# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_form1 _database_code_depnum_ccdc_archive 'CCDC 890752' #TrackingRef '- FORM1.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common 'fenobam monohydrate' _chemical_melting_point 'trasforms to form II at 353 K' _chemical_formula_moiety 'C11 H11 Cl N4 O2, H2 O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C11 H13 Cl N4 O3' _chemical_formula_iupac ? _chemical_formula_weight 284.70 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 7.7579(16) _cell_length_b 8.6433(16) _cell_length_c 10.536(2) _cell_angle_alpha 92.620(16) _cell_angle_beta 92.898(17) _cell_angle_gamma 114.618(19) _cell_volume 639.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2255 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25 _cell_special_details ; Least Squares Treatment of 25 SET4 setting angles. ; _exptl_crystal_description needle _exptl_crystal_colour ' colourless' _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.150 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.309 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.900 _exptl_absorpt_correction_T_max 0.955 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 4343 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2255 # number of observed reflections (> n sig(I)) _reflns_number_gt 1730 _reflns_threshold_expression >2\s(i) _computing_data_collection 'Locally modified CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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.The hydrogen atom H3 is located from difference Fourier map, followed by a refinemnet with DFIX restraint applied to N3-H3 bond with a value of 0.87. ; _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^)+(0.0676P)^2^+0.0303P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method shelxl _refine_ls_extinction_coef 0.011(4) _refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC^2^\L^3^/SIN(2\Q)]^-1/4^ _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 2255 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1272 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.259 _refine_diff_density_min -0.296 _refine_diff_density_rms 0.051 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl1 Cl Uani -0.04037(11) 0.76723(10) 1.00635(7) 1.000 0.0594(3) . . O1 O Uani -0.0906(2) 0.3647(2) 0.63577(18) 1.000 0.0494(6) . . O2 O Uani -0.5028(2) -0.0759(3) 0.3431(2) 1.000 0.0626(7) . . N1 N Uani 0.2302(3) 0.4773(3) 0.68315(19) 1.000 0.0380(7) . . N2 N Uani 0.1073(2) 0.2909(3) 0.50955(18) 1.000 0.0341(6) . . N3 N Uani -0.2260(3) 0.1244(3) 0.44528(19) 1.000 0.0385(7) . . N4 N Uani -0.0097(3) 0.0865(3) 0.33880(19) 1.000 0.0373(6) . . C1 C Uani 0.1383(4) 0.7121(3) 0.9553(2) 1.000 0.0398(8) . . C2 C Uani 0.3036(4) 0.7621(4) 1.0306(3) 1.000 0.0625(11) . . C3 C Uani 0.4430(4) 0.7172(5) 0.9871(3) 1.000 0.0748(13) . . C4 C Uani 0.4166(4) 0.6251(4) 0.8729(3) 1.000 0.0540(10) . . C5 C Uani 0.2473(3) 0.5737(3) 0.7978(2) 1.000 0.0349(7) . . C6 C Uani 0.1058(3) 0.6184(3) 0.8396(2) 1.000 0.0376(8) . . C7 C Uani 0.0673(3) 0.3758(3) 0.6110(2) 1.000 0.0333(7) . . C8 C Uani -0.0332(3) 0.1773(3) 0.4368(2) 1.000 0.0315(7) . . C9 C Uani -0.3308(3) -0.0020(3) 0.3551(2) 1.000 0.0412(8) . . C10 C Uani -0.1905(3) -0.0313(3) 0.2759(3) 1.000 0.0388(8) . . C11 C Uani 0.1721(4) 0.0962(4) 0.2997(3) 1.000 0.0465(10) . . O3 O Uani 0.5872(3) 0.4604(4) 0.6368(3) 1.000 0.0674(9) . . H1 H Uiso 0.332(5) 0.471(4) 0.659(3) 1.000 0.066(9) . . H2 H Uiso 0.32180 0.82420 1.10840 1.000 0.0750 calc R H3 H Uiso -0.262(3) 0.168(3) 0.505(2) 1.000 0.041(7) . . H3C H Uiso 0.55710 0.75030 1.03650 1.000 0.0890 calc R H4 H Uiso 0.51260 0.59680 0.84550 1.000 0.0650 calc R H6 H Uiso -0.00850 0.58580 0.79060 1.000 0.0450 calc R H10A H Uiso -0.203(3) -0.005(3) 0.190(2) 1.000 0.036(6) . . H10B H Uiso -0.210(3) -0.154(3) 0.267(2) 1.000 0.044(7) . . H11A H Uiso 0.271(4) 0.155(4) 0.372(3) 1.000 0.075(10) . . H11B H Uiso 0.200(5) 0.152(5) 0.223(4) 1.000 0.096(13) . . H11C H Uiso 0.169(4) -0.015(5) 0.286(3) 1.000 0.069(10) . . H3A H Uiso 0.670(7) 0.534(7) 0.592(5) 1.000 0.128(19) . . H3B H Uiso 0.609(7) 0.389(6) 0.646(5) 1.000 0.13(2) . . 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 Cl1 0.0748(6) 0.0665(6) 0.0524(5) -0.0054(4) 0.0088(4) 0.0455(5) O1 0.0298(9) 0.0612(13) 0.0545(11) -0.0222(10) -0.0033(8) 0.0197(9) O2 0.0323(10) 0.0744(15) 0.0632(13) -0.0226(12) -0.0067(9) 0.0088(10) N1 0.0290(10) 0.0432(13) 0.0382(11) -0.0128(10) -0.0034(9) 0.0138(10) N2 0.0291(10) 0.0355(11) 0.0358(11) -0.0074(9) -0.0043(8) 0.0135(9) N3 0.0307(10) 0.0450(13) 0.0358(12) -0.0116(10) -0.0023(9) 0.0140(10) N4 0.0333(10) 0.0399(12) 0.0359(11) -0.0091(10) -0.0013(8) 0.0143(9) C1 0.0485(14) 0.0340(14) 0.0366(13) -0.0022(12) 0.0036(11) 0.0176(12) C2 0.0618(19) 0.073(2) 0.0424(16) -0.0245(16) -0.0059(14) 0.0221(17) C3 0.0461(17) 0.100(3) 0.066(2) -0.035(2) -0.0206(15) 0.0255(18) C4 0.0354(14) 0.064(2) 0.0546(17) -0.0187(16) -0.0090(13) 0.0166(14) C5 0.0334(12) 0.0311(13) 0.0337(12) -0.0033(11) 0.0006(10) 0.0079(11) C6 0.0405(13) 0.0325(14) 0.0385(13) -0.0004(12) -0.0027(11) 0.0151(11) C7 0.0332(12) 0.0295(13) 0.0371(13) -0.0017(11) -0.0011(10) 0.0140(11) C8 0.0307(12) 0.0311(12) 0.0326(12) 0.0001(11) -0.0015(10) 0.0134(10) C9 0.0358(13) 0.0409(15) 0.0415(14) -0.0045(13) -0.0065(11) 0.0125(12) C10 0.0406(14) 0.0331(15) 0.0342(14) -0.0055(12) -0.0061(11) 0.0088(12) C11 0.0388(14) 0.0543(19) 0.0489(17) -0.0056(16) 0.0048(13) 0.0227(14) O3 0.0468(12) 0.0707(17) 0.0944(19) 0.0173(15) 0.0209(12) 0.0315(13) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.744(3) . . yes O1 C7 1.231(3) . . yes O2 C9 1.212(3) . . yes O3 H3B 0.71(5) . . no O3 H3A 0.87(6) . . no N1 C7 1.365(3) . . yes N1 C5 1.404(3) . . yes N2 C7 1.389(3) . . yes N2 C8 1.302(3) . . yes N3 C8 1.379(4) . . yes N3 C9 1.358(3) . . yes N4 C10 1.448(4) . . yes N4 C11 1.459(4) . . yes N4 C8 1.334(3) . . yes N1 H1 0.86(4) . . no N3 H3 0.84(2) . . no C1 C6 1.384(3) . . no C1 C2 1.366(4) . . no C2 C3 1.383(5) . . no C3 C4 1.369(5) . . no C4 C5 1.388(4) . . no C5 C6 1.391(4) . . no C9 C10 1.499(4) . . no C2 H2 0.9300 . . no C3 H3C 0.9300 . . no C4 H4 0.9300 . . no C6 H6 0.9300 . . no C10 H10B 1.01(2) . . no C10 H10A 0.95(2) . . no C11 H11C 0.96(4) . . no C11 H11A 1.00(3) . . no C11 H11B 0.95(4) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H3A O3 H3B 111(6) . . . no C5 N1 C7 127.6(2) . . . yes C7 N2 C8 118.9(2) . . . yes C8 N3 C9 112.3(2) . . . yes C8 N4 C11 125.8(2) . . . yes C10 N4 C11 122.7(2) . . . yes C8 N4 C10 111.5(2) . . . yes C7 N1 H1 115(2) . . . no C5 N1 H1 117(2) . . . no C9 N3 H3 129.4(17) . . . no C8 N3 H3 118.1(17) . . . no Cl1 C1 C2 119.1(2) . . . yes C2 C1 C6 122.7(3) . . . no Cl1 C1 C6 118.3(2) . . . yes C1 C2 C3 117.7(3) . . . no C2 C3 C4 121.4(3) . . . no C3 C4 C5 120.4(3) . . . no N1 C5 