Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: access to the synthesis of chromeno[4,3-<i>b</i>]pyrroles.
Li, Xiaohu; Huang, You; Chemical communications (Cambridge, England) 57 (2021) 9934–9937; doi:10.1039/d1cc04199a

data_7128948
_publ_section_title
;
 Phosphine-catalyzed sequential (2+3)/(2+4) annulation of \g-vinyl
 allenoates: access to the synthesis of chromeno[4,3-<i>b</i>]pyrroles.
;
_journal_issue                   77
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9934
_journal_page_last               9937
_journal_paper_doi               10.1039/d1cc04199a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C27 H29 N O7'
_chemical_formula_sum            'C27 H29 N O7'
_chemical_formula_weight         479.51
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                93.977(4)
_cell_angle_beta                 106.212(5)
_cell_angle_gamma                112.740(5)
_cell_formula_units_Z            2
_cell_length_a                   10.7992(6)
_cell_length_b                   10.9972(5)
_cell_length_c                   11.7181(7)
_cell_measurement_reflns_used    10540
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.9450
_cell_measurement_theta_min      1.8450
_cell_volume                     1207.49(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    2.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0464043000
_diffrn_orient_matrix_UB_12      -0.0686620000
_diffrn_orient_matrix_UB_13      -0.0073271000
_diffrn_orient_matrix_UB_21      0.0262885000
_diffrn_orient_matrix_UB_22      -0.0177158000
_diffrn_orient_matrix_UB_23      -0.0445947000
_diffrn_orient_matrix_UB_31      0.0534617000
_diffrn_orient_matrix_UB_32      -0.0081632000
_diffrn_orient_matrix_UB_33      0.0457949000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18298
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.850
_diffrn_reflns_theta_min         1.847
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         8080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0487P)^2^+0.2101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6225
_reflns_number_total             8080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04199a2.cif
_cod_data_source_block           r20201022a
_cod_depositor_comments          'Adding full bibliography for 7128948.cif.'
_cod_original_cell_volume        1207.49(12)
_cod_database_code               7128948
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 89.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.78
_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:
 C6(H6), C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B), C23(H23A,H23B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              52913
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.648
_oxdiff_exptl_absorpt_empirical_full_min 0.564