Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Dr Manuel Antonio Fernandes' _publ_contact_author_address ; School of Chemistry University of the Witwatersrand PO WITS Johannesburg 2050 SOUTH AFRICA ; _publ_contact_author_email MANUEL@HOBBES.GH.WITS.AC.ZA _publ_section_title ; Polymorphism and phase transformations in 2,6-disubstituted N-phenylformamides: the influence of hydrogen bonding, chloro-methyl exchange, intermolecular interactions and disorder ; loop_ _publ_author_name M.Layh 'Demetrius C. Levendis' J.L.Look T.S.P.Mkwizu B.Omondi data_26dicllt _database_code_depnum_ccdc_archive 'CCDC 275926' # 1a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 Cl2 N O' _chemical_formula_sum 'C7 H5 Cl2 N O' _chemical_formula_weight 190.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6036(10) _cell_length_b 12.7431(15) _cell_length_c 14.4016(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1578.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description spherical _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.599 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.756 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7037 _exptl_absorpt_correction_T_max 0.8635 _exptl_absorpt_process_details ; Absorption corrections carried out with SADABS ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10023 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1895 _reflns_number_gt 1447 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0418P)^2^+0.3165P] 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 SHELXL _refine_ls_extinction_coef 0.0379(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1895 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 -0.05474(16) 0.41687(12) 0.14902(10) 0.0329(3) Uani 1 1 d . . . C2 C -0.14078(18) 0.50795(13) 0.16298(11) 0.0394(4) Uani 1 1 d . . . C3 C -0.2408(2) 0.54606(15) 0.09580(13) 0.0515(5) Uani 1 1 d . . . H3 H -0.2998 0.6058 0.1072 0.062 Uiso 1 1 calc R . . C4 C -0.2524(2) 0.49469(16) 0.01178(13) 0.0550(5) Uani 1 1 d . . . H4 H -0.3190 0.5205 -0.0337 0.066 Uiso 1 1 calc R . . C5 C -0.1662(2) 0.40548(15) -0.00564(12) 0.0479(4) Uani 1 1 d . . . H5 H -0.1727 0.3719 -0.0628 0.058 Uiso 1 1 calc R . . C6 C -0.07007(18) 0.36694(13) 0.06329(11) 0.0363(4) Uani 1 1 d . . . C7 C 0.00185(18) 0.33864(14) 0.29866(11) 0.0411(4) Uani 1 1 d . . . H7 H 0.0783 0.3123 0.3379 0.049 Uiso 1 1 calc R . . N1 N 0.04859(16) 0.37737(12) 0.21706(9) 0.0363(3) Uani 1 1 d . . . O1 O -0.13177(13) 0.33469(12) 0.32633(9) 0.0570(4) Uani 1 1 d . . . Cl1 Cl -0.11812(7) 0.57910(4) 0.26503(4) 0.06106(19) Uani 1 1 d . . . Cl2 Cl 0.03796(6) 0.25462(3) 0.04131(3) 0.05046(17) Uani 1 1 d . . . H1 H 0.137(2) 0.3703(15) 0.2024(12) 0.043(5) Uiso 1 1 d . . . 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 0.0262(7) 0.0387(8) 0.0336(8) 0.0045(6) 0.0018(6) -0.0037(6) C2 0.0369(8) 0.0421(9) 0.0393(9) 0.0046(7) 0.0069(7) 0.0000(7) C3 0.0418(9) 0.0522(11) 0.0604(11) 0.0198(9) 0.0069(8) 0.0091(8) C4 0.0415(9) 0.0755(14) 0.0479(10) 0.0259(9) -0.0080(8) -0.0024(10) C5 0.0432(9) 0.0641(12) 0.0365(9) 0.0076(8) -0.0044(7) -0.0128(9) C6 0.0328(8) 0.0407(8) 0.0356(8) 0.0024(7) 0.0021(6) -0.0066(7) C7 0.0327(8) 0.0567(11) 0.0340(8) 0.0035(7) -0.0035(6) 0.0082(7) N1 0.0246(7) 0.0498(8) 0.0344(7) -0.0014(6) 0.0005(5) 0.0028(6) O1 0.0352(7) 0.0889(10) 0.0470(7) 0.0207(7) 0.0055(5) 0.0096(6) Cl1 0.0753(4) 0.0510(3) 0.0569(3) -0.0132(2) 0.0069(2) 0.0091(2) Cl2 0.0598(3) 0.0451(3) 0.0464(3) -0.00937(19) 0.0033(2) 0.0001(2) _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 1.391(2) . ? C1 C6 1.395(2) . ? C1 N1 1.4156(19) . ? C2 C3 1.383(2) . ? C2 Cl1 1.7379(17) . ? C3 C4 1.379(3) . ? C3 H3 0.9300 . ? C4 C5 1.380(3) . ? C4 H4 0.9300 . ? C5 C6 1.382(2) . ? C5 H5 0.9300 . ? C6 Cl2 1.7358(17) . ? C7 O1 1.2177(19) . ? C7 N1 1.337(2) . ? C7 H7 0.9300 . ? N1 H1 0.79(2) . ? 