Catalytic Asymmetric [3 + 2] Cycloaddition Reaction between Aurones and Isocyanoacetates: Access to Spiropyrrolines via Silver Catalysis.
Wang, Zhi-Peng; Xiang, Sichuan; Shao, Pan-Lin; He, Yun; The Journal of organic chemistry 83 (2018) 10995–11007; doi:10.1021/acs.joc.8b01622

data_4035654
_publ_section_title
;
 Catalytic Asymmetric [3 + 2] Cycloaddition Reaction between Aurones and
 Isocyanoacetates: Access to Spiropyrrolines via Silver Catalysis.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10995
_journal_page_last               11007
_journal_paper_doi               10.1021/acs.joc.8b01622
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H17 N O4'
_chemical_formula_sum            'C19 H17 N O4'
_chemical_formula_weight         321.30
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-09-04
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5097)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.50908(6)
_cell_length_b                   8.44660(10)
_cell_length_c                   29.2131(3)
_cell_measurement_reflns_used    11762
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      72.8800
_cell_measurement_theta_min      4.4920
_cell_volume                     1606.12(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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    -64.00  31.00   1.00    1.00    --  -37.03  77.00-180.00   95
  2  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00  60.00   95
  3  \w    -30.00  54.00   1.00    1.00    --   37.03 -57.00  90.00   84
  4  \w     24.00  91.00   1.00    1.00    --   37.03-126.00 -30.00   67
  5  \w    101.00 178.00   1.00    1.00    --  110.47  93.00  82.00   77
  6  \w    101.00 178.00   1.00    1.00    --  110.47 112.00  60.00   77
  7  \w     93.00 178.00   1.00    1.00    --  110.47  45.00-150.00   85
  8  \w     41.00 116.00   1.00    1.00    --  110.47-112.00  60.00   75
  9  \w     89.00 178.00   1.00    1.00    --  110.47  30.00-120.00   89
 10  \w     93.00 178.00   1.00    1.00    --  110.47  45.00  30.00   85
 11  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00 -30.00   95
 12  \w   -104.00 -20.00   1.00    1.00    --  -37.03 -57.00 120.00   84
 13  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00-120.00   95
 14  \w     43.00 137.00   1.00    1.00    --  110.47 -77.00  90.00   94
 15  \w     93.00 178.00   1.00    1.00    --  110.47  45.00 150.00   85
 16  \w     89.00 178.00   1.00    1.00    --  110.47  30.00   0.00   89
 17  \w     41.00 109.00   1.00    1.00    --  110.47 -95.00-120.00   68
 18  \w     89.00 178.00   1.00    1.00    --  110.47  30.00  90.00   89
 19  \w     92.00 177.00   1.00    1.00    --  110.47  61.00 -60.00   85
 20  \w    -54.00  30.00   1.00    1.00    --  -37.03  57.00 -90.00   84
 21  \w   -104.00 -20.00   1.00    1.00    --  -37.03 -57.00 150.00   84
 22  \w    -30.00  54.00   1.00    1.00    --   37.03 -57.00   0.00   84
 23  \w     44.00  73.00   1.00    1.00    --  110.47 -61.00 -30.00   29
 24  \w     93.00 178.00   1.00    1.00    --  110.47  45.00 -90.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1951315000
_diffrn_orient_matrix_UB_12      -0.0690150000
_diffrn_orient_matrix_UB_13      -0.0222118000
_diffrn_orient_matrix_UB_21      0.0991548000
_diffrn_orient_matrix_UB_22      -0.0170462000
_diffrn_orient_matrix_UB_23      0.0476414000
_diffrn_orient_matrix_UB_31      -0.0900799000
_diffrn_orient_matrix_UB_32      -0.1679462000
_diffrn_orient_matrix_UB_33      0.0042648000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            14590
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.999
_diffrn_reflns_theta_min         5.452
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1266 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.263
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.263
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0402
_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^)+(0.0187P)^2^+1.2481P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.0996
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3161
_reflns_number_total             3172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01622_si_003.cif
_cod_data_source_block           zzn083101
_cod_depositor_comments
;

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.13(C19 H17 N O4)'
_cod_original_formula_sum        'C2.53 H2 N0.13 O0.53'
_cod_original_formula_units_Z    30
_cod_original_formula_weight     42.84
_cod_database_code               4035654
_chemical_oxdiff_formula         'C1 H1 N1 O1'
_reflns_odcompleteness_completeness 99.83
_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:
 C5AA(H5AA), C4BA(H4BA)
2.b Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB)
2.c Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C3AA(H3AA), C4AA(H4AA), C6AA(H6AA), C9AA(H9AA), C0BA(H0BA),
 C3BA(H3BA), C6BA(H6BA), C7BA(H7BA)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              67087
_shelx_hkl_checksum              64737
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-08-31
_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.676