Electronic Supplementary MAterial for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 # SUBMISSION DETAILS _publ_contact_author_name 'Professor Gautam R. Desiraju' _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad 500 046, India ; _publ_contact_author_email desiraju@uohyd.ernet.in _publ_contact_author_phone '91 40 23010500 extn. 4828' _publ_contact_author_fax '91 40 3010567' _publ_requested_journal CrystEngComm # TITLE AND AUTHOR LIST _publ_section_title ; Dimorphs of 4'-Amino-4-Hydroxy-2-Methylbiphenyl: Assessment of Likelihood of Polymorphism in Flexible Molecules. ; loop_ _publ_author_name _publ_author_address 'Archan Dey' ;School of Chemistry University of Hyderabad Hyderabad 500 046, India ; 'Gautam R. Desiraju' ;School of Chemistry University of Hyderabad Hyderabad 500 046, India ; data_FORM-I _database_code_depnum_ccdc_archive 'CCDC 605385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-amino-2-methyl-4'-hydroxydiphenyl ; _chemical_name_common 4-amino-2-methyl-4'-hydroxydiphenyl _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N O' _chemical_formula_sum 'C13 H13 N O' _chemical_formula_weight 199.24 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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc ' 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 11.1587(4) _cell_length_b 18.9115(7) _cell_length_c 10.3217(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.8320(10) _cell_angle_gamma 90.00 _cell_volume 2048.98(13) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4120 _cell_measurement_theta_min 2.358 _cell_measurement_theta_max 25.893 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.082 _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 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART-CCD' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 22422 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0451 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4703 _reflns_number_gt 2967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0566P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 'not refined' _refine_ls_number_reflns 4703 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0771 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1172 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 O1 O 0.77578(10) 0.16204(6) 0.64405(13) 0.0365(3) Uani 1 1 d . . . H1 H 0.755(2) 0.1813(12) 0.714(2) 0.076(8) Uiso 1 1 d . . . C1 C 0.90589(14) 0.16391(8) 0.67888(16) 0.0277(4) Uani 1 1 d . . . C2 C 0.95577(15) 0.15997(8) 0.57324(17) 0.0298(4) Uani 1 1 d . . . H2 H 0.9002 0.1555 0.4807 0.036 Uiso 1 1 calc R . . C3 C 1.08598(15) 0.16255(8) 0.60174(16) 0.0285(4) Uani 1 1 d . . . H3 H 1.1185 0.1596 0.5279 0.034 Uiso 1 1 calc R . . C4 C 1.17129(14) 0.16944(8) 0.73652(16) 0.0253(3) Uani 1 1 d . . . C5 C 1.11834(15) 0.17147(8) 0.84127(16) 0.0275(4) Uani 1 1 d . . . H5 H 1.1736 0.1745 0.9342 0.033 Uiso 1 1 calc R . . C6 C 0.98826(15) 0.16924(8) 0.81414(16) 0.0298(4) Uani 1 1 d . . . H6 H 0.9553 0.1713 0.8877 0.036 Uiso 1 1 calc R . . C7 C 1.30962(14) 0.18089(8) 0.76360(16) 0.0253(3) Uani 1 1 d . . . C8 C 1.34457(15) 0.22999(8) 0.68150(17) 