Synthesis of benzooxepane-fused cyclobutene derivatives <i>via</i> Pd-catalyzed cascade reactions of haloarenes and diynylic ethers.
Zhu, Shugao; Huang, Wenliang; Liu, Shihan; Yu, Rongjing; Ma, Yufeng; Wang, Hong; Zhang, Rui; Liu, Bin; Lan, Yu; Shen, Ruwei; Chemical communications (Cambridge, England) 60 (2024) 5707–5710; doi:10.1039/d4cc00999a

data_7133033
_publ_section_title
;
 Synthesis of benzooxepane-fused cyclobutene derivatives <i>via</i>
 Pd-catalyzed cascade reactions of haloarenes and diynylic ethers.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5707
_journal_page_last               5710
_journal_paper_doi               10.1039/d4cc00999a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C33 H26 N4 O6'
_chemical_formula_sum            'C33 H26 N4 O6'
_chemical_formula_weight         574.58
_chemical_melting_point          510.85~512.05
_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             2022-07-22
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-23 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.553(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5972(12)
_cell_length_b                   10.0613(8)
_cell_length_c                   21.8687(17)
_cell_measurement_reflns_used    5524
_cell_measurement_temperature    243.00(10)
_cell_measurement_theta_max      30.5290
_cell_measurement_theta_min      2.1960
_cell_volume                     2771.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      243.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.775
_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    -19.00  17.00   0.50    1.00    --    5.03 -53.00 -67.00   72
  2  \w    -67.00 -25.00   0.50    1.00    --    5.03 -53.00 -67.00   84
  3  \w     -9.00  73.00   0.50    1.00    --    5.03  53.00  77.00  164
  4  \w    -20.00  26.00   0.50    1.00    --   -5.42 -99.00  60.00   92
  5  \w    -20.00  11.00   0.50    1.00    --   -5.42 -99.00-120.00   62
  6  \w    -13.00  28.00   0.50    1.00    --   -5.42 -99.00 150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0391378000
_diffrn_orient_matrix_UB_12      -0.0460930000
_diffrn_orient_matrix_UB_13      0.0094856000
_diffrn_orient_matrix_UB_21      0.0244603000
_diffrn_orient_matrix_UB_22      -0.0033875000
_diffrn_orient_matrix_UB_23      0.0292965000
_diffrn_orient_matrix_UB_31      -0.0323136000
_diffrn_orient_matrix_UB_32      0.0532608000
_diffrn_orient_matrix_UB_33      0.0101034000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.775
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25602
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.091
_diffrn_reflns_theta_min         1.863
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: cetonitrile, n-hexane'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         6910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0883P)^2^+0.1684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3834
_reflns_number_total             6910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00999a2.cif
_cod_data_source_block           hwl_7_5
_cod_depositor_comments          'Adding full bibliography for 7133033.cif.'
_cod_database_code               7133033
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00Y(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 N004(H004), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00R(H00R),
 C00T(H00T), C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C013(H013), C014(H014), C016(H016), C017(H017)
2.d Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00C), C015(H01A,H01B,H01C)
;
_shelx_res_checksum              61711
_shelx_hkl_checksum              7993
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 16.354
_oxdiff_exptl_absorpt_empirical_full_min 0.362