#------------------------------------------------------------------------------
#$Date: 2019-11-10 19:44:25 +0200 (Sun, 10 Nov 2019) $
#$Revision: 226076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/60/4516051.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_4516051
loop_
_publ_author_name
'De, Avik'
'Mondal, Raju'
_publ_section_title
;
 Toxic Metal Sequestration Exploiting a Unprecedented Low-Molecular-Weight
 Hydrogel-to-Metallogel Transformation.
;
_journal_issue                   6
_journal_name_full               'ACS omega'
_journal_page_first              6022
_journal_page_last               6030
_journal_paper_doi               10.1021/acsomega.8b00758
_journal_volume                  3
_journal_year                    2018
_chemical_formula_sum            'C25 H19 N11 O4'
_chemical_formula_weight         537.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 111.426(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.463(2)
_cell_length_b                   8.8637(9)
_cell_length_c                   14.0198(14)
_cell_measurement_reflns_used    846
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.72
_cell_volume                     2367.1(4)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_unetI/netI     0.0791
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15737
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.612
_diffrn_reflns_theta_min         2.138
_exptl_absorpt_coefficient_mu    0.109
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       Block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.1414
_refine_ls_R_factor_gt           0.0591
_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)+(0.0693P)²+1.4502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1369
_reflns_number_total             2718
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao8b00758_si_002.cif
_cod_data_source_block           AD121216_0M
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4516051
_shelx_shelxl_version_number     2016/6
_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'
'-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
N1 N 0.000000 1.4041(4) 0.250000 0.0325(8) Uani 1 2 d S T P
O1 O 0.09978(13) 0.9708(2) 0.17104(16) 0.0534(7) Uani 1 1 d . . .
N5 N 0.12972(14) 0.9031(3) -0.12839(18) 0.0440(7) Uani 1 1 d . . .
O2 O 0.07982(13) 1.4562(3) 0.06672(17) 0.0580(7) Uani 1 1 d . . .
N2 N 0.04182(13) 1.2467(3) 0.11926(19) 0.0424(7) Uani 1 1 d . . .
H2A H 0.022466 1.206736 0.158251 0.051 Uiso 1 1 calc R U .
N3 N 0.06319(14) 1.1579(3) 0.05590(19) 0.0490(7) Uani 1 1 d . . .
H3 H 0.057616 1.189457 -0.004580 0.059 Uiso 1 1 calc R U .
C7 C 0.13857(15) 0.7952(3) 0.0161(2) 0.0374(7) Uani 1 1 d . . .
H7A H 0.146743 0.726913 0.069568 0.045 Uiso 1 1 calc R U .
N4 N 0.10651(14) 1.0082(3) -0.07820(19) 0.0467(7) Uani 1 1 d . . .
N6 N 0.19453(13) 0.6688(3) -0.19356(19) 0.0434(7) Uani 1 1 d . . .
C13 C 0.000000 1.7189(5) 0.250000 0.0435(11) Uani 1 2 d S T P
H13A H -0.000001 1.823847 0.250000 0.065 Uiso 1 2 calc R U P
C10 C 0.05132(15) 1.3955(3) 0.1198(2) 0.0392(7) Uani 1 1 d . . .
C6 C 0.14919(14) 0.7727(3) -0.0736(2) 0.0346(7) Uani 1 1 d . . .
C12 C 0.02607(16) 1.6392(3) 0.1875(2) 0.0422(8) Uani 1 1 d . . .
H12A H 0.044623 1.689499 0.144946 0.051 Uiso 1 1 calc R U .
C11 C 0.02430(14) 1.4830(3) 0.1890(2) 0.0334(7) Uani 1 1 d . . .
C8 C 0.11300(16) 0.9414(3) 0.0106(2) 0.0373(7) Uani 1 1 d . . .
C5 C 0.17474(14) 0.6425(3) -0.1141(2) 0.0362(7) Uani 1 1 d . . .
C1 C 0.21781(17) 0.5492(4) -0.2302(3) 0.0498(9) Uani 1 1 d . . .
H1C H 0.232604 0.565347 -0.284693 0.060 Uiso 1 1 calc R U .
