#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151802.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_7151802
loop_
_publ_author_name
'Liu, Yang'
'Huang, Liping'
'Xie, Fuchun'
'Chen, Xuxing'
'Hu, Youhong'
_publ_section_title
;
 Synthesis of novel functional polycyclic chromones through Michael
 addition and double cyclizations.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2680
_journal_page_last               2684
_journal_paper_doi               10.1039/c0ob01000f
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C25 H15 N O2'
_chemical_formula_weight         361.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 109.240(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6312(12)
_cell_length_b                   12.1657(12)
_cell_length_c                   12.2949(12)
_cell_measurement_reflns_used    3490
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.796
_cell_measurement_theta_min      4.783
_cell_volume                     1783.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1142
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9222
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79183
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.311
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0502
_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/[σ²(Fo²)+(0.0752P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1443
_reflns_number_gt                2618
_reflns_number_total             3301
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01000f.txt
_cod_data_source_block           cd29368
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7151802
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
N1 N 0.43346(13) 0.66051(14) 0.59659(13) 0.0553(4) Uani 1 1 d . . .
O1 O 0.41999(11) 1.07635(10) 0.38166(10) 0.0586(4) Uani 1 1 d . . .
O2 O 0.19692(8) 0.95211(9) 0.08944(9) 0.0397(3) Uani 1 1 d . . .
C1 C 0.35912(13) 1.03615(13) 0.29136(14) 0.0381(4) Uani 1 1 d . . .
C2 C 0.33144(12) 1.09235(13) 0.18009(13) 0.0358(4) Uani 1 1 d . . .
C3 C 0.38351(14) 1.19092(13) 0.16701(16) 0.0434(4) Uani 1 1 d . . .
H3 H 0.4348 1.2241 0.2309 0.052 Uiso 1 1 calc R . .
C4 C 0.35933(14) 1.23858(15) 0.06075(15) 0.0468(4) Uani 1 1 d . . .
H4 H 0.3950 1.3035 0.0527 0.056 Uiso 1 1 calc R . .
C5 C 0.28195(17) 1.19056(15) -0.03486(17) 0.0537(5) Uani 1 1 d . . .
H5 H 0.2662 1.2234 -0.1068 0.064 Uiso 1 1 calc R . .
C6 C 0.22837(15) 1.09500(15) -0.02449(15) 0.0495(5) Uani 1 1 d . . .
H6 H 0.1759 1.0631 -0.0885 0.059 Uiso 1 1 calc R . .
C7 C 0.25412(13) 1.04706(13) 0.08329(13) 0.0371(4) Uani 1 1 d . . .
C8 C 0.22761(12) 0.89402(13) 0.18928(13) 0.0340(4) Uani 1 1 d . . .
C9 C 0.30899(12) 0.92640(12) 0.28633(12) 0.0331(4) Uani 1 1 d . . .
C10 C 0.34660(12) 0.85895(13) 0.38866(13) 0.0347(4) Uani 1 1 d . . .
H10 H 0.3741 0.8963 0.4584 0.042 Uiso 1 1 calc R . .
C11 C 0.34651(12) 0.74824(14) 0.39502(12) 0.0345(4) Uani 1 1 d . . .
C12 C 0.31482(12) 0.66875(13) 0.29921(13) 0.0351(4) Uani 1 1 d . . .
C13 C 0.37223(13) 0.56907(14) 0.31162(16) 0.0442(4) Uani 1 1 d . . .
H13 H 0.4245 0.5511 0.3826 0.053 Uiso 1 1 calc R . .
C14 C 0.35313(15) 0.49686(14) 0.22126(17) 0.0497(5) Uani 1 1 d . . .
H14 H 0.3924 0.4309 0.2313 0.060 Uiso 1 1 calc R . .
C15 C 0.27602(14) 0.52206(15) 0.11612(16) 0.0487(5) Uani 1 1 d . . .
H15 H 0.2643 0.4742 0.0542 0.058 Uiso 1 1 calc R . .
C16 C 0.21582(14) 0.61893(14) 0.10272(15) 0.0431(4) Uani 1 1 d . . .
H16 H 0.1633 0.6355 0.0315 0.052 Uiso 1 1 calc R . .
C17 C 0.23215(13) 0.69177(12) 0.19326(14) 0.0351(4) Uani 1 1 d . . .
