#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228748.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_2228748
loop_
_publ_author_name
'Zhou, Zhong-Gao'
'Fu, Shun-Guo'
'Lai, Wu-Leng'
'Wang, Chun-Feng'
_publ_section_title
;
 1-(2-Bromo-2-deoxy-β-<small>D</small>-xylofuranosyl)uracil
;
_journal_coeditor_code           HG2764
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o111
_journal_paper_doi               10.1107/S1600536810051081
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C9 H11 Br N2 O5'
_chemical_formula_moiety         'C9 H11 Br N2 O5'
_chemical_formula_sum            'C9 H11 Br N2 O5'
_chemical_formula_weight         307.11
_chemical_name_systematic
;
1-(2-Bromo-2-deoxy-β-D-xylofuranosyl)uracil
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8444(3)
_cell_length_b                   12.7237(10)
_cell_length_c                   17.4388(13)
_cell_measurement_reflns_used    3827
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.34
_cell_volume                     1074.90(13)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
SHELXTL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6683
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    3.837
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.342
_refine_ls_abs_structure_details 'Flack (1983), 834 Friedel pairs'
_refine_ls_abs_structure_Flack   0.016(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0210
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0196P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0480
_reflns_number_gt                1956
_reflns_number_total             2091
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2764.cif
_cod_data_source_block           I
_cod_database_code               2228748
_cod_database_fobs_code          2228748
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.27277(5) -0.100786(17) 0.715735(13) 0.03335(9) Uani d . 1 . .
N N1 0.5109(4) 0.10657(15) 0.81851(10) 0.0218(4) Uani d . 1 . .
N N2 0.4796(4) 0.08084(15) 0.94956(10) 0.0263(5) Uani d . 1 . .
H H2C 0.5395 0.0505 0.9904 0.032 Uiso calc R 1 . .
C C1 0.3861(5) 0.04049(18) 0.68858(12) 0.0225(5) Uani d . 1 . .
H H1A 0.2276 0.0878 0.6937 0.027 Uiso calc R 1 . .
C C2 0.6127(5) 0.07596(18) 0.74317(13) 0.0234(5) Uani d . 1 . .
H H2A 0.7521 0.0206 0.7484 0.028 Uiso calc R 1 . .
C C3 0.6883(5) 0.15620(18) 0.62383(11) 0.0262(5) Uani d . 1 . .
H H3A 0.8688 0.1469 0.5994 0.031 Uiso calc R 1 . .
C C4 0.5166(5) 0.0564(2) 0.61047(12) 0.0258(6) Uani d . 1 . .
H H4A 0.3762 0.0675 0.5708 0.031 Uiso calc R 1 . .
C C5 0.5620(5) 0.2564(2) 0.59440(14) 0.0354(6) Uani d . 1 . .
H H5A 0.6704 0.3160 0.6115 0.042 Uiso calc R 1 . .
H H5B 0.5616 0.2560 0.5388 0.042 Uiso calc R 1 . .
C C6 0.6060(5) 0.05312(19) 0.88240(13) 0.0241(5) Uani d . 1 . .
C C7 0.2656(5) 0.15228(17) 0.95953(11) 0.0257(5) Uani d . 1 . .
C C8 0.1829(5) 0.20597(17) 0.89049(12) 0.0244(5) Uani d . 1 . .
H H8A 0.0460 0.2571 0.8921 0.029 Uiso calc R 1 . .
C C9 0.3045(5) 0.18165(17) 0.82441(12) 0.0243(5) Uani d . 1 . .
H H9A 0.2486 0.2166 0.7802 0.029 Uiso calc R 1 . .
O O1 0.7292(4) 0.16509(12) 0.70608(7) 0.0290(4) Uani d . 1 . .
O O2 0.2882(4) 0.26569(14) 0.62192(11) 0.0494(5) Uani d . 1 . .
H H2B 0.2448 0.3279 0.6236 0.074 Uiso calc R 1 . .
O O3 0.7002(4) -0.02551(13) 0.58996(8) 0.0339(4) Uani d . 1 . .
