#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/12/2241266.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_2241266
loop_
_publ_author_name
'Nivedita Desai, R.'
'Sreenivasa, S.'
'Naveen, S.'
'Lokanath, N. K.'
'Suchetan, P. A.'
'Aruna Kumar, D. B.'
_publ_section_title
;
 Crystal structure of 2-(4-methylpiperazin-1-yl)quinoline-3-carbaldehyde
;
_journal_coeditor_code           GK2647
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o900
_journal_page_last               o901
_journal_paper_doi               10.1107/S2056989015020186
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C15 H17 N3 O'
_chemical_formula_moiety         'C15 H17 N3 O'
_chemical_formula_sum            'C15 H17 N3 O'
_chemical_formula_weight         255.32
_chemical_melting_point          384
_chemical_name_systematic
;
2-(4-Methylpiperazin-1-yl)quinoline-3-carbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.591(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3282(4)
_cell_length_b                   5.8935(2)
_cell_length_c                   18.9202(7)
_cell_measurement_reflns_used    143
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.5
_cell_measurement_theta_min      3.9
_cell_volume                     1336.18(8)
_computing_cell_refinement
;
APEX2 and SAINT-Plus (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker, 2009)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEXII CCD '
_diffrn_measurement_method       'phi and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9762
_diffrn_reflns_theta_full        64.47
_diffrn_reflns_theta_max         64.47
_diffrn_reflns_theta_min         3.90
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  0.8589
_exptl_absorpt_correction_T_min  0.8382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0542
_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)+(0.1151P)²+0.0654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1623
_reflns_number_gt                1859
_reflns_number_total             2181
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2647sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2241266
_cod_database_fobs_code          2241266
loop_
_symmetry_equiv_pos_as_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'
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
N N1 0.44347(10) 0.7887(2) 0.60405(6) 0.0446(4) Uani d . 1 1
N N2 0.31637(10) 0.4894(2) 0.58318(6) 0.0443(4) Uani d . 1 1
N N3 0.15374(11) 0.2821(2) 0.46867(7) 0.0492(4) Uani d . 1 1
O O1 0.33529(13) 0.4038(3) 0.79890(7) 0.0800(5) Uani d . 1 1
C C1 0.38623(12) 0.6362(3) 0.63074(7) 0.0415(4) Uani d . 1 1
C C2 0.39605(12) 0.6082(3) 0.70773(8) 0.0435(4) Uani d . 1 1
C C3 0.46317(13) 0.7537(3) 0.75426(8) 0.0456(4) Uani d . 1 1
H H3 0.4690 0.7410 0.8040 0.055 Uiso calc R 1 1
C C4 0.52382(12) 0.9229(3) 0.72789(8) 0.0429(4) Uani d . 1 1
C C5 0.59503(14) 1.0786(3) 0.77313(9) 0.0517(5) Uani d . 1 1
H H5 0.6035 1.0718 0.8232 0.062 Uiso calc R 1 1
C C6 0.65119(15) 1.2380(3) 0.74416(10) 0.0571(5) Uani d . 1 1
H H6 0.6980 1.3397 0.7744 0.068 Uiso calc R 1 1
C C7 0.63874(16) 1.2497(3) 0.66853(10) 0.0580(5) Uani d . 1 1
