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_7129884
_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 H18 I2 N2 O3, C H Cl3'
_chemical_formula_sum            'C28 H19 Cl3 I2 N2 O3'
_chemical_formula_weight         791.60
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-21
_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                94.433(2)
_cell_angle_beta                 101.832(2)
_cell_angle_gamma                98.841(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8911(5)
_cell_length_b                   11.6189(5)
_cell_length_c                   12.7499(7)
_cell_measurement_reflns_used    4503
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      24.49
_cell_measurement_theta_min      2.29
_cell_volume                     1408.10(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            34449
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.475
_diffrn_reflns_theta_min         2.136
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.552
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0752 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.3913.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_description       block
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0289P)^2^+1.9891P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4348
_reflns_number_total             5812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00155a2.cif
_cod_data_source_block           mo_1220_7_0m
_cod_database_code               7129884
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.784
_shelx_estimated_absorpt_t_min   0.629
_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 Ternary CH refined with riding coordinates:
 C011(H011)
2.b Secondary CH2 refined with riding coordinates:
 C00U(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C012(H012)
2.d Idealised tetrahedral OH refined as rotating group:
 O007(H007)
;
_shelx_res_checksum              45272
_shelx_hkl_checksum              1703
_olex2_submission_special_instructions 'No special instructions were received'