0.0306(4) Uani 1 1 d . . . H8 H 1.2795 0.2522 0.6083 0.037 Uiso 1 1 calc R . . C9 C 1.47009(15) 0.24749(9) 0.70274(17) 0.0318(4) Uani 1 1 d . . . H9 H 1.4907 0.2802 0.6436 0.038 Uiso 1 1 calc R . . C10 C 1.56554(14) 0.21668(9) 0.81152(16) 0.0286(4) Uani 1 1 d . . . C11 C 1.53357(15) 0.16691(8) 0.89292(16) 0.0285(4) Uani 1 1 d . . . H11 H 1.5994 0.1451 0.9659 0.034 Uiso 1 1 calc R . . C12 C 1.40726(14) 0.14802(8) 0.87039(16) 0.0267(3) Uani 1 1 d . . . C13 C 1.38136(17) 0.09088(9) 0.96127(19) 0.0414(4) Uani 1 1 d . . . H13A H 1.4567 0.0607 0.9978 0.062 Uiso 1 1 calc R . . H13B H 1.3087 0.0621 0.9068 0.062 Uiso 1 1 calc R . . H13C H 1.3620 0.1130 1.0377 0.062 Uiso 1 1 calc R . . N1 N 1.69539(14) 0.23418(9) 0.83411(17) 0.0344(4) Uani 1 1 d . . . H1A H 1.740(2) 0.2311(11) 0.922(2) 0.061(7) Uiso 1 1 d . . . H1B H 1.7006(19) 0.2777(12) 0.805(2) 0.059(7) Uiso 1 1 d . . . O20 O -0.28579(10) 0.11247(6) 0.22244(12) 0.0338(3) Uani 1 1 d . . . H20 H -0.306(2) 0.0865(12) 0.283(2) 0.073(8) Uiso 1 1 d . . . C21 C -0.16178(14) 0.09926(8) 0.23270(15) 0.0260(3) Uani 1 1 d . . . C22 C -0.09874(14) 0.03704(8) 0.28670(16) 0.0274(4) Uani 1 1 d . . . H22 H -0.1424 0.0001 0.3145 0.033 Uiso 1 1 calc R . . C23 C 0.02760(14) 0.02904(8) 0.29982(16) 0.0277(4) Uani 1 1 d . . . H23 H 0.0698 -0.0138 0.3372 0.033 Uiso 1 1 calc R . . C24 C 0.09591(14) 0.08195(8) 0.25983(15) 0.0254(3) Uani 1 1 d . . . C25 C 0.02981(14) 0.14350(8) 0.20352(15) 0.0273(3) Uani 1 1 d . . . H25 H 0.0728 0.1803 0.1744 0.033 Uiso 1 1 calc R . . C26 C -0.09742(14) 0.15194(8) 0.18929(16) 0.0277(4) Uani 1 1 d . . . H26 H -0.1409 0.1941 0.1496 0.033 Uiso 1 1 calc R . . C27 C 0.23539(14) 0.07385(8) 0.28862(16) 0.0263(3) Uani 1 1 d . . . C28 C 0.31990(15) 0.11986(8) 0.38154(16) 0.0302(4) Uani 1 1 d . . . H28 H 0.2864 0.1586 0.4170 0.036 Uiso 1 1 calc R . . C29 C 0.45047(15) 0.11102(9) 0.42367(17) 0.0320(4) Uani 1 1 d . . . H29 H 0.5055 0.1432 0.4870 0.038 Uiso 1 1 calc R . . C30 C 0.50034(15) 0.05462(9) 0.37239(16) 0.0293(4) Uani 1 1 d . . . C31 C 0.41780(15) 0.01010(9) 0.27535(16) 0.0300(4) Uani 1 1 d . . . H31 H 0.4523 -0.0275 0.2381 0.036 Uiso 1 1 calc R . . C32 C 0.28639(15) 0.01894(8) 0.23122(16) 0.0281(4) Uani 1 1 d . . . C33 C 0.20140(16) -0.02752(9) 0.11746(18) 0.0371(4) Uani 1 1 d . . . H33A H 0.2529 -0.0642 0.0946 0.056 Uiso 1 1 calc R . . H33B H 0.1598 0.0014 0.0357 0.056 Uiso 1 1 calc R . . H33C H 0.1365 -0.0497 0.1485 0.056 Uiso 1 1 calc R . . N20 N 0.63459(13) 0.04383(9) 0.41381(16) 0.0347(4) Uani 1 1 d . . . H20A H 0.6534(19) -0.0038(12) 0.424(2) 0.063(7) Uiso 1 1 d . . . H20B H 0.679(2) 0.0662(11) 0.489(2) 0.064(7) 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 O1 0.0229(6) 0.0496(8) 0.0357(7) -0.0079(6) 0.0084(5) -0.0028(5) C1 0.0220(8) 0.0285(9) 0.0314(9) -0.0036(7) 0.0074(7) -0.0014(6) C2 0.0286(9) 0.0324(9) 0.0251(8) -0.0037(7) 0.0049(7) 0.0011(7) C3 0.0293(9) 0.0317(9) 0.0259(8) -0.0013(7) 0.0112(7) 0.0029(7) C4 0.0265(8) 0.0215(8) 0.0280(8) -0.0004(6) 0.0094(7) 0.0009(6) C5 0.0271(9) 0.0303(9) 0.0239(8) -0.0033(6) 0.0073(7) -0.0035(6) C6 0.0302(9) 0.0336(9) 0.0279(9) -0.0045(7) 0.0128(7) -0.0046(7) C7 0.0265(8) 0.0245(8) 