# Electronic Supplementary Material (ESI) for CrystEngComm # 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_Fel_DMAA #TrackingRef '19719_web_deposit_cif_file_0_AndrewBond_1366639590.felodipine_submit.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'Felodipine : N,N-dimethylacetamide (1:1)' _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 Cl2 N O4, C4 H9 N O' _chemical_formula_sum 'C22 H28 Cl2 N2 O5' _chemical_formula_weight 471.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1075(4) _cell_length_b 15.7970(7) _cell_length_c 16.6894(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.699(1) _cell_angle_gamma 90.00 _cell_volume 2311.55(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9983 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 27.95 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.841 _exptl_absorpt_correction_T_max 0.939 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 30341 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 28.36 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.964 _reflns_number_total 5576 _reflns_number_gt 4624 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0709P)^2^+1.5042P] 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 5576 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.585 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.058 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.67134(7) 0.10258(4) 0.27305(3) 0.04524(17) Uani 1 1 d . A . Cl2 Cl 0.85590(6) 0.09983(3) 0.45935(3) 0.04086(15) Uani 1 1 d . . . O1 O 0.5424(2) 0.11557(10) 0.69679(12) 0.0553(5) Uani 1 1 d . . . O2 O 0.66757(16) 0.07953(8) 0.60400(9) 0.0306(3) Uani 1 1 d . . . O3 O 1.03137(19) 0.40537(10) 0.55184(11) 0.0457(4) Uani 1 1 d . . . O4 O 1.02433(19) 0.26539(10) 0.53526(12) 0.0488(4) Uani 1 1 d . . . N1 N 0.65981(18) 0.37144(10) 0.65926(10) 0.0283(3) Uani 1 1 d . . . H1 H 0.6141 0.4145 0.6758 0.034 Uiso 1 1 calc R . . C1 C 0.6125(2) 0.29034(12) 0.67144(11) 0.0272(4) Uani 1 1 d . A . C2 C 0.6614(2) 0.22355(11) 0.63457(11) 0.0238(3) Uani 1 1 d . . . C3 C 0.75985(19) 0.23612(10) 0.57464(10) 0.0215(3) Uani 1 1 d . A . H3A H 0.8423 0.1924 0.5870 0.026 Uiso 1 1 calc R . . C4 C 0.83456(19) 0.32397(11) 0.58675(10) 0.0233(3) Uani 1 1 d . . . C5 C 0.7752(2) 0.38796(11) 0.62240(11) 0.0254(4) Uani 1 1 d . A . C6 C 0.66670(19) 0.22618(10) 0.48362(10) 0.0227(3) Uani 1 1 d . . . C7 C 0.5404(2) 0.27896(11) 0.45321(11) 0.0270(4) Uani 1 1 d . A . H7A H 0.5118 0.3171 0.4903 0.032 Uiso 1 1 calc R . . C8 C 0.4558(2) 0.27731(13) 0.37034(12) 0.0322(4) Uani 1 1 d . . . H8A H 0.3698 0.3134 0.3516 0.039 Uiso 1 1 calc R A . C9 C 0.4971(2) 0.22286(13) 0.31512(12) 0.0333(4) Uani 1 1 d . A . H9A H 0.4410 0.2221 0.2581 0.040 Uiso 1 1 calc R . . C10 C 0.6210(2) 0.16954(12) 0.34378(11) 0.0302(4) Uani 1 1 d . . . C11 C 0.7052(2) 0.17010(11) 0.42755(11) 0.0265(4) Uani 1 1 d . A . C12 C 0.5108(3) 0.28731(14) 0.72907(14) 0.0384(5) Uani 1 1 d . . . H12A H 0.4180 0.2554 0.7026 0.058 Uiso 1 1 calc R A . H12B H 0.4833 0.3451 0.7409 0.058 Uiso 1 1 calc R . . H12C H 0.5648 0.2595 0.7812 0.058 Uiso 1 1 calc R . . C13 C 0.6162(2) 0.13656(12) 0.64966(12) 0.0294(4) Uani 1 1 d . A . C14 C 0.6309(3) -0.00801(12) 0.61660(14) 0.0367(5) Uani 0.764(7) 1 d P A 1 H14A H 0.5198 -0.0175 0.5944 0.044 Uiso 0.764(7) 1 calc PR A 1 H14B H 0.6602 -0.0215 0.6768 0.044 Uiso 0.764(7) 1 calc PR A 1 C15 C 0.7168(4) -0.06371(18) 0.5721(2) 0.0498(10) Uani 0.764(7) 1 d P A 1 H15A H 0.6934 -0.1232 0.5800 0.075 Uiso 0.764(7) 1 calc PR A 1 H15B H 0.8266 -0.0541 0.5947 0.075 Uiso 0.764(7) 1 calc PR A 1 H15C H 0.6866 -0.0502 0.5126 0.075 Uiso 0.764(7) 1 calc PR A 1 C14A C 0.6309(3) -0.00801(12) 0.61660(14) 0.0367(5) Uani 0.236(7) 1 d P A 2 H14C H 0.6724 -0.0447 0.5807 0.055 Uiso 0.236(7) 1 calc PR A 2 H14D H 0.5199 -0.0148 0.6027 0.055 Uiso 0.236(7) 1 calc PR A 2 H14E H 0.6757 -0.0236 0.6749 0.055 Uiso 0.236(7) 1 calc PR A 2 C16 C 0.9707(2) 0.33847(12) 0.55689(11) 0.0274(4) Uani 1 1 d . A . C17 C 1.1600(3) 0.27160(18) 0.5061(2) 0.0609(8) Uani 0.764(7) 1 d P A 1 H17A H 1.1895 0.2150 0.4920 0.091 Uiso 0.764(7) 1 calc PR A 1 H17B H 1.2432 0.2962 0.5500 0.091 Uiso 0.764(7) 1 calc PR A 1 H17C H 1.1390 0.3078 0.4566 0.091 Uiso 0.764(7) 1 calc PR A 1 C17A C 1.1600(3) 0.27160(18) 0.5061(2) 0.0609(8) Uani 0.236(7) 1 d P A 2 H17D H 1.2419 0.3015 0.5476 0.073 Uiso 0.236(7) 1 calc PR A 2 H17E H 1.1376 0.3033 0.4530 0.073 Uiso 0.236(7) 1 calc PR A 2 C15A C 1.2112(14) 0.1781(8) 0.4932(10) 0.069(4) Uani 0.236(7) 1 d P A 2 H15D H 1.3031 0.1796 0.4734 0.103 Uiso 0.236(7) 1 calc PR A 2 H15E H 1.1292 0.1492 0.4520 0.103 Uiso 0.236(7) 1 calc PR A 2 H15F H 1.2330 0.1475 0.5462 0.103 Uiso 0.236(7) 1 calc PR A 2 C18 C 0.8243(2) 0.47963(12) 0.62997(12) 0.0321(4) Uani 1 1 d . . . H18A H 0.8546 0.4964 0.5802 0.048 Uiso 1 1 calc R A . H18B H 0.9109 0.4868 0.6793 0.048 Uiso 1 1 calc R . . H18C H 0.7393 0.5152 0.6354 0.048 Uiso 1 1 calc R . . O5 O 0.53731(17) 0.50664(10) 0.72816(10) 0.0428(4) Uani 0.745(8) 1 d P B 1 N2 N 0.3201(3) 0.58115(16) 0.71577(18) 0.0247(7) Uani 0.745(8) 1 d P B 1 C19 C 0.4112(3) 0.53363(15) 0.68173(16) 0.0224(8) Uani 0.745(8) 1 d P B 1 C20 C 0.3520(2) 0.51307(13) 0.59114(12) 0.0339(4) Uani 0.745(8) 1 d P B 1 H20A H 0.2531 0.5408 0.5686 0.051 Uiso 0.745(8) 1 calc PR B 1 H20B H 0.3397 0.4516 0.5841 0.051 Uiso 0.745(8) 1 calc PR B 1 H20C H 0.4243 0.5333 0.5614 0.051 Uiso 0.745(8) 1 calc PR B 1 C21 C 0.3770(3) 0.60275(16) 0.80576(15) 0.0485(6) Uani 0.745(8) 1 d P B 1 H21A H 0.3006 0.6371 0.8224 0.073 Uiso 0.745(8) 1 calc PR B 1 H21B