Iodine-mediated formal [3 + 2] annulation for synthesis of furocoumarin from oxime esters
Pham, Quyen T.; Le, Phong Q.; Dang, Ha V.; Ha, Hiep Q.; Nguyen, Huong T. D.; Truong, Thanh; Le, Tri Minh; RSC Advances 10 (2020) 44332–44338; doi:10.1039/D0RA07566C

data_7241896
_publ_section_title
;
 Iodine-mediated formal [3 + 2] annulation for synthesis of furocoumarin
 from oxime esters
;
_journal_issue                   72
_journal_name_full               'RSC Advances'
_journal_page_first              44332
_journal_page_last               44338
_journal_paper_doi               10.1039/D0RA07566C
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C17 H10 O3'
_chemical_formula_sum            'C17 H10 O3'
_chemical_formula_weight         262.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-02 deposited with the CCDC.	2020-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2356(8)
_cell_length_b                   7.1744(4)
_cell_length_c                   25.3234(16)
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.48
_cell_measurement_theta_min      3.08
_cell_volume                     2404.6(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1303
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            25205
_diffrn_reflns_theta_full        26.3863
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         3.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  .7454
_exptl_absorpt_correction_T_min  0.6818
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4488
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088.6225
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.4854
_refine_diff_density_min         -0.4319
_refine_diff_density_rms         0.1212
_refine_ls_d_res_high            0.7996
_refine_ls_d_res_low             6.6178
_refine_ls_goodness_of_fit_ref   1.0693
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0693
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.8735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              0
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              0
_reflns_number_gt                1654
_reflns_number_total             2450
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0ra07566c2.cif
_cod_data_source_block           T2b_a
_cod_original_cell_volume        2404.6(3)
_cod_database_code               7241896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C17(H17), C6(H6), C8(H8), C9(H9), C13(H13), C16(H16), C7(H7),
 C15(H15), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'