# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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__20120320-RNaph12-BA-Etha- _database_code_depnum_ccdc_archive 'CCDC 884890' #TrackingRef 'RNaph12-BA.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H19 N O2 ' _chemical_formula_moiety 'C19 H19 N O2 ' _chemical_formula_weight 293.36 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,-Z 3 1/2+X,1/2+Y,+Z 4 1/2-X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 34.7123(6) _cell_length_b 6.19971(11) _cell_length_c 7.24791(13) _cell_angle_alpha 90.0000 _cell_angle_beta 91.5454(7) _cell_angle_gamma 90.0000 _cell_volume 1559.23(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 10859 _cell_measurement_theta_min 5.1 _cell_measurement_theta_max 68.2 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624.00 _exptl_absorpt_coefficient_mu 0.643 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.632 _exptl_absorpt_correction_T_max 0.968 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 13350 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_theta_max 68.22 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 68.22 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_ambient_temperature 213.1 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2830 _reflns_number_gt 2152 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1172 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2830 _refine_ls_number_parameters 201 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.4731P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.18 _refine_diff_density_min -0.16 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(2) _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1262 Friedel Pairs' _refine_ls_abs_structure_Flack -0.3(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.69502(5) 0.8089(3) 0.3062(2) 0.0516(5) Uani 1.00 1 d . . . O(2) O 0.69971(5) 0.4931(3) 0.4477(2) 0.0538(5) Uani 1.00 1 d . . . N(1) N 0.72192(5) 1.0885(3) 0.5761(2) 0.0423(5) Uani 1.00 1 d . . . C(1) C 0.68050(7) 0.6348(4) 0.3585(3) 0.0413(6) Uani 1.00 1 d . . . C(2) C 0.63838(7) 0.5939(4) 0.3195(3) 0.0389(5) Uani 1.00 1 d . . . C(3) C 0.62118(7) 0.4026(4) 0.3720(3) 0.0456(6) Uani 1.00 1 d . . . C(4) C 0.58209(8) 0.3699(5) 0.3418(3) 0.0521(7) Uani 1.00 1 d . . . C(5) C 0.55991(8) 0.5282(5) 0.2566(4) 0.0534(7) Uani 1.00 1 d . . . C(6) C 0.57678(8) 0.7198(4) 0.2027(4) 0.0518(7) Uani 1.00 1 d . . . C(7) C 0.61591(7) 0.7525(4) 0.2342(3) 0.0456(6) Uani 1.00 1 d . . . C(8) C 0.71166(7) 1.0523(4) 0.7741(3) 0.0459(6) Uani 1.00 1 d . . . C(9) C 0.72612(8) 0.8338(5) 0.8372(4) 0.0598(8) Uani 1.00 1 d . . . C(10) C 0.64201(7) 0.9375(4) 0.7358(3) 0.0435(6) Uani 1.00 1 d . . . C(11) C 0.66878(7) 1.0885(4) 0.7939(3) 0.0403(6) Uani 1.00 1 d . . . C(12) C 0.65565(8) 1.2843(4) 0.8680(3) 0.0472(6) Uani 1.00 1 d . . . C(13) C 0.61744(7) 1.3267(4) 0.8814(3) 0.0479(7) Uani 1.00 1 d . . . C(14) C 0.58950(7) 1.1769(4) 0.8202(3) 0.0414(6) Uani 1.00 1 d . . . C(15) C 0.54941(8) 1.2164(5) 0.8292(3) 0.0522(7) Uani 1.00 1 d . . . C(16) C 0.52328(8) 1.0673(5) 0.7680(4) 0.0577(8) Uani 1.00 1 d . . . C(17) C 0.53571(8) 0.8696(5) 0.6973(3) 0.0546(8) Uani 1.00 1 d . . . C(18) C 0.57420(7) 0.8251(5) 0.6860(3) 0.0476(6) Uani 1.00 1 d . . . C(19) C 0.60206(7) 0.9780(4) 0.7477(3) 0.0389(6) Uani 1.00 1 d . . . H(1) H 0.7134 1.2191 0.5392 0.051 Uiso 1.00 1 c R . . H(2) H 0.7108 0.9859 0.5049 0.051 Uiso 1.00 1 c R . . H(3) H 0.7477 1.0821 0.5659 0.051 Uiso 1.00 1 c R . . H(4) H 0.6362 0.2940 0.4288 0.055 Uiso 1.00 1 c R . . H(5) H 0.5706 0.2403 0.3792 0.062 Uiso 1.00 1 c R . . H(6) H 0.5334 0.5057 0.2352 0.064 Uiso 1.00 1 c R . . H(7) H 0.5617 0.8275 0.1448 0.062 Uiso 1.00 1 c R . . H(8) H 0.6273 0.8826 0.1976 0.055 Uiso 1.00 1 c R . . H(9) H 0.7253 1.1628 0.8497 0.055 Uiso 1.00 1 c R . . H(10) H 0.7537 0.8246 0.8194 0.072 Uiso 1.00 1 c R . . H(11) H 0.7131 0.7220 0.7657 0.072 Uiso 1.00 1 c R . . H(12) H 0.7209 0.8147 0.9669 0.072 Uiso 1.00 1 c R . . H(13) H 0.6504 0.8055 0.6874 0.052 Uiso 1.00 1 c R . . H(14) H 0.6737 1.3878 0.9091 0.057 Uiso 1.00 1 c R . . H(15) H 0.6095 1.4584 0.9324 0.058 Uiso 1.00 1 c R . . H(16) H 0.5407 1.3475 0.8782 0.063 Uiso 1.00 1 c R . . H(17) H 0.4968 1.0971 0.7731 0.069 Uiso 1.00 1 c R . . H(18) H 0.5174 0.7666 0.6573 0.065 Uiso 1.00 1 c R . . H(19) H 0.5822 0.6925 0.6372 0.057 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0501(11) 0.0515(11) 0.0533(12) -0.0106(9) 0.0043(8) 0.0039(9) O(2) 0.0355(9) 0.0554(11) 0.0702(13) 0.0026(8) -0.0025(8) 0.0078(10) N(1) 0.0308(10) 0.0426(11) 0.0535(13) -0.0001(9) 0.0038(9) 0.0013(10) C(1) 0.0369(13) 0.0479(16) 0.0390(14) 0.0020(12) 0.0001(11) -0.0053(12) C(2) 0.0353(12) 0.0432(14) 0.0384(13) 0.0033(11) 0.0019(10) -0.0083(12) C(3) 0.0404(14) 0.0493(16) 0.0467(16) 0.0007(12) -0.0032(12) -0.0018(13) C(4) 0.0435(15) 0.0608(19) 0.0521(18) -0.0086(14) 0.0055(13) -0.0069(14) C(5) 0.0337(13) 0.073(2) 0.0535(17) 0.0034(14) 0.0017(12) -0.0130(16) C(6) 0.0431(15) 0.0603(18) 0.0517(18) 0.0134(14) -0.0037(13) -0.0090(15) C(7) 0.0465(15) 0.0456(15) 0.0446(15) 0.0038(12) 0.0006(12) -0.0051(13) C(8) 0.0360(13) 0.0611(18) 0.0406(14) 0.0002(13) 0.0012(11) -0.0034(14) C(9) 0.0440(15) 0.083(2) 0.0529(18) 0.0093(15) 0.0037(13) 0.0173(16) C(10) 0.0395(14) 0.0464(15) 0.0448(16) 0.0014(11) 0.0019(11) -0.0057(12) C(11) 0.0358(13) 0.0513(15) 0.0337(13) 0.0013(12) -0.0005(10) -0.0023(13) C(12) 0.0449(15) 0.0469(16) 0.0500(16) -0.0057(13) 0.0047(12) -0.0077(14) C(13) 0.0450(15) 0.0498(16) 0.0493(17) 0.0008(13) 0.0053(12) -0.0097(14) C(14) 0.0372(14) 0.0487(16) 0.0386(14) 0.0016(12) 0.0060(11) -0.0021(12) C(15) 0.0440(15) 0.0600(18) 0.0530(18) 0.0080(13) 0.0066(13) -0.0046(15) C(16) 0.0370(14) 0.079(2) 0.0571(18) 0.0005(15) 0.0039(13) -0.0008(17) C(17) 0.0425(15) 0.069(2) 0.0523(18) -0.0094(14) -0.0012(13) -0.0003(15) C(18) 0.0437(15) 0.0548(16) 0.0445(16) -0.0050(13) 0.0021(12) -0.0013(14) C(19) 0.0332(13) 0.0467(15) 0.0367(14) -0.0014(11) -0.0005(10) -0.0009(12) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(1) 1.254(3) yes . . O(2) C(1) 1.269(3) yes . . N(1) C(8) 1.505(3) yes . . C(1) C(2) 1.503(3) yes . . C(2) C(3) 1.385(3) yes . . C(2) C(7) 1.390(3) yes . . C(3) C(4) 1.384(3) yes . . C(4) C(5) 1.382(4) yes . . C(5) C(6) 1.386(4) yes . . C(6) C(7) 1.386(3) yes . . C(8) C(9) 1.511(4) yes . . C(8) C(11) 1.516(3) yes . . C(10) C(11) 1.377(3) yes . . C(10) C(19) 1.414(3) yes . . C(11) C(12) 1.408(3) yes . . C(12) C(13) 1.358(3) yes . . C(13) C(14) 1.406(3) yes . . C(14) C(15) 1.416(3) yes . . C(14) C(19) 1.414(3) yes . . C(15) C(16) 1.361(4) yes . . C(16) C(17) 1.401(4) yes . . C(17) C(18) 1.369(3) yes . . C(18) C(19) 1.418(3) yes . . N(1) H(1) 0.900 no . . N(1) H(2) 0.900 no . . N(1) H(3) 0.900 no . . C(3) H(4) 0.940 no . . C(4) H(5) 0.940 no . . C(5) H(6) 0.940 no . . C(6) H(7) 0.940 no . . C(7) H(8) 0.940 no . . C(8) H(9) 0.990 no . . C(9) H(10) 0.970 no . . C(9) H(11) 0.970 no . . C(9) H(12) 0.970 no . . C(10) H(13) 0.940 no . . C(12) H(14) 0.940 no . . C(13) H(15) 0.940 no . . C(15) H(16) 0.940 no . . C(16) H(17) 0.940 no . . C(17) H(18) 0.940 no . . C(18) H(19) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O(1) C(1) O(2) 122.7(2) yes . . . O(1) C(1) C(2) 119.0(2) yes . . . O(2) C(1) C(2) 118.3(2) yes . . . C(1) C(2) C(3) 121.1(2) yes . . . C(1) C(2) C(7) 119.7(2) yes . . . C(3) C(2) C(7) 119.1(2) yes . . . C(2) C(3) C(4) 120.7(2) yes . . . C(3) C(4) C(5) 119.9(2) yes . . . C(4) C(5) C(6) 120.0(2) yes . . . C(5) C(6) C(7) 119.9(2) yes . . . C(2) C(7) C(6) 120.4(2) yes . . . N(1) C(8) C(9) 109.7(2) yes . . . N(1) C(8) C(11) 109.07(19) yes . . . C(9) C(8) C(11) 115.0(2) yes . . . C(11) C(10) C(19) 121.0(2) yes . . . C(8) C(11) C(10) 121.8(2) yes . . . C(8) C(11) C(12) 119.5(2) yes . . . C(10) C(11) C(12) 118.7(2) yes . . . C(11) C(12) C(13) 121.4(2) yes . . . C(12) C(13) C(14) 121.1(2) yes . . . C(13) C(14) C(15) 122.8(2) yes . . . C(13) C(14) C(19) 118.5(2) yes . . . C(15) C(14) C(19) 118.8(2) yes . . . C(14) C(15) C(16) 121.0(2) yes . . . C(15) C(16) C(17) 120.3(2) yes . . . C(16) C(17) C(18) 120.6(2) yes . . . C(17) C(18) C(19) 120.3(2) yes . . . C(10) C(19) C(14) 119.4(2) yes . . . C(10) C(19) C(18) 121.6(2) yes . . . C(14) C(19) C(18) 119.1(2) yes . . . C(8) N(1) H(1) 109.5 no . . . C(8) N(1) H(2) 109.5 no . . . C(8) N(1) H(3) 109.5 no . . . H(1) N(1) H(2) 109.5 no . . . H(1) N(1) H(3) 109.5 no . . . H(2) N(1) H(3) 109.5 no . . . C(2) C(3) H(4) 119.7 no . . . C(4) C(3) H(4) 119.7 no . . . C(3) C(4) H(5) 120.1 no . . . C(5) C(4) H(5) 120.0 no . . . C(4) C(5) H(6) 120.0 no . . . C(6) C(5) H(6) 120.0 no . . . C(5) C(6) H(7) 120.0 no . . . C(7) C(6) H(7) 120.1 no . . . C(2) C(7) H(8) 119.8 no . . . C(6) C(7) H(8) 119.8 no . . . N(1) C(8) H(9) 107.6 no . . . C(9) C(8) H(9) 107.6 no . . . C(11) C(8) H(9) 107.6 no . . . C(8) C(9) H(10) 109.5 no . . . C(8) C(9) H(11) 109.5 no . . . C(8) C(9) H(12) 109.5 no . . . H(10) C(9) H(11) 109.5 no . . . H(10) C(9) H(12) 109.5 no . . . H(11) C(9) H(12) 109.5 no . . . C(11) C(10) H(13) 119.5 no . . . C(19) C(10) H(13) 119.5 no . . . C(11) C(12) H(14) 119.3 no . . . C(13) C(12) H(14) 119.3 no . . . C(12) C(13) H(15) 119.5 no . . . C(14) C(13) H(15) 119.5 no . . . C(14) C(15) H(16) 119.5 no . . . C(16) C(15) H(16) 119.5 no . . . C(15) C(16) H(17) 119.9 no . . . C(17) C(16) H(17) 119.9 no . . . C(16) C(17) H(18) 119.7 no . . . C(18) C(17) H(18) 119.7 no . . . C(17) C(18) H(19) 119.8 no . . . C(19) C(18) H(19) 119.8 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O(1) C(1) C(2) C(3) 179.0(2) ? . . . . O(1) C(1) C(2) C(7) -2.9(3) ? . . . . O(2) C(1) C(2) C(3) -2.8(3) ? . . . . O(2) C(1) C(2) C(7) 175.3(2) ? . . . . C(1) C(2) C(3) C(4) 177.5(2) ? . . . . C(1) C(2) C(7) C(6) -177.9(2) ? . . . . C(3) C(2) C(7) C(6) 0.2(3) ? . . . . C(7) C(2) C(3) C(4) -0.6(3) ? . . . . C(2) C(3) C(4) C(5) 0.7(4) ? . . . . C(3) C(4) C(5) C(6) -0.4(4) ? . . . . C(4) C(5) C(6) C(7) 0.0(3) ? . . . . C(5) C(6) C(7) C(2) 0.1(3) ? . . . . N(1) C(8) C(11) C(10) 76.5(3) ? . . . . N(1) C(8) C(11) C(12) -101.3(2) ? . . . . C(9) C(8) C(11) C(10) -47.2(3) ? . . . . C(9) C(8) C(11) C(12) 135.0(2) ? . . . . C(11) C(10) C(19) C(14) 0.1(3) ? . . . . C(11) C(10) C(19) C(18) 179.2(2) ? . . . . C(19) C(10) C(11) C(8) -177.1(2) ? . . . . C(19) C(10) C(11) C(12) 0.7(3) ? . . . . C(8) C(11) C(12) C(13) 177.3(2) ? . . . . C(10) C(11) C(12) C(13) -0.6(3) ? . . . . C(11) C(12) C(13) C(14) -0.5(4) ? . . . . C(12) C(13) C(14) C(15) -179.0(2) ? . . . . C(12) C(13) C(14) C(19) 1.4(3) ? . . . . C(13) C(14) C(15) C(16) 179.8(2) ? . . . . C(13) C(14) C(19) C(10) -1.1(3) ? . . . . C(13) C(14) C(19) C(18) 179.8(2) ? . . . . C(15) C(14) C(19) C(10) 179.2(2) ? . . . . C(15) C(14) C(19) C(18) 0.2(3) ? . . . . C(19) C(14) C(15) C(16) -0.6(4) ? . . . . C(14) C(15) C(16) C(17) 1.0(4) ? . . . . C(15) C(16) C(17) C(18) -1.1(4) ? . . . . C(16) C(17) C(18) C(19) 0.7(4) ? . . . . C(17) C(18) C(19) C(10) -179.3(2) ? . . . . C(17) C(18) C(19) C(14) -0.2(3) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) O(2) 2.214(2) ? . . O(1) N(1) 2.758(2) ? . . O(1) N(1) 3.283(2) ? . 4_646 O(1) C(2) 2.380(3) ? . . O(1) C(7) 2.803(2) ? . . O(1) C(9) 3.598(3) ? . 1_554 O(2) O(1) 2.214(2) ? . . O(2) N(1) 2.778(2) ? . 1_545 O(2) N(1) 2.794(2) ? . 4_646 O(2) C(2) 2.383(3) ? . . O(2) C(3) 2.822(2) ? . . O(2) C(8) 3.529(3) ? . 4_646 O(2) C(9) 3.486(3) ? . 4_646 N(1) O(1) 2.758(2) ? . . N(1) O(1) 3.283(2) ? . 4_656 N(1) O(2) 2.778(2) ? . 1_565 N(1) O(2) 2.794(2) ? . 4_656 N(1) C(1) 3.514(3) ? . . N(1) C(1) 3.420(2) ? . 4_656 N(1) C(9) 2.465(3) ? . . N(1) C(10) 3.175(3) ? . . N(1) C(11) 2.460(3) ? . . N(1) C(12) 3.392(3) ? . . C(1) N(1) 3.514(3) ? . . C(1) N(1) 3.420(2) ? . 4_646 C(1) C(3) 2.516(3) ? . . C(1) C(7) 2.502(3) ? . . C(2) O(1) 2.380(3) ? . . C(2) O(2) 2.383(3) ? . . C(2) C(4) 2.406(3) ? . . C(2) C(5) 2.780(3) ? . . C(2) C(6) 2.409(3) ? . . C(3) O(2) 2.822(2) ? . . C(3) C(1) 2.516(3) ? . . C(3) C(5) 2.394(3) ? . . C(3) C(6) 2.765(3) ? . . C(3) C(7) 2.393(3) ? . . C(3) C(13) 3.586(3) ? . 1_544 C(4) C(2) 2.406(3) ? . . C(4) C(6) 2.397(4) ? . . C(4) C(7) 2.768(4) ? . . C(4) C(13) 3.596(3) ? . 1_544 C(5) C(2) 2.780(3) ? . . C(5) C(3) 2.394(3) ? . . C(5) C(7) 2.399(3) ? . . C(6) C(2) 2.409(3) ? . . C(6) C(3) 2.765(3) ? . . C(6) C(4) 2.397(4) ? . . C(6) C(18) 3.567(3) ? . . C(7) O(1) 2.803(2) ? . . C(7) C(1) 2.502(3) ? . . C(7) C(3) 2.393(3) ? . . C(7) C(4) 2.768(4) ? . . C(7) C(5) 2.399(3) ? . . C(8) O(2) 3.529(3) ? . 4_656 C(8) C(10) 2.529(3) ? . . C(8) C(12) 2.526(3) ? . . C(9) O(1) 3.598(3) ? . 1_556 C(9) O(2) 3.486(3) ? . 4_656 C(9) N(1) 2.465(3) ? . . C(9) C(10) 3.060(3) ? . . C(9) C(11) 2.553(4) ? . . C(10) N(1) 3.175(3) ? . . C(10) C(8) 2.529(3) ? . . C(10) C(9) 3.060(3) ? . . C(10) C(12) 2.396(3) ? . . C(10) C(13) 2.777(3) ? . . C(10) C(14) 2.441(3) ? . . C(10) C(18) 2.472(3) ? . . C(11) N(1) 2.460(3) ? . . C(11) C(9) 2.553(4) ? . . C(11) C(13) 2.413(3) ? . . C(11) C(14) 2.818(3) ? . . C(11) C(19) 2.430(3) ? . . C(12) N(1) 3.392(3) ? . . C(12) C(8) 2.526(3) ? . . C(12) C(10) 2.396(3) ? . . C(12) C(14) 2.407(3) ? . . C(12) C(19) 2.782(3) ? . . C(13) C(3) 3.586(3) ? . 1_566 C(13) C(4) 3.596(3) ? . 1_566 C(13) C(10) 2.777(3) ? . . C(13) C(11) 2.413(3) ? . . C(13) C(15) 2.478(3) ? . . C(13) C(19) 2.423(3) ? . . C(14) C(10) 2.441(3) ? . . C(14) C(11) 2.818(3) ? . . C(14) C(12) 2.407(3) ? . . C(14) C(16) 2.417(3) ? . . C(14) C(17) 2.796(3) ? . . C(14) C(18) 2.441(3) ? . . C(15) C(13) 2.478(3) ? . . C(15) C(17) 2.395(4) ? . . C(15) C(18) 2.784(4) ? . . C(15) C(19) 2.436(3) ? . . C(16) C(14) 2.417(3) ? . . C(16) C(18) 2.406(4) ? . . C(16) C(19) 2.798(3) ? . . C(17) C(14) 2.796(3) ? . . C(17) C(15) 2.395(4) ? . . C(17) C(19) 2.417(3) ? . . C(18) C(6) 3.567(3) ? . . C(18) C(10) 2.472(3) ? . . C(18) C(14) 2.441(3) ? . . C(18) C(15) 2.784(4) ? . . C(18) C(16) 2.406(4) ? . . C(19) C(11) 2.430(3) ? . . C(19) C(12) 2.782(3) ? . . C(19) C(13) 2.423(3) ? . . C(19) C(15) 2.436(3) ? . . C(19) C(16) 2.798(3) ? . . C(19) C(17) 2.417(3) ? . . O(1) H(1) 3.110 ? . . O(1) H(1) 3.387 ? . 4_646 O(1) H(2) 1.880 ? . . O(1) H(3) 3.094 ? . . O(1) H(3) 2.587 ? . 4_646 O(1) H(8) 2.500 ? . . O(1) H(9) 3.148 ? . 4_646 O(1) H(11) 3.415 ? . . O(1) H(12) 2.640 ? . 1_554 O(1) H(13) 3.203 ? . . O(2) H(1) 1.880 ? . 1_545 O(2) H(1) 3.324 ? . 4_646 O(2) H(2) 3.194 ? . 1_545 O(2) H(2) 3.105 ? . . O(2) H(2) 3.116 ? . 4_646 O(2) H(3) 3.150 ? . 1_545 O(2) H(3) 1.913 ? . 4_646 O(2) H(4) 2.527 ? . . O(2) H(9) 3.581 ? . 4_646 O(2) H(10) 2.762 ? . 4_646 O(2) H(11) 2.736 ? . . O(2) H(13) 3.139 ? . . O(2) H(14) 3.548 ? . 1_545 N(1) H(1) 3.329 ? . 4_646 N(1) H(2) 3.456 ? . 4_656 N(1) H(3) 3.477 ? . 4_646 N(1) H(3) 3.406 ? . 4_656 N(1) H(4) 3.383 ? . 1_565 N(1) H(9) 2.036 ? . . N(1) H(10) 2.626 ? . . N(1) H(10) 3.348 ? . 4_656 N(1) H(11) 2.677 ? . . N(1) H(11) 3.495 ? . 4_656 N(1) H(12) 3.303 ? . . N(1) H(13) 3.162 ? . . N(1) H(14) 3.505 ? . . C(1) H(1) 3.096 ? . 