#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/34/7153497.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_7153497
loop_
_publ_author_name
'Xie, Yun'
'Maxson, Tucker'
'Tor, Yitzhak'
_publ_section_title
;
 Fluorescent nucleoside analogue displays enhanced emission upon pairing
 with guanine.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5053
_journal_page_last               5055
_journal_paper_doi               10.1039/c0ob00413h
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H17 N3 O6'
_chemical_formula_weight         311.30
_chemical_name_common            ADDTop
_chemical_name_systematic
;
?
;
_space_group.centring_type       P
_space_group_IT_number           19
_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                   6.837(2)
_cell_length_b                   10.470(5)
_cell_length_c                   18.506(6)
_cell_measurement_temperature    100(2)
_cell_volume                     1324.7(9)
_computing_cell_refinement       'Bruker ApexII'
_computing_data_collection       'Bruker ApexII'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  KappaApexII
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         0.5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6001
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.50
_diffrn_reflns_theta_min         4.78
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_correction_T_min  0.8567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0358
_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/[σ²(Fo²)+(0.0581P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                2037
_reflns_number_total             2269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00413h.txt
_cod_data_source_block           tor41
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7153497
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.6260(3) 0.85690(18) 0.01043(11) 0.0158(4) Uani 1 1 d .
C2 C 0.6379(3) 0.84519(19) 0.08503(11) 0.0179(4) Uani 1 1 d .
H2 H 0.6483 0.9198 0.1140 0.022 Uiso 1 1 calc R
C3 C 0.6346(3) 0.72544(19) 0.11803(11) 0.0188(4) Uani 1 1 d .
C4 C 0.6201(3) 0.61478(19) 0.07447(12) 0.0195(4) Uani 1 1 d .
H4 H 0.6173 0.5325 0.0961 0.023 Uiso 1 1 calc R
C5 C 0.6100(3) 0.62722(19) 0.00076(12) 0.0180(4) Uani 1 1 d .
H5 H 0.6000 0.5525 -0.0281 0.022 Uiso 1 1 calc R
C6 C 0.6140(3) 0.7467(2) -0.03308(11) 0.0166(4) Uani 1 1 d .
C7 C 0.6088(3) 0.75658(18) -0.11061(11) 0.0163(4) Uani 1 1 d .
C8 C 0.6319(3) 0.98927(18) -0.09770(11) 0.0157(4) Uani 1 1 d .
C9 C 0.6385(3) 1.09785(19) 0.01676(11) 0.0167(4) Uani 1 1 d .
H101 H 0.6432 1.1700 -0.0186 0.020 Uiso 1 1 calc R
C10 C 0.4722(3) 1.1238(2) 0.07060(12) 0.0199(5) Uani 1 1 d .
H10A H 0.3708 1.1793 0.0489 0.024 Uiso 1 1 calc R
H10B H 0.4106 1.0430 0.0867 0.024 Uiso 1 1 calc R
C11 C 0.5747(3) 1.19108(18) 0.13362(11) 0.0162(4) Uani 1 1 d .
H11 H 0.5567 1.1414 0.1793 0.019 Uiso 1 1 calc R
C12 C 0.7923(3) 1.19400(19) 0.11207(11) 0.0159(4) Uani 1 1 d .
H12 H 0.8231 1.2794 0.0907 0.019 Uiso 1 1 calc R
C13 C 0.9361(3) 1.16672(19) 0.17246(11) 0.0180(5) Uani 1 1 d .
H13A H 1.0687 1.1567 0.1517 0.022 Uiso 1 1 calc R
H13B H 0.9390 1.2404 0.2060 0.022 Uiso 1 1 calc R
N1 N 0.6187(3) 0.87971(15) -0.13737(9) 0.0170(4) Uani 1 1 d .
H1 H 0.6162 0.8883 -0.1847 0.020 Uiso 1 1 calc R
N2 N 0.6296(3) 0.97765(15) -0.02370(9) 0.0158(4) Uani 1 1 d .
N3 N 0.6475(3) 0.71563(17) 0.19058(10) 0.0235(4) Uani 1 1 d .
H3A H 0.6579 0.7849 0.2172 0.028 Uiso 1 1 calc R
H3B H 0.6454 0.6400 0.2112 0.028 Uiso 1 1 calc R
O1 O 0.5974(2) 0.66558(13) -0.15316(8) 0.0205(3) Uani 1 1 d .
O2 O 0.6430(2) 1.09320(12) -0.12922(8) 0.0188(3) Uani 1 1 d .