C4 116.9(2) . . . yes C4 C5 C6 119.1(2) . . . no N1 C5 C6 124.1(2) . . . yes C1 C6 C5 118.8(2) . . . no O1 C7 N2 126.5(2) . . . yes O1 C7 N1 122.9(2) . . . yes N1 C7 N2 110.6(2) . . . yes N2 C8 N4 123.5(2) . . . yes N3 C8 N4 107.7(2) . . . yes N2 C8 N3 128.9(2) . . . yes O2 C9 C10 127.7(2) . . . yes N3 C9 C10 106.0(2) . . . yes O2 C9 N3 126.4(2) . . . yes N4 C10 C9 102.5(2) . . . yes C1 C2 H2 121.00 . . . no C3 C2 H2 121.00 . . . no C2 C3 H3C 119.00 . . . no C4 C3 H3C 119.00 . . . no C5 C4 H4 120.00 . . . no C3 C4 H4 120.00 . . . no C5 C6 H6 121.00 . . . no C1 C6 H6 121.00 . . . no N4 C10 H10A 110.9(15) . . . no C9 C10 H10A 111.5(15) . . . no C9 C10 H10B 113.6(14) . . . no N4 C10 H10B 115.3(14) . . . no H10A C10 H10B 103.3(19) . . . no N4 C11 H11B 110(3) . . . no N4 C11 H11C 111(2) . . . no N4 C11 H11A 108.1(19) . . . no H11A C11 H11C 106(3) . . . no H11B C11 H11C 109(3) . . . no H11A C11 H11B 114(3) . . . no 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 C5 N1 C7 N2 -175.3(2) . . . . no C7 N1 C5 C4 161.2(3) . . . . no C7 N1 C5 C6 -18.3(4) . . . . no C5 N1 C7 O1 4.7(4) . . . . no C8 N2 C7 N1 174.2(2) . . . . no C8 N2 C7 O1 -5.8(4) . . . . no C7 N2 C8 N4 -178.6(2) . . . . no C7 N2 C8 N3 -0.4(4) . . . . no C9 N3 C8 N4 0.8(3) . . . . no C9 N3 C8 N2 -177.6(2) . . . . no C8 N3 C9 C10 -2.0(3) . . . . no C8 N3 C9 O2 177.4(2) . . . . no C10 N4 C8 N2 179.4(2) . . . . no C11 N4 C8 N2 1.5(4) . . . . no C10 N4 C8 N3 0.8(3) . . . . no C11 N4 C10 C9 176.0(2) . . . . no C11 N4 C8 N3 -177.0(2) . . . . no C8 N4 C10 C9 -1.9(3) . . . . no C2 C1 C6 C5 -0.3(4) . . . . no Cl1 C1 C2 C3 -179.6(2) . . . . no C6 C1 C2 C3 0.6(4) . . . . no Cl1 C1 C6 C5 179.97(18) . . . . no C1 C2 C3 C4 -0.3(5) . . . . no C2 C3 C4 C5 -0.3(5) . . . . no C3 C4 C5 N1 -179.0(3) . . . . no C3 C4 C5 C6 0.6(4) . . . . no C4 C5 C6 C1 -0.3(4) . . . . no N1 C5 C6 C1 179.2(2) . . . . no N3 C9 C10 N4 2.3(3) . . . . no O2 C9 C10 N4 -177.1(3) . . . . 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 Cl1 C5 3.531(3) . 2_567 no Cl1 C6 3.629(3) . 2_567 no Cl1 H3C 3.1000 . 1_455 no Cl1 H10A 3.10(2) . 2_566 no Cl1 H11B 2.90(4) . 2_566 no O1 O3 2.942(3) . 1_455 no O1 N3 2.652(3) . . no O1 C6 2.863(3) . . no O1 O2 3.129(3) . 2_456 no O2 O1 3.129(3) . 2_456 no O2 N3 3.066(3) . 2_456 no O2 O3 3.128(4) . 2_556 no O3 O2 3.128(4) . 2_556 no O3 N2 3.007(4) . 2_666 no O3 O1 2.942(3) . 1_655 no O3 N1 2.898(4) . . no O3 C4 3.398(4) . . no O1 H6 2.3100 . . no O1 H3 2.07(2) . . no O1 H3A 2.84(6) . 1_455 no O1 H3B 2.43(6) . 1_455 no O2 H2 2.6800 . 1_444 no O2 H11C 2.85(4) . 1_455 no O2 H3B 2.49(5) . 2_556 no O2 H3 2.39(2) . 2_456 no O3 H4 2.6500 . . no O3 H1 2.04(4) . . no N1 O3 2.898(4) . . no N2 O3 3.007(4) . 2_666 no N3 O2 3.066(3) . 2_456 no N3 O1 2.652(3) . . no N1 H10B 2.81(2) . 2_556 no N2 H11A 2.52(3) . . no N2 H10B 2.90(2) . 2_556 no N2 H3A 2.14(6) . 2_666 no C1 C6 3.590(3) . 2_567 no C1 C1 3.592(3) . 2_567 no C4 O3 3.398(4) . . no C5 Cl1 3.531(3) . 2_567 no C6 O1 2.863(3) . . no C6 Cl1 3.629(3) . 2_567 no C6 C1 3.590(3) . 2_567 no C1 H10A 2.89(2) . 2_566 no C4 H11B 3.05(4) . 2_666 no C7 H3 2.59(2) . . no C7 H6 2.8100 . . no C7 H10B 2.90(2) . 2_556 no C7 H3A 2.93(6) . 2_666 no C8 H3A 2.93(6) . 2_666 no C11 H3A 3.05(6) . 2_666 no H1 H4 2.2900 . . no H1 H3B 2.54(7) . . no H1 O3 2.04(4) . . no H1 H3A 2.59(7) . . no H2 O2 2.6800 . 1_666 no H3 O1 2.07(2) . . no H3 C7 2.59(2) . . no H3 O2 2.39(2) . 2_456 no H3A C11 3.05(5) . 2_666 no H3A H11A 2.54(6) . 2_666 no H3A H1 2.59(7) . . no H3A N2 2.14(6) . 2_666 no H3A O1 2.84(6) . 1_655 no H3A C8 2.93(6) . 2_666 no H3A C7 2.93(6) . 2_666 no H3B H1 2.54(7) . . no H3B O1 2.43(6) . 1_655 no H3B O2 2.49(5) . 2_556 no H3C H10A 2.5800 . 1_666 no H3C Cl1 3.1000 . 1_655 no H4 O3 2.6500 . . no H4 H11B 2.5500 . 2_666 no H4 H1 2.2900 . . no H6 O1 2.3100 . . no H6 C7 2.8100 . . no H10A Cl1 3.10(2) . 2_566 no H10A H3C 2.5800 . 1_444 no H10A C1 2.89(2) . 2_566 no H10B N2 2.90(2) . 2_556 no H10B N1 2.81(2) . 2_556 no H10B C7 2.90(2) . 2_556 no H11A H3A 2.54(6) . 2_666 no H11A N2 2.52(3) . . no H11B Cl1 2.90(4) . 2_566 no H11B C4 3.05(4) . 2_666 no H11B H4 2.5500 . 2_666 no H11C O2 2.85(4) . 1_655 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 # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 O3 0.86(4) 2.04(4) 2.898(4) 170(3) . yes N3 H3 O1 0.84(2) 2.07(2) 2.652(3) 127(2) . yes N3 H3 O2 0.84(2) 2.39(2) 3.066(3) 138(2) 2_456 yes O3 H3A N2 0.87(6) 2.14(6) 3.007(4) 175(5) 2_666 yes O3 H3B O1 0.71(5) 2.43(6) 2.942(3) 130(5) 1_655 yes O3 H3B O2 0.71(5) 2.49(5) 3.128(4) 150(6) 2_556 yes C6 H6 O1 0.9300 2.3100 2.863(3) 118.00 . yes C11 H11A N2 1.00(3) 2.52(3) 2.907(4) 102(2) . yes data_tw_twin1_hklf4 _database_code_depnum_ccdc_archive 'CCDC 890753' #TrackingRef 'CIF_Form5_twin.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common 'fenobam hemihydrate' _chemical_melting_point ? _chemical_formula_moiety '2(C11 H11 Cl N4 O2), H2 O' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C22 H24 Cl2 N8 O5' _chemical_formula_iupac ? _chemical_formula_weight 551.39 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 9.8299(15) _cell_length_b 11.4813(19) _cell_length_c 11.6916(15) _cell_angle_alpha 105.930(13) _cell_angle_beta 97.779(12) _cell_angle_gamma 104.196(13) _cell_volume 1200.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 366 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 25.0 _cell_special_details ; Least Squares Treatment of 25 SET4 setting angles. ; _exptl_crystal_description needle _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 0.324 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_T_max 0.968 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 6887 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0797 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 6887 # number of observed reflections (> n sig(I)) _reflns_number_gt 4551 _reflns_threshold_expression >2\s(i) _computing_data_collection 'Locally modified CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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.SHELXL HKLF 5 Refinement has been carried out to account for twinning with a BASF value of 0.48235. Hydrogen atoms H2N, H6N and H1O were located from difference Fourier map and restrained in their respective bond lengths with the connecting heavy atoms. ; _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^)+(0.1276P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 6887 _refine_ls_number_parameters 367 _refine_ls_number_restraints 3 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.1148 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.2150 _refine_ls_wR_factor_gt 0.1924 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.461 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.102 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl1 