0.0265(8) -0.0018(6) 0.0111(7) 0.0017(6) C8 0.0300(9) 0.0320(9) 0.0295(9) 0.0037(7) 0.0096(7) 0.0032(7) C9 0.0348(10) 0.0323(9) 0.0320(9) 0.0039(7) 0.0162(8) -0.0013(7) C10 0.0265(9) 0.0331(9) 0.0289(8) -0.0074(7) 0.0131(7) -0.0024(7) C11 0.0263(9) 0.0318(9) 0.0262(8) -0.0015(7) 0.0075(7) 0.0029(7) C12 0.0276(8) 0.0263(8) 0.0265(8) -0.0008(6) 0.0098(7) 0.0006(7) C13 0.0387(11) 0.0405(11) 0.0428(11) 0.0108(8) 0.0110(9) 0.0010(8) N1 0.0267(8) 0.0439(10) 0.0342(9) -0.0044(7) 0.0126(7) -0.0077(7) O20 0.0231(6) 0.0439(7) 0.0352(7) 0.0092(6) 0.0108(5) 0.0042(5) C21 0.0215(8) 0.0339(9) 0.0225(8) -0.0014(6) 0.0074(6) -0.0003(6) C22 0.0267(8) 0.0278(8) 0.0292(8) 0.0012(7) 0.0113(7) -0.0035(6) C23 0.0273(9) 0.0239(8) 0.0325(9) 0.0016(7) 0.0108(7) 0.0012(6) C24 0.0258(8) 0.0268(8) 0.0241(8) -0.0036(6) 0.0092(7) -0.0006(6) C25 0.0289(9) 0.0278(8) 0.0262(8) 0.0004(6) 0.0106(7) -0.0043(7) C26 0.0278(9) 0.0278(9) 0.0266(8) 0.0039(6) 0.0079(7) 0.0035(7) C27 0.0266(8) 0.0282(8) 0.0261(8) 0.0030(6) 0.0114(7) -0.0001(6) C28 0.0281(9) 0.0317(9) 0.0326(9) -0.0032(7) 0.0128(7) -0.0026(7) C29 0.0281(9) 0.0371(10) 0.0317(9) -0.0022(7) 0.0113(7) -0.0064(7) C30 0.0243(8) 0.0388(9) 0.0270(8) 0.0083(7) 0.0115(7) -0.0010(7) C31 0.0294(9) 0.0339(9) 0.0316(9) 0.0028(7) 0.0166(7) 0.0031(7) C32 0.0283(9) 0.0313(9) 0.0269(8) 0.0011(6) 0.0120(7) -0.0014(7) C33 0.0359(10) 0.0410(10) 0.0368(10) -0.0085(8) 0.0153(8) -0.0029(8) N20 0.0236(8) 0.0456(10) 0.0353(9) 0.0069(7) 0.0103(7) 0.0006(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3727(18) . ? O1 H1 0.91(2) . ? C1 C2 1.384(2) . ? C1 C6 1.390(2) . ? C2 C3 1.382(2) . ? C2 H2 0.9500 . ? C3 C4 1.400(2) . ? C3 H3 0.9500 . ? C4 C5 1.398(2) . ? C4 C7 1.488(2) . ? C5 C6 1.383(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.399(2) . ? C7 C12 1.405(2) . ? C8 C9 1.382(2) . ? C8 H8 0.9500 . ? C9 C10 1.387(2) . ? C9 H9 0.9500 . ? C10 C11 1.387(2) . ? C10 N1 1.426(2) . ? C11 C12 1.395(2) . ? C11 H11 0.9500 . ? C12 C13 1.522(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 H1A 0.88(2) . ? N1 H1B 0.88(2) . ? O20 C21 1.3744(18) . ? O20 H20 0.88(2) . ? C21 C22 1.387(2) . ? C21 C26 1.388(2) . ? C22 C23 1.378(2) . ? C22 H22 0.9500 . ? C23 C24 1.402(2) . ? C23 H23 0.9500 . ? C24 C25 1.395(2) . ? C24 C27 1.490(2) . ? C25 C26 1.386(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.397(2) . ? C27 C32 1.408(2) . ? C28 C29 1.382(2) . ? C28 H28 0.9500 . ? C29 C30 1.388(2) . ? C29 H29 0.9500 . ? C30 C31 1.391(2) . ? C30 N20 1.426(2) . ? C31 C32 1.390(2) . ? C31 H31 0.9500 . ? C32 C33 1.515(2) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? N20 H20A 0.92(2) . ? N20 H20B 0.88(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 C1 O1 H1 108.5(15) . . ? O1 C1 C2 117.68(14) . . ? O1 C1 C6 123.02(15) . . ? C2 C1 C6 119.30(14) . . ? C3 C2 C1 120.34(15) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 121.74(15) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 116.61(14) . . ? C5 C4 C7 122.31(14) . . ? C3 C4 C7 120.83(14) . . ? C6 C5 C4 122.20(15) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C1 119.77(15) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C8 C7 C12 