#------------------------------------------------------------------------------
#$Date: 2025-11-12 03:12:23 +0100 (Wed 12 de Nov de 2025) $
#$Revision: 303274 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/08/7160849.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_7160849
loop_
_publ_author_name
'Qiao, Qiwei'
'Sun, Hong'
'Sudprasert, Pirada'
'Cheng, Jin'
_publ_section_title
;
 Base-promoted [4+2] cycloaddition of para-quinone methides (p-QMs) and
 3-cyanochromones: Facile Access to chromeno[2,3-b]chromenes
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01516B
_journal_year                    2025
_chemical_formula_sum            'C31 H31 N O4'
_chemical_formula_weight         481.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-09-22 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3834(5)
_cell_length_b                   16.1469(9)
_cell_length_c                   17.4024(10)
_cell_measurement_reflns_used    8690
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.84
_cell_measurement_theta_min      4.74
_cell_volume                     2636.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14428
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.865
_diffrn_reflns_theta_min         4.742
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4538
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0343
_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)+(0.0500P)²+0.2035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.886
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                4155
_reflns_number_total             4538
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01516b2.cif
_cod_data_source_block           S_a
_cod_database_code               7160849
_shelx_shelxl_version_number     2018/3
_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.
;
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'
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
O3 O 0.2403(2) 0.62763(11) 0.35195(10) 0.0416(4) Uani 1 1 d . . . . .
O2 O 0.40192(17) 0.62050(11) 0.44854(10) 0.0389(4) Uani 1 1 d . . . . .
O4 O 0.57278(19) 0.33932(13) 0.64375(11) 0.0480(5) Uani 1 1 d . . . . .
H4A H 0.543461 0.329526 0.688447 0.072 Uiso 1 1 calc R U . . .
O1 O 0.0942(2) 0.62793(12) 0.61414(11) 0.0502(5) Uani 1 1 d . . . . .
N1 N -0.0977(2) 0.66187(16) 0.44756(15) 0.0539(6) Uani 1 1 d . . . . .
C10 C 0.0110(3) 0.63603(14) 0.46328(16) 0.0377(6) Uani 1 1 d . . . . .
C18 C 0.3376(2) 0.39911(14) 0.63688(13) 0.0329(5) Uani 1 1 d . . . . .
C19 C 0.2642(2) 0.45896(13) 0.51454(13) 0.0305(5) Uani 1 1 d . . . . .
C12 C 0.1964(2) 0.54846(15) 0.33174(13) 0.0343(5) Uani 1 1 d . . . . .
C13 C 0.1025(3) 0.41436(17) 0.35530(16) 0.0444(6) Uani 1 1 d . . . . .
H13 H 0.071124 0.372636 0.389869 0.053 Uiso 1 1 calc R U . . .
C20 C 0.3926(2) 0.43435(14) 0.48254(14) 0.0335(5) Uani 1 1 d . . . . .
H20 H 0.410377 0.446502 0.429992 0.040 Uiso 1 1 calc R U . . .
C14 C 0.1509(2) 0.48973(15) 0.38447(14) 0.0328(5) Uani 1 1 d . . . . .
C11 C 0.1505(2) 0.50614(14) 0.46985(13) 0.0315(5) Uani 1 1 d . . . . .
H11 H 0.056363 0.486277 0.489522 0.038 Uiso 1 1 calc R U . . .
C21 C 0.2374(2) 0.43934(14) 0.59073(13) 0.0322(5) Uani 1 1 d . . . . .
H21 H 0.147816 0.453772 0.612315 0.039 Uiso 1 1 calc R U . . .
C22 C 0.4663(3) 0.37791(14) 0.60212(13) 0.0335(5) Uani 1 1 d . . . . .
C23 C 0.4963(2) 0.39263(15) 0.52426(14) 0.0345(5) Uani 1 1 d . . . . .
C15 C 0.1940(3) 0.53335(18) 0.25315(14) 0.0430(6) Uani 1 1 d . . . . .