H 0.4723 0.6348 0.8153 0.073 Uiso 0.745(8) 1 calc PR B 1 H21C H 0.3954 0.5506 0.8387 0.073 Uiso 0.745(8) 1 calc PR B 1 C22 C 0.1758(2) 0.61457(14) 0.66647(15) 0.0378(5) Uani 0.745(8) 1 d P B 1 H22A H 0.1273 0.6470 0.7024 0.057 Uiso 0.745(8) 1 calc PR B 1 H22B H 0.1090 0.5677 0.6408 0.057 Uiso 0.745(8) 1 calc PR B 1 H22C H 0.1934 0.6516 0.6229 0.057 Uiso 0.745(8) 1 calc PR B 1 O5A O 0.53731(17) 0.50664(10) 0.72816(10) 0.0428(4) Uani 0.255(8) 1 d P B 2 N2A N 0.3171(11) 0.5557(5) 0.6729(7) 0.039(3) Uani 0.255(8) 1 d P B 2 C19A C 0.4217(12) 0.5465(6) 0.7398(7) 0.044(3) Uani 0.255(8) 1 d P B 2 C20A C 0.3520(2) 0.51307(13) 0.59114(12) 0.0339(4) Uani 0.255(8) 1 d P B 2 H20D H 0.2650 0.5226 0.5425 0.051 Uiso 0.255(8) 1 calc PR B 2 H20E H 0.3684 0.4521 0.6002 0.051 Uiso 0.255(8) 1 calc PR B 2 H20F H 0.4435 0.5389 0.5815 0.051 Uiso 0.255(8) 1 calc PR B 2 C21A C 0.3770(3) 0.60275(16) 0.80576(15) 0.0485(6) Uani 0.255(8) 1 d P B 2 H21D H 0.2692 0.6186 0.7856 0.073 Uiso 0.255(8) 1 calc PR B 2 H21E H 0.4399 0.6540 0.8153 0.073 Uiso 0.255(8) 1 calc PR B 2 H21F H 0.3935 0.5712 0.8580 0.073 Uiso 0.255(8) 1 calc PR B 2 C22A C 0.1758(2) 0.61457(14) 0.66647(15) 0.0378(5) Uani 0.255(8) 1 d P B 2 H22D H 0.1083 0.6123 0.6097 0.057 Uiso 0.255(8) 1 calc PR B 2 H22E H 0.2106 0.6729 0.6798 0.057 Uiso 0.255(8) 1 calc PR B 2 H22F H 0.1202 0.5953 0.7058 0.057 Uiso 0.255(8) 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0501(3) 0.0564(4) 0.0336(3) -0.0208(2) 0.0186(2) -0.0142(2) Cl2 0.0443(3) 0.0382(3) 0.0396(3) -0.0102(2) 0.0106(2) 0.0110(2) O1 0.0852(13) 0.0309(8) 0.0731(12) 0.0066(8) 0.0611(11) 0.0002(8) O2 0.0418(7) 0.0195(6) 0.0348(7) -0.0001(5) 0.0176(6) -0.0043(5) O3 0.0452(9) 0.0346(8) 0.0628(11) 0.0040(7) 0.0237(8) -0.0110(6) O4 0.0473(9) 0.0353(8) 0.0786(12) -0.0114(8) 0.0423(9) -0.0100(7) N1 0.0333(8) 0.0218(7) 0.0305(8) -0.0032(6) 0.0101(6) 0.0023(6) C1 0.0298(9) 0.0266(9) 0.0251(8) 0.0013(7) 0.0074(7) 0.0008(7) C2 0.0274(8) 0.0232(8) 0.0212(8) 0.0012(6) 0.0075(7) -0.0013(6) C3 0.0249(8) 0.0193(7) 0.0205(8) -0.0001(6) 0.0066(6) -0.0013(6) C4 0.0262(8) 0.0215(8) 0.0204(8) 0.0012(6) 0.0032(6) -0.0035(6) C5 0.0280(8) 0.0227(8) 0.0221(8) 0.0011(6) 0.0011(7) -0.0016(6) C6 0.0261(8) 0.0205(8) 0.0219(8) -0.0001(6) 0.0075(6) -0.0065(6) C7 0.0295(9) 0.0241(8) 0.0263(9) -0.0007(7) 0.0059(7) -0.0042(7) C8 0.0300(9) 0.0308(10) 0.0312(10) 0.0031(8) 0.0006(8) -0.0048(7) C9 0.0361(10) 0.0379(11) 0.0228(9) -0.0005(7) 0.0028(8) -0.0134(8) C10 0.0356(10) 0.0324(9) 0.0249(9) -0.0084(7) 0.0125(7) -0.0136(8) C11 0.0282(8) 0.0248(8) 0.0278(9) -0.0023(7) 0.0096(7) -0.0051(7) C12 0.0483(12) 0.0335(10) 0.0417(11) -0.0028(9) 0.0262(10) 0.0029(9) C13 0.0362(10) 0.0245(9) 0.0305(9) 0.0020(7) 0.0140(8) -0.0007(7) C14 0.0504(12) 0.0189(9) 0.0451(12) 0.0007(8) 0.0203(10) -0.0063(8) C15 0.069(2) 0.0257(14) 0.064(2) -0.0026(13) 0.0348(17) -0.0041(13) C14A 0.0504(12) 0.0189(9) 0.0451(12) 0.0007(8) 0.0203(10) -0.0063(8) C16 0.0290(9) 0.0291(9) 0.0222(8) 0.0011(7) 0.0037(7) -0.0055(7) C17 0.0563(15) 0.0507(15) 0.095(2) -0.0133(14) 0.0534(16) -0.0132(12) C17A 0.0563(15) 0.0507(15) 0.095(2) -0.0133(14) 0.0534(16) -0.0132(12) C15A 0.059(7) 0.054(7) 0.115(12) -0.006(7) 0.061(8) -0.010(5) C18 0.0387(10) 0.0218(8) 0.0330(10) -0.0029(7) 0.0048(8) -0.0028(7) O5 0.0365(8) 0.0374(8) 0.0500(9) -0.0106(7) 0.0038(7) 0.0103(6) N2 0.0275(12) 0.0246(11) 0.0236(13) -0.0022(10) 0.0094(9) 0.0031(9) C19 0.0255(14) 0.0183(11) 0.0245(16) -0.0016(9) 0.0088(10) -0.0002(10) C20 0.0405(10) 0.0319(10) 0.0273(9) -0.0028(8) 0.0060(8) -0.0042(8) C21 0.0632(15) 0.0499(14) 0.0385(12) -0.0179(10) 0.0241(11) -0.0108(11) C22 0.0285(9) 0.0411(11) 0.0454(12) 0.0059(9) 0.0125(9) 0.0014(8) O5A 0.0365(8) 0.0374(8) 0.0500(9) -0.0106(7) 0.0038(7) 0.0103(6) N2A 0.044(5) 0.029(4) 0.046(6) 0.006(4) 0.017(4) -0.002(3) C19A 0.055(6) 0.036(5) 0.047(7) -0.009(4) 0.023(5) -0.016(4) C20A 0.0405(10) 0.0319(10) 0.0273(9) -0.0028(8) 0.0060(8) -0.0042(8) C21A 0.0632(15) 0.0499(14) 0.0385(12) -0.0179(10) 0.0241(11) -0.0108(11) C22A 0.0285(9) 0.0411(11) 0.0454(12) 0.0059(9) 0.0125(9) 0.0014(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C10 1.7363(19) . ? Cl2 C11 1.7332(19) . ? O1 C13 1.211(2) . ? O2 C13 1.343(2) . ? O2 C14 1.451(2) . ? O3 C16 1.206(2) . ? O4 C16 1.341(2) . ? O4 C17 1.448(3) . ? N1 C5 1.379(2) . ? N1 C1 1.384(2) . ? N1 H1 0.8800 . ? C1 C2 1.356(2) . ? C1 C12 1.506(3) . ? C2 C13 1.475(2) . ? C2 C3 1.526(2) . ? C3 C6 1.534(2) . ? C3 C4 1.535(2) . ? C3 H3A 1.0000 . ? C4 C5 1.357(3) . ? C4 C16 1.474(2) . ? C5 C18 1.511(2) . ? C6 C7 1.400(3) . ? C6 C11 1.400(2) . ? C7 C8 1.390(3) . ? C7 H7A 0.9500 . ? C8 C9 1.385(3) . ? C8 H8A 0.9500 . ? C9 C10 1.386(3) . ? C9 H9A 0.9500 . ? C10 C11 1.401(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C14 C15 1.501(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C15A H15D 0.9800 . ? C15A H15E 0.9800 . ? C15A H15F 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O5 C19 1.272(3) . ? N2 C19 1.353(4) . ? N2 C22 1.449(3) . ? N2 C21 1.490(4) . ? C19 C20 1.497(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? N2A C19A 1.264(16) . ? 