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 C6 117.26(14) . . ? C2 C1 N1 122.06(14) . . ? C6 C1 N1 120.65(14) . . ? C3 C2 C1 121.53(16) . . ? C3 C2 Cl1 118.57(14) . . ? C1 C2 Cl1 119.85(12) . . ? C4 C3 C2 119.48(18) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.76(17) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 118.92(17) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C1 122.01(16) . . ? C5 C6 Cl2 118.85(14) . . ? C1 C6 Cl2 119.13(12) . . ? O1 C7 N1 125.95(15) . . ? O1 C7 H7 117.0 . . ? N1 C7 H7 117.0 . . ? C7 N1 C1 123.43(13) . . ? C7 N1 H1 118.8(13) . . ? C1 N1 H1 117.1(13) . . ? 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 C1 C2 C3 1.8(2) . . . . ? N1 C1 C2 C3 179.67(15) . . . . ? C6 C1 C2 Cl1 -175.81(11) . . . . ? N1 C1 C2 Cl1 2.1(2) . . . . ? C1 C2 C3 C4 -2.0(3) . . . . ? Cl1 C2 C3 C4 175.57(14) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C4 C5 C6 C1 -1.6(2) . . . . ? C4 C5 C6 Cl2 179.88(13) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? N1 C1 C6 C5 -177.88(14) . . . . ? C2 C1 C6 Cl2 178.59(11) . . . . ? N1 C1 C6 Cl2 0.6(2) . . . . ? O1 C7 N1 C1 -2.2(3) . . . . ? C2 C1 N1 C7 67.4(2) . . . . ? C6 C1 N1 C7 -114.73(18) . . . . ? 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 N1 H1 O1 0.79(2) 2.09(2) 2.8721(19) 172.8(19) 6_656 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.320 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.042 data_26diclht _database_code_depnum_ccdc_archive 'CCDC 275927' # 1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H5 Cl2 N O' _chemical_formula_sum 'C7 H5 Cl2 N O' _chemical_formula_weight 190.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.3539(8) _cell_length_b 13.406(3) _cell_length_c 14.073(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.616(4) _cell_angle_gamma 90.00 _cell_volume 820.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.83 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.727 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5836 _exptl_absorpt_correction_T_max 0.7597 _exptl_absorpt_process_details ; Absorption corrections carried out with SADABS ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5389 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2020 _reflns_number_gt 1509 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0925P)^2^+0.2689P] 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_number_reflns 2020 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1573 _refine_ls_wR_factor_gt 0.1443 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.8474(4) 0.90210(15) 0.76312(14) 0.0450(5) Uani 1 1 d . . . C2 C 1.0037(5) 0.81554(17) 0.79006(16) 0.0518(5) Uani 1 1 d . . . C3 C 1.1280(6) 0.75252(19) 0.7239(2) 0.0653(7) Uani 1 1 d . . . H3 H 1.2316 0.6949 0.7434 0.078 Uiso 1 1 calc R . . C4 C 1.0958(7) 0.7766(2) 0.6289(2) 0.0712(8) Uani 1 1 d . . . H4 H 1.1757 0.7341 0.5840 0.085 Uiso 1 1 calc R . . C5 C 0.9476(8) 0.8624(2) 0.59931(18) 0.0723(8) Uani 1 1 d . . . H5 H 0.9295 0.8783 0.5350 0.087 Uiso 1 1 calc R . . C6 C 0.8254(6) 0.92497(18) 0.66634(16) 0.0562(5) Uani 1 1 d . . . C7 C 0.8737(5) 1.02740(16) 0.88619(16) 0.0482(5) Uani 1 1 d . . . H7 H 0.7654 1.0671 0.9272 0.058 Uiso 1 1 calc R . . N1 N 0.7130(4) 0.96485(14) 0.83038(13) 0.0480(4) Uani 1 1 d . . . O1 O 1.1517(4) 1.03686(14) 0.88788(15) 0.0669(5) Uani 1 1 d . . . Cl1 Cl 1.0445(2) 0.78459(5) 0.90934(5) 0.0800(3) Uani 1 1 d . . . Cl2 Cl 0.6473(2) 1.03480(7) 0.63049(5) 0.0920(3) Uani 1 1 d . . . H1 H 0.527(7) 0.964(2) 0.830(2) 0.064(8) Uiso 1 1 d . . . 