Diastereodivergent synthesis of chromeno[2,3-b]chromenes by tuning the full reactivity centers of isocyanoacetate
Wang, Lei; Huang, Zitong; Guo, Xiaoyu; Liu, Jian; Dong, Jinhuan; Xu, Xianxiu; Chemical Communications  (2022) –; doi:10.1039/D2CC01632J

data_7130057
_publ_section_title
;
 Diastereodivergent synthesis of chromeno[2,3-b]chromenes by tuning the
 full reactivity centers of isocyanoacetate
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01632J
_journal_year                    2022
_chemical_formula_moiety         'C29 H21 N O3'
_chemical_formula_sum            'C29 H21 N O3'
_chemical_formula_weight         431.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-04-11
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2021-04-15 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 117.937(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1119(5)
_cell_length_b                   14.6483(4)
_cell_length_c                   12.6716(5)
_cell_measurement_reflns_used    3638
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8910
_cell_measurement_theta_min      10.4710
_cell_volume                     2150.17(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9794
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     12.00 123.00   1.00    1.00    --   54.00  19.00  60.00  111
  2  \w     75.00 119.00   1.00    1.00    --  108.00  25.00  30.00   44
  3  \w    151.00 177.00   1.00    1.00    --  108.00 111.00 -60.00   26
  4  \w     88.00 174.00   1.00    1.00    --  108.00  63.00-150.00   86
  5  \w    111.00 137.00   1.00    1.00    --  108.00 -25.00-180.00   26
  6  \w     75.00 101.00   1.00    1.00    --   54.00-125.00-180.00   26
  7  \w     43.00 104.00   1.00    1.00    --  108.00-111.00 -90.00   61
  8  \w     37.00  63.00   1.00    1.00    --  108.00 -25.00-180.00   26
  9  \w     35.00  85.00   1.00    1.00    --   54.00  57.00 -90.00   50
 10  \w     38.00 108.00   1.00    1.00    --  108.00 -37.00  90.00   70
 11  \w     38.00 115.00   1.00    1.00    --  108.00-111.00 120.00   77
 12  \w     30.00  82.00   1.00    1.00    --   54.00-125.00  90.00   52
 13  \w     16.00  69.00   1.00    1.00    --   54.00 -57.00 120.00   53
 14  \w    -27.00  36.00   1.00    1.00    --    0.00  77.00  30.00   63
 15  \w    -42.00  12.00   1.00    1.00    --    0.00 -57.00-180.00   54
 16  \w     58.00 139.00   1.00    1.00    --  108.00 178.00 120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0475989000
_diffrn_orient_matrix_UB_12      -0.0977609000
_diffrn_orient_matrix_UB_13      -0.0337476000
_diffrn_orient_matrix_UB_21      -0.1076397000
_diffrn_orient_matrix_UB_22      0.0374830000
_diffrn_orient_matrix_UB_23      -0.1089355000
_diffrn_orient_matrix_UB_31      0.0618698000
_diffrn_orient_matrix_UB_32      -0.0100889000
_diffrn_orient_matrix_UB_33      -0.0770006000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8006
_diffrn_reflns_theta_full        67.05
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         3.82
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0056(3)
_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   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.3397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                3238
_reflns_number_total             3844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc01632j2.cif
_cod_data_source_block           exp_3248
_cod_original_cell_volume        2150.15(13)
_cod_database_code               7130057
_chemical_oxdiff_formula         'C1 H1 N1 O1'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C29(H29)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.681