############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_global _audit_creation_method SHELXTL-V6.1 _journal_date_recd_electronic 2008-04-29 _journal_date_accepted 2008-04-30 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2008 _journal_volume 64 _journal_issue 6 _journal_page_first o1005 _journal_page_last o1005 _journal_paper_category QO _journal_coeditor_code HB2729 _publ_contact_author_name 'Dr. Lough, Alan J.' _publ_contact_author_address ; Department of Chemistry University of Toronto Toronto Ontario Canada M5S 3H6 ; _publ_contact_author_email alough@chem.utoronto.ca _publ_contact_author_fax '416 978 8775' _publ_contact_author_phone '416 978 6275' _publ_section_title ; N-Isopropylbenzamide ; loop_ _publ_author_name _publ_author_address 'van Oosten, Erik M.' ; Department of Chemistry University of Toronto 80 St George Street Toronto Ontario Canada M5S 3H6 ; 'Lough, Alan J.' ; Department of Chemistry University of Toronto 80 St George Street Toronto Ontario Canada M5S 3H6 ; 'Vasdev, Neil' ; PET Centre Centre for Addiction and Mental Health and Department of Psychiatry University of Toronto 250 College Street Toronto Ontario Canada M5T 1R8 ; data_I _chemical_name_systematic ; N-Isopropylbenzamide ; _chemical_name_common ? _chemical_formula_moiety 'C10 H13 N O' _chemical_formula_sum 'C10 H13 N O' _chemical_formula_iupac 'C10 H13 N O' _chemical_formula_weight 163.21 _chemical_melting_point ? _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.0093(7) _cell_length_b 10.1250(13) _cell_length_c 9.6714(14) _cell_angle_alpha 90.00 _cell_angle_beta 104.133(7) _cell_angle_gamma 90.00 _cell_volume 475.68(11) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2462 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 25.0 _cell_measurement_temperature 150.0(10) _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.140 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 176 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing 1995)' _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_T_max 0.996 _exptl_special_details ; ; _diffrn_ambient_temperature 150.0(10) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 2462 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^ > \s(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. ; _reflns_number_total 887 _reflns_number_gt 621 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_gt 0.1288 _refine_ls_wR_factor_ref 0.1480 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.056 _refine_ls_number_reflns 887 _refine_ls_number_parameters 114 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0784P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.179 _refine_diff_density_min -0.207 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'COLLECT (Nonius, 2002)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' 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_disorder_assembly _atom_site_disorder_group O O1 0.6751(6) 0.1703(3) 0.8045(3) 0.0424(8) Uani d . 1 . . N N1 0.2696(8) 0.1717(4) 0.8673(4) 0.0411(10) Uani d . 1 . . H H1N 0.103(11) 0.188(5) 0.839(5) 0.049 Uiso d . 1 . . C C1 0.3226(9) 0.3127(4) 0.6749(5) 0.0350(11) Uani d . 1 . . C C2 0.4247(10) 0.3165(5) 0.5544(5) 0.0452(13) Uani d . 1 . . H H2A 0.5601 0.2545 0.5432 0.054 Uiso calc R 1 . . C C3 0.3286(11) 0.4116(6) 0.4493(5) 0.0535(14) Uani d . 