# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_o-chlorobenzylamine #data_k147 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 Cl N O2' _chemical_formula_weight 313.77 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.615(2) _cell_length_b 6.0317(7) _cell_length_c 29.072(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.908(2) _cell_angle_gamma 90.00 _cell_volume 3139.2(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2133 _cell_measurement_theta_min 2.3415 _cell_measurement_theta_max 24.4465 _exptl_crystal_description column _exptl_crystal_colour colorless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8812 _exptl_absorpt_correction_T_max 0.9852 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 67 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8350 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3066 _reflns_number_gt 2066 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0502P)^2^+0.9064P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3066 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0796 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _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 0.31842(11) 0.1887(3) 0.88767(6) 0.0330(5) Uani 1 1 d . . . C2 C 0.28685(12) -0.0220(3) 0.89020(7) 0.0399(5) Uani 1 1 d . . . H2 H 0.3068 -0.1134 0.9173 0.048 Uiso 1 1 calc R . . C3 C 0.22835(12) -0.0961(3) 0.85443(7) 0.0408(5) Uani 1 1 d . . . H3 H 0.2073 -0.2372 0.8572 0.049 Uiso 1 1 calc R . . C4 C 0.19837(11) 0.0334(3) 0.81313(7) 0.0360(5) Uani 1 1 d . . . C5 C 0.13755(12) -0.0365(4) 0.77501(8) 0.0484(6) Uani 1 1 d . . . H5 H 0.1144 -0.1752 0.7770 0.058 Uiso 1 1 calc R . . C6 C 0.11170(13) 0.0926(4) 0.73550(8) 0.0552(7) Uani 1 1 d . . . H6 H 0.0709 0.0427 0.7102 0.066 Uiso 1 1 calc R . . C7 C 0.14459(13) 0.2978(4) 0.73180(8) 0.0520(6) Uani 1 1 d . . . H7 H 0.1266 0.3853 0.7038 0.062 Uiso 1 1 calc R . . C8 C 0.20238(12) 0.3727(4) 0.76818(7) 0.0418(5) Uani 1 1 d . . . H8 H 0.2238 0.5135 0.7657 0.050 Uiso 1 1 calc R . . C9 C 0.23066(11) 0.2428(3) 0.80964(6) 0.0338(5) Uani 1 1 d . . . C10 C 0.29055(11) 0.3167(3) 0.84795(6) 0.0340(5) Uani 1 1 d . . . H10 H 0.3119 0.4583 0.8460 0.041 Uiso 1 1 calc R . . C11 C 0.38195(11) 0.2760(4) 0.92735(7) 0.0371(5) Uani 1 1 d . . . C12 C 0.41633(11) 0.7867(4) 0.08188(7) 0.0395(5) Uani 1 1 d . . . C13 C 0.37255(12) 0.9733(4) 0.08108(7) 0.0432(5) Uani 1 1 d . . . C14 C 0.38393(14) 1.1154(4) 0.11937(8) 0.0522(6) Uani 1 1 d . . . H14 H 0.3538 1.2440 0.1176 0.063 Uiso 1 1 calc R . . C15 C 0.43929(15) 1.0690(5) 0.16014(9) 0.0621(7) Uani 1 1 d . . . H15 H 0.4477 1.1660 0.1868 0.075 Uiso 1 1 calc R . . C16 C 0.48269(14) 0.8826(5) 0.16260(9) 0.0607(7) Uani 1 1 d . . . H16 H 0.5204 0.8495 0.1912 0.073 Uiso 1 1 calc R . . C17 C 0.47159(12) 0.7439(4) 0.12368(8) 0.0509(6) Uani 1 1 d . . . H17 H 0.5024 0.6168 0.1255 0.061 Uiso 1 1 calc R . . C18 C 0.40575(13) 0.6355(4) 0.03957(7) 0.0464(6) Uani 1 1 d . . . H18A H 0.4301 0.4914 0.0503 0.056 Uiso 1 1 calc R . . H18B H 0.3517 0.6081 0.0255 0.056 Uiso 1 1 calc R . . Cl1 Cl 0.29979(4) 1.03332(12) 0.03082(2) 0.0682(3) Uani 1 1 d . . . N1 N 0.43783(9) 0.7318(3) 0.00261(5) 0.0398(4) Uani 1 1 d . . . H1A H 0.4155 0.8642 -0.0073 0.060 Uiso 1 1 calc R . . H1B H 0.4298 0.6375 -0.0227 0.060 Uiso 1 1 calc R . . H1C H 0.4878 0.7526 0.0152 0.060 Uiso 1 1 calc R . . O1 O 0.41305(8) 0.1489(3) 0.96109(5) 0.0515(4) Uani 1 1 d . . . O2 O 0.40164(9) 0.4733(2) 0.92468(5) 0.0488(4) 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 0.0375(11) 0.0310(11) 0.0299(10) -0.0030(9) 0.0081(9) 0.0014(9) C2 0.0475(13) 0.0349(12) 0.0336(11) 0.0065(9) 0.0050(10) 0.0010(10) C3 0.0478(13) 0.0284(12) 0.0450(13) 0.0001(9) 0.0107(10) -0.0048(10) C4 0.0364(12) 0.0364(12) 0.0343(11) -0.0062(9) 0.0080(9) -0.0003(9) C5 0.0449(13) 0.0439(14) 0.0524(14) -0.0113(11) 0.0066(11) -0.0067(11) C6 0.0480(14) 0.0651(17) 0.0421(14) -0.0118(12) -0.0055(11) -0.0008(12) C7 0.0562(15) 0.0568(16) 0.0366(12) 0.0048(11) 0.0017(11) 0.0114(13) C8 0.0473(13) 0.0406(13) 0.0355(12) 0.0012(10) 0.0082(10) 0.0029(10) C9 0.0353(11) 0.0343(12) 0.0308(10) -0.0015(9) 0.0075(8) 0.0036(9) C10 0.0385(12) 0.0281(11) 0.0354(11) -0.0015(9) 0.0101(9) -0.0018(9) C11 0.0405(12) 0.0383(13) 0.0313(11) -0.0025(10) 0.0078(9) 0.0012(10) C12 0.0379(12) 0.0405(13) 0.0400(12) 0.0021(10) 0.0105(10) -0.0051(10) C13 0.0407(13) 0.0471(14) 0.0435(12) 0.0044(11) 0.0142(10) 0.0003(11) C14 0.0593(16) 0.0472(14) 0.0557(15) -0.0025(12) 0.0253(13) 0.0038(12) C15 0.0729(18) 0.0649(18) 0.0509(15) -0.0173(13) 0.0209(14) -0.0087(15) C16 0.0556(16) 0.079(2) 0.0422(14) -0.0013(14) 0.0039(11) -0.0012(14) C17 0.0493(14) 0.0529(15) 0.0498(14) 0.0035(12) 0.0122(11) 0.0046(12) C18 0.0523(14) 0.0366(13) 0.0494(13) -0.0017(11) 0.0122(11) -0.0065(11) Cl1 0.0550(4) 0.0807(5) 0.0617(4) 0.0085(4) 0.0041(3) 0.0177(3) N1 0.0458(11) 0.0320(10) 0.0355(9) -0.0021(8) 0.0008(8) 0.0010(8) O1 0.0494(10) 0.0487(10) 0.0453(9) 0.0120(8) -0.0060(7) -0.0021(8) O2 0.0608(10) 0.0358(9) 0.0409(8) -0.0033(7) -0.0013(7) -0.0074(8) _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 C10 1.368(3) . ? C1 C2 1.410(3) . ? C1 C11 1.503(3) . ? C2 C3 1.359(3) . ? C2 H2 0.9500 . ? C3 C4 1.413(3) . ? C3 H3 0.9500 . ? C4 C5 1.414(3) . ? C4 C9 1.414(3) . ? C5 C6 1.362(3) . ? C5 H5 0.9500 . ? C6 C7 1.398(3) . ? C6 H6 0.9500 . ? C7 C8 1.363(3) . ? C7 H7 0.9500 . ? C8 C9 1.413(3) . ? C8 H8 0.9500 . ? C9 C10 1.415(3) . ? C10 H10 0.9500 . ? C11 O2 1.254(2) . ? C11 O1 1.254(2) . ? C12 C17 1.384(3) . ? C12 C13 1.386(3) . ? C12 C18 1.500(3) . ? C13 C14 1.375(3) . ? C13 Cl1 1.737(2) . ? C14 C15 1.369(3) . ? C14 H14 0.9500 . ? C15 C16 1.375(4) . ? C15 H15 0.9500 . ? C16 C17 1.376(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 N1 1.483(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? 