# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ww12_0m _database_code_depnum_ccdc_archive 'CCDC 884444' #TrackingRef 'web_deposit_cif_file_0_WilliamD.Wulff_1338302533.34.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C42 H56 Cl N O5' _chemical_formula_sum 'C42 H56 Cl N O5' _chemical_melting_point ? _exptl_crystal_description chunk _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 690.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc ' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4992(7) _cell_length_b 24.3436(15) _cell_length_c 15.0944(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.2680(10) _cell_angle_gamma 90.00 _cell_volume 3910.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7647 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 24.17 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.173 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9659 _exptl_absorpt_correction_T_max 0.9753 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 28562 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_sigmaI/netI 0.0778 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.36 _reflns_number_total 7168 _reflns_number_gt 4732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.58, 2006)' _computing_cell_refinement 'APEX2 (BRUKER, V2008.5-0, 2006)' _computing_data_reduction 'SAINT (BRUKER, V7.34A, 2006)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0855P)^2^+0.9657P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7168 _refine_ls_number_parameters 517 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1983 _refine_ls_wR_factor_gt 0.1760 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.34903(7) 0.83912(4) 0.11461(6) 0.0647(3) Uani 1 1 d . . . O1 O 1.19373(18) 0.72235(8) 0.14714(15) 0.0569(5) Uani 1 1 d . . . O2 O 1.2598(2) 0.70436(10) 0.02828(19) 0.0821(7) Uani 1 1 d . . . O3 O 1.09727(19) 0.76021(9) 0.23669(14) 0.0616(6) Uani 1 1 d . . . O4 O 1.0606(2) 0.94855(9) 0.43693(14) 0.0635(6) Uani 1 1 d . . . O5 O 0.48063(18) 0.77986(10) -0.07399(16) 0.0699(6) Uani 1 1 d . . . N1 N 1.08724(19) 0.80074(9) 0.09502(14) 0.0422(5) Uani 1 1 d . . . C1 C 1.1311(3) 0.78505(11) 0.01916(19) 0.0474(6) Uani 1 1 d . . . C2 C 1.2026(3) 0.73337(12) 0.0614(2) 0.0572(7) Uani 1 1 d . . . C3 C 1.1205(2) 0.76317(12) 0.1662(2) 0.0502(7) Uani 1 1 d . . . C4 C 1.0214(3) 0.76984(14) -0.0759(2) 0.0611(8) Uani 1 1 d . . . H4A H 0.9717 0.7401 -0.0640 0.092 Uiso 1 1 calc R . . H4B H 1.0556 0.7578 -0.1231 0.092 Uiso 1 1 calc R . . H4C H 0.9677 0.8021 -0.1005 0.092 Uiso 1 1 calc R . . C5 C 1.2241(3) 0.82583(12) 0.0017(2) 0.0513(7) Uani 1 1 d . . . H5 H 1.2626 0.8059 -0.0383 0.062 Uiso 1 1 calc R . . C6 C 1.1693(3) 0.87802(13) -0.0511(2) 0.0559(7) Uani 1 1 d . . . C7 C 1.1666(3) 0.92722(13) -0.0045(2) 0.0635(8) Uani 1 1 d . . . H7 H 1.2044 0.9292 0.0634 0.076 Uiso 1 1 calc R . . C8 C 1.1093(4) 0.97308(15) -0.0566(3) 0.0785(10) Uani 1 1 d . . . H8 H 1.1063 1.0062 -0.0243 0.094 Uiso 1 1 calc R . . C9 C 1.0567(4) 0.97106(17) -0.1550(3) 0.0903(12) Uani 1 1 d . . . H9 H 1.0170 1.0027 -0.1904 0.108 Uiso 1 1 calc R . . C10 C 1.0615(4) 0.92324(17) -0.2023(3) 0.0887(12) Uani 1 1 d . . . H10 H 1.0256 0.9220 -0.2702 0.106 Uiso 1 1 calc R . . C11 C 1.1188(3) 0.87660(15) -0.1506(2) 0.0702(9) Uani 1 1 d . . . H11 H 1.1234 0.8439 -0.1834 0.084 Uiso 1 1 calc R . . C12 C 0.9921(2) 0.84410(11) 0.08289(18) 0.0431(6) Uani 1 1 d . . . H12 H 1.0057 0.8727 0.0402 0.052 Uiso 1 1 calc R . . C13 C 1.0107(2) 0.87262(11) 0.17766(19) 0.0463(6) Uani 1 1 d . . . C14 C 1.1266(3) 0.89451(11) 0.23484(19) 0.0481(6) Uani 1 1 d . . . H14 H 1.1954 0.8909 0.2150 0.058 Uiso 1 1 calc R . . C15 C 1.1449(3) 0.92172(11) 0.3206(2) 0.0509(7) Uani 1 1 d . . . C16 C 1.0411(3) 0.92534(11) 0.3484(2) 0.0531(7) Uani 1 1 d . . . C17 C 0.9203(3) 0.90842(12) 0.2889(2) 0.0543(7) Uani 1 1 d . . . C18 C 0.9106(3) 0.88085(12) 0.2049(2) 0.0523(7) Uani 1 1 d . . . H18 H 0.8306 0.8671 0.1647 0.063 Uiso 1 1 calc R . . C19 C 1.2713(3) 0.95002(12) 0.3770(2) 0.0555(7) Uani 1 1 d . . . C20 C 1.3673(3) 0.93982(15) 0.3300(3) 0.0723(9) Uani 1 1 d . . . H20A H 1.3822 0.9003 0.3283 0.109 Uiso 1 1 calc R . . H20B H 1.4465 0.9583 0.3673 0.109 Uiso 1 1 calc R . . H20C H 1.3342 0.9544 0.2646 0.109 Uiso 1 1 calc R . . C21 C 1.3317(3) 0.93097(14) 0.4811(2) 0.0687(9) Uani 1 1 d . . . H21A H 1.2829 0.9449 0.5172 0.103 Uiso 1 1 calc R . . H21B H 1.4179 0.9451 0.5094 0.103 Uiso 1 1 calc R . . H21C H 1.3332 0.8907 0.4833 0.103 Uiso 1 1 calc R . . C22 C 1.2493(3) 1.01279(13) 0.3751(3) 0.0748(10) Uani 1 1 d . . . H22A H 1.2213 1.0261 0.3090 0.112 Uiso 1 1 calc R . . H22B H 1.3278 1.0312 0.4142 0.112 Uiso 1 1 calc R . . H22C H 1.1847 1.0208 0.4009 0.112 Uiso 1 1 calc R . . C23 C 1.0652(4) 0.90961(16) 0.5096(2) 0.0822(11) Uani 1 1 d . . . H23A H 1.0091 0.8787 0.4802 0.123 Uiso 1 1 calc R . . H23B H 1.0382 0.9274 0.5568 0.123 Uiso 1 1 calc R . . H23C H 1.1514 0.8961 0.5413 0.123 Uiso 1 1 calc R . . C24 C 0.7953(3) 0.91844(15) 0.3030(3) 0.0700(9) Uani 1 1 d . . . C25 C 0.7975(4) 0.9695(2) 0.3630(4) 0.1178(18) Uani 1 1 d . . . H25A H 0.8300 1.0008 0.3387 0.177 Uiso 1 1 calc R . . H25B H 0.8518 0.9627 0.4300 0.177 Uiso 1 1 calc R . . H25C H 0.7121 0.9777 0.3588 0.177 Uiso 1 1 calc R . . C26 C 0.7610(5) 0.8671(2) 0.3479(4) 0.1243(18) Uani 1 1 d . . . H26A H 0.6766 0.8716 0.3485 0.186 Uiso 1 1 calc R . . H26B H 0.8219 0.8625 0.4136 0.186 Uiso 1 1 calc R . . H26C H 0.7627 0.8346 0.3101 0.186 Uiso 1 1 calc R . . C27 C 0.6893(4) 0.9288(2) 0.2069(3) 0.1047(16) Uani 1 1 d . . . H27A H 0.7127 0.9590 0.1739 0.157 Uiso 1 1 calc R . . H27B H 0.6127 0.9386 0.2170 0.157 Uiso 1 1 calc R . . H27C H 0.6744 0.8955 0.1676 0.157 Uiso 1 1 calc R . . C28 C 0.8581(2) 0.82366(11) 0.03306(19) 0.0441(6) Uani 1 1 d . . . C29 C 0.7702(2) 0.85768(13) -0.0306(2) 0.0515(7) Uani 1 1 d . . . H29 H 0.7975 0.8905 -0.0507 0.062 Uiso 1 1 calc R . . C30 C 0.6405(3) 0.84515(13) -0.0669(2) 0.0559(7) Uani 1 1 d . A . C31 C 0.6073(3) 0.79507(13) -0.0369(2) 