#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566768.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_1566768
loop_
_publ_author_name
'Naeem, Marilyn'
'Chadeayne, Andrew R.'
'Golen, James A.'
'Manke, David R.'
_publ_section_title
;
 Bis(oxotremorine) fumarate bis(fumaric acid)
;
_journal_coeditor_code           ZL4049
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x220364
_journal_paper_doi               10.1107/S2414314622003649
_journal_volume                  7
_journal_year                    2022
_chemical_formula_iupac          '2C12 H19 N2 O +, C4 H2 O4 2-, 2C4 H4 O4'
_chemical_formula_moiety         '2(C12 H19 N2 O +), C4 H2 O4 2-, 2(C4 H4 O4)'
_chemical_formula_sum            'C36 H48 N4 O14'
_chemical_formula_weight         760.78
_chemical_name_common
;
Bis(oxotremorine) fumarate bis(fumaric acid)
;
_chemical_name_systematic
;
1-[4-(2-Oxopyrrolidin-1-yl)but-2-ynyl]pyrrolidinium
(2E)-but-2-enedioate bis[(2E)-but-2-enedioic acid]
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                94.922(2)
_cell_angle_beta                 90.428(2)
_cell_angle_gamma                98.945(2)
_cell_formula_units_Z            1
_cell_length_a                   6.0921(3)
_cell_length_b                   8.5778(5)
_cell_length_c                   18.7260(11)
_cell_measurement_reflns_used    9070
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      2.56
_cell_volume                     962.88(9)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      297.15
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27417
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.765
_diffrn_reflns_theta_min         2.560
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0473P)²+0.2757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                2975
_reflns_number_total             3651
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl4049sup1.cif
_cod_data_source_block           I
_cod_database_code               1566768
_cod_database_fobs_code          1566768
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.996
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O2 0.1880(2) 0.32007(19) 0.36008(8) 0.0785(5) Uani d 1 . .
O O3 0.5181(2) 0.34987(18) 0.41423(7) 0.0648(4) Uani d 1 . .
O O4 0.69301(19) 0.57836(15) 0.18323(6) 0.0575(3) Uani d 1 . .
O O5 1.0269(2) 0.56449(19) 0.22771(8) 0.0732(4) Uani d 1 . .
C C15 0.7126(3) 0.45921(19) 0.29059(8) 0.0457(4) Uani d 1 . .
H H15 0.798508 0.415501 0.322444 0.055 Uiso calc 1 . .
C C13 0.3847(3) 0.36674(19) 0.36123(9) 0.0466(4) Uani d 1 . .
C C14 0.4977(3) 0.44695(18) 0.30158(8) 0.0453(4) Uani d 1 . .
H H14 0.411762 0.491313 0.269994 0.054 Uiso calc 1 . .
C C16 0.8265(3) 0.53832(18) 0.23060(8) 0.0445(4) Uani d 1 . .
O O1 0.3504(2) 0.16999(17) 0.50962(7) 0.0673(4) Uani d 1 . .
N N1 0.12900(19) 0.08762(16) 0.60010(6) 0.0421(3) Uani d 1 . .
N N2 0.65707(19) 0.00872(15) 0.85784(6) 0.0380(3) Uani d 1 . .
C C2 0.0229(3) 0.2911(2) 0.54231(10) 0.0578(5) Uani d 1 . .
H H2A -0.043039 0.281057 0.494497 0.069 Uiso calc 1 . .
H H2B 0.094453 0.399740 0.553553 0.069 Uiso calc 1 . .
C C1 0.1861(2) 0.17907(19) 0.54731(8) 0.0445(4) Uani d 1 . .
C C3 -0.1513(3) 0.2442(3) 0.59673(12) 0.0758(6) Uani d 1 . .
H H3A -0.168967 0.334814 0.629641 0.091 Uiso calc 1 . .
H H3B -0.293254 0.203854 0.572933 0.091 Uiso calc 1 . .
C C4 -0.0716(3) 0.1172(2) 0.63662(10) 0.0576(4) Uani d 1 . .
H H4A -0.039682 0.153881 0.686613 0.069 Uiso calc 1 . .
H H4B -0.181912 0.022144 0.633910 0.069 Uiso calc 1 . .
C C5 0.2587(3) -0.02922(19) 0.62190(8) 0.0458(4) Uani d 1 . .
H H5A 0.370750 -0.043844 0.586468 0.055 Uiso calc 1 . .
