# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'T. N. Guru Row' _publ_contact_author_email SSCTNG@SSCU.IISC.ERNET.IN _publ_section_title ; Directing role of functional groups in selective generation of C-H...pi interactions: In situ Cryocrystallographic studies on benzyl derivatives ; loop_ _publ_author_name 'T. N. Guru Row' 'Susanta K Nayak' 'R Sathishkumar' #=============================================================================== data_c _database_code_depnum_ccdc_archive 'CCDC 725239' #TrackingRef 'CIFall.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; Phenylmethanol ; _chemical_name_common Phenylmethanol _chemical_melting_point ? _chemical_formula_moiety 'C7 H8 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 'C7 H8 O' _chemical_formula_iupac ? _chemical_formula_weight 108.13 _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 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 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 5.840(5) _cell_length_b 4.871(4) _cell_length_c 10.764(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.656(16) _cell_angle_gamma 90.00 _cell_volume 306.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 300 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.97 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 116 _exptl_absorpt_coefficient_mu 0.077 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9557 _exptl_absorpt_correction_T_max 0.9772 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 210(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2819 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 24.99 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.970 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1039 # number of observed reflections (> n sig(I)) _reflns_number_gt 700 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1588P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(5) _refine_ls_number_reflns 1039 _refine_ls_number_parameters 73 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1185 _refine_ls_R_factor_gt 0.0897 _refine_ls_wR_factor_ref 0.2555 _refine_ls_wR_factor_gt 0.2386 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.129 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.571 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.071 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5378(6) 1.1228(7) 0.9480(3) 0.0706(11) Uani 1 1 d . . . H1 H 0.4864 0.9676 0.9569 0.106 Uiso 1 1 calc R . . C5 C 0.8437(8) 0.6374(11) 0.6052(4) 0.0609(13) Uani 1 1 d . . . H5 H 0.8170 0.5506 0.5291 0.073 Uiso 1 1 calc R . . C4 C 1.0275(8) 0.5917(15) 0.6727(4) 0.0693(15) Uani 1 1 d . . . H4 H 1.1368 0.4736 0.6413 0.083 Uiso 1 1 calc R . . C1 C 0.7402(9) 0.9637(9) 0.7731(4) 0.0565(13) Uani 1 1 d . . . C2 C 0.9340(10) 0.8815(13) 0.8319(6) 0.0855(19) Uani 1 1 d . . . H2 H 0.9709 0.9559 0.9095 0.103 Uiso 1 1 calc R . . C3 C 1.0707(9) 0.7046(17) 0.7859(6) 0.094(2) Uani 1 1 d . . . H3 H 1.2018 0.6530 0.8311 0.113 Uiso 1 1 calc R . . C7 C 0.5737(9) 1.1722(13) 0.8196(5) 0.0792(17) Uani 1 1 d . . . H7A H 0.6342 1.3558 0.8085 0.095 Uiso 1 1 calc R . . H7B H 0.4296 1.1583 0.7730 0.095 Uiso 1 1 calc R . . C6 C 0.6782(9) 0.8368(15) 0.6567(6) 0.091(2) Uani 1 1 d . . . H6 H 0.5406 0.8774 0.6151 0.109 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.111(2) 0.0391(16) 0.0638(19) 0.0010(16) 0.0424(17) 0.0003(19) C5 0.074(3) 0.059(3) 0.050(2) -0.001(2) 0.021(2) -0.008(3) C4 0.058(3) 0.092(4) 0.059(3) -0.001(3) 0.012(2) 0.005(3) C1 0.082(3) 0.037(2) 0.052(2) 0.0086(19) 0.024(2) 0.000(2) C2 0.077(4) 0.074(4) 0.104(5) -0.016(3) -0.019(3) 0.002(3) C3 0.063(3) 0.128(7) 0.092(4) -0.028(4) 0.011(3) -0.005(4) C7 0.089(3) 0.071(4) 0.079(4) 0.010(3) 0.027(3) 0.013(3) C6 0.075(3) 0.094(5) 0.104(5) 0.055(4) -0.003(3) -0.001(3) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.424(6) . ? O1 H1 0.8200 . ? C5 C4 1.298(6) . ? C5 C6 1.489(9) . ? C5 H5 0.9300 . ? C4 C3 1.353(8) . ? C4 H4 0.9300 . ? C1 C2 1.342(7) . ? C1 C6 1.434(8) . ? C1 C7 1.502(7) . ? C2 C3 1.284(9) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C6 H6 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O1 H1 109.5 . . ? C4 C5 C6 116.0(5) . . ? C4 C5 H5 122.0 . . ? C6 C5 H5 122.0 . . ? C5 C4 C3 124.3(6) . . ? C5 C4 H4 117.8 . . ? C3 C4 H4 117.8 . . ? C2 C1 C6 118.1(5) . . ? C2 C1 C7 126.1(5) . . ? C6 C1 C7 115.7(5) . . ? C3 C2 C1 122.9(6) . . ? C3 C2 H2 118.5 . . ? C1 C2 H2 118.5 . . ? C2 C3 C4 121.2(6) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? O1 C7 C1 108.9(4) . . ? O1 C7 H7A 109.9 . . ? C1 C7 H7A 109.9 . . ? O1 C7 H7B 109.9 . . ? C1 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C1 C6 C5 117.2(4) . . ? C1 C6 H6 121.4 . . ? C5 C6 H6 121.4 . . ? 