#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:32:31 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268950 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158231.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158231
loop_
_publ_author_name
'Yadav, Maruti B.'
'Jeong, Yeon Tae'
_publ_section_title
;
 A one-pot ring-closure and ring-opening sequence for the cascade
 synthesis of dihydrofurofurans and functionalized furans.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7409
_journal_page_last               7419
_journal_paper_doi               10.1039/d1ob01300a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C33 H26 N2 O4'
_chemical_formula_sum            'C33 H26 N2 O4'
_chemical_formula_weight         514.56
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-05-12 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 114.941(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.799(3)
_cell_length_b                   9.2371(19)
_cell_length_c                   18.139(3)
_cell_measurement_reflns_used    1344
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      20.189
_cell_measurement_theta_min      2.523
_cell_volume                     2704.1(9)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1844
_diffrn_reflns_av_sigmaI/netI    0.1458
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27646
_diffrn_reflns_theta_full        25.13
_diffrn_reflns_theta_max         25.13
_diffrn_reflns_theta_min         2.48
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.2063
_refine_ls_R_factor_gt           0.0629
_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/[σ²(Fo²)+(0.0778P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.2023
_reflns_number_gt                1952
_reflns_number_total             4808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01300a2.cif
_cod_data_source_block           d23287
_cod_depositor_comments
'Adding full bibliography for 7158230--7158231.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158231
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2523(3) 0.6197(5) 0.4080(3) 0.0440(12) Uani 1 1 d . . .
C2 C 0.2449(3) 0.5333(5) 0.4701(2) 0.0365(11) Uani 1 1 d . . .
C3 C 0.2653(3) 0.3907(5) 0.4857(2) 0.0345(11) Uani 1 1 d . . .
C4 C 0.2998(3) 0.2795(5) 0.4522(2) 0.0361(11) Uani 1 1 d . . .
C5 C 0.3205(3) 0.3102(5) 0.3885(3) 0.0463(12) Uani 1 1 d . . .
H5 H 0.3115 0.4045 0.3654 0.056 Uiso 1 1 calc R . .
C6 C 0.3546(3) 0.2029(5) 0.3582(3) 0.0541(14) Uani 1 1 d . . .
H6 H 0.3687 0.2258 0.3145 0.065 Uiso 1 1 calc R . .
C7 C 0.3687(3) 0.0648(5) 0.3894(3) 0.0536(14) Uani 1 1 d . . .
C8 C 0.4055(3) -0.0508(5) 0.3556(3) 0.0740(17) Uani 1 1 d . . .
H8A H 0.3611 -0.0994 0.3100 0.111 Uiso 1 1 calc R . .
H8B H 0.4351 -0.1217 0.3982 0.111 Uiso 1 1 calc R . .
H8C H 0.4442 -0.0061 0.3367 0.111 Uiso 1 1 calc R . .
C9 C 0.3466(3) 0.0359(5) 0.4523(3) 0.0584(14) Uani 1 1 d . . .
H9 H 0.3552 -0.0588 0.4749 0.070 Uiso 1 1 calc R . .
C10 C 0.3125(3) 0.1397(5) 0.4836(3) 0.0495(13) Uani 1 1 d . . .
H10 H 0.2977 0.1158 0.5267 0.059 Uiso 1 1 calc R . .
C11 C 0.2154(2) 0.4693(4) 0.5729(2) 0.0331(10) Uani 1 1 d . . .
C12 C 0.1893(2) 0.4379(5) 0.6385(2) 0.0345(11) Uani 1 1 d . . .
C13 C 0.1732(2) 0.2975(5) 0.6519(2) 0.0353(11) Uani 1 1 d . . .
H13 H 0.1826 0.2218 0.6213 0.042 Uiso 1 1 calc R . .
C14 C 0.1431(3) 0.2633(5) 0.7104(2) 0.0342(11) Uani 1 1 d . . .
C15 C 0.1303(2) 0.3764(4) 0.7570(2) 0.0331(10) Uani 1 1 d . . .
C16 C 0.1490(3) 0.5193(5) 0.7432(3) 0.0434(12) Uani 1 1 d . . .
H16 H 0.1416 0.5960 0.7744 0.052 Uiso 1 1 calc R . .
C17 C 0.1777(3) 0.5498(5) 0.6856(2) 0.0414(12) Uani 1 1 d . . .
H17 H 0.1899 0.6470 0.6773 0.050 Uiso 1 1 calc R . .
C18 C 0.0993(3) 0.3423(5) 0.8151(2) 0.0401(11) Uani 1 1 d . . .
