# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name # Name of author for correspondence ; Prof. Mino R Caira ; _publ_contact_author_address # Address of author for correspondence ; Department of Chemistry University of Cape Town Rondebosch 7701 South Africa ; _publ_contact_author_email Mino.Caira@uct.ac.za _publ_contact_author_fax '+27 21 650 5195' _publ_contact_author_phone '+27 21 650 3071' #============================================================================== # 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_accepted 'To be submitted 2011' _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_issue ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= #3. TITLE AND AUTHOR LIST _publ_section_title ; Co-crystals of the antiretroviral Nevirapine: crystal structures, thermal analysis and dissolution behaviour ; _publ_section_title_footnote ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address M.Caira ; Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa ; S.Bourne ; Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa ; H.Samsodien ; Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa ; E.Engel ; Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa ; W.Liebenberg ; Unit for Drug Research and Development, Faculty of Health Sciences, North-west University, Potchefstroom 2531, South Africa ; N.Stieger ; Unit for Drug Research and Development, Faculty of Health Sciences, North-west University, Potchefstroom 2531, South Africa ; ; M.Aucamp ; ; Unit for Drug Research and Development, Faculty of Health Sciences, North-west University, Potchefstroom 2531, South Africa ; data_c:\emilem~1\scdpro~1\n004\n00499 _database_code_depnum_ccdc_archive 'CCDC 853021' #TrackingRef 'NVGLTfin.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido [3,2-b:2',3'-e]diazepin-6-one pentanedioic acid 1:1 co-crystal ; _chemical_name_common 'nevirapine-glutaric acid 1:1 co-crystal' _chemical_melting_point '137 degrees C melting onset by DSC' _chemical_formula_moiety 'C15 H14 N4 O, C5 H8 O4' _chemical_formula_sum 'C20 H22 N4 O5' _chemical_formula_weight 398.42 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.363(4) _cell_length_b 12.292(6) _cell_length_c 12.305(6) _cell_angle_alpha 118.571(8) _cell_angle_beta 90.144(9) _cell_angle_gamma 98.023(8) _cell_volume 965.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3360 _cell_measurement_theta_min 1.89 _cell_measurement_theta_max 26.37 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9724 _exptl_absorpt_correction_T_max 0.9792 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Kappa Duo Apex II diffractometer' _diffrn_measurement_method 'phi- and omega scans of 0.5 deg' _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% 0 _diffrn_reflns_number 22292 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3906 _reflns_number_gt 2999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0365P)^2^+0.3526P] 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 0.0088(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3906 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.22065(19) 0.32132(13) 0.29182(13) 0.0227(3) Uani 1 1 d . . . N2 N 0.31174(15) 0.24255(11) 0.20042(11) 0.0224(3) Uani 1 1 d . . . H2 H 0.4167 0.2761 0.1866 0.027 Uiso 1 1 calc R . . C3 C 0.25853(18) 0.11112(13) 0.12320(13) 0.0210(3) Uani 1 1 d . . . C4 C 0.19602(18) 0.03219(13) 0.17195(13) 0.0211(3) Uani 1 1 d . . . N5 N 0.16634(15) 0.08343(11) 0.30023(11) 0.0218(3) Uani 1 1 d . . . C6 C 0.03318(18) 0.16357(13) 0.34272(12) 0.0208(3) Uani 1 1 d . . . C7 C 0.05266(18) 0.27292(13) 0.33221(12) 0.0216(3) Uani 1 1 d . . . O8 O 0.27230(14) 0.43621(9) 0.34365(10) 0.0312(3) Uani 1 1 d . . . C9 C -0.08453(19) 0.34738(14) 0.37390(13) 0.0242(3) Uani 1 1 d . . . H9 H -0.0745 0.4226 0.3686 0.029 Uiso 1 1 calc R . . C10 C -0.23585(19) 0.31189(14) 0.42315(13) 0.0260(3) Uani 1 1 d . . . H10 H -0.3351 0.3582 0.4469 0.031 Uiso 1 1 calc R . . C11 C -0.23638(19) 0.20670(14) 0.43627(13) 0.0264(3) Uani 1 1 d . . . H11 H -0.3353 0.1850 0.4753 0.032 Uiso 1 1 calc R . . N12 N -0.10622(16) 0.13280(11) 0.39754(11) 0.0250(3) Uani 1 1 d . . . N13 N 0.16181(16) -0.09213(11) 0.10423(11) 0.0252(3) Uani 1 1 d . . . C14 C 0.19152(19) -0.14147(14) -0.01654(14) 0.0270(3) Uani 1 1 d . . . H14 H 0.1733 -0.2303 -0.0657 0.032 Uiso 1 1 calc R . . C15 C 0.24690(19) -0.07056(14) -0.07315(14) 0.0264(3) Uani 1 1 d . . . H15 H 0.2624 -0.1106 -0.1596 0.032 Uiso 1 1 calc R . . C16 C 0.28005(18) 0.05930(14) -0.00398(13) 0.0229(3) Uani 1 1 d . . . C17 C 0.3363(2) 0.14025(15) -0.06255(14) 0.0288(3) Uani 1 1 d . . . H17A H 0.4636 0.1823 -0.0332 0.043 Uiso 1 1 calc R . . H17B H 0.2551 0.2034 -0.0396 0.043 Uiso 1 1 calc R . . H17C H 0.3270 0.0879 -0.1530 0.043 Uiso 1 1 calc R . . C18 C 0.1728(2) 0.00147(14) 0.35365(14) 0.0255(3) Uani 1 1 d . . . H18 H 0.0649 -0.0661 0.3336 0.031 Uiso 1 1 calc R . . C19 C 0.3594(2) -0.02682(14) 0.36802(14) 0.0272(3) Uani 1 1 d . . . H19A H 0.4637 0.0098 0.3388 0.033 Uiso 1 1 calc R . . H19B H 0.3679 -0.1110 0.3574 0.033 Uiso 1 1 calc R . . C20 C 0.2711(2) 0.06143(15) 0.48012(14) 0.0296(4) Uani 1 1 d . . . H20A H 0.2254 0.0313 0.5382 0.036 Uiso 1 1 calc R . . H20B H 0.3212 0.1521 0.5196 0.036 Uiso 1 1 calc R . . O21 O 0.57066(15) 0.57881(10) 0.34751(11) 0.0385(3) Uani 1 1 d . . . H21 H 0.4762 0.5280 0.3401 0.046 Uiso 1 1 calc R . . O22 O 0.64563(14) 0.41051(10) 0.18559(10) 0.0322(3) Uani 1 1 d . . . C23 C 0.68192(19) 0.52011(14) 0.26148(14) 0.0248(3) Uani 1 1 d . . . C24 C 0.8557(2) 0.60493(14) 0.26959(15) 0.0292(4) Uani 1 1 d . . . H24A H 0.9119 0.6485 0.3560 0.035 Uiso 1 1 calc R . . H24B H 0.8236 0.6697 0.2502 0.035 Uiso 1 1 calc R . . C25 C 0.99733(19) 0.53738(14) 0.18285(14) 0.0266(3) Uani 1 1 d . . . H25A H 1.0332 0.4741 0.2032 0.032 Uiso 1 1 calc R . . H25B H 0.9421 0.4928 0.0962 0.032 Uiso 1 1 calc R . . C26 C 1.1674(2) 0.62890(15) 0.19408(15) 0.0293(4) Uani 1 1 d . . . H26A H 1.1296 0.6929 0.1755 0.035 Uiso 1 1 calc R . . H26B H 1.2217 0.6727 0.2810 0.035 Uiso 1 1 calc R . . C27 C 1.31205(19) 0.56888(15) 0.10986(14) 0.0267(3) Uani 1 1 d . . . O28 O 1.29306(14) 0.45792(10) 0.03405(11) 0.0327(3) Uani 1 1 d . . . O29 O 1.46155(15) 0.64897(10) 0.12503(11) 0.0373(3) Uani 1 1 d . . . H29 H 1.5358 0.6117 0.0734 0.045 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 C1 0.0202(7) 0.0205(8) 0.0221(7) 0.0065(6) 0.0021(6) 0.0016(6) N2 0.0173(6) 0.0203(6) 0.0247(6) 0.0075(5) 0.0061(5) 0.0008(5) C3 0.0148(6) 0.0193(7) 0.0229(7) 0.0054(6) 0.0023(5) 0.0031(5) C4 0.0142(6) 0.0217(8) 0.0231(7) 0.0074(6) -0.0004(5) 0.0033(5) N5 0.0204(6) 0.0212(6) 0.0224(6) 0.0097(5) 0.0030(5) 0.0025(5) C6 0.0177(7) 0.0228(8) 0.0159(7) 0.0058(6) 0.0002(5) -0.0009(5) C7 0.0189(7) 0.0216(8) 0.0166(7) 0.0039(6) 0.0022(5) 0.0000(6) O8 0.0289(6) 0.0189(6) 0.0356(6) 0.0059(5) 0.0121(5) 0.0001(4) C9 0.0244(7) 0.0197(7) 0.0207(7) 0.0042(6) 0.0031(6) 0.0016(6) C10 0.0198(7) 0.0269(8) 0.0205(7) 0.0032(6) 0.0046(6) 0.0031(6) C11 0.0200(7) 0.0307(8) 0.0198(7) 0.0070(6) 0.0042(6) -0.0020(6) N12 0.0210(6) 0.0276(7) 0.0221(6) 0.0099(6) 0.0023(5) -0.0013(5) N13 0.0207(6) 0.0207(7) 0.0280(7) 0.0069(5) -0.0022(5) 0.0032(5) C14 0.0219(7) 0.0208(8) 0.0284(8) 0.0036(7) -0.0025(6) 0.0051(6) C15 0.0188(7) 0.0292(8) 0.0212(7) 0.0038(7) 0.0005(6) 0.0059(6) C16 0.0138(6) 0.0275(8) 0.0231(7) 0.0084(6) 0.0023(5) 0.0047(6) C17 0.0256(8) 0.0345(9) 0.0239(8) 0.0122(7) 0.0059(6) 0.0051(6) C18 0.0212(7) 0.0250(8) 0.0313(8) 0.0157(7) 0.0003(6) -0.0013(6) C19 0.0234(7) 0.0269(8) 0.0307(8) 0.0142(7) -0.0005(6) 0.0008(6) C20 0.0267(8) 0.0364(9) 0.0287(8) 0.0185(7) 0.0037(6) 0.0033(7) O21 0.0325(6) 0.0245(6) 0.0426(7) 0.0052(5) 0.0201(5) -0.0027(5) O22 0.0241(5) 0.0231(6) 0.0373(6) 0.0057(5) 0.0097(5) 0.0007(4) C23 0.0224(7) 0.0241(8) 0.0262(8) 0.0108(7) 0.0055(6) 0.0042(6) C24 0.0242(8) 0.0251(8) 0.0325(8) 0.0103(7) 0.0066(6) 0.0001(6) C25 0.0206(7) 0.0261(8) 0.0316(8) 0.0130(7) 0.0062(6) 0.0017(6) C26 0.0236(8) 0.0278(8) 0.0329(8) 0.0127(7) 0.0056(6) 0.0004(6) C27 0.0216(7) 0.0292(9) 0.0318(8) 0.0176(7) 0.0029(6) 0.0007(6) O28 0.0248(6) 0.0279(6) 0.0434(7) 0.0159(6) 0.0111(5) 0.0034(4) O29 0.0253(6) 0.0333(7) 0.0427(7) 0.0119(6) 0.0130(5) -0.0027(5) _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 O8 1.2382(18) . ? C1 N2 1.3401(18) . ? C1 C7 1.4871(19) . ? N2 C3 1.4211(19) . ? N2 H2 0.8800 . ? C3 C4 1.395(2) . ? C3 C16 1.399(2) . ? C4 N13 1.3292(19) . ? C4 N5 1.4232(19) . ? N5 C6 1.4088(19) . ? N5 C18 1.4477(19) . ? C6 N12 1.3382(18) . ? C6 C7 1.399(2) . ? C7 C9 1.390(2) . ? C9 C10 1.385(2) . ? C9 H9 0.9500 . ? C10 C11 1.377(2) . ? C10 H10 0.9500 . ? C11 N12 1.342(2) . ? C11 H11 0.9500 . ? N13 C14 1.342(2) . ? C14 C15 1.376(2) . ? C14 H14 0.9500 . ? C15 C16 1.387(2) . ? C15 H15 0.9500 . ? C16 C17 1.501(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.494(2) . ? C18 C20 1.496(2) . ? C18 H18 1.0000 . ? C19 C20 1.508(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? O21 C23 1.3234(18) . ? O21 H21 0.8400 . ? O22 C23 1.2056(18) . ? C23 C24 1.504(2) . ? C24 C25 1.522(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.520(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.499(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 O28 1.2162(19) . ? C27 O29 1.3178(18) . ? O29 H29 0.8400 . ? 