Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis.
Henderson, Alexander S.; Bower, John F.; Galan, M. Carmen; Organic & biomolecular chemistry 12 (2014) 9180–9183; doi:10.1039/c4ob02056a

data_7154192
_publ_section_title
;
 Carbohydrate-based N-heterocyclic carbenes for enantioselective
 catalysis.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9180
_journal_page_last               9183
_journal_paper_doi               10.1039/c4ob02056a
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C79 H84 Cl N2 O10 Rh'
_chemical_formula_sum            'C79 H84 Cl N2 O10 Rh'
_chemical_formula_weight         1359.84
_chemical_name_systematic
'[1,3-Bis(1,3,4,6-O-benzyl-2-deoxy--D-glucopyranoside)imidazol-2-ylidene](chloro)(1,5-cyclooctadiene)rhodium(I) '
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.11 svn.r2872 for OlexSys, GUI svn.r4767)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0756(2)
_cell_length_b                   15.9328(3)
_cell_length_c                   28.2582(6)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      2.51
_cell_volume                     6787.5(2)
_computing_cell_refinement       'Bruker Apex2'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            57669
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.93
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  0.1864
_exptl_absorpt_correction_T_min  0.1456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0479 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.7811.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2856
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.022(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     839
_refine_ls_number_reflns         15480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0653
_reflns_number_gt                13298
_reflns_number_total             15480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02056a2.cif
_cod_data_source_block           ah023pc_0m
_cod_database_code               7154192
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.022) H3(0.022) H4(0.021) H5(0.022) H6(0.025) H7(0.024)
 H8(0.023) H9A(0.029) H9B(0.029) H11(0.042) H12(0.058) H13(0.064) H14(0.07)
 H15(0.049) H16A(0.029) H16B(0.029) H17A(0.034) H17B(0.034) H19(0.037)
 H20(0.044) H21(0.049) H22(0.046) H23(0.038) H24A(0.032) H24B(0.032) H26(0.033)
 H27(0.04) H28(0.044) H29(0.041) H30(0.034) H31A(0.031) H31B(0.031) H33(0.047)
 H34(0.054) H35(0.055) H36(0.071) H37(0.056) H38(0.022) H39(0.025) H40(0.028)
 H41(0.026) H42(0.023) H43A(0.033) H43B(0.033) H45(0.032) H46(0.039) H47(0.042)
 H48(0.041) H49(0.032) H50A(0.034) H50B(0.034) H51A(0.041) H51B(0.041)
 H53(0.038) H54(0.04) H55(0.038) H56(0.034) H57(0.032) H58A(0.035) H58B(0.035)
 H60(0.035) H61(0.04) H62(0.044) H63(0.048) H64(0.04) H65A(0.031) H65B(0.031)
 H67(0.034) H68(0.041) H69(0.044) H70(0.042) H71(0.033) H72(0.025) H73(0.026)
 H74A(0.031) H74B(0.031) H75A(0.036) H75B(0.036) H76(0.029) H77(0.028)
 H78A(0.033) H78B(0.033) H79A(0.03) H79B(0.03)
 Fixed X: H2(0.9562) H3(0.8038) H4(1.0803) H5(1.0711) H6(1.2188) H7(1.2501)
