Phosphine-catalyzed Michael additions to α-methylene-γ-butyrolactones.
Salin, Alexey V.; Islamov, Daut R.; Organic & biomolecular chemistry 17 (2019) 7293–7299; doi:10.1039/c9ob01401b

data_7156979
_publ_section_title
;
 Phosphine-catalyzed Michael additions to \a-methylene-\g-butyrolactones.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7293
_journal_page_last               7299
_journal_paper_doi               10.1039/c9ob01401b
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C17 H17 O3 P'
_chemical_formula_sum            'C17 H17 O3 P'
_chemical_formula_weight         300.27
_chemical_name_common
3-((Diphenylphosphoryl)methyl)dihydrofuran-2(3H)-one
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-07 deposited with the CCDC.    2019-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.88520(10)
_cell_length_b                   10.66490(10)
_cell_length_c                   31.4503(2)
_cell_measurement_reflns_used    28988
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.3620
_cell_measurement_theta_min      2.8200
_cell_volume                     2980.22(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'MERCURY 4.1 (Macrae, 2006)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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    -82.00  -3.00   0.50    0.05    --  -47.57 102.00-154.00  158
  2  \w    -16.00  64.00   0.50    0.05    --   47.57-102.00 101.00  160
  3  \w    -84.00 -58.00   0.50    0.09    -- -105.86 102.00-154.00   52
  4  \w   -149.00-124.00   0.50    0.09    -- -105.86-102.00 101.00   50
  5  \w    106.00 131.00   0.50    0.09    --  105.86 102.00-154.00   50
  6  \w     35.00 110.00   0.50    0.09    --  105.86-102.00 101.00  150
  7  \w     42.00 119.00   0.50    0.05    --   47.57  77.00 120.00  154
  8  \w     26.00  58.00   0.50    0.05    --   47.57  77.00-180.00   64
  9  \w     41.00  66.00   0.50    0.05    --   47.57  57.00-180.00   50
 10  \w     73.00 117.00   0.50    0.05    --   47.57 125.00 -90.00   88
 11  \w     83.00 111.00   0.50    0.05    --   47.57  57.00-180.00   56
 12  \w     27.00  89.00   0.50    0.05    --   47.57  77.00  90.00  124
 13  \w     72.00 116.00   0.50    0.05    --   47.57 125.00  90.00   88
 14  \w     35.00 114.00   0.50    0.05    --   47.57  37.00  90.00  158
 15  \w   -164.00-138.00   0.50    0.09    -- -105.86 -59.00  75.04   52
 16  \w   -115.00 -89.00   0.50    0.09    -- -105.86 -68.00  93.33   52
 17  \w   -147.00 -94.00   0.50    0.09    -- -105.86 -42.00 151.20  106
 18  \w   -119.00 -94.00   0.50    0.09    -- -105.86 -50.00  95.73   50
 19  \w   -103.00 -78.00   0.50    0.09    -- -105.86 -88.00  98.93   50
 20  \w   -104.00 -78.00   0.50    0.09    -- -105.86 -91.00 101.02   52
 21  \w   -117.00 -91.00   0.50    0.09    -- -105.86 -63.00  59.88   52
 22  \w   -105.00 -80.00   0.50    0.09    -- -105.86 -83.00 135.10   50
 23  \w   -172.00 -93.00   0.50    0.09    -- -105.86 -45.00 178.62  158
 24  \w   -142.00 -93.00   0.50    0.09    -- -105.86 -45.00  60.00   98
 25  \w   -113.00 -88.00   0.50    0.09    -- -105.86 -65.00 170.10   50
 26  \w   -111.00 -86.00   0.50    0.09    -- -105.86 -69.00-169.93   50
 27  \w   -110.00 -85.00   0.50    0.09    -- -105.86 -72.00 107.99   50
 28  \w   -108.00 -83.00   0.50    0.09    -- -105.86 -77.00 139.69   50
 29  \w   -103.00 -78.00   0.50    0.09    -- -105.86 -88.00 174.18   50
 30  \w   -175.00 -94.00   0.50    0.09    -- -105.86 -30.00 120.00  162
 31  \w   -114.00 -89.00   0.50    0.09    -- -105.86 -64.00 157.64   50
 32  \w   -129.00-103.00   0.50    0.09    -- -105.86 -61.00 120.00   52
 33  \w   -108.00 -83.00   0.50    0.09    -- -105.86 -77.00  90.00   50
