Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents.
Chandrachud, Preeti P.; Wojtas, Lukasz; Lopchuk, Justin M.; Journal of the American Chemical Society 142 (2020) 21743–21750; doi:10.1021/jacs.0c09403

data_4135417
_publ_section_title
;
 Decarboxylative Amination: Diazirines as Single and Double Electrophilic
 Nitrogen Transfer Reagents.
;
_journal_issue                   52
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              21743
_journal_page_last               21750
_journal_paper_doi               10.1021/jacs.0c09403
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C24 H17 F17 N2'
_chemical_formula_sum            'C24 H17 F17 N2'
_chemical_formula_weight         656.40
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.217(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.7462(10)
_cell_length_b                   8.7463(4)
_cell_length_c                   11.8850(5)
_cell_measurement_reflns_used    9767
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.55
_cell_measurement_theta_min      3.61
_cell_volume                     2545.95(19)
_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)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            43108
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.453
_diffrn_reflns_theta_min         3.609
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.725
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0932 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.9267.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     1482
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+1.1190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4645
_reflns_number_total             5408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09403_si_005.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4135411--4135418.cif.'
_cod_database_code               4135417
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.846
_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. Restrained distances
 N11B-N10 \\sim N11A-N10
 with sigma of 0.02
 N10-C12B \\sim N10-C12A
 with sigma of 0.02
 N11A-H11A \\sim N11B-H11B
 with sigma of 0.02
 N10-H11B \\sim H11B-C12B
 with sigma of 0.02
3. Restrained planarity
 C13B, C14B, C15B, C16B, C17B, C18B
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
C9 \\sim N10 \\sim N11A \\sim C12A \\sim C13A \\sim C14A \\sim C15A \\sim C16A
\\sim C17A \\sim C18A \\sim C19A \\sim F20A \\sim F21A \\sim C22A \\sim F23A
\\sim F24A \\sim C25A \\sim F26A \\sim F27A \\sim C28A \\sim F29A \\sim F30A
\\sim C31A \\sim F32A \\sim F33A \\sim C34A \\sim F35A \\sim F36A \\sim C37A
\\sim F38A \\sim F39A \\sim C40A \\sim F41A \\sim F42A \\sim F43A \\sim N11B
\\sim C12B \\sim C13B \\sim C14B \\sim C15B \\sim C16B \\sim C17B \\sim C18B
\\sim C19B \\sim F20B \\sim F21B \\sim C22B \\sim F23B \\sim F24B \\sim C25B
\\sim F26B \\sim F27B \\sim C28B \\sim F29B \\sim F30B \\sim C31B \\sim F32B
\\sim F33B \\sim C34B \\sim F35B \\sim F36B \\sim C37B \\sim F38B \\sim F39B
\\sim C40B \\sim F41B \\sim F42B \\sim F43B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(C12A) = Uanis(C12B)
Uanis(C37A) = Uanis(C37B)
Uanis(C25A) = Uanis(C25B)
Uanis(C28B) = Uanis(C28A)
Uanis(C34B) = Uanis(C34A)
Uanis(C40B) = Uanis(C40A)
Uanis(F35A) = Uanis(F35B)
Uanis(F36B) = Uanis(F36A)
Uanis(F29A) = Uanis(F29B)
Uanis(F20A) = Uanis(F20B)
Uanis(C31A) = Uanis(C31B)
Uanis(C13A) = Uanis(C13B)
Uanis(C15B) = Uanis(C15A)
Uanis(C16A) = Uanis(C16B)
Uanis(C17B) = Uanis(C17A)
5. Rigid body (RIGU) restrains
 N11B, H11B, C12B, C13B, C14B, H14B, C15B, H15B, C16B, H16B, C17B, H17B, C18B,
 H18B, C19B, F20B, F21B, C22B, F23B, F24B, C25B, F26B, F27B, C28B, F29B, F30B,
 C31B, F32B, F33B, C34B, F35B, F36B, C37B, F38B, F39B, C40B, F41B, F42B, F43B,
 N10, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{N11A, C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A, F20A, F21A, C22A, F23A,
F24A, C25A, F26A, F27A, C28A, F29A, F30A, C31A, F32A, F33A, C34A, F35A, F36A,
C37A, F38A, F39A, C40A, F41A, F42A, F43A} sigma for 1-2: 0.01, 1-3: 0.02
as
{N11B, C12B, C13B, C14B, C15B, C16B, C17B, C18B, C19B, F20B, F21B, C22B, F23B,
F24B, C25B, F26B, F27B, C28B, F29B, F30B, C31B, F32B, F33B, C34B, F35B, F36B,
C37B, F38B, F39B, C40B, F41B, F42B, F43B}
7. Others
 Sof(N11B)=Sof(H11B)=Sof(C12B)=Sof(C13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=
 Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18B)=
 Sof(C19B)=Sof(F20B)=Sof(F21B)=Sof(C22B)=Sof(F23B)=Sof(F24B)=Sof(C25B)=
 Sof(F26B)=Sof(F27B)=Sof(C28B)=Sof(F29B)=Sof(F30B)=Sof(C31B)=Sof(F32B)=
 Sof(F33B)=Sof(C34B)=Sof(F35B)=Sof(F36B)=Sof(C37B)=Sof(F38B)=Sof(F39B)=
 Sof(C40B)=Sof(F41B)=Sof(F42B)=Sof(F43B)=1-FVAR(1)
 Sof(N11A)=Sof(H11A)=Sof(C12A)=Sof(C13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=Sof(F20A)=Sof(F21A)=Sof(C22A)=Sof(F23A)=Sof(F24A)=Sof(C25A)=
 Sof(F26A)=Sof(F27A)=Sof(C28A)=Sof(F29A)=Sof(F30A)=Sof(C31A)=Sof(F32A)=
 Sof(F33A)=Sof(C34A)=Sof(F35A)=Sof(F36A)=Sof(C37A)=Sof(F38A)=Sof(F39A)=
 Sof(C40A)=Sof(F41A)=Sof(F42A)=Sof(F43A)=FVAR(1)
8.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
8.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14A(H14A), C15A(H15A), C16A(H16A),
 C17A(H17A), C18A(H18A), C14B(H14B), C15B(H15B), C16B(H16B), C17B(H17B),
 C18B(H18B)
;
_shelx_res_checksum              23196
_shelx_hkl_checksum              12574
_olex2_submission_special_instructions 'No special instructions were received'