Photocatalytic (3 + 2) dipolar cycloadditions of aziridines driven by visible-light.
Mazzarella, Daniele; Bortolato, Tommaso; Pelosi, Giorgio; Dell'Amico, Luca; Chemical science 15 (2023) 271–277; doi:10.1039/d3sc05997a

data_1570430
_publ_section_title
;
 Photocatalytic (3 + 2) dipolar cycloadditions of aziridines driven by
 visible-light.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              271
_journal_page_last               277
_journal_paper_doi               10.1039/d3sc05997a
_journal_volume                  15
_journal_year                    2023
_chemical_formula_moiety         'C28 H20 F5 N O, C2 H3 N'
_chemical_formula_sum            'C30 H23 F5 N2 O'
_chemical_formula_weight         522.50
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-31 deposited with the CCDC.	2023-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.6350(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5292(2)
_cell_length_b                   12.5977(2)
_cell_length_c                   20.0573(4)
_cell_measurement_reflns_used    5440
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      63.028
_cell_measurement_theta_min      4.178
_cell_volume                     2585.49(8)
_computing_cell_refinement       SHELXT
_computing_data_reduction        SHELXT
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21770
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.540
_diffrn_reflns_theta_min         4.178
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1223 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.6263.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5100
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0733
_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^)+(0.1163P)^2^+0.5541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1918
_refine_ls_wR_factor_ref         0.2363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2762
_reflns_number_total             5100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05997a2.cif
_cod_data_source_block           cu_tbr4ss_0m
_cod_depositor_comments
'Adding full bibliography for 1570429--1570431.cif.'
_cod_database_code               1570430
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.773
_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
 N5-C6 = N1-C2
 1.1 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C0: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
4. Others
 Fixed Sof: C0(0.5) H0A(0.5) H0B(0.5) H0C(0.5) N1(0.5) C2(0.5) C3(0.5)
 H3A(0.5) H3B(0.5) H3C(0.5) N5(0.5) C6(0.5)
5.a Ternary CH refined with riding coordinates:
 C008(H008), C00D(H00D), C00F(H00F)
5.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B)
5.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00K(H00K), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z)
5.d Idealised Me refined as rotating group:
 C0(H0A,H0B,H0C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              82046
_olex2_exptl_crystal_mounting_method Cryoloop
_olex2_submission_special_instructions 'No special instructions were received'