#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:52:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180320 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/34/7153490.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_7153490
loop_
_publ_author_name
'Mkrtchyan, Satenik'
'Iaroshenko, Viktor O.'
'Dudkin, Sergii'
'Gevorgyan, Ashot'
'Vilches-Herrera, Marcelo'
'Ghazaryan, Gagik'
'Volochnyuk, Dmitriy M.'
'Ostrovskyi, Dmytro'
'Ahmed, Zeeshan'
'Villinger, Alexander'
'Sosnovskikh, Vyacheslav Ya'
'Langer, Peter'
_publ_section_title
;
 3-Methoxalylchromone--a novel versatile reagent for the regioselective
 purine isostere synthesis.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5280
_journal_page_last               5284
_journal_paper_doi               10.1039/c0ob00379d
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C17 H15 N3 O4 S'
_chemical_formula_sum            'C17 H15 N3 O4 S'
_chemical_formula_weight         357.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 98.6610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5148(4)
_cell_length_b                   8.3533(2)
_cell_length_c                   12.6393(3)
_cell_measurement_reflns_used    7769
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      60.018
_cell_measurement_theta_min      5.553
_cell_volume                     1619.37(7)
_computing_cell_refinement       'Bruker Apex v2.0-2'
_computing_data_collection       'Bruker Apex v2.0-2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and psi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17166
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_T_min  0.9061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.3579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                3884
_reflns_number_total             4697
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c0ob00379d.txt
_cod_data_source_block           is_sm285
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7153490
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
N1 N 0.99847(7) 0.24820(14) 1.09821(8) 0.0245(2) Uani 1 1 d .
N2 N 0.86445(6) 0.11616(13) 1.04315(8) 0.0222(2) Uani 1 1 d .
N3 N 1.12860(7) 0.39337(15) 1.10863(9) 0.0288(2) Uani 1 1 d .
O1 O 0.69203(6) -0.12374(12) 0.92851(8) 0.0315(2) Uani 1 1 d .
O2 O 0.70705(6) 0.01812(12) 1.08099(8) 0.0301(2) Uani 1 1 d .
O3 O 0.76386(6) -0.02370(14) 0.68650(8) 0.0363(2) Uani 1 1 d .
O4 O 0.61708(7) 0.02935(14) 0.57107(8) 0.0344(2) Uani 1 1 d .
S1 S 1.04782(2) 0.31529(4) 0.91214(2) 0.02542(10) Uani 1 1 d .
C1 C 1.06018(8) 0.31867(15) 1.05381(10) 0.0226(2) Uani 1 1 d .
C2 C 0.93569(8) 0.19007(14) 1.01977(9) 0.0208(2) Uani 1 1 d .
C3 C 0.95029(8) 0.21473(15) 0.91238(10) 0.0221(2) Uani 1 1 d .
C4 C 0.88896(8) 0.16809(16) 0.82779(10) 0.0246(2) Uani 1 1 d .
H4 H 0.8979 0.1837 0.7558 0.030 Uiso 1 1 calc R
C5 C 0.81273(8) 0.09665(15) 0.85232(9) 0.0224(2) Uani 1 1 d .
C6 C 0.80543(7) 0.07057(15) 0.96024(9) 0.0213(2) Uani 1 1 d .
C7 C 0.72896(7) -0.02297(15) 0.98693(10) 0.0229(2) Uani 1 1 d .
C8 C 0.63549(10) -0.0711(2) 1.11300(13) 0.0390(3) Uani 1 1 d .
H8A H 0.5828 -0.0533 1.0610 0.058 Uiso 1 1 calc R
H8B H 0.6254 -0.0350 1.1839 0.058 Uiso 1 1 calc R
H8C H 0.6498 -0.1854 1.1158 0.058 Uiso 1 1 calc R
C9 C 0.74345(8) 0.06053(15) 0.75911(10) 0.0238(2) Uani 1 1 d .
