#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/68/4516816.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_4516816
loop_
_publ_author_name
'Ossowski, Jakub'
'W\"achter, Tobias'
'Silies, Laura'
'Kind, Martin'
'Noworolska, Agnieszka'
'Blobner, Florian'
'Gnatek, Dominika'
'Rysz, Jakub'
'Bolte, Michael'
'Feulner, Peter'
'Terfort, Andreas'
'Cyganik, Piotr'
'Zharnikov, Michael'
_publ_section_title
;
 Thiolate versus Selenolate: Structure, Stability, and Charge Transfer
 Properties.
;
_journal_issue                   4
_journal_name_full               'ACS nano'
_journal_page_first              4508
_journal_page_last               4526
_journal_paper_doi               10.1021/acsnano.5b01109
_journal_volume                  9
_journal_year                    2015
_chemical_formula_moiety         'C11 H8 Br N O'
_chemical_formula_sum            'C11 H8 Br N O'
_chemical_formula_weight         250.09
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.291(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.5180(16)
_cell_length_b                   6.1510(3)
_cell_length_c                   8.6436(8)
_cell_measurement_reflns_used    19959
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      3.3
_cell_volume                     984.53(13)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17801
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         3.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.137
_exptl_absorpt_correction_T_max  0.6366
_exptl_absorpt_correction_T_min  0.3603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0626P)^2^+1.2900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                2432
_reflns_number_total             2533
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            nn5b01109_si_002.cif
_cod_data_source_block           te33
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4516816
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.04052(2) 0.17007(6) 0.13732(7) 0.04233(15) Uani 1 1 d .
O1 O 0.42783(15) 0.9553(4) 0.3582(4) 0.0350(5) Uani 1 1 d .
N1 N 0.45455(19) 0.7566(7) 0.5696(4) 0.0360(7) Uani 1 1 d .
H1A H 0.441(4) 0.671(10) 0.642(9) 0.055(19) Uiso 1 1 d .
H1B H 0.489(4) 0.843(10) 0.577(9) 0.06(2) Uiso 1 1 d .
C1 C 0.1702(2) 0.2656(6) 0.2959(4) 0.0299(7) Uani 1 1 d .
H1 H 0.1648 0.1233 0.3369 0.036 Uiso 1 1 calc R
C2 C 0.1201(2) 0.3476(6) 0.1954(5) 0.0310(7) Uani 1 1 d .
C3 C 0.12557(19) 0.5560(6) 0.1301(5) 0.0322(7) Uani 1 1 d .
H3 H 0.0894 0.6082 0.0611 0.039 Uiso 1 1 calc R
C4 C 0.1840(2) 0.6828(6) 0.1678(5) 0.0303(7) Uani 1 1 d .
H4 H 0.1885 0.8235 0.1236 0.036 Uiso 1 1 calc R
C5 C 0.23760(19) 0.6061(6) 0.2721(4) 0.0268(6) Uani 1 1 d .
C6 C 0.29888(18) 0.7342(6) 0.3135(4) 0.0282(6) Uani 1 1 d .
H6 H 0.3040 0.8757 0.2709 0.034 Uiso 1 1 calc R
C7 C 0.3505(2) 0.6575(5) 0.4132(5) 0.0282(7) Uani 1 1 d .
C8 C 0.3434(2) 0.4471(6) 0.4784(4) 0.0307(7) Uani 1 1 d .
H8 H 0.3795 0.3934 0.5469 0.037 Uiso 1 1 calc R
C9 C 0.2848(2) 0.3213(6) 0.4433(5) 0.0324(8) Uani 1 1 d .
H9 H 0.2801 0.1819 0.4895 0.039 Uiso 1 1 calc R
C10 C 0.23094(19) 0.3954(6) 0.3389(4) 0.0277(6) Uani 1 1 d .
