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_4135415
_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         'C27 H22 F17 N3 O2 S, 0.91(C H Cl3)'
_chemical_formula_sum            'C27.9 H22.9 Cl2.72 F17 N3 O2 S'
_chemical_formula_weight         883.65
_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             2019-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.5370(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.9093(7)
_cell_length_b                   6.11090(10)
_cell_length_c                   19.8414(4)
_cell_measurement_reflns_used    9169
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      77.29
_cell_measurement_theta_min      4.48
_cell_volume                     3393.00(12)
_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      120.06
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_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  0.0631
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29720
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.166
_diffrn_reflns_theta_min         3.158
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.013
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1085 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.8570.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_description       needle
_exptl_crystal_F_000             1770
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     659
_refine_ls_number_reflns         7129
_refine_ls_number_restraints     1740
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0505P)^2^+3.4551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5493
_reflns_number_total             7129
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09403_si_008.cif
_cod_data_source_block           H
_cod_depositor_comments
'Adding full bibliography for 4135411--4135418.cif.'
_cod_original_formula_sum        'C27.90 H22.90 Cl2.72 F17 N3 O2 S'
_cod_database_code               4135415
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.584
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F27-C26 \\sim F28-C26 \\sim F30A-C29 \\sim F30B-C29 \\sim F31A-C29 \\sim
F31B-C29 \\sim F34B-C32B ~
 F34A-C32A \\sim F33B-C32B \\sim F33A-C32A \\sim F36A-C35A \\sim F36B-C35B
\\sim F37A-C35A \\sim F37B-
 C35B \\sim F39B-C38B \\sim F40B-C38B \\sim F39A-C38A \\sim F40A-C38A \\sim
F43A-C41A \\sim F42B-C41B ~
 F42A-C41A \\sim F43B-C41B \\sim F46B-C44B \\sim F45B-C44B \\sim F45A-C44A
\\sim F46A-C44A \\sim F50B-
 C47B \\sim F48B-C47B \\sim F48A-C47A \\sim F49A-C47A \\sim F49B-C47B \\sim
F50A-C47A
 with sigma of 0.02
 C29-C26 \\sim C35A-C32A \\sim C35B-C32B \\sim C38B-C35B \\sim C38A-C35A \\sim
C41B-C38B \\sim C41A-
 C38A \\sim C44B-C41B \\sim C44A-C41A \\sim C47B-C44B \\sim C47A-C44A
 with sigma of 0.02
 C32A-C29 \\sim C32B-C29
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C26 \\sim F27 \\sim F28 \\sim C29 \\sim F30A \\sim F31A \\sim C32A \\sim F33A
\\sim F34A \\sim C35A \\sim F36A \\sim F37A \\sim C38A \\sim F39A \\sim F40A
\\sim C41A \\sim F42A \\sim F43A \\sim C44A \\sim F45A \\sim F46A \\sim C47A
\\sim F48A \\sim F49A \\sim F50A \\sim F30B \\sim F31B \\sim C32B \\sim F33B
\\sim F34B \\sim C35B \\sim F36B \\sim F37B \\sim C38B \\sim F39B \\sim F40B
\\sim C41B \\sim F42B \\sim F43B \\sim C44B \\sim F45B \\sim F46B \\sim C47B
\\sim F48B \\sim F49B \\sim F50B: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(F40B) = Uanis(F39A)
Uanis(C32A) = Uanis(C32B)
Uanis(F42B) = Uanis(F43A)
Uanis(C35B) = Uanis(C35A)
4. Rigid body (RIGU) restrains
 C26, F27, F28, C29, F30A, F31A, C32A, F33A, F34A, C35A, F36A, F37A, C38A,
 F39A, F40A, C41A, F42A, F43A, C44A, F45A, F46A, C47A, F48A, F49A, F50A, F30B,
 F31B, C32B, F33B, F34B, C35B, F36B, F37B, C38B, F39B, F40B, C41B, F42B, F43B,
 C44B, F45B, F46B, C47B, F48B, F49B, F50B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{F30A, F31A, C32A, F33A, F34A, C35A, F36A, F37A, C38A, F39A, F40A, C41A, F42A,
F43A, C44A, F45A, F46A, C47A, F48A, F49A, F50A} sigma for 1-2: 0.01, 1-3: 0.02
as
{F30B, F31B, C32B, F33B, F34B, C35B, F36B, F37B, C38B, F39B, F40B, C41B, F42B,
F43B, C44B, F45B, F46B, C47B, F48B, F49B, F50B}
6. Others
 Sof(F30B)=Sof(F31B)=Sof(C32B)=Sof(F33B)=Sof(F34B)=Sof(C35B)=Sof(F36B)=
 Sof(F37B)=Sof(C38B)=Sof(F39B)=Sof(F40B)=Sof(C41B)=Sof(F42B)=Sof(F43B)=
 Sof(C44B)=Sof(F45B)=Sof(F46B)=Sof(C47B)=Sof(F48B)=Sof(F49B)=Sof(F50B)=1-FVAR(1)
 Sof(F30A)=Sof(F31A)=Sof(C32A)=Sof(F33A)=Sof(F34A)=Sof(C35A)=Sof(F36A)=
 Sof(F37A)=Sof(C38A)=Sof(F39A)=Sof(F40A)=Sof(C41A)=Sof(F42A)=Sof(F43A)=
 Sof(C44A)=Sof(F45A)=Sof(F46A)=Sof(C47A)=Sof(F48A)=Sof(F49A)=Sof(F50A)=FVAR(1)
 Sof(C51)=Sof(H51)=Sof(Cl52)=Sof(Cl53)=Sof(Cl54)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C14(H14), C51(H51)
7.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B)
7.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C21(H21), C22(H22), C23(H23), C24(H24),
 C25(H25)
7.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              23082
_shelx_hkl_checksum              22502
_olex2_submission_special_instructions 'No special instructions were received'