Formal [3 + 2] cycloaddition of α-unsubstituted isocyanoacetates and methyleneindolinones: enantioselective synthesis of spirooxindoles
Peng, Xiao-Jiao; Ho, Yee Ann; Wang, Zhi-Peng; Shao, Pan-Lin; Zhao, Yu; He, Yun; Organic Chemistry Frontiers 4 (2017) 81–; doi:10.1039/C6QO00555A

data_1553571
_publ_section_title
;
 Formal [3 + 2] cycloaddition of \a-unsubstituted isocyanoacetates and
 methyleneindolinones: enantioselective synthesis of spirooxindoles
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              81
_journal_paper_doi               10.1039/C6QO00555A
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H17 Cl N2 O3'
_chemical_formula_sum            'C15 H17 Cl N2 O3'
_chemical_formula_weight         308.75
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-02-29
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5097)
;
_audit_update_record
;
2016-07-27 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2915(5)
_cell_length_b                   12.7983(10)
_cell_length_c                   15.9552(9)
_cell_measurement_reflns_used    1880
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6620
_cell_measurement_theta_min      4.0870
_cell_volume                     1488.92(18)
_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_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6234
_diffrn_reflns_point_group_measured_fraction_full 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_min         3.430
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 667 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0384P)^2^+0.1578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.500
_reflns_Friedel_fraction_full    0.736
_reflns_Friedel_fraction_max     0.597
_reflns_number_gt                2641
_reflns_number_total             3524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00555a2.cif
_cod_data_source_block           20160229-heyun-pengxiaojiao-pxj-cl-danjing1
_cod_original_cell_volume        1488.92(17)
_cod_database_code               1553571
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00e,H00i)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), C00D(H00D), C00F(H00F), C00H(H00H)
2.d Idealised Me refined as rotating group:
 C00B(H00a,H00b,H00c), C00K(H00j,H00k,H00l), C00L(H00m,H00n,H00o)
;
_shelx_res_checksum              44340
_shelx_hkl_checksum              68850
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'