#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:21:52 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/15/7061527.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_7061527
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         'C27 H26 Br N O7 S'
_chemical_formula_sum            'C27 H26 Br N O7 S'
_chemical_formula_weight         588.46
_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                95.335(2)
_cell_angle_beta                 105.086(2)
_cell_angle_gamma                114.424(2)
_cell_formula_units_Z            2
_cell_length_a                   11.3861(8)
_cell_length_b                   11.8929(9)
_cell_length_c                   13.0322(9)
_cell_measurement_reflns_used    7961
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.52
_cell_volume                     1510.51(19)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0439
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21709
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.098
_exptl_absorpt_coefficient_mu    1.470
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0206(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0478
_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)+(0.0687P)²+0.5665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1405
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4016
_reflns_number_total             5929
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj01135b2.cif
_cod_data_source_block           k
_cod_depositor_comments
'Adding full bibliography for 7061522--7061528.cif.'
_cod_database_code               7061527
_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   0.719
_shelx_estimated_absorpt_t_max   0.778
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
Br1 Br 0.7583(11) 0.0768(5) 0.1601(8) 0.0949(13) Uani 0.48(4) 1 d . . P A 1
Br1' Br 0.7381(10) 0.0728(5) 0.1428(10) 0.1010(14) Uani 0.52(4) 1 d . . P A 2
C1 C 1.0342(3) 0.4982(3) 0.1818(2) 0.0337(6) Uani 1 1 d . . . . .
C2 C 1.0289(3) 0.4040(3) 0.1063(2) 0.0463(8) Uani 1 1 d . . . . .
H2 H 1.0831 0.4260 0.0619 0.056 Uiso 1 1 calc R U . . .
C3 C 0.9442(4) 0.2791(3) 0.0970(3) 0.0577(9) Uani 1 1 d . . . . .
H3 H 0.9397 0.2161 0.0459 0.069 Uiso 1 1 calc R U . . .
C4 C 0.8656(4) 0.2475(3) 0.1646(3) 0.0520(8) Uani 1 1 d . . . . .
C5 C 0.8704(3) 0.3404(3) 0.2401(2) 0.0418(7) Uani 1 1 d . . . . .
H5 H 0.8182 0.3177 0.2860 0.050 Uiso 1 1 calc R U . . .
C6 C 0.9525(3) 0.4666(2) 0.2475(2) 0.0310(6) Uani 1 1 d . . . . .
C7 C 0.9528(3) 0.5700(2) 0.3237(2) 0.0283(6) Uani 1 1 d . . . . .
H7 H 0.9452 0.5412 0.3908 0.034 Uiso 1 1 calc R U . . .
C8 C 1.0854(3) 0.6935(2) 0.3549(2) 0.0303(6) Uani 1 1 d . . . . .
C9 C 1.1485(3) 0.7293(3) 0.2625(2) 0.0355(6) Uani 1 1 d . . . . .
C10 C 1.3003(3) 0.7941(3) 0.3217(2) 0.0374(7) Uani 1 1 d . . . . .
C11 C 1.4037(3) 0.8647(3) 0.2829(3) 0.0534(8) Uani 1 1 d . . . . .
H11 H 1.3844 0.8822 0.2141 0.064 Uiso 1 1 calc R U . . .
C12 C 1.5367(4) 0.9079(4) 0.3504(4) 0.0706(11) Uani 1 1 d . . . . .
H12 H 1.6078 0.9561 0.3263 0.085 Uiso 1 1 calc R U . . .
C13 C 1.5677(4) 0.8823(4) 0.4522(4) 0.0717(11) Uani 1 1 d . . . . .
H13 H 1.6586 0.9123 0.4947 0.086 Uiso 1 1 calc R U . . .
C14 C 1.4660(3) 0.8130(3) 0.4915(3) 0.0565(9) Uani 1 1 d . . . . .
H14 H 1.4859 0.7953 0.5601 0.068 Uiso 1 1 calc R U . . .
C15 C 1.3311(3) 0.7701(3) 0.4244(2) 0.0413(7) Uani 1 1 d . . . . .
C16 C 1.2034(3) 0.6959(3) 0.4461(2) 0.0360(7) Uani 1 1 d . . . . .
C17 C 1.0419(3) 0.7924(3) 0.3917(2) 0.0346(6) Uani 1 1 d . . . . .
H17 H 1.1034 0.8758 0.3844 0.041 Uiso 1 1 calc R U . . .
C18 C 1.0306(3) 0.8030(3) 0.5078(2) 0.0483(8) Uani 1 1 d . . . . .
H18A H 1.1138 0.8711 0.5597 0.058 Uiso 1 1 calc R U . . .
H18B H 1.0154 0.7244 0.5309 0.058 Uiso 1 1 calc R U . . .
C19 C 0.8467(3) 0.8222(3) 0.3500(3) 0.0482(8) Uani 1 1 d . . . . .
