#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/94/4509498.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_4509498
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, 0.5(C4 H4 O4), 0.5(C4 H2 O4)'
_chemical_formula_sum            'C11 H14 N2 O4'
_chemical_formula_weight         238.24
_chemical_name_common            '4-Dimethylaminopyridinium fumarate-fumaric'
_chemical_name_systematic
; 
  4-dimethylaminopyridinium fumarate-fumaric acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.381(3)
_cell_angle_beta                 89.228(3)
_cell_angle_gamma                70.789(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4036(13)
_cell_length_b                   8.1567(14)
_cell_length_c                   10.1469(17)
_cell_measurement_reflns_used    1328
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.208
_cell_measurement_theta_min      2.677
_cell_volume                     571.68(17)
_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 0.968
_diffrn_measured_fraction_theta_max 0.914
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4902
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0463
_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)+(0.0637P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                1985
_reflns_number_total             2583
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9001994sup1.cif
_cod_data_source_block           str0646
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4509498
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C10 C 0.9243(2) -0.34007(19) 0.83132(15) 0.0213(3) Uani 1 1 d
C11 C 0.9787(2) -0.4993(2) 0.93738(15) 0.0237(3) Uani 1 1 d
H13 H 0.974(3) -0.601(2) 0.9101(17) 0.035(5) Uiso 1 1 d
O3 O 0.95210(15) -0.20163(13) 0.85759(10) 0.0243(3) Uani 1 1 d
O4 O 0.85341(17) -0.35005(14) 0.72401(11) 0.0309(3) Uani 1 1 d
C6 C 0.7533(2) 0.0342(2) 0.53505(16) 0.0267(4) Uani 1 1 d
C7 C 0.6926(2) 0.1655(2) 0.42944(16) 0.0252(4) Uani 1 1 d
H1 H 0.456(3) 0.398(3) 0.2380(19) 0.051(6) Uiso 1 1 d
H2 H 0.643(4) 0.394(3) 0.155(2) 0.063(7) Uiso 1 1 d
H3 H 0.490(3) 0.568(3) 0.1732(19) 0.051(6) Uiso 1 1 d
H4 H 0.686(3) 0.691(3) 0.246(2) 0.054(6) Uiso 1 1 d
H5 H 0.611(3) 0.711(3) 0.389(2) 0.062(7) Uiso 1 1 d
H6 H 0.833(3) 0.601(2) 0.3632(18) 0.039(5) Uiso 1 1 d
H7 H 0.810(2) 0.454(2) 0.5663(16) 0.027(4) Uiso 1 1 d
H8 H 0.904(2) 0.225(2) 0.7353(17) 0.026(4) Uiso 1 1 d
H9 H 0.883(3) -0.043(3) 0.720(2) 0.062(6) Uiso 1 1 d
H10 H 0.744(2) -0.073(2) 0.5349(17) 0.029(5) Uiso 1 1 d
H11 H 0.644(2) 0.138(2) 0.3550(16) 0.025(4) Uiso 1 1 d
N1 N 0.65681(18) 0.46458(16) 0.33279(13) 0.0241(3) Uani 1 1 d
N2 N 0.83143(19) 0.05703(18) 0.64697(13) 0.0263(3) Uani 1 1 d
C1 C 0.5562(3) 0.4528(3) 0.21398(17) 0.0306(4) Uani 1 1 d
C2 C 0.6988(3) 0.6264(2) 0.3359(2) 0.0323(4) Uani 1 1 d
C3 C 0.7127(2) 0.33130(19) 0.43490(14) 0.0203(3) Uani 1 1 d
C4 C 0.7954(2) 0.3497(2) 0.55484(15) 0.0238(3) Uani 1 1 d
C5 C 0.8515(2) 0.2132(2) 0.65560(16) 0.0260(4) Uani 1 1 d
O2 O 1.19798(15) -0.15885(13) 1.01161(10) 0.0231(3) Uani 1 1 d
C8 C 1.2784(2) -0.04891(18) 0.94730(14) 0.0195(3) Uani 1 1 d
C9 C 1.4337(2) -0.03027(19) 1.02822(15) 0.0205(3) Uani 1 1 d
H14 H 1.436(2) -0.062(2) 1.1263(17) 0.027(4) Uiso 1 1 d
H15 H 1.109(3) -0.173(2) 0.9528(19) 0.048(6) Uiso 1 1 d
O1 O 1.23435(15) 0.02576(14) 0.83377(10) 0.0275(3) Uani 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
_geom_angle_site_symmetry_1
O4 C10 O3 123.87(13) .
