# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Alexander Butin' _publ_contact_author_email 'ALEXANDER BUTIN@MAIL.RU' _publ_section_title ; Furan ring opening - pyrrole ring closure: a new synthetic route to aryl(heteroaryl)-annulated pyrrolo[1,2-a][1,4]diazepines ; loop_ _publ_author_name 'Alexander Butin' 'Dmitry A. Cheshkov' 'Gennady D. Krapivin' 'Tatyana A. Nevolina' ; V.A.Shcherbinin ; 'Igor Trushkov' # Attachment 'KR99.CIF' data_kr99 _database_code_depnum_ccdc_archive 'CCDC 761545' #TrackingRef 'KR99.CIF' _audit_creation_method SHELXL97 _chemical_name_systematic ; 1-Methyl-4,5-dihydro-6H-pyrrolo[1,2-a][1,4]benzodiazepin-6-one ; _chemical_melting_point 508-509 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.286(1) _cell_length_b 8.661(2) _cell_length_c 19.599(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1067.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 9.7 _cell_measurement_theta_max 12.6 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'beta filter' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method \w/2\t--scans _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 100 _diffrn_standards_decay_% 0.06 _diffrn_reflns_number 2284 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0872 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1980 _reflns_number_gt 1045 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0283P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Heavy atom types Z>Si no present in molecule, because refinement Flack parameter "x" impossible, but ALL Friedel pairs were merged. ; _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1980 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_ref 0.0547 _refine_ls_wR_factor_gt 0.0493 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.864 _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 O1 O 0.26477(17) 0.30172(12) 0.44869(5) 0.0471(3) Uani 1 1 d . . . N1 N 0.6027(2) 0.38575(15) 0.44094(6) 0.0454(3) Uani 1 1 d . . . N2 N 0.53912(17) 0.69944(14) 0.38066(5) 0.0346(3) Uani 1 1 d . . . C1 C 0.3483(2) 0.45964(16) 0.35400(6) 0.0329(3) Uani 1 1 d . . . C2 C 0.2219(2) 0.37699(17) 0.30851(7) 0.0401(3) Uani 1 1 d . . . C3 C 0.1622(3) 0.43726(19) 0.24670(7) 0.0463(4) Uani 1 1 d . . . C4 C 0.2240(3) 0.58525(19) 0.22975(7) 0.0444(4) Uani 1 1 d . . . C5 C 0.3469(2) 0.66996(16) 0.27399(7) 0.0389(4) Uani 1 1 d . . . C6 C 0.4101(2) 0.60930(16) 0.33646(6) 0.0319(3) Uani 1 1 d . . . C7 C 0.7228(2) 0.64370(18) 0.41137(7) 0.0411(4) Uani 1 1 d . . . C8 C 0.7693(3) 0.4763(2) 0.40779(8) 0.0494(4) Uani 1 1 d . . . C9 C 0.4026(2) 0.37808(17) 0.41929(7) 0.0369(4) Uani 1 1 d . . . C10 C 0.8178(2) 0.7647(2) 0.44343(8) 0.0530(5) Uani 1 1 d . . . C11 C 0.6914(3) 0.8955(2) 0.43241(7) 0.0520(4) Uani 1 1 d . . . C12 C 0.5205(3) 0.85625(18) 0.39418(7) 0.0420(4) Uani 1 1 d . . . C13 C 0.3327(3) 0.95002(19) 0.37406(8) 0.0551(5) Uani 1 1 d . . . H1 H 0.6325 0.3358 0.4792 