1_545 C(1) H(2) 2.628 ? . . C(1) H(3) 2.559 ? . 4_646 C(1) H(4) 2.670 ? . . C(1) H(8) 2.648 ? . . C(1) H(10) 3.278 ? . 4_646 C(1) H(11) 3.178 ? . . C(1) H(12) 3.388 ? . 1_554 C(1) H(13) 2.833 ? . . C(2) H(4) 2.023 ? . . C(2) H(5) 3.253 ? . . C(2) H(7) 3.256 ? . . C(2) H(8) 2.028 ? . . C(2) H(13) 2.990 ? . . C(2) H(14) 3.490 ? . 1_544 C(2) H(15) 3.071 ? . 1_544 C(2) H(19) 3.118 ? . . C(3) H(1) 3.579 ? . 1_545 C(3) H(5) 2.025 ? . . C(3) H(6) 3.243 ? . . C(3) H(8) 3.472 ? . 1_545 C(3) H(8) 3.242 ? . . C(3) H(13) 3.516 ? . . C(3) H(15) 3.220 ? . 1_544 C(3) H(19) 2.982 ? . . C(4) H(4) 2.021 ? . . C(4) H(6) 2.023 ? . . C(4) H(7) 3.245 ? . . C(4) H(8) 3.574 ? . 1_545 C(4) H(15) 3.188 ? . 1_544 C(4) H(17) 3.305 ? . 2_646 C(4) H(19) 2.929 ? . . C(5) H(4) 3.241 ? . . C(5) H(5) 2.024 ? . . C(5) H(7) 2.027 ? . . C(5) H(8) 3.246 ? . . C(5) H(15) 2.982 ? . 1_544 C(5) H(16) 3.020 ? . 1_544 C(5) H(17) 3.322 ? . 2_646 C(5) H(18) 3.143 ? . 2_656 C(5) H(19) 3.022 ? . . C(6) H(5) 3.246 ? . . C(6) H(5) 3.480 ? . 1_565 C(6) H(6) 2.026 ? . . C(6) H(8) 2.025 ? . . C(6) H(15) 2.807 ? . 1_544 C(6) H(16) 3.502 ? . 1_544 C(6) H(17) 3.471 ? . 2_656 C(6) H(18) 3.463 ? . 2_656 C(6) H(19) 3.154 ? . . C(7) H(4) 3.242 ? . . C(7) H(5) 3.579 ? . 1_565 C(7) H(6) 3.248 ? . . C(7) H(7) 2.027 ? . . C(7) H(13) 3.481 ? . . C(7) H(15) 2.851 ? . 1_544 C(7) H(19) 3.197 ? . . C(8) H(1) 1.994 ? . . C(8) H(2) 1.994 ? . . C(8) H(3) 1.994 ? . . C(8) H(10) 2.050 ? . . C(8) H(10) 3.576 ? . 4_657 C(8) H(11) 2.050 ? . . C(8) H(12) 2.050 ? . . C(8) H(12) 3.379 ? . 4_657 C(8) H(13) 2.680 ? . . C(8) H(14) 2.662 ? . . C(9) H(1) 3.242 ? . . C(9) H(1) 3.558 ? . 4_646 C(9) H(2) 2.627 ? . . C(9) H(3) 2.622 ? . . C(9) H(3) 3.455 ? . 4_646 C(9) H(9) 2.042 ? . . C(9) H(9) 2.985 ? . 4_647 C(9) H(13) 2.821 ? . . C(9) H(14) 3.358 ? . 1_545 C(10) H(1) 3.378 ? . . C(10) H(2) 2.968 ? . . C(10) H(4) 3.139 ? . 1_565 C(10) H(8) 3.417 ? . 1_556 C(10) H(9) 3.297 ? . . C(10) H(11) 2.809 ? . . C(10) H(12) 3.261 ? . . C(10) H(14) 3.242 ? . . C(10) H(15) 3.494 ? . 1_545 C(10) H(19) 2.655 ? . . C(11) H(1) 2.573 ? . . C(11) H(2) 2.662 ? . . C(11) H(3) 3.237 ? . . C(11) H(4) 3.121 ? . 1_565 C(11) H(8) 3.534 ? . 1_556 C(11) H(9) 2.046 ? . . C(11) H(10) 3.371 ? . . C(11) H(11) 2.755 ? . . C(11) H(12) 2.757 ? . . C(11) H(13) 2.014 ? . . C(11) H(14) 2.040 ? . . C(11) H(15) 3.257 ? . . C(12) H(1) 3.181 ? . . C(12) H(4) 3.237 ? . 1_565 C(12) H(9) 2.540 ? . . C(12) H(11) 3.460 ? . 1_565 C(12) H(13) 3.248 ? . . C(12) H(13) 3.489 ? . 1_565 C(12) H(15) 1.996 ? . . C(13) H(4) 3.368 ? . 1_565 C(13) H(8) 3.593 ? . 1_556 C(13) H(13) 3.491 ? . 1_565 C(13) H(14) 1.995 ? . . C(13) H(16) 2.666 ? . . C(13) H(19) 3.107 ? . 1_565 C(14) H(4) 3.384 ? . 1_565 C(14) H(5) 3.269 ? . 1_565 C(14) H(7) 3.359 ? . 1_556 C(14) H(8) 3.513 ? . 1_556 C(14) H(13) 3.288 ? . . C(14) H(14) 3.251 ? . . C(14) H(15) 2.040 ? . . C(14) H(16) 2.050 ? . . C(14) H(17) 3.265 ? . . C(14) H(19) 3.290 ? . . C(14) H(19) 3.468 ? . 1_565 C(15) H(5) 3.366 ? . 1_565 C(15) H(6) 3.504 ? . 1_566 C(15) H(6) 3.409 ? . 2_666 C(15) H(7) 3.343 ? . 1_556 C(15) H(15) 2.661 ? . . C(15) H(17) 2.002 ? . . C(15) H(17) 3.417 ? . 2_657 C(15) H(18) 3.238 ? . . C(15) H(19) 3.469 ? . 1_565 C(16) H(5) 3.470 ? . 1_565 C(16) H(5) 3.567 ? . 2_666 C(16) H(6) 3.355 ? . 2_666 C(16) H(7) 3.355 ? . 1_556 C(16) H(7) 3.378 ? . 2_656 C(16) H(16) 1.999 ? . . C(16) H(17) 3.422 ? . 2_657 C(16) H(18) 2.038 ? . . C(16) H(19) 3.254 ? . . C(17) H(5) 3.495 ? . 1_565 C(17) H(6) 3.338 ? . 2_656 C(17) H(7) 3.353 ? . 1_556 C(17) H(16) 3.495 ? . 1_545 C(17) H(16) 3.243 ? . . C(17) H(17) 2.039 ? . . C(17) H(18) 3.188 ? . 2_656 C(17) H(19) 2.009 ? . . C(18) H(5) 3.402 ? . 1_565 C(18) H(7) 3.365 ? . 1_556 C(18) H(13) 2.649 ? . . C(18) H(15) 3.122 ? . 1_545 C(18) H(16) 3.485 ? . 1_545 C(18) H(17) 3.249 ? . . C(18) H(18) 2.008 ? . . C(19) H(4) 3.276 ? . 1_565 C(19) H(5) 3.288 ? . 1_565 C(19) H(7) 3.367 ? . 1_556 C(19) H(8) 3.406 ? . 1_556 C(19) H(13) 2.048 ? . . C(19) H(15) 3.495 ? . 1_545 C(19) H(15) 3.273 ? . . C(19) H(16) 3.284 ? . . C(19) H(18) 3.266 ? . . C(19) H(19) 2.054 ? . . H(1) O(1) 3.110 ? . . H(1) O(1) 3.387 ? . 4_656 H(1) O(2) 1.880 ? . 1_565 H(1) O(2) 3.324 ? . 4_656 H(1) N(1) 3.329 ? . 4_656 H(1) C(1) 3.096 ? . 1_565 H(1) C(3) 3.579 ? . 1_565 H(1) C(8) 1.994 ? . . H(1) C(9) 3.242 ? . . H(1) C(9) 3.558 ? . 4_656 H(1) C(10) 3.378 ? . . H(1) C(11) 2.573 ? . . H(1) C(12) 3.181 ? . . H(1) H(2) 1.470 ? . . H(1) H(2) 3.131 ? . 4_656 H(1) H(3) 1.470 ? . . H(1) H(3) 2.743 ? . 4_656 H(1) H(4) 2.815 ? . 1_565 H(1) H(9) 2.303 ? . . H(1) H(10) 3.450 ? . . H(1) H(10) 2.941 ? . 4_656 H(1) H(11) 3.492 ? . . H(1) H(11) 3.523 ? . 1_565 H(1) H(11) 3.420 ? . 4_656 H(1) H(13) 3.555 ? . . H(1) H(14) 3.222 ? . . H(2) O(1) 1.880 ? . . H(2) O(2) 3.105 ? . . H(2) O(2) 3.194 ? . 1_565 H(2) O(2) 3.116 ? . 4_656 H(2) N(1) 3.456 ? . 4_646 H(2) C(1) 2.628 ? . . H(2) C(8) 1.994 ? . . H(2) C(9) 2.627 ? . . H(2) C(10) 2.968 ? . . H(2) C(11) 2.662 ? . . H(2) H(1) 1.470 ? . . H(2) H(1) 3.131 ? . 4_646 H(2) H(3) 1.470 ? . . H(2) H(3) 2.940 ? . 4_646 H(2) H(4) 3.252 ? . 1_565 H(2) H(9) 2.763 ? . . H(2) H(10) 2.868 ? . . H(2) H(10) 3.407 ? . 4_656 H(2) H(11) 2.500 ? . . H(2) H(12) 3.522 ? . . H(2) H(13) 2.746 ? . . H(3) O(1) 3.094 ? . . H(3) O(1) 2.587 ? . 4_656 H(3) O(2) 3.150 ? . 1_565 H(3) O(2) 1.913 ? . 4_656 H(3) N(1) 3.406 ? . 4_646 H(3) N(1) 3.477 ? . 4_656 H(3) C(1) 2.559 ? . 4_656 H(3) C(8) 1.994 ? . . H(3) C(9) 2.622 ? . . H(3) C(9) 3.455 ? . 4_656 H(3) C(11) 3.237 ? . . H(3) H(1) 1.470 ? . . H(3) H(1) 2.743 ? . 4_646 H(3) H(2) 1.470 ? . . H(3) H(2) 2.940 ? . 4_656 H(3) H(3) 3.249 ? . 4_646 H(3) H(3) 3.249 ? . 4_656 H(3) H(9) 2.273 ? . . H(3) H(10) 2.439 ? . . H(3) H(10) 3.171 ? . 4_656 H(3) H(11) 2.935 ? . . H(3) H(11) 2.925 ? . 4_656 H(3) H(12) 3.494 ? . . H(4) O(2) 2.527 ? . . H(4) N(1) 3.383 ? . 1_545 H(4) C(1) 2.670 ? . . H(4) C(2) 2.023 ? . . H(4) C(4) 2.021 ? . . H(4) C(5) 3.241 ? . . H(4) C(7) 3.242 ? . . H(4) C(10) 3.139 ? . 1_545 H(4) C(11) 3.121 ? . 1_545 H(4) C(12) 3.237 ? . 1_545 H(4) C(13) 3.368 ? . 1_545 H(4) C(14) 3.384 ? . 1_545 H(4) C(19) 3.276 ? . 1_545 H(4) H(1) 2.815 ? . 1_545 H(4) H(2) 3.252 ? . 1_545 H(4) H(5) 2.320 ? . . H(4) H(8) 3.063 ? . 1_545 H(4) H(13) 3.589 ? . 1_545 H(4) H(19) 3.472 ? . . H(5) C(2) 3.253 ? . . H(5) C(3) 2.025 ? . . H(5) C(5) 2.024 ? . . H(5) C(6) 3.480 ? . 1_545 H(5) C(6) 3.246 ? . . H(5) C(7) 3.579 ? . 1_545 H(5) C(14) 3.269 ? . 1_545 H(5) C(15) 3.366 ? . 1_545 H(5) C(16) 3.470 ? . 1_545 H(5) C(16) 3.567 ? . 2_646 H(5) C(17) 3.495 ? . 1_545 H(5) C(18) 3.402 ? . 1_545 H(5) C(19) 3.288 ? . 1_545 H(5) H(4) 2.320 ? . . H(5) H(6) 2.323 ? . . H(5) H(7) 3.082 ? . 1_545 H(5) H(8) 3.265 ? . 1_545 H(5) H(17) 2.709 ? . 2_646 H(5) H(19) 3.388 ? . . H(6) C(3) 3.243 ? . . H(6) C(4) 2.023 ? . . H(6) C(6) 2.026 ? . . H(6) C(7) 3.248 ? . . H(6) C(15) 3.504 ? . 1_544 H(6) C(15) 3.409 ? . 2_646 H(6) C(16) 3.355 ? . 2_646 H(6) C(17) 3.338 ? . 2_656 H(6) H(5) 2.323 ? . . H(6) H(7) 2.326 ? . . H(6) H(15) 3.494 ? . 1_544 H(6) H(16) 2.786 ? . 1_544 H(6) H(16) 2.853 ? . 2_646 H(6) H(17) 2.741 ? . 2_646 H(6) H(18) 3.517 ? . . H(6) H(18) 2.532 ? . 2_656 H(6) H(19) 3.526 ? . . H(7) C(2) 3.256 ? . . H(7) C(4) 3.245 ? . . H(7) C(5) 2.027 ? . . H(7) C(7) 2.027 ? . . H(7) C(14) 3.359 ? . 1_554 H(7) C(15) 3.343 ? . 1_554 H(7) C(16) 3.355 ? . 1_554 H(7) C(16) 3.378 ? . 2_656 H(7) C(17) 3.353 ? . 1_554 H(7) C(18) 3.365 ? . 1_554 H(7) C(19) 3.367 ? . 1_554 H(7) H(5) 3.082 ? . 1_565 H(7) H(6) 2.326 ? . . H(7) H(8) 2.324 ? . . H(7) H(15) 3.241 ? . 1_544 H(7) H(17) 2.708 ? . 2_656 H(7) H(18) 3.156 ? . 2_656 H(8) O(1) 2.500 ? . . H(8) C(1) 2.648 ? . . H(8) C(2) 2.028 ? . . H(8) C(3) 3.242 ? . . H(8) C(3) 3.472 ? . 1_565 H(8) C(4) 3.574 ? . 1_565 H(8) C(5) 3.246 ? . . H(8) C(6) 2.025 ? . . H(8) C(10) 3.417 ? . 1_554 H(8) C(11) 3.534 ? . 1_554 H(8) C(13) 3.593 ? . 1_554 H(8) C(14) 3.513 ? . 1_554 H(8) C(19) 3.406 ? . 1_554 H(8) H(4) 3.063 ? . 1_565 H(8) H(5) 3.265 ? . 1_565 H(8) H(7) 2.324 ? . . H(8) H(15) 3.306 ? . 1_544 H(9) O(1) 3.148 ? . 4_656 H(9) O(2) 3.581 ? . 4_656 H(9) N(1) 2.036 ? . . H(9) C(9) 2.042 ? . . H(9) C(9) 2.985 ? . 4_657 H(9) C(10) 3.297 ? . . H(9) C(11) 2.046 ? . . H(9) C(12) 2.540 ? . . H(9) H(1) 2.303 ? . . H(9) H(2) 2.763 ? . . H(9) H(3) 2.273 ? . . H(9) H(10) 2.329 ? . . H(9) H(10) 2.683 ? . 4_657 H(9) H(11) 2.829 ? . . H(9) H(11) 3.543 ? . 1_565 H(9) H(11) 3.486 ? . 4_657 H(9) H(12) 2.326 ? . . H(9) H(12) 2.451 ? . 4_657 H(9) H(13) 3.590 ? . . H(9) H(14) 2.320 ? . . H(10) O(2) 2.762 ? . 4_656 H(10) N(1) 2.626 ? . . H(10) N(1) 3.348 ? . 4_646 H(10) C(1) 3.278 ? . 4_656 H(10) C(8) 2.050 ? . . H(10) C(8) 3.576 ? . 4_647 H(10) C(11) 3.371 ? . . H(10) H(1) 3.450 ? . . H(10) H(1) 2.941 ? . 4_646 H(10) H(2) 2.868 ? . . H(10) H(2) 3.407 ? . 4_646 H(10) H(3) 2.439 ? . . H(10) H(3) 3.171 ? . 4_646 H(10) H(9) 2.329 ? . . H(10) H(9) 2.683 ? . 4_647 H(10) H(11) 1.584 ? . . H(10) H(12) 1.584 ? . . H(10) H(12) 3.513 ? . 4_657 H(10) H(14) 3.180 ? . 4_647 H(11) O(1) 3.415 ? . . H(11) O(2) 2.736 ? . . H(11) N(1) 2.677 ? . . H(11) N(1) 3.495 ? . 4_646 H(11) C(1) 3.178 ? . . H(11) C(8) 2.050 ? . . H(11) C(10) 2.809 ? . . H(11) C(11) 2.755 ? . . H(11) C(12) 3.460 ? . 1_545 H(11) H(1) 3.523 ? . 1_545 H(11) H(1) 3.492 ? . . H(11) H(1) 3.420 ? . 4_646 H(11) H(2) 2.500 ? . . H(11) H(3) 2.935 ? . . H(11) H(3) 2.925 ? . 4_646 H(11) H(9) 3.543 ? . 1_545 H(11) H(9) 2.829 ? . . H(11) H(9) 3.486 ? . 4_647 H(11) H(10) 1.584 ? . . H(11) H(12) 1.584 ? . . H(11) H(13) 2.293 ? . . H(11) H(14) 2.705 ? . 1_545 H(12) O(1) 2.640 ? . 1_556 H(12) N(1) 3.303 ? . . H(12) C(1) 3.388 ? . 1_556 H(12) C(8) 2.050 ? . . H(12) C(8) 3.379 ? . 4_647 H(12) C(10) 3.261 ? . . H(12) C(11) 2.757 ? . . H(12) H(2) 3.522 ? . . H(12) H(3) 3.494 ? . . H(12) H(9) 2.326 ? . . H(12) H(9) 2.451 ? . 4_647 H(12) H(10) 1.584 ? . . H(12) H(10) 3.513 ? . 4_647 H(12) H(11) 1.584 ? . . H(12) H(13) 3.134 ? . . H(12) H(14) 3.134 ? . 1_545 H(13) O(1) 3.203 ? . . H(13) O(2) 3.139 ? . . H(13) N(1) 3.162 ? . . H(13) C(1) 2.833 ? . . H(13) C(2) 2.990 ? . . H(13) C(3) 3.516 ? . . H(13) C(7) 3.481 ? . . H(13) C(8) 2.680 ? . . H(13) C(9) 2.821 ? . . H(13) C(11) 2.014 ? . . H(13) C(12) 3.489 ? . 1_545 H(13) C(12) 3.248 ? . . H(13) C(13) 3.491 ? . 1_545 H(13) C(14) 3.288 ? . . H(13) C(18) 2.649 ? . . H(13) C(19) 2.048 ? . . H(13) H(1) 3.555 ? . . H(13) H(2) 2.746 ? . . H(13) H(4) 3.589 ? . 1_565 H(13) H(9) 3.590 ? . . H(13) H(11) 2.293 ? . . H(13) H(12) 3.134 ? . . H(13) H(14) 3.142 ? . 1_545 H(13) H(15) 3.152 ? . 1_545 H(13) H(19) 2.487 ? . . H(14) O(2) 3.548 ? . 1_565 H(14) N(1) 3.505 ? . . H(14) C(2) 3.490 ? . 1_566 H(14) C(8) 2.662 ? . . H(14) C(9) 3.358 ? . 1_565 H(14) C(10) 3.242 ? . . H(14) C(11) 2.040 ? . . H(14) C(13) 1.995 ? . . H(14) C(14) 3.251 ? . . H(14) H(1) 3.222 ? . . H(14) H(9) 2.320 ? . . H(14) H(10) 3.180 ? . 4_657 H(14) H(11) 2.705 ? . 1_565 H(14) H(12) 3.134 ? . 1_565 H(14) H(13) 3.142 ? . 1_565 H(14) H(15) 2.281 ? . . H(15) C(2) 3.071 ? . 1_566 H(15) C(3) 3.220 ? . 1_566 H(15) C(4) 3.188 ? . 1_566 H(15) C(5) 2.982 ? . 1_566 H(15) C(6) 2.807 ? . 1_566 H(15) C(7) 2.851 ? . 1_566 H(15) C(10) 3.494 ? . 1_565 H(15) C(11) 3.257 ? . . H(15) C(12) 1.996 ? . . H(15) C(14) 2.040 ? . . H(15) C(15) 2.661 ? . . H(15) C(18) 3.122 ? . 1_565 H(15) C(19) 3.273 ? . . H(15) C(19) 3.495 ? . 1_565 H(15) H(6) 3.494 ? . 1_566 H(15) H(7) 3.241 ? . 1_566 H(15) H(8) 3.306 ? . 1_566 H(15) H(13) 3.152 ? . 1_565 H(15) H(14) 2.281 ? . . H(15) H(16) 2.507 ? . . H(15) H(19) 2.734 ? . 1_565 H(16) C(5) 3.020 ? . 1_566 H(16) C(6) 3.502 ? . 1_566 H(16) C(13) 2.666 ? . . H(16) C(14) 2.050 ? . . H(16) C(16) 1.999 ? . . H(16) C(17) 3.243 ? . . H(16) C(17) 3.495 ? . 1_565 H(16) C(18) 3.485 ? . 1_565 H(16) C(19) 3.284 ? . . H(16) H(6) 2.786 ? . 1_566 H(16) H(6) 2.853 ? . 2_666 H(16) H(15) 2.507 ? . . H(16) H(16) 3.373 ? . 2_657 H(16) H(17) 2.292 ? . . H(16) H(17) 3.266 ? . 2_657 H(16) H(18) 3.146 ? . 1_565 H(16) H(19) 3.136 ? . 1_565 H(17) C(4) 3.305 ? . 2_666 H(17) C(5) 3.322 ? . 2_666 H(17) C(6) 3.471 ? . 2_656 H(17) C(14) 3.265 ? . . H(17) C(15) 2.002 ? . . H(17) C(15) 3.417 ? . 2_657 H(17) C(16) 3.422 ? . 2_657 H(17) C(17) 2.039 ? . . H(17) C(18) 3.249 ? . . H(17) H(5) 2.709 ? . 2_666 H(17) H(6) 2.741 ? . 2_666 H(17) H(7) 2.708 ? . 2_656 H(17) H(16) 2.292 ? . . H(17) H(16) 3.266 ? . 2_657 H(17) H(17) 3.291 ? . 2_657 H(17) H(18) 2.335 ? . . H(18) C(5) 3.143 ? . 2_656 H(18) C(6) 3.463 ? . 2_656 H(18) C(15) 3.238 ? . . H(18) C(16) 2.038 ? . . H(18) C(17) 3.188 ? . 2_656 H(18) C(18) 2.008 ? . . H(18) C(19) 3.266 ? . . H(18) H(6) 3.517 ? . . H(18) H(6) 2.532 ? . 2_656 H(18) H(7) 3.156 ? . 2_656 H(18) H(16) 3.146 ? . 1_545 H(18) H(17) 2.335 ? . . H(18) H(18) 2.553 ? . 2_656 H(18) H(19) 2.302 ? . . H(19) C(2) 3.118 ? . . H(19) C(3) 2.982 ? . . H(19) C(4) 2.929 ? . . H(19) C(5) 3.022 ? . . H(19) C(6) 3.154 ? . . H(19) C(7) 3.197 ? . . H(19) C(10) 2.655 ? . . H(19) C(13) 3.107 ? . 1_545 H(19) C(14) 3.468 ? . 1_545 H(19) C(14) 3.290 ? . . H(19) C(15) 3.469 ? . 1_545 H(19) C(16) 3.254 ? . . H(19) C(17) 2.009 ? . . H(19) C(19) 2.054 ? . . H(19) H(4) 3.472 ? . . H(19) H(5) 3.388 ? . . H(19) H(6) 3.526 ? . . H(19) H(13) 2.487 ? . . H(19) H(15) 2.734 ? . 1_545 H(19) H(16) 3.136 ? . 1_545 H(19) H(18) 2.302 ? . . data__pBrBA_R1-2Naphthy-Ethyam_ _database_code_depnum_ccdc_archive 'CCDC 884891' #TrackingRef 'RNaph12-pBrBA.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H18 Br N O2 ' _chemical_formula_moiety 'C19 H18 Br N O2 ' _chemical_formula_weight 372.26 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,-Z 3 1/2+X,1/2+Y,+Z 4 1/2-X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 38.2177(7) _cell_length_b 6.19540(11) _cell_length_c 7.19732(13) _cell_angle_alpha 90.0000 _cell_angle_beta 92.0811(7) _cell_angle_gamma 90.0000 _cell_volume 1703.01(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8045 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 68.2 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760.00 _exptl_absorpt_coefficient_mu 3.