117.88(14) . . ? C8 C7 C4 117.86(14) . . ? C12 C7 C4 124.19(14) . . ? C9 C8 C7 122.58(15) . . ? C9 C8 H8 118.7 . . ? C7 C8 H8 118.7 . . ? C8 C9 C10 119.10(15) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 119.40(14) . . ? C11 C10 N1 120.96(15) . . ? C9 C10 N1 119.57(15) . . ? C10 C11 C12 121.74(15) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C11 C12 C7 119.23(14) . . ? C11 C12 C13 118.14(14) . . ? C7 C12 C13 122.61(14) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 N1 H1A 109.8(14) . . ? C10 N1 H1B 109.9(13) . . ? H1A N1 H1B 109.5(19) . . ? C21 O20 H20 109.6(15) . . ? O20 C21 C22 123.04(14) . . ? O20 C21 C26 117.54(14) . . ? C22 C21 C26 119.41(14) . . ? C23 C22 C21 119.67(14) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 122.20(14) . . ? C22 C23 H23 118.9 . . ? C24 C23 H23 118.9 . . ? C25 C24 C23 117.05(14) . . ? C25 C24 C27 122.53(14) . . ? C23 C24 C27 120.21(13) . . ? C26 C25 C24 121.21(14) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C21 120.43(14) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C28 C27 C32 118.24(14) . . ? C28 C27 C24 119.27(14) . . ? C32 C27 C24 122.40(14) . . ? C29 C28 C27 122.31(15) . . ? C29 C28 H28 118.8 . . ? C27 C28 H28 118.8 . . ? C28 C29 C30 119.29(15) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C29 C30 C31 119.10(15) . . ? C29 C30 N20 120.79(15) . . ? C31 C30 N20 120.06(15) . . ? C32 C31 C30 122.04(15) . . ? C32 C31 H31 119.0 . . ? C30 C31 H31 119.0 . . ? C31 C32 C27 118.87(14) . . ? C31 C32 C33 119.85(14) . . ? C27 C32 C33 121.19(14) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C30 N20 H20A 110.4(13) . . ? C30 N20 H20B 114.5(14) . . ? H20A N20 H20B 109.1(19) . . ? 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 O1 C1 C2 C3 179.14(14) . . . . ? C6 C1 C2 C3 -1.1(2) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C2 C3 C4 C5 1.8(2) . . . . ? C2 C3 C4 C7 -172.50(14) . . . . ? C3 C4 C5 C6 -2.1(2) . . . . ? C7 C4 C5 C6 172.13(14) . . . . ? C4 C5 C6 C1 0.8(2) . . . . ? O1 C1 C6 C5 -179.43(14) . . . . ? C2 C1 C6 C5 0.8(2) . . . . ? C5 C4 C7 C8 -129.82(16) . . . . ? C3 C4 C7 C8 44.2(2) . . . . ? C5 C4 C7 C12 47.1(2) . . . . ? C3 C4 C7 C12 -138.93(16) . . . . ? C12 C7 C8 C9 -0.7(2) . . . . ? C4 C7 C8 C9 176.37(14) . . . . ? C7 C8 C9 C10 -1.6(2) . . . . ? C8 C9 C10 C11 2.7(2) . . . . ? C8 C9 C10 N1 179.80(15) . . . . ? C9 C10 C11 C12 -1.5(2) . . . . ? N1 C10 C11 C12 -178.58(14) . . . . ? C10 C11 C12 C7 -0.8(2) . . . . ? C10 C11 C12 C13 177.70(15) . . . . ? C8 C7 C12 C11 1.9(2) . . . . ? C4 C7 C12 C11 -174.99(14) . . . . ? C8 C7 C12 C13 -176.56(15) . . . . ? C4 C7 C12 C13 6.6(2) . . . . ? O20 C21 C22 C23 -176.85(14) . . . . ? C26 C21 C22 C23 1.7(2) . . . . ? C21 C22 C23 C24 -0.2(2) . . . . ? C22 C23 C24 C25 -0.9(2) . . . . ? C22 C23 C24 C27 173.98(15) . . . . ? C23 C24 C25 C26 0.6(2) . . . . ? C27 C24 C25 C26 -174.17(14) . . . . ? C24 C25 C26 C21 0.8(2) . . . . ? O20 C21 C26 C25 176.62(14) . . . . ? C22 C21 C26 C25 -2.0(2) . . . . ? C25 C24 C27 C28 60.9(2) . . . . ? C23 C24 C27 C28 -113.78(17) . . . . ? C25 C24 C27 C32 -122.65(17) . . . . ? C23 C24 C27 C32 62.7(2) . . . . ? C32 C27 C28 C29 -3.4(2) . . . . ? C24 