Aluminum(salen) Complexes as Catalysts for the Kinetic Resolution of Terminal Epoxides via CO2Coupling
North, Michael; Quek, Sophie C. Z.; Pridmore, Natalie E.; Whitwood, Adrian C.; Wu, Xiao; ACS Catalysis 5 (2015) 3398–; doi:10.1021/acscatal.5b00235

data_4512945
_publ_section_title
;
 Aluminum(salen) Complexes as Catalysts for the Kinetic Resolution of
 Terminal Epoxides via CO2Coupling
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3398
_journal_paper_doi               10.1021/acscatal.5b00235
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C36 H52 Br Co N2 O2'
_chemical_formula_sum            'C36 H52 Br Co N2 O2'
_chemical_formula_weight         683.63
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                65.979(3)
_cell_angle_beta                 89.9734(19)
_cell_angle_gamma                71.994(2)
_cell_formula_units_Z            2
_cell_length_a                   10.7950(2)
_cell_length_b                   12.6416(4)
_cell_length_c                   14.6957(4)
_cell_measurement_reflns_used    5365
_cell_measurement_temperature    110.00(14)
_cell_measurement_theta_max      70.4050
_cell_measurement_theta_min      7.3580
_cell_volume                     1723.83(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega   31.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000    0.0000 40

  2 omega   35.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 34

  3 omega   33.00  104.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000    0.0000 71

  4 omega   83.00  110.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 27

  5 omega   90.00  171.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 81

  6 omega   66.00   93.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 27

  7 omega   47.00   94.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 47

  8 omega   78.00  104.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 26

  9 omega   66.00  109.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 43

 10 omega   59.00   86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 27

 11 omega   45.00   72.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 27

 12 omega   42.00   83.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000   90.0000 41

 13 omega   36.00  138.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  120.0000 102

 14 omega   50.00  136.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 86

 15 omega   44.00  114.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 70

 16 omega   44.00   84.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000 -180.0000 40

 17 omega   38.00   92.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000 -120.0000 54

 18 omega   43.00  178.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000 -180.0000 135

 19 omega   38.00  110.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   60.0000 72

 20 omega   37.00   64.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000   30.0000 27

 21 omega   36.00   90.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000  -60.0000 54

 22 omega   30.00   93.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000 -150.0000 63

 23 omega   28.00  122.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   37.0000 -150.0000 94

 24 omega   -4.00   72.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -37.0000 -150.0000 76

 25 omega  -17.00   78.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -37.0000   30.0000 95

 26 omega  -18.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 45

 27 omega  -67.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  158.0000  165.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0271480000
_diffrn_orient_matrix_UB_12      0.1182693000
_diffrn_orient_matrix_UB_13      -0.0980611000
_diffrn_orient_matrix_UB_21      -0.0393731000
_diffrn_orient_matrix_UB_22      0.0778754000
_diffrn_orient_matrix_UB_23      0.0599568000
_diffrn_orient_matrix_UB_31      0.1439097000
_diffrn_orient_matrix_UB_32      -0.0069126000
_diffrn_orient_matrix_UB_33      0.0155447000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11806
_diffrn_reflns_point_group_measured_fraction_full 0.609
_diffrn_reflns_point_group_measured_fraction_max 0.590
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.155
_diffrn_reflns_theta_min         4.005
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.502
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_correction_T_min  0.386
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.317
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.2554
_exptl_crystal_size_mid          0.1625
_exptl_crystal_size_min          0.0289
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.017(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     794
_refine_ls_number_reflns         7887
_refine_ls_number_restraints     57
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0493P)^2^+0.2182P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.211
_reflns_friedel_fraction_full    0.219
_reflns_friedel_fraction_max     0.205
_reflns_number_gt                7278
_reflns_number_total             7887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs5b00235_si_001.cif
_cod_data_source_block           mn1409
_cod_depositor_comments          'Adding full bibliography for 4512945.cif.'
_cod_original_cell_volume        1723.82(9)
_cod_database_code               4512945
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C36 H52 Br1 Co1 N2 O2'
_chemical_oxdiff_usercomment     'Sophie Quek SQ1038 + TBAB'
_reflns_odcompleteness_completeness 99.92
_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
2. Restrained distances
 C66-C67 \\sim C66A-C67A \\sim C67-C68 \\sim C67A-C68A \\sim C68-C66 \\sim
C68A-C66A
 with sigma of 0.002
 C65-C66 \\sim C65-C66A \\sim C65-C67 \\sim C65-C67A \\sim C65-C68 \\sim
C65-C68A
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C66A) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C67A) \\sim Ueq, Uanis(C67)
\\sim Ueq: with sigma of 0.004 and sigma for terminal atoms of 0.008
Uanis(C68) = Uanis(C68A)
Uanis(C67) = Uanis(C67A)
Uanis(C66) = Uanis(C66A)
4. Others
 Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(H67C)=
 Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H68C)=1-FVAR(1)
 Sof(C66A)=Sof(H66D)=Sof(H66E)=Sof(H66F)=Sof(C67A)=Sof(H67D)=Sof(H67E)=
 Sof(H67F)=Sof(C68A)=Sof(H68D)=Sof(H68E)=Sof(H68F)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C37(H37), C42(H42)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C38(H38A,H38B), C39(H39A,
 H39B), C40(H40A,H40B), C41(H41A,H41B)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C11(H11), C22(H22), C24(H24), C26(H26), C43(H43), C45(H45),
 C47(H47), C58(H58), C60(H60), C62(H62)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C30(H30A,H30B,H30C), C31(H31A,
 H31B,H31C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,
 H53C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C66(H66A,
 H66B,H66C), C66A(H66D,H66E,H66F), C67(H67A,H67B,H67C), C67A(H67D,H67E,H67F),
 C68(H68A,H68B,H68C), C68A(H68D,H68E,H68F), C70(H70A,H70B,H70C), C71(H71A,H71B,
 H71C), C72(H72A,H72B,H72C)
;
_olex2_date_sample_data_collection 2014-07-25
_olex2_date_sample_submission    1405292400
_olex2_exptl_crystal_mounting_method 'Oil on loop'
_olex2_submission_special_instructions 'No special instructions were received'