Phosphine-catalyzed Formal Buchner [6+1] Annulation: De Novo Construction of Cycloheptatrienes
Lai, Jingxiong; Huang, You; Chemical Communications  (2023) –; doi:10.1039/D3CC04905A

data_7132205
_publ_section_title
;
 Phosphine-catalyzed Formal Buchner [6+1] Annulation: De Novo Construction
 of Cycloheptatrienes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04905A
_journal_year                    2023
_chemical_formula_moiety         'C28 H21 F3 O6'
_chemical_formula_sum            'C28 H21 F3 O6'
_chemical_formula_weight         510.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-08 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.720(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8322(6)
_cell_length_b                   13.7887(4)
_cell_length_c                   10.6237(4)
_cell_measurement_reflns_used    14197
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      32.4220
_cell_measurement_theta_min      1.9490
_cell_volume                     2316.60(14)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    1.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00    1.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00    1.00    --  -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      -0.0074841000
_diffrn_orient_matrix_UB_12      -0.0506530000
_diffrn_orient_matrix_UB_13      0.0026828000
_diffrn_orient_matrix_UB_21      0.0441668000
_diffrn_orient_matrix_UB_22      -0.0086932000
_diffrn_orient_matrix_UB_23      0.0002440000
_diffrn_orient_matrix_UB_31      0.0022829000
_diffrn_orient_matrix_UB_32      0.0020601000
_diffrn_orient_matrix_UB_33      0.0667920000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         1.959
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0628P)^2^+1.0009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1281
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3904
_reflns_number_total             4734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04905a2.cif
_cod_data_source_block           r20200605a
_cod_database_code               7132205
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.977
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 O6-C27 \\sim O6-C27A
 with sigma of 0.02
 C27-C28 \\sim C27A-C28A
 with sigma of 0.02
 O6-C28 \\sim O6-C28A
 with sigma of 0.04
3. Rigid bond restraints
 O6, C26
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C27 \\sim C27A \\sim C28 \\sim C28A: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C27) \\sim Ueq, Uanis(C27A) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C28A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(C27A)=Sof(H27C)=Sof(H27D)=Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C17(H17)
6.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C27A(H27C,H27D)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C16(H16),
 C18(H18), C19(H19), C21(H21), C23(H23)
6.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C28A(H28D,H28E,H28F)
;
_shelx_res_checksum              97934
_shelx_hkl_checksum              56494
_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 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.667