0.0552(7) Uani 1 1 d . . . C32 C 0.6934(3) 0.76073(12) 0.0312(2) 0.0517(7) Uani 1 1 d . B . C33 C 0.8193(2) 0.77613(11) 0.0628(2) 0.0484(6) Uani 1 1 d . . . H33 H 0.8808 0.7529 0.1067 0.058 Uiso 1 1 calc R . . C34 C 0.5466(3) 0.88959(16) -0.1257(2) 0.0684(9) Uani 1 1 d . . . C35A C 0.6063(10) 0.9310(5) -0.1654(8) 0.091(4) Uani 0.50 1 d P A 1 H35A H 0.6481 0.9128 -0.2031 0.136 Uiso 0.50 1 calc PR A 1 H35B H 0.6684 0.9517 -0.1130 0.136 Uiso 0.50 1 calc PR A 1 H35C H 0.5421 0.9563 -0.2066 0.136 Uiso 0.50 1 calc PR A 1 C36A C 0.4835(14) 0.9118(5) -0.0629(9) 0.071(3) Uani 0.50 1 d P A 1 H36A H 0.4211 0.9394 -0.0982 0.106 Uiso 0.50 1 calc PR A 1 H36B H 0.5464 0.9288 -0.0060 0.106 Uiso 0.50 1 calc PR A 1 H36C H 0.4416 0.8818 -0.0433 0.106 Uiso 0.50 1 calc PR A 1 C37A C 0.4351(8) 0.8656(6) -0.2161(9) 0.076(3) Uani 0.50 1 d P A 1 H37A H 0.3810 0.8957 -0.2517 0.115 Uiso 0.50 1 calc PR A 1 H37B H 0.3857 0.8398 -0.1947 0.115 Uiso 0.50 1 calc PR A 1 H37C H 0.4698 0.8464 -0.2577 0.115 Uiso 0.50 1 calc PR A 1 C38 C 0.4493(4) 0.74283(19) -0.1548(3) 0.0956(13) Uani 1 1 d . . . H38A H 0.4453 0.7634 -0.2116 0.143 Uiso 1 1 calc R . . H38B H 0.3676 0.7258 -0.1667 0.143 Uiso 1 1 calc R . . H38C H 0.5138 0.7142 -0.1407 0.143 Uiso 1 1 calc R . . C39 C 0.6608(3) 0.71292(13) 0.0857(2) 0.0628(8) Uani 1 1 d . . . C40A C 0.5960(10) 0.7388(4) 0.1441(8) 0.089(2) Uani 0.50 1 d P B 1 H40A H 0.5645 0.7100 0.1746 0.133 Uiso 0.50 1 calc PR B 1 H40B H 0.5255 0.7611 0.1025 0.133 Uiso 0.50 1 calc PR B 1 H40C H 0.6554 0.7622 0.1934 0.133 Uiso 0.50 1 calc PR B 1 C41A C 0.5718(7) 0.6689(3) 0.0230(7) 0.078(2) Uani 0.50 1 d P B 1 H41A H 0.6063 0.6543 -0.0225 0.116 Uiso 0.50 1 calc PR B 1 H41B H 0.4892 0.6852 -0.0123 0.116 Uiso 0.50 1 calc PR B 1 H41C H 0.5631 0.6390 0.0636 0.116 Uiso 0.50 1 calc PR B 1 C42A C 0.7798(8) 0.6799(4) 0.1494(8) 0.082(3) Uani 0.50 1 d P B 1 H42A H 0.7549 0.6507 0.1833 0.123 Uiso 0.50 1 calc PR B 1 H42B H 0.8390 0.7047 0.1961 0.123 Uiso 0.50 1 calc PR B 1 H42C H 0.8200 0.6636 0.1089 0.123 Uiso 0.50 1 calc PR B 1 C40B C 0.7051(17) 0.7306(6) 0.1917(7) 0.158(7) Uani 0.50 1 d P B 2 H40D H 0.7894 0.7159 0.2271 0.237 Uiso 0.50 1 calc PR B 2 H40E H 0.6467 0.7163 0.2194 0.237 Uiso 0.50 1 calc PR B 2 H40F H 0.7074 0.7708 0.1958 0.237 Uiso 0.50 1 calc PR B 2 C41B C 0.5195(10) 0.7043(7) 0.0640(10) 0.151(6) Uani 0.50 1 d P B 2 H41D H 0.4770 0.6925 -0.0026 0.227 Uiso 0.50 1 calc PR B 2 H41E H 0.4826 0.7388 0.0741 0.227 Uiso 0.50 1 calc PR B 2 H41F H 0.5095 0.6760 0.1068 0.227 Uiso 0.50 1 calc PR B 2 C42B C 0.7176(19) 0.6634(5) 0.0727(16) 0.196(9) Uani 0.50 1 d P B 2 H42D H 0.7484 0.6427 0.1329 0.295 Uiso 0.50 1 calc PR B 2 H42E H 0.7881 0.6721 0.0537 0.295 Uiso 0.50 1 calc PR B 2 H42F H 0.6556 0.6414 0.0227 0.295 Uiso 0.50 1 calc PR B 2 C35B C 0.6151(12) 0.9507(6) -0.1011(12) 0.145(6) Uani 0.50 1 d P A 2 H35D H 0.6828 0.9525 -0.1254 0.217 Uiso 0.50 1 calc PR A 2 H35E H 0.6500 0.9564 -0.0316 0.217 Uiso 0.50 1 calc PR A 2 H35F H 0.5529 0.9793 -0.1316 0.217 Uiso 0.50 1 calc PR A 2 C36B C 0.442(2) 0.9025(10) -0.0915(17) 0.203(13) Uani 0.50 1 d P A 2 H36D H 0.4055 0.9383 -0.1169 0.304 Uiso 0.50 1 calc PR A 2 H36E H 0.4761 0.9036 -0.0214 0.304 Uiso 0.50 1 calc PR A 2 H36F H 0.3774 0.8740 -0.1141 0.304 Uiso 0.50 1 calc PR A 2 C37B C 0.503(2) 0.8825(10) -0.2273(11) 0.243(15) Uani 0.50 1 d P A 2 H37D H 0.4790 0.8441 -0.2434 0.364 Uiso 0.50 1 calc PR A 2 H37E H 0.5698 0.8925 -0.2495 0.364 Uiso 0.50 1 calc PR A 2 H37F H 0.4296 0.9061 -0.2585 0.364 Uiso 0.50 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0474(4) 0.0810(6) 0.0640(5) 0.0024(4) 0.0192(4) -0.0060(4) O1 0.0552(12) 0.0543(11) 0.0614(13) 0.0066(9) 0.0223(10) 0.0087(9) O2 0.0964(18) 0.0644(14) 0.1050(19) -0.0001(13) 0.0602(16) 0.0236(13) O3 0.0639(13) 0.0787(14) 0.0460(12) 0.0097(10) 0.0251(10) 0.0007(11) O4 0.0800(15) 0.0645(13) 0.0493(12) -0.0125(10) 0.0283(11) -0.0010(11) O5 0.0398(11) 0.0935(16) 0.0738(15) -0.0109(12) 0.0185(10) -0.0092(11) N1 0.0419(11) 0.0501(12) 0.0369(12) -0.0016(9) 0.0176(9) 0.0004(10) C1 0.0488(15) 0.0535(16) 0.0474(15) -0.0044(12) 0.0268(13) 0.0014(13) C2 0.0549(17) 0.0548(17) 0.066(2) -0.0015(14) 0.0276(15) 0.0050(14) C3 0.0426(14) 0.0575(17) 0.0475(17) 0.0013(13) 0.0134(13) -0.0015(13) C4 0.0641(18) 0.076(2) 0.0484(17) -0.0084(15) 0.0275(15) 0.0024(16) C5 0.0436(14) 0.0599(17) 0.0571(18) -0.0003(13) 0.0268(13) 0.0020(13) C6 0.0506(16) 0.0655(19) 0.0584(18) 0.0032(14) 0.0283(14) -0.0033(14) C7 0.067(2) 0.0604(19) 0.070(2) 0.0003(15) 0.0350(17) -0.0060(16) C8 0.083(2) 0.063(2) 0.094(3) 0.0076(19) 0.038(2) -0.0018(19) C9 0.091(3) 0.076(3) 0.097(3) 0.028(2) 0.029(2) 0.003(2) C10 0.105(3) 0.084(3) 0.067(2) 0.017(2) 0.021(2) -0.001(2) C11 0.075(2) 0.079(2) 0.058(2) 0.0025(17) 0.0268(17) -0.0020(18) C12 0.0402(13) 0.0475(14) 0.0444(15) -0.0004(11) 0.0190(11) 0.0011(11) C13 0.0465(14) 0.0486(15) 0.0479(15) -0.0053(12) 0.0224(12) -0.0007(12) C14 0.0469(15) 0.0515(15) 0.0489(16) -0.0039(12) 0.0217(13) -0.0018(12) C15 0.0557(16) 0.0473(15) 0.0466(16) -0.0042(12) 0.0159(13) -0.0028(13) C16 0.0654(18) 0.0506(16) 0.0480(16) -0.0110(13) 0.0268(14) -0.0014(14) C17 0.0565(17) 0.0579(17) 0.0547(17) -0.0096(13) 0.0280(14) -0.0010(14) C18 0.0481(15) 0.0608(17) 0.0526(17) -0.0120(13) 0.0242(13) -0.0071(13) C19 0.0541(16) 0.0512(16) 0.0567(18) -0.0088(13) 0.0158(14) -0.0065(13) C20 0.0573(19) 0.086(2) 0.072(2) -0.0158(18) 0.0218(17) -0.0194(17) C21 0.063(2) 0.070(2) 0.062(2) -0.0039(16) 0.0116(16) -0.0010(16) C22 0.077(2) 0.0515(18) 0.085(2) -0.0076(17) 0.0185(19) -0.0113(17) C23 0.107(3) 0.094(3) 0.053(2) -0.0074(18) 0.039(2) -0.012(2) C24 0.0645(19) 0.085(2) 0.076(2) -0.0227(18) 0.0443(18) -0.0033(17) C25 0.080(3) 0.151(4) 0.124(4) -0.072(3) 0.039(3) 0.018(3) C26 0.108(4) 0.137(4) 0.171(5) -0.005(4) 0.101(4) -0.014(3) C27 0.059(2) 0.166(4) 0.094(3) -0.036(3) 0.034(2) 0.021(2) C28 0.0375(13) 0.0531(15) 0.0457(15) -0.0059(12) 0.0201(12) -0.0009(12) C29 0.0460(15) 0.0647(18) 0.0503(16) 0.0028(13) 