# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_chenc-17 #TrackingRef '19624_web_deposit_cif_file_0_ChaoChen_1366340981.chenc-17.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 N2' _chemical_formula_sum 'C21 H16 N2' _chemical_formula_weight 296.36 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4635(11) _cell_length_b 10.487(3) _cell_length_c 11.065(2) _cell_angle_alpha 71.601(18) _cell_angle_beta 88.482(15) _cell_angle_gamma 72.077(13) _cell_volume 779.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 37 _cell_measurement_theta_min 4.89 _cell_measurement_theta_max 14.24 _exptl_crystal_description prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.075 _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 295(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 ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3414 _diffrn_reflns_av_R_equivalents 0.0462 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2725 _reflns_number_gt 1809 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'XSCANS (Bruker, 1997)' _computing_cell_refinement 'XSCANS (Bruker, 1997)' _computing_data_reduction 'XSCANS (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _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^)+(0.0010P)^2^+0.6000P] 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 2725 _refine_ls_number_parameters 213 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL Chenc-17 in P-1 CELL 0.71073 7.4635 10.4872 11.0654 71.601 88.482 72.077 ZERR 2.00 0.0011 0.0025 0.0024 0.018 0.015 0.013 LATT 1 SFAC C H N UNIT 42 32 4 OMIT -2 50.1 OMIT -2 -1 1 L.S. 4 ACTA BOND $H FMAP 2 PLAN 10 TEMP 22 DFIX 0.93 0.01 C13 H13 WGHT 0.001000 0.600000 FVAR 0.53533 N1 3 0.378776 0.316629 0.531822 11.00000 0.04236 0.03944 = 0.04748 -0.01214 0.00294 -0.00899 N2 3 0.417197 0.343166 0.735250 11.00000 0.04492 0.03530 = 0.04607 -0.01132 0.00067 -0.00803 C1 1 0.443881 0.267894 0.652298 11.00000 0.03916 0.03564 = 0.04561 -0.00999 0.00497 -0.01193 C2 1 0.321991 0.480146 0.690654 11.00000 0.03921 0.03657 = 0.04534 -0.00972 0.00511 -0.01111 C3 1 0.130124 0.690260 0.508581 11.00000 0.04220 0.03900 = 0.05548 -0.00997 0.00518 -0.01096 AFIX 43 H3 2 0.108229 0.749324 0.558531 11.00000 -1.20000 AFIX 0 C4 1 0.053525 0.743427 0.385042 11.00000 0.03820 0.04346 = 0.05472 -0.00149 0.00318 -0.01248 C5 1 0.087712 0.652874 0.311536 11.00000 0.05213 0.05798 = 0.04490 -0.00183 -0.00226 -0.01443 AFIX 43 H5 2 0.036050 0.688930 0.227431 11.00000 -1.20000 AFIX 0 C6 1 0.194550 0.512905 0.358802 11.00000 0.05602 0.05379 = 0.04619 -0.01254 0.00274 -0.01266 AFIX 43 H6 2 0.213993 0.455537 0.307372 11.00000 -1.20000 AFIX 0 C7 1 0.274774 0.456557 0.486050 11.00000 0.03896 0.04306 = 0.04264 -0.01023 0.00554 -0.01339 C8 1 0.242836 0.545920 0.561871 11.00000 0.03604 0.03635 = 0.04627 -0.00812 0.00600 -0.01112 C9 1 0.561510 0.115548 0.705566 11.00000 0.03839 