# Electronic Supplementary Material (ESI) for RSC Advances # 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_3bb(C4) #TrackingRef '17685_web_deposit_cif_file_0_TarekAZeidan_1360705814.3bb-C4.cif' _iucr_refine_instructions_details ; TITL 3bb(C4 in P2(1)/c CELL 1.54178 9.6417 15.1369 16.1772 90.000 97.283 90.000 ZERR 4.00 0.0006 0.0011 0.0011 0.000 0.003 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 92 112 16 16 4 OMIT 1 1 0 L.S. 11 ACTA BOND $H FMAP 2 PLAN 6 SIZE 0.174 0.339 0.352 HTAB CONF TEMP -100.000 WGHT 0.043300 0.784500 FVAR 0.10969 C1 1 0.340826 0.202336 0.291005 11.00000 0.02826 0.01886 = 0.03120 0.00238 0.00312 0.00163 C2 1 0.249447 0.178093 0.347046 11.00000 0.03322 0.02895 = 0.03142 0.00458 0.00707 0.00326 AFIX 43 H2A 2 0.259762 0.202404 0.401621 11.00000 -1.20000 AFIX 0 C3 1 0.143639 0.118464 0.322848 11.00000 0.02904 0.03440 = 0.04273 0.00875 0.00906 0.00032 AFIX 43 H3A 2 0.080379 0.101797 0.360574 11.00000 -1.20000 AFIX 0 C4 1 0.130237 0.082995 0.243040 11.00000 0.02900 0.03240 = 0.04906 0.00218 0.00390 -0.00626 AFIX 43 H4A 2 0.059479 0.040484 0.226905 11.00000 -1.20000 AFIX 0 C5 1 0.218954 0.109046 0.186986 11.00000 0.03421 0.03119 = 0.03922 -0.00554 0.00460 -0.00481 AFIX 43 H5A 2 0.207671 0.084389 0.132545 11.00000 -1.20000 AFIX 0 C6 1 0.325789 0.171359 0.208738 11.00000 0.02768 0.02278 = 0.03333 -0.00061 0.00504 0.00129 C7 1 0.475558 0.269608 0.148617 11.00000 0.02737 0.02787 = 0.02397 -0.00226 0.00413 0.00007 C8 1 0.596211 0.400926 0.088924 11.00000 0.03464 0.02872 = 0.02630 -0.00184 0.00492 -0.00490 C9 1 0.552131 0.420507 0.161968 11.00000 0.03482 0.02462 = 0.02659 -0.00074 0.00490 -0.00216 AFIX 43 H9A 2 0.561841 0.477712 0.186164 11.00000 -1.20000 AFIX 0 C10 1 0.488292 0.347347 0.201276 11.00000 0.02761 0.02232 = 0.02486 -0.00080 0.00303 0.00008 C11 1 0.456872 0.342960 0.282641 11.00000 0.02407 0.02092 = 0.02452 -0.00018 0.00125 -0.00109 C12 1 0.391787 0.498232 0.300946 11.00000 0.03789 0.02039 = 0.02698 0.00175 0.00673 0.00148 AFIX 23 H12A 2 0.370645 0.497101 0.239450 11.00000 -1.20000 H12B 2 0.473706 0.537120 0.315831 11.00000 -1.20000 AFIX 0 C13 1 0.266945 0.534673 0.338459 11.00000 0.03708 0.02872 = 0.03070 0.00049 0.00327 0.00729 AFIX 23 H13A 2 0.250754 0.596762 0.320554 11.00000 -1.20000 H13B 2 0.182492 0.500162 0.317600 11.00000 -1.20000 AFIX 0 C14 1 0.437025 0.401207 0.422876 11.00000 0.04330 0.02734 = 0.02142 -0.00064 0.00114 0.00607 AFIX 23 H14A 2 0.521239 0.433412 0.448167 11.00000 -1.20000 H14B 2 0.447778 0.338306 0.439203 11.00000 -1.20000 AFIX 0 C15 1 0.309071 0.438950 0.454980 11.00000 0.04578 0.03333 = 0.02548 0.00080 0.00938 0.00051 AFIX 23 H15A 2 0.225712 0.403963 0.433036 11.00000 -1.20000 H15B 2 0.320257 0.435352 0.516571 11.00000 -1.20000 AFIX 0 C16 1 0.172751 0.570624 0.464553 11.00000 0.05490 0.05599 = 0.04387 -0.00242 0.01858 0.01906 AFIX 33 H16A 2 0.190126 0.567293 0.525486 11.00000 -1.50000 H16B 2 0.086365 0.538824 0.444751 11.00000 -1.50000 H16C 2 0.163359 0.632627 0.447315 11.00000 -1.50000 AFIX 0 C17 1 0.673583 0.458879 0.035205 11.00000 0.04953 0.03770 = 0.03142 -0.00235 0.01210 -0.01117 AFIX 33 H17A 2 0.686038 0.517652 0.060462 11.00000 -1.50000 H17B 2 0.620003 0.463938 -0.020264 11.00000 -1.50000 H17C 2 0.765308 0.432947 0.030285 11.00000 -1.50000 AFIX 0 C18 1 0.584665 0.214636 0.341155 11.00000 0.03138 0.02460 = 0.02082 -0.00039 0.00467 0.00105 C19 1 0.825130 0.243331 0.367122 11.00000 0.02916 0.04036 = 0.03939 0.00389 0.00025 0.00465 AFIX 23 H19A 2 0.888265 0.281893 0.404296 11.00000 -1.20000 H19B 2 0.828464 0.183206 0.391377 11.00000 -1.20000 AFIX 0 C20 1 0.939129 0.313215 0.263948 11.00000 0.03009 0.03217 = 0.04624 0.00055 0.00192 0.00197 C21 1 0.970722 0.303656 0.176623 11.00000 0.03665 0.04581 = 0.04609 -0.00167 0.00533 0.00007 AFIX 23 H21A 2 0.882682 0.310095 0.138353 11.00000 -1.20000 H21B 2 1.006939 0.243345 0.169262 11.00000 -1.20000 AFIX 0 C22 1 1.075960 0.369941 0.152201 11.00000 0.04840 0.05567 = 0.05149 0.00632 0.00986 -0.00569 AFIX 23 H22A 2 1.037268 0.430238 0.155501 11.00000 -1.20000 H22B 2 1.162229 0.366339 0.192373 11.00000 -1.20000 AFIX 0 C23 1 1.112496 0.354415 0.065123 11.00000 0.06579 0.09129 = 0.05772 0.01317 0.02003 -0.00709 AFIX 33 H23A 2 1.180418 0.398866 0.052159 11.00000 -1.50000 H23B 2 1.027728 0.358991 0.024953 11.00000 -1.50000 H23C 2 1.153003 0.295332 0.061857 11.00000 -1.50000 AFIX 0 N1 3 0.459548 0.256244 0.318748 11.00000 0.02842 0.01947 = 0.02583 0.00140 0.00312 0.00065 N2 3 0.408390 0.194628 0.148083 11.00000 0.03128 0.02730 = 0.03086 -0.00597 0.00643 -0.00375 N3 3 0.424732 0.408690 0.331872 11.00000 0.03242 0.02108 = 0.02169 0.00034 0.00342 0.00141 N4 3 0.289214 0.530708 0.429059 11.00000 0.03771 0.03067 = 0.02860 -0.00311 0.00730 0.00608 O1 4 0.601498 0.136107 0.347452 11.00000 0.03947 0.02228 = 0.03654 0.00164 0.00261 0.00538 O2 4 0.686582 0.276531 0.359899 11.00000 0.02786 0.02713 = 0.03317 -0.00155 0.00164 0.00122 O3 4 0.868683 0.240910 0.286954 11.00000 0.03274 0.03493 = 0.04715 -0.00496 0.00997 -0.00087 O4 4 0.970071 0.373771 0.310025 11.00000 0.06944 0.03981 = 0.05214 -0.00786 0.01086 -0.01264 S1 5 0.558037 0.291578 0.058804 11.00000 0.04277 0.03266 = 0.02786 -0.00846 0.01284 -0.00960 HKLF 4 REM 3bb(C4 in P2(1)/c REM R1 = 0.0317 for 3823 Fo > 4sig(Fo) and 0.0340 for all 4100 data REM 289 parameters refined using 0 restraints END WGHT 0.0413 0.7990 REM Highest difference peak 0.240, deepest hole -0.216, 1-sigma level 0.034 Q1 1 0.5138 0.2792 0.1112 11.00000 0.05 0.24 Q2 1 0.5140 0.3850 0.1881 11.00000 0.05 0.20 Q3 1 0.3204 0.1994 0.2463 11.00000 0.05 0.19 Q4 1 0.4870 0.3094 0.1765 11.00000 0.05 0.19 Q5 1 0.5825 0.3539 0.0749 11.00000 0.05 0.19 Q6 1 0.4606 0.2950 0.3051 11.00000 0.05 0.18 ; _audit_update_record ; 2013-02-12 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ;(butyryloxy) methyl 2-methyl-4-(4-methylpiperazin-1-yl)-4H-benzo[b]thieno[2,3-e][1,4]diazepine-5-carboxylate ; _chemical_name_common ? _chemical_melting_point 427 _chemical_formula_moiety 'C23 H28 N4 O4 S' _chemical_formula_sum 'C23 H28 N4 O4 S' _chemical_formula_weight 456.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 9.6417(6) _cell_length_b 15.1369(11) _cell_length_c 16.1772(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.283(3) _cell_angle_gamma 90.00 _cell_volume 2341.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7249 _cell_measurement_theta_min 4.01 _cell_measurement_theta_max 68.05 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 1.531 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6148 _exptl_absorpt_correction_T_max 0.7765 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15312 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.01 _diffrn_reflns_theta_max 68.33 _reflns_number_total 4100 _reflns_number_gt 3823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+0.7845P] 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 4100 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0856 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C1 C 0.34083(13) 0.20234(8) 0.29101(8) 0.0262(3) Uani 1 1 d . . . C2 C 0.24945(14) 0.17809(9) 0.34705(9) 0.0309(3) Uani 1 1 d . . . H2A H 0.2598 0.2024 0.4016 0.037 Uiso 1 1 calc R . . C3 C 0.14364(14) 0.11846(10) 0.32285(9) 0.0350(3) Uani 1 1 d . . . H3A H 0.0804 0.1018 0.3606 0.042 Uiso 1 1 calc R . . C4 C 0.13024(15) 0.08300(10) 0.24304(10) 0.0369(3) Uani 1 1 d . . . H4A H 0.0595 0.0405 0.2269 0.044 Uiso 1 1 calc R . . C5 C 0.21895(15) 0.10905(10) 0.18699(9) 0.0349(3) Uani 1 1 d . . . H5A H 0.2077 0.0844 0.1325 0.042 Uiso 1 1 calc R . . C6 C 0.32579(13) 0.17136(9) 0.20874(8) 0.0278(3) Uani 1 1 d . . . C7 C 0.47556(13) 0.26961(9) 0.14862(8) 0.0263(3) Uani 1 1 d . . . C8 C 0.59621(14) 0.40093(9) 0.08892(8) 0.0298(3) Uani 1 1 d . . . C9 C 0.55213(14) 0.42051(9) 0.16197(8) 0.0286(3) Uani 1 1 d . . . H9A H 0.5618 0.4777 0.1862 0.034 Uiso 1 1 calc R . . C10 C 0.48829(13) 0.34735(8) 0.20128(8) 0.0250(3) Uani 1 1 d . . . C11 C 0.45687(12) 0.34296(8) 0.28264(8) 0.0233(3) Uani 1 1 d . . . C12 C 0.39179(14) 0.49823(9) 0.30095(8) 0.0282(3) Uani 1 1 d . . . H12A H 0.3706 0.4971 0.2395 0.034 Uiso 1 1 calc R . . H12B H 0.4737 0.5371 0.3158 0.034 Uiso 1 1 calc R . . C13 C 0.26694(14) 0.53467(10) 0.33846(8) 0.0323(3) Uani 1 1 d . . . H13A H 0.2508 0.5968 0.3206 0.039 Uiso 1 1 calc R . . H13B H 0.1825 0.5002 0.3176 0.039 Uiso 1 1 calc