Reactions between N-Heterocyclic Carbene and Lutetium-Metallofullerenes: High Regioselectivity Directed by Electronic Effect in Addition to Steric Hindrance.
Shen, Wangqiang; Yang, Le; Wu, Yongbo; Bao, Lipiao; Li, Ying; Jin, Peng; Fang, Hongyun; Xie, Yunpeng; Lu, Xing; The Journal of organic chemistry 84 (2019) 606–612; doi:10.1021/acs.joc.8b02423

data_4035951
_publ_section_title
;
 Reactions between N-Heterocyclic Carbene and Lutetium-Metallofullerenes:
 High Regioselectivity Directed by Electronic Effect in Addition to Steric
 Hindrance.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              606
_journal_page_last               612
_journal_paper_doi               10.1021/acs.joc.8b02423
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C101 H24 Lu3 N3 O, C S2'
_chemical_formula_sum            'C102 H24 Lu3 N3 O S2'
_chemical_formula_weight         1896.27
_chemical_name_common            Me+O-NHC
_chemical_name_systematic        Me+O-NHC
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.423(3)
_cell_length_b                   15.6051(15)
_cell_length_c                   28.953(3)
_cell_measurement_reflns_used    9397
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.518
_cell_measurement_theta_min      2.966
_cell_volume                     11486(2)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'Apex2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL XT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            126856
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.369
_diffrn_reflns_theta_min         2.954
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.261
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.193
_exptl_crystal_description       block
_exptl_crystal_F_000             7280
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         4.900
_refine_diff_density_min         -4.448
_refine_diff_density_rms         0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1069
_refine_ls_number_reflns         10357
_refine_ls_number_restraints     744
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0789
_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^)+(0.0378P)^2^+353.8770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8968
_reflns_number_total             10357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02423_si_005.cif
_cod_data_source_block           Me+O-NHC
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        11487(2)
_cod_database_code               4035951
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.559
_shelx_estimated_absorpt_t_max   0.674
_shelx_res_checksum              61434
_shelx_hkl_checksum              5128
_shelx_fab_checksum              63049