Green Method To Preparing Oxindole-Fused Spirotetrahydrofuran Scaffolds through Methanesulfonic Acid-Catalyzed Cyclization Reactions of 3-Allyl-3-hydroxy-2-oxindole in Water.
Zhang, Jie-Huan; Wang, Ru-Bing; Li, De-Feng; Zhao, Li-Ming; ACS omega 2 (2017) 7022–7028; doi:10.1021/acsomega.7b01279

data_4516930
_publ_section_title
;
 Green Method To Preparing Oxindole-Fused Spirotetrahydrofuran Scaffolds
 through Methanesulfonic Acid-Catalyzed Cyclization Reactions of
 3-Allyl-3-hydroxy-2-oxindole in Water.
;
_journal_issue                   10
_journal_name_full               'ACS omega'
_journal_page_first              7022
_journal_page_last               7028
_journal_paper_doi               10.1021/acsomega.7b01279
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         'C14 H16 Br N O2'
_chemical_formula_sum            'C14 H16 Br N O2'
_chemical_formula_weight         308.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.002(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2162(18)
_cell_length_b                   11.9031(18)
_cell_length_c                   12.665(2)
_cell_measurement_reflns_used    1272
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.1930
_cell_measurement_theta_min      3.6390
_cell_volume                     1384.1(4)
_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                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -2.00  85.00   1.00    7.30    --   16.81  57.00 -60.00   87
  2  \w     33.00  60.00   1.00    7.30    --   16.81  19.00 -90.00   27
  3  \w    -25.00  56.00   1.00    7.30    --   16.81 -99.00-180.00   81
  4  \w     -6.00  19.00   1.00    7.30    --  -17.43 -99.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319507000
_diffrn_orient_matrix_UB_12      0.0536926000
_diffrn_orient_matrix_UB_13      -0.0053350000
_diffrn_orient_matrix_UB_21      -0.0637645000
_diffrn_orient_matrix_UB_22      0.0258982000
_diffrn_orient_matrix_UB_23      0.0162206000
_diffrn_orient_matrix_UB_31      0.0293167000
_diffrn_orient_matrix_UB_32      -0.0024848000
_diffrn_orient_matrix_UB_33      0.0535835000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6157
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.172
_diffrn_reflns_theta_min         2.802
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.963
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26228
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_refine_diff_density_max         1.739
_refine_diff_density_min         -1.082
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1689
_refine_ls_R_factor_gt           0.0914
_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^)+(0.1315P)^2^+0.2349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2174
_refine_ls_wR_factor_ref         0.2791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1519
_reflns_number_total             3147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b01279_si_002.cif
_cod_data_source_block           exp_1410
_cod_depositor_comments
;

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.67(C14 H16 Br N O2)'
_cod_original_formula_sum        'C9.33 H9.33 Br0.67 N0.67 O1.33'
_cod_original_formula_units_Z    6
_cod_original_formula_weight     205.45
_cod_database_code               4516930
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C00I
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
 C00I, C00E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
 C00D, C00I
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.00025
 C00E, C00I
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.0025
3. Uiso/Uaniso restraints and constraints
C00I: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
C00I: within 3.8A with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C00I) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C00I) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C00I) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C00I) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C00I) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C00I) \\sim Ueq: with sigma of 0.0005 and sigma for terminal atoms of
0.001
4.a Secondary CH2 refined with riding coordinates:
 C00D(H00b,H00d), C00I(H00n,H00o)
4.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00C(H00C)
4.c Idealised Me refined as rotating group:
 C00F(H00e,H00f,H00g), C00G(H00h,H00i,H00j), C00H(H00k,H00l,H00m)
;
_shelx_res_checksum              4891
_shelx_hkl_checksum              90786
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.261
_oxdiff_exptl_absorpt_empirical_full_min 0.606