0.050 Uiso 1 1 d . . . H2 H 0.1786 0.2717 0.3212 0.050 Uiso 1 1 d . . . H3 H 0.0745 0.3721 0.2161 0.050 Uiso 1 1 d . . . H4 H 0.1804 0.6311 0.1845 0.050 Uiso 1 1 d . . . H5 H 0.3882 0.7714 0.2615 0.050 Uiso 1 1 d . . . H81 H 0.9005 0.4581 0.4310 0.050 Uiso 1 1 d . . . H82 H 0.7830 0.4451 0.3588 0.050 Uiso 1 1 d . . . H10 H 0.9379 0.7542 0.4679 0.050 Uiso 1 1 d . . . H11 H 0.7162 0.9904 0.4493 0.050 Uiso 1 1 d . . . H131 H 0.1926 0.8904 0.3836 0.080 Uiso 1 1 d . . . H132 H 0.3407 0.9883 0.3260 0.080 Uiso 1 1 d . . . H133 H 0.3323 1.0429 0.4039 0.080 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0583(7) 0.0372(6) 0.0459(5) 0.0084(5) 0.0121(6) -0.0057(5) N1 0.0491(7) 0.0438(8) 0.0434(7) 0.0168(6) -0.0034(6) 0.0057(7) N2 0.0355(7) 0.0342(8) 0.0341(7) 0.0044(6) -0.0026(5) -0.0034(6) C1 0.0299(7) 0.0335(8) 0.0353(8) 0.0001(6) 0.0051(6) 0.0041(7) C2 0.0379(8) 0.0336(8) 0.0489(8) -0.0035(7) 0.0021(7) -0.0011(7) C3 0.0402(9) 0.0542(10) 0.0443(9) -0.0094(8) -0.0096(7) 0.0021(8) C4 0.0475(9) 0.0502(10) 0.0354(8) 0.0023(7) -0.0070(7) 0.0091(8) C5 0.0421(9) 0.0381(9) 0.0364(8) 0.0073(6) 0.0018(6) 0.0010(7) C6 0.0290(7) 0.0349(8) 0.0317(7) 0.0003(6) 0.0025(6) 0.0008(7) C7 0.0343(8) 0.0516(10) 0.0374(7) 0.0096(7) -0.0034(7) -0.0053(7) C8 0.0336(8) 0.0630(11) 0.0515(9) 0.0115(8) -0.0044(8) 0.0085(8) C9 0.0432(9) 0.0303(8) 0.0371(8) -0.0019(7) 0.0036(7) 0.0053(7) C10 0.0467(9) 0.0717(14) 0.0405(8) 0.0138(8) -0.0102(8) -0.0190(9) C11 0.0695(11) 0.0474(10) 0.0390(8) 0.0041(7) -0.0054(8) -0.0251(9) C12 0.0534(10) 0.0365(9) 0.0361(8) 0.0044(7) 0.0033(7) -0.0092(8) C13 0.0674(11) 0.0365(9) 0.0613(11) 0.0020(8) 0.0036(9) 0.0033(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.2330(17) . ? N1 C9 1.3291(19) . ? N1 C8 1.461(2) . ? N1 H1 0.8859 . ? N2 C7 1.3884(17) . ? N2 C12 1.3887(19) . ? N2 C6 1.4205(18) . ? C1 C2 1.392(2) . ? C1 C6 1.3962(19) . ? C1 C9 1.5010(19) . ? C2 C3 1.371(2) . ? C2 H2 0.9838 . ? C3 C4 1.380(2) . ? C3 H3 0.9910 . ? C4 C5 1.373(2) . ? C4 H4 1.0087 . ? C5 C6 1.3903(19) . ? C5 H5 0.9477 . ? C7 C10 1.360(2) . ? C7 C8 1.480(2) . ? C8 H81 0.9554 . ? C8 H82 1.0015 . ? C10 C11 1.400(2) . ? C10 H10 0.8991 . ? C11 C12 1.353(2) . ? C11 H11 0.8996 . ? C12 C13 1.486(2) . ? C13 H131 1.0375 . ? C13 H132 1.0001 . ? C13 H133 0.9940 . ? 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 C9 N1 C8 124.28(13) . . ? C9 N1 H1 116.5 . . ? C8 N1 H1 119.2 . . ? C7 N2 C12 109.12(13) . . ? C7 N2 C6 123.23(12) . . ? C12 N2 C6 127.28(12) . . ? C2 C1 C6 118.59(12) . . ? C2 C1 C9 115.71(13) . . ? C6 C1 C9 125.69(13) . . ? C3 C2 C1 121.74(14) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 118.2 . . ? C2 C3 C4 119.29(14) . . ? C2 C3 H3 118.0 . . ? C4 C3 H3 122.7 . . ? C5 C4 C3 120.17(14) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.98(14) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 119.22(13) . . ? C5 C6 N2 119.51(13) . . ? C1 C6 N2 121.26(12) . . ? C10 C7 N2 