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 C6 C5 C4 C3 2.5(9) . . . . ? C6 C1 C2 C3 3.4(10) . . . . ? C7 C1 C2 C3 -179.0(6) . . . . ? C1 C2 C3 C4 0.8(11) . . . . ? C5 C4 C3 C2 -4.1(11) . . . . ? C2 C1 C7 O1 -43.5(7) . . . . ? C6 C1 C7 O1 134.2(5) . . . . ? C2 C1 C6 C5 -4.5(7) . . . . ? C7 C1 C6 C5 177.6(4) . . . . ? C4 C5 C6 C1 1.7(7) . . . . ? #=============================================================================== data_h _database_code_depnum_ccdc_archive 'CCDC 725240' #TrackingRef 'CIFall.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; Phenylmethanamine ; _chemical_name_common Phenylmethanamine _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 N' # 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 'C7 H9 N' _chemical_formula_iupac ? _chemical_formula_weight 107.15 _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 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 Tetragonal _symmetry_space_group_name_Hall 'P 4cw' _symmetry_space_group_name_H-M 'P 43' _symmetry_Int_Tables_number 78 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -y,x,3/4+z 3 -x,-y,1/2+z 4 y,-x,1/4+z _cell_length_a 10.623(3) _cell_length_b 10.623(3) _cell_length_c 5.5031(18) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 621.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 450 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.068 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9785 _exptl_absorpt_correction_T_max 0.9799 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6292 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.67 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 654 # number of observed reflections (> n sig(I)) _reflns_number_gt 564 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.0416P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), 525 Friendelpairs' _refine_ls_number_reflns 654 _refine_ls_number_parameters 81 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0837 _refine_ls_wR_factor_gt 0.0790 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.124 _refine_diff_density_min -0.092 _refine_diff_density_rms 0.025 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.03586(18) 0.1845(2) 0.2131(4) 0.0472(5) Uani 1 1 d . . . H1A H 0.033(3) 0.153(2) 0.300(6) 0.062(8) Uiso 1 1 d . . . H1B H -0.072(2) 0.249(2) 0.296(6) 0.057(8) Uiso 1 1 d . . . C6 C 0.1026(2) 0.42400(19) -0.2114(4) 0.0421(5) Uani 1 1 d . . . H6 H 0.0453 0.4133 -0.3400 0.050 Uiso 1 1 calc R . . C1 C 0.10174(18) 0.33956(18) -0.0184(4) 0.0358(5) Uani 1 1 d . . . C4 C 0.2692(2) 0.5422(2) -0.0287(5) 0.0474(6) Uani 1 1 d . . . H4 H 0.3250 0.6109 -0.0310 0.057 Uiso 1 1 calc R . . C2 C 0.18715(18) 0.35792(19) 0.1689(4) 0.0394(5) Uani 1 1 d . . . H2 H 0.1889 0.3014 0.3003 0.047 Uiso 1 1 calc R . . C3 C 0.2696(2) 0.45852(19) 0.1645(4) 0.0455(6) Uani 1 1 d . . . H3 H 0.3264 0.4703 0.2936 0.055 Uiso 1 1 calc R . . C7 C 0.0100(2) 0.2307(2) -0.0202(4) 0.0435(5) Uani 1 1 d . . . H7A H -0.0632 0.2559 -0.1171 0.052 Uiso 1 1 calc R . . H7B H 0.0502 0.1602 -0.1048 0.052 Uiso 1 1 calc R . . C5 C 0.1862(2) 0.5233(2) -0.2171(4) 0.0466(6) Uani 1 1 d . . . H5 H 0.1865 0.5784 -0.3506 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0411(11) 0.0447(11) 0.0557(13) 0.0033(10) 0.0007(11) -0.0002(9) C6 0.0439(12) 0.0452(12) 0.0371(12) -0.0043(10) -0.0031(10) 0.0085(10) C1 0.0353(10) 0.0379(11) 0.0344(10) -0.0060(9) 0.0020(9) 0.0082(8) C4 0.0509(13) 0.0392(12) 0.0521(14) -0.0060(11) 0.0088(12) -0.0052(9) C2 0.0419(11) 0.0420(12) 0.0344(11) 0.0018(10) 0.0008(10) 0.0039(9) C3 0.0452(12) 0.0489(13) 0.0425(13) -0.0064(11) -0.0009(11) -0.0041(10) C7 0.0416(12) 0.0447(12) 0.0442(13) -0.0052(11) -0.0023(10) 0.0008(9) C5 0.0606(14) 0.0392(12) 0.0399(13) 0.0046(11) 0.0089(11) 0.0098(10) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.459(3) . ? N1 H1A 0.94(3) . ? N1 H1B 0.90(3) . ? C6 C5 1.379(3) . ? C6 C1 1.390(3) . ? C6 H6 0.9400 . ? C1 C2 1.387(3) . ? C1 C7 1.512(3) . ? C4 C5 1.376(3) . ? C4 C3 1.386(3) . ? C4 H4 0.9400 . ? C2 C3 1.382(3) . ? C2 H2 0.9400 . ? C3 H3 0.9400 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C5 H5 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 H1A 107.9(17) . . ? C7 N1 H1B 109.2(17) . . ? H1A N1 H1B 111(3) . . ? C5 C6 C1 121.0(2) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? C2 C1 C6 118.22(18) . . ? C2 C1 C7 122.26(18) . . ? C6 C1 C7 119.52(19) . . ? C5 C4 C3 119.1(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C3 C2 C1 120.7(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.5(2) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? N1 C7 C1 117.87(18) . . ? N1 C7 H7A 107.8 . . ? C1 C7 H7A 107.8 . . ? N1 C7 H7B 107.8 . . ? C1 C7 H7B 107.8 . . ? H7A C7 H7B 107.2 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? 