H18 H 0.0911 0.4168 0.8470 0.048 Uiso 1 1 calc R . .
C19 C 0.0813(3) 0.2026(5) 0.8249(2) 0.0377(11) Uani 1 1 d . . .
C20 C 0.0336(3) 0.2616(5) 0.9267(3) 0.0649(16) Uani 1 1 d . . .
H20A H 0.0842 0.3139 0.9612 0.097 Uiso 1 1 calc R . .
H20B H 0.0105 0.2144 0.9610 0.097 Uiso 1 1 calc R . .
H20C H -0.0071 0.3298 0.8898 0.097 Uiso 1 1 calc R . .
C21 C 0.0923(3) 0.0895(5) 0.7775(3) 0.0416(12) Uani 1 1 d . . .
H21 H 0.0783 -0.0072 0.7845 0.050 Uiso 1 1 calc R . .
C22 C 0.1227(3) 0.1196(5) 0.7224(3) 0.0433(12) Uani 1 1 d . . .
H22 H 0.1305 0.0433 0.6913 0.052 Uiso 1 1 calc R . .
C23 C 0.2130(3) 0.5860(5) 0.5266(2) 0.0348(11) Uani 1 1 d . . .
C24 C 0.1790(3) 0.7326(4) 0.5247(2) 0.0329(11) Uani 1 1 d . . .
C25 C 0.0953(3) 0.7601(5) 0.4661(3) 0.0419(12) Uani 1 1 d . . .
C26 C 0.2214(3) 0.8417(5) 0.5756(3) 0.0391(11) Uani 1 1 d . . .
C27 C 0.3078(3) 0.8379(5) 0.6398(3) 0.0396(11) Uani 1 1 d . . .
C28 C 0.3702(3) 0.7607(5) 0.6305(3) 0.0537(13) Uani 1 1 d . . .
H28 H 0.3581 0.7074 0.5820 0.064 Uiso 1 1 calc R . .
C29 C 0.4497(3) 0.7610(5) 0.6913(3) 0.0580(14) Uani 1 1 d . . .
H29 H 0.4916 0.7072 0.6840 0.070 Uiso 1 1 calc R . .
C30 C 0.4699(3) 0.8376(5) 0.7624(3) 0.0527(13) Uani 1 1 d . . .
C31 C 0.5570(3) 0.8347(6) 0.8288(3) 0.0772(17) Uani 1 1 d . . .
H31A H 0.5828 0.7414 0.8280 0.116 Uiso 1 1 calc R . .
H31B H 0.5552 0.8479 0.8817 0.116 Uiso 1 1 calc R . .
H31C H 0.5894 0.9130 0.8199 0.116 Uiso 1 1 calc R . .
C32 C 0.4076(3) 0.9144(5) 0.7711(3) 0.0580(14) Uani 1 1 d . . .
H32 H 0.4198 0.9668 0.8198 0.070 Uiso 1 1 calc R . .
C33 C 0.3278(3) 0.9167(5) 0.7103(3) 0.0518(13) Uani 1 1 d . . .
H33 H 0.2865 0.9729 0.7171 0.062 Uiso 1 1 calc R . .
N1 N 0.2559(3) 0.6916(4) 0.3578(3) 0.0688(14) Uani 1 1 d . . .
N2 N 0.0513(2) 0.6525(4) 0.4179(2) 0.0555(11) Uani 1 1 d . . .
H2A H -0.0001 0.6678 0.3825 0.067 Uiso 1 1 calc R . .
H2B H 0.0738 0.5664 0.4216 0.067 Uiso 1 1 calc R . .
O1 O 0.24691(16) 0.3505(3) 0.54891(16) 0.0365(7) Uani 1 1 d . . .
O2 O 0.05259(18) 0.1552(3) 0.88066(18) 0.0490(9) Uani 1 1 d . . .
O3 O 0.06171(19) 0.8833(3) 0.45973(18) 0.0547(9) Uani 1 1 d . . .
O4 O 0.18558(18) 0.9705(3) 0.57354(17) 0.0490(9) Uani 1 1 d . . .
H4' H 0.1293 0.9580 0.5408 0.059 Uiso 1 1 d R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 177.7(5) . . ?
C3 C2 C1 126.8(4) . . ?
C3 C2 C23 109.0(4) . . ?
C1 C2 C23 124.3(4) . . ?
C2 C3 O1 107.5(3) . . ?
C2 C3 C4 135.7(4) . . ?
O1 C3 C4 116.8(4) . . ?
C5 C4 C10 118.7(4) . . ?
