#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/62/2226256.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_2226256
loop_
_publ_author_name
'Liu, Shou-Xin'
'Zhang, Zhao-Hui'
'Yang, Yu-Feng'
'Zhen, Xiao-Li'
'Han, Jian-Rong'
_publ_section_title
;
 Dimethyl 2-(2-quinolylmethyl)malonate
;
_journal_coeditor_code           PV2271
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1383
_journal_paper_doi               10.1107/S1600536810013930
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H15 N O4'
_chemical_formula_moiety         'C15 H15 N O4'
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.28
_chemical_name_systematic
;
Dimethyl 2-(2-quinolylmethyl)malonate
;
_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                 107.92(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.626(2)
_cell_length_b                   16.198(3)
_cell_length_c                   8.1859(16)
_cell_measurement_reflns_used    4229
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.865
_cell_measurement_theta_min      2.014
_cell_volume                     1340.6(5)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8841
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.169
_refine_ls_extinction_coef       0.133(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.2353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                2094
_reflns_number_total             2355
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2271.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226256
_cod_database_fobs_code          2226256
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 0.42646(9) 0.11002(5) 0.37324(10) 0.0208(2) Uani d . 1 . .
O O2 0.28197(9) 0.17212(5) 0.48439(11) 0.0238(3) Uani d . 1 . .
O O3 0.57807(9) 0.20028(5) 0.71040(11) 0.0259(3) Uani d . 1 . .
O O4 0.58734(10) 0.12269(6) 0.94065(12) 0.0315(3) Uani d . 1 . .
N N1 0.24000(10) -0.02029(6) 0.47394(13) 0.0193(3) Uani d . 1 . .
C C1 0.14301(12) -0.06967(7) 0.37093(16) 0.0186(3) Uani d . 1 . .
C C2 0.13159(14) -0.07574(8) 0.19515(17) 0.0249(3) Uani d . 1 . .
H H2 0.1898 -0.0466 0.1519 0.030 Uiso calc R 1 . .
C C3 0.03559(14) -0.12414(8) 0.08742(17) 0.0275(3) Uani d . 1 . .
H H3 0.0287 -0.1271 -0.0285 0.033 Uiso calc R 1 . .
C C4 -0.05277(13) -0.16937(8) 0.15063(17) 0.0240(3) Uani d . 1 . .
H H4 -0.1164 -0.2029 0.0771 0.029 Uiso calc R 1 . .
C C5 -0.04480(13) -0.16388(8) 0.32021(17) 0.0217(3) Uani d . 1 . .
H H5 -0.1036 -0.1937 0.3612 0.026 Uiso calc R 1 . .
C C6 0.05144(13) -0.11361(7) 0.43356(16) 0.0186(3) Uani d . 1 . .
C C7 0.06142(13) -0.10242(8) 0.60895(16) 0.0220(3) Uani d . 1 . .
H H7 0.0030 -0.1293 0.6554 0.026 Uiso calc R 1 . .
C C8 0.15648(13) -0.05239(8) 0.70838(16) 0.0224(3) Uani d . 1 . .
H H8 0.1631 -0.0444 0.8232 0.027 Uiso calc R 1 . .
C C9 0.24603(12) -0.01216(7) 0.63656(15) 0.0189(3) Uani d . 1 . .
C C10 0.35008(13) 0.04359(8) 0.74929(15) 0.0210(3) Uani d . 1 . .
H H10A 0.4004 0.0127 0.8496 0.025 Uiso calc R 1 . .
H H10B 0.3065 0.0886 0.7886 0.025 Uiso calc R 1 . .
C C11 0.44620(12) 0.07996(7) 0.66261(15) 0.0183(3) Uani d . 1 . .
H H11 0.4954 0.0344 0.6324 0.022 Uiso calc R 1 . .
C C12 0.37365(12) 0.12590(7) 0.49881(15) 0.0182(3) Uani d . 1 . .
C C13 0.35706(15) 0.14582(9) 0.20836(16) 0.0306(3) Uani d . 1 . .
H H13A 0.2709 0.1213 0.1651 0.046 Uiso calc R 1 . .
H H13B 0.4060 0.1357 0.1295 0.046 Uiso calc R 1 . .
H H13C 0.3481 0.2042 0.2211 0.046 Uiso calc R 1 . .
C C14 0.54437(12) 0.13576(8) 0.78861(16) 0.0203(3) Uani d . 1 . .
C C15 0.67016(15) 0.25858(9) 0.81881(19) 0.0318(4) Uani d . 1 . .
H H15A 0.6337 0.2801 0.9038 0.048 Uiso calc R 1 . .
H H15B 0.6855 0.3030 0.7498 0.048 Uiso calc R 1 . .
H H15C 0.7522 0.2312 0.8747 0.048 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
C12 O1 C13 . . 115.21(10) ?
C14 O3 C15 . . 116.60(10) ?
C9 N1 C1 . . 118.22(11) ?
N1 C1 C2 . . 118.74(11) ?