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 C6 C1 C2 0.1(3) . . . . ? C5 C6 C1 C7 -179.12(19) . . . . ? C6 C1 C2 C3 0.8(3) . . . . ? C7 C1 C2 C3 -179.96(19) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C5 C4 C3 C2 -0.4(3) . . . . ? C2 C1 C7 N1 31.4(3) . . . . ? C6 C1 C7 N1 -149.4(2) . . . . ? C3 C4 C5 C6 1.4(3) . . . . ? C1 C6 C5 C4 -1.2(3) . . . . ? #===END #=============================================================================== data_e _database_code_depnum_ccdc_archive 'CCDC 725241' #TrackingRef 'CIFall.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 1-(Chloromethyl)benzene ; _chemical_name_common 1-(Chloromethyl)benzene _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 Cl' # 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 'C7 H7 Cl' _chemical_formula_iupac ? _chemical_formula_weight 126.58 _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 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 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 8.2424(19) _cell_length_b 11.268(3) _cell_length_c 7.8204(18) _cell_angle_alpha 90 _cell_angle_beta 112.657(3) _cell_angle_gamma 90 _cell_volume 670.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 350 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.97 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.455 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.8680 _exptl_absorpt_correction_T_max 0.8755 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6705 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1314 # number of observed reflections (> n sig(I)) _reflns_number_gt 1184 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+0.2522P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1314 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.237 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.037 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.61976(8) 0.64966(6) 0.11916(9) 0.0754(3) Uani 1 1 d . . . C1 C 0.9518(3) 0.60310(16) 0.1404(2) 0.0440(4) Uani 1 1 d . . . C6 C 1.0218(3) 0.51815(18) 0.2760(3) 0.0522(5) Uani 1 1 d . . . H6 H 0.9504 0.4559 0.2867 0.063 Uiso 1 1 calc R . . C2 C 1.0586(3) 0.69376(17) 0.1261(3) 0.0508(5) Uani 1 1 d . . . H2 H 1.0126 0.7521 0.0341 0.061 Uiso 1 1 calc R . . C5 C 1.1959(3) 0.5239(2) 0.3961(3) 0.0597(6) Uani 1 1 d . . . H5 H 1.2426 0.4656 0.4882 0.072 Uiso 1 1 calc R . . C7 C 0.7636(3) 0.5968(2) 0.0112(3) 0.0612(6) Uani 1 1 d . . . H7A H 0.7334 0.5144 -0.0287 0.073 Uiso 1 1 calc R . . H7B H 0.7462 0.6447 -0.0990 0.073 Uiso 1 1 calc R . . C4 C 1.3010(3) 0.6145(2) 0.3811(3) 0.0588(6) Uani 1 1 d . . . H4 H 1.4194 0.6184 0.4632 0.071 Uiso 1 1 calc R . . C3 C 1.2330(3) 0.69923(19) 0.2464(3) 0.0573(5) Uani 1 1 d . . . H3 H 1.3051 0.7611 0.2357 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0544(4) 0.0935(5) 0.0736(4) -0.0106(3) 0.0196(3) 0.0203(3) C1 0.0522(11) 0.0421(10) 0.0415(10) -0.0061(8) 0.0222(8) 0.0032(8) C6 0.0627(13) 0.0429(11) 0.0614(12) 0.0027(9) 0.0353(11) 0.0013(9) C2 0.0699(13) 0.0392(10) 0.0476(11) 0.0024(8) 0.0276(10) 0.0059(9) C5 0.0669(14) 0.0637(14) 0.0548(12) 0.0145(10) 0.0301(11) 0.0219(11) C7 0.0601(13) 0.0675(14) 0.0529(12) -0.0111(11) 0.0186(10) 0.0025(11) C4 0.0487(11) 0.0699(14) 0.0583(13) -0.0086(11) 0.0213(10) 0.0077(10) C3 0.0616(13) 0.0504(12) 0.0693(14) -0.0096(10) 0.0356(11) -0.0090(10) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C7 1.801(2) . ? C1 C6 1.379(3) . ? C1 C2 1.381(3) . ? C1 C7 1.492(3) . ? C6 C5 1.381(3) . ? C6 H6 0.9400 . ? C2 C3 1.383(3) . ? C2 H2 0.9400 . ? C5 C4 1.372(3) . ? C5 H5 0.9400 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C4 C3 1.372(3) . ? C4 H4 0.9400 . ? C3 H3 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.99(19) . . ? C6 C1 C7 120.36(19) . . ? C2 C1 C7 120.65(19) . . ? C1 C6 C5 120.5(2) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C1 C2 C3 120.39(19) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C5 C6 120.1(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C7 Cl1 111.56(14) . . ? C1 C7 H7A 109.3 . . ? Cl1 C7 H7A 109.3 . . ? C1 C7 H7B 109.3 . . ? Cl1 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C3 C2 120.1(2) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? 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 C2 C1 C6 C5 0.2(3) . . . . ? C7 C1 C6 C5 -179.87(19) . . . . ? C6 C1 C2 C3 -0.2(3) . . . . ? C7 C1 C2 C3 179.93(19) . . . . ? C1 C6 C5 C4 0.0(3) . . . . ? C6 C1 C7 Cl1 78.5(2) . . . . ? C2 C1 C7 Cl1 -101.6(2) . . . . ? C6 C5 C4 C3 -0.2(3) . . . . ? C5 C4 C3 C2 0.3(3) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? #=============================================================================== data_d _database_code_depnum_ccdc_archive 'CCDC 725242' #TrackingRef 'CIFall.