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_4030962
_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         'C19 H17 Br Cl N O3'
_chemical_formula_sum            'C19 H17 Br Cl N O3'
_chemical_formula_weight         422.70
_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                92.7930(16)
_cell_angle_beta                 106.4322(14)
_cell_angle_gamma                93.7434(16)
_cell_formula_units_Z            2
_cell_length_a                   7.6245(9)
_cell_length_b                   10.3617(12)
_cell_length_c                   11.7154(14)
_cell_measurement_reflns_used    8658
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.662
_cell_measurement_theta_min      2.588
_cell_volume                     883.67(18)
_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 0.996
_diffrn_measured_fraction_theta_max 0.986
_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  0.0557
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16127
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.662
_diffrn_reflns_theta_min         1.974
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.495
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.7420.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.322
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.006
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         5371
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0674P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3994
_reflns_number_total             5371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00249_si_003.cif
_cod_data_source_block           dk-vii-123b
_cod_depositor_comments
'Adding full bibliography for 4030962--4030963.cif.'
_cod_database_code               4030962
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All H(H) groups, All C(H,H,H) groups
2. Restrained distances
 C18-H18
 0.975 with sigma of 0.02
 H2-O2
 0.975 with sigma of 0.02
 C2-H2B \\sim C2-H2A
 with sigma of 0.005
 C18-H18 \\sim C17-H17 \\sim C15-H15 \\sim C14-H14
 with sigma of 0.005
 C4-H4B \\sim C4-H4A
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uiso(H14) = Uiso(H15) = Uiso(H17) = Uiso(H18)
Uiso(H2B) = Uiso(H2A) = Uiso(H3)
Uiso(H4A) = Uiso(H4B)
4.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C9(H9)
4.b Idealised Me refined as rotating group:
 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_original_sample_id DK-VII-123B
_olex2_submission_special_instructions 'No special instructions were received'