Synthesis of optically active 2-amino-1′-benzyl-2′,5-dioxo-5H-spiro[indeno[1,2-b]pyran-4,3′-indoline]-3-carbonitriles catalyzed by a bifunctional squaramide derived from quinine
Wang, Yuanyuan; Wei, Zhonglin; Cao, Jungang; Liang, Dapeng; Lin, Yingjie; Duan, Haifeng; New Journal of Chemistry 45 (2021) 2609–2613; doi:10.1039/D0NJ06092E

data_7060298
_publ_section_title
;
 Synthesis of optically active
 2-amino-1&#x2032;-benzyl-2&#x2032;,5-dioxo-5H-spiro[indeno[1,2-b]pyran-4,3&#x2032;-indoline]-3-carbonitriles
 catalyzed by a bifunctional squaramide derived from quinine
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2609
_journal_page_last               2613
_journal_paper_doi               10.1039/D0NJ06092E
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C27 H16 Cl N3 O3'
_chemical_formula_sum            'C27 H16 Cl N3 O3'
_chemical_formula_weight         465.88
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-06-22
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-06-28 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.460(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5954(5)
_cell_length_b                   14.4663(8)
_cell_length_c                   18.0480(10)
_cell_measurement_reflns_used    7930
_cell_measurement_temperature    190.15
_cell_measurement_theta_max      24.902
_cell_measurement_theta_min      2.312
_cell_volume                     2191.3(2)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      190.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCDC Detect Area'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26816
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.018
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_min         2.311
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_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    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0351P)^2^+1.3109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3073
_reflns_number_total             3867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj06092e2.cif
_cod_data_source_block           mo_20191230_0m_pl_pl
_cod_depositor_comments          'Adding full bibliography for 7060298.cif.'
_cod_database_code               7060298
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Riding coordinates:
 N00M(H00A,H00B)
2.b Secondary CH2 refined with riding coordinates:
 C027(H02A,H02B)
2.c Aromatic/amide H refined with riding coordinates:
 C02B(H02C), C02M(H02M), C02N(H02N), C02Z(H02Z), C030(H030), C031(H031),
 C03A(H03A), C03C(H03C), C03F(H03F), C03G(H03G), C03I(H03I), C03S(H03S)
;
_shelx_res_checksum              11404
_shelx_hkl_checksum              58544
_olex2_submission_special_instructions 'No special instructions were received'