C5 C4 C3 120.9(4) . . ?
C10 C4 C3 120.5(4) . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 122.2(5) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C9 117.0(4) . . ?
C6 C7 C8 121.6(4) . . ?
C9 C7 C8 121.5(5) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 122.3(5) . . ?
C10 C9 H9 118.9 . . ?
C7 C9 H9 118.9 . . ?
C9 C10 C4 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C4 C10 H10 120.0 . . ?
C23 C11 O1 110.3(3) . . ?
C23 C11 C12 135.7(4) . . ?
O1 C11 C12 113.8(3) . . ?
C13 C12 C17 119.4(4) . . ?
C13 C12 C11 119.2(4) . . ?
C17 C12 C11 121.3(4) . . ?
C12 C13 C14 121.2(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C22 121.9(4) . . ?
C13 C14 C15 119.3(4) . . ?
C22 C14 C15 118.7(4) . . ?
C16 C15 C18 122.4(4) . . ?
C16 C15 C14 118.2(4) . . ?
C18 C15 C14 119.3(4) . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C15 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C15 C18 H18 120.1 . . ?
C18 C19 O2 125.2(4) . . ?
C18 C19 C21 121.3(4) . . ?
O2 C19 C21 113.5(4) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C19 119.8(4) . . ?
C22 C21 H21 120.1 . . ?
C19 C21 H21 120.1 . . ?
C21 C22 C14 121.0(4) . . ?
C21 C22 H22 119.5 . . ?
C14 C22 H22 119.5 . . ?
C11 C23 C2 104.6(4) . . ?
C11 C23 C24 130.5(4) . . ?
C2 C23 C24 124.7(4) . . ?
C26 C24 C25 118.4(4) . . ?
C26 C24 C23 123.9(4) . . ?
C25 C24 C23 117.7(4) . . ?
O3 C25 N2 119.0(4) . . ?
O3 C25 C24 121.7(4) . . ?
N2 C25 C24 119.3(4) . . ?
O4 C26 C24 121.0(4) . . ?
O4 C26 C27 111.4(4) . . ?
C24 C26 C27 127.5(4) . . ?
C33 C27 C28 118.4(4) . . ?
C33 C27 C26 119.3(4) . . ?
C28 C27 C26 122.2(4) . . ?
C29 C28 C27 120.3(5) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 121.6(5) . . ?
C28 C29 H29 119.2 . . ?
C30 C29 H29 119.2 . . ?
C32 C30 C29 117.7(5) . . ?
C32 C30 C31 121.5(5) . . ?
C29 C30 C31 120.8(5) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 C33 121.5(5) . . ?
C30 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C27 C33 C32 120.5(5) . . ?
C27 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C25 N2 H2A 120.0 . . ?
C25 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C3 O1 C11 108.6(3) . . ?
C19 O2 C20 117.7(3) . . ?
C26 O4 H4' 106.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.151(5) . ?
C1 C2 1.431(6) . ?
C2 C3 1.364(5) . ?
C2 C23 1.451(5) . ?
C3 O1 1.369(4) . ?
C3 C4 1.457(5) . ?
C4 C5 1.382(5) . ?
C4 C10 1.391(6) . ?
C5 C6 1.390(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(6) . ?
C6 H6 0.9500 . ?
C7 C9 1.381(6) . ?
C7 C8 1.511(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C23 1.355(5) . ?
C11 O1 1.384(4) . ?
C11 C12 1.478(5) . ?
C12 C13 1.372(5) . ?
C12 C17 1.410(5) . ?
C13 C14 1.411(5) . ?
C13 H13 0.9500 . ?
C14 C22 1.417(6) . ?
C14 C15 1.423(5) . ?
C15 C16 1.409(5) . ?
C15 C18 1.415(5) . ?
C16 C17 1.373(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.359(5) . ?
C18 H18 0.9500 . ?
C19 O2 1.382(4) . ?
C19 C21 1.418(6) . ?
C20 O2 1.420(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.351(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.478(5) . ?
C24 C26 1.361(5) . ?
C24 C25 1.442(6) . ?
C25 O3 1.268(5) . ?
C25 N2 1.337(5) . ?
C26 O4 1.343(5) . ?
C26 C27 1.487(6) . ?
C27 C33 1.381(6) . ?
C27 C28 1.389(6) . ?
C28 C29 1.380(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(6) . ?
C29 H29 0.9500 . ?
C30 C32 1.379(6) . ?
C30 C31 1.509(6) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.383(6) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
O4 H4' 0.9317 . ?