O3 O 0.8156(2) 1.09857(13) 0.05751(8) 0.0176(3) Uani 1 1 d .
O4 O 0.5152(2) 1.32051(13) 0.14379(9) 0.0248(4) Uani 1 1 d .
H4A H 0.3937 1.3263 0.1379 0.037 Uiso 1 1 calc R
O5 O 0.8867(2) 1.05415(13) 0.21191(8) 0.0193(3) Uani 1 1 d .
H5A H 0.9394 0.9905 0.1923 0.029 Uiso 1 1 calc R
O6 O 0.6307(3) 0.46609(14) 0.26130(9) 0.0247(4) Uani 1 1 d .
H6B H 0.611(4) 0.413(2) 0.2242(15) 0.037 Uiso 1 1 d .
H6A H 0.722(4) 0.420(2) 0.2869(17) 0.037 Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 119.94(19)
C2 C1 N2 121.49(18)
C6 C1 N2 118.56(18)
C1 C2 C3 120.92(19)
C1 C2 H2 119.5
C3 C2 H2 119.5
N3 C3 C2 120.20(18)
N3 C3 C4 120.60(19)
C2 C3 C4 119.20(19)
C5 C4 C3 119.48(19)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 121.94(19)
C4 C5 H5 119.0
C6 C5 H5 119.0
C5 C6 C1 118.51(19)
C5 C6 C7 120.70(19)
C1 C6 C7 120.79(19)
O1 C7 N1 119.52(19)
O1 C7 C6 125.44(19)
N1 C7 C6 115.04(17)
O2 C8 N1 119.33(18)
O2 C8 N2 123.25(18)
N1 C8 N2 117.42(17)
O3 C9 N2 108.05(17)
O3 C9 C10 106.55(17)
N2 C9 C10 116.88(18)
O3 C9 H101 108.4
N2 C9 H101 108.4
C10 C9 H101 108.4
C11 C10 C9 103.66(17)
C11 C10 H10A 111.0
C9 C10 H10A 111.0
C11 C10 H10B 111.0
C9 C10 H10B 111.0
H10A C10 H10B 109.0
O4 C11 C10 113.99(17)
O4 C11 C12 106.89(16)
C10 C11 C12 104.71(17)
O4 C11 H11 110.3
C10 C11 H11 110.3
C12 C11 H11 110.3
O3 C12 C13 108.46(16)
O3 C12 C11 106.07(16)
C13 C12 C11 115.58(17)
O3 C12 H12 108.8
C13 C12 H12 108.8
C11 C12 H12 108.8
O5 C13 C12 112.30(17)
O5 C13 H13A 109.1
C12 C13 H13A 109.1
O5 C13 H13B 109.1
C12 C13 H13B 109.1
H13A C13 H13B 107.9
C8 N1 C7 126.46(17)
C8 N1 H1 116.8
C7 N1 H1 116.8
C8 N2 C1 121.63(16)
C8 N2 C9 115.61(16)
C1 N2 C9 122.72(16)
C3 N3 H3A 120.0
C3 N3 H3B 120.0
H3A N3 H3B 120.0
C9 O3 C12 106.39(15)
C11 O4 H4A 109.5
C13 O5 H5A 109.5
H6B O6 H6A 100(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.388(3)
C1 C6 1.410(3)
C1 N2 1.413(3)
C2 C3 1.395(3)
C2 H2 0.9500
C3 N3 1.349(3)
C3 C4 1.415(3)
C4 C5 1.372(3)
C4 H4 0.9500
C5 C6 1.399(3)
C5 H5 0.9500
C6 C7 1.439(3)
C7 O1 1.238(2)
C7 N1 1.383(2)
C8 O2 1.237(2)
C8 N1 1.365(2)
C8 N2 1.375(2)
C9 O3 1.427(3)
C9 N2 1.466(3)
C9 C10 1.536(3)
C9 H101 1.0000
C10 C11 1.532(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 O4 1.427(2)
C11 C12 1.541(3)
C11 H11 1.0000
C12 O3 1.429(3)
C12 C13 1.516(3)
C12 H12 1.0000
C13 O5 1.427(2)
C13 H13A 0.9900
C13 H13B 0.9900
N1 H1 0.8800
N3 H3A 0.8800
N3 H3B 0.8800
O4 H4A 0.8400
O5 H5A 0.8400
O6 H6B 0.89(3)
O6 H6A 0.92(3)
