Synthesis, Theoretical Analysis, and Experimental pKa Determination of a Fluorescent, Nonsymmetric, In-Out Proton Sponge.
Belding, Lee; Stoyanov, Peter; Dudding, Travis; The Journal of organic chemistry 81 (2016) 6–13; doi:10.1021/acs.joc.5b01743

data_4036366
_publ_section_title
;
 Synthesis, Theoretical Analysis, and Experimental pKa Determination of a
 Fluorescent, Nonsymmetric, In-Out Proton Sponge.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6
_journal_page_last               13
_journal_paper_doi               10.1021/acs.joc.5b01743
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C27 H41 N4, Cl'
_chemical_formula_sum            'C27 H41 Cl N4'
_chemical_formula_weight         457.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 113.1020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.592(2)
_cell_length_b                   11.1346(7)
_cell_length_c                   18.5547(11)
_cell_measurement_reflns_used    5847
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.96
_cell_measurement_theta_min      2.39
_cell_volume                     6383.5(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31761
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         1.944
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.9280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.951
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         7319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0742P)^2^+0.4309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4513
_reflns_number_total             7319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01743_si_001.cif
_cod_data_source_block           januscl_0m_a_sq
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4036366
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2014/6
_shelx_res_checksum              35377
_shelx_hkl_checksum              33627
_shelx_fab_checksum              87213