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 O8 C1 N2 121.03(13) . . ? O8 C1 C7 118.23(12) . . ? N2 C1 C7 120.73(13) . . ? C1 N2 C3 127.52(12) . . ? C1 N2 H2 116.2 . . ? C3 N2 H2 116.2 . . ? C4 C3 C16 119.43(13) . . ? C4 C3 N2 121.74(13) . . ? C16 C3 N2 118.72(13) . . ? N13 C4 C3 123.28(14) . . ? N13 C4 N5 116.44(13) . . ? C3 C4 N5 120.28(13) . . ? C6 N5 C4 116.01(11) . . ? C6 N5 C18 116.05(11) . . ? C4 N5 C18 116.54(12) . . ? N12 C6 C7 122.31(13) . . ? N12 C6 N5 116.99(13) . . ? C7 C6 N5 120.64(12) . . ? C9 C7 C6 118.11(13) . . ? C9 C7 C1 117.84(13) . . ? C6 C7 C1 123.70(13) . . ? C10 C9 C7 119.99(14) . . ? C10 C9 H9 120.0 . . ? C7 C9 H9 120.0 . . ? C11 C10 C9 117.26(14) . . ? C11 C10 H10 121.4 . . ? C9 C10 H10 121.4 . . ? N12 C11 C10 124.29(13) . . ? N12 C11 H11 117.9 . . ? C10 C11 H11 117.9 . . ? C6 N12 C11 117.77(13) . . ? C4 N13 C14 116.91(13) . . ? N13 C14 C15 123.63(14) . . ? N13 C14 H14 118.2 . . ? C15 C14 H14 118.2 . . ? C14 C15 C16 120.00(14) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C3 116.62(14) . . ? C15 C16 C17 121.73(14) . . ? C3 C16 C17 121.65(14) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N5 C18 C19 115.15(12) . . ? N5 C18 C20 115.38(13) . . ? C19 C18 C20 60.55(10) . . ? N5 C18 H18 117.8 . . ? C19 C18 H18 117.8 . . ? C20 C18 H18 117.8 . . ? C18 C19 C20 59.78(10) . . ? C18 C19 H19A 117.8 . . ? C20 C19 H19A 117.8 . . ? C18 C19 H19B 117.8 . . ? C20 C19 H19B 117.8 . . ? H19A C19 H19B 114.9 . . ? C18 C20 C19 59.67(10) . . ? C18 C20 H20A 117.8 . . ? C19 C20 H20A 117.8 . . ? C18 C20 H20B 117.8 . . ? C19 C20 H20B 117.8 . . ? H20A C20 H20B 114.9 . . ? C23 O21 H21 109.5 . . ? O22 C23 O21 122.87(13) . . ? O22 C23 C24 124.52(13) . . ? O21 C23 C24 112.62(13) . . ? C23 C24 C25 114.07(13) . . ? C23 C24 H24A 108.7 . . ? C25 C24 H24A 108.7 . . ? C23 C24 H24B 108.7 . . ? C25 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C26 C25 C24 111.23(13) . . ? C26 C25 H25A 109.4 . . ? C24 C25 H25A 109.4 . . ? C26 C25 H25B 109.4 . . ? C24 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C27 C26 C25 114.14(13) . . ? C27 C26 H26A 108.7 . . ? C25 C26 H26A 108.7 . . ? C27 C26 H26B 108.7 . . ? C25 C26 H26B 108.7 . . ? H26A C26 H26B 107.6 . . ? O28 C27 O29 123.24(14) . . ? O28 C27 C26 123.62(13) . . ? O29 C27 C26 113.13(14) . . ? C27 O29 H29 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 O8 C1 N2 C3 -172.28(14) . . . . ? C7 C1 N2 C3 6.7(2) . . . . ? C1 N2 C3 C4 -46.9(2) . . . . ? C1 N2 C3 C16 136.88(15) . . . . ? C16 C3 C4 N13 2.7(2) . . . . ? N2 C3 C4 N13 -173.40(12) . . . . ? C16 C3 C4 N5 -177.53(12) . . . . ? N2 C3 C4 N5 6.3(2) . . . . ? N13 C4 N5 C6 -118.98(14) . . . . ? C3 C4 N5 C6 61.28(17) . . . . ? N13 C4 N5 C18 23.20(17) . . . . ? C3 C4 N5 C18 -156.54(12) . . . . ? C4 N5 C6 N12 123.30(13) . . . . ? C18 N5 C6 N12 -19.07(18) . . . . ? C4 N5 C6 C7 -59.46(17) . . . . ? C18 N5 C6 C7 158.16(13) . . . . ? N12 C6 C7 C9 -3.9(2) . . . . ? N5 C6 C7 C9 178.98(12) . . . . ? N12 C6 C7 C1 169.18(13) . . . . ? N5 C6 C7 C1 -7.9(2) . . . . ? O8 C1 C7 C9 31.6(2) . . . . ? N2 C1 C7 C9 -147.34(14) . . . . ? O8 C1 C7 C6 -141.49(15) . . . . ? N2 C1 C7 C6 39.5(2) . . . . ? C6 C7 C9 C10 -0.5(2) . . . . ? C1 C7 C9 C10 -174.07(13) . . . . ? C7 C9 C10 C11 4.4(2) . . . . ? C9 C10 C11 N12 -4.3(2) . . . . ? C7 C6 N12 C11 4.2(2) . . . . ? N5 C6 N12 C11 -178.64(12) . . . . ? C10 C11 N12 C6 0.1(2) . . . . ? C3 C4 N13 C14 0.5(2) . . . . ? N5 C4 N13 C14 -179.21(12) . . . . ? C4 N13 C14 C15 -2.9(2) . . . . ? N13 C14 C15 C16 1.8(2) . . . . ? C14 C15 C16 C3 1.5(2) . . . . ? C14 C15 C16 C17 -178.54(13) . . . . ? C4 C3 C16 C15 -3.63(19) . . . . ? N2 C3 C16 C15 172.64(12) . . . . ? C4 C3 C16 C17 176.42(13) . . . . ? N2 C3 C16 C17 -7.3(2) . . . . ? C6 N5 C18 C19 -147.22(13) . . . . ? C4 N5 C18 C19 70.61(16) . . . . ? C6 N5 C18 C20 -79.45(16) . . . . ? C4 N5 C18 C20 138.38(13) . . . . ? N5 C18 C19 C20 106.19(15) . . . . ? N5 C18 C20 C19 -105.80(14) . . . . ? O22 C23 C24 C25 -7.3(2) . . . . ? O21 C23 C24 C25 172.75(13) . . . . ? C23 C24 C25 C26 178.88(14) . . . . ? C24 C25 C26 C27 -179.25(13) . . . . ? C25 C26 C27 O28 3.7(2) . . . . ? C25 C26 C27 O29 -177.14(13) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.264 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.038 # Attachment 'NVMLEfin.CIF' data_c:\n009\n009 _database_code_depnum_ccdc_archive 'CCDC 853022' #TrackingRef 'NVMLEfin.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e]diazepin-6-one (Z)-butenedioic acid 1:1 co-crystal ; _chemical_name_common 'nevirapine-maleic acid 1:1 co-crystal' _chemical_melting_point '184 degrees C by DSC' _chemical_formula_moiety 'C15 H14 N4 O, C4 H4 O4' _chemical_formula_sum 'C19 H18 N4 O5' _chemical_formula_weight 382.37 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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 7.4001(5) _cell_length_b 10.4599(7) _cell_length_c 23.2561(16) _cell_angle_alpha 90.00 _cell_angle_beta 98.9680(10) _cell_angle_gamma 90.00 _cell_volume 1778.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3653 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 26.46 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9874 _exptl_absorpt_correction_T_max 0.9968 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 Kappa Duo Apex II diffractometer' _diffrn_measurement_method 'phi- and omega scans of 0.5 deg' _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% 0 _diffrn_reflns_number 18372 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.46 _reflns_number_total 3653 _reflns_number_gt 2773 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0424P)^2^+1.0226P] 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 0.0023(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3653 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0942 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 0.9037(2) 0.41982(16) 0.16992(7) 0.0172(4) Uani 1 1 d . . . N2 N 0.7707(2) 0.41649(14) 0.12390(6) 0.0182(3) Uani 1 1 d . . . H2 H 0.6679 0.3791 0.1291 0.022 Uiso 1 1 calc R . . C3 C 0.7771(2) 0.46661(17) 0.06764(7) 0.0168(4) Uani 1 1 d . . . C4 C 0.8251(2) 0.59345(17) 0.05979(7) 0.0169(4) Uani 1 1 d . . . N5 N 0.8931(2) 0.67150(14) 0.10854(6) 0.0172(3) Uani 1 1 d . . . C6 C 1.0530(2) 0.62781(17) 0.14491(7) 0.0166(4) Uani 1 1 d . . . C7 C 1.0644(2) 0.50440(17) 0.16900(8) 0.0176(4) Uani 1 1 d . . . O8 O 0.89397(18) 0.35473(12) 0.21418(5) 0.0216(3) Uani 1 1 d . . . C9 C 1.2311(3) 0.46541(18) 0.20025(8) 0.0204(4) Uani 1 1 d . . . H9 H 1.2446 0.3815 0.2159 0.025 Uiso 1 1 calc R . . C10 C 1.3772(2) 0.54958(18) 0.20838(8) 0.0221(4) Uani 1 1 d . . . H10 H 1.4941 0.5237 0.2277 0.027 Uiso 1 1 calc R . . C11 C 1.3470(3) 0.67221(18) 0.18742(8) 0.0217(4) Uani 1 1 d . . . H11 H 1.4436 0.7324 0.1960 0.026 Uiso 1 1 calc R . . N12 N 1.1897(2) 0.71204(15) 0.15563(6) 0.0201(4) Uani 1 1 d . . . N13 N 0.8086(2) 0.64776(14) 0.00717(6) 0.0192(3) Uani 1 1 d . . . C14 C 0.7446(2) 0.57468(19) -0.03920(8) 0.0211(4) Uani 1 1 d . . . H14 H 0.7265 0.6131 -0.0767 0.025 Uiso 1 1 calc R . . C15 C 0.7043(2) 0.44713(18) -0.03495(8) 0.0200(4) Uani 1 1 d . . . H15 H 0.6647 0.3987 -0.0692 0.024 Uiso 1 1 calc R . . C16 C 0.7215(2) 0.38884(17) 0.01927(8) 0.0190(4) Uani 1 1 d . . . C17 C 0.6800(3) 0.24863(17) 0.02536(8) 0.0238(4) Uani 1 1 d . . . H17A H 0.5597 0.2390 0.0375 0.036 Uiso 1 1 calc R . . H17B H 0.7737 0.2100 0.0547 0.036 Uiso 1 1 calc R . . H17C H 0.6797 0.2058 -0.0121 0.036 Uiso 1 1 calc R . . C18 C 0.8774(3) 0.80827(17) 0.09902(8) 0.0193(4) Uani 1 1 d . . . H18 H 0.9613 0.8483 0.0744 0.023 Uiso 1 1 calc R . . C19 C 0.6889(3) 0.86272(18) 0.09479(8) 0.0241(4) Uani 1 1 d . . . H19A H 0.5874 0.8030 0.0982 0.029 Uiso 1 1 calc R . . H19B H 0.6563 0.9353 0.0678 0.029 Uiso 1 1 calc R . . C20 C 0.8282(3) 0.88619(19) 0.14842(8) 0.0242(4) Uani 1 1 d . . . H20B H 0.8810 0.9731 0.1543 0.029 Uiso 1 1 calc R . . H20A H 0.8120 0.8407 0.1846 0.029 Uiso 1 1 calc R . . O21 O 0.68736(18) 0.15385(12) 0.21749(6) 0.0253(3) Uani 1 1 d . . . H21 H 0.7472 0.2214 0.2152 0.030 Uiso 1 1 calc R . . O22 O 0.49201(17) 0.24923(12) 0.14722(6) 0.0242(3) Uani 1 1 d . . . C23 C 0.5367(2) 0.15657(17) 0.17826(8) 0.0188(4) Uani 1 1 d . . . C24 C 0.4315(2) 0.03795(17) 0.17538(8) 0.0186(4) Uani 1 1 d . . . H24 H 0.4747 -0.0301 0.2009 0.022 Uiso 1 1 calc R . . C25 C 0.2774(3) 0.02182(18) 0.13828(8) 0.0204(4) Uani 1 1 d . . . H25 H 0.2200 -0.0596 0.1372 0.025 Uiso 1 1 calc R . . C26 C 0.1882(2) 0.12289(18) 0.09826(8) 0.0215(4) Uani 1 1 d . . . O27 O 0.07698(18) 0.19612(14) 0.11240(6) 0.0278(3) Uani 1 1 d . . . O28 O 0.23806(19) 0.11715(13) 0.04585(6) 0.0264(3) Uani 1 1 d . . . H28 H 0.2007 0.1827 0.0267 0.032 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 C1 0.0199(9) 0.0159(9) 0.0149(9) -0.0019(7) -0.0002(7) 0.0018(7) N2 0.0167(7) 0.0196(8) 0.0171(8) 0.0013(6) -0.0014(6) -0.0042(6) C3 0.0128(8) 0.0200(9) 0.0165(9) 0.0012(7) -0.0013(7) 0.0016(7) C4 0.0122(8) 0.0218(9) 0.0156(9) -0.0008(7) -0.0011(7) 0.0012(7) N5 0.0186(7) 0.0161(8) 0.0154(7) -0.0006(6) -0.0016(6) -0.0015(6) C6 0.0185(9) 0.0201(9) 0.0106(8) -0.0021(7) 0.0009(7) -0.0009(7) C7 0.0184(9) 0.0203(9) 0.0131(8) -0.0035(7) -0.0008(7) -0.0019(7) O8 0.0250(7) 0.0207(7) 0.0171(7) 0.0017(5) -0.0027(5) -0.0027(5) C9 0.0220(9) 0.0219(10) 0.0167(9) -0.0002(7) 0.0008(7) -0.0004(8) C10 0.0172(9) 0.0296(10) 0.0180(9) -0.0007(8) -0.0019(7) -0.0002(8) C11 0.0182(9) 0.0272(10) 0.0184(9) -0.0048(8) -0.0012(7) -0.0060(8) N12 0.0218(8) 0.0204(8) 0.0172(8) -0.0019(6) -0.0002(6) -0.0038(6) N13 0.0177(8) 0.0224(8) 0.0167(8) 0.0014(6) 0.0001(6) -0.0006(6) C14 0.0183(9) 0.0299(10) 0.0145(9) 0.0003(8) 0.0006(7) 0.0011(8) C15 0.0176(9) 0.0258(10) 0.0155(9) -0.0056(7) -0.0006(7) 0.0014(7) C16 0.0122(8) 0.0220(9) 0.0215(9) -0.0034(7) -0.0015(7) 0.0016(7) C17 0.0240(10) 0.0225(10) 0.0223(10) -0.0032(8) -0.0041(8) -0.0003(8) C18 0.0212(9) 0.0179(9) 0.0181(9) -0.0002(7) 0.0007(7) -0.0005(7) C19 0.0232(10) 0.0232(10) 0.0246(10) -0.0004(8) -0.0004(8) 0.0024(8) C20 0.0273(10) 0.0221(10) 0.0229(10) -0.0033(8) 0.0027(8) 0.0012(8) O21 0.0251(7) 0.0210(7) 0.0261(7) 0.0055(6) -0.0075(6) -0.0052(6) O22 0.0215(7) 0.0206(7) 0.0283(7) 0.0058(6) -0.0031(6) -0.0013(5) C23 0.0176(9) 0.0219(9) 0.0163(9) 0.0007(7) 0.0008(7) 0.0026(7) C24 0.0203(9) 0.0180(9) 0.0171(9) 0.0015(7) 0.0016(7) 0.0029(7) C25 0.0220(9) 0.0191(9) 0.0204(9) 0.0004(7) 0.0037(8) -0.0039(7) C26 0.0191(9) 0.0227(10) 0.0211(10) 0.0007(8) -0.0019(8) -0.0065(8) O27 0.0203(7) 0.0319(8) 0.0311(8) 0.0024(6) 0.0036(6) 0.0045(6) O28 0.0318(8) 0.0273(8) 0.0189(7) 0.0008(6) 0.0003(6) 0.0000(6) _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 O8 1.246(2) . ? C1 N2 1.337(2) . ? C1 C7 1.485(2) . ? N2 C3 1.417(2) . ? N2 H2 0.8800 . ? C3 C4 1.393(3) . ? C3 C16 1.397(2) . ? C4 N13 1.337(2) . ? C4 N5 1.424(2) . ? N5 C6 1.419(2) . ? N5 C18 1.450(2) . ? C6 N12 1.335(2) . ? C6 C7 1.405(2) . ? C7 C9 1.391(2) . ? C9 C10 1.384(3) . ? C9 H9 0.9500 . ? C10 C11 1.378(3) . ? C10 H10 0.9500 . ? C11 N12 1.345(2) . ? C11 H11 0.9500 . ? N13 C14 1.346(2) . ? C14 C15 1.374(3) . ? C14 H14 0.9500 . ? C15 C16 1.389(3) . ? C15 H15 0.9500 . ? C16 C17 1.509(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.496(3) . ? C18 C20 1.499(3) . ? C18 H18 1.0000 . ? C19 C20 1.509(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20B 0.9900 . ? C20 H20A 0.9900 . ? O21 C23 1.326(2) . ? O21 H21 0.8400 . ? O22 C23 1.223(2) . ? C23 C24 1.461(3) . ? C24 C25 1.329(2) . ? C24 H24 0.9500 . ? C25 C26 1.493(3) . ? C25 H25 0.9500 . ? C26 O27 1.207(2) . ? C26 O28 1.329(2) . ? O28 H28 0.8400 . ? 