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 0.0407(10) 0.0488(11) 0.0459(11) -0.0067(8) 0.0058(8) -0.0080(8) C2 0.0596(13) 0.0479(11) 0.0484(11) -0.0052(9) 0.0070(9) -0.0050(9) C3 0.0757(16) 0.0502(13) 0.0710(16) -0.0117(12) 0.0159(13) 0.0008(11) C4 0.0890(19) 0.0609(15) 0.0656(16) -0.0221(12) 0.0255(15) -0.0102(13) C5 0.100(2) 0.0730(17) 0.0450(12) -0.0100(12) 0.0155(13) -0.0157(15) C6 0.0637(13) 0.0558(12) 0.0490(12) -0.0026(10) 0.0021(10) -0.0051(10) C7 0.0426(11) 0.0494(11) 0.0531(11) -0.0106(9) 0.0083(8) 0.0020(8) N1 0.0339(9) 0.0585(11) 0.0520(10) -0.0100(8) 0.0069(7) -0.0025(7) O1 0.0407(8) 0.0739(11) 0.0866(12) -0.0332(9) 0.0086(8) -0.0057(7) Cl1 0.1244(7) 0.0610(4) 0.0542(4) 0.0037(3) 0.0005(4) 0.0095(4) Cl2 0.1281(8) 0.0826(5) 0.0639(5) 0.0086(3) -0.0100(4) 0.0252(5) _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 1.389(3) . ? C1 C6 1.395(3) . ? C1 N1 1.413(3) . ? C2 C3 1.385(3) . ? C2 Cl1 1.730(2) . ? C3 C4 1.377(4) . ? C3 H3 0.9300 . ? C4 C5 1.373(5) . ? C4 H4 0.9300 . ? C5 C6 1.387(4) . ? C5 H5 0.9300 . ? C6 Cl2 1.729(3) . ? C7 O1 1.216(3) . ? C7 N1 1.327(3) . ? C7 H7 0.9300 . ? N1 H1 0.81(3) . ? 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 C6 117.45(19) . . ? C2 C1 N1 121.82(19) . . ? C6 C1 N1 120.7(2) . . ? C3 C2 C1 121.9(2) . . ? C3 C2 Cl1 118.7(2) . . ? C1 C2 Cl1 119.49(16) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 121.1(2) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 119.3(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C1 121.3(2) . . ? C5 C6 Cl2 119.9(2) . . ? C1 C6 Cl2 118.82(18) . . ? O1 C7 N1 125.11(19) . . ? O1 C7 H7 117.4 . . ? N1 C7 H7 117.4 . . ? C7 N1 C1 123.33(17) . . ? C7 N1 H1 121(2) . . ? C1 N1 H1 116(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _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 C1 C2 C3 -1.4(3) . . . . ? N1 C1 C2 C3 178.1(2) . . . . ? C6 C1 C2 Cl1 178.81(17) . . . . ? N1 C1 C2 Cl1 -1.6(3) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? Cl1 C2 C3 C4 179.9(2) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? C4 C5 C6 C1 -0.6(4) . . . . ? C4 C5 C6 Cl2 178.3(2) . . . . ? C2 C1 C6 C5 1.7(3) . . . . ? N1 C1 C6 C5 -177.9(2) . . . . ? C2 C1 C6 Cl2 -177.23(17) . . . . ? N1 C1 C6 Cl2 3.2(3) . . . . ? O1 C7 N1 C1 -1.6(4) . . . . ? C2 C1 N1 C7 76.8(3) . . . . ? C6 C1 N1 C7 -103.6(3) . . . . ? 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 N1 H1 O1 0.81(3) 2.10(3) 2.782(2) 142(3) 1_455 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.336 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.049 data_5b_bo5_s _database_code_depnum_ccdc_archive 'CCDC 275928' # 2a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2,6-chloromethyl-N-phenylformamide _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 Cl N O' _chemical_formula_sum 'C8 H8 Cl N O' _chemical_formula_weight 169.