0.03557 = 0.05174 -0.01239 0.00325 -0.01154 C10 1 0.612951 0.033222 0.626327 11.00000 0.04942 0.04130 = 0.05685 -0.01666 0.00453 -0.00933 AFIX 43 H10 2 0.573068 0.072588 0.539844 11.00000 -1.20000 AFIX 0 C11 1 0.723697 -0.107721 0.675194 11.00000 0.05588 0.04218 = 0.07550 -0.02255 0.00993 -0.00902 AFIX 43 H11 2 0.756513 -0.162441 0.621407 11.00000 -1.20000 AFIX 0 C12 1 0.784743 -0.166501 0.801778 11.00000 0.05449 0.03680 = 0.08347 -0.00933 -0.00208 -0.00401 AFIX 43 H12 2 0.860795 -0.260503 0.833455 11.00000 -1.20000 AFIX 0 C13 1 0.734016 -0.086957 0.882843 11.00000 0.07109 0.04613 = 0.06442 -0.00793 -0.00998 -0.00903 H13 2 0.783296 -0.122376 0.975602 11.00000 0.04079 C14 1 0.621101 0.054179 0.834528 11.00000 0.06340 0.04106 = 0.05696 -0.01488 -0.00163 -0.01020 AFIX 43 H14 2 0.585404 0.107663 0.889178 11.00000 -1.20000 AFIX 0 C15 1 0.302682 0.557371 0.784337 11.00000 0.04095 0.03483 = 0.04554 -0.01067 -0.00139 -0.00432 C16 1 0.247357 0.499714 0.904513 11.00000 0.05792 0.03920 = 0.05143 -0.01095 0.00294 -0.01162 AFIX 43 H16 2 0.218345 0.415714 0.923698 11.00000 -1.20000 AFIX 0 C17 1 0.234789 0.565345 0.996000 11.00000 0.06824 0.06164 = 0.04735 -0.01892 0.00694 -0.01207 AFIX 43 H17 2 0.194784 0.526534 1.075583 11.00000 -1.20000 AFIX 0 C18 1 0.281205 0.688003 0.969976 11.00000 0.06166 0.06464 = 0.06590 -0.03490 -0.00058 -0.01012 AFIX 43 H18 2 0.273830 0.731514 1.032130 11.00000 -1.20000 AFIX 0 C19 1 0.338542 0.746134 0.851823 11.00000 0.05571 0.04362 = 0.07905 -0.02441 -0.00439 -0.00954 AFIX 43 H19 2 0.370948 0.828615 0.834396 11.00000 -1.20000 AFIX 0 C20 1 0.348138 0.682394 0.758993 11.00000 0.05228 0.04174 = 0.05438 -0.01282 0.00092 -0.01359 AFIX 43 H20 2 0.385196 0.723096 0.678908 11.00000 -1.20000 AFIX 0 C21 1 -0.067004 0.897006 0.328302 11.00000 0.04981 0.04688 = 0.07710 0.00292 -0.00318 -0.00901 AFIX 137 H21A 2 -0.073822 0.944234 0.390618 11.00000 -1.50000 H21B 2 -0.191838 0.901569 0.303802 11.00000 -1.50000 H21C 2 -0.011691 0.942489 0.254547 11.00000 -1.50000 HKLF 4 REM Chenc-17 in P-1 REM R1 = 0.0571 for 1809 Fo > 4sig(Fo) and 0.0906 for all 2725 data REM 213 parameters refined using 1 restraints END ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3788(3) 0.3166(2) 0.53182(19) 0.0445(5) Uani 1 1 d . . . N2 N 0.4172(3) 0.3432(2) 0.73525(19) 0.0436(5) Uani 1 1 d . . . C1 C 0.4439(3) 0.2679(2) 0.6523(2) 0.0409(6) Uani 1 1 d . . . C2 C 0.3220(3) 0.4801(2) 0.6907(2) 0.0415(6) Uani 1 1 d . . . C3 C 0.1301(3) 0.6903(3) 0.5086(2) 0.0473(6) Uani 1 1 d . . . H3 H 0.1082 0.7493 0.5585 0.057 Uiso 1 1 calc R . . C4 C 0.0535(3) 0.7434(3) 0.3850(3) 0.0491(7) Uani 1 1 d . . . C5 C 0.0877(4) 0.6529(3) 0.3115(3) 0.0559(7) Uani 1 1 d . . . H5 H 0.0361 0.6889 0.2274 0.067 Uiso 1 1 calc R . . C6 C 0.1946(4) 0.5129(3) 0.3588(2) 0.0540(7) Uani 1 1 d . . . H6 H 0.2140 0.4555 0.3074 0.065 Uiso 1 1 calc R . . C7 C 0.2748(3) 0.4566(2) 