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_4032542
_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_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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_date             2016-12-13
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  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
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_cell_angle_alpha                90.00
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_cell_angle_gamma                90.00
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_cell_length_a                   7.57183(10)
_cell_length_b                   14.7939(2)
_cell_length_c                   16.2756(3)
_cell_measurement_reflns_used    10886
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.2040
_cell_measurement_theta_min      3.6680
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
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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 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_details
;
  1 omega   47.00   72.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.2344   57.0000 -120.0000 25

  2 omega  -29.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       31.3103  -77.0000  -90.0000 88

  3 omega   47.00  117.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       31.3103  178.0000  -60.0000 70

  4 omega   57.00  104.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       31.3103   38.0000   90.0000 47

  5 omega    2.00   79.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       31.3103   77.0000  150.0000 77

  6 omega   -4.00   74.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       31.3103  -99.0000   30.0000 78

  7 omega  -41.00  102.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       31.3103  -19.0000  -90.0000 143

  8 omega  -86.00  -61.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.7791  178.0000   90.0000 25
;
_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      0.0068068000
_diffrn_orient_matrix_UB_12      -0.0148392000
_diffrn_orient_matrix_UB_13      -0.0413110000
_diffrn_orient_matrix_UB_21      0.0546678000
_diffrn_orient_matrix_UB_22      -0.0363456000
_diffrn_orient_matrix_UB_23      0.0127326000
_diffrn_orient_matrix_UB_31      -0.0757503000
_diffrn_orient_matrix_UB_32      -0.0275447000
_diffrn_orient_matrix_UB_33      0.0054745000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21938
_diffrn_reflns_theta_full        32.28
_diffrn_reflns_theta_max         32.28
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.956
_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    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.3599
_exptl_crystal_size_mid          0.2015
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       0.0023(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0446P)^2^+0.3659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                5196
_reflns_number_total             5998
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00317_si_001.cif
_cod_data_source_block           P5
_cod_original_cell_volume        1823.15(5)
_cod_database_code               4032542
_chemical_oxdiff_formula         'C76 H60 N12 O24 S4 '
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32