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 O8 C1 N2 121.15(16) . . ? O8 C1 C7 119.14(15) . . ? N2 C1 C7 119.70(16) . . ? C1 N2 C3 127.08(15) . . ? C1 N2 H2 116.5 . . ? C3 N2 H2 116.5 . . ? C4 C3 C16 119.88(16) . . ? C4 C3 N2 121.29(15) . . ? C16 C3 N2 118.68(16) . . ? N13 C4 C3 122.40(16) . . ? N13 C4 N5 117.11(16) . . ? C3 C4 N5 120.49(16) . . ? C6 N5 C4 116.62(14) . . ? C6 N5 C18 116.63(14) . . ? C4 N5 C18 115.75(14) . . ? N12 C6 C7 122.38(15) . . ? N12 C6 N5 115.85(15) . . ? C7 C6 N5 121.76(15) . . ? C9 C7 C6 118.09(16) . . ? C9 C7 C1 117.69(16) . . ? C6 C7 C1 123.70(16) . . ? C10 C9 C7 119.66(17) . . ? C10 C9 H9 120.2 . . ? C7 C9 H9 120.2 . . ? C11 C10 C9 117.63(17) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? N12 C11 C10 124.16(17) . . ? N12 C11 H11 117.9 . . ? C10 C11 H11 117.9 . . ? C6 N12 C11 117.65(16) . . ? C4 N13 C14 117.54(16) . . ? N13 C14 C15 123.15(17) . . ? N13 C14 H14 118.4 . . ? C15 C14 H14 118.4 . . ? C14 C15 C16 120.11(16) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C3 116.69(17) . . ? C15 C16 C17 121.38(16) . . ? C3 C16 C17 121.93(17) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N5 C18 C19 115.93(16) . . ? N5 C18 C20 116.28(16) . . ? C19 C18 C20 60.53(12) . . ? N5 C18 H18 117.3 . . ? C19 C18 H18 117.3 . . ? C20 C18 H18 117.3 . . ? C18 C19 C20 59.85(12) . . ? C18 C19 H19A 117.8 . . ? C20 C19 H19A 117.8 . . ? C18 C19 H19B 117.8 . . ? C20 C19 H19B 117.8 . . ? H19A C19 H19B 114.9 . . ? C18 C20 C19 59.62(12) . . ? C18 C20 H20B 117.8 . . ? C19 C20 H20B 117.8 . . ? C18 C20 H20A 117.8 . . ? C19 C20 H20A 117.8 . . ? H20B C20 H20A 114.9 . . ? C23 O21 H21 109.5 . . ? O22 C23 O21 122.97(17) . . ? O22 C23 C24 123.55(16) . . ? O21 C23 C24 113.48(15) . . ? C25 C24 C23 122.34(16) . . ? C25 C24 H24 118.8 . . ? C23 C24 H24 118.8 . . ? C24 C25 C26 124.47(17) . . ? C24 C25 H25 117.8 . . ? C26 C25 H25 117.8 . . ? O27 C26 O28 125.26(17) . . ? O27 C26 C25 122.25(18) . . ? O28 C26 C25 112.40(17) . . ? C26 O28 H28 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 O8 C1 N2 C3 -168.02(17) . . . . ? C7 C1 N2 C3 13.2(3) . . . . ? C1 N2 C3 C4 -53.7(3) . . . . ? C1 N2 C3 C16 130.88(19) . . . . ? C16 C3 C4 N13 4.7(3) . . . . ? N2 C3 C4 N13 -170.76(16) . . . . ? C16 C3 C4 N5 -176.02(16) . . . . ? N2 C3 C4 N5 8.6(3) . . . . ? N13 C4 N5 C6 -122.44(17) . . . . ? C3 C4 N5 C6 58.2(2) . . . . ? N13 C4 N5 C18 20.5(2) . . . . ? C3 C4 N5 C18 -158.82(16) . . . . ? C4 N5 C6 N12 127.97(17) . . . . ? C18 N5 C6 N12 -14.7(2) . . . . ? C4 N5 C6 C7 -53.4(2) . . . . ? C18 N5 C6 C7 163.96(17) . . . . ? N12 C6 C7 C9 -6.6(3) . . . . ? N5 C6 C7 C9 174.84(16) . . . . ? N12 C6 C7 C1 164.87(17) . . . . ? N5 C6 C7 C1 -13.7(3) . . . . ? O8 C1 C7 C9 31.8(2) . . . . ? N2 C1 C7 C9 -149.45(17) . . . . ? O8 C1 C7 C6 -139.72(18) . . . . ? N2 C1 C7 C6 39.0(3) . . . . ? C6 C7 C9 C10 2.3(3) . . . . ? C1 C7 C9 C10 -169.74(17) . . . . ? C7 C9 C10 C11 3.4(3) . . . . ? C9 C10 C11 N12 -5.6(3) . . . . ? C7 C6 N12 C11 4.7(3) . . . . ? N5 C6 N12 C11 -176.63(16) . . . . ? C10 C11 N12 C6 1.5(3) . . . . ? C3 C4 N13 C14 -0.7(3) . . . . ? N5 C4 N13 C14 179.95(15) . . . . ? C4 N13 C14 C15 -3.1(3) . . . . ? N13 C14 C15 C16 2.8(3) . . . . ? C14 C15 C16 C3 1.2(3) . . . . ? C14 C15 C16 C17 -179.40(17) . . . . ? C4 C3 C16 C15 -4.7(3) . . . . ? N2 C3 C16 C15 170.83(15) . . . . ? C4 C3 C16 C17 175.88(16) . . . . ? N2 C3 C16 C17 -8.6(3) . . . . ? C6 N5 C18 C19 -143.81(16) . . . . ? C4 N5 C18 C19 73.2(2) . . . . ? C6 N5 C18 C20 -75.5(2) . . . . ? C4 N5 C18 C20 141.50(16) . . . . ? N5 C18 C19 C20 106.90(18) . . . . ? N5 C18 C20 C19 -106.33(18) . . . . ? O22 C23 C24 C25 0.1(3) . . . . ? O21 C23 C24 C25 -179.24(18) . . . . ? C23 C24 C25 C26 -3.8(3) . . . . ? C24 C25 C26 O27 -89.4(3) . . . . ? C24 C25 C26 O28 94.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.462 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.048 # Attachment 'NVSCfin.CIF' data_c:\blurby _database_code_depnum_ccdc_archive 'CCDC 853023' #TrackingRef 'NVSCfin.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e]diazepin-6-one 1,2-benzoisothiazol-3(2H)-one 1,1-dioxide 1:1 co-crystal ; _chemical_name_common 'nevirapine-saccharin 2:1 cocrystal' _chemical_melting_point '223 C' _chemical_formula_moiety '2(C15 H14 N4 O), C7 H5 N O3 S' _chemical_formula_sum 'C37 H33 N9 O5 S' _chemical_formula_weight 715.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5649(5) _cell_length_b 13.8069(7) _cell_length_c 13.8726(7) _cell_angle_alpha 64.090(3) _cell_angle_beta 79.292(2) _cell_angle_gamma 82.686(2) _cell_volume 1616.98(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6584 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 26.36 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9776 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method 'phi- and omega-scans of 1.00 deg.' _diffrn_detector_area_resol_mean n/a _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% 0 _diffrn_reflns_number 12967 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 26.36 _reflns_number_total 6584 _reflns_number_gt 4445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT 2000' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0586P)^2^+0.4061P] 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 6584 _refine_ls_number_parameters 471 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1206 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 N21 N 0.68021(18) 0.77617(13) 0.84743(13) 0.0320(4) Uani 1 1 d . . . H21 H 0.7435 0.7886 0.7891 0.038 Uiso 1 1 calc R . . S22 S 0.57626(5) 0.67215(4) 0.90033(4) 0.03008(15) Uani 1 1 d . . . C23 C 0.4894(2) 0.70860(16) 1.00400(16) 0.0283(5) Uani 1 1 d . . . C24 C 0.5466(2) 0.80001(16) 0.99489(16) 0.0299(5) Uani 1 1 d . . . C25 C 0.6605(2) 0.84204(17) 0.90136(16) 0.0317(5) Uani 1 1 d . . . O26 O 0.72760(17) 0.92052(12) 0.87531(12) 0.0424(4) Uani 1 1 d . . . O27 O 0.65936(15) 0.57273(11) 0.94241(12) 0.0360(4) Uani 1 1 d . . . O28 O 0.48277(16) 0.68183(12) 0.82741(11) 0.0383(4) Uani 1 1 d . . . C29 C 0.3826(2) 0.65552(18) 1.08637(17) 0.0343(5) Uani 1 1 d . . . H29 H 0.3440 0.5930 1.0916 0.041 Uiso 1 1 calc R . . C30 C 0.3347(2) 0.6986(2) 1.16132(18) 0.0419(6) Uani 1 1 d . . . H30 H 0.2620 0.6645 1.2197 0.050 Uiso 1 1 calc R . . C31 C 0.3910(2) 0.7906(2) 1.15236(19) 0.0433(6) Uani 1 1 d . . . H31 H 0.3557 0.8184 1.2044 0.052 Uiso 1 1 calc R . . C32 C 0.4963(2) 0.84172(18) 1.07016(18) 0.0374(5) Uani 1 1 d . . . H32 H 0.5342 0.9046 1.0646 0.045 Uiso 1 1 calc R . . C1A C 0.3943(2) 0.84140(16) 0.59637(16) 0.0277(5) Uani 1 1 d . . . N2A N 0.30022(17) 0.81120(13) 0.55519(13) 0.0282(4) Uani 1 1 d . . . H2A H 0.3348 0.7709 0.5208 0.034 Uiso 1 1 calc R . . C3A C 0.1509(2) 0.83704(15) 0.56095(15) 0.0245(4) Uani 1 1 d . . . C4A C 0.0641(2) 0.81893(15) 0.65969(15) 0.0244(4) Uani 1 1 d . . . N5A N 0.12543(17) 0.78841(13) 0.75492(13) 0.0263(4) Uani 1 1 d . . . C6A C 0.2226(2) 0.85857(15) 0.75272(15) 0.0255(4) Uani 1 1 d . . . C7A C 0.3419(2) 0.89201(15) 0.67243(15) 0.0265(4) Uani 1 1 d . . . O8A O 0.52423(15) 0.82796(12) 0.57131(12) 0.0368(4) Uani 1 1 d . . . C9A C 0.4288(2) 0.96380(16) 0.67521(17) 0.0331(5) Uani 1 1 d . . . H9A H 0.5091 0.9893 0.6210 0.040 Uiso 1 1 calc R . . C10A C 0.3982(2) 0.99794(17) 0.75686(19) 0.0382(5) Uani 1 1 d . . . H10A H 0.4536 1.0496 0.7583 0.046 Uiso 1 1 calc R . . C11A C 0.2846(2) 0.95462(17) 0.83619(19) 0.0373(5) Uani 1 1 d . . . H11A H 0.2676 0.9738 0.8955 0.045 Uiso 1 1 calc R . . N12A N 0.19688(18) 0.88746(14) 0.83524(14) 0.0328(4) Uani 1 1 d . . . N13A N -0.07880(17) 0.82904(12) 0.66883(13) 0.0266(4) Uani 1 1 d . . . C14A C -0.1370(2) 0.86311(15) 0.57787(16) 0.0285(5) Uani 1 1 d . . . H14A H -0.2379 0.8695 0.5835 0.034 Uiso 1 1 calc R . . C15A C -0.0582(2) 0.88943(15) 0.47669(17) 0.0293(5) Uani 1 1 d . . . H15A H -0.1045 0.9169 0.4143 0.035 Uiso 1 1 calc R . . C16A C 0.0890(2) 0.87556(15) 0.46664(16) 0.0271(5) Uani 1 1 d . . . C17A C 0.1785(2) 0.90077(17) 0.35833(16) 0.0351(5) Uani 1 1 d . . . H17A H 0.1187 0.9378 0.3010 0.053 Uiso 1 1 calc R . . H17B H 0.2209 0.8336 0.3551 0.053 Uiso 1 1 calc R . . H17C H 0.2543 0.9473 0.3481 0.053 Uiso 1 1 calc R . . C18A C 0.0336(2) 0.73620(16) 0.85685(15) 0.0286(5) Uani 1 1 d . . . H18A H -0.0422 0.7823 0.8794 0.034 Uiso 1 1 calc R . . C19A C 0.0002(2) 0.62324(16) 0.88635(17) 0.0338(5) Uani 1 1 d . . . H19A H 0.0401 0.5917 0.8345 0.041 Uiso 1 1 calc R . . H19B H -0.0950 0.5992 0.9268 0.041 Uiso 1 1 calc R . . C20A C 0.1023(2) 0.64530(17) 0.94381(17) 0.0355(5) Uani 1 1 d . . . H20A H 0.0697 0.6348 1.0196 0.043 Uiso 1 1 calc R . . H20B H 0.2048 0.6274 0.9273 0.043 Uiso 1 1 calc R . . C1B C 0.5865(2) 0.67606(16) 0.41130(16) 0.0289(5) Uani 1 1 d . . . N2B N 0.67507(17) 0.69888(13) 0.46195(13) 0.0295(4) Uani 1 1 d . . . H2B H 0.6388 0.7390 0.4962 0.035 Uiso 1 1 calc R . . C3B C 0.8216(2) 0.66520(15) 0.46629(16) 0.0260(4) Uani 1 1 d . . . C4B C 0.9171(2) 0.67883(15) 0.37170(16) 0.0272(5) Uani 1 1 d . . . N5B N 0.86546(17) 0.71282(13) 0.27150(13) 0.0292(4) Uani 1 1 d . . . C6B C 0.7707(2) 0.64254(16) 0.27035(16) 0.0299(5) Uani 1 1 d . . . C7B C 0.6441(2) 0.61662(16) 0.34406(16) 0.0306(5) Uani 1 1 d . . . O8B O 0.45725(15) 0.70168(12) 0.42095(12) 0.0393(4) Uani 1 1 d . . . C9B C 0.5612(2) 0.54124(18) 0.34373(18) 0.0372(5) Uani 1 1 d . . . H9B H 0.4759 0.5205 0.3936 0.045 Uiso 1 1 calc R . . C10B C 0.6033(2) 0.49643(18) 0.2704(2) 0.0415(6) Uani 1 1 d . . . H10B H 0.5516 0.4413 0.2719 0.050 Uiso 1 1 calc R . . C11B C 0.7219(2) 0.53422(19) 0.19566(19) 0.0408(6) Uani 1 1 d . . . H11B H 0.7454 0.5087 0.1409 0.049 Uiso 1 1 calc R . . N12B N 0.80707(19) 0.60471(15) 0.19450(14) 0.0371(4) Uani 1 1 d . . . N13B N 1.05707(17) 0.65921(13) 0.37083(14) 0.0311(4) Uani 1 1 d . . . C14B C 1.1065(2) 0.62363(16) 0.46545(18) 0.0328(5) Uani 1 1 d . . . H14B H 1.2066 0.6124 0.4653 0.039 Uiso 1 1 calc R . . C15B C 1.0203(2) 0.60248(16) 0.56289(17) 0.0320(5) Uani 1 1 d . . . H15B H 1.0605 0.5738 0.6282 0.038 Uiso 1 1 calc R . . C16B C 0.8734(2) 0.62344(15) 0.56496(16) 0.0290(5) Uani 1 1 d . . . C17B C 0.7765(2) 0.60054(18) 0.66961(16) 0.0366(5) Uani 1 1 d . . . H17D H 0.7168 0.6654 0.6640 0.055 Uiso 1 1 calc R . . H17E H 0.8335 0.5793 0.7282 0.055 Uiso 1 1 calc R . . H17F H 0.7157 0.5419 0.6851 0.055 Uiso 1 1 calc R . . C18B C 0.9693(2) 0.75867(17) 0.17485(16) 0.0350(5) Uani 1 1 d . . . H18B H 1.0473 0.7087 0.1612 0.042 Uiso 1 1 calc R . . C19B C 1.0063(2) 0.87137(18) 0.14343(18) 0.0404(5) Uani 1 1 d . . . H19C H 1.1057 0.8909 0.1110 0.048 Uiso 1 1 calc R . . H19D H 0.9585 0.9076 0.1895 0.048 Uiso 1 1 calc R . . C20B C 0.9167(3) 0.84810(18) 0.07836(18) 0.0422(6) Uani 1 1 d . . . H20C H 0.8141 0.8702 0.0844 0.051 Uiso 1 1 calc R . . H20D H 0.9612 0.8534 0.0059 0.051 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 N21 0.0320(10) 0.0349(10) 0.0263(9) -0.0134(8) 0.0048(8) -0.0044(8) S22 0.0284(3) 0.0338(3) 0.0273(3) -0.0138(2) -0.0016(2) 0.0007(2) C23 0.0250(11) 0.0335(11) 0.0237(10) -0.0112(9) -0.0037(9) 0.0040(9) C24 0.0281(11) 0.0328(11) 0.0271(11) -0.0113(9) -0.0063(9) 0.0032(9) C25 0.0316(12) 0.0323(12) 0.0269(11) -0.0090(10) -0.0048(9) 0.0008(10) O26 0.0469(10) 0.0360(9) 0.0413(9) -0.0139(7) -0.0004(7) -0.0098(7) O27 0.0331(8) 0.0329(8) 0.0405(9) -0.0159(7) -0.0045(7) 0.0038(6) O28 0.0402(9) 0.0468(9) 0.0331(8) -0.0207(7) -0.0103(7) 0.0011(7) C29 0.0279(11) 0.0404(12) 0.0293(11) -0.0105(10) -0.0019(9) -0.0029(9) C30 0.0314(12) 0.0556(15) 0.0297(12) -0.0139(11) 0.0019(10) 0.0041(11) C31 0.0405(14) 0.0577(16) 0.0372(13) -0.0294(12) -0.0041(11) 0.0111(12) C32 0.0427(13) 0.0381(12) 0.0359(12) -0.0212(11) -0.0068(11) 0.0043(10) C1A 0.0253(11) 0.0299(11) 0.0253(11) -0.0101(9) -0.0005(9) -0.0032(9) N2A 0.0242(9) 0.0335(9) 0.0306(9) -0.0194(8) 0.0010(7) -0.0004(7) C3A 0.0249(10) 0.0224(10) 0.0279(11) -0.0123(9) -0.0034(9) -0.0013(8) C4A 0.0245(10) 0.0221(10) 0.0274(11) -0.0118(9) -0.0023(8) -0.0018(8) N5A 0.0251(9) 0.0293(9) 0.0235(9) -0.0116(7) 0.0002(7) -0.0020(7) C6A 0.0244(10) 0.0252(10) 0.0261(10) -0.0112(9) -0.0049(9) 0.0037(8) C7A 0.0272(11) 0.0264(10) 0.0260(11) -0.0112(9) -0.0057(9) 0.0020(8) O8A 0.0249(8) 0.0515(9) 0.0384(9) -0.0249(8) 0.0000(7) -0.0022(7) C9A 0.0312(12) 0.0310(11) 0.0358(12) -0.0127(10) -0.0056(10) -0.0020(9) C10A 0.0385(13) 0.0366(12) 0.0489(14) -0.0251(11) -0.0111(11) -0.0011(10) C11A 0.0384(13) 0.0406(13) 0.0432(13) -0.0271(11) -0.0103(11) 0.0039(10) N12A 0.0323(10) 0.0378(10) 0.0338(10) -0.0214(9) -0.0050(8) 0.0025(8) N13A 0.0246(9) 0.0268(9) 0.0300(9) -0.0143(8) -0.0019(7) -0.0009(7) C14A 0.0262(11) 0.0257(11) 0.0364(12) -0.0152(9) -0.0073(10) 0.0005(8) C15A 0.0344(12) 0.0259(11) 0.0313(11) -0.0136(9) -0.0101(10) -0.0007(9) C16A 0.0339(12) 0.0229(10) 0.0264(11) -0.0118(9) -0.0032(9) -0.0044(8) C17A 0.0375(12) 0.0397(13) 0.0271(11) -0.0136(10) -0.0019(10) -0.0053(10) C18A 0.0274(11) 0.0308(11) 0.0234(10) -0.0101(9) 0.0025(9) -0.0014(9) C19A 0.0296(12) 0.0330(12) 0.0342(12) -0.0107(10) -0.0025(9) -0.0025(9) C20A 0.0356(12) 0.0385(12) 0.0281(11) -0.0108(10) -0.0036(10) -0.0017(10) C1B 0.0254(11) 0.0354(12) 0.0257(11) -0.0138(9) -0.0025(9) -0.0005(9) N2B 0.0263(9) 0.0358(10) 0.0318(9) -0.0217(8) -0.0005(8) 0.0020(7) C3B 0.0253(10) 0.0247(10) 0.0308(11) -0.0147(9) -0.0031(9) -0.0006(8) C4B 0.0286(11) 0.0239(10) 0.0278(11) -0.0110(9) -0.0019(9) -0.0003(8) N5B 0.0278(9) 0.0348(10) 0.0245(9) -0.0143(8) 0.0008(7) 0.0002(7) C6B 0.0301(11) 0.0319(11) 0.0294(11) -0.0150(9) -0.0092(9) 0.0073(9) C7B 0.0290(11) 0.0352(12) 0.0305(11) -0.0168(10) -0.0082(9) 0.0050(9) O8B 0.0280(8) 0.0552(10) 0.0427(9) -0.0300(8) -0.0034(7) 0.0026(7) C9B 0.0318(12) 0.0427(13) 0.0427(13) -0.0228(11) -0.0085(10) 0.0011(10) C10B 0.0384(13) 0.0438(14) 0.0555(15) -0.0313(12) -0.0176(12) 0.0066(11) C11B 0.0409(14) 0.0499(14) 0.0477(14) -0.0356(12) -0.0170(12) 0.0136(11) N12B 0.0367(10) 0.0458(11) 0.0354(10) -0.0251(9) -0.0092(8) 0.0103(9) N13B 0.0278(10) 0.0323(10) 0.0339(10) -0.0160(8) -0.0032(8) 0.0015(7) C14B 0.0268(11) 0.0306(11) 0.0422(13) -0.0158(10) -0.0088(10) 0.0015(9) C15B 0.0364(12) 0.0265(11) 0.0341(12) -0.0119(9) -0.0114(10) -0.0003(9) C16B 0.0359(12) 0.0232(10) 0.0294(11) -0.0121(9) -0.0043(9) -0.0040(9) C17B 0.0406(13) 0.0412(13) 0.0266(11) -0.0122(10) -0.0040(10) -0.0068(10) C18B 0.0335(12) 0.0390(13) 0.0284(11) -0.0145(10) 0.0030(10) 0.0021(10) C19B 0.0376(13) 0.0452(14) 0.0326(12) -0.0126(11) -0.0010(10) -0.0027(10) C20B 0.0482(14) 0.0451(14) 0.0314(12) -0.0155(11) -0.0047(11) -0.0003(11) _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 N21 C25 1.386(3) . ? N21 S22 1.6617(17) . ? N21 H21 0.8800 . ? S22 O28 1.4242(15) . ? S22 O27 1.4322(14) . ? S22 C23 1.759(2) . ? C23 C29 1.382(3) . ? C23 C24 1.385(3) . ? C24 C32 1.386(3) . ? C24 C25 1.478(3) . ? C25 O26 1.210(2) . ? C29 C30 1.393(3) . ? C29 H29 0.9500 . ? C30 C31 1.389(3) . ? C30 H30 0.9500 . ? C31 C32 1.365(3) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C1A O8A 1.240(2) . ? C1A N2A 1.343(3) . ? C1A C7A 1.487(3) . ? N2A C3A 1.424(2) . ? N2A H2A 0.8800 . ? C3A C16A 1.394(3) . ? C3A C4A 1.399(3) . ? C4A N13A 1.344(2) . ? C4A N5A 1.416(2) . ? N5A C6A 1.413(2) . ? N5A C18A 1.449(2) . ? C6A N12A 1.341(2) . ? C6A C7A 1.403(3) . ? C7A C9A 1.389(3) . ? C9A C10A 1.378(3) . ? C9A H9A 0.9500 . ? C10A C11A 1.377(3) . ? C10A H10A 0.9500 . ? C11A N12A 1.333(3) . ? C11A H11A 0.9500 . ? N13A C14A 1.341(2) . ? C14A C15A 1.379(3) . ? C14A H14A 0.9500 . ? C15A C16A 1.386(3) . ? C15A H15A 0.9500 . ? C16A C17A 1.501(3) . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C18A C19A 1.491(3) . ? C18A C20A 1.491(3) . ? C18A H18A 1.0000 . ? C19A C20A 1.503(3) . ? C19A H19A 0.9900 . ? C19A H19B 0.9900 . ? C20A H20A 0.9900 . ? C20A H20B 0.9900 . ? C1B O8B 1.241(2) . ? C1B N2B 1.339(3) . ? C1B C7B 1.487(3) . ? N2B C3B 1.423(2) . ? N2B H2B 0.8800 . ? C3B C16B 1.394(3) . ? C3B C4B 1.405(3) . ? C4B N13B 1.331(2) . ? C4B N5B 1.422(2) . ? N5B C6B 1.416(3) . ? N5B C18B 1.452(3) . ? C6B N12B 1.341(3) . ? C6B C7B 1.404(3) . ? C7B C9B 1.388(3) . ? C9B C10B 1.383(3) . ? C9B H9B 0.9500 . ? C10B C11B 1.369(3) . ? C10B H10B 0.9500 . ? C11B N12B 1.340(3) . ? C11B H11B 0.9500 . ? N13B C14B 1.340(3) . ? C14B C15B 1.377(3) . ? C14B H14B 0.9500 . ? C15B C16B 1.395(3) . ? C15B H15B 0.9500 . ? C16B C17B 1.497(3) . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C18B C20B 1.489(3) . ? C18B C19B 1.492(3) . ? C18B H18B 1.0000 . ? C19B C20B 1.504(3) . ? C19B H19C 0.9900 . ? C19B H19D 0.9900 . ? C20B H20C 0.9900 . ? C20B H20D 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 N21 S22 115.53(14) . . ? C25 N21 H21 122.2 . . ? S22 N21 H21 122.2 . . ? O28 S22 O27 116.83(9) . . ? O28 S22 N21 110.90(9) . . ? O27 S22 N21 110.46(9) . . ? O28 S22 C23 111.97(9) . . ? O27 S22 C23 111.60(9) . . ? N21 S22 C23 92.48(9) . . ? C29 C23 C24 122.64(19) . . ? C29 C23 S22 127.39(17) . . ? C24 C23 S22 109.95(15) . . ? C23 C24 C32 119.8(2) . . ? C23 C24 C25 113.09(18) . . ? C32 C24 C25 127.1(2) . . ? O26 C25 N21 124.70(19) . . ? O26 C25 C24 126.35(19) . . ? N21 C25 C24 108.94(18) . . ? C23 C29 C30 116.4(2) . . ? C23 C29 H29 121.8 . . ? C30 C29 H29 121.8 . . ? C31 C30 C29 121.3(2) . . ? C31 C30 H30 119.3 . . ? C29 C30 H30 119.3 . . ? C32 C31 C30 121.3(2) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C31 C32 C24 118.6(2) . . ? C31 C32 H32 120.7 . . ? C24 C32 H32 120.7 . . ? O8A C1A N2A 120.73(18) . . ? O8A C1A C7A 119.66(18) . . ? N2A C1A C7A 119.61(17) . . ? C1A N2A C3A 127.35(16) . . ? C1A N2A H2A 116.3 . . ? C3A N2A H2A 116.3 . . ? C16A C3A C4A 119.44(17) . . ? C16A C3A N2A 118.92(17) . . ? C4A C3A N2A 121.54(17) . . ? N13A C4A C3A 122.27(18) . . ? N13A C4A N5A 117.33(17) . . ? C3A C4A N5A 120.41(17) . . ? C6A N5A C4A 117.02(15) . . ? C6A N5A C18A 115.89(15) . . ? C4A N5A C18A 116.38(15) . . ? N12A C6A C7A 121.99(18) . . ? N12A C6A N5A 115.59(17) . . ? C7A C6A N5A 122.36(17) . . ? C9A C7A C6A 118.10(18) . . ? C9A C7A C1A 117.55(18) . . ? C6A C7A C1A 123.51(18) . . ? C10A C9A C7A 119.8(2) . . ? C10A C9A H9A 120.1 . . ? C7A C9A H9A 120.1 . . ? C11A C10A C9A 117.7(2) . . ? C11A C10A H10A 121.1 . . ? C9A C10A H10A 121.1 . . ? N12A C11A C10A 124.2(2) . . ? N12A C11A H11A 117.9 . . ? C10A C11A H11A 117.9 . . ? C11A N12A C6A 117.89(18) . . ? C14A N13A C4A 117.45(16) . . ? N13A C14A C15A 123.53(18) . . ? N13A C14A H14A 118.2 . . ? C15A C14A H14A 118.2 . . ? C14A C15A C16A 119.56(19) . . ? C14A C15A H15A 120.2 . . ? C16A C15A H15A 120.2 . . ? C15A C16A C3A 117.51(18) . . ? C15A C16A C17A 121.24(18) . . ? C3A C16A C17A 121.25(18) . . ? C16A C17A H17A 109.5 . . ? C16A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C16A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? N5A C18A C19A 115.90(17) . . ? N5A C18A C20A 115.60(17) . . ? C19A C18A C20A 60.52(14) . . ? N5A C18A H18A 117.5 . . ? C19A C18A H18A 117.5 . . ? C20A C18A H18A 117.5 . . ? C18A C19A C20A 59.76(14) . . ? C18A C19A H19A 117.8 . . ? C20A C19A H19A 117.8 . . ? C18A C19A H19B 117.8 . . ? C20A C19A H19B 117.8 . . ? H19A C19A H19B 114.9 . . ? C18A C20A C19A 59.72(14) . . ? C18A C20A H20A 117.8 . . ? C19A C20A H20A 117.8 . . ? C18A C20A H20B 117.8 . . ? C19A C20A H20B 117.8 . . ? H20A C20A H20B 114.9 . . ? O8B C1B N2B 121.44(18) . . ? O8B C1B C7B 119.42(18) . . ? N2B C1B C7B 119.12(17) . . ? C1B N2B C3B 127.01(16) . . ? C1B N2B H2B 116.5 . . ? C3B N2B H2B 116.5 . . ? C16B C3B C4B 119.09(18) . . ? C16B C3B N2B 119.69(17) . . ? C4B C3B N2B 121.13(17) . . ? N13B C4B C3B 122.86(18) . . ? N13B C4B N5B 116.94(17) . . ? C3B C4B N5B 120.19(17) . . ? C6B N5B C4B 114.74(16) . . ? C6B N5B C18B 116.01(16) . . ? C4B N5B C18B 115.76(16) . . ? N12B C6B C7B 122.5(2) . . ? N12B C6B N5B 116.63(18) . . ? C7B C6B N5B 120.85(17) . . ? C9B C7B C6B 117.85(19) . . ? C9B C7B C1B 118.80(19) . . ? C6B C7B C1B 122.86(19) . . ? C10B C9B C7B 119.7(2) . . ? C10B C9B H9B 120.1 . . ? C7B C9B H9B 120.1 . . ? C11B C10B C9B 117.8(2) . . ? C11B C10B H10B 121.1 . . ? C9B C10B H10B 121.1 . . ? N12B C11B C10B 124.5(2) . . ? N12B C11B H11B 117.8 . . ? C10B C11B H11B 117.8 . . ? C11B N12B C6B 117.26(19) . . ? C4B N13B C14B 117.50(17) . . ? N13B C14B C15B 123.62(19) . . ? N13B C14B H14B 118.2 . . ? C15B C14B H14B 118.2 . . ? C14B C15B C16B 119.48(19) . . ? C14B C15B H15B 120.3 . . ? C16B C15B H15B 120.3 . . ? C3B C16B C15B 117.30(18) . . ? C3B C16B C17B 121.85(18) . . ? C15B C16B C17B 120.85(19) . . ? C16B C17B H17D 109.5 . . ? C16B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C16B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? N5B C18B C20B 116.90(18) . . ? N5B C18B C19B 115.88(17) . . ? C20B C18B C19B 60.60(14) . . ? N5B C18B H18B 117.1 . . ? C20B C18B H18B 117.1 . . ? C19B C18B H18B 117.1 . . ? C18B C19B C20B 59.59(15) . . ? C18B C19B H19C 117.8 . . ? C20B C19B H19C 117.8 . . ? C18B C19B H19D 117.8 . . ? C20B C19B H19D 117.8 . . ? H19C C19B H19D 115.0 . . ? C18B C20B C19B 59.81(15) . . ? C18B C20B H20C 117.8 . . ? C19B C20B H20C 117.8 . . ? C18B C20B H20D 117.8 . . ? C19B C20B H20D 117.8 . . ? H20C C20B H20D 114.9 . . ? 