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.4446(2) _cell_length_b 12.9028(3) _cell_length_c 14.4186(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1571.04(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5143 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 28.19 _exptl_crystal_description chunk _exptl_crystal_colour clear _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.421 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8666 _exptl_absorpt_correction_T_max 0.9205 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11245 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 27.99 _reflns_number_total 1894 _reflns_number_gt 1696 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0505P)^2^+1.0680P] 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_number_reflns 1894 _refine_ls_number_parameters 105 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1086 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.05300(16) 0.58009(11) 0.14937(9) 0.0198(3) Uani 1 1 d . A . C2 C 0.14015(17) 0.48978(12) 0.16421(10) 0.0238(3) Uani 1 1 d D . . C3 C 0.24340(19) 0.45409(13) 0.09646(11) 0.0311(4) Uani 1 1 d . A . H3 H 0.3047 0.3936 0.1074 0.037 Uiso 1 1 calc R . . C4 C 0.25738(19) 0.50624(14) 0.01313(11) 0.0336(4) Uani 1 1 d . . . H4 H 0.3280 0.4814 -0.0331 0.040 Uiso 1 1 calc R A . C5 C 0.16877(18) 0.59460(13) -0.00323(10) 0.0292(3) Uani 1 1 d . A . H5 H 0.1772 0.6295 -0.0611 0.035 Uiso 1 1 calc R . . C6 C 0.06754(16) 0.63239(11) 0.06480(10) 0.0224(3) Uani 1 1 d D . . C7 C -0.01267(17) 0.65401(12) 0.30021(10) 0.0253(3) Uani 1 1 d . A . H7 H -0.0950 0.6784 0.3394 0.030 Uiso 1 1 calc R . . Cl1 Cl 0.11595(16) 0.41946(11) 0.26651(6) 0.03299(18) Uani 0.573(1) 1 d PD A 1 C8 C -0.0263(6) 0.7275(3) 0.0479(4) 0.03299(18) Uani 0.573(1) 1 d PD A 1 H8A H -0.0021 0.7546 -0.0140 0.049 Uiso 0.573(1) 1 calc PR A 1 H8B H 0.0004 0.7797 0.0947 0.049 Uiso 0.573(1) 1 calc PR A 1 H8C H -0.1394 0.7111 0.0519 0.049 Uiso 0.573(1) 1 calc PR A 1 Cl1A Cl -0.04280(19) 0.74302(10) 0.04337(13) 0.03299(18) Uani 0.427(1) 1 d PD A 2 C8A C 0.1286(11) 0.4242(6) 0.2497(4) 0.03299(18) Uani 0.427(1) 1 d PD A 2 H8D H 0.1989 0.3642 0.2435 0.049 Uiso 0.427(1) 1 calc PR A 2 H8E H 0.0193 0.4005 0.2575 0.049 Uiso 0.427(1) 1 calc PR A 2 H8F H 0.1603 0.4652 0.3038 0.049 Uiso 0.427(1) 1 calc PR A 2 N1 N -0.05550(14) 0.61747(10) 0.21718(8) 0.0221(3) Uani 1 1 d . . . H1 H -0.150(2) 0.6226(15) 0.2026(13) 0.029(5) Uiso 1 1 d . . . O1 O 0.12208(13) 0.65903(10) 0.33058(8) 0.0341(3) Uani 1 1 d . . . 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 0.0150(6) 0.0253(7) 0.0193(6) -0.0028(5) -0.0010(5) -0.0023(5) C2 0.0210(6) 0.0269(7) 0.0236(7) -0.0021(5) -0.0043(5) -0.0006(5) C3 0.0238(7) 0.0346(8) 0.0351(8) -0.0123(7) -0.0046(6) 0.0058(6) C4 0.0243(7) 0.0480(10) 0.0286(8) -0.0162(7) 0.0043(6) -0.0010(7) C5 0.0259(7) 0.0412(9) 0.0204(7) -0.0060(6) 0.0026(6) -0.0091(7) C6 0.0197(6) 0.0260(7) 0.0215(6) -0.0015(5) -0.0021(5) -0.0057(5) C7 0.0208(7) 0.0331(8) 0.0220(7) -0.0008(6) 0.0034(5) 0.0051(6) Cl1 0.0384(4) 0.0308(3) 0.0298(3) 0.0073(3) -0.0020(3) 0.0031(2) C8 0.0384(4) 0.0308(3) 0.0298(3) 0.0073(3) -0.0020(3) 0.0031(2) Cl1A 0.0384(4) 0.0308(3) 0.0298(3) 0.0073(3) -0.0020(3) 0.0031(2) C8A 0.0384(4) 0.0308(3) 0.0298(3) 0.0073(3) -0.0020(3) 0.0031(2) N1 0.0136(5) 0.0311(7) 0.0215(6) 0.0008(5) 0.0007(4) 0.0025(5) O1 0.0221(5) 0.0531(8) 0.0272(6) -0.0111(5) -0.0035(4) 0.0061(5) _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 1.395(2) . ? C1 C6 1.3990(19) . ? C1 N1 1.4241(17) . ? C2 C3 1.388(2) . ? C2 C8A 1.497(4) . ? C2 Cl1 1.7437(17) . ? C3 C4 1.382(2) . ? C3 H3 0.9500 . