229 0.049 Uiso calc R 1 1
C C14 0.6721(3) 0.66767(18) 0.74419(10) 0.0388(5) Uani d . 1 1
H H14 0.7999 0.6945 0.7635 0.047 Uiso calc R 1 1
C C15 0.6127(3) 0.70472(17) 0.67950(10) 0.0341(5) Uani d . 1 1
C C16 0.7326(3) 0.78261(18) 0.64020(11) 0.0404(5) Uani d . 1 1
H H16 0.8604 0.8134 0.6572 0.049 Uiso calc R 1 1
C C17 0.6643(4) 0.81326(18) 0.57795(11) 0.0423(5) Uani d . 1 1
H H17 0.7423 0.8667 0.5513 0.051 Uiso calc R 1 1
C C18 0.4767(4) 0.76476(18) 0.55348(10) 0.0436(6) Uani d . 1 1
H H18 0.4330 0.7860 0.5094 0.052 Uiso calc R 1 1
C C19 0.4227(3) 0.66226(17) 0.65098(10) 0.0315(4) Uani d . 1 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N1 C1 117.09(17)
N1 C1 C2 118.50(18)
N1 C1 C6 122.59(17)
C2 C1 C6 118.90(18)
C10 N2 C11 128.30(17)
C10 N2 H2A 115.8
C11 N2 H2A 115.8
C3 C2 C1 120.5(2)
C3 C2 H2 119.8
C1 C2 H2 119.8
C18 N3 C19 116.89(19)
C2 C3 C4 120.37(19)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 120.8(2)
C5 C4 H4 119.6
C3 C4 H4 119.6
C4 C5 C6 120.1(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C7 C6 C5 122.86(19)
C7 C6 C1 117.81(18)
C5 C6 C1 119.30(18)
C8 C7 C6 119.55(19)
C8 C7 H7 120.2
C6 C7 H7 120.2
C7 C8 C9 118.52(19)
C7 C8 H8 120.7
C9 C8 H8 120.7
N1 C9 C8 124.35(19)
N1 C9 C10 117.73(18)
C8 C9 C10 117.92(17)
O1 C10 N2 124.89(19)
O1 C10 C9 120.68(19)
N2 C10 C9 114.42(16)
C12 C11 N2 123.71(19)
C12 C11 C19 120.01(19)
N2 C11 C19 116.26(17)
C11 C12 C13 119.4(2)
C11 C12 H12 120.3
C13 C12 H12 120.3
C14 C13 C12 122.1(2)
C14 C13 H13 118.9
C12 C13 H13 118.9
C13 C14 C15 119.8(2)
C13 C14 H14 120.1
C15 C14 H14 120.1
C14 C15 C16 123.5(2)
C14 C15 C19 119.3(2)
C16 C15 C19 117.19(18)
C17 C16 C15 119.7(2)
C17 C16 H16 120.2
C15 C16 H16 120.2
C16 C17 C18 119.0(2)
C16 C17 H17 120.5
C18 C17 H17 120.5
N3 C18 C17 124.4(2)
N3 C18 H18 117.8
C17 C18 H18 117.8
N3 C19 C11 117.95(18)
N3 C19 C15 122.76(19)
C11 C19 C15 119.28(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.227(2)
N1 C9 1.321(2)
N1 C1 1.369(2)
C1 C2 1.417(3)
C1 C6 1.417(3)
N2 C10 1.354(3)
N2 C11 1.402(2)
N2 H2A 0.8800
C2 C3 1.367(3)
C2 H2 0.9500
N3 C18 1.318(3)
N3 C19 1.371(2)
C3 C4 1.400(3)
C3 H3 0.9500
C4 C5 1.369(3)
C4 H4 0.9500
C5 C6 1.412(3)
C5 H5 0.9500
C6 C7 1.405(3)
C7 C8 1.367(3)
C7 H7 0.9500
C8 C9 1.412(3)
C8 H8 0.9500
C9 C10 1.505(3)
C11 C12 1.377(3)
C11 C19 1.421(3)
C12 C13 1.406(3)
C12 H12 0.9500
C13 C14 1.358(3)
C13 H13 0.9500
C14 C15 1.405(3)
C14 H14 0.9500
C15 C16 1.411(3)
C15 C19 1.421(3)
C16 C17 1.357(3)
C16 H16 0.9500
C17 C18 1.405(3)
C17 H17 0.9500
C18 H18 0.9500
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
N2 H2A N1 0.88 2.27 2.693(2) 109.0
N2 H2A N3 0.88 2.27 2.684(2) 109.0
C12 H12 O1 0.95 2.25 2.867(2) 122.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4465671
