A vinylogous Norrish reaction as a strategy for light-mediated ring expansion.
Gorobets, Evgueni; Papatzimas, James W.; Dourado, Jorge; Yousefalizadeh, Goonay; Lee, JinGyu; Brownsey, Duncan K.; Stamplecoskie, Kevin; Davis, Rebecca; Derksen, Darren J.; Chemical communications (Cambridge, England)  (2022) –; doi:10.1039/d2cc00513a

data_7129703
_publ_section_title
;
 A vinylogous Norrish reaction as a strategy for light-mediated ring
 expansion.
;
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d2cc00513a
_journal_year                    2022
_chemical_formula_moiety         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34
_chemical_melting_point          484
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-10-06 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                95.958(5)
_cell_angle_beta                 90.704(4)
_cell_angle_gamma                98.055(4)
_cell_formula_units_Z            2
_cell_length_a                   5.3474(3)
_cell_length_b                   10.8303(7)
_cell_length_c                   13.5741(8)
_cell_measurement_reflns_used    1320
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.7735
_cell_measurement_theta_min      3.2745
_cell_volume                     773.88(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1799
_diffrn_reflns_av_unetI/netI     0.1145
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16188
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.201
_diffrn_reflns_theta_min         3.275
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0840 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.8567.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1772
_refine_ls_R_factor_gt           0.0879
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1262
_reflns_number_total             2925
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00513a2.cif
_cod_data_source_block           l
_cod_database_code               7129703
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
2.a Riding coordinates:
 O3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C9(H9), C13(H13), C14(H14), C16(H16), C17(H17)
;
_shelx_res_checksum              35647
_olex2_submission_special_instructions 'No special instructions were received'