# Generated by libcif.py : May 2005
# Written by Jerome Kieffer : Jerome.Kieffer@Sanofi-Aventis.com 
# X-Ray Crystallography & Solid State Modeling Laboratory
# Sanofi-Aventis Montpellier (France)
data_
_atom_sites_solution_hydrogens		geom 
_atom_sites_solution_primary		direct 
_atom_sites_solution_secondary		difmap 
_audit_creation_date		'May 22 16:38:46 2005' 
_audit_creation_method		SHELXL-97 
_cell_angle_alpha		90.01 
_cell_angle_beta		95.68(3) 
_cell_angle_gamma		89.98 
_cell_formula_units_Z		4 
_cell_length_a		11.429(2) 
_cell_length_b		6.5902(13) 
_cell_length_c		11.396(2) 
_cell_measurement_reflns_used		? 
_cell_measurement_temperature		293(2) 
_cell_measurement_theta_max		? 
_cell_measurement_theta_min		? 
_cell_volume		854.1(3) 
_chemical_compound_source		'see text' 
_chemical_formula_moiety		'C9 H8 O4' 
_chemical_formula_sum		'C9 H8 O4' 
_chemical_formula_weight		180.15 
_chemical_melting_point		? 
_chemical_name_common		Aspirine 
_chemical_name_systematic		? 
_computing_cell_refinement		? 
_computing_data_collection		? 
_computing_data_reduction		? 
_computing_molecular_graphics		? 
_computing_publication_material		'PLATON (Spek, 2003)' 
_computing_structure_refinement		'SHELXL-97 (Sheldrick, 1997)' 
_computing_structure_solution		'SHELXS-97 (Sheldrick, 1990)' 
_diffrn_ambient_temperature		293(2) 
_diffrn_detector_area_resol_mean		? 
_diffrn_measured_fraction_theta_full		0.948 
_diffrn_measured_fraction_theta_max		0.948 
_diffrn_measurement_device_type		KappaCCD 
_diffrn_measurement_method		? 
_diffrn_radiation_monochromator		graphite 
_diffrn_radiation_probe		x-ray 
_diffrn_radiation_source		'fine-focus sealed tube' 
_diffrn_radiation_type		CuK\a 
_diffrn_radiation_wavelength		1.54178 
_diffrn_reflns_av_R_equivalents		0.0106 
_diffrn_reflns_av_sigmaI/netI		0.0135 
_diffrn_reflns_limit_h_max		13 
_diffrn_reflns_limit_h_min		-13 
_diffrn_reflns_limit_k_max		7 
_diffrn_reflns_limit_k_min		0 
_diffrn_reflns_limit_l_max		13 
_diffrn_reflns_limit_l_min		0 
_diffrn_reflns_number		1613 
_diffrn_reflns_theta_full		66.93 
_diffrn_reflns_theta_max		66.93 
_diffrn_reflns_theta_min		3.89 
_diffrn_standards_decay_%		? 
_diffrn_standards_interval_count		? 
_diffrn_standards_interval_time		? 
_diffrn_standards_number		? 
_exptl_absorpt_coefficient_mu		0.951 
_exptl_absorpt_correction_T_max		? 
_exptl_absorpt_correction_T_min		? 
_exptl_absorpt_correction_type		? 
_exptl_absorpt_process_details		? 
_exptl_crystal_F_000		376 
_exptl_crystal_colour		? 
_exptl_crystal_density_diffrn		1.401 
_exptl_crystal_density_meas		? 
_exptl_crystal_density_method		'not measured' 
_exptl_crystal_description		? 
_exptl_crystal_size_max		? 
_exptl_crystal_size_mid		? 
_exptl_crystal_size_min		? 
_exptl_special_details 
;
 Recristallisé dans un 
 mélange eau-éthanol 
;
_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. 
;
_refine_diff_density_max		0.189 
_refine_diff_density_min		-0.155 
_refine_diff_density_rms		0.047 
_refine_ls_R_factor_all		0.0457 
_refine_ls_R_factor_gt		0.0400 
_refine_ls_abs_structure_Flack		. 
_refine_ls_extinction_coef		0.0067(13) 
_refine_ls_extinction_expression		Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^ 
_refine_ls_extinction_method		SHELXL 
_refine_ls_goodness_of_fit_ref		2.004 
_refine_ls_hydrogen_treatment		mixed 
_refine_ls_matrix_type		full 
_refine_ls_number_parameters		128 
_refine_ls_number_reflns		1527 
_refine_ls_number_restraints		1 
_refine_ls_restrained_S_all		2.004 
_refine_ls_shift/su_max		0.368 
_refine_ls_shift/su_mean		0.054 
_refine_ls_structure_factor_coef		Fsqd 
_refine_ls_wR_factor_gt		0.1351 
_refine_ls_wR_factor_ref		0.1404 
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_refine_ls_weighting_scheme		calc 
_refine_special_details 
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_reflns_number_gt		1363 
_reflns_number_total		1527 
_reflns_threshold_expression		>2sigma(I) 
_symmetry_Int_Tables_number		14 
_symmetry_cell_setting		Monoclinic 
_symmetry_space_group_name_H-M		'P 21/c' 
_symmetry_space_group_name_Hall		'-P 2ybc' 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 C C 0.0181 0.0091 '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' 
 O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 