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 C10 C1 C2 119.04(18) . . ? C10 C1 C11 119.15(18) . . ? C2 C1 C11 121.81(17) . . ? C3 C2 C1 120.98(18) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 121.02(19) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 123.1(2) . . ? C3 C4 C9 118.57(18) . . ? C5 C4 C9 118.33(19) . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 120.7(2) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.2(2) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C4 119.35(18) . . ? C8 C9 C10 121.74(19) . . ? C4 C9 C10 118.91(18) . . ? C1 C10 C9 121.45(19) . . ? C1 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? O2 C11 O1 123.26(19) . . ? O2 C11 C1 117.82(18) . . ? O1 C11 C1 118.91(19) . . ? C17 C12 C13 117.3(2) . . ? C17 C12 C18 120.4(2) . . ? C13 C12 C18 122.37(19) . . ? C14 C13 C12 122.2(2) . . ? C14 C13 Cl1 117.57(18) . . ? C12 C13 Cl1 120.20(17) . . ? C15 C14 C13 119.1(2) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 120.3(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C17 120.0(2) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 121.1(2) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? N1 C18 C12 111.57(17) . . ? N1 C18 H18A 109.3 . . ? C12 C18 H18A 109.3 . . ? N1 C18 H18B 109.3 . . ? C12 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C18 N1 H1A 109.5 . . ? C18 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C18 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? 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 C10 C1 C2 C3 -1.6(3) . . . . ? C11 C1 C2 C3 178.54(19) . . . . ? C1 C2 C3 C4 1.4(3) . . . . ? C2 C3 C4 C5 -180.0(2) . . . . ? C2 C3 C4 C9 0.1(3) . . . . ? C3 C4 C5 C6 -178.6(2) . . . . ? C9 C4 C5 C6 1.3(3) . . . . ? C4 C5 C6 C7 -0.2(4) . . . . ? C5 C6 C7 C8 -1.0(4) . . . . ? C6 C7 C8 C9 1.1(3) . . . . ? C7 C8 C9 C4 0.0(3) . . . . ? C7 C8 C9 C10 -180.0(2) . . . . ? C3 C4 C9 C8 178.75(19) . . . . ? C5 C4 C9 C8 -1.2(3) . . . . ? C3 C4 C9 C10 -1.3(3) . . . . ? C5 C4 C9 C10 178.74(19) . . . . ? C2 C1 C10 C9 0.4(3) . . . . ? C11 C1 C10 C9 -179.79(17) . . . . ? C8 C9 C10 C1 -178.99(19) . . . . ? C4 C9 C10 C1 1.1(3) . . . . ? C10 C1 C11 O2 7.6(3) . . . . ? C2 C1 C11 O2 -172.63(19) . . . . ? C10 C1 C11 O1 -171.79(19) . . . . ? C2 C1 C11 O1 8.0(3) . . . . ? C17 C12 C13 C14 1.7(3) . . . . ? C18 C12 C13 C14 -177.9(2) . . . . ? C17 C12 C13 Cl1 -177.62(16) . . . . ? C18 C12 C13 Cl1 2.8(3) . . . . ? C12 C13 C14 C15 -1.5(4) . . . . ? Cl1 C13 C14 C15 177.90(19) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C14 C15 C16 C17 1.3(4) . . . . ? C15 C16 C17 C12 -1.0(4) . . . . ? C13 C12 C17 C16 -0.5(3) . . . . ? C18 C12 C17 C16 179.1(2) . . . . ? C17 C12 C18 N1 -102.5(2) . . . . ? C13 C12 C18 N1 77.1(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 H1A O1 0.91 1.94 2.774(2) 151.1 1_564 N1 H1B O2 0.91 1.78 2.679(2) 171.7 1_554 N1 H1C O1 0.91 1.88 2.781(2) 169.4 5_666 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.178 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 965542' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_m-chlorobenzylamine #data_k148 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 Cl N O2' _chemical_formula_weight 313.77 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 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 10.5204(7) _cell_length_b 8.7184(6) _cell_length_c 33.531(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3075.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6516 _cell_measurement_theta_min 2.2855 _cell_measurement_theta_max 27.5575 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8853 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 206 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17697 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.93 _reflns_number_total 3610 _reflns_number_gt 2827 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0840P)^2^+0.8037P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3610 _refine_ls_number_parameters 200 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.492 _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 0.4107(2) 0.2225(3) 0.40308(6) 0.0330(5) Uani 1 1 d . . . C2 C 0.5031(2) 0.3059(3) 0.38169(7) 0.0444(6) Uani 1 1 d . . . H2 H 0.5532 0.3805 0.3951 0.053 Uiso 1 1 calc R . . C3 C 0.5215(3) 0.2807(3) 0.34204(8) 0.0525(7) Uani 1 1 d . . . H3 H 0.5842 0.3380 0.3281 0.063 Uiso 1 1 calc R . . C4 C 0.4488(3) 0.1707(3) 0.32145(7) 0.0470(6) Uani 1 1 d . . . C5 C 0.4632(4) 0.1424(4) 0.27992(9) 0.0702(10) Uani 1 1 d . . . H5 H 0.5250 0.1979 0.2652 0.084 Uiso 1 1 calc R . . C6 C 0.3901(5) 0.0377(4) 0.26127(9) 0.0811(12) Uani 1 1 d . . . H6 H 0.4004 0.0209 0.2335 0.097 Uiso 1 1 calc R . . C7 C 0.2992(4) -0.0464(4) 0.28248(10) 0.0796(11) Uani 1 1 d . . . H7 H 0.2487 -0.1203 0.2690 0.095 Uiso 1 1 calc R . . C8 C 0.2826(3) -0.0232(4) 0.32215(9) 0.0616(8) Uani 1 1 d . . . H8 H 0.2209 -0.0814 0.3363 0.074 Uiso 1 1 calc R . . C9 C 0.3560(3) 0.0862(3) 0.34248(7) 0.0423(6) Uani 1 1 d . . . C10 C 0.3396(2) 0.1152(3) 0.38378(7) 0.0370(5) Uani 1 1 d . . . H10 H 0.2778 0.0585 0.3983 0.044 Uiso 1 1 calc R . . C11 C 0.3913(2) 0.2532(3) 0.44680(7) 0.0333(5) Uani 1 1 d . . . C12 C 0.3551(2) 0.0424(2) 0.57002(7) 0.0340(5) Uani 1 1 d . . . C13 C 0.3294(2) 0.0623(3) 0.61015(7) 0.0400(5) Uani 1 1 d . . . H13 H 0.2653 0.0031 0.6228 0.048 Uiso 1 1 calc R . . C14 C 0.3983(3) 0.1694(3) 0.63158(8) 0.0479(6) Uani 1 1 d U . . C15 C 0.4925(3) 0.2551(3) 0.61435(9) 0.0516(7) Uani 1 1 d . . . H15 H 0.5391 0.3278 0.6296 0.062 Uiso 1 1 calc R . . C16 C 0.5186(2) 0.2338(3) 0.57444(8) 0.0489(6) Uani 1 1 d . . . H16 H 0.5838 0.2921 0.5620 0.059 Uiso 1 1 calc R . . C17 C 0.4504(2) 0.1283(3) 0.55247(7) 0.0393(5) Uani 1 1 d . . . H17 H 0.4691 0.1146 0.5250 0.047 Uiso 1 1 calc R . . C18 C 