Design, Synthesis and Resolution of Spirocyclic Bisoxindoles Based C2-Symmetric Diols.
Sun, Guodong; Wang, Zhongqing; Luo, Zhonghua; Lin, YiCao; Deng, Zhuofei; Li, Ridong; Zhang, Jiancun; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01155

data_4038644
_publ_section_title
;
 Design, Synthesis and Resolution of Spirocyclic Bisoxindoles Based
 C2-Symmetric Diols.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01155
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H12 Cl2 N2 O4, 2(H2 O)'
_chemical_formula_sum            'C17 H16 Cl2 N2 O6'
_chemical_formula_weight         415.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.7629(6)
_cell_length_b                   13.4736(5)
_cell_length_c                   8.8054(3)
_cell_measurement_reflns_used    4521
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.76
_cell_volume                     1751.48(11)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      250.0
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.993
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12206
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.693
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0583 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.9052.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.787
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.31(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.366
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.365
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0980
_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^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2960
_refine_ls_wR_factor_ref         0.3139
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2629
_reflns_number_total             3077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01155_si_002.cif
_cod_data_source_block           zz
_cod_database_code               4038644
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, H2 of C8, All O(H,H) groups
 At 1.2 times of:
  H3 of C3, H2A of C2
2. Rigid body (RIGU) restrains
 C5, C6, C7, C8, N1, C9, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1, C2, C3, C4, C5, C6, O2, Cl1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Everything fixed:
 H2
3.b Free rotating group:
 O3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              21296
_shelx_hkl_checksum              23213
_shelx_fab_checksum              58705
_olex2_submission_special_instructions 'No special instructions were received'