Domino Prins/pinacol reaction for the stereoselective synthesis of spiro[pyran-4,4'-quinoline]-2',3'-dione derivatives.
Subba Reddy, B. V.; Gopal Reddy, S.; Durgaprasad, M.; Bhadra, Manika Pal; Sridhar, B.; Organic & biomolecular chemistry 13 (2015) 8729–8733; doi:10.1039/c5ob01077b

data_7154590
_publ_section_title
;
 Domino Prins/pinacol reaction for the stereoselective synthesis of
 spiro[pyran-4,4'-quinoline]-2',3'-dione derivatives.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8729
_journal_page_last               8733
_journal_paper_doi               10.1039/c5ob01077b
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C18 H23 N O3'
_chemical_formula_sum            'C18 H23 N O3'
_chemical_formula_weight         301.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-23
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_audit_update_record
;
2015-04-23 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.909(2)
_cell_length_b                   9.2315(8)
_cell_length_c                   6.9138(6)
_cell_measurement_reflns_used    8716
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.35
_cell_volume                     1589.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0202
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17913
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.301
_diffrn_reflns_theta_min         1.635
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0744P)^2^+0.1058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1087
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                3626
_reflns_number_total             3849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01077b2.cif
_cod_data_source_block           ay91
_cod_depositor_comments          'Adding full bibliography for 7154590.cif.'
_cod_database_code               7154590
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.049) H3(0.056) H4(0.055) H5(0.048) H8A(0.044) H8B(0.044)
 H9A(0.055) H9B(0.055) H10(0.043) H11A(0.044) H11B(0.044) H13A(0.09) H13B(0.09)
 H13C(0.09) H14A(0.091) H14B(0.091) H14C(0.091) H15A(0.081) H15B(0.081)
 H15C(0.081) H18A(0.069) H18B(0.069) H18C(0.069)
 Fixed X: H2(0.5469) H3(0.511) H4(0.4189) H5(0.3635) H8A(0.426) H8B(0.3823)
 H9A(0.3601) H9B(0.3532) H10(0.3005) H11A(0.3135) H11B(0.3221) H13A(0.2243)
 H13B(0.2186) H13C(0.1703) H14A(0.161) H14B(0.2036) H14C(0.2119) H15A(0.2365)
 H15B(0.2339) H15C(0.1815) H18A(0.5635) H18B(0.5682) H18C(0.5766)
 Fixed Y: H2(0.5212) H3(0.2917) H4(0.2602) H5(0.4601) H8A(0.8403) H8B(0.7287)
 H9A(1.0104) H9B(0.9612) H10(0.933) H11A(0.6367) H11B(0.7009) H13A(0.61)
 H13B(0.7203) H13C(0.6943) H14A(0.9473) H14B(0.9857) H14C(1.0385) H15A(0.8533)
 H15B(0.6887) H15C(0.7825) H18A(0.895) H18B(0.7378) H18C(0.7649)
 Fixed Z: H2(0.0698) H3(0.0512) H4(0.0331) H5(0.0198) H8A(-0.2168) H8B(-
 0.2845) H9A(-0.1451) H9B(-0.3609) H10(0.0904) H11A(-0.008) H11B(0.1996) H13A(-
 0.0478) H13B(-0.219) H13C(-0.0777) H14A(0.0222) H14B(-0.1368) H14C(0.0767)
 H15A(0.3365) H15B(0.2814) H15C(0.2805) H18A(0.0079) H18B(-0.076) H18C(0.1458)
;
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_shelx_res_checksum              30322
_shelx_shelxl_version_number     2014/7