0.2814(2) -0.0737(3) 0.54615(8) 0.0417(6) Uani 1 1 d . . . H18A H 0.3414 -0.1370 0.5305 0.050 Uiso 1 1 calc R . . H18B H 0.2351 -0.1425 0.5646 0.050 Uiso 1 1 calc R . . Cl1 Cl 0.36560(10) 0.19521(14) 0.68179(2) 0.0854(4) Uani 1 1 d U . . N1 N 0.18911(18) -0.0003(2) 0.51867(5) 0.0358(5) Uani 1 1 d . . . H1A H 0.1291 0.0505 0.5331 0.054 Uiso 1 1 calc R . . H1B H 0.1510 -0.0735 0.5035 0.054 Uiso 1 1 calc R . . H1C H 0.2306 0.0672 0.5026 0.054 Uiso 1 1 calc R . . O1 O 0.46607(17) 0.3437(2) 0.46386(5) 0.0482(5) Uani 1 1 d . . . O2 O 0.30066(17) 0.1908(2) 0.46408(5) 0.0497(5) 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 0.0340(10) 0.0346(11) 0.0304(10) 0.0021(9) -0.0017(8) 0.0045(9) C2 0.0466(14) 0.0443(14) 0.0424(13) 0.0013(11) 0.0007(11) -0.0092(11) C3 0.0594(16) 0.0535(16) 0.0446(14) 0.0084(12) 0.0127(12) -0.0121(13) C4 0.0644(17) 0.0413(13) 0.0354(12) 0.0011(10) 0.0061(11) 0.0029(12) C5 0.110(3) 0.0599(18) 0.0403(15) 0.0020(14) 0.0178(16) 0.0018(19) C6 0.149(4) 0.0607(19) 0.0332(14) -0.0091(13) 0.0007(18) 0.005(2) C7 0.128(3) 0.062(2) 0.0489(17) -0.0147(16) -0.0148(19) -0.010(2) C8 0.084(2) 0.0520(17) 0.0487(15) -0.0074(13) -0.0060(15) -0.0112(15) C9 0.0541(14) 0.0348(12) 0.0381(12) 0.0000(9) -0.0024(10) 0.0016(11) C10 0.0389(12) 0.0360(12) 0.0363(12) 0.0017(9) 0.0010(9) -0.0013(10) C11 0.0322(11) 0.0355(11) 0.0322(11) 0.0003(9) -0.0028(9) 0.0061(9) C12 0.0312(10) 0.0301(10) 0.0407(12) 0.0022(9) -0.0045(9) 0.0053(9) C13 0.0344(11) 0.0439(13) 0.0417(12) 0.0058(10) -0.0006(9) 0.0003(10) C14 0.0460(13) 0.0588(16) 0.0388(10) -0.0048(11) -0.0085(10) 0.0085(12) C15 0.0473(14) 0.0475(14) 0.0601(16) -0.0089(13) -0.0170(13) -0.0037(12) C16 0.0391(13) 0.0479(14) 0.0598(16) 0.0083(12) -0.0043(12) -0.0081(11) C17 0.0360(11) 0.0422(13) 0.0397(12) 0.0050(10) -0.0012(9) 0.0022(10) C18 0.0433(13) 0.0313(12) 0.0505(14) -0.0011(10) -0.0047(10) 0.0014(10) Cl1 0.0836(6) 0.1291(8) 0.0434(4) -0.0213(4) -0.0038(4) 0.0033(5) N1 0.0356(10) 0.0373(10) 0.0345(10) -0.0049(8) -0.0005(8) -0.0044(8) O1 0.0465(10) 0.0539(11) 0.0443(10) -0.0127(8) -0.0016(8) -0.0061(8) O2 0.0454(10) 0.0706(13) 0.0332(9) 0.0052(8) 0.0045(7) -0.0083(9) _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 C10 1.361(3) . ? C1 C2 1.411(3) . ? C1 C11 1.504(3) . ? C2 C3 1.361(4) . ? C2 H2 0.9500 . ? C3 C4 1.408(4) . ? C3 H3 0.9500 . ? C4 C9 1.411(4) . ? C4 C5 1.422(4) . ? C5 C6 1.347(5) . ? C5 H5 0.9500 . ? C6 C7 1.399(6) . ? C6 H6 0.9500 . ? C7 C8 1.357(4) . ? C7 H7 0.9500 . ? C8 C9 1.403(4) . ? C8 H8 0.9500 . ? C9 C10 1.418(3) . ? C10 H10 0.9500 . ? C11 O2 1.241(3) . ? C11 O1 1.253(3) . ? C12 C17 1.383(3) . ? C12 C13 1.383(3) . ? C12 C18 1.505(3) . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 C15 1.370(4) . ? C14 Cl1 1.733(3) . ? C15 C16 1.379(4) . ? C15 H15 0.9500 . ? C16 C17 1.379(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 N1 1.483(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? 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 C10 C1 C2 119.4(2) . . ? C10 C1 C11 120.8(2) . . ? C2 C1 C11 119.8(2) . . ? C3 C2 C1 120.8(2) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 120.8(2) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C9 119.1(2) . . ? C3 C4 C5 122.7(3) . . ? C9 C4 C5 118.2(3) . . ? C6 C5 C4 120.7(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 120.6(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.4(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C8 C9 C4 119.5(2) . . ? C8 C9 C10 121.9(2) . . ? C4 C9 C10 118.6(2) . . ? C1 C10 C9 121.3(2) . . ? C1 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? O2 C11 O1 123.0(2) . . ? O2 C11 C1 118.7(2) . . ? O1 C11 C1 118.2(2) . . ? C17 C12 C13 119.2(2) . . ? C17 C12 C18 120.8(2) . . ? C13 C12 C18 120.1(2) . . ? C14 C13 C12 119.2(2) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C15 C14 C13 121.9(2) . . ? C15 C14 Cl1 118.9(2) . . ? C13 C14 Cl1 119.2(2) . . ? C14 C15 C16 118.7(2) . . ? C14 C15 H15 120.7 . . ? C16 C15 H15 120.7 . . ? C15 C16 C17 120.3(2) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C12 120.7(2) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? N1 C18 C12 112.19(18) . . ? N1 C18 H18A 109.2 . . ? C12 C18 H18A 109.2 . . ? N1 C18 H18B 109.2 . . ? C12 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C18 N1 H1A 109.5 . . ? C18 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C18 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? 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 C10 C1 C2 C3 0.3(4) . . . . ? C11 C1 C2 C3 -179.5(2) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C2 C3 C4 C9 0.0(4) . . . . ? C2 C3 C4 C5 178.9(3) . . . . ? C3 C4 C5 C6 -178.9(3) . . . . ? C9 C4 C5 C6 0.0(5) . . . . ? C4 C5 C6 C7 -0.6(6) . . . . ? C5 C6 C7 C8 0.4(6) . . . . ? C6 C7 C8 C9 0.3(6) . . . . ? C7 C8 C9 C4 -0.9(5) . . . . ? C7 C8 C9 C10 178.9(3) . . . . ? C3 C4 C9 C8 179.7(3) . . . . ? C5 C4 C9 C8 0.7(4) . . . . ? C3 C4 C9 C10 -0.1(4) . . . . ? C5 C4 C9 C10 -179.1(3) . . . . ? C2 C1 C10 C9 -0.5(4) . . . . ? C11 C1 C10 C9 179.4(2) . . . . ? C8 C9 C10 C1 -179.4(3) . . . . ? C4 C9 C10 C1 0.4(4) . . . . ? C10 C1 C11 O2 -7.5(3) . . . . ? C2 C1 C11 O2 172.3(2) . . . . ? C10 C1 C11 O1 174.2(2) . . . . ? C2 C1 C11 O1 -6.0(3) . . . . ? C17 C12 C13 C14 1.0(3) . . . . ? C18 C12 C13 C14 180.0(2) . . . . ? C12 C13 C14 C15 -0.9(4) . . . . ? C12 C13 C14 Cl1 179.63(18) . . . . ? C13 C14 C15 C16 0.3(4) . . . . ? Cl1 C14 C15 C16 179.8(2) . . . . ? C14 C15 C16 C17 0.2(4) . . . . ? C15 C16 C17 C12 0.0(4) . . . . ? C13 C12 C17 C16 -0.6(3) . . . . ? C18 C12 C17 C16 -179.5(2) . . . . ? C17 C12 C18 N1 -74.2(3) . . . . ? C13 C12 C18 N1 106.9(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 H1A O1 0.91 1.95 2.777(3) 150.2 4_456 N1 H1B O1 0.91 1.95 2.809(3) 156.8 8_655 N1 H1C O2 0.91 1.84 2.739(3) 171.6 . _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.362 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 965543' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_o-bromobenzylamine #data_im1775a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 Br N O2' _chemical_formula_weight 358.23 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.6370(18) _cell_length_b 11.658(4) _cell_length_c 15.392(5) _cell_angle_alpha 67.925(12) _cell_angle_beta 82.161(15) _cell_angle_gamma 85.996(18) _cell_volume 763.