Cl Uani 0.07255(11) -0.24282(12) 0.56541(10) 1.000 0.0303(4) . . O3 O Uani 0.5145(3) 0.4341(3) 0.3290(3) 1.000 0.0283(10) . . O4 O Uani 0.4249(3) 0.1309(3) 0.5318(2) 1.000 0.0216(9) . . N5 N Uani 0.7567(3) 0.4482(3) 0.5831(3) 1.000 0.0199(11) . . N6 N Uani 0.5459(4) 0.3289(3) 0.4672(3) 1.000 0.0205(11) . . N7 N Uani 0.6463(3) 0.2783(3) 0.6423(3) 1.000 0.0188(11) . . N8 N Uani 0.5541(4) 0.1088(3) 0.6985(3) 1.000 0.0179(11) . . C12 C Uani 0.7309(4) 0.5041(4) 0.4895(4) 1.000 0.0214(14) . . C13 C Uani 0.5839(4) 0.4204(4) 0.4156(4) 1.000 0.0204(14) . . C14 C Uani 0.6484(4) 0.3455(4) 0.5692(3) 1.000 0.0170(12) . . C15 C Uani 0.8874(4) 0.4945(4) 0.6776(4) 1.000 0.0284(14) . . C16 C Uani 0.5316(4) 0.1696(4) 0.6150(3) 1.000 0.0164(12) . . C17 C Uani 0.4607(4) 0.0027(4) 0.7137(3) 1.000 0.0194(12) . . C18 C Uani 0.3273(4) -0.0633(4) 0.6364(4) 1.000 0.0209(12) . . C19 C Uani 0.2416(4) -0.1639(4) 0.6616(4) 1.000 0.0227(14) . . C20 C Uani 0.2824(5) -0.2001(4) 0.7608(4) 1.000 0.0248(16) . . C21 C Uani 0.4178(5) -0.1337(4) 0.8356(4) 1.000 0.0289(16) . . C22 C Uani 0.5058(5) -0.0339(4) 0.8127(4) 1.000 0.0245(14) . . Cl2 Cl Uani 0.79544(13) 0.72809(11) 1.32293(9) 1.000 0.0323(4) . . O1 O Uani 1.2033(3) 0.0739(3) 1.0353(3) 1.000 0.0251(10) . . O2 O Uani 0.9187(3) 0.3534(3) 1.0654(2) 1.000 0.0244(9) . . N1 N Uani 0.9564(4) 0.0649(3) 0.7845(3) 1.000 0.0213(11) . . N2 N Uani 1.0428(4) 0.1752(3) 0.9794(3) 1.000 0.0195(11) . . N3 N Uani 0.8539(4) 0.2233(3) 0.8608(3) 1.000 0.0193(11) . . N4 N Uani 0.7693(4) 0.3893(3) 0.9194(3) 1.000 0.0193(11) . . C1 C Uani 1.1165(4) 0.0877(4) 0.9599(4) 1.000 0.0209(14) . . C2 C Uani 1.0674(5) 0.0131(4) 0.8261(4) 1.000 0.0220(14) . . C3 C Uani 0.9443(4) 0.1596(4) 0.8754(3) 1.000 0.0195(12) . . C4 C Uani 0.8798(5) 0.0258(5) 0.6582(4) 1.000 0.0289(16) . . C5 C Uani 0.8546(4) 0.3241(4) 0.9589(4) 1.000 0.0186(12) . . C6 C Uani 0.7342(4) 0.4957(4) 0.9847(3) 1.000 0.0174(11) . . C7 C Uani 0.6443(4) 0.5418(4) 0.9192(4) 1.000 0.0222(14) . . C8 C Uani 0.5997(4) 0.6421(4) 0.9759(4) 1.000 0.0239(16) . . C9 C Uani 0.6443(4) 0.7010(4) 1.1018(4) 1.000 0.0231(14) . . C10 C Uani 0.7366(4) 0.6546(4) 1.1651(4) 1.000 0.0220(14) . . C11 C Uani 0.7819(4) 0.5535(4) 1.1097(3) 1.000 0.0190(12) . . O1S O Uani 0.2473(4) 0.2461(4) 0.2700(3) 1.000 0.0427(12) . . H6N H Uiso 0.477(4) 0.266(4) 0.449(4) 1.000 0.0210 . . H8N H Uiso 0.635(5) 0.143(4) 0.746(4) 1.000 0.018(12) . . H12A H Uiso 0.80270 0.50230 0.44030 1.000 0.0260 calc R H12B H Uiso 0.73050 0.59110 0.52410 1.000 0.0260 calc R H15A H Uiso 0.88090 0.56380 0.74280 1.000 0.0420 calc R H15B H Uiso 0.96850 0.52310 0.64420 1.000 0.0420 calc R H15C H Uiso 0.89920 0.42740 0.70840 1.000 0.0420 calc R H18 H Uiso 0.29650 -0.04030 0.56930 1.000 0.0250 calc R H20 H Uiso 0.22160 -0.26660 0.77720 1.000 0.0300 calc R H21 H Uiso 0.44900 -0.15740 0.90200 1.000 0.0350 calc R H22 H Uiso 0.59590 0.00950 0.86360 1.000 0.0290 calc R H2A H Uiso 1.020(4) -0.078(4) 0.811(3) 1.000 0.016(10) . . H2B H Uiso 1.139(4) 0.020(4) 0.778(4) 1.000 0.027(12) . . H2N H Uiso 1.037(4) 0.231(4) 1.047(3) 1.000 0.0210 . . H4A H Uiso 0.79550 -0.04420 0.64380 1.000 0.0440 calc R H4B H Uiso 0.94130 0.00040 0.60530 1.000 0.0440 calc R H4C H Uiso 0.85210 0.09540 0.64230 1.000 0.0440 calc R H4N H Uiso 0.728(4) 0.356(4) 0.841(4) 1.000 0.013(11) . . H7 H Uiso 0.61380 0.50380 0.83520 1.000 0.0270 calc R H8 H Uiso 0.53910 0.67150 0.93020 1.000 0.0290 calc R H9 H Uiso 0.61340 0.76850 1.14160 1.000 0.0280 calc R H11 H Uiso 0.84320 0.52430 1.15490 1.000 0.0230 calc R H1O H Uiso 0.241(7) 0.191(5) 0.202(4) 1.000 0.07(2) . . H2O H Uiso 0.322(8) 0.303(7) 0.264(6) 1.000 0.10(3) . . 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 Cl1 0.0220(6) 0.0289(6) 0.0345(7) 0.0076(5) 0.0059(5) 0.0008(5) O3 0.0291(17) 0.0282(19) 0.0239(17) 0.0095(14) -0.0041(14) 0.0061(15) O4 0.0180(15) 0.0263(18) 0.0188(15) 0.0093(13) -0.0007(13) 0.0039(13) N5 0.0130(17) 0.025(2) 0.0212(18) 0.0118(16) 0.0001(15) 0.0017(16) N6 0.0166(19) 0.022(2) 0.0206(19) 0.0054(17) 0.0026(16) 0.0041(16) N7 0.0155(18) 0.024(2) 0.0153(17) 0.0068(16) 0.0020(14) 0.0034(16) N8 0.0107(18) 0.022(2) 0.0205(19) 0.0079(16) 0.0019(15) 0.0037(16) C12 0.020(2) 0.022(3) 0.020(2) 0.0074(19) 0.0032(18) 0.0022(19) C13 0.021(2) 0.026(3) 0.016(2) 0.0060(19) 0.0061(18) 0.010(2) C14 0.016(2) 0.020(2) 0.017(2) 0.0039(18) 0.0055(17) 0.0102(18) C15 0.022(2) 0.033(3) 0.027(2) 0.011(2) 0.000(2) 0.004(2) C16 0.016(2) 0.023(2) 0.011(2) 0.0049(17) 0.0051(17) 0.0068(19) C17 0.023(2) 0.019(2) 0.018(2) 0.0032(18) 0.0077(18) 0.0106(19) C18 0.026(2) 0.024(2) 0.016(2) 0.0063(18) 0.0075(18) 0.012(2) C19 0.021(2) 0.023(3) 0.026(2) 0.0043(19) 0.0118(19) 0.0102(19) C20 0.031(3) 0.024(3) 0.027(2) 0.011(2) 0.016(2) 0.013(2) C21 0.035(3) 0.033(3) 0.027(2) 0.014(2) 0.010(2) 0.018(2) C22 0.026(2) 0.030(3) 0.023(2) 0.010(2) 0.0056(19) 0.016(2) Cl2 0.0443(7) 0.0299(7) 0.0208(6) 0.0032(5) 0.0088(5) 0.0122(6) O1 0.0204(16) 0.0271(18) 0.0281(17) 0.0098(14) -0.0028(13) 0.0109(14) O2 0.0262(16) 0.0289(18) 0.0148(15) 0.0020(13) -0.0010(13) 0.0110(14) N1 0.0226(19) 0.026(2) 0.0179(18) 0.0067(16) 0.0053(15) 0.0116(17) N2 0.0189(18) 0.024(2) 0.0142(18) 0.0033(15) 0.0019(15) 0.0082(16) N3 0.0190(18) 0.019(2) 0.0177(18) 0.0018(15) 0.0014(14) 0.0078(16) N4 0.0197(18) 0.023(2) 0.0130(18) 0.0042(16) -0.0016(15) 0.0069(16) C1 0.011(2) 0.025(3) 0.029(2) 0.012(2) 0.0063(18) 0.0045(19) C2 0.026(2) 0.022(3) 0.019(2) 0.007(2) 0.0053(19) 0.008(2) C3 0.019(2) 0.021(2) 0.016(2) 0.0058(18) 0.0045(17) 0.0013(19) C4 0.030(3) 0.038(3) 0.015(2) 0.006(2) -0.0022(19) 0.010(2) C5 0.015(2) 0.020(2) 0.020(2) 0.0072(18) 0.0043(18) 0.0027(18) C6 0.0095(19) 0.022(2) 0.022(2) 0.0077(18) 0.0042(16) 0.0059(18) C7 0.019(2) 0.025(3) 0.023(2) 0.013(2) 0.0014(18) 0.003(2) C8 0.017(2) 0.027(3) 0.033(3) 0.017(2) 0.0031(19) 0.009(2) C9 0.022(2) 0.020(2) 0.033(3) 0.011(2) 0.0111(19) 0.0107(19) C10 0.017(2) 0.024(3) 0.023(2) 0.0095(19) 0.0062(18) -0.0009(19) C11 0.018(2) 0.025(2) 0.014(2) 0.0057(18) 0.0028(17) 0.0075(19) O1S 0.048(2) 0.033(2) 0.037(2) 0.0018(18) 0.0171(18) 0.0007(19) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C19 1.745(4) . . yes Cl2 C10 1.752(5) . . yes O3 C13 1.212(5) . . yes O4 C16 1.225(5) . . yes O1 C1 1.212(5) . . yes O2 C5 1.231(5) . . yes O1S H1O 0.85(5) . . no O1S H2O 0.88(8) . . no N5 C15 1.453(5) . . yes N5 C14 1.335(6) . . yes N5 C12 1.437(6) . . yes N6 C13 1.350(6) . . yes N6 C14 1.389(5) . . yes N7 C14 1.298(5) . . yes N7 C16 1.387(6) . . yes N8 C16 1.371(5) . . yes N8 C17 1.405(6) . . yes N6 H6N 0.81(4) . . no N8 H8N 0.84(5) . . no N1 C3 1.338(5) . . yes N1 C2 1.454(6) . . yes N1 C4 1.455(6) . . yes N2 C3 1.387(5) . . yes N2 C1 1.365(6) . . yes N3 C3 1.304(6) . . yes N3 C5 1.386(6) . . yes N4 C6 1.400(6) . . yes N4 C5 1.367(6) . . yes N2 H2N 0.89(4) . . no N4 H4N 0.88(4) . . no