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 1-(bromomethyl)benzene ; _chemical_name_common 1-(bromomethyl)benzene _chemical_melting_point ? _chemical_formula_moiety 'C7 H7 Br' # 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 'C7 H7 Br' _chemical_formula_iupac 'C7 H7 Br' _chemical_formula_weight 171.03 _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 Br Br -0.2901 2.4595 '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 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 4.592(2) _cell_length_b 7.737(4) _cell_length_c 9.507(5) _cell_angle_alpha 90 _cell_angle_beta 94.213(8) _cell_angle_gamma 90 _cell_volume 336.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 300 _cell_measurement_theta_min 0.99 _cell_measurement_theta_max 27.91 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 168 _exptl_absorpt_coefficient_mu 5.987 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.1551 _exptl_absorpt_correction_T_max 0.1653 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3323 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0677 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.62 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1267 # number of observed reflections (> n sig(I)) _reflns_number_gt 969 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0986P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(1) _refine_ls_number_reflns 1267 _refine_ls_number_parameters 73 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0817 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1510 _refine_ls_wR_factor_gt 0.1400 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.949 _refine_diff_density_min -0.561 _refine_diff_density_rms 0.160 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C7 C 0.550(2) 0.3591(15) 0.1940(11) 0.048(3) Uani 1 1 d . . . H7B H 0.5939 0.3397 0.0959 0.057 Uiso 1 1 calc R . . H7A H 0.7335 0.3538 0.2532 0.057 Uiso 1 1 calc R . . Br1 Br 0.37047(18) 0.5887(2) 0.21163(8) 0.0475(3) Uani 1 1 d . . . C3 C 0.126(3) 0.064(3) 0.4155(10) 0.060(5) Uani 1 1 d . . . H3 H 0.0956 0.0477 0.5113 0.072 Uiso 1 1 calc R . . C6 C 0.192(2) 0.1253(10) 0.1359(9) 0.034(3) Uani 1 1 d . . . H6 H 0.2119 0.1474 0.0398 0.041 Uiso 1 1 calc R . . C1 C 0.3514(17) 0.2240(13) 0.2374(9) 0.032(2) Uani 1 1 d . . . C5 C 0.004(2) -0.0059(13) 0.1739(11) 0.042(2) Uani 1 1 d . . . H5 H -0.1038 -0.0701 0.1041 0.050 Uiso 1 1 calc R . . C2 C 0.312(2) 0.1866(13) 0.3781(10) 0.044(2) Uani 1 1 d . . . H2 H 0.4189 0.2493 0.4491 0.053 Uiso 1 1 calc R . . C4 C -0.023(3) -0.0399(14) 0.3128(13) 0.056(3) Uani 1 1 d . . . H4 H -0.1399 -0.1322 0.3397 0.067 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C7 0.040(5) 0.051(7) 0.053(6) -0.008(5) 0.007(4) 0.001(4) Br1 0.0572(5) 0.0347(5) 0.0507(5) -0.0021(7) 0.0050(3) 0.0009(8) C3 0.068(6) 0.088(15) 0.025(4) 0.016(8) 0.012(4) 0.020(9) C6 0.058(5) 0.013(7) 0.030(4) -0.001(3) -0.003(4) 0.004(4) C1 0.035(5) 0.031(5) 0.031(5) -0.005(4) 0.007(4) 0.008(4) C5 0.051(6) 0.029(5) 0.044(6) 0.003(5) -0.004(5) 0.000(5) C2 0.056(6) 0.042(6) 0.033(5) -0.001(5) -0.004(5) 0.007(5) C4 0.060(7) 0.036(6) 0.073(8) 0.011(6) 0.004(6) -0.004(5) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C7 C1 1.465(14) . ? C7 Br1 1.971(11) . ? C7 H7B 0.9800 . ? C7 H7A 0.9800 . ? C3 C2 1.34(2) . ? C3 C4 1.405(19) . ? C3 H3 0.9400 . ? C6 C1 1.395(12) . ? C6 C5 1.398(13) . ? C6 H6 0.9400 . ? C1 C2 1.394(13) . ? C5 C4 1.361(16) . ? C5 H5 0.9400 . ? C2 H2 0.9400 . ? C4 H4 0.9400 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C7 Br1 110.3(6) . . ? C1 C7 H7B 109.6 . . ? Br1 C7 H7B 109.6 . . ? C1 C7 H7A 109.6 . . ? Br1 C7 H7A 109.6 . . ? H7B C7 H7A 108.1 . . ? C2 C3 C4 120.5(10) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C1 C6 C5 121.4(9) . . ? C1 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C2 C1 C6 116.8(9) . . ? C2 C1 C7 123.1(9) . . ? C6 C1 C7 120.1(8) . . ? C4 C5 C6 119.5(9) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C3 C2 C1 122.2(9) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C5 C4 C3 119.3(11) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? 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 C6 C1 C2 -0.5(13) . . . . ? C5 C6 C1 C7 179.2(9) . . . . ? Br1 C7 C1 C2 -77.6(10) . . . . ? Br1 C7 C1 C6 102.7(9) . . . . ? C1 C6 C5 C4 -0.8(14) . . . . ? C4 C3 C2 C1 4(2) . . . . ? C6 C1 C2 C3 -1.2(15) . . . . ? C7 C1 C2 C3 179.1(12) . . . . ? C6 C5 C4 C3 3.8(17) . . . . ? C2 C3 C4 C5 -5(2) . . . . ? #=============================================================================== data_g _database_code_depnum_ccdc_archive 'CCDC 725243' #TrackingRef 'CIFall.