R . . C14 C 0.43703(15) 0.40121(9) 0.42288(8) 0.0309(3) Uani 1 1 d . . . H14A H 0.5212 0.4334 0.4482 0.037 Uiso 1 1 calc R . . H14B H 0.4478 0.3383 0.4392 0.037 Uiso 1 1 calc R . . C15 C 0.30907(16) 0.43895(10) 0.45498(8) 0.0344(3) Uani 1 1 d . . . H15A H 0.2257 0.4040 0.4330 0.041 Uiso 1 1 calc R . . H15B H 0.3203 0.4354 0.5166 0.041 Uiso 1 1 calc R . . C16 C 0.17275(19) 0.57062(13) 0.46455(11) 0.0505(4) Uani 1 1 d . . . H16A H 0.1901 0.5673 0.5255 0.076 Uiso 1 1 calc R . . H16B H 0.0864 0.5388 0.4448 0.076 Uiso 1 1 calc R . . H16C H 0.1634 0.6326 0.4473 0.076 Uiso 1 1 calc R . . C17 C 0.67358(16) 0.45888(10) 0.03520(9) 0.0389(3) Uani 1 1 d . . . H17A H 0.6860 0.5177 0.0605 0.058 Uiso 1 1 calc R . . H17B H 0.6200 0.4639 -0.0203 0.058 Uiso 1 1 calc R . . H17C H 0.7653 0.4329 0.0303 0.058 Uiso 1 1 calc R . . C18 C 0.58467(13) 0.21464(8) 0.34116(8) 0.0255(3) Uani 1 1 d . . . C19 C 0.82513(14) 0.24333(11) 0.36712(9) 0.0367(3) Uani 1 1 d . . . H19A H 0.8883 0.2819 0.4043 0.044 Uiso 1 1 calc R . . H19B H 0.8285 0.1832 0.3914 0.044 Uiso 1 1 calc R . . C20 C 0.93913(14) 0.31321(10) 0.26395(10) 0.0364(3) Uani 1 1 d . . . C21 C 0.97072(16) 0.30366(11) 0.17662(10) 0.0428(4) Uani 1 1 d . . . H21A H 0.8827 0.3101 0.1384 0.051 Uiso 1 1 calc R . . H21B H 1.0069 0.2433 0.1693 0.051 Uiso 1 1 calc R . . C22 C 1.07596(18) 0.36994(13) 0.15220(11) 0.0516(4) Uani 1 1 d . . . H22A H 1.0373 0.4302 0.1555 0.062 Uiso 1 1 calc R . . H22B H 1.1622 0.3663 0.1924 0.062 Uiso 1 1 calc R . . C23 C 1.1125(2) 0.35441(17) 0.06512(13) 0.0706(6) Uani 1 1 d . . . H23A H 1.1804 0.3989 0.0522 0.106 Uiso 1 1 calc R . . H23B H 1.0277 0.3590 0.0250 0.106 Uiso 1 1 calc R . . H23C H 1.1530 0.2953 0.0619 0.106 Uiso 1 1 calc R . . N1 N 0.45955(11) 0.25624(7) 0.31875(6) 0.0246(2) Uani 1 1 d . . . N2 N 0.40839(12) 0.19463(8) 0.14808(7) 0.0296(3) Uani 1 1 d . . . N3 N 0.42473(11) 0.40869(7) 0.33187(6) 0.0251(2) Uani 1 1 d . . . N4 N 0.28921(12) 0.53071(8) 0.42906(7) 0.0321(3) Uani 1 1 d . . . O1 O 0.60150(10) 0.13611(6) 0.34745(6) 0.0330(2) Uani 1 1 d . . . O2 O 0.68658(9) 0.27653(6) 0.35990(6) 0.0296(2) Uani 1 1 d . . . O3 O 0.86868(10) 0.24091(7) 0.28695(7) 0.0379(2) Uani 1 1 d . . . O4 O 0.97007(14) 0.37377(8) 0.31003(8) 0.0535(3) Uani 1 1 d . . . S1 S 0.55804(4) 0.29158(2) 0.05880(2) 0.03371(11) Uani 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 C1 0.0283(6) 0.0189(6) 0.0312(7) 0.0024(5) 0.0031(5) 0.0016(5) C2 0.0332(7) 0.0289(7) 0.0314(7) 0.0046(5) 0.0071(5) 0.0033(5) C3 0.0290(7) 0.0344(8) 0.0427(8) 0.0088(6) 0.0091(6) 0.0003(6) C4 0.0290(7) 0.0324(8) 0.0491(9) 0.0022(6) 0.0039(6) -0.0063(6) C5 0.0342(7) 0.0312(8) 0.0392(8) -0.0055(6) 0.0046(6) -0.0048(6) C6 0.0277(6) 0.0228(7) 0.0333(7) -0.0006(5) 0.0050(5) 0.0013(5) C7 0.0274(6) 0.0279(7) 0.0240(6) -0.0023(5) 0.0041(5) 0.0001(5) C8 0.0346(7) 0.0287(7) 0.0263(7) -0.0018(5) 0.0049(5) -0.0049(5) C9 0.0348(7) 0.0246(7) 0.0266(7) -0.0007(5) 0.0049(5) -0.0022(5) C10 0.0276(6) 0.0223(7) 0.0249(6) -0.0008(5) 0.0030(5) 0.0001(5) C11 0.0241(6) 0.0209(6) 0.0245(6) -0.0002(5) 0.0012(5) -0.0011(5) C12 0.0379(7) 0.0204(7) 0.0270(7) 0.0017(5) 0.0067(5) 0.0015(5) C13 0.0371(7) 0.0287(7) 0.0307(7) 0.0005(5) 0.0033(6) 0.0073(6) C14 0.0433(8) 0.0273(7) 0.0214(6) -0.0006(5) 0.0011(5) 0.0061(6) C15 0.0458(8) 0.0333(8) 0.0255(7) 0.0008(5) 0.0094(6) 0.0005(6) C16 0.0549(10) 0.0560(11) 0.0439(9) -0.0024(8) 0.0186(8) 0.0191(8) C17 0.0495(8) 0.0377(9) 0.0314(8) -0.0024(6) 0.0121(6) -0.0112(7) C18 0.0314(6) 0.0246(7) 0.0208(6) -0.0004(5) 0.0047(5) 0.0010(5) C19 0.0292(7) 0.0404(9) 0.0394(8) 0.0039(6) 0.0002(6) 0.0046(6) C20 0.0301(7) 0.0322(8) 0.0462(9) 0.0005(6) 0.0019(6) 0.0020(6) C21 0.0367(8) 0.0458(9) 0.0461(9) -0.0017(7) 0.0053(6) 0.0001(7) C22 0.0484(9) 0.0557(11) 0.0515(10) 0.0063(8) 0.0099(8) -0.0057(8) C23 0.0658(12) 0.0913(17) 0.0577(12) 0.0132(11) 0.0200(10) -0.0071(12) N1 0.0284(5) 0.0195(5) 0.0258(6) 0.0014(4) 0.0031(4) 0.0006(4) N2 0.0313(6) 0.0273(6) 0.0309(6) -0.0060(4) 0.0064(5) -0.0038(5) N3 0.0324(6) 0.0211(6) 0.0217(5) 0.0003(4) 0.0034(4) 0.0014(4) N4 0.0377(6) 0.0307(6) 0.0286(6) -0.0031(5) 0.0073(5) 0.0061(5) O1 0.0395(5) 0.0223(5) 0.0365(5) 0.0016(4) 0.0026(4) 0.0054(4) O2 0.0279(5) 0.0271(5) 0.0332(5) -0.0015(4) 0.0016(4) 0.0012(4) O3 0.0327(5) 0.0349(6) 0.0471(6) -0.0050(4) 0.0100(4) -0.0009(4) O4 0.0694(8) 0.0398(7) 0.0521(7) -0.0079(5) 0.0109(6) -0.0126(6) S1 0.0428(2) 0.0327(2) 0.02786(19) -0.00846(13) 0.01284(14) -0.00960(14) _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 C1 C2 1.3912(19) . ? C1 C6 1.4011(19) . ? C1 N1 1.4308(16) . ? C2 C3 1.381(2) . ? C2 H2A 0.9500 . ? C3 C4 1.389(2) . ? C3 H3A 0.9500 . ? C4 C5 1.381(2) . ? C4 H4A 0.9500 . ? C5 C6 1.4081(19) . ? C5 H5A 0.9500 . ? C6 N2 1.3854(17) . ? C7 N2 1.3062(17) . ? C7 C10 1.4488(18) . ? C7 S1 1.7740(13) . ? C8 C9 1.3387(19) . ? C8 C17 1.4985(19) . ? C8 S1 1.7513(14) . ? C9 C10 1.4522(18) . ? C9 H9A 0.9500 . ? C10 C11 1.3892(18) . ? C11 N3 1.3352(16) . ? C11 N1 1.4356(16) . ? C12 N3 1.4656(16) . ? C12 C13 1.5188(18) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.4554(18) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N3 1.4663(17) . ? C14 C15 1.5102(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N4 1.4565(19) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N4 1.4557(18) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O1 1.2023(16) . ? C18 O2 1.3637(16) . ? C18 N1 1.3684(16) . ? C19 O3 1.4134(18) . ? C19 O2 1.4181(16) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O4 1.1952(19) . ? C20 O3 1.3645(18) . ? C20 C21 1.489(2) . ? C21 C22 1.515(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.513(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C1 C6 122.20(13) . . ? C2 C1 N1 119.58(12) . . ? C6 C1 N1 118.11(11) . . ? C3 C2 C1 119.59(13) . . ? C3 C2 H2A 120.2 . . ? C1 C2 H2A 120.2 . . ? C2 C3 C4 119.63(13) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C5 C4 C3 120.51(13) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 121.45(14) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? N2 C6 C1 126.02(12) . . ? N2 C6 C5 117.47(12) . . ? C1 C6 C5 116.48(12) . . ? N2 C7 C10 135.61(12) . . ? N2 C7 S1 115.52(10) . . ? C10 C7 S1 108.42(9) . . ? C9 C8 C17 128.27(13) . . ? C9 C8 S1 112.07(10) . . ? C17 C8 S1 119.63(10) . . ? C8 C9 C10 114.66(12) . . ? C8 C9 H9A 122.7 . . ? C10 C9 H9A 122.7 . . ? C11 C10 C7 120.39(11) . . ? C11 C10 C9 127.36(12) . . ? C7 C10 C9 111.77(11) . . ? N3 C11 C10 128.65(11) . . ? N3 C11 N1 115.61(11) . . ? C10 C11 N1 115.75(11) . . ? N3 C12 C13 110.36(11) . . ? N3 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? N3 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N4 C13 C12 111.36(11) . . ? N4 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? N4 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? N3 C14 C15 110.52(11) . . ? N3 C14 H14A 109.5 . . ? C15 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? N4 C15 C14 110.19(11) . . ? N4 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? N4 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N4 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C18 O2 125.08(12) . . ? O1 C18 N1 125.63(12) . . ? O2 C18 N1 109.20(11) . . ? O3 C19 O2 108.66(11) . . ? O3 C19 H19A 110.0 . . ? O2 C19 H19A 110.0 . . ? O3 C19 H19B 110.0 . . ? O2 C19 H19B 110.0 . . ? H19A C19 H19B 108.3 . . ? O4 C20 O3 122.59(15) . . ? O4 C20 C21 126.95(15) . . ? O3 C20 C21 110.46(13) . . ? C20 C21 C22 114.04(14) . . ? C20 C21 H21A 108.7 . . ? C22 C21 H21A 108.7 . . ? C20 C21 H21B 108.7 . . ? C22 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? C23 C22 C21 112.50(16) . . ? C23 C22 H22A 109.1 . . ? C21 C22 H22A 109.1 . . ? C23 C22 H22B 109.1 . . ? C21 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C18 N1 C1 117.64(10) . . ? C18 N1 C11 119.89(10) . . ? C1 N1 C11 114.92(10) . . ? C7 N2 C6 123.04(11) . . ? C11 N3 C12 122.83(11) . . ? C11 N3 C14 123.09(11) . . ? C12 N3 C14 113.62(10) . . ? C13 N4 C16 110.94(12) . . ? C13 N4 C15 109.06(11) . . ? C16 N4 C15 111.23(12) . . ? C18 O2 C19 114.81(11) . . ? C20 O3 C19 116.46(12) . . ? C8 S1 C7 92.84(6) . . ? 