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(2) . ? C5 H5 0.9500 . ? C6 C8 1.481(4) . ? C6 Cl1A 1.7324(18) . ? C7 O1 1.2210(18) . ? C7 N1 1.3366(19) . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C8A H8D 0.9800 . ? C8A H8E 0.9800 . ? C8A H8F 0.9800 . ? N1 H1 0.83(2) . ? 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 C6 119.37(13) . . ? C2 C1 N1 121.14(12) . . ? C6 C1 N1 119.44(13) . . ? C3 C2 C1 120.04(14) . . ? C3 C2 C8A 115.6(4) . . ? C1 C2 C8A 124.3(4) . . ? C3 C2 Cl1 119.76(13) . . ? C1 C2 Cl1 120.18(12) . . ? C4 C3 C2 120.27(15) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.20(14) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.09(15) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.00(14) . . ? C5 C6 C8 120.3(3) . . ? C1 C6 C8 119.7(3) . . ? C5 C6 Cl1A 119.61(13) . . ? C1 C6 Cl1A 120.38(13) . . ? O1 C7 N1 126.31(14) . . ? O1 C7 H7 116.8 . . ? N1 C7 H7 116.8 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C2 C8A H8D 109.5 . . ? C2 C8A H8E 109.5 . . ? H8D C8A H8E 109.5 . . ? C2 C8A H8F 109.5 . . ? H8D C8A H8F 109.5 . . ? H8E C8A H8F 109.5 . . ? C7 N1 C1 124.08(12) . . ? C7 N1 H1 117.3(13) . . ? C1 N1 H1 118.3(13) . . ? 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 C1 C2 C3 1.8(2) . . . . ? N1 C1 C2 C3 179.03(13) . . . . ? C6 C1 C2 C8A -176.8(4) . . . . ? N1 C1 C2 C8A 0.5(4) . . . . ? C6 C1 C2 Cl1 -176.52(11) . . . . ? N1 C1 C2 Cl1 0.75(19) . . . . ? C1 C2 C3 C4 -1.7(2) . . . . ? C8A C2 C3 C4 177.0(4) . . . . ? Cl1 C2 C3 C4 176.62(13) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 1.2(2) . . . . ? C4 C5 C6 C1 -1.1(2) . . . . ? C4 C5 C6 C8 179.4(3) . . . . ? C4 C5 C6 Cl1A -179.95(13) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? N1 C1 C6 C5 -177.69(13) . . . . ? C2 C1 C6 C8 179.1(3) . . . . ? N1 C1 C6 C8 1.8(3) . . . . ? C2 C1 C6 Cl1A 178.45(12) . . . . ? N1 C1 C6 Cl1A 1.13(19) . . . . ? O1 C7 N1 C1 -1.4(3) . . . . ? C2 C1 N1 C7 67.2(2) . . . . ? C6 C1 N1 C7 -115.57(16) . . . . ? 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 N1 H1 O1 0.83(2) 2.04(2) 2.8592(17) 171.2(18) 6_556 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.378 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.050 data_26clmeht _database_code_depnum_ccdc_archive 'CCDC 275929' # 2b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2,6-chloromethyl-N-phenylformamide _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 Cl N O' _chemical_formula_sum 'C8 H8 Cl N O' _chemical_formula_weight 169.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/a _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 13.498(3) _cell_length_b 4.3186(10) _cell_length_c 14.938(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.365(4) _cell_angle_gamma 90.00 _cell_volume 810.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 3.242 _cell_measurement_theta_max 28.144 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.408 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min 0.7919 _exptl_absorpt_correction_T_max 0.9681 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9940 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1951 _reflns_number_gt 1619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0504P)^2^+0.3441P] 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_number_reflns 1951 _refine_ls_number_parameters 