Supplementary information (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Mihail Barboiu' 'Yves-Marie Legrand' 'Mathieu Michau' 'van der Lee, Arie' _publ_contact_author_name 'Mihail Barboiu' _publ_contact_author_address ; Institute Europeen Membranes CNRS IEM 5635 Pl Eugene Bat,CC 47 Montpellier F-34095 5 FRANCE ; _publ_contact_author_email BARBOIU@IEMM.UNIV-MONTP2.FR _publ_requested_journal CrystEngComm _publ_section_title ; Homomeric and heteromeric self-assembly of hybrid ureido-imidazole compounds ; data_1 _database_code_depnum_ccdc_archive 'CCDC 651227' _audit_creation_date 07-05-31 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'mdbm17 in P 21/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.6630(18) _cell_length_b 6.0080(10) _cell_length_c 13.328(2) _cell_angle_alpha 90 _cell_angle_beta 92.231(8) _cell_angle_gamma 90 _cell_volume 933.2(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0010 0.0007 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 ; International Tables Vol C 4.2.6.8 and 6.1.1.4, dispersion factors from Interpolated values from CXRO/LLNL data ; H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 ; International Tables Vol C 4.2.6.8 and 6.1.1.4, dispersion factors from Interpolated values from CXRO/LLNL data ; N 0.0028 0.0016 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 ; International Tables Vol C 4.2.6.8 and 6.1.1.4, dispersion factors from Interpolated values from CXRO/LLNL data ; O 0.0046 0.0029 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 ; International Tables Vol C 4.2.6.8 and 6.1.1.4, dispersion factors from Interpolated values from CXRO/LLNL data ; _cell_formula_units_Z 4 # Given Formula = C13 H25 N2 O1 # Dc = 1.60 Fooo = 424.00 Mu = 1.01 M = 225.35 # Found Formula = C10 H10 N4 O1 # Dc = 1.44 FOOO = 424.00 Mu = 1.00 M = 202.22 _chemical_formula_sum 'C10 H10 N4 O1' _chemical_formula_moiety 'C10 H10 N4 O1' _chemical_compound_source ? _chemical_formula_weight 202.22 _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2 _cell_measurement_theta_max 13 _cell_measurement_temperature 120 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_min 0.1 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.100 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.51091 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 8098 _reflns_number_total 2532 _diffrn_reflns_av_R_equivalents 0.129 # Number of reflections with Friedels Law is 2532 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2678 _diffrn_reflns_theta_min 2.674 _diffrn_reflns_theta_max 20.945 _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 20.526 _diffrn_measured_fraction_theta_full 0.954 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -16 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.37 _refine_diff_density_max 0.47 _refine_ls_number_reflns 2275 _refine_ls_number_restraints 0 _refine_ls_number_parameters 136 #_refine_ls_R_factor_ref 0.0529 _refine_ls_wR_factor_ref 0.0576 _refine_ls_goodness_of_fit_ref 0.9603 #_reflns_number_all 2530 _refine_ls_R_factor_all 0.0568 _refine_ls_wR_factor_all 0.0594 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2275 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_gt 0.0576 _refine_ls_shift/su_max 0.000664 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.54 0.629 0.895 ; _refine_special_details ; All atoms were refined anisotropically. Positional coordinated of the hydrogen atoms were refined independently ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.02308(7) 0.18323(13) 0.89373(6) 0.0119 1.0000 Uani . . . . . . C2 C -0.02064(8) -0.01923(15) 0.86042(7) 0.0128 1.0000 Uani . . . . . . C3 C 0.04738(8) -0.08448(15) 0.78591(7) 0.0131 1.0000 Uani . . . . . . N4 N 0.13362(7) 0.07165(13) 0.77216(6) 0.0121 1.0000 Uani . . . . . . C5 C 0.11490(7) 0.22846(14) 0.83931(6) 0.0094 1.0000 Uani . . . . . . N6 N 0.18267(7) 0.41589(13) 0.84954(6) 0.0112 1.0000 Uani . . . . . . C7 C 0.19232(8) 0.54141(14) 0.93612(6) 0.0104 1.0000 Uani . . . . . . O8 O 0.12913(6) 0.51705(12) 1.00620(5) 0.0152 1.0000 Uani . . . . . . N9 N 0.27976(7) 0.69216(13) 0.93316(6) 0.0125 1.0000 Uani . . . . . . C10 C 0.30922(8) 0.84775(15) 1.00915(7) 0.0117 1.0000 Uani . . . . . . C11 C 0.30120(9) 0.79824(16) 1.11067(7) 0.0157 1.0000 Uani . . . . . . C12 C 0.33539(9) 0.95532(19) 1.18239(8) 0.0193 1.0000 Uani . . . . . . C13 C 0.37852(10) 1.16011(18) 1.15402(9) 0.0220 1.0000 Uani . . . . . . C14 C 0.38822(10) 1.20733(17) 1.05277(9) 0.0215 1.0000 Uani . . . . . . C15 C 0.35355(9) 1.05254(16) 0.98034(8) 0.0164 1.0000 Uani . . . . . . H16 H 0.2724 0.6568 1.1294 0.0180 1.0000 Uiso . . . . . . H17 H 0.3278 0.9251 1.2504 0.0211 1.0000 Uiso . . . . . . H18 H 0.4009 1.2677 1.2018 0.0242 1.0000 Uiso . . . . . . H19 H 0.4204 1.3433 1.0325 0.0234 1.0000 Uiso . . . . . . H20 H 0.3629 1.0790 0.9129 0.0185 1.0000 Uiso . . . . . . H21 H 0.3179 0.6977 0.8766 0.0126 1.0000 Uiso . . . . . . H22 H 0.2274 0.4528 0.8016 0.0118 1.0000 Uiso . . . . . . H23 H -0.0075 0.2652 0.9407 0.0138 1.0000 Uiso . . . . . . H24 H -0.0876 -0.0879 0.8875 0.0131 1.0000 Uiso . . . . . . H25 H 0.0396 -0.2190 0.7495 0.0130 1.0000 Uiso . . . . . . 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 N1 0.0133(4) 0.0120(4) 0.0109(3) -0.0024(3) 0.0052(3) -0.0010(3) C2 0.0138(4) 0.0116(4) 0.0132(4) -0.0001(3) 0.0019(3) -0.0018(3) C3 0.0133(4) 0.0108(4) 0.0153(4) -0.0021(3) 0.0010(3) 0.0011(3) N4 0.0127(4) 0.0115(4) 0.0124(3) -0.0031(3) 0.0039(3) 0.0015(3) C5 0.0106(4) 0.0096(4) 0.0081(3) -0.0001(3) 0.0017(3) 0.0015(3) N6 0.0136(4) 0.0110(3) 0.0095(3) -0.0015(3) 0.0050(3) -0.0023(3) C7 0.0102(4) 0.0099(4) 0.0111(4) -0.0015(3) 0.0016(3) 0.0013(3) O8 0.0139(3) 0.0183(3) 0.0138(3) -0.0056(2) 0.0070(2) -0.0022(2) N9 0.0144(4) 0.0123(3) 0.0110(3) -0.0019(3) 0.0036(3) -0.0032(3) C10 0.0100(4) 0.0105(4) 0.0146(4) -0.0018(3) 0.0002(3) 0.0010(3) C11 0.0175(4) 0.0152(4) 0.0144(4) -0.0024(3) 0.0020(3) 0.0002(3) C12 0.0184(5) 0.0227(5) 0.0167(4) -0.0073(4) -0.0017(3) 0.0036(4) C13 0.0183(5) 0.0174(5) 0.0295(5) -0.0111(4) -0.0068(4) 0.0031(3) C14 0.0192(5) 0.0113(4) 0.0337(6) -0.0016(4) -0.0049(4) -0.0013(3) C15 0.0152(4) 0.0122(4) 0.0216(5) 0.0020(3) -0.0023(3) 0.0003(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.059(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C2 . 