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 C6 C1 C2 C3 3.0(2) . . . . ? N1 C1 C2 C3 -173.04(12) . . . . ? C1 C2 C3 C4 0.4(2) . . . . ? C2 C3 C4 C5 -2.1(2) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C2 C1 C6 N2 177.39(13) . . . . ? N1 C1 C6 N2 -6.5(2) . . . . ? C2 C1 C6 C5 -4.4(2) . . . . ? N1 C1 C6 C5 171.65(11) . . . . ? C4 C5 C6 N2 -178.98(13) . . . . ? C4 C5 C6 C1 2.7(2) . . . . ? C17 C8 C9 C10 -175.94(14) . . . . ? S1 C8 C9 C10 2.23(16) . . . . ? N2 C7 C10 C11 20.7(2) . . . . ? S1 C7 C10 C11 -167.63(10) . . . . ? N2 C7 C10 C9 -166.61(15) . . . . ? S1 C7 C10 C9 5.02(13) . . . . ? C8 C9 C10 C11 167.18(13) . . . . ? C8 C9 C10 C7 -4.84(17) . . . . ? C7 C10 C11 N3 -159.55(12) . . . . ? C9 C10 C11 N3 29.0(2) . . . . ? C7 C10 C11 N1 20.59(17) . . . . ? C9 C10 C11 N1 -150.82(12) . . . . ? N3 C12 C13 N4 54.54(15) . . . . ? N3 C14 C15 N4 -57.32(15) . . . . ? O4 C20 C21 C22 12.4(2) . . . . ? O3 C20 C21 C22 -166.85(13) . . . . ? C20 C21 C22 C23 176.23(16) . . . . ? O1 C18 N1 C1 -7.74(19) . . . . ? O2 C18 N1 C1 175.67(10) . . . . ? O1 C18 N1 C11 -155.93(12) . . . . ? O2 C18 N1 C11 27.49(15) . . . . ? C2 C1 N1 C18 96.47(14) . . . . ? C6 C1 N1 C18 -79.72(15) . . . . ? C2 C1 N1 C11 -113.79(13) . . . . ? C6 C1 N1 C11 70.02(15) . . . . ? N3 C11 N1 C18 -107.34(13) . . . . ? C10 C11 N1 C18 72.54(15) . . . . ? N3 C11 N1 C1 103.65(13) . . . . ? C10 C11 N1 C1 -76.47(14) . . . . ? C10 C7 N2 C6 -1.6(2) . . . . ? S1 C7 N2 C6 -172.79(10) . . . . ? C1 C6 N2 C7 -26.0(2) . . . . ? C5 C6 N2 C7 155.83(13) . . . . ? C10 C11 N3 C12 11.8(2) . . . . ? N1 C11 N3 C12 -168.33(11) . . . . ? C10 C11 N3 C14 -159.90(13) . . . . ? N1 C11 N3 C14 19.97(17) . . . . ? C13 C12 N3 C11 136.98(12) . . . . ? C13 C12 N3 C14 -50.60(15) . . . . ? C15 C14 N3 C11 -135.24(13) . . . . ? C15 C14 N3 C12 52.36(15) . . . . ? C12 C13 N4 C16 176.56(13) . . . . ? C12 C13 N4 C15 -60.60(15) . . . . ? C14 C15 N4 C13 61.69(15) . . . . ? C14 C15 N4 C16 -175.64(12) . . . . ? O1 C18 O2 C19 16.01(18) . . . . ? N1 C18 O2 C19 -167.38(10) . . . . ? O3 C19 O2 C18 85.56(14) . . . . ? O4 C20 O3 C19 4.1(2) . . . . ? C21 C20 O3 C19 -176.62(12) . . . . ? O2 C19 O3 C20 93.18(14) . . . . ? C9 C8 S1 C7 0.69(11) . . . . ? C17 C8 S1 C7 179.04(12) . . . . ? N2 C7 S1 C8 170.23(11) . . . . ? C10 C7 S1 C8 -3.29(10) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 68.33 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.240 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 924294' ####################################################################### # # 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_3bc(C6) #TrackingRef '17686_web_deposit_cif_file_1_TarekAZeidan_1360705814.3bc-C6.cif' _cell_special_details ? #Added by publCIF _iucr_refine_instructions_details ; TITL 3bc(C6) in P2(1)/c CELL 1.54178 14.4300 14.9488 16.2240 90.000 92.753 90.000 ZERR 4.00 0.0015 0.0015 0.0014 0.000 0.007 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 140 208 16 16 4 OMIT 10 1 14 L.S. 9 ACTA BOND $H FMAP 2 PLAN 6 SIZE 0.101 0.161 0.318 HTAB CONF TEMP -100.000 WGHT 0.052000 0.370000 FVAR 0.07441 C1 1 0.608364 0.705232 1.299356 11.00000 0.03316 0.02012 = 0.02952 0.00076 0.00197 -0.00072 C2 1 0.669990 0.680412 1.363462 11.00000 0.04212 0.02983 = 0.02845 0.00226 -0.00051 0.00063 AFIX 43 H2A 2 0.663455 0.704007 1.417242 11.00000 -1.20000 AFIX 0 C3 1 0.741035 0.621188 1.348914 11.00000 0.03787 0.03674 = 0.03819 0.00772 -0.00481 0.00264 AFIX 43 H3A 2 0.783825 0.604276 1.392465 11.00000 -1.20000 AFIX 0 C4 1 0.749324 0.586613 1.270059 11.00000 0.03211 0.03079 = 0.04500 -0.00096 0.00018 0.00351 AFIX 43 H4A 2 0.796435 0.544044 1.260302 11.00000 -1.20000 AFIX 0 C5 1 0.689835 0.613574 1.206075 11.00000 0.03671 0.03177 = 0.03605 -0.00592 0.00143 0.00144 AFIX 43 H5A 2 0.697117 0.589669 1.152518 11.00000 -1.20000 AFIX 0 C6 1 0.618268 0.675853 1.218012 11.00000 0.03307 0.02395 = 0.02948 -0.00231 -0.00101 -0.00250 C7 1 0.518495 0.776746 1.144426 11.00000 0.03161 0.02735 = 0.02226 -0.00229 0.00074 -0.00251 C8 1 0.436919 0.910770 1.075181 11.00000 0.03556 0.02845 = 0.02398 0.00135 0.00260 -0.00047 C9 1 0.467683 0.929462 1.152823 11.00000 0.03983 0.02227 = 0.02448 -0.00036 0.00217 -0.00016 AFIX 43 H9A 2 0.461816 0.987032 1.176818 11.00000 -1.20000 AFIX 0 C10 1 0.510659 0.854458 1.197108 11.00000 0.03316 0.02230 = 0.02293 -0.00041 0.00170 -0.00120 C11 1 0.532222 0.848211 1.281516 11.00000 0.03050 0.01953 = 0.02430 0.00015 0.00377 0.00082 C12 1 0.572653 1.005468 1.309664 11.00000 0.04709 0.02106 = 0.02570 0.00075 -0.00050 -0.00186 AFIX 23 H12A 2 0.515640 1.041763 1.313531 11.00000 -1.20000 H12B 2 0.590074 1.005618 1.251383 11.00000 -1.20000 AFIX 0 C13 1 0.650179 1.046970 1.363198 11.00000 0.04534 0.02655 = 0.03128 -0.00248 0.00399 -0.00533 AFIX 23 H13A 2 0.709408 1.016835 1.352170 11.00000 -1.20000 H13B 2 0.656325 1.110919 1.348568 11.00000 -1.20000 AFIX 0 C14 1 0.623820 0.945618 1.472612 11.00000 0.04401 0.02984 = 0.02441 -0.00116 -0.00319 0.00155 AFIX 23 H14A 2 0.614358 0.940258 1.532444 11.00000 -1.20000 H14B 2 0.681581 0.913411 1.460599 11.00000 -1.20000 AFIX 0 C15 1 0.543126 0.903964 1.424571 11.00000 0.04280 0.02687 = 0.02126 -0.00114 0.00511 -0.00280 AFIX 23 H15A 2 0.539036 0.839726 1.438785 11.00000 -1.20000 H15B 2 0.484817 0.933260 1.439729 11.00000 -1.20000 AFIX 0 C16 1 0.705597 1.082929 1.501120 11.00000 0.04915 0.04406 = 0.04259 -0.01066 -0.00438 -0.00789 AFIX 33 H16A 2 0.692440 1.076807 1.559552 11.00000 -1.50000 H16B 2 0.708027 1.146502 1.486636 11.00000 -1.50000 H16C 2 0.765400 1.054874 1.491114 11.00000 -1.50000 AFIX 0 C17 1 0.384465 0.970561 1.015322 11.00000 0.04380 0.03355 = 0.02810 0.00296 -0.00093 0.00298 AFIX 33 H17A 2 0.375959 1.029351 1.040597 11.00000 -1.50000 H17B 2 0.323702 0.944130 1.000831 11.00000 -1.50000 H17C 2 0.419423 0.977316 0.965382 11.00000 -1.50000 AFIX 0 C18 1 0.446595 0.719909 1.327610 11.00000 0.03733 0.02551 = 0.01666 -0.00265 0.00079 -0.00290 C19 1 0.287249 0.752234 1.328768 11.00000 0.03425 0.04474 = 0.03026 -0.00360 0.00273 -0.00728 AFIX 23 H19A 2 0.246210 0.793439 1.357884 11.00000 -1.20000 H19B 2 0.283932 0.692460 1.354731 11.00000 -1.20000 AFIX 0 C20 1 0.205627 0.815202 1.211667 11.00000 0.03490 0.03772 = 0.03725 -0.00274 0.00327 -0.00626 C21 1 0.198308 0.806270 1.119627 11.00000 0.03854 0.05068 = 0.03626 -0.00334 0.00272 0.00016 AFIX 23 H21A 2 0.181632 0.743579 1.105974 11.00000 -1.20000 H21B 2 0.260341 0.817627 1.098258 11.00000 -1.20000 AFIX 0 C22 1 0.129105 0.867164 1.074171 11.00000 0.04128 0.04530 = 0.03870 -0.00255 0.00177 -0.00251 AFIX 23 H22A 2 0.144217 0.930442 1.086809 11.00000 -1.20000 H22B 2 0.065808 0.854839 1.092261 11.00000 -1.20000 AFIX 0 C23 1 0.132937 0.850750 0.981571 11.00000 0.03875 0.05178 = 0.03785 -0.00266 -0.00088 -0.00249 AFIX 23 H23A 2 0.196049 0.866475 0.965034 11.00000 -1.20000 H23B 2 0.124652 0.785811 0.971774 11.00000 -1.20000 AFIX 0 C24 1 0.063900 0.899830 0.924581 11.00000 0.04227 0.05176 = 0.04292 -0.00270 -0.00052 0.00059 AFIX 23 H24A 2 0.070620 0.965150 0.932964 11.00000 -1.20000 H24B 2 -0.000034 0.882709 0.937617 11.00000 -1.20000 AFIX 0 C25 1 0.080661 0.876551 0.834730 11.00000 0.03756 0.05007 = 0.04222 -0.00125 -0.00104 0.00199 AFIX 23 H25A 2 0.141471 0.901721 0.820985 11.00000 -1.20000 H25B 2 0.085330 0.810673 0.830256 11.00000 -1.20000 AFIX 0 C26 1 0.008738 0.908539 0.770458 11.00000 0.04082 0.05203 = 0.04328 -0.00035 -0.00194 0.00540 AFIX 23 H26A 2 0.007382 0.974752 0.770295 11.00000 -1.20000 H26B 2 -0.053255 0.886965 0.784990 11.00000 -1.20000 AFIX 0 C27 1 0.029540 0.875053 0.684558 11.00000 0.03857 0.05026 = 0.04337 0.00083 -0.00163 0.00408 AFIX 23 H27A 2 0.090817 0.898620 0.670188 11.00000 -1.20000 H27B 2 0.034348 0.809015 0.686445 11.00000 -1.20000 AFIX 0 C28 1 -0.041362 0.900535 0.616102 11.00000 0.04291 0.05202 = 0.04220 -0.00146 -0.00219 0.00783 AFIX 23 H28A 2 -0.043426 0.966523 0.611184 11.00000 -1.20000 H28B 2 -0.103471 0.880000 0.631365 11.00000 -1.20000 AFIX 0 C29 1 -0.020047 0.860688 0.532740 11.00000 0.04251 0.05117 = 0.04323 -0.00017 -0.00106 0.00633 AFIX 23 H29A 2 0.041538 0.882275 0.517082 11.00000 -1.20000 H29B 2 -0.016497 0.794795 0.538135 11.00000 -1.20000 AFIX 0 C30 1 -0.091255 0.883875 0.464272 11.00000 0.04545 0.05279 = 0.04042 -0.00081 -0.00006 0.00775 AFIX 23 H30A 2 -0.093056 0.949753 0.458159 11.00000 -1.20000 H30B 2 -0.153031 0.864521 0.481470 11.00000 -1.20000 AFIX 0 C31 1 -0.075028 0.842987 0.380301 11.00000 0.04742 0.04998 = 0.04387 -0.00386 -0.00089 0.00797 AFIX 23 H31A 2 -0.012897 0.860856 0.362813 11.00000 -1.20000 H31B 2 -0.075998 0.776965 0.384968 11.00000 -1.20000 AFIX 0 C32 1 -0.147833 0.872256 