 34  \w   -108.00 -83.00   0.50    0.09    -- -105.86 -77.00 150.00   50
 35  \w   -115.00 -90.00   0.50    0.09    -- -105.86 -59.00  75.04   50
 36  \w   -114.00 -89.00   0.50    0.09    -- -105.86 -61.00  90.00   50
 37  \w   -116.00 -91.00   0.50    0.09    -- -105.86 -61.00  60.00   50
 38  \w   -105.00 -80.00   0.50    0.09    -- -105.86 -83.00 164.69   50
 39  \w   -104.00 -79.00   0.50    0.09    -- -105.86 -87.00 179.79   50
 40  \w   -111.00 -86.00   0.50    0.09    -- -105.86 -70.00-163.23   50
 41  \w   -103.00 -78.00   0.50    0.09    -- -105.86 -88.00-159.81   50
 42  \w   -119.00 -94.00   0.50    0.09    -- -105.86 -49.00  68.72   50
 43  \w   -168.00-142.00   0.50    0.09    -- -105.86 -70.00-163.23   52
 44  \w   -105.00 -80.00   0.50    0.09    -- -105.86 -83.00 166.41   50
 45  \w   -103.00 -78.00   0.50    0.09    -- -105.86 -89.00-176.85   50
 46  \w   -109.00 -84.00   0.50    0.09    -- -105.86 -77.00-180.00   50
 47  \w   -174.00 -95.00   0.50    0.09    -- -105.86 -48.00  50.69  158
 48  \w   -146.00 -92.00   0.50    0.09    -- -105.86 -51.00  91.92  108
 49  \w   -110.00 -85.00   0.50    0.09    -- -105.86 -73.00-175.39   50
 50  \w     33.00 128.00   0.50    0.09    --  105.86 -77.00-180.00  190
 51  \w     83.00 108.00   0.50    0.09    --  105.86  77.00  60.00   50
 52  \w    153.00 178.00   0.50    0.09    --  105.86  77.00 150.00   50
 53  \w     83.00 109.00   0.50    0.09    --  105.86  77.00 150.00   52
 54  \w    152.00 178.00   0.50    0.09    --  105.86  77.00 120.00   52
 55  \w     90.00 116.00   0.50    0.09    --  105.86  61.00  90.00   52
 56  \w     83.00 109.00   0.50    0.09    --  105.86  77.00 120.00   52
 57  \w     31.00 117.00   0.50    0.09    --  105.86 -30.00  90.00  172
 58  \w     36.00 108.00   0.50    0.09    --  105.86 -45.00  60.00  144
 59  \w    142.00 167.00   0.50    0.09    --  105.86  77.00  90.00   50
 60  \w     84.00 110.00   0.50    0.09    --  105.86  77.00  90.00   52
 61  \w    141.00 166.00   0.50    0.09    --  105.86  77.00  60.00   50
 62  \w    106.00 178.00   0.50    0.09    --  105.86  45.00 -60.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0854025000
_diffrn_orient_matrix_UB_12      -0.0228381000
_diffrn_orient_matrix_UB_13      -0.0419246000
_diffrn_orient_matrix_UB_21      -0.1466791000
_diffrn_orient_matrix_UB_22      0.0460053000
_diffrn_orient_matrix_UB_23      0.0209499000
_diffrn_orient_matrix_UB_31      0.0355549000
_diffrn_orient_matrix_UB_32      0.1349835000
_diffrn_orient_matrix_UB_33      -0.0142466000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            48852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.638
_diffrn_reflns_theta_min         2.810
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0694P)^2^+2.8679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2901
_reflns_number_total             3118
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01401b2.cif
_cod_data_source_block           sal10
_cod_depositor_comments
'Adding full bibliography for 7156978--7156981.cif.'
_cod_database_code               7156979
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C17 H17 O3 P'
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.550
_diffrn_oxdiff_digest_frames
;
011a994f68e95db14fabe698ac64114fc5000667d56
;
_diffrn_oxdiff_digest_hkl
;
01116d7f5ebeee673d6e338c8adaeae6a48b33
;
_reflns_odcompleteness_completeness 99.97
_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
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
_shelx_res_checksum              8951
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.874
_oxdiff_exptl_absorpt_empirical_full_min 0.516