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 C25 N21 S22 O28 115.54(15) . . . . ? C25 N21 S22 O27 -113.31(15) . . . . ? C25 N21 S22 C23 0.87(16) . . . . ? O28 S22 C23 C29 67.0(2) . . . . ? O27 S22 C23 C29 -66.0(2) . . . . ? N21 S22 C23 C29 -179.22(18) . . . . ? O28 S22 C23 C24 -114.84(15) . . . . ? O27 S22 C23 C24 112.07(15) . . . . ? N21 S22 C23 C24 -1.11(16) . . . . ? C29 C23 C24 C32 -0.2(3) . . . . ? S22 C23 C24 C32 -178.44(16) . . . . ? C29 C23 C24 C25 179.31(18) . . . . ? S22 C23 C24 C25 1.1(2) . . . . ? S22 N21 C25 O26 179.10(17) . . . . ? S22 N21 C25 C24 -0.4(2) . . . . ? C23 C24 C25 O26 -180.0(2) . . . . ? C32 C24 C25 O26 -0.5(3) . . . . ? C23 C24 C25 N21 -0.5(2) . . . . ? C32 C24 C25 N21 179.0(2) . . . . ? C24 C23 C29 C30 -0.2(3) . . . . ? S22 C23 C29 C30 177.66(16) . . . . ? C23 C29 C30 C31 0.6(3) . . . . ? C29 C30 C31 C32 -0.5(3) . . . . ? C30 C31 C32 C24 0.0(3) . . . . ? C23 C24 C32 C31 0.3(3) . . . . ? C25 C24 C32 C31 -179.11(19) . . . . ? O8A C1A N2A C3A -168.50(18) . . . . ? C7A C1A N2A C3A 11.2(3) . . . . ? C1A N2A C3A C16A 131.6(2) . . . . ? C1A N2A C3A C4A -52.0(3) . . . . ? C16A C3A C4A N13A 5.5(3) . . . . ? N2A C3A C4A N13A -170.83(17) . . . . ? C16A C3A C4A N5A -174.75(16) . . . . ? N2A C3A C4A N5A 8.9(3) . . . . ? N13A C4A N5A C6A -122.77(18) . . . . ? C3A C4A N5A C6A 57.5(2) . . . . ? N13A C4A N5A C18A 20.4(2) . . . . ? C3A C4A N5A C18A -159.40(17) . . . . ? C4A N5A C6A N12A 128.70(18) . . . . ? C18A N5A C6A N12A -14.6(2) . . . . ? C4A N5A C6A C7A -54.1(2) . . . . ? C18A N5A C6A C7A 162.53(17) . . . . ? N12A C6A C7A C9A -5.0(3) . . . . ? N5A C6A C7A C9A 178.03(17) . . . . ? N12A C6A C7A C1A 164.24(18) . . . . ? N5A C6A C7A C1A -12.7(3) . . . . ? O8A C1A C7A C9A 28.2(3) . . . . ? N2A C1A C7A C9A -151.45(19) . . . . ? O8A C1A C7A C6A -141.0(2) . . . . ? N2A C1A C7A C6A 39.3(3) . . . . ? C6A C7A C9A C10A 1.5(3) . . . . ? C1A C7A C9A C10A -168.38(19) . . . . ? C7A C9A C10A C11A 3.0(3) . . . . ? C9A C10A C11A N12A -4.7(3) . . . . ? C10A C11A N12A C6A 1.3(3) . . . . ? C7A C6A N12A C11A 3.6(3) . . . . ? N5A C6A N12A C11A -179.23(17) . . . . ? C3A C4A N13A C14A -3.5(3) . . . . ? N5A C4A N13A C14A 176.76(15) . . . . ? C4A N13A C14A C15A -1.0(3) . . . . ? N13A C14A C15A C16A 3.4(3) . . . . ? C14A C15A C16A C3A -1.3(3) . . . . ? C14A C15A C16A C17A 178.56(18) . . . . ? C4A C3A C16A C15A -2.9(3) . . . . ? N2A C3A C16A C15A 173.51(17) . . . . ? C4A C3A C16A C17A 177.26(18) . . . . ? N2A C3A C16A C17A -6.3(3) . . . . ? C6A N5A C18A C19A -143.81(17) . . . . ? C4A N5A C18A C19A 72.6(2) . . . . ? C6A N5A C18A C20A -75.8(2) . . . . ? C4A N5A C18A C20A 140.67(18) . . . . ? N5A C18A C19A C20A 106.10(19) . . . . ? N5A C18A C20A C19A -106.60(19) . . . . ? O8B C1B N2B C3B 173.43(19) . . . . ? C7B C1B N2B C3B -5.2(3) . . . . ? C1B N2B C3B C16B -133.6(2) . . . . ? C1B N2B C3B C4B 50.0(3) . . . . ? C16B C3B C4B N13B -3.9(3) . . . . ? N2B C3B C4B N13B 172.56(17) . . . . ? C16B C3B C4B N5B 174.80(17) . . . . ? N2B C3B C4B N5B -8.8(3) . . . . ? N13B C4B N5B C6B 118.25(19) . . . . ? C3B C4B N5B C6B -60.5(2) . . . . ? N13B C4B N5B C18B -21.1(2) . . . . ? C3B C4B N5B C18B 160.20(17) . . . . ? C4B N5B C6B N12B -123.28(18) . . . . ? C18B N5B C6B N12B 15.9(2) . . . . ? C4B N5B C6B C7B 58.0(2) . . . . ? C18B N5B C6B C7B -162.74(18) . . . . ? N12B C6B C7B C9B 6.0(3) . . . . ? N5B C6B C7B C9B -175.42(18) . . . . ? N12B C6B C7B C1B -165.85(19) . . . . ? N5B C6B C7B C1B 12.7(3) . . . . ? O8B C1B C7B C9B -35.8(3) . . . . ? N2B C1B C7B C9B 142.9(2) . . . . ? O8B C1B C7B C6B 136.0(2) . . . . ? N2B C1B C7B C6B -45.3(3) . . . . ? C6B C7B C9B C10B -1.4(3) . . . . ? C1B C7B C9B C10B 170.74(19) . . . . ? C7B C9B C10B C11B -4.2(3) . . . . ? C9B C10B C11B N12B 6.1(3) . . . . ? C10B C11B N12B C6B -1.8(3) . . . . ? C7B C6B N12B C11B -4.4(3) . . . . ? N5B C6B N12B C11B 176.96(18) . . . . ? C3B C4B N13B C14B 0.9(3) . . . . ? N5B C4B N13B C14B -177.80(16) . . . . ? C4B N13B C14B C15B 2.7(3) . . . . ? N13B C14B C15B C16B -3.3(3) . . . . ? C4B C3B C16B C15B 3.2(3) . . . . ? N2B C3B C16B C15B -173.30(17) . . . . ? C4B C3B C16B C17B -176.20(18) . . . . ? N2B C3B C16B C17B 7.3(3) . . . . ? C14B C15B C16B C3B 0.1(3) . . . . ? C14B C15B C16B C17B 179.51(18) . . . . ? C6B N5B C18B C20B 76.2(2) . . . . ? C4B N5B C18B C20B -144.97(18) . . . . ? C6B N5B C18B C19B 144.78(18) . . . . ? C4B N5B C18B C19B -76.4(2) . . . . ? N5B C18B C19B C20B -107.7(2) . . . . ? N5B C18B C20B C19B 106.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.235 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.051 # Attachment 'NVSLIfin.CIF' data_c:\pampoen2 _database_code_depnum_ccdc_archive 'CCDC 853024' #TrackingRef 'NVSLIfin.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e]diazepin-6-one 2-hydroxybenzoic acid 2:1 co-crystal ; _chemical_name_common 'nevirapine-salicylic acid 2:1 co-crystal' _chemical_melting_point '203 degrees C melting onset by DSC' _chemical_formula_moiety '2(C15 H14 N4 O), C7 H6 O3' _chemical_formula_sum 'C37 H34 N8 O5' _chemical_formula_weight 670.72 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1549(14) _cell_length_b 12.6194(15) _cell_length_c 13.4644(16) _cell_angle_alpha 113.374(2) _cell_angle_beta 99.133(2) _cell_angle_gamma 107.324(2) _cell_volume 1575.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7552 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 28.14 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9668 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details 'program SADABS (Sheldrick, 1996)' _exptl_special_details ; Main residue disorder amounts to 20% for this structure. The high residual electron density difference peak of 1.30 e -3 is an artefact located near (0.2A from H23B) the overlapped, disordered salicylic acid molecules and has no chemical signficance. ; _diffrn_ambient_temperature 100(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 Kappa Duo Apex II diffractometer' _diffrn_measurement_method 'phi- and omega scans of 0.5 deg' _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% 0 _diffrn_reflns_number 23138 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 28.14 _reflns_number_total 7552 _reflns_number_gt 5331 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT 2000' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.1216P)^2^+0.7467P] 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 7552 _refine_ls_number_parameters 474 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.2077 _refine_ls_wR_factor_gt 0.1851 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 C1A C 0.37880(18) 0.78457(17) 0.40207(15) 0.0183(4) Uani 1 1 d . . . N2A N 0.40268(15) 0.71576(14) 0.45205(13) 0.0180(3) Uani 1 1 d . . . H2A H 0.3483 0.6965 0.4888 0.022 Uiso 1 1 calc R . . C3A C 0.50508(17) 0.67084(16) 0.45228(15) 0.0167(4) Uani 1 1 d . . . C4A C 0.53143(17) 0.60834(16) 0.35145(16) 0.0171(4) Uani 1 1 d . . . N5A N 0.46791(15) 0.60312(14) 0.24889(13) 0.0184(3) Uani 1 1 d . . . C6A C 0.49254(17) 0.72082(17) 0.25119(15) 0.0176(4) Uani 1 1 d . . . C7A C 0.45969(18) 0.81133(17) 0.32985(16) 0.0182(4) Uani 1 1 d . . . O8A O 0.29338(14) 0.82769(13) 0.41663(12) 0.0238(3) Uani 1 1 d . . . C9A C 0.49051(19) 0.92712(18) 0.33059(17) 0.0219(4) Uani 1 1 d . . . H9A H 0.4706 0.9907 0.3834 0.026 Uiso 1 1 calc R . . C10A C 0.5504(2) 0.94908(19) 0.25399(18) 0.0246(4) Uani 1 1 d . . . H10A H 0.5774 1.0290 0.2560 0.030 Uiso 1 1 calc R . . C11A C 0.56921(19) 0.8503(2) 0.17458(17) 0.0236(4) Uani 1 1 d . . . H11A H 0.6029 0.8624 0.1176 0.028 Uiso 1 1 calc R . . N12A N 0.54311(15) 0.73852(16) 0.17262(14) 0.0217(4) Uani 1 1 d . . . N13A N 0.61617(15) 0.55192(15) 0.34787(14) 0.0214(4) Uani 1 1 d . . . C14A C 0.67924(18) 0.55837(17) 0.44511(18) 0.0224(4) Uani 1 1 d . . . H14A H 0.7364 0.5152 0.4421 0.027 Uiso 1 1 calc R . . C15A C 0.66513(18) 0.62446(17) 0.54897(17) 0.0210(4) Uani 1 1 d . . . H15A H 0.7152 0.6300 0.6162 0.025 Uiso 1 1 calc R . . C16A C 0.57657(18) 0.68320(16) 0.55444(16) 0.0186(4) Uani 1 1 d . . . C17A C 0.5579(2) 0.75703(19) 0.66526(16) 0.0250(4) Uani 1 1 d . . . H17A H 0.4677 0.7151 0.6637 0.038 Uiso 1 1 calc R . . H17B H 0.5722 0.8420 0.6765 0.038 Uiso 1 1 calc R . . H17C H 0.6216 0.7622 0.7280 0.038 Uiso 1 1 calc R . . C18A C 0.45967(19) 0.50215(17) 0.14335(16) 0.0220(4) Uani 1 1 d . . . H18A H 0.5413 0.5115 0.1199 0.026 Uiso 1 1 calc R . . C19A C 0.3294(2) 0.43643(19) 0.05100(17) 0.0262(4) Uani 1 1 d . . . H19A H 0.3300 0.4051 -0.0289 0.031 Uiso 1 1 calc R . . H19B H 0.2587 0.4667 0.0664 0.031 Uiso 1 1 calc R . . C20A C 0.37025(19) 0.37281(18) 0.11618(16) 0.0230(4) Uani 1 1 d . . . H20A H 0.3245 0.3641 0.1715 0.028 Uiso 1 1 calc R . . H20B H 0.3959 0.3025 0.0762 0.028 Uiso 1 1 calc R . . C21A C 0.7375(2) 0.2785(2) 0.0419(2) 0.0160(5) Uani 0.739(3) 1 d P A 1 C22A C 0.8135(3) 0.3564(3) 0.0073(2) 0.0225(6) Uani 0.739(3) 1 d P A 1 H22A H 0.8329 0.4439 0.0454 0.027 Uiso 0.739(3) 1 calc PR A 1 C23A C 0.8632(3) 0.3096(3) -0.0829(3) 0.0348(8) Uani 0.739(3) 1 d P A 1 H23A H 0.9166 0.3632 -0.1064 0.042 Uiso 0.739(3) 1 calc PR A 1 C24A C 0.8291(3) 0.1771(3) -0.1374(2) 0.0236(6) Uani 0.739(3) 1 d P A 1 H24A H 0.8579 0.1417 -0.2009 0.028 Uiso 0.739(3) 1 calc PR A 1 C25A C 0.7588(3) 0.1011(3) -0.1031(3) 0.0285(7) Uani 0.739(3) 1 d P A 1 H25A H 0.7427 0.0142 -0.1394 0.034 Uiso 0.739(3) 1 calc PR A 1 C26A C 0.7073(3) 0.1496(2) -0.0116(2) 0.0217(6) Uani 0.739(3) 1 d P A 1 O27A O 0.6312(2) 0.06784(19) 0.0140(2) 0.0355(6) Uani 0.739(3) 1 d P A 1 H27A H 0.6045 0.1058 0.0668 0.043 Uiso 0.739(3) 1 calc PR A 1 C28A C 0.6820(3) 0.3277(3) 0.1337(2) 0.0177(5) Uani 0.739(3) 1 d P A 1 O29A O 0.6049(2) 0.2592(2) 0.16100(18) 0.0311(5) Uani 0.739(3) 1 d P A 1 O30A O 0.71959(19) 0.45185(18) 0.18465(17) 0.0274(5) Uani 0.739(3) 1 d P A 1 H30A H 0.6843 0.4730 0.2359 0.033 Uiso 0.739(3) 1 calc PR A 1 C1B C 0.13069(18) 0.72033(17) 0.59145(15) 0.0169(4) Uani 1 1 d . . . N2B N 0.10663(15) 0.78852(14) 0.54086(13) 