Enantioselective N-heterocyclic carbene-catalyzed synthesis of indenopyrones.
Chen, Kun-Quan; Zhang, Han-Ming; Wang, Dong-Ling; Sun, De-Qun; Ye, Song; Organic & biomolecular chemistry 13 (2015) 6694–6697; doi:10.1039/c5ob00859j

data_7154427
_publ_section_title
;
 Enantioselective N-heterocyclic carbene-catalyzed synthesis of
 indenopyrones.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6694
_journal_page_last               6697
_journal_paper_doi               10.1039/c5ob00859j
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H17 Cl O3'
_chemical_formula_sum            'C25 H17 Cl O3'
_chemical_formula_weight         400.83
_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
_audit_creation_date             2014-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2015-04-27 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.8099(10)
_cell_length_b                   21.073(4)
_cell_length_c                   32.234(6)
_cell_measurement_reflns_used    8786
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4850
_cell_measurement_theta_min      1.1545
_cell_volume                     3946.5(12)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0205
_diffrn_orient_matrix_UB_12      0.0586
_diffrn_orient_matrix_UB_13      0.1605
_diffrn_orient_matrix_UB_21      -0.0027
_diffrn_orient_matrix_UB_22      -0.0446
_diffrn_orient_matrix_UB_23      0.0159
_diffrn_orient_matrix_UB_31      0.0308
_diffrn_orient_matrix_UB_32      -0.0004
_diffrn_orient_matrix_UB_33      0.0041
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            27021
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.154
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       rod
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2870 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         8664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0477
_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^)+(0.0312P)^2^+1.1465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                8224
_reflns_number_total             8664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00859j2.cif
_cod_data_source_block           mx3313
_cod_depositor_comments          'Adding full bibliography for 7154427.cif.'
_cod_database_code               7154427
_shelxl_version_number           2013-4
_diffrn_number_total             5193
_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:
 C1A(H1A), C2A(H2A), C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C12(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C9A(H9A), C11A(H11A), C14A(H14A), C15A(H15A), C16A(H16A),
 C17A(H17A), C18A(H18A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C7(H7),
  C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23)
;
_shelx_res_checksum              12275