123 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1111 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.003 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 0.21614(11) 0.5970(3) 0.26193(10) 0.0293(3) Uani 1 1 d U A . C2 C 0.13667(11) 0.4688(4) 0.28999(11) 0.0337(3) Uani 1 1 d U . . C3 C 0.05369(13) 0.3058(4) 0.22300(13) 0.0450(4) Uani 1 1 d U A . H3 H -0.0003 0.2180 0.2417 0.054 Uiso 1 1 calc R . . C4 C 0.04883(14) 0.2700(5) 0.12995(13) 0.0525(5) Uani 1 1 d U . . H4 H -0.0082 0.1574 0.0851 0.063 Uiso 1 1 calc R A . C5 C 0.12640(15) 0.3969(5) 0.10141(12) 0.0514(5) Uani 1 1 d U A . H5 H 0.1227 0.3726 0.0371 0.062 Uiso 1 1 calc R . . C6 C 0.21004(12) 0.5604(4) 0.16736(11) 0.0376(4) Uani 1 1 d U . . C7 C 0.38573(12) 0.6113(3) 0.39388(11) 0.0348(3) Uani 1 1 d U A . H7 H 0.4409 0.7338 0.4372 0.042 Uiso 1 1 calc R . . Cl1 Cl 0.31038(13) 0.7287(4) 0.13461(12) 0.0587(4) Uani 0.750(2) 1 d PU A 1 C8 C 0.1382(11) 0.498(3) 0.3911(7) 0.058(2) Uani 0.750(2) 1 d PU A 1 H8A H 0.0770 0.3879 0.3963 0.087 Uiso 0.750(2) 1 calc PR A 1 H8B H 0.1346 0.7171 0.4066 0.087 Uiso 0.750(2) 1 calc PR A 1 H8C H 0.2041 0.4075 0.4362 0.087 Uiso 0.750(2) 1 calc PR A 1 Cl1A Cl 0.1446(8) 0.551(2) 0.4067(6) 0.0535(12) Uani 0.250(2) 1 d PU A 2 C8A C 0.2951(16) 0.691(5) 0.1341(11) 0.061(5) Uani 0.250(2) 1 d PU A 2 H8D H 0.2773 0.6430 0.0659 0.092 Uiso 0.250(2) 1 calc PR A 2 H8E H 0.3640 0.5984 0.1718 0.092 Uiso 0.250(2) 1 calc PR A 2 H8F H 0.2990 0.9161 0.1431 0.092 Uiso 0.250(2) 1 calc PR A 2 N1 N 0.30304(10) 0.7585(3) 0.33011(9) 0.0317(3) Uani 1 1 d U . . O1 O 0.39537(10) 0.3295(3) 0.40036(10) 0.0559(4) Uani 1 1 d U . . H1 H 0.3064(16) 0.950(5) 0.3325(14) 0.050(5) Uiso 1 1 d . . . 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 0.0282(6) 0.0233(6) 0.0339(7) 0.0014(5) 0.0082(5) 0.0051(5) C2 0.0305(7) 0.0330(7) 0.0354(7) 0.0030(6) 0.0092(6) 0.0035(6) C3 0.0301(8) 0.0416(9) 0.0548(10) 0.0027(7) 0.0053(7) -0.0019(6) C4 0.0390(9) 0.0505(11) 0.0512(10) -0.0107(8) -0.0036(8) 0.0023(8) C5 0.0497(10) 0.0621(12) 0.0333(8) -0.0086(8) 0.0043(7) 0.0156(9) C6 0.0361(8) 0.0405(8) 0.0371(8) 0.0042(6) 0.0142(6) 0.0114(6) C7 0.0286(7) 0.0262(7) 0.0442(8) -0.0041(6) 0.0068(6) -0.0021(5) Cl1 0.0560(6) 0.0748(7) 0.0577(7) 0.0184(5) 0.0356(5) 0.0136(5) C8 0.045(3) 0.072(5) 0.058(4) 0.004(3) 0.020(3) -0.011(2) Cl1A 0.046(2) 0.076(3) 0.0441(16) 0.0007(18) 0.0227(15) -0.0081(17) C8A 0.071(9) 0.092(11) 0.021(5) -0.023(6) 0.017(5) -0.017(7) N1 0.0320(6) 0.0202(6) 0.0405(7) -0.0014(5) 0.0104(5) -0.0001(5) O1 0.0407(7) 0.0252(6) 0.0753(9) -0.0017(6) -0.0103(6) 0.0013(5) _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 1.394(2) . ? C1 C2 1.400(2) . ? C1 N1 1.4245(18) . ? C2 C3 1.391(2) . ? C2 C8 1.509(9) . ? C2 Cl1A 1.744(8) . ? C3 C4 1.376(3) . ? C3 H3 0.9500 . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 C8A 1.52(2) . ? C6 Cl1 1.756(2) . ? C7 O1 1.224(2) . ? C7 N1 1.335(2) . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C8A H8D 0.9800 . ? C8A H8E 0.9800 . ? C8A H8F 0.9800 . ? N1 H1 0.83(2) . ? 