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.363 _exptl_absorpt_correction_T_max 0.511 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 9154 _diffrn_reflns_av_R_equivalents 0.061 _diffrn_reflns_theta_max 68.23 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_ambient_temperature 213.1 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3025 _reflns_number_gt 2563 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1096 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3025 _refine_ls_number_parameters 210 _refine_ls_goodness_of_fit_ref 1.207 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0247P)^2^+2.2772P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.43 _refine_diff_density_min -0.51 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00176(15) _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1325 Friedel Pairs' _refine_ls_abs_structure_Flack -0.02(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Br Br -0.676 1.280 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br(1) Br 0.028238(11) -0.25100(14) -0.27562(8) 0.0720(2) Uani 1.00 1 d . . . O(1) O 0.20430(7) -0.2862(5) -0.0604(4) 0.0448(8) Uani 1.00 1 d . . . O(2) O 0.20090(8) 0.0331(5) -0.1983(4) 0.0404(7) Uani 1.00 1 d . . . N(1) N 0.22410(8) 0.3126(5) 0.0765(4) 0.0325(8) Uani 1.00 1 d . . . C(1) C 0.21424(10) 0.2755(8) 0.2736(5) 0.0369(10) Uani 1.00 1 d . . . C(2) C 0.22707(12) 0.0554(9) 0.3368(6) 0.0490(13) Uani 1.00 1 d . . . C(3) C 0.15119(10) 0.1616(6) 0.2319(5) 0.0318(9) Uani 1.00 1 d . . . C(4) C 0.17516(10) 0.3106(6) 0.2906(5) 0.0305(9) Uani 1.00 1 d . . . C(5) C 0.16341(12) 0.5101(7) 0.3636(6) 0.0373(10) Uani 1.00 1 d . . . C(6) C 0.12850(12) 0.5512(7) 0.3747(6) 0.0376(10) Uani 1.00 1 d . . . C(7) C 0.10289(12) 0.4010(6) 0.3125(6) 0.0332(9) Uani 1.00 1 d . . . C(8) C 0.06680(12) 0.4389(8) 0.3186(7) 0.0460(12) Uani 1.00 1 d . . . C(9) C 0.04327(12) 0.2860(10) 0.2589(7) 0.0564(14) Uani 1.00 1 d . . . C(10) C 0.05448(12) 0.0896(8) 0.1870(7) 0.0476(12) Uani 1.00 1 d . . . C(11) C 0.08938(11) 0.0459(7) 0.1780(6) 0.0398(10) Uani 1.00 1 d . . . C(12) C 0.11450(10) 0.1998(6) 0.2408(5) 0.0288(9) Uani 1.00 1 d . . . C(13) C 0.14885(10) -0.1756(6) -0.1895(5) 0.0281(9) Uani 1.00 1 d . . . C(14) C 0.13236(11) -0.3658(6) -0.1377(6) 0.0326(9) Uani 1.00 1 d . . . C(15) C 0.09622(11) -0.3900(7) -0.1649(6) 0.0376(10) Uani 1.00 1 d . . . C(16) C 0.07753(10) -0.2228(9) -0.2454(5) 0.0412(11) Uani 1.00 1 d . . . C(17) C 0.09309(12) -0.0337(8) -0.3021(6) 0.0419(11) Uani 1.00 1 d . . . C(18) C 0.12917(11) -0.0101(7) -0.2734(5) 0.0334(9) Uani 1.00 1 d . . . C(19) C 0.18759(10) -0.1424(6) -0.1476(5) 0.0300(9) Uani 1.00 1 d . . . H(1) H 0.2473 0.2915 0.0667 0.039 Uiso 1.00 1 c R . . H(2) H 0.2187 0.4488 0.0430 0.039 Uiso 1.00 1 c R . . H(3) H 0.2123 0.2196 0.0013 0.039 Uiso 1.00 1 c R . . H(4) H 0.2265 0.3850 0.3520 0.044 Uiso 1.00 1 c R . . H(5) H 0.2521 0.0456 0.3215 0.059 Uiso 1.00 1 c R . . H(6) H 0.2153 -0.0554 0.2626 0.059 Uiso 1.00 1 c R . . H(7) H 0.2220 0.0350 0.4667 0.059 Uiso 1.00 1 c R . . H(8) H 0.1590 0.0296 0.1840 0.038 Uiso 1.00 1 c R . . H(9) H 0.1798 0.6143 0.4044 0.045 Uiso 1.00 1 c R . . H(10) H 0.1213 0.6831 0.4251 0.045 Uiso 1.00 1 c R . . H(11) H 0.0587 0.5712 0.3644 0.055 Uiso 1.00 1 c R . . H(12) H 0.0192 0.3134 0.2663 0.068 Uiso 1.00 1 c R . . H(13) H 0.0379 -0.0130 0.1446 0.057 Uiso 1.00 1 c R . . H(14) H 0.0968 -0.0869 0.1299 0.048 Uiso 1.00 1 c R . . H(15) H 0.1457 -0.4787 -0.0841 0.039 Uiso 1.00 1 c R . . H(16) H 0.0849 -0.5175 -0.1290 0.045 Uiso 1.00 1 c R . . H(17) H 0.0796 0.0767 -0.3589 0.050 Uiso 1.00 1 c R . . H(18) H 0.1403 0.1174 -0.3105 0.040 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br(1) 0.0222(2) 0.1174(5) 0.0761(4) -0.0004(3) -0.0047(2) -0.0326(4) O(1) 0.0255(13) 0.0458(19) 0.062(2) 0.0011(14) -0.0078(13) 0.0095(18) O(2) 0.0331(16) 0.0468(18) 0.0410(18) -0.0108(14) -0.0025(14) 0.0020(15) N(1) 0.0217(15) 0.038(2) 0.0378(19) -0.0037(13) -0.0014(14) 0.0005(15) C(1) 0.0268(18) 0.057(3) 0.026(2) -0.001(2) -0.0046(15) -0.003(2) C(2) 0.035(2) 0.075(3) 0.037(2) 0.014(2) 0.005(2) 0.018(2) C(3) 0.026(2) 0.041(2) 0.029(2) 0.0006(17) 0.0041(17) -0.0051(18) C(4) 0.0267(19) 0.043(2) 0.0226(19) -0.0006(17) 0.0034(15) -0.0034(17) C(5) 0.038(2) 0.037(2) 0.036(2) -0.0055(19) 0.0034(19) -0.010(2) C(6) 0.043(2) 0.036(2) 0.035(2) -0.0039(19) 0.008(2) -0.007(2) C(7) 0.028(2) 0.038(2) 0.034(2) 0.0058(17) 0.0037(18) 0.0008(19) C(8) 0.031(2) 0.050(2) 0.057(3) 0.007(2) 0.008(2) -0.009(2) C(9) 0.027(2) 0.071(4) 0.071(3) 0.016(2) 0.008(2) -0.003(3) C(10) 0.028(2) 0.066(3) 0.049(3) -0.010(2) -0.002(2) -0.012(2) C(11) 0.033(2) 0.042(2) 0.045(2) -0.004(2) 0.004(2) -0.010(2) C(12) 0.0266(19) 0.036(2) 0.024(2) -0.0000(16) -0.0000(15) -0.0036(17) C(13) 0.0189(18) 0.042(2) 0.024(2) 0.0032(15) -0.0013(15) -0.0061(16) C(14) 0.025(2) 0.036(2) 0.036(2) -0.0030(17) -0.0015(18) -0.0009(19) C(15) 0.029(2) 0.048(2) 0.036(2) -0.0075(19) 0.003(2) -0.007(2) C(16) 0.0222(18) 0.066(3) 0.035(2) 0.001(2) -0.0005(16) -0.015(2) C(17) 0.032(2) 0.055(2) 0.038(2) 0.009(2) 0.000(2) -0.002(2) C(18) 0.035(2) 0.037(2) 0.027(2) 0.0040(18) -0.0034(18) 0.0002(19) C(19) 0.0194(19) 0.040(2) 0.030(2) -0.0028(17) 0.0003(16) -0.0040(18) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Br(1) C(16) 1.897(3) yes . . O(1) C(19) 1.252(5) yes . . O(2) C(19) 1.260(5) yes . . N(1) C(1) 1.499(5) yes . . C(1) C(2) 1.513(7) yes . . C(1) C(4) 1.519(5) yes . . C(3) C(4) 1.357(5) yes . . C(3) C(12) 1.426(5) yes . . C(4) C(5) 1.422(6) yes . . C(5) C(6) 1.363(6) yes . . C(6) C(7) 1.411(6) yes . . C(7) C(8) 1.401(6) yes . . C(7) C(12) 1.426(5) yes . . C(8) C(9) 1.365(7) yes . . C(9) C(10) 1.396(8) yes . . C(10) C(11) 1.365(6) yes . . C(11) C(12) 1.415(5) yes . . C(13) C(14) 1.393(5) yes . . C(13) C(18) 1.396(5) yes . . C(13) C(19) 1.514(5) yes . . C(14) C(15) 1.396(5) yes . . C(15) C(16) 1.375(6) yes . . C(16) C(17) 1.382(7) yes . . C(17) C(18) 1.395(6) yes . . N(1) H(1) 0.900 no . . N(1) H(2) 0.900 no . . N(1) H(3) 0.900 no . . C(1) H(4) 0.990 no . . C(2) H(5) 0.970 no . . C(2) H(6) 0.970 no . . C(2) H(7) 0.970 no . . C(3) H(8) 0.940 no . . C(5) H(9) 0.940 no . . C(6) H(10) 0.940 no . . C(8) H(11) 0.940 no . . C(9) H(12) 0.940 no . . C(10) H(13) 0.940 no . . C(11) H(14) 0.940 no . . C(14) H(15) 0.940 no . . C(15) H(16) 0.940 no . . C(17) H(17) 0.940 no . . C(18) H(18) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 N(1) C(1) C(2) 109.4(3) yes . . . N(1) C(1) C(4) 109.6(3) yes . . . C(2) C(1) C(4) 114.4(3) yes . . . C(4) C(3) C(12) 121.8(3) yes . . . C(1) C(4) C(3) 122.2(3) yes . . . C(1) C(4) C(5) 118.6(3) yes . . . C(3) C(4) C(5) 119.2(3) yes . . . C(4) C(5) C(6) 120.4(4) yes . . . C(5) C(6) C(7) 121.8(4) yes . . . C(6) C(7) C(8) 123.5(4) yes . . . C(6) C(7) C(12) 118.0(3) yes . . . C(8) C(7) C(12) 118.5(4) yes . . . C(7) C(8) C(9) 120.8(4) yes . . . C(8) C(9) C(10) 120.9(4) yes . . . C(9) C(10) C(11) 120.3(4) yes . . . C(10) C(11) C(12) 120.3(4) yes . . . C(3) C(12) C(7) 118.7(3) yes . . . C(3) C(12) C(11) 122.0(3) yes . . . C(7) C(12) C(11) 119.2(3) yes . . . C(14) C(13) C(18) 119.7(3) yes . . . C(14) C(13) C(19) 120.7(3) yes . . . C(18) C(13) C(19) 119.6(3) yes . . . C(13) C(14) C(15) 120.5(3) yes . . . C(14) C(15) C(16) 118.3(4) yes . . . Br(1) C(16) C(15) 118.5(3) yes . . . Br(1) C(16) C(17) 118.7(3) yes . . . C(15) C(16) C(17) 122.7(3) yes . . . C(16) C(17) C(18) 118.6(4) yes . . . C(13) C(18) C(17) 120.1(4) yes . . . O(1) C(19) O(2) 123.8(3) yes . . . O(1) C(19) C(13) 118.7(3) yes . . . O(2) C(19) C(13) 117.5(3) yes . . . C(1) N(1) H(1) 109.5 no . . . C(1) N(1) H(2) 109.5 no . . . C(1) N(1) H(3) 109.5 no . . . H(1) N(1) H(2) 109.5 no . . . H(1) N(1) H(3) 109.5 no . . . H(2) N(1) H(3) 109.5 no . . . N(1) C(1) H(4) 107.7 no . . . C(2) C(1) H(4) 107.7 no . . . C(4) C(1) H(4) 107.7 no . . . C(1) C(2) H(5) 109.5 no . . . C(1) C(2) H(6) 109.5 no . . . C(1) C(2) H(7) 109.5 no . . . H(5) C(2) H(6) 109.5 no . . . H(5) C(2) H(7) 109.5 no . . . H(6) C(2) H(7) 109.5 no . . . C(4) C(3) H(8) 119.1 no . . . C(12) C(3) H(8) 119.1 no . . . C(4) C(5) H(9) 119.8 no . . . C(6) C(5) H(9) 119.8 no . . . C(5) C(6) H(10) 119.1 no . . . C(7) C(6) H(10) 119.1 no . . . C(7) C(8) H(11) 119.6 no . . . C(9) C(8) H(11) 119.6 no . . . C(8) C(9) H(12) 119.5 no . . . C(10) C(9) H(12) 119.5 no . . . C(9) C(10) H(13) 119.9 no . . . C(11) C(10) H(13) 119.8 no . . . C(10) C(11) H(14) 119.9 no . . . C(12) C(11) H(14) 119.9 no . . . C(13) C(14) H(15) 119.7 no . . . C(15) C(14) H(15) 119.7 no . . . C(14) C(15) H(16) 120.8 no . . . C(16) C(15) H(16) 120.8 no . . . C(16) C(17) H(17) 120.7 no . . . C(18) C(17) H(17) 120.7 no . . . C(13) C(18) H(18) 119.9 no . . . C(17) C(18) H(18) 119.9 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N(1) C(1) C(4) C(3) 77.0(5) ? . . . . N(1) C(1) C(4) C(5) -100.4(4) ? . . . . C(2) C(1) C(4) C(3) -46.4(5) ? . . . . C(2) C(1) C(4) C(5) 136.2(4) ? . . . . C(4) C(3) C(12) C(7) 0.4(6) ? . . . . C(4) C(3) C(12) C(11) 179.3(4) ? . . . . C(12) C(3) C(4) C(1) -177.2(3) ? . . . . C(12) C(3) C(4) C(5) 0.2(5) ? . . . . C(1) C(4) C(5) C(6) 177.6(3) ? . . . . C(3) C(4) C(5) C(6) 0.1(5) ? . . . . C(4) C(5) C(6) C(7) -1.0(6) ? . . . . C(5) C(6) C(7) C(8) -178.8(4) ? . . . . C(5) C(6) C(7) C(12) 1.5(6) ? . . . . C(6) C(7) C(8) C(9) -179.0(4) ? . . . . C(6) C(7) C(12) C(3) -1.2(6) ? . . . . C(6) C(7) C(12) C(11) 179.8(4) ? . . . . C(8) C(7) C(12) C(3) 179.1(4) ? . . . . C(8) C(7) C(12) C(11) 0.1(4) ? . . . . C(12) C(7) C(8) C(9) 0.6(7) ? . . . . C(7) C(8) C(9) C(10) -1.2(8) ? . . . . C(8) C(9) C(10) C(11) 1.0(8) ? . . . . C(9) C(10) C(11) C(12) -0.3(6) ? . . . . C(10) C(11) C(12) C(3) -179.3(4) ? . . . . C(10) C(11) C(12) C(7) -0.3(5) ? . . . . C(14) C(13) C(18) C(17) 1.1(6) ? . . . . C(18) C(13) C(14) C(15) -1.6(6) ? . . . . C(14) C(13) C(19) O(1) -2.2(6) ? . . . . C(14) C(13) C(19) O(2) 179.9(3) ? . . . . C(19) C(13) C(14) C(15) 175.5(3) ? . . . . C(18) C(13) C(19) O(1) 174.9(3) ? . . . . C(18) C(13) C(19) O(2) -3.0(5) ? . . . . C(19) C(13) C(18) C(17) -176.0(3) ? . . . . C(13) C(14) C(15) C(16) 0.6(6) ? . . . . C(14) C(15) C(16) Br(1) -178.1(3) ? . . . . C(14) C(15) C(16) C(17) 0.8(6) ? . . . . Br(1) C(16) C(17) C(18) 177.6(3) ? . . . . C(15) C(16) C(17) C(18) -1.2(7) ? . . . . C(16) C(17) C(18) C(13) 0.2(5) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Br(1) C(15) 2.824(4) ? . . Br(1) C(17) 2.833(4) ? . . O(1) O(2) 2.215(4) ? . . O(1) N(1) 2.769(4) ? . 1_545 O(1) N(1) 2.810(4) ? . 4_545 O(1) C(1) 3.541(4) ? . 4_545 O(1) C(2) 3.490(5) ? . 4_545 O(1) C(13) 2.384(4) ? . . O(1) C(14) 2.829(4) ? . . O(2) O(1) 2.215(4) ? . . O(2) N(1) 2.751(4) ? . . O(2) N(1) 3.266(4) ? . 4_545 O(2) C(2) 3.530(5) ? . 1_554 O(2) C(13) 2.375(4) ? . . O(2) C(18) 2.788(5) ? . . N(1) O(1) 2.769(4) ? . 1_565 N(1) O(1) 2.810(4) ? . 4_555 N(1) O(2) 2.751(4) ? . . N(1) O(2) 3.266(4) ? . 4_555 N(1) C(2) 2.459(6) ? . . N(1) C(3) 3.181(5) ? . . N(1) C(4) 2.466(5) ? . . N(1) C(5) 3.390(5) ? . . N(1) C(19) 3.511(5) ? . . N(1) C(19) 3.407(4) ? . 4_555 C(1) O(1) 3.541(4) ? . 4_555 C(1) C(3) 2.518(5) ? . . C(1) C(5) 2.529(6) ? . . C(2) O(1) 3.490(5) ? . 4_555 C(2) O(2) 3.530(5) ? . 1_556 C(2) N(1) 2.459(6) ? . . C(2) C(3) 3.042(5) ? . . C(2) C(4) 2.549(6) ? . . C(3) N(1) 3.181(5) ? . . C(3) C(1) 2.518(5) ? . . C(3) C(2) 3.042(5) ? . . C(3) C(5) 2.397(6) ? . . C(3) C(6) 2.775(6) ? . . C(3) C(7) 2.454(6) ? . . C(3) C(11) 2.485(5) ? . . C(4) N(1) 2.466(5) ? . . C(4) C(2) 2.549(6) ? . . C(4) C(6) 2.418(6) ? . . C(4) C(7) 2.828(5) ? . . C(4) C(12) 2.432(5) ? . . C(5) N(1) 3.390(5) ? . . C(5) C(1) 2.529(6) ? . . C(5) C(3) 2.397(6) ? . . C(5) C(7) 2.425(6) ? . . C(5) C(12) 2.802(6) ? . . C(6) C(3) 2.775(6) ? . . C(6) C(4) 2.418(6) ? . . C(6) C(8) 2.478(6) ? . . C(6) C(12) 2.432(6) ? . . C(6) C(14) 3.545(6) ? . 1_566 C(6) C(15) 3.596(6) ? . 1_566 C(7) C(3) 2.454(6) ? . . C(7) C(4) 2.828(5) ? . . C(7) C(5) 2.425(6) ? . . C(7) C(9) 2.405(6) ? . . C(7) C(10) 2.800(6) ? . . C(7) C(11) 2.451(6) ? . . C(8) C(6) 2.478(6) ? . . C(8) C(10) 2.402(7) ? . . C(8) C(11) 2.786(7) ? . . C(8) C(12) 2.430(6) ? . . C(9) C(7) 2.405(6) ? . . C(9) C(11) 2.394(7) ? . . C(9) C(12) 2.782(6) ? . . C(10) C(7) 2.800(6) ? . . C(10) C(8) 2.402(7) ? . . C(10) C(12) 2.411(6) ? . . C(11) C(3) 2.485(5) ? . . C(11) C(7) 2.451(6) ? . . C(11) C(8) 2.786(7) ? . . C(11) C(9) 2.394(7) ? . . C(11) C(16) 3.487(6) ? . . C(11) C(17) 3.498(6) ? . . C(12) C(4) 2.432(5) ? . . C(12) C(5) 2.802(6) ? . . C(12) C(6) 2.432(6) ? . . C(12) C(8) 2.430(6) ? . . C(12) C(9) 2.782(6) ? . . C(12) C(10) 2.411(6) ? . . C(13) O(1) 2.384(4) ? . . C(13) O(2) 2.375(4) ? . . C(13) C(15) 2.422(5) ? . . C(13) C(16) 2.756(5) ? . . C(13) C(17) 2.418(6) ? . . C(14) O(1) 2.829(4) ? . . C(14) C(6) 3.545(6) ? . 1_544 C(14) C(16) 2.379(5) ? . . C(14) C(17) 2.785(6) ? . . C(14) C(18) 2.411(6) ? . . C(14) C(19) 2.527(5) ? . . C(15) Br(1) 2.824(4) ? . . C(15) C(6) 3.596(6) ? . 1_544 C(15) C(13) 2.422(5) ? . . C(15) C(17) 2.420(6) ? . . C(15) C(18) 2.794(6) ? . . C(16) C(11) 3.487(6) ? . . C(16) C(13) 2.756(5) ? . . C(16) C(14) 2.379(5) ? . . C(16) C(18) 2.387(6) ? . . C(17) Br(1) 2.833(4) ? . . C(17) C(11) 3.498(6) ? . . C(17) C(13) 2.418(6) ? . . C(17) C(14) 2.785(6) ? . . C(17) C(15) 2.420(6) ? . . C(18) O(2) 2.788(5) ? . . C(18) C(14) 2.411(6) ? . . C(18) C(15) 2.794(6) ? . . C(18) C(16) 2.387(6) ? . . C(18) C(19) 2.516(5) ? . . C(19) N(1) 3.511(5) ? . . C(19) N(1) 3.407(4) ? . 4_545 C(19) C(14) 2.527(5) ? . . C(19) C(18) 2.516(5) ? . . Br(1) H(11) 3.083 ? . 1_544 Br(1) H(11) 3.537 ? . 2_545 Br(1) H(12) 3.253 ? . 2_545 Br(1) H(13) 3.373 ? . . Br(1) H(13) 3.103 ? . 2_555 Br(1) H(16) 2.893 ? . . Br(1) H(17) 2.903 ? . . O(1) H(1) 3.204 ? . 1_545 O(1) H(1) 1.915 ? . 4_545 O(1) H(2) 1.876 ? . 1_545 O(1) H(2) 3.283 ? . 4_545 O(1) H(3) 3.107 ? . 1_545 O(1) H(3) 3.178 ? . . O(1) H(3) 3.200 ? . 4_545 O(1) H(4) 3.595 ? . 4_545 O(1) H(5) 2.760 ? . 4_545 O(1) H(6) 2.749 ? . . O(1) H(8) 3.185 ? . . O(1) H(9) 3.560 ? . 1_545 O(1) H(15) 2.538 ? . . O(2) H(1) 3.016 ? . . O(2) H(1) 2.632 ? . 4_545 O(2) H(2) 3.166 ? . . O(2) H(2) 3.275 ? . 4_545 O(2) H(3) 1.882 ? . . O(2) H(4) 3.159 ? . 4_545 O(2) H(6) 3.388 ? . . O(2) H(7) 2.570 ? . 1_554 O(2) H(8) 3.234 ? . . O(2) H(18) 2.482 ? . . N(1) H(1) 3.572 ? . 4_545 N(1) H(1) 3.339 ? . 4_555 N(1) H(2) 3.277 ? . 4_545 N(1) H(3) 3.561 ? . 4_555 N(1) H(4) 2.032 ? . . N(1) H(5) 2.619 ? . . N(1) H(5) 3.362 ? . 4_555 N(1) H(6) 2.672 ? . . N(1) H(6) 3.522 ? . 4_555 N(1) H(7) 3.297 ? . . N(1) H(8) 3.163 ? . . N(1) H(9) 3.496 ? . . N(1) H(15) 3.426 ? . 1_565 C(1) H(1) 1.989 ? . . C(1) H(2) 1.989 ? . . C(1) H(3) 1.989 ? . . C(1) H(5) 2.052 ? . . C(1) H(5) 3.560 ? . 4_556 C(1) H(6) 2.052 ? . . C(1) H(7) 2.052 ? . . C(1) H(7) 3.418 ? . 4_556 C(1) H(8) 2.664 ? . . C(1) H(9) 2.667 ? . . C(2) H(1) 2.573 ? . . C(2) H(1) 3.504 ? . 4_545 C(2) H(2) 3.235 ? . . C(2) H(2) 3.553 ? . 4_545 C(2) H(3) 2.662 ? . . C(2) H(4) 2.045 ? . . C(2) H(4) 2.998 ? . 4_546 C(2) H(8) 2.792 ? . . C(2) H(9) 3.321 ? . 1_545 C(3) H(2) 3.452 ? . . C(3) H(3) 2.936 ? . . C(3) H(4) 3.282 ? . . C(3) H(6) 2.796 ? . . C(3) H(7) 3.235 ? . . C(3) H(9) 3.242 ? . . C(3) H(10) 3.485 ? . 1_545 C(3) H(14) 2.669 ? . . C(3) H(15) 3.185 ? . 1_565 C(3) H(18) 3.346 ? . 1_556 C(4) H(1) 3.244 ? . . C(4) H(2) 2.624 ? . . C(4) H(3) 2.623 ? . . C(4) H(4) 2.049 ? . . C(4) H(5) 3.369 ? . . C(4) H(6) 2.749 ? . . C(4) H(7) 2.750 ? . . C(4) H(8) 1.992 ? . . C(4) H(9) 2.058 ? . . C(4) H(10) 3.263 ? . . C(4) H(15) 3.166 ? . 1_565 C(4) H(18) 3.425 ? . 1_556 C(5) H(2) 3.206 ? . . C(5) H(4) 2.538 ? . . C(5) H(6) 3.437 ? . 1_565 C(5) H(8) 3.247 ? . . C(5) H(8) 3.470 ? . 1_565 C(5) H(10) 1.997 ? . . C(5) H(15) 3.269 ? . 1_565 C(5) H(18) 3.515 ? . 1_556 C(6) H(8) 3.485 ? . 1_565 C(6) H(9) 2.004 ? . . C(6) H(11) 2.668 ? . . C(6) H(14) 3.074 ? . 1_565 C(6) H(15) 3.395 ? . 1_565 C(6) H(18) 3.533 ? . 1_556 C(7) H(8) 3.300 ? . . C(7) H(9) 3.269 ? . . C(7) H(10) 2.041 ? . . C(7) H(11) 2.037 ? . . C(7) H(12) 3.250 ? . . C(7) H(14) 3.301 ? . . C(7) H(14) 3.439 ? . 