#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:21:52 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276646 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/15/7061523.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_7061523
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         'C24 H18 Br N O8'
_chemical_formula_sum            'C24 H18 Br N O8'
_chemical_formula_weight         528.30
_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                 111.815(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5899(9)
_cell_length_b                   26.536(2)
_cell_length_c                   8.5020(8)
_cell_measurement_reflns_used    5545
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.77
_cell_measurement_theta_min      2.58
_cell_volume                     2218.1(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0548
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19387
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.209
_exptl_absorpt_coefficient_mu    1.906
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0508
_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)+(0.0288P)²+2.1624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2721
_reflns_number_total             4351
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj01135b2.cif
_cod_data_source_block           4d
_cod_depositor_comments
'Adding full bibliography for 7061522--7061528.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7061523
_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   0.679
_shelx_estimated_absorpt_t_max   0.725
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
Br1 Br -0.36167(5) 0.22428(2) 0.19751(6) 0.0808(2) Uani 1 1 d . . . . .
C1 C 0.0452(3) 0.19434(11) 0.6392(4) 0.0338(8) Uani 1 1 d . . . . .
C2 C 0.0150(4) 0.24246(13) 0.5758(5) 0.0517(10) Uani 1 1 d . . . . .
H2 H 0.0771 0.2685 0.6188 0.062 Uiso 1 1 calc R U . . .
C3 C -0.1084(4) 0.25143(14) 0.4481(6) 0.0587(11) Uani 1 1 d . . . . .
H3 H -0.1313 0.2838 0.4052 0.070 Uiso 1 1 calc R U . . .
C4 C -0.1977(4) 0.21233(14) 0.3842(5) 0.0486(10) Uani 1 1 d . . . . .
C5 C -0.1694(3) 0.16443(12) 0.4487(4) 0.0376(8) Uani 1 1 d . . . . .
H5 H -0.2317 0.1385 0.4047 0.045 Uiso 1 1 calc R U . . .
C6 C -0.0468(3) 0.15511(11) 0.5802(4) 0.0298(7) Uani 1 1 d . . . . .
C7 C -0.0012(3) 0.10425(10) 0.6579(4) 0.0273(7) Uani 1 1 d . . . . .
H7 H -0.0631 0.0782 0.5898 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1442(3) 0.09366(10) 0.6669(3) 0.0245(7) Uani 1 1 d . . . . .
C9 C 0.2339(3) 0.14148(11) 0.7156(4) 0.0280(7) Uani 1 1 d . . . . .
C10 C 0.2729(3) 0.15272(11) 0.5670(4) 0.0288(7) Uani 1 1 d . . . . .
C11 C 0.3465(3) 0.19322(12) 0.5452(4) 0.0425(9) Uani 1 1 d . . . . .
H11 H 0.3787 0.2179 0.6284 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3710(4) 0.19625(14) 0.3979(5) 0.0516(10) Uani 1 1 d . . . . .
H12 H 0.4210 0.2232 0.3816 0.062 Uiso 1 1 calc R U . . .
C13 C 0.3227(4) 0.16003(13) 0.2738(4) 0.0464(9) Uani 1 1 d . . . . .
H13 H 0.3412 0.1627 0.1754 0.056 Uiso 1 1 calc R U . . .
C14 C 0.2475(3) 0.11984(13) 0.2933(4) 0.0386(8) Uani 1 1 d . . . . .
H14 H 0.2143 0.0955 0.2094 0.046 Uiso 1 1 calc R U . . .
C15 C 0.2231(3) 0.11701(11) 0.4416(4) 0.0283(7) Uani 1 1 d . . . . .
C16 C 0.1456(3) 0.07872(11) 0.4931(4) 0.0279(7) Uani 1 1 d . . . . .
C17 C 0.0164(3) 0.09855(11) 0.8461(4) 0.0290(7) Uani 1 1 d . . . . .
H17 H 0.0505 0.1305 0.9041 0.035 Uiso 1 1 calc R U . . .
C18 C -0.1121(3) 0.08477(13) 0.8742(4) 0.0350(8) Uani 1 1 d . . . . .
C19 C -0.3211(4) 0.11682(16) 0.8751(6) 0.0660(12) Uani 1 1 d . . . . .
H19A H -0.3639 0.0858 0.8250 0.099 Uiso 1 1 calc R U . . .
H19B H -0.3817 0.1444 0.8266 0.099 Uiso 1 1 calc R U . . .
H19C H -0.2997 0.1158 0.9951 0.099 Uiso 1 1 calc R U . . .
C20 C 0.2085(3) 0.05749(11) 0.8189(4) 0.0274(7) Uani 1 1 d . . . . .
C21 C 0.3429(3) 0.08288(12) 0.9226(4) 0.0328(8) Uani 1 1 d . . . . .
C22 C 0.2315(3) 0.00312(11) 0.7821(4) 0.0321(7) Uani 1 1 d . . . . .
H22A H 0.2669 -0.0154 0.8880 0.039 Uiso 1 1 calc R U . . .
H22B H 0.1451 -0.0119 0.7131 0.039 Uiso 1 1 calc R U . . .
C23 C 0.3283(3) -0.00189(12) 0.6926(4) 0.0301(7) Uani 1 1 d . . . . .
C24 C 0.4180(4) -0.05718(14) 0.5450(5) 0.0583(11) Uani 1 1 d . . . . .
H24A H 0.3955 -0.0359 0.4471 0.087 Uiso 1 1 calc R U . . .
H24B H 0.4117 -0.0918 0.5106 0.087 Uiso 1 1 calc R U . . .
H24C H 0.5090 -0.0501 0.6213 0.087 Uiso 1 1 calc R U . . .