H H5B 0.162152 -0.129865 0.623917 0.055 Uiso calc 1 . .
C C6 0.3680(2) 0.01937(19) 0.69249(8) 0.0453(4) Uani d 1 . .
C C7 0.4569(3) 0.0611(2) 0.74894(9) 0.0476(4) Uani d 1 . .
C C8 0.5696(3) 0.1275(2) 0.81681(9) 0.0526(4) Uani d 1 . .
H H8A 0.466071 0.177765 0.846459 0.063 Uiso calc 1 . .
H H8B 0.691969 0.208802 0.806785 0.063 Uiso calc 1 . .
C C9 0.8224(3) -0.0784(2) 0.82116(8) 0.0463(4) Uani d 1 . .
H H9A 0.963732 -0.010026 0.817488 0.056 Uiso calc 1 . .
H H9B 0.769788 -0.122425 0.773541 0.056 Uiso calc 1 . .
C C10 0.8423(3) -0.2081(3) 0.86974(11) 0.0690(5) Uani d 1 . .
H H10A 0.867468 -0.304045 0.841843 0.083 Uiso calc 1 . .
H H10B 0.964896 -0.175271 0.903809 0.083 Uiso calc 1 . .
C C11 0.6245(3) -0.2359(3) 0.90830(12) 0.0729(6) Uani d 1 . .
H H11A 0.548597 -0.343053 0.896019 0.087 Uiso calc 1 . .
H H11B 0.649915 -0.220532 0.959802 0.087 Uiso calc 1 . .
C C12 0.4880(3) -0.1170(2) 0.88405(9) 0.0561(4) Uani d 1 . .
H H12A 0.383755 -0.164457 0.845940 0.067 Uiso calc 1 . .
H H12B 0.406420 -0.074741 0.923545 0.067 Uiso calc 1 . .
H H4 0.773(3) 0.632(3) 0.1495(10) 0.089(7) Uiso d 1 . .
H H3 0.440(4) 0.291(3) 0.4458(11) 0.098(8) Uiso d 1 . .
H H2 0.724(3) 0.068(2) 0.8967(10) 0.053(5) Uiso d 1 . .
O O6 0.8934(4) 0.7598(3) 0.10050(12) 0.0504(5) Uani d 0.855(4) A 1
O O7 1.1822(4) 0.7858(2) 0.02939(11) 0.0519(4) Uani d 0.855(4) A 1
C C17 1.0122(5) 0.7065(2) 0.05155(12) 0.0381(5) Uani d 0.855(4) A 1
C C18 0.9417(3) 0.5389(2) 0.02174(10) 0.0442(5) Uani d 0.855(4) A 1
H H18 0.804798 0.487027 0.035288 0.053 Uiso calc 0.855(4) A 1
O O6A 0.939(3) 0.737(2) 0.0861(11) 0.0504(5) Uani d 0.145(4) A 2
O O7A 1.239(2) 0.8253(18) 0.0278(9) 0.0519(4) Uani d 0.145(4) A 2
C C17A 1.096(3) 0.7175(18) 0.0433(9) 0.0381(5) Uani d 0.145(4) A 2
C C18A 1.074(2) 0.5595(14) 0.0004(6) 0.0442(5) Uani d 0.145(4) A 2
H H18A 1.189497 0.548224 -0.030918 0.053 Uiso calc 0.145(4) A 2
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
C13 O3 H3 . . 108.7(16) ?
C16 O4 H4 . . 110.0(15) ?
C14 C15 H15 . . 117.9 ?
C14 C15 C16 . . 124.13(15) ?
C16 C15 H15 . . 117.9 ?
O2 C13 O3 . . 123.57(15) ?
O2 C13 C14 . . 122.35(15) ?
O3 C13 C14 . . 114.08(14) ?
C15 C14 C13 . . 123.90(15) ?
C15 C14 H14 . . 118.1 ?
C13 C14 H14 . . 118.1 ?
O4 C16 C15 . . 114.39(13) ?
O5 C16 O4 . . 123.90(15) ?
O5 C16 C15 . . 121.70(15) ?
C1 N1 C4 . . 114.58(13) ?
C1 N1 C5 . . 123.48(13) ?
C4 N1 C5 . . 121.90(13) ?
C8 N2 C12 . . 116.01(13) ?
C8 N2 H2 . . 103.0(11) ?
C9 N2 C8 . . 116.32(12) ?
C9 N2 C12 . . 104.70(13) ?