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 C13 O2 C14 115.33(15) . . ? C16 O4 C17 116.00(17) . . ? C5 N1 C1 123.10(15) . . ? C5 N1 H1 118.4 . . ? C1 N1 H1 118.4 . . ? C2 C1 N1 119.99(16) . . ? C2 C1 C12 126.84(17) . . ? N1 C1 C12 113.15(16) . . ? C1 C2 C13 120.41(16) . . ? C1 C2 C3 121.31(16) . . ? C13 C2 C3 118.26(15) . . ? C2 C3 C6 111.71(13) . . ? C2 C3 C4 110.46(14) . . ? C6 C3 C4 109.25(13) . . ? C2 C3 H3A 108.4 . . ? C6 C3 H3A 108.4 . . ? C4 C3 H3A 108.4 . . ? C5 C4 C16 120.24(16) . . ? C5 C4 C3 121.09(15) . . ? C16 C4 C3 118.65(15) . . ? C4 C5 N1 119.77(16) . . ? C4 C5 C18 127.36(17) . . ? N1 C5 C18 112.84(16) . . ? C7 C6 C11 117.65(16) . . ? C7 C6 C3 118.55(15) . . ? C11 C6 C3 123.71(16) . . ? C8 C7 C6 122.01(18) . . ? C8 C7 H7A 119.0 . . ? C6 C7 H7A 119.0 . . ? C9 C8 C7 119.75(19) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? C8 C9 C10 119.38(18) . . ? C8 C9 H9A 120.3 . . ? C10 C9 H9A 120.3 . . ? C9 C10 C11 121.00(17) . . ? C9 C10 Cl1 118.41(15) . . ? C11 C10 Cl1 120.58(16) . . ? C6 C11 C10 120.19(17) . . ? C6 C11 Cl2 121.42(14) . . ? C10 C11 Cl2 118.39(14) . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 O2 121.64(17) . . ? O1 C13 C2 126.53(18) . . ? O2 C13 C2 111.83(15) . . ? O2 C14 C15 108.40(18) . . ? O2 C14 H14A 110.0 . . ? C15 C14 H14A 110.0 . . ? O2 C14 H14B 110.0 . . ? C15 C14 H14B 110.0 . . ? H14A C14 H14B 108.4 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O4 121.89(18) . . ? O3 C16 C4 127.09(18) . . ? O4 C16 C4 111.01(15) . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? H15D C15A H15E 109.5 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 109.5 . . ? C5 C18 H18A 109.5 . . ? C5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 N2 C22 122.0(3) . . ? C19 N2 C21 117.7(2) . . ? C22 N2 C21 120.2(2) . . ? O5 C19 N2 119.0(3) . . ? O5 C19 C20 124.2(2) . . ? N2 C19 C20 116.7(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -11.2(3) . . . . ? C5 N1 C1 C12 167.22(17) . . . . ? N1 C1 C2 C13 177.71(17) . . . . ? C12 C1 C2 C13 -0.4(3) . . . . ? N1 C1 C2 C3 -4.2(3) . . . . ? C12 C1 C2 C3 177.66(18) . . . . ? C1 C2 C3 C6 -102.75(19) . . . . ? C13 C2 C3 C6 75.4(2) . . . . ? C1 C2 C3 C4 19.1(2) . . . . ? C13 C2 C3 C4 -162.80(15) . . . . ? C2 C3 C4 C5 -21.8(2) . . . . ? C6 C3 C4 C5 101.48(18) . . . . ? C2 C3 C4 C16 159.76(15) . . . . ? C6 C3 C4 C16 -76.98(19) . . . . ? C16 C4 C5 N1 -172.07(16) . . . . ? C3 C4 C5 N1 9.5(3) . . . . ? C16 C4 C5 C18 5.8(3) . . . . ? C3 C4 C5 C18 -172.64(17) . . . . ? C1 N1 C5 C4 8.4(3) . . . . ? C1 N1 C5 C18 -169.79(16) . . . . ? C2 C3 C6 C7 58.0(2) . . . . ? C4 C3 C6 C7 -64.50(19) . . . . ? C2 C3 C6 C11 -125.42(17) . . . . ? C4 C3 C6 C11 112.07(18) . . . . ? C11 C6 C7 C8 -0.6(3) . . . . ? C3 C6 C7 C8 176.14(16) . . . . ? C6 C7 C8 C9 -0.8(3) . . . . ? C7 C8 C9 C10 1.2(3) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C8 C9 C10 Cl1 -179.47(14) . . . . ? C7 C6 C11 C10 1.7(2) . . . . ? C3 C6 C11 C10 -174.95(16) . . . . ? C7 C6 C11 Cl2 -178.10(13) . . . . ? C3 C6 C11 Cl2 5.3(2) . . . . ? C9 C10 C11 C6 -1.3(3) . . . . ? Cl1 C10 C11 C6 178.00(13) . . . . ? C9 C10 C11 Cl2 178.47(14) . . . . ? Cl1 C10 C11 Cl2 -2.2(2) . . . . ? C14 O2 C13 O1 -1.2(3) . . . . ? C14 O2 C13 C2 178.67(17) . . . . ? C1 C2 C13 O1 -4.0(3) . . . . ? C3 C2 C13 O1 177.8(2) . . . . ? C1 C2 C13 O2 176.14(17) . . . . ? C3 C2 C13 O2 -2.0(2) . . . . ? C13 O2 C14 C15 -171.0(2) . . . . ? C17 O4 C16 O3 0.4(3) . . . . ? C17 O4 C16 C4 -179.0(2) . . . . ? C5 C4 C16 O3 -8.6(3) . . . . ? C3 C4 C16 O3 169.92(19) . . . . ? C5 C4 C16 O4 170.87(17) . . . . ? C3 C4 C16 O4 -10.7(2) . . . . ? C22 N2 C19 O5 179.4(2) . . . . ? C21 N2 C19 O5 2.9(3) . . . . ? C22 N2 C19 C20 -3.2(3) . . . . ? C21 N2 C19 C20 -179.73(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O5 0.88 1.92 2.797(2) 171.2 . _database_code_depnum_ccdc_archive 'CCDC 935390' ####################################################################### # # 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_Fel_DMEU #TrackingRef '19719_web_deposit_cif_file_0_AndrewBond_1366639590.felodipine_submit.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ; Felodipine : 1,3-dimethylimidazolidine-2-one (1:1) ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 Cl2 N O4, C5 H10 N2 O' _chemical_formula_sum 'C23 H29 Cl2 N3 O5' _chemical_formula_weight 498.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.6544(12) _cell_length_b 11.4450(5) _cell_length_c 14.5730(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.715(1) _cell_angle_gamma 90.00 _cell_volume 4778.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9806 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 28.31 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 0.311 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.817 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ? _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 36365 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 28.43 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.992 _reflns_number_total 5967 _reflns_number_gt 5178 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0508P)^2^+7.1017P] 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 5967 _refine_ls_number_parameters 311 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.773 _refine_diff_density_min -0.609 _refine_diff_density_rms 0.050 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.250297(17) 1.10851(5) 0.41855(4) 0.04229(14) Uani 1 1 d . A . Cl2 Cl 0.291752(17) 1.06986(5) 0.61351(3) 0.03714(13) Uani 1 1 d . . . O1 O 0.33146(6) 0.62641(14) 0.65453(15) 0.0612(5) Uani 1 1 d . . . O2 O 0.30525(4) 0.80863(13) 0.66861(9) 0.0353(3) Uani 1 1 d . . . O3 O 0.47802(6) 1.14577(15) 0.62043(15) 0.0608(5) Uani 1 1 d . . . O4 O 0.40091(5) 1.15080(11) 0.64081(9) 0.0337(3) Uani 1 1 d . . . N1 N 0.46663(5) 0.77610(15) 0.62776(12) 0.0352(4) Uani 1 1 d . . . H1 H 0.4914 0.7317 0.6211 0.042 Uiso 1 1 calc R . . C1 C 0.42420(7) 0.72245(17) 0.63936(13) 0.0322(4) Uani 1 1 