Tuning charge-assisted and weak hydrogen bonds in molecular complexes of the proton sponge DMAN by acid co-former substitution
Saunders, Lucy K.; Nowell, Harriott; Spencer, Helen C. E.; Hatcher, Lauren E.; Shepherd, Helena J.; Thomas, Lynne H.; Jones, Charlotte L.; Teat, Simon J.; Raithby, Paul R.; Wilson, Chick C.; CrystEngComm 20 (2018) 3074–; doi:10.1039/C8CE00443A

data_7230588
_publ_section_title
;
 Tuning charge-assisted and weak hydrogen bonds in molecular complexes of
 the proton sponge DMAN by acid co-former substitution
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3074
_journal_paper_doi               10.1039/C8CE00443A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C14 H19 N2, 2(C8 H5 N1 O2), C8 H4 N1 O2'
_chemical_formula_sum            'C38 H33 N5 O6'
_chemical_formula_weight         655.69
_chemical_name_systematic        'DMAN 4-cyanobenzoate 4-cyanobenzoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-04-13 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.447(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6378(4)
_cell_length_b                   9.17650(10)
_cell_length_c                   18.3236(3)
_cell_measurement_reflns_used    11399
_cell_measurement_temperature    150
_cell_measurement_theta_max      71.8350
_cell_measurement_theta_min      4.8220
_cell_volume                     3362.66(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23758
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.910
_diffrn_reflns_theta_min         4.422
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_recrystallization_method 'grown from isopropanol at 30 degreesC'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         6514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0418
_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/[\s^2^(Fo^2^)+(0.0729P)^2^+0.6089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5571
_reflns_number_total             6514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00443a2.cif
_cod_data_source_block           complex_6
_cod_depositor_comments
'Adding full bibliography for 7230587--7230595.cif.'
_cod_database_code               7230588
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              53249