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_1553759
_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         'C22 H20 Br N3 O5, C H2 Cl2'
_chemical_formula_sum            'C23 H22 Br Cl2 N3 O5'
_chemical_formula_weight         571.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-11-03 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.785(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.593(4)
_cell_length_b                   15.307(7)
_cell_length_c                   16.705(8)
_cell_measurement_reflns_used    3209
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      22.791
_cell_measurement_theta_min      2.382
_cell_volume                     2447.6(19)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      100.01(10)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0361
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14118
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        23.188
_diffrn_reflns_theta_max         23.188
_diffrn_reflns_theta_min         1.806
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.937
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0837 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.7955.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_description       plate
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0665P)^2^+1.3275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2567
_reflns_number_total             3436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00163k2.cif
_cod_data_source_block           cdz
_cod_original_cell_volume        2448(2)
_cod_database_code               1553759
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Cl2A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: H22C(0.65) H22D(0.65) H22A(0.35) H22B(0.35) Cl1A(0.35) Cl2A(0.35)
 Cl1B(0.65) Cl2B(0.65)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C22(H22C,H22D), C22(H22A,H22B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C18(H18), C19(H19), C20(H20), C21(H21)
4.c Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'