Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds
Marichev, Kostiantyn O.; Adly, Frady G.; Carranco, Alejandra M.; Garcia, Estevan C.; Arman, Hadi; Doyle, Michael P.; ACS Catalysis 8 (2018) 10392–; doi:10.1021/acscatal.8b03391

data_4515756
_publ_section_title
;
 Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of
 Enoldiazocarbonyl Compounds
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              10392
_journal_paper_doi               10.1021/acscatal.8b03391
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C22 H22 N4 O'
_chemical_formula_sum            'C22 H22 N4 O'
_chemical_formula_weight         358.43
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.865(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4088(2)
_cell_length_b                   7.0686(2)
_cell_length_c                   19.8625(5)
_cell_measurement_reflns_used    8559
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      29.4630
_cell_measurement_theta_min      2.8800
_cell_volume                     897.75(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (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_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    -85.00  26.00   1.00   25.00    --    4.20 -38.00  60.00  111
  2  \w    -97.00  17.00   1.00   25.00    --   -7.60 -38.00 150.00  114
  3  \w    -97.00  82.00   1.00   25.00    --   -7.60   0.00-180.00  179
  4  \w    -37.00  45.00   1.00   25.00    --   -7.60  57.00   0.00   82
  5  \w    -32.00  82.00   1.00   25.00    --   -7.60  38.00 -90.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0494243000
_diffrn_orient_matrix_UB_12      0.0867314000
_diffrn_orient_matrix_UB_13      -0.0072451000
_diffrn_orient_matrix_UB_21      -0.0990510000
_diffrn_orient_matrix_UB_22      0.0449581000
_diffrn_orient_matrix_UB_23      -0.0038724000
_diffrn_orient_matrix_UB_31      0.0069672000
_diffrn_orient_matrix_UB_32      0.0229897000
_diffrn_orient_matrix_UB_33      0.0348357000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16945
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.060
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
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    1.326
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_recrystallization_method
'Slow evaporation of a 3:1 solutin of acetone and hexane.'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0400P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                3942
_reflns_number_total             4025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03391_si_002.cif
_cod_data_source_block           cd1707a
_cod_database_code               4515756
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C22H22N4O
_chemical_oxdiff_usercomment     KM-3-87
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.973
_reflns_odcompleteness_completeness 99.90
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C1(H1A,H1B), C3(H3A,H3B), C0AA(H0AA,H0AB), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C22(H22), C12(H12), C13(H13), C21(H21), C15(H15), C18(H18), C16(H16),
 C20(H20), C19(H19), C14(H14)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.060
_oxdiff_exptl_absorpt_empirical_full_min 0.889