A concise route to indoloazocines via a sequential Ugi-gold-catalyzed intramolecular hydroarylation
Sachin G. Modha; Dipak D. Vachhani; Jeroen Jacobs; Luc Van Meervelt; Erik V. Van der Eycken; Chem.Commun. 48 (2012) 6550–; doi:10.1039/c2cc32586a

data_7107884
_publ_section_title
;
 A concise route to indoloazocines via a sequential Ugi-gold-catalyzed
 intramolecular hydroarylation
;
_journal_name_full               Chem.Commun.
_journal_page_first              6550
_journal_paper_doi               10.1039/c2cc32586a
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H29 Cl2 N3 O4'
_chemical_formula_sum            'C28 H29 Cl2 N3 O4'
_chemical_formula_weight         542.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             012-01-25
_audit_creation_method
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4032(7)
_cell_length_b                   14.2768(8)
_cell_length_c                   16.2935(7)
_cell_measurement_reflns_used    4907
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1429
_cell_measurement_theta_min      2.8730
_cell_volume                     2652.6(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_details
;
1 omega -28.00 -1.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -17.1513 57.0000 -90.0000 27

2 omega -18.00 25.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -17.1513 -99.0000 150.0000 43

3 omega -16.00 16.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- -17.1513 -99.0000 -30.0000 32

4 omega 18.00 91.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 18.8701 0.0000 0.0000 73

5 omega -54.00 -7.00 1.0000 15.0000
omega____ theta____ kappa____ phi______ frames
- 18.8701 0.0000 0.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0168370000
_diffrn_orient_matrix_UB_12      -0.0465274000
_diffrn_orient_matrix_UB_13      0.0098845000
_diffrn_orient_matrix_UB_21      -0.0577198000
_diffrn_orient_matrix_UB_22      -0.0156276000
_diffrn_orient_matrix_UB_23      -0.0086342000
_diffrn_orient_matrix_UB_31      0.0159466000
_diffrn_orient_matrix_UB_32      -0.0077968000
_diffrn_orient_matrix_UB_33      -0.0414938000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12398
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_min         2.88
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.1885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                4875
_reflns_number_total             6146
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc32586a.txt
_cod_data_source_block           test
_cod_database_code               7107884
_chemical_oxdiff_formula         'C28 O4 N3 Cl2 H29'
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32