Diastereodivergent and Enantioselective Access to Spiroepoxides via Organocatalytic Epoxidation of Unsaturated Pyrazolones.
Meninno, Sara; Roselli, Angelo; Capobianco, Amedeo; Overgaard, Jacob; Lattanzi, Alessandra; Organic letters 19 (2017) 5030–5033; doi:10.1021/acs.orglett.7b02189

data_1547177
_publ_section_title
;
 Diastereodivergent and Enantioselective Access to Spiroepoxides via
 Organocatalytic Epoxidation of Unsaturated Pyrazolones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5030
_journal_page_last               5033
_journal_paper_doi               10.1021/acs.orglett.7b02189
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H13 Cl N2 O2'
_chemical_formula_sum            'C17 H13 Cl N2 O2'
_chemical_formula_weight         312.74
_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     direct
_audit_creation_date             2017-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3966(2)
_cell_length_b                   10.4923(3)
_cell_length_c                   16.3473(4)
_cell_measurement_reflns_used    7941
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.8250
_cell_measurement_theta_min      3.0780
_cell_volume                     1440.19(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (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(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_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    -70.00  51.00   1.00   10.00    --   10.32 -19.00  30.00  121
  2  \w    -63.00  38.00   1.00   10.00    --   10.32 -57.00   0.00  101
  3  \w     34.00  97.00   1.00   10.00    --   10.32-178.00 -60.00   63
  4  \w    -87.00   6.00   1.00   10.00    --  -11.34 -77.00  30.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0435010000
_diffrn_orient_matrix_UB_12      0.0574951000
_diffrn_orient_matrix_UB_13      0.0046410000
_diffrn_orient_matrix_UB_21      -0.0576059000
_diffrn_orient_matrix_UB_22      0.0223786000
_diffrn_orient_matrix_UB_23      0.0282969000
_diffrn_orient_matrix_UB_31      0.0438587000
_diffrn_orient_matrix_UB_32      -0.0276662000
_diffrn_orient_matrix_UB_33      0.0325581000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15951
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.488
_diffrn_reflns_theta_min         2.307
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43b (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    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1200 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0313P)^2^+0.2858P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                3236
_reflns_number_total             3613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02189_si_001.cif
_cod_data_source_block           exp_253
_cod_depositor_comments
'Adding full bibliography for 1547176--1547177.cif.'
_cod_original_cell_volume        1440.19(7)
_cod_database_code               1547177
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C17 H13 Cl1 N2 O2'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C008(H00A,H00B,H00C)
;
_olex2_date_sample_data_collection 2017-01-18
_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 1.112
_oxdiff_exptl_absorpt_empirical_full_min 0.951