0.315165 11.00000 0.04559 0.04464 = 0.04175 -0.00187 0.00052 0.00245 AFIX 23 H32A 2 -0.209638 0.856046 0.334562 11.00000 -1.20000 H32B 2 -0.145651 0.938284 0.310963 11.00000 -1.20000 AFIX 0 C33 1 -0.139397 0.833822 0.229799 11.00000 0.05413 0.04986 = 0.04173 -0.00160 -0.00062 0.00289 AFIX 23 H33A 2 -0.143805 0.767821 0.232770 11.00000 -1.20000 H33B 2 -0.077583 0.849039 0.209829 11.00000 -1.20000 AFIX 0 C34 1 -0.213698 0.868412 0.168485 11.00000 0.06047 0.05683 = 0.04421 0.00142 -0.00317 -0.00130 AFIX 23 H34A 2 -0.275268 0.855412 0.190105 11.00000 -1.20000 H34B 2 -0.207619 0.934222 0.164569 11.00000 -1.20000 AFIX 0 C35 1 -0.210397 0.829393 0.082985 11.00000 0.10013 0.09068 = 0.04464 -0.00159 -0.01169 0.00831 AFIX 33 H35A 2 -0.260093 0.855520 0.047396 11.00000 -1.50000 H35B 2 -0.218725 0.764413 0.085663 11.00000 -1.50000 H35C 2 -0.150228 0.842883 0.060320 11.00000 -1.50000 AFIX 0 N1 3 0.529783 0.759917 1.315505 11.00000 0.03432 0.01906 = 0.02411 0.00047 0.00203 -0.00018 N2 3 0.563019 0.700484 1.149606 11.00000 0.03559 0.02764 = 0.02846 -0.00608 -0.00066 0.00273 N3 3 0.554055 0.913537 1.335327 11.00000 0.03808 0.02166 = 0.02021 -0.00011 0.00154 -0.00136 N4 3 0.632900 1.039383 1.450844 11.00000 0.03998 0.02824 = 0.02667 -0.00453 -0.00094 -0.00243 O1 4 0.433808 0.640837 1.335253 11.00000 0.04773 0.02363 = 0.03143 -0.00057 0.00376 -0.00802 O2 4 0.380024 0.784378 1.334095 11.00000 0.03160 0.02981 = 0.03071 -0.00410 0.00324 -0.00322 O3 4 0.258542 0.746913 1.243910 11.00000 0.04102 0.04542 = 0.03246 -0.00927 -0.00273 0.00134 O4 4 0.171112 0.871629 1.252537 11.00000 0.07535 0.04389 = 0.04311 -0.00584 0.00506 0.01140 S1 5 0.463200 0.800627 1.047047 11.00000 0.04182 0.03157 = 0.02345 -0.00505 -0.00306 0.00387 HKLF 4 REM 3bc(C6) in P2(1)/c REM R1 = 0.0370 for 4951 Fo > 4sig(Fo) and 0.0472 for all 6061 data REM 397 parameters refined using 0 restraints END WGHT 0.0519 0.3397 REM Highest difference peak 0.247, deepest hole -0.225, 1-sigma level 0.040 Q1 1 0.3171 0.9719 1.0292 11.00000 0.05 0.25 Q2 1 0.4187 1.0421 1.0253 11.00000 0.05 0.24 Q3 1 0.3846 0.9513 0.9566 11.00000 0.05 0.20 Q4 1 0.6196 0.7042 1.2563 11.00000 0.05 0.19 Q5 1 0.5184 0.8165 1.1714 11.00000 0.05 0.18 Q6 1 0.4558 0.8676 1.0645 11.00000 0.05 0.16 ; _audit_update_record ; 2013-02-12 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; (hexanoyloxy) methyl 2-methyl-4-(4-methylpiperazin-1-yl)-5H-benzo[b]thieno[2,3-e][1,4]diazepine-5-\ carboxylate ; _chemical_name_common ? _chemical_melting_point 406 _chemical_formula_moiety 'C35 H52 N4 O4 S' _chemical_formula_sum 'C35 H52 N4 O4 S' _chemical_formula_weight 624.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 14.4300(15) _cell_length_b 14.9488(15) _cell_length_c 16.2240(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.753(7) _cell_angle_gamma 90.00 _cell_volume 3495.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2709 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 68.84 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 1.151 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7110 _exptl_absorpt_correction_T_max 0.8926 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20769 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 69.56 _reflns_number_total 6061 _reflns_number_gt 4951 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.3700P] 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 6061 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.002 _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 C1 C 0.60836(10) 0.70523(10) 1.29936(9) 0.0276(3) Uani 1 1 d . . . C2 C 0.66999(11) 0.68041(11) 1.36346(10) 0.0335(3) Uani 1 1 d . . . H2A H 0.6635 0.7040 1.4172 0.040 Uiso 1 1 calc R . . C3 C 0.74104(11) 0.62119(12) 1.34891(10) 0.0378(4) Uani 1 1 d . . . H3A H 0.7838 0.6043 1.3925 0.045 Uiso 1 1 calc R . . C4 C 0.74932(11) 0.58661(11) 1.27006(10) 0.0360(4) Uani 1 1 d . . . H4A H 0.7964 0.5440 1.2603 0.043 Uiso 1 1 calc R . . C5 C 0.68983(11) 0.61357(11) 1.20607(10) 0.0349(3) Uani 1 1 d . . . H5A H 0.6971 0.5897 1.1525 0.042 Uiso 1 1 calc R . . C6 C 0.61827(10) 0.67585(10) 1.21801(9) 0.0289(3) Uani 1 1 d . . . C7 C 0.51849(10) 0.77675(10) 1.14443(9) 0.0271(3) Uani 1 1 d . . . C8 C 0.43692(10) 0.91077(10) 1.07518(9) 0.0293(3) Uani 1 1 d . . . C9 C 0.46768(10) 0.92946(10) 1.15282(9) 0.0288(3) Uani 1 1 d . . . H9A H 0.4618 0.9870 1.1768 0.035 Uiso 1 1 calc R . . C10 C 0.51066(10) 0.85446(10) 1.19711(9) 0.0261(3) Uani 1 1 d . . . C11 C 0.53222(10) 0.84821(9) 1.28152(9) 0.0247(3) Uani 1 1 d . . . C12 C 0.57265(11) 1.00547(10) 1.30966(9) 0.0314(3) Uani 1 1 d . . . H12A H 0.5156 1.0418 1.3135 0.038 Uiso 1 1 calc R . . H12B H 0.5901 1.0056 1.2514 0.038 Uiso 1 1 calc R . . C13 C 0.65018(11) 1.04697(11) 1.36320(9) 0.0343(3) Uani 1 1 d . . . H13A H 0.7094 1.0168 1.3522 0.041 Uiso 1 1 calc R . . H13B H 0.6563 1.1109 1.3486 0.041 Uiso 1 1 calc R . . C14 C 0.62382(11) 0.94562(10) 1.47261(9) 0.0329(3) Uani 1 1 d . . . H14A H 0.6144 0.9403 1.5324 0.039 Uiso 1 1 calc R . . H14B H 0.6816 0.9134 1.4606 0.039 Uiso 1 1 calc R . . C15 C 0.54313(11) 0.90396(10) 1.42457(8) 0.0302(3) Uani 1 1 d . . . H15A H 0.5390 0.8397 1.4388 0.036 Uiso 1 1 calc R . . H15B H 0.4848 0.9333 1.4397 0.036 Uiso 1 1 calc R . . C16 C 0.70560(13) 1.08293(13) 1.50112(11) 0.0455(4) Uani 1 1 d . . . H16A H 0.6924 1.0768 1.5596 0.068 Uiso 1 1 calc R . . H16B H 0.7080 1.1465 1.4866 0.068 Uiso 1 1 calc R . . H16C H 0.7654 1.0549 1.4911 0.068 Uiso 1 1 calc R . . C17 C 0.38447(12) 0.97056(11) 1.01532(9) 0.0352(3) Uani 1 1 d . . . H17A H 0.3760 1.0294 1.0406 0.053 Uiso 1 1 calc R . . H17B H 0.3237 0.9441 1.0008 0.053 Uiso 1 1 calc R . . H17C H 0.4194 0.9773 0.9654 0.053 Uiso 1 1 calc R . . C18 C 0.44660(10) 0.71991(10) 1.32761(8) 0.0265(3) Uani 1 1 d . . . C19 C 0.28725(11) 0.75223(12) 1.32877(10) 0.0364(4) Uani 1 1 d . . . H19A H 0.2462 0.7934 1.3579 0.044 Uiso 1 1 calc R . . H19B H 0.2839 0.6925 1.3547 0.044 Uiso 1 1 calc R . . C20 C 0.20563(11) 0.81520(12) 1.21167(10) 0.0366(4) Uani 1 1 d . . . C21 C 0.19831(12) 0.80627(13) 1.11963(10) 0.0418(4) Uani 1 1 d . . . H21A H 0.1816 0.7436 1.1060 0.050 Uiso 1 1 calc R . . H21B H 0.2603 0.8176 1.0983 0.050 Uiso 1 1 calc R . . C22 C 0.12911(12) 0.86716(13) 1.07417(10) 0.0418(4) Uani 1 1 d . . . H22A H 0.1442 0.9304 1.0868 0.050 Uiso 1 1 calc R . . H22B H 0.0658 0.8548 1.0923 0.050 Uiso 1 1 calc R . . C23 C 0.13294(12) 0.85075(13) 0.98157(10) 0.0429(4) Uani 1 1 d . . . H23A H 0.1960 0.8665 0.9650 0.051 Uiso 1 1 calc R . . H23B H 0.1247 0.7858 0.9718 0.051 Uiso 1 1 calc R . . C24 C 0.06390(13) 0.89983(14) 0.92458(11) 0.0457(4) Uani 1 1 d . . . H24A H 0.0706 0.9652 0.9330 0.055 Uiso 1 1 calc R . . H24B H 0.0000 0.8827 0.9376 0.055 Uiso 1 1 calc R . . C25 C 0.08066(12) 0.87655(13) 0.83473(11) 0.0434(4) Uani 1 1 d . . . H25A H 0.1415 0.9017 0.8210 0.052 Uiso 1 1 calc R . . H25B H 0.0853 0.8107 0.8303 0.052 Uiso 1 1 calc R . . C26 C 0.00874(13) 0.90854(14) 0.77046(11) 0.0455(4) Uani 1 1 d . . . H26A H 0.0074 0.9748 0.7703 0.055 Uiso 1 1 calc R . . H26B H -0.0533 0.8870 0.7850 0.055 Uiso 1 1 calc R . . C27 C 0.02954(12) 0.87505(13) 0.68456(11) 0.0442(4) Uani 1 1 d . . . H27A H 0.0908 0.8986 0.6702 0.053 Uiso 1 1 calc R . . H27B H 0.0343 0.8090 0.6864 0.053 Uiso 1 1 calc R . . C28 C -0.04136(13) 0.90054(14) 0.61610(11) 0.0458(4) Uani 1 1 d . . . H28A H -0.0434 0.9665 0.6112 0.055 Uiso 1 1 calc R . . H28B H -0.1035 0.8800 0.6314 0.055 Uiso 1 1 calc R . . C29 C -0.02005(13) 0.86069(14) 0.53274(11) 0.0457(4) Uani 1 1 d . . . H29A H 0.0415 0.8823 0.5171 0.055 Uiso 1 1 calc R . . H29B H -0.0165 0.7948 0.5381 0.055 Uiso 1 1 calc R . . C30 C -0.09125(13) 0.88387(14) 0.46427(11) 0.0463(4) Uani 1 1 d . . . H30A H -0.0931 0.9498 0.4582 0.056 Uiso 1 1 calc R . . H30B H -0.1530 0.8645 0.4815 0.056 Uiso 1 1 calc R . . C31 C -0.07503(13) 0.84299(14) 0.38030(11) 0.0472(4) Uani 1 1 d . . . H31A H -0.0129 0.8609 0.3628 0.057 Uiso 1 1 calc R . . H31B H -0.0760 0.7770 0.3850 0.057 Uiso 1 1 calc R . . C32 C -0.14783(13) 0.87226(13) 0.31517(11) 0.0440(4) Uani 1 1 d . . . H32A H -0.2096 0.8560 0.3346 0.053 Uiso 1 1 calc R . . H32B H -0.1457 0.9383 0.3110 0.053 Uiso 1 1 calc R . . C33 C -0.13940(14) 0.83382(14) 0.22980(11) 0.0487(4) Uani 1 1 d . . . H33A H -0.1438 0.7678 0.2328 0.058 Uiso 1 1 calc R . . H33B H -0.0776 0.8490 0.2098 0.058 Uiso 1 1 calc R . . C34 C -0.21370(15) 0.86841(15) 