C27 C28 C29 173.29(14) . . . . ? C27 C28 C29 C30 0.0(2) . . . . ? C28 C29 C30 C31 2.7(2) . . . . ? C28 C29 C30 N20 -179.90(14) . . . . ? C29 C30 C31 C32 -2.1(2) . . . . ? N20 C30 C31 C32 -179.53(14) . . . . ? C30 C31 C32 C27 -1.2(2) . . . . ? C30 C31 C32 C33 175.34(15) . . . . ? C28 C27 C32 C31 3.9(2) . . . . ? C24 C27 C32 C31 -172.65(14) . . . . ? C28 C27 C32 C33 -172.66(15) . . . . ? C24 C27 C32 C33 10.8(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.226 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.042 data_FORM-II _database_code_depnum_ccdc_archive 'CCDC 605386' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-amino-2-methyl-4'-hydroxydiphenyl ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H13 N O' _chemical_formula_sum 'C13 H13 N O' _chemical_formula_weight 199.24 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 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 11.1587(2) _cell_length_b 9.5748(2) _cell_length_c 19.9175(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.3320(10) _cell_angle_gamma 90.00 _cell_volume 2115.05(7) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3274 _cell_measurement_theta_min 2.201 _cell_measurement_theta_max 27.239 _exptl_crystal_description block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _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 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 16432 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0475 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4855 _reflns_number_gt 2929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0578P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4855 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.0984 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 O1 O 0.38007(10) 0.56281(12) 0.23858(5) 0.0308(3) Uani 1 1 d . . . H1A H 0.3930(18) 0.484(2) 0.2171(9) 0.055(6) Uiso 1 1 d . . . C1 C 0.46399(14) 0.57071(15) 0.29460(7) 0.0242(3) Uani 1 1 d . . . C2 C 0.46924(15) 0.69317(15) 0.33181(7) 0.0277(4) Uani 1 1 d . . . H2 H 0.4182 0.7671 0.3183 0.033 Uiso 1 1 calc R . . C3 C 0.55045(15) 0.70520(15) 0.38902(7) 0.0272(4) Uani 1 1 d . . . H3 H 0.5525 0.7874 0.4140 0.033 Uiso 1 1 calc R . . C4 C 0.62980(14) 0.59697(15) 0.41043(7) 0.0239(3) Uani 1 1 d . . . C5 C 0.62377(15) 0.47541(15) 0.37129(7) 0.0267(4) Uani 1 1 d . . . H5 H 0.6760 0.4020 0.3840 0.032 Uiso 1 1 calc R . . C6 C 0.54237(15) 0.46160(15) 0.31442(7) 0.0260(4) Uani 1 1 d . . . H6 H 0.5398 0.3795 0.2893 0.031 Uiso 1 1 calc R . . C7 C 0.71551(15) 0.61313(14) 0.47243(7) 0.0240(3) Uani 1 1 d . . . C8 C 0.67237(15) 0.62062(15) 0.53559(7) 0.0261(3) Uani 1 1 d . . . H8 H 0.5901 0.6109 0.5383 0.031 Uiso 1 1 calc R . . C9 C 0.74887(15) 0.64203(15) 0.59417(7) 0.0281(4) Uani 1 1 d . . . H9 H 0.7180 0.6445 0.6357 0.034 Uiso 1 1 calc R . . C10 C 0.87136(15) 0.65986(14) 0.59113(7) 0.0257(3) Uani 1 1 d . . . C11 C 0.91638(15) 0.65032(15) 0.52864(7) 0.0271(4) Uani 1 1 d . . . H11 H 0.9988 0.6596 0.5264 0.033 Uiso 1 1 calc R . . C12 C 0.83999(15) 0.62713(15) 0.46943(7) 0.0254(3) Uani 1 1 d . . . C13 C 0.89237(16) 0.62358(18) 0.40285(8) 0.0357(4) Uani 1 1 d . . . H13A