A gold(I)-catalysed three-component reaction via trapping oxonium ylides with allenamides
Liu, Gengxin; Yu, Sifan; Hu, Wenhao; Qiu, Huang; Chemical Communications  (2019) –; doi:10.1039/C9CC06599G

data_7124202
_publ_section_title
;
 A gold(I)-catalysed three-component reaction via trapping oxonium ylides
 with allenamides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06599G
_journal_year                    2019
_chemical_formula_moiety         'C21 H20 I N O5'
_chemical_formula_sum            'C21 H20 I N O5'
_chemical_formula_weight         493.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-28 deposited with the CCDC.    2019-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6909(2)
_cell_length_b                   8.22250(10)
_cell_length_c                   30.5829(3)
_cell_measurement_reflns_used    11248
_cell_measurement_temperature    99.98(13)
_cell_measurement_theta_max      75.6750
_cell_measurement_theta_min      2.8840
_cell_volume                     3945.76(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -114.00 -27.00   0.50    0.05    -- -100.00  62.00-134.00  174
  2  \w   -125.00 -29.00   0.50    0.05    -- -100.00  79.00  92.00  192
  3  \w   -107.00 -54.00   0.50    0.05    -- -100.00  82.00 -19.00  106
  4  \w   -118.00 -82.00   0.50    0.05    --  -46.62-125.00 -60.00   72
  5  \w   -118.00 -90.00   0.50    0.05    --  -46.62-125.00  60.00   56
  6  \w   -115.00 -71.00   0.50    0.05    --  -46.62-125.00  30.00   88
  7  \w   -119.00 -71.00   0.50    0.05    --  -46.62-125.00-150.00   96
  8  \w   -118.00 -93.00   0.50    0.05    --  -46.62-125.00 150.00   50
  9  \w   -119.00 -94.00   0.50    0.05    --  -46.62-125.00   0.00   50
 10  \w     87.00 115.00   0.50    0.05    --  107.00-125.00-180.00   56
 11  \w     35.00  60.00   0.50    0.05    --  107.00-125.00-180.00   50
 12  \w    102.00 163.00   0.50    0.05    --  107.00  30.00-180.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1377981000
_diffrn_orient_matrix_UB_12      -0.0650799000
_diffrn_orient_matrix_UB_13      0.0072120000
_diffrn_orient_matrix_UB_21      -0.0800392000
_diffrn_orient_matrix_UB_22      0.0282466000
_diffrn_orient_matrix_UB_23      -0.0431833000
_diffrn_orient_matrix_UB_31      0.0986274000
_diffrn_orient_matrix_UB_32      -0.0678114000
_diffrn_orient_matrix_UB_33      -0.0249294000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14042
_diffrn_reflns_point_group_measured_fraction_full 0.766
_diffrn_reflns_point_group_measured_fraction_max 0.766
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         2.890
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.036
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29044
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.661
_exptl_crystal_description       plate
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.390(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         5398
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0431P)^2^+20.2249P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1139
_reflns_Friedel_coverage         0.501
_reflns_Friedel_fraction_full    0.522
_reflns_Friedel_fraction_max     0.522
_reflns_number_gt                5146
_reflns_number_total             5398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06599g2.cif
_cod_data_source_block           yusif_181225
_cod_database_code               7124202
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.356
_shelx_estimated_absorpt_t_min   0.111
_reflns_odcompleteness_completeness 99.98
_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 Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C20(H20A,H20B), C45(H45A,H45B), C46(H46A,H46B), C9(H9A,H9B),
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C34(H34), C56(H56), C30(H30), C5(H5), C55(H55), C53(H53), C10(H10),
 C6(H6), C39(H39), C38(H38), C52(H52), C24(H24), C54(H54), C27(H27), C28(H28),
 C2(H2), C33(H33), C3(H3), C31(H31), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              29310
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.735
_oxdiff_exptl_absorpt_empirical_full_min 0.552