#------------------------------------------------------------------------------
#$Date: 2018-02-22 09:09:56 +0200 (Thu, 22 Feb 2018) $
#$Revision: 206574 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/10/2021022.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021022
loop_
_publ_author_name
'Swinton Darious, Robert'
'Jasmine, Nithianantham Jeeva'
'Karthikeyan, Ammasai'
'Thomas Muthiah, Packianathan'
'Perdih, Franc'
_publ_section_title
;
 Supramolecular architectures in cytosinium 6-chloronicotinate monohydrate
 and 5-bromo-6-methylisocytosinium hydrogen sulfate
;
_journal_coeditor_code           OV3108
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618002462
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         'C5 H7 Br N3 O, H O4 S'
_chemical_formula_sum            'C5 H8 Br N3 O5 S'
_chemical_formula_weight         302.11
_chemical_name_common
;
2-amino-5-bromo-4-hydroxy-6-methylpyrimidinium hydrogensulfate
;
_chemical_name_systematic
;
2-amino-5-bromo-4-oxy-6-methylpyrimidinium hydrogensulfate
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.026(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1671(4)
_cell_length_b                   4.87860(10)
_cell_length_c                   12.0863(3)
_cell_measurement_reflns_used    2315
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.5700
_cell_measurement_theta_min      3.6270
_cell_volume                     948.01(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_molecular_graphics
;
PLATON (Spek, 2009), Mercury (Macrae et al., 2008)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELX-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Agilent SuperNova Dual Source diffractometer with an Atlas detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3324
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.060
_diffrn_reflns_theta_min         5.503
_exptl_absorpt_coefficient_mu    8.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2013)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.773
_refine_diff_density_min         -1.381
_refine_ls_extinction_coef       0.0044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0783P)²+1.5150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                1710
_reflns_number_total             1781
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3108sup1.cif
_cod_data_source_block           II
_cod_database_code               2021022
_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   0.139
_shelx_estimated_absorpt_t_max   0.293
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Br Br1 0.96681(2) 1.14944(7) 0.63903(3) 0.0147(2) Uani d 1
S S1 0.60155(4) 0.23576(15) 0.71074(6) 0.0059(2) Uani d 1
O O1 0.85408(14) 0.7141(5) 0.73247(19) 0.0122(5) Uani d 1
O O2 0.69097(13) 0.2886(5) 0.72425(19) 0.0108(5) Uani d 1
O O3 0.55917(15) 0.3378(5) 0.6078(2) 0.0136(5) Uani d 1
O O4 0.56372(14) 0.3299(5) 0.80906(19) 0.0101(5) Uani d 1
O O5 0.59581(13) -0.0835(5) 0.70865(19) 0.0093(5) Uani d 1
H H5 0.5457 -0.1313 0.7046 0.014 Uiso calc 1
N N1 0.74531(16) 1.0117(6) 0.4460(2) 0.0100(6) Uani d 1
H H1 0.7197 1.0760 0.3836 0.012 Uiso calc 1
N N2 0.63331(17) 0.7267(6) 0.4640(2) 0.0125(6) Uani d 1
H H2A 0.6076 0.7918 0.4017 0.015 Uiso calc 1
H H2B 0.6094 0.5998 0.5014 0.015 Uiso calc 1
N N3 0.74822(16) 0.7180(6) 0.5950(2) 0.0079(5) Uani d 1
H H3 0.7245 0.5830 0.6282 0.010 Uiso calc 1
C C2 0.7071(2) 0.8186(7) 0.5010(3) 0.0083(6) Uani d 1
C C4 0.82565(19) 0.8106(7) 0.6444(3) 0.0083(6) Uani d 1
C C5 0.86285(18) 1.0192(7) 0.5796(2) 0.0074(6) Uani d 1
C C6 0.8233(2) 1.1151(7) 0.4828(3) 0.0097(6) Uani d 1
C C7 0.8550(2) 1.3261(7) 0.4091(3) 0.0124(7) Uani d 1
H H7A 0.8780 1.2359 0.3467 0.019 Uiso calc 1
H H7B 0.8986 1.4339 0.4515 0.019 Uiso calc 1
H H7C 0.8093 1.4473 0.3807 0.019 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O3 S1 O2 114.20(14)
O3 S1 O4 112.95(14)
O2 S1 O4 110.26(14)
O3 S1 O5 107.93(13)
O2 S1 O5 103.56(13)
O4 S1 O5 107.25(13)
S1 O5 H5 109.5
C2 N1 C6 123.2(3)
C2 N1 H1 118.4
C6 N1 H1 118.4
C2 N2 H2A 120.0
C2 N2 H2B 120.0
H2A N2 H2B 120.0
C2 N3 C4 125.5(3)
C2 N3 H3 117.3
C4 N3 H3 117.3
N2 C2 N1 121.5(3)
N2 C2 N3 121.0(3)
N1 C2 N3 117.5(3)
O1 C4 N3 119.3(3)
O1 C4 C5 127.3(3)
N3 C4 C5 113.4(3)
C6 C5 C4 121.5(3)
C6 C5 Br1 122.5(2)
C4 C5 Br1 116.0(2)
C5 C6 N1 118.8(3)
C5 C6 C7 126.5(3)
N1 C6 C7 114.8(3)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.868(3)
S1 O3 1.445(2)
S1 O2 1.461(2)
S1 O4 1.466(2)
S1 O5 1.560(2)
O1 C4 1.210(4)
O5 H5 0.8400
N1 C2 1.340(4)
N1 C6 1.387(4)
N1 H1 0.8800
N2 C2 1.309(4)
N2 H2A 0.8800
N2 H2B 0.8800
N3 C2 1.347(4)
N3 C4 1.404(4)
N3 H3 0.8800
C4 C5 1.452(4)
C5 C6 1.357(5)
C6 C7 1.487(5)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O2 4_575 0.88 2.04 2.900(3) 165.0
N2 H2A O4 4_575 0.88 2.24 3.002(4) 145.0
N2 H2A O5 4_565 0.88 2.53 3.160(3) 129.0
N2 H2B O3 . 0.88 2.04 2.915(4) 172.0
N3 H3 O2 . 0.88 1.96 2.827(4) 169.0
O5 H5 O4 2_646 0.84 1.77 2.600(3) 170.0
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
C6 N1 C2 N2 179.7(3)
C6 N1 C2 N3 -1.6(5)
C4 N3 C2 N2 -176.9(3)
C4 N3 C2 N1 4.3(5)
C2 N3 C4 O1 175.8(3)
C2 N3 C4 C5 -4.4(5)
O1 C4 C5 C6 -178.4(3)
N3 C4 C5 C6 1.8(4)
O1 C4 C5 Br1 0.7(4)
N3 C4 C5 Br1 -179.2(2)
C4 C5 C6 N1 0.5(5)
Br1 C5 C6 N1 -178.5(2)
C4 C5 C6 C7 -179.6(3)
Br1 C5 C6 C7 1.4(5)
C2 N1 C6 C5 -0.7(5)
C2 N1 C6 C7 179.4(3)

_cod_database_fobs_code 2021022
