#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/39/4103921.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_4103921
loop_
_publ_author_name
'Takashi Hirano'
'Yosuke Hasumi'
'Kazuhiro Ohtsuka'
'Shojiro Maki'
'Haruki Niwa'
'Minoru Yamaji'
'Daisuke Hashizume'
_publ_section_title
;
 Spectroscopic Studies of the Light-Color Modulation Mechanism of Firefly
 (Beetle) Bioluminescence
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2385
_journal_page_last               2396
_journal_paper_doi               10.1021/ja808836b
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C12 H10 N2 O2 S2'
_chemical_formula_sum            'C12 H10 N2 O2 S2'
_chemical_formula_weight         278.34
_chemical_melting_point          553(2)
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.2443(2)
_cell_length_b                   10.0849(2)
_cell_length_c                   21.2607(4)
_cell_measurement_reflns_used    67455
_cell_measurement_temperature    90
_cell_measurement_theta_max      31.02
_cell_measurement_theta_min      1.92
_cell_volume                     2410.91(8)
_computing_cell_refinement       HKL2000
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        HKL2000
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC-8 with Saturn70 CCD'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            62676
_diffrn_reflns_theta_full        31.02
_diffrn_reflns_theta_max         31.02
_diffrn_reflns_theta_min         1.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
Absorption corrections were not applied.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0317
_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)+(0.0389P)²+1.2390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                3079
_reflns_number_total             3848
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja808836b_si_002.cif
_cod_data_source_block           1-OH
_cod_database_code               4103921
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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
S1 S 0.09265(3) 0.41682(3) 0.119832(15) 0.01670(8) Uani 1 1 d
S2 S 0.41286(3) 0.53809(3) 0.222943(15) 0.01539(8) Uani 1 1 d
O1 O 0.33299(9) 0.21112(11) 0.03660(5) 0.0259(2) Uani 1 1 d
O2 O 0.42519(9) 0.90335(10) 0.39640(4) 0.01705(19) Uani 1 1 d
H2 H 0.4956(18) 0.8893(19) 0.3936(9) 0.031(5) Uiso 1 1 d
N1 N 0.32208(10) 0.36549(11) 0.11583(5) 0.0167(2) Uani 1 1 d
N2 N 0.18508(10) 0.58910(11) 0.22627(5) 0.0160(2) Uani 1 1 d
C1 C 0.23877(11) 0.43108(12) 0.14522(6) 0.0145(2) Uani 1 1 d
C2 C 0.27356(12) 0.28791(13) 0.06712(6) 0.0171(2) Uani 1 1 d
C3 C 0.14095(11) 0.31145(12) 0.05431(6) 0.0151(2) Uani 1 1 d
C4 C 0.26587(11) 0.51823(12) 0.19756(6) 0.0149(2) Uani 1 1 d
C5 C 0.23799(11) 0.66745(13) 0.27130(6) 0.0148(2) Uani 1 1 d
C6 C 0.17839(11) 0.75899(14) 0.31013(6) 0.0179(2) Uani 1 1 d
H6 H 0.0928(15) 0.7661(16) 0.3069(8) 0.019(4) Uiso 1 1 d
C7 C 0.24367(12) 0.83566(13) 0.35108(6) 0.0176(2) Uani 1 1 d
H7 H 0.2041(13) 0.9001(15) 0.3779(7) 0.011(4) Uiso 1 1 d
C8 C 0.36857(11) 0.82217(12) 0.35480(6) 0.0145(2) Uani 1 1 d
C9 C 0.42960(11) 0.73028(13) 0.31827(6) 0.0148(2) Uani 1 1 d
H9 H 0.5128(16) 0.7187(18) 0.3210(8) 0.026(5) Uiso 1 1 d
C10 C 0.36290(11) 0.65456(12) 0.27644(6) 0.0136(2) Uani 1 1 d
