Transition-Metal-Free Approach to Polysubstituted Furans.
You, Changming; Zhang, Zhenming; Tu, Yongliang; Tang, Hong; Wang, Yuanfeng; Long, Da; Zhao, Junfeng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03006

data_4037848
_publ_section_title
;
 Transition-Metal-Free Approach to Polysubstituted Furans.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03006
_journal_year                    2020
_chemical_formula_moiety         'C14 H11 N O3'
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.23
_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     dual
_audit_creation_date             2018-05-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.024(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.9806(10)
_cell_length_b                   28.9942(17)
_cell_length_c                   7.2032(7)
_cell_measurement_reflns_used    4819
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2300
_cell_measurement_theta_min      3.6690
_cell_volume                     2404.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_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    -88.00 -35.00   1.00   12.68    --  -15.76-178.00  60.00   53
  2  \w     -2.00  86.00   1.00   12.68    --   17.01  37.00  60.00   88
  3  \w     -2.00  86.00   1.00   12.68    --   17.01  37.00  90.00   88
  4  \w    -52.00  36.00   1.00   12.68    --   17.01 -37.00 -90.00   88
  5  \w    -87.00  -7.00   1.00   12.68    --  -15.76 -19.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0087903000
_diffrn_orient_matrix_UB_12      0.0218435000
_diffrn_orient_matrix_UB_13      -0.0380946000
_diffrn_orient_matrix_UB_21      0.0602264000
_diffrn_orient_matrix_UB_22      -0.0014933000
_diffrn_orient_matrix_UB_23      0.0473905000
_diffrn_orient_matrix_UB_31      0.0094518000
_diffrn_orient_matrix_UB_32      -0.0109327000
_diffrn_orient_matrix_UB_33      -0.0824185000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19605
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.321
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+1.0440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3324
_reflns_number_total             4885
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03006_si_002.cif
_cod_data_source_block           ycm20180508
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C14 H11 N O3)'
_cod_original_formula_sum        'C28 H22 N2 O6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     482.47
_cod_database_code               4037848
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.995
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C3(H3), C4(H4), C6(H6), C10(H10), C26(H26), C23(H23), C27(H27),
 C24(H24), C5(H5), C20(H20), C11(H11)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_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 1.876
_oxdiff_exptl_absorpt_empirical_full_min 0.576