N1 C1 C6 . . 122.59(11) ?
C2 C1 C6 . . 118.65(12) ?
C3 C2 C1 . . 120.65(12) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C2 C3 C4 . . 120.61(12) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C5 C4 C3 . . 119.93(12) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.78(12) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C7 . . 123.60(12) ?
C5 C6 C1 . . 119.35(11) ?
C7 C6 C1 . . 117.04(12) ?
C8 C7 C6 . . 119.63(11) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 C9 . . 119.76(11) ?
C7 C8 H8 . . 120.1 ?
C9 C8 H8 . . 120.1 ?
N1 C9 C8 . . 122.73(12) ?
N1 C9 C10 . . 118.51(11) ?
C8 C9 C10 . . 118.74(11) ?
C9 C10 C11 . . 114.61(10) ?
C9 C10 H10A . . 108.6 ?
C11 C10 H10A . . 108.6 ?
C9 C10 H10B . . 108.6 ?
C11 C10 H10B . . 108.6 ?
H10A C10 H10B . . 107.6 ?
C14 C11 C12 . . 111.33(10) ?
C14 C11 C10 . . 109.35(10) ?
C12 C11 C10 . . 111.59(10) ?
C14 C11 H11 . . 108.1 ?
C12 C11 H11 . . 108.1 ?
C10 C11 H11 . . 108.1 ?
O2 C12 O1 . . 124.13(11) ?
O2 C12 C11 . . 124.46(11) ?
O1 C12 C11 . . 111.39(10) ?
O1 C13 H13A . . 109.5 ?
O1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
O4 C14 O3 . . 124.21(12) ?
O4 C14 C11 . . 124.03(12) ?
O3 C14 C11 . . 111.76(10) ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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 C12 . 1.3389(15) ?
O1 C13 . 1.4454(16) ?
O2 C12 . 1.2054(15) ?
O3 C14 . 1.3309(15) ?
O3 C15 . 1.4500(16) ?
O4 C14 . 1.2052(16) ?
N1 C9 . 1.3195(16) ?
N1 C1 . 1.3705(17) ?
C1 C2 . 1.4098(18) ?
C1 C6 . 1.4222(18) ?
C2 C3 . 1.3710(19) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.4089(19) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.3673(18) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.4093(19) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.4184(18) ?
C7 C8 . 1.3542(19) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.4212(18) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.5039(18) ?
C10 C11 . 1.5296(17) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C14 . 1.5189(18) ?
C11 C12 . 1.5197(17) ?
C11 H11 . 0.9800 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
_geom_hbond_publ_flag
C11 H11 O1 3_656 0.98 2.49 3.410(2) 157.0 yes
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
C9 N1 C1 C2 . . . . 177.02(11) ?
C9 N1 C1 C6 . . . . -1.52(17) ?
N1 C1 C2 C3 . . . . -179.71(12) ?
C6 C1 C2 C3 . . . . -1.11(19) ?
C1 C2 C3 C4 . . . . -0.6(2) ?
C2 C3 C4 C5 . . . . 1.3(2) ?
C3 C4 C5 C6 . . . . -0.27(19) ?
C4 C5 C6 C7 . . . . 177.20(12) ?
C4 C5 C6 C1 . . . . -1.43(18) ?
N1 C1 C6 C5 . . . . -179.36(11) ?
C2 C1 C6 C5 . . . . 2.10(17) ?
N1 C1 C6 C7 . . . . 1.92(17) ?
C2 C1 C6 C7 . . . . -176.62(11) ?
C5 C6 C7 C8 . . . . -179.49(12) ?
C1 C6 C7 C8 . . . . -0.82(18) ?
C6 C7 C8 C9 . . . . -0.55(19) ?
C1 N1 C9 C8 . . . . 0.03(17) ?
C1 N1 C9 C10 . . . . -178.51(10) ?
C7 C8 C9 N1 . . . . 1.02(19) ?
C7 C8 C9 C10 . . . . 179.55(11) ?
N1 C9 C10 C11 . . . . -4.71(16) ?
C8 C9 C10 C11 . . . . 176.70(11) ?
C9 C10 C11 C14 . . . . 179.17(10) ?
C9 C10 C11 C12 . . . . 55.55(14) ?
C13 O1 C12 O2 . . . . -6.25(17) ?
C13 O1 C12 C11 . . . . 175.19(10) ?
C14 C11 C12 O2 . . . . -79.24(15) ?
C10 C11 C12 O2 . . . . 43.25(16) ?
C14 C11 C12 O1 . . . . 99.32(11) ?
C10 C11 C12 O1 . . . . -138.19(11) ?
C15 O3 C14 O4 . . . . -1.50(18) ?
C15 O3 C14 C11 . . . . 179.13(10) ?
C12 C11 C14 O4 . . . . 159.19(13) ?
C10 C11 C14 O4 . . . . 35.42(17) ?
C12 C11 C14 O3 . . . . -21.44(14) ?
C10 C11 C14 O3 . . . . -145.21(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744909
2 PubChem 57422023