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2811 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 30.91 _exptl_crystal_description Needle _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.558 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 2.698 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5758 _exptl_absorpt_correction_T_max 0.7378 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Rigaku Saturn' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5471 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 30.91 _reflns_number_total 3268 _reflns_number_gt 2811 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0640P)^2^+4.9229P] 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 3268 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0757 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1759 _refine_ls_wR_factor_gt 0.1611 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.000 _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 0.6538(11) 0.3449(5) 0.3034(4) 0.0207(10) Uani 1 1 d . . . H1 H 0.5918 0.2946 0.2735 0.025 Uiso 1 1 calc R . . C2 C 0.5538(11) 0.3219(5) 0.3965(4) 0.0179(9) Uani 1 1 d . . . C3 C 0.6417(11) 0.3969(5) 0.4416(3) 0.0187(9) Uani 1 1 d . . . H3 H 0.5682 0.3821 0.5055 0.022 Uiso 1 1 calc R . . C4 C 0.8330(12) 0.4910(5) 0.3936(4) 0.0231(11) Uani 1 1 d . . . H4 H 0.8915 0.5408 0.4245 0.028 Uiso 1 1 calc R . . C5 C 1.1502(12) 0.6092(5) 0.2480(4) 0.0238(11) Uani 1 1 d . . . H5 H 1.2150 0.6587 0.2781 0.029 Uiso 1 1 calc R . . C6 C 1.2539(13) 0.6285(5) 0.1569(5) 0.0310(13) Uani 1 1 d . . . H6 H 1.3894 0.6925 0.1241 0.037 Uiso 1 1 calc R . . C7 C 1.1671(14) 0.5567(5) 0.1094(4) 0.0296(12) Uani 1 1 d . . . H7 H 1.2469 0.5708 0.0461 0.036 Uiso 1 1 calc R . . C8 C 0.9650(12) 0.4656(5) 0.1558(4) 0.0256(11) Uani 1 1 d . . . H8 H 0.9029 0.4177 0.1240 0.031 Uiso 1 1 calc R . . C9 C 0.8487(11) 0.4429(4) 0.2511(4) 0.0179(9) Uani 1 1 d . . . C10 C 0.9435(11) 0.5144(5) 0.2985(4) 0.0212(10) Uani 1 1 d . . . C11 C 0.3553(10) 0.2140(5) 0.4523(4) 0.0176(9) Uani 1 1 d . . . O12 O 0.3491(8) 0.1297(3) 0.4182(3) 0.0210(7) Uani 1 1 d . . . O13 O 0.2171(8) 0.2120(3) 0.5276(3) 0.0231(8) Uani 1 1 d . . . C21 C 0.2309(11) 0.0136(5) 0.2404(4) 0.0178(9) Uani 1 1 d . . . C22 C 0.3539(12) 0.0549(5) 0.1459(4) 0.0207(10) Uani 1 1 d . . . C23 C 0.5813(11) -0.0049(5) 0.1115(4) 0.0225(10) Uani 1 1 d . . . H23 H 0.6568 0.0267 0.0466 0.027 Uiso 1 1 calc R . . C24 C 0.6985(12) -0.1134(5) 0.1747(4) 0.0227(10) Uani 1 1 d . . . H24 H 0.8548 -0.1564 0.1526 0.027 Uiso 1 1 calc R . . C25 C 0.5863(11) -0.1583(5) 0.2697(4) 0.0208(10) Uani 1 1 d . . . H25 H 0.6665 -0.2317 0.3124 0.025 Uiso 1 1 calc R . . C26 C 0.3542(11) -0.0949(5) 0.3022(3) 0.0190(10) Uani 1 1 d . . . H26 H 0.2792 -0.1260 0.3672 0.023 Uiso 1 1 calc R . . C27 C -0.0187(11) 0.0842(4) 0.2703(3) 0.0180(9) Uani 1 1 d . . . H27A H -0.1879 0.0811 0.2384 0.022 Uiso 1 1 calc R . . H27B H 0.0351 0.1720 0.2494 0.022 Uiso 1 1 calc R . . N28 N -0.1058(9) 0.0351(4) 0.3748(3) 0.0167(8) Uani 1 1 d . . . H28A H -0.1153 -0.0488 0.3966 0.025 Uiso 1 1 calc R . . H28B H -0.2833 0.0675 0.3878 0.025 Uiso 1 1 calc R . . H28C H 0.0282 0.0569 0.4035 0.025 Uiso 1 1 calc R . . Br29 Br 0.20010(13) 0.20166(5) 0.05683(4) 0.02772(18) 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 0.021(2) 0.017(2) 0.026(2) -0.010(2) -0.0009(19) -0.001(2) C2 0.014(2) 0.016(2) 0.023(2) -0.0066(19) -0.0017(17) 0.0033(18) C3 0.019(2) 0.018(2) 0.018(2) -0.0076(19) 0.0022(18) 0.0010(19) C4 0.023(3) 0.022(2) 0.027(3) -0.013(2) -0.001(2) -0.002(2) C5 0.018(2) 0.015(2) 0.036(3) -0.007(2) -0.003(2) 0.002(2) C6 0.023(3) 0.021(3) 0.039(3) -0.003(2) 0.007(2) -0.001(2) C7 0.031(3) 0.026(3) 0.024(3) -0.005(2) 0.006(2) 0.001(2) C8 0.024(3) 0.027(3) 0.023(3) -0.007(2) 0.001(2) 0.002(2) C9 0.015(2) 0.010(2) 0.025(2) -0.0037(18) -0.0019(18) 0.0055(18) C10 0.020(2) 0.015(2) 0.026(3) -0.006(2) -0.0022(19) 0.002(2) C11 0.013(2) 0.017(2) 0.022(2) -0.0080(19) -0.0001(17) 0.0055(18) O12 0.0201(17) 0.0176(17) 0.0268(18) -0.0105(15) 0.0005(14) -0.0033(14) O13 0.027(2) 0.0162(16) 0.0235(18) -0.0064(14) 0.0057(15) -0.0026(15) C21 0.016(2) 0.015(2) 0.024(2) -0.0091(19) -0.0006(18) -0.0019(18) C22 0.023(2) 0.017(2) 0.023(2) -0.0084(19) -0.0012(19) -0.008(2) C23 0.017(2) 0.030(3) 0.025(2) -0.016(2) 0.0027(18) -0.005(2) C24 0.021(2) 0.021(2) 0.030(3) -0.015(2) -0.001(2) 0.001(2) C25 0.022(2) 0.017(2) 0.025(2) -0.010(2) -0.0027(19) -0.002(2) C26 0.019(2) 0.019(2) 0.017(2) -0.0051(19) 0.0008(17) -0.0011(19) C27 0.019(2) 0.013(2) 0.019(2) -0.0042(18) -0.0021(18) 0.0004(19) N28 0.0143(18) 0.0148(18) 0.0182(19) -0.0048(15) 0.0016(14) 0.0030(15) Br29 0.0291(3) 0.0255(3) 0.0229(3) -0.0044(2) 0.00209(19) 0.0002(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.374(7) . ? C1 C9 1.423(7) . ? C2 C3 1.413(7) . ? C2 C11 1.517(7) . ? C3 C4 1.373(7) . ? C4 C10 1.411(7) . ? C5 C6 1.357(8) . ? C5 C10 1.429(7) . ? C6 C7 1.408(9) . ? C7 C8 1.379(8) . ? C8 C9 1.423(7) . ? C9 C10 1.420(7) . ? C11 O13 1.239(6) . ? C11 O12 1.279(6) . ? C21 C22 1.400(7) . ? C21 C26 1.406(7) . ? C21 C27 1.495(7) . ? C22 C23 1.378(8) . ? C22 Br29 1.910(6) . ? C23 C24 1.402(8) . ? C24 C25 1.392(7) . ? C25 C26 1.405(8) . ? C27 N28 1.498(6) . ? 