Synthesis of spiropyrazoline oxindoles by a formal [4 + 1] annulation reaction between 3-bromooxindoles and in situ-derived 1,2-diaza-1,3-dienes
Chen, Dong-Zhen; Xiao, Wen-Jing; Chen, Jia-Rong; Organic Chemistry Frontiers 4 (2017) 1289–; doi:10.1039/C7QO00163K

data_1553760
_publ_section_title
;
 Synthesis of spiropyrazoline oxindoles by a formal [4 + 1] annulation
 reaction between 3-bromooxindoles and in situ-derived
 1,2-diaza-1,3-dienes
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1289
_journal_paper_doi               10.1039/C7QO00163K
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C19 H16 Br N3 O3, C H Cl3'
_chemical_formula_sum            'C20 H17 Br Cl3 N3 O3'
_chemical_formula_weight         533.62
_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
_audit_creation_date             2017-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-02-27 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                99.608(16)
_cell_angle_beta                 94.163(15)
_cell_angle_gamma                96.363(16)
_cell_formula_units_Z            2
_cell_length_a                   6.299(8)
_cell_length_b                   11.774(15)
_cell_length_c                   14.904(19)
_cell_measurement_reflns_used    935
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.35
_cell_measurement_theta_min      2.78
_cell_volume                     1078(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0947
_diffrn_reflns_av_unetI/netI     0.1679
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7173
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.392
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.305
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_correction_T_min  0.8022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.015
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.199
_refine_ls_extinction_coef       0.016(5)
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.2000
_refine_ls_R_factor_gt           0.1125
_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^)+(0.1400P)^2^+9.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2823
_refine_ls_wR_factor_ref         0.3492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1905
_reflns_number_total             3798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00163k2.cif
_cod_data_source_block           mo_170110a_0m
_cod_database_code               1553760
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.802
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
3.a Ternary CH refined with riding coordinates:
 C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17), N3(H3A)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              1731
_shelx_hkl_checksum              33718
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'