1 . . H H3A 0.3957 0.4126 0.3655 0.064 Uiso calc R 1 . . C C4 0.1377(10) 0.5034(5) 0.4666(6) 0.0516(14) Uani d . 1 . . H H4A 0.0734 0.5682 0.3951 0.062 Uiso calc R 1 . . C C5 0.0391(11) 0.5014(5) 0.5883(6) 0.0523(14) Uani d . 1 . . H H5A -0.0912 0.5656 0.6010 0.063 Uiso calc R 1 . . C C6 0.1296(9) 0.4064(5) 0.6915(5) 0.0451(13) Uani d . 1 . . H H6A 0.0597 0.4051 0.7744 0.054 Uiso calc R 1 . . C C7 0.4356(8) 0.2117(4) 0.7864(4) 0.0362(12) Uani d . 1 . . C C8 0.3461(10) 0.0743(5) 0.9808(5) 0.0474(13) Uani d . 1 . . H H8A 0.5489 0.0586 0.9996 0.057 Uiso calc R 1 . . C C9 0.1984(13) -0.0561(5) 0.9351(6) 0.0648(16) Uani d . 1 . . H H9A 0.2525 -0.0903 0.8512 0.097 Uiso calc R 1 . . H H9B -0.0011 -0.0417 0.9116 0.097 Uiso calc R 1 . . H H9C 0.2488 -0.1200 1.0132 0.097 Uiso calc R 1 . . C C10 0.2833(11) 0.1271(6) 1.1160(5) 0.0556(15) Uani d . 1 . . H H10A 0.3743 0.2126 1.1400 0.083 Uiso calc R 1 . . H H10B 0.3510 0.0647 1.1942 0.083 Uiso calc R 1 . . H H10C 0.0839 0.1380 1.1013 0.083 Uiso calc R 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 O1 0.0319(17) 0.0442(18) 0.0515(17) 0.0024(15) 0.0112(13) 0.0032(16) N1 0.0326(19) 0.046(2) 0.047(2) 0.003(2) 0.0149(18) 0.012(2) C1 0.033(2) 0.035(2) 0.039(3) -0.006(2) 0.012(2) 0.000(2) C2 0.049(3) 0.044(3) 0.046(3) 0.001(2) 0.019(2) 0.003(2) C3 0.057(3) 0.061(3) 0.046(3) -0.003(3) 0.019(3) 0.012(3) C4 0.049(3) 0.051(3) 0.050(3) -0.002(3) 0.004(3) 0.020(3) C5 0.053(3) 0.040(3) 0.066(3) 0.007(3) 0.017(3) 0.013(3) C6 0.046(3) 0.042(3) 0.051(3) 0.003(2) 0.017(2) 0.005(3) C7 0.035(3) 0.034(3) 0.037(2) -0.004(2) 0.005(2) -0.008(2) C8 0.041(3) 0.054(3) 0.048(3) 0.012(3) 0.012(2) 0.017(3) C9 0.085(4) 0.043(3) 0.064(3) 0.010(3) 0.014(3) 0.012(3) C10 0.062(3) 0.062(4) 0.044(3) -0.001(3) 0.015(2) 0.012(3) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C7 . 1.242(5) ? N1 C7 . 1.337(6) ? N1 C8 . 1.455(6) ? N1 H1N . 0.83(5) ? C1 C2 . 1.383(6) ? C1 C6 . 1.392(6) ? C1 C7 . 1.493(6) ? C2 C3 . 1.398(8) ? C2 H2A . 0.9500 ? C3 C4 . 1.373(7) ? C3 H3A . 0.9500 ? C4 C5 . 1.384(7) ? C4 H4A . 0.9500 ? C5 C6 . 1.380(7) ? C5 H5A . 0.9500 ? C6 H6A . 0.9500 ? C8 C10 . 1.516(7) ? C8 C9 . 1.525(8) ? C8 H8A . 1.0000 ? C9 H9A . 0.9800 ? C9 H9B . 0.9800 ? C9 H9C . 0.9800 ? C10 H10A . 0.9800 ? C10 H10B . 0.9800 ? C10 H10C . 0.9800 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 N1 C8 . . 124.0(4) ? C7 N1 H1N . . 118(4) ? C8 N1 H1N . . 117(4) ? C2 C1 C6 . . 119.2(4) ? C2 C1 C7 . . 118.3(4) ? C6 C1 C7 . . 122.4(4) ? C1 C2 C3 . . 120.0(5) ? C1 C2 H2A . . 120.0 ? C3 C2 H2A . . 120.0 ? C4 C3 C2 . . 120.3(5) ? C4 C3 H3A . . 119.9 ? C2 C3 H3A . . 119.9 ? C3 C4 C5 . . 119.8(5) ? C3 C4 H4A . . 120.1 ? C5 C4 H4A . . 120.1 ? C6 C5 C4 . . 120.2(5) ? C6 C5 H5A . . 119.9 ? C4 C5 H5A . . 119.9 ? C5 C6 C1 . . 120.5(4) ? C5 C6 H6A . . 119.8 ? C1 C6 H6A . . 119.8 ? O1 C7 N1 . . 122.2(4) ? O1 C7 C1 . . 121.0(4) ? N1 C7 C1 . . 116.7(4) ? N1 C8 C10 . . 109.9(4) ? N1 C8 C9 . . 110.4(4) ? C10 C8 C9 . . 111.5(4) ? N1 C8 H8A . . 108.3 ? C10 C8 H8A . . 108.3 ? C9 C8 H8A . . 108.3 ? C8 C9 H9A . . 109.5 ? C8 C9 H9B . . 109.5 ? H9A C9 H9B . . 109.5 ? C8 C9 H9C . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? C8 C10 H10A . . 109.5 ? C8 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? C8 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1N O1 1_455 0.83(5) 2.10(5) 2.890(5) 160(5)