Crystal structures and hydrogen bonding in the proton-transfer salts of nicotine with 3,5-dinitrosalicylic acid and 5-sulfosalicylic acid
Smith, Graham; Wermuth, Urs D.; Acta Crystallographica Section E 70 (2014) 430–434; doi:10.1107/S1600536814023253

data_2240130
_publ_section_title
;
 Crystal structures and hydrogen bonding in the proton-transfer salts of
 nicotine with 3,5-dinitrosalicylic acid and 5-sulfosalicylic acid
;
_journal_coeditor_code           LH5736
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              430
_journal_page_last               434
_journal_paper_doi               10.1107/S1600536814023253
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C10 H15 N2 +, C7 H3 N2 O7 -'
_chemical_formula_moiety         'C10 H15 N2 +, C7 H3 N2 O7 -'
_chemical_formula_sum            'C17 H18 N4 O7'
_chemical_formula_weight         390.35
_chemical_name_common            'nicotinium 3,5-dinitrosalicylate'
_chemical_name_systematic
;
(1<i>R</i>,2<i>S</i>)-1-Methyl-2-(pyridin-3-yl)pyrrolidin-1-ium
2-carboxy-4,6-dinitrophenolate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.8096(5)
_cell_length_b                   17.6403(15)
_cell_length_c                   29.3604(19)
_cell_measurement_reflns_used    1206
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      22.43
_cell_measurement_theta_min      3.62
_cell_volume                     3526.9(5)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2013)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200.0(10)
_diffrn_detector_area_resol_mean 16.077
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Oxford Diffraction Gemini-S CCD-detector diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0827
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8840
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.193
_refine_ls_abs_structure_details
;
Flack (1983), 2983 Friedel pairs
;
_refine_ls_abs_structure_Flack   -0.2(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         6476
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0723
_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/[\s^2^(Fo^2^)+(0.0329P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                4303
_reflns_number_total             6476
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            lh5736sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        3526.9(4)
_cod_database_code               2240130
_cod_database_fobs_code          2240130