Modified Atomic Orbital Overlap: Molecular Level Proof of the Nucleophilic Cleavage Propensity of Dinitrophenol-Based Probes.
Venkateswarulu, Mangili; Kumar, Sunil; Ghosh, Subrata; The Journal of organic chemistry 82 (2017) 4713–4720; doi:10.1021/acs.joc.7b00317

data_4032545
_publ_section_title
;
 Modified Atomic Orbital Overlap: Molecular Level Proof of the
 Nucleophilic Cleavage Propensity of Dinitrophenol-Based Probes.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4713
_journal_page_last               4720
_journal_paper_doi               10.1021/acs.joc.7b00317
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C18 H15 N3 O7 S'
_chemical_formula_sum            'C18 H15 N3 O7 S'
_chemical_formula_weight         417.39
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-13
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.232(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1841(3)
_cell_length_b                   31.9088(12)
_cell_length_c                   7.3248(4)
_cell_measurement_reflns_used    1690
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.7410
_cell_measurement_theta_min      2.7630
_cell_volume                     1912.82(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9987
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.7615
_diffrn_measured_fraction_theta_max 0.7648
_diffrn_measurement_details
;
  1 omega    1.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687  -99.0000 -180.0000 26

  2 omega   42.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687   57.0000  -90.0000 51

  3 omega   39.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687  -99.0000 -180.0000 40

  4 omega    0.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687   57.0000  -90.0000 37

  5 omega   58.00  136.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  178.0000  150.0000 78

  6 omega  -11.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  -25.0000  -90.0000 105

  7 omega  115.00  144.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  111.0000  -90.0000 29

  8 omega  101.00  133.00   1.0000   20.1350
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -120.0000 32

  9 omega  129.00  167.00   1.0000   20.1350
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -180.0000 38

 10 omega   26.00   82.00   1.0000   20.1350
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -32.0000 -150.0000 56

 11 omega  147.00  175.00   1.0000   20.1350
omega____ theta____ kappa____ phi______ frames
    -      108.0000  139.0000   62.0000 28

 12 omega   41.00  153.00   1.0000   20.1350
omega____ theta____ kappa____ phi______ frames
    -      108.0000   11.0000  -90.0000 112

 13 omega   86.00  113.00   1.0000   20.1350
omega____ theta____ kappa____ phi______ frames
    -      108.0000  139.0000   62.0000 27

 14 omega  136.00  169.00   1.0000   20.1350
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -120.0000 33

 15 omega  119.00  171.00   1.0000   20.1350
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -150.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0781386000
_diffrn_orient_matrix_UB_12      -0.0407472000
_diffrn_orient_matrix_UB_13      -0.0720072000
_diffrn_orient_matrix_UB_21      0.1340130000
_diffrn_orient_matrix_UB_22      -0.0258181000
_diffrn_orient_matrix_UB_23      0.0963739000
_diffrn_orient_matrix_UB_31      -0.1065112000
_diffrn_orient_matrix_UB_32      -0.0026670000
_diffrn_orient_matrix_UB_33      0.1724427000
_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  0.0220
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3924
_diffrn_reflns_theta_full        66.90
_diffrn_reflns_theta_max         66.90
_diffrn_reflns_theta_min         2.77
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.933
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.1613
_exptl_crystal_size_mid          0.0945
_exptl_crystal_size_min          0.0681
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+0.7295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1759
_reflns_number_gt                2096
_reflns_number_total             2608
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00317_si_001.cif
_cod_data_source_block           P8
_cod_original_cell_volume        1912.82(15)
_cod_database_code               4032545
_chemical_oxdiff_formula         'C72 H60 N12 O28 S4 '
_reflns_odcompleteness_completeness 76.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97