0.4860(2) 0.0424(6) Uani 1 1 d . . . C8 C 0.2428(3) 0.5459(2) 0.5619(2) 0.0410(6) Uani 1 1 d . . . C9 C 0.5615(3) 0.1155(2) 0.7056(2) 0.0424(6) Uani 1 1 d . . . C10 C 0.6130(4) 0.0332(3) 0.6263(3) 0.0502(7) Uani 1 1 d . . . H10 H 0.5731 0.0726 0.5398 0.060 Uiso 1 1 calc R . . C11 C 0.7237(4) -0.1077(3) 0.6752(3) 0.0586(7) Uani 1 1 d . . . H11 H 0.7565 -0.1624 0.6214 0.070 Uiso 1 1 calc R . . C12 C 0.7847(4) -0.1665(3) 0.8018(3) 0.0631(8) Uani 1 1 d . . . H12 H 0.8608 -0.2605 0.8335 0.076 Uiso 1 1 calc R . . C13 C 0.7340(5) -0.0870(3) 0.8828(3) 0.0650(8) Uani 1 1 d D . . H13 H 0.783(3) -0.122(2) 0.9756(11) 0.041(6) Uiso 1 1 d D . . C14 C 0.6211(4) 0.0542(3) 0.8345(3) 0.0554(7) Uani 1 1 d . . . H14 H 0.5854 0.1077 0.8892 0.067 Uiso 1 1 calc R . . C15 C 0.3027(3) 0.5574(2) 0.7843(2) 0.0428(6) Uani 1 1 d . . . C16 C 0.2474(4) 0.4997(3) 0.9045(2) 0.0513(7) Uani 1 1 d . . . H16 H 0.2183 0.4157 0.9237 0.062 Uiso 1 1 calc R . . C17 C 0.2348(4) 0.5653(3) 0.9960(3) 0.0608(8) Uani 1 1 d . . . H17 H 0.1948 0.5265 1.0756 0.073 Uiso 1 1 calc R . . C18 C 0.2812(4) 0.6880(3) 0.9700(3) 0.0629(8) Uani 1 1 d . . . H18 H 0.2738 0.7315 1.0321 0.075 Uiso 1 1 calc R . . C19 C 0.3385(4) 0.7461(3) 0.8518(3) 0.0596(8) Uani 1 1 d . . . H19 H 0.3709 0.8286 0.8344 0.072 Uiso 1 1 calc R . . C20 C 0.3481(4) 0.6824(3) 0.7590(3) 0.0504(7) Uani 1 1 d . . . H20 H 0.3852 0.7231 0.6789 0.060 Uiso 1 1 calc R . . C21 C -0.0670(4) 0.8970(3) 0.3283(3) 0.0649(8) Uani 1 1 d . . . H21A H -0.0738 0.9442 0.3906 0.097 Uiso 1 1 calc R . . H21B H -0.1918 0.9016 0.3038 0.097 Uiso 1 1 calc R . . H21C H -0.0117 0.9425 0.2545 0.097 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0424(12) 0.0394(11) 0.0475(12) -0.0121(9) 0.0029(10) -0.0090(9) N2 0.0449(12) 0.0353(11) 0.0461(12) -0.0113(9) 0.0007(10) -0.0080(9) C1 0.0392(14) 0.0356(13) 0.0456(15) -0.0100(11) 0.0050(11) -0.0119(11) C2 0.0392(14) 0.0366(13) 0.0453(14) -0.0097(11) 0.0051(11) -0.0111(11) C3 0.0422(14) 0.0390(13) 0.0555(16) -0.0100(12) 0.0052(12) -0.0110(11) C4 0.0382(14) 0.0435(14) 0.0547(16) -0.0015(12) 0.0032(12) -0.0125(12) C5 0.0521(17) 0.0580(17) 0.0449(15) -0.0018(13) -0.0023(13) -0.0144(14) C6 0.0560(17) 0.0538(16) 0.0462(16) -0.0125(13) 0.0027(13) -0.0127(13) C7 0.0390(14) 0.0431(14) 0.0426(14) -0.0102(11) 0.0055(11) -0.0134(11) C8 0.0360(13) 0.0364(12) 0.0463(14) -0.0081(11) 0.0060(11) -0.0111(10) C9 0.0384(14) 0.0356(13) 0.0517(15) -0.0124(11) 0.0033(11) -0.0115(11) C10 0.0494(16) 0.0413(14) 0.0568(16) -0.0167(12) 0.0045(13) -0.0093(12) C11 0.0559(18) 0.0422(15) 0.076(2) -0.0226(14) 0.0099(15) -0.0090(13) C12 0.0545(18) 0.0368(15) 0.083(2) -0.0093(15) -0.0021(16) -0.0040(13) C13 0.071(2) 0.0461(16) 0.0644(19) -0.0079(15) -0.0100(16) -0.0090(15) C14 0.0634(18) 0.0411(14) 0.0570(17) -0.0149(13) -0.0016(14) -0.0102(13) C15 0.0409(14) 0.0348(13) 0.0455(15) -0.0107(11) -0.0014(11) -0.0043(11) C16 0.0579(17) 