H19A H 0.7486 0.7811 0.3137 0.058 Uiso 1 1 calc R U . . .
H19B H 0.8847 0.9057 0.3345 0.058 Uiso 1 1 calc R U . . .
C20 C 0.8344(3) 0.6089(3) 0.2806(2) 0.0304(6) Uani 1 1 d . . . . .
C21 C 0.7809(3) 0.5689(3) 0.1553(2) 0.0354(6) Uani 1 1 d . . . . .
C22 C 0.6337(5) 0.3988(4) 0.0008(3) 0.0872(15) Uani 1 1 d . . . . .
H22A H 0.5926 0.4463 -0.0379 0.105 Uiso 1 1 calc R U . . .
H22B H 0.7104 0.4065 -0.0226 0.105 Uiso 1 1 calc R U . . .
C23 C 0.5366(6) 0.2698(5) -0.0251(4) 0.118(2) Uani 1 1 d . . . . .
H23A H 0.5746 0.2244 0.0183 0.177 Uiso 1 1 calc R U . . .
H23B H 0.5131 0.2342 -0.1011 0.177 Uiso 1 1 calc R U . . .
H23C H 0.4561 0.2632 -0.0100 0.177 Uiso 1 1 calc R U . . .
C24 C 0.7213(3) 0.5405(3) 0.3291(2) 0.0342(6) Uani 1 1 d . . . . .
H24A H 0.7019 0.4520 0.3191 0.041 Uiso 1 1 calc R U . . .
H24B H 0.7564 0.5765 0.4070 0.041 Uiso 1 1 calc R U . . .
C25 C 0.5892(3) 0.5466(3) 0.2824(2) 0.0370(7) Uani 1 1 d . . . . .
C26 C 0.3686(3) 0.4848(4) 0.2964(3) 0.0577(9) Uani 1 1 d . . . . .
H26A H 0.3129 0.4248 0.2267 0.069 Uiso 1 1 calc R U . . .
H26B H 0.3781 0.5679 0.2879 0.069 Uiso 1 1 calc R U . . .
C27 C 0.3042(4) 0.4456(4) 0.3809(3) 0.0702(11) Uani 1 1 d . . . . .
H27A H 0.3041 0.3674 0.3940 0.105 Uiso 1 1 calc R U . . .
H27B H 0.2120 0.4339 0.3561 0.105 Uiso 1 1 calc R U . . .
H27C H 0.3550 0.5102 0.4473 0.105 Uiso 1 1 calc R U . . .
N1 N 0.9061(2) 0.7479(2) 0.31204(18) 0.0339(5) Uani 1 1 d . . . . .
O1 O 1.1240(2) 0.61884(19) 0.18584(16) 0.0483(5) Uani 1 1 d . . . . .
O2 O 1.1103(2) 0.8053(2) 0.20269(17) 0.0476(5) Uani 1 1 d . . . . .
H2A H 1.0282 0.7817 0.1890 0.071 Uiso 1 1 calc R U . . .
O3 O 1.1913(2) 0.6455(2) 0.52182(16) 0.0492(5) Uani 1 1 d . . . . .
O4 O 0.8301(2) 0.6350(2) 0.09800(16) 0.0494(5) Uani 1 1 d . . . . .
O5 O 0.6825(2) 0.4520(2) 0.11933(15) 0.0480(5) Uani 1 1 d . . . . .
O6 O 0.5639(2) 0.5980(3) 0.2114(2) 0.0616(7) Uani 1 1 d . . . . .
O7 O 0.5025(2) 0.4878(2) 0.33250(17) 0.0496(6) Uani 1 1 d . . . . .
S1 S 0.88667(9) 0.83574(8) 0.49933(7) 0.0543(3) 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
O1 C1 C6 124.2(2) . . ?
O1 C1 C2 115.4(2) . . ?
C6 C1 C2 120.4(3) . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 Br1 120.0(3) . . ?
C5 C4 Br1 119.0(3) . . ?
C3 C4 Br1' 118.4(3) . . ?
C5 C4 Br1' 120.5(3) . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 121.2(2) . . ?
C1 C6 C7 119.7(2) . . ?
C6 C7 C8 112.3(2) . . ?
C6 C7 C20 116.4(2) . . ?
C8 C7 C20 105.1(2) . . ?
C6 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C20 C7 H7 107.6 . . ?
C7 C8 C16 113.9(2) . . ?
C7 C8 C17 102.2(2) . . ?
C16 C8 C17 111.3(2) . . ?
C7 C8 C9 116.4(2) . . ?
C16 C8 C9 103.1(2) . . ?
C17 C8 C9 110.1(2) . . ?
O2 C9 O1 107.5(2) . . ?
O2 C9 C10 110.8(2) . . ?
O1 C9 C10 105.0(2) . . ?
O2 C9 C8 116.6(2) . . ?
O1 C9 C8 112.6(2) . . ?
