#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/94/4509495.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4509495
loop_
_publ_author_name
'Mohamed, Sharmarke'
'Tocher, Derek A.'
'Vickers, Martin'
'Karamertzanis, Panagiotis G.'
'Price, Sarah L.'
_publ_section_title
;
 Salt or Cocrystal? A New Series of Crystal Structures Formed from Simple
 Pyridines and Carboxylic Acids
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2881
_journal_paper_doi               10.1021/cg9001994
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C7 H11 N2, C4 H3 O4'
_chemical_formula_sum            'C11 H14 N2 O4'
_chemical_formula_weight         238.24
_chemical_name_common            '4-dimethylaminopyridinium maleate'
_chemical_name_systematic
; 
 4-dimethylaminopyridinium maleate 
;
_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                 114.237(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.127(3)
_cell_length_b                   7.599(2)
_cell_length_c                   12.576(3)
_cell_measurement_reflns_used    934
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.2630
_cell_measurement_theta_min      3.1754
_cell_volume                     1143.9(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
;    
SHELXTL (Bruker, 2000) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6290
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0608
_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)+(0.0585P)²+0.0742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                1709
_reflns_number_total             2624
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9001994sup1.cif
_cod_data_source_block           str0613
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4509495
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C8 C 0.21128(18) 0.5735(3) 0.06647(18) 0.0271(5) Uani 1 1 d .
C9 C 0.32327(18) 0.4884(3) 0.10241(19) 0.0312(6) Uani 1 1 d .
C10 C 0.37300(19) 0.4171(3) 0.04042(18) 0.0311(6) Uani 1 1 d .
C11 C 0.3336(2) 0.3912(3) -0.08798(18) 0.0284(5) Uani 1 1 d .
H12 H 0.3633(19) 0.493(3) 0.187(2) 0.043(7) Uiso 1 1 d .
H13 H 0.4472(19) 0.369(3) 0.0808(18) 0.036(6) Uiso 1 1 d .
H14 H 0.196(2) 0.512(4) -0.106(3) 0.077(10) Uiso 1 1 d .
O1 O 0.18796(13) 0.6281(2) 0.14701(12) 0.0366(4) Uani 1 1 d .
O2 O 0.14645(12) 0.5884(2) -0.04125(12) 0.0323(4) Uani 1 1 d .
O3 O 0.23640(14) 0.4549(2) -0.15654(13) 0.0363(4) Uani 1 1 d .
O4 O 0.39284(14) 0.3128(2) -0.12544(13) 0.0407(5) Uani 1 1 d .
N1 N -0.31301(14) 1.0445(2) -0.02233(14) 0.0261(4) Uani 1 1 d .
N2 N -0.00775(16) 0.7977(3) 0.08676(15) 0.0292(5) Uani 1 1 d .
C1 C -0.35366(19) 1.1129(3) 0.06183(18) 0.0311(5) Uani 1 1 d .
H3 H -0.3660 1.0150 0.1059 0.047 Uiso 1 1 calc R
H1 H -0.4241 1.1759 0.0204 0.047 Uiso 1 1 calc R
H2 H -0.2982 1.1936 0.1156 0.047 Uiso 1 1 calc R
C2 C -0.38717(18) 1.0545(3) -0.14679(17) 0.0343(6) Uani 1 1 d .
H5 H -0.3480 1.1125 -0.1888 0.052 Uiso 1 1 calc R
H4 H -0.4540 1.1224 -0.1570 0.052 Uiso 1 1 calc R
H6 H -0.4090 0.9355 -0.1777 0.052 Uiso 1 1 calc R
C3 C -0.21277(17) 0.9666(3) 0.01306(16) 0.0233(5) Uani 1 1 d .
C4 C -0.17508(19) 0.8908(3) -0.06699(18) 0.0275(5) Uani 1 1 d .
C5 C -0.0746(2) 0.8090(3) -0.02800(19) 0.0304(5) Uani 1 1 d .
C6 C -0.04051(19) 0.8692(3) 0.16530(18) 0.0287(5) Uani 1 1 d .
C7 C -0.14000(18) 0.9526(3) 0.13336(17) 0.0256(5) Uani 1 1 d .
H7 H -0.2194(19) 0.895(3) -0.147(2) 0.042(7) Uiso 1 1 d .