C18 C 0.15795(13) 0.79196(13) 0.17729(14) 0.0368(4) Uani 1 1 d . . .
H18 H 0.1079 0.7902 0.0972 0.044 Uiso 1 1 calc R . .
C19 C 0.08221(12) 0.79303(13) 0.25199(14) 0.0386(4) Uani 1 1 d . . .
C20 C 0.03878(14) 0.88955(16) 0.27749(16) 0.0514(5) Uani 1 1 d . . .
H20 H 0.0616 0.9561 0.2554 0.062 Uiso 1 1 calc R . .
C21 C -0.03816(16) 0.88919(18) 0.33539(18) 0.0633(6) Uani 1 1 d . . .
H21 H -0.0671 0.9554 0.3509 0.076 Uiso 1 1 calc R . .
C22 C -0.07234(16) 0.79244(19) 0.37022(19) 0.0639(6) Uani 1 1 d . . .
H22 H -0.1260 0.7922 0.4069 0.077 Uiso 1 1 calc R . .
C23 C -0.02615(18) 0.69636(18) 0.3500(2) 0.0703(7) Uani 1 1 d . . .
H23 H -0.0458 0.6304 0.3765 0.084 Uiso 1 1 calc R . .
C24 C 0.04956(17) 0.69616(16) 0.29060(19) 0.0599(6) Uani 1 1 d . . .
H24 H 0.0791 0.6298 0.2763 0.072 Uiso 1 1 calc R . .
C25 C 0.39541(13) 0.70084(14) 0.50833(15) 0.0403(4) 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
C8 O2 C7 119.17(12) . . ?
O1 C1 C2 123.06(15) . . ?
O1 C1 C9 122.26(14) . . ?
C2 C1 C9 114.68(13) . . ?
C7 C2 C3 117.87(15) . . ?
C7 C2 C1 120.13(14) . . ?
C3 C2 C1 121.98(15) . . ?
C4 C3 C2 120.41(16) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.27(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.65(17) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 118.57(17) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
O2 C7 C2 121.46(14) . . ?
O2 C7 C6 116.33(14) . . ?
C2 C7 C6 122.21(15) . . ?
C9 C8 O2 123.65(14) . . ?
C9 C8 C18 125.34(14) . . ?
O2 C8 C18 111.00(12) . . ?
C8 C9 C10 122.64(14) . . ?
C8 C9 C1 119.56(14) . . ?
C10 C9 C1 117.75(13) . . ?
C11 C10 C9 127.66(14) . . ?
C11 C10 H10 116.2 . . ?
C9 C10 H10 116.2 . . ?
C10 C11 C25 116.49(14) . . ?
C10 C11 C12 127.88(14) . . ?
C25 C11 C12 115.20(14) . . ?
C13 C12 C17 118.42(15) . . ?
C13 C12 C11 119.24(14) . . ?
C17 C12 C11 122.27(14) . . ?
C14 C13 C12 121.39(17) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 119.99(16) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.62(16) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 121.31(16) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C16 C17 C12 119.13(15) . . ?
C16 C17 C18 119.38(14) . . ?
C12 C17 C18 121.45(14) . . ?
C8 C18 C17 109.65(13) . . ?
C8 C18 C19 113.36(13) . . ?
C17 C18 C19 114.40(13) . . ?
C8 C18 H18 106.3 . . ?
C17 C18 H18 106.3 . . ?
C19 C18 H18 106.3 . . ?
C20 C19 C24 117.56(16) . . ?
C20 C19 C18 121.32(15) . . ?
C24 C19 C18 121.01(15) . . ?
C19 C20 C21 121.08(17) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 120.77(18) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 118.76(18) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C24 120.63(19) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 121.11(17) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
N1 C25 C11 178.10(18) . . ?
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
N1 C25 1.143(2) . ?
O1 C1 1.2248(19) . ?
O2 C8 1.3575(18) . ?
O2 C7 1.3778(19) . ?
C1 C2 1.465(2) . ?
C1 C9 1.470(2) . ?
C2 C7 1.381(2) . ?
C2 C3 1.402(2) . ?
C3 C4 1.369(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.352(2) . ?
C8 C18 1.501(2) . ?
C9 C10 1.445(2) . ?