C11 C 0.13092(14) 0.38605(14) -0.00852(6) 0.0197(3) Uani 1 1 d
H11A H 0.1708(15) 0.4700(19) -0.0062(9) 0.027(5) Uiso 1 1 d
H11B H 0.0604(14) 0.3962(15) -0.0228(7) 0.007(3) Uiso 1 1 d
H11C H 0.1734(16) 0.3366(19) -0.0397(9) 0.030(5) Uiso 1 1 d
C12 C 0.07186(13) 0.18111(14) 0.05291(7) 0.0210(3) Uani 1 1 d
H12A H 0.0792(15) 0.1352(18) 0.0931(8) 0.023(4) Uiso 1 1 d
H12B H 0.1039(15) 0.1245(17) 0.0197(8) 0.024(4) Uiso 1 1 d
H12C H -0.0139(17) 0.1992(19) 0.0445(9) 0.032(5) 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 S1 C3 90.22(6)
C10 S2 C4 88.50(6)
C8 O2 H2 107.8(14)
C1 N1 C2 110.82(11)
C4 N2 C5 109.77(11)
N1 C1 C4 121.56(11)
N1 C1 S1 119.23(10)
C4 C1 S1 119.19(9)
O1 C2 N1 122.39(12)
O1 C2 C3 122.68(12)
N1 C2 C3 114.91(11)
C12 C3 C2 111.39(11)
C12 C3 C11 111.52(11)
C2 C3 C11 107.54(11)
C12 C3 S1 111.28(9)
C2 C3 S1 104.04(8)
C11 C3 S1 110.78(9)
N2 C4 C1 122.93(11)
N2 C4 S2 116.73(9)
C1 C4 S2 120.29(9)
N2 C5 C6 125.33(11)
N2 C5 C10 115.47(11)
C6 C5 C10 119.17(11)
C7 C6 C5 119.03(12)
C7 C6 H6 122.2(10)
C5 C6 H6 118.7(10)
C6 C7 C8 120.75(12)
C6 C7 H7 120.2(9)
C8 C7 H7 119.1(9)
O2 C8 C9 122.16(11)
O2 C8 C7 116.28(11)
C9 C8 C7 121.56(11)
C8 C9 C10 117.18(11)
C8 C9 H9 122.5(11)
C10 C9 H9 120.4(11)
C9 C10 C5 122.28(11)
C9 C10 S2 128.18(10)
C5 C10 S2 109.52(9)
C3 C11 H11A 110.7(11)
C3 C11 H11B 115.7(10)
H11A C11 H11B 110.3(15)
C3 C11 H11C 108.1(11)
H11A C11 H11C 105.2(15)
H11B C11 H11C 106.3(14)
C3 C12 H12A 110.4(10)
C3 C12 H12B 109.2(10)
H12A C12 H12B 108.9(15)
C3 C12 H12C 109.8(11)
H12A C12 H12C 109.0(14)
H12B C12 H12C 109.5(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7353(13)
S1 C3 1.8342(13)
S2 C10 1.7287(12)
S2 C4 1.7501(12)
O1 C2 1.2113(16)
O2 C8 1.3630(15)
O2 H2 0.81(2)
N1 C1 1.3059(16)
N1 C2 1.4078(16)
N2 C4 1.3071(16)
N2 C5 1.3766(16)
C1 C4 1.4504(17)
C2 C3 1.5343(18)
C3 C12 1.5272(18)
C3 C11 1.5374(18)
C5 C6 1.4081(18)
C5 C10 1.4148(17)
C6 C7 1.3766(18)
C6 H6 0.967(16)
C7 C8 1.4132(18)
C7 H7 0.972(15)
C8 C9 1.3904(18)
C9 C10 1.3916(17)
C9 H9 0.945(18)
C11 H11A 0.959(18)
C11 H11B 0.855(16)
C11 H11C 0.958(19)
C12 H12A 0.974(18)
C12 H12B 0.977(18)
C12 H12C 0.998(19)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.81(2) 2.07(2) 2.8792(14) 176(2) 7_666
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 C4 179.85(11)
C2 N1 C1 S1 -1.74(15)
C3 S1 C1 N1 -3.46(11)
C3 S1 C1 C4 174.98(10)
C1 N1 C2 O1 -174.31(13)
C1 N1 C2 C3 7.60(16)
O1 C2 C3 C12 52.50(17)
N1 C2 C3 C12 -129.42(12)
O1 C2 C3 C11 -69.97(16)
N1 C2 C3 C11 108.11(12)
O1 C2 C3 S1 172.48(12)
N1 C2 C3 S1 -9.44(13)
C1 S1 C3 C12 126.76(10)
C1 S1 C3 C2 6.71(9)
C1 S1 C3 C11 -108.57(10)
C5 N2 C4 C1 -176.47(11)
C5 N2 C4 S2 0.77(14)
N1 C1 C4 N2 177.22(12)
S1 C1 C4 N2 -1.18(17)
N1 C1 C4 S2 0.08(17)
S1 C1 C4 S2 -178.32(7)
C10 S2 C4 N2 -1.00(11)
C10 S2 C4 C1 176.31(11)
C4 N2 C5 C6 178.26(13)
C4 N2 C5 C10 -0.04(16)
N2 C5 C6 C7 -176.79(13)
C10 C5 C6 C7 1.45(19)
C5 C6 C7 C8 -0.7(2)
C6 C7 C8 O2 179.46(12)
C6 C7 C8 C9 -1.0(2)
O2 C8 C9 C10 -178.69(11)
C7 C8 C9 C10 1.81(18)
C8 C9 C10 C5 -1.00(18)
C8 C9 C10 S2 177.18(10)
N2 C5 C10 C9 177.79(11)
C6 C5 C10 C9 -0.62(19)
N2 C5 C10 S2 -0.68(14)
C6 C5 C10 S2 -179.10(10)
C4 S2 C10 C9 -177.49(12)
C4 S2 C10 C5 0.88(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660153
