#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:52:34 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180320 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/34/7153488.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_7153488
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         'C12 H8 O5'
_chemical_formula_sum            'C12 H8 O5'
_chemical_formula_weight         232.18
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.438(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4760(8)
_cell_length_b                   6.7599(5)
_cell_length_c                   14.5944(10)
_cell_measurement_reflns_used    2224
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      53.578
_cell_measurement_theta_min      4.929
_cell_volume                     1031.67(13)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10806
_diffrn_reflns_theta_full        29.92
_diffrn_reflns_theta_max         29.92
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.8907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0494
_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)+(0.0720P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                1868
_reflns_number_total             2982
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c0ob00379d.txt
_cod_data_source_block           is_g104
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7153488
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.10120(11) -0.44385(16) 0.69318(7) 0.0302(3) Uani 1 1 d .
O2 O 0.11329(11) 0.09810(16) 0.56780(7) 0.0282(3) Uani 1 1 d .
O3 O 0.15225(14) -0.39750(19) 0.41281(8) 0.0438(3) Uani 1 1 d .
O4 O 0.34455(11) -0.02913(19) 0.46591(7) 0.0377(3) Uani 1 1 d .
O5 O 0.18696(12) 0.00107(18) 0.35402(7) 0.0346(3) Uani 1 1 d .
C1 C 0.12179(16) -0.4255(2) 0.60366(10) 0.0273(4) Uani 1 1 d .
H1 H 0.1294 -0.5432 0.5688 0.033 Uiso 1 1 calc R
C2 C 0.13237(14) -0.2505(2) 0.55975(9) 0.0239(3) Uani 1 1 d .
C3 C 0.11412(14) -0.0639(2) 0.60692(9) 0.0212(3) Uani 1 1 d .
C4 C 0.09575(14) -0.0853(2) 0.70638(9) 0.0219(3) Uani 1 1 d .
C5 C 0.09152(14) -0.2730(2) 0.74491(10) 0.0243(3) Uani 1 1 d .
C6 C 0.07683(15) -0.3018(3) 0.83857(10) 0.0321(4) Uani 1 1 d .
H6 H 0.0756 -0.4311 0.8640 0.039 Uiso 1 1 calc R
C7 C 0.06415(17) -0.1372(3) 0.89283(10) 0.0346(4) Uani 1 1 d .
H7 H 0.0541 -0.1535 0.9567 0.041 Uiso 1 1 calc R
C8 C 0.06582(17) 0.0529(3) 0.85584(10) 0.0332(4) Uani 1 1 d .
H8 H 0.0562 0.1646 0.8943 0.040 Uiso 1 1 calc R
C9 C 0.08145(15) 0.0789(2) 0.76299(10) 0.0265(4) Uani 1 1 d .
H9 H 0.0824 0.2085 0.7378 0.032 Uiso 1 1 calc R
C10 C 0.16650(15) -0.2546(2) 0.46289(10) 0.0282(4) Uani 1 1 d .
C11 C 0.24251(16) -0.0761(2) 0.42974(10) 0.0285(4) Uani 1 1 d .
C12 C 0.25345(19) 0.1647(3) 0.31280(13) 0.0457(5) Uani 1 1 d .
H12A H 0.2625 0.2741 0.3567 0.068 Uiso 1 1 calc R
H12B H 0.2042 0.2093 0.2574 0.068 Uiso 1 1 calc R
H12C H 0.3383 0.1208 0.2965 0.068 Uiso 1 1 calc R
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'
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
C1 O1 C5 118.31(12)
C11 O5 C12 116.53(14)
O1 C1 C2 124.34(14)
O1 C1 H1 117.8
C2 C1 H1 117.8
C1 C2 C3 121.13(13)
C1 C2 C10 117.88(13)
C3 C2 C10 120.96(13)
O2 C3 C2 123.20(12)
O2 C3 C4 122.79(13)
C2 C3 C4 114.02(12)
C5 C4 C9 118.62(13)
C5 C4 C3 119.63(13)
C9 C4 C3 121.75(13)
O1 C5 C4 122.33(12)
O1 C5 C6 115.61(13)
C4 C5 C6 122.05(14)
C7 C6 C5 118.03(15)
C7 C6 H6 121.0
C5 C6 H6 121.0
C6 C7 C8 121.22(14)
C6 C7 H7 119.4
C8 C7 H7 119.4
C9 C8 C7 120.03(15)
C9 C8 H8 120.0
C7 C8 H8 120.0
C8 C9 C4 120.04(14)
C8 C9 H9 120.0
C4 C9 H9 120.0
O3 C10 C2 124.17(15)
O3 C10 C11 118.77(13)
C2 C10 C11 116.42(13)
O4 C11 O5 126.50(16)
O4 C11 C10 122.04(14)
O5 C11 C10 111.17(14)
O5 C12 H12A 109.5
O5 C12 H12B 109.5
H12A C12 H12B 109.5
O5 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3425(17)
O1 C5 1.3867(18)
O2 C3 1.2348(16)
O3 C10 1.2151(19)
O4 C11 1.206(2)
O5 C11 1.3249(19)
O5 C12 1.456(2)
C1 C2 1.353(2)
C1 H1 0.9500
C2 C3 1.455(2)
C2 C10 1.479(2)
C3 C4 1.4827(18)
C4 C5 1.390(2)
C4 C9 1.397(2)
C5 C6 1.398(2)
C6 C7 1.377(2)
C6 H6 0.9500
C7 C8 1.395(2)
C7 H7 0.9500
C8 C9 1.386(2)
C8 H8 0.9500
C9 H9 0.9500
C10 C11 1.539(2)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 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
C5 O1 C1 C2 -0.8(2)
O1 C1 C2 C3 -3.7(3)
O1 C1 C2 C10 174.65(14)
C1 C2 C3 O2 -174.33(15)
C10 C2 C3 O2 7.3(2)
C1 C2 C3 C4 5.3(2)
C10 C2 C3 C4 -173.02(13)
O2 C3 C4 C5 176.83(14)
C2 C3 C4 C5 -2.8(2)
O2 C3 C4 C9 -2.7(2)
C2 C3 C4 C9 177.68(14)
C1 O1 C5 C4 3.4(2)
C1 O1 C5 C6 -176.76(14)
C9 C4 C5 O1 178.11(14)
C3 C4 C5 O1 -1.4(2)
C9 C4 C5 C6 -1.7(2)
C3 C4 C5 C6 178.77(14)
O1 C5 C6 C7 -178.71(14)
C4 C5 C6 C7 1.1(2)
C5 C6 C7 C8 0.0(3)
C6 C7 C8 C9 -0.5(3)
C7 C8 C9 C4 -0.1(3)
C5 C4 C9 C8 1.2(2)
C3 C4 C9 C8 -179.32(15)
C1 C2 C10 O3 20.8(3)
C3 C2 C10 O3 -160.76(16)
C1 C2 C10 C11 -149.85(15)
C3 C2 C10 C11 28.5(2)
C12 O5 C11 O4 -2.9(2)
C12 O5 C11 C10 -176.76(13)
O3 C10 C11 O4 -113.06(18)
C2 C10 C11 O4 58.2(2)
O3 C10 C11 O5 61.2(2)
C2 C10 C11 O5 -127.63(14)
