Rhodium(III)-Catalyzed C-H Activation/Annulation with Vinyl Esters as an Acetylene Equivalent.
Webb, Nicola J.; Marsden, Stephen P.; Raw, Steven A.; Organic letters 16 (2014) 4718–4721; doi:10.1021/ol502095z

data_1517490
_publ_section_title
;
 Rhodium(III)-Catalyzed C-H Activation/Annulation with Vinyl Esters as an
 Acetylene Equivalent.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4718
_journal_page_last               4721
_journal_paper_doi               10.1021/ol502095z
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C16 H20 N2 O3, 0.25(H2 O)'
_chemical_formula_sum            'C16 H20.5 N2 O3.25'
_chemical_formula_weight         292.84
_chemical_name_systematic
;
 tert-Butyl 5-oxo-3a,4,5,9b-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-3(2H)-carboxylate 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-13
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.343(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.1273(5)
_cell_length_b                   12.4095(5)
_cell_length_c                   24.1328(9)
_cell_measurement_reflns_used    6133
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.5120
_cell_measurement_theta_min      2.1470
_cell_volume                     3032.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.3095
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.8474
_diffrn_measurement_details
;
  1 omega  -57.00   37.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        9.2970  -19.0000 -120.0000 94

  2 omega  -18.00   27.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.0782  -99.0000   90.0000 45

  3 omega  -62.00    8.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.0782  -77.0000  -60.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0210895000
_diffrn_orient_matrix_UB_12      0.0297171000
_diffrn_orient_matrix_UB_13      0.0232943000
_diffrn_orient_matrix_UB_21      -0.0148068000
_diffrn_orient_matrix_UB_22      0.0446746000
_diffrn_orient_matrix_UB_23      -0.0174075000
_diffrn_orient_matrix_UB_31      -0.0651366000
_diffrn_orient_matrix_UB_32      -0.0197036000
_diffrn_orient_matrix_UB_33      -0.0043494000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            18513
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.88
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.3092
_exptl_crystal_size_mid          0.2031
_exptl_crystal_size_min          0.1568
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         7396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0515P)^2^+0.9115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                6032
_reflns_number_total             7396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502095z_si_001.cif
_cod_data_source_block           Compound12
_cod_depositor_comments
;
Adding full bibliography for 1517489--1517490.cif.

2019-08-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C16 H20 N2 O3), 0.5(H2 O)'
_cod_original_formula_sum        'C32 H41 N4 O6.50'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     585.69
_cod_database_code               1517490
_chemical_oxdiff_formula         'C5 H12 N2 O4'
_chemical_oxdiff_usercomment     '100 K'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O4(0.5) H4A(0.5) H4C(0.5)
3.a Free rotating group:
 O4(H4A,H4C)
;