<i>N</i>-Benzylhydroxylamine as a novel synthetic block in "C1N1" embedding reaction <i>via</i> α-C(sp<sup>3</sup>)-H activation strategy.
Tang, Yong-Xing; Zhou, You; Wu, Hao-Xuan; Wang, Li-Sheng; Wu, Chun-Yan; Zhuang, Shi-Yi; Wu, An-Xin; Chemical communications (Cambridge, England) 60 (2024) 7180–7183; doi:10.1039/d4cc02105c

data_7133200
_publ_section_title
;
 <i>N</i>-Benzylhydroxylamine as a novel synthetic block in "C1N1"
 embedding reaction <i>via</i> &#x3b1;-C(sp<sup>3</sup>)-H activation
 strategy.
;
_journal_issue                   56
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7180
_journal_page_last               7183
_journal_paper_doi               10.1039/d4cc02105c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C22 H18 Cl N2, C2 H F3 O2, C2 F3 O2'
_chemical_formula_sum            'C26 H19 Cl F6 N2 O4'
_chemical_formula_weight         572.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-08
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2024-03-22 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.652(3)
_cell_length_b                   14.997(2)
_cell_length_c                   21.130(3)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.28
_cell_volume                     5276.8(14)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34374
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.066
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0043(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         4625
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0611
_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^)+(0.0898P)^2^+4.1136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1894
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3441
_reflns_number_total             4625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02105c2.cif
_cod_data_source_block           y
_cod_depositor_comments
'Adding full bibliography for 7133200--7133201.cif.'
_cod_original_cell_volume        5277.0(14)
_cod_database_code               7133200
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2. Restrained distances 
 F3-C23 \\sim F3A-C23 
 with sigma of 0.02 
 F1-C23 \\sim F1A-C23 
 with sigma of 0.02 
 C23-F2 \\sim C23-F2A 
 with sigma of 0.02 
 F6-C25 \\sim F6A-C25 
 with sigma of 0.02 
 F4-C25 \\sim F4A-C25 
 with sigma of 0.02 
 F5-C25 \\sim F5A-C25 
 with sigma of 0.02 
3. Uiso/Uaniso restraints and constraints 
Uanis(F6) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6A) \\sim 
Ueq, Uanis(F4A) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) 
\\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A) \\sim Ueq, 
Uanis(F3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02 
Uanis(F3) = Uanis(F2A) 
4. Others 
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1) 
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1) 
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(2) 
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2) 
5.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14), 
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), N2(H2A) 
5.b Idealised Me refined as rotating group: 
 C16(H16A,H16B,H16C) 
5.c Idealised tetrahedral OH refined as rotating group: 
 O1(H1) 
;
_olex2_submission_special_instructions 'No special instructions were received'