H 0.9783 0.6344 0.4106 0.054 Uiso 1 1 calc R . . H13B H 0.8587 0.6983 0.3746 0.054 Uiso 1 1 calc R . . H13C H 0.8734 0.5358 0.3809 0.054 Uiso 1 1 calc R . . N1 N 0.94991(15) 0.68057(15) 0.65134(7) 0.0315(3) Uani 1 1 d . . . H1B H 0.9210(17) 0.7433(19) 0.6778(9) 0.044(6) Uiso 1 1 d . . . H1C H 1.0266(19) 0.7054(19) 0.6425(9) 0.048(6) Uiso 1 1 d . . . O2 O 0.40997(11) 0.33229(11) 0.16526(5) 0.0292(3) Uani 1 1 d . . . H2A H 0.4006(18) 0.248(2) 0.1848(10) 0.055(6) Uiso 1 1 d . . . C21 C 0.34412(14) 0.34548(15) 0.10287(7) 0.0240(3) Uani 1 1 d . . . C22 C 0.35801(15) 0.46713(15) 0.06624(7) 0.0282(4) Uani 1 1 d . . . H22 H 0.4130 0.5347 0.0832 0.034 Uiso 1 1 calc R . . C23 C 0.29020(15) 0.48768(15) 0.00466(7) 0.0266(4) Uani 1 1 d . . . H23 H 0.3000 0.5696 -0.0192 0.032 Uiso 1 1 calc R . . C24 C 0.20728(14) 0.38785(15) -0.02245(7) 0.0234(3) Uani 1 1 d . . . C26 C 0.26461(15) 0.24378(15) 0.07623(7) 0.0262(4) Uani 1 1 d . . . H26 H 0.2568 0.1608 0.0996 0.031 Uiso 1 1 calc R . . C25 C 0.19685(14) 0.26571(15) 0.01493(7) 0.0257(3) Uani 1 1 d . . . H25 H 0.1426 0.1972 -0.0020 0.031 Uiso 1 1 calc R . . C27 C 0.12861(14) 0.40782(14) -0.08726(7) 0.0224(3) Uani 1 1 d . . . C28 C 0.00362(14) 0.40034(14) -0.08690(7) 0.0243(3) Uani 1 1 d . . . H28 H -0.0277 0.3890 -0.0459 0.029 Uiso 1 1 calc R . . C29 C -0.07521(15) 0.40919(14) -0.14548(7) 0.0242(3) Uani 1 1 d . . . H29 H -0.1580 0.4060 -0.1434 0.029 Uiso 1 1 calc R . . C30 C -0.02978(15) 0.42296(14) -0.20761(7) 0.0235(3) Uani 1 1 d . . . C31 C 0.09407(14) 0.43328(15) -0.20849(7) 0.0257(3) Uani 1 1 d . . . H31 H 0.1247 0.4444 -0.2497 0.031 Uiso 1 1 calc R . . C32 C 0.17411(14) 0.42752(15) -0.14968(7) 0.0253(3) Uani 1 1 d . . . C33 C 0.30759(16) 0.43897(19) -0.15484(8) 0.0394(4) Uani 1 1 d . . . H33A H 0.3250 0.4037 -0.1978 0.059 Uiso 1 1 calc R . . H33B H 0.3510 0.3854 -0.1194 0.059 Uiso 1 1 calc R . . H33C H 0.3317 0.5351 -0.1506 0.059 Uiso 1 1 calc R . . N2 N -0.10796(14) 0.42001(14) -0.26925(7) 0.0278(3) Uani 1 1 d . . . H2C H -0.1857(19) 0.4331(19) -0.2616(9) 0.048(6) Uiso 1 1 d . . . H2B H -0.0865(16) 0.4891(19) -0.2989(9) 0.042(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 O1 0.0346(7) 0.0304(6) 0.0255(6) -0.0036(5) -0.0057(5) 0.0033(5) C1 0.0262(9) 0.0262(8) 0.0200(8) 0.0011(6) 0.0015(6) -0.0021(6) C2 0.0316(10) 0.0238(8) 0.0274(9) 0.0006(6) 0.0012(7) 0.0060(7) C3 0.0342(10) 0.0216(8) 0.0253(8) -0.0043(6) 0.0009(7) 0.0014(7) C4 0.0275(9) 0.0235(8) 0.0204(8) -0.0005(6) 0.0014(6) -0.0023(6) C5 0.0310(9) 0.0225(8) 0.0261(8) 0.0017(6) 0.0010(7) 0.0031(7) C6 0.0340(9) 0.0214(8) 0.0223(8) -0.0034(6) 0.0016(7) -0.0010(6) C7 0.0312(9) 0.0177(7) 0.0226(8) -0.0001(5) 0.0004(7) 0.0015(6) C8 0.0267(9) 0.0244(8) 0.0273(9) -0.0018(6) 0.0031(7) 0.0037(6) C9 0.0380(10) 0.0256(8) 0.0209(8) -0.0012(6) 0.0044(7) 0.0048(7) C10 0.0343(10) 0.0183(7) 0.0230(8) -0.0002(6) -0.0030(7) 0.0015(6) C11 0.0271(9) 0.0250(8) 0.0288(9) 0.0011(6) 0.0011(7) 0.0000(6) C12 0.0312(9) 0.0226(8) 0.0222(8) 0.0002(6) 0.0016(7) 0.0009(6) C13 0.0340(10) 0.0446(10) 0.0291(9) 0.0020(7) 0.0063(8) -0.0025(8) N1 0.0381(10) 0.0307(8) 0.0238(7) -0.0037(6) -0.0043(7) -0.0004(7) O2 0.0375(7) 