d . A . C2 C 0.38464(6) 0.78725(15) 0.64097(11) 0.0272(3) Uani 1 1 d . . . C3 C 0.38502(6) 0.91916(15) 0.62435(11) 0.0238(3) Uani 1 1 d . A . H3A H 0.3667 0.9579 0.6738 0.029 Uiso 1 1 calc R . . C4 C 0.43492(6) 0.96669(16) 0.62766(11) 0.0267(3) Uani 1 1 d . . . C5 C 0.47247(6) 0.89487(17) 0.62598(12) 0.0300(4) Uani 1 1 d . A . C6 C 0.36198(6) 0.94740(14) 0.53146(11) 0.0231(3) Uani 1 1 d . . . C7 C 0.38350(6) 0.90620(15) 0.45240(11) 0.0265(3) Uani 1 1 d . A . H7A H 0.4116 0.8625 0.4582 0.032 Uiso 1 1 calc R . . C8 C 0.36499(7) 0.92743(16) 0.36558(12) 0.0314(4) Uani 1 1 d . . . H8A H 0.3806 0.8992 0.3129 0.038 Uiso 1 1 calc R A . C9 C 0.32383(7) 0.98973(17) 0.35565(12) 0.0318(4) Uani 1 1 d . A . H9A H 0.3109 1.0040 0.2963 0.038 Uiso 1 1 calc R . . C10 C 0.30169(6) 1.03096(16) 0.43299(12) 0.0283(3) Uani 1 1 d . . . C11 C 0.32061(6) 1.01120(15) 0.52040(11) 0.0254(3) Uani 1 1 d . A . C12 C 0.42800(8) 0.59211(19) 0.65107(18) 0.0458(5) Uani 1 1 d . . . H12A H 0.4084 0.5672 0.7021 0.069 Uiso 1 1 calc R A . H12B H 0.4606 0.5710 0.6642 0.069 Uiso 1 1 calc R . . H12C H 0.4175 0.5533 0.5945 0.069 Uiso 1 1 calc R . . C13 C 0.33936(7) 0.73015(17) 0.65493(13) 0.0326(4) Uani 1 1 d . A . C14A C 0.25802(8) 0.7644(3) 0.6738(2) 0.0596(7) Uani 0.50 1 d P A 1 H14A H 0.2494 0.7268 0.6156 0.089 Uiso 0.50 1 calc PR A 1 H14B H 0.2366 0.8293 0.6856 0.089 Uiso 0.50 1 calc PR A 1 H14C H 0.2561 0.7073 0.7237 0.089 Uiso 0.50 1 calc PR A 1 C14 C 0.25802(8) 0.7644(3) 0.6738(2) 0.0596(7) Uani 0.50 1 d PD A 2 H14D H 0.2382 0.8167 0.7109 0.072 Uiso 0.50 1 calc PR A 2 H14E H 0.2575 0.6851 0.7008 0.072 Uiso 0.50 1 calc PR A 2 C15 C 0.24097(15) 0.7623(4) 0.5699(3) 0.0477(10) Uani 0.50 1 d PD A 2 H15A H 0.2089 0.7331 0.5663 0.071 Uiso 0.50 1 calc PR A 2 H15B H 0.2614 0.7110 0.5344 0.071 Uiso 0.50 1 calc PR A 2 H15C H 0.2422 0.8416 0.5446 0.071 Uiso 0.50 1 calc PR A 2 C16 C 0.44162(7) 1.09380(17) 0.62927(13) 0.0320(4) Uani 1 1 d . A . C17A C 0.40424(8) 1.27673(18) 0.64255(16) 0.0429(5) Uani 0.50 1 d P B 1 H17A H 0.4172 1.3063 0.5843 0.052 Uiso 0.50 1 calc PR B 1 H17B H 0.4246 1.3028 0.6939 0.052 Uiso 0.50 1 calc PR B 1 C15A C 0.35577(13) 1.3198(4) 0.6550(4) 0.0449(10) Uani 0.50 1 d PD B 1 H15D H 0.3558 1.4054 0.6567 0.067 Uiso 0.50 1 calc PR B 1 H15E H 0.3435 1.2893 0.7127 0.067 Uiso 0.50 1 calc PR B 1 H15F H 0.3361 1.2929 0.6038 0.067 Uiso 0.50 1 calc PR B 1 C17 C 0.40424(8) 1.27673(18) 0.64255(16) 0.0429(5) Uani 0.50 1 d PD B 2 H17C H 0.4224 1.3012 0.6966 0.064 Uiso 0.50 1 calc PR B 2 H17D H 0.3729 1.3105 0.6454 0.064 Uiso 0.50 1 calc PR B 2 H17E H 0.4197 1.3040 0.5869 0.064 Uiso 0.50 1 calc PR B 2 C18 C 0.52299(7) 0.9309(2) 0.62420(15) 0.0387(4) Uani 1 1 d . . . H18A H 0.5284 0.9938 0.6687 0.058 Uiso 1 1 calc R A . H18B H 0.5307 0.9586 0.5626 0.058 Uiso 1 1 calc R . . H18C H 0.5427 0.8638 0.6401 0.058 Uiso 1 1 calc R . . O5 O 0.54555(5) 0.62717(15) 0.60417(14) 0.0542(4) Uani 1 1 d . . . N2 N 0.62444(6) 0.59915(15) 0.58668(13) 0.0395(4) Uani 1 1 d . . . N3 N 0.58053(6) 0.44665(15) 0.61874(14) 0.0411(4) Uani 1 1 d . . . C19 C 0.58001(7) 0.56429(17) 0.60287(14) 0.0352(4) Uani 1 1 d . . . C20 C 0.65714(8) 0.5058(2) 0.60466(18) 0.0457(5) Uani 1 1 d . . . H20A H 0.6715 0.5131 0.6666 0.055 Uiso 1 1 calc R . . H20B H 0.6821 0.5039 0.5582 0.055 Uiso 1 1 calc R . . C21 C 0.62598(7) 0.39860(19) 0.59772(17) 0.0420(5) Uani 1 1 d . . . H21A H 0.6264 0.3646 0.5353 0.050 Uiso 1 1 calc R . . H21B H 0.6354 0.3381 0.6428 0.050 Uiso 1 1 calc R . . C22 C 0.63833(8) 0.72049(19) 0.59451(17) 0.0471(5) Uani 1 1 d . . . H22A H 0.6129 0.7707 0.5721 0.071 Uiso 1 1 calc R . . H22B H 0.6663 0.7340 0.5578 0.071 Uiso 1 1 calc R . . H22C H 0.6452 0.7389 0.6590 0.071 Uiso 1 1 calc R . . C23 C 0.53845(8) 0.3764(2) 0.61174(18) 0.0490(5) Uani 1 1 d . . . H23A H 0.5115 0.4232 0.6303 0.073 Uiso 1 1 calc R . . H23B H 0.5414 0.3082 0.6520 0.073 Uiso 1 1 calc R . . H23C H 0.5340 0.3503 0.5482 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0322(2) 0.0529(3) 0.0416(3) 0.0112(2) -0.00573(19) 0.0036(2) Cl2 0.0358(2) 0.0481(3) 0.0276(2) -0.00155(18) 0.00445(17) 0.0127(2) O1 0.0470(9) 0.0326(8) 0.1044(15) -0.0012(9) 0.0168(9) -0.0117(7) O2 0.0251(6) 0.0405(8) 0.0404(7) -0.0028(6) 0.0053(5) -0.0072(5) O3 0.0383(9) 0.0407(9) 0.1034(15) -0.0039(9) 0.0055(9) -0.0146(7) O4 0.0372(7) 0.0266(6) 0.0373(7) -0.0005(5) 0.0015(5) -0.0042(5) N1 0.0265(7) 0.0361(9) 0.0429(9) 0.0095(7) 0.0038(6) 0.0037(6) C1 0.0329(9) 0.0320(9) 0.0318(9) 0.0090(7) 0.0030(7) -0.0006(7) C2 0.0294(8) 0.0282(8) 0.0240(8) 0.0047(6) 0.0035(6) -0.0026(7) C3 0.0238(8) 0.0266(8) 0.0209(7) 0.0015(6) 0.0031(6) -0.0024(6) C4 0.0265(8) 0.0326(9) 0.0212(7) 0.0024(6) 0.0010(6) -0.0053(7) C5 0.0277(8) 0.0383(10) 0.0240(8) 0.0055(7) 0.0013(6) -0.0032(7) C6 0.0260(8) 0.0220(7) 0.0214(7) 0.0015(6) 0.0027(6) -0.0053(6) C7 0.0303(8) 0.0246(8) 0.0246(8) -0.0002(6) 0.0050(6) -0.0046(6) C8 0.0406(10) 0.0322(9) 0.0216(8) -0.0031(7) 0.0063(7) -0.0080(8) C9 0.0408(10) 0.0319(9) 0.0228(8) 0.0034(7) -0.0026(7) -0.0109(8) C10 0.0283(8) 0.0273(8) 0.0293(8) 0.0041(7) -0.0028(7) -0.0050(7) C11 0.0275(8) 0.0267(8) 0.0220(7) 0.0002(6) 0.0036(6) -0.0038(6) C12 0.0405(11) 0.0338(11) 0.0634(14) 0.0170(10) 0.0055(10) 0.0037(9) C13 0.0329(9) 0.0335(10) 0.0316(9) 0.0027(7) 0.0055(7) -0.0063(7) C14A 0.0295(11) 0.0646(16) 0.0851(19) -0.0251(14) 0.0155(11) -0.0169(11) C14 0.0295(11) 0.0646(16) 0.0851(19) -0.0251(14) 0.0155(11) -0.0169(11) C15 0.036(2) 0.044(2) 0.062(3) 0.000(2) -0.0013(19) -0.0046(18) C16 0.0321(9) 0.0344(9) 0.0294(9) 0.0001(7) -0.0004(7) -0.0069(7) C17A 