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 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
 O7 O 0.28561(5) 0.08781(11) 0.41208(5) 0.04867(16) Uani 1 1 d . . . 
 C1 C 0.15338(8) 0.06414(14) 0.56733(7) 0.0432(2) Uani 1 1 d . . . 
 O12 O 0.12040(6) 0.35994(12) 0.44918(6) 0.05794(18) Uani 1 1 d D . . 
 H12A H 0.0684(13) 0.470(2) 0.4373(14) 0.100(5) Uiso 1 1 d D . . 
 O11 O 0.01036(7) 0.31163(12) 0.59651(6) 0.06037(19) Uani 1 1 d . . . 
 C2 C 0.11641(9) -0.05031(15) 0.66007(8) 0.0492(2) Uani 1 1 d . . . 
 H2A H 0.0553(9) -0.0035(7) 0.6997(6) 0.059 Uiso 1 1 calc R . . 
 C10 C 0.09036(8) 0.25680(14) 0.53736(8) 0.0444(2) Uani 1 1 d . . . 
 C6 C 0.24580(8) -0.01219(14) 0.50896(8) 0.0449(2) Uani 1 1 d . . . 
 C5 C 0.29848(9) -0.19476(17) 0.54151(10) 0.0543(2) Uani 1 1 d . . . 
 H5A H 0.3625(9) -0.2463(8) 0.4994(6) 0.065 Uiso 1 1 calc R . . 
 O9 O 0.40339(7) 0.28001(14) 0.53457(7) 0.0683(2) Uani 1 1 d . . . 
 C8 C 0.36579(8) 0.23853(15) 0.43631(8) 0.0482(2) Uani 1 1 d . . . 
 C4 C 0.26050(10) -0.30458(16) 0.63376(10) 0.0581(3) Uani 1 1 d . . . 
 H4A H 0.2964(6) -0.428(2) 0.6559(4) 0.070 Uiso 1 1 calc R . . 
 C3 C 0.16973(10) -0.23221(15) 0.69342(10) 0.0549(3) Uani 1 1 d . . . 
 H3A H 0.1427(4) -0.3111(11) 0.7605(9) 0.066 Uiso 1 1 calc R . . 
 C13 C 0.39712(11) 0.3379(2) 0.32688(10) 0.0667(3) Uani 1 1 d . . . 
 H13A H 0.3280 0.3969 0.2858 0.100 Uiso 1 1 calc R . . 
 H13B H 0.4293 0.2388 0.2773 0.100 Uiso 1 1 calc R . . 
 H13C H 0.4543 0.4421 0.3467 0.100 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 
 O7 0.0484(3) 0.0563(3) 0.0421(3) -0.0053(3) 0.0086(2) -0.0028(3) 
 C1 0.0412(4) 0.0465(4) 0.0416(4) -0.0031(4) 0.0028(3) -0.0021(3) 
 O12 0.0581(4) 0.0579(4) 0.0600(4) 0.0148(3) 0.0170(3) 0.0111(3) 
 O11 0.0638(4) 0.0617(4) 0.0590(4) 0.0086(3) 0.0227(3) 0.0163(3) 
 C2 0.0451(4) 0.0531(5) 0.0500(4) 0.0011(4) 0.0078(4) -0.0002(4) 
 C10 0.0413(4) 0.0491(4) 0.0430(4) -0.0027(4) 0.0058(4) -0.0012(4) 
 C6 0.0433(4) 0.0483(4) 0.0430(4) -0.0052(4) 0.0039(3) -0.0037(4) 
 C5 0.0484(5) 0.0548(5) 0.0601(5) -0.0058(4) 0.0077(4) 0.0060(4) 
 O9 0.0697(5) 0.0867(5) 0.0480(4) -0.0040(3) 0.0037(3) -0.0256(4) 
 C8 0.0420(4) 0.0573(5) 0.0461(5) -0.0025(4) 0.0082(4) 0.0005(4) 
 C4 0.0582(5) 0.0483(5) 0.0672(6) 0.0045(5) 0.0039(5) 0.0063(4) 
 C3 0.0534(5) 0.0537(5) 0.0579(5) 0.0083(4) 0.0068(4) -0.0022(4) 
 C13 0.0642(6) 0.0839(7) 0.0525(5) 0.0082(5) 0.0089(5) -0.0097(6) 

