A photochemical ring expansion of 6- to 8-membered nitrogen heterocycles by [1,3]-sigmatropic rearrangement.
Manning, Morgan A.; Sun, Wei; Light, Mark E.; Harrowven, David C.; Chemical communications (Cambridge, England) 57 (2021) 4556–4559; doi:10.1039/d1cc00393c

data_7128107
_publ_section_title
;
 A photochemical ring expansion of 6- to 8-membered nitrogen heterocycles
 by [1,3]-sigmatropic rearrangement.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4556
_journal_page_last               4559
_journal_paper_doi               10.1039/d1cc00393c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C27 H23 N O2'
_chemical_formula_sum            'C27 H23 N O2'
_chemical_formula_weight         393.46
_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             2019-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-29 deposited with the CCDC.	2021-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.7420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.24960(10)
_cell_length_b                   16.9896(3)
_cell_length_c                   16.7783(3)
_cell_measurement_reflns_used    11783
_cell_measurement_temperature    100.01(16)
_cell_measurement_theta_max      31.8480
_cell_measurement_theta_min      3.0420
_cell_volume                     2066.37(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -55.00 -16.00   1.00    8.00    --  -22.70  38.00 120.00   39
  2  \w     -6.00  58.00   1.00    8.00    --  -22.70  38.00 120.00   64
  3  \w   -105.00 -74.00   1.00    8.00    --  -22.70 -38.00-180.00   31
  4  \w    -53.00  60.00   1.00    8.00    --  -22.70  38.00 150.00  113
  5  \w    -78.00  13.00   1.00    8.00    --  -22.70 -57.00 -30.00   91
  6  \w    -54.00  62.00   1.00    8.00    --  -22.70  38.00 -90.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0510993000
_diffrn_orient_matrix_UB_12      0.0015105000
_diffrn_orient_matrix_UB_13      -0.0357445000
_diffrn_orient_matrix_UB_21      0.0736378000
_diffrn_orient_matrix_UB_22      -0.0204094000
_diffrn_orient_matrix_UB_23      0.0190252000
_diffrn_orient_matrix_UB_31      -0.0391644000
_diffrn_orient_matrix_UB_32      -0.0363972000
_diffrn_orient_matrix_UB_33      -0.0121854000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21609
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.500
_diffrn_reflns_theta_min         3.055
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of Et2O and DCM  by slow evaporation'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.8629P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4743
_reflns_number_total             5231
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc00393c2.cif
_cod_data_source_block           2019sot0030_k1_100k
_cod_depositor_comments
'Adding full bibliography for 7128107--7128108.cif.'
_cod_database_code               7128107
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C27H23N1O2
_chemical_oxdiff_usercomment     SW/distero
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.a Ternary CH refined with riding coordinates:
 C1(H1), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              52824
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id SW/distero
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.767
_oxdiff_exptl_absorpt_empirical_full_min 0.462