Michael reaction for asymmetric synthesis of a drug-like oxa-spirocyclic indanone scaffold
Xiang Li; Lei Yang; Cheng Peng; Xin Xie; Hai-Jun Leng; Biao Wang; Zheng-Wei Tang; Gu He; Liang Ouyang; Wei Huang; Bo Han; Chem.Commun. 49 (2013) 8692–; doi:10.1039/c3cc44004d

data_7109757
_publ_section_title
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 Michael reaction for asymmetric synthesis of a drug-like oxa-spirocyclic
 indanone scaffold
;
_journal_name_full               Chem.Commun.
_journal_page_first              8692
_journal_paper_doi               10.1039/c3cc44004d
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H14 Cl N O6'
_chemical_formula_sum            'C20 H14 Cl N O6'
_chemical_formula_weight         399.77
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-15
_audit_creation_method
;
Olex2 1.2
(compiled Dec 5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1843(16)
_cell_length_b                   10.679(2)
_cell_length_c                   21.790(4)
_cell_measurement_reflns_used    7410
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      29.131
_cell_measurement_theta_min      1.907
_cell_volume                     1904.4(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      143(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16915
_diffrn_reflns_theta_full        29.14
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         2.67
_diffrn_source                   'Rotating Anode'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.9183
_exptl_absorpt_correction_T_min  0.9109
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(5)
_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     254
_refine_ls_number_reflns         5110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0436P)^2^+0.1060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                4848
_reflns_number_total             5110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44004d.txt
_cod_data_source_block           y3030
_cod_database_code               7109757
_olex2_refinement_description
;
1. Others
Fixed Uiso: H3(0.033) H4(0.041) H5(0.045) H6(0.038) H10(0.024) H11(0.026)
H12(0.031) H15(0.033) H16(0.041) H17(0.044) H18(0.041) H20A(0.054) H20B(0.054)
H20C(0.054)
Fixed X: H3(-0.1405) H4(-0.2161) H5(-0.0347) H6(0.2255) H10(0.5794)
H11(0.3389) H12(0.5748) H15(0.7775) H16(0.9723) H17(0.8904) H18(0.6126)
H20A(0.3046) H20B(0.4922) H20C(0.4278)
Fixed Y: H3(0.2649) H4(0.1) H5(-0.0634) H6(-0.0683) H10(0.2953) H11(0.4896)
H12(0.4007) H15(0.4471) H16(0.5919) H17(0.786) H18(0.8368) H20A(0.5619)
H20B(0.6043) H20C(0.5118)
Fixed Z: H3(0.3227) H4(0.2581) H5(0.2377) H6(0.2821) H10(0.392) H11(0.4082)
H12(0.4955) H15(0.417) H16(0.3855) H17(0.347) H18(0.3415) H20A(0.5184)
H20B(0.5174) H20C(0.5699)
;