0.0392(14) 0.0514(16) -0.0109(12) 0.0029(13) -0.0116(12) C17 0.068(2) 0.0616(18) 0.0474(16) -0.0189(14) 0.0069(14) -0.0121(15) C18 0.0617(19) 0.0646(19) 0.066(2) -0.0349(16) -0.0006(16) -0.0101(15) C19 0.0557(18) 0.0436(15) 0.079(2) -0.0244(15) -0.0044(15) -0.0095(13) C20 0.0523(16) 0.0417(14) 0.0544(16) -0.0128(12) 0.0009(13) -0.0136(12) C21 0.0498(17) 0.0469(16) 0.077(2) 0.0029(14) -0.0032(15) -0.0090(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.314(3) . ? N1 C7 1.365(3) . ? N2 C2 1.325(3) . ? N2 C1 1.362(3) . ? C1 C9 1.497(3) . ? C2 C8 1.424(3) . ? C2 C15 1.484(3) . ? C3 C4 1.368(4) . ? C3 C8 1.423(3) . ? C3 H3 0.9300 . ? C4 C5 1.399(4) . ? C4 C21 1.516(3) . ? C5 C6 1.372(4) . ? C5 H5 0.9300 . ? C6 C7 1.411(3) . ? C6 H6 0.9300 . ? C7 C8 1.410(3) . ? C9 C10 1.385(3) . ? C9 C14 1.388(3) . ? C10 C11 1.388(3) . ? C10 H10 0.9300 . ? C11 C12 1.366(4) . ? C11 H11 0.9300 . ? C12 C13 1.380(4) . ? C12 H12 0.9300 . ? C13 C14 1.394(4) . ? C13 H13 1.011(10) . ? C14 H14 0.9300 . ? C15 C16 1.386(3) . ? C15 C20 1.396(3) . ? C16 C17 1.379(4) . ? C16 H16 0.9300 . ? C17 C18 1.376(4) . ? C17 H17 0.9300 . ? C18 C19 1.375(4) . ? C18 H18 0.9300 . ? C19 C20 1.381(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 N1 C7 116.3(2) . . ? C2 N2 C1 117.8(2) . . ? N1 C1 N2 126.4(2) . . ? N1 C1 C9 118.0(2) . . ? N2 C1 C9 115.6(2) . . ? N2 C2 C8 121.4(2) . . ? N2 C2 C15 115.3(2) . . ? C8 C2 C15 123.3(2) . . ? C4 C3 C8 121.0(3) . . ? C4 C3 H3 119.5 . . ? C8 C3 H3 119.5 . . ? C3 C4 C5 118.6(2) . . ? C3 C4 C21 121.1(3) . . ? C5 C4 C21 120.3(3) . . ? C6 C5 C4 122.5(3) . . ? C6 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? C5 C6 C7 119.5(3) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? N1 C7 C8 122.3(2) . . ? N1 C7 C6 118.7(2) . . ? C8 C7 C6 119.0(2) . . ? C7 C8 C3 119.3(2) . . ? C7 C8 C2 115.7(2) . . ? C3 C8 C2 124.9(2) . . ? C10 C9 C14 118.8(2) . . ? C10 C9 C1 120.3(2) . . ? C14 C9 C1 120.9(2) . . ? C9 C10 C11 120.4(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 120.3(3) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 119.6(3) . . ? C12 C13 H13 123.6(13) . . ? C14 C13 H13 116.6(13) . . ? C9 C14 C13 120.6(3) . . ? C9 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C20 118.3(2) . . ? C16 C15 C2 119.0(2) . . ? C20 C15 C2 122.6(2) . . ? C17 C16 C15 120.8(3) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C18 C17 C16 120.3(3) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 119.8(3) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 120.2(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 120.6(3) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? C4 C21 H21A 109.5 . . ? C4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.628 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 934862' ####################################################################### # # 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_chenc-20 #TrackingRef '19697_web_deposit_cif_file_0_ChaoChen_1366613234.CHENC-20.