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 C9 121.1(5) . . ? C1 C2 C3 120.0(4) . . ? C1 C2 C11 120.4(4) . . ? C3 C2 C11 119.6(4) . . ? C4 C3 C2 120.3(5) . . ? C3 C4 C10 120.6(5) . . ? C6 C5 C10 120.0(5) . . ? C5 C6 C7 122.1(5) . . ? C8 C7 C6 119.3(5) . . ? C7 C8 C9 120.5(5) . . ? C10 C9 C8 119.5(5) . . ? C10 C9 C1 118.1(5) . . ? C8 C9 C1 122.3(5) . . ? C4 C10 C9 119.8(5) . . ? C4 C10 C5 121.6(5) . . ? C9 C10 C5 118.6(5) . . ? O13 C11 O12 124.8(5) . . ? O13 C11 C2 118.5(4) . . ? O12 C11 C2 116.7(4) . . ? C22 C21 C26 116.4(5) . . ? C22 C21 C27 119.8(5) . . ? C26 C21 C27 123.8(4) . . ? C23 C22 C21 124.0(5) . . ? C23 C22 Br29 116.8(4) . . ? C21 C22 Br29 119.2(4) . . ? C22 C23 C24 118.3(5) . . ? C25 C24 C23 120.2(5) . . ? C24 C25 C26 119.9(5) . . ? C25 C26 C21 121.2(5) . . ? C21 C27 N28 113.1(4) . . ? _diffrn_measured_fraction_theta_max 0.674 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.857 _refine_diff_density_max 1.570 _refine_diff_density_min -1.056 _refine_diff_density_rms 0.162 _database_code_depnum_ccdc_archive 'CCDC 965544' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_m-bromobenzylamine #data_k244 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 Br N O2' _chemical_formula_weight 358.23 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' Br Br -0.2901 2.4595 '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 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 10.6279(9) _cell_length_b 8.7139(7) _cell_length_c 33.989(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3147.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4203 _cell_measurement_theta_min 2.260 _cell_measurement_theta_max 24.849 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 2.618 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4132 _exptl_absorpt_correction_T_max 0.9256 _exptl_absorpt_process_details ; SADABS; Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number 149 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17795 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3586 _reflns_number_gt 2312 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0400P)^2^+3.2614P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3586 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Br1 Br 0.13606(5) 0.78470(7) 0.182554(12) 0.0858(2) Uani 1 1 d . . . C1 C 0.6595(3) 0.6125(4) 0.11456(9) 0.0395(7) Uani 1 1 d . . . H1 H 0.7207 0.5559 0.1002 0.047 Uiso 1 1 calc R . . C2 C 0.5899(3) 0.7208(3) 0.09555(8) 0.0334(6) Uani 1 1 d . . . C3 C 0.4996(3) 0.8053(4) 0.11713(10) 0.0459(8) Uani 1 1 d . . . H3 H 0.4505 0.8809 0.1041 0.055 Uiso 1 1 calc R . . C4 C 0.4820(4) 0.7799(4) 0.15622(10) 0.0549(9) Uani 1 1 d . . . H4 H 0.4209 0.8381 0.1701 0.066 Uiso 1 1 calc R . . C5 C 0.5381(5) 0.6371(5) 0.21734(11) 0.0720(12) Uani 1 1 d . . . H5 H 0.4771 0.6921 0.2321 0.086 Uiso 1 1 calc R . . C6 C 0.6102(5) 0.5298(5) 0.23531(12) 0.0818(15) Uani 1 1 d . . . H6 H 0.6004 0.5119 0.2627 0.098 Uiso 1 1 calc R . . C7 C 0.6979(5) 0.4461(5) 0.21424(12) 0.0815(14) Uani 1 1 d . . . H7 H 0.7468 0.3702 0.2272 0.098 Uiso 1 1 calc R . . C8 C 0.7149(4) 0.4714(4) 0.17497(11) 0.0628(11) Uani 1 1 d . . . H8 H 0.7759 0.4135 0.1609 0.075 Uiso 1 1 calc R . . C9 C 0.5532(4) 0.6683(4) 0.17633(9) 0.0481(8) Uani 1 1 d . . . C10 C 0.6431(3) 0.5822(4) 0.15521(9) 0.0427(8) Uani 1 1 d . . . C11 C 0.6077(3) 0.7527(4) 0.05247(9) 0.0367(7) Uani 1 1 d . . . C12 C 0.1455(3) 0.9560(3) 0.06899(9) 0.0350(7) Uani 1 1 d . . . C13 C 0.1708(3) 0.9305(4) 0.10848(9) 0.0409(7) Uani 1 1 d . . . H13 H 0.2355 0.9863 0.1214 0.049 Uiso 1 1 calc R . . C14 C 0.1004(3) 0.8227(4) 0.12880(10) 0.0462(8) Uani 1 1 d . . . C15 C 0.0057(3) 0.7415(4) 0.11108(11) 0.0508(9) Uani 1 1 d . . . H15 H -0.0414 0.6682 0.1256 0.061 Uiso 1 1 calc R . . C16 C -0.0202(3) 0.7676(4) 0.07206(10) 0.0471(8) Uani 1 1 d . . . H16 H -0.0860 0.7125 0.0595 0.057 Uiso 1 1 calc R . . C17 C 0.0493(3) 0.8736(4) 0.05104(9) 0.0396(7) Uani 1 1 d . . . H17 H 0.0311 0.8905 0.0240 0.047 Uiso 1 1 calc R . . C18 C 0.2206(3) 1.0724(3) 0.04618(10) 0.0406(7) Uani 1 1 d . . . H18A H 0.1623 1.1386 0.0311 0.049 Uiso 1 1 calc R . . H18B H 0.2673 1.1385 0.0648 0.049 Uiso 1 1 calc R . . N1 N 0.3115(2) 0.9995(3) 0.01853(7) 0.0371(6) Uani 1 1 d . . . H1A H 0.3693 0.9448 0.0324 0.056 Uiso 1 1 calc R . . H1B H 0.3512 1.0736 0.0043 0.056 Uiso 1 1 calc R . . H1C H 0.2694 0.9356 0.0019 0.056 Uiso 1 1 calc R . . O1 O 0.6985(2) 0.6908(3) 0.03525(6) 0.0493(6) Uani 1 1 d . . . O2 O 0.5333(2) 0.8433(3) 0.03584(6) 0.0487(6) 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 Br1 0.0833(3) 0.1294(5) 0.0448(2) 0.0224(3) 0.0058(2) 0.0008(3) C1 0.0416(18) 0.0365(17) 0.0404(17) -0.0021(14) 0.0007(13) 0.0016(14) C2 0.0326(14) 0.0342(16) 0.0332(15) -0.0019(13) -0.0017(12) -0.0045(13) C3 0.0491(19) 0.0431(19) 0.0454(18) -0.0021(16) 0.0018(15) 0.0080(16) C4 0.062(2) 0.054(2) 0.048(2) -0.0079(18) 0.0144(17) 0.0134(19) C5 0.112(4) 0.061(3) 0.043(2) -0.006(2) 0.015(2) -0.005(3) C6 0.153(5) 0.058(3) 0.034(2) 0.0072(19) -0.002(3) -0.002(3) C7 0.133(4) 0.059(3) 0.052(2) 0.009(2) -0.015(3) 0.012(3) C8 0.087(3) 0.054(2) 0.048(2) 0.0061(18) -0.005(2) 0.013(2) C9 0.065(2) 0.0391(19) 0.0408(19) -0.0015(15) 0.0053(17) -0.0056(17) C10 0.052(2) 0.0343(17) 0.0417(17) 0.0020(14) -0.0033(15) -0.0036(16) C11 0.0332(15) 0.0387(18) 0.0383(16) 0.0004(14) -0.0024(13) -0.0066(14) C12 0.0338(16) 0.0264(15) 0.0448(17) -0.0032(13) 0.0054(13) 0.0040(13) C13 0.0331(16) 0.0434(18) 0.0461(19) -0.0085(15) -0.0009(13) 0.0009(14) C14 0.0455(18) 0.052(2) 0.0408(18) 0.0040(16) 0.0071(15) 0.0062(17) C15 0.0458(19) 0.048(2) 0.059(2) 0.0044(17) 0.0133(16) -0.0038(17) C16 0.0382(17) 0.0420(19) 0.061(2) -0.0089(17) 0.0038(16) -0.0069(16) C17 0.0348(16) 0.0419(18) 0.0420(17) -0.0024(15) -0.0014(14) 0.0064(14) C18 0.0413(18) 0.0312(16) 0.0493(19) -0.0004(14) 0.0027(14) 0.0017(14) N1 