C10 C11 1.349(2) . ?
C10 H10 0.9300 . ?
C11 C25 1.445(2) . ?
C11 C12 1.474(2) . ?
C12 C13 1.395(2) . ?
C12 C17 1.403(2) . ?
C13 C14 1.374(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.510(2) . ?
C18 C19 1.529(2) . ?
C18 H18 0.9800 . ?
C19 C20 1.375(2) . ?
C19 C24 1.383(2) . ?
C20 C21 1.381(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
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
O1 C1 C2 C7 -173.97(15) . . . . ?
C9 C1 C2 C7 6.7(2) . . . . ?
O1 C1 C2 C3 7.8(2) . . . . ?
C9 C1 C2 C3 -171.58(13) . . . . ?
C7 C2 C3 C4 -1.3(2) . . . . ?
C1 C2 C3 C4 177.02(14) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C8 O2 C7 C2 -8.8(2) . . . . ?
C8 O2 C7 C6 172.20(13) . . . . ?
C3 C2 C7 O2 -178.10(13) . . . . ?
C1 C2 C7 O2 3.5(2) . . . . ?
C3 C2 C7 C6 0.8(2) . . . . ?
C1 C2 C7 C6 -177.53(14) . . . . ?
C5 C6 C7 O2 179.12(15) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C7 O2 C8 C9 3.0(2) . . . . ?
C7 O2 C8 C18 -178.15(12) . . . . ?
O2 C8 C9 C10 -174.74(13) . . . . ?
C18 C8 C9 C10 6.6(2) . . . . ?
O2 C8 C9 C1 7.8(2) . . . . ?
C18 C8 C9 C1 -170.87(13) . . . . ?
O1 C1 C9 C8 168.47(15) . . . . ?
C2 C1 C9 C8 -12.2(2) . . . . ?
O1 C1 C9 C10 -9.1(2) . . . . ?
C2 C1 C9 C10 170.25(12) . . . . ?
C8 C9 C10 C11 28.8(2) . . . . ?
C1 C9 C10 C11 -153.73(15) . . . . ?
C9 C10 C11 C25 176.30(14) . . . . ?
C9 C10 C11 C12 4.2(2) . . . . ?
C10 C11 C12 C13 144.94(15) . . . . ?
C25 C11 C12 C13 -27.24(19) . . . . ?
C10 C11 C12 C17 -31.9(2) . . . . ?
C25 C11 C12 C17 155.87(14) . . . . ?
C17 C12 C13 C14 3.2(2) . . . . ?
C11 C12 C13 C14 -173.78(14) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 -1.7(2) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C12 2.7(2) . . . . ?
C15 C16 C17 C18 -175.06(14) . . . . ?
C13 C12 C17 C16 -4.4(2) . . . . ?
C11 C12 C17 C16 172.48(13) . . . . ?
C13 C12 C17 C18 173.29(13) . . . . ?
C11 C12 C17 C18 -9.8(2) . . . . ?
C9 C8 C18 C17 -64.3(2) . . . . ?
O2 C8 C18 C17 116.85(14) . . . . ?
C9 C8 C18 C19 64.9(2) . . . . ?
O2 C8 C18 C19 -113.95(14) . . . . ?
C16 C17 C18 C8 -116.87(15) . . . . ?
C12 C17 C18 C8 65.41(18) . . . . ?
C16 C17 C18 C19 114.49(16) . . . . ?
C12 C17 C18 C19 -63.23(18) . . . . ?
C8 C18 C19 C20 31.3(2) . . . . ?
C17 C18 C19 C20 158.07(15) . . . . ?
C8 C18 C19 C24 -152.58(17) . . . . ?
C17 C18 C19 C24 -25.8(2) . . . . ?
C24 C19 C20 C21 -2.6(3) . . . . ?
C18 C19 C20 C21 173.61(16) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C20 C21 C22 C23 2.1(3) . . . . ?
C21 C22 C23 C24 -3.1(4) . . . . ?
C22 C23 C24 C19 1.3(3) . . . . ?
C20 C19 C24 C23 1.6(3) . . . . ?
C18 C19 C24 C23 -174.61(18) . . . . ?
C10 C11 C25 N1 -179(100) . . . . ?
C12 C11 C25 N1 -6(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190633