H8 H -0.0404(18) 0.756(3) -0.0782(18) 0.029(6) Uiso 1 1 d .
H9 H 0.061(2) 0.736(3) 0.1085(18) 0.035(7) Uiso 1 1 d .
H10 H 0.0138(17) 0.858(3) 0.2501(18) 0.028(6) Uiso 1 1 d .
H11 H -0.1604(18) 1.003(3) 0.190(2) 0.033(6) Uiso 1 1 d .
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
O1 C8 O2 123.8(2)
O1 C8 C9 115.99(18)
O2 C8 C9 120.25(19)
C10 C9 C8 131.4(2)
C10 C9 H12 119.0(14)
C8 C9 H12 109.6(14)
C9 C10 C11 131.0(2)
C9 C10 H13 118.8(13)
C11 C10 H13 110.2(13)
O4 C11 O3 122.2(2)
O4 C11 C10 119.4(2)
O3 C11 C10 118.5(2)
C8 O2 H14 108.6(13)
C11 O3 H14 110.0(16)
C3 N1 C1 121.09(17)
C3 N1 C2 120.53(17)
C1 N1 C2 118.30(18)
C6 N2 C5 119.8(2)
C6 N2 H9 122.7(13)
C5 N2 H9 117.5(13)
N1 C1 H3 109.5
N1 C1 H1 109.5
H3 C1 H1 109.5
N1 C1 H2 109.5
H3 C1 H2 109.5
H1 C1 H2 109.5
N1 C2 H5 109.5
N1 C2 H4 109.5
H5 C2 H4 109.5
N1 C2 H6 109.5
H5 C2 H6 109.5
H4 C2 H6 109.5
N1 C3 C4 121.72(18)
N1 C3 C7 121.65(19)
C4 C3 C7 116.6(2)
C5 C4 C3 120.2(2)
C5 C4 H7 119.1(14)
C3 C4 H7 120.7(14)
N2 C5 C4 121.7(2)
N2 C5 H8 112.8(12)
C4 C5 H8 125.5(12)
N2 C6 C7 122.1(2)
N2 C6 H10 116.1(12)
C7 C6 H10 121.8(12)
C6 C7 C3 119.6(2)
C6 C7 H11 120.4(13)
C3 C7 H11 119.9(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C8 O1 1.244(2)
C8 O2 1.275(2)
C8 C9 1.496(3)
C9 C10 1.321(3)
C9 H12 0.98(2)
C10 C11 1.493(3)
C10 H13 0.97(2)
C11 O4 1.218(3)
C11 O3 1.305(3)
O2 H14 1.36(3)
O3 H14 1.07(3)
N1 C3 1.341(3)
N1 C1 1.463(3)
N1 C2 1.467(2)
N2 C6 1.343(3)
N2 C5 1.349(3)
N2 H9 0.95(2)
C1 H3 0.9800
C1 H1 0.9800
C1 H2 0.9800
C2 H5 0.9800
C2 H4 0.9800
C2 H6 0.9800
C3 C4 1.414(3)
C3 C7 1.423(3)
C4 C5 1.355(3)
C4 H7 0.94(2)
C5 H8 1.00(2)
C6 C7 1.356(3)
C6 H10 1.01(2)
C7 H11 0.94(2)
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
O3 H14 O2 1.07(3) 1.36(3) 2.435(2) 179(3)
N2 H9 O1 0.95(2) 1.74(2) 2.690(2) 178(2)
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
O1 C8 C9 C10 179.7(3)
O2 C8 C9 C10 -1.1(4)
C8 C9 C10 C11 -2.0(5)
C9 C10 C11 O4 -176.2(3)
C9 C10 C11 O3 4.2(4)
C1 N1 C3 C4 176.27(19)
C2 N1 C3 C4 -0.4(3)
C1 N1 C3 C7 -2.3(3)
C2 N1 C3 C7 -178.98(19)
N1 C3 C4 C5 -178.2(2)
C7 C3 C4 C5 0.4(3)
C6 N2 C5 C4 -0.2(3)
C3 C4 C5 N2 -0.2(3)
C5 N2 C6 C7 0.5(3)
N2 C6 C7 C3 -0.3(3)
N1 C3 C7 C6 178.5(2)
C4 C3 C7 C6 -0.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146929