H H3B 0.6137 -0.0730 0.5692 0.051 Uiso calc R 1 . .
O O4 0.7873(4) -0.01293(12) 0.88008(8) 0.0332(4) Uani d . 1 . .
O O5 0.1654(4) 0.16566(13) 1.02337(8) 0.0351(4) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 C9 . . 121.24(18) ?
C6 N1 C2 . . 118.83(18) ?
C9 N1 C2 . . 119.68(17) ?
C6 N2 C7 . . 127.57(18) ?
C6 N2 H2C . . 116.2 ?
C7 N2 H2C . . 116.2 ?
C4 C1 C2 . . 102.81(19) ?
C4 C1 Br1 . . 117.50(16) ?
C2 C1 Br1 . . 109.06(15) ?
C4 C1 H1A . . 109.0 ?
C2 C1 H1A . . 109.0 ?
Br1 C1 H1A . . 109.0 ?
O1 C2 N1 . . 109.36(18) ?
O1 C2 C1 . . 103.78(18) ?
N1 C2 C1 . . 113.54(18) ?
O1 C2 H2A . . 110.0 ?
N1 C2 H2A . . 110.0 ?
C1 C2 H2A . . 110.0 ?
O1 C3 C5 . . 109.06(19) ?
O1 C3 C4 . . 106.75(17) ?
C5 C3 C4 . . 115.4(2) ?
O1 C3 H3A . . 108.5 ?
C5 C3 H3A . . 108.5 ?
C4 C3 H3A . . 108.5 ?
O3 C4 C1 . . 112.99(19) ?
O3 C4 C3 . . 107.85(18) ?
C1 C4 C3 . . 101.55(17) ?
O3 C4 H4A . . 111.3 ?
C1 C4 H4A . . 111.3 ?
C3 C4 H4A . . 111.3 ?
O2 C5 C3 . . 109.7(2) ?
O2 C5 H5A . . 109.7 ?
C3 C5 H5A . . 109.7 ?
O2 C5 H5B . . 109.7 ?
C3 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
O4 C6 N2 . . 122.0(2) ?
O4 C6 N1 . . 123.6(2) ?
N2 C6 N1 . . 114.4(2) ?
O5 C7 N2 . . 119.96(19) ?
O5 C7 C8 . . 125.7(2) ?
N2 C7 C8 . . 114.38(18) ?
C9 C8 C7 . . 119.4(2) ?
C9 C8 H8A . . 120.3 ?
C7 C8 H8A . . 120.3 ?
C8 C9 N1 . . 122.9(2) ?
C8 C9 H9A . . 118.5 ?
N1 C9 H9A . . 118.5 ?
C2 O1 C3 . . 109.45(16) ?
C5 O2 H2B . . 109.5 ?
C4 O3 H3B . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 . 1.938(2) ?
N1 C6 . 1.384(3) ?
N1 C9 . 1.387(3) ?
N1 C2 . 1.456(3) ?
N2 C6 . 1.368(3) ?
N2 C7 . 1.390(3) ?
N2 H2C . 0.8600 ?
C1 C4 . 1.515(3) ?
C1 C2 . 1.522(3) ?
C1 H1A . 0.9800 ?
C2 O1 . 1.422(3) ?
C2 H2A . 0.9800 ?
C3 O1 . 1.452(2) ?
C3 C5 . 1.504(4) ?
C3 C4 . 1.536(3) ?
C3 H3A . 0.9800 ?
C4 O3 . 1.416(3) ?
C4 H4A . 0.9800 ?
C5 O2 . 1.416(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 O4 . 1.216(3) ?
C7 O5 . 1.226(2) ?
C7 C8 . 1.441(3) ?
C8 C9 . 1.331(3) ?
C8 H8A . 0.9300 ?
C9 H9A . 0.9300 ?
O2 H2B . 0.8200 ?
O3 H3B . 0.8200 ?
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
O2 H2B O4 3_656 0.82 2.03 2.841(2) 169
N2 H2C O3 2_655 0.86 2.17 2.983(2) 158
O3 H3B O5 2_554 0.82 1.96 2.769(2) 167
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 163635