0.0531(13) 0.0267(10) 0.0490(12) -0.0041(8) -0.0013(10) -0.0046(9) C15A 0.042(2) 0.0273(19) 0.065(3) -0.0056(18) 0.001(2) 0.0025(17) C17 0.0531(13) 0.0267(10) 0.0490(12) -0.0041(8) -0.0013(10) -0.0046(9) C18 0.0255(9) 0.0495(12) 0.0412(11) 0.0053(9) -0.0002(7) -0.0042(8) O5 0.0338(8) 0.0398(9) 0.0890(13) 0.0038(8) 0.0000(8) 0.0047(7) N2 0.0327(8) 0.0305(8) 0.0553(11) 0.0040(7) 0.0014(7) -0.0056(7) N3 0.0315(8) 0.0305(8) 0.0615(11) -0.0042(8) 0.0068(8) -0.0054(7) C19 0.0319(9) 0.0325(9) 0.0413(10) -0.0006(8) 0.0008(8) -0.0023(7) C20 0.0328(10) 0.0388(11) 0.0656(14) -0.0031(10) 0.0088(9) -0.0017(8) C21 0.0369(10) 0.0327(10) 0.0565(13) -0.0047(9) 0.0062(9) -0.0009(8) C22 0.0490(12) 0.0338(11) 0.0584(14) 0.0039(9) -0.0010(10) -0.0134(9) C23 0.0390(11) 0.0429(12) 0.0651(15) -0.0035(11) 0.0033(10) -0.0140(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C10 1.7300(19) . ? Cl2 C11 1.7331(17) . ? O1 C13 1.209(2) . ? O2 C13 1.344(2) . ? O2 C14A 1.448(2) . ? O3 C16 1.209(2) . ? O4 C16 1.349(2) . ? O4 C17A 1.445(2) . ? N1 C5 1.370(3) . ? N1 C1 1.374(2) . ? N1 H1 0.8800 . ? C1 C2 1.355(3) . ? C1 C12 1.505(3) . ? C2 C13 1.469(2) . ? C2 C3 1.529(2) . ? C3 C4 1.530(2) . ? C3 C6 1.533(2) . ? C3 H3A 1.0000 . ? C4 C5 1.354(3) . ? C4 C16 1.468(3) . ? C5 C18 1.506(2) . ? C6 C7 1.395(2) . ? C6 C11 1.400(2) . ? C7 C8 1.387(2) . ? C7 H7A 0.9500 . ? C8 C9 1.384(3) . ? C8 H8A 0.9500 . ? C9 C10 1.383(3) . ? C9 H9A 0.9500 . ? C10 C11 1.397(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C14A H14A 0.9800 . ? C14A H14B 0.9800 . ? C14A H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C17A C15A 1.487(4) . ? C17A H17A 0.9900 . ? C17A H17B 0.9900 . ? C15A H15D 0.9800 . ? C15A H15E 0.9800 . ? C15A H15F 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? O5 C19 1.222(2) . ? N2 C19 1.358(3) . ? N2 C20 1.443(3) . ? N2 C22 1.449(3) . ? N3 C19 1.366(3) . ? N3 C21 1.450(3) . ? N3 C23 1.452(3) . ? C20 C21 1.520(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 C13 O2 C14A 117.14(17) . . ? C16 O4 C17A 115.32(16) . . ? C5 N1 C1 123.65(16) . . ? C5 N1 H1 118.2 . . ? C1 N1 H1 118.2 . . ? C2 C1 N1 119.94(17) . . ? C2 C1 C12 126.86(18) . . ? N1 C1 C12 113.19(17) . . ? C1 C2 C13 119.96(17) . . ? C1 C2 C3 122.02(16) . . ? C13 C2 C3 117.97(15) . . ? C2 C3 C4 110.76(14) . . ? C2 C3 C6 110.13(14) . . ? C4 C3 C6 110.17(13) . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? C6 C3 H3A 108.6 . . ? C5 C4 C16 119.88(16) . . ? C5 C4 C3 121.73(16) . . ? C16 C4 C3 118.35(16) . . ? C4 C5 N1 120.31(17) . . ? C4 C5 C18 126.74(18) . . ? N1 C5 C18 112.94(17) . . ? C7 C6 C11 117.61(15) . . ? C7 C6 C3 117.90(15) . . ? C11 C6 C3 124.49(14) . . ? C8 C7 C6 121.74(17) . . ? C8 C7 H7A 119.1 . . ? C6 C7 H7A 119.1 . . ? C9 C8 C7 120.08(16) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C10 C9 C8 119.30(16) . . ? C10 C9 H9A 120.4 . . ? C8 C9 H9A 120.4 . . ? C9 C10 C11 120.74(17) . . ? C9 C10 Cl1 118.31(14) . . ? C11 C10 Cl1 120.95(14) . . ? C10 C11 C6 120.53(15) . . ? C10 C11 Cl2 117.89(14) . . ? C6 C11 Cl2 121.57(13) . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 O2 121.39(18) . . ? O1 C13 C2 126.99(19) . . ? O2 C13 C2 111.62(16) . . ? O2 C14A H14A 109.5 . . ? O2 C14A H14B 109.5 . . ? H14A C14A H14B 109.5 . . ? O2 C14A H14C 109.5 . . ? H14A C14A H14C 109.5 . . ? H14B C14A H14C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O4 121.60(19) . . ? O3 C16 C4 126.79(19) . . ? O4 C16 C4 111.60(15) . . ? O4 C17A C15A 105.7(2) . . ? O4 C17A H17A 110.6 . . ? C15A C17A H17A 110.6 . . ? O4 C17A H17B 110.6 . . ? C15A C17A H17B 110.6 . . ? H17A C17A H17B 108.7 . . ? C17A C15A H15D 109.5 . . ? C17A C15A H15E 109.5 . . ? H15D C15A H15E 109.5 . . ? C17A C15A H15F 109.5 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 109.5 . . ? C5 C18 H18A 109.5 . . ? C5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 N2 C20 111.05(17) . . ? C19 N2 C22 121.70(19) . . ? C20 N2 C22 121.20(18) . . ? C19 N3 C21 110.23(17) . . ? C19 N3 C23 121.79(19) . . ? C21 N3 C23 121.50(18) . . ? O5 C19 N2 126.09(19) . . ? O5 C19 N3 125.78(19) . . ? N2 C19 N3 108.12(17) . . ? N2 C20 C21 101.88(17) . . ? N2 C20 H20A 111.4 . . ? C21 C20 H20A 111.4 . . ? N2 C20 H20B 111.4 . . ? C21 C20 H20B 111.4 . . ? H20A C20 H20B 109.3 . . ? N3 C21 C20 102.01(17) . . ? N3 C21 H21A 111.4 . . ? C20 C21 H21A 111.4 . . ? N3 C21 H21B 111.4 . . ? C20 C21 H21B 111.4 . . ? H21A C21 H21B 109.2 . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 C23 H23A 109.5 . . ? N3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 6.4(3) . . . . ? C5 N1 C1 C12 -172.50(19) . . . . ? N1 C1 C2 C13 -178.96(17) . . . . ? C12 C1 C2 C13 -0.3(3) . . . . ? N1 C1 C2 C3 3.8(3) . . . . ? C12 C1 C2 C3 -177.50(19) . . . . ? C1 C2 C3 C4 -12.4(2) . . . . ? C13 C2 C3 C4 170.33(15) . . . . ? C1 C2 C3 C6 109.72(19) . . . . ? C13 C2 C3 C6 -67.55(19) . . . . ? C2 C3 C4 C5 12.8(2) . . . . ? C6 C3 C4 C5 -109.31(18) . . . . ? C2 C3 C4 C16 -169.48(15) . . . . ? C6 C3 C4 C16 68.42(19) . . . . ? C16 C4 C5 N1 177.68(16) . . . . ? C3 C4 C5 N1 -4.6(3) . . . . ? C16 C4 C5 C18 -0.9(3) . . . . ? C3 C4 C5 C18 176.77(16) . . . . ? C1 N1 C5 C4 -5.9(3) . . . . ? C1 N1 C5 C18 172.85(17) . . . . ? C2 C3 C6 C7 -64.30(19) . . . . ? C4 C3 C6 C7 58.17(19) . . . . ? C2 C3 C6 C11 115.30(18) . . . . ? C4 C3 C6 C11 -122.23(17) . . . . ? C11 C6 C7 C8 0.2(2) . . . . ? C3 C6 C7 C8 179.83(15) . . . . ? C6 C7 C8 C9 -0.8(3) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C8 C9 C10 Cl1 -179.99(14) . . . . ? C9 C10 C11 C6 -1.1(3) . . . . ? Cl1 C10 C11 C6 179.40(13) . . . . ? C9 C10 