0.16848(12) 0.0540(5) Uani 1 1 d . . . H34A H -0.2753 0.8554 0.1901 0.065 Uiso 1 1 calc R . . H34B H -0.2076 0.9342 0.1646 0.065 Uiso 1 1 calc R . . C35 C -0.2104(2) 0.8294(2) 0.08298(14) 0.0790(8) Uani 1 1 d . . . H35A H -0.2601 0.8555 0.0474 0.118 Uiso 1 1 calc R . . H35B H -0.2187 0.7644 0.0857 0.118 Uiso 1 1 calc R . . H35C H -0.1502 0.8429 0.0603 0.118 Uiso 1 1 calc R . . N1 N 0.52978(8) 0.75992(8) 1.31550(7) 0.0258(3) Uani 1 1 d . . . N2 N 0.56302(9) 0.70048(9) 1.14961(8) 0.0306(3) Uani 1 1 d . . . N3 N 0.55405(9) 0.91354(8) 1.33533(7) 0.0266(3) Uani 1 1 d . . . N4 N 0.63290(9) 1.03938(9) 1.45084(8) 0.0317(3) Uani 1 1 d . . . O1 O 0.43381(8) 0.64084(7) 1.33525(6) 0.0342(3) Uani 1 1 d . . . O2 O 0.38002(7) 0.78438(7) 1.33410(6) 0.0307(2) Uani 1 1 d . . . O3 O 0.25854(8) 0.74691(8) 1.24391(7) 0.0398(3) Uani 1 1 d . . . O4 O 0.17111(11) 0.87163(9) 1.25254(8) 0.0540(4) Uani 1 1 d . . . S1 S 0.46320(3) 0.80063(3) 1.04705(2) 0.03243(11) Uani 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 C1 0.0332(7) 0.0201(7) 0.0295(7) 0.0008(6) 0.0020(6) -0.0007(5) C2 0.0421(9) 0.0298(9) 0.0285(8) 0.0023(6) -0.0005(7) 0.0006(6) C3 0.0379(9) 0.0367(10) 0.0382(9) 0.0077(7) -0.0048(7) 0.0026(6) C4 0.0321(8) 0.0308(9) 0.0450(9) -0.0010(7) 0.0002(7) 0.0035(6) C5 0.0367(8) 0.0318(9) 0.0360(8) -0.0059(7) 0.0014(7) 0.0014(6) C6 0.0331(8) 0.0240(8) 0.0295(8) -0.0023(6) -0.0010(6) -0.0025(5) C7 0.0316(7) 0.0273(8) 0.0223(7) -0.0023(6) 0.0007(6) -0.0025(5) C8 0.0356(8) 0.0285(8) 0.0240(7) 0.0014(6) 0.0026(6) -0.0005(6) C9 0.0398(8) 0.0223(8) 0.0245(7) -0.0004(6) 0.0022(6) -0.0002(6) C10 0.0332(7) 0.0223(8) 0.0229(7) -0.0004(6) 0.0017(6) -0.0012(5) C11 0.0305(7) 0.0195(7) 0.0243(7) 0.0001(5) 0.0038(6) 0.0008(5) C12 0.0471(9) 0.0211(8) 0.0257(7) 0.0007(6) -0.0005(6) -0.0019(6) C13 0.0453(9) 0.0266(8) 0.0313(8) -0.0025(6) 0.0040(7) -0.0053(6) C14 0.0440(9) 0.0298(9) 0.0244(7) -0.0012(6) -0.0032(6) 0.0016(6) C15 0.0428(8) 0.0269(8) 0.0213(7) -0.0011(6) 0.0051(6) -0.0028(6) C16 0.0491(10) 0.0441(11) 0.0426(9) -0.0107(8) -0.0044(8) -0.0079(8) C17 0.0438(9) 0.0335(9) 0.0281(7) 0.0030(7) -0.0009(7) 0.0030(6) C18 0.0373(8) 0.0255(8) 0.0167(6) -0.0027(5) 0.0008(6) -0.0029(6) C19 0.0342(8) 0.0447(10) 0.0303(8) -0.0036(7) 0.0027(7) -0.0073(6) C20 0.0349(8) 0.0377(10) 0.0373(9) -0.0027(7) 0.0033(7) -0.0063(6) C21 0.0385(9) 0.0507(11) 0.0363(9) -0.0033(8) 0.0027(7) 0.0002(7) C22 0.0413(9) 0.0453(11) 0.0387(9) -0.0025(8) 0.0018(7) -0.0025(7) C23 0.0387(9) 0.0518(11) 0.0378(9) -0.0027(8) -0.0009(7) -0.0025(7) C24 0.0423(9) 0.0518(12) 0.0429(10) -0.0027(8) -0.0005(8) 0.0006(7) C25 0.0376(9) 0.0501(11) 0.0422(9) -0.0013(8) -0.0010(7) 0.0020(7) C26 0.0408(9) 0.0520(12) 0.0433(10) -0.0004(8) -0.0019(8) 0.0054(7) C27 0.0386(9) 0.0503(11) 0.0434(10) 0.0008(8) -0.0016(8) 0.0041(7) C28 0.0429(10) 0.0520(12) 0.0422(10) -0.0015(8) -0.0022(8) 0.0078(7) C29 0.0425(10) 0.0512(12) 0.0432(10) -0.0002(8) -0.0011(8) 0.0063(8) C30 0.0454(10) 0.0528(12) 0.0404(9) -0.0008(8) -0.0001(8) 0.0077(8) C31 0.0474(10) 0.0500(12) 0.0439(10) -0.0039(8) -0.0009(8) 0.0080(8) C32 0.0456(10) 0.0446(11) 0.0417(9) -0.0019(8) 0.0005(8) 0.0025(7) C33 0.0541(11) 0.0499(12) 0.0417(10) -0.0016(8) -0.0006(9) 0.0029(8) C34 0.0605(12) 0.0568(13) 0.0442(10) 0.0014(9) -0.0032(9) -0.0013(9) C35 0.100(2) 0.091(2) 0.0446(12) -0.0016(13) -0.0117(13) 0.0083(15) N1 0.0343(6) 0.0191(6) 0.0241(6) 0.0005(5) 0.0020(5) -0.0002(5) N2 0.0356(7) 0.0276(7) 0.0285(6) -0.0061(5) -0.0007(5) 0.0027(5) N3 0.0381(7) 0.0217(7) 0.0202(6) -0.0001(5) 0.0015(5) -0.0014(5) N4 0.0400(7) 0.0282(7) 0.0267(6) -0.0045(5) -0.0009(5) -0.0024(5) O1 0.0477(6) 0.0236(6) 0.0314(5) -0.0006(4) 0.0038(5) -0.0080(4) O2 0.0316(5) 0.0298(6) 0.0307(5) -0.0041(4) 0.0032(4) -0.0032(4) O3 0.0410(6) 0.0454(7) 0.0325(6) -0.0093(5) -0.0027(5) 0.0013(5) O4 0.0754(10) 0.0439(8) 0.0431(7) -0.0058(6) 0.0051(7) 0.0114(7) S1 0.0418(2) 0.0316(2) 0.02345(18) -0.00505(15) -0.00306(15) 0.00387(15) _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 C1 C2 1.386(2) . ? C1 C6 1.405(2) . ? C1 N1 1.4322(18) . ? C2 C3 1.383(2) . ? C2 H2A 0.9500 . ? C3 C4 1.390(2) . ? C3 H3A 0.9500 . ? C4 C5 1.375(2) . ? C4 H4A 0.9500 . ? C5 C6 1.411(2) . ? C5 H5A 0.9500 . ? C6 N2 1.385(2) . ? C7 N2 1.309(2) . ? C7 C10 1.450(2) . ? C7 S1 1.7717(15) . ? C8 C9 1.345(2) . ? C8 C17 1.498(2) . ? C8 S1 1.7549(16) . ? C9 C10 1.454(2) . ? C9 H9A 0.9500 . ? C10 C11 1.393(2) . ? C11 N3 1.3374(19) . ? C11 N1 1.4315(18) . ? C12 N3 1.4645(19) . ? C12 C13 1.516(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.4598(19) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.453(2) . ? C14 C15 1.505(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N3 1.4709(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N4 1.452(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O1 1.2037(19) . ? C18 N1 1.3638(19) . ? C18 O2 1.3683(18) . ? C19 O2 1.4211(18) . ? C19 O3 1.4208(19) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O4 1.196(2) . ? C20 O3 1.364(2) . ? C20 C21 1.498(2) . ? C21 C22 1.516(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.526(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.516(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.529(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.513(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.524(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.522(2) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.523(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.517(2) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.522(2) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.518(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.510(3) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.518(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.508(3) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 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 C1 C6 122.05(14) . . ? C2 C1 N1 120.04(13) . . ? C6 C1 N1 117.87(13) . . ? C3 C2 C1 119.82(15) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 119.48(15) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 120.50(15) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 121.62(15) . . ? C4 C5 H5A 119.2 . . ? C6 C5 H5A 119.2 . . ? N2 C6 C1 126.10(14) . . ? N2 C6 C5 117.55(14) . . ? C1 C6 C5 116.33(14) . . ? N2 C7 C10 135.38(14) . . ? N2 C7 S1 115.55(11) . . ? C10 C7 S1 108.64(11) . . ? C9 C8 C17 128.10(14) . . ? C9 C8 S1 111.89(12) . . ? C17 C8 S1 119.99(11) . . ? C8 C9 C10 114.60(13) . . ? C8 C9 H9A 122.7 . . ? C10 C9 H9A 122.7 . . ? C11 C10 C7 120.39(13) . . ? C11 C10 C9 127.39(13) . . ? C7 C10 C9 111.71(12) . . ? N3 C11 C10 128.86(13) . . ? N3 C11 N1 115.54(12) . . ? C10 C11 N1 115.60(13) . . ? N3 C12 C13 111.19(12) . . ? N3 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? N3 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? N4 C13 C12 111.74(13) . . ? N4 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? N4 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? N4 C14 C15 110.48(13) . . ? N4 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? N4 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? N3 C15 C14 110.65(12) . . ? N3 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N4 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C18 N1 125.86(14) . . ? O1 C18 O2 124.89(14) . . ? N1 C18 O2 109.16(12) . . ? O2 C19 O3 107.93(12) . . ? O2 C19 H19A 110.1 . . ? O3 C19 H19A 110.1 . . ? O2 C19 H19B 110.1 . . ? O3 C19 H19B 110.1 . . ? H19A C19 H19B 108.4 . . ? O4 C20 O3 123.74(16) . . ? O4 C20 C21 127.17(17) . . ? O3 C20 C21 109.09(14) . . ? C20 C21 C22 116.40(15) . . ? C20 C21 H21A 108.2 . . ? C22 C21 H21A 108.2 . . ? C20 C21 H21B 108.2 . . ? C22 C21 H21B 108.2 . . ? H21A C21 H21B 107.3 . . ? C21 C22 C23 109.16(15) . . ? C21 C22 H22A 109.8 . . ? C23 C22 H22A 109.8 . . ? C21 C22 H22B 109.8 . . ? C23 C22 H22B 109.8 . . ? H22A C22 H22B 108.3 . . ? C24 C23 C22 117.97(15) . . ? C24 C23 H23A 107.8 . . ? C22 C23 H23A 107.8 . . ? C24 C23 H23B 107.8 . . ? C22 C23 H23B 107.8 . . ? H23A C23 H23B 107.2 . . ? C23 C24 C25 110.00(15) . . ? C23 C24 H24A 109.7 . . ? C25 C24 H24A 109.7 . . ? C23 C24 H24B 109.7 . . ? C25 C24 H24B 109.7 . . ? H24A C24 H24B 108.2 . . ? C26 C25 C24 116.77(15) . . ? C26 C25 H25A 108.1 . . ? C24 C25 H25A 108.1 . . ? C26 C25 H25B 108.1 . . ? C24 C25 H25B 108.1 . . ? H25A