 H8(1.1161) H9A(1.0285) H9B(0.9425) H11(1.0624) H12(1.1331) H13(1.167)
 H14(1.1313) H15(1.0609) H16A(1.3673) H16B(1.3335) H17A(1.4489) H17B(1.4448)
 H19(1.3063) H20(1.314) H21(1.4291) H22(1.5394) H23(1.5314) H24A(1.3842)
 H24B(1.3144) H26(1.3522) H27(1.4368) H28(1.5345) H29(1.5482) H30(1.4644)
 H31A(1.0362) H31B(1.0582) H33(1.1957) H34(1.2957) H35(1.3031) H36(1.214)
 H37(1.1168) H38(0.7766) H39(0.703) H40(0.5534) H41(0.632) H42(0.6666)
 H43A(0.7954) H43B(0.7002) H45(0.9043) H46(0.9465) H47(0.8566) H48(0.7231)
 H49(0.6814) H50A(0.47) H50B(0.5419) H51A(0.3799) H51B(0.4516) H53(0.2576)
 H54(0.1582) H55(0.1852) H56(0.3115) H57(0.411) H58A(0.5539) H58B(0.5787)
 H60(0.3813) H61(0.2385) H62(0.2129) H63(0.3322) H64(0.4768) H65A(0.8156)
 H65B(0.7215) H67(0.6137) H68(0.6013) H69(0.7196) H70(0.8531) H71(0.8669)
 H72(0.9826) H73(0.8387) H74A(0.8616) H74B(0.7685) H75A(0.7666) H75B(0.8147)
 H76(0.8902) H77(1.0298) H78A(0.9762) H78B(1.0768) H79A(1.0927) H79B(1.0251)
 Fixed Y: H2(0.5738) H3(0.6242) H4(0.731) H5(0.5509) H6(0.535) H7(0.7128)
 H8(0.6282) H9A(0.4777) H9B(0.5111) H11(0.6396) H12(0.6253) H13(0.4929)
 H14(0.3739) H15(0.388) H16A(0.5789) H16B(0.6427) H17A(0.5568) H17B(0.4757)
 H19(0.4914) H20(0.4046) H21(0.3079) H22(0.3011) H23(0.3866) H24A(0.7125)
 H24B(0.7494) H26(0.5425) H27(0.4906) H28(0.5783) H29(0.7183) H30(0.771)
 H31A(0.7942) H31B(0.6969) H33(0.6602) H34(0.6979) H35(0.8363) H36(0.9369)
 H37(0.9004) H38(0.8356) H39(0.75) H40(0.7778) H41(0.8528) H42(0.6874)
 H43A(0.9029) H43B(0.8625) H45(0.7501) H46(0.6402) H47(0.6044) H48(0.674)
 H49(0.7836) H50A(0.8861) H50B(0.9514) H51A(0.977) H51B(1.0263) H53(0.8989)
 H54(0.9054) H55(0.9955) H56(1.0812) H57(1.0745) H58A(0.8444) H58B(0.7486)
 H60(0.8521) H61(0.8272) H62(0.731) H63(0.6624) H64(0.6856) H65A(0.6358)
 H65B(0.5934) H67(0.5707) H68(0.5289) H69(0.546) H70(0.6018) H71(0.6435)
 H72(0.7492) H73(0.7753) H74A(0.9117) H74B(0.8787) H75A(0.9718) H75B(1.0259)
 H76(1.0301) H77(1.0141) H78A(0.9776) H78B(0.9852) H79A(0.8468) H79B(0.849)
 Fixed Z: H2(0.7475) H3(0.7338) H4(0.8203) H5(0.8109) H6(0.7989) H7(0.7932)
 H8(0.7384) H9A(0.8679) H9B(0.8952) H11(0.9502) H12(1.0231) H13(1.0524)
 H14(1.0083) H15(0.9351) H16A(0.8131) H16B(0.8531) H17A(0.8898) H17B(0.8563)
 H19(0.9583) H20(1.0235) H21(1.032) H22(0.9739) H23(0.9072) H24A(0.7523)
 H24B(0.7147) H26(0.6884) H27(0.6259) H28(0.5849) H29(0.6077) H30(0.6705)
 H31A(0.6933) H31B(0.6845) H33(0.6394) H34(0.5805) H35(0.5551) H36(0.5894)
 H37(0.6504) H38(0.7899) H39(0.7092) H40(0.7417) H41(0.8253) H42(0.7866)
 H43A(0.6376) H43B(0.6479) H45(0.6539) H46(0.6041) H47(0.5396) H48(0.5275)
 H49(0.577) H50A(0.7879) H50B(0.768) H51A(0.6843) H51B(0.7153) H53(0.7291)
 H54(0.7919) H55(0.8551) H56(0.8556) H57(0.792) H58A(0.8875) H58B(0.8991)
 H60(0.8556) H61(0.883) H62(0.9435) H63(0.9789) H64(0.9509) H65A(0.8475)
 H65B(0.8358) H67(0.9032) H68(0.9814) H69(1.0334) H70(1.0061) H71(0.9274)
 H72(0.8904) H73(0.8843) H74A(0.943) H74B(0.923) H75A(0.8632) H75B(0.9035)
 H76(0.825) H77(0.8451) H78A(0.9363) H78B(0.9188) H79A(0.9102) H79B(0.9538)
;
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'