#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227324.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227324
loop_
_publ_author_name
'Chandraprakash, K.'
'Ramesh, P.'
'Ravichandran, K.'
'Mohan, P. S.'
'Ponnuswamy, M. N.'
_publ_section_title
;
 2-Methoxyquinoline-3-carbaldehyde
;
_journal_coeditor_code           CI5162
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2510
_journal_paper_doi               10.1107/S1600536810034744
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H9 N O2'
_chemical_formula_moiety         'C11 H9 N O2'
_chemical_formula_sum            'C11 H9 N O2'
_chemical_formula_weight         187.19
_chemical_name_common            2-Methoxyquinoline-3-carbaldehyde
_chemical_name_systematic
;
2-Methoxyquinoline-3-carbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 90.612(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8206(6)
_cell_length_b                   4.8446(3)
_cell_length_c                   21.6828(14)
_cell_measurement_reflns_used    1216
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.40
_cell_measurement_theta_min      1.88
_cell_volume                     926.50(10)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8812
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0622P)²+0.1045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                1658
_reflns_number_total             2305
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5162.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227324
_cod_database_fobs_code          2227324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
O O1 -0.04660(11) 0.2962(2) 0.42027(4) 0.0664(3) Uani d . 1 . .
O O2 0.32252(12) 0.2311(3) 0.52502(5) 0.0860(4) Uani d . 1 . .
N N1 0.05048(11) 0.6258(2) 0.35559(5) 0.0522(3) Uani d . 1 . .
C C2 0.06704(13) 0.4656(3) 0.40308(5) 0.0498(3) Uani d . 1 . .
C C3 0.20052(14) 0.4490(3) 0.44096(5) 0.0505(3) Uani d . 1 . .
C C4 0.31810(14) 0.6144(3) 0.42593(6) 0.0546(3) Uani d . 1 . .
H H4 0.4064 0.6107 0.4497 0.066 Uiso calc R 1 . .
C C5 0.30810(14) 0.7921(3) 0.37465(6) 0.0502(3) Uani d . 1 . .
C C6 0.42741(16) 0.9652(3) 0.35643(7) 0.0639(4) Uani d . 1 . .
H H6 0.5179 0.9658 0.3789 0.077 Uiso calc R 1 . .
C C7 0.41177(18) 1.1312(3) 0.30644(7) 0.0682(4) Uani d . 1 . .
H H7 0.4913 1.2450 0.2947 0.082 Uiso calc R 1 . .
C C8 0.27587(18) 1.1311(3) 0.27260(6) 0.0656(4) Uani d . 1 . .
H H8 0.2658 1.2462 0.2385 0.079 Uiso calc R 1 . .
C C9 0.15831(16) 0.9657(3) 0.28878(6) 0.0594(3) Uani d . 1 . .
H H9 0.0691 0.9678 0.2655 0.071 Uiso calc R 1 . .
C C10 0.17083(14) 0.7915(2) 0.34040(5) 0.0476(3) Uani d . 1 . .
C C11 -0.17739(17) 0.2814(4) 0.38058(7) 0.0822(5) Uani d . 1 . .
H H11A -0.2189 0.4630 0.3750 0.123 Uiso calc R 1 . .
H H11B -0.2521 0.1638 0.3989 0.123 Uiso calc R 1 . .
H H11C -0.1487 0.2076 0.3413 0.123 Uiso calc R 1 . .
C C12 0.21226(17) 0.2551(3) 0.49311(6) 0.0634(4) Uani d . 1 . .
H H12 0.1288 0.1449 0.5017 0.076 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C11 . . 117.35(10) ?
C2 N1 C10 . . 117.35(10) ?
N1 C2 O1 . . 120.34(10) ?
N1 C2 C3 . . 125.09(11) ?
O1 C2 C3 . . 114.57(11) ?
C4 C3 C2 . . 117.15(11) ?
C4 C3 C12 . . 120.99(12) ?
C2 C3 C12 . . 121.83(11) ?
C3 C4 C5 . . 120.70(11) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 123.08(12) ?
C6 C5 C10 . . 119.56(12) ?
C4 C5 C10 . . 117.36(11) ?
C7 C6 C5 . . 120.57(13) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 119.91(13) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 121.09(13) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 120.39(13) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
N1 C10 C9 . . 119.18(12) ?
N1 C10 C5 . . 122.35(11) ?
C9 C10 C5 . . 118.47(12) ?
O1 C11 H11A . . 109.5 ?
O1 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O1 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O2 C12 C3 . . 123.89(13) ?
O2 C12 H12 . . 118.1 ?
C3 C12 H12 . . 118.1 ?
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
O1 C2 . 1.3510(15) ?
O1 C11 . 1.4336(16) ?
O2 C12 . 1.1932(16) ?
N1 C2 . 1.2964(16) ?
N1 C10 . 1.3736(16) ?
C2 C3 . 1.4307(16) ?
C3 C4 . 1.3534(17) ?
C3 C12 . 1.4728(18) ?
C4 C5 . 1.4081(18) ?
C4 H4 . 0.93 ?
C5 C6 . 1.4055(18) ?
C5 C10 . 1.4136(17) ?
C6 C7 . 1.356(2) ?
C6 H6 . 0.93 ?
C7 C8 . 1.399(2) ?
C7 H7 . 0.93 ?
C8 C9 . 1.360(2) ?
C8 H8 . 0.93 ?
C9 C10 . 1.4050(18) ?
C9 H9 . 0.93 ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
C12 H12 . 0.93 ?
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
C4 H4 O2 3_666 0.93 2.56 3.4157(16) 152
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
C10 N1 C2 O1 . . . . -179.57(11) ?
C10 N1 C2 C3 . . . . 0.28(19) ?
C11 O1 C2 N1 . . . . 6.24(19) ?
C11 O1 C2 C3 . . . . -173.63(13) ?
N1 C2 C3 C4 . . . . 0.2(2) ?
O1 C2 C3 C4 . . . . -179.94(11) ?
N1 C2 C3 C12 . . . . -178.08(13) ?
O1 C2 C3 C12 . . . . 1.78(18) ?
C2 C3 C4 C5 . . . . -0.62(19) ?
C12 C3 C4 C5 . . . . 177.68(12) ?
C3 C4 C5 C6 . . . . -179.05(13) ?
C3 C4 C5 C10 . . . . 0.56(19) ?
C4 C5 C6 C7 . . . . 179.67(14) ?
C10 C5 C6 C7 . . . . 0.1(2) ?
C5 C6 C7 C8 . . . . 0.1(2) ?
C6 C7 C8 C9 . . . . -0.3(2) ?
C7 C8 C9 C10 . . . . 0.4(2) ?
C2 N1 C10 C9 . . . . 179.19(11) ?
C2 N1 C10 C5 . . . . -0.34(18) ?
C8 C9 C10 N1 . . . . -179.80(12) ?
C8 C9 C10 C5 . . . . -0.25(19) ?
C6 C5 C10 N1 . . . . 179.55(12) ?
C4 C5 C10 N1 . . . . -0.06(18) ?
C6 C5 C10 C9 . . . . 0.02(18) ?
C4 C5 C10 C9 . . . . -179.60(11) ?
C4 C3 C12 O2 . . . . 0.3(2) ?
C2 C3 C12 O2 . . . . 178.47(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 732875
