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_1570431
_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_absolute_configuration syn
_chemical_formula_moiety
'0.25(C33 H31 N2 O2), 0.25(C32.999 H29.52 N2 O2), 0.5(C33 H30 N2 O2)'
_chemical_formula_sum            'C33 H30.13 N2 O2'
_chemical_formula_weight         486.72
_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   geom
_audit_creation_date             2023-10-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2023-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                96.793(5)
_cell_angle_beta                 95.640(7)
_cell_angle_gamma                99.888(5)
_cell_formula_units_Z            4
_cell_length_a                   6.8195(6)
_cell_length_b                   19.5313(9)
_cell_length_c                   20.5319(17)
_cell_measurement_reflns_used    3340
_cell_measurement_temperature    200.15
_cell_measurement_theta_max      61.528
_cell_measurement_theta_min      2.183
_cell_volume                     2655.5(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_diffrn_ambient_temperature      200.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1418
_diffrn_reflns_av_unetI/netI     0.1249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            58286
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.070
_diffrn_reflns_theta_min         2.183
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1393 before and 0.0846 after correction.
The Ratio of minimum to maximum transmission is 0.7841.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       needle
_exptl_crystal_F_000             1033
_exptl_crystal_size_max          .02
_exptl_crystal_size_mid          .01
_exptl_crystal_size_min          .01
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 1915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1481
_refine_ls_number_reflns         19166
_refine_ls_number_restraints     849
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.2066
_refine_ls_R_factor_gt           0.1264
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3063
_refine_ls_wR_factor_ref         0.3943
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                8169
_reflns_number_total             19166
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05997a2.cif
_cod_data_source_block           cu_dm2_c3_rd
_cod_depositor_comments
'Adding full bibliography for 1570429--1570431.cif.'
_cod_original_cell_volume        2655.5(3)
_cod_database_code               1570431
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H02H,H02A,H02B} of C02H, All C(H,H) groups, All C(H,H,H,
  H) groups
 At 1.5 times of:
  {H03E,H03G,H03I} of C03J, {H02C,H02D,H02E} of C02V, {H03A,H03B,H03C} of
  C036, {H02V,H02X,H02Y} of C02X
2. Uiso/Uaniso restraints and constraints
O003 \\sim C00K \\sim C00A \\sim N00L \\sim C00G \\sim C00O \\sim C01D \\sim
C02H \\sim C023 \\sim N008 \\sim C030 \\sim C13 \\sim O00M \\sim C02D \\sim
C010 \\sim C01L \\sim C03F \\sim C03K \\sim C12 \\sim C14 \\sim C02Z \\sim C3
\\sim C10 \\sim C00X \\sim C01M \\sim C036 \\sim C00J \\sim C9 \\sim C03X \\sim
C01I \\sim C17 \\sim C20 \\sim C02Q \\sim C041 \\sim C042 \\sim C00Z \\sim C02O
\\sim C033 \\sim C02F \\sim C0 \\sim C8 \\sim C02U \\sim C16 \\sim C028 \\sim
C02T \\sim C03U \\sim C03B \\sim C5 \\sim C7 \\sim C021 \\sim C6: within 1.7A
with sigma of 0.004 and sigma for terminal atoms of 0.008 within 1.7A
C21 \\sim C18 \\sim C15 \\sim C4 \\sim C22 \\sim C19 \\sim C21A \\sim C19A
\\sim C4A \\sim C15A \\sim C18A \\sim C22A: within 1.7A with sigma of 0.004 and
sigma for terminal atoms of 0.008 within 1.7A
C032 \\sim C03D \\sim C03O \\sim C03I \\sim C03E \\sim C03Z: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008 within 1.7A
C03R \\sim C038 \\sim C03P \\sim C03T \\sim C02Y \\sim C01B: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008 within 1.7A
