Synthesis of Densely Substituted Sulfonylfurans and Dihydrofurans via Cascade Reactions of α-Functionalized Nitroalkenes with β-Ketosulfones.
Mane, Vaijinath; Sivanandan, Sudheesh T.; Santana, Rafael G.; Beatriz, Adilson; da Silva Júnior, Eufrânio N; Namboothiri, Irishi N. N.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00606

data_4038534
_publ_section_title
;
 Synthesis of Densely Substituted Sulfonylfurans and Dihydrofurans via
 Cascade Reactions of \a-Functionalized Nitroalkenes with \b-Ketosulfones.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00606
_journal_year                    2020
_chemical_formula_moiety         'C26 H32 N2 O8 S'
_chemical_formula_sum            'C26 H32 N2 O8 S'
_chemical_formula_weight         532.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-12
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.673(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3582(8)
_cell_length_b                   11.1376(3)
_cell_length_c                   28.4519(10)
_cell_measurement_reflns_used    4475
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      3.0
_cell_volume                     6035.8(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 214
	           Slice: -88.0000 - 19.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -36.0000
	             XTD: 44.9856
	          2theta: -19.9528
scan:
	Number of images: 164
	           Slice: -101.0000 - -19.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -72.0000
	             Phi: -108.0000
	             XTD: 44.9856
	          2theta: -19.9528
scan:
	Number of images: 61
	           Slice: 28.0000 - 58.5000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -180.0000
	             XTD: 44.9856
	          2theta: -19.9528
scan:
	Number of images: 225
	           Slice: -47.0000 - 65.5000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 72.0000
	             Phi: -108.0000
	             XTD: 44.9856
	          2theta: -19.9528
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      -0.087302
_diffrn_orient_matrix_UB_12      0.163679
_diffrn_orient_matrix_UB_13      -0.184617
_diffrn_orient_matrix_UB_21      -0.083548
_diffrn_orient_matrix_UB_22      0.011747
_diffrn_orient_matrix_UB_23      -0.060675
_diffrn_orient_matrix_UB_31      0.076481
_diffrn_orient_matrix_UB_32      -0.064991
_diffrn_orient_matrix_UB_33      0.151118
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18224
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.382
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0786P)^2^+5.2615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4212
_reflns_number_total             5294
_reflns_shell_number_unique_all  8510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00606_si_001.cif
_cod_data_source_block           inn-mvd-326_mo
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4038534
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 90.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.15
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00P(H00P), C00Q(H00Q), C00W(H00W), C00X(H00X)
2.b Aromatic/amide H refined with riding coordinates:
 N00A(H00A), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L),
 C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V)
2.c Idealised Me refined as rotating group:
 C00K(H00B,H00C,H00D), C00U(H00E,H00G,H00K), C00Y(H00M,H00N,H00O), C00Z(H,H00U,
 H00Y), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F)
;
_shelx_fab_checksum              89574
_shelx_shelxl_version_number     2018/3
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.396
_oxdiff_exptl_absorpt_empirical_full_min 0.470