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; Phenylmethanethiol ; _chemical_name_common Phenylmethanethiol _chemical_melting_point ? _chemical_formula_moiety 'C7 H8 S' # 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 'C7 H8 S' _chemical_formula_iupac ? _chemical_formula_weight 124.20 _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 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 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 5.5515(7) _cell_length_b 14.8529(19) _cell_length_c 8.0053(10) _cell_angle_alpha 90 _cell_angle_beta 100.668(2) _cell_angle_gamma 90 _cell_volume 648.68(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 450 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.381 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.8879 _exptl_absorpt_correction_T_max 0.9009 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6142 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1270 # number of observed reflections (> n sig(I)) _reflns_number_gt 1229 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.1739P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_coef ? _refine_ls_number_reflns 1270 _refine_ls_number_parameters 77 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0272 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.259 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.039 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H1S H 1.001(3) 0.5198(12) 1.177(2) 0.053(5) Uiso 1 1 d . . . S1 S 1.07447(6) 0.59518(2) 1.22863(4) 0.03124(14) Uani 1 1 d . . . C6 C 0.5275(2) 0.60210(8) 0.86913(17) 0.0260(3) Uani 1 1 d . . . H6 H 0.4223 0.5824 0.9395 0.031 Uiso 1 1 calc R . . C1 C 0.7426(2) 0.64719(8) 0.93913(15) 0.0228(3) Uani 1 1 d . . . C5 C 0.4684(2) 0.58620(8) 0.69545(17) 0.0287(3) Uani 1 1 d . . . H5 H 0.3244 0.5559 0.6503 0.034 Uiso 1 1 calc R . . C4 C 0.6231(2) 0.61525(8) 0.58926(16) 0.0283(3) Uani 1 1 d . . . H4 H 0.5846 0.6039 0.4731 0.034 Uiso 1 1 calc R . . C3 C 0.8367(2) 0.66158(8) 0.65732(16) 0.0275(3) Uani 1 1 d . . . H3 H 0.9400 0.6820 0.5863 0.033 Uiso 1 1 calc R . . C7 C 0.8100(2) 0.66145(9) 1.12823(16) 0.0280(3) Uani 1 1 d . . . H7A H 0.6706 0.6458 1.1797 0.034 Uiso 1 1 calc R . . H7B H 0.8452 0.7248 1.1503 0.034 Uiso 1 1 calc R . . C2 C 0.8957(2) 0.67729(8) 0.83081(15) 0.0251(3) Uani 1 1 d . . . H2 H 1.0389 0.7082 0.8755 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0319(2) 0.0359(2) 0.0242(2) 0.00155(12) 0.00054(14) 0.00453(12) C6 0.0229(6) 0.0252(6) 0.0312(7) 0.0045(5) 0.0082(5) 0.0018(4) C1 0.0233(6) 0.0211(6) 0.0241(6) 0.0011(4) 0.0050(4) 0.0055(4) C5 0.0238(6) 0.0270(6) 0.0334(7) -0.0006(5) 0.0005(5) -0.0007(5) C4 0.0315(6) 0.0287(6) 0.0229(6) -0.0004(5) 0.0007(5) 0.0031(5) C3 0.0281(6) 0.0297(6) 0.0257(6) 0.0038(5) 0.0080(5) 0.0009(5) C7 0.0298(6) 0.0304(6) 0.0248(6) -0.0006(5) 0.0072(5) 0.0055(5) C2 0.0227(6) 0.0255(6) 0.0269(6) 0.0003(5) 0.0043(5) -0.0016(4) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.8258(13) . ? S1 H1S 1.238(18) . ? C6 C5 1.3884(19) . ? C6 C1 1.3932(18) . ? C6 H6 0.9300 . ? C1 C2 1.3956(17) . ? C1 C7 1.5056(17) . ? C5 C4 1.3847(19) . ? C5 H5 0.9300 . ? C4 C3 1.3916(18) . ? C4 H4 0.9300 . ? C3 C2 1.3865(17) . ? C3 H3 0.9300 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C2 H2 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 S1 H1S 98.7(8) . . ? C5 C6 C1 120.70(11) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? C6 C1 C2 118.66(11) . . ? C6 C1 C7 120.47(11) . . ? C2 C1 C7 120.86(11) . . ? C4 C5 C6 120.23(11) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C4 C3 119.61(12) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C2 C3 C4 120.11(11) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C1 C7 S1 113.38(8) . . ? C1 C7 H7A 108.9 . . ? S1 C7 H7A 108.9 . . ? C1 C7 H7B 108.9 . . ? S1 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C3 C2 C1 120.67(11) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? 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 C6 C1 C2 0.96(17) . . . . ? C5 C6 C1 C7 -177.90(11) . . . . ? C1 C6 C5 C4 -0.11(18) . . . . ? C6 C5 C4 C3 -0.87(18) . . . . ? C5 C4 C3 C2 0.97(18) . . . . ? C6 C1 C7 S1 110.44(11) . . . . ? C2 C1 C7 S1 -68.40(13) . . . . ? C4 C3 C2 C1 -0.11(18) . . . . ? C6 C1 C2 C3 -0.85(17) . . . . ? C7 C1 C2 C3 178.00(11) . . . . ? # Attachment 'CIFall.txt' data_a _database_code_depnum_ccdc_archive 'CCDC 725244' #TrackingRef 'CIFall.