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H20 N2 O' _chemical_formula_sum 'C19 H20 N2 O' _chemical_formula_weight 292.37 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.482(2) _cell_length_b 9.231(3) _cell_length_c 12.345(3) _cell_angle_alpha 71.15(3) _cell_angle_beta 75.16(2) _cell_angle_gamma 86.82(3) _cell_volume 779.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 46 _cell_measurement_theta_min 5.11 _cell_measurement_theta_max 12.60 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.078 _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 295(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 ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3573 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0640 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2871 _reflns_number_gt 1462 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'XSCANS (Bruker, 1997)' _computing_cell_refinement 'XSCANS (Bruker, 1997)' _computing_data_reduction 'XSCANS (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _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^)+(0.0010P)^2^+0.4000P] 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 2871 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1237 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL CHENC-20 in P-1 CELL 0.71073 7.4823 9.2312 12.3450 71.149 75.164 86.816 ZERR 2.00 0.0024 0.0029 0.0030 0.025 0.020 0.031 LATT 1 SFAC C H N O UNIT 38 40 4 2 OMIT 2 1 1 L.S. 8 DAMP 300 ACTA BOND $H FMAP 2 PLAN 10 TEMP 22 WGHT 0.001000 0.400000 FVAR 0.42958 O1 4 0.595241 0.112048 0.107488 11.00000 0.11889 0.07292 = 0.06360 -0.03666 -0.02029 0.03200 N1 3 0.266729 0.539447 0.420049 11.00000 0.06095 0.04538 = 0.05424 -0.02111 -0.01267 0.00854 N2 3 0.332658 0.312367 0.564179 11.00000 0.06831 0.04785 = 0.05455 -0.01788 -0.01733 0.00761 C1 1 0.199986 0.603588 0.502053 11.00000 0.05181 0.04520 = 0.05398 -0.01770 -0.00999 0.00522 C2 1 0.189297 0.525368 0.622741 11.00000 0.05611 0.04890 = 0.04870 -0.01601 -0.01022 0.00447 C3 1 0.111925 0.584766 0.715120 11.00000 0.08422 0.05993 = 0.05982 -0.02396 -0.01228 0.01831 AFIX 43 H3 2 0.063317 0.682127 0.698393 11.00000 -1.20000 AFIX 0 C4 1 0.107449 0.501962 0.827842 11.00000 0.10874 0.07955 = 0.05391 -0.02920 -0.01126 0.02226 AFIX 43 H4 2 0.055669 0.542752 0.888229 11.00000 -1.20000 AFIX 0 C5 1 0.179482 0.355926 0.855028 11.00000 0.10853 0.07473 = 0.04895 -0.01591 -0.01656 0.01476 AFIX 43 H5 2 0.174547 0.299514 0.933299 11.00000 -1.20000 AFIX 0 C6 1 0.257230 0.295504 0.767098 11.00000 0.09104 0.06293 = 0.05734 -0.01732 -0.01992 0.01197 AFIX 43 H6 2 0.307524 0.198832 0.785310 11.00000 -1.20000 AFIX 0 C7 1 0.261406 0.378720 0.649627 11.00000 0.05956 0.05238 = 0.05005 -0.01887 -0.01381 0.00445 C8 1 0.329042 0.393733 