############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_global _audit_creation_method 'from SHELXL97 CIF and IUCr SHELXL97-template' _journal_date_recd_electronic 2008-08-05 _journal_date_accepted 2008-08-22 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2008 _journal_volume 64 _journal_issue 10 _journal_page_first o1865 _journal_page_last o1866 _journal_paper_category QO _journal_coeditor_code FJ2144 _publ_contact_author_name 'Dr. Craig Forsyth' _publ_contact_author_address ; School of Chemistry Monash University Wellington Road, Clayton, Victoria 3800 Australia ; _publ_contact_author_email 'craig.forsyth@sci.monash.edu.au' _publ_contact_author_fax '+613 99054597' _publ_contact_author_phone '+613 99054588' _publ_section_title ; 8-Chloro-5-(4-phenethylpiperazin-1-yl)pyrido[2,3-b][1,5]benzoxazepine ; loop_ _publ_author_name _publ_author_address 'Capuano, Ben' ; Department of Medicinal Chemistry Victorian College of Pharmacy Monash University (Parkville Campus) 381 Royal Park Parade, Parkville, Victoria 3052 Australia ; 'Crosby, Ian T.' ; Department of Medicinal Chemistry Victorian College of Pharmacy Monash University (Parkville Campus) 381 Royal Park Parade, Parkville, Victoria 3052 Australia ; 'Forsyth, Craig M.' ; School of Chemistry Monash University Clayton, Victoria 3800 Australia ; 'Lloyd, Edward J.' ; Department of Medicinal Chemistry Victorian College of Pharmacy Monash University (Parkville Campus) 381 Royal Park Parade, Parkville, Victoria 3052 Australia ; 'Vom, Amelia' ; Department of Medicinal Chemistry Victorian College of Pharmacy Monash University (Parkville Campus) 381 Royal Park Parade, Parkville, Victoria 3052 Australia ; 'Yuriev, Elizabeth' ; Department of Medicinal Chemistry Victorian College of Pharmacy Monash University (Parkville Campus) 381 Royal Park Parade, Parkville, Victoria 3052 Australia ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-Chloro-5-(4-phenethylpiperazin-1-yl)pyrido[2,3-b][1,5]benzoxazepine ; _chemical_name_common ? _chemical_formula_moiety 'C24 H23 Cl N4 O' _chemical_formula_sum 'C24 H23 Cl N4 O' _chemical_formula_iupac 'C24 H23 Cl N4 O' _chemical_formula_weight 418.91 _chemical_melting_point ? _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9253(2) _cell_length_b 15.0549(3) _cell_length_c 15.9996(3) _cell_angle_alpha 107.774(2) _cell_angle_beta 95.4870(10) _cell_angle_gamma 108.7830(10) _cell_volume 2104.93(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25726 _cell_measurement_theta_min 1.53 _cell_measurement_theta_max 27.50 _cell_measurement_temperature 123(2) _exptl_crystal_description prismatic _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '1 deg