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; benzene ; _chemical_name_common benzene _chemical_melting_point ? _chemical_formula_moiety 'C6 H6' # 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 'C6 H6' _chemical_formula_iupac ? _chemical_formula_weight 78.11 _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 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 Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z 5 -x,-y,-z 6 1/2+x,y,1/2-z 7 1/2-x,1/2+y,z 8 x,1/2-y,1/2+z _cell_length_a 6.914(2) _cell_length_b 7.476(3) _cell_length_c 9.563(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 494.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 475 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.97 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.050 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 168 _exptl_absorpt_coefficient_mu 0.059 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9808 _exptl_absorpt_correction_T_max 0.9854 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4674 _diffrn_reflns_av_R_equivalents 0.0747 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.26 _diffrn_reflns_theta_max 28.02 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 583 # number of observed reflections (> n sig(I)) _reflns_number_gt 335 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.0119P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_coef ? _refine_ls_number_reflns 583 _refine_ls_number_parameters 28 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1197 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.174 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.030 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1297(2) 0.5762(2) 0.40803(18) 0.0490(5) Uani 1 1 d . . . H1 H 0.2172 0.6275 0.3460 0.059 Uiso 1 1 calc R . . C2 C 0.1235(3) 0.6328(2) 0.54518(17) 0.0499(5) Uani 1 1 d . . . H2 H 0.2068 0.7225 0.5756 0.060 Uiso 1 1 calc R . . C3 C 0.0057(2) 0.4432(2) 0.36289(17) 0.0492(5) Uani 1 1 d . . . H3 H 0.0095 0.4051 0.2704 0.059 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0490(10) 0.0447(9) 0.0534(10) 0.0109(8) 0.0051(8) 0.0008(9) C2 0.0504(9) 0.0399(9) 0.0594(11) -0.0026(8) -0.0070(10) -0.0044(8) C3 0.0571(10) 0.0463(9) 0.0440(9) -0.0020(8) -0.0056(9) 0.0081(9) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.379(3) . ? C1 C3 1.382(2) . ? C1 H1 0.9300 . ? C2 C3 1.376(2) 5_566 ? C2 H2 0.9300 . ? C3 C2 1.376(2) 5_566 ? C3 H3 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 119.90(15) . . ? C2 C1 H1 120.1 . . ? C3 C1 H1 120.1 . . ? C3 C2 C1 120.07(16) 5_566 . ? C3 C2 H2 120.0 5_566 . ? C1 C2 H2 120.0 . . ? C2 C3 C1 120.03(16) 5_566 . ? C2 C3 H3 120.0 5_566 . ? C1 C3 H3 120.0 . . ? 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 C3 C1 C2 C3 0.1(3) . . . 5_566 ? C2 C1 C3 C2 -0.1(3) . . . 5_566 ? #=============================================================================== data_b _database_code_depnum_ccdc_archive 'CCDC 725245' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; toluene ; _chemical_name_common toluene _chemical_melting_point ? _chemical_formula_moiety 'C7 H8' # 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 'C7 H8' _chemical_formula_iupac ? _chemical_formula_weight 92.13 _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 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 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 7.5889(11) _cell_length_b 5.8186(9) _cell_length_c 26.982(4) _cell_angle_alpha 90 _cell_angle_beta 106.136(2) _cell_angle_gamma 90 _cell_volume 1144.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 500 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.069 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.060 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9881 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11155 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0157 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.99 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2236 # number of observed reflections (> n sig(I)) _reflns_number_gt 1990 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.3795P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_coef ? _refine_ls_number_reflns 2236 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1165 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.204 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.039 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.25252(15) 0.5751(2) 0.34020(4) 0.0271(3) Uani 1 1 d . . . C1' C 0.76924(15) 0.8880(2) 0.47034(4) 0.0272(3) Uani 1 1 d . . . C6' C 0.67752(16) 1.0969(2) 0.46714(5) 0.0315(3) Uani 1 1 d . . . H6' H 0.6409 1.1506 0.4960 0.038 Uiso 1 1 calc R . . C2 C 0.13489(17) 0.3866(2) 0.33222(5) 0.0357(3) Uani 1 1 d . . . H2 H 0.0602 0.3617 0.3547 0.043 Uiso 