A phosphine-catalysed one-pot domino sequence to access cyclopentene-fused coumarins.
Chen, Yan-Shan; Zheng, Yu; Chen, Zhi-Jun; Xie, Zhen-Zhen; He, Xian-Chen; Xiao, Jun-An; Chen, Kai; Xiang, Hao-Yue; Yang, Hua; Organic & biomolecular chemistry 19 (2021) 7074–7080; doi:10.1039/d1ob01143j

data_7158195
_publ_section_title
;
 A phosphine-catalysed one-pot domino sequence to access
 cyclopentene-fused coumarins.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7074
_journal_page_last               7080
_journal_paper_doi               10.1039/d1ob01143j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C16 H14 O4'
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.27
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-29 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                115.446(4)
_cell_angle_beta                 93.730(4)
_cell_angle_gamma                103.262(4)
_cell_formula_units_Z            4
_cell_length_a                   10.2334(13)
_cell_length_b                   12.1426(15)
_cell_length_c                   12.2272(15)
_cell_measurement_reflns_used    9588
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.944
_cell_measurement_theta_min      3.022
_cell_volume                     1312.0(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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     0.71076
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27398
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0686 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.9478.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         6038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+0.2391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1323
_reflns_number_gt                3735
_reflns_number_total             6038
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01143j2.cif
_cod_data_source_block           xiao_1113_0m
_cod_depositor_comments
;
Adding full bibliography for 7158194--7158196.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H28 O8'
_cod_original_formula_weight         540.54
_cod_original_formula_moiety         '2(C16 H14 O4)'
_cod_original_formula_units_Z            2
_cod_database_code               7158195
_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.a Ternary CH refined with riding coordinates:
 C25(H25), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C17(H17), C26(H26), C19(H19), C18(H18), C1(H1), C4(H4), C3(H3),
 C2(H2), C10(H10)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C31(H31A,H31B,H31C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'