1_565 C(7) H(15) 3.423 ? . 1_565 C(7) H(16) 3.266 ? . 1_565 C(7) H(17) 3.251 ? . 1_556 C(7) H(18) 3.493 ? . 1_556 C(8) H(10) 2.664 ? . . C(8) H(12) 2.002 ? . . C(8) H(13) 3.244 ? . . C(8) H(14) 3.450 ? . 1_565 C(8) H(16) 3.331 ? . 1_565 C(8) H(17) 3.253 ? . 1_556 C(9) H(11) 2.003 ? . . C(9) H(13) 2.034 ? . . C(9) H(14) 3.243 ? . . C(9) H(16) 3.484 ? . 1_565 C(9) H(17) 3.302 ? . 1_556 C(10) H(11) 3.458 ? . 1_545 C(10) H(11) 3.247 ? . . C(10) H(12) 2.031 ? . . C(10) H(14) 2.006 ? . . C(10) H(16) 3.556 ? . 1_565 C(10) H(17) 3.374 ? . 1_556 C(11) H(8) 2.661 ? . . C(11) H(10) 3.089 ? . 1_545 C(11) H(11) 3.455 ? . 1_545 C(11) H(12) 3.236 ? . . C(11) H(13) 2.006 ? . . C(11) H(16) 3.493 ? . 1_565 C(11) H(17) 3.373 ? . 1_556 C(12) H(8) 2.054 ? . . C(12) H(10) 3.471 ? . 1_545 C(12) H(10) 3.282 ? . . C(12) H(11) 3.282 ? . . C(12) H(13) 3.261 ? . . C(12) H(14) 2.052 ? . . C(12) H(15) 3.325 ? . 1_565 C(12) H(16) 3.348 ? . 1_565 C(12) H(17) 3.307 ? . 1_556 C(12) H(18) 3.380 ? . 1_556 C(13) H(8) 2.986 ? . . C(13) H(9) 3.448 ? . 1_544 C(13) H(10) 3.059 ? . 1_544 C(13) H(14) 3.144 ? . . C(13) H(15) 2.031 ? . . C(13) H(16) 3.274 ? . . C(13) H(17) 3.270 ? . . C(13) H(18) 2.035 ? . . C(14) H(8) 3.497 ? . . C(14) H(10) 3.174 ? . 1_544 C(14) H(14) 2.956 ? . . C(14) H(16) 2.044 ? . . C(14) H(18) 3.452 ? . 1_545 C(14) H(18) 3.260 ? . . C(15) H(10) 3.168 ? . 1_544 C(15) H(14) 2.833 ? . . C(15) H(15) 2.033 ? . . C(15) H(17) 3.263 ? . . C(16) H(10) 3.008 ? . 1_544 C(16) H(11) 3.145 ? . 1_544 C(16) H(13) 3.488 ? . . C(16) H(14) 2.898 ? . . C(16) H(15) 3.229 ? . . C(16) H(16) 2.024 ? . . C(16) H(17) 2.030 ? . . C(16) H(18) 3.239 ? . . C(17) H(10) 2.872 ? . 1_544 C(17) H(14) 3.125 ? . . C(17) H(16) 3.265 ? . . C(17) H(16) 3.450 ? . 1_565 C(17) H(18) 2.034 ? . . C(18) H(8) 3.453 ? . . C(18) H(10) 2.892 ? . 1_544 C(18) H(14) 3.232 ? . . C(18) H(15) 3.259 ? . . C(18) H(17) 2.041 ? . . C(19) H(1) 2.569 ? . 4_545 C(19) H(2) 3.096 ? . 1_545 C(19) H(3) 2.645 ? . . C(19) H(5) 3.290 ? . 4_545 C(19) H(6) 3.147 ? . . C(19) H(7) 3.303 ? . 1_554 C(19) H(8) 2.866 ? . . C(19) H(9) 3.562 ? . 1_544 C(19) H(15) 2.678 ? . . C(19) H(18) 2.662 ? . . H(1) O(1) 3.204 ? . 1_565 H(1) O(1) 1.915 ? . 4_555 H(1) O(2) 3.016 ? . . H(1) O(2) 2.632 ? . 4_555 H(1) N(1) 3.339 ? . 4_545 H(1) N(1) 3.572 ? . 4_555 H(1) C(1) 1.989 ? . . H(1) C(2) 2.573 ? . . H(1) C(2) 3.504 ? . 4_555 H(1) C(4) 3.244 ? . . H(1) C(19) 2.569 ? . 4_555 H(1) H(1) 3.252 ? . 4_545 H(1) H(1) 3.252 ? . 4_555 H(1) H(2) 1.469 ? . . H(1) H(2) 2.628 ? . 4_545 H(1) H(3) 1.470 ? . . H(1) H(3) 3.117 ? . 4_555 H(1) H(4) 2.301 ? . . H(1) H(5) 2.386 ? . . H(1) H(5) 3.208 ? . 4_555 H(1) H(6) 2.868 ? . . H(1) H(6) 2.969 ? . 4_555 H(1) H(7) 3.456 ? . . H(2) O(1) 1.876 ? . 1_565 H(2) O(1) 3.283 ? . 4_555 H(2) O(2) 3.166 ? . . H(2) O(2) 3.275 ? . 4_555 H(2) N(1) 3.277 ? . 4_555 H(2) C(1) 1.989 ? . . H(2) C(2) 3.235 ? . . H(2) C(2) 3.553 ? . 4_555 H(2) C(3) 3.452 ? . . H(2) C(4) 2.624 ? . . H(2) C(5) 3.206 ? . . H(2) C(19) 3.096 ? . 1_565 H(2) H(1) 1.469 ? . . H(2) H(1) 2.628 ? . 4_555 H(2) H(3) 1.470 ? . . H(2) H(3) 3.153 ? . 4_555 H(2) H(4) 2.268 ? . . H(2) H(5) 3.422 ? . . H(2) H(5) 2.950 ? . 4_555 H(2) H(6) 3.505 ? . . H(2) H(6) 3.460 ? . 1_565 H(2) H(6) 3.408 ? . 4_555 H(2) H(9) 3.210 ? . . H(2) H(15) 2.938 ? . 1_565 H(3) O(1) 3.178 ? . . H(3) O(1) 3.107 ? . 1_565 H(3) O(1) 3.200 ? . 4_555 H(3) O(2) 1.882 ? . . H(3) N(1) 3.561 ? . 4_545 H(3) C(1) 1.989 ? . . H(3) C(2) 2.662 ? . . H(3) C(3) 2.936 ? . . H(3) C(4) 2.623 ? . . H(3) C(19) 2.645 ? . . H(3) H(1) 1.470 ? . . H(3) H(1) 3.117 ? . 4_545 H(3) H(2) 1.470 ? . . H(3) H(2) 3.153 ? . 4_545 H(3) H(4) 2.760 ? . . H(3) H(5) 2.922 ? . . H(3) H(5) 3.399 ? . 4_555 H(3) H(6) 2.537 ? . . H(3) H(7) 3.546 ? . . H(3) H(8) 2.731 ? . . H(3) H(15) 3.200 ? . 1_565 H(3) H(18) 3.546 ? . . H(4) O(1) 3.595 ? . 4_555 H(4) O(2) 3.159 ? . 4_555 H(4) N(1) 2.032 ? . . H(4) C(2) 2.045 ? . . H(4) C(2) 2.998 ? . 4_556 H(4) C(3) 3.282 ? . . H(4) C(4) 2.049 ? . . H(4) C(5) 2.538 ? . . H(4) H(1) 2.301 ? . . H(4) H(2) 2.268 ? . . H(4) H(3) 2.760 ? . . H(4) H(5) 2.333 ? . . H(4) H(5) 2.653 ? . 4_556 H(4) H(6) 2.832 ? . . H(4) H(6) 3.550 ? . 1_565 H(4) H(6) 3.511 ? . 4_556 H(4) H(7) 2.329 ? . . H(4) H(7) 2.500 ? . 4_556 H(4) H(8) 3.570 ? . . H(4) H(9) 2.323 ? . . H(5) O(1) 2.760 ? . 4_555 H(5) N(1) 2.619 ? . . H(5) N(1) 3.362 ? . 4_545 H(5) C(1) 2.052 ? . . H(5) C(1) 3.560 ? . 4_546 H(5) C(4) 3.369 ? . . H(5) C(19) 3.290 ? . 4_555 H(5) H(1) 2.386 ? . . H(5) H(1) 3.208 ? . 4_545 H(5) H(2) 3.422 ? . . H(5) H(2) 2.950 ? . 4_545 H(5) H(3) 2.922 ? . . H(5) H(3) 3.399 ? . 4_545 H(5) H(4) 2.333 ? . . H(5) H(4) 2.653 ? . 4_546 H(5) H(6) 1.584 ? . . H(5) H(7) 1.584 ? . . H(5) H(7) 3.520 ? . 4_556 H(5) H(9) 3.235 ? . 4_546 H(6) O(1) 2.749 ? . . H(6) O(2) 3.388 ? . . H(6) N(1) 2.672 ? . . H(6) N(1) 3.522 ? . 4_545 H(6) C(1) 2.052 ? . . H(6) C(3) 2.796 ? . . H(6) C(4) 2.749 ? . . H(6) C(5) 3.437 ? . 1_545 H(6) C(19) 3.147 ? . . H(6) H(1) 2.868 ? . . H(6) H(1) 2.969 ? . 4_545 H(6) H(2) 3.460 ? . 1_545 H(6) H(2) 3.505 ? . . H(6) H(2) 3.408 ? . 4_545 H(6) H(3) 2.537 ? . . H(6) H(4) 3.550 ? . 1_545 H(6) H(4) 2.832 ? . . H(6) H(4) 3.511 ? . 4_546 H(6) H(5) 1.584 ? . . H(6) H(7) 1.584 ? . . H(6) H(8) 2.267 ? . . H(6) H(9) 2.677 ? . 1_545 H(7) O(2) 2.570 ? . 1_556 H(7) N(1) 3.297 ? . . H(7) C(1) 2.052 ? . . H(7) C(1) 3.418 ? . 4_546 H(7) C(3) 3.235 ? . . H(7) C(4) 2.750 ? . . H(7) C(19) 3.303 ? . 1_556 H(7) H(1) 3.456 ? . . H(7) H(3) 3.546 ? . . H(7) H(4) 2.329 ? . . H(7) H(4) 2.500 ? . 4_546 H(7) H(5) 1.584 ? . . H(7) H(5) 3.520 ? . 4_546 H(7) H(6) 1.584 ? . . H(7) H(8) 3.096 ? . . H(7) H(9) 3.089 ? . 1_545 H(7) H(18) 3.600 ? . 1_556 H(8) O(1) 3.185 ? . . H(8) O(2) 3.234 ? . . H(8) N(1) 3.163 ? . . H(8) C(1) 2.664 ? . . H(8) C(2) 2.792 ? . . H(8) C(4) 1.992 ? . . H(8) C(5) 3.470 ? . 1_545 H(8) C(5) 3.247 ? . . H(8) C(6) 3.485 ? . 1_545 H(8) C(7) 3.300 ? . . H(8) C(11) 2.661 ? . . H(8) C(12) 2.054 ? . . H(8) C(13) 2.986 ? . . H(8) C(14) 3.497 ? . . H(8) C(18) 3.453 ? . . H(8) C(19) 2.866 ? . . H(8) H(3) 2.731 ? . . H(8) H(4) 3.570 ? . . H(8) H(6) 2.267 ? . . H(8) H(7) 3.096 ? . . H(8) H(9) 3.111 ? . 1_545 H(8) H(10) 3.143 ? . 1_545 H(8) H(14) 2.502 ? . . H(9) O(1) 3.560 ? . 1_565 H(9) N(1) 3.496 ? . . H(9) C(1) 2.667 ? . . H(9) C(2) 3.321 ? . 1_565 H(9) C(3) 3.242 ? . . H(9) C(4) 2.058 ? . . H(9) C(6) 2.004 ? . . H(9) C(7) 3.269 ? . . H(9) C(13) 3.448 ? . 1_566 H(9) C(19) 3.562 ? . 1_566 H(9) H(2) 3.210 ? . . H(9) H(4) 2.323 ? . . H(9) H(5) 3.235 ? . 4_556 H(9) H(6) 2.677 ? . 1_565 H(9) H(7) 3.089 ? . 1_565 H(9) H(8) 3.111 ? . 1_565 H(9) H(10) 2.287 ? . . H(10) C(3) 3.485 ? . 1_565 H(10) C(4) 3.263 ? . . H(10) C(5) 1.997 ? . . H(10) C(7) 2.041 ? . . H(10) C(8) 2.664 ? . . H(10) C(11) 3.089 ? . 1_565 H(10) C(12) 3.282 ? . . H(10) C(12) 3.471 ? . 1_565 H(10) C(13) 3.059 ? . 1_566 H(10) C(14) 3.174 ? . 1_566 H(10) C(15) 3.168 ? . 1_566 H(10) C(16) 3.008 ? . 1_566 H(10) C(17) 2.872 ? . 1_566 H(10) C(18) 2.892 ? . 1_566 H(10) H(8) 3.143 ? . 1_565 H(10) H(9) 2.287 ? . . H(10) H(11) 2.513 ? . . H(10) H(14) 2.698 ? . 1_565 H(10) H(17) 3.328 ? . 1_566 H(10) H(18) 3.359 ? . 1_566 H(11) Br(1) 3.083 ? . 1_566 H(11) Br(1) 3.537 ? . 2_565 H(11) C(6) 2.668 ? . . H(11) C(7) 2.037 ? . . H(11) C(9) 2.003 ? . . H(11) C(10) 3.247 ? . . H(11) C(10) 3.458 ? . 1_565 H(11) C(11) 3.455 ? . 1_565 H(11) C(12) 3.282 ? . . H(11) C(16) 3.145 ? . 1_566 H(11) H(10) 2.513 ? . . H(11) H(12) 2.292 ? . . H(11) H(13) 3.111 ? . 1_565 H(11) H(14) 3.103 ? . 1_565 H(12) Br(1) 3.253 ? . 2_565 H(12) C(7) 3.250 ? . . H(12) C(8) 2.002 ? . . H(12) C(10) 2.031 ? . . H(12) C(11) 3.236 ? . . H(12) H(11) 2.292 ? . . H(12) H(13) 2.327 ? . . H(13) Br(1) 3.373 ? . . H(13) Br(1) 3.103 ? . 2_555 H(13) C(8) 3.244 ? . . H(13) C(9) 2.034 ? . . H(13) C(11) 2.006 ? . . H(13) C(12) 3.261 ? . . H(13) C(16) 3.488 ? . . H(13) H(11) 3.111 ? . 1_545 H(13) H(12) 2.327 ? . . H(13) H(13) 3.507 ? . 2_555 H(13) H(14) 2.301 ? . . H(14) C(3) 2.669 ? . . H(14) C(6) 3.074 ? . 1_545 H(14) C(7) 3.439 ? . 1_545 H(14) C(7) 3.301 ? . . H(14) C(8) 3.450 ? . 1_545 H(14) C(9) 3.243 ? . . H(14) C(10) 2.006 ? . . H(14) C(12) 2.052 ? . . H(14) C(13) 3.144 ? . . H(14) C(14) 2.956 ? . . H(14) C(15) 2.833 ? . . H(14) C(16) 2.898 ? . . H(14) C(17) 3.125 ? . . H(14) C(18) 3.232 ? . . H(14) H(8) 2.502 ? . . H(14) H(10) 2.698 ? . 1_545 H(14) H(11) 3.103 ? . 1_545 H(14) H(13) 2.301 ? . . H(14) H(15) 3.460 ? . . H(14) H(16) 3.276 ? . . H(15) O(1) 2.538 ? . . H(15) N(1) 3.426 ? . 1_545 H(15) C(3) 3.185 ? . 1_545 H(15) C(4) 3.166 ? . 1_545 H(15) C(5) 3.269 ? . 1_545 H(15) C(6) 3.395 ? . 1_545 H(15) C(7) 3.423 ? . 1_545 H(15) C(12) 3.325 ? . 1_545 H(15) C(13) 2.031 ? . . H(15) C(15) 2.033 ? . . H(15) C(16) 3.229 ? . . H(15) C(18) 3.259 ? . . H(15) C(19) 2.678 ? . . H(15) H(2) 2.938 ? . 1_545 H(15) H(3) 3.200 ? . 1_545 H(15) H(14) 3.460 ? . . H(15) H(16) 2.344 ? . . H(15) H(18) 2.989 ? . 1_545 H(16) Br(1) 2.893 ? . . H(16) C(7) 3.266 ? . 1_545 H(16) C(8) 3.331 ? . 1_545 H(16) C(9) 3.484 ? . 1_545 H(16) C(10) 3.556 ? . 1_545 H(16) C(11) 3.493 ? . 1_545 H(16) C(12) 3.348 ? . 1_545 H(16) C(13) 3.274 ? . . H(16) C(14) 2.044 ? . . H(16) C(16) 2.024 ? . . H(16) C(17) 3.450 ? . 1_545 H(16) C(17) 3.265 ? . . H(16) H(14) 3.276 ? . . H(16) H(15) 2.344 ? . . H(16) H(17) 3.012 ? . 1_545 H(16) H(18) 3.390 ? . 1_545 H(17) Br(1) 2.903 ? . . H(17) C(7) 3.251 ? . 1_554 H(17) C(8) 3.253 ? . 1_554 H(17) C(9) 3.302 ? . 1_554 H(17) C(10) 3.374 ? . 1_554 H(17) C(11) 3.373 ? . 1_554 H(17) C(12) 3.307 ? . 1_554 H(17) C(13) 3.270 ? . . H(17) C(15) 3.263 ? . . H(17) C(16) 2.030 ? . . H(17) C(18) 2.041 ? . . H(17) H(10) 3.328 ? . 1_544 H(17) H(16) 3.012 ? . 1_565 H(17) H(18) 2.343 ? . . H(18) O(2) 2.482 ? . . H(18) C(3) 3.346 ? . 1_554 H(18) C(4) 3.425 ? . 1_554 H(18) C(5) 3.515 ? . 1_554 H(18) C(6) 3.533 ? . 1_554 H(18) C(7) 3.493 ? . 1_554 H(18) C(12) 3.380 ? . 1_554 H(18) C(13) 2.035 ? . . H(18) C(14) 3.260 ? . . H(18) C(14) 3.452 ? . 1_565 H(18) C(16) 3.239 ? . . H(18) C(17) 2.034 ? . . H(18) C(19) 2.662 ? . . H(18) H(3) 3.546 ? . . H(18) H(7) 3.600 ? . 1_554 H(18) H(10) 3.359 ? . 1_544 H(18) H(15) 2.989 ? . 1_565 H(18) H(16) 3.390 ? . 1_565 H(18) H(17) 2.343 ? . . data__20111014_R1NaphEthyAm_pCl _database_code_depnum_ccdc_archive 'CCDC 884892' #TrackingRef 'RNaph12-pClBA.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H18 Cl N O2 ' _chemical_formula_moiety 'C19 H18 Cl N O2 ' _chemical_formula_weight 327.81 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,-Z 3 1/2+X,1/2+Y,+Z 4 1/2-X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 37.4749(7) _cell_length_b 6.19581(11) _cell_length_c 7.19661(13) _cell_angle_alpha 90.0000 _cell_angle_beta 92.8197(8) _cell_angle_gamma 90.0000 _cell_volume 1668.94(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6567 _cell_measurement_theta_min 4.7 _cell_measurement_theta_max 68.1 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688.00 _exptl_absorpt_coefficient_mu 2.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.347 _exptl_absorpt_correction_T_max 0.432 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 8785 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_theta_max 68.22 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 68.22 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_ambient_temperature 213.1 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2916 _reflns_number_gt 2620 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1111 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2916 _refine_ls_number_parameters 210 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.42 _refine_diff_density_min -0.24 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0058(4) _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1257 Friedel Pairs' _refine_ls_abs_structure_Flack 0.019(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.364 0.702 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl(1) Cl 0.028150(14) 0.74588(16) 0.20773(10) 0.0716(2) Uani 1.00 1 d . . . O(1) O 0.20352(4) 0.7151(2) 0.4353(2) 0.0497(4) Uani 1.00 1 d . . . O(2) O 0.20000(4) 1.0337(2) 0.2980(2) 0.0451(4) Uani 1.00 1 d . . . N(1) N 0.22346(4) 0.3139(2) 0.5754(2) 0.0358(4) Uani 1.00 1 d . . . C(1) C 0.21316(5) 0.2761(4) 0.7722(3) 0.0411(5) Uani 1.00 1 d . . . C(2) C 0.22655(7) 0.0551(5) 0.8356(3) 0.0562(7) Uani 1.00 1 d . . . C(3) C 0.14871(6) 0.1606(3) 0.7233(2) 0.0368(5) Uani 1.00 1 d . . . C(4) C 0.17337(6) 0.3109(3) 0.7843(2) 0.0366(5) Uani 1.00 1 d . . . C(5) C 0.16093(6) 0.5089(4) 0.8569(3) 0.0414(5) Uani 1.00 1 d . . . C(6) C 0.12573(6) 0.5514(4) 0.8652(3) 0.0438(5) Uani 1.00 1 d . . . C(7) C 0.09964(6) 0.3984(3) 0.8014(3) 0.0383(5) Uani 1.00 1 d . . . C(8) C 0.06268(6) 0.4367(4) 0.8046(3) 0.0508(6) Uani 1.00 1 d . . . C(9) C 0.03857(7) 0.2839(5) 0.7407(3) 0.0594(7) Uani 1.00 1 d . . . C(10) C 0.05028(7) 0.0881(4) 0.6696(3) 0.0536(6) Uani 1.00 1 d . . . C(11) C 0.08596(6) 0.0443(4) 0.6650(3) 0.0445(5) Uani 1.00 1 d . . . C(12) C 0.11177(5) 0.1980(3) 0.7292(2) 0.0349(5) Uani 1.00 1 d . . . C(13) C 0.14702(6) 0.8243(3) 0.3031(2) 0.0343(4) Uani 1.00 1 d . . . C(14) C 0.13020(6) 0.6340(3) 0.3542(3) 0.0383(5) Uani 1.00 1 d . . . C(15) C 0.09378(6) 0.6074(4) 0.3236(3) 0.0435(5) Uani 1.00 1 d . . . C(16) C 0.07426(6) 0.7739(4) 0.2412(3) 0.0464(6) Uani 1.00 1 d . . . C(17) C 0.09026(6) 0.9621(4) 0.1840(3) 0.0446(5) Uani 1.00 1 d . . . C(18) C 0.12671(6) 0.9868(3) 0.2164(3) 0.0399(5) Uani 1.00 1 d . . . C(19) C 0.18641(6) 0.8593(3) 0.3470(2) 0.0357(4) Uani 1.00 1 d . . . H(1) H 0.2130 0.2137 0.5003 0.043 Uiso 1.00 1 c R . . H(2) H 0.2473 0.3044 0.5698 0.043 Uiso 1.00 1 c R . . H(3) H 0.2162 0.4461 0.5382 0.043 Uiso 1.00 1 c R . . H(4) H 0.2256 0.3856 0.8519 0.049 Uiso 1.00 1 c R . . H(5) H 0.2204 0.0310 0.9633 0.067 Uiso 1.00 1 c R . . H(6) H 0.2523 0.0487 0.8275 0.067 Uiso 1.00 1 c R . . H(7) H 0.2155 -0.0553 0.7564 0.067 Uiso 1.00 1 c R . . H(8) H 0.1567 0.0287 0.6761 0.044 Uiso 1.00 1 c R . . H(9) H 0.1776 0.6127 0.9003 0.050 Uiso 1.00 1 c R . . H(10) H 0.1184 0.6840 0.9138 0.053 Uiso 1.00 1 c R . . H(11) H 0.0544 0.5684 0.8510 0.061 Uiso 1.00 1 c R . . H(12) H 0.0140 0.3113 0.7447 0.071 Uiso 1.00 1 c R . . H(13) H 0.0335 -0.0144 0.6247 0.064 Uiso 1.00 1 c R . . H(14) H 0.0935 -0.0892 0.6187 0.053 Uiso 1.00 1 c R . . H(15) H 0.1438 0.5222 0.4103 0.046 Uiso 1.00 1 c R . . H(16) H 0.0825 0.4789 0.3581 0.052 Uiso 1.00 1 c R . . H(17) H 0.0766 1.0713 0.1241 0.054 Uiso 1.00 1 c R . . H(18) H 0.1379 1.1146 0.1795 0.048 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl(1) 0.0276(2) 0.1105(6) 0.0761(4) -0.0016(3) -0.0031(2) -0.0240(4) O(1) 0.0308(7) 0.0516(9) 0.0659(11) 0.0032(7) -0.0043(7) 0.0099(9) O(2) 0.0413(8) 0.0517(10) 0.0423(9) -0.0139(7) 0.0016(7) 0.0017(7) N(1) 0.0259(8) 0.0395(9) 0.0422(10) -0.0025(6) 0.0027(7) 0.0008(8) C(1) 0.0323(10) 0.0565(15) 0.0340(11) -0.0020(10) -0.0024(8) -0.0040(11) C(2) 0.0394(12) 