1 1 calc R . . C6 C 0.35819(16) 0.6069(2) 0.30610(5) 0.0306(3) Uani 1 1 d . . . H6 H 0.4385 0.7352 0.3104 0.037 Uiso 1 1 calc R . . C2' C 0.82180(16) 0.8146(2) 0.42747(5) 0.0312(3) Uani 1 1 d . . . H2' H 0.8843 0.6723 0.4287 0.037 Uiso 1 1 calc R . . C7' C 0.81190(18) 0.7461(2) 0.51889(5) 0.0359(3) Uani 1 1 d . . . H7'1 H 0.9409 0.7672 0.5381 0.054 Uiso 1 1 calc R . . H7'2 H 0.7891 0.5835 0.5099 0.054 Uiso 1 1 calc R . . H7'3 H 0.7334 0.7952 0.5403 0.054 Uiso 1 1 calc R . . C4' C 0.69189(18) 1.1533(2) 0.38027(5) 0.0393(3) Uani 1 1 d . . . H4' H 0.6653 1.2430 0.3497 0.047 Uiso 1 1 calc R . . C5' C 0.63874(18) 1.2281(2) 0.42248(5) 0.0376(3) Uani 1 1 d . . . H5' H 0.5754 1.3699 0.4209 0.045 Uiso 1 1 calc R . . C3' C 0.78423(18) 0.9464(3) 0.38285(5) 0.0372(3) Uani 1 1 d . . . H3' H 0.8220 0.8945 0.3540 0.045 Uiso 1 1 calc R . . C7 C 0.26777(19) 0.7386(2) 0.38430(5) 0.0363(3) Uani 1 1 d . . . H7A H 0.2081 0.8842 0.3711 0.054 Uiso 1 1 calc R . . H7B H 0.3975 0.7664 0.4019 0.054 Uiso 1 1 calc R . . H7C H 0.2077 0.6717 0.4087 0.054 Uiso 1 1 calc R . . C4 C 0.23276(18) 0.2673(2) 0.25885(5) 0.0378(3) Uani 1 1 d . . . H4 H 0.2273 0.1621 0.2315 0.045 Uiso 1 1 calc R . . C5 C 0.34844(17) 0.4547(2) 0.26591(5) 0.0357(3) Uani 1 1 d . . . H5 H 0.4219 0.4796 0.2431 0.043 Uiso 1 1 calc R . . C3 C 0.12506(19) 0.2343(2) 0.29191(5) 0.0412(4) Uani 1 1 d . . . H3 H 0.0438 0.1068 0.2871 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0244(6) 0.0276(6) 0.0275(6) 0.0058(5) 0.0043(4) 0.0034(5) C1' 0.0231(6) 0.0270(6) 0.0292(6) 0.0012(5) 0.0032(4) -0.0053(5) C6' 0.0297(6) 0.0294(6) 0.0342(7) -0.0035(5) 0.0067(5) -0.0033(5) C2 0.0315(7) 0.0388(7) 0.0350(7) 0.0109(6) 0.0063(5) -0.0054(5) C6 0.0282(6) 0.0309(6) 0.0321(6) 0.0004(5) 0.0074(5) -0.0044(5) C2' 0.0281(6) 0.0300(6) 0.0340(7) -0.0007(5) 0.0063(5) -0.0003(5) C7' 0.0367(7) 0.0359(7) 0.0335(7) 0.0062(5) 0.0071(5) -0.0029(6) C4' 0.0364(7) 0.0418(8) 0.0324(7) 0.0125(6) -0.0025(5) -0.0065(6) C5' 0.0323(7) 0.0279(7) 0.0465(8) 0.0045(6) 0.0009(6) 0.0003(5) C3' 0.0350(7) 0.0475(8) 0.0280(6) -0.0013(6) 0.0067(5) -0.0070(6) C7 0.0407(7) 0.0360(7) 0.0339(7) 0.0019(5) 0.0134(6) 0.0042(6) C4 0.0407(7) 0.0320(7) 0.0331(7) -0.0036(5) -0.0025(6) 0.0050(6) C5 0.0310(7) 0.0437(8) 0.0318(7) -0.0025(6) 0.0077(5) 0.0022(6) C3 0.0408(7) 0.0310(7) 0.0421(8) 0.0061(6) -0.0045(6) -0.0107(6) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.3906(16) . ? C1 C2 1.3929(18) . ? C1 C7 1.5024(17) . ? C1' C2' 1.3912(17) . ? C1' C6' 1.3918(18) . ? C1' C7' 1.5056(16) . ? C6' C5' 1.3873(18) . ? C6' H6' 0.9500 . ? C2 C3 1.389(2) . ? C2 H2 0.9500 . ? C6 C5 1.3861(18) . ? C6 H6 0.9500 . ? C2' C3' 1.3885(18) . ? C2' H2' 0.9500 . ? C7' H7'1 0.9800 . ? C7' H7'2 0.9800 . ? C7' H7'3 0.9800 . ? C4' C5' 1.380(2) . ? C4' C3' 1.385(2) . ? C4' H4' 0.9500 . ? C5' H5' 0.9500 . ? C3' H3' 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C4 C5 1.3795(19) . ? C4 C3 1.380(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C3 H3 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 117.71(11) . . ? C6 C1 C7 120.55(11) . . ? C2 C1 C7 121.74(11) . . ? C2' C1' C6' 118.07(11) . . ? C2' C1' C7' 120.87(11) . . ? C6' C1' C7' 121.06(11) . . ? C5' C6' C1' 121.08(12) . . ? C5' C6' H6' 119.5 . . ? C1' C6' H6' 119.5 . . ? C3 C2 C1 121.09(12) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C5 C6 C1 121.17(12) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C3' C2' C1' 120.95(12) . . ? C3' C2' H2' 119.5 . . ? C1' C2' H2' 119.5 . . ? C1' C7' H7'1 109.5 . . ? C1' C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? C1' C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? C5' C4' C3' 119.52(12) . . ? C5' C4' H4' 120.2 . . ? C3' C4' H4' 120.2 . . ? C4' C5' C6' 120.20(12) . . ? C4' C5' H5' 119.9 . . ? C6' C5' H5' 119.9 . . ? C4' C3' C2' 120.18(12) . . ? C4' C3' H3' 119.9 . . ? C2' C3' H3' 119.9 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C4 C3 119.29(12) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.43(12) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C4 C3 C2 120.31(12) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? 