0.0173(3) Uani 1 1 d . . . H2B H 0.1631 0.8106 0.5067 0.021 Uiso 1 1 calc R . . C3B C 0.00084(17) 0.82877(16) 0.53628(15) 0.0162(4) Uani 1 1 d . . . C4B C -0.03044(17) 0.88960(16) 0.63478(15) 0.0161(4) Uani 1 1 d . . . N5B N 0.03252(15) 0.89819(14) 0.73955(13) 0.0168(3) Uani 1 1 d . . . C6B C 0.01095(17) 0.78133(16) 0.73855(15) 0.0160(4) Uani 1 1 d . . . C7B C 0.04854(17) 0.69295(17) 0.66254(15) 0.0162(4) Uani 1 1 d . . . O8B O 0.21734(14) 0.67846(13) 0.57815(12) 0.0220(3) Uani 1 1 d . . . C9B C 0.01940(19) 0.57785(17) 0.66245(16) 0.0201(4) Uani 1 1 d . . . H9B H 0.0423 0.5155 0.6115 0.024 Uiso 1 1 calc R . . C10B C -0.0435(2) 0.55449(19) 0.73746(18) 0.0233(4) Uani 1 1 d . . . H10B H -0.0692 0.4749 0.7360 0.028 Uiso 1 1 calc R . . C11B C -0.06726(19) 0.65134(19) 0.81415(17) 0.0231(4) Uani 1 1 d . . . H11B H -0.1033 0.6384 0.8698 0.028 Uiso 1 1 calc R . . N12B N -0.04273(15) 0.76230(15) 0.81511(14) 0.0200(3) Uani 1 1 d . . . N13B N -0.11953(15) 0.94040(14) 0.63522(14) 0.0199(3) Uani 1 1 d . . . C14B C -0.18212(18) 0.93055(17) 0.53659(18) 0.0219(4) Uani 1 1 d . . . H14B H -0.2432 0.9693 0.5368 0.026 Uiso 1 1 calc R . . C15B C -0.16249(19) 0.86698(17) 0.43456(17) 0.0216(4) Uani 1 1 d . . . H15B H -0.2124 0.8592 0.3661 0.026 Uiso 1 1 calc R . . C16B C -0.06872(18) 0.81413(16) 0.43265(16) 0.0187(4) Uani 1 1 d . . . C17B C -0.0432(2) 0.74516(19) 0.32435(17) 0.0257(4) Uani 1 1 d . . . H17D H -0.1025 0.7429 0.2608 0.039 Uiso 1 1 calc R . . H17E H -0.0593 0.6590 0.3104 0.039 Uiso 1 1 calc R . . H17F H 0.0489 0.7884 0.3309 0.039 Uiso 1 1 calc R . . C18B C 0.02795(19) 0.99515(17) 0.84109(16) 0.0200(4) Uani 1 1 d . . . H2 H -0.0602 0.9833 0.8533 0.024 Uiso 1 1 calc R . . C19B C 0.1465(2) 1.05925(18) 0.94465(17) 0.0245(4) Uani 1 1 d . . . H19C H 0.2199 1.0308 0.9391 0.029 Uiso 1 1 calc R . . H19D H 0.1321 1.0867 1.0200 0.029 Uiso 1 1 calc R . . C20B C 0.12112(19) 1.12662(17) 0.87791(16) 0.0210(4) Uani 1 1 d . . . H20C H 0.0911 1.1953 0.9123 0.025 Uiso 1 1 calc R . . H20D H 0.1790 1.1393 0.8315 0.025 Uiso 1 1 calc R . . C21B C 0.7282(13) 0.2703(11) 0.0315(11) 0.123(4) Uiso 0.261(3) 1 d PG A 2 C22B C 0.8054(7) 0.3079(8) -0.0295(6) 0.123(4) Uiso 0.261(3) 1 d PG A 2 C23B C 0.8265(13) 0.2192(9) -0.1187(10) 0.123(4) Uiso 0.261(3) 1 d PG A 2 H23B H 0.8792 0.2449 -0.1604 0.147 Uiso 0.261(3) 1 calc PR A 2 C24B C 0.7704(17) 0.0927(8) -0.1469(13) 0.123(4) Uiso 0.261(3) 1 d PG A 2 H24B H 0.7849 0.0320 -0.2078 0.147 Uiso 0.261(3) 1 calc PR A 2 C25B C 0.6933(14) 0.0550(9) -0.0859(14) 0.123(4) Uiso 0.261(3) 1 d PG A 2 H25B H 0.6550 -0.0314 -0.1051 0.147 Uiso 0.261(3) 1 calc PR A 2 C26B C 0.6722(15) 0.1438(12) 0.0033(14) 0.123(4) Uiso 0.261(3) 1 d PG A 2 H26B H 0.6194 0.1180 0.0450 0.147 Uiso 0.261(3) 1 calc PR A 2 O27B O 0.8727(9) 0.4198(8) -0.0144(8) 0.067(3) Uiso 0.261(3) 1 d PG A 2 H27B H 0.8601 0.4736 0.0394 0.081 Uiso 0.261(3) 1 calc PR A 2 C28B C 0.7272(14) 0.3831(14) 0.1189(12) 0.058(3) Uiso 0.261(3) 1 d P A 2 O29B O 0.7730(13) 0.4875(13) 0.1376(12) 0.107(4) Uiso 0.261(3) 1 d P A 2 O30B O 0.6510(13) 0.3413(14) 0.1744(12) 0.096(4) Uiso 0.261(3) 1 d P A 2 H30B H 0.6525 0.4030 0.2311 0.116 Uiso 0.261(3) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1A 0.0199(9) 0.0181(8) 0.0159(8) 0.0054(7) 0.0064(7) 0.0091(7) N2A 0.0205(8) 0.0195(7) 0.0198(8) 0.0100(6) 0.0111(6) 0.0120(6) C3A 0.0159(8) 0.0127(8) 0.0200(9) 0.0062(7) 0.0061(7) 0.0055(6) C4A 0.0147(8) 0.0132(8) 0.0199(9) 0.0051(7) 0.0058(7) 0.0044(6) N5A 0.0197(8) 0.0167(7) 0.0161(8) 0.0036(6) 0.0082(6) 0.0080(6) C6A 0.0133(8) 0.0197(9) 0.0169(9) 0.0062(7) 0.0045(7) 0.0065(7) C7A 0.0168(8) 0.0197(9) 0.0182(9) 0.0078(7) 0.0061(7) 0.0086(7) O8A 0.0287(7) 0.0290(7) 0.0277(7) 0.0168(6) 0.0172(6) 0.0205(6) C9A 0.0235(10) 0.0224(9) 0.0221(9) 0.0100(8) 0.0086(8) 0.0120(8) C10A 0.0230(10) 0.0247(10) 0.0297(11) 0.0157(9) 0.0096(8) 0.0093(8) C11A 0.0188(9) 0.0336(11) 0.0253(10) 0.0174(9) 0.0112(8) 0.0122(8) N12A 0.0180(8) 0.0282(9) 0.0210(8) 0.0111(7) 0.0095(6) 0.0108(7) N13A 0.0175(8) 0.0173(7) 0.0272(9) 0.0072(7) 0.0084(7) 0.0080(6) C14A 0.0165(9) 0.0176(9) 0.0331(11) 0.0113(8) 0.0077(8) 0.0077(7) C15A 0.0180(9) 0.0176(9) 0.0260(10) 0.0117(8) 0.0036(7) 0.0052(7) C16A 0.0183(9) 0.0120(8) 0.0218(9) 0.0066(7) 0.0054(7) 0.0036(7) C17A 0.0334(11) 0.0229(10) 0.0188(9) 0.0091(8) 0.0066(8) 0.0131(8) C18A 0.0218(9) 0.0192(9) 0.0201(9) 0.0032(8) 0.0125(8) 0.0072(7) C19A 0.0322(11) 0.0231(10) 0.0171(9) 0.0070(8) 0.0086(8) 0.0059(8) C20A 0.0232(10) 0.0196(9) 0.0205(9) 0.0048(8) 0.0074(8) 0.0074(8) C21A 0.0152(11) 0.0221(12) 0.0136(11) 0.0066(10) 0.0059(9) 0.0129(10) C22A 0.0262(13) 0.0270(14) 0.0254(14) 0.0174(12) 0.0110(11) 0.0164(11) C23A 0.0444(18) 0.052(2) 0.0347(17) 0.0314(16) 0.0256(15) 0.0319(16) C24A 0.0283(14) 0.0352(16) 0.0098(11) 0.0060(11) 0.0038(10) 0.0233(12) C25A 0.0184(13) 0.0343(15) 0.0306(15) 0.0084(13) 0.0074(12) 0.0172(12) C26A 0.0210(13) 0.0174(12) 0.0191(13) 0.0029(10) -0.0020(10) 0.0101(10) O27A 0.0285(11) 0.0228(10) 0.0572(15) 0.0159(10) 0.0231(10) 0.0118(9) C28A 0.0167(12) 0.0271(14) 0.0128(11) 0.0067(10) 0.0090(10) 0.0148(11) O29A 0.0340(11) 0.0282(11) 0.0389(12) 0.0176(10) 0.0223(10) 0.0145(9) O30A 0.0284(10) 0.0233(10) 0.0293(11) 0.0055(9) 0.0186(9) 0.0134(8) C1B 0.0189(9) 0.0162(8) 0.0158(8) 0.0063(7) 0.0061(7) 0.0084(7) N2B 0.0190(8) 0.0185(7) 0.0185(8) 0.0096(6) 0.0091(6) 0.0100(6) C3B 0.0154(8) 0.0133(8) 0.0212(9) 0.0091(7) 0.0062(7) 0.0057(6) C4B 0.0162(8) 0.0119(8) 0.0187(9) 0.0066(7) 0.0060(7) 0.0043(6) N5B 0.0176(7) 0.0163(7) 0.0161(7) 0.0059(6) 0.0071(6) 0.0077(6) C6B 0.0139(8) 0.0173(8) 0.0174(8) 0.0080(7) 0.0048(7) 0.0072(7) C7B 0.0162(8) 0.0185(8) 0.0148(8) 0.0080(7) 0.0049(7) 0.0077(7) O8B 0.0260(7) 0.0257(7) 0.0257(7) 0.0146(6) 0.0147(6) 0.0181(6) C9B 0.0219(9) 0.0200(9) 0.0220(9) 0.0105(8) 0.0068(7) 0.0121(7) C10B 0.0243(10) 0.0237(9) 0.0305(10) 0.0187(9) 0.0107(8) 0.0115(8) C11B 0.0210(9) 0.0325(11) 0.0279(10) 0.0206(9) 0.0130(8) 0.0146(8) N12B 0.0189(8) 0.0246(8) 0.0228(8) 0.0134(7) 0.0108(7) 0.0112(6) N13B 0.0165(7) 0.0171(7) 0.0279(9) 0.0107(7) 0.0089(7) 0.0078(6) C14B 0.0165(9) 0.0192(9) 0.0332(11) 0.0148(8) 0.0075(8) 0.0079(7) C15B 0.0189(9) 0.0187(9) 0.0254(10) 0.0130(8) 0.0025(8) 0.0040(7) C16B 0.0202(9) 0.0135(8) 0.0195(9) 0.0076(7) 0.0042(7) 0.0041(7) C17B 0.0342(11) 0.0245(10) 0.0199(10) 0.0108(8) 0.0064(8) 0.0140(9) C18B 0.0215(9) 0.0181(9) 0.0214(9) 0.0067(8) 0.0129(8) 0.0095(7) C19B 0.0310(11) 0.0225(9) 0.0181(9) 0.0080(8) 0.0093(8) 0.0094(8) C20B 0.0235(9) 0.0182(9) 0.0200(9) 0.0066(7) 0.0088(8) 0.0090(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A O8A 1.235(2) . ? C1A N2A 1.350(2) . ? C1A C7A 1.494(2) . ? N2A C3A 1.418(2) . ? N2A H2A 0.8800 . ? C3A C16A 1.400(3) . ? C3A C4A 1.402(3) . ? C4A N13A 1.338(2) . ? C4A N5A 1.415(2) . ? N5A C6A 1.414(2) . ? N5A C18A 1.450(2) . ? C6A N12A 1.337(2) . ? C6A C7A 1.405(3) . ? C7A C9A 1.393(3) . ? C9A C10A 1.386(3) . ? C9A H9A 0.9500 . ? C10A C11A 1.382(3) . ? C10A H10A 0.9500 . ? C11A N12A 1.341(3) . ? C11A H11A 0.9500 . ? N13A C14A 1.343(3) . ? C14A C15A 1.378(3) . ? C14A H14A 0.9500 . ? C15A C16A 1.395(3) . ? C15A H15A 0.9500 . ? C16A C17A 1.500(3) . ? C17A H17A 0.9800 . ? C17A H17B 0.9800 . ? C17A H17C 0.9800 . ? C18A C20A 1.495(3) . ? C18A C19A 1.495(3) . ? C18A H18A 1.0000 . ? C19A C20A 1.507(3) . ? C19A H19A 0.9900 . ? C19A H19B 0.9900 . ? C20A H20A 0.9900 . ? C20A H20B 0.9900 . ? C21A C22A 1.376(4) . ? C21A C26A 1.395(3) . ? C21A C28A 1.469(3) . ? C22A C23A 1.403(4) . ? C22A H22A 0.9500 . ? C23A C24A 1.428(4) . ? C23A H23A 0.9500 . ? C24A C25A 1.329(4) . ? C24A H24A 0.9500 . ? C25A C26A 1.436(4) . ? C25A H25A 0.9500 . ? C26A O27A 1.326(4) . ? O27A H27A 0.8400 . ? C28A O29A 1.238(4) . ? C28A O30A 1.329(3) . ? O30A H30A 0.8400 . ? C1B O8B 1.237(2) . ? C1B N2B 1.350(2) . ? C1B C7B 1.492(2) . ? N2B C3B 1.419(2) . ? N2B H2B 0.8800 . ? C3B C16B 1.396(3) . ? C3B C4B 1.403(2) . ? C4B N13B 1.333(2) . ? C4B N5B 1.419(2) . ? N5B C6B 1.416(2) . ? N5B C18B 1.449(2) . ? C6B N12B 1.336(2) . ? C6B C7B 1.406(2) . ? C7B C9B 1.390(2) . ? C9B C10B 1.392(3) . ? C9B H9B 0.9500 . ? C10B C11B 1.381(3) . ? C10B H10B 0.9500 . ? C11B N12B 1.339(2) . ? C11B H11B 0.9500 . ? N13B C14B 1.338(3) . ? C14B C15B 1.380(3) . ? C14B H14B 0.9500 . ? C15B C16B 1.396(3) . ? C15B H15B 0.9500 . ? C16B C17B 1.496(3) . ? C17B H17D 0.9800 . ? C17B H17E 0.9800 . ? C17B H17F 0.9800 . ? C18B C19B 1.493(3) . ? C18B C20B 1.495(3) . ? C18B H2 1.0000 . ? C19B C20B 1.510(3) . ? C19B H19C 0.9900 . ? C19B H19D 0.9900 . ? C20B H20C 0.9900 . ? C20B H20D 0.9900 . ? C21B C22B 1.3900 . ? C21B C26B 1.3900 . ? C21B C28B 1.448(18) . ? C22B O27B 1.3006 . ? C22B C23B 1.3900 . ? C23B C24B 1.3900 . ? C23B H23B 0.9500 . ? C24B C25B 1.3900 . ? C24B H24B 0.9500 . ? C25B C26B 1.3900 . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? O27B H27B 0.8400 . ? C28B O29B 1.165(17) . ? C28B O30B 1.343(18) . ? O30B H30B 0.8400 . ? 