Palladium-catalyzed arene C–H activation/ketone C–H functionalization reaction: route to spirodihydroindenones
Zhang, Bo-Sheng; Hua, Hui-Liang; Gao, Lu-Yao; Liu, Ce; Qiu, Yi-Feng; Zhou, Ping-Xin; Zhou, Zhao-Zhao; Zhao, Jia-Hui; Liang, Yong-Min; Organic Chemistry Frontiers 4 (2017) 1376–; doi:10.1039/C7QO00164A

data_1553761
_publ_section_title
;
 Palladium-catalyzed arene C--H activation/ketone C--H functionalization
 reaction: route to spirodihydroindenones
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1376
_journal_paper_doi               10.1039/C7QO00164A
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H16 O'
_chemical_formula_sum            'C17 H16 O'
_chemical_formula_weight         236.30
_chemical_melting_point          361.0(10)
_chemical_name_systematic
2',3'-dihydrospiro[cyclopentane-1,1'-cyclopenta[a]naphthalen]-2-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-02-04 deposited with the CCDC.
2017-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7380(5)
_cell_length_b                   11.6560(8)
_cell_length_c                   14.0895(8)
_cell_measurement_reflns_used    813
_cell_measurement_temperature    298.84(10)
_cell_measurement_theta_max      25.2970
_cell_measurement_theta_min      4.2750
_cell_volume                     1270.79(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.84(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   58.00  104.40   1.4500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000  -30.0000 32

  2 omega  -53.00   61.55   1.4500    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  -90.0000 79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0339805000
_diffrn_orient_matrix_UB_12      0.0558859000
_diffrn_orient_matrix_UB_13      0.0068667000
_diffrn_orient_matrix_UB_21      0.0850471000
_diffrn_orient_matrix_UB_22      0.0217120000
_diffrn_orient_matrix_UB_23      0.0055230000
_diffrn_orient_matrix_UB_31      0.0048102000
_diffrn_orient_matrix_UB_32      0.0102180000
_diffrn_orient_matrix_UB_33      -0.0495672000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3502
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0474P)^2^+0.0657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                1723
_reflns_number_total             2423
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00164a2.cif
_cod_data_source_block           zhangbsh_0719
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '360-362' was changed to
'361.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1553761
_reflns_odcompleteness_completeness 99.41
_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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C14(H14A,H14B), C16(H16A,H16B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C3(H3), C2(H2), C7(H7), C4(H4)
;
_olex2_date_sample_data_collection 2016-07-20
_olex2_submission_special_instructions 'No special instructions were received'