Asymmetric synthesis of polysubstituted methylenecyclobutanes via catalytic [2+2] cycloaddition reactions of N-allenamides.
Zhong, Xia; Tang, Qiong; Zhou, Pengfei; Zhong, Ziwei; Dong, Shunxi; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 54 (2018) 10511–10514; doi:10.1039/c8cc06416d

data_7122225
_publ_section_title
;
 Asymmetric synthesis of polysubstituted methylenecyclobutanes via
 catalytic [2+2] cycloaddition reactions of N-allenamides.
;
_journal_issue                   74
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10511
_journal_page_last               10514
_journal_paper_doi               10.1039/c8cc06416d
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H31 N O6 S'
_chemical_formula_sum            'C34 H31 N O6 S'
_chemical_formula_weight         581.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-23 deposited with the CCDC.
2018-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.455(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5709(7)
_cell_length_b                   7.9832(4)
_cell_length_c                   17.4107(11)
_cell_measurement_reflns_used    1828
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1920
_cell_measurement_theta_min      3.4000
_cell_volume                     1550.12(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   18.00   84.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000  120.0000 66

  2 omega   12.00   55.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -99.0000 -180.0000 43

  3 omega  -43.00   84.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856    0.0000  -90.0000 127
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0287731000
_diffrn_orient_matrix_UB_12      -0.0210073000
_diffrn_orient_matrix_UB_13      0.0401287000
_diffrn_orient_matrix_UB_21      0.0564037000
_diffrn_orient_matrix_UB_22      0.0011645000
_diffrn_orient_matrix_UB_23      -0.0087850000
_diffrn_orient_matrix_UB_31      0.0063199000
_diffrn_orient_matrix_UB_32      0.0863785000
_diffrn_orient_matrix_UB_33      0.0098449000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7641
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.138
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1206 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5609
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0632
_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^)+(0.0793P)^2^+0.0884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1720
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.788
_reflns_Friedel_fraction_max     0.754
_reflns_number_gt                4011
_reflns_number_total             5609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06416d2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7122225--7122226.cif.'
_cod_database_code               7122225
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32)
2.d Fitted hexagon refined as free rotating group:
 C21(C22,C23,C24,C25,C26)
2.e X=CH2 refined with riding coordinates:
 C33(H33A,H33B)
2.f Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;
_olex2_submission_special_instructions 'No special instructions were received'