#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/50/2105048.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2105048 loop_ _publ_author_name 'Tilborg, Ana\"elle' 'Jacquemin, Denis' 'Norberg, Bernadette' 'Perp\`ete, Eric' 'Michaux, Catherine' 'Wouters, Johan' _publ_section_title ; Structural study of piracetam polymorphs and cocrystals: crystallography redetermination and quantum mechanics calculations ; _journal_coeditor_code ZB5018 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 499 _journal_page_last 507 _journal_volume 67 _journal_year 2011 _chemical_formula_moiety 'C6 H10 N2 O2' _chemical_formula_sum 'C6 H10 N2 O2' _chemical_formula_weight 142.16 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 92.087(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.5030(10) _cell_length_b 6.4180(10) _cell_length_c 16.416(3) _cell_measurement_reflns_used 240 _cell_measurement_temperature 290(2) _cell_measurement_theta_max 32.61 _cell_measurement_theta_min 3.34 _cell_volume 684.7(2) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution Sir92 _diffrn_ambient_temperature 290(2) _diffrn_detector_area_resol_mean 10.3712 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0112 _diffrn_reflns_av_sigmaI/netI 0.0096 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 4113 _diffrn_reflns_theta_full 67.36 _diffrn_reflns_theta_max 67.36 _diffrn_reflns_theta_min 5.39 _exptl_absorpt_coefficient_mu 0.876 _exptl_absorpt_correction_T_max 0.9175 _exptl_absorpt_correction_T_min 0.8442 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 304 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.169 _refine_diff_density_min -0.149 _refine_ls_extinction_coef 0.0125(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 100 _refine_ls_number_reflns 1202 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0345 _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/[\s^2^(Fo^2^)+(0.0568P)^2^+0.1732P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0977 _refine_ls_wR_factor_ref 0.0989 _reflns_number_gt 1132 _reflns_number_total 1202 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL at_piracetamCu in P2(1)/n CELL 1.54178 6.5030 6.4180 16.4160 90.000 92.087 90.000 ZERR 4.00 0.0010 0.0010 0.0030 0.000 0.004 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 24 40 8 8 MERG 2 FMAP 2 10 53 PLAN 10 SIZE 0.10 0.20 0.20 ACTA HTAB 2.00000 BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.056800 0.173200 EXTI 0.012461 FVAR 15.27161 C1 1 0.008096 0.065558 0.333497 11.00000 0.03499 0.04115 = 0.03183 -0.00418 0.00138 0.00465 C2 1 -0.111185 -0.110902 0.368983 11.00000 0.03711 0.05116 = 0.05450 0.00184 0.00382 -0.00331 AFIX 23 H2A 2 -0.202440 -0.173139 0.327737 11.00000 -1.20000 H2B 2 -0.192810 -0.061831 0.413404 11.00000 -1.20000 AFIX 0 C3 1 0.047646 -0.267486 0.399619 11.00000 0.05069 0.04513 = 0.06916 0.01256 0.00467 -0.00222 AFIX 23 H3A 2 0.040918 -0.393181 0.366819 11.00000 -1.20000 H3B 2 0.024743 -0.304250 0.455881 11.00000 -1.20000 AFIX 0 C4 1 0.255077 -0.161421 0.392355 11.00000 0.04246 0.03991 = 0.05179 0.00782 -0.00287 0.00399 AFIX 23 H4A 2 0.313930 -0.126030 0.445713 11.00000 -1.20000 H4B 2 0.350410 -0.250804 0.364644 11.00000 -1.20000 AFIX 0 C5 1 0.367229 0.175201 0.328608 11.00000 0.03489 0.04167 = 0.03453 0.00166 0.00466 -0.00067 AFIX 23 H5A 2 0.317184 0.269492 0.286173 11.00000 -1.20000 H5B 2 0.486743 0.103384 0.308776 11.00000 -1.20000 AFIX 0 C6 1 0.430394 0.300594 0.404191 11.00000 0.03382 0.03254 = 0.03777 0.00287 0.00339 0.00188 N1 3 0.209962 0.025334 0.344892 11.00000 0.03216 0.03414 = 0.03729 -0.00020 -0.00004 0.00181 N2 3 0.613422 0.392028 0.402931 11.00000 0.03778 0.04585 = 0.04851 -0.00815 0.00835 -0.00707 O1 4 -0.063054 0.221359 0.298937 11.00000 0.04219 0.05228 = 0.05262 0.00969 0.00153 0.01218 O2 4 0.312604 0.318695 0.460388 11.00000 0.04580 0.05565 = 0.04589 -0.01178 0.01399 -0.01024 H2C 2 0.699201 0.361811 0.364612 11.00000 0.05150 H2D 2 0.654019 0.479786 0.444283 11.00000 0.06294 HKLF 4 REM at_piracetamCu in P2(1)/n REM R1 = 0.0345 for 1132 Fo > 4sig(Fo) and 0.0358 for all 1202 data REM 100 parameters refined using 0 restraints END WGHT 0.0567 0.1733 REM Highest difference peak 0.169, deepest hole -0.149, 1-sigma level 0.037 Q1 1 0.1358 0.0107 0.3237 11.00000 0.05 0.17 Q2 1 0.1301 0.0656 0.3593 11.00000 0.05 0.15 Q3 1 0.0357 -0.3907 0.4284 11.00000 0.05 0.15 Q4 1 0.2407 -0.0587 0.3603 11.00000 0.05 0.15 Q5 1 -0.2518 -0.1025 0.3646 11.00000 0.05 0.15 Q6 1 0.0560 -0.1985 0.4432 11.00000 0.05 0.14 Q7 1 -0.0614 -0.0396 0.3426 11.00000 0.05 0.14 Q8 1 0.4016 0.2394 0.3659 11.00000 0.05 0.13 Q9 1 0.2734 0.0865 0.3374 11.00000 0.05 0.12 Q10 1 0.4436 0.1641 0.2953 11.00000 0.05 0.12 ; _[local]_cod_data_source_file zb5018.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2105048 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' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity C C1 0.00810(19) 0.0656(2) 0.33350(7) 0.0360(3) Uani d . 1 1 C C2 -0.1112(2) -0.1109(2) 0.36898(9) 0.0475(4) Uani d . 1 1 H H2A -0.2024 -0.1731 0.3277 0.057 Uiso calc R 1 1 H H2B -0.1928 -0.0618 0.4134 0.057 Uiso calc R 1 1 C C3 0.0476(2) -0.2675(3) 0.39962(11) 0.0549(4) Uani d . 1 1 H H3A 0.0409 -0.3932 0.3668 0.066 Uiso calc R 1 1 H H3B 0.0247 -0.3042 0.4559 0.066 Uiso calc R 1 1 C C4 0.2551(2) -0.1614(2) 0.39235(9) 0.0448(4) Uani d . 1 1 H H4A 0.3139 -0.1260 0.4457 0.054 Uiso calc R 1 1 H H4B 0.3504 -0.2508 0.3646 0.054 Uiso calc R 1 1 C C5 0.36723(19) 0.1752(2) 0.32861(8) 0.0370(3) Uani d . 