0.0255(13) 0.0006(14) C30 0.0421(14) 0.080(2) 0.0472(16) 0.0031(14) 0.0186(13) 0.0080(14) C31 0.0381(14) 0.075(2) 0.0558(18) -0.0117(15) 0.0210(13) -0.0073(14) C32 0.0460(15) 0.0602(17) 0.0533(17) -0.0084(13) 0.0240(13) -0.0075(13) C33 0.0422(14) 0.0556(16) 0.0495(16) -0.0059(13) 0.0197(12) -0.0032(12) C34 0.0511(17) 0.091(2) 0.065(2) 0.0132(18) 0.0240(16) 0.0110(17) C35A 0.067(5) 0.106(9) 0.094(7) 0.061(7) 0.025(6) 0.015(6) C36A 0.085(8) 0.067(5) 0.065(5) 0.000(4) 0.034(5) 0.031(5) C37A 0.058(4) 0.092(6) 0.058(6) -0.003(5) -0.001(4) 0.022(4) C38 0.065(2) 0.124(3) 0.082(3) -0.023(2) 0.010(2) -0.021(2) C39 0.0516(17) 0.0603(19) 0.083(2) -0.0026(16) 0.0326(17) -0.0107(15) C40A 0.104(7) 0.091(6) 0.096(7) -0.005(5) 0.066(6) -0.014(6) C41A 0.050(4) 0.060(4) 0.127(7) -0.018(4) 0.038(4) -0.009(3) C42A 0.061(4) 0.075(6) 0.101(7) 0.026(5) 0.022(5) -0.017(4) C40B 0.253(17) 0.148(11) 0.063(6) 0.000(6) 0.049(9) -0.117(13) C41B 0.088(7) 0.214(15) 0.141(10) 0.069(10) 0.031(7) -0.050(9) C42B 0.28(2) 0.075(8) 0.36(3) 0.061(13) 0.26(2) 0.048(11) C35B 0.086(7) 0.106(9) 0.213(17) 0.057(11) 0.023(11) 0.030(7) C36B 0.146(17) 0.25(2) 0.29(3) 0.16(2) 0.18(2) 0.125(16) C37B 0.38(4) 0.25(3) 0.059(8) 0.029(12) 0.029(18) 0.20(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C5 1.794(3) . ? O1 C2 1.362(4) . ? O1 C3 1.402(3) . ? O2 C2 1.196(3) . ? O3 C3 1.193(3) . ? O4 C16 1.388(3) . ? O4 C23 1.435(4) . ? O5 C31 1.398(3) . ? O5 C38 1.448(4) . ? N1 C3 1.352(3) . ? N1 C1 1.466(3) . ? N1 C12 1.481(3) . ? C1 C2 1.506(4) . ? C1 C5 1.553(4) . ? C1 C4 1.554(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.505(4) . ? C5 H5 1.0000 . ? C6 C11 1.390(4) . ? C6 C7 1.396(4) . ? C7 C8 1.381(5) . ? C7 H7 0.9500 . ? C8 C9 1.377(6) . ? C8 H8 0.9500 . ? C9 C10 1.377(6) . ? C9 H9 0.9500 . ? C10 C11 1.393(5) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 C28 1.520(4) . ? C12 C13 1.530(4) . ? C12 H12 1.0000 . ? C13 C18 1.377(4) . ? C13 C14 1.390(4) . ? C14 C15 1.397(4) . ? C14 H14 0.9500 . ? C15 C16 1.411(4) . ? C15 C19 1.541(4) . ? C16 C17 1.400(4) . ? C17 C18 1.401(4) . ? C17 C24 1.551(4) . ? C18 H18 0.9500 . ? C19 C21 1.529(4) . ? C19 C20 1.541(5) . ? C19 C22 1.547(4) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C27 1.521(5) . ? C24 C25 1.533(5) . ? C24 C26 1.542(6) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C33 1.375(4) . ? C28 C29 1.377(4) . ? C29 C30 1.413(4) . ? C29 H29 0.9500 . ? C30 C31 1.403(4) . ? C30 C34 1.549(4) . ? C31 C32 1.401(4) . ? C32 C33 1.393(4) . ? C32 C39 1.552(4) . ? C33 H33 0.9500 . ? C34 C37B 1.432(17) . ? C34 C35A 1.470(10) . ? C34 C36A 1.497(13) . ? C34 C36B 1.508(19) . ? C34 C37A 1.588(11) . ? C34 C35B 1.658(15) . ? C35A H35A 0.9800 . ? C35A H35B 0.9800 . ? C35A H35C 0.9800 . ? C36A H36A 0.9800 . ? C36A H36B 0.9800 . ? C36A H36C 0.9800 . ? C37A H37A 0.9800 . ? C37A H37B 0.9800 . ? C37A H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C42B 1.419(12) . ? C39 C40A 1.492(9) . ? C39 C41A 1.536(7) . ? C39 C40B 1.545(10) . ? C39 C41B 1.545(10) . ? C39 C42A 1.564(10) . ? C40A H40A 0.9800 . ? C40A H40B 0.9800 . ? C40A H40C 0.9800 . ? C41A H41A 0.9800 . ? C41A H41B 0.9800 . ? C41A H41C 0.9800 . ? C42A H42A 0.9800 . ? C42A H42B 0.9800 . ? C42A H42C 0.9800 . ? C40B H40D 0.9800 . ? C40B H40E 0.9800 . ? C40B H40F 0.9800 . ? C41B H41D 0.9800 . ? C41B H41E 0.9800 . ? C41B H41F 0.9800 . ? C42B H42D 0.9800 . ? C42B H42E 0.9800 . ? C42B H42F 0.9800 . ? C35B H35D 0.9800 . ? C35B H35E 0.9800 . ? C35B H35F 0.9800 . ? C36B H36D 0.9800 . ? C36B H36E 0.9800 . ? C36B H36F 0.9800 . ? C37B H37D 0.9800 . ? C37B H37E 0.9800 . ? C37B H37F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C3 108.8(2) . . ? C16 O4 C23 114.3(2) . . ? C31 O5 C38 113.0(2) . . ? C3 N1 C1 111.6(2) . . ? C3 N1 C12 123.6(2) . . ? C1 N1 C12 123.1(2) . . ? N1 C1 C2 100.4(2) . . ? N1 C1 C5 115.4(2) . . ? C2 C1 C5 107.8(2) . . ? N1 C1 C4 112.6(2) . . ? C2 C1 C4 108.3(2) . . ? C5 C1 C4 111.5(2) . . ? O2 C2 O1 122.1(3) . . ? O2 C2 C1 127.9(3) . . ? O1 C2 C1 110.0(2) . . ? O3 C3 N1 131.2(3) . . ? O3 C3 O1 119.7(3) . . ? N1 C3 O1 109.1(2) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C1 116.9(2) . . ? C6 C5 Cl1 112.0(2) . . ? C1 C5 Cl1 108.00(19) . . ? C6 C5 H5 106.4 . . ? C1 C5 H5 106.4 . . ? Cl1 C5 H5 106.4 . . ? C11 C6 C7 119.1(3) . . ? C11 C6 C5 118.1(3) . . ? C7 C6 C5 122.8(3) . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 120.4(4) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.1(4) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.2(4) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C6 C11 C10 120.0(3) . . ? C6 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? N1 C12 C28 113.0(2) . . ? N1 C12 C13 111.9(2) . . ? C28 C12 C13 111.6(2) . . ? N1 C12 H12 106.6 . . ? C28 C12 H12 106.6 . . ? C13 C12 H12 106.6 . . ? C18 C13 C14 118.2(2) . . ? C18 C13 C12 120.6(2) . . ? C14 C13 C12 121.1(2) . . ? C13 C14 C15 122.0(3) . . ? C13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C14 C15 C16 117.3(3) . . ? C14 C15 C19 120.2(3) . . ? C16 C15 C19 122.3(2) . . ? O4 C16 C17 119.8(3) . . ? O4 C16 C15 117.7(3) . . ? C17 C16 C15 122.4(2) . . ? C16 C17 C18 116.2(3) . . ? C16 C17 C24 127.7(3) . . ? C18 C17 C24 116.1(3) . . ? C13 C18 C17 123.4(3) . . ? C13 C18 H18 118.3 . . ? C17 C18 H18 118.3 . . ? C21 C19 C15 113.5(3) . . ? C21 C19 C20 107.3(3) . . ? C15 C19 C20 111.3(2) . . ? C21 C19 C22 109.0(3) . . ? C15 C19 C22 108.5(2) . . ? C20 C19 C22 106.9(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O4 C23 H23A 109.5 . . ? O4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C27 C24 C25 104.9(3) . . ? C27 C24 C26 107.9(4) . . ? C25 C24 C26 110.4(4) . . ? C27 C24 C17 110.1(3) . . ? C25 C24 C17 113.6(3) . . ? C26 C24 C17 109.7(3) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C33 C28 C29 119.4(2) . . ? C33 C28 C12 120.5(2) . . ? C29 C28 C12 119.1(2) . . ? C28 C29 C30 121.9(3) . . ? C28 C29 H29 119.1 . . ? C30 C29 H29 119.1 . . ? C31 C30 C29 116.0(3) . . ? C31 C30 C34 