Anionic Annulation of 3-Cyanophthalides with Allene Carboxylates: A Carbon-Conserved Synthesis of Naphtho[ b]furanones.
Jana, Supriti; Mal, Dipakranjan; The Journal of organic chemistry 83 (2018) 4537–4544; doi:10.1021/acs.joc.8b00272

data_4034933
_publ_section_title
;
 Anionic Annulation of 3-Cyanophthalides with Allene Carboxylates: A
 Carbon-Conserved Synthesis of Naphtho[ b]furanones.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4537
_journal_page_last               4544
_journal_paper_doi               10.1021/acs.joc.8b00272
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H16 O5'
_chemical_formula_sum            'C21 H16 O5'
_chemical_formula_weight         348.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                75.351(14)
_cell_angle_beta                 75.327(12)
_cell_angle_gamma                73.555(13)
_cell_formula_units_Z            2
_cell_length_a                   7.702(3)
_cell_length_b                   10.567(4)
_cell_length_c                   11.247(5)
_cell_measurement_reflns_used    2435
_cell_measurement_temperature    100
_cell_measurement_theta_max      3.00
_cell_measurement_theta_min      29.00
_cell_volume                     832.9(6)
_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      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  apex
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.1144
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9476
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.049
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.1819
_refine_ls_R_factor_gt           0.0840
_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^)+(0.1399P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2024
_refine_ls_wR_factor_ref         0.2806
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1166
_reflns_number_total             2885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00272_si_002.cif
_cod_data_source_block           SHELX
_cod_original_cell_volume        833.0(6)
_cod_database_code               4034933
_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, All O(H) groups
2. Others
 Fixed Sof: C20(0.8) H20A(0.8) H20B(0.8) C21(0.8) H21A(0.8) H21B(0.8)
 H21C(0.8) C20A(0.2) H20C(0.2) H20D(0.2) C21A(0.2) H21D(0.2) H21E(0.2) H21F(0.2)
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C20A(H20C,H20D)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C15(H15), C4(H4), C16(H16), C1(H1A), C17(H17), C3(H3),
 C2(H2)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21A(H21D,H21E,H21F)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              9762
_shelx_hkl_checksum              84331
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'