#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:58:41 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299075 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/03/7160334.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_7160334
loop_
_publ_author_name
'Yuan, Lili'
'Wang, Jie'
'Tang, Qiang'
'Wang, Yiping'
'Ma, Beibei'
'Shang, Yongjia'
'He, Xinwei'
_publ_section_title
;
 DBU-catalyzed annulation strategy for modular assembly of
 2,3-difunctionalized dihydrobenzofurans.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1832
_journal_page_last               1836
_journal_paper_doi               10.1039/d4ob01406e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C18 H17 N O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-05-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-08-19 deposited with the CCDC.	2025-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.7360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.440(2)
_cell_length_b                   7.9493(7)
_cell_length_c                   15.9676(13)
_cell_measurement_reflns_used    6529
_cell_measurement_temperature    293.15(10)
_cell_measurement_theta_max      27.575
_cell_measurement_theta_min      2.394
_cell_volume                     3196.5(5)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15(10)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13429
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.642
_diffrn_reflns_theta_min         1.617
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0370 after correction.
The Ratio of minimum to maximum transmission is 0.8770.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0752P)²+1.2970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1464
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2959
_reflns_number_total             3708
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01406e2.cif
_cod_data_source_block           131202b_0m
_cod_depositor_comments          'Adding full bibliography for 7160334.cif.'
_cod_database_code               7160334
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.987
_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 Riding coordinates:
 C18(H18A,H18B,H18C)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.40982(5) 0.35838(18) 0.06506(9) 0.0442(3) Uani 1 1 d . . . . .
H1 H 0.433838 0.451675 0.063937 0.053 Uiso 1 1 calc R U . . .
C2 C 0.44003(6) 0.19013(18) 0.07814(9) 0.0446(3) Uani 1 1 d . . . . .
H2 H 0.430606 0.125349 0.023327 0.054 Uiso 1 1 calc R U . . .
C3 C 0.41923(5) 0.10588(18) 0.14547(9) 0.0426(3) Uani 1 1 d . . . . .
C4 C 0.42668(6) -0.05515(19) 0.17976(9) 0.0485(3) Uani 1 1 d . . . . .
H4 H 0.446384 -0.132921 0.159245 0.058 Uiso 1 1 calc R U . . .
C5 C 0.40441(6) -0.1002(2) 0.24542(10) 0.0532(4) Uani 1 1 d . . . . .
C6 C 0.37568(6) 0.0195(2) 0.27487(10) 0.0561(4) Uani 1 1 d . . . . .
H6 H 0.360883 -0.010416 0.318659 0.067 Uiso 1 1 calc R U . . .
C7 C 0.36808(6) 0.1817(2) 0.24178(10) 0.0530(4) Uani 1 1 d . . . . .
H7 H 0.348751 0.260426 0.262483 0.064 Uiso 1 1 calc R U . . .
C8 C 0.39048(5) 0.22131(18) 0.17677(9) 0.0442(3) Uani 1 1 d . . . . .
C9 C 0.50015(6) 0.2081(2) 0.11616(10) 0.0545(4) Uani 1 1 d . . . . .
H9A H 0.508383 0.276520 0.168902 0.065 Uiso 1 1 calc R U . . .
H9B H 0.515756 0.097844 0.132602 0.065 Uiso 1 1 calc R U . . .
C10 C 0.41254(10) -0.2761(2) 0.28306(14) 0.0780(6) Uani 1 1 d . . . . .
H10A H 0.432110 -0.270877 0.344459 0.117 Uiso 1 1 calc R U . . .
H10B H 0.432027 -0.341431 0.252737 0.117 Uiso 1 1 calc R U . . .
H10C H 0.378655 -0.327696 0.275884 0.117 Uiso 1 1 calc R U . . .
C11 C 0.36152(6) 0.36059(19) -0.01815(9) 0.0470(3) Uani 1 1 d . . . . .
C12 C 0.33128(5) 0.51876(19) -0.04309(9) 0.0462(3) Uani 1 1 d . . . . .
C13 C 0.28446(7) 0.5164(2) -0.11341(11) 0.0634(4) Uani 1 1 d . . . . .
H13 H 0.272474 0.415908 -0.142476 0.076 Uiso 1 1 calc R U . . .
C14 C 0.25593(7) 0.6618(3) -0.13999(12) 0.0695(5) Uani 1 1 d . . . . .
H14 H 0.224777 0.657683 -0.186915 0.083 Uiso 1 1 calc R U . . .
C15 C 0.27228(6) 0.8137(2) -0.09890(11) 0.0565(4) Uani 1 1 d . . . . .
C16 C 0.31871(7) 0.8151(2) -0.02893(12) 0.0600(4) Uani 1 1 d . . . . .
H16 H 0.330624 0.915890 -0.000054 0.072 Uiso 1 1 calc R U . . .
C17 C 0.34758(6) 0.6702(2) -0.00128(11) 0.0548(4) Uani 1 1 d . . . . .
H17 H 0.378462 0.674492 0.046170 0.066 Uiso 1 1 calc R U . . .
C18 C 0.24085(8) 0.9720(3) -0.12862(15) 0.0767(5) Uani 1 1 d . . . . .
H18A H 0.248703 1.051112 -0.080982 0.115 Uiso 1 1 d R U . . .
H18B H 0.203623 0.946072 -0.146722 0.115 Uiso 1 1 d R U . . .
H18C H 0.250163 1.019772 -0.177152 0.115 Uiso 1 1 d R U . . .
N1 N 0.52405(5) 0.28642(18) 0.05247(9) 0.0559(3) Uani 1 1 d . . . . .
O1 O 0.38852(4) 0.37745(13) 0.13857(6) 0.0518(3) Uani 1 1 d . . . . .
