Synthesis of Functionalized Indenones via Rh-Catalyzed C-H Activation Cascade Reaction.
Lv, Ningning; Chen, Zhengkai; Liu, Yue; Liu, Zhanxiang; Zhang, Yuhong; Organic letters 19 (2017) 2588–2591; doi:10.1021/acs.orglett.7b00906

data_1546216
_publ_section_title
;
 Synthesis of Functionalized Indenones via Rh-Catalyzed C-H Activation
 Cascade Reaction.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2588
_journal_page_last               2591
_journal_paper_doi               10.1021/acs.orglett.7b00906
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C12 H8 F3 N O3'
_chemical_formula_sum            'C12 H8 F3 N O3'
_chemical_formula_weight         271.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-30
_audit_creation_method
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Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3137(12)
_cell_length_b                   12.4860(7)
_cell_length_c                   4.8092(4)
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    175.3
_cell_measurement_theta_max      29.4651
_cell_measurement_theta_min      3.2566
_cell_volume                     1099.70(13)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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_temperature      175.3
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -23.00   70.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6871   77.0000   90.0000 93

  2 omega  -36.00   63.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5621   38.0000  -30.0000 99

  3 omega  -72.00   12.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5621  -38.0000  150.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0358545000
_diffrn_orient_matrix_UB_12      0.0051270000
_diffrn_orient_matrix_UB_13      -0.0540015000
_diffrn_orient_matrix_UB_21      0.0107579000
_diffrn_orient_matrix_UB_22      -0.0466287000
_diffrn_orient_matrix_UB_23      0.0736522000
_diffrn_orient_matrix_UB_31      -0.0099098000
_diffrn_orient_matrix_UB_32      -0.0320535000
_diffrn_orient_matrix_UB_33      -0.1158217000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6668
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.331
_diffrn_reflns_theta_min         3.263
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1975
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0576P)^2^+0.2580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                1695
_reflns_number_total             1975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00906_si_003.cif
_cod_data_source_block           161230_lnn_1_149_13
_cod_original_cell_volume        1099.69(13)
_cod_database_code               1546216
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.942
_reflns_odcompleteness_completeness 99.56
_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, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_shelx_res_checksum              12238
_shelx_hkl_checksum              12263
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'