1,4-Addition Ugi Reaction Using Cyclic α,β-Unsaturated Ketone as Substrate.
Lu, Kui; Ma, Yantao; Gao, Meile; Liu, Yan; Li, Ming; Xu, Chuanming; Zhao, Xia; Yu, Peng; Organic letters 18 (2016) 5038–5041; doi:10.1021/acs.orglett.6b02493

data_1544189
_publ_section_title
;
 1,4-Addition Ugi Reaction Using Cyclic \a,\b-Unsaturated Ketone as
 Substrate.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5038
_journal_page_last               5041
_journal_paper_doi               10.1021/acs.orglett.6b02493
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C24 H27 Br N2 O2'
_chemical_formula_sum            'C24 H27 Br N2 O2'
_chemical_formula_weight         455.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-18
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.636(3)
_cell_length_b                   10.254(2)
_cell_length_c                   30.557(6)
_cell_measurement_reflns_used    9003
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.0510
_cell_measurement_theta_min      1.9985
_cell_volume                     4272.6(15)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
    Number of images: 180
               Slice: -110.0000 - 70.0000
         Image width: 1.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.7664
              2theta: -20.1115
scan:
    Number of images: 150
               Slice: -110.0000 - 40.0000
         Image width: 1.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.7664
              2theta: -20.1115
scan:
    Number of images: 100
               Slice: -110.0000 - -10.0000
         Image width: 1.0000
            Exp time: 2.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 44.7664
              2theta: -20.1115
;
_diffrn_measurement_device
;
Saturn70 (4x4 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0086
_diffrn_orient_matrix_UB_12      -0.0095
_diffrn_orient_matrix_UB_13      0.0967
_diffrn_orient_matrix_UB_21      -0.0403
_diffrn_orient_matrix_UB_22      0.0612
_diffrn_orient_matrix_UB_23      0.0030
_diffrn_orient_matrix_UB_31      -0.0273
_diffrn_orient_matrix_UB_32      -0.0176
_diffrn_orient_matrix_UB_33      -0.0040
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            40516
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.990
_diffrn_reflns_theta_min         2.002
_diffrn_source                   'rotating anode'
_diffrn_source_current           16.0000
_diffrn_source_power             0.8000
_diffrn_source_voltage           50.0000
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.947
_exptl_absorpt_correction_T_max  0.8000
_exptl_absorpt_correction_T_min  0.6968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.089
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0751P)^2^+2.5430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4143
_reflns_number_total             5135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02493_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1544189.cif.
;
_cod_database_code               1544189
_shelx_estimated_absorpt_t_max   0.800
_shelx_estimated_absorpt_t_min   0.697
_diffrn_number_total             20169
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              50961
_shelx_hkl_checksum              76842
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'