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_7116472
_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         'C28 H25 N O2'
_chemical_formula_sum            'C28 H25 N O2'
_chemical_formula_weight         407.49
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-03-10
_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                 93.3654(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.89753(16)
_cell_length_b                   24.4163(4)
_cell_length_c                   9.00094(16)
_cell_measurement_reflns_used    4570
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.5420
_cell_measurement_theta_min      3.6230
_cell_volume                     2171.43(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0518767000
_diffrn_orient_matrix_UB_12      -0.0252582000
_diffrn_orient_matrix_UB_13      0.1427523000
_diffrn_orient_matrix_UB_21      -0.1128987000
_diffrn_orient_matrix_UB_22      -0.0297545000
_diffrn_orient_matrix_UB_23      -0.0933828000
_diffrn_orient_matrix_UB_31      0.0940541000
_diffrn_orient_matrix_UB_32      -0.0496484000
_diffrn_orient_matrix_UB_33      -0.0166569000
_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  0.0142
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.997
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8618
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.245
_diffrn_reflns_theta_min         3.621
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.915
_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    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'crystallised by the slow evaporation of a solution of the compound in a mixture of ethyl acetate and petroleum ether'
_exptl_crystal_size_max          0.1796
_exptl_crystal_size_mid          0.0711
_exptl_crystal_size_min          0.0495
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0492P)^2^+0.6285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3753
_reflns_number_total             4262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc09496d2.cif
_cod_data_source_block           ikhwld
_cod_database_code               7116472
_nottingham_internal_coll_name   IKHWLD
_nottingham_internal_coll_number 13348
_nottingham_internal_coll_client IK/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '120.0000, 30.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   06/03/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user pczwl
_nottingham_internal_process_date 07/03/2014
_nottingham_internal_solution_user wl
_nottingham_internal_solution_date 7/3/2014
_nottingham_internal_refinement_user wl
_nottingham_internal_refinement_date 7/3/2014
_nottingham_internal_validation_user wl
_nottingham_internal_validation_date 17/3/2014
_nottingham_internal_archive_date 17/3/2014
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C28 H25 N O2'
_reflns_odcompleteness_completeness 99.70
_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, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(1)
 Sof(H31A)=Sof(H31B)=Sof(H31C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C22(H22), C23(H23),
 C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C31(H31D,H31E,
 H31F)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'