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_4035655
_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         '0.13(C26 H22 Cl N O4)'
_chemical_formula_sum            'C3.3 H2.79 Cl0.13 N0.13 O0.51'
_chemical_formula_weight         56.82
_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             2017-10-11
_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            63
_cell_length_a                   9.82226(11)
_cell_length_b                   14.71407(18)
_cell_length_c                   30.9505(3)
_cell_measurement_reflns_used    11945
_cell_measurement_temperature    99.97(12)
_cell_measurement_theta_max      72.9560
_cell_measurement_theta_min      4.2770
_cell_volume                     4473.13(9)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -66.00  34.00   1.00    1.89    --  -37.03  19.00  90.00  100
  2  \w     24.00  91.00   1.00    1.89    --   37.03-126.00-150.00   67
  3  \w     20.00 104.00   1.00    1.89    --   37.03  57.00   0.00   84
  4  \w    -30.00  54.00   1.00    1.89    --   37.03 -57.00-120.00   84
  5  \w     24.00  91.00   1.00    1.89    --   37.03-126.00 -90.00   67
  6  \w     41.00 132.00   1.00   11.00    --  110.47 -30.00-150.00   91
  7  \w     44.00 129.00   1.00   11.00    --  110.47 -61.00 150.00   85
  8  \w     41.00 109.00   1.00   11.00    --  110.47 -95.00  90.00   68
  9  \w    101.00 178.00   1.00   11.00    --  110.47 112.00 -60.00   77
 10  \w     41.00 109.00   1.00   11.00    --  110.47 -95.00   0.00   68
 11  \w     89.00 178.00   1.00   11.00    --  110.47  30.00  30.00   89
 12  \w     20.00  85.00   1.00    1.89    --   37.03  57.00 120.00   65
;
_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      0.0181283000
_diffrn_orient_matrix_UB_12      0.0024449000
_diffrn_orient_matrix_UB_13      -0.0494125000
_diffrn_orient_matrix_UB_21      0.0134516000
_diffrn_orient_matrix_UB_22      0.1042734000
_diffrn_orient_matrix_UB_23      0.0016670000
_diffrn_orient_matrix_UB_31      0.1552154000
_diffrn_orient_matrix_UB_32      -0.0094086000
_diffrn_orient_matrix_UB_33      0.0056298000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18982
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.066
_diffrn_reflns_theta_min         4.146
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43676
_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             1870
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 3194 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         8517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0450P)^2^+0.9090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                8073
_reflns_number_total             8517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01622_si_002.cif
_cod_data_source_block           zzn1011
_cod_original_cell_volume        4473.14(9)
_cod_original_formula_sum        'C3.30 H2.79 Cl0.13 N0.13 O0.51'
_cod_database_code               4035655
_chemical_oxdiff_formula         'C1 H1 N1 O1 Cl1'
_reflns_odcompleteness_completeness 99.91
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C33(H33), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C20(H20A,H20B), C35(H35A,H35B), C46(H46A,H46B)
2.c Aromatic/amide H refined with riding coordinates:
 C48(H48), C5(H5), C26(H26), C2(H2), C39(H39), C13(H13), C52(H52), C16(H16),
 C31(H31), C22(H22), C4(H4), C50(H50), C3(H3), C14(H14), C30(H30), C51(H51),
 C24(H24), C15(H15), C25(H25), C40(H40), C49(H49), C42(H42), C23(H23), C41(H41),
  C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              79646
_shelx_hkl_checksum              73210
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-10-11
_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 2.203
_oxdiff_exptl_absorpt_empirical_full_min 0.581