107.30(13) . . ? C10 C7 C8 133.61(14) . . ? N2 C7 C8 118.95(13) . . ? N1 C8 C7 111.29(13) . . ? N1 C8 H81 108.5 . . ? C7 C8 H81 108.1 . . ? N1 C8 H82 110.1 . . ? C7 C8 H82 109.1 . . ? H81 C8 H82 109.8 . . ? O1 C9 N1 122.87(13) . . ? O1 C9 C1 119.40(13) . . ? N1 C9 C1 117.64(13) . . ? C7 C10 C11 107.63(13) . . ? C7 C10 H10 122.5 . . ? C11 C10 H10 129.8 . . ? C12 C11 C10 109.44(15) . . ? C12 C11 H11 124.8 . . ? C10 C11 H11 125.7 . . ? C11 C12 N2 106.51(15) . . ? C11 C12 C13 129.82(15) . . ? N2 C12 C13 123.43(14) . . ? C12 C13 H131 110.8 . . ? C12 C13 H132 113.0 . . ? H131 C13 H132 112.2 . . ? C12 C13 H133 106.8 . . ? H131 C13 H133 107.2 . . ? H132 C13 H133 106.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.89 2.03 2.8902(16) 164.6 4_556 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.097 _refine_diff_density_min -0.097 _refine_diff_density_rms 0.027 _chemical_name_common 1-Methyl-4,5-dihydro-6H-pyrrolo(1,2-a)(1,4)benzodiazepin-6-one # Attachment 'KR100.CIF' data_kr100 _database_code_depnum_ccdc_archive 'CCDC 761546' #TrackingRef 'KR100.CIF' _audit_creation_method SHELXL97 _chemical_name_systematic ; 1-tert-Butyl-4,5-dihydro-6H-pyrrolo[1,2-a][1,4]benzodiazepin-6-one ; _chemical_melting_point 491-492 _chemical_formula_moiety 'C16 H18 N2 O' _chemical_formula_sum 'C16 H18 N2 O' _chemical_formula_weight 254.32 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.016(1) _cell_length_b 8.846(2) _cell_length_c 12.300(3) _cell_angle_alpha 72.26(3) _cell_angle_beta 81.27(3) _cell_angle_gamma 79.73(3) _cell_volume 711.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.6 _cell_measurement_theta_max 12.3 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'beta filter' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method \w/2\t--scans _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 100 _diffrn_standards_decay_% 0.7 _diffrn_reflns_number 3023 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0660 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.97 _reflns_number_total 2783 _reflns_number_gt 1479 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.054(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2783 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0897 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _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 O1 O 0.12538(14) 0.49201(11) 0.62337(9) 0.0498(3) Uani 1 1 d . . . N1 N 0.17073(15) 0.31839(12) 0.51780(9) 0.0384(3) Uani 1 1 d . . . N2 N 0.34094(15) 0.01863(12) 0.67792(9) 0.0360(3) Uani 1 1 d . . . C1 C 0.40401(17) 0.29334(15) 0.65095(11) 0.0358(3) Uani 1 1 d . . . C2 C 0.5241(2) 0.39446(17) 0.66401(13) 0.0464(4) Uani 1 1 d . . . C3 C 0.7043(2) 0.3348(2) 0.70363(14) 0.0531(4) Uani 1 1 d . . . C4 C 0.76749(19) 0.17238(19) 0.72884(12) 0.0482(4) Uani 1 1 d . . . C5 C 0.64915(18) 0.06944(16) 0.71941(11) 0.0414(3) Uani 1 1 d . . . C6 C 0.46387(17) 0.12804(15) 0.68413(11) 