Unexpected Formation of 1,2- and 1,4-Bismethoxyl Sc3N@Ih-C80 Derivatives via Regioselective Anion Addition: Unambiguous Structural Identification and Mechanism Study
Hu, Yajing; Yao, Yang-Rong; Liu, Xuechen; Yu, Ao; Xie, Xiao-Ming; Abella, Laura; Rodriguez-Fortea, Antonio; Poblet, Josep M.; Akasaka, Takeshi; Peng, Ping; Zhang, Qianyan; Xie, Su-Yuan; Li, Fang-Fang; Lu, Xing; Chemical Science  (2021) –; doi:10.1039/D1SC01178B

data_1562372
_publ_section_title
;
 Unexpected Formation of 1,2- and 1,4-Bismethoxyl Sc3N@Ih-C80 Derivatives
 via Regioselective Anion Addition: Unambiguous Structural Identification
 and Mechanism Study
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01178B
_journal_year                    2021
_chemical_formula_moiety         'C14 H8 O2'
_chemical_formula_sum            'C14 H8 O2'
_chemical_formula_weight         208.20
_chemical_name_common            Anthraquinone
_chemical_name_systematic        9,10-Anthracenedione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-03-31
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.664(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8728(7)
_cell_length_b                   3.9608(5)
_cell_length_c                   15.7845(19)
_cell_measurement_reflns_used    409
_cell_measurement_temperature    268
_cell_measurement_theta_max      28.9223
_cell_measurement_theta_min      3.3035
_cell_volume                     480.23(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_diffrn_ambient_temperature      268.00(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_details
;
  1 omega  -93.00  -35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.8710 -178.0000  120.0000 58

  2 omega   -1.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835   57.0000  120.0000 88

  3 omega  -48.00   40.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6835  -57.0000  -30.0000 88
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2169
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.874
_diffrn_reflns_theta_min         3.310
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0547
_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^)+(0.0684P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1601
_reflns_Friedel_coverage         0.000
_reflns_number_gt                602
_reflns_number_total             1078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01178b2.cif
_cod_data_source_block           anthraquinone-268k
_cod_database_code               1562372
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C4(H4)
;
_shelx_res_checksum              56562
_shelx_hkl_checksum              84680
_olex2_submission_special_instructions 'No special instructions were received'