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_7129005
_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      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-14
_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                98.838(6)
_cell_angle_beta                 91.269(6)
_cell_angle_gamma                93.319(6)
_cell_formula_units_Z            1
_cell_length_a                   4.6849(8)
_cell_length_b                   5.6677(10)
_cell_length_c                   15.258(3)
_cell_measurement_reflns_used    4848
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.70
_cell_volume                     399.46(13)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6666
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_min         2.703
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1568 before and 0.0786 after correction. The Ratio of minimum to maximum transmission is 0.7051. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_description       block
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0273P)^2^+0.0730P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0949
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.914
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                3100
_reflns_number_total             3455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04573c2.cif
_cod_data_source_block           cxy0884_0m
_cod_depositor_comments
'Adding full bibliography for 7129004--7129005.cif.'
_cod_original_cell_volume        399.46(12)
_cod_database_code               7129005
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.957
_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.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C14(H14A,H14B), C17(H17A,H17B), C18(H18A,H18B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'