0.0340(3) Uani 1 1 d . . . C7 C 0.27311(17) 0.03172(15) 0.57464(12) 0.0369(3) Uani 1 1 d . . . C8 C 0.28297(18) 0.18346(15) 0.48071(11) 0.0397(3) Uani 1 1 d . . . C9 C 0.21988(17) 0.37375(14) 0.59739(11) 0.0363(3) Uani 1 1 d . . . C10 C 0.19511(19) -0.10250(16) 0.58657(13) 0.0437(3) Uani 1 1 d . . . C11 C 0.2109(2) -0.19972(17) 0.70000(14) 0.0483(4) Uani 1 1 d . . . C12 C 0.2984(2) -0.12573(15) 0.75736(12) 0.0424(3) Uani 1 1 d . . . C13 C 0.3181(2) -0.17490(18) 0.88594(14) 0.0574(4) Uani 1 1 d . . . C14 C 0.1647(4) -0.2854(3) 0.94711(18) 0.0887(7) Uani 1 1 d . . . C15 C 0.5161(3) -0.2683(3) 0.91794(19) 0.0930(7) Uani 1 1 d . . . C16 C 0.2760(3) -0.0290(2) 0.93232(14) 0.0697(5) Uani 1 1 d . . . H1 H 0.0750 0.3779 0.4783 0.080 Uiso 1 1 d . . . H2 H 0.4802 0.5093 0.6430 0.080 Uiso 1 1 d . . . H3 H 0.7885 0.4081 0.7095 0.080 Uiso 1 1 d . . . H4 H 0.8964 0.1243 0.7545 0.080 Uiso 1 1 d . . . H5 H 0.6945 -0.0436 0.7367 0.080 Uiso 1 1 d . . . H81 H 0.4170 0.2069 0.4579 0.080 Uiso 1 1 d . . . H82 H 0.2207 0.1757 0.4139 0.080 Uiso 1 1 d . . . H10 H 0.1418 -0.1220 0.5251 0.080 Uiso 1 1 d . . . H11 H 0.1606 -0.2979 0.7314 0.080 Uiso 1 1 d . . . H141 H 0.1692 -0.3113 1.0341 0.080 Uiso 1 1 d . . . H142 H 0.1869 -0.3786 0.9169 0.080 Uiso 1 1 d . . . H143 H 0.0314 -0.2301 0.9261 0.080 Uiso 1 1 d . . . H151 H 0.5096 -0.3222 1.0003 0.110 Uiso 1 1 d . . . H152 H 0.6235 -0.2026 0.8849 0.110 Uiso 1 1 d . . . H153 H 0.5565 -0.3513 0.8803 0.110 Uiso 1 1 d . . . H161 H 0.2801 -0.0699 1.0152 0.080 Uiso 1 1 d . . . H162 H 0.3761 0.0485 0.8980 0.080 Uiso 1 1 d . . . H163 H 0.1318 0.0359 0.9143 0.080 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0454(5) 0.0370(5) 0.0730(7) -0.0258(5) -0.0170(5) 0.0056(4) N1 0.0357(6) 0.0342(6) 0.0454(7) -0.0126(5) -0.0114(5) 0.0033(4) N2 0.0384(6) 0.0289(5) 0.0420(6) -0.0098(5) -0.0110(5) -0.0025(4) C1 0.0330(6) 0.0364(7) 0.0382(7) -0.0106(6) -0.0031(5) -0.0062(5) C2 0.0455(8) 0.0416(7) 0.0531(9) -0.0080(6) -0.0088(6) -0.0158(6) C3 0.0453(8) 0.0603(9) 0.0558(9) -0.0083(7) -0.0109(7) -0.0225(7) C4 0.0339(7) 0.0677(10) 0.0410(8) -0.0097(7) -0.0098(6) -0.0075(7) C5 0.0389(7) 0.0456(8) 0.0389(8) -0.0121(6) -0.0092(6) 0.0010(6) C6 0.0326(6) 0.0355(7) 0.0349(7) -0.0118(5) -0.0052(5) -0.0026(5) C7 0.0327(6) 0.0377(7) 0.0435(7) -0.0183(6) -0.0099(5) 0.0036(5) C8 0.0376(7) 0.0402(7) 0.0406(8) -0.0132(6) -0.0082(6) 0.0030(6) C9 0.0327(6) 0.0300(6) 0.0450(8) -0.0088(6) -0.0033(5) -0.0054(5) C10 0.0380(7) 0.0418(8) 0.0573(9) -0.0229(7) -0.0112(6) -0.0010(6) C11 0.0465(8) 0.0363(7) 0.0639(10) -0.0153(7) -0.0083(7) -0.0069(6) C12 0.0454(8) 0.0296(6) 0.0500(8) -0.0078(6) -0.0084(6) -0.0030(6) C13 0.0709(10) 0.0466(9) 0.0495(9) 0.0012(7) -0.0158(8) -0.0127(8) C14 0.1137(16) 0.0845(14) 0.0630(12) 0.0054(10) -0.0103(11) -0.0473(13) C15 0.0933(14) 0.0833(14) 0.0782(14) 0.0151(11) -0.0342(12) 0.0038(12) C16 0.0957(13) 0.0764(12) 