0.0357(13) 0.0376(14) 0.0380(14) 0.0049(12) 0.0023(11) -0.0056(12) O1 0.0416(12) 0.0702(16) 0.0362(12) -0.0033(11) 0.0025(10) 0.0067(12) O2 0.0455(13) 0.0541(14) 0.0465(13) 0.0120(11) -0.0034(10) 0.0044(12) _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 Br1 C14 1.895(3) . ? C1 C2 1.363(4) . ? C1 C10 1.417(4) . ? C1 H1 0.9500 . ? C2 C3 1.414(4) . ? C2 C11 1.503(4) . ? C3 C4 1.360(5) . ? C3 H3 0.9500 . ? C4 C9 1.410(5) . ? C4 H4 0.9500 . ? C5 C6 1.354(6) . ? C5 C9 1.429(5) . ? C5 H5 0.9500 . ? C6 C7 1.384(6) . ? C6 H6 0.9500 . ? C7 C8 1.365(5) . ? C7 H7 0.9500 . ? C8 C10 1.402(5) . ? C8 H8 0.9500 . ? C9 C10 1.411(5) . ? C11 O1 1.251(4) . ? C11 O2 1.253(4) . ? C12 C13 1.387(4) . ? C12 C17 1.390(4) . ? C12 C18 1.506(4) . ? C13 C14 1.385(5) . ? C13 H13 0.9500 . ? C14 C15 1.370(5) . ? C15 C16 1.373(5) . ? C15 H15 0.9500 . ? C16 C17 1.382(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 N1 1.490(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? 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 C10 121.6(3) . . ? C2 C1 H1 119.2 . . ? C10 C1 H1 119.2 . . ? C1 C2 C3 118.9(3) . . ? C1 C2 C11 121.4(3) . . ? C3 C2 C11 119.7(3) . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C9 120.8(3) . . ? C3 C4 H4 119.6 . . ? C9 C4 H4 119.6 . . ? C6 C5 C9 120.5(4) . . ? C6 C5 H5 119.8 . . ? C9 C5 H5 119.8 . . ? C5 C6 C7 120.8(4) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.6(4) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C10 120.5(4) . . ? C7 C8 H8 119.7 . . ? C10 C8 H8 119.7 . . ? C4 C9 C10 118.9(3) . . ? C4 C9 C5 122.9(3) . . ? C10 C9 C5 118.1(3) . . ? C8 C10 C9 119.4(3) . . ? C8 C10 C1 121.9(3) . . ? C9 C10 C1 118.7(3) . . ? O1 C11 O2 123.2(3) . . ? O1 C11 C2 118.3(3) . . ? O2 C11 C2 118.5(3) . . ? C13 C12 C17 119.0(3) . . ? C13 C12 C18 120.2(3) . . ? C17 C12 C18 120.8(3) . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C15 C14 C13 121.9(3) . . ? C15 C14 Br1 118.7(3) . . ? C13 C14 Br1 119.4(3) . . ? C14 C15 C16 119.1(3) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C15 C16 C17 120.2(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 120.7(3) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? N1 C18 C12 112.4(2) . . ? N1 C18 H18A 109.1 . . ? C12 C18 H18A 109.1 . . ? N1 C18 H18B 109.1 . . ? C12 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C18 N1 H1A 109.5 . . ? C18 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C18 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? 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 C10 C1 C2 C3 0.4(5) . . . . ? C10 C1 C2 C11 179.9(3) . . . . ? C1 C2 C3 C4 0.1(5) . . . . ? C11 C2 C3 C4 -179.5(3) . . . . ? C2 C3 C4 C9 -0.1(6) . . . . ? C9 C5 C6 C7 -1.3(7) . . . . ? C5 C6 C7 C8 0.9(8) . . . . ? C6 C7 C8 C10 -0.4(7) . . . . ? C3 C4 C9 C10 -0.3(6) . . . . ? C3 C4 C9 C5 -179.9(4) . . . . ? C6 C5 C9 C4 -179.2(4) . . . . ? C6 C5 C9 C10 1.2(6) . . . . ? C7 C8 C10 C9 0.4(6) . . . . ? C7 C8 C10 C1 179.2(4) . . . . ? C4 C9 C10 C8 179.7(3) . . . . ? C5 C9 C10 C8 -0.7(5) . . . . ? C4 C9 C10 C1 0.8(5) . . . . ? C5 C9 C10 C1 -179.6(3) . . . . ? C2 C1 C10 C8 -179.7(3) . . . . ? C2 C1 C10 C9 -0.8(5) . . . . ? C1 C2 C11 O1 -8.5(4) . . . . ? C3 C2 C11 O1 171.0(3) . . . . ? C1 C2 C11 O2 173.6(3) . . . . ? C3 C2 C11 O2 -6.9(4) . . . . ? C17 C12 C13 C14 0.7(4) . . . . ? C18 C12 C13 C14 -179.9(3) . . . . ? C12 C13 C14 C15 -0.6(5) . . . . ? C12 C13 C14 Br1 179.0(2) . . . . ? C13 C14 C15 C16 0.1(5) . . . . ? Br1 C14 C15 C16 -179.5(3) . . . . ? C14 C15 C16 C17 0.4(5) . . . . ? C15 C16 C17 C12 -0.4(5) . . . . ? C13 C12 C17 C16 -0.2(4) . . . . ? C18 C12 C17 C16 -179.6(3) . . . . ? C13 C12 C18 N1 106.3(3) . . . . ? C17 C12 C18 N1 -74.3(4) . . . . ? 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 H1A O2 0.91 1.96 2.785(3) 150.3 . N1 H1B O2 0.91 1.97 2.830(3) 156.4 5_675 N1 H1C O1 0.91 1.84 2.745(3) 173.9 4_465 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.553 _refine_diff_density_min -0.574 _refine_diff_density_rms 0.059 _database_code_depnum_ccdc_archive 'CCDC 965545' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_o-methylbenzylamine #data_im1770a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 N O2' _chemical_formula_weight 293.35 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.404(5) _cell_length_b 6.0250(15) _cell_length_c 28.832(8) _cell_angle_alpha 90.00 _cell_angle_beta 104.628(3) _cell_angle_gamma 90.00 _cell_volume 3093.4(14) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1631 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 30.91 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9791 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Rigaku Saturn' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7027 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0991 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 30.91 _reflns_number_total 3124 _reflns_number_gt 1631 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0730P)^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_number_reflns 3124 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1497 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.000 _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 0.21064(14) 0.3016(4) 0.15246(9) 0.0180(6) Uani 1 1 d . . . H1 H 0.1897 0.4435 0.1552 0.022 Uiso 1 1 calc R . . C2 C 0.18248(14) 0.1775(4) 0.11173(9) 0.0168(6) Uani 1 1 d . . . C3 C 0.21267(15) -0.0363(4) 0.10821(10) 0.0204(6) Uani 1 1 d . . . H3 H 0.1925 -0.1249 0.0807 0.025 Uiso 1 1 calc R . . C4 C 0.27043(15) -0.1169(4) 0.14390(10) 0.0211(6) Uani 1 1 d . . . H4 H 0.2904 -0.2598 0.1407 0.025 Uiso 1 1 calc R . . C5 C 0.36167(15) -0.0660(4) 0.22312(10) 0.0222(6) Uani 1 1 d . . . H5 H 0.3842 -0.2054 0.2202 0.027 Uiso 1 1 calc R . . C6 C 0.38788(15) 0.0603(4) 0.26330(10) 0.0262(7) Uani 1 1 d . . . H6 