Synthesis of (E)-3-styryl-2,5-dihydro-1H-pyrrole derivatives via Pd-catalyzed addition of indoles to hydroxy 1,6-enynes
Zhong, Mei-Jin; Zhu, Hai-Tao; Gao, Pin; Qiu, Yi-Feng; Liang, Yong-Min; RSC Advances 4 (2014) 8914–; doi:10.1039/c3ra47647b

data_7239476
_publ_section_title
;
 Synthesis of (E)-3-styryl-2,5-dihydro-1H-pyrrole derivatives via
 Pd-catalyzed addition of indoles to hydroxy 1,6-enynes
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              8914
_journal_paper_doi               10.1039/c3ra47647b
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C35 H32 N2 O2 S'
_chemical_formula_sum            'C35 H32 N2 O2 S'
_chemical_formula_weight         544.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-07-19
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.077(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1191(6)
_cell_length_b                   9.9999(7)
_cell_length_c                   30.7760(14)
_cell_measurement_reflns_used    2449
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.6170
_cell_measurement_theta_min      3.2430
_cell_volume                     3096.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.8902
_diffrn_measurement_details
;
  1 omega   -8.00   22.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000  120.0000 30

  2 omega  -20.00    5.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  -99.0000  -90.0000 25

  3 omega   36.00  104.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000   90.0000 68

  4 omega   63.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000 -180.0000 40

  5 omega  -32.00   97.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512    0.0000  -30.0000 129
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0192351000
_diffrn_orient_matrix_UB_12      0.0596236000
_diffrn_orient_matrix_UB_13      -0.0114487000
_diffrn_orient_matrix_UB_21      0.0582437000
_diffrn_orient_matrix_UB_22      0.0321392000
_diffrn_orient_matrix_UB_23      0.0097336000
_diffrn_orient_matrix_UB_31      0.0347617000
_diffrn_orient_matrix_UB_32      -0.0209116000
_diffrn_orient_matrix_UB_33      -0.0176591000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            14276
_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         26.022
_diffrn_reflns_theta_min         2.996
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.029
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6095
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1936
_refine_ls_R_factor_gt           0.1021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1880P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2845
_refine_ls_wR_factor_ref         0.3641
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2503
_reflns_number_total             6095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3ra47647b.txt
_cod_data_source_block           zhmj0718
_cod_database_code               7239476
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(C31) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C36) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C21) \\sim Ueq, Uanis(N22) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C24(H24), C25(H25), C26(H26),
  C27(H27), C31(H31), C32(H32), C34(H34), C35(H35)
3.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C36(H36A,H36B,H36C)
;
_shelx_hkl_checksum              90033
_shelx_res_checksum              11670
_shelxl_version_number           2013-2