0.456760 11.00000 0.05618 0.04355 = 0.05346 -0.01508 -0.01305 0.00355 C9 1 0.134690 0.764372 0.463013 11.00000 0.06597 0.04914 = 0.06072 -0.02133 -0.01338 0.01082 AFIX 23 H9A 2 0.205601 0.828477 0.486539 11.00000 -1.20000 H9B 2 0.006521 0.765332 0.505724 11.00000 -1.20000 AFIX 0 C10 1 0.147738 0.836322 0.333096 11.00000 0.06336 0.04705 = 0.05631 -0.01742 -0.01158 0.01055 AFIX 23 H10A 2 0.090988 0.767409 0.305766 11.00000 -1.20000 H10B 2 0.276922 0.851651 0.289945 11.00000 -1.20000 AFIX 0 C11 1 0.053195 0.988321 0.307211 11.00000 0.07889 0.05219 = 0.06718 -0.01857 -0.01506 0.02171 AFIX 23 H11A 2 -0.075132 0.972509 0.352062 11.00000 -1.20000 H11B 2 0.111318 1.056882 0.334147 11.00000 -1.20000 AFIX 0 C12 1 0.059946 1.064061 0.177973 11.00000 0.10400 0.06325 = 0.07414 -0.02088 -0.02509 0.02602 AFIX 137 H12A 2 0.186456 1.084317 0.133172 11.00000 -1.50000 H12B 2 -0.004172 1.158625 0.167993 11.00000 -1.50000 H12C 2 0.001848 0.997410 0.150564 11.00000 -1.50000 AFIX 0 C13 1 0.396893 0.323705 0.361801 11.00000 0.05916 0.04280 = 0.05435 -0.01828 -0.01606 0.00921 C14 1 0.393061 0.398414 0.247467 11.00000 0.08964 0.04668 = 0.05621 -0.01704 -0.01935 0.01766 AFIX 43 H14 2 0.346223 0.496322 0.228138 11.00000 -1.20000 AFIX 0 C15 1 0.457022 0.332278 0.159647 11.00000 0.10129 0.05578 = 0.05096 -0.01725 -0.01863 0.01628 AFIX 43 H15 2 0.451880 0.384742 0.082339 11.00000 -1.20000 AFIX 0 C16 1 0.528282 0.188436 0.187354 11.00000 0.07623 0.05258 = 0.05792 -0.02701 -0.01502 0.01375 C17 1 0.532409 0.111390 0.301282 11.00000 0.08657 0.05290 = 0.06554 -0.02595 -0.02466 0.02353 AFIX 43 H17 2 0.579794 0.013663 0.320294 11.00000 -1.20000 AFIX 0 C18 1 0.466913 0.177634 0.387777 11.00000 0.08162 0.04865 = 0.05473 -0.01871 -0.02311 0.01389 AFIX 43 H18 2 0.469424 0.123716 0.465329 11.00000 -1.20000 AFIX 0 C19 1 0.624743 0.196243 -0.013753 11.00000 0.14817 0.10209 = 0.06179 -0.04020 -0.01355 0.03657 AFIX 137 H19A 2 0.507953 0.226325 -0.031623 11.00000 -1.50000 H19B 2 0.686065 0.133818 -0.060251 11.00000 -1.50000 H19C 2 0.700284 0.285866 -0.031869 11.00000 -1.50000 HKLF 4 REM CHENC-20 in P-1 REM R1 = 0.0599 for 1462 Fo > 4sig(Fo) and 0.1237 for all 2871 data REM 201 parameters refined using 0 restraints END ; 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 0.5952(3) 0.11205(19) 0.10749(15) 0.0832(6) Uani 1 1 d . . . N1 N 0.2667(3) 0.53945(19) 0.42005(16) 0.0529(5) Uani 1 1 d . . . N2 N 0.3327(3) 0.3124(2) 0.56418(16) 0.0564(6) Uani 1 1 d . . . C1 C 0.2000(3) 0.6036(2) 0.5021(2) 0.0507(6) Uani 1 1 d . . . C2 C 0.1893(3) 0.5254(2) 0.6227(2) 0.0518(6) Uani 1 1 d . . . C3 C 0.1119(4) 0.5848(3) 0.7151(2) 0.0686(8) Uani 1 1 d . . . H3 H 0.0633 0.6821 0.6984 0.082 Uiso 1 1 calc R . . C4 C 0.1074(4) 0.5020(3) 0.8278(2) 0.0814(9) Uani 1 1 d . . . H4 H 0.0557 0.5428 0.8882 0.098 Uiso 1 1 calc R . . C5 C 0.1795(4) 0.3559(3) 0.8550(2) 0.0795(9) Uani 1 1 d . . . H5 