H15 H 0.226134 0.574466 0.218149 0.052 Uiso 1 1 calc R U . . .
C28 C 0.3053(3) 0.38092(17) 0.72223(15) 0.0424(6) Uani 1 1 d . . . . .
C8 C 0.1531(2) 0.60274(14) 0.48251(13) 0.0317(5) Uani 1 1 d . . . . .
C9 C 0.2615(3) 0.64524(15) 0.42922(14) 0.0345(5) Uani 1 1 d . . . . .
H9 H 0.253778 0.706500 0.436573 0.041 Uiso 1 1 calc R U . . .
C1 C 0.4395(3) 0.63637(14) 0.52331(15) 0.0392(6) Uani 1 1 d . . . . .
C2 C 0.3390(3) 0.64065(15) 0.58181(15) 0.0393(6) Uani 1 1 d . . . . .
C7 C 0.1884(3) 0.62532(14) 0.56651(14) 0.0371(6) Uani 1 1 d . . . . .
C16 C 0.0991(3) 0.39906(19) 0.27717(17) 0.0521(7) Uani 1 1 d . . . . .
H16 H 0.065129 0.347397 0.258572 0.063 Uiso 1 1 calc R U . . .
C17 C 0.1450(3) 0.45849(19) 0.22641(16) 0.0478(7) Uani 1 1 d . . . . .
H17 H 0.142728 0.447854 0.172730 0.057 Uiso 1 1 calc R U . . .
C3 C 0.5842(3) 0.64690(18) 0.5383(2) 0.0520(7) Uani 1 1 d . . . . .
H3 H 0.652217 0.643407 0.497981 0.062 Uiso 1 1 calc R U . . .
C24 C 0.6365(3) 0.36336(17) 0.48692(16) 0.0435(6) Uani 1 1 d . . . . .
C4 C 0.3868(4) 0.65625(18) 0.65725(18) 0.0557(8) Uani 1 1 d . . . . .
H4 H 0.319981 0.659310 0.698169 0.067 Uiso 1 1 calc R U . . .
C5 C 0.5281(4) 0.66696(19) 0.6717(2) 0.0682(10) Uani 1 1 d . . . . .
H5 H 0.559590 0.677588 0.722634 0.082 Uiso 1 1 calc R U . . .
C29 C 0.4058(4) 0.4307(2) 0.77396(18) 0.0671(9) Uani 1 1 d . . . . .
H29A H 0.504745 0.415907 0.762274 0.101 Uiso 0.5 1 calc R U P . .
H29B H 0.391597 0.490016 0.764775 0.101 Uiso 0.5 1 calc R U P . .
H29C H 0.385366 0.418054 0.827919 0.101 Uiso 0.5 1 calc R U P . .
H29D H 0.349726 0.466745 0.807705 0.101 Uiso 0.5 1 calc R U P . .
H29E H 0.462875 0.392636 0.805204 0.101 Uiso 0.5 1 calc R U P . .
H29F H 0.469106 0.464597 0.742059 0.101 Uiso 0.5 1 calc R U P . .
C6 C 0.6263(4) 0.66238(19) 0.6122(3) 0.0658(10) Uani 1 1 d . . . . .
H6 H 0.724629 0.670151 0.622955 0.079 Uiso 1 1 calc R U . . .
C25 C 0.6528(4) 0.26953(19) 0.4965(2) 0.0630(9) Uani 1 1 d . . . . .
H25A H 0.567673 0.241723 0.476448 0.094 Uiso 1 1 calc R U . . .
H25B H 0.664248 0.256196 0.551046 0.094 Uiso 1 1 calc R U . . .
H25C H 0.736802 0.250645 0.467981 0.094 Uiso 1 1 calc R U . . .
C30 C 0.3186(4) 0.2881(2) 0.74027(19) 0.0661(9) Uani 1 1 d . . . . .
H30A H 0.415257 0.269266 0.728006 0.099 Uiso 0.5 1 calc R U P . .
H30B H 0.299483 0.278780 0.794953 0.099 Uiso 0.5 1 calc R U P . .