C12 C13 1.511(6) . . no C17 C18 1.388(6) . . no C17 C22 1.390(6) . . no C18 C19 1.381(6) . . no C19 C20 1.378(6) . . no C20 C21 1.392(7) . . no C21 C22 1.370(7) . . no C12 H12B 0.9700 . . no C12 H12A 0.9700 . . no C15 H15A 0.9600 . . no C15 H15C 0.9600 . . no C15 H15B 0.9600 . . no C18 H18 0.9300 . . no C20 H20 0.9300 . . no C21 H21 0.9300 . . no C22 H22 0.9300 . . no C1 C2 1.507(6) . . no C6 C11 1.388(5) . . no C6 C7 1.384(6) . . no C7 C8 1.366(6) . . no C8 C9 1.396(6) . . no C9 C10 1.388(6) . . no C10 C11 1.373(6) . . no C2 H2B 0.96(4) . . no C2 H2A 0.99(5) . . no C4 H4C 0.9600 . . no C4 H4A 0.9600 . . no C4 H4B 0.9600 . . no C7 H7 0.9300 . . no C8 H8 0.9300 . . no C9 H9 0.9300 . . no C11 H11 0.9300 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H1O O1S H2O 95(6) . . . no C12 N5 C14 111.5(3) . . . yes C14 N5 C15 124.4(3) . . . yes C12 N5 C15 124.1(3) . . . yes C13 N6 C14 112.3(4) . . . yes C14 N7 C16 118.1(3) . . . yes C16 N8 C17 128.8(4) . . . yes C13 N6 H6N 133(3) . . . no C14 N6 H6N 115(3) . . . no C17 N8 H8N 119(3) . . . no C16 N8 H8N 112(3) . . . no C3 N1 C4 125.3(4) . . . yes C2 N1 C3 110.7(3) . . . yes C2 N1 C4 123.8(4) . . . yes C1 N2 C3 112.0(3) . . . yes C3 N3 C5 118.3(3) . . . yes C5 N4 C6 129.9(3) . . . yes C3 N2 H2N 115(3) . . . no C1 N2 H2N 132(3) . . . no C5 N4 H4N 114(3) . . . no C6 N4 H4N 116(3) . . . no N5 C12 C13 102.9(4) . . . yes O3 C13 C12 126.8(4) . . . yes O3 C13 N6 127.5(4) . . . yes N6 C13 C12 105.7(4) . . . yes N5 C14 N6 107.6(4) . . . yes N6 C14 N7 129.1(4) . . . yes N5 C14 N7 123.3(3) . . . yes N7 C16 N8 108.9(3) . . . yes O4 C16 N7 127.6(4) . . . yes O4 C16 N8 123.5(4) . . . yes N8 C17 C22 117.1(4) . . . yes N8 C17 C18 122.9(4) . . . yes C18 C17 C22 120.0(4) . . . no C17 C18 C19 118.3(4) . . . no Cl1 C19 C20 119.7(4) . . . yes C18 C19 C20 122.7(4) . . . no Cl1 C19 C18 117.5(3) . . . yes C19 C20 C21 117.7(4) . . . no C20 C21 C22 121.0(4) . . . no C17 C22 C21 120.2(4) . . . no C13 C12 H12B 111.00 . . . no H12A C12 H12B 109.00 . . . no C13 C12 H12A 111.00 . . . no N5 C12 H12A 111.00 . . . no N5 C12 H12B 111.00 . . . no H15B C15 H15C 109.00 . . . no H15A C15 H15B 109.00 . . . no N5 C15 H15B 110.00 . . . no N5 C15 H15C 110.00 . . . no H15A C15 H15C 109.00 . . . no N5 C15 H15A 109.00 . . . no C17 C18 H18 121.00 . . . no C19 C18 H18 121.00 . . . no C19 C20 H20 121.00 . . . no C21 C20 H20 121.00 . . . no C22 C21 H21 119.00 . . . no C20 C21 H21 120.00 . . . no C17 C22 H22 120.00 . . . no C21 C22 H22 120.00 . . . no O1 C1 N2 126.7(4) . . . yes N2 C1 C2 105.6(4) . . . yes O1 C1 C2 127.7(4) . . . yes N1 C2 C1 103.1(4) . . . yes N1 C3 N2 108.4(4) . . . yes N1 C3 N3 122.6(3) . . . yes N2 C3 N3 129.0(4) . . . yes N3 C5 N4 108.8(4) . . . yes O2 C5 N4 123.6(4) . . . yes O2 C5 N3 127.7(4) . . . yes N4 C6 C11 123.5(4) . . . yes N4 C6 C7 116.9(3) . . . yes C7 C6 C11 119.6(4) . . . no C6 C7 C8 121.1(4) . . . no C7 C8 C9 120.6(4) . . . no C8 C9 C10 117.2(4) . . . no Cl2 C10 C11 119.0(3) . . . yes C9 C10 C11 122.9(4) . . . no Cl2 C10 C9 118.0(3) . . . yes C6 C11 C10 118.6(4) . . . no N1 C2 H2A 106(2) . . . no C1 C2 H2A 113(2) . . . no C1 C2 H2B 116(3) . . . no N1 C2 H2B 109(3) . . . no H2A C2 H2B 108(4) . . . no N1 C4 H4B 109.00 . . . no N1 C4 H4C 109.00 . . . no H4A C4 H4B 110.00 . . . no H4A C4 H4C 109.00 . . . no H4B C4 H4C 109.00 . . . no N1 C4 H4A 109.00 . . . no C6 C7 H7 119.00 . . . no C8 C7 H7 120.00 . . . no C9 C8 H8 120.00 . . . no C7 C8 H8 120.00 . . . no C8 C9 H9 121.00 . . . no C10 C9 H9 121.00 . . . no C6 C11 H11 121.00 . . . no C10 C11 H11 121.00 . . . no 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 C14 N5 C12 C13 1.7(4) . . . . no C15 N5 C12 C13 179.1(4) . . . . no C15 N5 C14 N7 2.7(6) . . . . no C12 N5 C14 N6 -0.4(5) . . . . no C15 N5 C14 N6 -177.8(4) . . . . no C12 N5 C14 N7 -180.0(4) . . . . no C13 N6 C14 N5 -1.3(5) . . . . no C14 N6 C13 O3 -176.9(4) . . . . no C14 N6 C13 C12 2.3(5) . . . . no C13 N6 C14 N7 178.2(4) . . . . no C16 N7 C14 N5 -176.6(4) . . . . no C16 N7 C14 N6 4.0(6) . . . . no C14 N7 C16 N8 176.4(3) . . . . no C14 N7 C16 O4 -4.2(6) . . . . no C16 N8 C17 C18 4.0(7) . . . . no C17 N8 C16 N7 173.2(4) . . . . no C17 N8 C16 O4 -6.3(7) . . . . no C16 N8 C17 C22 -174.7(4) . . . . no C4 N1 C3 N3 4.2(7) . . . . no C3 N1 C2 C1 2.8(5) . . . . no C4 N1 C2 C1 177.4(4) . . . . no C2 N1 C3 N2 -0.3(5) . . . . no C4 N1 C3 N2 -174.8(4) . . . . no C2 N1 C3 N3 178.7(4) . . . . no C3 N2 C1 C2 4.3(5) . . . . no C1 N2 C3 N1 -2.7(5) . . . . no C1 N2 C3 N3 178.4(4) . . . . no C3 N2 C1 O1 -175.8(4) . . . . no C5 N3 C3 N2 2.2(7) . . . . no C3 N3 C5 O2 -9.9(7) . . . . no C5 N3 C3 N1 -176.7(4) . . . . no C3 N3 C5 N4 170.6(4) . . . . no C6 N4 C5 O2 -1.1(7) . . . . no C5 N4 C6 C7 179.8(4) . . . . no C5 N4 C6 C11 -1.7(7) . . . . no C6 N4 C5 N3 178.5(4) . . . . no N5 C12 C13 O3 176.8(4) . . . . no N5 C12 C13 N6 -2.4(4) . . . . no N8 C17 C22 C21 177.6(4) . . . . no C22 C17 C18 C19 0.8(6) . . . . no N8 C17 C18 C19 -177.9(4) . . . . no C18 C17 C22 C21 -1.2(7) . . . . no C17 C18 C19 C20 0.8(7) . . . . no C17 C18 C19 Cl1 178.4(3) . . . . no Cl1 C19 C20 C21 -179.5(4) . . . . no C18 C19 C20 C21 -2.0(7) . . . . no C19 C20 C21 C22 1.5(7) . . . . no C20 C21 C22 C17 0.0(7) . . . . no O1 C1 C2 N1 175.9(4) . . . . no N2 C1 C2 N1 -4.2(5) . . . . no N4 C6 C7 C8 177.4(4) . . . . no C11 C6 C7 C8 -1.1(7) . . . . no N4 C6 C11 C10 -177.7(4) . . . . no C7 C6 C11 C10 0.8(6) . . . . no C6 C7 C8 C9 0.2(7) . . . . no C7 C8 C9 C10 1.0(7) . . . . no C8 C9 C10 Cl2 179.4(3) . . . . no C8 C9 C10 C11 -1.4(7) . . . . no Cl2 C10 C11 C6 179.8(3) . . . . no C9 C10 C11 C6 0.5(7) . . . . 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 Cl1 Cl2 3.5373(17) . 1_444 no Cl1 C2 3.623(5) . 1_455 no Cl1 C15 3.596(5) . 2_656 no Cl1 N5 3.446(4) . 2_656 no Cl1 C14 3.623(4) . 2_656 no Cl2 Cl1 3.5373(17) . 1_666 no Cl2 C4 3.642(6) . 2_767 no Cl2 C12 3.618(5) . 1_556 no Cl2 O4 3.377(3) . 2_667 no Cl1 H15B 3.0600 . 1_445 no O1 C22 3.356(6) . 2_757 no O1 N2 3.207(5) . 2_757 no O1 O1S 2.812(5) . 1_656 no O1 C1 3.252(5) . 2_757 no O1 C2 3.385(6) . 2_757 no O1 C3 3.228(6) . 2_757 no O1 C8 3.407(6) . 2_767 no O1S O1 2.812(5) . 1_454 no O1S C13 3.348(6) . . no O1S N6 3.230(5) . . no O1S O3 2.819(5) . . no O1S C12 3.360(6) . 2_666 no O2 N2 2.667(5) . . no O2 C11 2.899(5) . . no O2 C15 3.106(5) . 2_767 no O3 C8 3.385(6) . 2_666 no O3 C7 3.219(6) . 2_666 no O3 C14 3.352(5) . 2_666 no O3 C13 3.388(5) . 2_666 no O3 O1S 2.819(5) . . no O4 C17 3.341(4) . 2_656 no O4 C4 3.241(6) . 2_656 no O4 N6 2.648(5) . . no O4 Cl2 3.377(3) . 2_667 no O4 C18 2.855(6) . . no O1 H22 2.6700 . 2_757 no O1 H1O 1.97(5) . 1_656 no O1S H15A 2.8000 . 2_666 no O1S H2A 2.71(4) . 2_656 no O1S H4A 2.7400 . 2_656 no O1S H6N 2.78(4) . . no O1S H12B 2.5500 . 2_666 no O2 H2N 2.02(4) . . no O2 H15A 2.5600 . 2_767 no O2 H11 2.3000 . . no O2 H20 2.7000 . 