A diazirine's central carbon is sp<sup>2</sup>-hybridized, facilitating conjugation to dye molecules.
Michelini, Lorenzo; Slaney, Tanya; Virk, Seerat; Rafic, Estefanía; Qie, L. Charlie; Corejova, Klara; Lepage, Mathieu L.; Musolino, Stefania F.; Oliver, Allen G.; Etchenique, Roberto; Hong, W. David; DiLabio, Gino A.; Wulff, Jeremy E.; Chemical science 16 (2025) 970–979; doi:10.1039/d4sc06427e

data_1573376
_publ_section_title
;
 A diazirine's central carbon is sp<sup>2</sup>-hybridized, facilitating
 conjugation to dye molecules.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              970
_journal_page_last               979
_journal_paper_doi               10.1039/d4sc06427e
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H7 F6 N5'
_chemical_formula_sum            'C9 H7 F6 N5'
_chemical_formula_weight         299.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-07-11 deposited with the CCDC.	2024-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0705(7)
_cell_length_b                   18.6804(12)
_cell_length_c                   5.7580(4)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.54
_cell_measurement_theta_min      4.73
_cell_volume                     1083.20(13)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            18518
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.604
_diffrn_reflns_theta_min         4.734
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  0.8904
_exptl_absorpt_correction_T_min  0.7818
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al. 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2143
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0227
_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^)+(0.0361P)^2^+0.2222P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0586
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2142
_reflns_number_total             2143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06427e2.cif
_cod_data_source_block           uvic1812
_cod_depositor_comments          'Adding full bibliography for 1573376.cif.'
_cod_database_code               1573376
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.707
_shelx_estimated_absorpt_t_max   0.855
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              92553
_shelx_hkl_checksum              21879