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.
;
#======================================================================