Chloromethanesulfonylethene and dichloromethanesulfonylethene: new reagents for tandem Diels-Alder/Ramberg-Bäcklund reactions.
Block, Eric; Jeon, Hak Rim; Zhang, Shao-Zhong; Dikarev, Evgeny V.; Organic letters 6 (2004) 437–440; doi:10.1021/ol0363523

data_1506902
_publ_section_title
;
 Chloromethanesulfonylethene and dichloromethanesulfonylethene: new
 reagents for tandem Diels-Alder/Ramberg-B\"acklund reactions.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              437
_journal_page_last               440
_journal_paper_doi               10.1021/ol0363523
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C7 H8 (S O2 C H2 Cl)2'
_chemical_formula_sum            'C9 H12 Cl2 O4 S2'
_chemical_formula_weight         319.21
_chemical_melting_point          ?
_chemical_name_systematic
;
 5-endo-6-exo-bis(chloromethanesulfonyl)bicyclo[2.2.1]hept-2-ene
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.946(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9279(6)
_cell_length_b                   7.8341(4)
_cell_length_c                   15.8873(9)
_cell_measurement_reflns_used    9019
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.246
_cell_measurement_theta_min      2.316
_cell_volume                     1229.01(12)
_computing_cell_refinement       'SMART, SAINT'
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXP-93 (Sheldrick, 1993)'
_computing_publication_material  'SHELXCIF-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '0.3 deg wide \w exposures'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10324
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count na
_diffrn_standards_interval_time  na
_diffrn_standards_number         'none (area detector data)'
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.9419
_exptl_absorpt_correction_T_min  0.7935
_exptl_absorpt_correction_type   'multiscan (SADABS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    calculated
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.23(4)
_refine_ls_extinction_coef       noref
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5383
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0553P)^2^+0.0578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                5260
_reflns_number_total             5383
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0363523si20031205_064943.cif
_cod_data_source_block           S2Cl2O4C9H12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1229.0(1)
_cod_database_code               1506902