C9 C 0.09246(15) 1.0234(3) 0.0867(2) 0.0368(7) Uani 1 1 d . . .
C4 C 0.17648(18) 0.5005(4) -0.0725(3) 0.0504(9) Uani 1 1 d . . .
H4B H 0.162125 0.486047 -0.017402 0.061 Uiso 1 1 calc R U .
C3 C 0.1997(2) 0.3814(4) -0.1138(3) 0.0624(10) Uani 1 1 d . . .
H3B H 0.200713 0.284654 -0.087613 0.075 Uiso 1 1 calc R U .
C2 C 0.22151(18) 0.4059(4) -0.1939(3) 0.0577(10) Uani 1 1 d . . .
H2B H 0.238267 0.327327 -0.222505 0.069 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 0.0033 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
C11 N1 C11 116.8(3) . 2
N4 N5 C6 112.1(2) . .
C10 N2 N3 119.4(2) . .
C10 N2 H2A 120.3 . .
N3 N2 H2A 120.3 . .
C9 N3 N2 121.0(3) . .
C9 N3 H3 119.5 . .
N2 N3 H3 119.5 . .
C6 C7 C8 105.6(3) . .
C6 C7 H7A 127.2 . .
C8 C7 H7A 127.2 . .
C8 N4 N5 104.2(2) . .
C5 N6 C1 116.1(3) . .
C12 C13 C12 118.2(4) 2 .
C12 C13 H13A 120.9 2 .
C12 C13 H13A 120.9 . .
O2 C10 N2 122.1(3) . .
O2 C10 C11 122.5(3) . .
N2 C10 C11 115.4(2) . .
N5 C6 C7 106.4(3) . .
N5 C6 C5 121.4(2) . .
C7 C6 C5 132.1(3) . .
C13 C12 C11 119.0(3) . .
C13 C12 H12A 120.5 . .
C11 C12 H12A 120.5 . .
N1 C11 C12 123.5(3) . .
N1 C11 C10 117.2(2) . .
C12 C11 C10 119.4(3) . .
N4 C8 C7 111.7(2) . .
N4 C8 C9 119.8(3) . .
C7 C8 C9 128.5(3) . .
N6 C5 C4 122.8(3) . .
N6 C5 C6 116.4(3) . .
C4 C5 C6 120.8(3) . .
N6 C1 C2 125.1(3) . .
N6 C1 H1C 117.5 . .
C2 C1 H1C 117.5 . .
O1 C9 N3 122.3(3) . .
O1 C9 C8 122.8(3) . .
N3 C9 C8 114.8(3) . .
C3 C4 C5 118.9(3) . .
C3 C4 H4B 120.6 . .
C5 C4 H4B 120.6 . .
C2 C3 C4 119.4(3) . .
C2 C3 H3B 120.3 . .
C4 C3 H3B 120.3 . .
C1 C2 C3 117.8(3) . .
C1 C2 H2B 121.1 . .
C3 C2 H2B 121.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C11 1.333(3) .
N1 C11 1.333(3) 2
O1 C9 1.228(3) .
N5 N4 1.354(3) .
N5 C6 1.364(4) .
O2 C10 1.225(3) .
N2 C10 1.333(4) .
N2 N3 1.373(3) .
N2 H2A 0.8600 .
N3 C9 1.333(4) .
N3 H3 0.8600 .
C7 C6 1.367(4) .
C7 C8 1.389(4) .
C7 H7A 0.9300 .
N4 C8 1.341(3) .
N6 C5 1.338(3) .
N6 C1 1.339(4) .
C13 C12 1.375(4) 2
C13 C12 1.375(4) .
C13 H13A 0.9300 .
C10 C11 1.496(4) .
C6 C5 1.465(4) .
C12 C11 1.386(4) .
C12 H12A 0.9300 .
C8 C9 1.473(4) .
C5 C4 1.382(4) .
C1 C2 1.360(5) .
C1 H1C 0.9300 .
C4 C3 1.370(4) .
C4 H4B 0.9300 .
C3 C2 1.368(5) .
C3 H3B 0.9300 .
C2 H2B 0.9300 .