H30C H 0.249579 0.257042 0.709361 0.099 Uiso 0.5 1 calc R U P . .
H30D H 0.227623 0.267459 0.760207 0.099 Uiso 0.5 1 calc R U P . .
H30E H 0.343396 0.257945 0.693261 0.099 Uiso 0.5 1 calc R U P . .
H30F H 0.393300 0.279683 0.778852 0.099 Uiso 0.5 1 calc R U P . .
C26 C 0.7646(3) 0.4065(2) 0.5242(2) 0.0689(9) Uani 1 1 d . . . . .
H26A H 0.852235 0.389641 0.497800 0.103 Uiso 1 1 calc R U . . .
H26B H 0.770416 0.390815 0.578480 0.103 Uiso 1 1 calc R U . . .
H26C H 0.753186 0.466682 0.520040 0.103 Uiso 1 1 calc R U . . .
C27 C 0.6384(5) 0.3819(3) 0.4017(2) 0.0929(15) Uani 1 1 d . . . . .
H27A H 0.556732 0.355044 0.376980 0.139 Uiso 1 1 calc R U . . .
H27B H 0.726947 0.360782 0.379176 0.139 Uiso 1 1 calc R U . . .
H27C H 0.632760 0.441901 0.393755 0.139 Uiso 1 1 calc R U . . .
C31 C 0.1541(4) 0.4059(3) 0.74240(19) 0.0843(13) Uani 1 1 d . . . . .
H31A H 0.087147 0.376339 0.709011 0.126 Uiso 1 1 calc R U . . .
H31B H 0.142819 0.465715 0.735059 0.126 Uiso 1 1 calc R U . . .
H31C H 0.134688 0.391790 0.796155 0.126 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
C12 O3 C9 118.45(18) . . ?
C1 O2 C9 114.28(19) . . ?
C22 O4 H4A 109.5 . . ?
N1 C10 C8 179.1(3) . . ?
C22 C18 C21 116.6(2) . . ?
C22 C18 C28 122.7(2) . . ?
C21 C18 C28 120.6(2) . . ?
C21 C19 C20 118.5(2) . . ?
C21 C19 C11 118.39(19) . . ?
C20 C19 C11 123.2(2) . . ?
C14 C12 O3 123.6(2) . . ?
C14 C12 C15 121.8(2) . . ?
O3 C12 C15 114.6(2) . . ?
C16 C13 C14 121.4(3) . . ?
C16 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C19 C20 C23 122.6(2) . . ?
C19 C20 H20 118.7 . . ?
C23 C20 H20 118.7 . . ?
C12 C14 C13 117.1(2) . . ?
C12 C14 C11 122.2(2) . . ?
C13 C14 C11 120.7(2) . . ?
C14 C11 C19 114.37(18) . . ?
C14 C11 C8 108.15(18) . . ?
C19 C11 C8 114.37(18) . . ?
C14 C11 H11 106.5 . . ?
C19 C11 H11 106.5 . . ?
C8 C11 H11 106.5 . . ?
C19 C21 C18 122.3(2) . . ?
C19 C21 H21 118.8 . . ?
C18 C21 H21 118.8 . . ?
O4 C22 C18 120.6(2) . . ?
O4 C22 C23 115.9(2) . . ?
C18 C22 C23 123.5(2) . . ?
C20 C23 C22 116.5(2) . . ?
C20 C23 C24 121.8(2) . . ?
C22 C23 C24 121.7(2) . . ?
C17 C15 C12 119.5(3) . . ?
C17 C15 H15 120.2 . . ?
C12 C15 H15 120.2 . . ?
C31 C28 C29 107.5(3) . . ?
C31 C28 C30 106.7(3) . . ?
C29 C28 C30 110.0(3) . . ?
C31 C28 C18 110.8(2) . . ?
C29 C28 C18 110.2(2) . . ?
C30 C28 C18 111.5(2) . . ?
C10 C8 C9 107.35(19) . . ?
C10 C8 C7 108.8(2) . . ?
