Asymmetric [3 + 2] Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Aldehydes by Synergistic Palladium and Organocatalysis.
Halskov, Kim Søholm; Næsborg, Line; Tur, Fernando; Jørgensen, Karl Anker; Organic letters 18 (2016) 2220–2223; doi:10.1021/acs.orglett.6b00852

data_1555551
_publ_section_title
;
 Asymmetric [3 + 2] Cycloaddition of Vinylcyclopropanes and
 \a,\b-Unsaturated Aldehydes by Synergistic Palladium and Organocatalysis.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2220
_journal_page_last               2223
_journal_paper_doi               10.1021/acs.orglett.6b00852
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C16 H18 N2 O2'
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.33
_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_Int_Tables_number      4
_audit_creation_date             2016-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.552(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.94706(18)
_cell_length_b                   11.2291(3)
_cell_length_c                   14.9983(3)
_cell_measurement_reflns_used    5223
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.9980
_cell_measurement_theta_min      2.4230
_cell_volume                     1470.83(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3590
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9931
_diffrn_measured_fraction_theta_max 0.8824
_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    -81.00 -34.00   1.00   60.00    --   18.69 178.00  60.00   47
  2  \w    -82.00 -35.00   1.00   60.00    --   18.69-178.00 -90.00   47
  3  \w    -28.00 109.00   1.00   60.00    --   18.69  38.00 -60.00  137
  4  \w    -23.00 111.00   1.00   60.00    --   18.69  57.00  30.00  134
  5  \w    -20.00  69.00   1.00   60.00    --   18.69 -99.00 -30.00   89
  6  \w    -28.00   9.00   1.00   60.00    --   18.69  38.00-180.00   37
  7  \w   -119.00 -34.00   1.00   60.00    --  -19.62 178.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0505777000
_diffrn_orient_matrix_UB_12      -0.0480624000
_diffrn_orient_matrix_UB_13      -0.0020843000
_diffrn_orient_matrix_UB_21      0.0635359000
_diffrn_orient_matrix_UB_22      0.0381466000
_diffrn_orient_matrix_UB_23      0.0155384000
_diffrn_orient_matrix_UB_31      -0.0005693000
_diffrn_orient_matrix_UB_32      -0.0151093000
_diffrn_orient_matrix_UB_33      0.0458286000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16869
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         2.29
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.2207
_exptl_crystal_description       block
_exptl_crystal_F_000             576.2642
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.2422
_refine_diff_density_min         -0.2448
_refine_diff_density_rms         0.0556
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.9(6)
_refine_ls_d_res_high            0.7390
_refine_ls_d_res_low             8.9099
_refine_ls_goodness_of_fit_ref   1.0567
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    58
_refine_ls_number_parameters     378
_refine_ls_number_reflns         6730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0567
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.0850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.838
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              15
_reflns_limit_k_min              -14
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                5544
_reflns_number_total             6730
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol6b00852_si_002.cif
_cod_data_source_block           2016_03_03_notwinB
_cod_original_cell_volume        1470.82(6)
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               1555551
_chemical_oxdiff_formula         C16H18N2O2
_reflns_odcompleteness_completeness 99.97
_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, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00h), C00F(H00i), C00G(H00G), C00J(H00J), C00K(H00K), C00M(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C00R(H00c,H00d), C00W(H00l,H00r), C00Z(H00w,H00z), C010(H01a,H01b)
2.c Aromatic/amide H refined with riding coordinates:
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00X(H00X), C00Y(H00Y), C011(H011), C012(H012)
2.d X=CH2 refined with riding coordinates:
 N005(H00a,H00b), N008(H00e,H00f)
2.e Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003)
;
_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 1.519
_oxdiff_exptl_absorpt_empirical_full_min 0.745