C9 N2 H2 . . 108.6(11) ?
C12 N2 H2 . . 107.8(11) ?
H2A C2 H2B . . 108.8 ?
C1 C2 H2A . . 110.7 ?
C1 C2 H2B . . 110.7 ?
C1 C2 C3 . . 105.11(15) ?
C3 C2 H2A . . 110.7 ?
C3 C2 H2B . . 110.7 ?
O1 C1 N1 . . 123.90(15) ?
O1 C1 C2 . . 126.98(15) ?
N1 C1 C2 . . 109.11(14) ?
C2 C3 H3A . . 110.4 ?
C2 C3 H3B . . 110.4 ?
H3A C3 H3B . . 108.6 ?
C4 C3 C2 . . 106.81(15) ?
C4 C3 H3A . . 110.4 ?
C4 C3 H3B . . 110.4 ?
N1 C4 C3 . . 104.08(14) ?
N1 C4 H4A . . 110.9 ?
N1 C4 H4B . . 110.9 ?
C3 C4 H4A . . 110.9 ?
C3 C4 H4B . . 110.9 ?
H4A C4 H4B . . 109.0 ?
N1 C5 H5A . . 109.3 ?
N1 C5 H5B . . 109.3 ?
N1 C5 C6 . . 111.67(13) ?
H5A C5 H5B . . 107.9 ?
C6 C5 H5A . . 109.3 ?
C6 C5 H5B . . 109.3 ?
C7 C6 C5 . . 178.83(17) ?
C6 C7 C8 . . 174.81(17) ?
N2 C8 H8A . . 108.7 ?
N2 C8 H8B . . 108.7 ?
C7 C8 N2 . . 114.07(14) ?
C7 C8 H8A . . 108.7 ?
C7 C8 H8B . . 108.7 ?
H8A C8 H8B . . 107.6 ?
N2 C9 H9A . . 111.2 ?
N2 C9 H9B . . 111.2 ?
N2 C9 C10 . . 102.94(13) ?
H9A C9 H9B . . 109.1 ?
C10 C9 H9A . . 111.2 ?
C10 C9 H9B . . 111.2 ?
C9 C10 H10A . . 110.5 ?
C9 C10 H10B . . 110.5 ?
H10A C10 H10B . . 108.7 ?
C11 C10 C9 . . 106.06(15) ?
C11 C10 H10A . . 110.5 ?
C11 C10 H10B . . 110.5 ?
C10 C11 H11A . . 110.5 ?
C10 C11 H11B . . 110.5 ?
H11A C11 H11B . . 108.7 ?
C12 C11 C10 . . 106.27(15) ?
C12 C11 H11A . . 110.5 ?
C12 C11 H11B . . 110.5 ?
N2 C12 C11 . . 103.58(13) ?
N2 C12 H12A . . 111.0 ?
N2 C12 H12B . . 111.0 ?
C11 C12 H12A . . 111.0 ?
C11 C12 H12B . . 111.0 ?
H12A C12 H12B . . 109.0 ?
O6 C17 C18 . . 116.8(2) ?
O7 C17 O6 . . 123.1(2) ?
O7 C17 C18 . . 120.1(2) ?
C17 C18 H18 . . 117.8 ?
C18 C18 C17 2_765 . 124.4(2) ?
C18 C18 H18 2_765 . 117.8 ?
O6A C17A C18A . . 116.1(16) ?
O7A C17A O6A . . 123.5(16) ?
O7A C17A C18A . . 119.4(16) ?
C17A C18A H18A . . 114.6 ?
C18A C18A C17A 2_765 . 130.7(16) ?
C18A C18A H18A 2_765 . 114.6 ?
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
O2 C13 . 1.2026(19) ?
O3 C13 . 1.310(2) ?
O3 H3 . 0.902(10) ?
O4 C16 . 1.3016(19) ?
O4 H4 . 0.914(10) ?
O5 C16 . 1.2092(19) ?
C15 H15 . 0.9300 ?
C15 C14 . 1.316(2) ?
C15 C16 . 1.483(2) ?
C13 C14 . 1.480(2) ?
C14 H14 . 0.9300 ?
O1 C1 . 1.2372(19) ?
N1 C1 . 1.3293(19) ?
N1 C4 . 1.451(2) ?
N1 C5 . 1.452(2) ?
N2 C8 . 1.486(2) ?
N2 C9 . 1.4833(19) ?