0.083(2) 0.0460(14) 0.0127(12) 0.0027(10) 0.0192(14) C(3) 0.0347(11) 0.0414(12) 0.0345(11) 0.0022(9) 0.0028(9) -0.0040(9) C(4) 0.0340(11) 0.0480(13) 0.0280(10) 0.0008(9) 0.0031(8) -0.0016(9) C(5) 0.0419(12) 0.0441(13) 0.0384(12) -0.0059(9) 0.0039(9) -0.0078(10) C(6) 0.0501(13) 0.0418(12) 0.0402(13) -0.0002(10) 0.0081(10) -0.0080(10) C(7) 0.0388(12) 0.0440(12) 0.0326(11) 0.0031(9) 0.0061(9) -0.0024(10) C(8) 0.0415(13) 0.0595(16) 0.0522(15) 0.0096(11) 0.0106(11) -0.0079(12) C(9) 0.0314(11) 0.083(2) 0.0637(17) 0.0058(12) 0.0060(10) -0.0083(16) C(10) 0.0376(13) 0.0663(17) 0.0571(16) -0.0080(11) 0.0039(11) -0.0062(13) C(11) 0.0361(12) 0.0531(14) 0.0446(13) -0.0038(10) 0.0032(10) -0.0075(11) C(12) 0.0341(10) 0.0432(13) 0.0277(10) 0.0007(8) 0.0038(8) -0.0011(9) C(13) 0.0297(10) 0.0425(12) 0.0307(10) 0.0017(8) 0.0018(8) -0.0044(9) C(14) 0.0337(11) 0.0421(12) 0.0390(12) -0.0029(9) 0.0001(9) -0.0030(10) C(15) 0.0348(12) 0.0521(14) 0.0440(13) -0.0071(10) 0.0056(10) -0.0058(11) C(16) 0.0274(10) 0.0692(17) 0.0426(12) -0.0002(11) 0.0017(9) -0.0192(12) C(17) 0.0353(11) 0.0576(15) 0.0404(13) 0.0110(10) -0.0043(9) -0.0055(11) C(18) 0.0411(12) 0.0434(13) 0.0353(12) 0.0022(9) 0.0007(9) -0.0032(10) C(19) 0.0287(10) 0.0474(13) 0.0313(10) -0.0018(9) 0.0046(8) -0.0060(10) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cl(1) C(16) 1.742(2) yes . . O(1) C(19) 1.254(2) yes . . O(2) C(19) 1.252(2) yes . . N(1) C(1) 1.504(2) yes . . C(1) C(2) 1.520(3) yes . . C(1) C(4) 1.513(2) yes . . C(3) C(4) 1.368(3) yes . . C(3) C(12) 1.406(2) yes . . C(4) C(5) 1.421(3) yes . . C(5) C(6) 1.349(3) yes . . C(6) C(7) 1.422(3) yes . . C(7) C(8) 1.407(3) yes . . C(7) C(12) 1.429(3) yes . . C(8) C(9) 1.372(3) yes . . C(9) C(10) 1.396(4) yes . . C(10) C(11) 1.366(3) yes . . C(11) C(12) 1.418(3) yes . . C(13) C(14) 1.395(3) yes . . C(13) C(18) 1.391(3) yes . . C(13) C(19) 1.510(3) yes . . C(14) C(15) 1.382(3) yes . . C(15) C(16) 1.382(3) yes . . C(16) C(17) 1.383(3) yes . . C(17) C(18) 1.383(3) yes . . N(1) H(1) 0.900 no . . N(1) H(2) 0.900 no . . N(1) H(3) 0.900 no . . C(1) H(4) 0.990 no . . C(2) H(5) 0.970 no . . C(2) H(6) 0.970 no . . C(2) H(7) 0.970 no . . C(3) H(8) 0.940 no . . C(5) H(9) 0.940 no . . C(6) H(10) 0.940 no . . C(8) H(11) 0.940 no . . C(9) H(12) 0.940 no . . C(10) H(13) 0.940 no . . C(11) H(14) 0.940 no . . C(14) H(15) 0.940 no . . C(15) H(16) 0.940 no . . C(17) H(17) 0.940 no . . C(18) H(18) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 N(1) C(1) C(2) 109.06(18) yes . . . N(1) C(1) C(4) 109.35(15) yes . . . C(2) C(1) C(4) 114.99(19) yes . . . C(4) C(3) C(12) 121.9(2) yes . . . C(1) C(4) C(3) 122.4(2) yes . . . C(1) C(4) C(5) 119.08(19) yes . . . C(3) C(4) C(5) 118.5(2) yes . . . C(4) C(5) C(6) 121.6(2) yes . . . C(5) C(6) C(7) 120.9(2) yes . . . C(6) C(7) C(8) 123.0(2) yes . . . C(6) C(7) C(12) 118.09(19) yes . . . C(8) C(7) C(12) 118.9(2) yes . . . C(7) C(8) C(9) 120.7(2) yes . . . C(8) C(9) C(10) 120.6(2) yes . . . C(9) C(10) C(11) 120.5(2) yes . . . C(10) C(11) C(12) 120.8(2) yes . . . C(3) C(12) C(7) 119.02(19) yes . . . C(3) C(12) C(11) 122.4(2) yes . . . C(7) C(12) C(11) 118.54(18) yes . . . C(14) C(13) C(18) 119.1(2) yes . . . C(14) C(13) C(19) 121.08(19) yes . . . C(18) C(13) C(19) 119.82(19) yes . . . C(13) C(14) C(15) 121.0(2) yes . . . C(14) C(15) C(16) 118.5(2) yes . . . Cl(1) C(16) C(15) 119.1(2) yes . . . Cl(1) C(16) C(17) 118.98(19) yes . . . C(15) C(16) C(17) 122.0(2) yes . . . C(16) C(17) C(18) 118.8(2) yes . . . C(13) C(18) C(17) 120.6(2) yes . . . O(1) C(19) O(2) 123.5(2) yes . . . O(1) C(19) C(13) 118.28(19) yes . . . O(2) C(19) C(13) 118.17(18) yes . . . C(1) N(1) H(1) 109.5 no . . . C(1) N(1) H(2) 109.5 no . . . C(1) N(1) H(3) 109.5 no . . . H(1) N(1) H(2) 109.5 no . . . H(1) N(1) H(3) 109.5 no . . . H(2) N(1) H(3) 109.5 no . . . N(1) C(1) H(4) 107.7 no . . . C(2) C(1) H(4) 107.7 no . . . C(4) C(1) H(4) 107.7 no . . . C(1) C(2) H(5) 109.5 no . . . C(1) C(2) H(6) 109.5 no . . . C(1) C(2) H(7) 109.5 no . . . H(5) C(2) H(6) 109.5 no . . . H(5) C(2) H(7) 109.5 no . . . H(6) C(2) H(7) 109.5 no . . . C(4) C(3) H(8) 119.0 no . . . C(12) C(3) H(8) 119.0 no . . . C(4) C(5) H(9) 119.2 no . . . C(6) C(5) H(9) 119.2 no . . . C(5) C(6) H(10) 119.6 no . . . C(7) C(6) H(10) 119.5 no . . . C(7) C(8) H(11) 119.7 no . . . C(9) C(8) H(11) 119.6 no . . . C(8) C(9) H(12) 119.7 no . . . C(10) C(9) H(12) 119.7 no . . . C(9) C(10) H(13) 119.8 no . . . C(11) C(10) H(13) 119.8 no . . . C(10) C(11) H(14) 119.6 no . . . C(12) C(11) H(14) 119.6 no . . . C(13) C(14) H(15) 119.5 no . . . C(15) C(14) H(15) 119.5 no . . . C(14) C(15) H(16) 120.8 no . . . C(16) C(15) H(16) 120.7 no . . . C(16) C(17) H(17) 120.6 no . . . C(18) C(17) H(17) 120.6 no . . . C(13) C(18) H(18) 119.7 no . . . C(17) C(18) H(18) 119.7 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N(1) C(1) C(4) C(3) 77.4(2) ? . . . . N(1) C(1) C(4) C(5) -100.8(2) ? . . . . C(2) C(1) C(4) C(3) -45.6(2) ? . . . . C(2) C(1) C(4) C(5) 136.1(2) ? . . . . C(4) C(3) C(12) C(7) -0.2(3) ? . . . . C(4) C(3) C(12) C(11) 179.5(2) ? . . . . C(12) C(3) C(4) C(1) -177.67(19) ? . . . . C(12) C(3) C(4) C(5) 0.6(3) ? . . . . C(1) C(4) C(5) C(6) 177.8(2) ? . . . . C(3) C(4) C(5) C(6) -0.6(3) ? . . . . C(4) C(5) C(6) C(7) 0.1(2) ? . . . . C(5) C(6) C(7) C(8) -179.0(2) ? . . . . C(5) C(6) C(7) C(12) 0.3(3) ? . . . . C(6) C(7) C(8) C(9) 179.8(2) ? . . . . C(6) C(7) C(12) C(3) -0.3(3) ? . . . . C(6) C(7) C(12) C(11) -179.94(15) ? . . . . C(8) C(7) C(12) C(3) 179.1(2) ? . . . . C(8) C(7) C(12) C(11) -0.6(3) ? . . . . C(12) C(7) C(8) C(9) 0.4(3) ? . . . . C(7) C(8) C(9) C(10) -0.6(4) ? . . . . C(8) C(9) C(10) C(11) 0.9(4) ? . . . . C(9) C(10) C(11) C(12) -1.1(3) ? . . . . C(10) C(11) C(12) C(3) -178.7(2) ? . . . . C(10) C(11) C(12) C(7) 0.9(3) ? . . . . C(14) C(13) C(18) C(17) 1.1(3) ? . . . . C(18) C(13) C(14) C(15) -1.4(3) ? . . . . C(14) C(13) C(19) O(1) -1.9(3) ? . . . . C(14) C(13) C(19) O(2) -179.8(2) ? . . . . C(19) C(13) C(14) C(15) 176.2(2) ? . . . . C(18) C(13) C(19) O(1) 175.7(2) ? . . . . C(18) C(13) C(19) O(2) -2.2(3) ? . . . . C(19) C(13) C(18) C(17) -176.6(2) ? . . . . C(13) C(14) C(15) C(16) -0.1(2) ? . . . . C(14) C(15) C(16) Cl(1) -178.20(18) ? . . . . C(14) C(15) C(16) C(17) 2.0(3) ? . . . . Cl(1) C(16) C(17) C(18) 177.87(18) ? . . . . C(15) C(16) C(17) C(18) -2.3(3) ? . . . . C(16) C(17) C(18) C(13) 0.7(3) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Cl(1) Cl(1) 3.5736(9) ? . 2_555 O(1) N(1) 2.771(2) ? . . O(1) N(1) 2.809(2) ? . 4_556 O(1) C(1) 3.547(2) ? . 4_556 O(1) C(2) 3.486(3) ? . 4_556 O(2) N(1) 2.756(2) ? . 1_565 O(2) N(1) 3.264(2) ? . 4_556 O(2) C(2) 3.523(3) ? . 1_564 N(1) O(1) 2.771(2) ? . . N(1) O(1) 2.809(2) ? . 4_546 N(1) O(2) 2.756(2) ? . 1_545 N(1) O(2) 3.264(2) ? . 4_546 N(1) C(19) 3.512(2) ? . 1_545 N(1) C(19) 3.408(2) ? . 4_546 C(1) O(1) 3.547(2) ? . 4_546 C(2) O(1) 3.486(3) ? . 4_546 C(2) O(2) 3.523(3) ? . 1_546 C(6) C(14) 3.552(3) ? . 1_556 C(6) C(15) 3.581(3) ? . 1_556 C(11) C(16) 3.488(3) ? . 1_545 C(11) C(17) 3.511(3) ? . 1_545 C(14) C(6) 3.552(3) ? . 1_554 C(15) C(6) 3.581(3) ? . 1_554 C(16) C(11) 3.488(3) ? . 1_565 C(17) C(11) 3.511(3) ? . 1_565 C(19) N(1) 3.512(2) ? . 1_565 C(19) N(1) 3.408(2) ? . 4_556 Cl(1) H(11) 3.002 ? . 1_554 Cl(1) H(11) 3.291 ? . 2_556 Cl(1) H(12) 3.148 ? . 2_556 Cl(1) H(13) 3.345 ? . 1_565 Cl(1) H(13) 3.045 ? . 2_566 O(1) H(1) 3.159 ? . . O(1) H(1) 3.142 ? . 1_565 O(1) H(1) 3.140 ? . 4_556 O(1) H(2) 3.155 ? . . O(1) H(2) 1.925 ? . 4_556 O(1) H(3) 1.875 ? . . O(1) H(3) 3.329 ? . 4_556 O(1) H(6) 2.773 ? . 4_556 O(1) H(7) 2.732 ? . 1_565 O(1) H(8) 3.187 ? . 1_565 O(1) H(9) 3.586 ? . . O(2) H(1) 1.879 ? . 1_565 O(2) H(2) 3.073 ? . 1_565 O(2) H(2) 2.575 ? . 4_556 O(2) H(3) 3.128 ? . 1_565 O(2) H(3) 3.344 ? . 4_556 O(2) H(4) 3.176 ? . 4_556 O(2) H(5) 2.563 ? . 1_564 O(2) H(7) 3.367 ? . 1_565 O(2) H(8) 3.236 ? . 1_565 N(1) H(1) 3.497 ? . 4_556 N(1) H(2) 3.516 ? . 4_546 N(1) H(2) 3.412 ? . 4_556 N(1) H(3) 3.340 ? . 4_546 N(1) H(6) 3.407 ? . 4_556 N(1) H(7) 3.483 ? . 4_556 N(1) H(15) 3.411 ? . . C(1) H(5) 3.442 ? . 4_557 C(1) H(6) 3.530 ? . 4_557 C(2) H(2) 3.488 ? . 4_546 C(2) H(3) 3.587 ? . 4_546 C(2) H(4) 2.997 ? . 4_547 C(2) H(9) 3.343 ? . 1_545 C(3) H(10) 3.471 ? . 1_545 C(3) H(15) 3.176 ? . . C(3) H(18) 3.340 ? . 1_546 C(4) H(15) 3.145 ? . . C(4) H(18) 3.422 ? . 1_546 C(5) H(7) 3.485 ? . 1_565 C(5) H(8) 3.474 ? . 1_565 C(5) H(15) 3.247 ? . . C(5) H(18) 3.507 ? . 1_546 C(6) H(8) 3.478 ? . 1_565 C(6) H(14) 3.059 ? . 1_565 C(6) H(15) 3.381 ? . . C(6) H(18) 3.542 ? . 1_546 C(7) H(14) 3.440 ? . 1_565 C(7) H(15) 3.422 ? . . C(7) H(16) 3.261 ? . . C(7) H(17) 3.232 ? . 1_546 C(7) H(18) 3.488 ? . 1_546 C(8) H(14) 3.450 ? . 1_565 C(8) H(16) 3.344 ? . . C(8) H(17) 3.250 ? . 1_546 C(9) H(16) 3.493 ? . . C(9) H(17) 3.315 ? . 1_546 C(10) H(11) 3.475 ? . 1_545 C(10) H(16) 3.552 ? . . C(10) H(17) 3.371 ? . 1_546 C(11) H(10) 3.074 ? . 1_545 C(11) H(11) 3.470 ? . 1_545 C(11) H(16) 3.481 ? . . C(11) H(17) 3.344 ? . 1_546 C(12) H(10) 3.455 ? . 1_545 C(12) H(15) 3.319 ? . . C(12) H(16) 3.328 ? . . C(12) H(17) 3.286 ? . 1_546 C(12) H(18) 3.378 ? . 1_546 C(13) H(8) 2.974 ? . 1_565 C(13) H(9) 3.430 ? . 1_554 C(13) H(10) 3.076 ? . 1_554 C(13) H(14) 3.149 ? . 1_565 C(14) H(8) 3.479 ? . 1_565 C(14) H(10) 3.194 ? . 1_554 C(14) H(14) 2.952 ? . 1_565 C(14) H(18) 3.472 ? . 1_545 C(15) H(10) 3.168 ? . 1_554 C(15) H(14) 2.837 ? . 1_565 C(16) H(10) 2.996 ? . 1_554 C(16) H(11) 3.139 ? . 1_554 C(16) H(13) 3.476 ? . 1_565 C(16) H(14) 2.903 ? . 1_565 C(17) H(10) 2.839 ? . 1_554 C(17) H(14) 3.141 ? . 1_565 C(17) H(16) 3.456 ? . 1_565 C(18) H(8) 3.451 ? . 1_565 C(18) H(10) 2.879 ? . 1_554 C(18) H(14) 3.242 ? . 1_565 C(19) H(1) 2.631 ? . 1_565 C(19) H(2) 2.548 ? . 4_556 C(19) H(3) 3.089 ? . . C(19) H(5) 3.275 ? . 1_564 C(19) H(6) 3.293 ? . 4_556 C(19) H(7) 3.136 ? . 1_565 C(19) H(8) 2.866 ? . 1_565 C(19) H(9) 3.560 ? . 1_554 H(1) O(1) 3.142 ? . 1_545 H(1) O(1) 3.159 ? . . H(1) O(1) 3.140 ? . 4_546 H(1) O(2) 1.879 ? . 1_545 H(1) N(1) 3.497 ? . 4_546 H(1) C(19) 2.631 ? . 1_545 H(1) H(2) 2.994 ? . 4_546 H(1) H(3) 3.153 ? . 4_546 H(1) H(6) 3.445 ? . 4_556 H(1) H(15) 3.260 ? . . H(2) O(1) 3.155 ? . . H(2) O(1) 1.925 ? . 4_546 H(2) O(2) 3.073 ? . 1_545 H(2) O(2) 2.575 ? . 4_546 H(2) N(1) 3.412 ? . 4_546 H(2) N(1) 3.516 ? . 4_556 H(2) C(2) 3.488 ? . 4_556 H(2) C(19) 2.548 ? . 4_546 H(2) H(1) 2.994 ? . 4_556 H(2) H(2) 3.266 ? . 4_546 H(2) H(2) 3.266 ? . 4_556 H(2) H(3) 2.740 ? . 4_546 H(2) H(6) 3.236 ? . 4_556 H(2) H(7) 2.921 ? . 4_556 H(3) O(1) 1.875 ? . . H(3) O(1) 3.329 ? . 4_546 H(3) O(2) 3.128 ? . 1_545 H(3) O(2) 3.344 ? . 4_546 H(3) N(1) 3.340 ? . 4_556 H(3) C(2) 3.587 ? . 4_556 H(3) C(19) 3.089 ? . . H(3) H(1) 3.153 ? . 4_556 H(3) H(2) 2.740 ? . 4_556 H(3) H(6) 3.006 ? . 4_556 H(3) H(7) 3.466 ? . 1_565 H(3) H(7) 3.404 ? . 4_556 H(3) H(15) 2.859 ? . . H(4) O(2) 3.176 ? . 4_546 H(4) C(2) 2.997 ? . 4_557 H(4) H(5) 2.533 ? . 4_557 H(4) H(6) 2.616 ? . 4_557 H(4) H(7) 3.548 ? . 1_565 H(4) H(7) 3.514 ? . 4_557 H(5) O(2) 2.563 ? . 1_546 H(5) C(1) 3.442 ? . 4_547 H(5) C(19) 3.275 ? . 1_546 H(5) H(4) 2.533 ? . 4_547 H(5) H(6) 3.477 ? . 4_547 H(5) H(9) 3.069 ? . 1_545 H(5) H(18) 3.568 ? . 1_546 H(6) O(1) 2.773 ? . 4_546 H(6) N(1) 3.407 ? . 4_546 H(6) C(1) 3.530 ? . 4_547 H(6) C(19) 3.293 ? . 4_546 H(6) H(1) 3.445 ? . 4_546 H(6) H(2) 3.236 ? . 4_546 H(6) H(3) 3.006 ? . 4_546 H(6) H(4) 2.616 ? . 4_547 H(6) H(5) 3.477 ? . 4_557 H(6) H(9) 3.223 ? . 4_547 H(7) O(1) 2.732 ? . 1_545 H(7) O(2) 3.367 ? . 1_545 H(7) N(1) 3.483 ? . 4_546 H(7) C(5) 3.485 ? . 1_545 H(7) C(19) 3.136 ? . 1_545 H(7) H(2) 2.921 ? . 4_546 H(7) H(3) 3.466 ? . 1_545 H(7) H(3) 3.404 ? . 4_546 H(7) H(4) 3.548 ? . 1_545 H(7) H(4) 3.514 ? . 4_547 H(7) H(9) 2.732 ? . 1_545 H(8) O(1) 3.187 ? . 1_545 H(8) O(2) 3.236 ? . 1_545 H(8) C(5) 3.474 ? . 1_545 H(8) C(6) 3.478 ? . 1_545 H(8) C(13) 2.974 ? . 1_545 H(8) C(14) 3.479 ? . 1_545 H(8) C(18) 3.451 ? . 1_545 H(8) C(19) 2.866 ? . 1_545 H(8) H(9) 3.120 ? . 1_545 H(8) H(10) 3.129 ? . 1_545 H(9) O(1) 3.586 ? . . H(9) C(2) 3.343 ? . 1_565 H(9) C(13) 3.430 ? . 1_556 H(9) C(19) 3.560 ? . 1_556 H(9) H(5) 3.069 ? . 1_565 H(9) H(6) 3.223 ? . 4_557 H(9) H(7) 2.732 ? . 1_565 H(9) H(8) 3.120 ? . 1_565 H(10) C(3) 3.471 ? . 1_565 H(10) C(11) 3.074 ? . 1_565 H(10) C(12) 3.455 ? . 1_565 H(10) C(13) 3.076 ? . 1_556 H(10) C(14) 3.194 ? . 1_556 H(10) C(15) 3.168 ? . 1_556 H(10) C(16) 2.996 ? . 1_556 H(10) C(17) 2.839 ? . 1_556 H(10) C(18) 2.879 ? . 1_556 H(10) H(8) 3.129 ? . 1_565 H(10) H(14) 2.676 ? . 1_565 H(10) H(17) 3.276 ? . 1_556 H(10) H(18) 3.342 ? . 1_556 H(11) Cl(1) 3.002 ? . 1_556 H(11) Cl(1) 3.291 ? . 2_556 H(11) C(10) 3.475 ? . 1_565 H(11) C(11) 3.470 ? . 1_565 H(11) C(16) 3.139 ? . 1_556 H(11) H(13) 3.134 ? . 1_565 H(11) H(14) 3.112 ? . 1_565 H(12) Cl(1) 3.148 ? . 2_556 H(13) Cl(1) 3.345 ? . 1_545 H(13) Cl(1) 3.045 ? . 2_546 H(13) C(16) 3.476 ? . 1_545 H(13) H(11) 3.134 ? . 1_545 H(13) H(13) 3.013 ? . 2_556 H(14) C(6) 3.059 ? . 1_545 H(14) C(7) 3.440 ? . 1_545 H(14) C(8) 3.450 ? . 1_545 H(14) C(13) 3.149 ? . 1_545 H(14) C(14) 2.952 ? . 1_545 H(14) C(15) 2.837 ? . 1_545 H(14) C(16) 2.903 ? . 1_545 H(14) C(17) 3.141 ? . 1_545 H(14) C(18) 3.242 ? . 1_545 H(14) H(10) 2.676 ? . 1_545 H(14) H(11) 3.112 ? . 1_545 H(14) H(15) 3.447 ? . 1_545 H(14) H(16) 3.282 ? . 1_545 H(15) N(1) 3.411 ? . . H(15) C(3) 3.176 ? . . H(15) C(4) 3.145 ? . . H(15) C(5) 3.247 ? . . H(15) C(6) 3.381 ? . . H(15) C(7) 3.422 ? . . H(15) C(12) 3.319 ? . . H(15) H(1) 3.260 ? . . H(15) H(3) 2.859 ? . . H(15) H(14) 3.447 ? . 1_565 H(15) H(18) 3.025 ? . 1_545 H(16) C(7) 3.261 ? . . H(16) C(8) 3.344 ? . . H(16) C(9) 3.493 ? . . H(16) C(10) 3.552 ? . . H(16) C(11) 3.481 ? . . H(16) C(12) 3.328 ? . . H(16) C(17) 3.456 ? . 1_545 H(16) H(14) 3.282 ? . 1_565 H(16) H(17) 3.038 ? . 1_545 H(16) H(18) 3.363 ? . 1_545 H(17) C(7) 3.232 ? . 1_564 H(17) C(8) 3.250 ? . 1_564 H(17) C(9) 3.315 ? . 1_564 H(17) C(10) 3.371 ? . 1_564 H(17) C(11) 3.344 ? . 1_564 H(17) C(12) 3.286 ? . 1_564 H(17) H(10) 3.276 ? . 1_554 H(17) H(16) 3.038 ? . 1_565 H(18) C(3) 3.340 ? . 1_564 H(18) C(4) 3.422 ? . 1_564 H(18) C(5) 3.507 ? . 1_564 H(18) C(6) 3.542 ? . 1_564 H(18) C(7) 3.488 ? . 1_564 H(18) C(12) 3.378 ? . 1_564 H(18) C(14) 3.472 ? . 1_565 H(18) H(5) 3.568 ? . 1_564 H(18) H(10) 3.342 ? . 1_554 H(18) H(15) 3.025 ? . 1_565 H(18) H(16) 3.363 ? . 1_565 data__R12NaphEthAm_4FBA_EthaTol _database_code_depnum_ccdc_archive 'CCDC 884893' #TrackingRef 'RNaph12-pFBA.