α-Amidino Rhodium Carbenes: Key Intermediates for the Preparation of (E)-2-Aminomethylene-3-oxoindoles and Pyranoindoles.
Qian, Jing; Sheng, Guorong; Huang, Kai; Liu, Shaojie; Lu, Ping; Wang, Yanguang; Organic letters 18 (2016) 3682–3685; doi:10.1021/acs.orglett.6b01728

data_1555643
_publ_section_title
;
 \a-Amidino Rhodium Carbenes: Key Intermediates for the Preparation of
 (E)-2-Aminomethylene-3-oxoindoles and Pyranoindoles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3682
_journal_page_last               3685
_journal_paper_doi               10.1021/acs.orglett.6b01728
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C21 H18 N2 O4 S'
_chemical_formula_sum            'C21 H18 N2 O4 S'
_chemical_formula_weight         394.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                87.384(5)
_cell_angle_beta                 86.032(4)
_cell_angle_gamma                74.912(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3603(3)
_cell_length_b                   7.5430(4)
_cell_length_c                   17.2163(9)
_cell_measurement_reflns_used    2038
_cell_measurement_temperature    170.1
_cell_measurement_theta_max      29.4010
_cell_measurement_theta_min      3.1652
_cell_volume                     920.29(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.1
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0351174000
_diffrn_orient_matrix_UB_12      0.0590228000
_diffrn_orient_matrix_UB_13      0.0315669000
_diffrn_orient_matrix_UB_21      0.0016470000
_diffrn_orient_matrix_UB_22      -0.0774469000
_diffrn_orient_matrix_UB_23      0.0251684000
_diffrn_orient_matrix_UB_31      0.0936011000
_diffrn_orient_matrix_UB_32      -0.0033483000
_diffrn_orient_matrix_UB_33      0.0087772000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5753
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70707
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3336
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.2361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                2763
_reflns_number_total             3336
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01728_si_002.cif
_cod_data_source_block           160113_qj2_sj63
_cod_database_code               1555643
_chemical_oxdiff_formula         'C10 H10 N2 O8 S1'
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C16(H16),
 C17(H17), C19(H19), C20(H20)
3.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;