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_7130058
_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 H19 F2 N O3'
_chemical_formula_sum            'C29 H19 F2 N O3'
_chemical_formula_weight         467.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-15 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                102.608(9)
_cell_angle_beta                 104.040(8)
_cell_angle_gamma                106.219(8)
_cell_formula_units_Z            2
_cell_length_a                   7.0756(5)
_cell_length_b                   12.6433(14)
_cell_length_c                   13.6801(14)
_cell_measurement_reflns_used    2408
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3730
_cell_measurement_theta_min      8.9660
_cell_volume                     1084.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     -4.00  22.00   1.00    1.00    --    0.00  90.00-130.00   26
  2  \w     -9.00  16.00   1.00    1.00    --    0.00 -90.00 114.00   25
  3  \w      6.00  68.00   1.00    1.00    --   54.00 -90.00 114.00   62
  4  \w     40.00 101.00   1.00    1.00    --  108.00 -90.00 114.00   61
  5  \w    116.00 141.00   1.00    1.00    --  108.00  90.00-130.00   25
  6  \w    -18.00   9.00   1.00    1.00    --    0.00 -77.00 -60.00   27
  7  \w    -20.00  28.00   1.00    1.00    --    0.00 -77.00  30.00   48
  8  \w    -16.00  11.00   1.00    1.00    --    0.00 -77.00-180.00   27
  9  \w     55.00  81.00   1.00    1.00    --   54.00-125.00   0.00   26
 10  \w    -13.00  72.00   1.00    1.00    --   54.00 -57.00 150.00   85
 11  \w    -18.00   8.00   1.00    1.00    --   54.00 -37.00-120.00   26
 12  \w     33.00 115.00   1.00    1.00    --   54.00  57.00  60.00   82
 13  \w     22.00  80.00   1.00    1.00    --   54.00 -37.00-120.00   58
 14  \w    104.00 177.00   1.00    1.00    --  108.00  77.00  60.00   73
 15  \w    105.00 177.00   1.00    1.00    --  108.00 111.00 -30.00   72
 16  \w    103.00 178.00   1.00    1.00    --  108.00  77.00 150.00   75
 17  \w    130.00 177.00   1.00    1.00    --  108.00  77.00-150.00   47
 18  \w     39.00  78.00   1.00    1.00    --  108.00 -50.00 120.00   39
 19  \w     73.00 129.00   1.00    1.00    --  108.00 178.00   0.00   56
 20  \w     81.00 106.00   1.00    1.00    --  108.00 -91.00  30.00   25
 21  \w    111.00 177.00   1.00    1.00    --  108.00 111.00-180.00   66
 22  \w     87.00 134.00   1.00    1.00    --  108.00 -77.00 -90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1557376000
_diffrn_orient_matrix_UB_12      -0.0339705000
_diffrn_orient_matrix_UB_13      -0.0502271000
_diffrn_orient_matrix_UB_21      -0.0230834000
_diffrn_orient_matrix_UB_22      0.0794833000
_diffrn_orient_matrix_UB_23      -0.0694513000
_diffrn_orient_matrix_UB_31      0.1807162000
_diffrn_orient_matrix_UB_32      0.1014656000
_diffrn_orient_matrix_UB_33      0.0868376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4820
_diffrn_reflns_theta_full        67.05
_diffrn_reflns_theta_max         67.05
_diffrn_reflns_theta_min         3.83
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0047(5)
_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   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.3312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                2686
_reflns_number_total             3096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc01632j2.cif
_cod_data_source_block           exp_225
_cod_original_cell_volume        1084.92(18)
_cod_database_code               7130058
_chemical_oxdiff_formula         'C1 H1 N1 O1'
_diffrn_oxdiff_digest_frames
;
0179ea4ff228f7e10dd05cef770cf74dfa00027cef9
;
_diffrn_oxdiff_digest_hkl
;
010d8512ea717b1f753982687a5ffa7e236317
;
_reflns_odcompleteness_completeness 79.82
_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), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.645