125.1(3) . . ? C29 C30 C34 118.4(3) . . ? O5 C31 C32 118.4(3) . . ? O5 C31 C30 118.1(3) . . ? C32 C31 C30 123.5(3) . . ? C33 C32 C31 116.4(3) . . ? C33 C32 C39 116.7(3) . . ? C31 C32 C39 126.2(2) . . ? C28 C33 C32 122.5(3) . . ? C28 C33 H33 118.7 . . ? C32 C33 H33 118.7 . . ? C37B C34 C35A 71.0(12) . . ? C37B C34 C36A 131.6(11) . . ? C35A C34 C36A 115.1(9) . . ? C37B C34 C36B 112.9(14) . . ? C35A C34 C36B 123.5(11) . . ? C36A C34 C36B 21.3(12) . . ? C37B C34 C30 114.6(8) . . ? C35A C34 C30 112.4(5) . . ? C36A C34 C30 106.9(6) . . ? C36B C34 C30 115.0(9) . . ? C37B C34 C37A 36.2(12) . . ? C35A C34 C37A 104.6(7) . . ? C36A C34 C37A 104.5(7) . . ? C36B C34 C37A 83.3(11) . . ? C30 C34 C37A 113.3(6) . . ? C37B C34 C35B 107.0(12) . . ? C35A C34 C35B 38.8(6) . . ? C36A C34 C35B 80.6(9) . . ? C36B C34 C35B 96.2(12) . . ? C30 C34 C35B 109.2(5) . . ? C37A C34 C35B 133.1(7) . . ? C34 C35A H35A 109.5 . . ? C34 C35A H35B 109.5 . . ? C34 C35A H35C 109.5 . . ? C34 C36A H36A 109.5 . . ? C34 C36A H36B 109.5 . . ? C34 C36A H36C 109.5 . . ? C34 C37A H37A 109.5 . . ? C34 C37A H37B 109.5 . . ? C34 C37A H37C 109.5 . . ? O5 C38 H38A 109.5 . . ? O5 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O5 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C42B C39 C40A 143.0(7) . . ? C42B C39 C41A 63.7(9) . . ? C40A C39 C41A 107.1(5) . . ? C42B C39 C40B 113.0(11) . . ? C40A C39 C40B 46.7(7) . . ? C41A C39 C40B 135.6(6) . . ? C42B C39 C41B 110.9(10) . . ? C40A C39 C41B 57.5(7) . . ? C41A C39 C41B 51.2(6) . . ? C40B C39 C41B 99.5(9) . . ? C42B C39 C32 110.3(6) . . ? C40A C39 C32 105.8(4) . . ? C41A C39 C32 115.8(4) . . ? C40B C39 C32 106.8(4) . . ? C41B C39 C32 115.9(5) . . ? C42B C39 C42A 46.1(9) . . ? C40A C39 C42A 111.7(6) . . ? C41A C39 C42A 104.1(5) . . ? C40B C39 C42A 68.8(8) . . ? C41B C39 C42A 131.7(6) . . ? C32 C39 C42A 112.4(4) . . ? C39 C40A H40A 109.5 . . ? C39 C40A H40B 109.5 . . ? C39 C40A H40C 109.5 . . ? C39 C41A H41A 109.5 . . ? C39 C41A H41B 109.5 . . ? C39 C41A H41C 109.5 . . ? C39 C42A H42A 109.5 . . ? C39 C42A H42B 109.5 . . ? C39 C42A H42C 109.5 . . ? C39 C40B H40D 109.5 . . ? C39 C40B H40E 109.5 . . ? H40D C40B H40E 109.5 . . ? C39 C40B H40F 109.5 . . ? H40D C40B H40F 109.5 . . ? H40E C40B H40F 109.5 . . ? C39 C41B H41D 109.5 . . ? C39 C41B H41E 109.5 . . ? H41D C41B H41E 109.5 . . ? C39 C41B H41F 109.5 . . ? H41D C41B H41F 109.5 . . ? H41E C41B H41F 109.5 . . ? C39 C42B H42D 109.5 . . ? C39 C42B H42E 109.5 . . ? H42D C42B H42E 109.5 . . ? C39 C42B H42F 109.5 . . ? H42D C42B H42F 109.5 . . ? H42E C42B H42F 109.5 . . ? C34 C35B H35D 109.5 . . ? C34 C35B H35E 109.5 . . ? H35D C35B H35E 109.5 . . ? C34 C35B H35F 109.5 . . ? H35D C35B H35F 109.5 . . ? H35E C35B H35F 109.5 . . ? C34 C36B H36D 109.5 . . ? C34 C36B H36E 109.5 . . ? H36D C36B H36E 109.5 . . ? C34 C36B H36F 109.5 . . ? H36D C36B H36F 109.5 . . ? H36E C36B H36F 109.5 . . ? C34 C37B H37D 109.5 . . ? C34 C37B H37E 109.5 . . ? H37D C37B H37E 109.5 . . ? C34 C37B H37F 109.5 . . ? H37D C37B H37F 109.5 . . ? H37E C37B H37F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C1 C2 -3.2(3) . . . . ? C12 N1 C1 C2 -168.7(2) . . . . ? C3 N1 C1 C5 -118.8(3) . . . . ? C12 N1 C1 C5 75.7(3) . . . . ? C3 N1 C1 C4 111.7(3) . . . . ? C12 N1 C1 C4 -53.8(3) . . . . ? C3 O1 C2 O2 -179.5(3) . . . . ? C3 O1 C2 C1 0.1(3) . . . . ? N1 C1 C2 O2 -178.6(3) . . . . ? C5 C1 C2 O2 -57.4(4) . . . . ? C4 C1 C2 O2 63.3(4) . . . . ? N1 C1 C2 O1 1.8(3) . . . . ? C5 C1 C2 O1 123.0(2) . . . . ? C4 C1 C2 O1 -116.3(3) . . . . ? C1 N1 C3 O3 -176.0(3) . . . . ? C12 N1 C3 O3 -10.6(5) . . . . ? C1 N1 C3 O1 3.6(3) . . . . ? C12 N1 C3 O1 169.0(2) . . . . ? C2 O1 C3 O3 177.4(3) . . . . ? C2 O1 C3 N1 -2.2(3) . . . . ? N1 C1 C5 C6 -75.7(3) . . . . ? C2 C1 C5 C6 173.0(2) . . . . ? C4 C1 C5 C6 54.3(3) . . . . ? N1 C1 C5 Cl1 51.7(3) . . . . ? C2 C1 C5 Cl1 -59.6(3) . . . . ? C4 C1 C5 Cl1 -178.30(19) . . . . ? C1 C5 C6 C11 -84.3(3) . . . . ? Cl1 C5 C6 C11 150.3(2) . . . . ? C1 C5 C6 C7 95.3(3) . . . . ? Cl1 C5 C6 C7 -30.0(3) . . . . ? C11 C6 C7 C8 3.0(5) . . . . ? C5 C6 C7 C8 -176.7(3) . . . . ? C6 C7 C8 C9 -1.4(5) . . . . ? C7 C8 C9 C10 -0.4(6) . . . . ? C8 C9 C10 C11 0.5(6) . . . . ? C7 C6 C11 C10 -2.9(5) . . . . ? C5 C6 C11 C10 176.8(3) . . . . ? C9 C10 C11 C6 1.2(6) . . . . ? C3 N1 C12 C28 -81.3(3) . . . . ? C1 N1 C12 C28 82.5(3) . . . . ? C3 N1 C12 C13 45.7(3) . . . . ? C1 N1 C12 C13 -150.5(2) . . . . ? N1 C12 C13 C18 -132.5(3) . . . . ? C28 C12 C13 C18 -4.8(4) . . . . ? N1 C12 C13 C14 52.4(3) . . . . ? C28 C12 C13 C14 -179.9(2) . . . . ? C18 C13 C14 C15 3.4(4) . . . . ? C12 C13 C14 C15 178.6(2) . . . . ? C13 C14 C15 C16 1.2(4) . . . . ? C13 C14 C15 C19 -174.3(3) . . . . ? C23 O4 C16 C17 77.7(4) . . . . ? C23 O4 C16 C15 -104.7(3) . . . . ? C14 C15 C16 O4 175.2(2) . . . . ? C19 C15 C16 O4 -9.4(4) . . . . ? C14 C15 C16 C17 -7.2(4) . . . . ? C19 C15 C16 C17 168.2(3) . . . . ? O4 C16 C17 C18 -174.3(3) . . . . ? C15 C16 C17 C18 8.2(4) . . . . ? O4 C16 C17 C24 8.2(5) . . . . ? C15 C16 C17 C24 -169.4(3) . . . . ? C14 C13 C18 C17 -2.3(5) . . . . ? C12 C13 C18 C17 -177.6(3) . . . . ? C16 C17 C18 C13 -3.3(5) . . . . ? C24 C17 C18 C13 174.6(3) . . . . ? C14 C15 C19 C21 -125.2(3) . . . . ? C16 C15 C19 C21 59.5(4) . . . . ? C14 C15 C19 C20 -4.0(4) . . . . ? C16 C15 C19 C20 -179.3(3) . . . . ? C14 C15 C19 C22 113.4(3) . . . . ? C16 C15 C19 C22 -61.9(4) . . . . ? C16 C17 C24 C27 143.1(4) . . . . ? C18 C17 C24 C27 -34.4(4) . . . . ? C16 C17 C24 C25 25.8(5) . . . . ? C18 C17 C24 C25 -151.7(4) . . . . ? C16 C17 C24 C26 -98.2(4) . . . . ? C18 C17 C24 C26 84.2(4) . . . . ? N1 C12 C28 C33 48.8(3) . . . . ? C13 C12 C28 C33 -78.3(3) . . . . ? N1 C12 C28 C29 -142.4(2) . . . . ? C13 C12 C28 C29 90.4(3) . . . . ? C33 C28 C29 C30 -0.2(4) . . . . ? C12 C28 C29 C30 -169.1(2) . . . . ? C28 C29 C30 C31 -2.2(4) . . . . ? C28 C29 C30 C34 170.8(3) . . . . ? C38 O5 C31 C32 -85.8(4) . . . . ? C38 O5 C31 C30 96.8(4) . . . . ? C29 C30 C31 O5 -177.4(2) . . . . ? C34 C30 C31 O5 