An efficient route to highly enantioenrichedtetrahydroazulenes and beta-tetralones by desymmetrization reactions of delta,delta-diaryldiazoaceto-acetates
Yuxiao Liu; Yongming Deng; Peter Y. Zavalij; Renhua Liu; Michael P. Doyle; Chem.Commun. 51 (2015) 565–; doi:10.1039/C4cc08255A

data_7116384
_publ_section_title
;
 An efficient route to highly enantioenrichedtetrahydroazulenes and
 beta-tetralones by desymmetrization reactions of
 delta,delta-diaryldiazoaceto-acetates
;
_journal_name_full               Chem.Commun.
_journal_page_first              565
_journal_paper_doi               10.1039/C4cc08255A
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 Cl2 O3'
_chemical_formula_sum            'C21 H20 Cl2 O3'
_chemical_formula_weight         391.27
_chemical_name_systematic
;
organic
;
_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_cell_setting           orthorhombic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2014 & ZCIF'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9383(8)
_cell_length_b                   11.4949(8)
_cell_length_c                   15.5104(11)
_cell_measurement_reflns_used    26196
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.3
_cell_volume                     1950.2(2)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_data_reduction        'Apex2, Saint'
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  'Apex2, SHELXL-2014, Platon (Spek, 1990)'
_computing_structure_refinement  'ShelXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0010869
_diffrn_orient_matrix_UB_12      0.0672333
_diffrn_orient_matrix_UB_13      0.0409146
_diffrn_orient_matrix_UB_21      -0.0875948
_diffrn_orient_matrix_UB_22      -0.0149957
_diffrn_orient_matrix_UB_23      0.0146858
_diffrn_orient_matrix_UB_31      0.0261400
_diffrn_orient_matrix_UB_32      -0.0531290
_diffrn_orient_matrix_UB_33      0.0476127
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32314
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.994
_diffrn_reflns_theta_min         2.205
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Flack x determined using 2428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0249
_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^)+(0.0100P)^2^+0.7200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0525
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5582
_reflns_number_total             5686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc08255a2.cif
_cod_data_source_block           2601
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7116384
_shelx_estimated_absorpt_t_min   0.844
_shelx_estimated_absorpt_t_max   0.873
_shelxl_version_number           2014-3
_shelx_res_checksum              23904
_shelx_hkl_checksum              69835