C10 C9 C8 103.8(2) . . ?
C15 C10 C11 120.4(3) . . ?
C15 C10 C9 111.5(2) . . ?
C11 C10 C9 127.9(3) . . ?
C12 C11 C10 117.3(3) . . ?
C12 C11 H11 121.3 . . ?
C10 C11 H11 121.3 . . ?
C13 C12 C11 122.4(3) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 117.4(3) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C10 C15 C14 121.8(3) . . ?
C10 C15 C16 109.4(2) . . ?
C14 C15 C16 128.8(3) . . ?
O3 C16 C15 127.2(3) . . ?
O3 C16 C8 125.1(2) . . ?
C15 C16 C8 107.7(2) . . ?
N1 C17 C8 102.5(2) . . ?
N1 C17 C18 108.7(2) . . ?
C8 C17 C18 116.6(2) . . ?
N1 C17 H17 109.6 . . ?
C8 C17 H17 109.6 . . ?
C18 C17 H17 109.6 . . ?
C17 C18 S1 106.3(2) . . ?
C17 C18 H18A 110.5 . . ?
S1 C18 H18A 110.5 . . ?
C17 C18 H18B 110.5 . . ?
S1 C18 H18B 110.5 . . ?
H18A C18 H18B 108.7 . . ?
N1 C19 S1 107.2(2) . . ?
N1 C19 H19A 110.3 . . ?
S1 C19 H19A 110.3 . . ?
N1 C19 H19B 110.3 . . ?
S1 C19 H19B 110.3 . . ?
H19A C19 H19B 108.5 . . ?
N1 C20 C21 108.0(2) . . ?
N1 C20 C24 117.5(2) . . ?
C21 C20 C24 111.3(2) . . ?
N1 C20 C7 103.21(19) . . ?
C21 C20 C7 108.0(2) . . ?
C24 C20 C7 108.1(2) . . ?
O4 C21 O5 124.4(3) . . ?
O4 C21 C20 123.4(3) . . ?
O5 C21 C20 112.0(2) . . ?
C23 C22 O5 110.5(3) . . ?
C23 C22 H22A 109.6 . . ?
O5 C22 H22A 109.6 . . ?
C23 C22 H22B 109.6 . . ?
O5 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C20 116.1(2) . . ?
C25 C24 H24A 108.3 . . ?
C20 C24 H24A 108.3 . . ?
C25 C24 H24B 108.3 . . ?
C20 C24 H24B 108.3 . . ?
H24A C24 H24B 107.4 . . ?
O6 C25 O7 123.4(3) . . ?
O6 C25 C24 126.3(2) . . ?
O7 C25 C24 110.3(2) . . ?
O7 C26 C27 107.3(3) . . ?
O7 C26 H26A 110.3 . . ?
C27 C26 H26A 110.3 . . ?
O7 C26 H26B 110.3 . . ?
C27 C26 H26B 110.3 . . ?
H26A C26 H26B 108.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C19 N1 C17 106.8(2) . . ?
C19 N1 C20 122.5(2) . . ?
C17 N1 C20 110.8(2) . . ?
C1 O1 C9 123.55(19) . . ?
C9 O2 H2A 109.5 . . ?
C21 O5 C22 116.6(2) . . ?
C25 O7 C26 117.2(2) . . ?
C18 S1 C19 91.50(13) . . ?
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
Br1 C4 1.872(6) . ?
Br1' C4 1.920(6) . ?
C1 O1 1.361(3) . ?
C1 C6 1.387(4) . ?
C1 C2 1.391(4) . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.505(4) . ?
C7 C8 1.529(4) . ?
C7 C20 1.587(4) . ?
C7 H7 0.9800 . ?
C8 C16 1.533(4) . ?
C8 C17 1.536(4) . ?
C8 C9 1.563(4) . ?
C9 O2 1.375(3) . ?
C9 O1 1.452(3) . ?
C9 C10 1.507(4) . ?
C10 C15 1.380(4) . ?
C10 C11 1.385(4) . ?
C11 C12 1.382(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.397(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.474(4) . ?
C16 O3 1.211(3) . ?
C17 N1 1.460(3) . ?
C17 C18 1.550(4) . ?
C17 H17 0.9800 . ?
C18 S1 1.814(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N1 1.439(4) . ?
C19 S1 1.856(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 N1 1.467(3) . ?
C20 C21 1.536(4) . ?
C20 C24 1.541(3) . ?
C21 O4 1.205(3) . ?
C21 O5 1.314(3) . ?
C22 C23 1.413(6) . ?
C22 O5 1.475(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.502(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O6 1.194(3) . ?
C25 O7 1.318(3) . ?
C26 O7 1.458(4) . ?
C26 C27 1.484(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O2 H2A 0.8200 . ?
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
O2 H2A N1 0.82 2.34 2.915(3) 127.6 .
O2 H2A O4 0.82 2.12 2.832(3) 144.7 .