frames in \f and \w' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25726 _diffrn_reflns_av_R_equivalents 0.0844 _diffrn_reflns_av_sigmaI/netI 0.0831 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.986 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^ > \s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 9532 _reflns_number_gt 6353 _reflns_threshold_expression >2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0927 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_gt 0.1360 _refine_ls_wR_factor_ref 0.1584 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_number_reflns 9532 _refine_ls_number_parameters 541 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.477 _refine_diff_density_min -0.324 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' _computing_data_collection 'COLLECT (Bruker, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'CIFTAB (Sheldrick, 2008)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl1 0.43755(6) 1.38055(4) 1.08930(3) 0.03010(15) Uani d . 1 . . Cl Cl2 0.12302(6) 0.14811(4) 0.23248(3) 0.03132(15) Uani d . 1 . . O O1 0.82246(16) 1.34506(11) 0.83292(9) 0.0255(3) Uani d . 1 . . O O2 -0.04349(15) 0.18117(10) 0.58032(8) 0.0248(3) Uani d . 1 . . N N1 0.55743(18) 1.17733(13) 0.80785(10) 0.0223(4) Uani d . 1 . . N N2 1.02695(19) 1.32173(13) 0.88624(11) 0.0265(4) Uani d . 1 . . N N3 0.59265(18) 1.05244(13) 0.69781(10) 0.0245(4) Uani d . 1 . . N N4 0.47574(18) 0.86689(13) 0.54748(10) 0.0252(4) Uani d . 1 . . N N5 0.05941(18) 0.35809(13) 0.53319(10) 0.0224(4) Uani d . 1 . . N N6 0.13408(19) 0.17182(13) 0.67722(10) 0.0245(4) Uani d . 1 . . N N7 0.10986(18) 0.48198(12) 0.67195(10) 0.0221(4) Uani d . 1 . . N N8 0.11770(18) 0.67465(12) 0.77966(10) 0.0219(4) Uani d . 1 . . C C1 0.6055(2) 1.26737(16) 0.88188(12) 0.0217(4) Uani d . 1 . . C C2 0.5157(2) 1.27768(16) 0.94409(12) 0.0230(4) Uani d . 1 . . H H2 0.4327 1.2217 0.9400 0.028 Uiso calc R 1 . . C C3 0.5486(2) 1.36993(16) 1.01146(12) 0.0238(5) Uani d . 1 . . C C4 0.6674(2) 1.45349(16) 1.01968(13) 0.0279(5) Uani d . 1 . . H H4 0.6862 1.5163 1.0654 0.034 Uiso calc R 1 . . C C5 0.7592(2) 1.44418(16) 0.95978(13) 0.0276(5) Uani d . 1 . . H H5 0.8423 1.5005 0.9646 0.033 Uiso calc R 1 . . C C6 0.7283(2) 1.35212(16) 0.89302(12) 0.0230(4) Uani d . 1 . . C C7 0.8879(2) 1.28001(16) 0.84410(12) 0.0228(4) Uani d . 1 . . C C8 1.0898(2) 1.25901(17) 0.89859(13) 0.0280(5) Uani d . 1 . . H H8 1.1890 1.2871 0.9293 0.034 Uiso calc R 1 . . C C9 1.0194(2) 1.15579(17) 0.86940(12) 0.0260(5) Uani d . 1 . . H H9 1.0689 1.1145 0.8800 0.031 Uiso calc R 1 . . C C10 0.8740(2) 1.11413(16) 0.82406(12) 0.0226(4) Uani d . 