#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:21:52 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/15/7061522.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_7061522
loop_
_publ_author_name
'Liu, Xueyan'
'Sun, Jing'
'Yan, Chao-Guo'
_publ_section_title
;
 Convenient construction of polycyclic architectures via multicomponent
 reaction of amino acids, dialkyl but-2-ynedioates and
 2-(o-hydroxyarylidene)-1,3-indanediones
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11877
_journal_page_last               11882
_journal_paper_doi               10.1039/D2NJ01135B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C25 H21 N O8'
_chemical_formula_sum            'C25 H21 N O8'
_chemical_formula_weight         463.43
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-05-18 deposited with the CCDC.	2022-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.734(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3841(6)
_cell_length_b                   23.6505(15)
_cell_length_c                   10.8848(8)
_cell_measurement_reflns_used    6364
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.22
_cell_volume                     2211.4(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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.523
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0469
_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)+(0.0489P)²+0.8506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3213
_reflns_number_total             4330
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj01135b2.cif
_cod_data_source_block           4a
_cod_depositor_comments
'Adding full bibliography for 7061522--7061528.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7061522
_shelx_shelxl_version_number     2014/7
_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_min   0.975
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_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_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 0.7366(2) 0.15279(8) 0.78234(19) 0.0413(5) Uani 1 1 d . . . . .
C2 C 0.8686(3) 0.18567(11) 0.8294(3) 0.0672(7) Uani 1 1 d . . . . .
H2 H 0.9020 0.2041 0.7702 0.081 Uiso 1 1 calc R U . . .
C3 C 0.9500(3) 0.19068(13) 0.9657(3) 0.0877(9) Uani 1 1 d . . . . .
H3 H 1.0390 0.2130 0.9993 0.105 Uiso 1 1 calc R U . . .
C4 C 0.9014(3) 0.16301(12) 1.0529(3) 0.0763(8) Uani 1 1 d . . . . .
H4 H 0.9585 0.1662 1.1450 0.092 Uiso 1 1 calc R U . . .
C5 C 0.7675(2) 0.13029(9) 1.0042(2) 0.0505(5) Uani 1 1 d . . . . .
H5 H 0.7344 0.1119 1.0636 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6829(2) 0.12492(7) 0.86673(18) 0.0358(4) Uani 1 1 d . . . . .
C7 C 0.5380(2) 0.08999(7) 0.80322(17) 0.0312(4) Uani 1 1 d . . . . .
H7 H 0.4926 0.0836 0.8689 0.037 Uiso 1 1 calc R U . . .
C8 C 0.41627(19) 0.11904(7) 0.67794(16) 0.0289(4) Uani 1 1 d . . . . .
C9 C 0.4927(2) 0.15376(7) 0.60060(16) 0.0325(4) Uani 1 1 d . . . . .
C10 C 0.4521(2) 0.21448(7) 0.61179(16) 0.0326(4) Uani 1 1 d . . . . .
C11 C 0.5021(2) 0.26230(8) 0.56729(19) 0.0423(5) Uani 1 1 d . . . . .
H11 H 0.5649 0.2596 0.5197 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4555(3) 0.31411(8) 0.5962(2) 0.0487(5) Uani 1 1 d . . . . .
H12 H 0.4856 0.3468 0.5656 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3651(2) 0.31867(8) 0.66959(19) 0.0473(5) Uani 1 1 d . . . . .
H13 H 0.3376 0.3543 0.6890 0.057 Uiso 1 1 calc R U . . .
C14 C 0.3152(2) 0.27117(8) 0.71428(18) 0.0398(4) Uani 1 1 d . . . . .
H14 H 0.2545 0.2741 0.7637 0.048 Uiso 1 1 calc R U . . .
C15 C 0.35881(19) 0.21887(7) 0.68287(16) 0.0318(4) Uani 1 1 d . . . . .
C16 C 0.32193(19) 0.16246(7) 0.71817(16) 0.0313(4) Uani 1 1 d . . . . .
C17 C 0.5628(2) 0.03212(7) 0.74745(18) 0.0357(4) Uani 1 1 d . . . . .