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 O8A C1A N2A 121.38(17) . . ? O8A C1A C7A 119.50(16) . . ? N2A C1A C7A 119.11(16) . . ? C1A N2A C3A 127.63(15) . . ? C1A N2A H2A 116.2 . . ? C3A N2A H2A 116.2 . . ? C16A C3A C4A 119.28(17) . . ? C16A C3A N2A 119.16(16) . . ? C4A C3A N2A 121.46(16) . . ? N13A C4A C3A 122.08(17) . . ? N13A C4A N5A 117.61(16) . . ? C3A C4A N5A 120.32(16) . . ? C6A N5A C4A 115.51(14) . . ? C6A N5A C18A 116.07(15) . . ? C4A N5A C18A 116.80(15) . . ? N12A C6A C7A 122.53(17) . . ? N12A C6A N5A 116.71(16) . . ? C7A C6A N5A 120.71(16) . . ? C9A C7A C6A 118.04(17) . . ? C9A C7A C1A 118.11(16) . . ? C6A C7A C1A 123.38(16) . . ? C10A C9A C7A 119.72(18) . . ? C10A C9A H9A 120.1 . . ? C7A C9A H9A 120.1 . . ? C11A C10A C9A 117.45(18) . . ? C11A C10A H10A 121.3 . . ? C9A C10A H10A 121.3 . . ? N12A C11A C10A 124.33(18) . . ? N12A C11A H11A 117.8 . . ? C10A C11A H11A 117.8 . . ? C6A N12A C11A 117.61(16) . . ? C4A N13A C14A 118.24(17) . . ? N13A C14A C15A 123.26(18) . . ? N13A C14A H14A 118.4 . . ? C15A C14A H14A 118.4 . . ? C14A C15A C16A 119.35(18) . . ? C14A C15A H15A 120.3 . . ? C16A C15A H15A 120.3 . . ? C15A C16A C3A 117.56(17) . . ? C15A C16A C17A 121.61(18) . . ? C3A C16A C17A 120.83(17) . . ? C16A C17A H17A 109.5 . . ? C16A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C16A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? N5A C18A C20A 115.49(15) . . ? N5A C18A C19A 115.73(16) . . ? C20A C18A C19A 60.55(13) . . ? N5A C18A H18A 117.6 . . ? C20A C18A H18A 117.6 . . ? C19A C18A H18A 117.6 . . ? C18A C19A C20A 59.70(13) . . ? C18A C19A H19A 117.8 . . ? C20A C19A H19A 117.8 . . ? C18A C19A H19B 117.8 . . ? C20A C19A H19B 117.8 . . ? H19A C19A H19B 114.9 . . ? C18A C20A C19A 59.74(13) . . ? C18A C20A H20A 117.8 . . ? C19A C20A H20A 117.8 . . ? C18A C20A H20B 117.8 . . ? C19A C20A H20B 117.8 . . ? H20A C20A H20B 114.9 . . ? C22A C21A C26A 120.9(2) . . ? C22A C21A C28A 121.2(2) . . ? C26A C21A C28A 117.9(2) . . ? C21A C22A C23A 121.6(3) . . ? C21A C22A H22A 119.2 . . ? C23A C22A H22A 119.2 . . ? C22A C23A C24A 116.3(3) . . ? C22A C23A H23A 121.8 . . ? C24A C23A H23A 121.8 . . ? C25A C24A C23A 122.8(3) . . ? C25A C24A H24A 118.6 . . ? C23A C24A H24A 118.6 . . ? C24A C25A C26A 120.3(3) . . ? C24A C25A H25A 119.8 . . ? C26A C25A H25A 119.8 . . ? O27A C26A C21A 124.6(3) . . ? O27A C26A C25A 117.4(2) . . ? C21A C26A C25A 117.9(3) . . ? C26A O27A H27A 109.5 . . ? O29A C28A O30A 122.3(2) . . ? O29A C28A C21A 122.9(3) . . ? O30A C28A C21A 114.8(2) . . ? C28A O30A H30A 109.5 . . ? O8B C1B N2B 121.28(16) . . ? O8B C1B C7B 119.76(16) . . ? N2B C1B C7B 118.94(15) . . ? C1B N2B C3B 127.54(15) . . ? C1B N2B H2B 116.2 . . ? C3B N2B H2B 116.2 . . ? C16B C3B C4B 119.18(17) . . ? C16B C3B N2B 119.25(16) . . ? C4B C3B N2B 121.46(16) . . ? N13B C4B C3B 122.73(17) . . ? N13B C4B N5B 117.01(16) . . ? C3B C4B N5B 120.26(16) . . ? C6B N5B C4B 115.01(14) . . ? C6B N5B C18B 115.60(14) . . ? C4B N5B C18B 115.53(15) . . ? N12B C6B C7B 122.68(16) . . ? N12B C6B N5B 116.50(15) . . ? C7B C6B N5B 120.79(15) . . ? C9B C7B C6B 117.93(16) . . ? C9B C7B C1B 117.86(16) . . ? C6B C7B C1B 123.86(16) . . ? C7B C9B C10B 119.63(17) . . ? C7B C9B H9B 120.2 . . ? C10B C9B H9B 120.2 . . ? C11B C10B C9B 117.54(17) . . ? C11B C10B H10B 121.2 . . ? C9B C10B H10B 121.2 . . ? N12B C11B C10B 124.19(17) . . ? N12B C11B H11B 117.9 . . ? C10B C11B H11B 117.9 . . ? C6B N12B C11B 117.73(16) . . ? C4B N13B C14B 117.81(16) . . ? N13B C14B C15B 123.40(18) . . ? N13B C14B H14B 118.3 . . ? C15B C14B H14B 118.3 . . ? C14B C15B C16B 119.54(18) . . ? C14B C15B H15B 120.2 . . ? C16B C15B H15B 120.2 . . ? C15B C16B C3B 117.21(17) . . ? C15B C16B C17B 121.52(17) . . ? C3B C16B C17B 121.27(17) . . ? C16B C17B H17D 109.5 . . ? C16B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C16B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? N5B C18B C19B 116.56(16) . . ? N5B C18B C20B 115.68(15) . . ? C19B C18B C20B 60.69(13) . . ? N5B C18B H2 117.3 . . ? C19B C18B H2 117.3 . . ? C20B C18B H2 117.3 . . ? C18B C19B C20B 59.72(13) . . ? C18B C19B H19C 117.8 . . ? C20B C19B H19C 117.8 . . ? C18B C19B H19D 117.8 . . ? C20B C19B H19D 117.8 . . ? H19C C19B H19D 114.9 . . ? C18B C20B C19B 59.59(13) . . ? C18B C20B H20C 117.8 . . ? C19B C20B H20C 117.8 . . ? C18B C20B H20D 117.8 . . ? C19B C20B H20D 117.8 . . ? H20C C20B H20D 114.9 . . ? C22B C21B C26B 120.0 . . ? C22B C21B C28B 106.9(8) . . ? C26B C21B C28B 133.1(8) . . ? O27B C22B C21B 130.5 . . ? O27B C22B C23B 109.3 . . ? C21B C22B C23B 120.0 . . ? C24B C23B C22B 120.0 . . ? C24B C23B H23B 120.0 . . ? C22B C23B H23B 120.0 . . ? C25B C24B C23B 120.0 . . ? C25B C24B H24B 120.0 . . ? C23B C24B H24B 120.0 . . ? C24B C25B C26B 120.0 . . ? C24B C25B H25B 120.0 . . ? C26B C25B H25B 120.0 . . ? C25B C26B C21B 120.0 . . ? C25B C26B H26B 120.0 . . ? C21B C26B H26B 120.0 . . ? C22B O27B H27B 109.5 . . ? O29B C28B O30B 124.7(15) . . ? O29B C28B C21B 130.8(15) . . ? O30B C28B C21B 104.4(12) . . ? C28B O30B H30B 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 O8A C1A N2A C3A -173.38(17) . . . . ? C7A C1A N2A C3A 5.2(3) . . . . ? C1A N2A C3A C16A 134.94(19) . . . . ? C1A N2A C3A C4A -48.6(3) . . . . ? C16A C3A C4A N13A 4.9(3) . . . . ? N2A C3A C4A N13A -171.56(16) . . . . ? C16A C3A C4A N5A -175.09(15) . . . . ? N2A C3A C4A N5A 8.4(3) . . . . ? N13A C4A N5A C6A -119.56(17) . . . . ? C3A C4A N5A C6A 60.5(2) . . . . ? N13A C4A N5A C18A 22.3(2) . . . . ? C3A C4A N5A C18A -157.68(16) . . . . ? C4A N5A C6A N12A 123.29(17) . . . . ? C18A N5A C6A N12A -18.9(2) . . . . ? C4A N5A C6A C7A -59.2(2) . . . . ? C18A N5A C6A C7A 158.63(17) . . . . ? N12A C6A C7A C9A -4.8(3) . . . . ? N5A C6A C7A C9A 177.83(16) . . . . ? N12A C6A C7A C1A 167.20(17) . . . . ? N5A C6A C7A C1A -10.1(3) . . . . ? O8A C1A C7A C9A 33.4(3) . . . . ? N2A C1A C7A C9A -145.19(18) . . . . ? O8A C1A C7A C6A -138.59(19) . . . . ? N2A C1A C7A C6A 42.8(3) . . . . ? C6A C7A C9A C10A 0.8(3) . . . . ? C1A C7A C9A C10A -171.69(17) . . . . ? C7A C9A C10A C11A 4.0(3) . . . . ? C9A C10A C11A N12A -5.5(3) . . . . ? C7A C6A N12A C11A 3.6(3) . . . . ? N5A C6A N12A C11A -178.93(16) . . . . ? C10A C11A N12A C6A 1.7(3) . . . . ? C3A C4A N13A C14A -1.4(3) . . . . ? N5A C4A N13A C14A 178.64(15) . . . . ? C4A N13A C14A C15A -2.8(3) . . . . ? N13A C14A C15A C16A 3.2(3) . . . . ? C14A C15A C16A C3A 0.4(3) . . . . ? C14A C15A C16A C17A -179.60(17) . . . . ? C4A C3A C16A C15A -4.3(3) . . . . ? N2A C3A C16A C15A 172.30(15) . . . . ? C4A C3A C16A C17A 175.75(16) . . . . ? N2A C3A C16A C17A -7.7(3) . . . . ? C6A N5A C18A C20A -149.63(17) . . . . ? C4A N5A C18A C20A 68.7(2) . . . . ? C6A N5A C18A C19A -81.6(2) . . . . ? C4A N5A C18A C19A 136.70(17) . . . . ? N5A C18A C19A C20A -106.05(18) . . . . ? N5A C18A C20A C19A 106.45(19) . . . . ? C26A C21A C22A C23A 0.2(4) . . . . ? C28A C21A C22A C23A -177.8(3) . . . . ? C21A C22A C23A C24A 0.8(4) . . . . ? C22A C23A C24A C25A -2.6(4) . . . . ? C23A C24A C25A C26A 3.4(4) . . . . ? C22A C21A C26A O27A -177.6(3) . . . . ? C28A C21A C26A O27A 0.4(4) . . . . ? C22A C21A C26A C25A 0.5(3) . . . . ? C28A C21A C26A C25A 178.6(2) . . . . ? C24A C25A C26A O27A 176.0(3) . . . . ? C24A C25A C26A C21A -2.3(4) . . . . ? C22A C21A C28A O29A 174.2(3) . . . . ? C26A C21A C28A O29A -3.9(4) . . . . ? C22A C21A C28A O30A -4.9(3) . . . . ? C26A C21A C28A O30A 177.0(2) . . . . ? O8B C1B N2B C3B 171.35(17) . . . . ? C7B C1B N2B C3B -7.2(3) . . . . ? C1B N2B C3B C16B -134.03(19) . . . . ? C1B N2B C3B C4B 49.8(3) . . . . ? C16B C3B C4B N13B -3.6(3) . . . . ? N2B C3B C4B N13B 172.57(16) . . . . ? C16B C3B C4B N5B 175.75(15) . . . . ? N2B C3B C4B N5B -8.0(2) . . . . ? N13B C4B N5B C6B 118.59(17) . . . . ? C3B C4B N5B C6B -60.8(2) . . . . ? N13B C4B N5B C18B -20.1(2) . . . . ? C3B C4B N5B C18B 160.45(16) . . . . ? C4B N5B C6B N12B -122.61(17) . . . . ? C18B N5B C6B N12B 16.1(2) . . . . ? C4B N5B C6B C7B 59.3(2) . . . . ? C18B N5B C6B C7B -162.06(16) . . . . ? N12B C6B C7B C9B 4.7(3) . . . . ? N5B C6B C7B C9B -177.26(16) . . . . ? N12B C6B C7B C1B -168.23(17) . . . . ? N5B C6B C7B C1B 9.8(3) . . . . ? O8B C1B C7B C9B -33.0(3) . . . . ? N2B C1B C7B C9B 145.60(18) . . . . ? O8B C1B C7B C6B 139.94(19) . . . . ? N2B C1B C7B C6B -41.4(3) . . . . ? C6B C7B C9B C10B -0.8(3) . . . . ? C1B C7B C9B C10B 172.54(17) . . . . ? C7B C9B C10B C11B -3.8(3) . . . . ? C9B C10B C11B N12B 5.2(3) . . . . ? C7B C6B N12B C11B -3.5(3) . . . . ? N5B C6B N12B C11B 178.37(16) . . . . ? C10B C11B N12B C6B -1.6(3) . . . . ? C3B C4B N13B C14B 1.0(3) . . . . ? N5B C4B N13B C14B -178.45(15) . . . . ? C4B N13B C14B C15B 2.4(3) . . . . ? N13B C14B C15B C16B -3.0(3) . . . . ? C14B C15B C16B C3B 0.2(3) . . . . ? C14B C15B C16B C17B -179.56(17) . . . . ? C4B C3B C16B C15B 2.9(3) . . . . ? N2B C3B C16B C15B -173.39(15) . . . . ? C4B C3B C16B C17B -177.35(16) . . . . ? N2B C3B C16B C17B 6.3(3) . . . . ? C6B N5B C18B C19B 76.7(2) . . . . ? C4B N5B C18B C19B -144.88(16) . . . . ? C6B N5B C18B C20B 145.14(16) . . . . ? C4B N5B C18B C20B -76.4(2) . . . . ? N5B C18B C19B C20B 105.96(18) . . . . ? N5B C18B C20B C19B -107.40(19) . . . . ? C26B C21B C22B O27B -175.6 . . . . ? C28B C21B C22B O27B 3.3(12) . . . . ? C26B C21B C22B C23B 0.0 . . . . ? C28B C21B C22B C23B 178.9(12) . . . . ? O27B C22B C23B C24B 176.4 . . . . ? C21B C22B C23B C24B 0.0 . . . . ? C22B C23B C24B C25B 0.0 . . . . ? C23B C24B C25B C26B 0.0 . . . . ? C24B C25B C26B C21B 0.0 . . . . ? C22B C21B C26B C25B 0.0 . . . . ? C28B C21B C26B C25B -178.5(16) . . . . ? C22B C21B C28B O29B 4(2) . . . . ? C26B C21B C28B O29B -177.7(13) . . . . ? C22B C21B C28B O30B 179.6(10) . . . . ? C26B C21B C28B O30B -1.7(15) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.14 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.298 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.085 # Attachment 'NVTTAfin.CIF' data_v:\xrd-s\nv\nvtta(~1\nvtta) _database_code_depnum_ccdc_archive 'CCDC 853025' #TrackingRef 'NVTTAfin.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e]diazepin-6-one rac-2,3-dihydroxybutanedioic acid 1:1 co-crystal ; _chemical_name_common 'nevirapine-rac-tartaric acid 1:1 co-crystal' _chemical_melting_point '228 C' _chemical_formula_moiety 'C15 H14 N4 O, C4 H6 O6' _chemical_formula_sum 'C19 H20 N4 O7' _chemical_formula_weight 416.39 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.877(2) _cell_length_b 19.286(4) _cell_length_c 9.6971(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.66(3) _cell_angle_gamma 90.00 _cell_volume 1847.