C11 Cl2 177.91(14) . . . . ? Cl1 C10 C11 Cl2 -1.5(2) . . . . ? C7 C6 C11 C10 0.8(2) . . . . ? C3 C6 C11 C10 -178.84(15) . . . . ? C7 C6 C11 Cl2 -178.26(13) . . . . ? C3 C6 C11 Cl2 2.1(2) . . . . ? C14A O2 C13 O1 -5.9(3) . . . . ? C14A O2 C13 C2 173.76(18) . . . . ? C1 C2 C13 O1 -9.9(3) . . . . ? C3 C2 C13 O1 167.5(2) . . . . ? C1 C2 C13 O2 170.48(16) . . . . ? C3 C2 C13 O2 -12.2(2) . . . . ? C17A O4 C16 O3 -0.5(3) . . . . ? C17A O4 C16 C4 -179.57(16) . . . . ? C5 C4 C16 O3 7.7(3) . . . . ? C3 C4 C16 O3 -170.1(2) . . . . ? C5 C4 C16 O4 -173.33(15) . . . . ? C3 C4 C16 O4 8.9(2) . . . . ? C16 O4 C17A C15A 179.6(2) . . . . ? C20 N2 C19 O5 170.9(2) . . . . ? C22 N2 C19 O5 18.0(3) . . . . ? C20 N2 C19 N3 -8.3(3) . . . . ? C22 N2 C19 N3 -161.2(2) . . . . ? C21 N3 C19 O5 171.3(2) . . . . ? C23 N3 C19 O5 19.2(4) . . . . ? C21 N3 C19 N2 -9.5(2) . . . . ? C23 N3 C19 N2 -161.6(2) . . . . ? C19 N2 C20 C21 21.3(2) . . . . ? C22 N2 C20 C21 174.3(2) . . . . ? C19 N3 C21 C20 22.0(2) . . . . ? C23 N3 C21 C20 174.1(2) . . . . ? N2 C20 C21 N3 -24.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O5 0.88 1.98 2.856(2) 177.8 . _database_code_depnum_ccdc_archive 'CCDC 935391' ####################################################################### # # 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_Fel_TMU #TrackingRef '19719_web_deposit_cif_file_0_AndrewBond_1366639590.felodipine_submit.cif' #============================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'Felodipine : tetramethylurea (1:1)' _chemical_melting_point ? _chemical_formula_moiety 'C18 H19 Cl2 N O4, C5 H12 N2 O' _chemical_formula_sum 'C23 H31 Cl2 N3 O5' _chemical_formula_weight 500.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 16.3261(18) _cell_length_b 11.4866(11) _cell_length_c 14.7468(17) _cell_angle_alpha 90.00 _cell_angle_beta 111.959(3) _cell_angle_gamma 90.00 _cell_volume 2564.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 4758 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 21.98 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.290 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.524 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ** Crystal handled as a 2-component non-merohedral twin ** #------------------------------------------------------------------------------ CELL_NOW: #------------------------------------------------------------------------------ Domain 2 rotated from first domain by 180.0 degrees about reciprocal axis 1.000 0.000 0.000 and real axis 1.000 -0.001 0.413 Twin law to convert hkl from first to 1.000 -0.003 0.826 second domain (SHELXL TWIN matrix): -0.001 -1.000 0.000 0.000 0.000 -1.000 #------------------------------------------------------------------------------ TWINABS: #------------------------------------------------------------------------------ 8264 data ( 2160 unique ) involve component 1 only, mean I/sigma 6.8 8201 data ( 2148 unique ) involve component 2 only, mean I/sigma 3.6 12947 data ( 3709 unique ) involve 2 components, mean I/sigma 6.1 Statistics for singles for twin component 1 #------------------------------------------- Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -17.0 0.0420 0.850 - 0.977 0.923 - 1.568 0.618 7355 4586 2 -2.0 0.0618 1.001 - 1.487 0.911 - 1.181 0.669 838 531 Statistics for singles for twin component 2 #------------------------------------------- Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -17.0 0.0717 0.850 - 0.977 0.920 - 1.570 0.598 7324 3650 2 -2.0 0.1013 1.001 - 1.487 0.916 - 1.182 0.675 806 362 Statistics for all composite reflections #--------------------------------------- Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -17.0 0.0726 0.850 - 0.977 0.919 - 1.560 0.649 9323 5639 2 -2.0 0.0738 1.001 - 1.487 0.910 - 1.181 0.728 3530 2547 Statistics for all single and composite reflections #-------------------------------------------------- Run 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -17.0 0.0587 0.850 - 0.977 0.919 - 1.570 0.624 24002 13904 2 -2.0 0.0730 1.001 - 1.487 0.910 - 1.182 0.710 5174 3432 #------------------------------------------------------------------------------ Refinement: #------------------------------------------------------------------------------ HKLF-5 refinement using single reflections from dominant twin component 1, plus all overlaps. Refined BASF: 0.2677(14) ; _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? #------------------------------------------------------------------------------ # total number of reflections = sum of all single component 1 + all composites # data merged in TWINABS: R(int) is for all single component 1 + all composites #------------------------------------------------------------------------------ _diffrn_reflns_number 21211 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0631 #------------------------------------------------------------------------------ _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 25.06 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 5566 _reflns_number_gt 3270 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 v2010.1-2 (Bruker, 2010)' _computing_cell_refinement 'SAINT v.7.68a (Bruker, 2010)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXTL v.6.12 (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0907P)^2^] 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 5566 _refine_ls_number_parameters 307 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1033 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1420 