#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/28/4102864.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_4102864
loop_
_publ_author_name
'Panče Naumov'
'Manoj Kochunnoonny'
_publ_section_title
;
 Spectral-Structural Effects of the Keto-Enol-Enolate and Phenol-Phenolate
 Equilibria of Oxyluciferin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11566
_journal_page_last               11579
_journal_paper_doi               10.1021/ja102885g
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         C10H6N2OS2
_chemical_formula_sum            'C10 H6 N2 O S2'
_chemical_formula_weight         234.29
_chemical_name_common            6'-dehydroxyoxyluciferin
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 91.958(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.193(4)
_cell_length_b                   3.8471(8)
_cell_length_c                   14.112(3)
_cell_measurement_temperature    293(2)
_cell_volume                     987.1(4)
_computing_cell_refinement       'APEX2 software (Bruker, 2007)'
_computing_data_collection       'APEX2 software (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX2 diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer confocal TXS mirror'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_av_sigmaI/netI    0.0763
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10582
_diffrn_reflns_theta_full        26.13
_diffrn_reflns_theta_max         26.13
_diffrn_reflns_theta_min         1.12
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9186
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0647
_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)+(0.1113P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1965
_reflns_number_gt                1278
_reflns_number_total             1952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja102885g_si_002.cif
_cod_data_source_block           hoxy3a
_cod_original_cell_volume        987.2(4)
_cod_original_formula_sum        C10H6N2OS2
_cod_database_code               4102864
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
S1' S 0.20435(6) 0.1737(3) 0.61325(7) 0.0463(4) Uani 1 1 d U
S1 S 0.17552(6) -0.2497(3) 0.32751(7) 0.0489(4) Uani 1 1 d U
O10' O -0.02639(17) -0.2437(9) 0.3894(2) 0.0594(9) Uani 1 1 d U
H10' H -0.0394 -0.1479 0.4380 0.089 Uiso 1 1 calc R
N3 N 0.08844(18) -0.0767(8) 0.4569(2) 0.0406(8) Uani 1 1 d U
C9' C 0.3322(2) 0.1669(11) 0.5426(3) 0.0454(10) Uani 1 1 d .
N3' N 0.28552(18) 0.0471(9) 0.4700(2) 0.0467(9) Uani 1 1 d U
C2 C 0.1581(2) -0.0802(9) 0.4360(3) 0.0380(9) Uani 1 1 d U
C5 C 0.0844(2) -0.3192(10) 0.3074(3) 0.0475(11) Uani 1 1 d U
H5 H 0.0634 -0.4144 0.2523 0.057 Uiso 1 1 calc R
C4 C 0.0469(2) -0.2157(10) 0.3833(3) 0.0421(10) Uani 1 1 d U
C8' C 0.2982(2) 0.2441(10) 0.6275(3) 0.0425(10) Uani 1 1 d .
C2' C 0.2187(2) 0.0394(10) 0.4977(3) 0.0402(9) Uani 1 1 d U
C7' C 0.3385(2) 0.3598(12) 0.7067(3) 0.0534(12) Uani 1 1 d .
H7' H 0.3155 0.4099 0.7629 0.064 Uiso 1 1 calc R
C5' C 0.4469(3) 0.3291(13) 0.6166(4) 0.0658(15) Uani 1 1 d .
H5' H 0.4974 0.3624 0.6135 0.079 Uiso 1 1 calc R
C4' C 0.4074(2) 0.2114(12) 0.5379(4) 0.0585(13) Uani 1 1 d .
H4' H 0.4312 0.1625 0.4821 0.070 Uiso 1 1 calc R
C6' C 0.4122(3) 0.3980(12) 0.7000(4) 0.0611(13) Uani 1 1 d .
H6' H 0.4400 0.4722 0.7527 0.073 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1' 0.0519(7) 0.0605(7) 0.0261(6) -0.0047(5) -0.0053(5) -0.0039(5)
S1 0.0608(8) 0.0579(8) 0.0276(6) -0.0073(5) -0.0022(5) 0.0002(5)
O10' 0.056(2) 0.090(3) 0.0317(18) -0.0176(16) -0.0087(15) -0.0047(15)
N3 0.055(2) 0.045(2) 0.0205(17) -0.0015(14) -0.0061(15) -0.0018(15)
C9' 0.055(3) 0.045(2) 0.036(2) 0.0019(19) -0.005(2) 0.0011(19)
N3' 0.052(2) 0.053(2) 0.034(2) -0.0004(16) -0.0014(17) 0.0004(16)
C2 0.058(3) 0.034(2) 0.022(2) 0.0012(16) -0.0058(18) 0.0014(18)
C5 0.067(3) 0.048(2) 0.026(2) -0.0067(19) -0.008(2) -0.0023(19)
C4 0.053(3) 0.048(2) 0.025(2) -0.0010(18) -0.0044(19) 0.0013(18)
C8' 0.052(3) 0.039(2) 0.035(2) 0.0002(18) -0.0086(19) 0.0015(17)
C2' 0.057(2) 0.037(2) 0.026(2) 0.0024(17) -0.0053(18) -0.0006(18)
C7' 0.064(3) 0.058(3) 0.037(3) -0.013(2) -0.013(2) 0.002(2)
C5' 0.051(3) 0.063(3) 0.082(4) 0.010(3) -0.013(3) -0.007(2)
C4' 0.050(3) 0.068(3) 0.057(3) 0.003(2) 0.003(2) 0.000(2)
C6' 0.063(3) 0.061(3) 0.058(3) -0.001(2) -0.022(3) -0.002(2)
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
C8' S1' C2' 88.7(2)
C5 S1 C2 89.99(19)
C2 N3 C4 109.7(3)
C4' C9' N3' 125.9(4)
C4' C9' C8' 118.9(4)
N3' C9' C8' 115.2(4)
C2' N3' C9' 110.0(3)
N3 C2 C2' 125.4(4)
N3 C2 S1 114.7(3)
C2' C2 S1 119.9(3)
C4 C5 S1 109.8(3)
O10' C4 C5 123.9(4)
O10' C4 N3 120.3(4)
C5 C4 N3 115.8(4)
C7' C8' C9' 121.4(4)
C7' C8' S1' 129.4(4)
C9' C8' S1' 109.3(3)
N3' C2' C2 121.8(4)
N3' C2' S1' 116.8(3)
C2 C2' S1' 121.4(3)
C6' C7' C8' 118.3(4)
C4' C5' C6' 120.7(5)
C5' C4' C9' 119.3(5)
C7' C6' C5' 121.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1' C8' 1.734(4)
S1' C2' 1.738(4)
S1 C5 1.693(4)
S1 C2 1.704(4)
O10' C4 1.344(5)
N3 C2 1.311(4)
N3 C4 1.372(5)
C9' C4' 1.382(6)
C9' N3' 1.388(5)
C9' C8' 1.399(6)
N3' C2' 1.291(5)
C2 C2' 1.456(6)
C5 C4 1.349(6)
C8' C7' 1.388(6)
C7' C6' 1.355(6)
C5' C4' 1.378(7)
C5' C6' 1.380(7)
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
O10' H10' N3 0.82 1.96 2.768(4) 169.6 3_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660128