C25 H25B 107.3 . . ? C25 C26 C27 111.57(15) . . ? C25 C26 H26A 109.3 . . ? C27 C26 H26A 109.3 . . ? C25 C26 H26B 109.3 . . ? C27 C26 H26B 109.3 . . ? H26A C26 H26B 108.0 . . ? C28 C27 C26 115.47(15) . . ? C28 C27 H27A 108.4 . . ? C26 C27 H27A 108.4 . . ? C28 C27 H27B 108.4 . . ? C26 C27 H27B 108.4 . . ? H27A C27 H27B 107.5 . . ? C27 C28 C29 113.13(15) . . ? C27 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? C27 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C30 C29 C28 113.73(15) . . ? C30 C29 H29A 108.8 . . ? C28 C29 H29A 108.8 . . ? C30 C29 H29B 108.8 . . ? C28 C29 H29B 108.8 . . ? H29A C29 H29B 107.7 . . ? C29 C30 C31 115.85(16) . . ? C29 C30 H30A 108.3 . . ? C31 C30 H30A 108.3 . . ? C29 C30 H30B 108.3 . . ? C31 C30 H30B 108.3 . . ? H30A C30 H30B 107.4 . . ? C32 C31 C30 112.11(15) . . ? C32 C31 H31A 109.2 . . ? C30 C31 H31A 109.2 . . ? C32 C31 H31B 109.2 . . ? C30 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? C33 C32 C31 116.44(16) . . ? C33 C32 H32A 108.2 . . ? C31 C32 H32A 108.2 . . ? C33 C32 H32B 108.2 . . ? C31 C32 H32B 108.2 . . ? H32A C32 H32B 107.3 . . ? C32 C33 C34 112.71(16) . . ? C32 C33 H33A 109.1 . . ? C34 C33 H33A 109.1 . . ? C32 C33 H33B 109.1 . . ? C34 C33 H33B 109.1 . . ? H33A C33 H33B 107.8 . . ? C35 C34 C33 114.75(19) . . ? C35 C34 H34A 108.6 . . ? C33 C34 H34A 108.6 . . ? C35 C34 H34B 108.6 . . ? C33 C34 H34B 108.6 . . ? H34A C34 H34B 107.6 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C18 N1 C11 119.86(12) . . ? C18 N1 C1 119.09(12) . . ? C11 N1 C1 114.93(11) . . ? C7 N2 C6 123.01(13) . . ? C11 N3 C12 122.70(12) . . ? C11 N3 C15 122.58(12) . . ? C12 N3 C15 113.64(12) . . ? C16 N4 C14 111.54(13) . . ? C16 N4 C13 111.09(13) . . ? C14 N4 C13 109.47(12) . . ? C18 O2 C19 114.83(12) . . ? C20 O3 C19 117.49(13) . . ? C8 S1 C7 92.91(7) . . ? 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 C6 C1 C2 C3 -3.5(2) . . . . ? N1 C1 C2 C3 174.25(14) . . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C2 C3 C4 C5 2.6(3) . . . . ? C3 C4 C5 C6 -0.7(3) . . . . ? C2 C1 C6 N2 -176.69(15) . . . . ? N1 C1 C6 N2 5.5(2) . . . . ? C2 C1 C6 C5 5.2(2) . . . . ? N1 C1 C6 C5 -172.62(13) . . . . ? C4 C5 C6 N2 178.64(14) . . . . ? C4 C5 C6 C1 -3.1(2) . . . . ? C17 C8 C9 C10 175.73(14) . . . . ? S1 C8 C9 C10 -3.10(17) . . . . ? N2 C7 C10 C11 -20.6(3) . . . . ? S1 C7 C10 C11 167.61(11) . . . . ? N2 C7 C10 C9 167.02(16) . . . . ? S1 C7 C10 C9 -4.78(15) . . . . ? C8 C9 C10 C11 -166.49(15) . . . . ? C8 C9 C10 C7 5.24(19) . . . . ? C7 C10 C11 N3 159.68(14) . . . . ? C9 C10 C11 N3 -29.2(3) . . . . ? C7 C10 C11 N1 -21.0(2) . . . . ? C9 C10 C11 N1 150.07(14) . . . . ? N3 C12 C13 N4 -52.60(17) . . . . ? N4 C14 C15 N3 57.44(16) . . . . ? O4 C20 C21 C22 -9.3(3) . . . . ? O3 C20 C21 C22 170.14(14) . . . . ? C20 C21 C22 C23 178.47(15) . . . . ? C21 C22 C23 C24 175.46(16) . . . . ? C22 C23 C24 C25 178.44(16) . . . . ? C23 C24 C25 C26 170.90(16) . . . . ? C24 C25 C26 C27 -175.63(17) . . . . ? C25 C26 C27 C28 177.51(17) . . . . ? C26 C27 C28 C29 -176.57(17) . . . . ? C27 C28 C29 C30 178.76(17) . . . . ? C28 C29 C30 C31 -177.93(17) . . . . ? C29 C30 C31 C32 -178.14(17) . . . . ? C30 C31 C32 C33 -178.70(17) . . . . ? C31 C32 C33 C34 -178.69(17) . . . . ? C32 C33 C34 C35 -177.9(2) . . . . ? O1 C18 N1 C11 159.93(14) . . . . ? O2 C18 N1 C11 -23.21(17) . . . . ? O1 C18 N1 C1 8.8(2) . . . . ? O2 C18 N1 C1 -174.32(12) . . . . ? N3 C11 N1 C18 104.27(15) . . . . ? C10 C11 N1 C18 -75.13(17) . . . . ? N3 C11 N1 C1 -103.48(15) . . . . ? C10 C11 N1 C1 77.12(16) . . . . ? C2 C1 N1 C18 -95.20(17) . . . . ? C6 C1 N1 C18 82.63(17) . . . . ? C2 C1 N1 C11 112.32(15) . . . . ? C6 C1 N1 C11 -69.85(17) . . . . ? C10 C7 N2 C6 1.3(3) . . . . ? S1 C7 N2 C6 172.73(11) . . . . ? C1 C6 N2 C7 26.8(2) . . . . ? C5 C6 N2 C7 -155.04(15) . . . . ? C10 C11 N3 C12 -9.6(2) . . . . ? N1 C11 N3 C12 171.05(13) . . . . ? C10 C11 N3 C15 157.69(15) . . . . ? N1 C11 N3 C15 -21.6(2) . . . . ? C13 C12 N3 C11 -142.43(14) . . . . ? C13 C12 N3 C15 49.21(17) . . . . ? C14 C15 N3 C11 139.84(14) . . . . ? C14 C15 N3 C12 -51.78(17) . . . . ? C15 C14 N4 C16 175.40(13) . . . . ? C15 C14 N4 C13 -61.24(16) . . . . ? C12 C13 N4 C16 -177.43(14) . . . . ? C12 C13 N4 C14 58.94(17) . . . . ? O1 C18 O2 C19 -16.2(2) . . . . ? N1 C18 O2 C19 166.86(12) . . . . ? O3 C19 O2 C18 -85.34(16) . . . . ? O4 C20 O3 C19 -11.4(2) . . . . ? C21 C20 O3 C19 169.17(13) . . . . ? O2 C19 O3 C20 -99.31(16) . . . . ? C9 C8 S1 C7 0.18(12) . . . . ? C17 C8 S1 C7 -178.77(12) . . . . ? N2 C7 S1 C8 -170.93(12) . . . . ? C10 C7 S1 C8 2.69(11) . . . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 69.56 _diffrn_measured_fraction_theta_full 0.922 _refine_diff_density_max 0.247 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 924295' ####################################################################### # # 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_3bh(C16) #TrackingRef '17687_web_deposit_cif_file_2_TarekAZeidan_1360705814.3bh-C16.cif' _iucr_refine_instructions_details ; TITL 3bh(C16) in P2(1)/c CELL 1.54178 10.5728 14.8243 16.8046 90.000 104.795 90.000 ZERR 4.00 0.0002 0.0003 0.0003 0.000 0.001 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 100 128 16 16 4 L.S. 9 ACTA BOND $H FMAP 2 PLAN 6 SIZE 0.169 0.186 0.273 HTAB CONF TEMP -100.000 WGHT 0.085000 0.070000 EXTI 0.000949 FVAR 0.11447 C1 1 -0.166210 0.307849 0.281104 11.00000 0.05766 0.03076 = 0.04007 -0.00127 0.01477 -0.00039 C2 1 -0.256413 0.330632 0.325442 11.00000 0.06506 0.04064 = 0.04355 -0.00563 0.01897 -0.00197 AFIX 43 H2A 2 -0.249504 0.305238 0.378286 11.00000 -1.20000 AFIX 0 C3 1 -0.355745 0.390310 0.292012 11.00000 0.05909 0.04616 = 0.06015 -0.01126 0.01986 -0.00007 AFIX 43 H3A 2 -0.417540 0.406448 0.321836 11.00000 -1.20000 AFIX 0 C4 1 -0.365223 0.426908 0.214285 11.00000 0.05847 0.04646 = 0.05925 -0.00525 0.01061 0.00551 AFIX 43 H4A 2 -0.432354 0.469209 0.191845 11.00000 -1.20000 AFIX 0 C5 1 -0.277896 0.402156 0.169773 11.00000 0.06380 0.04124 = 0.05019 0.00288 0.01184 0.00662 AFIX 43 H5A 2 -0.285904 0.427758 0.116891 11.00000 -1.20000 AFIX 0 C6 1 -0.177667 0.340108 0.200812 11.00000 0.05734 0.03200 = 0.04490 0.00155 0.01401 0.00003 C7 1 -0.034465 0.240466 0.157024 11.00000 0.05303 0.03603 = 0.03325 0.00338 0.01196 -0.00201 C8 1 0.078160 0.105782 0.109972 11.00000 0.05663 0.03546 = 0.03458 0.00116 0.01101 0.00079 C9 1 0.037729 0.086713 0.177125 11.00000 0.06184 0.03243 = 0.03589 0.00084 0.01627 0.00036 AFIX 43 H9A 2 0.047068 0.028493 0.201555 11.00000 -1.20000 AFIX 0 C10 1 -0.021465 0.161442 0.209972 11.00000 0.05632 0.03014 = 0.03250 0.00008 0.01335 -0.00270 C11 1 -0.052528 0.166118 0.285306 11.00000 0.04926 0.02800 = 0.03530 -0.00013 0.00987 0.00029 C12 1 -0.108439 0.006318 0.300181 11.00000 0.06553 0.03074 = 0.03663 0.00074 0.01709 -0.00209 AFIX 23 H12A 2 -0.028987 -0.031236 0.319053 11.00000 -1.20000 H12B 2 -0.132838 0.006903 0.239251 11.00000 -1.20000 AFIX 0 C13 1 -0.219337 -0.033715 0.331057 11.00000 0.06576 0.04050 = 0.03941 0.00122 0.01271 -0.00860 AFIX 23 H13A 2 -0.301198 -0.000563 0.306256 11.00000 -1.20000 H13B 2 -0.232327 -0.097482 0.313353 11.00000 -1.20000 AFIX 0 C14 1 -0.178106 0.064932 0.445700 11.00000 0.06727 0.04704 = 0.03195 0.00224 0.01818 0.00053 AFIX 23 H14A 2 -0.163261 0.068908 0.506196 11.00000 -1.20000 H14B 2 -0.259369 0.098283 0.419934 11.00000 -1.20000 AFIX 0 C15 1 -0.064715 0.106722 0.420467 11.00000 0.06839 0.04033 = 0.03132 -0.00213 0.01397 -0.00734 AFIX 23 H15A 2 -0.057709 0.171209 0.436298 11.00000 -1.20000 H15B 2 0.017336 0.076347 0.449822 11.00000 -1.20000 AFIX 0 C16 1 -0.294731 -0.072880 0.450678 11.00000 0.07346 0.07204 = 0.04795 0.00771 0.02062 -0.02030 AFIX 33 H16A 2 -0.302809 -0.136073 0.432976 11.00000 -1.50000 H16B 2 -0.378149 -0.041843 0.428536 11.00000 -1.50000 H16C 2 -0.271843 -0.070092 0.510933 11.00000 -1.50000 AFIX 0 C17 1 0.150931 0.046428 0.064598 11.00000 0.06841 0.04626 = 0.04384 0.00298 0.02243 0.00725 AFIX 33 H17A 2 0.162857 -0.013421 0.090196 11.00000 -1.50000 H17B 2 0.236629 0.073045 0.066874 11.00000 -1.50000 H17C 2 0.100881 0.040859 0.007061 11.00000 -1.50000 AFIX 0 C18 1 0.060731 0.299392 0.353599 11.00000 0.06478 0.03502 = 0.02950 0.00159 0.01477 -0.00065 C19 1 0.285678 0.275302 0.403533 11.00000 0.05964 0.05052 = 0.04185 -0.00002 0.01091 -0.00391 AFIX 23 H19A 2 0.284248 0.335393 0.428990 11.00000 -1.20000 