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.468 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.057 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.08105(7) 0.23063(10) 0.41983(9) 0.0790(4) Uani 1 1 d . . . Cl2 Cl 0.16228(6) 0.22294(8) 0.25985(6) 0.0560(3) Uani 1 1 d . . . O1 O 0.4004(2) 0.5610(2) 0.3227(2) 0.0826(9) Uani 1 1 d . . . O2 O 0.28672(19) 0.4411(2) 0.2570(2) 0.0769(9) Uani 1 1 d . . . O3 O 0.30577(17) 0.0231(2) 0.2691(2) 0.0615(7) Uani 1 1 d . . . O4 O 0.43600(16) -0.06709(19) 0.33190(18) 0.0574(7) Uani 1 1 d . . . N1 N 0.55569(17) 0.2569(2) 0.4232(2) 0.0422(7) Uani 1 1 d . . . H1A H 0.6108 0.2613 0.4623 0.051 Uiso 1 1 calc R . . C1 C 0.5105(2) 0.3586(3) 0.3927(2) 0.0357(8) Uani 1 1 d . . . C2 C 0.4219(2) 0.3558(3) 0.3461(2) 0.0343(8) Uani 1 1 d . . . C3 C 0.3702(2) 0.2424(2) 0.3360(2) 0.0318(8) Uani 1 1 d . . . H3A H 0.3250 0.2389 0.2688 0.038 Uiso 1 1 calc R . . C4 C 0.4306(2) 0.1374(3) 0.3504(2) 0.0318(8) Uani 1 1 d . . . C5 C 0.5195(2) 0.1471(3) 0.3961(2) 0.0353(8) Uani 1 1 d . . . C6 C 0.3225(2) 0.2399(2) 0.4081(2) 0.0301(7) Uani 1 1 d . . . C7 C 0.3744(2) 0.2475(2) 0.5072(2) 0.0360(8) Uani 1 1 d . . . H7A H 0.4360 0.2526 0.5265 0.043 Uiso 1 1 calc R . . C8 C 0.3383(3) 0.2477(3) 0.5780(3) 0.0513(10) Uani 1 1 d . . . H8A H 0.3751 0.2514 0.6445 0.062 Uiso 1 1 calc R . . C9 C 0.2481(3) 0.2424(3) 0.5508(3) 0.0536(10) Uani 1 1 d . . . H9A H 0.2228 0.2429 0.5985 0.064 Uiso 1 1 calc R . . C10 C 0.1948(2) 0.2363(3) 0.4524(3) 0.0476(9) Uani 1 1 d . . . C11 C 0.2328(2) 0.2334(3) 0.3813(2) 0.0367(8) Uani 1 1 d . . . C12 C 0.5684(2) 0.4648(3) 0.4157(3) 0.0566(10) Uani 1 1 d . . . H12A H 0.5542 0.5137 0.4614 0.085 Uiso 1 1 calc R . . H12B H 0.5586 0.5079 0.3560 0.085 Uiso 1 1 calc R . . H12C H 0.6299 0.4412 0.4446 0.085 Uiso 1 1 calc R . . C13 C 0.3721(3) 0.4629(3) 0.3096(3) 0.0510(10) Uani 1 1 d . . . C14 C 0.2253(5) 0.5414(5) 0.1936(7) 0.166(3) Uani 1 1 d D . . H14A H 0.2588 0.6074 0.1832 0.199 Uiso 1 1 calc R . . H14B H 0.1827 0.5135 0.1310 0.199 Uiso 1 1 calc R . . C15 C 0.1828(7) 0.5679(7) 0.2678(7) 0.241(5) Uani 1 1 d D . . H15A H 0.1345 0.6224 0.2395 0.362 Uiso 1 1 calc R . . H15B H 0.2265 0.6017 0.3261 0.362 Uiso 1 1 calc R . . H15C H 0.1603 0.4964 0.2848 0.362 Uiso 1 1 calc R . . C16 C 0.3846(3) 0.0281(3) 0.3134(2) 0.0388(8) Uani 1 1 d . . . C17 C 0.3941(3) -0.1765(3) 0.2977(3) 0.0673(12) Uani 1 1 d . . . H17A H 0.4385 -0.2344 0.3016 0.101 Uiso 1 1 calc R . . H17B H 0.3535 -0.1687 0.2304 0.101 Uiso 1 1 calc R . . H17C H 0.3619 -0.2007 0.3381 0.101 Uiso 1 1 calc R . . C18 C 0.5875(2) 0.0514(3) 0.4238(3) 0.0526(10) Uani 1 1 d . . . H18A H 0.5736 -0.0049 0.4649 0.079 Uiso 1 1 calc R . . H18B H 0.6455 0.0843 0.4591 0.079 Uiso 1 1 calc R . . H18C H 0.5873 0.0131 0.3650 0.079 Uiso 1 1 calc R . . O5 O 0.74743(19) 0.2631(3) 0.5030(3) 0.1075(13) Uani 1 1 d . . . N2 N 0.8733(2) 0.1759(3) 0.5991(3) 0.0783(11) Uani 1 1 d . . . N3 N 0.8759(2) 0.3479(3) 0.5218(3) 0.0983(15) Uani 1 1 d . . . C19 C 0.8277(3) 0.2626(4) 0.5401(3) 0.0695(12) Uani 1 1 d . . . C20 C 0.8240(4) 0.0932(5) 0.6358(5) 0.139(2) Uani 1 1 d . . . H20A H 0.7731 0.1321 0.6409 0.208 Uiso 1 1 calc R . . H20B H 0.8620 0.0650 0.6997 0.208 Uiso 1 1 calc R . . H20C H 0.8044 0.0282 0.5909 0.208 Uiso 1 1 calc R . . C21 C 0.9551(3) 0.1304(4) 0.5995(4) 0.1062(18) Uani 1 1 d . . . H21A H 0.9749 0.1771 0.5568 0.159 Uiso 1 1 calc R . . H21B H 0.9467 0.0505 0.5764 0.159 Uiso 1 1 calc R . . H21C H 0.9991 0.1328 0.6654 0.159 Uiso 1 1 calc R . . C22 C 0.8280(4) 0.4341(6) 0.4449(5) 0.187(4) Uani 1 1 d . . . H22A H 0.7868 0.3937 0.3885 0.281 Uiso 1 1 calc R . . H22B H 0.8701 0.4771 0.4257 0.281 Uiso 1 1 calc R . . H22C H 0.7960 0.4878 0.4703 0.281 Uiso 1 1 calc R . . C23 C 0.9571(3) 0.3916(4) 0.5924(4) 0.0979(17) Uani 1 1 d . . . H23A H 0.9700 0.3518 0.6542 0.147 Uiso 1 1 calc R . . H23B H 0.9514 0.4745 0.6014 0.147 Uiso 1 1 calc R . . H23C H 1.0047 0.3782 0.5694 0.147 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0431(6) 0.1197(9) 0.0878(9) -0.0003(7) 0.0400(6) -0.0061(6) Cl2 0.0323(5) 0.0914(7) 0.0383(5) 0.0024(5) 0.0064(4) -0.0064(5) O1 0.097(2) 0.0361(16) 0.115(3) 0.0054(16) 0.0394(19) -0.0030(16) O2 0.058(2) 0.0562(17) 0.105(2) 0.0213(15) 0.0174(18) 0.0176(15) O3 0.0405(16) 0.0535(15) 0.0822(19) -0.0245(14) 0.0134(14) -0.0145(13) O4 0.0628(18) 0.0327(14) 0.0627(17) -0.0072(12) 0.0074(14) -0.0050(13) N1 0.0307(15) 0.0493(19) 0.0443(17) -0.0027(14) 0.0115(13) -0.0093(14) C1 0.041(2) 0.039(2) 0.035(2) -0.0019(16) 0.0230(17) -0.0072(18) C2 0.046(2) 0.0342(19) 0.0288(19) -0.0025(14) 0.0205(17) -0.0029(17) C3 0.0335(18) 0.0425(19) 0.0204(16) 0.0004(14) 0.0112(14) -0.0045(15) C4 0.037(2) 0.0357(19) 0.0263(19) -0.0008(14) 0.0156(16) -0.0031(16) C5 0.039(2) 0.043(2) 0.029(2) 0.0001(15) 0.0184(16) -0.0047(17) C6 0.0329(19) 0.0311(18) 0.0284(18) 0.0020(14) 0.0140(15) -0.0028(14) C7 0.0344(19) 0.048(2) 0.0284(19) -0.0001(16) 0.0148(15) -0.0014(16) C8 0.058(3) 0.068(3) 0.0292(19) -0.0017(17) 0.0167(19) -0.003(2) C9 0.056(3) 0.073(3) 0.043(2) 0.0021(19) 0.031(2) -0.001(2) C10 0.038(2) 0.060(2) 0.052(2) -0.0011(18) 0.0253(19) -0.0024(18) C11 0.0358(19) 0.046(2) 0.0294(18) 0.0014(15) 0.0131(15) -0.0062(16) C12 0.058(2) 0.054(2) 0.069(3) -0.014(2) 0.036(2) -0.0213(19) C13 0.059(3) 0.051(3) 0.050(3) 0.0032(19) 0.029(2) 0.002(2) C14 0.170(7) 0.089(4) 0.288(10) 0.010(5) 0.140(7) 0.025(4) C15 0.306(14) 0.165(8) 0.276(13) 0.052(8) 0.134(11) 0.055(8) C16 0.049(2) 0.044(2) 0.029(2) -0.0062(16) 0.0211(18) -0.009(2) C17 0.082(3) 0.047(2) 0.070(3) -0.006(2) 0.025(2) -0.013(2) C18 