1 . . H H10 0.8224 1.0436 0.8029 0.027 Uiso calc R 1 . . C C11 0.8060(2) 1.17713(15) 0.81026(12) 0.0209(4) Uani d . 1 . . C C12 0.6466(2) 1.13941(15) 0.77075(12) 0.0208(4) Uani d . 1 . . C C13 0.6737(2) 1.03001(16) 0.62703(12) 0.0262(5) Uani d . 1 . . H H13A 0.7797 1.0629 0.6530 0.031 Uiso calc R 1 . . H H13B 0.6506 1.0567 0.5804 0.031 Uiso calc R 1 . . C C14 0.4348(2) 1.00197(16) 0.66368(14) 0.0295(5) Uani d . 1 . . H H14A 0.4021 1.0285 0.6193 0.035 Uiso calc R 1 . . H H14B 0.3838 1.0148 0.7137 0.035 Uiso calc R 1 . . C C15 0.6332(2) 0.91819(16) 0.58523(13) 0.0266(5) Uani d . 1 . . H H15A 0.6870 0.9036 0.5370 0.032 Uiso calc R 1 . . H H15B 0.6617 0.8924 0.6313 0.032 Uiso calc R 1 . . C C16 0.3981(2) 0.88978(16) 0.61953(13) 0.0277(5) Uani d . 1 . . H H16A 0.4238 0.8630 0.6655 0.033 Uiso calc R 1 . . H H16B 0.2919 0.8558 0.5946 0.033 Uiso calc R 1 . . C C17 0.4348(2) 0.75783(16) 0.50652(13) 0.0283(5) Uani d . 1 . . H H17A 0.3273 0.7252 0.4932 0.034 Uiso calc R 1 . . H H17B 0.4753 0.7336 0.5502 0.034 Uiso calc R 1 . . C C18 0.4887(3) 0.72652(17) 0.42041(14) 0.0345(6) Uani d . 1 . . H H18A 0.4413 0.7450 0.3746 0.041 Uiso calc R 1 . . H H18B 0.5951 0.7634 0.4323 0.041 Uiso calc R 1 . . C C19 0.4567(2) 0.61571(17) 0.38432(13) 0.0270(5) Uani d . 1 . . C C20 0.5436(2) 0.57522(18) 0.42136(13) 0.0321(5) Uani d . 1 . . H H20 0.6227 0.6183 0.4708 0.039 Uiso calc R 1 . . C C21 0.5179(3) 0.47376(19) 0.38809(15) 0.0398(6) Uani d . 1 . . H H21 0.5809 0.4482 0.4133 0.048 Uiso calc R 1 . . C C22 0.4013(3) 0.40982(19) 0.31860(17) 0.0458(7) Uani d . 1 . . H H22 0.3828 0.3399 0.2961 0.055 Uiso calc R 1 . . C C23 0.3108(3) 0.4477(2) 0.28147(15) 0.0447(7) Uani d . 1 . . H H23 0.2294 0.4037 0.2338 0.054 Uiso calc R 1 . . C C24 0.3391(2) 0.55034(19) 0.31401(14) 0.0367(6) Uani d . 1 . . H H24 0.2773 0.5760 0.2878 0.044 Uiso calc R 1 . . C C25 0.0493(2) 0.26283(15) 0.47717(12) 0.0209(4) Uani d . 1 . . C C26 0.0878(2) 0.25284(16) 0.39394(12) 0.0233(4) Uani d . 1 . . H H26 0.1293 0.3107 0.3789 0.028 Uiso calc R 1 . . C C27 0.0653(2) 0.15853(16) 0.33345(12) 0.0235(5) Uani d . 1 . . C C28 0.0012(2) 0.07163(16) 0.35102(13) 0.0251(5) Uani d . 1 . . H H28 -0.0174 0.0076 0.3073 0.030 Uiso calc R 1 . . C C29 -0.0354(2) 0.08040(16) 0.43400(12) 0.0238(5) Uani d . 1 . . H H29 -0.0781 0.0221 0.4483 0.029 Uiso calc R 1 . . C C30 -0.0094(2) 0.17435(15) 0.49555(12) 0.0226(4) Uani d . 1 . . C C31 0.0867(2) 0.22962(16) 0.64466(12) 0.0225(4) Uani d . 1 . . C C32 0.2615(2) 0.21837(17) 0.73820(13) 0.0273(5) Uani d . 1 . . H H32 0.2987 0.1789 0.7629 0.033 Uiso calc R 1 . . C C33 0.3407(2) 0.32015(16) 0.76676(12) 0.0244(5) Uani d . 1 . . H H33 0.4299 0.3497 0.8100 0.029 Uiso calc R 1 . . C C34 0.2875(2) 0.37851(16) 0.73110(12) 0.0222(4) Uani d . 