O2 O 0.34869(5) 0.23254(16) -0.06032(8) 0.0719(4) Uani 1 1 d . . . . .
O3 O 0.52002(7) 0.2139(2) -0.01560(10) 0.0873(5) Uani 1 1 d . . . . .
O4 O 0.54576(7) 0.42153(19) 0.07135(11) 0.0883(5) Uani 1 1 d . . . . .
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
C2 C1 H1 110.4 . . ?
C11 C1 H1 110.4 . . ?
C11 C1 C2 112.79(12) . . ?
O1 C1 H1 110.4 . . ?
O1 C1 C2 107.05(10) . . ?
O1 C1 C11 105.78(11) . . ?
C1 C2 H2 110.8 . . ?
C3 C2 C1 101.31(11) . . ?
C3 C2 H2 110.8 . . ?
C3 C2 C9 108.68(11) . . ?
C9 C2 C1 114.04(12) . . ?
C9 C2 H2 110.8 . . ?
C4 C3 C2 130.96(13) . . ?
C8 C3 C2 108.93(12) . . ?
C8 C3 C4 120.03(13) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.53(14) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C10 119.62(16) . . ?
C6 C5 C4 118.61(14) . . ?
C6 C5 C10 121.77(15) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 C5 122.72(14) . . ?
C7 C6 H6 118.6 . . ?
C6 C7 H7 121.5 . . ?
C8 C7 C6 117.01(14) . . ?
C8 C7 H7 121.5 . . ?
C3 C8 C7 122.11(14) . . ?
O1 C8 C3 112.94(12) . . ?
O1 C8 C7 124.91(13) . . ?
C2 C9 H9A 109.2 . . ?
C2 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N1 C9 C2 112.03(12) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C1 118.77(12) . . ?
O2 C11 C1 119.30(13) . . ?
O2 C11 C12 121.91(13) . . ?
C13 C12 C11 118.69(14) . . ?
C17 C12 C11 123.23(13) . . ?
C17 C12 C13 118.07(14) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.41(16) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.73(15) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 117.61(15) . . ?
C14 C15 C18 121.30(16) . . ?
C16 C15 C18 121.09(17) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.30(16) . . ?
C17 C16 H16 119.4 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.88(14) . . ?
C16 C17 H17 119.6 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 N1 C9 118.46(15) . . ?
O3 N1 O4 123.57(15) . . ?
O4 N1 C9 117.96(15) . . ?
C8 O1 C1 106.96(10) . . ?
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 H1 0.9800 . ?
C1 C2 1.5391(19) . ?
C1 C11 1.537(2) . ?
C1 O1 1.4563(16) . ?
C2 H2 0.9800 . ?
C2 C3 1.5057(18) . ?
C2 C9 1.526(2) . ?
C3 C4 1.383(2) . ?
C3 C8 1.3787(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(2) . ?
C5 C6 1.386(2) . ?
C5 C10 1.511(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(2) . ?
C8 O1 1.3770(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 N1 1.4875(19) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.478(2) . ?
C11 O2 1.2105(19) . ?
C12 C13 1.395(2) . ?
C12 C17 1.380(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 C16 1.385(2) . ?
C15 C18 1.503(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(2) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9599 . ?
C18 H18C 0.9601 . ?
N1 O3 1.206(2) . ?
N1 O4 1.2120(19) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 173.20(14) . . . . ?
C1 C2 C3 C8 -10.02(14) . . . . ?
C1 C2 C9 N1 -69.35(17) . . . . ?
C1 C11 C12 C13 -173.66(14) . . . . ?
C1 C11 C12 C17 7.6(2) . . . . ?
C2 C1 C11 C12 -175.06(11) . . . . ?
C2 C1 C11 O2 6.41(19) . . . . ?
C2 C1 O1 C8 -16.48(14) . . . . ?
C2 C3 C4 C5 177.19(14) . . . . ?
C2 C3 C8 C7 -177.63(13) . . . . ?
C2 C3 C8 O1 0.30(16) . . . . ?
C2 C9 N1 O3 -62.4(2) . . . . ?
C2 C9 N1 O4 116.34(17) . . . . ?
C3 C2 C9 N1 178.47(13) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C3 C4 C5 C10 -179.94(15) . . . . ?
C3 C8 O1 C1 10.39(16) . . . . ?
C4 C3 C8 C7 -0.4(2) . . . . ?
C4 C3 C8 O1 177.49(12) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C3 0.0(2) . . . . ?
C6 C7 C8 O1 -177.67(13) . . . . ?
C7 C8 O1 C1 -171.75(14) . . . . ?
C8 C3 C4 C5 0.7(2) . . . . ?
C9 C2 C3 C4 -66.4(2) . . . . ?
C9 C2 C3 C8 110.39(14) . . . . ?
C10 C5 C6 C7 179.49(16) . . . . ?
C11 C1 C2 C3 -100.08(13) . . . . ?
C11 C1 C2 C9 143.37(12) . . . . ?
C11 C1 O1 C8 104.03(12) . . . . ?
C11 C12 C13 C14 -178.36(16) . . . . ?
C11 C12 C17 C16 177.98(15) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C12 C17 C16 -0.7(2) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C13 C14 C15 C18 179.87(18) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C12 0.5(3) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C18 C15 C16 C17 179.81(16) . . . . ?
O1 C1 C2 C3 15.85(13) . . . . ?
O1 C1 C2 C9 -100.69(13) . . . . ?
O1 C1 C11 C12 68.25(15) . . . . ?
O1 C1 C11 O2 -110.29(15) . . . . ?
O2 C11 C12 C13 4.8(2) . . . . ?
O2 C11 C12 C17 -173.86(16) . . . . ?