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H18 F N O2 ' _chemical_formula_moiety 'C19 H18 F N O2 ' _chemical_formula_weight 311.36 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,-Z 3 1/2+X,1/2+Y,+Z 4 1/2-X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 35.5961(9) _cell_length_b 6.21689(18) _cell_length_c 7.1819(2) _cell_angle_alpha 90.0000 _cell_angle_beta 92.5391(14) _cell_angle_gamma 90.0000 _cell_volume 1587.77(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3391 _cell_measurement_theta_min 5.0 _cell_measurement_theta_max 68.0 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656.00 _exptl_absorpt_coefficient_mu 0.757 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.509 _exptl_absorpt_correction_T_max 0.927 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 8554 _diffrn_reflns_av_R_equivalents 0.084 _diffrn_reflns_theta_max 68.22 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 68.22 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_ambient_temperature 213.1 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2845 _reflns_number_gt 1717 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1914 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2845 _refine_ls_number_parameters 210 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0501P)^2^+2.1704P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.25 _refine_diff_density_min -0.28 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0040(4) _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1268 Friedel Pairs' _refine_ls_abs_structure_Flack -0.1(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.073 0.053 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F(1) F 0.52749(8) 0.5359(5) -0.2905(4) 0.0780(11) Uani 1.00 1 d . . . O(1) O 0.69643(10) 0.8381(5) -0.1994(4) 0.0585(9) Uani 1.00 1 d . . . O(2) O 0.70095(10) 0.5193(6) -0.0588(5) 0.0627(10) Uani 1.00 1 d . . . N(1) N 0.72257(11) 0.1203(7) 0.0737(5) 0.0520(10) Uani 1.00 1 d . . . C(1) C 0.71209(14) 0.0818(8) 0.2728(6) 0.0532(13) Uani 1.00 1 d . . . C(2) C 0.72623(15) -0.1346(10) 0.3368(7) 0.0659(15) Uani 1.00 1 d . . . C(3) C 0.64451(13) -0.0348(8) 0.2286(6) 0.0492(12) Uani 1.00 1 d . . . C(4) C 0.67032(13) 0.1164(8) 0.2873(6) 0.0467(11) Uani 1.00 1 d . . . C(5) C 0.65767(14) 0.3131(8) 0.3584(6) 0.0547(13) Uani 1.00 1 d . . . C(6) C 0.61988(15) 0.3535(9) 0.3692(7) 0.0565(13) Uani 1.00 1 d . . . C(7) C 0.59320(14) 0.2002(8) 0.3091(6) 0.0472(11) Uani 1.00 1 d . . . C(8) C 0.55366(15) 0.2402(9) 0.3165(7) 0.0602(14) Uani 1.00 1 d . . . C(9) C 0.52823(16) 0.0873(10) 0.2555(7) 0.0664(16) Uani 1.00 1 d . . . C(10) C 0.54077(15) -0.1103(10) 0.1862(7) 0.0655(16) Uani 1.00 1 d . . . C(11) C 0.57863(13) -0.1514(9) 0.1760(6) 0.0545(13) Uani 1.00 1 d . . . C(12) C 0.60523(14) 0.0028(8) 0.2369(6) 0.0468(11) Uani 1.00 1 d . . . C(13) C 0.64093(12) 0.6253(8) -0.1914(6) 0.0439(11) Uani 1.00 1 d . . . C(14) C 0.62418(14) 0.4350(8) -0.1403(6) 0.0525(12) Uani 1.00 1 d . . . C(15) C 0.58572(14) 0.4016(9) -0.1724(6) 0.0557(14) Uani 1.00 1 d . . . C(16) C 0.56608(14) 0.5662(10) -0.2582(7) 0.0603(15) Uani 1.00 1 d . . . C(17) C 0.58079(15) 0.7573(9) -0.3139(7) 0.0576(14) Uani 1.00 1 d . . . C(18) C 0.61945(15) 0.7848(8) -0.2781(6) 0.0537(13) Uani 1.00 1 d . . . C(19) C 0.68251(14) 0.6642(8) -0.1479(6) 0.0515(12) Uani 1.00 1 d . . . H(1) H 0.7145 0.0094 0.0020 0.062 Uiso 1.00 1 c R . . H(2) H 0.7477 0.1315 0.0692 0.062 Uiso 1.00 1 c R . . H(3) H 0.7118 0.2428 0.0314 0.062 Uiso 1.00 1 c R . . H(4) H 0.7252 0.1918 0.3515 0.064 Uiso 1.00 1 c R . . H(5) H 0.7169 -0.1659 0.4588 0.079 Uiso 1.00 1 c R . . H(6) H 0.7535 -0.1340 0.3439 0.079 Uiso 1.00 1 c R . . H(7) H 0.7174 -0.2439 0.2489 0.079 Uiso 1.00 1 c R . . H(8) H 0.6529 -0.1666 0.1816 0.059 Uiso 1.00 1 c R . . H(9) H 0.6752 0.4178 0.3989 0.066 Uiso 1.00 1 c R . . H(10) H 0.6119 0.4855 0.4175 0.068 Uiso 1.00 1 c R . . H(11) H 0.5451 0.3719 0.3632 0.072 Uiso 1.00 1 c R . . H(12) H 0.5023 0.1147 0.2601 0.080 Uiso 1.00 1 c R . . H(13) H 0.5232 -0.2152 0.1465 0.079 Uiso 1.00 1 c R . . H(14) H 0.5867 -0.2833 0.1280 0.065 Uiso 1.00 1 c R . . H(15) H 0.6390 0.3263 -0.0831 0.063 Uiso 1.00 1 c R . . H(16) H 0.5739 0.2735 -0.1372 0.067 Uiso 1.00 1 c R . . H(17) H 0.5658 0.8641 -0.3728 0.069 Uiso 1.00 1 c R . . H(18) H 0.6310 0.9135 -0.3136 0.064 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0373(18) 0.097(2) 0.099(2) -0.0026(17) -0.0024(16) -0.017(2) O(1) 0.051(2) 0.066(2) 0.058(2) -0.013(2) -0.0015(16) 0.0036(18) O(2) 0.039(2) 0.069(2) 0.080(2) 0.0064(18) -0.0041(17) 0.010(2) N(1) 0.039(2) 0.061(2) 0.056(2) -0.005(2) 0.0031(18) 0.001(2) C(1) 0.036(2) 0.068(3) 0.055(2) -0.001(2) 0.004(2) -0.002(2) C(2) 0.043(3) 0.087(4) 0.068(3) 0.010(3) 0.002(2) 0.013(3) C(3) 0.036(2) 0.060(3) 0.052(2) 0.004(2) 0.004(2) -0.002(2) C(4) 0.034(2) 0.057(2) 0.049(2) 0.004(2) -0.000(2) -0.010(2) C(5) 0.045(3) 0.058(3) 0.061(3) -0.004(2) 0.005(2) -0.005(2) C(6) 0.054(3) 0.055(3) 0.060(3) -0.004(2) 0.005(2) -0.009(2) C(7) 0.041(2) 0.052(2) 0.049(2) 0.005(2) 0.007(2) -0.004(2) C(8) 0.046(3) 0.071(3) 0.064(3) 0.006(2) 0.004(2) -0.003(2) C(9) 0.047(3) 0.085(4) 0.067(3) 0.004(3) -0.003(2) -0.006(3) C(10) 0.043(3) 0.086(4) 0.067(3) -0.010(3) -0.001(2) -0.003(3) C(11) 0.034(2) 0.072(3) 0.058(3) -0.002(2) 0.004(2) -0.008(2) C(12) 0.042(2) 0.052(2) 0.047(2) -0.004(2) 0.001(2) -0.004(2) C(13) 0.027(2) 0.055(2) 0.050(2) 0.003(2) 0.0032(19) -0.004(2) C(14) 0.046(3) 0.055(3) 0.057(2) -0.003(2) -0.001(2) -0.002(2) C(15) 0.037(3) 0.068(3) 0.062(3) -0.008(2) -0.000(2) -0.007(2) C(16) 0.024(2) 0.086(4) 0.070(3) 0.003(2) -0.003(2) -0.019(3) C(17) 0.042(3) 0.064(3) 0.065(3) 0.006(2) -0.009(2) 0.001(2) C(18) 0.052(3) 0.059(3) 0.051(2) 0.006(2) 0.002(2) 0.000(2) C(19) 0.038(3) 0.063(3) 0.054(2) -0.006(2) 0.006(2) -0.003(2) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR2004 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F(1) C(16) 1.396(5) yes . . O(1) C(19) 1.252(6) yes . . O(2) C(19) 1.270(6) yes . . N(1) C(1) 1.513(6) yes . . C(1) C(2) 1.501(8) yes . . C(1) C(4) 1.510(6) yes . . C(3) C(4) 1.368(6) yes . . C(3) C(12) 1.422(6) yes . . C(4) C(5) 1.406(7) yes . . C(5) C(6) 1.374(7) yes . . C(6) C(7) 1.400(7) yes . . C(7) C(8) 1.433(7) yes . . C(7) C(12) 1.406(7) yes . . C(8) C(9) 1.371(8) yes . . C(9) C(10) 1.406(8) yes . . C(10) C(11) 1.377(7) yes . . C(11) C(12) 1.404(7) yes . . C(13) C(14) 1.382(7) yes . . C(13) C(18) 1.383(6) yes . . C(13) C(19) 1.518(6) yes . . C(14) C(15) 1.394(7) yes . . C(15) C(16) 1.370(7) yes . . C(16) C(17) 1.365(8) yes . . C(17) C(18) 1.399(7) yes . . N(1) H(1) 0.900 no . . N(1) H(2) 0.900 no . . N(1) H(3) 0.900 no . . C(1) H(4) 0.990 no . . C(2) H(5) 0.970 no . . C(2) H(6) 0.970 no . . C(2) H(7) 0.970 no . . C(3) H(8) 0.940 no . . C(5) H(9) 0.940 no . . C(6) H(10) 0.940 no . . C(8) H(11) 0.940 no . . C(9) H(12) 0.940 no . . C(10) H(13) 0.940 no . . C(11) H(14) 0.940 no . . C(14) H(15) 0.940 no . . C(15) H(16) 0.940 no . . C(17) H(17) 0.940 no . . C(18) H(18) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 N(1) C(1) C(2) 109.7(4) yes . . . N(1) C(1) C(4) 109.1(3) yes . . . C(2) C(1) C(4) 115.1(4) yes . . . C(4) C(3) C(12) 121.5(4) yes . . . C(1) C(4) C(3) 122.0(4) yes . . . C(1) C(4) C(5) 118.7(4) yes . . . C(3) C(4) C(5) 119.2(4) yes . . . C(4) C(5) C(6) 120.6(4) yes . . . C(5) C(6) C(7) 120.7(5) yes . . . C(6) C(7) C(8) 121.6(4) yes . . . C(6) C(7) C(12) 119.6(4) yes . . . C(8) C(7) C(12) 118.7(4) yes . . . C(7) C(8) C(9) 120.2(5) yes . . . C(8) C(9) C(10) 120.2(5) yes . . . C(9) C(10) C(11) 120.5(5) yes . . . C(10) C(11) C(12) 120.3(5) yes . . . C(3) C(12) C(7) 118.4(4) yes . . . C(3) C(12) C(11) 121.7(4) yes . . . C(7) C(12) C(11) 119.9(4) yes . . . C(14) C(13) C(18) 119.8(4) yes . . . C(14) C(13) C(19) 120.7(4) yes . . . C(18) C(13) C(19) 119.5(4) yes . . . C(13) C(14) C(15) 121.1(4) yes . . . C(14) C(15) C(16) 116.2(4) yes . . . F(1) C(16) C(15) 116.9(5) yes . . . F(1) C(16) C(17) 117.1(4) yes . . . C(15) C(16) C(17) 125.9(4) yes . . . C(16) C(17) C(18) 116.1(4) yes . . . C(13) C(18) C(17) 121.0(4) yes . . . O(1) C(19) O(2) 124.0(4) yes . . . O(1) C(19) C(13) 118.1(4) yes . . . O(2) C(19) C(13) 117.9(4) yes . . . C(1) N(1) H(1) 109.5 no . . . C(1) N(1) H(2) 109.5 no . . . C(1) N(1) H(3) 109.5 no . . . H(1) N(1) H(2) 109.5 no . . . H(1) N(1) H(3) 109.5 no . . . H(2) N(1) H(3) 109.5 no . . . N(1) C(1) H(4) 107.5 no . . . C(2) C(1) H(4) 107.5 no . . . C(4) C(1) H(4) 107.5 no . . . C(1) C(2) H(5) 109.5 no . . . C(1) C(2) H(6) 109.5 no . . . C(1) C(2) H(7) 109.5 no . . . H(5) C(2) H(6) 109.5 no . . . H(5) C(2) H(7) 109.5 no . . . H(6) C(2) H(7) 109.5 no . . . C(4) C(3) H(8) 119.3 no . . . C(12) C(3) H(8) 119.3 no . . . C(4) C(5) H(9) 119.7 no . . . C(6) C(5) H(9) 119.7 no . . . C(5) C(6) H(10) 119.7 no . . . C(7) C(6) H(10) 119.6 no . . . C(7) C(8) H(11) 119.9 no . . . C(9) C(8) H(11) 119.9 no . . . C(8) C(9) H(12) 119.9 no . . . C(10) C(9) H(12) 119.9 no . . . C(9) C(10) H(13) 119.7 no . . . C(11) C(10) H(13) 119.7 no . . . C(10) C(11) H(14) 119.8 no . . . C(12) C(11) H(14) 119.8 no . . . C(13) C(14) H(15) 119.5 no . . . C(15) C(14) H(15) 119.5 no . . . C(14) C(15) H(16) 121.9 no . . . C(16) C(15) H(16) 121.9 no . . . C(16) C(17) H(17) 122.0 no . . . C(18) C(17) H(17) 122.0 no . . . C(13) C(18) H(18) 119.5 no . . . C(17) C(18) H(18) 119.5 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N(1) C(1) C(4) C(3) 78.1(5) ? . . . . N(1) C(1) C(4) C(5) -100.1(5) ? . . . . C(2) C(1) C(4) C(3) -45.8(6) ? . . . . C(2) C(1) C(4) C(5) 136.1(4) ? . . . . C(4) C(3) C(12) C(7) -0.6(6) ? . . . . C(4) C(3) C(12) C(11) 179.7(4) ? . . . . C(12) C(3) C(4) C(1) -177.8(4) ? . . . . C(12) C(3) C(4) C(5) 0.3(6) ? . . . . C(1) C(4) C(5) C(6) 178.2(4) ? . . . . C(3) C(4) C(5) C(6) 0.1(6) ? . . . . C(4) C(5) C(6) C(7) -0.2(6) ? . . . . C(5) C(6) C(7) C(8) -179.0(4) ? . . . . C(5) C(6) C(7) C(12) -0.0(7) ? . . . . C(6) C(7) C(8) C(9) 179.6(5) ? . . . . C(6) C(7) C(12) C(3) 0.4(6) ? . . . . C(6) C(7) C(12) C(11) -179.8(3) ? . . . . C(8) C(7) C(12) C(3) 179.4(4) ? . . . . C(8) C(7) C(12) C(11) -0.8(7) ? . . . . C(12) C(7) C(8) C(9) 0.6(7) ? . . . . C(7) C(8) C(9) C(10) 0.3(6) ? . . . . C(8) C(9) C(10) C(11) -1.0(8) ? . . . . C(9) C(10) C(11) C(12) 0.8(8) ? . . . . C(10) C(11) C(12) C(3) 179.9(3) ? . . . . C(10) C(11) C(12) C(7) 0.1(5) ? . . . . C(14) C(13) C(18) C(17) 0.5(7) ? . . . . C(18) C(13) C(14) C(15) -0.9(7) ? . . . . C(14) C(13) C(19) O(1) 179.0(4) ? . . . . C(14) C(13) C(19) O(2) -2.0(7) ? . . . . C(19) C(13) C(14) C(15) 177.2(4) ? . . . . C(18) C(13) C(19) O(1) -2.8(6) ? . . . . C(18) C(13) C(19) O(2) 176.1(4) ? . . . . C(19) C(13) C(18) C(17) -177.6(4) ? . . . . C(13) C(14) C(15) C(16) 0.7(7) ? . . . . C(14) C(15) C(16) F(1) -179.7(4) ? . . . . C(14) C(15) C(16) C(17) -0.1(6) ? . . . . F(1) C(16) C(17) C(18) 179.3(4) ? . . . . C(15) C(16) C(17) C(18) -0.3(7) ? . . . . C(16) C(17) C(18) C(13) 0.0(6) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F(1) F(1) 3.516(4) ? . 2_654 F(1) C(8) 3.528(6) ? . 1_554 F(1) C(8) 3.422(6) ? . 2_655 F(1) C(9) 3.438(7) ? . 2_655 F(1) C(10) 3.386(6) ? . 2_665 F(1) C(15) 2.357(5) ? . . F(1) C(17) 2.356(6) ? . . O(1) O(2) 2.227(5) ? . . O(1) N(1) 2.762(5) ? . 1_565 O(1) N(1) 3.276(5) ? . 4_655 O(1) C(2) 3.544(6) ? . 1_564 O(1) C(13) 2.381(5) ? . . O(1) C(18) 2.793(6) ? . . O(2) O(1) 2.227(5) ? . . O(2) N(1) 2.754(5) ? . . O(2) N(1) 2.800(5) ? . 4_655 O(2) C(1) 3.538(6) ? . 4_655 O(2) C(2) 3.476(6) ? . 4_655 O(2) C(13) 2.393(5) ? . . O(2) C(14) 2.819(6) ? . . N(1) O(1) 2.762(5) ? . 1_545 N(1) O(1) 3.276(5) ? . 4_645 N(1) O(2) 2.754(5) ? . . N(1) O(2) 2.800(5) ? . 4_645 N(1) C(2) 2.465(7) ? . . N(1) C(3) 3.188(6) ? . . N(1) C(4) 2.463(6) ? . . N(1) C(5) 3.372(6) ? . . N(1) C(19) 3.522(6) ? . 1_545 N(1) C(19) 3.408(6) ? . 4_645 C(1) O(2) 3.538(6) ? . 4_645 C(1) C(3) 2.519(6) ? . . C(1) C(5) 2.511(7) ? . . C(2) O(1) 3.544(6) ? . 1_546 C(2) O(2) 3.476(6) ? . 4_645 C(2) N(1) 2.465(7) ? . . C(2) C(3) 3.042(7) ? . . C(2) C(4) 2.542(7) ? . . C(3) N(1) 3.188(6) ? . . C(3) C(1) 2.519(6) ? . . C(3) C(2) 3.042(7) ? . . C(3) C(5) 2.393(7) ? . . C(3) C(6) 2.774(7) ? . . C(3) C(7) 2.429(7) ? . . C(3) C(11) 2.467(6) ? . . C(4) N(1) 2.463(6) ? . . C(4) C(2) 2.542(7) ? . . C(4) C(6) 2.416(7) ? . . C(4) C(7) 2.805(6) ? . . C(4) C(12) 2.434(6) ? . . C(5) N(1) 3.372(6) ? . . C(5) C(1) 2.511(7) ? . . C(5) C(3) 2.393(7) ? . . C(5) C(7) 2.411(7) ? . . C(5) C(12) 2.797(7) ? . . C(6) C(3) 2.774(7) ? . . C(6) C(4) 2.416(7) ? . . C(6) C(8) 2.473(7) ? . . C(6) C(12) 2.426(7) ? . . C(6) C(14) 3.555(6) ? . 1_556 C(6) C(15) 3.572(7) ? . 1_556 C(7) C(3) 2.429(7) ? . . C(7) C(4) 2.805(6) ? . . C(7) C(5) 2.411(7) ? . . C(7) C(9) 2.431(7) ? . . C(7) C(10) 2.800(7) ? . . C(7) C(11) 2.432(7) ? . . C(8) F(1) 3.528(6) ? . 1_556 C(8) F(1) 3.422(6) ? . 2_655 C(8) C(6) 2.473(7) ? . . C(8) C(10) 2.407(8) ? . . C(8) C(11) 2.795(8) ? . . C(8) C(12) 2.443(7) ? . . C(9) F(1) 3.438(7) ? . 2_655 C(9) C(7) 2.431(7) ? . . C(9) C(11) 2.416(7) ? . . C(9) C(12) 2.800(7) ? . . C(10) F(1) 3.386(6) ? . 2_645 C(10) C(7) 2.800(7) ? . . C(10) C(8) 2.407(8) ? . . C(10) C(12) 2.412(7) ? . . C(11) C(3) 2.467(6) ? . . C(11) C(7) 2.432(7) ? . . C(11) C(8) 2.795(8) ? . . C(11) C(9) 2.416(7) ? . . C(11) C(16) 3.590(7) ? . 1_545 C(11) C(17) 3.568(7) ? . 1_545 C(12) C(4) 2.434(6) ? . . C(12) C(5) 2.797(7) ? . . C(12) C(6) 2.426(7) ? . . C(12) C(8) 2.443(7) ? . . C(12) C(9) 2.800(7) ? . . C(12) C(10) 2.412(7) ? . . C(13) O(1) 2.381(5) ? . . C(13) O(2) 2.393(5) ? . . C(13) C(15) 2.416(6) ? . . C(13) C(16) 2.711(6) ? . . C(13) C(17) 2.422(6) ? . . C(14) O(2) 2.819(6) ? . . C(14) C(6) 3.555(6) ? . 1_554 C(14) C(16) 2.346(7) ? . . C(14) C(17) 2.790(7) ? . . C(14) C(18) 2.392(7) ? . . C(14) C(19) 2.521(7) ? . . C(15) F(1) 2.357(5) ? . . C(15) C(6) 3.572(7) ? . 1_554 C(15) C(13) 2.416(6) ? . . C(15) C(17) 2.437(7) ? . . C(15) C(18) 2.788(7) ? . . C(16) C(11) 3.590(7) ? . 1_565 C(16) C(13) 2.711(6) ? . . C(16) C(14) 2.346(7) ? . . C(16) C(18) 2.345(7) ? . . C(17) F(1) 2.356(6) ? . . C(17) C(11) 3.568(7) ? . 1_565 C(17) C(13) 2.422(6) ? . . C(17) C(14) 2.790(7) ? . . C(17) C(15) 2.437(7) ? . . C(18) O(1) 2.793(6) ? . . C(18) C(14) 2.392(7) ? . . C(18) C(15) 2.788(7) ? . . C(18) C(16) 2.345(7) ? . . C(18) C(19) 2.508(7) ? . . C(19) N(1) 3.522(6) ? . 1_565 C(19) N(1) 3.408(6) ? . 4_655 C(19) C(14) 2.521(7) ? . . C(19) C(18) 2.508(7) ? . . F(1) H(11) 2.785 ? . 1_554 F(1) H(11) 2.806 ? . 2_655 F(1) H(12) 2.837 ? . 2_655 F(1) H(13) 3.509 ? . 1_565 F(1) H(13) 2.623 ? . 2_665 F(1) H(16) 2.539 ? . . F(1) H(17) 2.539 ? . . O(1) H(1) 1.886 ? . 1_565 O(1) H(2) 3.173 ? . 1_565 O(1) H(2) 2.512 ? . 4_655 O(1) H(3) 3.049 ? . 1_565 O(1) H(3) 3.484 ? . 4_655 O(1) H(4) 3.175 ? . 4_655 O(1) H(5) 2.592 ? . 1_564 O(1) H(7) 3.312 ? . 1_565 O(1) H(8) 3.204 ? . 1_565 O(1) H(18) 2.479 ? . . O(2) H(1) 3.233 ? . . O(2) H(1) 3.112 ? . 1_565 O(2) H(1) 3.021 ? . 4_655 O(2) H(2) 3.049 ? . . O(2) H(2) 1.960 ? . 4_655 O(2) H(3) 1.871 ? . . O(2) H(3) 3.401 ? . 4_655 O(2) H(6) 2.833 ? . 4_655 O(2) H(7) 2.698 ? . 1_565 O(2) H(8) 3.159 ? . 1_565 O(2) H(9) 3.508 ? . . O(2) H(15) 2.511 ? . . N(1) H(1) 3.359 ? . 4_655 N(1) H(2) 3.391 ? . 4_645 N(1) H(2) 3.517 ? . 4_655 N(1) H(3) 3.420 ? . 4_645 N(1) H(4) 2.043 ? . . N(1) H(5) 3.303 ? . . N(1) H(6) 2.700 ? . . N(1) H(6) 3.504 ? . 4_655 N(1) H(7) 2.601 ? . . N(1) H(7) 3.330 ? . 4_655 N(1) H(8) 3.177 ? . . N(1) H(9) 3.473 ? . . N(1) H(15) 3.386 ? . . C(1) H(1) 2.002 ? . . C(1) H(2) 2.002 ? . . C(1) H(3) 2.002 ? . . C(1) H(5) 2.041 ? . . C(1) H(5) 3.482 ? . 