N2 C12 . 1.490(2) ?
N2 H2 . 0.908(19) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C2 C1 . 1.495(2) ?
C2 C3 . 1.510(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C3 C4 . 1.509(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C5 C6 . 1.473(2) ?
C6 C7 . 1.185(2) ?
C7 C8 . 1.467(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 C10 . 1.515(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C10 C11 . 1.511(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C11 C12 . 1.509(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
O6 C17 . 1.270(3) ?
O7 C17 . 1.243(2) ?
C17 C18 . 1.492(3) ?
C18 C18 2_765 1.295(4) ?
C18 H18 . 0.9300 ?
O6A C17A . 1.273(14) ?
O7A C17A . 1.222(14) ?
C17A C18A . 1.502(14) ?
C18A C18A 2_765 1.25(2) ?
C18A H18A . 0.9300 ?
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
C14 H14 O5 1_455 0.93 2.65 3.498(2) 151.6 yes
C3 H3B O1 1_455 0.97 2.43 3.381(3) 166.1 yes
C5 H5B O2 2_556 0.97 2.51 3.434(2) 158.6 yes
C8 H8A O4 2_666 0.97 2.54 3.191(2) 124.6 yes
C8 H8A O6 2_666 0.97 2.53 3.456(3) 160.9 yes
C8 H8B O5 2_766 0.97 2.52 3.480(2) 172.6 yes
C9 H9A O6 2_766 0.97 2.56 3.228(3) 126.0 yes
C10 H10A O5 2_756 0.97 2.66 3.624(3) 174.5 yes
C11 H11A O4 2_656 0.97 2.64 3.553(3) 156.9 yes
C12 H12B O7 1_446 0.97 2.68 3.399(2) 131.6 yes
C12 H12B O7A 1_446 0.97 2.37 3.139(15) 135.4 yes
O4 H4 O6 . 0.914(10) 1.584(11) 2.483(2) 167(2) yes
O3 H3 O1 . 0.902(10) 1.687(11) 2.5739(16) 167(2) yes
N2 H2 O6 2_766 0.908(19) 2.554(18) 3.172(3) 125.8(14) yes
N2 H2 O7 2_766 0.908(19) 1.809(19) 2.705(2) 168.3(17) yes
N2 H2 O6A 2_766 0.908(19) 2.43(3) 3.131(19) 133.6(15) yes
N2 H2 O7A 2_766 0.908(19) 1.61(2) 2.489(15) 161.7(17) 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
O2 C13 C14 C15 . . . . -159.84(18) ?
O3 C13 C14 C15 . . . . 19.3(2) ?
C14 C15 C16 O4 . . . . -8.4(2) ?
C14 C15 C16 O5 . . . . 170.45(18) ?
C16 C15 C14 C13 . . . . 179.50(15) ?
N2 C9 C10 C11 . . . . 25.88(19) ?
C2 C3 C4 N1 . . . . -4.8(2) ?
C1 N1 C4 C3 . . . . 2.4(2) ?
C1 N1 C5 C6 . . . . 109.44(16) ?
C1 C2 C3 C4 . . . . 5.5(2) ?
C3 C2 C1 O1 . . . . 176.15(18) ?
C3 C2 C1 N1 . . . . -4.2(2) ?
C4 N1 C1 O1 . . . . -179.16(16) ?
C4 N1 C1 C2 . . . . 1.17(19) ?
C4 N1 C5 C6 . . . . -68.36(19) ?
C5 N1 C1 O1 . . . . 2.9(2) ?
C5 N1 C1 C2 . . . . -176.77(14) ?
C5 N1 C4 C3 . . . . -179.65(16) ?
C8 N2 C9 C10 . . . . -169.44(14) ?
C8 N2 C12 C11 . . . . 168.12(15) ?
C9 N2 C8 C7 . . . . 59.62(19) ?
C9 N2 C12 C11 . . . . 38.48(17) ?
C9 C10 C11 C12 . . . . -2.6(2) ?
C10 C11 C12 N2 . . . . -21.6(2) ?
C12 N2 C8 C7 . . . . -64.18(19) ?
C12 N2 C9 C10 . . . . -39.98(16) ?
O6 C17 C18 C18 . . . 2_765 -171.2(3) ?
O7 C17 C18 C18 . . . 2_765 7.4(4) ?
O6A C17A C18A C18A . . . 2_765 -1(3) ?
O7A C17A C18A C18A . . . 2_765 -169(2) ?
