Tertiary amine-catalyzed and direct synthesis of α-chloroalkanesulfonylhydrazines from azodicarboxylates and sulfonyl chlorides.
Zhou, Bingnan; Xu, Jiaxi; Organic & biomolecular chemistry 14 (2016) 4918–4926; doi:10.1039/c6ob00648e

data_7155097
_publ_section_title
;
 Tertiary amine-catalyzed and direct synthesis of
 \a-chloroalkanesulfonylhydrazines from azodicarboxylates and sulfonyl
 chlorides.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4918
_journal_page_last               4926
_journal_paper_doi               10.1039/c6ob00648e
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C15 H18 Cl N3 O9 S'
_chemical_formula_sum            'C15 H18 Cl N3 O9 S'
_chemical_formula_weight         451.83
_chemical_melting_point          400.6(5)
_chemical_name_common            'hydrazine 4ab'
_chemical_name_systematic
;
diethyl 1-(1-chloroethanesulfonyl)-2-(4-nitrobenzoyl)hydrazine-1,2-dicarboxylate 
;
_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             2015-07-06
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2016-03-14 deposited with the CCDC.
2016-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.346(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4540(9)
_cell_length_b                   10.0078(3)
_cell_length_c                   16.7460(8)
_cell_measurement_reflns_used    2777
_cell_measurement_temperature    106.1
_cell_measurement_theta_max      29.3990
_cell_measurement_theta_min      3.2691
_cell_volume                     1969.3(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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_temperature      106.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -50.00    0.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000 -180.0000 50

  2 omega  -35.00   12.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000   60.0000 47

  3 omega   22.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000  -90.0000 60

  4 omega  -42.00   23.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000  -60.0000 65
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0387381000
_diffrn_orient_matrix_UB_12      -0.0311660000
_diffrn_orient_matrix_UB_13      0.0361973000
_diffrn_orient_matrix_UB_21      -0.0436363000
_diffrn_orient_matrix_UB_22      -0.0439715000
_diffrn_orient_matrix_UB_23      0.0021017000
_diffrn_orient_matrix_UB_31      0.0155144000
_diffrn_orient_matrix_UB_32      -0.0460129000
_diffrn_orient_matrix_UB_33      -0.0265124000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8504
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.45
_refine_diff_density_max         1.602
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0497P)^2^+3.9214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1418
_reflns_number_gt                3233
_reflns_number_total             3868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00648e2.cif
_cod_data_source_block           exp_3424
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '127-128 deg' was changed to
'400.6(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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155097.cif.
;
_cod_original_cell_volume        1969.33(18)
_cod_database_code               7155097
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32