10.1(4) . . . . ? C29 C30 C31 C32 5.3(4) . . . . ? C34 C30 C31 C32 -167.2(3) . . . . ? O5 C31 C32 C33 177.1(2) . . . . ? C30 C31 C32 C33 -5.7(4) . . . . ? O5 C31 C32 C39 -13.1(4) . . . . ? C30 C31 C32 C39 164.2(3) . . . . ? C29 C28 C33 C32 -0.1(4) . . . . ? C12 C28 C33 C32 168.6(2) . . . . ? C31 C32 C33 C28 2.9(4) . . . . ? C39 C32 C33 C28 -167.9(3) . . . . ? C31 C30 C34 C37B -88.0(14) . . . . ? C29 C30 C34 C37B 99.7(14) . . . . ? C31 C30 C34 C35A -166.5(6) . . . . ? C29 C30 C34 C35A 21.1(7) . . . . ? C31 C30 C34 C36A 66.3(7) . . . . ? C29 C30 C34 C36A -106.0(7) . . . . ? C31 C30 C34 C36B 45.2(12) . . . . ? C29 C30 C34 C36B -127.1(12) . . . . ? C31 C30 C34 C37A -48.2(6) . . . . ? C29 C30 C34 C37A 139.5(5) . . . . ? C31 C30 C34 C35B 152.0(7) . . . . ? C29 C30 C34 C35B -20.3(8) . . . . ? C33 C32 C39 C42B -65.1(11) . . . . ? C31 C32 C39 C42B 125.1(11) . . . . ? C33 C32 C39 C40A 106.8(5) . . . . ? C31 C32 C39 C40A -63.0(6) . . . . ? C33 C32 C39 C41A -134.8(4) . . . . ? C31 C32 C39 C41A 55.4(5) . . . . ? C33 C32 C39 C40B 58.1(9) . . . . ? C31 C32 C39 C40B -111.8(9) . . . . ? C33 C32 C39 C41B 167.8(8) . . . . ? C31 C32 C39 C41B -2.0(9) . . . . ? C33 C32 C39 C42A -15.4(6) . . . . ? C31 C32 C39 C42A 174.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.624 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.046 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com data_ww13_0m _database_code_depnum_ccdc_archive 'CCDC 884445' #TrackingRef 'web_deposit_cif_file_1_WilliamD.Wulff_1338302533.41.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C16 H20 Cl N O' _chemical_formula_sum 'C16 H20 Cl N O' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 277.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab ' _symmetry_int_tables_number 19 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 5.1885(10) _cell_length_b 14.530(3) _cell_length_c 19.501(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1470.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9982 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 25.22 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9046 _exptl_absorpt_correction_T_max 0.9574 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were placed in calculated positions and refined using a riding model. C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C) C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C) CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C) N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N) O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O) O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O) ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 22271 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.31 _reflns_number_total 2683 _reflns_number_gt 2488 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0279P)^2^+0.2739P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(6) _refine_ls_number_reflns 2683 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0648 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.25964(10) -0.06704(3) 0.11947(2) 0.04281(13) Uani 1 1 d . . . O1 O -0.0696(2) -0.07346(9) 0.27124(6) 0.0444(3) Uani 1 1 d . . . N1 N 0.1669(2) 0.06454(9) 0.26346(6) 0.0268(3) Uani 1 1 d . . . C1 C 0.1054(3) -0.02498(11) 0.25122(8) 0.0313(4) Uani 1 1 d . . . C2 C 0.3406(3) -0.03843(11) 0.20559(8) 0.0309(4) Uani 1 1 d . . . H2 H 0.4672 -0.0826 0.2259 0.037 Uiso 1 1 calc R . . C3 C 0.4090(3) 0.06366(10) 0.22250(7) 0.0244(3) Uani 1 1 d . . . H3 H 0.5629 0.0667 0.2533 0.029 Uiso 1 1 calc R . . C4 C 0.0860(3) 0.12180(11) 0.32133(8) 0.0306(4) Uani 1 1 d . . . H4A H -0.0775 0.0976 0.3403 0.037 Uiso 1 1 calc R . . H4B H 0.0546 0.1854 0.3052 0.037 Uiso 1 1 calc R . . C5 C 0.2889(3) 0.12307(10) 0.37704(7) 0.0279(3) Uani 1 1 d . . . C6 C 0.3457(4) 0.04183(12) 0.41182(8) 0.0385(4) Uani 1 1 d . . . H6 H 0.2530 -0.0128 0.4015 0.046 Uiso 1 1 calc R . . C7 C 0.5365(4) 0.04034(12) 0.46139(9) 0.0427(5) Uani 1 1 d . . . H7 H 0.5744 -0.0155 0.4847 0.051 Uiso 1 1 calc R . . C8 C 0.6723(4) 0.11913(13) 0.47739(8) 0.0397(4) Uani 1 1 d . . . H8 H 0.8035 0.1177 0.5114 0.048 Uiso 1 1 calc R . . C9 C 0.6156(4) 0.20005(12) 0.44356(9) 0.0381(4) Uani 1 1 d . . . H9 H 0.7069 0.2548 0.4545 0.046 Uiso 1 1 calc R . . C10 C 0.4248(4) 0.20166(11) 0.39335(8) 0.0327(4) Uani 1 1 d . . . H10 H 0.3878 0.2576 0.3701 0.039 Uiso 1 1 calc R . . C11 C 0.4343(3) 0.13237(10) 0.16428(7) 0.0247(3) Uani 1 1 d . . . H11 H 0.2943 0.1201 0.1302 0.030 Uiso 1 1 calc R . . C12 C 0.6951(3) 0.11773(10) 0.12878(8) 0.0292(4) Uani 1 1 d . . . H12A H 0.8351 0.1258 0.1627 0.035 Uiso 1 1 calc R . . H12B H 0.7043 0.0539 0.1112 0.035 Uiso 1 1 calc R . . C13 C 0.7363(4) 0.18457(10) 0.06953(7) 0.0310(4) Uani 1 1 d . . . H13A H 0.6087 0.1718 0.0330 0.037 Uiso 1 1 calc R . . H13B H 0.9106 0.1753 0.0500 0.037 Uiso 1 1 calc R . . C14 C 0.7082(3) 0.28412(11) 0.09336(8) 0.0323(4) Uani 1 1 d . . . H14A H 0.8493 0.2992 0.1257 0.039 Uiso 1 1 calc R . . H14B H 0.7228 0.3258 0.0534 0.039 Uiso 1 1 calc R . . C15 C 0.4507(3) 0.29934(11) 0.12838(9) 0.0328(4) Uani 1 1 d . . . H15A H 0.3103 0.2910 0.0946 0.039 Uiso 1 1 calc R . . H15B H 0.4420 0.3633 0.1457 0.039 Uiso 1 1 calc R . . C16 C 0.4115(3) 0.23224(10) 0.18821(8) 0.0298(4) Uani 1 1 d . . . H16A H 0.5422 0.2444 0.2241 0.036 Uiso 1 1 calc R . . H16B H 0.2390 0.2422 0.2086 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0582(3) 0.0376(2) 0.0326(2) -0.01158(18) -0.0028(2) 0.0004(2) O1 0.0423(7) 0.0439(7) 0.0469(7) 0.0074(6) 0.0026(6) -0.0110(7) N1 0.0291(7) 0.0310(7) 0.0203(6) 0.0001(6) 0.0007(5) -0.0007(6) C1 0.0341(9) 0.0320(9) 0.0278(8) 0.0053(7) -0.0060(8) -0.0013(7) C2 0.0366(9) 0.0288(8) 0.0275(8) 0.0020(6) -0.0038(7) 0.0035(7) C3 0.0234(7) 0.0285(8) 0.0215(7) 0.0000(6) -0.0007(6) 0.0019(7) C4 0.0321(9) 0.0373(9) 0.0223(8) -0.0012(7) 0.0036(7) 0.0052(8) C5 0.0341(9) 0.0323(8) 0.0174(7) -0.0013(6) 0.0052(7) 0.0046(7) C6 0.0557(12) 0.0305(9) 0.0294(8) 