0.0392(9) -0.0140(8) -0.0049(8) -0.0234(10) _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 O1 C9 1.2362(15) . ? N1 C9 1.3311(16) . ? N1 C8 1.4630(17) . ? N1 H1 0.8836 . ? N2 C7 1.3884(16) . ? N2 C12 1.4007(18) . ? N2 C6 1.4315(16) . ? C1 C2 1.3906(18) . ? C1 C6 1.3966(18) . ? C1 C9 1.5014(18) . ? C2 C3 1.380(2) . ? C2 H2 0.9729 . ? C3 C4 1.379(2) . ? C3 H3 0.9758 . ? C4 C5 1.377(2) . ? C4 H4 0.9829 . ? C5 C6 1.3931(18) . ? C5 H5 0.9614 . ? C7 C10 1.3534(18) . ? C7 C8 1.4851(19) . ? C8 H81 0.9796 . ? C8 H82 1.0131 . ? C10 C11 1.407(2) . ? C10 H10 0.9644 . ? C11 C12 1.363(2) . ? C11 H11 0.9442 . ? C12 C13 1.528(2) . ? C13 C15 1.525(3) . ? C13 C16 1.530(2) . ? C13 C14 1.537(3) . ? C14 H141 1.0275 . ? C14 H142 0.9818 . ? C14 H143 1.0071 . ? C15 H151 0.9774 . ? C15 H152 0.9951 . ? C15 H153 0.9629 . ? C16 H161 0.9751 . ? C16 H162 1.0235 . ? C16 H163 1.0889 . ? 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 C9 N1 C8 124.22(10) . . ? C9 N1 H1 116.0 . . ? C8 N1 H1 119.0 . . ? C7 N2 C12 108.87(10) . . ? C7 N2 C6 120.32(11) . . ? C12 N2 C6 129.82(11) . . ? C2 C1 C6 118.92(12) . . ? C2 C1 C9 116.09(11) . . ? C6 C1 C9 124.96(11) . . ? C3 C2 C1 121.19(13) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 118.7 . . ? C4 C3 C2 119.36(13) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.49(13) . . ? C5 C4 H4 116.9 . . ? C3 C4 H4 122.6 . . ? C4 C5 C6 120.43(13) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 119.35(12) . . ? C5 C6 N2 119.60(11) . . ? C1 C6 N2 121.00(11) . . ? C10 C7 N2 108.16(12) . . ? C10 C7 C8 133.02(12) . . ? N2 C7 C8 118.62(11) . . ? N1 C8 C7 110.36(11) . . ? N1 C8 H81 107.2 . . ? C7 C8 H81 111.8 . . ? N1 C8 H82 107.2 . . ? C7 C8 H82 108.5 . . ? H81 C8 H82 111.7 . . ? O1 C9 N1 122.37(12) . . ? O1 C9 C1 120.00(12) . . ? N1 C9 C1 117.53(11) . . ? C7 C10 C11 107.39(12) . . ? C7 C10 H10 123.2 . . ? C11 C10 H10 129.4 . . ? C12 C11 C10 109.59(13) . . ? C12 C11 H11 126.2 . . ? C10 C11 H11 124.1 . . ? C11 C12 N2 105.96(13) . . ? C11 C12 C13 127.52(13) . . ? N2 C12 C13 125.89(12) . . ? C15 C13 C12 113.73(16) . . ? C15 C13 C16 109.41(16) . . ? C12 C13 C16 111.12(13) . . ? C15 C13 C14 107.04(16) . . ? C12 C13 C14 107.65(13) . . ? C16 C13 C14 107.62(17) . . ? C13 C14 H141 108.1 . . ? C13 C14 H142 109.0 . . ? H141 C14 H142 115.4 . . ? C13 C14 H143 109.9 . . ? H141 C14 H143 109.9 . . ? H142 C14 H143 104.4 . . ? C13 C15 H151 110.3 . . ? C13 C15 H152 112.1 . . ? H151 C15 H152 116.6 . . ? C13 C15 H153 111.7 . . ? H151 C15 H153 106.2 . . ? H152 C15 H153 99.3 . . ? C13 C16 H161 106.6 . . ? C13 C16 H162 112.3 . . ? H161 C16 H162 109.5 . . ? C13 C16 H163 110.6 . . ? H161 C16 H163 109.2 . . ? H162 C16 H163 108.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.88 1.99 2.8674(18) 174.7 2_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.170 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.031 _chemical_name_common ;1-tert-Butyl-4,5-dihydro-6H-pyrrolo(1,2-a)(1,4)benzodiazepin- 6-one ;