2_657 no O3 H2O 2.00(8) . . no O3 H8 2.8600 . 2_666 no O3 H7 2.5100 . 2_666 no O4 H18 2.2500 . . no O4 H6N 2.04(5) . . no O4 H4A 2.5500 . 2_656 no N1 N2 2.210(5) . . no N2 O1 3.207(5) . 2_757 no N2 N1 2.210(5) . . no N2 O2 2.667(5) . . no N2 C1 3.350(6) . 2_757 no N2 C9 3.431(6) . 2_767 no N3 N8 3.038(5) . . no N4 N7 3.082(5) . . no N5 N6 2.199(5) . . no N5 Cl1 3.446(4) . 2_656 no N6 C19 3.383(6) . 2_656 no N6 C13 3.450(6) . 2_666 no N6 N5 2.199(5) . . no N6 O1S 3.230(5) . . no N6 O4 2.648(5) . . no N7 N4 3.082(5) . . no N8 N3 3.038(5) . . no N3 H8N 2.20(5) . . no N3 H4C 2.5700 . . no N4 H8N 2.85(5) . . no N6 H2O 2.91(7) . . no N7 H15C 2.5200 . . no N7 H4N 2.20(4) . . no N8 H4N 2.83(5) . . no C1 C9 3.249(6) . 2_767 no C1 N2 3.350(6) . 2_757 no C1 C8 3.447(6) . 2_767 no C1 O1 3.252(5) . 2_757 no C1 C1 3.088(6) . 2_757 no C1 C2 3.557(6) . 2_757 no C2 C9 3.576(7) . 2_767 no C2 O1 3.385(6) . 2_757 no C2 C1 3.557(6) . 2_757 no C2 C19 3.349(6) . 1_655 no C2 Cl1 3.623(5) . 1_655 no C3 C10 3.506(6) . 2_767 no C3 O1 3.228(6) . 2_757 no C4 Cl2 3.642(6) . 2_767 no C4 O4 3.241(6) . 2_656 no C6 C8 3.428(6) . 2_667 no C7 C9 3.382(6) . 2_667 no C7 C8 3.384(6) . 2_667 no C7 O3 3.219(6) . 2_666 no C8 O3 3.385(6) . 2_666 no C8 O1 3.407(6) . 2_767 no C8 C6 3.428(6) . 2_667 no C8 C1 3.447(6) . 2_767 no C8 C7 3.384(6) . 2_667 no C9 C2 3.576(7) . 2_767 no C9 N2 3.431(6) . 2_767 no C9 C1 3.249(6) . 2_767 no C9 C7 3.382(6) . 2_667 no C10 C3 3.506(6) . 2_767 no C11 O2 2.899(5) . . no C12 O1S 3.360(6) . 2_666 no C12 Cl2 3.618(5) . 1_554 no C13 C13 3.215(6) . 2_666 no C13 O3 3.388(5) . 2_666 no C13 C20 3.447(6) . 2_656 no C13 N6 3.450(6) . 2_666 no C13 O1S 3.348(6) . . no C14 C19 3.407(6) . 2_656 no C14 O3 3.352(5) . 2_666 no C14 C18 3.549(6) . 2_656 no C14 Cl1 3.623(4) . 2_656 no C15 Cl1 3.596(5) . 2_656 no C15 O2 3.106(5) . 2_767 no C16 C18 3.467(6) . 2_656 no C17 O4 3.341(4) . 2_656 no C18 C14 3.549(6) . 2_656 no C18 O4 2.855(6) . . no C18 C16 3.467(6) . 2_656 no C19 C2 3.349(6) . 1_455 no C19 C14 3.407(6) . 2_656 no C19 N6 3.383(6) . 2_656 no C20 C13 3.447(6) . 2_656 no C22 O1 3.356(6) . 2_757 no C1 H1O 2.73(5) . 1_656 no C4 H18 3.0400 . 2_656 no C5 H11 2.8000 . . no C5 H2N 2.54(4) . . no C5 H8N 2.95(5) . . no C13 H2O 2.71(8) . . no C16 H6N 2.54(5) . . no C16 H18 2.7700 . . no C16 H4N 2.96(4) . . no C17 H9 3.0200 . 2_667 no C18 H2B 2.81(4) . 1_455 no C19 H2B 2.68(4) . 1_455 no H1O C1 2.73(5) . 1_454 no H1O H2A 2.54(8) . 2_656 no H1O O1 1.97(5) . 1_454 no H2A O1S 2.71(4) . 2_656 no H2A H1O 2.54(8) . 2_656 no H2B C19 2.68(4) . 1_655 no H2B H4B 2.5300 . . no H2B C18 2.81(4) . 1_655 no H2N O2 2.02(4) . . no H2N C5 2.54(4) . . no H2O N6 2.91(7) . . no H2O C13 2.71(8) . . no H2O O3 2.00(8) . . no H4A O4 2.5500 . 2_656 no H4A O1S 2.7400 . 2_656 no H4B H2B 2.5300 . . no H4C N3 2.5700 . . no H4C H18 2.5200 . 2_656 no H4N N7 2.20(4) . . no H4N N8 2.83(5) . . no H4N H8N 2.28(7) . . no H4N H15C 2.5800 . . no H4N C16 2.96(4) . . no H4N H7 2.2600 . . no H6N C16 2.54(5) . . no H6N O1S 2.78(4) . . no H6N O4 2.04(5) . . no H7 O3 2.5100 . 2_666 no H7 H4N 2.2600 . . no H8 H21 2.4300 . 1_565 no H8 O3 2.8600 . 2_666 no H8N C5 2.95(5) . . no H8N H4N 2.28(7) . . no H8N H22 2.3200 . . no H8N N3 2.20(5) . . no H8N N4 2.85(5) . . no H9 C17 3.0200 . 2_667 no H11 C5 2.8000 . . no H11 O2 2.3000 . . no H12B O1S 2.5500 . 2_666 no H15A O1S 2.8000 . 2_666 no H15A O2 2.5600 . 2_767 no H15B Cl1 3.0600 . 1_665 no H15C H4N 2.5800 . . no H15C N7 2.5200 . . no H18 C16 2.7700 . . no H18 C4 3.0400 . 2_656 no H18 O4 2.2500 . . no H18 H4C 2.5200 . 2_656 no H20 O2 2.7000 . 2_657 no H21 H8 2.4300 . 1_545 no H22 O1 2.6700 . 2_757 no H22 H8N 2.3200 . . 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 # #D H A D - H H...A D...A D - H...A symm(A) # O1S H1O O1 0.85(5) 1.97(5) 2.812(5) 171(6) 1_454 yes N2 H2N O2 0.89(4) 2.02(4) 2.667(5) 129(3) . yes O1S H2O O3 0.88(8) 2.00(8) 2.819(5) 154(6) . yes N4 H4N N7 0.88(4) 2.20(4) 3.082(5) 174(3) . yes N6 H6N O4 0.81(4) 2.04(5) 2.648(5) 131(4) . yes N8 H8N N3 0.84(5) 2.20(5) 3.038(5) 176(5) . yes C4 H4A O4 0.9600 2.5500 3.241(6) 129.00 2_656 yes C7 H7 O3 0.9300 2.5100 3.219(6) 133.00 2_666 yes C11 H11 O2 0.9300 2.3000 2.899(5) 122.00 . yes C12 H12B O1S 0.9700 2.5500 3.360(6) 140.00 2_666 yes C15 H15A O2 0.9600 2.5600 3.106(5) 117.00 2_767 yes C15 H15C N7 0.9600 2.5200 2.870(6) 101.00 . yes C18 H18 O4 0.9300 2.2500 2.855(6) 122.00 . yes data_FormIII_Cc _database_code_depnum_ccdc_archive 'CCDC 890754' #TrackingRef '- FORM3.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common fenobam _chemical_melting_point '456 K' _chemical_formula_moiety 'C11 H11 Cl N4 O2' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C11 H11 Cl N4 O2' _chemical_formula_iupac ? _chemical_formula_weight 266.69 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C c' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 x,-y,1/2+z 3 1/2+x,1/2+y,z 4 1/2+x,1/2-y,1/2+z _cell_length_a 12.8327(14) _cell_length_b 7.6792(14) _cell_length_c 11.9725(14) _cell_angle_alpha 90 _cell_angle_beta 101.188(9) _cell_angle_gamma 90 _cell_volume 1157.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296 _cell_measurement_reflns_used 2226 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 26.0 _cell_special_details ; Least Squares Treatment of 25 SET4 setting angles. ; _exptl_crystal_description ' block' _exptl_crystal_colour ' pale yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.330 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.9221 _exptl_absorpt_correction_T_max 0.9491 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 296 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 8023 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2226 # number of observed reflections (> n sig(I)) _reflns_number_gt 2112 _reflns_threshold_expression >2\s(i) _computing_data_collection 'Locally modified CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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.The hydrogen atom H3A is located from difference Fourier map, followed by a refinemnet with DFIX restraint applied to N3-H3A bond with a value of 0.87.In addition, program generated floating origin restraints are also included in the refinement. ; _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^)+(0.0351P)^2^+0.1677P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(5) # Permitted for _chemical_absolute_configuration: # Absolute configuration details # rm = Det. by chiral ref. mol. with known abs.conf # ad = Det. by anomalous dispersion # rmad = Det. by 'rm' and 'ad' # syn = Det. with reference to synthesis # unk = Unknown/Arbitrary _chemical_absolute_configuration ? _refine_ls_number_reflns 2226 _refine_ls_number_parameters 168 _refine_ls_number_restraints 3 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.0286 