data_moxy1_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '5-methyloxyluciferin' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 N2 O2 S2' _chemical_formula_weight 264.31 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' 'S' 'S' 0.1246 0.1234 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n 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' _cell_length_a 6.3027(4) _cell_length_b 14.8046(10) _cell_length_c 11.6515(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.419(4) _cell_angle_gamma 90.00 _cell_volume 1086.86(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.225 _exptl_crystal_size_mid 0.025 _exptl_crystal_size_min 0.025 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.478 _exptl_absorpt_correction_type 'sphere' _exptl_absorpt_correction_T_min 0.9021 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'multilayer confocal TXS mirror' _diffrn_measurement_device_type 'Bruker SMART APEX2 diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9595 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2476 _reflns_number_gt 1896 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 software (Bruker, 2007)' _computing_cell_refinement 'APEX2 software (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 2005)' _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+0.3843P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2476 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.76231(9) 0.04126(4) 0.83157(4) 0.04127(17) Uani 1 1 d . . . S2 S 1.03535(8) 0.13750(4) 0.51334(4) 0.03864(16) Uani 1 1 d . . . O2 O 1.7053(3) 0.33957(12) 0.47186(14) 0.0471(4) Uani 1 1 d . . . N1 N 0.6656(3) 0.03320(12) 0.61816(13) 0.0351(4) Uani 1 1 d . . . O1 O 0.3466(3) -0.04990(13) 0.61976(14) 0.0542(5) Uani 1 1 d . . . C3 C 0.8093(3) 0.06503(14) 0.69110(16) 0.0328(4) Uani 1 1 d . . . N2 N 1.1291(3) 0.15265(11) 0.73038(13) 0.0333(4) Uani 1 1 d . . . C2 C 0.5122(3) -0.01159(14) 0.67547(16) 0.0351(4) Uani 1 1 d . . . C4 C 0.9916(3) 0.11751(13) 0.65804(15) 0.0322(4) Uani 1 1 d . . . C11 C 0.3851(4) -0.05729(17) 0.87313(19) 0.0477(6) Uani 1 1 d . . . H11A H 0.3104 -0.0111 0.9134 0.072 Uiso 1 1 calc R . . H11B H 0.4642 -0.0938 0.9272 0.072 Uiso 1 1 calc R . . H11C H 0.2852 -0.0945 0.8313 0.072 Uiso 1 1 calc R . . C8 C 1.5945(3) 0.28997(15) 0.65291(17) 0.0381(5) Uani 1 1 d . . . H8 H 1.7095 0.3206 0.6859 0.046 Uiso 1 1 calc R . . C10 C 1.3985(3) 0.24417(14) 0.48132(16) 0.0366(5) Uani 1 1 d . . . H10 H 1.3804 0.2430 0.4019 0.044 Uiso 1 1 calc R . . C6 C 1.2849(3) 0.19920(13) 0.67205(15) 0.0315(4) Uani 1 1 d . . . C9 C 1.5639(3) 0.29063(14) 0.53270(16) 0.0351(4) Uani 1 1 d . . . C5 C 1.2589(3) 0.19885(13) 0.55208(15) 0.0319(4) Uani 1 1 d . . . C7 C 1.4571(3) 0.24487(14) 0.72172(16) 0.0372(5) Uani 1 1 d . . . H7 H 1.4785 0.2447 0.8010 0.045 Uiso 1 1 calc R . . C1 C 0.5332(3) -0.01470(14) 0.79170(17) 0.0364(5) Uani 1 1 d . . . H2O H 1.675(4) 0.341(2) 0.409(2) 0.063(9) Uiso 1 1 d . . . H1O H 0.361(5) -0.043(2) 0.548(3) 0.075(9) Uiso 1 1 d . . . 