C02I \\sim C11 \\sim C037 \\sim C02K \\sim C03Y \\sim C1: within 1.7A with
sigma of 0.004 and sigma for terminal atoms of 0.008 within 1.7A
C2 \\sim C1C \\sim C1D \\sim C11A \\sim C1B \\sim C26: within 1.7A with sigma
of 0.004 and sigma for terminal atoms of 0.008 within 1.7A
3. Others
 Sof(H01A)=Sof(C5)=Sof(H5)=Sof(C0)=Sof(H0)=Sof(C9)=Sof(C8)=Sof(H8)=Sof(C7)=
 Sof(H7)=Sof(C6)=Sof(H6)=1-FVAR(1)
 Sof(H01L)=Sof(C03U)=Sof(H03U)=Sof(C033)=Sof(H033)=Sof(C00J)=Sof(C02F)=
 Sof(H02F)=Sof(C03B)=Sof(H03D)=Sof(C021)=Sof(H021)=FVAR(1)
 Sof(H00B)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C20)=Sof(H20)=
 Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=1-FVAR(2)
 Sof(H00O)=Sof(C03F)=Sof(H03F)=Sof(C03X)=Sof(H03X)=Sof(C02U)=Sof(H02U)=
 Sof(C01I)=Sof(H01I)=Sof(C03K)=Sof(H03K)=Sof(C030)=FVAR(2)
 Sof(H00C)=Sof(C21A)=Sof(H21A)=Sof(C19A)=Sof(H19A)=Sof(C22A)=Sof(C4A)=Sof(H4A)=
 Sof(C15A)=Sof(H15A)=Sof(C18A)=Sof(H18A)=1-FVAR(3)
 Sof(H00Q)=Sof(C21)=Sof(H21)=Sof(C18)=Sof(H18)=Sof(C15)=Sof(H15)=Sof(C4)=
 Sof(H4)=Sof(C22)=Sof(C19)=Sof(H19)=FVAR(3)
 Sof(H02H)=Sof(C041)=Sof(H041)=Sof(C3)=Sof(H3)=Sof(C02D)=Sof(C02Z)=Sof(H02Z)=
 Sof(C02Q)=Sof(H02Q)=Sof(C028)=Sof(H028)=FVAR(4)
 Sof(H02A)=Sof(H02B)=Sof(C042)=Sof(H042)=Sof(C10)=Sof(H10)=Sof(C24)=Sof(C25)=
 Sof(H25)=Sof(C1A)=Sof(H1A)=Sof(C23)=Sof(H23)=1-FVAR(5)
 Sof(H01E)=Sof(H01F)=Sof(C26)=Sof(H26)=Sof(C1D)=Sof(H1D)=Sof(C1C)=Sof(H1C)=
 Sof(C1B)=Sof(C2)=Sof(H2)=Sof(C11A)=Sof(H11A)=1-FVAR(6)
 Sof(H01C)=Sof(H01D)=Sof(C03Y)=Sof(H03Y)=Sof(C11)=Sof(H11)=Sof(C037)=Sof(H037)=
 Sof(C1)=Sof(H1)=Sof(C02K)=Sof(H02K)=Sof(C02I)=FVAR(6)
4.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00G(H00G), C00O(H00O), C00O(H00B), C00P(H00P), C00Q(H00Q),
 C00Q(H00C), C00R(H00R), C00V(H00V), C00W(H00W), C016(H016), C018(H018),
 C01G(H01J), C01L(H01L), C01L(H01A), C01P(H01Q), C01Q(H01Y), C01V(H01V),
 C01Y(H01Z), C020(H020), C023(H023), C024(H024), C02L(H02L)
4.b Secondary CH2 refined with riding coordinates:
 C00U(H00D,H00E), C01H(H01K,H01P), C01J(H01C,H01D), C01J(H01E,H01F), C02H(H02A,
 H02B), C03V(H03O,H03P)
4.c Aromatic/amide H refined with riding coordinates:
 C00X(H00X), C00Z(H00Z), C012(H012), C013(H013), C019(H019), C01A(H01B),
 C01C(H01G), C01E(H01H), C01M(H01M), C01N(H01N), C01O(H01O), C01R(H01R),
 C01S(H01S), C01T(H01T), C01U(H01U), C01W(H01W), C01X(H01X), C01Z(H01),
 C022(H022), C025(H025), C026(H026), C027(H027), C029(H029), C02C(H02I),
 C02G(H02G), C02H(H02H), C02J(H02J), C02M(H02M), C02N(H02N), C02O(H02O),
 C02P(H02P), C02R(H02R), C02S(H02S), C02T(H02T), C02W(H02W), C02Y(H02),
 C03R(H03R), C03T(H03T), C03P(H03Q), C038(H038), C031(H031), C034(H034),
 C035(H035), C039(H039), C03A(H03J), C03C(H03L), C03G(H03N), C03H(H03H),
 C03I(H03S), C03E(H03V), C03D(H03Z), C03O(H03), C03Z(H9), C03F(H03F),
 C03X(H03X), C02U(H02U), C01I(H01I), C03K(H03K), C03M(H03M), C03U(H03U),
 C033(H033), C02F(H02F), C03B(H03D), C021(H021), C03W(H03W), C03Y(H03Y),
 C11(H11), C037(H037), C1(H1), C02K(H02K), C041(H041), C3(H3), C02Z(H02Z),
 C02Q(H02Q), C028(H028), C042(H042), C10(H10), C25(H25), C1A(H1A), C23(H23),
 C5(H5), C0(H0), C8(H8), C7(H7), C6(H6), C12(H12), C14(H14), C20(H20), C16(H16),
  C17(H17), C21(H21), C18(H18), C15(H15), C4(H4), C19(H19), C21A(H21A),
 C19A(H19A), C4A(H4A), C15A(H15A), C18A(H18A), C26(H26), C1D(H1D), C1C(H1C),
 C2(H2), C11A(H11A)
4.d Fitted hexagon refined as free rotating group:
 C02Y(C03R,C03T,C01B,C03P,C038), C03I(C032,C03E,C03D,C03O,C03Z), C03F(C03X,
 C02U,C01I,C03K,C030), C03U(C033,C00J,C02F,C03B,C021), C03Y(C11,C037,C1,C02K,
 C02I), C041(C3,C02D,C02Z,C02Q,C028), C042(C10,C24,C25,C1A,C23), C5(C0,C9,C8,C7,
 C6), C21(C18,C15,C4,C22,C19), C21A(C19A,C22A,C4A,C15A,C18A), C26(C1D,C1C,C1B,
 C2,C11A)
4.e Idealised Me refined as rotating group:
 C02V(H02C,H02D,H02E), C02X(H02V,H02X,H02Y), C036(H03A,H03B,H03C), C03J(H03E,
 H03G,H03I)
;
_shelx_res_checksum              15057
_olex2_submission_special_instructions 'No special instructions were received'