O4 C10 C11 118.16(13) .
O3 C10 C11 117.97(13) .
C11 C11 C10 125.24(19) 2_747
C11 C11 H13 119.6(11) 2_747
C10 C11 H13 115.1(11) .
N2 C6 C7 121.78(15) .
N2 C6 H10 115.7(11) .
C7 C6 H10 122.5(11) .
C6 C7 C3 119.99(15) .
C6 C7 H11 116.3(10) .
C3 C7 H11 123.7(10) .
C3 N1 C1 121.92(14) .
C3 N1 C2 120.76(14) .
C1 N1 C2 117.31(13) .
C6 N2 C5 119.68(13) .
C6 N2 H9 120.2(13) .
C5 N2 H9 120.0(13) .
N1 C1 H1 111.1(11) .
N1 C1 H2 110.8(15) .
H1 C1 H2 112.3(19) .
N1 C1 H3 107.4(13) .
H1 C1 H3 105.4(16) .
H2 C1 H3 109.6(18) .
N1 C2 H4 109.5(13) .
N1 C2 H5 115.7(12) .
H4 C2 H5 104.1(17) .
N1 C2 H6 110.9(11) .
H4 C2 H6 104.7(16) .
H5 C2 H6 111.2(17) .
N1 C3 C7 122.29(14) .
N1 C3 C4 121.38(14) .
C7 C3 C4 116.33(13) .
C5 C4 C3 120.17(15) .
C5 C4 H7 118.6(10) .
C3 C4 H7 121.3(10) .
N2 C5 C4 122.04(15) .
N2 C5 H8 117.4(10) .
C4 C5 H8 120.5(10) .
C8 O2 H15 108.5(12) .
O1 C8 O2 124.35(14) .
O1 C8 C9 123.26(14) .
O2 C8 C9 112.36(12) .
C9 C9 C8 121.28(17) 2_857
C9 C9 H14 120.2(10) 2_857
C8 C9 H14 118.6(10) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C10 O4 1.2399(18) .
C10 O3 1.2782(17) .
C10 C11 1.502(2) .
C11 C11 1.311(3) 2_747
C11 H13 0.924(19) .
C6 N2 1.346(2) .
C6 C7 1.360(2) .
C6 H10 0.897(18) .
C7 C3 1.418(2) .
C7 H11 0.931(17) .
N1 C3 1.3433(19) .
N1 C1 1.457(2) .
N1 C2 1.457(2) .
N2 C5 1.346(2) .
N2 H9 0.99(2) .
C1 H1 1.00(2) .
C1 H2 0.94(2) .
C1 H3 0.94(2) .
C2 H4 0.97(2) .
C2 H5 1.00(2) .
C2 H6 0.98(2) .
C3 C4 1.419(2) .
C4 C5 1.350(2) .
C4 H7 0.914(17) .
C5 H8 0.934(17) .
O2 C8 1.3228(17) .
O2 H15 0.94(2) .
C8 O1 1.2139(17) .
C8 C9 1.482(2) .
C9 C9 1.325(3) 2_857
C9 H14 0.990(17) .
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 H9 O3 0.99(2) 1.71(2) 2.6975(17) 173(2)
O2 H15 O3 0.94(2) 1.61(2) 2.5566(15) 177.6(19)
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
_geom_torsion_site_symmetry_4
O4 C10 C11 C11 -166.7(2) 2_747
O3 C10 C11 C11 12.6(3) 2_747
N2 C6 C7 C3 0.7(2) .
C7 C6 N2 C5 -0.3(2) .
C1 N1 C3 C7 5.6(2) .
C2 N1 C3 C7 -173.12(14) .
C1 N1 C3 C4 -174.39(14) .
C2 N1 C3 C4 6.9(2) .
C6 C7 C3 N1 179.28(14) .
C6 C7 C3 C4 -0.8(2) .
N1 C3 C4 C5 -179.53(14) .
C7 C3 C4 C5 0.5(2) .
C6 N2 C5 C4 0.0(2) .
C3 C4 C5 N2 -0.2(2) .
O1 C8 C9 C9 -18.2(3) 2_857
O2 C8 C9 C9 160.15(17) 2_857
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146932