H H7 0.6768 1.3606 0.6490 0.070 Uiso calc R 1 1
C C8 0.57153(14) 1.1003(3) 0.62334(9) 0.0516(5) Uani d . 1 1
H H8 0.5648 1.1094 0.5734 0.062 Uiso calc R 1 1
C C9 0.51232(12) 0.9326(3) 0.65156(8) 0.0430(4) Uani d . 1 1
C C10 0.19665(13) 0.5037(3) 0.58101(8) 0.0477(4) Uani d . 1 1
H H10A 0.1659 0.6413 0.5560 0.057 Uiso calc R 1 1
H H10B 0.1861 0.5100 0.6302 0.057 Uiso calc R 1 1
C C11 0.13648(13) 0.3007(3) 0.54226(9) 0.0517(5) Uani d . 1 1
H H11A 0.1635 0.1642 0.5694 0.062 Uiso calc R 1 1
H H11B 0.0573 0.3142 0.5399 0.062 Uiso calc R 1 1
C C12 0.27299(14) 0.2697(3) 0.47221(9) 0.0522(5) Uani d . 1 1
H H12A 0.2846 0.2582 0.4234 0.063 Uiso calc R 1 1
H H12B 0.3038 0.1347 0.4988 0.063 Uiso calc R 1 1
C C13 0.33266(14) 0.4768(3) 0.50926(8) 0.0516(5) Uani d . 1 1
H H13A 0.4117 0.4670 0.5106 0.062 Uiso calc R 1 1
H H13B 0.3031 0.6123 0.4824 0.062 Uiso calc R 1 1
C C14 0.09682(18) 0.0831(4) 0.43236(9) 0.0660(6) Uani d . 1 1
H H14A 0.1106 0.0708 0.3846 0.099 Uiso calc R 1 1
H H14B 0.0181 0.0973 0.4285 0.099 Uiso calc R 1 1
H H14C 0.1242 -0.0501 0.4600 0.099 Uiso calc R 1 1
C C15 0.34545(14) 0.4132(3) 0.73732(9) 0.0561(5) Uani d . 1 1
H H15 0.3201 0.2913 0.7067 0.067 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C9 118.40(12)
C1 N2 C13 116.58(12)
C1 N2 C10 116.60(12)
C13 N2 C10 109.84(11)
C14 N3 C12 110.53(15)
C14 N3 C11 110.40(13)
C12 N3 C11 109.34(12)
N1 C1 N2 118.89(12)
N1 C1 C2 122.74(14)
N2 C1 C2 118.32(13)
C3 C2 C1 118.36(14)
C3 C2 C15 119.41(14)
C1 C2 C15 121.90(15)
C2 C3 C4 120.69(14)
C2 C3 H3 119.7
C4 C3 H3 119.7
C3 C4 C5 123.55(14)
C3 C4 C9 117.08(14)
C5 C4 C9 119.36(15)
C6 C5 C4 120.59(15)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C7 120.09(16)
C5 C6 H6 120.0
C7 C6 H6 120.0
C8 C7 C6 120.80(16)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 120.59(15)
C7 C8 H8 119.7
C9 C8 H8 119.7
N1 C9 C8 118.78(13)
N1 C9 C4 122.64(14)
C8 C9 C4 118.56(15)
N2 C10 C11 110.18(13)
N2 C10 H10A 109.6
C11 C10 H10A 109.6
N2 C10 H10B 109.6
C11 C10 H10B 109.6
H10A C10 H10B 108.1
N3 C11 C10 111.00(13)
N3 C11 H11A 109.4
C10 C11 H11A 109.4
N3 C11 H11B 109.4
C10 C11 H11B 109.4
H11A C11 H11B 108.0
N3 C12 C13 110.89(14)
N3 C12 H12A 109.5
C13 C12 H12A 109.5
N3 C12 H12B 109.5
C13 C12 H12B 109.5
H12A C12 H12B 108.0
N2 C13 C12 108.90(13)
N2 C13 H13A 109.9
C12 C13 H13A 109.9
N2 C13 H13B 109.9
C12 C13 H13B 109.9
H13A C13 H13B 108.3
N3 C14 H14A 109.5
N3 C14 H14B 109.5
H14A C14 H14B 109.5
N3 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O1 C15 C2 123.51(18)
O1 C15 H15 118.2
C2 C15 H15 118.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.315(2)
N1 C9 1.375(2)
N2 C1 1.391(2)
N2 C13 1.4607(18)
N2 C10 1.4693(19)
N3 C14 1.454(2)
N3 C12 1.458(2)
N3 C11 1.461(2)
O1 C15 1.202(2)
C1 C2 1.442(2)
C2 C3 1.361(2)
C2 C15 1.479(2)
C3 C4 1.406(2)
C3 H3 0.9300
C4 C5 1.411(2)
C4 C9 1.419(2)
C5 C6 1.357(3)
C5 H5 0.9300
C6 C7 1.404(3)
C6 H6 0.9300
C7 C8 1.364(3)
C7 H7 0.9300
C8 C9 1.406(2)
C8 H8 0.9300
C10 C11 1.505(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.510(2)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15 0.9300