C11 C 0.4138(2) 0.8011(6) 0.4464(4) 0.0290(7) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0326(2) 0.0372(2) 0.0571(3) -0.00632(17) -0.0052(2) -0.01162(14)
O1 0.0366(12) 0.0331(12) 0.0353(13) 0.0008(12) -0.0065(12) -0.0094(10)
N1 0.0319(15) 0.0401(17) 0.0361(16) 0.0022(15) -0.0062(14) -0.0087(16)
C1 0.0342(16) 0.0239(14) 0.0317(17) -0.0014(13) -0.0012(13) -0.0050(14)
C2 0.0280(17) 0.0287(16) 0.0363(18) -0.0052(13) -0.0015(15) -0.0057(12)
C3 0.0302(15) 0.0290(15) 0.0375(17) -0.0018(15) -0.0053(15) -0.0009(12)
C4 0.0299(17) 0.0271(15) 0.0338(19) -0.0013(13) -0.0005(14) -0.0005(12)
C5 0.0264(15) 0.0235(14) 0.0305(16) -0.0019(13) -0.0011(12) -0.0004(12)
C6 0.0280(15) 0.0242(14) 0.0322(16) -0.0024(13) -0.0002(13) -0.0030(13)
C7 0.0284(16) 0.0263(15) 0.0300(16) -0.0043(12) -0.0037(13) -0.0031(11)
C8 0.0329(17) 0.0290(16) 0.0303(17) -0.0001(13) -0.0054(13) 0.0005(13)
C9 0.041(2) 0.0234(15) 0.0328(19) -0.0002(12) -0.0039(16) -0.0008(13)
C10 0.0309(15) 0.0229(14) 0.0294(16) -0.0023(13) -0.0004(13) -0.0024(12)
C11 0.0300(16) 0.0283(15) 0.0286(17) -0.0038(12) -0.0023(13) -0.0040(12)
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'
Br Br -0.2901 2.4595 '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
C11 N1 H1A 123(5)
C11 N1 H1B 111(5)
H1A N1 H1B 124(7)
C2 C1 C10 119.4(3)
C2 C1 H1 120.3
C10 C1 H1 120.3
C1 C2 C3 122.9(3)
C1 C2 Br1 118.7(3)
C3 C2 Br1 118.4(3)
C4 C3 C2 118.8(3)
C4 C3 H3 120.6
C2 C3 H3 120.6
C3 C4 C5 120.7(3)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C10 119.9(3)
C4 C5 C6 122.0(3)
C10 C5 C6 118.1(3)
C7 C6 C5 121.4(3)
C7 C6 H6 119.3
C5 C6 H6 119.3
C6 C7 C8 120.0(3)
C6 C7 C11 117.6(3)
C8 C7 C11 122.5(3)
C9 C8 C7 120.2(3)
C9 C8 H8 119.9
C7 C8 H8 119.9
C8 C9 C10 121.1(3)
C8 C9 H9 119.5
C10 C9 H9 119.5
C9 C10 C5 119.2(3)
C9 C10 C1 122.5(3)
C5 C10 C1 118.3(3)
O1 C11 N1 121.8(3)
O1 C11 C7 119.9(3)
N1 C11 C7 118.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.900(4)
O1 C11 1.245(5)
N1 C11 1.330(5)
N1 H1A 0.85(7)
N1 H1B 0.83(7)
C1 C2 1.365(5)
C1 C10 1.427(5)
C1 H1 0.9500
C2 C3 1.405(5)
C3 C4 1.371(5)
C3 H3 0.9500
C4 C5 1.419(5)
C4 H4 0.9500
C5 C10 1.424(5)
C5 C6 1.426(5)
C6 C7 1.368(5)
C6 H6 0.9500
C7 C8 1.419(5)
C7 C11 1.494(5)
C8 C9 1.365(5)
C8 H8 0.9500
C9 C10 1.417(5)
C9 H9 0.9500
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 H1A O1 0.85(7) 2.04(8) 2.860(5) 160(6) 4_576
N1 H1B O1 0.83(7) 2.06(7) 2.874(4) 168(8) 3_676
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
C10 C1 C2 C3 0.5(6)
C10 C1 C2 Br1 179.1(3)
C1 C2 C3 C4 0.5(6)
Br1 C2 C3 C4 -178.1(3)
C2 C3 C4 C5 -0.7(6)
C3 C4 C5 C10 -0.1(6)
C3 C4 C5 C6 -180.0(4)
C4 C5 C6 C7 -179.4(4)
C10 C5 C6 C7 0.7(5)
C5 C6 C7 C8 -0.4(6)
C5 C6 C7 C11 178.4(3)
C6 C7 C8 C9 -0.6(6)
C11 C7 C8 C9 -179.4(4)
C7 C8 C9 C10 1.4(6)
C8 C9 C10 C5 -1.1(6)
C8 C9 C10 C1 178.0(4)
C4 C5 C10 C9 -179.8(4)
C6 C5 C10 C9 0.1(5)
C4 C5 C10 C1 1.0(5)
C6 C5 C10 C1 -179.1(3)
C2 C1 C10 C9 179.7(4)
C2 C1 C10 C5 -1.2(6)
C6 C7 C11 O1 -17.9(6)
C8 C7 C11 O1 160.9(4)
C6 C7 C11 N1 163.3(4)
C8 C7 C11 N1 -17.9(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 57428037
