Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of non- or weakly activated 1,3-dienes involving C-H functionalization.
Khan, Imtiaz; Chidipudi, Suresh Reddy; Lam, Hon Wai; Chemical communications (Cambridge, England) 51 (2015) 2613–2616; doi:10.1039/c4cc09496d

data_7116471
_publ_section_title
;
 Synthesis of spiroindanes by palladium-catalyzed oxidative annulation of
 non- or weakly activated 1,3-dienes involving C-H functionalization.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2613
_journal_page_last               2616
_journal_paper_doi               10.1039/c4cc09496d
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C24 H23 Cl O2'
_chemical_formula_sum            'C24 H23 Cl O2'
_chemical_formula_weight         378.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-03-05
_audit_creation_method
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Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
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_audit_update_record
;
2014-03-18 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.180(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4763(3)
_cell_length_b                   6.01195(15)
_cell_length_c                   26.1383(8)
_cell_measurement_reflns_used    6115
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0780
_cell_measurement_theta_min      3.3910
_cell_volume                     1945.18(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1081724000
_diffrn_orient_matrix_UB_12      -0.0771082000
_diffrn_orient_matrix_UB_13      -0.0165528000
_diffrn_orient_matrix_UB_21      0.0475897000
_diffrn_orient_matrix_UB_22      -0.0229881000
_diffrn_orient_matrix_UB_23      0.0570433000
_diffrn_orient_matrix_UB_31      -0.0390779000
_diffrn_orient_matrix_UB_32      -0.2433282000
_diffrn_orient_matrix_UB_33      -0.0002046000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13248
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.212
_diffrn_reflns_theta_min         3.408
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    1.855
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_recrystallization_method
'crystallised from a mixture of ethyl acetate and petroleum ether'
_exptl_crystal_size_max          0.9153
_exptl_crystal_size_mid          0.0591
_exptl_crystal_size_min          0.0175
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.7160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3455
_reflns_number_total             3899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc09496d2.cif
_cod_data_source_block           ikhwlb
_cod_database_code               7116471
_nottingham_internal_coll_name   IKHWLB
_nottingham_internal_coll_number 13172
_nottingham_internal_coll_client IK/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '25.0000, 100.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   24/01/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user pczwl
_nottingham_internal_process_date 27/01/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_solution_date 24/1/2014
_nottingham_internal_refinement_user pczwl
_nottingham_internal_refinement_date 27/1/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_validation_date 5/3/2014
_nottingham_internal_archive_date 5/3/2014
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C24 H23 Cl O2'
_reflns_odcompleteness_completeness 99.97
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C21(H21), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'