H19B 2 0.344706 0.235640 0.443956 11.00000 -1.20000 AFIX 0 C20 1 0.389550 0.208151 0.309353 11.00000 0.05799 0.04134 = 0.05309 0.00070 0.01188 -0.00213 C21 1 0.406036 0.218510 0.224890 11.00000 0.05686 0.05197 = 0.04915 0.00179 0.01320 -0.00093 AFIX 23 H21A 2 0.434487 0.281020 0.218045 11.00000 -1.20000 H21B 2 0.320201 0.209325 0.185046 11.00000 -1.20000 AFIX 0 C22 1 0.504475 0.153405 0.204461 11.00000 0.06367 0.05073 = 0.05314 0.00060 0.01493 0.00267 AFIX 23 H22A 2 0.589042 0.159424 0.246265 11.00000 -1.20000 H22B 2 0.473009 0.090821 0.206909 11.00000 -1.20000 AFIX 0 C23 1 0.525378 0.170655 0.120030 11.00000 0.06157 0.06224 = 0.05951 -0.00493 0.01926 -0.00245 AFIX 23 H23A 2 0.552843 0.234142 0.117034 11.00000 -1.20000 H23B 2 0.441220 0.162359 0.078289 11.00000 -1.20000 AFIX 0 C24 1 0.626891 0.109455 0.099138 11.00000 0.07462 0.10392 = 0.07367 -0.01132 0.02751 0.01677 AFIX 23 H24A 2 0.709204 0.113791 0.143167 11.00000 -1.20000 H24B 2 0.595973 0.046255 0.097104 11.00000 -1.20000 AFIX 0 C25 1 0.653457 0.132805 0.019437 11.00000 0.12323 0.15885 = 0.09187 -0.00921 0.05793 0.02853 AFIX 33 H25A 2 0.719214 0.091412 0.008380 11.00000 -1.50000 H25B 2 0.686224 0.194832 0.021598 11.00000 -1.50000 H25C 2 0.572546 0.127654 -0.024512 11.00000 -1.50000 AFIX 0 N1 3 -0.054068 0.255222 0.319268 11.00000 0.05398 0.02740 = 0.03713 -0.00167 0.01204 -0.00124 N2 3 -0.097595 0.316943 0.150817 11.00000 0.05808 0.03647 = 0.04143 0.00600 0.01547 0.00163 N3 3 -0.081110 0.098837 0.331438 11.00000 0.05916 0.03178 = 0.02967 -0.00017 0.01435 -0.00074 N4 3 -0.192436 -0.029091 0.420245 11.00000 0.06066 0.04260 = 0.03392 0.00368 0.01428 -0.00746 O1 4 0.072676 0.379855 0.361260 11.00000 0.06785 0.03136 = 0.04984 -0.00312 0.01361 -0.00451 O2 4 0.157897 0.238388 0.381686 11.00000 0.05604 0.03769 = 0.03933 0.00187 0.01095 -0.00188 O3 4 0.331495 0.283148 0.331704 11.00000 0.06246 0.04369 = 0.05052 0.00313 0.01938 0.00072 O4 4 0.421824 0.144964 0.354873 11.00000 0.11700 0.05487 = 0.05817 0.01083 0.02764 0.01860 S1 5 0.042657 0.217333 0.077404 11.00000 0.06548 0.04155 = 0.04027 0.01043 0.02142 0.00573 HKLF 4 REM 3bh(C16) in P2(1)/c REM R1 = 0.0505 for 3200 Fo > 4sig(Fo) and 0.0744 for all 4476 data REM 308 parameters refined using 0 restraints END WGHT 0.0851 0.0595 REM Highest difference peak 0.341, deepest hole -0.260, 1-sigma level 0.054 Q1 1 0.6338 0.0271 0.0821 11.00000 0.05 0.34 Q2 1 -0.0434 0.1611 0.2374 11.00000 0.05 0.31 Q3 1 0.0206 0.2336 0.1238 11.00000 0.05 0.25 Q4 1 0.0076 0.1205 0.1913 11.00000 0.05 0.24 Q5 1 -0.0357 0.1925 0.1818 11.00000 0.05 0.23 Q6 1 0.0771 0.1144 0.1584 11.00000 0.05 0.22 ; _audit_update_record ; 2013-02-12 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; (palmitoyloxy) methyl 2-methyl-4-(4-methylpiperazin-1-yl)-4H-benzo[b]thieno[2,3-e][1,4]diazepine-5-carboxylate ; _chemical_name_common ? _chemical_melting_point 328 _chemical_formula_moiety 'C25 H32 N4 O4 S' _chemical_formula_sum 'C25 H32 N4 O4 S' _chemical_formula_weight 484.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.5728(2) _cell_length_b 14.8243(3) _cell_length_c 16.8046(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.795(1) _cell_angle_gamma 90.00 _cell_volume 2546.53(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1888 _cell_measurement_theta_min 4.33 _cell_measurement_theta_max 61.63 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 1.437 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6951 _exptl_absorpt_correction_T_max 0.7933 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17085 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 69.48 _reflns_number_total 4476 _reflns_number_gt 3200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.0700P] 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 SHELXL _refine_ls_extinction_coef 0.00095(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4476 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1497 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1662(3) 0.30785(15) 0.28110(15) 0.0424(6) Uani 1 1 d . . . C2 C -0.2564(3) 0.33063(16) 0.32544(17) 0.0488(6) Uani 1 1 d . . . H2A H -0.2495 0.3052 0.3783 0.059 Uiso 1 1 calc R . . C3 C -0.3557(3) 0.39031(18) 0.29201(18) 0.0543(7) Uani 1 1 d . . . H3A H -0.4175 0.4064 0.3218 0.065 Uiso 1 1 calc R . . C4 C -0.3652(3) 0.42691(18) 0.21429(18) 0.0555(7) Uani 1 1 d . . . H4A H -0.4324 0.4692 0.1918 0.067 Uiso 1 1 calc R . . C5 C -0.2779(3) 0.40216(17) 0.16977(18) 0.0522(7) Uani 1 1 d . . . H5A H -0.2859 0.4278 0.1169 0.063 Uiso 1 1 calc R . . C6 C -0.1777(3) 0.34011(15) 0.20081(16) 0.0446(6) Uani 1 1 d . . . C7 C -0.0345(2) 0.24047(15) 0.15702(14) 0.0406(5) Uani 1 1 d . . . C8 C 0.0782(3) 0.10578(16) 0.10997(15) 0.0423(6) Uani 1 1 d . . . C9 C 0.0377(3) 0.08671(15) 0.17712(15) 0.0427(6) Uani 1 1 d . . . H9A H 0.0471 0.0285 0.2016 0.051 Uiso 1 1 calc R . . C10 C -0.0215(2) 0.16144(14) 0.20997(14) 0.0393(5) Uani 1 1 d . . . C11 C -0.0525(2) 0.16612(14) 0.28531(14) 0.0377(5) Uani 1 1 d . . . C12 C -0.1084(3) 0.00632(15) 0.30018(15) 0.0436(6) Uani 1 1 d . . . H12A H -0.0290 -0.0312 0.3191 0.052 Uiso 1 1 calc R . . H12B H -0.1328 0.0069 0.2393 0.052 Uiso 1 1 calc R . . C13 C -0.2193(3) -0.03372(17) 0.33106(15) 0.0487(6) Uani 1 1 d . . . H13A H -0.3012 -0.0006 0.3063 0.058 Uiso 1 1 calc R . . H13B H -0.2323 -0.0975 0.3134 0.058 Uiso 1 1 calc R . . C14 C -0.1781(3) 0.06493(17) 0.44570(16) 0.0477(6) Uani 1 1 d . . . H14A H -0.1633 0.0689 0.5062 0.057 Uiso 1 1 calc R . . H14B H -0.2594 0.0983 0.4199 0.057 Uiso 1 1 calc R . . C15 C -0.0647(3) 0.10672(17) 0.42047(14) 0.0465(6) Uani 1 1 d . . . H15A H -0.0577 0.1712 0.4363 0.056 Uiso 1 1 calc R . . H15B H 0.0173 0.0763 0.4498 0.056 Uiso 1 1 calc R . . C16 C -0.2947(3) -0.0729(2) 0.45068(18) 0.0635(8) Uani 1 1 d . . . H16A H -0.3028 -0.1361 0.4330 0.095 Uiso 1 1 calc R . . H16B H -0.3781 -0.0418 0.4285 0.095 Uiso 1 1 calc R . . H16C H -0.2718 -0.0701 0.5109 0.095 Uiso 1 1 calc R . . C17 C 0.1509(3) 0.04643(17) 0.06460(16) 0.0514(7) Uani 1 1 d . . . H17A H 0.1629 -0.0134 0.0902 0.077 Uiso 1 1 calc R . . H17B H 0.2366 0.0730 0.0669 0.077 Uiso 1 1 calc R . . H17C H 0.1009 0.0409 0.0071 0.077 Uiso 1 1 calc R . . C18 C 0.0607(3) 0.29939(15) 0.35360(14) 0.0426(6) Uani 1 1 d . . . C19 C 0.2857(3) 0.27530(18) 0.40353(16) 0.0510(6) Uani 1 1 d . . . H19A H 0.2842 0.3354 0.4290 0.061 Uiso 1 1 calc R . . H19B H 0.3447 0.2356 0.4440 0.061 Uiso 1 1 calc R . . C20 C 0.3895(3) 0.20815(17) 0.30935(17) 0.0512(7) Uani 1 1 d . . . C21 C 0.4060(3) 0.21851(19) 0.22489(17) 0.0527(7) Uani 1 1 d . . . H21A H 0.4345 0.2810 0.2180 0.063 Uiso 1 1 calc R . . H21B H 0.3202 0.2093 0.1850 0.063 Uiso 1 1 calc R . . C22 C 0.5045(3) 0.15340(19) 0.20446(18) 0.0558(7) Uani 1 1 d . . . H22A H 0.5890 0.1594 0.2463 0.067 Uiso 1 1 calc R . . H22B H 0.4730 0.0908 0.2069 0.067 Uiso 1 1 calc R . . C23 C 0.5254(3) 0.1707(2) 0.12003(19) 0.0604(8) Uani 1 1 d . . . H23A H 0.5528 0.2341 0.1170 0.072 Uiso 1 1 calc R . . H23B H 0.4412 0.1624 0.0783 0.072 Uiso 1 1 calc R . . C24 C 0.6269(4) 0.1095(3) 0.0991(2) 0.0825(11) Uani 1 1 d . . . H24A H 0.7092 0.1138 0.1432 0.099 Uiso 1 1 calc R . . H24B H 0.5960 0.0463 0.0971 0.099 Uiso 1 1 calc R . . C25 C 0.6535(4) 0.1328(4) 0.0194(3) 0.1191(17) Uani 1 1 d . . . H25A H 0.7192 0.0914 0.0084 0.179 Uiso 1 1 calc R . . H25B H 0.6862 0.1948 0.0216 0.179 Uiso 1 1 calc R . . H25C H 0.5725 0.1277 -0.0245 0.179 Uiso 1 1 calc R . . N1 N -0.0541(2) 0.25522(12) 0.31927(12) 0.0394(5) Uani 1 1 d . . . N2 N -0.0976(2) 0.31694(13) 0.15082(13) 0.0448(5) Uani 1 1 d . . . N3 N -0.0811(2) 0.09884(12) 0.33144(12) 0.0397(5) Uani 1 1 d . . . N4 N -0.1924(2) -0.02909(14) 0.42024(12) 0.0453(5) Uani 1 1 d . . . O1 O 0.07268(18) 0.37985(11) 0.36126(11) 0.0499(5) Uani 1 1 d . . . O2 O 0.15790(18) 0.23839(11) 0.38169(10) 0.0446(4) Uani 1 1 d . . . O3 O 0.33150(19) 0.28315(12) 0.33170(11) 0.0513(5) Uani 1 1 d . . . O4 O 0.4218(2) 0.14496(14) 0.35487(13) 0.0757(7) Uani 1 1 d . . . S1 S 0.04266(7) 0.21733(4) 0.07740(4) 0.0477(2) Uani 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 C1 0.0577(16) 0.0308(11) 0.0401(15) -0.0013(9) 0.0148(11) -0.0004(11) C2 0.0651(18) 0.0406(13) 0.0436(16) -0.0056(10) 0.0190(12) -0.0020(12) C3 0.0591(18) 0.0462(14) 0.0601(19) -0.0113(12) 0.0199(13) -0.0001(13) C4 0.0585(18) 0.0465(15) 0.0592(19) -0.0053(12) 0.0106(13) 0.0055(13) C5 0.0638(19) 0.0412(13) 