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 
 O7 C8 1.3613(12) . ? 
 O7 C6 1.4000(11) . ? 
 C1 C2 1.3976(13) . ? 
 C1 C6 1.3965(14) . ? 
 C1 C10 1.4826(13) . ? 
 O12 C10 1.2878(12) . ? 
 O11 C10 1.2420(12) . ? 
 C2 C3 1.3808(15) . ? 
 C6 C5 1.3796(14) . ? 
 C5 C4 1.3814(16) . ? 
 O9 C8 1.1907(12) . ? 
 C8 C13 1.4835(15) . ? 
 C4 C3 1.3803(16) . ? 

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 
 C8 O7 C6 116.65(7) . . ? 
 C2 C1 C6 117.74(9) . . ? 
 C2 C1 C10 117.40(8) . . ? 
 C6 C1 C10 124.86(8) . . ? 
 C3 C2 C1 121.24(10) . . ? 
 O11 C10 O12 122.51(9) . . ? 
 O11 C10 C1 119.39(8) . . ? 
 O12 C10 C1 118.09(8) . . ? 
 C5 C6 C1 121.09(9) . . ? 
 C5 C6 O7 117.10(8) . . ? 
 C1 C6 O7 121.76(8) . . ? 
 C4 C5 C6 120.00(10) . . ? 
 O9 C8 O7 122.10(9) . . ? 
 O9 C8 C13 126.47(10) . . ? 
 O7 C8 C13 111.43(8) . . ? 
 C3 C4 C5 120.14(10) . . ? 
 C4 C3 C2 119.79(10) . . ? 

loop_ 
 _publ_author_name 
 _publ_author_footnote 
 _publ_author_address 
 ? ? ? 

loop_ 
 _diffrn_standard_refln_index_h 
 _diffrn_standard_refln_index_k 
 _diffrn_standard_refln_index_l 
 ? ? ? 