H17 H 0.6478 0.0350 0.7172 0.043 Uiso 1 1 calc R U . . .
C18 C 0.6012(2) -0.01234(8) 0.85589(18) 0.0374(4) Uani 1 1 d . . . . .
C19 C 0.7987(3) -0.04422(10) 1.0597(2) 0.0654(7) Uani 1 1 d . . . . .
H19A H 0.7307 -0.0396 1.1065 0.078 Uiso 1 1 calc R U . . .
H19B H 0.7943 -0.0834 1.0321 0.078 Uiso 1 1 calc R U . . .
C20 C 0.9565(3) -0.02960(15) 1.1478(3) 0.0943(11) Uani 1 1 d . . . . .
H20A H 1.0221 -0.0319 1.0993 0.141 Uiso 1 1 calc R U . . .
H20B H 0.9935 -0.0554 1.2222 0.141 Uiso 1 1 calc R U . . .
H20C H 0.9588 0.0082 1.1806 0.141 Uiso 1 1 calc R U . . .
C21 C 0.3423(2) 0.08762(7) 0.44920(18) 0.0377(4) Uani 1 1 d . . . . .
C22 C 0.3286(2) 0.07113(7) 0.58017(17) 0.0335(4) Uani 1 1 d . . . . .
C23 C 0.1580(2) 0.06059(8) 0.55144(19) 0.0428(5) Uani 1 1 d . . . . .
H23A H 0.1247 0.0264 0.4983 0.051 Uiso 1 1 calc R U . . .
H23B H 0.1488 0.0541 0.6359 0.051 Uiso 1 1 calc R U . . .
C24 C 0.0504(2) 0.10753(9) 0.47913(18) 0.0424(5) Uani 1 1 d . . . . .
C25 C -0.2122(3) 0.13739(14) 0.3918(3) 0.0853(9) Uani 1 1 d . . . . .
H25A H -0.1857 0.1723 0.4410 0.128 Uiso 1 1 calc R U . . .
H25B H -0.3117 0.1246 0.3862 0.128 Uiso 1 1 calc R U . . .
H25C H -0.2168 0.1433 0.3030 0.128 Uiso 1 1 calc R U . . .
N1 N 0.4177(2) 0.01926(7) 0.63409(18) 0.0494(5) Uani 1 1 d . . . . .
O1 O 0.65627(14) 0.14613(6) 0.64422(13) 0.0422(3) Uani 1 1 d . . . . .
O2 O 0.43301(15) 0.13421(5) 0.46595(12) 0.0406(3) Uani 1 1 d . . . . .
O3 O 0.28372(17) 0.06456(6) 0.34318(13) 0.0541(4) Uani 1 1 d . . . . .
O4 O 0.23641(16) 0.15075(6) 0.77312(13) 0.0454(3) Uani 1 1 d . . . . .
O5 O 0.50844(17) -0.04507(6) 0.86587(16) 0.0585(4) Uani 1 1 d . . . . .
O6 O 0.74731(15) -0.00757(6) 0.94216(13) 0.0469(4) Uani 1 1 d . . . . .
O7 O 0.08955(16) 0.15035(6) 0.44254(15) 0.0565(4) Uani 1 1 d . . . . .
O8 O -0.09495(16) 0.09516(7) 0.46006(17) 0.0674(5) Uani 1 1 d . . . . .
H1 H 0.369(4) -0.0032(15) 0.652(4) 0.120(14) Uiso 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 C6 122.5(2) . . ?
C2 C1 O1 118.71(19) . . ?
C6 C1 O1 118.72(16) . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.01(18) . . ?
C1 C6 C7 117.51(16) . . ?
C5 C6 C7 124.47(18) . . ?
C6 C7 C8 111.91(14) . . ?
C6 C7 C17 114.53(14) . . ?
C8 C7 C17 102.78(13) . . ?
C6 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
C17 C7 H7 109.1 . . ?
C16 C8 C9 104.38(13) . . ?
C16 C8 C7 110.72(13) . . ?
