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_4032544
_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      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                91.541(4)
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_cell_angle_gamma                93.835(3)
_cell_formula_units_Z            4
_cell_length_a                   9.6002(3)
_cell_length_b                   13.5064(6)
_cell_length_c                   14.3807(7)
_cell_measurement_reflns_used    5881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.7310
_cell_measurement_theta_min      4.5490
_cell_volume                     1859.48(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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 0.9797
_diffrn_measured_fraction_theta_max 0.9841
_diffrn_measurement_details
;
  1 omega   14.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687  -57.0000  -30.0000 49

  2 omega   29.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687  -57.0000   90.0000 35

  3 omega   -3.00  151.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844   12.0000  120.0000 154

  4 omega  151.00  178.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000   90.0000 27

  5 omega  110.00  136.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  111.0000  150.0000 26

  6 omega  102.00  175.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  150.0000 73

  7 omega  101.00  138.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  111.0000   30.0000 37

  8 omega  101.00  173.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  120.0000 72

  9 omega  132.00  158.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000  -60.0000 26

 10 omega  137.00  169.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000  -90.0000 32

 11 omega  119.00  150.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  111.0000 -180.0000 31

 12 omega  104.00  132.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  111.0000  -90.0000 28

 13 omega  105.00  144.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  120.0000 -130.0000 39

 14 omega   80.00  116.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000  -60.0000 36

 15 omega   96.00  177.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   27.0000 -154.1343 81

 16 omega  120.00  146.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000 -180.0000 26

 17 omega   78.00  120.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -125.0000  -12.8376 42

 18 omega  110.00  145.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000   30.0000 35

 19 omega  110.00  136.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 26

 20 omega   67.00  109.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000    0.0000 42

 21 omega   68.00   98.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000   60.0000 30

 22 omega   59.00  113.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  120.0000 54

 23 omega   43.00   81.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 38

 24 omega   40.00   92.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000   30.0000 52

 25 omega   28.00   53.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  120.0000 25

 26 omega   24.00   50.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000   60.0000 26

 27 omega   23.00   64.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000    0.0000 41

 28 omega   -8.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  -91.0000 -120.0000 120

 29 omega   34.00  153.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -89.0000 -180.0000 119

 30 omega   43.00  131.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000  -90.0000 88

 31 omega   67.00  136.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   43.0000   90.0000 69

 32 omega   61.00  148.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844  178.0000  -90.0000 87

 33 omega   37.00  143.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       66.7844   63.0000  -30.0000 106

 34 omega   38.00  115.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000 -180.0000 77

 35 omega   31.00   82.00   1.0000    7.8050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   27.0000 -154.1343 51

 36 omega  -18.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687  -57.0000 -180.0000 82

 37 omega  -47.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687  -57.0000  -30.0000 58

 38 omega  -51.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687  -57.0000   90.0000 78

 39 omega  -50.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       25.5687  -57.0000 -180.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0167497000
_diffrn_orient_matrix_UB_12      0.0157078000
_diffrn_orient_matrix_UB_13      -0.1050332000
_diffrn_orient_matrix_UB_21      0.0180744000
_diffrn_orient_matrix_UB_22      -0.1117010000
_diffrn_orient_matrix_UB_23      -0.0153451000
_diffrn_orient_matrix_UB_31      -0.1589625000
_diffrn_orient_matrix_UB_32      -0.0188430000
_diffrn_orient_matrix_UB_33      -0.0148710000
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11440
_diffrn_reflns_theta_full        66.90
_diffrn_reflns_theta_max         66.90
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.989
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
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    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.1976
_exptl_crystal_size_mid          0.0794
_exptl_crystal_size_min          0.0681
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         6518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0488P)^2^+0.2953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                5508
_reflns_number_total             6518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00317_si_001.cif
_cod_data_source_block           P7
_cod_original_cell_volume        1859.48(13)
_cod_database_code               4032544
_chemical_oxdiff_formula         'C72 H60 N12 O28 S4 '
_reflns_odcompleteness_completeness 97.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.613
_oxdiff_exptl_absorpt_empirical_full_min 0.766