0.0015(7) -0.0041(8) -0.0031(8) C7 0.0627(13) 0.0365(10) 0.0289(9) 0.0057(7) -0.0095(9) 0.0068(9) C8 0.0476(11) 0.0488(11) 0.0227(8) -0.0027(7) -0.0047(8) 0.0058(9) C9 0.0470(11) 0.0376(9) 0.0298(9) -0.0044(8) -0.0008(8) -0.0045(9) C10 0.0451(10) 0.0303(8) 0.0227(8) 0.0012(7) 0.0015(7) 0.0031(8) C11 0.0245(8) 0.0290(8) 0.0206(7) -0.0007(6) -0.0003(6) 0.0013(7) C12 0.0291(9) 0.0325(8) 0.0259(8) 0.0008(6) 0.0031(7) 0.0046(7) C13 0.0289(8) 0.0400(9) 0.0242(7) 0.0000(6) 0.0046(7) 0.0037(8) C14 0.0319(9) 0.0369(9) 0.0281(8) 0.0042(7) 0.0030(7) -0.0029(8) C15 0.0359(9) 0.0302(8) 0.0323(9) 0.0034(7) 0.0055(8) 0.0037(7) C16 0.0339(9) 0.0294(8) 0.0262(8) 0.0009(6) 0.0081(7) 0.0023(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7804(16) . ? O1 C1 1.2135(19) . ? N1 C1 1.360(2) . ? N1 C4 1.4635(19) . ? N1 C3 1.4889(18) . ? C1 C2 1.523(2) . ? C2 C3 1.560(2) . ? C2 H2 1.0000 . ? C3 C11 1.517(2) . ? C3 H3 1.0000 . ? C4 C5 1.513(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.379(2) . ? C5 C6 1.393(2) . ? C6 C7 1.384(2) . ? C6 H6 0.9500 . ? C7 C8 1.380(3) . ? C7 H7 0.9500 . ? C8 C9 1.380(2) . ? C8 H8 0.9500 . ? C9 C10 1.393(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.529(2) . ? C11 C12 1.535(2) . ? C11 H11 1.0000 . ? C12 C13 1.524(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.526(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.517(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.534(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 127.71(13) . . ? C1 N1 C3 95.48(12) . . ? C4 N1 C3 131.33(13) . . ? O1 C1 N1 132.38(16) . . ? O1 C1 C2 135.48(16) . . ? N1 C1 C2 92.13(13) . . ? C1 C2 C3 86.38(12) . . ? C1 C2 Cl1 113.07(11) . . ? C3 C2 Cl1 118.36(11) . . ? C1 C2 H2 112.2 . . ? C3 C2 H2 112.2 . . ? Cl1 C2 H2 112.2 . . ? N1 C3 C11 117.95(12) . . ? N1 C3 C2 85.97(11) . . ? C11 C3 C2 119.14(12) . . ? N1 C3 H3 110.5 . . ? C11 C3 H3 110.5 . . ? C2 C3 H3 110.5 . . ? N1 C4 C5 111.18(13) . . ? N1 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N1 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C10 C5 C6 118.78(15) . . ? C10 C5 C4 122.09(14) . . ? C6 C5 C4 119.11(14) . . ? C7 C6 C5 120.30(16) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C8 C7 C6 120.68(16) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 119.32(16) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 120.15(16) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C5 C10 C9 120.77(15) . . ? C5 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C3 C11 C16 112.91(12) . . ? C3 C11 C12 108.82(12) . . ? C16 C11 C12 109.73(13) . . ? C3 C11 H11 108.4 . . ? C16 C11 H11 108.4 . . ? C12 C11 H11 108.4 . . ? C13 C12 C11 112.17(13) . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12B 109.2 . . ? C11 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 111.07(12) . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 111.06(14) . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C14 C15 C16 111.51(14) . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C11 C16 C15 111.14(13) . . ? C11 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? C11 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 O1 21.3(3) . . . . ? C3 N1 C1 O1 177.15(18) . . . . ? C4 N1 C1 C2 -157.48(14) . . . . ? C3 N1 C1 C2 -1.59(12) . . . . ? O1 C1 C2 C3 -177.16(19) . . . . ? N1 C1 C2 C3 1.51(11) . . . . ? O1 C1 C2 Cl1 63.5(2) . . . . ? N1 C1 C2 Cl1 -117.85(11) . . . . ? C1 N1 C3 C11 122.57(14) . . . . ? C4 N1 C3 C11 -82.92(18) . . . . ? C1 N1 C3 C2 1.56(11) . . . . ? C4 N1 C3 C2 156.07(15) . . . . ? C1 C2 C3 N1 -1.39(10) . . . . ? Cl1 C2 C3 N1 112.95(12) . . . . ? C1 C2 C3 C11 -121.30(14) . . . . ? Cl1 C2 C3 C11 -6.96(19) . . . . ? C1 N1 C4 C5 96.21(18) . . . . ? C3 N1 C4 C5 -51.0(2) . . . . ? N1 C4 C5 C10 113.12(16) . . . . ? N1 C4 C5 C6 -65.13(19) . . . . ? C10 C5 C6 C7 -0.5(2) . . . . ? C4 C5 C6 C7 177.81(16) . . . . ? C5 C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 C9 0.2(3) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C6 C5 C10 C9 0.1(2) . . . . ? C4 C5 C10 C9 -178.16(15) . . . . ? C8 C9 C10 C5 0.5(3) . . . . ? N1 C3 C11 C16 58.94(18) . . . . ? C2 C3 C11 C16 160.75(13) . . . . ? N1 C3 C11 C12 -178.97(12) . . . . ? C2 C3 C11 C12 -77.16(16) . . . . ? C3 C11 C12 C13 -179.82(12) . . . . ? C16 C11 C12 C13 -55.82(16) . . . . ? C11 C12 C13 C14 55.58(18) . . . . ? C12 C13 C14 C15 -54.87(18) . . . . ? C13 C14 C15 C16 55.66(18) . . . . ? C3 C11 C16 C15 177.35(14) . . . . ? C12 C11 C16 C15 55.77(17) . . . . ? C14 C15 C16 C11 -56.70(18) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.117 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.030 _contact_Crystallographer_name 'Richard Staples' _contact_Crystallographer_email staples@chemistry.msu.com data_ww14_0m _database_code_depnum_ccdc_archive 'CCDC 884446' #TrackingRef 'web_deposit_cif_file_2_WilliamD.Wulff_1338302533.11 .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C24 H18 Cl N O4' _chemical_formula_sum 'C24 H18 Cl N O4' _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(2) _chemical_formula_weight 419.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab ' _symmetry_int_tables_number 19 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.8652(18) _cell_length_b 13.560(3) _cell_length_c 19.207(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2048.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8340 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 25.16 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9073 _exptl_absorpt_correction_T_max 0.9679 _exptl_absorpt_process_details SADABS _exptl_special_details ; Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and Phi scans of 0.5\% per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4.0 and completeness to 0.83\%A to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS-97 program and refined by least squares method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14. All H atoms were found by difference Fourier methods and refined isotrpically. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w,and/f 0.5 deg' _diffrn_detector_area_resol_mean 836.6 _diffrn_reflns_number 16607 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.37 _reflns_number_total 3735 _reflns_number_gt 3280 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_cell_refinement 'APEX2 (BRUKER, V2010.11-3, 2010)' _computing_data_reduction 'SAINT (BRUKER, V7.68A, 2010)' _computing_structure_solution 'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_structure_refinement 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_molecular_graphics 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _computing_publication_material 'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0264P)^2^+0.1999P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(5) _refine_ls_number_reflns 3735 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0636 _refine_ls_wR_factor_gt 0.0599 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.09330(7) 0.46939(4) 0.76426(2) 0.04914(15) Uani 1 1 d . . . O1 O -0.14698(16) 0.70340(10) 0.86226(6) 0.0379(3) Uani 1 1 d . . . O2 O -0.03284(18) 0.84474(10) 0.89483(7) 0.0481(4) Uani 1 1 d . . . O3 O 0.12331(18) 0.75274(9) 1.00656(7) 0.0431(3) Uani 1 1 d . . . O4 O -0.25529(19) 0.55802(11) 0.83717(7) 0.0483(4) Uani 1 1 d . . . N1 N 0.08172(18) 0.60607(10) 0.95120(6) 0.0271(3) Uani 1 1 d . . . C1 C 0.0218(2) 0.55603(13) 0.88827(8) 0.0284(4) Uani 1 1 d . . . H1 H -0.006(2) 0.4898(13) 0.9001(8) 0.028(5) Uiso 1 1 d . . . C2 C -0.1393(2) 0.60215(14) 0.86139(8) 0.0328(4) Uani 1 1 d . . . C3 C -0.0356(2) 0.75823(14) 0.90199(9) 0.0347(4) Uani 1 1 d . . . C4 C 0.0676(2) 0.70477(13) 0.95850(8) 0.0315(4) Uani 1 1 d . . . C5 C 0.1640(2) 0.55149(13) 0.83162(9) 0.0303(4) Uani 1 1 d . . . H5 H 0.264(2) 0.5192(12) 0.8521(8) 0.022(4) Uiso 1 1 d . . . C6 C 0.2214(2) 0.64932(13) 0.80319(8) 0.0290(4) Uani 1 1 d . . . C7 C 0.1451(3) 0.69405(15) 0.74577(9) 0.0396(5) Uani 1 1 d . . . H7 H 0.054(3) 0.6584(14) 0.7224(10) 0.050(6) Uiso 1 1 d . . . C8 C 0.2060(3) 0.78261(17) 0.72113(11) 0.0522(6) Uani 1 1 d . . . H8 H 0.147(3) 0.8145(16) 0.6797(11) 0.069(7) Uiso 1 1 d . . . C9 C 0.3413(3) 0.82826(16) 0.75270(12) 0.0568(7) Uani 1 1 d . . . H9 H 0.380(3) 0.8870(17) 0.7342(11) 0.066(7) Uiso 1 1 d . . . C10 C 0.4178(3) 0.78536(15) 0.80974(11) 0.0510(6) Uani 1 1 d . . . H10 H 0.520(3) 0.8114(15) 0.8288(10) 0.057(7) Uiso 1 1 d . . . C11 C 0.3582(3) 0.69591(14) 0.83492(10) 0.0359(4) Uani 1 1 d . . . H11 H 0.412(2) 0.6660(12) 0.8713(9) 0.030(5) Uiso 1 1 d . . . C12 C 0.1610(2) 0.54804(13) 1.00875(8) 0.0272(4) Uani 1 1 d . . . H12 H 0.237(2) 0.5962(12) 1.0316(8) 0.025(4) Uiso 1 1 d . . . C13 C 0.2674(2) 0.46317(13) 0.98091(8) 0.0290(4) Uani 1 1 d . . . C14 C 0.4385(2) 0.47711(15) 0.96619(9) 0.0359(4) Uani 1 1 d . . . H14 H 0.490(2) 0.5443(14) 0.9731(9) 0.038(5) Uiso 1 1 d . . . C15 C 0.5342(3) 0.40147(17) 0.93826(11) 0.0459(5) Uani 1 1 d . . . H15 H 0.653(3) 0.4091(15) 0.9270(11) 0.056(6) Uiso 1 1 d . . . C16 C 0.4613(3) 0.31139(17) 0.92489(11) 0.0507(6) Uani 1 1 d . . . H16 H 0.531(3) 0.2619(16) 0.9059(10) 0.053(6) Uiso 1 1 d . . . C17 C 0.2931(3) 0.29543(16) 0.94047(12) 0.0483(5) Uani 1 1 d . . . H17 H 0.239(3) 0.2371(17) 0.9318(10) 0.055(7) Uiso 1 1 d . . . C18 C 0.1961(3) 0.37068(14) 0.96912(10) 0.0383(5) Uani 1 1 d . . . H18 H 0.079(2) 0.3601(13) 0.9779(9) 0.033(5) Uiso 1 1 d . . . C19 C 0.0310(2) 0.51366(12) 1.06175(8) 0.0273(4) Uani 1 1 d . . . C20 C 0.0924(2) 0.46787(15) 1.12156(9) 0.0358(4) Uani 1 1 d . . . H20 H 0.217(3) 0.4616(15) 1.1269(9) 0.044(5) Uiso 1 1 d . . . C21 C -0.0181(3) 0.43129(15) 1.17101(10) 0.0417(5) Uani 1 1 d . . . H21 H 0.025(3) 0.4011(14) 1.2113(10) 0.048(6) Uiso 1 1 d . . . C22 C -0.1902(3) 0.44004(15) 1.16219(10) 0.0384(5) Uani 1 1 d . . . H22 H -0.266(2) 0.4192(13) 1.1967(9) 0.036(5) Uiso 1 1 d . . . C23 C -0.2536(3) 0.48631(15) 1.10411(10) 0.0377(5) Uani 1 1 d . . . H23 H -0.370(3) 0.4927(13) 1.0977(10) 0.042(6) Uiso 1 1 d . . . C24 C -0.1430(2) 0.52386(14) 1.05395(9) 0.0313(4) Uani 1 1 d . . . H24 H -0.189(2) 0.5583(13) 1.0135(10) 0.044(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0633(4) 0.0483(3) 0.0359(3) -0.0161(2) 0.0065(2) -0.0135(3) O1 0.0367(7) 0.0414(8) 0.0356(7) 0.0051(6) 0.0021(6) 0.0080(7) O2 0.0538(9) 0.0325(8) 0.0580(9) 0.0096(7) 0.0109(7) 0.0101(7) O3 0.0618(10) 0.0299(6) 0.0377(7) -0.0082(6) -0.0021(7) -0.0014(6) O4 0.0399(9) 0.0634(10) 0.0417(8) -0.0038(7) -0.0094(7) -0.0073(7) N1 0.0334(8) 0.0248(7) 0.0230(7) -0.0003(6) 0.0002(7) -0.0003(6) C1 0.0344(10) 0.0273(10) 0.0234(9) -0.0013(7) 0.0000(8) -0.0042(8) C2 0.0343(11) 0.0418(11) 0.0223(9) 0.0033(8) 0.0037(8) -0.0016(9) C3 0.0349(10) 0.0341(11) 0.0350(10) 0.0037(8) 0.0131(8) 0.0044(8) C4 0.0383(10) 0.0266(9) 0.0296(9) 0.0000(8) 0.0071(8) 0.0001(8) C5 0.0336(10) 0.0308(10) 0.0265(9) -0.0044(8) -0.0004(8) -0.0007(8) C6 0.0302(10) 0.0306(9) 0.0262(9) -0.0002(8) 0.0072(8) 0.0050(8) C7 0.0371(11) 0.0474(12) 0.0343(10) 0.0067(9) 0.0082(9) 0.0101(10) C8 0.0631(15) 0.0499(14) 0.0436(12) 0.0154(11) 0.0172(11) 0.0226(12) C9 0.0854(19) 0.0302(12) 0.0549(14) 0.0014(10) 0.0335(14) 0.0011(12) C10 0.0647(16) 0.0410(12) 0.0471(12) -0.0120(10) 0.0184(12) -0.0143(12) C11 0.0446(12) 0.0330(10) 0.0303(9) -0.0037(9) 0.0045(9) -0.0005(10) C12 0.0312(9) 0.0254(9) 0.0249(9) -0.0013(7) -0.0043(8) -0.0011(8) C13 0.0340(10) 0.0303(10) 0.0226(8) 0.0026(8) -0.0007(7) 0.0033(8) C14 0.0353(11) 0.0382(11) 0.0341(10) 0.0044(9) -0.0007(8) 0.0034(9) C15 0.0394(12) 0.0534(14) 0.0448(12) 0.0080(10) 0.0077(10) 0.0128(10) C16 0.0646(15) 0.0439(13) 0.0437(12) 0.0028(10) 0.0144(11) 0.0228(12) C17 0.0682(15) 0.0278(11) 0.0489(12) -0.0016(10) 0.0087(11) 0.0030(11) C18 0.0449(13) 0.0315(11) 0.0383(11) 0.0012(8) 0.0060(9) -0.0017(9) C19 0.0328(9) 0.0263(9) 0.0227(8) -0.0026(7) -0.0022(8) 0.0021(7) C20 0.0324(11) 0.0478(11) 0.0273(9) 0.0021(8) -0.0023(8) 0.0062(10) C21 0.0500(14) 0.0496(12) 0.0256(10) 0.0092(9) -0.0029(9) 0.0092(10) C22 