C9 C8 C7 112.17(13) . . ?
C16 C8 C22 118.68(14) . . ?
C9 C8 C22 104.47(13) . . ?
C7 C8 C22 106.36(13) . . ?
O2 C9 O1 103.13(13) . . ?
O2 C9 C10 112.79(14) . . ?
O1 C9 C10 111.62(14) . . ?
O2 C9 C8 108.25(13) . . ?
O1 C9 C8 115.20(13) . . ?
C10 C9 C8 105.99(14) . . ?
C11 C10 C15 120.90(17) . . ?
C11 C10 C9 128.25(17) . . ?
C15 C10 C9 110.76(15) . . ?
C12 C11 C10 117.52(19) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C11 C12 C13 121.71(18) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 120.94(18) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 117.62(19) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C10 C15 C14 121.29(17) . . ?
C10 C15 C16 110.27(15) . . ?
C14 C15 C16 128.42(17) . . ?
O4 C16 C15 127.63(16) . . ?
O4 C16 C8 124.24(15) . . ?
C15 C16 C8 108.09(14) . . ?
N1 C17 C18 111.37(16) . . ?
N1 C17 C7 106.24(14) . . ?
C18 C17 C7 109.52(14) . . ?
N1 C17 H17 109.9 . . ?
C18 C17 H17 109.9 . . ?
C7 C17 H17 109.9 . . ?
O5 C18 O6 125.04(17) . . ?
O5 C18 C17 124.37(17) . . ?
O6 C18 C17 110.44(16) . . ?
C20 C19 O6 109.2(2) . . ?
C20 C19 H19A 109.8 . . ?
O6 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
O6 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 O2 121.37(17) . . ?
O3 C21 C22 127.27(18) . . ?
O2 C21 C22 111.36(14) . . ?
N1 C22 C23 109.17(16) . . ?
N1 C22 C21 109.68(15) . . ?
C23 C22 C21 109.00(15) . . ?
N1 C22 C8 106.11(14) . . ?
C23 C22 C8 119.07(15) . . ?
C21 C22 C8 103.48(14) . . ?
C24 C23 C22 114.73(15) . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23B 108.6 . . ?
C22 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
O7 C24 O8 124.57(19) . . ?
O7 C24 C23 124.76(18) . . ?
O8 C24 C23 110.67(18) . . ?
O8 C25 H25A 109.5 . . ?
O8 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O8 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C17 N1 C22 110.66(15) . . ?
C17 N1 H1 112(3) . . ?
C22 N1 H1 112(3) . . ?
C1 O1 C9 112.80(13) . . ?
C21 O2 C9 111.59(13) . . ?
C18 O6 C19 117.15(16) . . ?
C24 O8 C25 116.65(19) . . ?
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 C2 1.375(3) . ?
C1 C6 1.380(3) . ?
C1 O1 1.393(2) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.500(2) . ?
C7 C8 1.544(2) . ?
C7 C17 1.552(2) . ?
C7 H7 0.9800 . ?
C8 C16 1.530(2) . ?
C8 C9 1.544(2) . ?
C8 C22 1.546(2) . ?
C9 O2 1.419(2) . ?
C9 O1 1.424(2) . ?
C9 C10 1.503(2) . ?
C10 C11 1.385(2) . ?
C10 C15 1.386(2) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.468(2) . ?
C16 O4 1.210(2) . ?
C17 N1 1.455(2) . ?
C17 C18 1.512(2) . ?
C17 H17 0.9800 . ?
C18 O5 1.202(2) . ?
C18 O6 1.318(2) . ?
C19 C20 1.445(3) . ?
C19 O6 1.457(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O3 1.192(2) . ?
C21 O2 1.359(2) . ?
C21 C22 1.532(3) . ?
C22 N1 1.468(2) . ?
C22 C23 1.523(3) . ?
C23 C24 1.494(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O7 1.199(2) . ?
C24 O8 1.327(2) . ?
C25 O8 1.450(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N1 H1 0.78(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.78(3) 2.38(4) 2.771(2) 112(3) .
