Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles.
Gupta, Vijay; Sahu, Debashish; Jain, Shailja; Vanka, Kumar; Singh, Ravi P.; Organic & biomolecular chemistry 17 (2019) 8853–8857; doi:10.1039/c9ob01345h

data_7157076
_publ_section_title
;
 Diastereoselective multi-component tandem condensation: synthesis of
 2-amino-4-(2-furanone)-4H-chromene-3-carbonitriles.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8853
_journal_page_last               8857
_journal_paper_doi               10.1039/c9ob01345h
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C15 H12 N2 O3, C H Cl3'
_chemical_formula_sum            'C16 H13 Cl3 N2 O3'
_chemical_formula_weight         387.63
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-01-07 deposited with the CCDC.    2019-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                86.9640(12)
_cell_angle_beta                 71.0335(12)
_cell_angle_gamma                70.4039(12)
_cell_formula_units_Z            2
_cell_length_a                   8.0552(4)
_cell_length_b                   10.2825(5)
_cell_length_c                   11.7512(6)
_cell_measurement_reflns_used    6425
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.71
_cell_volume                     865.45(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      297.99
_diffrn_measured_fraction_theta_full 0.993
_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  0.0268
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12828
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.366
_diffrn_reflns_theta_min         1.836
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1076 before and 0.0380 after correction.
The Ratio of minimum to maximum transmission is 0.9131.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   0.942
_exptl_transmission_factor_min   0.914
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4327
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0455
_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^)+(0.0590P)^2^+0.3510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3254
_reflns_number_total             4327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01345h2.cif
_cod_data_source_block           vijay05_0m
_cod_depositor_comments
'Adding full bibliography for 7157076--7157078.cif.'
_cod_database_code               7157076
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C38(H38)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C27(H27), C29(H29), C31(H31), C36(H36)
2.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;
_shelx_res_checksum              23175
_olex2_submission_special_instructions 'No special instructions were received'