0.0264(6) 0.0215(6) -0.0004(4) -0.0072(5) -0.0001(5) C21 0.0256(9) 0.0254(8) 0.0200(8) -0.0031(6) -0.0022(6) 0.0041(6) C22 0.0305(9) 0.0245(8) 0.0281(9) -0.0041(6) -0.0038(7) -0.0038(7) C23 0.0297(9) 0.0226(8) 0.0263(8) 0.0025(6) -0.0015(7) -0.0028(6) C24 0.0242(9) 0.0244(8) 0.0213(8) -0.0008(6) 0.0006(6) 0.0014(6) C26 0.0319(9) 0.0227(8) 0.0232(8) 0.0030(6) -0.0011(7) 0.0000(7) C25 0.0274(9) 0.0247(8) 0.0243(8) -0.0022(6) -0.0008(7) -0.0036(6) C27 0.0269(9) 0.0176(7) 0.0217(8) -0.0005(5) -0.0016(6) -0.0005(6) C28 0.0301(9) 0.0220(8) 0.0208(8) 0.0012(6) 0.0028(7) -0.0016(6) C29 0.0236(9) 0.0227(8) 0.0257(8) 0.0008(6) 0.0009(6) -0.0012(6) C30 0.0303(9) 0.0175(7) 0.0213(8) -0.0001(5) -0.0041(6) 0.0007(6) C31 0.0291(9) 0.0281(8) 0.0198(8) 0.0013(6) 0.0028(7) 0.0011(7) C32 0.0269(9) 0.0244(8) 0.0242(8) 0.0000(6) 0.0007(7) 0.0006(6) C33 0.0300(10) 0.0566(12) 0.0315(10) 0.0027(8) 0.0035(8) 0.0002(8) N2 0.0293(9) 0.0304(8) 0.0221(7) 0.0022(5) -0.0045(6) 0.0002(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 O1 C1 1.3774(18) . ? O1 H1A 0.89(2) . ? C1 C2 1.385(2) . ? C1 C6 1.391(2) . ? C2 C3 1.380(2) . ? C2 H2 0.9300 . ? C3 C4 1.399(2) . ? C3 H3 0.9300 . ? C4 C5 1.398(2) . ? C4 C7 1.484(2) . ? C5 C6 1.378(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.397(2) . ? C7 C12 1.403(2) . ? C8 C9 1.383(2) . ? C8 H8 0.9300 . ? C9 C10 1.385(2) . ? C9 H9 0.9300 . ? C10 C11 1.396(2) . ? C10 N1 1.419(2) . ? C11 C12 1.395(2) . ? C11 H11 0.9300 . ? C12 C13 1.507(2) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? N1 H1B 0.883(19) . ? N1 H1C 0.92(2) . ? O2 C21 1.3778(17) . ? O2 H2A 0.91(2) . ? C21 C26 1.383(2) . ? C21 C22 1.392(2) . ? C22 C23 1.382(2) . ? C22 H22 0.9300 . ? C23 C24 1.397(2) . ? C23 H23 0.9300 . ? C24 C25 1.398(2) . ? C24 C27 1.491(2) . ? C26 C25 1.379(2) . ? C26 H26 0.9300 . ? C25 H25 0.9300 . ? C27 C28 1.397(2) . ? C27 C32 1.407(2) . ? C28 C29 1.384(2) . ? C28 H28 0.9300 . ? C29 C30 1.394(2) . ? C29 H29 0.9300 . ? C30 C31 1.388(2) . ? C30 N2 1.4258(19) . ? C31 C32 1.393(2) . ? C31 H31 0.9300 . ? C32 C33 1.508(2) . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? N2 H2C 0.91(2) . ? N2 H2B 0.936(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1A 107.8(13) . . ? O1 C1 C2 117.70(13) . . ? O1 C1 C6 122.58(13) . . ? C2 C1 C6 119.72(14) . . ? C3 C2 C1 119.84(14) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 121.72(14) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 117.18(14) . . ? C5 C4 C7 122.52(13) . . ? C3 C4 C7 120.30(13) . . ? C6 C5 C4 121.67(14) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 119.86(13) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C8 C7 C12 118.32(14) . . ? C8 C7 C4 119.99(15) . . ? C12 C7 C4 121.63(13) . . ? C9 C8 C7 121.68(16) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C10 120.11(14) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 119.00(14) . . ? C9 C10 N1 120.04(14) . . ? C11 C10 N1 120.88(16) . . ? C12 C11 C10 121.19(15) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C7 119.65(14) . . ? C11 C12 C13 119.16(15) . . ? C7 C12 C13 121.13(14) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 N1 H1B 111.5(12) . . ? C10 