Stereoselective Synthesis of 1-Methyl-3',4',5',6'-tetrahydrospiro[indoline-3,2'-pyran]-2-one Derivatives via Prins Cyclization.
Damera, Krishna; Yu, Bingchen; Wang, Binghe; The Journal of organic chemistry 80 (2015) 5457–5463; doi:10.1021/acs.joc.5b00249

data_4030963
_publ_section_title
;
 Stereoselective Synthesis of
 1-Methyl-3',4',5',6'-tetrahydrospiro[indoline-3,2'-pyran]-2-one
 Derivatives via Prins Cyclization.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5457
_journal_page_last               5463
_journal_paper_doi               10.1021/acs.joc.5b00249
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C20 H20 Br N O4'
_chemical_formula_sum            'C20 H20 Br N O4'
_chemical_formula_weight         418.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-11-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.07 svn.r3078 for OlexSys, GUI svn.r4941)
;
_cell_angle_alpha                95.567(4)
_cell_angle_beta                 108.801(4)
_cell_angle_gamma                95.300(4)
_cell_formula_units_Z            2
_cell_length_a                   7.737(2)
_cell_length_b                   10.668(3)
_cell_length_c                   11.524(3)
_cell_measurement_reflns_used    7955
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.23
_cell_measurement_theta_min      2.513
_cell_volume                     888.4(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.1-1 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10782
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.289
_diffrn_reflns_theta_min         2.513
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.340
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0701 before and 0.0364 after correction.
The Ratio of minimum to maximum transmission is 0.8114.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.523
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.134
_refine_diff_density_max         1.267
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5179
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0613P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4152
_reflns_number_total             5179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00249_si_002.cif
_cod_data_source_block           dk-vii-111b
_cod_depositor_comments
'Adding full bibliography for 4030962--4030963.cif.'
_cod_database_code               4030963
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All H(H) groups
2. Restrained distances
 C4-H4b
 1 with sigma of 0.02
 O2-H2
 0.95 with sigma of 0.01
 C3-H3 \\sim C4-H4b \\sim C4-H4a \\sim C2-H2a \\sim C2-H2b
 with sigma of 0.005
 C1-H1 \\sim C3-H3
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uiso(H4a) = Uiso(H4b) = Uiso(H2a) = Uiso(H2b)
Uiso(H3) = Uiso(H2a) = Uiso(H2b) = Uiso(H4b) = Uiso(H4a)
Uiso(H19a) = Uiso(H19b) = Uiso(H19c)
Uiso(H20b) = Uiso(H20c) = Uiso(H20a)
4.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C9(H9), C14(H14), C17(H17), C18(H18)
4.b Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C19(H19a,H19b,H19c)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_special_instructions 'No special instructions were received'