#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/66/2206618.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_2206618
loop_
_publ_author_name
'Sheng-Zhen Xu'
'Min-Hui Cao'
'Yang-Gen Hu'
'Ming-Wu Ding'
'Wen-Jing Xiao'
_publ_section_title
;
 2-Ethoxy-3-isopropylbenzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one
;
_journal_coeditor_code           AT6024
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2789
_journal_page_last               o2790
_journal_paper_doi               10.1107/S1600536805024177
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H16 N2 O2 S'
_chemical_formula_moiety         'C15 H16 N2 O2 S'
_chemical_formula_sum            'C15 H16 N2 O2 S'
_chemical_formula_weight         288.36
_chemical_melting_point          439
_chemical_name_systematic
;
2-Ethoxy-3-isopropylbenzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                   13.3930(16)
_cell_length_b                   6.8922(8)
_cell_length_c                   15.4970(18)
_cell_measurement_reflns_used    1811
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.36
_cell_measurement_theta_min      2.63
_cell_volume                     1430.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8299
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.0436
_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)+(0.0653P)²+0.1581P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.113
_refine_ls_wR_factor_ref         0.122
_reflns_number_gt                1339
_reflns_number_total             1768
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at6024.cif
_cod_data_source_block           I
_cod_database_code               2206618
_cod_database_fobs_code          2206618
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_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_type_symbol
C1 0.49801(18) 0.2500 0.36424(14) 0.0429(5) Uani d S 1 C
C2 0.4099(2) 0.2500 0.31674(15) 0.0513(6) Uani d S 1 C
H2 0.4113 0.2500 0.2567 0.062 Uiso calc SR 1 H
C3 0.32083(19) 0.2500 0.36069(17) 0.0527(6) Uani d S 1 C
H3 0.2612 0.2500 0.3299 0.063 Uiso calc SR 1 H
C4 0.31837(18) 0.2500 0.45112(16) 0.0521(6) Uani d S 1 C
H4 0.2572 0.2500 0.4796 0.063 Uiso calc SR 1 H
C5 0.40519(16) 0.2500 0.49810(15) 0.0442(5) Uani d S 1 C
H5 0.4033 0.2500 0.5581 0.053 Uiso calc SR 1 H
C6 0.49593(16) 0.2500 0.45486(13) 0.0379(5) Uani d S 1 C
C7 0.59575(15) 0.2500 0.49016(13) 0.0365(5) Uani d S 1 C
C8 0.66755(17) 0.2500 0.42693(13) 0.0421(5) Uani d S 1 C
C9 0.77150(17) 0.2500 0.44766(14) 0.0451(6) Uani d S 1 C
C10 0.71121(15) 0.2500 0.59498(13) 0.0375(5) Uani d S 1 C
C11 0.66507(18) 0.2500 0.74256(14) 0.0473(6) Uani d S 1 C
H11A 0.6233 0.1357 0.7370 0.057 Uiso calc PR 0.50 H
H11B 0.6233 0.3643 0.7370 0.057 Uiso calc PR 0.50 H
C12 0.7166(2) 0.2500 0.82715(15) 0.0608(7) Uani d S 1 C
H12A 0.7697 0.1564 0.8263 0.091 Uiso calc PR 0.50 H
H12B 0.6699 0.2170 0.8718 0.091 Uiso calc PR 0.50 H
H12C 0.7437 0.3766 0.8382 0.091 Uiso calc PR 0.50 H
C13 0.89701(16) 0.2500 0.56478(16) 0.0486(6) Uani d S 1 C
H13 0.9362 0.2500 0.5114 0.058 Uiso calc SR 1 H
C14 0.92519(14) 0.0658(3) 0.61179(14) 0.0714(6) Uani d . 1 C
H14A 0.8929 0.0632 0.6671 0.107 Uiso calc R 1 H
H14B 0.9963 0.0617 0.6196 0.107 Uiso calc R 1 H
H14C 0.9043 -0.0445 0.5785 0.107 Uiso calc R 1 H
N1 0.78992(13) 0.2500 0.53721(11) 0.0402(4) Uani d S 1 N
N2 0.61726(12) 0.2500 0.57616(11) 0.0373(4) Uani d S 1 N