N1 H1C 111.9(11) . . ? H1B N1 H1C 110.3(16) . . ? C21 O2 H2A 113.2(12) . . ? O2 C21 C26 122.49(13) . . ? O2 C21 C22 118.05(13) . . ? C26 C21 C22 119.45(14) . . ? C23 C22 C21 120.17(14) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 121.33(14) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C23 C24 C25 117.19(14) . . ? C23 C24 C27 123.27(13) . . ? C25 C24 C27 119.51(13) . . ? C25 C26 C21 119.88(14) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? C26 C25 C24 121.94(14) . . ? C26 C25 H25 119.0 . . ? C24 C25 H25 119.0 . . ? C28 C27 C32 117.98(14) . . ? C28 C27 C24 118.79(13) . . ? C32 C27 C24 123.16(14) . . ? C29 C28 C27 122.30(14) . . ? C29 C28 H28 118.9 . . ? C27 C28 H28 118.9 . . ? C28 C29 C30 119.64(15) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C31 C30 C29 118.56(14) . . ? C31 C30 N2 120.41(14) . . ? C29 C30 N2 120.97(15) . . ? C30 C31 C32 122.24(14) . . ? C30 C31 H31 118.9 . . ? C32 C31 H31 118.9 . . ? C31 C32 C27 119.21(15) . . ? C31 C32 C33 119.08(14) . . ? C27 C32 C33 121.69(14) . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C30 N2 H2C 111.0(12) . . ? C30 N2 H2B 110.8(11) . . ? H2C N2 H2B 109.0(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 O1 C1 C2 C3 178.90(14) . . . . ? C6 C1 C2 C3 -1.3(2) . . . . ? C1 C2 C3 C4 0.9(2) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C2 C3 C4 C7 -179.65(15) . . . . ? C3 C4 C5 C6 -0.7(2) . . . . ? C7 C4 C5 C6 179.05(14) . . . . ? C4 C5 C6 C1 0.3(2) . . . . ? O1 C1 C6 C5 -179.50(14) . . . . ? C2 C1 C6 C5 0.7(2) . . . . ? C5 C4 C7 C8 -112.17(17) . . . . ? C3 C4 C7 C8 67.59(19) . . . . ? C5 C4 C7 C12 70.5(2) . . . . ? C3 C4 C7 C12 -109.71(17) . . . . ? C12 C7 C8 C9 0.4(2) . . . . ? C4 C7 C8 C9 -177.01(13) . . . . ? C7 C8 C9 C10 1.5(2) . . . . ? C8 C9 C10 C11 -2.5(2) . . . . ? C8 C9 C10 N1 -179.43(13) . . . . ? C9 C10 C11 C12 1.8(2) . . . . ? N1 C10 C11 C12 178.68(13) . . . . ? C10 C11 C12 C7 0.0(2) . . . . ? C10 C11 C12 C13 177.49(14) . . . . ? C8 C7 C12 C11 -1.1(2) . . . . ? C4 C7 C12 C11 176.23(13) . . . . ? C8 C7 C12 C13 -178.51(13) . . . . ? C4 C7 C12 C13 -1.2(2) . . . . ? O2 C21 C22 C23 -177.32(14) . . . . ? C26 C21 C22 C23 1.9(2) . . . . ? C21 C22 C23 C24 -0.4(2) . . . . ? C22 C23 C24 C25 -0.7(2) . . . . ? C22 C23 C24 C27 177.44(14) . . . . ? O2 C21 C26 C25 176.90(14) . . . . ? C22 C21 C26 C25 -2.3(2) . . . . ? C21 C26 C25 C24 1.2(2) . . . . ? C23 C24 C25 C26 0.3(2) . . . . ? C27 C24 C25 C26 -177.91(14) . . . . ? C23 C24 C27 C28 -121.96(16) . . . . ? C25 C24 C27 C28 56.17(19) . . . . ? C23 C24 C27 C32 61.1(2) . . . . ? C25 C24 C27 C32 -120.78(16) . . . . ? C32 C27 C28 C29 1.1(2) . . . . ? C24 C27 C28 C29 -175.96(12) . . . . ? C27 C28 C29 C30 1.5(2) . . . . ? C28 C29 C30 C31 -2.7(2) . . . . ? C28 C29 C30 N2 174.44(13) . . . . ? C29 C30 C31 C32 1.3(2) . . . . ? N2 C30 C31 C32 -175.81(13) . . . . ? C30 C31 C32 C27 1.3(2) . . . . ? C30 C31 C32 C33 179.77(14) . . . . ? C28 C27 C32 C31 -2.5(2) . . . . ? C24 C27 C32 C31 174.49(13) . . . . ? C28 C27 C32 C33 179.09(14) . . . . ? C24 C27 C32 C33 -3.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.242 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.043