Self [3 + 4] Cycloadditions of Isatin N, N'-Cyclic Azomethine Imine 1,3-Dipole with N-( o-Chloromethyl)aryl Amides.
Jin, Qiaomei; Zhang, Jian; Jiang, Cuihua; Zhang, Dongjian; Gao, Meng; Hu, Shihe; The Journal of organic chemistry 83 (2018) 8410–8416; doi:10.1021/acs.joc.8b01055

data_4035582
_publ_section_title
;
 Self [3 + 4] Cycloadditions of Isatin N, N'-Cyclic Azomethine Imine
 1,3-Dipole with N-( o-Chloromethyl)aryl Amides.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8410
_journal_page_last               8416
_journal_paper_doi               10.1021/acs.joc.8b01055
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C27 H24 N4 O4'
_chemical_formula_sum            'C27 H24 N4 O4'
_chemical_formula_weight         468.50
_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             2017-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.635(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.693(5)
_cell_length_b                   17.549(7)
_cell_length_c                   10.385(4)
_cell_measurement_reflns_used    835
_cell_measurement_temperature    173
_cell_measurement_theta_max      18.290
_cell_measurement_theta_min      2.321
_cell_volume                     2248.1(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      173
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13752
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.651
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0842 before and 0.0692 after correction. The Ratio of minimum to maximum transmission is 0.8726. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0790P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1680
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2253
_reflns_number_total             3943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01055_si_001.cif
_cod_data_source_block           mo_20171071-3a_0m
_cod_original_cell_volume        2248.0(16)
_cod_database_code               4035582
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.982
_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 Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C7(H7a,H7b), C16(H16a,H16b), C17(H17a,H17b)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C5(H5), C1(H1), C10(H10), C24(H24), C23(H23), C4(H4), C9(H9),
 C11(H11), C21(H21), C3(H3), C2(H2), C22(H22)
2.c Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c)
;
_olex2_submission_special_instructions 'No special instructions were received'