H 0.1745 0.2995 0.9333 0.095 Uiso 1 1 calc R . . C6 C 0.2572(4) 0.2955(3) 0.7671(2) 0.0711(8) Uani 1 1 d . . . H6 H 0.3075 0.1988 0.7853 0.085 Uiso 1 1 calc R . . C7 C 0.2614(3) 0.3787(3) 0.6496(2) 0.0535(6) Uani 1 1 d . . . C8 C 0.3290(3) 0.3937(2) 0.4568(2) 0.0514(6) Uani 1 1 d . . . C9 C 0.1347(4) 0.7644(2) 0.4630(2) 0.0585(7) Uani 1 1 d . . . H9A H 0.2056 0.8285 0.4865 0.070 Uiso 1 1 calc R . . H9B H 0.0065 0.7653 0.5057 0.070 Uiso 1 1 calc R . . C10 C 0.1477(3) 0.8363(2) 0.3331(2) 0.0564(7) Uani 1 1 d . . . H10A H 0.0910 0.7674 0.3058 0.068 Uiso 1 1 calc R . . H10B H 0.2769 0.8517 0.2899 0.068 Uiso 1 1 calc R . . C11 C 0.0532(4) 0.9883(3) 0.3072(2) 0.0677(8) Uani 1 1 d . . . H11A H -0.0751 0.9725 0.3521 0.081 Uiso 1 1 calc R . . H11B H 0.1113 1.0569 0.3341 0.081 Uiso 1 1 calc R . . C12 C 0.0599(4) 1.0641(3) 0.1780(2) 0.0812(9) Uani 1 1 d . . . H12A H 0.1865 1.0843 0.1332 0.122 Uiso 1 1 calc R . . H12B H -0.0042 1.1586 0.1680 0.122 Uiso 1 1 calc R . . H12C H 0.0018 0.9974 0.1506 0.122 Uiso 1 1 calc R . . C13 C 0.3969(3) 0.3237(2) 0.3618(2) 0.0514(6) Uani 1 1 d . . . C14 C 0.3931(4) 0.3984(3) 0.2475(2) 0.0645(8) Uani 1 1 d . . . H14 H 0.3462 0.4963 0.2281 0.077 Uiso 1 1 calc R . . C15 C 0.4570(4) 0.3323(3) 0.1596(2) 0.0700(8) Uani 1 1 d . . . H15 H 0.4519 0.3847 0.0823 0.084 Uiso 1 1 calc R . . C16 C 0.5283(4) 0.1884(3) 0.1874(2) 0.0608(7) Uani 1 1 d . . . C17 C 0.5324(4) 0.1114(3) 0.3013(2) 0.0664(8) Uani 1 1 d . . . H17 H 0.5798 0.0137 0.3203 0.080 Uiso 1 1 calc R . . C18 C 0.4669(4) 0.1776(3) 0.3878(2) 0.0605(7) Uani 1 1 d . . . H18 H 0.4694 0.1237 0.4653 0.073 Uiso 1 1 calc R . . C19 C 0.6247(5) 0.1962(3) -0.0138(2) 0.1044(12) Uani 1 1 d . . . H19A H 0.5080 0.2263 -0.0316 0.157 Uiso 1 1 calc R . . H19B H 0.6861 0.1338 -0.0603 0.157 Uiso 1 1 calc R . . H19C H 0.7003 0.2859 -0.0319 0.157 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1189(16) 0.0729(11) 0.0636(11) -0.0367(9) -0.0203(11) 0.0320(11) N1 0.0609(13) 0.0454(10) 0.0542(11) -0.0211(9) -0.0127(10) 0.0085(9) N2 0.0683(14) 0.0478(11) 0.0545(11) -0.0179(9) -0.0173(10) 0.0076(10) C1 0.0518(15) 0.0452(12) 0.0540(14) -0.0177(11) -0.0100(12) 0.0052(11) C2 0.0561(15) 0.0489(13) 0.0487(13) -0.0160(10) -0.0102(11) 0.0045(12) C3 0.084(2) 0.0599(15) 0.0598(15) -0.0240(12) -0.0123(14) 0.0183(14) C4 0.109(2) 0.0796(18) 0.0539(16) -0.0292(13) -0.0113(16) 0.0223(17) C5 0.109(2) 0.0747(18) 0.0490(15) -0.0159(13) -0.0166(15) 0.0148(17) C6 0.091(2) 0.0629(16) 0.0573(16) -0.0173(13) -0.0199(15) 0.0120(15) C7 0.0596(16) 0.0524(13) 0.0501(13) -0.0189(11) -0.0138(12) 0.0044(12) C8 0.0562(15) 0.0436(12) 0.0535(14) -0.0151(11) -0.0131(12) 0.0036(11) C9 0.0660(17) 0.0491(13) 0.0607(15) -0.0213(11) -0.0134(13) 0.0108(12) C10 0.0634(16) 0.0470(12) 0.0563(14) -0.0174(11) -0.0116(12) 0.0105(12) C11 0.0789(19) 0.0522(14) 0.0672(16) -0.0186(12) -0.0151(14) 0.0217(14) C12 0.104(2) 