Catalytic enantioselective ene-type reactions of vinylogous hydrazone: construction of α-methylene-γ-butyrolactone derivatives.
Zhang, Hang; Yao, Qian; Cao, Weidi; Ge, Shulin; Xu, Jinxiu; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 54 (2018) 12511–12514; doi:10.1039/c8cc07567k

data_7122454
_publ_section_title
;
 Catalytic enantioselective ene-type reactions of vinylogous hydrazone:
 construction of \a-methylene-\g-butyrolactone derivatives.
;
_journal_issue                   88
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12511
_journal_page_last               12514
_journal_paper_doi               10.1039/c8cc07567k
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H20 I N3 O2'
_chemical_formula_sum            'C18 H20 I N3 O2'
_chemical_formula_weight         437.27
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-16 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5952(3)
_cell_length_b                   8.1944(3)
_cell_length_c                   34.4405(11)
_cell_measurement_reflns_used    3611
_cell_measurement_temperature    294.2(2)
_cell_measurement_theta_max      71.7880
_cell_measurement_theta_min      5.9050
_cell_volume                     1861.29(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      air
_diffrn_ambient_temperature      294.2(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_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   -104.00 -10.00   1.00    1.00    --  -36.29 -77.00 -60.00   94
  2  \w    -33.00 106.00   1.00    1.00    --   36.29   0.00-120.00  139
  3  \w      1.00  75.00   1.00    1.00    --   36.29 -99.00  60.00   74
  4  \w    -33.00  55.00   1.00    1.00    --   36.29 -38.00  30.00   88
  5  \w     39.00 115.00   1.00    3.95    --  108.71-111.00 120.00   76
  6  \w     37.00 147.00   1.00    3.95    --  108.71 -15.00-150.00  110
  7  \w     41.00 135.00   1.00    3.95    --  108.71 -77.00-150.00   94
  8  \w     39.00 109.00   1.00    3.95    --  108.71 -94.00 150.00   70
  9  \w     40.00 126.00   1.00    3.95    --  108.71 -45.00 -60.00   86
 10  \w     37.00 147.00   1.00    3.95    --  108.71 -15.00 -30.00  110
 11  \w     87.00 178.00   1.00    3.95    --  108.71  30.00   0.00   91
 12  \w   -104.00 -27.00   1.00    1.00    --  -36.29 -77.00  60.00   77
 13  \w    -35.00  66.00   1.00    1.00    --   36.29 -19.00 150.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0226578000
_diffrn_orient_matrix_UB_12      0.1592376000
_diffrn_orient_matrix_UB_13      0.0233741000
_diffrn_orient_matrix_UB_21      -0.0028782000
_diffrn_orient_matrix_UB_22      -0.0985098000
_diffrn_orient_matrix_UB_23      0.0381166000
_diffrn_orient_matrix_UB_31      0.2324238000
_diffrn_orient_matrix_UB_32      -0.0168995000
_diffrn_orient_matrix_UB_33      -0.0017996000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            10231
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.747
_diffrn_reflns_theta_min         5.137
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.821
_refine_diff_density_min         -1.668
_refine_diff_density_rms         0.188
_refine_ls_abs_structure_details
;
 Flack x determined using 1120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3604
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0722
_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^)+(0.1505P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1912
_refine_ls_wR_factor_ref         0.2003
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3223
_reflns_number_total             3604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07567k2.cif
_cod_data_source_block           fxm-zhsub03
_cod_depositor_comments
'Adding full bibliography for 7122454--7122457.cif.'
_cod_database_code               7122454
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00J(H00J,H00K), C00K(H00L,H00M), C00M(H00N,H00O), C00N(H00P,
 H00Q), C00O(H00R,H00S)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00C), C00E(H00E), C00G(H00G), C00I(H00I)
2.c Idealised Me refined as rotating group:
 C00H(H00D,H00F,H00H)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.833
_oxdiff_exptl_absorpt_empirical_full_min 0.466