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0618 _refine_ls_wR_factor_gt 0.0604 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.152 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.037 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl1 Cl Uani 0.32001(4) 1.24245(6) 0.49208(4) 1.000 0.0297(1) . . O1 O Uani 0.49977(11) 0.67814(17) 0.43275(11) 1.000 0.0271(4) . . O2 O Uani 0.64213(9) 0.14206(16) 0.58922(11) 1.000 0.0232(4) . . N1 N Uani 0.52418(11) 0.82841(19) 0.27427(13) 1.000 0.0194(4) . . N2 N Uani 0.59853(12) 0.56501(19) 0.30329(13) 1.000 0.0204(5) . . N3 N Uani 0.61002(12) 0.38070(19) 0.47054(12) 1.000 0.0188(4) . . N4 N Uani 0.68897(11) 0.30244(19) 0.33090(12) 1.000 0.0204(5) . . C1 C Uani 0.37307(14) 1.1865(2) 0.37365(16) 1.000 0.0198(5) . . C2 C Uani 0.36585(15) 1.3035(2) 0.28439(16) 1.000 0.0234(6) . . C3 C Uani 0.41304(15) 1.2587(2) 0.19382(17) 1.000 0.0228(6) . . C4 C Uani 0.46466(13) 1.1025(2) 0.19235(14) 1.000 0.0197(5) . . C5 C Uani 0.47017(13) 0.9840(2) 0.28243(14) 1.000 0.0175(5) . . C6 C Uani 0.42373(14) 1.0271(2) 0.37473(15) 1.000 0.0191(5) . . C7 C Uani 0.53801(14) 0.6875(2) 0.34651(16) 1.000 0.0196(5) . . C8 C Uani 0.62931(13) 0.4281(2) 0.36390(14) 1.000 0.0181(5) . . C9 C Uani 0.65094(14) 0.2217(2) 0.50473(16) 1.000 0.0182(5) . . C10 C Uani 0.70973(14) 0.1624(2) 0.41309(15) 1.000 0.0193(5) . . C11 C Uani 0.72125(16) 0.2968(3) 0.22106(16) 1.000 0.0238(6) . . H1 H Uiso 0.55310 0.81920 0.21550 1.000 0.0230 calc R H2 H Uiso 0.33040 1.40900 0.28530 1.000 0.0280 calc R H3 H Uiso 0.40970 1.33550 0.13320 1.000 0.0270 calc R H3A H Uiso 0.5732(17) 0.441(3) 0.5020(19) 1.000 0.038(7) . . H4 H Uiso 0.49630 1.07490 0.13100 1.000 0.0240 calc R H6 H Uiso 0.42670 0.95080 0.43560 1.000 0.0230 calc R H10A H Uiso 0.78520 0.15010 0.44310 1.000 0.0230 calc R H10B H Uiso 0.68190 0.05260 0.37990 1.000 0.0230 calc R H11A H Uiso 0.67320 0.22380 0.17000 1.000 0.0360 calc R H11B H Uiso 0.79190 0.25050 0.23050 1.000 0.0360 calc R H11C H Uiso 0.71990 0.41230 0.19020 1.000 0.0360 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 Cl1 0.0421(3) 0.0283(2) 0.0226(2) 0.0016(2) 0.0161(2) 0.0111(2) O1 0.0371(8) 0.0209(7) 0.0280(8) 0.0034(6) 0.0177(7) 0.0064(6) O2 0.0253(7) 0.0238(7) 0.0221(6) 0.0025(6) 0.0085(6) -0.0003(5) N1 0.0254(8) 0.0177(7) 0.0171(8) -0.0003(6) 0.0091(6) 0.0029(6) N2 0.0222(8) 0.0192(8) 0.0213(8) 0.0003(6) 0.0081(6) 0.0002(6) N3 0.0227(8) 0.0164(7) 0.0195(8) -0.0009(6) 0.0097(6) 0.0009(6) N4 0.0240(9) 0.0192(8) 0.0198(8) 0.0014(6) 0.0090(7) 0.0035(6) C1 0.0203(9) 0.0232(9) 0.0165(9) -0.0032(7) 0.0054(7) 0.0000(7) C2 0.0225(10) 0.0202(9) 0.0264(11) -0.0007(8) 0.0021(8) 0.0050(8) C3 0.0250(10) 0.0218(11) 0.0202(11) 0.0051(8) 0.0011(8) -0.0008(8) C4 0.0183(8) 0.0255(9) 0.0159(8) -0.0013(7) 0.0046(7) -0.0018(7) C5 0.0158(8) 0.0174(9) 0.0187(8) -0.0022(7) 0.0018(7) -0.0032(7) C6 0.0208(9) 0.0195(8) 0.0170(8) -0.0006(7) 0.0036(7) -0.0004(7) C7 0.0211(9) 0.0172(9) 0.0208(9) -0.0006(8) 0.0051(8) -0.0018(7) C8 0.0184(9) 0.0172(9) 0.0199(9) -0.0022(7) 0.0071(7) -0.0021(7) C9 0.0159(9) 0.0168(8) 0.0215(9) -0.0023(8) 0.0029(7) -0.0023(7) C10 0.0201(9) 0.0172(8) 0.0214(9) -0.0004(7) 0.0063(7) 0.0007(7) C11 0.0249(10) 0.0276(10) 0.0218(10) -0.0034(8) 0.0114(8) 0.0006(8) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.7417(19) . . yes O1 C7 1.228(2) . . yes O2 C9 1.206(2) . . yes N1 C5 1.394(2) . . yes N1 C7 1.375(2) . . yes N2 C7 1.383(2) . . yes N2 C8 1.295(2) . . yes N3 C8 1.395(2) . . yes N3 C9 1.360(2) . . yes N4 C8 1.338(2) . . yes N4 C10 1.447(2) . . yes N4 C11 1.454(2) . . yes N1 H1 0.8600 . . no N3 H3A 0.81(2) . . no C1 C6 1.385(2) . . no C1 C2 1.385(2) . . no C2 C3 1.384(3) . . no C3 C4 1.372(2) . . no C4 C5 1.402(2) . . no C5 C6 1.393(2) . . no C9 C10 1.517(3) . . no C2 H2 0.9300 . . no C3 H3 0.9300 . . no C4 H4 0.9300 . . no C6 H6 0.9300 . . no C10 H10A 0.9700 . . no C10 H10B 0.9700 . . no C11 H11A 0.9600 . . no C11 H11B 0.9600 . . no C11 H11C 0.9600 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C7 129.46(15) . . . yes C7 N2 C8 118.36(15) . . . yes C8 N3 C9 112.51(14) . . . yes C8 N4 C10 112.06(14) . . . yes C8 N4 C11 124.63(15) . . . yes C10 N4 C11 123.07(15) . . . yes C7 N1 H1 115.00 . . . no C5 N1 H1 115.00 . . . no C9 N3 H3A 127.1(16) . . . no C8 N3 H3A 120.2(16) . . . no Cl1 C1 C2 119.33(13) . . . yes C2 C1 C6 122.78(17) . . . no Cl1 C1 C6 117.87(14) . . . yes C1 C2 C3 117.98(15) . . . no C2 C3 C4 120.87(16) . . . no C3 C4 C5 120.66(16) . . . no C4 C5 C6 119.36(15) . . . no N1 C5 C4 116.99(15) . . . yes N1 C5 C6 123.65(15) . . . yes C1 C6 C5 118.35(16) . . . no O1 C7 N2 128.30(16) . . . yes N1 C7 N2 108.26(15) . . . yes O1 C7 N1 123.43(16) . . . yes N2 C8 N3 129.47(16) . . . yes N2 C8 N4 123.35(16) . . . yes N3 C8 N4 107.18(14) . . . yes O2 C9 C10 126.52(15) . . . yes N3 C9 C10 105.60(14) . . . yes O2 C9 N3 127.88(17) . . . yes N4 C10 C9 102.53(13) . . . yes C1 C2 H2 121.00 . . . no C3 C2 H2 121.00 . . . no C2 C3 H3 120.00 . . . no C4 C3 H3 120.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 120.00 . . . no C1 C6 H6 121.00 . . . no C5 C6 H6 121.00 . . . no N4 C10 H10A 111.00 . . . no N4 C10 H10B 111.00 . . . no C9 C10 H10A 111.00 . . . no C9 C10 H10B 111.00 . . . no H10A C10 H10B 109.00 . . . no N4 C11 H11A 109.00 . . . no N4 C11 H11B 109.00 . . . no N4 C11 H11C 109.00 . . . no H11A C11 H11B 110.00 . . . no H11A C11 H11C 109.00 . . . no H11B C11 H11C 109.00 . . . no 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 C5 N1 C7 N2 -179.24(16) . . . . no C7 N1 C5 C4 -176.98(17) . . . . no C7 N1 C5 C6 3.9(3) . . . . no C5 N1 C7 O1 1.8(3) . . . . no C8 N2 C7 N1 173.75(15) . . . . no C8 N2 C7 O1 -7.3(3) . . . . no C7 N2 C8 N4 -179.29(16) . . . . no C7 N2 C8 N3 0.5(3) . . . . no C9 N3 C8 N4 -3.5(2) . . . . no C9 N3 C8 N2 176.68(18) . . . . no C8 N3 C9 C10 3.75(19) . . . . no C8 N3 C9 O2 -175.54(18) . . . . no C10 N4 C8 N2 -178.52(16) . . . . no C11 N4 C8 N2 -4.1(3) . . . . no C10 N4 C8 N3 1.65(19) . . . . no C11 N4 C10 C9 -174.01(16) . . . . no C11 N4 C8 N3 176.08(16) . . . . no C8 N4 C10 C9 0.52(18) . . . . no C2 C1 C6 C5 0.7(3) . . . . no Cl1 C1 C2 C3 177.07(14) . . . . no C6 C1 C2 C3 -1.0(3) . . . . no Cl1 C1 C6 C5 -177.48(13) . . . . no C1 C2 C3 C4 0.5(3) . . . . no C2 C3 C4 C5 0.4(3) . . . . no C3 C4 C5 N1 -179.94(16) . . . . no C3 C4 C5 C6 -0.8(3) . . . . no C4 C5 C6 C1 0.3(3) . . . . no N1 C5 C6 C1 179.35(16) . . . . no N3 C9 C10 N4 -2.52(18) . . . . no O2 C9 C10 N4 176.78(17) . . . . 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 Cl1 C8 3.5656(18) . 3_455 no Cl1 C10 3.5746(18) . 3_465 no Cl1 C11 3.250(2) . 4_465 no Cl1 H10B 3.1100 . 3_465 no Cl1 H11A 3.1200 . 4_465 no Cl1 H11B 2.9500 . 4_465 no Cl1 H11C 3.1400 . 4_465 no O1 N3 2.679(2) . . no O1 C6 2.890(2) . . no O2 C2 3.358(2) . 4_565 no O2 C4 3.366(2) . 