1 . . H H34 0.3399 0.4488 0.7495 0.027 Uiso calc R 1 . . C C35 0.1563(2) 0.33270(15) 0.66807(12) 0.0205(4) Uani d . 1 . . C C36 0.0998(2) 0.38808(15) 0.62012(12) 0.0211(4) Uani d . 1 . . C C37 0.0757(2) 0.50015(15) 0.76178(12) 0.0235(5) Uani d . 1 . . H H37A 0.1046 0.4567 0.7895 0.028 Uiso calc R 1 . . H H37B -0.0305 0.4830 0.7564 0.028 Uiso calc R 1 . . C C38 0.0800(2) 0.54901(15) 0.62959(12) 0.0246(5) Uani d . 1 . . H H38A -0.0260 0.5346 0.6170 0.029 Uiso calc R 1 . . H H38B 0.1126 0.5384 0.5720 0.029 Uiso calc R 1 . . C C39 0.1557(2) 0.60878(15) 0.82070(12) 0.0238(5) Uani d . 1 . . H H39A 0.1299 0.6206 0.8803 0.029 Uiso calc R 1 . . H H39B 0.2621 0.6246 0.8295 0.029 Uiso calc R 1 . . C C40 0.1610(2) 0.65674(15) 0.69272(12) 0.0230(4) Uani d . 1 . . H H40A 0.2672 0.6715 0.7023 0.028 Uiso calc R 1 . . H H40B 0.1406 0.7027 0.6649 0.028 Uiso calc R 1 . . C C41 0.1924(2) 0.78003(15) 0.83789(12) 0.0251(5) Uani d . 1 . . H H41A 0.1826 0.8231 0.8035 0.030 Uiso calc R 1 . . H H41B 0.2974 0.7935 0.8554 0.030 Uiso calc R 1 . . C C42 0.1336(2) 0.80871(16) 0.92268(13) 0.0273(5) Uani d . 1 . . H H42A 0.0302 0.7997 0.9056 0.033 Uiso calc R 1 . . H H42B 0.1379 0.7633 0.9556 0.033 Uiso calc R 1 . . C C43 0.2189(2) 0.91604(16) 0.98384(12) 0.0245(5) Uani d . 1 . . C C44 0.3466(2) 0.93923(17) 1.04455(13) 0.0263(5) Uani d . 1 . . H H44 0.3809 0.8875 1.0460 0.032 Uiso calc R 1 . . C C45 0.4243(2) 1.03739(17) 1.10308(13) 0.0286(5) Uani d . 1 . . H H45 0.5102 1.0520 1.1449 0.034 Uiso calc R 1 . . C C46 0.3771(2) 1.11341(17) 1.10059(13) 0.0313(5) Uani d . 1 . . H H46 0.4300 1.1803 1.1407 0.038 Uiso calc R 1 . . C C47 0.2520(2) 1.09162(17) 1.03929(13) 0.0302(5) Uani d . 1 . . H H47 0.2199 1.1439 1.0366 0.036 Uiso calc R 1 . . C C48 0.1736(2) 0.99370(16) 0.98195(13) 0.0279(5) Uani d . 1 . . H H48 0.0873 0.9794 0.9406 0.033 Uiso calc R 1 . . 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 Cl1 0.0300(3) 0.0328(3) 0.0256(3) 0.0151(2) 0.0060(2) 0.0043(2) Cl2 0.0398(3) 0.0298(3) 0.0227(3) 0.0145(3) 0.0059(2) 0.0056(2) O1 0.0273(8) 0.0225(8) 0.0304(8) 0.0101(7) 0.0088(6) 0.0127(6) O2 0.0203(7) 0.0238(8) 0.0245(7) 0.0041(6) 0.0025(5) 0.0060(6) N1 0.0191(9) 0.0228(10) 0.0223(8) 0.0083(8) 0.0006(6) 0.0050(7) N2 0.0218(9) 0.0254(10) 0.0269(9) 0.0048(8) 0.0048(7) 0.0062(7) N3 0.0176(9) 0.0247(10) 0.0246(9) 0.0065(8) 0.0023(7) 0.0020(7) N4 0.0220(9) 0.0218(10) 0.0260(9) 0.0075(8) 0.0031(7) 0.0020(7) N5 0.0236(9) 0.0216(10) 0.0213(8) 0.0098(8) 0.0010(7) 0.0060(7) N6 0.0314(10) 0.0224(10) 0.0240(9) 0.0136(8) 0.0074(7) 0.0100(7) N7 0.0289(10) 0.0198(9) 0.0201(8) 0.0131(8) 0.0030(7) 0.0071(7) N8 0.0252(9) 0.0193(9) 0.0227(8) 0.0101(8) 0.0032(7) 