C9 C8 C7 108.88(19) . . ?
C10 C8 C11 108.37(19) . . ?
C9 C8 C11 111.56(19) . . ?
C7 C8 C11 111.70(18) . . ?
O3 C9 O2 107.77(19) . . ?
O3 C9 C8 113.4(2) . . ?
O2 C9 C8 110.26(19) . . ?
O3 C9 H9 108.4 . . ?
O2 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
O2 C1 C2 122.0(2) . . ?
O2 C1 C3 116.8(2) . . ?
C2 C1 C3 121.2(3) . . ?
C1 C2 C4 118.4(3) . . ?
C1 C2 C7 121.0(2) . . ?
C4 C2 C7 120.5(3) . . ?
O1 C7 C2 125.1(2) . . ?
O1 C7 C8 120.0(2) . . ?
C2 C7 C8 114.9(2) . . ?
C17 C16 C13 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C13 C16 H16 120.0 . . ?
C16 C17 C15 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C15 C17 H17 120.0 . . ?
C6 C3 C1 118.7(3) . . ?
C6 C3 H3 120.7 . . ?
C1 C3 H3 120.7 . . ?
C27 C24 C25 107.5(3) . . ?
C27 C24 C26 108.4(3) . . ?
C25 C24 C26 109.0(2) . . ?
C27 C24 C23 111.3(2) . . ?
C25 C24 C23 110.0(2) . . ?
C26 C24 C23 110.6(2) . . ?
C5 C4 C2 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C2 C4 H4 119.8 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
H29D C29 H29E 109.5 . . ?
H29D C29 H29F 109.5 . . ?
H29E C29 H29F 109.5 . . ?
C3 C6 C5 121.3(3) . . ?
C3 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
H30D C30 H30E 109.5 . . ?
H30D C30 H30F 109.5 . . ?
H30E C30 H30F 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
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
O3 C12 1.388(3) . ?
O3 C9 1.389(3) . ?
O2 C1 1.372(3) . ?
O2 C9 1.417(3) . ?
O4 C22 1.383(3) . ?
O4 H4A 0.8400 . ?
O1 C7 1.212(3) . ?
N1 C10 1.136(3) . ?
C10 C8 1.476(3) . ?
C18 C22 1.393(3) . ?
C18 C21 1.396(3) . ?
C18 C28 1.544(3) . ?
C19 C21 1.386(3) . ?
C19 C20 1.386(3) . ?
C19 C11 1.524(3) . ?
C12 C14 1.387(3) . ?
C12 C15 1.389(3) . ?
C13 C16 1.382(4) . ?
C13 C14 1.395(4) . ?
C13 H13 0.9500 . ?
C20 C23 1.388(3) . ?
C20 H20 0.9500 . ?
C14 C11 1.509(3) . ?
C11 C8 1.576(3) . ?
C11 H11 1.0000 . ?
C21 H21 0.9500 . ?
C22 C23 1.404(3) . ?
C23 C24 1.541(3) . ?
C15 C17 1.375(4) . ?
C15 H15 0.9500 . ?
C28 C31 1.516(4) . ?
C28 C29 1.532(4) . ?
C28 C30 1.536(4) . ?
C8 C9 1.538(3) . ?
C8 C7 1.543(3) . ?
C9 H9 1.0000 . ?
C1 C2 1.389(4) . ?
C1 C3 1.392(4) . ?
C2 C4 1.410(4) . ?
C2 C7 1.460(4) . ?
C16 C17 1.373(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C3 C6 1.369(5) . ?
C3 H3 0.9500 . ?
C24 C27 1.513(5) . ?
C24 C25 1.532(4) . ?
C24 C26 1.534(4) . ?
C4 C5 1.360(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(6) . ?
C5 H5 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C29 H29D 0.9800 . ?
C29 H29E 0.9800 . ?
C29 H29F 0.9800 . ?
C6 H6 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C30 H30D 0.9800 . ?
C30 H30E 0.9800 . ?
C30 H30F 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