O1 0.84015(13) 0.2500 0.39468(11) 0.0659(6) Uani d S 1 O
O2 0.74189(11) 0.2500 0.67665(9) 0.0469(4) Uani d S 1 O
S1 0.61938(5) 0.2500 0.32309(4) 0.0538(2) Uani d S 1 S
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . . 120.8(2)
C2 C1 S1 . . 126.61(18)
C6 C1 S1 . . 112.56(17)
C3 C2 C1 . . 118.3(2)
C3 C2 H2 . . 120.8
C1 C2 H2 . . 120.8
C2 C3 C4 . . 121.1(2)
C2 C3 H3 . . 119.5
C4 C3 H3 . . 119.5
C5 C4 C3 . . 120.7(2)
C5 C4 H4 . . 119.6
C3 C4 H4 . . 119.6
C4 C5 C6 . . 119.1(2)
C4 C5 H5 . . 120.5
C6 C5 H5 . . 120.5
C5 C6 C1 . . 120.0(2)
C5 C6 C7 . . 128.88(19)
C1 C6 C7 . . 111.11(19)
N2 C7 C8 . . 123.34(19)
N2 C7 C6 . . 124.45(18)
C8 C7 C6 . . 112.21(19)
C7 C8 C9 . . 121.5(2)
C7 C8 S1 . . 113.69(17)
C9 C8 S1 . . 124.85(17)
O1 C9 N1 . . 121.7(2)
O1 C9 C8 . . 125.2(2)
N1 C9 C8 . . 113.08(18)
N2 C10 O2 . . 121.04(19)
N2 C10 N1 . . 126.60(19)
O2 C10 N1 . . 112.35(18)
O2 C11 C12 . . 107.01(19)
O2 C11 H11A . . 110.3
C12 C11 H11A . . 110.3
O2 C11 H11B . . 110.3
C12 C11 H11B . . 110.3
H11A C11 H11B . . 108.6
C11 C12 H12A . . 109.5
C11 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C11 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
N1 C13 C14 . . 112.14(13)
N1 C13 C14 . 7_565 112.14(13)
C14 C13 C14 . 7_565 114.3(2)
N1 C13 H13 . . 105.8
C14 C13 H13 . . 105.8
C14 C13 H13 7_565 . 105.8
C13 C14 H14A . . 109.5
C13 C14 H14B . . 109.5
H14A C14 H14B . . 109.5
C13 C14 H14C . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
C10 N1 C9 . . 120.26(18)
C10 N1 C13 . . 123.07(18)
C9 N1 C13 . . 116.67(18)
C10 N2 C7 . . 115.25(18)
C10 O2 C11 . . 116.80(17)
C8 S1 C1 . . 90.43(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.390(3)
C1 C6 . 1.405(3)
C1 S1 . 1.746(2)
C2 C3 . 1.374(4)
C2 H2 . 0.9300
C3 C4 . 1.402(4)
C3 H3 . 0.9300
C4 C5 . 1.372(3)
C4 H4 . 0.9300
C5 C6 . 1.388(3)
C5 H5 . 0.9300
C6 C7 . 1.444(3)
C7 N2 . 1.364(3)
C7 C8 . 1.373(3)
C8 C9 . 1.429(3)
C8 S1 . 1.734(2)
C9 O1 . 1.233(3)
C9 N1 . 1.409(3)
C10 N2 . 1.292(3)
C10 O2 . 1.331(2)
C10 N1 . 1.383(3)
C11 O2 . 1.450(3)
C11 C12 . 1.482(3)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 N1 . 1.496(3)
C13 C14 . 1.512(2)
C13 C14 7_565 1.512(2)
C13 H13 . 0.9800
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 0.9600
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
C14 H14A O2 . 0.96 2.40 2.941(2) 115
C13 H13 O1 . 0.98 2.22 2.744(3) 112
C2 H2 O1 4_455 0.93 2.53 3.407(3) 157
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_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . 0.0
S1 C1 C2 C3 . 180.0
C1 C2 C3 C4 . 0.0
C2 C3 C4 C5 . 0.0
C3 C4 C5 C6 . 0.0
C4 C5 C6 C1 . 0.0
C4 C5 C6 C7 . 180.0
C2 C1 C6 C5 . 0.0
S1 C1 C6 C5 . 180.0
C2 C1 C6 C7 . 180.0
S1 C1 C6 C7 . 0.0
C5 C6 C7 N2 . 0.0
C1 C6 C7 N2 . 180.0
C5 C6 C7 C8 . 180.0
C1 C6 C7 C8 . 0.0
N2 C7 C8 C9 . 0.0
C6 C7 C8 C9 . 180.0
N2 C7 C8 S1 . 180.0
C6 C7 C8 S1 . 0.0
C7 C8 C9 O1 . 180.0
S1 C8 C9 O1 . 0.0
C7 C8 C9 N1 . 0.0
S1 C8 C9 N1 . 180.0
N2 C10 N1 C9 . 0.0
O2 C10 N1 C9 . 180.0
N2 C10 N1 C13 . 180.0
O2 C10 N1 C13 . 0.0
O1 C9 N1 C10 . 180.0
C8 C9 N1 C10 . 0.0
O1 C9 N1 C13 . 0.0
C8 C9 N1 C13 . 180.0
C14 C13 N1 C10 . 65.06(16)
C14 C13 N1 C10 7_565 -65.06(16)
C14 C13 N1 C9 . -114.94(16)
C14 C13 N1 C9 7_565 114.94(16)
O2 C10 N2 C7 . 180.0
N1 C10 N2 C7 . 0.0
C8 C7 N2 C10 . 0.0
C6 C7 N2 C10 . 180.0
N2 C10 O2 C11 . 0.0
N1 C10 O2 C11 . 180.0
C12 C11 O2 C10 . 180.0
C7 C8 S1 C1 . 0.0
C9 C8 S1 C1 . 180.0
C2 C1 S1 C8 . 180.0
C6 C1 S1 C8 . 0.0
