Rh(III)-Catalyzed Carbocyclization of 3-(Indolin-1-yl)-3-oxopropanenitriles with Alkynes and Alkenes through C-H Activation.
Zhou, Tao; Wang, Yanwei; Li, Bin; Wang, Baiquan; Organic letters 18 (2016) 5066–5069; doi:10.1021/acs.orglett.6b02521

data_1555807
_publ_section_title
;
 Rh(III)-Catalyzed Carbocyclization of
 3-(Indolin-1-yl)-3-oxopropanenitriles with Alkynes and Alkenes through
 C-H Activation.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5066
_journal_page_last               5069
_journal_paper_doi               10.1021/acs.orglett.6b02521
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C19 H20 N2 O3'
_chemical_formula_sum            'C19 H20 N2 O3'
_chemical_formula_weight         324.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6778(12)
_cell_length_b                   15.1304(17)
_cell_length_c                   20.376(2)
_cell_measurement_reflns_used    10073
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     3291.9(6)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9677
	          2theta: -15.0844
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9677
	          2theta: -15.0844
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9677
	          2theta: -15.0844
;
_diffrn_measurement_device
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.091261
_diffrn_orient_matrix_UB_12      0.010992
_diffrn_orient_matrix_UB_13      0.017926
_diffrn_orient_matrix_UB_21      0.000327
_diffrn_orient_matrix_UB_22      -0.057072
_diffrn_orient_matrix_UB_23      0.033330
_diffrn_orient_matrix_UB_31      0.011017
_diffrn_orient_matrix_UB_32      -0.024071
_diffrn_orient_matrix_UB_33      -0.041325
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0066
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         3.074
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1376
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+1.0815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3421
_reflns_number_total             3765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02521_si_002.cif
_cod_data_source_block           m20160328c
_cod_original_cell_volume        3292.0(6)
_cod_database_code               1555807
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C17A, C17B}
3. Restrained distances
 C17A-C18A = C18A-C19A = C17B-C18B = C18B-C19B = C16-C17A
 1.54 with sigma of 0.01
 C14-C15
 1.5 with sigma of 0.01
 C15-O3A \\sim C15-O3B
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C18A) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(C18B) \\sim Ueq,
Uanis(C19B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C17A) = Uanis(C17B)
Uanis(O3A) = Uanis(O3B)
5. Others
 Sof(H16C)=Sof(H16D)=Sof(C17B)=Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18C)=
 Sof(H18D)=Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(1)
 Sof(H16A)=Sof(H16B)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18A)=
 Sof(H18B)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
 Sof(O3B)=1-FVAR(2)
 Sof(O3A)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B), C16(H16A,H16B), C16(H16C,
 H16D), C17A(H17A,H17B), C18A(H18A,H18B), C17B(H17C,H17D), C18B(H18C,H18D)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
6.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F)
;
_shelx_res_checksum              52631
_shelx_hkl_checksum              84371
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'