Construction of polycyclic bridged indene derivatives by a tandem 1,3-rearrangement/intramolecular Friedel-Crafts cyclization of propargyl acetates
Zhu, Shifa; Zhang, Jiantao; Liao, Zhehui; Chen, Lianfen; Jiang, Huanfeng; Chemical Communications  (2019) –; doi:10.1039/C9CC03715B

data_7123578
_publ_section_title
;
 Construction of polycyclic bridged indene derivatives by a tandem
 1,3-rearrangement/intramolecular Friedel-Crafts cyclization of propargyl
 acetates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03715B
_journal_year                    2019
_chemical_formula_moiety         'C25 H23 Cl O5'
_chemical_formula_sum            'C25 H23 Cl O5'
_chemical_formula_weight         438.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-08 deposited with the CCDC.    2019-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                69.694(11)
_cell_angle_beta                 76.371(11)
_cell_angle_gamma                62.034(13)
_cell_formula_units_Z            2
_cell_length_a                   10.7102(14)
_cell_length_b                   11.1405(13)
_cell_length_c                   11.3689(13)
_cell_measurement_reflns_used    2995
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9250
_cell_measurement_theta_min      4.1530
_cell_volume                     1119.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.958
_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     16.00  49.00   1.00    1.00    --   40.23  38.00  60.00   33
  2  \w     83.00 163.00   1.00    1.00    --  108.20  45.00 -30.00   80
  3  \w    105.00 175.00   1.00    1.00    --  108.20 129.00   5.00   70
  4  \w     95.00 160.00   1.00    1.00    --  108.20 125.00 -30.00   65
  5  \w     87.00 162.00   1.00    1.00    --  108.20  30.00  30.00   75
  6  \w     85.00 177.00   1.00    1.00    --  108.20  61.00  60.00   92
  7  \w     83.00 110.00   1.00    1.00    --  108.20 -45.00  30.00   27
  8  \w     67.00 109.00   1.00    1.00    --  108.20 -95.00 -60.00   42
  9  \w     66.00 140.00   1.00    1.00    --  108.20 -77.00   0.00   74
 10  \w     52.00  84.00   1.00    1.00    --   40.23-125.00 -30.00   32
 11  \w     37.00 119.00   1.00    1.00    --  108.20-125.00-150.00   82
 12  \w     39.00 137.00   1.00    1.00    --  108.20 -61.00 -90.00   98
 13  \w     57.00 107.00   1.00    1.00    --  108.20  15.00-180.00   50
 14  \w     53.00  80.00   1.00    1.00    --  108.20 -45.00  30.00   27
 15  \w     51.00  80.00   1.00    1.00    --   40.23 -99.00 150.00   29
 16  \w    -29.00  63.00   1.00    1.00    --   40.23 -38.00-120.00   92
 17  \w    -67.00  33.00   1.00    1.00    --  -40.23  57.00-180.00  100
 18  \w   -114.00 -20.00   1.00    1.00    --  -40.23 -77.00  60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0417767000
_diffrn_orient_matrix_UB_12      -0.1182854000
_diffrn_orient_matrix_UB_13      0.1237666000
_diffrn_orient_matrix_UB_21      0.0849376000
_diffrn_orient_matrix_UB_22      -0.1097543000
_diffrn_orient_matrix_UB_23      -0.0753656000
_diffrn_orient_matrix_UB_31      0.1333049000
_diffrn_orient_matrix_UB_32      0.0221457000
_diffrn_orient_matrix_UB_33      -0.0064219000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0653
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7321
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.435
_diffrn_reflns_theta_min         4.162
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.919
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0971
_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^)+(0.1789P)^2^+2.2617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2885
_refine_ls_wR_factor_ref         0.3048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3577
_reflns_number_total             4371
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03715b2.cif
_cod_data_source_block           zft_2
_cod_database_code               7123578
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.841
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C8(H8), C5(H5), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C21(H21), C11(H11), C14(H14), C20(H20), C13(H13), C19(H19),
 C12(H12), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C23(H23A,H23B,H23C)
;
_olex2_date_sample_data_collection 2018-12-19
_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 6.867
_oxdiff_exptl_absorpt_empirical_full_min 0.553