Organocatalytic cis-Selective Approach to Bicyclic δ-Lactones
Kowalczyk, Dorota; Albrecht, Lukasz; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01570D

data_7155813
_publ_section_title
;
 Organocatalytic cis-Selective Approach to Bicyclic \d-Lactones
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01570D
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H23 Cl O4'
_chemical_formula_sum            'C25 H23 Cl O4'
_chemical_formula_weight         422.88
_chemical_name_systematic
'3-[2-(4-Chlorophenyl)-2-oxoethyl]- 7,7-dimethyl-4-phenyl-4,6,7,8-tetrahydro-2H-chromene-2,5(3H)-dione'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2017-06-14 deposited with the CCDC.
2017-08-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8155(2)
_cell_length_b                   11.5974(3)
_cell_length_c                   31.3321(10)
_cell_measurement_reflns_used    8211
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.5300
_cell_measurement_theta_min      4.0520
_cell_volume                     2113.18(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_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    -92.00 -28.00   0.50   16.00    --  -84.25 125.00  30.00  128
  2  \w    -27.00  42.00   0.50    7.00    --    0.00  92.00 177.00  138
  3  \w     87.00 167.00   0.50   16.00    --  105.75  77.00  90.00  160
  4  \w    131.00 167.00   0.50   16.00    --  105.75  77.00  60.00   72
  5  \w     86.00 117.00   0.50   16.00    --  105.75  77.00  60.00   62
  6  \w     86.00 120.00   0.50   16.00    --  105.75  77.00 -30.00   68
  7  \w    143.00 168.00   0.50   16.00    --  105.75  77.00  30.00   50
  8  \w    134.00 168.00   0.50   16.00    --  105.75  77.00 -30.00   68
  9  \w     86.00 132.00   0.50   16.00    --  105.75  77.00  30.00   92
 10  \w    -33.00  -7.00   0.50    7.00    --    0.00   0.00 -60.00   52
 11  \w    -49.00   2.00   0.50    7.00    --    0.00   0.00-150.00  102
 12  \w   -136.00-105.00   0.50   16.00    --  -84.25 -77.00 120.00   62
 13  \w    -45.00 -15.00   0.50   16.00    --  -84.25  38.00-180.00   60
 14  \w    -38.00 -11.00   0.50   16.00    --  -84.25  38.00 120.00   54
 15  \w     42.00 118.00   0.50   16.00    --  105.75 -77.00 150.00  152
 16  \w     48.00  90.00   0.50   16.00    --  105.75 -57.00  60.00   84
 17  \w    151.00 176.00   0.50   16.00    --  105.75 125.00-120.00   50
 18  \w     32.00  60.00   0.50   16.00    --  105.75 -38.00-180.00   56
 19  \w     91.00 118.00   0.50   16.00    --  105.75 125.00-120.00   54
 20  \w     67.00  96.00   0.50   16.00    --  105.75 -19.00 -90.00   58
 21  \w    -70.00  13.00   0.50    7.00    --    0.00 -57.00  60.00  166
 22  \w    -49.00   8.00   0.50    7.00    --    0.00   0.00 -90.00  114
 23  \w    -20.00  64.00   0.50    7.00    --    0.00  77.00   0.00  168
 24  \w   -148.00-123.00   0.50   16.00    --  -84.25 -77.00 -30.00   50
 25  \w   -157.00 -79.00   0.50   16.00    --  -84.25 -19.00-150.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2313818000
_diffrn_orient_matrix_UB_12      0.0105050000
_diffrn_orient_matrix_UB_13      0.0235780000
_diffrn_orient_matrix_UB_21      -0.1238292000
_diffrn_orient_matrix_UB_22      -0.0543245000
_diffrn_orient_matrix_UB_23      -0.0385504000
_diffrn_orient_matrix_UB_31      0.0356206000
_diffrn_orient_matrix_UB_32      -0.1207665000
_diffrn_orient_matrix_UB_33      0.0194091000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            15558
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         72.098
_diffrn_reflns_theta_min         4.065
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.840
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.480
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.920
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
;
 Flack x determined using 1311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0615
_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^)+(0.1049P)^2^+0.5808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1593
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                3620
_reflns_number_total             4088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01570d2.cif
_cod_data_source_block           la_dk_179_3
_cod_database_code               7155813
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C25 H20 O4 Cl'
_diffrn_oxdiff_ac3_digest_frames
;
012478ae837d01ebb7538ea3d3fd537b3802276b2bf
;
_diffrn_oxdiff_ac3_digest_hkl
;
01ba6ab07bcf00a2a47f782650828541f86f7f
;
_reflns_odcompleteness_completeness 99.73
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_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 1.693
_oxdiff_exptl_absorpt_empirical_full_min 0.623