0.0083(7) C1 0.0212(10) 0.0249(11) 0.0203(10) 0.0126(9) -0.0013(7) 0.0073(8) C2 0.0211(11) 0.0236(11) 0.0233(10) 0.0090(9) -0.0012(8) 0.0083(8) C3 0.0265(11) 0.0286(12) 0.0199(10) 0.0161(10) 0.0038(8) 0.0076(8) C4 0.0350(13) 0.0218(12) 0.0249(11) 0.0137(10) -0.0007(9) 0.0042(8) C5 0.0301(12) 0.0199(11) 0.0304(11) 0.0074(9) 0.0017(9) 0.0090(9) C6 0.0237(11) 0.0255(12) 0.0234(10) 0.0125(9) 0.0030(8) 0.0107(8) C7 0.0230(11) 0.0232(11) 0.0226(10) 0.0087(9) 0.0055(8) 0.0086(8) C8 0.0207(11) 0.0389(14) 0.0228(10) 0.0115(10) 0.0030(8) 0.0088(9) C9 0.0236(11) 0.0329(13) 0.0245(10) 0.0143(10) 0.0051(8) 0.0101(9) C10 0.0239(11) 0.0225(11) 0.0213(10) 0.0087(9) 0.0077(8) 0.0068(8) C11 0.0182(10) 0.0226(11) 0.0196(9) 0.0062(9) 0.0036(7) 0.0061(8) C12 0.0187(10) 0.0229(11) 0.0216(10) 0.0078(9) 0.0025(7) 0.0097(8) C13 0.0233(11) 0.0273(12) 0.0226(10) 0.0048(9) 0.0039(8) 0.0067(9) C14 0.0189(11) 0.0278(13) 0.0330(11) 0.0094(9) -0.0001(8) 0.0000(9) C15 0.0211(11) 0.0295(13) 0.0248(10) 0.0084(9) 0.0046(8) 0.0048(9) C16 0.0174(10) 0.0268(12) 0.0308(11) 0.0070(9) 0.0025(8) 0.0017(9) C17 0.0268(12) 0.0231(12) 0.0284(11) 0.0069(10) 0.0066(9) 0.0026(9) C18 0.0446(15) 0.0251(13) 0.0303(12) 0.0113(11) 0.0112(10) 0.0061(9) C19 0.0288(12) 0.0280(12) 0.0220(10) 0.0088(10) 0.0110(8) 0.0061(9) C20 0.0304(13) 0.0361(14) 0.0253(11) 0.0086(11) 0.0085(9) 0.0079(9) C21 0.0511(16) 0.0411(16) 0.0432(14) 0.0258(13) 0.0256(12) 0.0227(12) C22 0.0585(18) 0.0264(14) 0.0490(15) 0.0109(13) 0.0326(13) 0.0077(11) C23 0.0328(14) 0.0386(16) 0.0348(13) -0.0027(12) 0.0079(10) -0.0077(11) C24 0.0261(12) 0.0428(15) 0.0320(12) 0.0101(11) 0.0045(9) 0.0044(10) C25 0.0196(10) 0.0216(11) 0.0201(10) 0.0096(9) -0.0023(7) 0.0053(8) C26 0.0236(11) 0.0228(11) 0.0232(10) 0.0093(9) -0.0008(8) 0.0088(8) C27 0.0254(11) 0.0282(12) 0.0165(9) 0.0128(9) -0.0002(8) 0.0057(8) C28 0.0262(11) 0.0209(11) 0.0237(10) 0.0108(9) -0.0023(8) 0.0021(8) C29 0.0189(10) 0.0201(11) 0.0268(11) 0.0039(9) -0.0033(8) 0.0068(8) C30 0.0193(10) 0.0248(12) 0.0208(10) 0.0080(9) -0.0007(7) 0.0057(8) C31 0.0227(11) 0.0250(12) 0.0197(10) 0.0094(9) 0.0061(8) 0.0070(8) C32 0.0337(12) 0.0309(13) 0.0257(11) 0.0193(10) 0.0081(9) 0.0132(9) C33 0.0222(11) 0.0309(12) 0.0226(10) 0.0119(9) 0.0037(8) 0.0110(9) C34 0.0223(11) 0.0237(11) 0.0203(10) 0.0086(9) 0.0056(8) 0.0073(8) C35 0.0211(10) 0.0215(11) 0.0209(10) 0.0097(9) 0.0057(7) 0.0080(8) C36 0.0171(10) 0.0214(11) 0.0240(10) 0.0067(9) 0.0029(7) 0.0079(8) C37 0.0273(11) 0.0219(11) 0.0251(10) 0.0120(9) 0.0087(8) 0.0097(8) C38 0.0321(12) 0.0222(11) 0.0207(10) 0.0137(10) 0.0005(8) 0.0072(8) C39 0.0276(11) 0.0241(12) 0.0210(10) 0.0120(9) 0.0048(8) 0.0073(8) C40 0.0272(11) 0.0234(11) 0.0211(10) 