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3753 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 26.35 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method n/a _diffrn_detector_area_resol_mean n/a _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% 0 _diffrn_reflns_number 12293 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 26.35 _reflns_number_total 3753 _reflns_number_gt 3012 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT 2000' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'PLATON (Spek, 1990)' _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^)+(0.0348P)^2^+0.8302P] 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 3753 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0518 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0795 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.25372(14) 0.24068(7) 0.81210(15) 0.0215(3) Uani 1 1 d . . . N2 N 0.25717(12) 0.17275(6) 0.84086(12) 0.0215(3) Uani 1 1 d . . . H2 H 0.3003 0.1465 0.7815 0.026 Uiso 1 1 calc R . . C3 C 0.20002(14) 0.13776(7) 0.95502(14) 0.0198(3) Uani 1 1 d . . . C4 C 0.06506(14) 0.14748(7) 0.99219(14) 0.0196(3) Uani 1 1 d . . . N5 N -0.01244(12) 0.20101(6) 0.93143(12) 0.0197(3) Uani 1 1 d . . . C6 C 0.04124(14) 0.26894(7) 0.94907(14) 0.0191(3) Uani 1 1 d . . . C7 C 0.16873(14) 0.28720(7) 0.89705(14) 0.0198(3) Uani 1 1 d . . . O8 O 0.32256(11) 0.26531(5) 0.71689(11) 0.0293(3) Uani 1 1 d . . . C9 C 0.21385(15) 0.35451(8) 0.91934(15) 0.0240(3) Uani 1 1 d . . . H9 H 0.2989 0.3688 0.8844 0.029 Uiso 1 1 calc R . . C10 C 0.13544(16) 0.40071(8) 0.99215(16) 0.0270(3) Uani 1 1 d . . . H10 H 0.1667 0.4462 1.0122 0.032 Uiso 1 1 calc R . . C11 C 0.00996(16) 0.37838(8) 1.03473(16) 0.0273(3) Uani 1 1 d . . . H11 H -0.0462 0.4105 1.0815 0.033 Uiso 1 1 calc R . . N12 N -0.03748(12) 0.31398(6) 1.01404(13) 0.0241(3) Uani 1 1 d . . . N13 N 0.00670(13) 0.10723(6) 1.08725(12) 0.0231(3) Uani 1 1 d . . . C14 C 0.08077(16) 0.05698(8) 1.14699(15) 0.0275(4) Uani 1 1 d . . . H14 H 0.0372 0.0258 1.2079 0.033 Uiso 1 1 calc R . . C15 C 0.21667(16) 0.04860(7) 1.12417(15) 0.0259(3) Uani 1 1 d . . . H15 H 0.2669 0.0145 1.1737 0.031 Uiso 1 1 calc R . . C16 C 0.28011(15) 0.09056(7) 1.02771(14) 0.0216(3) Uani 1 1 d . . . C17 C 0.42991(15) 0.08660(8) 1.00353(16) 0.0277(3) Uani 1 1 d . . . H17B H 0.4462 0.0668 0.9122 0.042 Uiso 1 1 calc R . . H17A H 0.4723 0.0572 1.0742 0.042 Uiso 1 1 calc R . . H17C H 0.4689 0.1333 1.0084 0.042 Uiso 1 1 calc R . . C18 C -0.15866(14) 0.19496(7) 0.94046(15) 0.0215(3) Uani 1 1 d . . . H18 H -0.2004 0.2074 1.0306 0.026 Uiso 1 1 calc R . . C19 C -0.22198(16) 0.13682(8) 0.86170(16) 0.0281(4) Uani 1 1 d . . . H19B H -0.3012 0.1134 0.9026 0.034 Uiso 1 1 calc R . . H19A H -0.1617 0.1062 0.8082 0.034 Uiso 1 1 calc R . . C20 C -0.23954(16) 0.21045(8) 0.81305(17) 0.0290(3) Uani 1 1 d . . . H20B H -0.1900 0.2250 0.7298 0.035 Uiso 1 1 calc R . . H20A H -0.3295 0.2323 0.8242 0.035 Uiso 1 1 calc R . . C21 C 0.52974(14) 0.14212(7) 0.58364(14) 0.0198(3) Uani 1 1 d . . . C22 C 0.64516(14) 0.11342(7) 0.49800(14) 0.0199(3) Uani 1 1 d . . . H22 H 0.7169 0.1498 0.4916 0.024 Uiso 1 1 calc R . . C23 C 0.59429(14) 0.09648(7) 0.35060(14) 0.0201(3) Uani 1 1 d . . . H23 H 0.5489 0.1383 0.3102 0.024 Uiso 1 1 calc R . . C24 C 0.71442(15) 0.07642(8) 0.26157(14) 0.0223(3) Uani 1 1 d . . . O25 O 0.50433(11) 0.20794(5) 0.55698(11) 0.0262(2) Uani 1 1 d . . . H25 H 0.4429 0.2221 0.6090 0.031 Uiso 1 1 calc R . . O26 O 0.46652(10) 0.10738(5) 0.66538(10) 0.0261(2) Uani 1 1 d . . . O27 O 0.70293(10) 0.05392(5) 0.55977(10) 0.0231(2) Uani 1 1 d . . . H27 H 0.6435 0.0231 0.5673 0.028 Uiso 1 1 calc R . . O28 O 0.50118(10) 0.04082(5) 0.35345(10) 0.0232(2) Uani 1 1 d . . . H28 H 0.5402 0.0041 0.3295 0.028 Uiso 1 1 calc R . . O29 O 0.79040(11) 0.12955(5) 0.23280(11) 0.0323(3) Uani 1 1 d . . . H29 H 0.8532 0.1170 0.1807 0.039 Uiso 1 1 calc R . . O30 O 0.73238(12) 0.01718(6) 0.22566(12) 0.0354(3) 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 0.0177(7) 0.0250(7) 0.0218(7) 0.0021(6) 0.0038(6) 0.0016(6) N2 0.0226(6) 0.0206(6) 0.0213(6) 0.0015(5) 0.0085(5) 0.0038(5) C3 0.0225(7) 0.0173(7) 0.0196(7) -0.0012(5) 0.0044(6) -0.0013(6) C4 0.0213(7) 0.0188(7) 0.0188(7) -0.0020(5) 0.0023(6) -0.0015(6) N5 0.0163(6) 0.0188(6) 0.0242(6) -0.0001(5) 0.0037(5) -0.0010(5) C6 0.0182(7) 0.0207(7) 0.0184(7) 0.0010(6) 0.0006(6) 0.0003(6) C7 0.0196(7) 0.0203(7) 0.0196(7) 0.0025(6) 0.0020(6) 0.0018(6) O8 0.0318(6) 0.0263(6) 0.0301(6) 0.0070(5) 0.0151(5) 0.0050(5) C9 0.0189(7) 0.0251(8) 0.0280(8) 0.0042(6) 0.0031(6) -0.0012(6) C10 0.0267(8) 0.0210(7) 0.0332(8) -0.0024(6) 0.0015(7) -0.0031(6) C11 0.0256(8) 0.0232(8) 0.0331(9) -0.0056(6) 0.0061(7) 0.0023(6) N12 0.0214(6) 0.0225(6) 0.0285(7) -0.0039(5) 0.0064(5) -0.0001(5) N13 0.0248(6) 0.0227(6) 0.0221(6) 0.0008(5) 0.0066(5) -0.0029(5) C14 0.0368(9) 0.0227(8) 0.0230(8) 0.0045(6) 0.0062(7) -0.0032(7) C15 0.0342(9) 0.0204(7) 0.0231(8) 0.0022(6) 0.0001(6) 0.0022(6) C16 0.0252(8) 0.0183(7) 0.0214(7) -0.0037(6) 0.0012(6) 0.0017(6) C17 0.0258(8) 0.0287(8) 0.0286(8) 0.0020(7) 0.0012(6) 0.0055(6) C18 0.0172(7) 0.0228(7) 0.0245(7) -0.0029(6) 0.0037(6) -0.0018(6) C19 0.0241(8) 0.0250(8) 0.0352(9) -0.0050(7) 0.0035(7) -0.0049(6) C20 0.0244(8) 0.0304(8) 0.0320(9) -0.0003(7) -0.0023(7) -0.0007(7) C21 0.0195(7) 0.0214(7) 0.0186(7) -0.0029(6) 0.0009(6) -0.0019(6) C22 0.0186(7) 0.0199(7) 0.0214(7) 0.0000(6) 0.0040(6) -0.0006(6) C23 0.0211(7) 0.0194(7) 0.0201(7) 0.0017(6) 0.0042(6) -0.0022(6) C24 0.0240(8) 0.0242(8) 0.0188(7) 0.0002(6) 0.0036(6) -0.0023(6) O25 0.0283(6) 0.0224(5) 0.0281(6) 0.0005(4) 0.0126(5) 0.0036(4) O26 0.0277(6) 0.0244(5) 0.0265(6) 0.0012(4) 0.0112(5) -0.0004(4) O27 0.0200(5) 0.0237(5) 0.0256(5) 0.0011(4) 0.0013(4) -0.0001(4) O28 0.0219(5) 0.0228(5) 0.0249(5) -0.0020(4) 0.0044(4) -0.0038(4) O29 0.0353(7) 0.0260(6) 0.0360(6) -0.0022(5) 0.0220(5) -0.0052(5) O30 0.0389(7) 0.0263(6) 0.0413(7) -0.0085(5) 0.0187(5) -0.0034(5) _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 O8 1.2470(17) . ? C1 N2 1.3397(18) . ? C1 C7 1.485(2) . ? N2 C3 1.4191(17) . ? N2 H2 0.8800 . ? C3 C16 1.392(2) . ? C3 C4 1.3976(19) . ? C4 N13 1.3405(18) . ? C4 N5 1.4101(18) . ? N5 C6 1.4229(18) . ? N5 C18 1.4526(18) . ? C6 N12 1.3294(18) . ? C6 C7 1.407(2) . ? C7 C9 1.389(2) . ? C9 C10 1.380(2) . ? C9 H9 0.9500 . ? C10 C11 1.380(2) . ? C10 H10 0.9500 . ? C11 N12 1.3417(19) . ? C11 H11 0.9500 . ? N13 C14 1.342(2) . ? C14 C15 1.373(2) . ? C14 H14 0.9500 . ? C15 C16 1.391(2) . ? C15 H15 0.9500 . ? C16 C17 1.503(2) . ? C17 H17B 0.9800 . ? C17 H17A 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.490(2) . ? C18 C20 1.494(2) . ? C18 H18 1.0000 . ? C19 C20 1.506(2) . ? C19 H19B 0.9900 . ? C19 H19A 0.9900 . ? C20 H20B 0.9900 . ? C20 H20A 0.9900 . ? C21 O26 1.2158(17) . ? C21 O25 1.3190(17) . ? C21 C22 1.5224(19) . ? C22 O27 1.4118(17) . ? C22 C23 1.545(2) . ? C22 H22 1.0000 . ? C23 O28 1.4141(16) . ? C23 C24 1.525(2) . ? C23 H23 1.0000 . ? C24 O30 1.2080(18) . ? C24 O29 1.3022(17) . ? O25 H25 0.8400 . ? O27 H27 0.8400 . ? O28 H28 0.8400 . ? O29 H29 0.8400 . ? 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 O8 C1 N2 120.92(13) . . ? O8 C1 C7 119.82(13) . . ? N2 C1 C7 119.25(12) . . ? C1 N2 C3 128.17(12) . . ? C1 N2 H2 115.9 . . ? C3 N2 H2 115.9 . . ? C16 C3 C4 119.68(13) . . ? C16 C3 N2 118.49(12) . . ? C4 C3 N2 121.78(13) . . ? N13 C4 C3 121.25(13) . . ? N13 C4 N5 118.40(12) . . ? C3 C4 N5 120.34(12) . . ? C4 N5 C6 115.10(12) . . ? C4 N5 C18 116.83(11) . . ? C6 N5 C18 115.85(11) . . ? N12 C6 C7 122.50(13) . . ? N12 C6 N5 116.06(12) . . ? C7 C6 N5 121.41(12) . . ? C9 C7 C6 117.72(13) . . ? C9 C7 C1 117.96(13) . . ? C6 C7 C1 124.19(13) . . ? C10 C9 C7 120.15(13) . . ? C10 C9 H9 119.9 . . ? C7 C9 H9 119.9 . . ? C11 C10 C9 117.57(14) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? N12 C11 C10 123.89(14) . . ? N12 C11 H11 118.1 . . ? C10 C11 H11 118.1 . . ? C6 N12 C11 118.07(12) . . ? C4 N13 C14 118.59(13) . . ? N13 C14 C15 123.02(14) . . ? N13 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C14 C15 C16 119.26(14) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C3 117.58(14) . . ? C15 C16 C17 121.82(13) . . ? C3 C16 C17 120.59(13) . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17A 109.5 . . ? H17B C17 H17A 109.5 . . ? C16 C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? N5 C18 C19 116.18(12) . . ? N5 C18 C20 117.18(12) . . ? C19 C18 C20 60.61(10) . . ? N5 C18 H18 117.0 . . ? C19 C18 H18 117.0 . . ? C20 C18 H18 117.0 . . ? C18 C19 C20 59.80(10) . . ? C18 C19 H19B 117.8 . . ? C20 C19 H19B 117.8 . . ? C18 C19 H19A 117.8 . . ? C20 C19 H19A 117.8 . . ? H19B C19 H19A 114.9 . . ? C18 C20 C19 59.58(10) . . ? C18 C20 H20B 117.8 . . ? C19 C20 H20B 117.8 . . ? C18 C20 H20A 117.8 . . ? C19 C20 H20A 117.8 . . ? H20B C20 H20A 115.0 . . ? O26 C21 O25 124.06(13) . . ? O26 C21 C22 123.29(13) . . ? O25 C21 C22 112.64(11) . . ? O27 C22 C21 111.45(11) . . ? O27 C22 C23 110.26(11) . . ? C21 C22 C23 110.13(12) . . ? O27 C22 H22 108.3 . . ? C21 C22 H22 108.3 . . ? C23 C22 H22 108.3 . . ? O28 C23 C24 109.20(11) . . ? O28 C23 C22 110.31(11) . . ? C24 C23 C22 109.31(12) . . ? O28 C23 H23 109.3 . . ? C24 C23 H23 109.3 . . ? C22 C23 H23 109.3 . . ? O30 C24 O29 126.55(13) . . ? O30 C24 C23 121.38(13) . . ? O29 C24 C23 112.06(12) . . ? C21 O25 H25 109.5 . . ? C22 O27 H27 109.5 . . ? C23 O28 H28 109.5 . . ? C24 O29 H29 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 O8 C1 N2 C3 171.12(14) . . . . ? C7 C1 N2 C3 -7.6(2) . . . . ? C1 N2 C3 C16 -132.06(16) . . . . ? C1 N2 C3 C4 50.5(2) . . . . ? C16 C3 C4 N13 -6.9(2) . . . . ? N2 C3 C4 N13 170.45(13) . . . . ? C16 C3 C4 N5 172.05(13) . . . . ? N2 C3 C4 N5 -10.6(2) . . . . ? N13 C4 N5 C6 121.09(14) . . . . ? C3 C4 N5 C6 -57.93(17) . . . . ? N13 C4 N5 C18 -19.84(18) . . . . ? C3 C4 N5 C18 161.14(13) . . . . ? C4 N5 C6 N12 -120.40(14) . . . . ? C18 N5 C6 N12 20.93(18) . . . . ? C4 N5 C6 C7 61.24(17) . . . . ? C18 N5 C6 C7 -157.43(13) . . . . ? N12 C6 C7 C9 2.0(2) . . . . ? N5 C6 C7 C9 -179.70(13) . . . . ? N12 C6 C7 C1 -173.70(13) . . . . ? N5 C6 C7 C1 4.6(2) . . . . ? O8 C1 C7 C9 -31.9(2) . . . . ? N2 C1 C7 C9 146.86(14) . . . . ? O8 C1 C7 C6 143.85(15) . . . . ? N2 C1 C7 C6 -37.4(2) . . . . ? C6 C7 C9 C10 1.0(2) . . . . ? C1 C7 C9 C10 176.97(14) . . . . ? C7 C9 C10 C11 -3.1(2) . . . . ? C9 C10 C11 N12 2.6(2) . . . . ? C7 C6 N12 C11 -2.6(2) . . . . ? N5 C6 N12 C11 179.04(13) . . . . ? C10 C11 N12 C6 0.2(2) . . . . ? C3 C4 N13 C14 0.1(2) . . . . ? N5 C4 N13 C14 -178.90(13) . . . . ? C4 N13 C14 C15 5.8(2) . . . . ? N13 C14 C15 C16 -4.7(2) . . . . ? C14 C15 C16 C3 -2.3(2) . . . . ? C14 C15 C16 C17 176.63(14) . . . . ? C4 C3 C16 C15 7.8(2) . . . . ? N2 C3 C16 C15 -169.67(12) . . . . ? C4 C3 C16 C17 -171.11(13) . . . . ? N2 C3 C16 C17 11.4(2) . . . . ? C4 N5 C18 C19 -66.96(17) . . . . ? C6 N5 C18 C19 152.39(13) . . . . ? C4 N5 C18 C20 -135.73(13) . . . . ? C6 N5 C18 C20 83.63(15) . . . . ? N5 C18 C19 C20 -107.89(14) . . . . ? N5 C18 C20 C19 106.26(14) . . . . ? O26 C21 C22 O27 -22.88(19) . . . . ? O25 C21 C22 O27 158.58(12) . . . . ? O26 C21 C22 C23 99.82(16) . . . . ? O25 C21 C22 C23 -78.72(15) . . . . ? O27 C22 C23 O28 56.49(14) . . . . ? C21 C22 C23 O28 -66.90(14) . . . . ? O27 C22 C23 C24 -63.59(14) . . . . ? C21 C22 C23 C24 173.01(11) . . . . ? O28 C23 C24 O30 -12.88(19) . . . . ? C22 C23 C24 O30 107.88(16) . . . . ? O28 C23 C24 O29 167.53(12) . . . . ? C22 C23 C24 O29 -71.72(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.222 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.042