Photo- and dioxygen-enabled radical C(sp<sup>3</sup>)-N(sp<sup>2</sup>) cross-coupling between guanidines and perfluoroalkyl iodides.
Liu, Shulin; Wang, Rui; Zhu, Bo; Guan, Wei; Liang, Fushun; Organic & biomolecular chemistry 17 (2019) 8695–8700; doi:10.1039/c9ob01520e

data_7157065
_publ_section_title
;
 Photo- and dioxygen-enabled radical C(sp<sup>3</sup>)-N(sp<sup>2</sup>)
 cross-coupling between guanidines and perfluoroalkyl iodides.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8695
_journal_page_last               8700
_journal_paper_doi               10.1039/c9ob01520e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C7 H8 F7 N3 O'
_chemical_formula_sum            'C7 H8 F7 N3 O'
_chemical_formula_weight         283.16
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-05-06 deposited with the CCDC.    2019-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.87(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.986(18)
_cell_length_b                   9.949(16)
_cell_length_c                   10.414(17)
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1125(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      293
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8201
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.645
_diffrn_reflns_theta_min         3.239
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.180
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1485
_refine_ls_R_factor_gt           0.0681
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.2164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1213
_reflns_number_total             2594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01520e2.cif
_cod_data_source_block           test
_cod_depositor_comments
'Adding full bibliography for 7157064--7157065.cif.'
_cod_database_code               7157065
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(F6A)=1-FVAR(1)
 Sof(F6)=FVAR(1)
3.a X=CH2 refined with riding coordinates:
 N2(H2D,H2E)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_shelx_res_checksum              95789
_olex2_submission_special_instructions 'No special instructions were received'