#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/75/2217583.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_2217583
loop_
_publ_author_name
'Djukic, Brandon'
'Harrington, Laura E.'
'Britten, James F.'
'Lemaire, Martin T.'
_publ_section_title
;
 5,7-Di-2-pyridyl-2,3-dihydrothieno[3,4-b][1,4]dioxine
;
_journal_coeditor_code           LH2589
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o463
_journal_page_last               o463
_journal_paper_doi               10.1107/S1600536808001190
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C16 H12 N2 O2 S'
_chemical_formula_moiety         'C16 H12 N2 O2 S'
_chemical_formula_sum            'C16 H12 N2 O2 S'
_chemical_formula_weight         296.34
_chemical_name_systematic
;
5,7-Di-2-pyridyl-2,3-dihydrothieno[3,4-b][1,4]dioxine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.752(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5189(12)
_cell_length_b                   9.8752(12)
_cell_length_c                   13.1961(18)
_cell_measurement_reflns_used    8327
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.31
_cell_measurement_theta_min      2.58
_cell_volume                     1358.2(3)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEXII'
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22945
_diffrn_reflns_theta_full        33.28
_diffrn_reflns_theta_max         33.28
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         5134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0374
_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)+(0.0623P)²+0.2445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                4316
_reflns_number_total             5134
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2589.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2217583
_cod_database_fobs_code          2217583
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_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_occupancy
S S1 0.52108(2) 0.40887(2) 0.128549(18) 0.02244(7) Uani d 1
O O1 0.21374(7) 0.28139(9) -0.04158(6) 0.03008(17) Uani d 1
N N1 0.32131(9) 0.54483(9) 0.22458(7) 0.02895(18) Uani d 1
C C1 0.24126(12) 0.61030(12) 0.27867(9) 0.0343(2) Uani d 1
H H1 0.2820(16) 0.6590(17) 0.3407(13) 0.046(4) Uiso d 1
O O2 0.44345(8) 0.16437(8) -0.10327(6) 0.02944(16) Uani d 1
N N2 0.76947(9) 0.27018(10) 0.12037(8) 0.03112(19) Uani d 1
C C2 0.10899(12) 0.60791(12) 0.25650(10) 0.0343(2) Uani d 1
H H2 0.0574(15) 0.6560(17) 0.2998(12) 0.043(4) Uiso d 1
C C3 0.05533(11) 0.53586(12) 0.17120(10) 0.0338(2) Uani d 1
H H3 -0.0338(17) 0.5319(17) 0.1520(13) 0.044(4) Uiso d 1
C C4 0.13538(11) 0.46837(11) 0.11278(9) 0.0294(2) Uani d 1
H H4 0.0956(16) 0.4152(16) 0.0528(13) 0.043(4) Uiso d 1
C C5 0.26776(9) 0.47352(9) 0.14214(7) 0.02228(17) Uani d 1
C C6 0.35800(9) 0.39961(9) 0.08746(7) 0.02107(17) Uani d 1
C C7 0.33364(9) 0.31265(9) 0.00561(7) 0.02180(17) Uani d 1
C C8 0.21613(12) 0.21560(15) -0.13906(9) 0.0373(3) Uani d 1
H H8B 0.1311(17) 0.1762(17) -0.1607(13) 0.045(4) Uiso d 1
H H8A 0.2400(17) 0.2820(17) -0.1874(14) 0.048(4) Uiso d 1
C C9 0.31708(12) 0.10680(12) -0.13079(10) 0.0343(2) Uani d 1
H H9B 0.3068(16) 0.0402(16) -0.0763(13) 0.042(4) Uiso d 1
H H9A 0.3192(16) 0.0601(16) -0.1964(13) 0.040(4) Uiso d 1
C C10 0.44657(9) 0.25377(9) -0.02383(7) 0.02233(17) Uani d 1
C C11 0.55669(9) 0.29531(9) 0.03618(7) 0.02234(17) Uani d 1
C C12 0.68890(10) 0.25174(10) 0.03345(8) 0.02406(18) Uani d 1
C C13 0.72798(11) 0.19200(11) -0.05374(9) 0.0289(2) Uani d 1
H H13 0.6694(17) 0.1792(18) -0.1144(13) 0.049(5) Uiso d 1
C C14 0.85394(11) 0.14936(13) -0.04938(10) 0.0341(2) Uani d 1
H H14 0.8846(18) 0.1135(18) -0.1082(14) 0.051(5) Uiso d 1
C C15 0.93616(11) 0.16398(14) 0.04084(11) 0.0389(3) Uani d 1
H H15 1.0276(17) 0.1367(18) 0.0466(13) 0.050(5) Uiso d 1
C C16 0.89017(11) 0.22521(14) 0.12321(10) 0.0375(3) Uani d 1
H H16 0.9492(17) 0.2418(17) 0.1890(14) 0.051(5) Uiso 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'
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
_geom_angle_publ_flag
C6 S1 C11 92.56(5) n
C7 O1 C8 112.47(8) n
C1 N1 C5 117.10(10) ?
N1 C1 C2 124.42(11) ?
N1 C1 H1 116.0(9) ?
C2 C1 H1 119.5(9) ?
C10 O2 C9 111.87(8) n
C16 N2 C12 117.70(10) ?
C1 C2 C3 117.94(10) ?
C1 C2 H2 119.8(10) ?
C3 C2 H2 122.3(10) ?
C2 C3 C4 119.15(11) ?
C2 C3 H3 121.6(10) ?
C4 C3 H3 119.3(10) ?
C3 C4 C5 119.10(10) ?
C3 C4 H4 118.4(10) ?
C5 C4 H4 122.5(10) ?
N1 C5 C4 122.27(9) ?
N1 C5 C6 115.39(9) n
C4 C5 C6 122.32(9) ?
