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#$Date: 2021-01-28 01:01:37 +0200 (Thu, 28 Jan 2021) $
#$Revision: 261273 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/84/4518427.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_4518427
loop_
_publ_author_name
'Nag, Abhijit'
'Islam, Md Rabiul'
'Pradeep, Thalappil'
_publ_section_title
;
 Selective Extraction of Gold by Niacin
;
_journal_name_full               'ACS Sustainable Chemistry & Engineering'
_journal_paper_doi               10.1021/acssuschemeng.0c07409
_journal_year                    2021
_chemical_formula_moiety         'C12 H11 N2 O4, Au Cl4 '
_chemical_formula_sum            'C12 H11 Au Cl4 N2 O4'
_chemical_formula_weight         585.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 105.095(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2567(18)
_cell_length_b                   10.516(4)
_cell_length_c                   11.444(4)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.38
_cell_measurement_theta_min      3.01
_cell_volume                     843.2(5)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14924
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.980
_diffrn_reflns_theta_min         3.580
_exptl_absorpt_coefficient_mu    9.376
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.4461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.308
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       0.0376(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.278
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.278
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0271
_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)+(0.0120P)²+1.5569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1944
_reflns_number_total             2426
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sc0c07409_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4518427
_shelx_shelxl_version_number     2018/3
_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   0.256
_shelx_estimated_absorpt_t_max   0.454
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.500000 0.500000 0.500000 0.02985(12) Uani 1 2 d S . P . .
Cl1 Cl 0.3946(2) 0.34093(11) 0.36351(10) 0.0525(3) Uani 1 1 d . . . . .
Cl2 Cl 0.38990(19) 0.64560(11) 0.34919(10) 0.0472(3) Uani 1 1 d . . . . .
C1 C 0.6855(5) 0.0656(4) 0.3031(3) 0.0313(7) Uani 1 1 d . . . . .
C2 C 0.7830(6) 0.1660(4) 0.3712(4) 0.0392(9) Uani 1 1 d . . . . .
H2 H 0.805504 0.240623 0.333565 0.047 Uiso 1 1 calc R U . . .
C3 C 0.8110(7) 0.0506(6) 0.5510(4) 0.0483(11) Uani 1 1 d . . . . .
H3 H 0.853016 0.047350 0.634956 0.058 Uiso 1 1 calc R U . . .
C4 C 0.7147(7) -0.0507(5) 0.4873(4) 0.0467(10) Uani 1 1 d . . . . .
H4 H 0.691808 -0.123248 0.527781 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6520(6) -0.0437(4) 0.3626(4) 0.0374(8) Uani 1 1 d . . . . .
H5 H 0.587641 -0.112034 0.318600 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6137(6) 0.0827(4) 0.1691(3) 0.0350(8) Uani 1 1 d . . . . .
N1 N 0.8440(6) 0.1539(4) 0.4914(3) 0.0441(9) Uani 1 1 d D . . . .
O1 O 0.6007(5) 0.1918(3) 0.1276(3) 0.0478(8) Uani 1 1 d . . . . .
O2 O 0.5708(6) -0.0195(3) 0.1082(3) 0.0498(9) Uani 1 1 d . . . . .
H H 0.500000 0.000000 0.000000 0.10(5) Uiso 1 2 d S . P . .
H1 H 0.917(7) 0.213(4) 0.533(5) 0.067(18) Uiso 1 1 d 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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
Cl1 Au1 Cl1 180.0 3_666 . ?
Cl1 Au1 Cl2 89.16(6) 3_666 3_666 ?
Cl1 Au1 Cl2 90.84(6) . 3_666 ?
Cl1 Au1 Cl2 90.84(5) 3_666 . ?
Cl1 Au1 Cl2 89.16(5) . . ?
Cl2 Au1 Cl2 180.00(7) 3_666 . ?
C5 C1 C2 118.8(4) . . ?
C5 C1 C6 122.9(4) . . ?
C2 C1 C6 118.3(4) . . ?
N1 C2 C1 119.2(4) . . ?
N1 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
N1 C3 C4 119.5(4) . . ?
N1 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C1 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C1 C5 H5 120.1 . . ?
O1 C6 O2 126.1(4) . . ?
O1 C6 C1 118.5(4) . . ?
O2 C6 C1 115.4(4) . . ?
C2 N1 C3 123.2(4) . . ?
C2 N1 H1 119(4) . . ?
C3 N1 H1 118(4) . . ?
C6 O2 H 112.9(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
Au1 Cl1 2.2805(12) 3_666 ?
Au1 Cl1 2.2805(12) . ?
Au1 Cl2 2.2898(11) 3_666 ?
Au1 Cl2 2.2898(11) . ?
C1 C5 1.389(6) . ?
C1 C2 1.391(5) . ?
C1 C6 1.496(5) . ?
C2 N1 1.336(5) . ?
C2 H2 0.9300 . ?
C3 N1 1.337(7) . ?
C3 C4 1.375(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 O1 1.236(5) . ?
C6 O2 1.275(5) . ?
N1 H1 0.87(2) . ?
O2 H 1.228(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
_geom_hbond_publ_flag
C3 H3 Cl1 0.93 2.81 3.651(4) 150.8 4_666 yes
C4 H4 Cl1 0.93 2.75 3.683(5) 176.6 3_656 yes
O2 H O1 1.228(3) 2.486(3) 3.220(5) 116.02(17) 3_655 yes
O2 H O2 1.228(3) 1.228(3) 2.457(7) 180.0(3) 3_655 yes
N1 H1 O1 0.87(2) 1.79(2) 2.650(5) 169(6) 4_666 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 N1 0.9(6) . . . . ?
C6 C1 C2 N1 178.3(4) . . . . ?
N1 C3 C4 C5 -0.5(7) . . . . ?
C3 C4 C5 C1 -0.6(7) . . . . ?
C2 C1 C5 C4 0.4(6) . . . . ?
C6 C1 C5 C4 -176.9(4) . . . . ?
C5 C1 C6 O1 159.7(4) . . . . ?
C2 C1 C6 O1 -17.6(6) . . . . ?
C5 C1 C6 O2 -20.2(6) . . . . ?
C2 C1 C6 O2 162.6(4) . . . . ?
C1 C2 N1 C3 -2.1(7) . . . . ?
C4 C3 N1 C2 1.9(7) . . . . ?