0.0502(17) 0.0029(11) 0.0118(13) 0.0066(13) C6 0.0573(17) 0.0320(12) 0.0449(16) 0.0015(9) 0.0140(11) 0.0000(11) C7 0.0530(15) 0.0360(12) 0.0333(14) 0.0034(9) 0.0120(10) -0.0020(11) C8 0.0566(16) 0.0355(12) 0.0346(14) 0.0012(9) 0.0110(10) 0.0008(11) C9 0.0618(17) 0.0324(11) 0.0359(14) 0.0008(9) 0.0163(11) 0.0004(11) C10 0.0563(16) 0.0301(11) 0.0325(14) 0.0001(8) 0.0134(10) -0.0027(10) C11 0.0493(14) 0.0280(11) 0.0353(14) -0.0001(8) 0.0099(10) 0.0003(10) C12 0.0655(18) 0.0307(11) 0.0366(14) 0.0007(9) 0.0171(11) -0.0021(11) C13 0.0658(18) 0.0405(13) 0.0394(15) 0.0012(10) 0.0127(12) -0.0086(12) C14 0.0673(18) 0.0470(14) 0.0319(14) 0.0022(10) 0.0182(11) 0.0005(13) C15 0.0684(18) 0.0403(13) 0.0313(15) -0.0021(9) 0.0140(11) -0.0073(12) C16 0.073(2) 0.072(2) 0.0479(19) 0.0077(14) 0.0206(14) -0.0203(16) C17 0.0684(19) 0.0463(14) 0.0438(16) 0.0030(11) 0.0224(12) 0.0072(13) C18 0.0648(17) 0.0350(12) 0.0295(14) 0.0016(9) 0.0148(11) -0.0007(11) C19 0.0596(18) 0.0505(15) 0.0418(16) 0.0000(11) 0.0109(12) -0.0039(13) C20 0.0580(17) 0.0413(14) 0.0531(18) 0.0007(11) 0.0119(12) -0.0021(12) C21 0.0569(17) 0.0520(15) 0.0492(17) 0.0018(11) 0.0132(12) -0.0009(13) C22 0.0637(19) 0.0507(16) 0.0531(19) 0.0006(12) 0.0149(13) 0.0027(14) C23 0.0616(19) 0.0622(18) 0.060(2) -0.0049(13) 0.0193(14) -0.0025(15) C24 0.075(2) 0.104(3) 0.074(3) -0.011(2) 0.0275(18) 0.017(2) C25 0.123(4) 0.159(5) 0.092(4) -0.009(3) 0.058(3) 0.029(3) N1 0.0540(13) 0.0274(9) 0.0371(12) -0.0017(7) 0.0120(9) -0.0012(9) N2 0.0581(14) 0.0365(11) 0.0414(13) 0.0060(8) 0.0155(10) 0.0016(10) N3 0.0592(13) 0.0318(10) 0.0297(11) -0.0002(7) 0.0144(9) -0.0007(9) N4 0.0607(14) 0.0426(11) 0.0339(12) 0.0037(8) 0.0143(9) -0.0075(10) O1 0.0679(13) 0.0314(9) 0.0498(12) -0.0031(7) 0.0136(8) -0.0045(8) O2 0.0560(11) 0.0377(9) 0.0393(10) 0.0019(7) 0.0110(7) -0.0019(8) O3 0.0625(12) 0.0437(10) 0.0505(12) 0.0031(8) 0.0194(9) 0.0007(9) O4 0.117(2) 0.0549(13) 0.0582(15) 0.0108(10) 0.0276(12) 0.0186(13) S1 0.0655(5) 0.0415(3) 0.0403(4) 0.0104(2) 0.0214(3) 0.0057(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 C1 C2 1.393(3) . ? C1 C6 1.407(3) . ? C1 N1 1.427(3) . ? C2 C3 1.378(4) . ? C2 H2A 0.9500 . ? C3 C4 1.394(4) . ? C3 H3A 0.9500 . ? C4 C5 1.378(4) . ? C4 H4A 0.9500 . ? C5 C6 1.400(4) . ? C5 H5A 0.9500 . ? C6 N2 1.380(3) . ? C7 N2 1.306(3) . ? C7 C10 1.456(3) . ? C7 S1 1.769(2) . ? C8 C9 1.335(3) . ? C8 C17 1.499(3) . ? C8 S1 1.752(2) . ? C9 C10 1.449(3) . ? C9 H9A 0.9500 . ? C10 C11 1.388(3) . ? C11 N3 1.344(3) . ? C11 N1 1.441(3) . ? C12 N3 1.471(3) . ? C12 C13 1.519(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.454(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.455(3) . ? C14 C15 1.503(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N3 1.466(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N4 1.461(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O1 1.203(3) . ? C18 O2 1.360(3) . ? C18 N1 1.370(3) . ? C19 O3 1.416(3) . ? C19 O2 1.416(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O4 1.202(3) . ? C20 O3 1.368(3) . ? C20 C21 1.482(4) . ? C21 C22 1.522(4) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.512(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.514(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.478(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 C1 C6 121.8(3) . . ? C2 C1 N1 119.7(2) . . ? C6 C1 N1 118.3(2) . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? N2 C6 C5 117.4(2) . . ? N2 C6 C1 125.7(2) . . ? C5 C6 C1 116.9(2) . . ? N2 C7 C10 135.5(2) . . ? N2 C7 S1 115.64(17) . . ? C10 C7 S1 108.44(17) . . ? C9 C8 C17 128.5(2) . . ? C9 C8 S1 112.00(18) . . ? C17 C8 S1 119.47(18) . . ? C8 C9 C10 115.0(2) . . ? C8 C9 H9A 122.5 . . ? C10 C9 H9A 122.5 . . ? C11 C10 C9 127.7(2) . . ? C11 C10 C7 120.6(2) . . ? C9 C10 C7 111.4(2) . . ? N3 C11 C10 129.0(2) . . ? N3 C11 N1 115.1(2) . . ? C10 C11 N1 115.86(19) . . ? N3 C12 C13 109.9(2) . . ? N3 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? N3 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N4 C13 C12 111.6(2) . . ? N4 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? N4 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? N4 C14 C15 110.0(2) . . ? N4 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? N4 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N3 C15 C14 111.1(2) . . ? N3 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? N3 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N4 C16 H16A 109.5 . . ? N4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C18 O2 125.0(3) . . ? O1 C18 N1 125.2(2) . . ? O2 C18 N1 109.75(19) . . ? O3 C19 O2 108.8(2) . . ? O3 C19 H19A 109.9 . . ? O2 C19 H19A 109.9 . . ? O3 C19 H19B 109.9 . . ? O2 C19 H19B 109.9 . . ? H19A C19 H19B 108.3 . . ? O4 C20 O3 122.2(3) . . ? O4 C20 C21 127.3(3) . . ? O3 C20 C21 110.5(2) . . ? C20 C21 C22 113.9(2) . . ? C20 C21 H21A 108.8 . . ? C22 C21 H21A 108.8 . . ? C20 C21 H21B 108.8 . . ? C22 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? C23 C22 C21 112.1(2) . . ? C23 C22 H22A 109.2 . . ? C21 C22 H22A 109.2 . . ? C23 C22 H22B 109.2 . . ? C21 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C22 C23 C24 113.5(3) . . ? C22 C23 H23A 108.9 . . ? C24 C23 H23A 108.9 . . ? C22 C23 H23B 108.9 . . ? C24 C23 H23B 108.9 . . ? H23A C23 H23B 107.7 . . ? C25 C24 C23 112.3(3) . . ? C25 C24 H24A 109.1 . . ? C23 C24 H24A 109.1 . . ? C25 C24 H24B 109.1 . . ? C23 C24 H24B 109.1 . . ? H24A C24 H24B 107.9 . . ? 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 . . ? C18 N1 C1 118.22(19) . . ? C18 N1 C11 120.4(2) . . ? C1 N1 C11 114.5(2) . . ? C7 N2 C6 123.2(2) . . ? C11 N3 C15 122.95(19) . . ? C11 N3 C12 122.59(19) . . ? C15 N3 C12 113.58(18) . . ? C13 N4 C14 109.06(19) . . ? C13 N4 C16 111.9(2) . . ? C14 N4 C16 110.7(2) . . ? C18 O2 C19 114.8(2) . . ? C20 O3 C19 116.3(2) . . ? C8 S1 C7 92.87(11) . . ? 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 C6 C1 C2 C3 -3.7(4) . . . . ? N1 C1 C2 C3 172.2(2) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 1.6(4) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? C4 C5 C6 N2 177.8(2) . . . . ? C4 C5 C6 C1 -3.2(4) . . . . ? C2 C1 C6 N2 -176.0(2) . . . . ? N1 C1 C6 N2 8.1(4) . . . . ? C2 C1 C6 C5 5.1(4) . . . . ? N1 C1 C6 C5 -170.8(2) . . . . ? C17 C8 C9 C10 175.4(3) . . . . ? S1 C8 C9 C10 -2.1(3) . . . . ? C8 C9 C10 C11 -168.6(3) . . . . ? C8 C9 C10 C7 5.2(3) . . . . ? N2 C7 C10 C11 -19.2(5) . . . . ? S1 C7 C10 C11 168.6(2) . . . . ? N2 C7 C10 C9 166.5(3) . . . . ? S1 C7 C10 C9 -5.7(3) . . . . ? C9 C10 C11 N3 -26.7(4) . . . . ? C7 C10 C11 N3 160.1(3) . . . . ? C9 C10 C11 N1 153.0(2) . . . . ? C7 C10 C11 N1 -20.2(4) . . . . ? N3 C12 C13 N4 -54.6(3) . . . . ? N4 C14 C15 N3 57.1(3) . . . . ? O4 C20 C21 C22 -16.9(4) . . . . ? O3 C20 C21 C22 162.4(2) . . . . ? C20 C21 C22 C23 -175.9(2) . . . . ? C21 C22 C23 C24 177.7(3) . . . . ? C22 C23 C24 C25 -175.2(3) . . . . ? O1 C18 N1 C1 7.4(4) . . . . ? O2 C18 N1 C1 -175.83(19) . . . . ? O1 C18 N1 C11 156.9(2) . . . . ? O2 C18 N1 C11 -26.3(3) . . . . ? C2 C1 N1 C18 -95.9(3) . . . . ? C6 C1 N1 C18 80.1(3) . . . . ? C2 C1 N1 C11 112.8(2) . . . . ? C6 C1 N1 C11 -71.2(3) . . . . ? N3 C11 N1 C18 105.0(3) . . . . ? C10 C11 N1 C18 -74.8(3) . . . . ? N3 C11 N1 C1 -104.4(3) . . . . ? C10 C11 N1 C1 75.8(3) . . . . ? C10 C7 N2 C6 -0.9(5) . . . . ? S1 C7 N2 C6 170.9(2) . . . . ? C5 C6 N2 C7 -154.6(3) . . . . ? C1 C6 N2 C7 26.5(4) . . . . ? C10 C11 N3 C15 156.5(3) . . . . ? N1 C11 N3 C15 -23.2(3) . . . . ? C10 C11 N3 C12 -12.0(4) . . . . ? N1 C11 N3 C12 168.2(2) . . . . ? C14 C15 N3 C11 138.4(2) . . . . ? C14 C15 N3 C12 -52.1(3) . . . . ? C13 C12 N3 C11 -140.4(2) . . . . ? C13 C12 N3 C15 50.0(3) . . . . ? C12 C13 N4 C14 61.0(3) . . . . ? C12 C13 N4 C16 -176.2(2) . . . . ? C15 C14 N4 C13 -61.6(3) . . . . ? C15 C14 N4 C16 175.0(2) . . . . ? O1 C18 O2 C19 -15.2(3) . . . . ? N1 C18 O2 C19 168.04(19) . . . . ? O3 C19 O2 C18 -83.8(2) . . . . ? O4 C20 O3 C19 -13.2(4) . . . . ? C21 C20 O3 C19 167.5(2) . . . . ? O2 C19 O3 C20 -85.8(3) . . . . ? C9 C8 S1 C7 -1.2(2) . . . . ? C17 C8 S1 C7 -178.9(2) . . . . ? N2 C7 S1 C8 -170.0(2) . . . . ? C10 C7 S1 C8 3.94(19) . . . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 69.48 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.341 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.054 _database_code_depnum_ccdc_archive 'CCDC 924296'