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 119.33(13) . . ? C6 C1 N1 120.62(13) . . ? C2 C1 N1 120.04(13) . . ? C3 C2 C1 119.25(15) . . ? C3 C2 C8 118.4(5) . . ? C1 C2 C8 122.3(5) . . ? C3 C2 Cl1A 124.2(3) . . ? C1 C2 Cl1A 116.4(3) . . ? C4 C3 C2 120.87(16) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.35(16) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 119.64(16) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 120.57(16) . . ? C5 C6 C8A 118.2(6) . . ? C1 C6 C8A 121.2(6) . . ? C5 C6 Cl1 121.49(14) . . ? C1 C6 Cl1 117.94(13) . . ? O1 C7 N1 124.54(14) . . ? O1 C7 H7 117.7 . . ? N1 C7 H7 117.7 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C8A H8D 109.5 . . ? C6 C8A H8E 109.5 . . ? H8D C8A H8E 109.5 . . ? C6 C8A H8F 109.5 . . ? H8D C8A H8F 109.5 . . ? H8E C8A H8F 109.5 . . ? C7 N1 C1 122.24(12) . . ? C7 N1 H1 115.2(14) . . ? C1 N1 H1 122.5(14) . . ? 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 C1 C2 C3 0.4(2) . . . . ? N1 C1 C2 C3 -178.55(13) . . . . ? C6 C1 C2 C8 179.7(7) . . . . ? N1 C1 C2 C8 0.8(7) . . . . ? C6 C1 C2 Cl1A -175.1(4) . . . . ? N1 C1 C2 Cl1A 5.9(4) . . . . ? C1 C2 C3 C4 -0.1(2) . . . . ? C8 C2 C3 C4 -179.5(7) . . . . ? Cl1A C2 C3 C4 175.0(5) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C4 C5 C6 C8A 178.8(11) . . . . ? C4 C5 C6 Cl1 -179.57(15) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? N1 C1 C6 C5 178.59(14) . . . . ? C2 C1 C6 C8A -179.1(11) . . . . ? N1 C1 C6 C8A -0.1(11) . . . . ? C2 C1 C6 Cl1 179.22(12) . . . . ? N1 C1 C6 Cl1 -1.8(2) . . . . ? O1 C7 N1 C1 0.0(3) . . . . ? C6 C1 N1 C7 -99.71(18) . . . . ? C2 C1 N1 C7 79.27(18) . . . . ? 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 N1 H1 O1 0.83(2) 2.07(2) 2.7896(18) 145.7(19) 1_565 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.265 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.042 data_26-dime _database_code_depnum_ccdc_archive 'CCDC 275930' # 3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2,6-dimethyl-N-phenylformamide _chemical_melting_point ? _chemical_formula_moiety 'C9 H11 N O' _chemical_formula_sum 'C9 H11 N O' _chemical_formula_weight 149.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.5023(4) _cell_length_b 8.5886(8) _cell_length_c 21.297(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 823.53(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 902 _cell_measurement_theta_min 3.72 _cell_measurement_theta_max 26.99 _exptl_crystal_description Blocky _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6763 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0104 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.50 _reflns_number_total 943 _reflns_number_gt 855 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SHELEXTL' _computing_structure_solution 'Bruker SHELEXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELEXTL' _computing_publication_material 'Bruker SHELEXTL' _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^)+(0.1326P)^2^+0.0991P] 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), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _refine_ls_number_reflns 943 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 0.664 _refine_ls_restrained_S_all 0.664 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.003 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 0.1609(4) 0.98853(18) 0.12107(7) 0.0427(4) Uani 1 1 d . . . C2 C -0.0162(4) 0.93884(19) 0.07104(7) 0.0471(4) Uani 1 1 d . . . C3 C -0.1376(5) 0.7899(2) 0.07424(9) 0.0576(5) Uani 1 1 d . . . H3 H -0.2598 0.7551 0.0420 0.069 Uiso 1 1 calc R . . C4 C -0.0798(6) 0.6932(2) 0.12442(10) 0.0624(6) Uani 1 1 d . . . H4 H -0.1620 0.5939 0.1257 0.075 Uiso 1 1 calc R . . C5 C 0.0999(5) 0.7436(2) 0.17263(9) 0.0584(5) Uani 1 1 d . . . H5 H 0.1399 0.6771 0.2060 0.070 Uiso 1 1 calc R . . C6 C 0.2224(4) 0.8920(2) 