H 0.4284 0.0072 0.2881 0.031 Uiso 1 1 calc R . . C7 C 0.35554(16) 0.2679(4) 0.26835(9) 0.0257(7) Uani 1 1 d . . . H7 H 0.3735 0.3520 0.2968 0.031 Uiso 1 1 calc R . . C8 C 0.29840(15) 0.3483(4) 0.23233(9) 0.0207(6) Uani 1 1 d . . . H8 H 0.2775 0.4899 0.2356 0.025 Uiso 1 1 calc R . . C9 C 0.27008(14) 0.2230(4) 0.19028(9) 0.0179(6) Uani 1 1 d . . . C10 C 0.30084(15) 0.0104(4) 0.18565(10) 0.0196(6) Uani 1 1 d . . . C11 C 0.12131(14) 0.2730(4) 0.07168(9) 0.0186(6) Uani 1 1 d . . . O12 O 0.09197(10) 0.1506(3) 0.03621(7) 0.0242(5) Uani 1 1 d . . . O13 O 0.10218(11) 0.4716(3) 0.07541(7) 0.0236(5) Uani 1 1 d . . . C21 C 0.41745(15) 0.7014(4) 0.08301(9) 0.0206(6) Uani 1 1 d . . . C22 C 0.37165(15) 0.5147(4) 0.08118(10) 0.0224(6) Uani 1 1 d . . . C23 C 0.38619(16) 0.3693(5) 0.11961(10) 0.0267(7) Uani 1 1 d . . . H23 H 0.3558 0.2407 0.1182 0.032 Uiso 1 1 calc R . . C24 C 0.44391(16) 0.4071(5) 0.16004(11) 0.0289(7) Uani 1 1 d . . . H24 H 0.4534 0.3039 0.1858 0.035 Uiso 1 1 calc R . . C25 C 0.48773(16) 0.5956(5) 0.16289(11) 0.0282(7) Uani 1 1 d . . . H25 H 0.5261 0.6257 0.1911 0.034 Uiso 1 1 calc R . . C26 C 0.47514(15) 0.7405(4) 0.12425(10) 0.0250(7) Uani 1 1 d . . . H26 H 0.5061 0.8679 0.1258 0.030 Uiso 1 1 calc R . . C27 C 0.40710(16) 0.8611(4) 0.04160(10) 0.0235(6) Uani 1 1 d . . . H27A H 0.3528 0.8894 0.0282 0.028 Uiso 1 1 calc R . . H27B H 0.4315 1.0041 0.0532 0.028 Uiso 1 1 calc R . . C28 C 0.30406(16) 0.4751(5) 0.03946(10) 0.0282(7) Uani 1 1 d . . . H28A H 0.2701 0.6026 0.0359 0.042 Uiso 1 1 calc R . . H28B H 0.2777 0.3409 0.0455 0.042 Uiso 1 1 calc R . . H28C H 0.3207 0.4560 0.0100 0.042 Uiso 1 1 calc R . . N29 N 0.44009(12) 0.7712(3) 0.00299(8) 0.0209(5) Uani 1 1 d . . . H29A H 0.4903 0.7500 0.0149 0.031 Uiso 1 1 calc R . . H29B H 0.4322 0.8694 -0.0218 0.031 Uiso 1 1 calc R . . H29C H 0.4178 0.6395 -0.0077 0.031 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 0.0195(13) 0.0155(12) 0.0200(15) 0.0012(11) 0.0068(12) 0.0012(11) C2 0.0173(13) 0.0173(13) 0.0163(14) 0.0022(11) 0.0049(12) -0.0011(11) C3 0.0227(14) 0.0193(13) 0.0178(15) -0.0011(11) 0.0025(12) -0.0024(12) C4 0.0268(15) 0.0179(13) 0.0201(15) 0.0005(12) 0.0090(13) 0.0008(12) C5 0.0199(14) 0.0227(14) 0.0240(16) 0.0058(12) 0.0058(13) 0.0034(12) C6 0.0228(15) 0.0282(16) 0.0240(16) 0.0069(13) -0.0008(13) 0.0002(13) C7 0.0275(15) 0.0294(16) 0.0189(16) -0.0033(13) 0.0033(13) -0.0062(13) C8 0.0228(14) 0.0185(14) 0.0206(16) -0.0003(11) 0.0049(13) -0.0007(11) C9 0.0177(13) 0.0174(13) 0.0184(15) 0.0024(11) 0.0039(12) -0.0024(11) C10 0.0212(13) 0.0203(13) 0.0184(15) 0.0034(11) 0.0068(12) -0.0012(11) C11 0.0185(13) 0.0210(14) 0.0162(14) 0.0037(12) 0.0044(12) -0.0026(11) O12 0.0228(10) 0.0243(10) 0.0226(11) -0.0019(9) 0.0004(9) -0.0008(8) O13 0.0287(11) 0.0176(9) 0.0207(11) 0.0027(8) -0.0009(9) 0.0027(8) C21 0.0193(13) 0.0224(14) 0.0210(16) -0.0014(12) 0.0069(13) 0.0005(12) C22 0.0221(14) 0.0258(15) 0.0222(16) -0.0008(12) 0.0108(13) -0.0004(12) C23 0.0298(16) 0.0245(15) 0.0288(18) 0.0026(13) 0.0128(15) -0.0037(13) C24 0.0327(17) 0.0295(16) 0.0269(17) 0.0053(14) 0.0119(15) 0.0077(14) C25 0.0271(16) 0.0340(16) 0.0212(17) 0.0000(14) 0.0020(14) 0.0052(14) C26 0.0231(15) 0.0243(15) 0.0282(17) -0.0059(13) 0.0076(14) -0.0019(12) C27 0.0263(15) 0.0208(14) 0.0238(16) 0.0024(12) 0.0068(13) 0.0036(12) C28 0.0268(15) 0.0320(16) 0.0261(17) -0.0007(14) 0.0074(14) -0.0044(13) N29 0.0221(12) 0.0186(11) 0.0199(12) 0.0025(10) 0.0016(10) -0.0007(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.378(3) . ? C1 C9 1.417(4) . ? C2 C3 1.416(3) . ? C2 C11 1.508(4) . ? C3 C4 1.368(4) . ? C4 C10 1.418(4) . ? C5 C6 1.368(4) . ? C5 C10 1.422(4) . ? C6 C7 1.408(4) . ? C7 C8 1.367(4) . ? C8 C9 1.411(3) . ? C9 C10 1.421(3) . ? C11 O13 1.260(3) . ? C11 O12 1.265(3) . ? C21 C22 1.399(4) . ? C21 C26 1.400(4) . ? C21 C27 1.507(4) . ? C22 C23 1.384(4) . ? C22 C28 1.515(4) . ? C23 C24 1.383(4) . ? C24 C25 1.384(4) . ? C25 C26 1.388(4) . ? C27 N29 1.498(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 C9 121.7(2) . . ? C1 C2 C3 119.0(2) . . ? C1 C2 C11 119.5(2) . . ? C3 C2 C11 121.5(2) . . ? C4 C3 C2 120.9(3) . . ? C3 C4 C10 120.8(2) . . ? C6 C5 C10 120.3(3) . . ? C5 C6 C7 120.9(3) . . ? C8 C7 C6 120.0(3) . . ? C7 C8 C9 120.6(2) . . ? C8 C9 C1 121.9(2) . . ? C8 C9 C10 119.6(2) . . ? C1 C9 C10 118.5(2) . . ? C4 C10 C9 119.1(2) . . ? C4 C10 C5 122.4(2) . . ? C9 C10 C5 118.5(3) . . ? O13 C11 O12 123.4(2) . . ? O13 C11 C2 117.9(2) . . ? O12 C11 C2 118.7(2) . . ? C22 C21 C26 119.2(2) . . ? C22 C21 C27 121.9(2) . . ? C26 C21 C27 118.8(2) . . ? C23 C22 C21 119.1(3) . . ? C23 C22 C28 119.3(2) . . ? C21 C22 C28 121.5(2) . . ? C24 C23 C22 121.5(3) . . ? C23 C24 C25 119.8(3) . . ? C24 C25 C26 119.5(3) . . ? C25 C26 C21 120.9(3) . . ? N29 C27 C21 111.3(2) . . ? _diffrn_measured_fraction_theta_max 0.638 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.778 _refine_diff_density_max 0.256 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.066 _database_code_depnum_ccdc_archive 'CCDC 965546' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_m-methylbenzylamine #data_im1772a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H19 N O2' _chemical_formula_weight 293.35 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.604(4) _cell_length_b 6.2630(14) _cell_length_c 15.601(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.680(3) _cell_angle_gamma 90.00 _cell_volume 1524.