2_565 no O2 N1 2.924(2) . 2_565 no O1 H3A 2.14(2) . . no O1 H10A 2.7900 . 3_455 no O1 H3 2.8600 . 2_575 no O1 H6 2.3000 . . no O2 H1 2.0900 . 2_565 no O2 H4 2.6300 . 2_565 no N1 O2 2.924(2) . 2_564 no N2 C3 3.421(2) . 1_545 no N3 O1 2.679(2) . . no N3 C1 3.383(2) . 1_545 no N4 C6 3.423(2) . 3_545 no N4 C4 3.397(2) . 1_545 no N1 H10B 2.7700 . 1_565 no N2 H11C 2.5400 . . no C1 N3 3.383(2) . 1_565 no C2 C8 3.465(3) . 1_565 no C2 O2 3.358(2) . 4_464 no C3 N2 3.421(2) . 1_565 no C3 C8 3.369(3) . 1_565 no C4 N4 3.397(2) . 1_565 no C4 C11 3.570(3) . 1_565 no C4 O2 3.366(2) . 2_564 no C5 C10 3.451(3) . 1_565 no C5 C11 3.450(3) . 3_455 no C6 O1 2.890(2) . . no C6 C11 3.378(3) . 3_455 no C6 N4 3.423(2) . 3_455 no C6 C9 3.376(3) . 1_565 no C8 Cl1 3.5656(18) . 3_545 no C8 C3 3.369(3) . 1_545 no C8 C2 3.465(3) . 1_545 no C9 C6 3.376(3) . 1_545 no C10 Cl1 3.5746(18) . 3_535 no C10 C5 3.451(3) . 1_545 no C11 C4 3.570(3) . 1_545 no C11 Cl1 3.250(2) . 4_564 no C11 C6 3.378(3) . 3_545 no C11 C5 3.450(3) . 3_545 no C4 H6 3.0500 . 2_574 no C4 H11A 2.8900 . 1_565 no C5 H10B 2.7900 . 1_565 no C5 H11B 2.8800 . 3_455 no C6 H11B 3.0400 . 3_455 no C7 H3A 2.63(2) . . no C7 H6 2.8000 . . no C9 H1 3.0500 . 2_565 no C10 H2 3.0700 . 3_535 no H1 H4 2.2600 . . no H1 O2 2.0900 . 2_564 no H1 C9 3.0500 . 2_564 no H2 C10 3.0700 . 3_465 no H3 O1 2.8600 . 2_574 no H3 H10A 2.5200 . 4_464 no H3A O1 2.14(2) . . no H3A C7 2.63(2) . . no H4 H1 2.2600 . . no H4 H11A 2.5000 . 1_565 no H4 O2 2.6300 . 2_564 no H4 H6 2.3400 . 2_574 no H6 O1 2.3000 . . no H6 C7 2.8000 . . no H6 C4 3.0500 . 2_575 no H6 H4 2.3400 . 2_575 no H10A O1 2.7900 . 3_545 no H10A H3 2.5200 . 4_565 no H10B N1 2.7700 . 1_545 no H10B C5 2.7900 . 1_545 no H10B Cl1 3.1100 . 3_535 no H11A C4 2.8900 . 1_545 no H11A H4 2.5000 . 1_545 no H11A Cl1 3.1200 . 4_564 no H11B C5 2.8800 . 3_545 no H11B C6 3.0400 . 3_545 no H11B Cl1 2.9500 . 4_564 no H11C N2 2.5400 . . no H11C Cl1 3.1400 . 4_564 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 # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 O2 0.8600 2.0900 2.924(2) 165.00 2_564 yes N3 H3A O1 0.81(2) 2.14(2) 2.679(2) 124(2) . yes C6 H6 O1 0.9300 2.3000 2.890(2) 121.00 . yes C11 H11C N2 0.9600 2.5400 2.880(3) 101.00 . yes data_sp21n2 _database_code_depnum_ccdc_archive 'CCDC 890755' #TrackingRef '- FORM4.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common fenobam _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Cl N4 O2' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C11 H11 Cl N4 O2' _chemical_formula_iupac ? _chemical_formula_weight 266.69 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yac' _symmetry_space_group_name_H-M 'P 2/n' _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,y,1/2-z 3 -x,-y,-z 4 1/2+x,-y,1/2+z _cell_length_a 9.8920(7) _cell_length_b 9.5113(7) _cell_length_c 12.8459(9) _cell_angle_alpha 90 _cell_angle_beta 101.984(8) _cell_angle_gamma 90 _cell_volume 1182.27(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2084 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description ' plate' _exptl_crystal_colour ' pale yellow' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.323 _exptl_crystal_density_meas_temp ? # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, DIFABS, DELABS # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.9382 _exptl_absorpt_correction_T_max 0.9684 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 18.4 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? # number of measured reflections (redundant set) _diffrn_reflns_number 8352 _diffrn_reflns_av_R_equivalents 0.0841 _diffrn_reflns_av_sigmaI/netI 0.0838 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2084 # number of observed reflections (> n sig(I)) _reflns_number_gt 1241 _reflns_threshold_expression >2\s(i) _computing_data_collection 'Locally modified CAD4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating -R-factor-obs 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.The hydrogen atom H3 is located from difference Fourier map, followed by a refinemnet with DFIX restraint applied to N3-H3 bond with a value of 0.87. ; _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^)+(0.0663P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # Permitted for _refine_ls_hydrogen_treatment : # refall - refined all H parameters # refxyz - refined H coordinates only # refU - refined H U only # noref - no refinement of H parameters # constr - H parameters constrained # mixed - some constrained, some independent # undef - H-atom parameters not defined _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack . _refine_ls_number_reflns 2084 _refine_ls_number_parameters 168 _refine_ls_number_restraints 1 _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.1155 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1661 _refine_ls_wR_factor_gt 0.1412 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.436 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.057 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl1 Cl Uani 0.18509(12) -0.03835(13) 0.38406(10) 1.000 0.0743(5) . . O1 O Uani 0.6458(3) 0.4348(3) 0.6560(2) 1.000 0.0596(11) . . O2 O Uani 1.0542(3) 0.7147(3) 0.7633(2) 1.000 0.0698(11) . . N1 N Uani 0.5662(3) 0.3194(3) 0.5012(2) 1.000 0.0440(11) . . N2 N Uani 0.7294(3) 0.4843(3) 0.5031(2) 1.000 0.0436(11) . . N3 N Uani 0.8781(3) 0.5874(3) 0.6594(3) 1.000 0.0440(11) . . N4 N Uani 0.9036(3) 0.6449(3) 0.4982(3) 1.000 0.0487(11) . . C1 C Uani 0.3013(4) 0.0464(4) 0.4844(3) 1.000 0.0486(14) . . C2 C Uani 0.3108(4) 0.0065(4) 0.5887(4) 1.000 0.0531(14) . . C3 C Uani 0.4046(4) 0.0743(4) 0.6661(3) 1.000 0.0538(16) . . C4 C Uani 0.4878(4) 0.1814(4) 0.6404(3) 1.000 0.0472(12) . . C5 C Uani 0.4790(4) 0.2210(4) 0.5347(3) 1.000 0.0414(12) . . C6 C Uani 0.3828(4) 0.1512(4) 0.4552(3) 1.000 0.0464(12) . . C7 C Uani 0.6487(4) 0.4150(4) 0.5627(3) 1.000 0.0423(12) . . C8 C Uani 0.8278(4) 0.5666(4) 0.5505(3) 1.000 0.0421(12) . . C9 C Uani 0.9883(4) 0.6781(4) 0.6771(3) 1.000 0.0479(14) . . C10 C Uani 1.0099(4) 0.7219(4) 0.5692(3) 1.000 0.0521(14) . . C11 C Uani 0.8754(5) 0.6615(4) 0.3839(3) 1.000 0.0624(16) . . H1 H Uiso 0.56780 0.31930 0.43450 1.000 0.0530 calc R H2 H Uiso 0.25490 -0.06460 0.60630 1.000 0.0640 calc R H3 H Uiso 0.861(4) 0.540(3) 0.710(2) 1.000 0.047(12) . . H3A H Uiso 0.41270 0.04830 0.73690 1.000 0.0650 calc R H4 H Uiso 0.54970 0.22700 0.69420 1.000 0.0570 calc R H6 H Uiso 0.37420 0.17540 0.38400 1.000 0.0560 calc R H10A H Uiso 0.99780 0.82250 0.55890 1.000 0.0620 calc R H10B H Uiso 1.10110 0.69560 0.55940 1.000 0.0620 calc R H11A H Uiso 0.82570 0.58090 0.35100 1.000 0.0930 calc R H11B H Uiso 0.96100 0.67010 0.36030 1.000 0.0930 calc R H11C H Uiso 0.82080 0.74450 0.36450 1.000 0.0930 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 Cl1 0.0601(7) 