C7 C6 C5 129.33(9) ?
C7 C6 S1 110.53(7) ?
C5 C6 S1 120.07(7) ?
O1 C7 C6 124.20(9) ?
O1 C7 C10 122.50(8) ?
C6 C7 C10 113.28(9) ?
O1 C8 C9 110.71(10) ?
O1 C8 H8B 108.2(10) ?
C9 C8 H8B 110.2(10) ?
O1 C8 H8A 108.5(10) ?
C9 C8 H8A 106.7(10) ?
H8B C8 H8A 112.5(15) ?
O2 C9 C8 110.69(10) ?
O2 C9 H9B 105.4(10) ?
C8 C9 H9B 112.5(10) ?
O2 C9 H9A 106.0(10) ?
C8 C9 H9A 111.7(9) ?
H9B C9 H9A 110.1(13) ?
O2 C10 C11 124.44(9) ?
O2 C10 C7 122.58(9) ?
C11 C10 C7 112.98(8) ?
C10 C11 C12 128.97(9) ?
C10 C11 S1 110.66(7) ?
C12 C11 S1 120.30(7) ?
N2 C12 C13 122.44(10) ?
N2 C12 C11 115.59(9) n
C13 C12 C11 121.96(9) ?
C14 C13 C12 118.59(11) ?
C14 C13 H13 120.2(10) ?
C12 C13 H13 121.2(10) ?
C15 C14 C13 119.24(11) ?
C15 C14 H14 120.1(12) ?
C13 C14 H14 120.6(12) ?
C14 C15 C16 118.50(11) ?
C14 C15 H15 121.7(10) ?
C16 C15 H15 119.7(10) ?
N2 C16 C15 123.48(12) ?
N2 C16 H16 116.1(10) ?
C15 C16 H16 120.3(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 1.7303(10) n
S1 C11 1.7340(10) n
O1 C7 1.3644(12) n
O1 C8 1.4444(13) ?
N1 C1 1.3412(14) ?
N1 C5 1.3533(13) ?
C1 C2 1.3828(18) ?
C1 H1 0.996(18) ?
O2 C10 1.3674(12) n
O2 C9 1.4463(14) ?
N2 C16 1.3408(15) ?
N2 C12 1.3435(14) ?
C2 C3 1.3857(17) ?
C2 H2 0.965(16) ?
C3 C4 1.3867(15) ?
C3 H3 0.938(17) ?
C4 C5 1.3950(15) ?
C4 H4 0.994(17) ?
C5 C6 1.4626(13) n
C6 C7 1.3767(13) ?
C7 C10 1.4229(13) ?
C8 C9 1.5042(18) ?
C8 H8B 0.982(17) ?
C8 H8A 0.971(18) ?
C9 H9B 0.991(16) ?
C9 H9A 0.984(16) ?
C10 C11 1.3747(14) ?
C11 C12 1.4609(13) n
C12 C13 1.4029(14) ?
C13 C14 1.3841(16) ?
C13 H13 0.950(18) ?
C14 C15 1.3814(19) ?
C14 H14 0.948(18) ?
C15 C16 1.3868(18) ?
C15 H15 0.992(18) ?
C16 H16 1.010(18) ?
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
_geom_torsion_publ_flag
C5 N1 C1 C2 0.93(18) ?
N1 C1 C2 C3 -1.7(2) ?
C1 C2 C3 C4 0.77(19) ?
C2 C3 C4 C5 0.74(18) ?
C1 N1 C5 C4 0.72(15) ?
C1 N1 C5 C6 -177.85(9) ?
C3 C4 C5 N1 -1.55(16) ?
C3 C4 C5 C6 176.92(10) ?
N1 C5 C6 C7 175.73(10) ?
C4 C5 C6 C7 -2.84(16) ?
N1 C5 C6 S1 -0.78(12) n
C4 C5 C6 S1 -179.35(8) ?
C11 S1 C6 C7 -0.26(7) ?
C11 S1 C6 C5 176.86(8) ?
C8 O1 C7 C6 165.76(10) ?
C8 O1 C7 C10 -16.38(14) ?
C5 C6 C7 O1 1.22(16) ?
S1 C6 C7 O1 177.99(8) ?
C5 C6 C7 C10 -176.82(9) ?
S1 C6 C7 C10 -0.04(10) ?
C7 O1 C8 C9 45.42(14) ?
C10 O2 C9 C8 46.89(13) ?
O1 C8 C9 O2 -62.83(14) ?
C9 O2 C10 C11 161.49(10) ?
C9 O2 C10 C7 -17.88(13) ?
O1 C7 C10 O2 1.80(14) ?
C6 C7 C10 O2 179.87(8) ?
O1 C7 C10 C11 -177.64(9) ?
C6 C7 C10 C11 0.44(12) ?
O2 C10 C11 C12 -3.24(16) ?
C7 C10 C11 C12 176.18(9) ?
O2 C10 C11 S1 179.96(7) ?
C7 C10 C11 S1 -0.62(10) ?
C6 S1 C11 C10 0.51(7) ?
C6 S1 C11 C12 -176.61(8) ?
C16 N2 C12 C13 -2.13(16) ?
C16 N2 C12 C11 176.57(10) ?
C10 C11 C12 N2 -157.14(10) ?
S1 C11 C12 N2 19.39(12) n
C10 C11 C12 C13 21.56(15) ?
S1 C11 C12 C13 -161.91(8) ?
N2 C12 C13 C14 0.69(16) ?
C11 C12 C13 C14 -177.93(10) ?
C12 C13 C14 C15 1.45(17) ?
C13 C14 C15 C16 -2.0(2) ?
C12 N2 C16 C15 1.51(19) ?
C14 C15 C16 N2 0.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119255