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_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
 C8 O7 C6 C1 84.74(11) . . . . no 
 C8 O7 C6 C5 -97.99(11) . . . . no 
 C6 O7 C8 O9 2.27(14) . . . . no 
 C6 O7 C8 C13 -177.64(9) . . . . no 
 C2 C1 C6 O7 177.40(9) . . . . no 
 C2 C1 C6 C5 0.24(14) . . . . no 
 C10 C1 C6 O7 -1.83(14) . . . . no 
 C10 C1 C6 C5 -178.99(10) . . . . no 
 C2 C1 C10 O11 1.82(13) . . . . no 
 C2 C1 C10 O12 -177.35(9) . . . . no 
 C6 C1 C10 O11 -178.95(9) . . . . no 
 C6 C1 C10 O12 1.89(14) . . . . no 
 C10 C1 C2 C3 179.62(10) . . . . no 
 C6 C1 C2 C3 0.34(14) . . . . no 
 C1 C2 C3 C4 -0.68(16) . . . . no 
 C2 C3 C4 C5 0.46(17) . . . . no 
 C3 C4 C5 C6 0.11(17) . . . . no 
 C4 C5 C6 C1 -0.46(16) . . . . no 
 C4 C5 C6 O7 -177.75(10) . . . . no 

loop_ 
 _geom_contact_atom_site_label_1 
 _geom_contact_atom_site_label_2 
 _geom_contact_distance 
 _geom_contact_site_symmetry_1 
 _geom_contact_site_symmetry_2 
 _geom_contact_publ_flag 
 O7 O12 2.6680(11) . . no 
 O9 C1 3.2464(14) . . no 
 O9 C5 3.3544(16) . . no 
 O11 C10 3.3755(14) . 3_566 no 
 O11 C3 3.3206(15) . 2_556 no 
 O11 O12 2.6524(12) . 3_566 no 
 O11 C2 3.3790(14) . 2_556 no 
 O12 C8 2.9341(13) . . no 
 O12 O7 2.6680(11) . . no 
 O12 C4 3.3481(15) . 1_565 no 
 O12 O11 2.6524(12) . 3_566 no 
 O7 H3A 2.9000 . 4_544 no 
 O9 H5A 2.7500 . 3_656 no 
 O9 H4A 2.7300 . 1_565 no 
 O9 H13B 2.7600 . 4_555 no 
 O9 H13C 2.7200 . 3_666 no 
 O11 H12A 1.721(14) . 3_566 no 
 O11 H2A 2.4200 . . no 
 O11 H2A 2.7900 . 2_556 no 
 O11 H3A 2.6300 . 2_556 no 
 O12 H12A 2.853(15) . 3_566 no 
 C1 O9 3.2464(14) . . no 
 C2 O11 3.3790(14) . 2_546 no 
 C2 C10 3.3832(15) . 3_556 no 
 C3 O11 3.3206(15) . 2_546 no 
 C4 C10 3.5945(16) . 1_545 no 
 C4 O12 3.3481(15) . 1_545 no 
 C5 O9 3.3544(16) . . no 
 C8 C10 3.4594(15) . . no 
 C8 O12 2.9341(13) . . no 
 C10 C2 3.3832(15) . 3_556 no 
 C10 C8 3.4594(15) . . no 
 C10 O11 3.3755(14) . 3_566 no 
 C10 C4 3.5945(16) . 1_565 no 
 C1 H13A 3.0400 . 4_555 no 
 C2 H13A 2.8700 . 4_555 no 
 C3 H13A 2.9800 . 4_555 no 
 C10 H12A 2.593(14) . 3_566 no 
 H2A O11 2.4200 . . no 
 H2A O11 2.7900 . 2_546 no 
 H3A O11 2.6300 . 2_546 no 
 H3A O7 2.9000 . 4_545 no 
 H4A O9 2.7300 . 1_545 no 
 H5A O9 2.7500 . 3_656 no 
 H12A O11 1.721(14) . 3_566 no 
 H12A O12 2.853(15) . 3_566 no 
 H12A C10 2.593(14) . 3_566 no 
 H12A H12A 2.26(2) . 3_566 no 
 H13A C1 3.0400 . 4_554 no 
 H13A C2 2.8700 . 4_554 no 
 H13A C3 2.9800 . 4_554 no 
 H13B O9 2.7600 . 4_554 no 
 H13C O9 2.7200 . 3_666 no 

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 
 _geom_hbond_publ_flag 
 O12 H12A O11 0.939(14) 1.721(14) 2.6524(12) 171.1(14) 3_566 yes 
 C2 H2A O11 0.9200 2.4200 2.7403(14) 101.00 . yes 