0.0117(9) 0.0047(8) 0.0093(8) C41 0.0273(12) 0.0214(11) 0.0257(10) 0.0091(9) 0.0040(8) 0.0075(8) C42 0.0294(12) 0.0228(12) 0.0272(11) 0.0085(10) 0.0074(8) 0.0062(9) C43 0.0273(12) 0.0263(12) 0.0206(10) 0.0111(10) 0.0078(8) 0.0074(8) C44 0.0285(12) 0.0297(13) 0.0278(11) 0.0144(10) 0.0100(8) 0.0146(9) C45 0.0247(12) 0.0361(14) 0.0237(10) 0.0091(10) 0.0051(8) 0.0112(9) C46 0.0299(13) 0.0275(13) 0.0290(11) 0.0078(10) 0.0084(9) 0.0026(9) C47 0.0346(13) 0.0259(12) 0.0301(11) 0.0152(10) 0.0064(9) 0.0059(9) C48 0.0292(12) 0.0265(12) 0.0273(11) 0.0122(10) 0.0030(8) 0.0077(9) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C3 . 1.745(2) ? Cl2 C27 . 1.7442(19) ? O1 C7 . 1.381(2) ? O1 C6 . 1.408(2) ? O2 C31 . 1.393(2) ? O2 C30 . 1.410(2) ? N1 C12 . 1.297(3) ? N1 C1 . 1.401(2) ? N2 C7 . 1.326(3) ? N2 C8 . 1.338(3) ? N3 C12 . 1.363(2) ? N3 C14 . 1.466(3) ? N3 C13 . 1.469(2) ? N4 C16 . 1.463(2) ? N4 C17 . 1.467(3) ? N4 C15 . 1.470(3) ? N5 C36 . 1.301(2) ? N5 C25 . 1.406(2) ? N6 C31 . 1.320(3) ? N6 C32 . 1.348(3) ? N7 C36 . 1.369(3) ? N7 C38 . 1.462(3) ? N7 C37 . 1.472(2) ? N8 C41 . 1.464(2) ? N8 C39 . 1.466(3) ? N8 C40 . 1.467(2) ? C1 C6 . 1.402(3) ? C1 C2 . 1.405(3) ? C2 C3 . 1.387(3) ? C2 H2 . 0.9500 ? C3 C4 . 1.380(3) ? C4 C5 . 1.391(3) ? C4 H4 . 0.9500 ? C5 C6 . 1.384(3) ? C5 H5 . 0.9500 ? C7 C11 . 1.395(3) ? C8 C9 . 1.384(3) ? C8 H8 . 0.9500 ? C9 C10 . 1.393(3) ? C9 H9 . 0.9500 ? C10 C11 . 1.384(3) ? C10 H10 . 0.9500 ? C11 C12 . 1.495(3) ? C13 C15 . 1.506(3) ? C13 H13A . 0.9900 ? C13 H13B . 0.9900 ? C14 C16 . 1.520(3) ? C14 H14A . 0.9900 ? C14 H14B . 0.9900 ? C15 H15A . 0.9900 ? C15 H15B . 0.9900 ? C16 H16A . 0.9900 ? C16 H16B . 0.9900 ? C17 C18 . 1.521(3) ? C17 H17A . 0.9900 ? C17 H17B . 0.9900 ? C18 C19 . 1.501(3) ? C18 H18A . 0.9900 ? C18 H18B . 0.9900 ? C19 C20 . 1.388(3) ? C19 C24 . 1.389(3) ? C20 C21 . 1.381(3) ? C20 H20 . 0.9500 ? C21 C22 . 1.373(4) ? C21 H21 . 0.9500 ? C22 C23 . 1.386(4) ? C22 H22 . 0.9500 ? C23 C24 . 1.392(3) ? C23 H23 . 0.9500 ? C24 H24 . 0.9500 ? C25 C26 . 1.398(3) ? C25 C30 . 1.405(3) ? C26 C27 . 1.385(3) ? C26 H26 . 0.9500 ? C27 C28 . 1.385(3) ? C28 C29 . 1.389(3) ? C28 H28 . 0.9500 ? C29 C30 . 1.379(3) ? C29 H29 . 0.9500 ? C31 C35 . 1.390(3) ? C32 C33 . 1.380(3) ? C32 H32 . 0.9500 ? C33 C34 . 1.387(3) ? C33 H33 . 0.9500 ? C34 C35 . 1.391(3) ? C34 H34 . 0.9500 ? C35 C36 . 1.486(3) ? C37 C39 . 1.508(3) ? C37 H37A . 0.9900 ? C37 H37B . 0.9900 ? C38 C40 . 1.517(3) ? C38 H38A . 0.9900 ? C38 H38B . 0.9900 ? C39 H39A . 0.9900 ? C39 H39B . 0.9900 ? C40 H40A . 0.9900 ? C40 H40B . 0.9900 ? C41 C42 . 1.524(3) ? C41 H41A . 0.9900 ? C41 H41B . 0.9900 ? C42 C43 . 1.510(3) ? C42 H42A . 0.9900 ? C42 H42B . 0.9900 ? C43 C48 . 