A four-step cascade reaction involving O[1,3] sigmatropic shift and Smiles rearrangements as key steps
Zhang, Guangyu; Xu, Jiaxi; New Journal of Chemistry 46 (2022) 9322–9330; doi:10.1039/D2NJ01393B

data_7061448
_publ_section_title
;
 A four-step cascade reaction involving O[1,3] sigmatropic shift and
 Smiles rearrangements as key steps
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9322
_journal_page_last               9330
_journal_paper_doi               10.1039/D2NJ01393B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C20 H14 N4 O8'
_chemical_formula_sum            'C20 H14 N4 O8'
_chemical_formula_weight         438.35
_chemical_melting_point          442.6(5)
_chemical_name_common
;
2-arylaminophenyl benzoate
;
_chemical_name_systematic
;
 5-Methyl-2-((2,4,6-trinitrophenyl)amino)phenyl benzoate 
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-11-18
_audit_creation_method
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  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2022-02-04 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.124(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4462(7)
_cell_length_b                   6.6861(4)
_cell_length_c                   23.1127(9)
_cell_measurement_reflns_used    1449
_cell_measurement_temperature    113.10(14)
_cell_measurement_theta_max      25.9880
_cell_measurement_theta_min      4.4800
_cell_volume                     1904.06(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      113.10(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.8192
_diffrn_measurement_details
;
  1 omega  -23.00   17.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -57.0000   90.0000 40

  2 omega   15.00   41.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -99.0000   60.0000 26

  3 omega  -53.00   72.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852    0.0000  120.0000 125

  4 omega   37.00   81.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  178.0000 -120.0000 44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0477901000
_diffrn_orient_matrix_UB_12      0.0590428000
_diffrn_orient_matrix_UB_13      -0.0047345000
_diffrn_orient_matrix_UB_21      0.0199926000
_diffrn_orient_matrix_UB_22      0.0492888000
_diffrn_orient_matrix_UB_23      -0.0234716000
_diffrn_orient_matrix_UB_31      -0.0251372000
_diffrn_orient_matrix_UB_32      -0.0730784000
_diffrn_orient_matrix_UB_33      -0.0196758000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8526
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.94
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97515
_exptl_absorpt_correction_type   multi-scan
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
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_refine_ls_number_parameters     290
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0317P)^2^+0.4771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1097
_reflns_number_gt                2595
_reflns_number_total             3649
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2nj01393b2.cif
_cod_data_source_block           exp_7608
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '169-170 deg' was changed
to '442.6(5)' -- it was converted from degrees Celsius (C) to kelvins
(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7061448.cif.
;
_cod_original_cell_volume        1904.04(16)
_cod_database_code               7061448
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07