1 1 H H5A 0.3172 0.2695 0.2862 0.044 Uiso calc R 1 1 H H5B 0.4867 0.1034 0.3088 0.044 Uiso calc R 1 1 C C6 0.43039(18) 0.30059(19) 0.40419(8) 0.0347(3) Uani d . 1 1 N N1 0.20996(15) 0.02533(16) 0.34489(6) 0.0346(3) Uani d . 1 1 N N2 0.61342(18) 0.3920(2) 0.40293(8) 0.0439(3) Uani d . 1 1 O O1 -0.06305(14) 0.22136(17) 0.29894(6) 0.0490(3) Uani d . 1 1 O O2 0.31260(15) 0.31870(17) 0.46039(6) 0.0488(3) Uani d . 1 1 H H2C 0.699(3) 0.362(3) 0.3646(11) 0.052(5) Uiso d . 1 1 H H2D 0.654(3) 0.480(3) 0.4443(13) 0.063(5) Uiso d . 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0350(7) 0.0411(7) 0.0318(6) 0.0047(5) 0.0014(5) -0.0042(5) C2 0.0371(7) 0.0512(9) 0.0545(8) -0.0033(6) 0.0038(6) 0.0018(7) C3 0.0507(9) 0.0451(8) 0.0692(11) -0.0022(7) 0.0047(7) 0.0126(7) C4 0.0425(8) 0.0399(8) 0.0518(8) 0.0040(6) -0.0029(6) 0.0078(6) C5 0.0349(7) 0.0417(7) 0.0345(7) -0.0007(5) 0.0047(5) 0.0017(5) C6 0.0338(6) 0.0325(7) 0.0378(7) 0.0019(5) 0.0034(5) 0.0029(5) N1 0.0322(5) 0.0341(6) 0.0373(6) 0.0018(4) 0.0000(4) -0.0002(4) N2 0.0378(6) 0.0458(7) 0.0485(7) -0.0071(5) 0.0083(5) -0.0081(5) O1 0.0422(6) 0.0523(6) 0.0526(6) 0.0122(4) 0.0015(4) 0.0097(5) O2 0.0458(6) 0.0557(7) 0.0459(6) -0.0102(5) 0.0140(4) -0.0118(5) 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' N N 0.0311 0.0180 '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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 N1 124.66(12) O1 C1 C2 126.88(12) N1 C1 C2 108.46(11) C1 C2 C3 105.88(11) C1 C2 H2A 110.6 C3 C2 H2A 110.6 C1 C2 H2B 110.6 C3 C2 H2B 110.6 H2A C2 H2B 108.7 C2 C3 C4 105.87(12) C2 C3 H3A 110.6 C4 C3 H3A 110.6 C2 C3 H3B 110.6 C4 C3 H3B 110.6 H3A C3 H3B 108.7 N1 C4 C3 104.42(11) N1 C4 H4A 110.9 C3 C4 H4A 110.9 N1 C4 H4B 110.9 C3 C4 H4B 110.9 H4A C4 H4B 108.9 N1 C5 C6 112.03(10) N1 C5 H5A 109.2 C6 C5 H5A 109.2 N1 C5 H5B 109.2 C6 C5 H5B 109.2 H5A C5 H5B 107.9 O2 C6 N2 123.70(12) O2 C6 C5 120.39(11) N2 C6 C5 115.86(11) C1 N1 C5 122.95(11) C1 N1 C4 114.20(11) C5 N1 C4 121.39(10) C6 N2 H2C 120.5(11) C6 N2 H2D 119.7(11) H2C N2 H2D 119.7(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.2315(17) C1 N1 1.3443(16) C1 C2 1.502(2) C2 C3 1.514(2) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.520(2) C3 H3A 0.9700 C3 H3B 0.9700 C4 N1 1.4537(17) C4 H4A 0.9700 C4 H4B 0.9700 C5 N1 1.4361(16) C5 C6 1.5228(18) C5 H5A 0.9700 C5 H5B 0.9700 C6 O2 1.2259(16) C6 N2 1.3279(17) N2 H2C 0.878(19) N2 H2D 0.91(2) 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 O1 C1 C2 C3 176.77(14) N1 C1 C2 C3 -2.66(15) C1 C2 C3 C4 8.34(17) C2 C3 C4 N1 -10.69(16) N1 C5 C6 O2 -23.18(17) N1 C5 C6 N2 159.25(11) O1 C1 N1 C5 9.56(19) C2 C1 N1 C5 -171.00(12) O1 C1 N1 C4 175.91(12) C2 C1 N1 C4 -4.65(15) C6 C5 N1 C1 93.02(14) C6 C5 N1 C4 -72.38(15) C3 C4 N1 C1 9.85(16) C3 C4 N1 C5 176.44(12) _cod_database_fobs_code 2105048