1.388(3) ? C43 C44 . 1.394(3) ? C44 C45 . 1.392(3) ? C44 H44 . 0.9500 ? C45 C46 . 1.379(3) ? C45 H45 . 0.9500 ? C46 C47 . 1.386(3) ? C46 H46 . 0.9500 ? C47 C48 . 1.385(3) ? C47 H47 . 0.9500 ? C48 H48 . 0.9500 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 O1 C6 . . 108.51(15) ? C31 O2 C30 . . 107.85(14) ? C12 N1 C1 . . 122.45(17) ? C7 N2 C8 . . 116.26(19) ? C12 N3 C14 . . 119.65(17) ? C12 N3 C13 . . 122.36(17) ? C14 N3 C13 . . 111.97(15) ? C16 N4 C17 . . 109.81(16) ? C16 N4 C15 . . 108.62(15) ? C17 N4 C15 . . 111.58(17) ? C36 N5 C25 . . 121.46(18) ? C31 N6 C32 . . 116.07(18) ? C36 N7 C38 . . 120.12(15) ? C36 N7 C37 . . 120.21(17) ? C38 N7 C37 . . 112.65(16) ? C41 N8 C39 . . 110.58(15) ? C41 N8 C40 . . 110.43(16) ? C39 N8 C40 . . 107.81(16) ? N1 C1 C6 . . 124.50(18) ? N1 C1 C2 . . 117.77(18) ? C6 C1 C2 . . 117.31(18) ? C3 C2 C1 . . 119.8(2) ? C3 C2 H2 . . 120.1 ? C1 C2 H2 . . 120.1 ? C4 C3 C2 . . 122.16(19) ? C4 C3 Cl1 . . 118.81(15) ? C2 C3 Cl1 . . 119.03(17) ? C3 C4 C5 . . 118.86(19) ? C3 C4 H4 . . 120.6 ? C5 C4 H4 . . 120.6 ? C6 C5 C4 . . 119.4(2) ? C6 C5 H5 . . 120.3 ? C4 C5 H5 . . 120.3 ? C5 C6 C1 . . 122.44(19) ? C5 C6 O1 . . 118.19(19) ? C1 C6 O1 . . 119.34(17) ? N2 C7 O1 . . 116.16(19) ? N2 C7 C11 . . 125.0(2) ? O1 C7 C11 . . 118.86(18) ? N2 C8 C9 . . 124.1(2) ? N2 C8 H8 . . 117.9 ? C9 C8 H8 . . 117.9 ? C8 C9 C10 . . 118.2(2) ? C8 C9 H9 . . 120.9 ? C10 C9 H9 . . 120.9 ? C11 C10 C9 . . 119.0(2) ? C11 C10 H10 . . 120.5 ? C9 C10 H10 . . 120.5 ? C10 C11 C7 . . 117.41(18) ? C10 C11 C12 . . 122.08(19) ? C7 C11 C12 . . 120.12(19) ? N1 C12 N3 . . 119.41(18) ? N1 C12 C11 . . 123.82(17) ? N3 C12 C11 . . 116.22(17) ? N3 C13 C15 . . 109.85(17) ? N3 C13 H13A . . 109.7 ? C15 C13 H13A . . 109.7 ? N3 C13 H13B . . 109.7 ? C15 C13 H13B . . 109.7 ? H13A C13 H13B . . 108.2 ? N3 C14 C16 . . 109.06(17) ? N3 C14 H14A . . 109.9 ? C16 C14 H14A . . 109.9 ? N3 C14 H14B . . 109.9 ? C16 C14 H14B . . 109.9 ? H14A C14 H14B . . 108.3 ? N4 C15 C13 . . 111.03(18) ? N4 C15 H15A . . 109.4 ? C13 C15 H15A . . 109.4 ? N4 C15 H15B . . 109.4 ? C13 C15 H15B . . 109.4 ? H15A C15 H15B . . 108.0 ? N4 C16 C14 . . 112.14(18) ? N4 C16 H16A . . 109.2 ? C14 C16 H16A . . 109.2 ? N4 C16 H16B . . 109.2 ? C14 C16 H16B . . 109.2 ? H16A C16 H16B . . 107.9 ? N4 C17 C18 . . 113.11(18) ? N4 C17 H17A . . 109.0 ? C18 C17 H17A . . 109.0 ? N4 C17 H17B . . 109.0 ? C18 C17 H17B . . 109.0 ? H17A C17 H17B . . 107.8 ? C19 C18 C17 . . 111.98(18) ? C19 C18 H18A . . 109.2 ? C17 C18 H18A . . 109.2 ? C19 C18 H18B . . 109.2 ? C17 C18 H18B . . 109.2 ? H18A C18 H18B . . 107.9 ? C20 C19 C24 . . 117.9(2) ? C20 C19 C18 . . 120.6(2) ? C24 C19 C18 . . 121.5(2) ? C21 C20 C19 . . 121.6(2) ? C21 C20 H20 . . 