0.0632(16) 0.0741(18) -0.0209(14) -0.0251(16) 0.0260(16) C13 0.0592(16) 0.0428(12) 0.0543(13) -0.0183(10) -0.0161(12) 0.0092(11) C14 0.090(2) 0.0467(13) 0.0562(15) -0.0170(12) -0.0193(14) 0.0177(14) C15 0.101(2) 0.0558(15) 0.0510(14) -0.0172(12) -0.0186(15) 0.0163(15) C16 0.0762(18) 0.0526(13) 0.0579(14) -0.0270(12) -0.0150(13) 0.0138(13) C17 0.0866(19) 0.0529(14) 0.0655(16) -0.0259(12) -0.0247(14) 0.0235(14) C18 0.0816(18) 0.0486(13) 0.0547(14) -0.0187(11) -0.0231(13) 0.0139(13) C19 0.148(3) 0.102(2) 0.0618(18) -0.0402(16) -0.0135(19) 0.037(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C16 1.370(3) . ? O1 C19 1.411(3) . ? N1 C1 1.312(3) . ? N1 C8 1.370(3) . ? N2 C8 1.302(3) . ? N2 C7 1.366(3) . ? C1 C2 1.413(3) . ? C1 C9 1.501(3) . ? C2 C7 1.398(3) . ? C2 C3 1.403(3) . ? C3 C4 1.347(3) . ? C3 H3 0.9300 . ? C4 C5 1.393(4) . ? C4 H4 0.9300 . ? C5 C6 1.364(3) . ? C5 H5 0.9300 . ? C6 C7 1.398(3) . ? C6 H6 0.9300 . ? C8 C13 1.483(3) . ? C9 C10 1.504(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.512(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.510(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.363(3) . ? C13 C18 1.387(3) . ? C14 C15 1.381(3) . ? C14 H14 0.9300 . ? C15 C16 1.373(3) . ? C15 H15 0.9300 . ? C16 C17 1.363(3) . ? C17 C18 1.369(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 C16 O1 C19 117.6(2) . . ? C1 N1 C8 116.7(2) . . ? C8 N2 C7 116.0(2) . . ? N1 C1 C2 121.8(2) . . ? N1 C1 C9 117.4(2) . . ? C2 C1 C9 120.8(2) . . ? C7 C2 C3 118.9(2) . . ? C7 C2 C1 116.5(2) . . ? C3 C2 C1 124.5(2) . . ? C4 C3 C2 120.5(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.8(3) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 120.1(2) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 120.1(2) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? N2 C7 C6 118.7(2) . . ? N2 C7 C2 121.7(2) . . ? C6 C7 C2 119.6(2) . . ? N2 C8 N1 127.2(2) . . ? N2 C8 C13 118.0(2) . . ? N1 C8 C13 114.9(2) . . ? C1 C9 C10 116.79(19) . . ? C1 C9 H9A 108.1 . . ? C10 C9 H9A 108.1 . . ? C1 C9 H9B 108.1 . . ? C10 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? C9 C10 C11 111.8(2) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 113.8(2) . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C10 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 117.8(2) . . ? C14 C13 C8 122.1(2) . . ? C18 C13 C8 120.2(2) . . ? C13 C14 C15 121.6(2) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C16 C15 C14 119.5(2) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C17 C16 O1 115.8(2) . . ? C17 C16 C15 119.8(2) . . ? O1 C16 C15 124.4(2) . . ? C16 C17 C18 120.1(2) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 121.2(2) . . ? C17 C18 H18 119.4 . . ? C13 C18 H18 119.4 . . ? O1 C19 H19A 109.5 . . ? O1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.171 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 935164'