A soluble iron(II)-phthalocyanine-catalyzed intramolecular C(sp<sup>3</sup>)-H amination with alkyl azides.
You, Tingjie; Zeng, Si-Hao; Fan, Jianqiang; Wu, Liangliang; Kang, Fangyuan; Liu, Yungen; Che, Chi-Ming; Chemical communications (Cambridge, England) 57 (2021) 10711–10714; doi:10.1039/d1cc04573c

data_7129004
_publ_section_title
;
 A soluble iron(II)-phthalocyanine-catalyzed intramolecular
 C(sp<sup>3</sup>)-H amination with alkyl azides.
;
_journal_issue                   82
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10711
_journal_page_last               10714
_journal_paper_doi               10.1039/d1cc04573c
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H13 F6 N5 O'
_chemical_formula_sum            'C16 H13 F6 N5 O'
_chemical_formula_weight         405.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-09 deposited with the CCDC.	2021-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.094(2)
_cell_length_b                   6.5624(5)
_cell_length_c                   9.4316(7)
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.30
_cell_volume                     1615.1(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13312
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         2.159
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0718 before and 0.0541 after correction. The Ratio of minimum to maximum transmission is 0.9490. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.905
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0525P)^2^+1.3683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1117
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3459
_reflns_number_total             3691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04573c2.cif
_cod_data_source_block           cxy0823
_cod_depositor_comments
'Adding full bibliography for 7129004--7129005.cif.'
_cod_database_code               7129004
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F3) = Uanis(F3A)
Uanis(F7) = Uanis(F7A)
3. Others
 Sof(H8)=Sof(H16)=Sof(F3A)=Sof(F7A)=1-FVAR(1)
 Sof(F3)=Sof(F7)=Sof(H9)=Sof(H15)=FVAR(1)
4.a Riding coordinates:
 N2(H2)
4.b Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
4.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B)
4.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C15(H15), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'