4_656 C(1) H(6) 2.041 ? . . C(1) H(6) 3.450 ? . 4_656 C(1) H(7) 2.041 ? . . C(1) H(8) 2.669 ? . . C(1) H(9) 2.648 ? . . C(2) H(1) 2.583 ? . . C(2) H(2) 2.673 ? . . C(2) H(2) 3.423 ? . 4_645 C(2) H(3) 3.238 ? . . C(2) H(3) 3.600 ? . 4_645 C(2) H(4) 2.032 ? . . C(2) H(4) 2.971 ? . 4_646 C(2) H(8) 2.798 ? . . C(2) H(9) 3.363 ? . 1_545 C(3) H(1) 3.047 ? . . C(3) H(3) 3.319 ? . . C(3) H(4) 3.283 ? . . C(3) H(5) 3.110 ? . . C(3) H(7) 2.899 ? . . C(3) H(9) 3.239 ? . . C(3) H(10) 3.497 ? . 1_545 C(3) H(14) 2.648 ? . . C(3) H(15) 3.170 ? . . C(3) H(18) 3.360 ? . 1_546 C(4) H(1) 2.719 ? . . C(4) H(2) 3.230 ? . . C(4) H(3) 2.532 ? . . C(4) H(4) 2.040 ? . . C(4) H(5) 2.678 ? . . C(4) H(6) 3.354 ? . . C(4) H(7) 2.818 ? . . C(4) H(8) 2.003 ? . . C(4) H(9) 2.042 ? . . C(4) H(10) 3.262 ? . . C(4) H(15) 3.124 ? . . C(4) H(18) 3.482 ? . 1_546 C(5) H(3) 3.133 ? . . C(5) H(4) 2.521 ? . . C(5) H(7) 3.587 ? . 1_565 C(5) H(8) 3.242 ? . . C(5) H(8) 3.477 ? . 1_565 C(5) H(10) 2.013 ? . . C(5) H(15) 3.212 ? . . C(5) H(18) 3.581 ? . 1_546 C(6) H(8) 3.499 ? . 1_565 C(6) H(9) 2.012 ? . . C(6) H(11) 2.662 ? . . C(6) H(14) 3.051 ? . 1_565 C(6) H(15) 3.352 ? . . C(6) H(18) 3.571 ? . 1_546 C(7) H(8) 3.276 ? . . C(7) H(9) 3.257 ? . . C(7) H(10) 2.036 ? . . C(7) H(11) 2.068 ? . . C(7) H(12) 3.282 ? . . C(7) H(14) 3.280 ? . . C(7) H(14) 3.468 ? . 1_565 C(7) H(15) 3.407 ? . . C(7) H(16) 3.280 ? . . C(7) H(17) 3.276 ? . 1_546 C(7) H(18) 3.465 ? . 1_546 C(8) H(10) 2.647 ? . . C(8) H(12) 2.012 ? . . C(8) H(13) 3.251 ? . . C(8) H(14) 3.483 ? . 1_565 C(8) H(16) 3.374 ? . . C(8) H(17) 3.248 ? . 1_546 C(9) H(11) 2.012 ? . . C(9) H(13) 2.042 ? . . C(9) H(14) 3.264 ? . . C(9) H(16) 3.514 ? . . C(9) H(17) 3.244 ? . 1_546 C(10) H(11) 3.462 ? . 1_545 C(10) H(11) 3.257 ? . . C(10) H(12) 2.044 ? . . C(10) H(13) 3.292 ? . 2_655 C(10) H(14) 2.017 ? . . C(10) H(16) 3.567 ? . . C(10) H(17) 3.256 ? . 1_546 C(11) H(8) 2.645 ? . . C(11) H(10) 3.053 ? . 1_545 C(11) H(11) 3.487 ? . 1_545 C(11) H(12) 3.260 ? . . C(11) H(13) 2.016 ? . . C(11) H(16) 3.469 ? . . C(11) H(17) 3.294 ? . 1_546 C(12) H(8) 2.052 ? . . C(12) H(10) 3.472 ? . 1_545 C(12) H(10) 3.273 ? . . C(12) H(11) 3.292 ? . . C(12) H(13) 3.259 ? . . C(12) H(14) 2.041 ? . . C(12) H(15) 3.318 ? . . C(12) H(16) 3.321 ? . . C(12) H(17) 3.304 ? . 1_546 C(12) H(18) 3.363 ? . 1_546 C(13) H(8) 2.989 ? . 1_565 C(13) H(9) 3.483 ? . 1_554 C(13) H(10) 3.076 ? . 1_554 C(13) H(14) 3.115 ? . 1_565 C(13) H(15) 2.017 ? . . C(13) H(16) 3.272 ? . . C(13) H(17) 3.278 ? . . C(13) H(18) 2.020 ? . . C(14) H(3) 3.511 ? . . C(14) H(8) 3.510 ? . 1_565 C(14) H(10) 3.202 ? . 1_554 C(14) H(14) 2.964 ? . 1_565 C(14) H(16) 2.052 ? . . C(14) H(18) 3.485 ? . 1_545 C(14) H(18) 3.238 ? . . C(15) H(10) 3.171 ? . 1_554 C(15) H(11) 3.580 ? . 1_554 C(15) H(14) 2.913 ? . 1_565 C(15) H(15) 2.028 ? . . C(15) H(17) 3.279 ? . . C(16) H(10) 2.944 ? . 1_554 C(16) H(11) 3.038 ? . 1_554 C(16) H(13) 3.579 ? . 2_665 C(16) H(14) 2.988 ? . 1_565 C(16) H(15) 3.201 ? . . C(16) H(16) 2.031 ? . . C(16) H(17) 2.027 ? . . C(16) H(18) 3.200 ? . . C(17) H(10) 2.826 ? . 1_554 C(17) H(11) 3.531 ? . 1_554 C(17) H(14) 3.182 ? . 1_565 C(17) H(16) 3.278 ? . . C(17) H(16) 3.464 ? . 1_565 C(17) H(18) 2.034 ? . . C(18) H(8) 3.474 ? . 1_565 C(18) H(10) 2.874 ? . 1_554 C(18) H(14) 3.217 ? . 1_565 C(18) H(15) 3.238 ? . . C(18) H(17) 2.058 ? . . C(19) H(1) 2.637 ? . 1_565 C(19) H(2) 2.531 ? . 4_655 C(19) H(3) 3.080 ? . . C(19) H(5) 3.302 ? . 1_564 C(19) H(6) 3.300 ? . 4_655 C(19) H(7) 3.111 ? . 1_565 C(19) H(8) 2.835 ? . 1_565 C(19) H(9) 3.596 ? . 1_554 C(19) H(15) 2.664 ? . . C(19) H(18) 2.643 ? . . H(1) O(1) 1.886 ? . 1_545 H(1) O(2) 3.112 ? . 1_545 H(1) O(2) 3.233 ? . . H(1) O(2) 3.021 ? . 4_645 H(1) N(1) 3.359 ? . 4_645 H(1) C(1) 2.002 ? . . H(1) C(2) 2.583 ? . . H(1) C(3) 3.047 ? . . H(1) C(4) 2.719 ? . . H(1) C(19) 2.637 ? . 1_545 H(1) H(2) 1.470 ? . . H(1) H(2) 2.767 ? . 4_645 H(1) H(3) 1.470 ? . . H(1) H(3) 3.124 ? . 4_645 H(1) H(4) 2.765 ? . . H(1) H(5) 3.455 ? . . H(1) H(6) 2.908 ? . . H(1) H(6) 3.555 ? . 4_655 H(1) H(7) 2.370 ? . . H(1) H(7) 3.446 ? . 4_655 H(1) H(8) 2.812 ? . . H(1) H(15) 3.366 ? . . H(2) O(1) 3.173 ? . 1_545 H(2) O(1) 2.512 ? . 4_645 H(2) O(2) 3.049 ? . . H(2) O(2) 1.960 ? . 4_645 H(2) N(1) 3.517 ? . 4_645 H(2) N(1) 3.391 ? . 4_655 H(2) C(1) 2.002 ? . . H(2) C(2) 2.673 ? . . H(2) C(2) 3.423 ? . 4_655 H(2) C(4) 3.230 ? . . H(2) C(19) 2.531 ? . 4_645 H(2) H(1) 1.470 ? . . H(2) H(1) 2.767 ? . 4_655 H(2) H(2) 3.270 ? . 4_645 H(2) H(2) 3.270 ? . 4_655 H(2) H(3) 1.469 ? . . H(2) H(3) 2.921 ? . 4_645 H(2) H(4) 2.245 ? . . H(2) H(5) 3.567 ? . . H(2) H(6) 2.573 ? . . H(2) H(6) 3.304 ? . 4_655 H(2) H(7) 2.899 ? . . H(2) H(7) 2.760 ? . 4_655 H(3) O(1) 3.049 ? . 1_545 H(3) O(1) 3.484 ? . 4_645 H(3) O(2) 1.871 ? . . H(3) O(2) 3.401 ? . 4_645 H(3) N(1) 3.420 ? . 4_655 H(3) C(1) 2.002 ? . . H(3) C(2) 3.238 ? . . H(3) C(2) 3.600 ? . 4_655 H(3) C(3) 3.319 ? . . H(3) C(4) 2.532 ? . . H(3) C(5) 3.133 ? . . H(3) C(14) 3.511 ? . . H(3) C(19) 3.080 ? . . H(3) H(1) 1.470 ? . . H(3) H(1) 3.124 ? . 4_655 H(3) H(2) 1.469 ? . . H(3) H(2) 2.921 ? . 4_655 H(3) H(4) 2.349 ? . . H(3) H(6) 3.526 ? . . H(3) H(6) 3.110 ? . 4_655 H(3) H(7) 3.407 ? . . H(3) H(7) 3.555 ? . 1_565 H(3) H(7) 3.297 ? . 4_655 H(3) H(8) 3.497 ? . . H(3) H(9) 3.185 ? . . H(3) H(15) 2.734 ? . . H(4) O(1) 3.175 ? . 4_645 H(4) N(1) 2.043 ? . . H(4) C(2) 2.032 ? . . H(4) C(2) 2.971 ? . 4_656 H(4) C(3) 3.283 ? . . H(4) C(4) 2.040 ? . . H(4) C(5) 2.521 ? . . H(4) H(1) 2.765 ? . . H(4) H(2) 2.245 ? . . H(4) H(3) 2.349 ? . . H(4) H(5) 2.376 ? . . H(4) H(5) 2.576 ? . 4_656 H(4) H(6) 2.264 ? . . H(4) H(6) 2.527 ? . 4_656 H(4) H(7) 2.817 ? . . H(4) H(7) 3.593 ? . 1_565 H(4) H(7) 3.472 ? . 4_656 H(4) H(8) 3.575 ? . . H(4) H(9) 2.303 ? . . H(5) O(1) 2.592 ? . 1_546 H(5) N(1) 3.303 ? . . H(5) C(1) 2.041 ? . . H(5) C(1) 3.482 ? . 4_646 H(5) C(3) 3.110 ? . . H(5) C(4) 2.678 ? . . H(5) C(19) 3.302 ? . 1_546 H(5) H(1) 3.455 ? . . H(5) H(2) 3.567 ? . . H(5) H(4) 2.376 ? . . H(5) H(4) 2.576 ? . 4_646 H(5) H(6) 1.584 ? . . H(5) H(6) 3.383 ? . 4_646 H(5) H(7) 1.584 ? . . H(5) H(8) 2.959 ? . . H(5) H(9) 3.005 ? . 1_545 H(5) H(18) 3.566 ? . 1_546 H(6) O(2) 2.833 ? . 4_645 H(6) N(1) 2.700 ? . . H(6) N(1) 3.504 ? . 4_645 H(6) C(1) 2.041 ? . . H(6) C(1) 3.450 ? . 4_646 H(6) C(4) 3.354 ? . . H(6) C(19) 3.300 ? . 4_645 H(6) H(1) 2.908 ? . . H(6) H(1) 3.555 ? . 4_645 H(6) H(2) 2.573 ? . . H(6) H(2) 3.304 ? . 4_645 H(6) H(3) 3.526 ? . . H(6) H(3) 3.110 ? . 4_645 H(6) H(4) 2.264 ? . . H(6) H(4) 2.527 ? . 4_646 H(6) H(5) 1.584 ? . . H(6) H(5) 3.383 ? . 4_656 H(6) H(7) 1.584 ? . . H(6) H(9) 3.088 ? . 4_646 H(7) O(1) 3.312 ? . 1_545 H(7) O(2) 2.698 ? . 1_545 H(7) N(1) 2.601 ? . . H(7) N(1) 3.330 ? . 4_645 H(7) C(1) 2.041 ? . . H(7) C(3) 2.899 ? . . H(7) C(4) 2.818 ? . . H(7) C(5) 3.587 ? . 1_545 H(7) C(19) 3.111 ? . 1_545 H(7) H(1) 2.370 ? . . H(7) H(1) 3.446 ? . 4_645 H(7) H(2) 2.899 ? . . H(7) H(2) 2.760 ? . 4_645 H(7) H(3) 3.555 ? . 1_545 H(7) H(3) 3.407 ? . . H(7) H(3) 3.297 ? . 4_645 H(7) H(4) 3.593 ? . 1_545 H(7) H(4) 2.817 ? . . H(7) H(4) 3.472 ? . 4_646 H(7) H(5) 1.584 ? . . H(7) H(6) 1.584 ? . . H(7) H(8) 2.372 ? . . H(7) H(9) 2.824 ? . 1_545 H(8) O(1) 3.204 ? . 1_545 H(8) O(2) 3.159 ? . 1_545 H(8) N(1) 3.177 ? . . H(8) C(1) 2.669 ? . . H(8) C(2) 2.798 ? . . H(8) C(4) 2.003 ? . . H(8) C(5) 3.477 ? . 1_545 H(8) C(5) 3.242 ? . . H(8) C(6) 3.499 ? . 1_545 H(8) C(7) 3.276 ? . . H(8) C(11) 2.645 ? . . H(8) C(12) 2.052 ? . . H(8) C(13) 2.989 ? . 1_545 H(8) C(14) 3.510 ? . 1_545 H(8) C(18) 3.474 ? . 1_545 H(8) C(19) 2.835 ? . 1_545 H(8) H(1) 2.812 ? . . H(8) H(3) 3.497 ? . . H(8) H(4) 3.575 ? . . H(8) H(5) 2.959 ? . . H(8) H(7) 2.372 ? . . H(8) H(9) 3.103 ? . 1_545 H(8) H(10) 3.147 ? . 1_545 H(8) H(14) 2.481 ? . . H(9) O(2) 3.508 ? . . H(9) N(1) 3.473 ? . . H(9) C(1) 2.648 ? . . H(9) C(2) 3.363 ? . 1_565 H(9) C(3) 3.239 ? . . H(9) C(4) 2.042 ? . . H(9) C(6) 2.012 ? . . H(9) C(7) 3.257 ? . . H(9) C(13) 3.483 ? . 1_556 H(9) C(19) 3.596 ? . 1_556 H(9) H(3) 3.185 ? . . H(9) H(4) 2.303 ? . . H(9) H(5) 3.005 ? . 1_565 H(9) H(6) 3.088 ? . 4_656 H(9) H(7) 2.824 ? . 1_565 H(9) H(8) 3.103 ? . 1_565 H(9) H(10) 2.305 ? . . H(10) C(3) 3.497 ? . 1_565 H(10) C(4) 3.262 ? . . H(10) C(5) 2.013 ? . . H(10) C(7) 2.036 ? . . H(10) C(8) 2.647 ? . . H(10) C(11) 3.053 ? . 1_565 H(10) C(12) 3.273 ? . . H(10) C(12) 3.472 ? . 1_565 H(10) C(13) 3.076 ? . 1_556 H(10) C(14) 3.202 ? . 1_556 H(10) C(15) 3.171 ? . 1_556 H(10) C(16) 2.944 ? . 1_556 H(10) C(17) 2.826 ? . 1_556 H(10) C(18) 2.874 ? . 1_556 H(10) H(8) 3.147 ? . 1_565 H(10) H(9) 2.305 ? . . H(10) H(11) 2.492 ? . . H(10) H(14) 2.650 ? . 1_565 H(10) H(17) 3.273 ? . 1_556 H(10) H(18) 3.340 ? . 1_556 H(11) F(1) 2.785 ? . 1_556 H(11) F(1) 2.806 ? . 2_655 H(11) C(6) 2.662 ? . . H(11) C(7) 2.068 ? . . H(11) C(9) 2.012 ? . . H(11) C(10) 3.257 ? . . H(11) C(10) 3.462 ? . 1_565 H(11) C(11) 3.487 ? . 1_565 H(11) C(12) 3.292 ? . . H(11) C(15) 3.580 ? . 1_556 H(11) C(16) 3.038 ? . 1_556 H(11) C(17) 3.531 ? . 1_556 H(11) H(10) 2.492 ? . . H(11) H(12) 2.308 ? . . H(11) H(13) 3.085 ? . 1_565 H(11) H(14) 3.140 ? . 1_565 H(12) F(1) 2.837 ? . 2_655 H(12) C(7) 3.282 ? . . H(12) C(8) 2.012 ? . . H(12) C(10) 2.044 ? . . H(12) C(11) 3.260 ? . . H(12) H(11) 2.308 ? . . H(12) H(12) 3.457 ? . 2_656 H(12) H(13) 2.340 ? . . H(12) H(16) 2.984 ? . 2_655 H(12) H(17) 3.023 ? . 2_645 H(13) F(1) 3.509 ? . 1_545 H(13) F(1) 2.623 ? . 2_645 H(13) C(8) 3.251 ? . . H(13) C(9) 2.042 ? . . H(13) C(10) 3.292 ? . 2_655 H(13) C(11) 2.016 ? . . H(13) C(12) 3.259 ? . . H(13) C(16) 3.579 ? . 2_645 H(13) H(11) 3.085 ? . 1_545 H(13) H(12) 2.340 ? . . H(13) H(13) 2.616 ? . 2_655 H(13) H(14) 2.311 ? . . H(14) C(3) 2.648 ? . . H(14) C(6) 3.051 ? . 1_545 H(14) C(7) 3.468 ? . 1_545 H(14) C(7) 3.280 ? . . H(14) C(8) 3.483 ? . 1_545 H(14) C(9) 3.264 ? . . H(14) C(10) 2.017 ? . . H(14) C(12) 2.041 ? . . H(14) C(13) 3.115 ? . 1_545 H(14) C(14) 2.964 ? . 1_545 H(14) C(15) 2.913 ? . 1_545 H(14) C(16) 2.988 ? . 1_545 H(14) C(17) 3.182 ? . 1_545 H(14) C(18) 3.217 ? . 1_545 H(14) H(8) 2.481 ? . . H(14) H(10) 2.650 ? . 1_545 H(14) H(11) 3.140 ? . 1_545 H(14) H(13) 2.311 ? . . H(14) H(15) 3.449 ? . 1_545 H(14) H(16) 3.369 ? . 1_545 H(15) O(2) 2.511 ? . . H(15) N(1) 3.386 ? . . H(15) C(3) 3.170 ? . . H(15) C(4) 3.124 ? . . H(15) C(5) 3.212 ? . . H(15) C(6) 3.352 ? . . H(15) C(7) 3.407 ? . . H(15) C(12) 3.318 ? . . H(15) C(13) 2.017 ? . . H(15) C(15) 2.028 ? . . H(15) C(16) 3.201 ? . . H(15) C(18) 3.238 ? . . H(15) C(19) 2.664 ? . . H(15) H(1) 3.366 ? . . H(15) H(3) 2.734 ? . . H(15) H(14) 3.449 ? . 1_565 H(15) H(16) 2.353 ? . . H(15) H(18) 3.060 ? . 1_545 H(16) F(1) 2.539 ? . . H(16) C(7) 3.280 ? . . H(16) C(8) 3.374 ? . . H(16) C(9) 3.514 ? . . H(16) C(10) 3.567 ? . . H(16) C(11) 3.469 ? . . H(16) C(12) 3.321 ? . . H(16) C(13) 3.272 ? . . H(16) C(14) 2.052 ? . . H(16) C(16) 2.031 ? . . H(16) C(17) 3.464 ? . 1_545 H(16) C(17) 3.278 ? . . H(16) H(12) 2.984 ? . 2_655 H(16) H(14) 3.369 ? . 1_565 H(16) H(15) 2.353 ? . . H(16) H(17) 3.063 ? . 1_545 H(16) H(18) 3.312 ? . 1_545 H(17) F(1) 2.539 ? . . H(17) C(7) 3.276 ? . 1_564 H(17) C(8) 3.248 ? . 1_564 H(17) C(9) 3.244 ? . 1_564 H(17) C(10) 3.256 ? . 1_564 H(17) C(11) 3.294 ? . 1_564 H(17) C(12) 3.304 ? . 1_564 H(17) C(13) 3.278 ? . . H(17) C(15) 3.279 ? . . H(17) C(16) 2.027 ? . . H(17) C(18) 2.058 ? . . H(17) H(10) 3.273 ? . 1_554 H(17) H(12) 3.023 ? . 2_665 H(17) H(16) 3.063 ? . 1_565 H(17) H(18) 2.360 ? . . H(18) O(1) 2.479 ? . . H(18) C(3) 3.360 ? . 1_564 H(18) C(4) 3.482 ? . 1_564 H(18) C(5) 3.581 ? . 1_564 H(18) C(6) 3.571 ? . 1_564 H(18) C(7) 3.465 ? . 1_564 H(18) C(12) 3.363 ? . 1_564 H(18) C(13) 2.020 ? . . H(18) C(14) 3.238 ? . . H(18) C(14) 3.485 ? . 1_565 H(18) C(16) 3.200 ? . . H(18) C(17) 2.034 ? . . H(18) C(19) 2.643 ? . . H(18) H(5) 3.566 ? . 1_564 H(18) H(10) 3.340 ? . 1_554 H(18) H(15) 3.060 ? . 1_565 H(18) H(16) 3.312 ? . 1_565 H(18) H(17) 2.360 ? . . data__pIBA_R12NaphEthyAmChloEtha _database_code_depnum_ccdc_archive 'CCDC 884894' #TrackingRef 'RNaph12-pIBA.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H18 I N O2 ' _chemical_formula_moiety 'C19 H18 I N O2 ' _chemical_formula_weight 419.26 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2+X,1/2-Y,-Z 3 -X,1/2+Y,1/2-Z 4 1/2-X,-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 5.96084(15) _cell_length_b 12.8706(2) _cell_length_c 22.8019(4) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1749.35(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7207 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 68.3 _cell_measurement_temperature 213.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832.00 _exptl_absorpt_coefficient_mu 14.449 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.139 _exptl_absorpt_correction_T_max 0.236 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 18299 _diffrn_reflns_av_R_equivalents 0.166 _diffrn_reflns_theta_max 68.25 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_ambient_temperature 213.1 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3189 _reflns_number_gt 2323 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0625 _refine_ls_wR_factor_ref 0.1574 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3189 _refine_ls_number_parameters 210 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 1.42 _refine_diff_density_min -1.23 _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0013(2) _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1315 Friedel Pairs' _refine_ls_abs_structure_Flack -0.028(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; I I -0.326 6.836 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I(1) I 0.24848(13) 0.63710(4) 0.81219(2) 0.0470(2) Uani 1.00 1 d . . . O(1) O 0.0937(10) 0.3304(5) 0.5581(2) 0.0438(17) Uani 1.00 1 d . . . O(2) O -0.2447(11) 0.3138(4) 0.5995(2) 0.0376(12) Uani 1.00 1 d . . . N(1) N 0.5015(10) 0.3512(5) 0.5019(2) 0.0342(17) Uani 1.00 1 d . . . C(1) C 0.6760(13) 0.5693(6) 0.5469(3) 0.031(2) Uani 1.00 1 d . . . C(2) C 0.5217(14) 0.5427(6) 0.5053(3) 0.0294(19) Uani 1.00 1 d . . . C(3) C 0.3230(14) 0.6020(6) 0.5013(4) 0.040(2) Uani 1.00 1 d . . . C(4) C 0.2834(18) 0.6813(6) 0.5384(3) 0.037(2) Uani 1.00 1 d . . . C(5) C 0.4313(15) 0.7069(6) 0.5825(3) 0.036(2) Uani 1.00 1 d . . . C(6) C 0.6373(14) 0.6514(6) 0.5867(3) 0.030(2) Uani 1.00 1 d . . . C(7) C 0.7910(16) 0.6808(6) 0.6303(3) 0.036(2) Uani 1.00 1 d . . . C(8) C 0.749(2) 0.7565(7) 0.6706(3) 0.052(2) Uani 1.00 1 d . . . C(9) C 0.5403(18) 0.8106(8) 0.6675(4) 0.051(2) Uani 1.00 1 d . . . C(10) C 0.3886(15) 0.7881(7) 0.6235(4) 0.042(2) Uani 1.00 1 d . . . C(11) C 0.5537(14) 0.4459(6) 0.4669(3) 0.031(2) Uani 1.00 1 d . . . C(12) C 0.7826(16) 0.4334(7) 0.4401(3) 0.049(2) Uani 1.00 1 d . . . C(13) C 0.0336(13) 0.4096(6) 0.6515(3) 0.0269(18) Uani 1.00 1 d . . . C(14) C 0.2452(17) 0.4555(6) 0.6530(3) 0.0389(19) Uani 1.00 1 d . . . C(15) C 0.3060(14) 0.5188(7) 0.6983(3) 0.039(2) Uani 1.00 1 d . . . C(16) C 0.1591(15) 0.5336(6) 0.7443(3) 0.036(2) Uani 1.00 1 d . . . C(17) C -0.0491(15) 0.4903(7) 0.7441(3) 0.038(2) Uani 1.00 1 d . . . C(18) C -0.1122(14) 0.4258(7) 0.6981(3) 0.036(2) Uani 1.00 1 d . . . C(19) C -0.0431(15) 0.3469(6) 0.6001(3) 0.032(2) Uani 1.00 1 d . . . H(1) H 0.3645 0.3576 0.5181 0.041 Uiso 1.00 1 c R . . H(2) H 0.6046 0.3436 0.5305 0.041 Uiso 1.00 1 c R . . H(3) H 0.5041 0.2950 0.4784 0.041 Uiso 1.00 1 c R . . H(4) H 0.8115 0.5321 0.5490 0.037 Uiso 1.00 1 c R . . H(5) H 0.2166 0.5859 0.4723 0.049 Uiso 1.00 1 c R . . H(6) H 0.1511 0.7203 0.5341 0.045 Uiso 1.00 1 c R . . H(7) H 0.9301 0.6465 0.6318 0.043 Uiso 1.00 1 c R . . H(8) H 0.8544 0.7727 0.6998 0.062 Uiso 1.00 1 c R . . H(9) H 0.5059 0.8618 0.6955 0.061 Uiso 1.00 1 c R . . H(10) H 0.2555 0.8269 0.6205 0.050 Uiso 1.00 1 c R . . H(11) H 0.4436 0.4497 0.4345 0.038 Uiso 1.00 1 c R . . H(12) H 0.7862 0.3705 0.4166 0.059 Uiso 1.00 1 c R . . H(13) H 0.8941 0.4288 0.4710 0.059 Uiso 1.00 1 c R . . H(14) H 0.8151 0.4929 0.4154 0.059 Uiso 1.00 1 c R . . H(15) H 0.3475 0.4426 0.6225 0.047 Uiso 1.00 1 c R . . H(16) H 0.4466 0.5519 0.6982 0.047 Uiso 1.00 1 c R . . H(17) H -0.1497 0.5040 0.7749 0.046 Uiso 1.00 1 c R . . H(18) H -0.2533 0.3933 0.6985 0.043 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I(1) 0.0766(5) 0.0352(4) 0.0293(3) -0.0017(5) -0.0007(4) -0.0089(2) O(1) 0.047(3) 0.044(4) 0.040(3) -0.006(3) 0.003(3) -0.019(3) O(2) 0.043(3) 0.035(3) 0.034(2) -0.006(4) -0.005(3) 0.002(2) N(1) 0.035(4) 0.029(4) 0.038(4) -0.004(3) -0.001(3) -0.005(3) C(1) 0.043(5) 0.017(4) 0.032(4) 0.007(3) 0.006(3) -0.001(3) C(2) 0.043(5) 0.023(4) 0.023(4) 0.001(3) -0.002(3) -0.001(3) C(3) 0.050(6) 0.030(5) 0.042(5) -0.002(4) -0.003(4) 0.009(4) C(4) 0.049(6) 0.025(4) 0.038(4) 0.003(4) 0.004(4) 0.009(3) C(5) 0.052(5) 0.017(4) 0.039(5) 0.001(4) 0.008(4) 0.005(4) C(6) 0.044(5) 0.017(4) 0.030(4) -0.002(3) -0.005(3) 0.000(3) C(7) 0.052(6) 0.020(4) 0.035(4) 0.002(4) 0.002(4) -0.002(3) C(8) 0.057(6) 0.051(6) 0.048(5) -0.012(7) -0.003(6) -0.011(4) C(9) 0.071(7) 0.038(6) 0.045(6) -0.010(5) 0.010(5) -0.019(5) C(10) 0.042(5) 0.024(5) 0.059(6) 0.003(4) 0.003(4) 0.007(4) C(11) 0.043(5) 0.019(4) 0.032(4) -0.002(4) -0.008(4) -0.002(3) C(12) 0.073(7) 0.035(5) 0.040(4) -0.018(6) 0.023(5) -0.011(4) C(13) 0.044(5) 0.013(4) 0.024(4) -0.005(3) -0.001(3) 0.005(3) C(14) 0.051(5) 0.035(4) 0.031(4) -0.004(6) 0.003(5) -0.008(3) C(15) 0.043(6) 0.038(5) 0.037(5) -0.000(4) -0.004(3) -0.006(4) C(16) 0.067(6) 0.023(4) 0.019(4) 0.016(4) 0.000(4) 0.005(3) C(17) 0.038(5) 0.055(6) 0.022(4) 0.007(4) 0.006(3) -0.008(4) C(18) 0.043(5) 0.030(5) 0.035(5) -0.002(4) 0.005(3) -0.006(4) C(19) 0.049(5) 0.026(5) 0.020(4) 0.000(4) -0.004(3) -0.002(3) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SHELXS97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 I(1) C(16) 2.111(8) yes . . O(1) C(19) 1.274(10) yes . . O(2) C(19) 1.275(11) yes . . N(1) C(11) 1.490(10) yes . . C(1) C(2) 1.364(11) yes . . C(1) C(6) 1.412(11) yes . . C(2) C(3) 1.413(12) yes . . C(2) C(11) 1.535(11) yes . . C(3) C(4) 1.346(12) yes . . C(4) C(5) 1.377(13) yes . . C(5) C(6) 1.424(12) yes . . C(5) C(10) 1.425(12) yes . . C(6) C(7) 1.404(11) yes . . C(7) C(8) 1.364(12) yes . . C(8) C(9) 1.426(15) yes . . C(9) C(10) 1.383(14) yes . . C(11) C(12) 1.503(12) yes . . C(13) C(14) 1.393(12) yes . . C(13) C(18) 1.388(11) yes . . C(13) C(19) 1.495(11) yes . . C(14) C(15) 1.365(11) yes . . C(15) C(16) 1.378(11) yes . . C(16) C(17) 1.360(12) yes . . C(17) C(18) 1.390(12) yes . . N(1) H(1) 0.900 no . . N(1) H(2) 0.900 no . . N(1) H(3) 0.900 no . . C(1) H(4) 0.940 no . . C(3) H(5) 0.940 no . . C(4) H(6) 0.940 no . . C(7) H(7) 0.940 no . . C(8) H(8) 0.940 no . . C(9) H(9) 0.940 no . . C(10) H(10) 0.940 no . . C(11) H(11) 0.990 no . . C(12) H(12) 0.970 no . . C(12) H(13) 0.970 no . . C(12) H(14) 0.970 no . . C(14) H(15) 0.940 no . . C(15) H(16) 0.940 no . . C(17) H(17) 0.940 no . . C(18) H(18) 0.940 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(6) 121.7(7) yes . . . C(1) C(2) C(3) 118.3(7) yes . . . C(1) C(2) C(11) 121.1(7) yes . . . C(3) C(2) C(11) 120.4(7) yes . . . C(2) C(3) C(4) 121.1(8) yes . . . C(3) C(4) C(5) 121.9(9) yes . . . C(4) C(5) C(6) 118.8(8) yes . . . C(4) C(5) C(10) 122.7(8) yes . . . C(6) C(5) C(10) 118.5(7) yes . . . C(1) C(6) C(5) 118.2(7) yes . . . C(1) C(6) C(7) 123.4(7) yes . . . C(5) C(6) C(7) 118.4(7) yes . . . C(6) C(7) C(8) 123.3(8) yes . . . C(7) C(8) C(9) 118.5(9) yes . . . C(8) C(9) C(10) 120.2(9) yes . . . C(5) C(10) C(9) 120.9(8) yes . . . N(1) C(11) C(2) 109.4(6) yes . . . N(1) C(11) C(12) 108.7(6) yes . . . C(2) C(11) C(12) 115.6(7) yes . . . C(14) C(13) C(18) 118.9(7) yes . . . C(14) C(13) C(19) 121.7(7) yes . . . C(18) C(13) C(19) 119.3(7) yes . . . C(13) C(14) C(15) 120.8(8) yes . . . C(14) C(15) C(16) 119.3(8) yes . . . I(1) C(16) C(15) 119.0(6) yes . . . I(1) C(16) C(17) 119.4(6) yes . . . C(15) C(16) C(17) 121.4(7) yes . . . C(16) C(17) C(18) 119.5(8) yes . . . C(13) C(18) C(17) 119.9(8) yes . . . O(1) C(19) O(2) 122.7(7) yes . . . O(1) C(19) C(13) 118.9(7) yes . . . O(2) C(19) C(13) 118.4(7) yes . . . C(11) N(1) H(1) 109.5 no . . . C(11) N(1) H(2) 109.5 no . . . C(11) N(1) H(3) 109.5 no . . . H(1) N(1) H(2) 109.5 no . . . H(1) N(1) H(3) 109.5 no . . . H(2) N(1) H(3) 109.5 no . . . C(2) C(1) H(4) 119.2 no . . . C(6) C(1) H(4) 119.2 no . . . C(2) C(3) H(5) 119.5 no . . . C(4) C(3) H(5) 119.5 no . . . C(3) C(4) H(6) 119.1 no . . . C(5) C(4) H(6) 119.1 no . . . C(6) C(7) H(7) 118.3 no . . . C(8) C(7) H(7) 118.3 no . . . C(7) C(8) H(8) 120.8 no . . . C(9) C(8) H(8) 120.8 no . . . C(8) C(9) H(9) 119.9 no . . . C(10) C(9) H(9) 119.9 no . . . C(5) C(10) H(10) 119.6 no . . . C(9) C(10) H(10) 119.6 no . . . N(1) C(11) H(11) 107.7 no . . . C(2) C(11) H(11) 107.7 no . . . C(12) C(11) H(11) 107.6 no . . . C(11) C(12) H(12) 109.5 no . . . C(11) C(12) H(13) 109.5 no . . . C(11) C(12) H(14) 109.5 no . . . H(12) C(12) H(13) 109.5 no . . . H(12) C(12) H(14) 109.5 no . . . H(13) C(12) H(14) 109.5 no . . . C(13) C(14) H(15) 119.6 no . . . C(15) C(14) H(15) 119.6 no . . . C(14) C(15) H(16) 120.4 no . . . C(16) C(15) H(16) 120.4 no . . . C(16) C(17) H(17) 120.2 no . . . C(18) C(17) H(17) 120.2 no . . . C(13) C(18) H(18) 120.1 no . . . C(17) C(18) H(18) 120.1 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(6) C(5) -0.2(9) ? . . . . C(2) C(1) C(6) C(7) 179.6(7) ? . . . . C(6) C(1) C(2) C(3) 2.4(12) ? . . . . C(6) C(1) C(2) C(11) -173.0(7) ? . . . . C(1) C(2) C(3) C(4) -1.6(12) ? . . . . C(1) C(2) C(11) N(1) 75.8(9) ? . . . . C(1) C(2) C(11) C(12) -47.1(10) ? . . . . C(3) C(2) C(11) N(1) -99.5(8) ? . . . . C(3) C(2) C(11) C(12) 137.6(8) ? . . . . C(11) C(2) C(3) C(4) 173.8(8) ? . . . . C(2) C(3) C(4) C(5) -1.4(14) ? . . . . C(3) C(4) C(5) C(6) 3.6(13) ? . . . . C(3) C(4) C(5) C(10) -177.7(8) ? . . . . C(4) C(5) C(6) C(1) -2.7(12) ? . . . . C(4) C(5) C(6) C(7) 177.5(8) ? . . . . C(4) C(5) C(10) C(9) 179.3(9) ? . . . . C(6) C(5) C(10) C(9) -2.0(13) ? . . . . C(10) C(5) C(6) C(1) 178.5(7) ? . . . . C(10) C(5) C(6) C(7) -1.3(12) ? . . . . C(1) C(6) C(7) C(8) -176.6(8) ? . . . . C(5) C(6) C(7) C(8) 3.2(12) ? . . . . C(6) C(7) C(8) C(9) -1.7(13) ? . . . . C(7) C(8) C(9) C(10) -1.7(14) ? . . . . C(8) C(9) C(10) C(5) 3.6(14) ? . . . . C(14) C(13) C(18) C(17) 2.5(12) ? . . . . C(18) C(13) C(14) C(15) -2.6(12) ? . . . . C(14) C(13) C(19) O(1) 3.9(12) ? . . . . C(14) C(13) C(19) O(2) -174.7(7) ? . . . . C(19) C(13) C(14) C(15) 175.1(7) ? . . . . C(18) C(13) C(19) O(1) -178.4(8) ? . . . . C(18) C(13) C(19) O(2) 3.0(11) ? . . . . C(19) C(13) C(18) C(17) -175.2(8) ? . . . . C(13) C(14) C(15) C(16) 2.9(12) ? . . . . C(14) C(15) C(16) I(1) -177.2(6) ? . . . . C(14) C(15) C(16) C(17) -3.1(13) ? . . . . I(1) C(16) C(17) C(18) 177.1(6) ? . . . . C(15) C(16) C(17) C(18) 3.1(13) ? . . . . C(16) C(17) C(18) C(13) -2.8(13) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 I(1) O(2) 3.037(5) ? . 3_556 I(1) C(19) 3.576(8) ? . 3_556 O(1) N(1) 2.761(8) ? . . O(1) N(1) 2.764(9) ? . 2_456 O(1) C(12) 3.527(10) ? . 1_455 O(1) C(12) 3.578(11) ? . 2_456 O(2) I(1) 3.037(5) ? . 3_546 O(2) N(1) 2.734(8) ? . 1_455 O(2) N(1) 3.466(8) ? . 2_456 O(2) C(1) 3.533(9) ? . 1_455 N(1) O(1) 2.761(8) ? . . N(1) O(1) 2.764(9) ? . 2_556 N(1) O(2) 2.734(8) ? . 1_655 N(1) O(2) 3.466(8) ? . 2_556 N(1) C(19) 3.518(10) ? . 1_655 N(1) C(19) 3.461(10) ? . 2_556 C(1) O(2) 3.533(9) ? . 1_655 C(1) C(19) 3.532(11) ? . 1_655 C(12) O(1) 3.527(10) ? . 1_655 C(12) O(1) 3.578(11) ? . 2_556 C(19) I(1) 3.576(8) ? . 3_546 C(19) N(1) 3.518(10) ? . 1_455 C(19) N(1) 3.461(10) ? . 2_456 C(19) C(1) 3.532(11) ? . 1_455 I(1) H(11) 3.214 ? . 4_565 I(1) H(18) 3.306 ? . 3_556 O(1) H(1) 1.887 ? . . O(1) H(1) 3.278 ? . 2_456 O(1) H(2) 2.988 ? . 1_455 O(1) H(2) 3.115 ? . . O(1) H(2) 3.018 ? . 2_456 O(1) H(3) 3.082 ? . . O(1) H(3) 1.894 ? . 2_456 O(1) H(4) 3.100 ? . 1_455 O(1) H(12) 2.888 ? . 2_456 O(1) H(13) 2.640 ? . 1_455 O(2) H(1) 3.032 ? . 1_455 O(2) H(1) 3.533 ? . 2_456 O(2) H(2) 1.853 ? . 1_455 O(2) H(3) 3.151 ? . 1_455 O(2) H(3) 2.705 ? . 2_456 O(2) H(4) 3.055 ? . 1_455 O(2) H(13) 3.386 ? . 1_455 O(2) H(15) 2.989 ? . 1_455 N(1) H(1) 3.480 ? . 2_556 N(1) H(2) 3.526 ? . 2_456 N(1) H(3) 3.540 ? . 2_456 N(1) H(3) 3.566 ? . 2_556 N(1) H(15) 3.128 ? . . C(1) H(6) 3.447 ? . 1_655 C(1) H(6) 3.280 ? . 2_566 C(1) H(15) 3.078 ? . . C(2) H(6) 3.272 ? . 2_566 C(2) H(15) 3.143 ? . . C(3) H(4) 3.360 ? . 1_455 C(3) H(6) 3.115 ? . 2_566 C(3) H(13) 3.462 ? . 1_455 C(3) H(15) 3.445 ? . . C(4) H(4) 3.414 ? . 1_455 C(4) H(6) 3.023 ? . 2_566 C(4) H(7) 3.028 ? . 1_455 C(5) H(5) 3.401 ? . 2_566 C(5) H(6) 3.108 ? . 2_566 C(5) H(7) 3.285 ? . 1_455 C(5) H(15) 3.557 ? . . C(5) H(16) 3.309 ? . . C(6) H(6) 3.407 ? . 1_655 C(6) H(6) 3.212 ? . 2_566 C(6) H(15) 3.297 ? . . C(6) H(16) 3.065 ? . . C(7) H(6) 3.112 ? . 1_655 C(7) H(10) 3.355 ? . 1_655 C(7) H(16) 3.060 ? . . C(8) H(10) 3.355 ? . 1_655 C(8) H(16) 3.251 ? . . C(9) H(14) 3.431 ? . 2_466 C(9) H(16) 3.448 ? . . C(10) H(5) 3.349 ? . 2_566 C(10) H(7) 3.290 ? . 1_455 C(10) H(14) 2.987 ? . 2_466 C(10) H(16) 3.502 ? . . C(12) H(5) 3.329 ? . 1_655 C(12) H(10) 3.384 ? . 2_566 C(13) H(4) 3.115 ? . 1_455 C(13) H(7) 3.143 ? . 1_455 C(14) H(1) 3.400 ? . . C(14) H(7) 3.132 ? . 1_455 C(14) H(18) 3.263 ? . 1_655 C(15) H(7) 3.166 ? . 1_455 C(15) H(9) 3.346 ? . 3_646 C(15) H(18) 3.083 ? . 1_655 C(16) H(7) 3.249 ? . 1_455 C(16) H(8) 3.592 ? . 3_646 C(16) H(9) 3.280 ? . 3_646 C(17) H(7) 3.258 ? . 1_455 C(17) H(8) 3.291 ? . 3_646 C(17) H(9) 3.470 ? . 3_546 C(17) H(16) 3.280 ? . 1_455 C(18) H(7) 3.227 ? . 1_455 C(18) H(8) 3.416 ? . 3_646 C(18) H(9) 3.474 ? . 3_546 C(18) H(16) 3.091 ? . 1_455 C(19) H(1) 3.069 ? . . C(19) H(2) 2.633 ? . 1_455 C(19) H(3) 2.572 ? . 2_456 C(19) H(4) 2.792 ? . 1_455 C(19) H(12) 3.439 ? . 2_456 C(19) H(13) 3.149 ? . 1_455 H(1) O(1) 1.887 ? . . H(1) O(1) 3.278 ? . 2_556 H(1) O(2) 3.032 ? . 1_655 H(1) O(2) 3.533 ? . 2_556 H(1) N(1) 3.480 ? . 2_456 H(1) C(14) 3.400 ? . . H(1) C(19) 3.069 ? . . H(1) H(2) 3.215 ? . 2_456 H(1) H(3) 2.912 ? . 2_456 H(1) H(12) 3.325 ? . 2_456 H(1) H(13) 3.139 ? . 1_455 H(1) H(15) 2.622 ? . . H(2) O(1) 3.115 ? . . H(2) O(1) 2.988 ? . 1_655 H(2) O(1) 3.018 ? . 2_556 H(2) O(2) 1.853 ? . 1_655 H(2) N(1) 3.526 ? . 2_556 H(2) C(19) 2.633 ? . 1_655 H(2) H(1) 3.215 ? . 2_556 H(2) H(3) 2.983 ? . 2_556 H(2) H(12) 3.557 ? . 2_456 H(2) H(15) 2.894 ? . . H(3) O(1) 3.082 ? . . H(3) O(1) 1.894 ? . 2_556 H(3) O(2) 3.151 ? . 1_655 H(3) O(2) 2.705 ? . 2_556 H(3) N(1) 3.566 ? . 2_456 H(3) N(1) 3.540 ? . 2_556 H(3) C(19) 2.572 ? . 2_556 H(3) H(1) 2.912 ? . 2_556 H(3) H(2) 2.983 ? . 2_456 H(3) H(3) 3.346 ? . 2_456 H(3) H(3) 3.346 ? . 2_556 H(3) H(12) 3.458 ? . 2_456 H(3) H(13) 3.172 ? . 2_456 H(4) O(1) 3.100 ? . 1_655 H(4) O(2) 3.055 ? . 1_655 H(4) C(3) 3.360 ? . 1_655 H(4) C(4) 3.414 ? . 1_655 H(4) C(13) 3.115 ? . 1_655 H(4) C(19) 2.792 ? . 1_655 H(4) H(5) 3.061 ? . 1_655 H(4) H(6) 3.175 ? . 1_655 H(4) H(15) 3.433 ? . . H(5) C(5) 3.401 ? . 2_466 H(5) C(10) 3.349 ? . 2_466 H(5) C(12) 3.329 ? . 1_455 H(5) H(4) 3.061 ? . 1_455 H(5) H(6) 3.598 ? . 2_566 H(5) H(13) 2.791 ? . 1_455 H(5) H(14) 2.974 ? . 1_455 H(6) C(1) 3.447 ? . 1_455 H(6) C(1) 3.280 ? . 2_466 H(6) C(2) 3.272 ? . 2_466 H(6) C(3) 3.115 ? . 2_466 H(6) C(4) 3.023 ? . 2_466 H(6) C(5) 3.108 ? . 2_466 H(6) C(6) 3.407 ? . 1_455 H(6) C(6) 3.212 ? . 2_466 H(6) C(7) 3.112 ? . 1_455 H(6) H(4) 3.175 ? . 1_455 H(6) H(5) 3.598 ? . 2_466 H(6) H(6) 3.447 ? . 2_466 H(6) H(6) 3.447 ? . 2_566 H(6) H(7) 2.757 ? . 1_455 H(7) C(4) 3.028 ? . 1_655 H(7) C(5) 3.285 ? . 1_655 H(7) C(10) 3.290 ? . 1_655 H(7) C(13) 3.143 ? . 1_655 H(7) C(14) 3.132 ? . 1_655 H(7) C(15) 3.166 ? . 1_655 H(7) C(16) 3.249 ? . 1_655 H(7) C(17) 3.258 ? . 1_655 H(7) C(18) 3.227 ? . 1_655 H(7) H(6) 2.757 ? . 1_655 H(7) H(10) 3.036 ? . 1_655 H(7) H(16) 3.476 ? . . H(8) C(16) 3.592 ? . 3_656 H(8) C(17) 3.291 ? . 3_656 H(8) C(18) 3.416 ? . 3_656 H(8) H(10) 3.079 ? . 1_655 H(8) H(17) 3.506 ? . 3_656 H(9) C(15) 3.346 ? . 3_656 H(9) C(16) 3.280 ? . 3_656 H(9) C(17) 3.470 ? . 3_556 H(9) C(18) 3.474 ? . 3_556 H(9) H(14) 3.345 ? . 2_466 H(9) H(16) 3.455 ? . 3_656 H(9) H(17) 2.883 ? . 3_556 H(9) H(18) 2.875 ? . 3_556 H(10) C(7) 3.355 ? . 1_455 H(10) C(8) 3.355 ? . 1_455 H(10) C(12) 3.384 ? . 2_466 H(10) H(7) 3.036 ? . 1_455 H(10) H(8) 3.079 ? . 1_455 H(10) H(14) 2.485 ? . 2_466 H(10) H(17) 3.359 ? . 3_556 H(11) I(1) 3.214 ? . 4_564 H(11) H(13) 3.391 ? . 1_455 H(12) O(1) 2.888 ? . 2_556 H(12) C(19) 3.439 ? . 2_556 H(12) H(1) 3.325 ? . 2_556 H(12) H(2) 3.557 ? . 2_556 H(12) H(3) 3.458 ? . 2_556 H(13) O(1) 2.640 ? . 1_655 H(13) O(2) 3.386 ? . 1_655 H(13) C(3) 3.462 ? . 1_655 H(13) C(19) 3.149 ? . 1_655 H(13) H(1) 3.139 ? . 1_655 H(13) H(3) 3.172 ? . 2_556 H(13) H(5) 2.791 ? . 1_655 H(13) H(11) 3.391 ? . 1_655 H(14) C(9) 3.431 ? . 2_566 H(14) C(10) 2.987 ? . 2_566 H(14) H(5) 2.974 ? . 1_655 H(14) H(9) 3.345 ? . 2_566 H(14) H(10) 2.485 ? . 2_566 H(14) H(17) 3.351 ? . 4_564 H(15) O(2) 2.989 ? . 1_655 H(15) N(1) 3.128 ? . . H(15) C(1) 3.078 ? . . H(15) C(2) 3.143 ? . . H(15) C(3) 3.445 ? . . H(15) C(5) 3.557 ? . . H(15) C(6) 3.297 ? . . H(15) H(1) 2.622 ? . . H(15) H(2) 2.894 ? . . H(15) H(4) 3.433 ? . . H(15) H(18) 3.011 ? . 1_655 H(16) C(5) 3.309 ? . . H(16) C(6) 3.065 ? . . H(16) C(7) 3.060 ? . . H(16) C(8) 3.251 ? . . H(16) C(9) 3.448 ? . . H(16) C(10) 3.502 ? . . H(16) C(17) 3.280 ? . 1_655 H(16) C(18) 3.091 ? . 1_655 H(16) H(7) 3.476 ? . . H(16) H(9) 3.455 ? . 3_646 H(16) H(17) 3.039 ? . 1_655 H(16) H(18) 2.715 ? . 1_655 H(17) H(8) 3.506 ? . 3_646 H(17) H(9) 2.883 ? . 3_546 H(17) H(10) 3.359 ? . 3_546 H(17) H(14) 3.351 ? . 4_565 H(17) H(16) 3.039 ? . 1_455 H(18) I(1) 3.306 ? . 3_546 H(18) C(14) 3.263 ? . 1_455 H(18) C(15) 3.083 ? . 1_455 H(18) H(9) 2.875 ? . 3_546 H(18) H(15) 3.011 ? . 1_455 H(18) H(16) 2.715 ? . 1_455 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================