0.0867(9) 0.0679(8) -0.0222(7) -0.0053(6) -0.0101(6) O1 0.073(2) 0.070(2) 0.0386(17) -0.0152(14) 0.0179(16) -0.0205(16) O2 0.073(2) 0.082(2) 0.0513(18) -0.0121(16) 0.0058(17) -0.0224(17) N1 0.0505(19) 0.0457(19) 0.0334(17) -0.0051(15) 0.0031(16) 0.0004(16) N2 0.0477(19) 0.0437(18) 0.0380(18) -0.0014(15) 0.0058(17) 0.0007(15) N3 0.054(2) 0.0448(19) 0.0343(18) 0.0031(16) 0.0114(17) -0.0037(16) N4 0.057(2) 0.0499(19) 0.0409(18) 0.0074(16) 0.0140(17) -0.0009(17) C1 0.041(2) 0.047(2) 0.053(3) -0.010(2) -0.001(2) 0.0074(19) C2 0.044(2) 0.053(2) 0.063(3) -0.003(2) 0.013(2) 0.0045(19) C3 0.056(3) 0.062(3) 0.040(2) -0.005(2) 0.002(2) 0.008(2) C4 0.052(2) 0.049(2) 0.039(2) -0.0035(19) 0.006(2) -0.001(2) C5 0.040(2) 0.039(2) 0.043(2) -0.0053(18) 0.0035(19) 0.0080(17) C6 0.046(2) 0.049(2) 0.041(2) -0.0045(19) 0.002(2) 0.011(2) C7 0.045(2) 0.037(2) 0.043(2) -0.0015(19) 0.005(2) 0.0050(18) C8 0.051(2) 0.039(2) 0.038(2) 0.0026(18) 0.013(2) 0.0110(19) C9 0.050(2) 0.043(2) 0.053(3) -0.004(2) 0.016(2) -0.0048(19) C10 0.060(2) 0.047(2) 0.055(3) 0.004(2) 0.025(2) -0.005(2) C11 0.083(3) 0.062(3) 0.045(2) 0.014(2) 0.020(2) 0.010(2) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.737(4) . . yes O1 C7 1.219(5) . . yes O2 C9 1.214(5) . . yes N1 C5 1.400(5) . . yes N1 C7 1.360(5) . . yes N2 C7 1.383(5) . . yes N2 C8 1.298(5) . . yes N3 C8 1.398(5) . . yes N3 C9 1.372(5) . . yes N4 C8 1.333(5) . . yes N4 C10 1.441(5) . . yes N4 C11 1.445(5) . . yes N1 H1 0.8600 . . no N3 H3 0.84(3) . . no C1 C6 1.382(6) . . no C1 C2 1.377(6) . . no C2 C3 1.372(6) . . no C3 C4 1.392(6) . . no C4 C5 1.394(5) . . no C5 C6 1.409(5) . . no C9 C10 1.505(5) . . no C2 H2 0.9300 . . no C3 H3A 0.9300 . . no C4 H4 0.9300 . . no C6 H6 0.9300 . . no C10 H10A 0.9700 . . no C10 H10B 0.9700 . . no C11 H11A 0.9600 . . no C11 H11B 0.9600 . . no C11 H11C 0.9600 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C7 127.0(3) . . . yes C7 N2 C8 119.4(3) . . . yes C8 N3 C9 111.1(3) . . . yes C8 N4 C10 112.2(3) . . . yes C8 N4 C11 124.3(3) . . . yes C10 N4 C11 123.3(3) . . . yes C7 N1 H1 117.00 . . . no C5 N1 H1 116.00 . . . no C9 N3 H3 120(2) . . . no C8 N3 H3 128(2) . . . no Cl1 C1 C2 119.7(3) . . . yes C2 C1 C6 122.5(4) . . . no Cl1 C1 C6 117.8(3) . . . yes C1 C2 C3 118.4(4) . . . no C2 C3 C4 121.1(4) . . . no C3 C4 C5 120.6(4) . . . no C4 C5 C6 118.3(4) . . . no N1 C5 C4 124.2(3) . . . yes N1 C5 C6 117.3(3) . . . yes C1 C6 C5 119.2(3) . . . no O1 C7 N2 127.2(4) . . . yes N1 C7 N2 110.1(3) . . . yes O1 C7 N1 122.7(4) . . . yes N2 C8 N3 129.1(3) . . . yes N2 C8 N4 123.1(3) . . . yes N3 C8 N4 107.7(3) . . . yes O2 C9 C10 127.5(4) . . . yes N3 C9 C10 106.4(3) . . . yes O2 C9 N3 126.1(4) . . . yes N4 C10 C9 102.6(3) . . . yes C1 C2 H2 121.00 . . . no C3 C2 H2 121.00 . . . no C2 C3 H3A 119.00 . . . no C4 C3 H3A 119.00 . . . no C3 C4 H4 120.00 . . . no C5 C4 H4 120.00 . . . no C1 C6 H6 120.00 . . . no C5 C6 H6 120.00 . . . no N4 C10 H10A 111.00 . . . no N4 C10 H10B 111.00 . . . no C9 C10 H10A 111.00 . . . no C9 C10 H10B 111.00 . . . no H10A C10 H10B 109.00 . . . no N4 C11 H11A 109.00 . . . no N4 C11 H11B 109.00 . . . no N4 C11 H11C 109.00 . . . no H11A C11 H11B 109.00 . . . no H11A C11 H11C 109.00 . . . no H11B C11 H11C 109.00 . . . no 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 C5 N1 C7 N2 174.1(3) . . . . no C7 N1 C5 C4 -16.7(6) . . . . no C7 N1 C5 C6 167.8(4) . . . . no C5 N1 C7 O1 -7.3(6) . . . . no C8 N2 C7 N1 -171.1(3) . . . . no C8 N2 C7 O1 10.4(6) . . . . no C7 N2 C8 N4 -175.0(3) . . . . no C7 N2 C8 N3 7.7(6) . . . . no C9 N3 C8 N4 -0.9(4) . . . . no C9 N3 C8 N2 176.8(4) . . . . no C8 N3 C9 C10 1.0(4) . . . . no C8 N3 C9 O2 -179.1(4) . . . . no C10 N4 C8 N2 -177.4(3) . . . . no C11 N4 C8 N2 8.0(6) . . . . no C10 N4 C8 N3 0.5(4) . . . . no C11 N4 C10 C9 174.8(3) . . . . no C11 N4 C8 N3 -174.2(3) . . . . no C8 N4 C10 C9 0.1(4) . . . . no C2 C1 C6 C5 -0.4(6) . . . . no Cl1 C1 C2 C3 179.3(3) . . . . no C6 C1 C2 C3 0.3(6) . . . . no Cl1 C1 C6 C5 -179.4(3) . . . . no C1 C2 C3 C4 0.4(6) . . . . no C2 C3 C4 C5 -0.9(6) . . . . no C3 C4 C5 N1 -174.6(4) . . . . no C3 C4 C5 C6 0.8(6) . . . . no C4 C5 C6 C1 -0.2(6) . . . . no N1 C5 C6 C1 175.6(3) . . . . no N3 C9 C10 N4 -0.6(4) . . . . no O2 C9 C10 N4 179.4(4) . . . . 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 Cl1 C4 3.584(4) . 3_656 no Cl1 C3 3.525(4) . 4_454 no Cl1 C4 3.595(4) . 4_454 no Cl1 H10A 2.9300 . 3_666 no Cl1 H3A 2.9500 . 4_454 no Cl1 H4 3.1000 . 4_454 no O1 N3 2.711(4) . . no O1 C4 2.857(5) . . no O1 N3 2.832(4) . 2_656 no O1 O1 2.831(4) . 2_656 no O2 N1 3.051(4) . 4_565 no O1 H4 2.2900 . . no O1 H3 2.32(4) . . no O1 H3 2.00(3) . 2_656 no O2 H1 2.2000 . 4_565 no O2 H6 2.8000 . 4_565 no N1 C7 3.294(5) . 3_666 no N1 O2 3.051(4) . 4_464 no N3 O1 2.832(4) . 2_656 no N3 O1 2.711(4) . . no N2 H10B 2.6300 . 3_766 no N2 H11A 2.5200 . . no C1 C5 3.387(6) . 3_656 no C1 C6 3.591(6) . 3_656 no C2 C5 3.590(6) . 3_656 no C2 C6 3.530(6) . 3_656 no C3 Cl1 3.525(4) . 4_555 no C3 C6 3.579(6) . 3_656 no C4 Cl1 3.584(4) . 3_656 no C4 Cl1 3.595(4) . 4_555 no C4 O1 2.857(5) . . no C5 C2 3.590(6) . 3_656 no C5 C1 3.387(6) . 3_656 no C6 C2 3.530(6) . 3_656 no C6 C1 3.591(6) . 3_656 no C6 C8 3.389(6) . 3_666 no C6 C3 3.579(6) . 3_656 no C7 N1 3.294(5) . 3_666 no C7 C7 3.449(6) . 3_666 no C8 C6 3.389(6) . 3_666 no C2 H11C 2.8300 . 3_666 no C3 H11C 2.7800 . 3_666 no C7 H3 2.79(3) . . no C7 H4 2.7700 . . no C8 H10B 3.0200 . 3_766 no H1 H6 2.3300 . . no H1 O2 2.2000 . 4_464 no H3 O1 2.32(4) . . no H3 C7 2.79(3) . . no H3 O1 2.00(3) . 2_656 no H3A Cl1 2.9500 . 4_555 no H4 O1 2.2900 . . no H4 C7 2.7700 . . no H4 Cl1 3.1000 . 4_555 no H6 H1 2.3300 . . no H6 O2 2.8000 . 4_464 no H10A Cl1 2.9300 . 3_666 no H10B N2 2.6300 . 3_766 no H10B C8 3.0200 . 3_766 no H11A N2 2.5200 . . no H11C C2 2.8300 . 3_666 no H11C C3 2.7800 . 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 # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 O2 0.8600 2.2000 3.051(4) 170.00 4_464 yes N3 H3 O1 0.84(3) 2.32(4) 2.711(4) 109(3) . yes N3 H3 O1 0.84(3) 2.00(3) 2.832(4) 170(3) 2_656 yes C4 H4 O1 0.9300 2.2900 2.857(5) 119.00 . yes C11 H11A N2 0.9600 2.5200 2.862(5) 101.00 . yes # Loop Mechanism for Extra Tables(s) #loop_ #_publ_manuscript_incl_extra_item #'_geom_extra_tableA_col_1' #'_geom_extra_tableA_col_2' #'_geom_extra_tableA_col_3' #'_geom_extra_table_head_A' #'_geom_table_footnote_A' #'_geom_extra_tableB_col_1' #'_geom_extra_tableB_col_2' #'_geom_extra_tableB_col_3' #'_geom_extra_table_head_B' #'_geom_table_footnote_B' # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 # ? ? ? # #loop_ #_geom_extra_tableB_col_1 #_geom_extra_tableB_col_2 #_geom_extra_tableB_col_3 # ? ? ? # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; # #_geom_table_footnote_A #; # ? #; # #_geom_table_footnote_B #; # ? #; #===END