0.17233(8) 0.0478(4) Uani 1 1 d . . . C7 C 0.1312(4) 1.2722(2) 0.12630(9) 0.0499(5) Uani 1 1 d . . . H7 H 0.2373 1.3650 0.1283 0.060 Uiso 1 1 calc R . . C8 C -0.0720(6) 1.0392(2) 0.01430(8) 0.0635(6) Uani 1 1 d . . . H8A H -0.1790 0.9804 -0.0166 0.095 Uiso 1 1 calc R . . H8B H 0.1143 1.0727 -0.0030 0.095 Uiso 1 1 calc R . . H8C H -0.1868 1.1285 0.0263 0.095 Uiso 1 1 calc R . . C9 C 0.4143(5) 0.9478(3) 0.22572(8) 0.0653(6) Uani 1 1 d . . . H9A H 0.6167 0.9554 0.2118 0.098 Uiso 1 1 calc R . . H9B H 0.4018 0.8754 0.2600 0.098 Uiso 1 1 calc R . . H9C H 0.3467 1.0483 0.2394 0.098 Uiso 1 1 calc R . . N1 N 0.2877(4) 1.14129(18) 0.12034(8) 0.0475(4) Uani 1 1 d . . . O1 O -0.1388(3) 1.28105(16) 0.12938(8) 0.0664(5) Uani 1 1 d . . . H1 H 0.464(6) 1.151(2) 0.1241(8) 0.049(5) Uiso 1 1 d . . . 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 0.0355(8) 0.0411(8) 0.0514(9) -0.0017(7) 0.0063(8) 0.0022(7) C2 0.0452(10) 0.0448(8) 0.0513(8) -0.0047(7) 0.0015(8) 0.0030(8) C3 0.0551(11) 0.0490(10) 0.0687(11) -0.0129(9) -0.0009(10) -0.0034(10) C4 0.0613(12) 0.0391(8) 0.0869(14) 0.0002(9) 0.0099(12) -0.0022(9) C5 0.0554(11) 0.0509(9) 0.0689(11) 0.0138(9) 0.0083(10) 0.0076(10) C6 0.0391(9) 0.0518(9) 0.0526(9) 0.0018(7) 0.0040(8) 0.0079(8) C7 0.0431(9) 0.0404(9) 0.0661(11) -0.0028(8) -0.0006(9) -0.0087(7) C8 0.0755(14) 0.0620(11) 0.0528(9) -0.0001(9) -0.0081(11) 0.0008(12) C9 0.0565(12) 0.0805(13) 0.0590(10) 0.0047(10) -0.0061(10) 0.0062(12) N1 0.0336(8) 0.0477(8) 0.0612(9) -0.0004(7) 0.0009(7) -0.0049(6) O1 0.0422(7) 0.0483(7) 0.1086(12) -0.0112(7) 0.0030(8) -0.0001(6) _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 1.399(2) . ? C1 C2 1.398(2) . ? C1 N1 1.431(2) . ? C2 C3 1.393(3) . ? C2 C8 1.505(2) . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 C5 1.377(3) . ? C4 H4 0.9300 . ? C5 C6 1.389(3) . ? C5 H5 0.9300 . ? C6 C9 1.506(3) . ? C7 O1 1.220(3) . ? C7 N1 1.333(2) . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? N1 H1 0.80(3) . ? 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 121.81(16) . . ? C6 C1 N1 118.23(15) . . ? C2 C1 N1 119.96(14) . . ? C3 C2 C1 117.83(16) . . ? C3 C2 C8 119.99(16) . . ? C1 C2 C8 122.16(16) . . ? C4 C3 C2 121.17(19) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 119.96(18) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 121.24(17) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 117.97(16) . . ? C1 C6 C9 120.92(18) . . ? C5 C6 C9 121.11(17) . . ? O1 C7 N1 125.78(17) . . ? O1 C7 H7 117.1 . . ? N1 C7 H7 117.1 . . ? C2 C8 H8A 109.5 . . ? C2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 N1 C1 124.15(14) . . ? C7 N1 H1 115.0(15) . . ? C1 N1 H1 119.5(15) . . ? 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 C1 C2 C3 1.5(2) . . . . ? N1 C1 C2 C3 -179.25(15) . . . . ? C6 C1 C2 C8 -177.09(17) . . . . ? N1 C1 C2 C8 2.1(3) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? C8 C2 C3 C4 177.2(2) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? N1 C1 C6 C5 -179.70(15) . . . . ? C2 C1 C6 C9 179.91(17) . . . . ? N1 C1 C6 C9 0.7(2) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? C4 C5 C6 C9 178.9(2) . . . . ? O1 C7 N1 C1 -4.6(3) . . . . ? C6 C1 N1 C7 -111.3(2) . . . . ? C2 C1 N1 C7 69.4(2) . . . . ? 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 N1 H1 O1 0.80(3) 2.11(3) 2.854(2) 154(2) 1_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.109 _refine_diff_density_min -0.111 _refine_diff_density_rms 0.026