#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:21:52 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/15/7061525.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_7061525
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         'C23 H19 N O6'
_chemical_formula_sum            'C23 H19 N O6'
_chemical_formula_weight         405.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_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                101.220(4)
_cell_angle_beta                 102.899(4)
_cell_angle_gamma                107.946(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7790(10)
_cell_length_b                   10.3103(13)
_cell_length_c                   13.8093(18)
_cell_measurement_reflns_used    7375
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      2.17
_cell_volume                     984.8(2)
_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 0.986
_diffrn_measured_fraction_theta_max 0.987
_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  0.0261
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13780
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.889
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3828
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0444
_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)+(0.0602P)²+0.2321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2987
_reflns_number_total             3828
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj01135b2.cif
_cod_data_source_block           7b
_cod_depositor_comments
'Adding full bibliography for 7061522--7061528.cif.'
_cod_database_code               7061525
_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   0.976
_shelx_estimated_absorpt_t_max   0.980
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.1419(2) 0.52888(18) 0.84717(15) 0.0495(4) Uani 1 1 d . . . . .
C2 C 0.0553(3) 0.3951(2) 0.8576(2) 0.0728(6) Uani 1 1 d . . . . .
H2 H -0.0400 0.3235 0.8026 0.087 Uiso 1 1 calc R U . . .
C3 C 0.1153(5) 0.3719(3) 0.9525(3) 0.0902(9) Uani 1 1 d . . . . .
H3 H 0.0574 0.2839 0.9620 0.108 Uiso 1 1 calc R U . . .
C4 C 0.2577(5) 0.4757(3) 1.0322(2) 0.0861(8) Uani 1 1 d . . . . .
H4 H 0.2977 0.4574 1.0950 0.103 Uiso 1 1 calc R U . . .
C5 C 0.3429(3) 0.6076(2) 1.02027(16) 0.0637(5) Uani 1 1 d . . . . .
H5 H 0.4412 0.6775 1.0749 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2833(2) 0.63675(18) 0.92769(13) 0.0461(4) Uani 1 1 d . . . . .
C7 C 0.3554(2) 0.78032(16) 0.91076(11) 0.0400(4) Uani 1 1 d . . . . .
H7 H 0.4777 0.8384 0.9632 0.048 Uiso 1 1 calc R U . . .
C8 C 0.37781(19) 0.77000(15) 0.80193(11) 0.0353(3) Uani 1 1 d . . . . .
C9 C 0.2196(2) 0.63943(16) 0.71919(12) 0.0398(4) Uani 1 1 d . . . . .
C10 C 0.3177(2) 0.55199(17) 0.67139(12) 0.0429(4) Uani 1 1 d . . . . .
C11 C 0.2367(3) 0.4246(2) 0.59380(15) 0.0631(5) Uani 1 1 d . . . . .
H11 H 0.1060 0.3827 0.5633 0.076 Uiso 1 1 calc R U . . .
C12 C 0.3552(4) 0.3622(3) 0.56321(19) 0.0835(7) Uani 1 1 d . . . . .
H12 H 0.3038 0.2769 0.5106 0.100 Uiso 1 1 calc R U . . .
C13 C 0.5497(4) 0.4230(3) 0.6088(2) 0.0862(7) Uani 1 1 d . . . . .
H13 H 0.6264 0.3772 0.5872 0.103 Uiso 1 1 calc R U . . .
C14 C 0.6310(3) 0.5497(2) 0.68532(16) 0.0640(5) Uani 1 1 d . . . . .
H14 H 0.7618 0.5913 0.7155 0.077 Uiso 1 1 calc R U . . .
C15 C 0.5119(2) 0.61392(18) 0.71639(12) 0.0443(4) Uani 1 1 d . . . . .
C16 C 0.5615(2) 0.74855(17) 0.79540(12) 0.0402(4) Uani 1 1 d . . . . .
C17 C 0.1573(3) 1.0406(2) 0.83628(18) 0.0709(6) Uani 1 1 d . . . . .
H17A H 0.0355 0.9749 0.7913 0.106 Uiso 1 1 calc R U . . .
H17B H 0.2099 1.1100 0.8030 0.106 Uiso 1 1 calc R U . . .
H17C H 0.1436 1.0874 0.8997 0.106 Uiso 1 1 calc R U . . .
C18 C 0.2194(2) 0.85919(17) 0.91189(13) 0.0455(4) Uani 1 1 d . . . . .
H18A H 0.0895 0.7954 0.8755 0.055 Uiso 1 1 calc R U . . .
H18B H 0.2281 0.9043 0.9823 0.055 Uiso 1 1 calc R U . . .
C19 C 0.1846(2) 0.83215(19) 0.67046(13) 0.0476(4) Uani 1 1 d . . . . .
C20 C 0.3443(2) 0.89976(16) 0.77362(12) 0.0406(4) Uani 1 1 d . . . . .
C21 C 0.5098(3) 1.01677(18) 0.76322(13) 0.0506(4) Uani 1 1 d . . . . .
H21A H 0.4717 1.0966 0.7567 0.061 Uiso 1 1 calc R U . . .
H21B H 0.6145 1.0490 0.8266 0.061 Uiso 1 1 calc R U . . .
C22 C 0.5795(2) 0.97548(18) 0.67396(13) 0.0466(4) Uani 1 1 d . . . . .