0.041(2) 0.056(2) 0.060(3) 0.003(2) 0.0183(19) 0.0038(19) O5 0.0323(17) 0.087(2) 0.176(4) 0.030(2) 0.007(2) -0.0114(15) N2 0.052(2) 0.075(2) 0.108(3) 0.027(2) 0.029(2) -0.004(2) N3 0.049(2) 0.099(3) 0.106(3) 0.048(2) -0.018(2) -0.025(2) C19 0.038(2) 0.073(3) 0.083(3) 0.017(2) 0.006(2) -0.010(2) C20 0.103(5) 0.119(5) 0.189(6) 0.065(4) 0.050(5) -0.020(4) C21 0.056(3) 0.104(4) 0.152(5) 0.019(3) 0.032(3) 0.005(3) C22 0.093(5) 0.171(6) 0.212(8) 0.126(6) -0.042(5) -0.036(4) C23 0.048(3) 0.100(4) 0.123(4) 0.027(3) 0.005(3) -0.017(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C10 1.736(4) . ? Cl2 C11 1.734(3) . ? O1 C13 1.207(4) . ? O2 C13 1.341(4) . ? O2 C14 1.583(7) . ? O3 C16 1.207(4) . ? O4 C16 1.343(4) . ? O4 C17 1.430(4) . ? N1 C1 1.365(4) . ? N1 C5 1.387(4) . ? N1 H1A 0.8700 . ? C1 C2 1.350(4) . ? C1 C12 1.502(4) . ? C2 C13 1.462(5) . ? C2 C3 1.529(4) . ? C3 C4 1.522(4) . ? C3 C6 1.535(4) . ? C3 H3A 0.9900 . ? C4 C5 1.356(4) . ? C4 C16 1.460(4) . ? C5 C18 1.507(4) . ? C6 C11 1.369(4) . ? C6 C7 1.392(4) . ? C7 C8 1.378(5) . ? C7 H7A 0.9400 . ? C8 C9 1.374(5) . ? C8 H8A 0.9400 . ? C9 C10 1.387(5) . ? C9 H9A 0.9400 . ? C10 C11 1.405(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? C14 C15 1.528(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C18 H18C 0.9700 . ? O5 C19 1.216(5) . ? N2 C19 1.349(5) . ? N2 C21 1.433(5) . ? N2 C20 1.472(5) . ? N3 C19 1.346(5) . ? N3 C23 1.436(5) . ? N3 C22 1.489(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 H20C 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? 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 C13 O2 C14 119.8(4) . . ? C16 O4 C17 117.6(3) . . ? C1 N1 C5 124.3(3) . . ? C1 N1 H1A 117.8 . . ? C5 N1 H1A 117.8 . . ? C2 C1 N1 119.4(3) . . ? C2 C1 C12 126.8(3) . . ? N1 C1 C12 113.8(3) . . ? C1 C2 C13 120.7(3) . . ? C1 C2 C3 121.2(3) . . ? C13 C2 C3 118.0(3) . . ? C4 C3 C2 110.8(3) . . ? C4 C3 C6 111.0(2) . . ? C2 C3 C6 110.6(2) . . ? C4 C3 H3A 108.1 . . ? C2 C3 H3A 108.1 . . ? C6 C3 H3A 108.1 . . ? C5 C4 C16 124.2(3) . . ? C5 C4 C3 121.4(3) . . ? C16 C4 C3 114.3(3) . . ? C4 C5 N1 118.6(3) . . ? C4 C5 C18 128.2(3) . . ? N1 C5 C18 113.2(3) . . ? C11 C6 C7 118.1(3) . . ? C11 C6 C3 124.5(3) . . ? C7 C6 C3 117.3(3) . . ? C8 C7 C6 122.1(3) . . ? C8 C7 H7A 118.9 . . ? C6 C7 H7A 118.9 . . ? C9 C8 C7 119.6(3) . . ? C9 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C8 C9 C10 119.6(3) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C9 C10 C11 120.1(3) . . ? C9 C10 Cl1 118.7(3) . . ? C11 C10 Cl1 121.2(3) . . ? C6 C11 C10 120.5(3) . . ? C6 C11 Cl2 121.8(3) . . ? C10 C11 Cl2 117.7(3) . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O1 C13 O2 121.4(3) . . ? O1 C13 C2 126.9(4) . . ? O2 C13 C2 111.8(3) . . ? C15 C14 O2 94.6(6) . . ? C15 C14 H14A 112.8 . . ? O2 C14 H14A 112.8 . . ? C15 C14 H14B 112.8 . . ? O2 C14 H14B 112.8 . . ? H14A C14 H14B 110.3 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O3 C16 O4 122.0(3) . . ? O3 C16 C4 122.6(3) . . ? O4 C16 C4 115.4(3) . . ? O4 C17 H17A 109.5 . . ? O4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C5 C18 H18A 109.5 . . ? C5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C19 N2 C21 124.1(4) . . ? C19 N2 C20 117.9(4) . . ? C21 N2 C20 113.6(4) . . ? C19 N3 C23 124.1(4) . . ? C19 N3 C22 117.2(4) . . ? C23 N3 C22 113.5(4) . . ? O5 C19 N3 121.3(4) . . ? O5 C19 N2 122.3(4) . . ? N3 C19 N2 116.4(4) . . ? N2 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 C23 H23A 109.5 . . ? N3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 11.2(5) . . . . ? C5 N1 C1 C12 -168.5(3) . . . . ? N1 C1 C2 C13 -178.0(3) . . . . ? C12 C1 C2 C13 1.7(5) . . . . ? N1 C1 C2 C3 6.2(4) . . . . ? C12 C1 C2 C3 -174.2(3) . . . . ? C1 C2 C3 C4 -19.9(4) . . . . ? C13 C2 C3 C4 164.2(3) . . . . ? C1 C2 C3 C6 103.7(3) . . . . ? C13 C2 C3 C6 -72.2(3) . . . . ? C2 C3 C4 C5 19.2(4) . . . . ? C6 C3 C4 C5 -104.2(3) . . . . ? C2 C3 C4 C16 -162.2(2) . . . . ? C6 C3 C4 C16 74.4(3) . . . . ? C16 C4 C5 N1 176.5(3) . . . . ? C3 C4 C5 N1 -5.0(4) . . . . ? C16 C4 C5 C18 -4.0(5) . . . . ? C3 C4 C5 C18 174.4(3) . . . . ? C1 N1 C5 C4 -11.8(4) . . . . ? C1 N1 C5 C18 168.7(3) . . . . ? C4 C3 C6 C11 -118.0(3) . . . . ? C2 C3 C6 C11 118.5(3) . . . . ? C4 C3 C6 C7 63.5(3) . . . . ? C2 C3 C6 C7 -60.1(3) . . . . ? C11 C6 C7 C8 0.5(5) . . . . ? C3 C6 C7 C8 179.1(3) . . . . ? C6 C7 C8 C9 -1.2(5) . . . . ? C7 C8 C9 C10 0.3(5) . . . . ? C8 C9 C10 C11 1.2(5) . . . . ? C8 C9 C10 Cl1 -179.6(3) . . . . ? C7 C6 C11 C10 1.0(5) . . . . ? C3 C6 C11 C10 -177.5(3) . . . . ? C7 C6 C11 Cl2 -179.7(2) . . . . ? C3 C6 C11 Cl2 1.8(4) . . . . ? C9 C10 C11 C6 -1.9(5) . . . . ? Cl1 C10 C11 C6 178.9(2) . . . . ? C9 C10 C11 Cl2 178.8(3) . . . . ? Cl1 C10 C11 Cl2 -0.5(4) . . . . ? C14 O2 C13 O1 12.0(6) . . . . ? C14 O2 C13 C2 -167.9(4) . . . . ? C1 C2 C13 O1 -6.4(5) . . . . ? C3 C2 C13 O1 169.6(3) . . . . ? C1 C2 C13 O2 173.6(3) . . . . ? C3 C2 C13 O2 -10.4(4) . . . . ? C13 O2 C14 C15 -100.7(6) . . . . ? C17 O4 C16 O3 -0.4(5) . . . . ? C17 O4 C16 C4 179.6(3) . . . . ? C5 C4 C16 O3 -176.6(3) . . . . ? C3 C4 C16 O3 4.9(5) . . . . ? C5 C4 C16 O4 3.4(4) . . . . ? C3 C4 C16 O4 -175.2(2) . . . . ? C23 N3 C19 O5 145.1(5) . . . . ? C22 N3 C19 O5 -7.7(8) . . . . ? C23 N3 C19 N2 -36.7(7) . . . . ? C22 N3 C19 N2 170.5(6) . . . . ? C21 N2 C19 O5 141.7(5) . . . . ? C20 N2 C19 O5 -13.1(8) . . . . ? C21 N2 C19 N3 -36.4(7) . . . . ? C20 N2 C19 N3 168.7(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O5 0.87 2.08 2.904(4) 157.4 . #===END _database_code_depnum_ccdc_archive 'CCDC 935392'