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_7230591
_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, C7 H4 N1 O4'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42
_chemical_name_systematic        'DMAN 2-nitrobenzoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-03-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.652(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3320(4)
_cell_length_b                   18.3951(7)
_cell_length_c                   10.3744(4)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    100
_cell_measurement_theta_max      41.11
_cell_measurement_theta_min      2.76
_cell_volume                     1916.03(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Detector'
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.8856
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34754
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        32.097
_diffrn_reflns_theta_max         41.120
_diffrn_reflns_theta_min         2.759
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7481
_exptl_absorpt_correction_T_min  0.6771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction  
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method
'slow evaporation from methanol 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         0.424
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+0.3845P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4927
_reflns_number_total             6559
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00443a2.cif
_cod_data_source_block           complex_9
_cod_depositor_comments
'Adding full bibliography for 7230587--7230595.cif.'
_cod_database_code               7230591
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              20123