Heteropolyacid catalyzed O-alkylation of oximes with alcohols via a carbocation in dimethyl carbonate and mechanism insight
Zhuang, Hongfeng; Hou, Qin; Han, Feng; Lv, Haotian; Miao, Chengxia; Green Chemistry 25 (2023) 310–317; doi:10.1039/D2GC03214G

data_7245956
_publ_section_title
;
 Heteropolyacid catalyzed O-alkylation of oximes with alcohols via a
 carbocation in dimethyl carbonate and mechanism insight
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              310
_journal_page_last               317
_journal_paper_doi               10.1039/D2GC03214G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C38 H29 N O'
_chemical_formula_sum            'C38 H29 N O'
_chemical_formula_weight         515.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_block_doi                 10.5517/ccdc.csd.cc2cm78j
_audit_creation_date             2022-07-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2022-07-28 deposited with the CCDC.	2022-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.053(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7566(10)
_cell_length_b                   23.006(2)
_cell_length_c                   13.3290(13)
_cell_measurement_reflns_used    4153
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.899
_cell_measurement_theta_min      2.272
_cell_volume                     2827.9(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9750
_diffrn_measured_fraction_theta_max 0.9741
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16981
_diffrn_reflns_theta_full        27.5365
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0868 before and 0.0402 after correction.
The Ratio of minimum to maximum transmission is 0.9328.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.2111
_exptl_crystal_description       columnar
_exptl_crystal_F_000             1088.4484
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.2667
_refine_diff_density_min         -0.2783
_refine_diff_density_rms         0.0623
_refine_ls_d_res_high            0.7687
_refine_ls_d_res_low             7.1953
_refine_ls_goodness_of_fit_ref   1.0678
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    58
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0678
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.3626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -12
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -7
_reflns_number_gt                3925
_reflns_number_total             6365
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2gc03214g2.cif
_cod_data_source_block           220106ZLL2_0m
_cod_depositor_comments          'Adding full bibliography for 7245956.cif.'
_cod_original_cell_volume        2828.0(5)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7245956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C011(H011), C012(H012), C013(H013), C014(H014)
;
_olex2_submission_special_instructions 'No special instructions were received'