N1 N 0.1198(3) 0.06045(10) 0.9166(3) 0.0329(6) Uani 1 1 d D . . . .
H1 H 0.0840 0.0303 0.9248 0.036(9) Uiso 1 1 d DR . . . .
O1 O 0.1722(2) 0.18380(7) 0.7622(3) 0.0355(5) Uani 1 1 d . . . . .
O2 O 0.0871(2) 0.04235(8) 0.4132(3) 0.0408(6) Uani 1 1 d . . . . .
O3 O -0.1354(3) 0.04470(10) 0.9182(4) 0.0683(8) Uani 1 1 d . . . . .
O4 O -0.1965(2) 0.12356(8) 0.8425(3) 0.0509(7) Uani 1 1 d . . . . .
O5 O 0.4329(2) 0.06752(9) 1.0429(3) 0.0512(6) Uani 1 1 d . . . . .
O6 O 0.3491(2) 0.13076(8) 0.8634(2) 0.0330(5) Uani 1 1 d . . . . .
O7 O 0.3998(2) 0.03147(8) 0.6776(3) 0.0414(6) Uani 1 1 d . . . . .
O8 O 0.3242(2) -0.04780(8) 0.6293(3) 0.0391(5) 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'
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
C2 C1 C6 121.6(3) . . ?
C2 C1 O1 120.0(3) . . ?
C6 C1 O1 118.3(3) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 Br1 119.2(3) . . ?
C5 C4 Br1 119.1(3) . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 124.6(3) . . ?
C1 C6 C7 116.6(3) . . ?
C6 C7 C8 109.8(2) . . ?
C6 C7 C17 116.0(2) . . ?
C8 C7 C17 101.4(2) . . ?
C6 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
C17 C7 H7 109.8 . . ?
C16 C8 C7 111.5(2) . . ?
C16 C8 C9 104.2(2) . . ?
C7 C8 C9 111.5(2) . . ?
C16 C8 C20 119.0(2) . . ?
C7 C8 C20 106.0(2) . . ?
C9 C8 C20 104.4(2) . . ?
O6 C9 O1 104.1(2) . . ?
O6 C9 C10 111.8(2) . . ?
O1 C9 C10 112.1(2) . . ?
O6 C9 C8 108.3(2) . . ?
O1 C9 C8 114.9(2) . . ?
C10 C9 C8 105.8(2) . . ?
C15 C10 C11 120.4(3) . . ?
C15 C10 C9 111.7(3) . . ?
C11 C10 C9 127.9(3) . . ?
C12 C11 C10 118.4(3) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 117.7(3) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C10 C15 C14 121.4(3) . . ?
C10 C15 C16 109.9(3) . . ?
C14 C15 C16 128.6(3) . . ?
O2 C16 C15 127.6(3) . . ?
O2 C16 C8 124.0(3) . . ?
C15 C16 C8 108.3(2) . . ?
N1 C17 C18 110.7(2) . . ?
N1 C17 C7 106.2(2) . . ?
C18 C17 C7 114.7(2) . . ?
N1 C17 H17 108.4 . . ?
C18 C17 H17 108.4 . . ?
C7 C17 H17 108.4 . . ?
O3 C18 O4 124.0(3) . . ?
O3 C18 C17 125.0(3) . . ?
O4 C18 C17 111.0(3) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C22 110.7(2) . . ?
N1 C20 C21 107.7(2) . . ?
C22 C20 C21 110.6(2) . . ?
N1 C20 C8 105.3(2) . . ?
C22 C20 C8 118.2(2) . . ?
C21 C20 C8 103.6(2) . . ?
O5 C21 O6 120.1(3) . . ?
O5 C21 C20 128.9(3) . . ?
O6 C21 C20 110.9(3) . . ?
C23 C22 C20 112.6(2) . . ?
C23 C22 H22A 109.1 . . ?
C20 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C20 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
O7 C23 O8 124.0(3) . . ?
O7 C23 C22 124.6(3) . . ?
O8 C23 C22 111.4(3) . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C17 N1 C20 110.3(2) . . ?
C17 N1 H1 112.2 . . ?
C20 N1 H1 111.9 . . ?
C1 O1 C9 111.3(2) . . ?
C18 O4 C19 117.2(3) . . ?
C21 O6 C9 111.5(2) . . ?
C23 O8 C24 115.8(3) . . ?
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 1.894(4) . ?
C1 C2 1.377(4) . ?
C1 C6 1.387(4) . ?
C1 O1 1.391(4) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(4) . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(4) . ?
C7 C8 1.539(4) . ?
C7 C17 1.548(4) . ?
C7 H7 0.9800 . ?
C8 C16 1.535(4) . ?
C8 C9 1.546(4) . ?
C8 C20 1.550(4) . ?
C9 O6 1.418(3) . ?
C9 O1 1.428(3) . ?
C9 C10 1.498(4) . ?
C10 C15 1.377(4) . ?
C10 C11 1.379(4) . ?
C11 C12 1.373(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.471(4) . ?
C16 O2 1.210(3) . ?
C17 N1 1.447(4) . ?
C17 C18 1.511(4) . ?
C17 H17 0.9800 . ?
C18 O3 1.183(4) . ?
C18 O4 1.323(4) . ?
C19 O4 1.456(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N1 1.469(4) . ?
C20 C22 1.515(4) . ?
C20 C21 1.525(4) . ?
C21 O5 1.182(4) . ?
C21 O6 1.377(4) . ?
C22 C23 1.492(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O7 1.202(3) . ?
C23 O8 1.326(4) . ?
C24 O8 1.445(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1 0.8995 . ?
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 O3 0.90 2.34 3.100(4) 141.6 3_557
