A combination of polarity reversal, Diels-Alder cycloaddition and skeletal remodeling to access pyridine fused nitrones
Han, Hua-Bin; Li, Chaoyang; Niu, Xin-Yue; Wang, Yuxia; Zhang, Wenjing; Wang, Qi-Lin; Chemical Communications  (2022) –; doi:10.1039/D2CC00155A

data_7129883
_publ_section_title
;
 A combination of polarity reversal, Diels-Alder cycloaddition and
 skeletal remodeling to access pyridine fused nitrones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00155A
_journal_year                    2022
_chemical_formula_moiety         'C27 H19 Cl N2 O3'
_chemical_formula_sum            'C27 H19 Cl N2 O3'
_chemical_formula_weight         454.89
_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             2021-11-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.298(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7534(3)
_cell_length_b                   13.7503(4)
_cell_length_c                   13.8861(4)
_cell_measurement_reflns_used    4495
_cell_measurement_temperature    292.99(10)
_cell_measurement_theta_max      73.4000
_cell_measurement_theta_min      4.5410
_cell_volume                     2200.68(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_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     24.00  57.00   1.00    1.00    --   40.73  38.00  90.00   33
  2  \w     89.00 115.00   1.00    1.00    --   40.73  38.00  90.00   26
  3  \w     86.00 168.00   1.00    1.50    --  106.95  77.00 150.00   82
  4  \w    118.00 150.00   1.00    1.50    --  106.95 125.00  60.00   32
  5  \w     81.00 158.00   1.00    1.50    --  106.95  45.00  90.00   77
  6  \w     48.00 125.00   1.00    1.50    --  106.95 -61.00 -60.00   77
  7  \w     41.00 108.00   1.00    1.50    --  106.95 -61.00  60.00   67
  8  \w     58.00  92.00   1.00    1.00    --   40.73-125.00 120.00   34
  9  \w     31.00 108.00   1.00    1.50    --  106.95 -95.00-120.00   77
 10  \w    -68.00  32.00   1.00    1.00    --  -40.73  57.00 150.00  100
 11  \w    -93.00  -6.00   1.00    1.00    --  -40.73 125.00-120.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0043646000
_diffrn_orient_matrix_UB_12      0.0907619000
_diffrn_orient_matrix_UB_13      -0.0641844000
_diffrn_orient_matrix_UB_21      0.1322938000
_diffrn_orient_matrix_UB_22      -0.0121720000
_diffrn_orient_matrix_UB_23      0.0111224000
_diffrn_orient_matrix_UB_31      -0.0191074000
_diffrn_orient_matrix_UB_32      -0.0644296000
_diffrn_orient_matrix_UB_33      -0.0924994000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8758
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.639
_diffrn_reflns_theta_min         3.835
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0755P)^2^+0.3822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3567
_reflns_number_total             4315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00155a2.cif
_cod_data_source_block           199
_cod_database_code               7129883
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              84173
_shelx_hkl_checksum              79851
_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 1.974
_oxdiff_exptl_absorpt_empirical_full_min 0.551