Efficient synthesis of (E)-2-nitromethylcinnamates via phosphine-catalyzed tandem α-addition and 1,3-rearrangement
Huang, Guofei; Ren, Xiaoyu; Jiang, Chunhui; Wu, Jia-Hong; Gao, Guowei; Wang, Tianli; Organic Chemistry Frontiers 6 (2019) 2872–; doi:10.1039/C9QO00478E

data_1554931
_publ_section_title
;
 Efficient synthesis of (E)-2-nitromethylcinnamates via
 phosphine-catalyzed tandem \a-addition and 1,3-rearrangement
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2872
_journal_paper_doi               10.1039/C9QO00478E
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C18 H19 N O4 S'
_chemical_formula_sum            'C18 H19 N O4 S'
_chemical_formula_weight         345.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-19 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4772(6)
_cell_length_b                   10.4880(5)
_cell_length_c                   19.6463(5)
_cell_measurement_reflns_used    4641
_cell_measurement_temperature    296.8(2)
_cell_measurement_theta_max      72.7040
_cell_measurement_theta_min      4.5300
_cell_volume                     3601.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_environment      air
_diffrn_ambient_temperature      296.8(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -108.00  -7.00   1.00    1.82    --  -36.29 -19.00-180.00  101
  2  \w   -104.00 -20.00   1.00    1.82    --  -36.29 -57.00-120.00   84
  3  \w     23.00  90.00   1.00    1.82    --   36.29-125.00  30.00   67
  4  \w      1.00  75.00   1.00    1.82    --   36.29 -99.00  90.00   74
  5  \w      1.00  75.00   1.00    1.82    --   36.29 -99.00-150.00   74
  6  \w      1.00  75.00   1.00    1.82    --   36.29 -99.00  30.00   74
  7  \w      1.00  75.00   1.00    1.82    --   36.29 -99.00 150.00   74
  8  \w     39.00 109.00   1.00    7.28    --  108.71 -94.00-180.00   70
  9  \w     39.00 109.00   1.00    7.28    --  108.71 -94.00 120.00   70
 10  \w     40.00 126.00   1.00    7.28    --  108.71 -45.00  30.00   86
 11  \w     41.00 135.00   1.00    7.28    --  108.71 -77.00 -60.00   94
 12  \w     82.00 157.00   1.00    7.28    --  108.71  77.00  60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0769729000
_diffrn_orient_matrix_UB_12      -0.0258100000
_diffrn_orient_matrix_UB_13      -0.0356718000
_diffrn_orient_matrix_UB_21      0.0188657000
_diffrn_orient_matrix_UB_22      0.1030784000
_diffrn_orient_matrix_UB_23      -0.0534081000
_diffrn_orient_matrix_UB_31      0.0386274000
_diffrn_orient_matrix_UB_32      -0.1013750000
_diffrn_orient_matrix_UB_33      -0.0450098000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13783
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.981
_diffrn_reflns_theta_min         4.501
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1241P)^2^+1.4702P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2864
_reflns_number_total             3508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00478e2.cif
_cod_data_source_block           wtl-hgf-r1
_cod_database_code               1554931
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H),
 C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C00N(H00F,H00J,H00N), C00O(H00O,H00P,H00Q)
;
_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 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.777