C10 C 0.65721(8) 0.13689(14) 0.74924(9) 0.0209(2) Uani 1 1 d .
C11 C 0.59796(8) 0.11804(15) 0.65392(9) 0.0244(2) Uani 1 1 d .
C12 C 0.51603(9) 0.19055(16) 0.64238(11) 0.0288(3) Uani 1 1 d .
H12 H 0.4767 0.1785 0.5776 0.035 Uiso 1 1 calc R
C13 C 0.49212(9) 0.27965(17) 0.72509(11) 0.0295(3) Uani 1 1 d .
H13 H 0.4361 0.3279 0.7171 0.035 Uiso 1 1 calc R
C14 C 0.54937(9) 0.29955(16) 0.82030(11) 0.0277(3) Uani 1 1 d .
H14 H 0.5322 0.3598 0.8773 0.033 Uiso 1 1 calc R
C15 C 0.63104(8) 0.23124(15) 0.83116(10) 0.0231(2) Uani 1 1 d .
H15 H 0.6706 0.2481 0.8953 0.028 Uiso 1 1 calc R
C16 C 1.19771(8) 0.46048(17) 1.05655(11) 0.0302(3) Uani 1 1 d .
H16A H 1.1843 0.4426 0.9792 0.045 Uiso 1 1 calc R
H16B H 1.2531 0.4084 1.0844 0.045 Uiso 1 1 calc R
H16C H 1.2023 0.5757 1.0709 0.045 Uiso 1 1 calc R
C17 C 1.13652(10) 0.4045(2) 1.22473(11) 0.0381(3) Uani 1 1 d .
H17A H 1.0788 0.4219 1.2452 0.057 Uiso 1 1 calc R
H17B H 1.1748 0.4943 1.2501 0.057 Uiso 1 1 calc R
H17C H 1.1613 0.3048 1.2570 0.057 Uiso 1 1 calc R
H1 H 0.6694(15) -0.003(3) 0.5914(18) 0.065(7) 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 0.0033 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'
S S 0.1246 0.1234 '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
C1 N1 C2 109.43(10)
C2 N2 C6 116.68(10)
C1 N3 C16 122.00(11)
C1 N3 C17 119.56(11)
C16 N3 C17 118.41(11)
C7 O2 C8 115.34(11)
C11 O4 H1 104.3(15)
C3 S1 C1 88.15(6)
N1 C1 N3 124.08(11)
N1 C1 S1 116.60(9)
N3 C1 S1 119.31(9)
N2 C2 N1 121.66(10)
N2 C2 C3 122.19(11)
N1 C2 C3 116.15(10)
C4 C3 C2 120.58(11)
C4 C3 S1 129.67(9)
C2 C3 S1 109.65(9)
C3 C4 C5 117.19(11)
C3 C4 H4 121.4
C5 C4 H4 121.4
C4 C5 C6 118.42(11)
C4 C5 C9 116.15(11)
C6 C5 C9 125.38(11)
N2 C6 C5 124.83(11)
N2 C6 C7 116.29(10)
C5 C6 C7 118.80(11)
O1 C7 O2 124.44(11)
O1 C7 C6 122.99(11)
O2 C7 C6 112.57(10)
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O3 C9 C10 121.06(11)
O3 C9 C5 117.67(11)
C10 C9 C5 120.95(10)
C15 C10 C11 117.87(11)
C15 C10 C9 122.65(11)
C11 C10 C9 119.47(11)
O4 C11 C12 117.36(11)
O4 C11 C10 122.16(11)
C12 C11 C10 120.48(11)
C13 C12 C11 119.99(12)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 120.65(12)
C12 C13 H13 119.7
C14 C13 H13 119.7
C15 C14 C13 119.57(12)
C15 C14 H14 120.2