C23 C 0.7992(3) 1.0635(3) 0.58645(19) 0.0790(6) Uani 1 1 d . . . . .
H23A H 0.8637 0.9986 0.5942 0.118 Uiso 1 1 calc R U . . .
H23B H 0.8875 1.1529 0.5875 0.118 Uiso 1 1 calc R U . . .
H23C H 0.6994 1.0249 0.5217 0.118 Uiso 1 1 calc R U . . .
N1 N 0.2836(2) 0.96381(14) 0.85879(11) 0.0472(3) Uani 1 1 d . . . . .
O1 O 0.07604(15) 0.55689(12) 0.75424(9) 0.0517(3) Uani 1 1 d . . . . .
O2 O 0.71752(15) 0.82906(14) 0.85003(10) 0.0601(4) Uani 1 1 d . . . . .
O3 O 0.11748(16) 0.68910(13) 0.64579(9) 0.0525(3) Uani 1 1 d . . . . .
O4 O 0.1182(2) 0.89276(16) 0.61622(10) 0.0696(4) Uani 1 1 d . . . . .
O5 O 0.51758(19) 0.86019(14) 0.61316(10) 0.0636(4) Uani 1 1 d . . . . .
O6 O 0.7196(2) 1.08467(14) 0.67064(11) 0.0663(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
C6 C1 C2 122.13(19) . . ?
C6 C1 O1 119.14(15) . . ?
C2 C1 O1 118.62(18) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.15(17) . . ?
C1 C6 C7 117.64(15) . . ?
C5 C6 C7 124.13(17) . . ?
C6 C7 C18 113.92(13) . . ?
C6 C7 C8 111.82(12) . . ?
C18 C7 C8 102.09(12) . . ?
C6 C7 H7 109.6 . . ?
C18 C7 H7 109.6 . . ?
C8 C7 H7 109.6 . . ?
C16 C8 C7 112.02(12) . . ?
C16 C8 C20 118.12(12) . . ?
C7 C8 C20 105.39(11) . . ?
C16 C8 C9 104.25(11) . . ?
C7 C8 C9 112.06(12) . . ?
C20 C8 C9 104.90(12) . . ?
O3 C9 O1 103.00(11) . . ?
O3 C9 C10 111.97(13) . . ?
O1 C9 C10 111.64(13) . . ?
O3 C9 C8 108.03(12) . . ?
O1 C9 C8 116.12(12) . . ?
C10 C9 C8 106.15(12) . . ?
C15 C10 C11 120.87(16) . . ?
C15 C10 C9 111.06(13) . . ?
C11 C10 C9 128.06(15) . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C11 C12 C13 121.5(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 120.94(19) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 117.9(2) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C10 C15 C14 120.95(16) . . ?
C10 C15 C16 110.16(13) . . ?
C14 C15 C16 128.88(16) . . ?
O2 C16 C15 127.70(15) . . ?
O2 C16 C8 123.90(14) . . ?
C15 C16 C8 108.35(12) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C7 103.20(12) . . ?
N1 C18 H18A 111.1 . . ?
C7 C18 H18A 111.1 . . ?
N1 C18 H18B 111.1 . . ?
C7 C18 H18B 111.1 . . ?
H18A C18 H18B 109.1 . . ?
O4 C19 O3 121.09(16) . . ?
O4 C19 C20 126.98(17) . . ?
O3 C19 C20 111.90(13) . . ?
N1 C20 C21 107.51(12) . . ?
N1 C20 C19 112.88(13) . . ?
C21 C20 C19 110.35(14) . . ?
N1 C20 C8 104.37(12) . . ?
C21 C20 C8 118.76(13) . . ?
C19 C20 C8 102.96(12) . . ?
C22 C21 C20 115.42(14) . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C20 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
O5 C22 O6 124.13(16) . . ?
O5 C22 C21 125.24(16) . . ?
O6 C22 C21 110.62(15) . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 N1 C17 113.75(15) . . ?
C18 N1 C20 108.89(12) . . ?
C17 N1 C20 118.27(14) . . ?
C1 O1 C9 114.93(12) . . ?
C19 O3 C9 111.77(12) . . ?
C22 O6 C23 117.55(16) . . ?
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 C6 1.379(3) . ?
C1 C2 1.387(3) . ?
C1 O1 1.391(2) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(2) . ?
C7 C18 1.521(2) . ?
C7 C8 1.538(2) . ?
C7 H7 0.9800 . ?
C8 C16 1.531(2) . ?
C8 C20 1.544(2) . ?
C8 C9 1.544(2) . ?
C9 O3 1.4193(19) . ?
C9 O1 1.4220(19) . ?
C9 C10 1.499(2) . ?
C10 C15 1.382(2) . ?
C10 C11 1.382(2) . ?
C11 C12 1.370(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.469(2) . ?
C16 O2 1.2074(18) . ?
C17 N1 1.458(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N1 1.446(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O4 1.194(2) . ?
C19 O3 1.347(2) . ?
C19 C20 1.532(2) . ?
C20 N1 1.477(2) . ?
C20 C21 1.526(2) . ?
C21 C22 1.493(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O5 1.195(2) . ?
C22 O6 1.321(2) . ?
C23 O6 1.445(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