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 C2' C1' C6' C5' 0.28(18) . . . . ? C7' C1' C6' C5' 179.78(11) . . . . ? C6 C1 C2 C3 0.67(18) . . . . ? C7 C1 C2 C3 -178.65(12) . . . . ? C2 C1 C6 C5 -0.74(18) . . . . ? C7 C1 C6 C5 178.59(11) . . . . ? C6' C1' C2' C3' 0.16(18) . . . . ? C7' C1' C2' C3' -179.33(11) . . . . ? C3' C4' C5' C6' 0.0(2) . . . . ? C1' C6' C5' C4' -0.36(19) . . . . ? C5' C4' C3' C2' 0.46(19) . . . . ? C1' C2' C3' C4' -0.54(19) . . . . ? C3 C4 C5 C6 0.76(19) . . . . ? C1 C6 C5 C4 0.03(19) . . . . ? C5 C4 C3 C2 -0.8(2) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? #=============================================================================== data_f _database_code_depnum_ccdc_archive 'CCDC 744556' #TrackingRef 'CIFall.txt' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 2-phenylacetonitrile ; _chemical_name_common 2-phenylacetonitrile _chemical_melting_point ? _chemical_formula_moiety 'C8 H7 N' # 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 'C8 H7 N' _chemical_formula_iupac ? _chemical_formula_weight 117.15 _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 N N 0.0061 0.0033 '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 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 8.134(3) _cell_length_b 8.783(2) _cell_length_c 9.412(3) _cell_angle_alpha 90 _cell_angle_beta 96.368(6) _cell_angle_gamma 90 _cell_volume 668.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 340 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.97 _cell_special_details ; ; _exptl_crystal_description cylidrical _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 248 _exptl_absorpt_coefficient_mu 0.069 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9581 _exptl_absorpt_correction_T_max 0.9795 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6560 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.97 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1309 # number of observed reflections (> n sig(I)) _reflns_number_gt 1013 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.1283P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1309 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.194 _refine_diff_density_min -0.151 _refine_diff_density_rms 0.038 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.15178(18) 0.22060(17) 0.01143(17) 0.0366(4) Uani 1 1 d . . . H2 H 0.1039 0.2756 -0.0697 0.044 Uiso 1 1 calc R . . C8 C -0.19361(17) 0.32334(18) 0.11989(15) 0.0331(4) Uani 1 1 d . . . C1 C 0.05080(17) 0.15763(15) 0.10522(16) 0.0321(4) Uani 1 1 d . . . N1 N -0.23777(17) 0.43983(16) 0.15284(15) 0.0467(4) Uani 1 1 d . . . C6 C 0.12223(19) 0.07825(17) 0.22364(16) 0.0370(4) Uani 1 1 d . . . H6 H 0.0543 0.0357 0.2893 0.044 Uiso 1 1 calc R . . C7 C -0.13611(18) 0.17406(17) 0.0781(2) 0.0434(4) Uani 1 1 d . . . H7A H -0.1714 0.1577 -0.0249 0.052 Uiso 1 1 calc R . . H7B H -0.1886 0.0944 0.1322 0.052 Uiso 1 1 calc R . . C5 C 0.29242(19) 0.06078(18) 0.24653(16) 0.0400(4) Uani 1 1 d . . . H5 H 0.3408 0.0056 0.3274 0.048 Uiso 1 1 calc R . . C3 C 0.32177(18) 0.20403(18) 0.03495(17) 0.0392(4) Uani 1 1 d . . . H3 H 0.3902 0.2481 -0.0295 0.047 Uiso 1 1 calc R . . C4 C 0.39182(19) 0.12335(18) 0.15219(16) 0.0396(4) Uani 1 1 d . . . H4 H 0.5084 0.1109 0.1679 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0374(8) 0.0328(8) 0.0382(8) 0.0048(6) -0.0022(6) -0.0012(6) C8 0.0262(7) 0.0364(9) 0.0368(8) 0.0039(7) 0.0032(6) -0.0011(6) C1 0.0274(7) 0.0244(7) 0.0441(9) -0.0063(6) 0.0029(6) -0.0013(6) N1 0.0413(8) 0.0438(9) 0.0559(9) -0.0045(7) 0.0090(7) 0.0060(6) C6 0.0389(9) 0.0369(9) 0.0366(8) 0.0004(6) 0.0106(7) -0.0021(6) C7 0.0286(8) 0.0326(8) 0.0682(11) -0.0072(8) 0.0018(7) -0.0005(6) C5 0.0397(9) 0.0440(9) 0.0345(8) 0.0043(7) -0.0035(7) 0.0031(7) C3 0.0353(8) 0.0434(9) 0.0401(9) 0.0009(7) 0.0091(7) -0.0076(7) C4 0.0263(7) 0.0479(10) 0.0436(9) -0.0031(7) 0.0002(7) 0.0000(7) #=============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 C3 1.383(2) . ? C2 C1 1.386(2) . ? C2 H2 0.9500 . ? C8 N1 1.1388(19) . ? C8 C7 1.461(2) . ? C1 C6 1.386(2) . ? C1 C7 1.520(2) . ? C6 C5 1.386(2) . ? C6 H6 0.9500 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C5 C4 1.380(2) . ? C5 H5 0.9500 . ? C3 C4 1.380(2) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C2 C1 120.56(14) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? N1 C8 C7 179.69(17) . . ? C2 C1 C6 119.18(13) . . ? C2 C1 C7 120.49(14) . . ? C6 C1 C7 120.32(14) . . ? C5 C6 C1 120.21(14) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C8 C7 C1 112.59(12) . . ? C8 C7 H7A 109.1 . . ? C1 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C1 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C4 C5 C6 120.16(14) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C4 C3 C2 119.90(14) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 119.98(14) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? 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 C3 C2 C1 C6 0.3(2) . . . . ? C3 C2 C1 C7 -179.14(13) . . . . ? C2 C1 C6 C5 -0.8(2) . . . . ? C7 C1 C6 C5 178.68(14) . . . . ? C2 C1 C7 C8 -79.02(19) . . . . ? C6 C1 C7 C8 101.52(17) . . . . ? C1 C6 C5 C4 0.5(2) . . . . ? C1 C2 C3 C4 0.4(2) . . . . ? C6 C5 C4 C3 0.2(2) . . . . ? C2 C3 C4 C5 -0.7(2) . . . . ?