C13 C14 H14 120.2
C14 C15 C10 121.41(12)
C14 C15 H15 119.3
C10 C15 H15 119.3
N3 C16 H16A 109.5
N3 C16 H16B 109.5
H16A C16 H16B 109.5
N3 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
N3 C17 H17A 109.5
N3 C17 H17B 109.5
H17A C17 H17B 109.5
N3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3190(15)
N1 C2 1.3699(16)
N2 C2 1.3373(15)
N2 C6 1.3388(16)
N3 C1 1.3322(16)
N3 C16 1.4524(16)
N3 C17 1.4570(17)
O1 C7 1.2062(16)
O2 C7 1.3298(15)
O2 C8 1.4445(16)
O3 C9 1.2350(15)
O4 C11 1.3517(15)
O4 H1 0.86(2)
S1 C3 1.7310(12)
S1 C1 1.7721(13)
C2 C3 1.4243(16)
C3 C4 1.3762(18)
C4 C5 1.4005(17)
C4 H4 0.9500
C5 C6 1.4027(16)
C5 C9 1.5010(17)
C6 C7 1.5008(16)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.4704(17)
C10 C15 1.4088(16)
C10 C11 1.4099(17)
C11 C12 1.3957(18)
C12 C13 1.379(2)
C12 H12 0.9500
C13 C14 1.3939(19)
C13 H13 0.9500
C14 C15 1.3776(17)
C14 H14 0.9500
C15 H15 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
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
C2 N1 C1 N3 177.00(12)
C2 N1 C1 S1 -1.51(14)
C16 N3 C1 N1 176.05(13)
C17 N3 C1 N1 -2.0(2)
C16 N3 C1 S1 -5.48(18)
C17 N3 C1 S1 176.49(11)
C3 S1 C1 N1 1.39(11)
C3 S1 C1 N3 -177.20(11)
C6 N2 C2 N1 177.04(11)
C6 N2 C2 C3 -2.16(18)
C1 N1 C2 N2 -178.40(11)
C1 N1 C2 C3 0.86(15)
N2 C2 C3 C4 2.59(19)
N1 C2 C3 C4 -176.66(11)
N2 C2 C3 S1 179.39(9)
N1 C2 C3 S1 0.15(14)
C1 S1 C3 C4 175.65(13)
C1 S1 C3 C2 -0.78(9)
C2 C3 C4 C5 0.11(18)
S1 C3 C4 C5 -175.99(10)
C3 C4 C5 C6 -2.88(18)
C3 C4 C5 C9 174.63(11)
C2 N2 C6 C5 -0.87(18)
C2 N2 C6 C7 175.61(10)
C4 C5 C6 N2 3.48(19)
C9 C5 C6 N2 -173.78(12)
C4 C5 C6 C7 -172.92(11)
C9 C5 C6 C7 9.82(18)
C8 O2 C7 O1 1.98(19)
C8 O2 C7 C6 -178.16(11)
N2 C6 C7 O1 -148.68(12)
C5 C6 C7 O1 28.03(18)
N2 C6 C7 O2 31.47(15)
C5 C6 C7 O2 -151.83(11)
C4 C5 C9 O3 55.87(17)
C6 C5 C9 O3 -126.81(14)
C4 C5 C9 C10 -117.68(13)
C6 C5 C9 C10 59.64(18)
O3 C9 C10 C15 178.77(12)
C5 C9 C10 C15 -7.90(18)
O3 C9 C10 C11 -2.14(19)
C5 C9 C10 C11 171.19(11)
C15 C10 C11 O4 -179.76(12)
C9 C10 C11 O4 1.11(19)
C15 C10 C11 C12 -0.32(18)
C9 C10 C11 C12 -179.45(12)
O4 C11 C12 C13 178.61(12)
C10 C11 C12 C13 -0.9(2)
C11 C12 C13 C14 0.6(2)
C12 C13 C14 C15 0.9(2)
C13 C14 C15 C10 -2.1(2)
C11 C10 C15 C14 1.81(18)
C9 C10 C15 C14 -179.09(12)