0.0421(12) 0.0468(12) 0.0263(10) 0.0015(9) 0.0073(9) 0.0022(10) C23 0.0312(11) 0.0454(12) 0.0366(11) 0.0006(9) 0.0026(9) 0.0045(9) C24 0.0330(9) 0.0371(10) 0.0239(9) 0.0031(8) -0.0026(8) 0.0037(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C5 1.7953(18) . ? O1 C2 1.374(2) . ? O1 C3 1.379(2) . ? O2 C3 1.181(2) . ? O3 C4 1.211(2) . ? O4 C2 1.186(2) . ? N1 C4 1.350(2) . ? N1 C1 1.464(2) . ? N1 C12 1.493(2) . ? C1 C2 1.504(3) . ? C1 C5 1.562(2) . ? C1 H1 0.952(17) . ? C3 C4 1.537(2) . ? C5 C6 1.504(2) . ? C5 H5 0.983(18) . ? C6 C11 1.388(3) . ? C6 C7 1.394(2) . ? C7 C8 1.377(3) . ? C7 H7 0.98(2) . ? C8 C9 1.372(3) . ? C8 H8 1.02(2) . ? C9 C10 1.379(3) . ? C9 H9 0.92(2) . ? C10 C11 1.388(3) . ? C10 H10 0.95(2) . ? C11 H11 0.913(17) . ? C12 C19 1.516(2) . ? C12 C13 1.520(2) . ? C12 H12 0.987(17) . ? C13 C14 1.388(3) . ? C13 C18 1.392(3) . ? C14 C15 1.381(3) . ? C14 H14 1.007(19) . ? C15 C16 1.374(3) . ? C15 H15 0.97(2) . ? C16 C17 1.374(3) . ? C16 H16 0.94(2) . ? C17 C18 1.388(3) . ? C17 H17 0.91(2) . ? C18 H18 0.944(18) . ? C19 C24 1.383(2) . ? C19 C20 1.392(2) . ? C20 C21 1.380(3) . ? C20 H20 0.99(2) . ? C21 C22 1.369(3) . ? C21 H21 0.938(19) . ? C22 C23 1.373(3) . ? C22 H22 0.937(19) . ? C23 C24 1.394(3) . ? C23 H23 0.93(2) . ? C24 H24 0.978(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C3 121.17(15) . . ? C4 N1 C1 121.25(14) . . ? C4 N1 C12 118.66(13) . . ? C1 N1 C12 120.09(13) . . ? N1 C1 C2 111.21(14) . . ? N1 C1 C5 111.25(14) . . ? C2 C1 C5 112.38(14) . . ? N1 C1 H1 108.3(10) . . ? C2 C1 H1 106.3(11) . . ? C5 C1 H1 107.1(10) . . ? O4 C2 O1 118.37(18) . . ? O4 C2 C1 124.93(18) . . ? O1 C2 C1 116.62(16) . . ? O2 C3 O1 118.87(18) . . ? O2 C3 C4 122.72(19) . . ? O1 C3 C4 118.16(15) . . ? O3 C4 N1 125.59(16) . . ? O3 C4 C3 118.42(16) . . ? N1 C4 C3 115.93(15) . . ? C6 C5 C1 115.67(14) . . ? C6 C5 Cl1 112.23(12) . . ? C1 C5 Cl1 107.72(12) . . ? C6 C5 H5 107.3(10) . . ? C1 C5 H5 108.2(9) . . ? Cl1 C5 H5 105.1(9) . . ? C11 C6 C7 118.87(18) . . ? C11 C6 C5 118.32(16) . . ? C7 C6 C5 122.80(17) . . ? C8 C7 C6 120.1(2) . . ? C8 C7 H7 122.1(11) . . ? C6 C7 H7 117.7(12) . . ? C9 C8 C7 120.8(2) . . ? C9 C8 H8 120.5(13) . . ? C7 C8 H8 118.7(13) . . ? C8 C9 C10 119.9(2) . . ? C8 C9 H9 118.3(14) . . ? C10 C9 H9 121.7(15) . . ? C9 C10 C11 119.9(2) . . ? C9 C10 H10 121.2(13) . . ? C11 C10 H10 118.4(13) . . ? C10 C11 C6 120.4(2) . . ? C10 C11 H11 119.9(11) . . ? C6 C11 H11 119.6(11) . . ? N1 C12 C19 112.17(14) . . ? N1 C12 C13 111.62(13) . . ? C19 C12 C13 112.01(13) . . ? N1 C12 H12 103.5(9) . . ? C19 C12 H12 108.2(9) . . ? C13 C12 H12 108.9(10) . . ? C14 C13 C18 118.70(18) . . ? C14 C13 C12 120.16(16) . . ? C18 C13 C12 121.14(16) . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 120.2(11) . . ? C13 C14 H14 119.2(10) . . ? C16 C15 C14 120.4(2) . . ? C16 C15 H15 117.2(13) . . ? C14 C15 H15 122.4(13) . . ? C15 C16 C17 120.1(2) . . ? C15 C16 H16 117.6(13) . . ? C17 C16 H16 122.3(13) . . ? C16 C17 C18 120.0(2) . . ? C16 C17 H17 123.0(13) . . ? C18 C17 H17 117.0(14) . . ? C17 C18 C13 120.3(2) . . ? C17 C18 H18 119.6(11) . . ? C13 C18 H18 120.0(11) . . ? C24 C19 C20 118.52(17) . . ? C24 C19 C12 124.30(15) . . ? C20 C19 C12 117.18(16) . . ? C21 C20 C19 120.63(18) . . ? C21 C20 H20 121.5(11) . . ? C19 C20 H20 117.9(11) . . ? C22 C21 C20 120.42(19) . . ? C22 C21 H21 119.8(13) . . ? C20 C21 H21 119.8(13) . . ? C21 C22 C23 119.9(2) . . ? C21 C22 H22 121.2(12) . . ? C23 C22 H22 118.7(12) . . ? C22 C23 C24 120.10(19) . . ? C22 C23 H23 120.5(12) . . ? C24 C23 H23 119.4(12) . . ? C19 C24 C23 120.37(17) . . ? C19 C24 H24 120.3(12) . . ? C23 C24 H24 119.4(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 -37.4(2) . . . . ? C12 N1 C1 C2 142.90(15) . . . . ? C4 N1 C1 C5 88.71(19) . . . . ? C12 N1 C1 C5 -91.00(17) . . . . ? C3 O1 C2 O4 166.32(15) . . . . ? C3 O1 C2 C1 -16.8(2) . . . . ? N1 C1 C2 O4 -141.50(17) . . . . ? C5 C1 C2 O4 93.0(2) . . . . ? N1 C1 C2 O1 41.8(2) . . . . ? C5 C1 C2 O1 -83.65(19) . . . . ? C2 O1 C3 O2 170.90(17) . . . . ? C2 O1 C3 C4 -14.7(2) . . . . ? C1 N1 C4 O3 -175.01(17) . . . . ? C12 N1 C4 O3 4.7(3) . . . . ? C1 N1 C4 C3 8.0(2) . . . . ? C12 N1 C4 C3 -172.29(14) . . . . ? O2 C3 C4 O3 16.7(3) . . . . ? O1 C3 C4 O3 -157.46(16) . . . . ? O2 C3 C4 N1 -166.05(18) . . . . ? O1 C3 C4 N1 19.8(2) . . . . ? N1 C1 C5 C6 -64.42(19) . . . . ? C2 C1 C5 C6 61.0(2) . . . . ? N1 C1 C5 Cl1 169.13(11) . . . . ? C2 C1 C5 Cl1 -65.42(17) . . . . ? C1 C5 C6 C11 91.9(2) . . . . ? Cl1 C5 C6 C11 -144.00(14) . . . . ? C1 C5 C6 C7 -89.3(2) . . . . ? Cl1 C5 C6 C7 34.8(2) . . . . ? C11 C6 C7 C8 0.4(3) . . . . ? C5 C6 C7 C8 -178.42(17) . . . . ? C6 C7 C8 C9 -0.4(3) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? C8 C9 C10 C11 0.2(3) . . . . ? C9 C10 C11 C6 -0.2(3) . . . . ? C7 C6 C11 C10 -0.1(3) . . . . ? C5 C6 C11 C10 178.77(17) . . . . ? C4 N1 C12 C19 89.91(18) . . . . ? C1 N1 C12 C19 -90.38(17) . . . . ? C4 N1 C12 C13 -143.46(15) . . . . ? C1 N1 C12 C13 36.3(2) . . . . ? N1 C12 C13 C14 89.80(18) . . . . ? C19 C12 C13 C14 -143.48(16) . . . . ? N1 C12 C13 C18 -89.67(19) . . . . ? C19 C12 C13 C18 37.1(2) . . . . ? C18 C13 C14 C15 2.1(3) . . . . ? C12 C13 C14 C15 -177.38(16) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? C14 C15 C16 C17 -1.2(3) . . . . ? C15 C16 C17 C18 0.6(3) . . . . ? C16 C17 C18 C13 1.3(3) . . . . ? C14 C13 C18 C17 -2.7(3) . . . . ? C12 C13 C18 C17 176.82(17) . . . . ? N1 C12 C19 C24 7.5(2) . . . . ? C13 C12 C19 C24 -118.98(19) . . . . ? N1 C12 C19 C20 -173.35(15) . . . . ? C13 C12 C19 C20 60.2(2) . . . . ? C24 C19 C20 C21 1.6(3) . . . . ? C12 C19 C20 C21 -177.59(17) . . . . ? C19 C20 C21 C22 -0.4(3) . . . . ? C20 C21 C22 C23 -0.6(3) . . . . ? C21 C22 C23 C24 0.4(3) . . . . ? C20 C19 C24 C23 -1.9(3) . . . . ? C12 C19 C24 C23 177.30(16) . . . . ? C22 C23 C24 C19 0.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.113 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.028 _contact_Crystallographer_email staples@chemistry.msu.com