Sequential one-pot three component rhodium-catalysed isomerisation/1,3-dipolar cycloaddition cascades to fused-ring heterocycles
Windle, Jonathan; Allison, Matthew; Shepherd, Helena; Sridharan, Visuvanathar; RSC Adv. 4 (2014) 2624–; doi:10.1039/C3RA45906C

data_7239413
_publ_section_title
;
 Sequential one-pot three component rhodium-catalysed
 isomerisation/1,3-dipolar cycloaddition cascades to fused-ring
 heterocycles
;
_journal_issue                   6
_journal_name_full               'RSC Adv.'
_journal_page_first              2624
_journal_paper_doi               10.1039/C3RA45906C
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C17 H20 N2 O3'
_chemical_formula_sum            'C17 H20 N2 O3'
_chemical_formula_weight         300.35
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-03
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.345(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5132(9)
_cell_length_b                   9.0524(4)
_cell_length_c                   14.4988(10)
_cell_measurement_reflns_used    2776
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      73.8510
_cell_measurement_theta_min      4.0340
_cell_volume                     1529.69(19)
_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      101(2)
_diffrn_detector_area_resol_mean 5.3095
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9622
_diffrn_measurement_details
;
  1 omega -107.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000 -180.0000 86

  2 omega  -54.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000   30.0000 49

  3 omega  -90.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000  120.0000 85

  4 omega   38.00  131.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -61.0000    0.0000 93

  5 omega  100.00  133.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      104.9775  125.0000  -30.0000 33

  6 omega  150.00  175.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      104.9775  125.0000  -30.0000 25

  7 omega   35.00   97.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -45.0000 -120.0000 62

  8 omega   51.00   82.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -30.0000 -180.0000 31

  9 omega   37.00   89.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      104.9775  -45.0000 -180.0000 52

 10 omega   79.00  173.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      104.9775   61.0000  150.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0900150000
_diffrn_orient_matrix_UB_12      0.0241116000
_diffrn_orient_matrix_UB_13      -0.1045860000
_diffrn_orient_matrix_UB_21      0.0912962000
_diffrn_orient_matrix_UB_22      0.0764018000
_diffrn_orient_matrix_UB_23      -0.0317048000
_diffrn_orient_matrix_UB_31      0.0319845000
_diffrn_orient_matrix_UB_32      -0.1500988000
_diffrn_orient_matrix_UB_33      -0.0327742000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5359
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.56
_diffrn_reflns_theta_min         4.01
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78019
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0511
_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^)+(0.0532P)^2^+0.1715P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1111
_reflns_number_gt                2244
_reflns_number_total             2696
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra45906c.txt
_cod_data_source_block           jw19_a_manual
_cod_original_cell_volume        1529.67(17)
_cod_database_code               7239413
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9), C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C3(H3), C1(H1), C2(H2)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;