The Diversity-Oriented One-Pot Synthesis to Construct Functionalized Chroman-2-one Derivatives and Other Heterocyclic Compounds.
Chen, Ying-Han; Sun, Xue-Li; Guan, Hua-Shi; Liu, Yan-Kai; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00461

data_4032448
_publ_section_title
;
 The Diversity-Oriented One-Pot Synthesis to Construct Functionalized
 Chroman-2-one Derivatives and Other Heterocyclic Compounds.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00461
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H18.5 N O4 S'
_chemical_formula_sum            'C22 H19 N O4 S'
_chemical_formula_weight         393.44
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.231(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.032(2)
_cell_length_b                   5.5995(10)
_cell_length_c                   13.2174(17)
_cell_measurement_reflns_used    439
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      47.0800
_cell_measurement_theta_min      9.5090
_cell_volume                     952.0(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.1191
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3270
_diffrn_reflns_theta_full        71.62
_diffrn_reflns_theta_max         71.62
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.754
_exptl_absorpt_correction_T_max  0.7205
_exptl_absorpt_correction_T_min  0.7205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_coef       0.0101(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2354
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1370
_refine_ls_R_factor_gt           0.0760
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.2180
_reflns_number_gt                1210
_reflns_number_total             2354
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00461_si_002.cif
_cod_data_source_block           a
_cod_database_code               4032448
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2B-C1B \\sim C2A-C1A
 with sigma of 0.02
3. Rigid bond restraints
 C3, C4
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C4, S1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O4, N1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
Uanis(C1B) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2B) \\sim Ueq, Uanis(C2A)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C2B) = Uanis(C2A)
Uanis(C1A) = Uanis(C1B)
5. Others
 Sof(H3B)=Sof(C2B)=Sof(C1B)=Sof(H1B)=1-FVAR(1)
 Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C1A)=Sof(H1A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C16(H16), C14(H14), C6(H6), C5(H5)
6.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3B), C3(H3A), C8(H8), C19(H19), C21(H21), C22(H22), C11(H11), C18(H18),
 C9(H9), C20(H20), C10(H10), C1B(H1B), C2A(H2A), C1A(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'