A convenient domino Ferrier rearrangement-intramolecular cyclization for the synthesis of novel benzopyran-fused pyranoquinolines.
Moshapo, Paseka T.; Sokamisa, Mokela; Mmutlane, Edwin M.; Mampa, Richard M.; Kinfe, Henok H.; Organic & biomolecular chemistry 14 (2016) 5627–5638; doi:10.1039/c5ob02536b

data_7154916
_publ_section_title
;
 A convenient domino Ferrier rearrangement-intramolecular cyclization for
 the synthesis of novel benzopyran-fused pyranoquinolines.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5627
_journal_page_last               5638
_journal_paper_doi               10.1039/c5ob02536b
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C33 H31 N O4'
_chemical_formula_sum            'C33 H31 N O4'
_chemical_formula_weight         505.58
_chemical_name_systematic
(4bS,4b1S,6R,7S,7aR,12bS)-7-(benzyloxy)-6-((benzyloxy)methyl)-4b1,6,7,7a,12b,13-hexahydro-4bH-benzo[h]chromeno[2,3,4-de]chromene
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.11.03 svn.r3071 for OlexSys, GUI svn.r4932)
;
_audit_update_record
;
2015-11-28 deposited with the CCDC.
2016-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.9468(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1243(3)
_cell_length_b                   11.1741(3)
_cell_length_c                   13.3627(5)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.276
_cell_measurement_theta_min      2.935
_cell_volume                     1322.24(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23644
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         2.935
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       plates
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.626
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 2214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.087(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         6519
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0554
_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^)+(0.0516P)^2^+0.1540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5480
_reflns_number_total             6519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02536b5.cif
_cod_data_source_block           15a
_cod_depositor_comments
;
          Adding full bibliography for 7154916.cif.

2018-02-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.5(C33 H31 N O4)'
_cod_original_formula_sum        'C16.50 H15.50 N0.50 O2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     252.79
_cod_database_code               7154916
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1), C2(H2), C3(H3), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C30(H30), C31(H31),
  C32(H32), C33(H33), C34(H34)
;
_shelx_res_checksum              26119
_shelx_hkl_checksum              74005
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'