119.2 ? C19 C20 H20 . . 119.2 ? C22 C21 C20 . . 120.0(3) ? C22 C21 H21 . . 120.0 ? C20 C21 H21 . . 120.0 ? C21 C22 C23 . . 119.7(2) ? C21 C22 H22 . . 120.1 ? C23 C22 H22 . . 120.1 ? C22 C23 C24 . . 120.0(2) ? C22 C23 H23 . . 120.0 ? C24 C23 H23 . . 120.0 ? C19 C24 C23 . . 120.8(2) ? C19 C24 H24 . . 119.6 ? C23 C24 H24 . . 119.6 ? C26 C25 C30 . . 117.01(18) ? C26 C25 N5 . . 118.53(18) ? C30 C25 N5 . . 124.21(17) ? C27 C26 C25 . . 119.9(2) ? C27 C26 H26 . . 120.0 ? C25 C26 H26 . . 120.0 ? C26 C27 C28 . . 122.30(19) ? C26 C27 Cl2 . . 119.27(17) ? C28 C27 Cl2 . . 118.42(15) ? C27 C28 C29 . . 118.42(18) ? C27 C28 H28 . . 120.8 ? C29 C28 H28 . . 120.8 ? C30 C29 C28 . . 119.5(2) ? C30 C29 H29 . . 120.3 ? C28 C29 H29 . . 120.3 ? C29 C30 C25 . . 122.73(18) ? C29 C30 O2 . . 118.25(18) ? C25 C30 O2 . . 119.02(17) ? N6 C31 C35 . . 125.67(19) ? N6 C31 O2 . . 116.04(18) ? C35 C31 O2 . . 118.28(18) ? N6 C32 C33 . . 123.6(2) ? N6 C32 H32 . . 118.2 ? C33 C32 H32 . . 118.2 ? C32 C33 C34 . . 118.69(19) ? C32 C33 H33 . . 120.7 ? C34 C33 H33 . . 120.7 ? C33 C34 C35 . . 119.05(19) ? C33 C34 H34 . . 120.5 ? C35 C34 H34 . . 120.5 ? C31 C35 C34 . . 116.89(19) ? C31 C35 C36 . . 120.65(17) ? C34 C35 C36 . . 122.14(19) ? N5 C36 N7 . . 119.44(19) ? N5 C36 C35 . . 124.18(18) ? N7 C36 C35 . . 115.85(16) ? N7 C37 C39 . . 110.22(16) ? N7 C37 H37A . . 109.6 ? C39 C37 H37A . . 109.6 ? N7 C37 H37B . . 109.6 ? C39 C37 H37B . . 109.6 ? H37A C37 H37B . . 108.1 ? N7 C38 C40 . . 108.73(15) ? N7 C38 H38A . . 109.9 ? C40 C38 H38A . . 109.9 ? N7 C38 H38B . . 109.9 ? C40 C38 H38B . . 109.9 ? H38A C38 H38B . . 108.3 ? N8 C39 C37 . . 110.54(16) ? N8 C39 H39A . . 109.5 ? C37 C39 H39A . . 109.5 ? N8 C39 H39B . . 109.5 ? C37 C39 H39B . . 109.5 ? H39A C39 H39B . . 108.1 ? N8 C40 C38 . . 111.45(16) ? N8 C40 H40A . . 109.3 ? C38 C40 H40A . . 109.3 ? N8 C40 H40B . . 109.3 ? C38 C40 H40B . . 109.3 ? H40A C40 H40B . . 108.0 ? N8 C41 C42 . . 113.44(17) ? N8 C41 H41A . . 108.9 ? C42 C41 H41A . . 108.9 ? N8 C41 H41B . . 108.9 ? C42 C41 H41B . . 108.9 ? H41A C41 H41B . . 107.7 ? C43 C42 C41 . . 112.03(17) ? C43 C42 H42A . . 109.2 ? C41 C42 H42A . . 109.2 ? C43 C42 H42B . . 109.2 ? C41 C42 H42B . . 109.2 ? H42A C42 H42B . . 107.9 ? C48 C43 C44 . . 118.2(2) ? C48 C43 C42 . . 121.78(19) ? C44 C43 C42 . . 120.0(2) ? C45 C44 C43 . . 120.7(2) ? C45 C44 H44 . . 119.7 ? C43 C44 H44 . . 119.7 ? C46 C45 C44 . . 120.2(2) ? C46 C45 H45 . . 119.9 ? C44 C45 H45 . . 119.9 ? C45 C46 C47 . . 119.6(2) ? C45 C46 H46 . . 120.2 ? C47 C46 H46 . . 120.2 ? C48 C47 C46 . . 120.1(2) ? C48 C47 H47 . . 119.9 ? C46 C47 H47 . . 119.9 ? C47 C48 C43 . . 121.1(2) ? C47 C48 H48 . . 119.4 ? C43 C48 H48 . . 119.4 ?