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 0.0438(3) 0.0531(4) 0.0268(2) 0.0023(2) -0.0008(2) -0.0127(2) S2 0.0397(3) 0.0504(3) 0.0256(2) 0.0011(2) -0.00165(19) -0.0100(2) O2 0.0463(9) 0.0608(11) 0.0340(8) 0.0076(8) 0.0020(7) -0.0159(8) N1 0.0356(9) 0.0434(10) 0.0263(8) -0.0013(7) 0.0004(6) -0.0029(7) O1 0.0498(10) 0.0798(13) 0.0327(8) 0.0003(8) -0.0043(7) -0.0248(9) C3 0.0354(10) 0.0354(10) 0.0277(9) 0.0000(8) 0.0023(8) 0.0006(8) N2 0.0359(9) 0.0372(9) 0.0269(8) -0.0006(7) 0.0026(6) -0.0008(7) C2 0.0349(10) 0.0400(11) 0.0302(9) -0.0016(8) -0.0015(8) -0.0028(9) C4 0.0346(10) 0.0352(10) 0.0267(9) 0.0002(8) 0.0021(7) 0.0018(8) C11 0.0479(13) 0.0586(15) 0.0367(11) 0.0036(10) 0.0036(9) -0.0135(11) C8 0.0375(11) 0.0441(12) 0.0326(10) -0.0007(9) -0.0044(8) -0.0064(9) C10 0.0404(11) 0.0444(12) 0.0250(9) 0.0024(8) -0.0010(8) -0.0019(9) C6 0.0345(10) 0.0343(10) 0.0259(9) 0.0008(8) 0.0020(7) 0.0018(8) C9 0.0338(10) 0.0382(11) 0.0336(10) 0.0033(8) 0.0036(8) -0.0003(9) C5 0.0336(10) 0.0356(10) 0.0264(9) -0.0002(8) -0.0009(7) -0.0012(8) C7 0.0416(12) 0.0442(12) 0.0256(9) -0.0004(8) -0.0031(8) -0.0012(9) C1 0.0384(11) 0.0393(11) 0.0316(10) 0.0017(9) 0.0011(8) -0.0040(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C3 1.7071(19) . ? S1 C1 1.719(2) . ? S2 C5 1.727(2) . ? S2 C4 1.7404(19) . ? O2 C9 1.361(2) . ? O2 H2O 0.76(3) . ? N1 C3 1.314(2) . ? N1 C2 1.361(3) . ? O1 C2 1.341(2) . ? O1 H1O 0.85(3) . ? C3 C4 1.447(3) . ? N2 C4 1.302(2) . ? N2 C6 1.391(2) . ? C2 C1 1.358(3) . ? C11 C1 1.488(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C8 C7 1.369(3) . ? C8 C9 1.409(3) . ? C8 H8 0.9300 . ? C10 C9 1.374(3) . ? C10 C5 1.393(3) . ? C10 H10 0.9300 . ? C6 C7 1.392(3) . ? C6 C5 1.403(2) . ? C7 H7 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 S1 C1 90.27(10) . . ? C5 S2 C4 89.08(9) . . ? C9 O2 H2O 112(2) . . ? C3 N1 C2 110.12(16) . . ? C2 O1 H1O 109(2) . . ? N1 C3 C4 124.02(17) . . ? N1 C3 S1 114.40(15) . . ? C4 C3 S1 121.57(15) . . ? C4 N2 C6 110.38(15) . . ? O1 C2 C1 121.60(18) . . ? O1 C2 N1 121.49(17) . . ? C1 C2 N1 116.91(17) . . ? N2 C4 C3 124.20(17) . . ? N2 C4 S2 116.13(15) . . ? C3 C4 S2 119.66(14) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C8 C9 120.83(18) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C9 C10 C5 117.83(17) . . ? C9 C10 H10 121.1 . . ? C5 C10 H10 121.1 . . ? N2 C6 C7 126.16(16) . . ? N2 C6 C5 114.73(17) . . ? C7 C6 C5 119.11(17) . . ? O2 C9 C10 122.62(17) . . ? O2 C9 C8 116.49(18) . . ? C10 C9 C8 120.89(18) . . ? C10 C5 C6 121.86(18) . . ? C10 C5 S2 128.45(15) . . ? C6 C5 S2 109.68(14) . . ? C8 C7 C6 119.43(17) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C2 C1 C11 127.08(19) . . ? C2 C1 S1 108.29(15) . . ? C11 C1 S1 124.62(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.350 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.053 #====================================================================== # TEXT _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; Sheldrick, G.M. (1996). SADABS, University of G\"ottingen, Germany. Bruker (2007). APEX2 software (Version 2.1-4) and SAINT (Version 7.34A). Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (2008). Acta Cryst. A64, 112--122. Brandenburg, K (2005). DIAMOND (Version 3.1). Crystal Impact GbR, Bonn, Germany. Farrugia, L. J. (1999). Win-GX (Version 1.70.01). J. Appl. Cryst.32, 837--838. ; #======================================================================