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3501 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 30.91 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9693 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Rigaku Saturn' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11871 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 30.91 _reflns_number_total 4208 _reflns_number_gt 3501 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0689P)^2^+0.3558P] 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 4208 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _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 0.32169(6) 0.24710(17) 0.70773(6) 0.0163(2) Uani 1 1 d . . . H1 H 0.3123 0.3813 0.7344 0.020 Uiso 1 1 calc R . . C2 C 0.25533(6) 0.10274(16) 0.70138(6) 0.0156(2) Uani 1 1 d . . . C3 C 0.26916(6) -0.09792(17) 0.66170(7) 0.0184(2) Uani 1 1 d . . . H3 H 0.2233 -0.1971 0.6569 0.022 Uiso 1 1 calc R . . C4 C 0.34835(7) -0.15021(17) 0.63010(7) 0.0185(2) Uani 1 1 d . . . H4 H 0.3567 -0.2857 0.6042 0.022 Uiso 1 1 calc R . . C5 C 0.50053(7) -0.05218(18) 0.60405(7) 0.0205(2) Uani 1 1 d . . . H5 H 0.5108 -0.1869 0.5782 0.025 Uiso 1 1 calc R . . C6 C 0.56578(7) 0.0940(2) 0.61042(7) 0.0230(2) Uani 1 1 d . . . H6 H 0.6207 0.0597 0.5887 0.028 Uiso 1 1 calc R . . C7 C 0.55198(7) 0.29523(19) 0.64903(7) 0.0226(2) Uani 1 1 d . . . H7 H 0.5977 0.3951 0.6532 0.027 Uiso 1 1 calc R . . C8 C 0.47276(7) 0.34671(18) 0.68050(7) 0.0196(2) Uani 1 1 d . . . H8 H 0.4639 0.4824 0.7061 0.024 Uiso 1 1 calc R . . C9 C 0.40403(6) 0.19831(17) 0.67497(6) 0.0160(2) Uani 1 1 d . . . C10 C 0.41764(6) -0.00394(17) 0.63583(6) 0.0168(2) Uani 1 1 d . . . C11 C 0.16753(6) 0.16698(16) 0.73160(6) 0.0156(2) Uani 1 1 d . . . O12 O 0.16053(5) 0.33548(12) 0.77446(5) 0.02003(17) Uani 1 1 d . . . O13 O 0.10410(5) 0.05042(12) 0.70893(5) 0.01954(17) Uani 1 1 d . . . C21 C 0.08804(6) 0.59899(18) 0.55674(7) 0.0187(2) Uani 1 1 d . . . C22 C 0.14937(6) 0.44371(17) 0.53860(7) 0.0180(2) Uani 1 1 d . . . H22 H 0.1487 0.3123 0.5690 0.022 Uiso 1 1 calc R . . C23 C 0.21168(6) 0.47835(18) 0.47651(7) 0.0186(2) Uani 1 1 d . . . C24 C 0.20900(7) 0.66961(18) 0.43036(7) 0.0218(2) Uani 1 1 d . . . H24 H 0.2491 0.6930 0.3860 0.026 Uiso 1 1 calc R . . C25 C 0.14877(8) 0.82592(19) 0.44820(7) 0.0239(2) Uani 1 1 d . . . H25 H 0.1481 0.9556 0.4166 0.029 Uiso 1 1 calc R . . C26 C 0.08932(7) 0.79182(19) 0.51250(7) 0.0226(2) Uani 1 1 d . . . H26 H 0.0494 0.9007 0.5263 0.027 Uiso 1 1 calc R . . C27 C 0.02062(7) 0.5591(2) 0.62326(7) 0.0232(2) Uani 1 1 d . . . H27A H -0.0326 0.6353 0.6064 0.028 Uiso 1 1 calc R . . H27B H 0.0075 0.4045 0.6250 0.028 Uiso 1 1 calc R . . C28 C 0.28007(7) 0.3142(2) 0.46031(8) 0.0255(2) Uani 1 1 d . . . H28A H 0.2715 0.1914 0.4982 0.038 Uiso 1 1 calc R . . H28B H 0.3366 0.3771 0.4718 0.038 Uiso 1 1 calc R . . H28C H 0.2766 0.2674 0.4004 0.038 Uiso 1 1 calc R . . N29 N 0.04815(5) 0.63117(14) 0.71064(6) 0.01704(18) Uani 1 1 d . . . H29A H 0.0882 0.5395 0.7321 0.026 Uiso 1 1 calc R . . H29B H 0.0020 0.6334 0.7458 0.026 Uiso 1 1 calc R . . H29C H 0.0710 0.7646 0.7073 0.026 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 0.0161(4) 0.0162(4) 0.0167(4) -0.0003(4) 0.0015(3) 0.0014(4) C2 0.0136(4) 0.0171(5) 0.0162(4) 0.0006(4) 0.0010(3) 0.0017(4) C3 0.0148(4) 0.0191(5) 0.0213(5) -0.0012(4) -0.0001(4) 0.0001(4) C4 0.0172(5) 0.0172(5) 0.0212(5) -0.0036(4) 0.0005(4) 0.0020(4) C5 0.0176(5) 0.0224(5) 0.0214(5) -0.0024(4) 0.0029(4) 0.0033(4) C6 0.0156(5) 0.0293(6) 0.0242(5) 0.0001(4) 0.0043(4) 0.0025(4) C7 0.0164(5) 0.0259(5) 0.0255(5) 0.0010(4) 0.0030(4) -0.0031(4) C8 0.0173(5) 0.0208(5) 0.0208(5) -0.0008(4) 0.0014(4) -0.0011(4) C9 0.0146(4) 0.0181(5) 0.0153(4) 0.0011(4) 0.0000(3) 0.0006(4) C10 0.0148(4) 0.0192(5) 0.0164(4) -0.0001(4) 0.0006(3) 0.0021(4) C11 0.0144(4) 0.0167(4) 0.0158(4) 0.0023(3) 0.0014(3) 0.0017(3) O12 0.0184(4) 0.0204(4) 0.0213(4) -0.0036(3) 0.0010(3) 0.0034(3) O13 0.0138(3) 0.0197(4) 0.0253(4) -0.0009(3) 0.0033(3) -0.0010(3) C21 0.0146(4) 0.0249(5) 0.0165(4) -0.0009(4) -0.0004(4) -0.0004(4) C22 0.0177(5) 0.0196(5) 0.0167(4) 0.0010(4) -0.0003(4) -0.0016(4) C23 0.0150(4) 0.0232(5) 0.0175(5) -0.0010(4) -0.0001(3) -0.0002(4) C24 0.0185(5) 0.0268(5) 0.0200(5) 0.0027(4) 0.0018(4) -0.0056(4) C25 0.0268(6) 0.0215(5) 0.0234(5) 0.0055(4) -0.0040(4) -0.0025(4) C26 0.0204(5) 0.0233(5) 0.0240(5) -0.0007(4) -0.0030(4) 0.0041(4) C27 0.0147(5) 0.0347(6) 0.0203(5) -0.0039(4) 0.0022(4) -0.0032(4) C28 0.0224(5) 0.0303(6) 0.0238(5) -0.0016(5) 0.0037(4) 0.0056(4) N29 0.0139(4) 0.0180(4) 0.0194(4) -0.0008(3) 0.0031(3) 0.0009(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.3773(14) . ? C1 C9 1.4216(14) . ? C2 C3 1.4185(15) . ? C2 C11 1.5088(14) . ? C3 C4 1.3754(14) . ? C4 C10 1.4191(15) . ? C5 C6 1.3720(16) . ? C5 C10 1.4231(14) . ? C6 C7 1.4145(17) . ? C7 C8 1.3739(15) . ? C8 C9 1.4210(14) . ? C9 C10 1.4232(15) . ? C11 O12 1.2547(13) . ? C11 O13 1.2764(12) . ? C21 C26 1.3913(16) . ? C21 C22 1.3957(15) . ? C21 C27 1.5074(15) . ? C22 C23 1.3974(14) . ? C23 C24 1.3980(16) . ? C23 C28 1.5052(16) . ? C24 C25 1.3875(17) . ? C25 C26 1.3909(16) . ? C27 N29 1.4944(14) . ? 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 C9 120.99(9) . . ? C1 C2 C3 119.66(9) . . ? C1 C2 C11 119.15(9) . . ? C3 C2 C11 121.06(9) . . ? C4 C3 C2 120.62(10) . . ? C3 C4 C10 120.71(10) . . ? C6 C5 C10 120.66(10) . . ? C5 C6 C7 120.58(10) . . ? C8 C7 C6 120.23(10) . . ? C7 C8 C9 120.43(10) . . ? C8 C9 C1 121.48(10) . . ? C8 C9 C10 119.46(9) . . ? C1 C9 C10 119.06(9) . . ? C4 C10 C5 122.41(10) . . ? C4 C10 C9 118.95(9) . . ? C5 C10 C9 118.64(9) . . ? O12 C11 O13 123.82(9) . . ? O12 C11 C2 118.41(9) . . ? O13 C11 C2 117.71(9) . . ? C26 C21 C22 119.37(10) . . ? C26 C21 C27 119.98(10) . . ? C22 C21 C27 120.65(10) . . ? C21 C22 C23 121.11(10) . . ? C22 C23 C24 118.25(10) . . ? C22 C23 C28 120.73(10) . . ? C24 C23 C28 121.03(10) . . ? C25 C24 C23 121.15(10) . . ? C24 C25 C26 119.71(11) . . ? C25 C26 C21 120.30(10) . . ? N29 C27 C21 112.49(9) . . ? _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.390 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.052 #===END _database_code_depnum_ccdc_archive 'CCDC 965547'