1.3853(12) yes N1 . C5 . 1.3443(11) yes N1 . H23 . 0.883 no C2 . C3 . 1.3530(13) yes C2 . H24 . 0.965 no C3 . N4 . 1.3926(12) yes C3 . H25 . 0.946 no N4 . C5 . 1.3234(11) yes C5 . N6 . 1.3795(11) yes N6 . C7 . 1.3794(11) yes N6 . H22 . 0.869 no C7 . O8 . 1.2210(11) yes C7 . N9 . 1.3657(12) yes N9 . C10 . 1.4109(11) yes N9 . H21 . 0.891 no C10 . C11 . 1.3921(13) yes C10 . C15 . 1.3943(13) yes C11 . C12 . 1.3905(13) yes C11 . H16 . 0.951 no C12 . C13 . 1.3873(17) yes C12 . H17 . 0.933 no C13 . C14 . 1.3879(17) yes C13 . H18 . 0.937 no C14 . C15 . 1.3892(14) yes C14 . H19 . 0.943 no C15 . H20 . 0.924 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C5 . 107.19(7) yes C2 . N1 . H23 . 124.3 no C5 . N1 . H23 . 128.5 no N1 . C2 . C3 . 105.70(8) yes N1 . C2 . H24 . 123.3 no C3 . C2 . H24 . 131.0 no C2 . C3 . N4 . 110.40(8) yes C2 . C3 . H25 . 125.2 no N4 . C3 . H25 . 124.3 no C3 . N4 . C5 . 104.57(8) yes N1 . C5 . N4 . 112.13(8) yes N1 . C5 . N6 . 125.25(8) yes N4 . C5 . N6 . 122.61(8) yes C5 . N6 . C7 . 123.82(7) yes C5 . N6 . H22 . 119.6 no C7 . N6 . H22 . 116.4 no N6 . C7 . O8 . 122.85(8) yes N6 . C7 . N9 . 112.03(8) yes O8 . C7 . N9 . 125.12(8) yes C7 . N9 . C10 . 125.45(8) yes C7 . N9 . H21 . 116.6 no C10 . N9 . H21 . 117.8 no N9 . C10 . C11 . 122.17(8) yes N9 . C10 . C15 . 118.01(8) yes C11 . C10 . C15 . 119.73(9) yes C10 . C11 . C12 . 119.65(9) yes C10 . C11 . H16 . 119.0 no C12 . C11 . H16 . 121.4 no C11 . C12 . C13 . 120.79(10) yes C11 . C12 . H17 . 120.1 no C13 . C12 . H17 . 119.1 no C12 . C13 . C14 . 119.37(9) yes C12 . C13 . H18 . 121.4 no C14 . C13 . H18 . 119.3 no C13 . C14 . C15 . 120.41(10) yes C13 . C14 . H19 . 120.2 no C15 . C14 . H19 . 119.3 no C10 . C15 . C14 . 120.03(10) yes C10 . C15 . H20 . 118.6 no C14 . C15 . H20 . 121.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N6 . H22 . N4 3_556 161 0.87 2.06 2.893(2) yes N1 . H23 . O8 2_567 153 0.88 2.07 2.891(2) yes # Attachment 'yml59_histaPhuree.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 651228' _audit_creation_date 07-05-29 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title yml59 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.3860(10) _cell_length_b 11.4412(4) _cell_length_c 27.4207(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2944.6(3) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pcab ' _symmetry_space_group_name_Hall '-P 2bc 2ac' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y,z+1/2 x+1/2,-y,-z+1/2 x+1/2,-y+1/2,z -x+1/2,y+1/2,-z -x,-y+1/2,z+1/2 x,y+1/2,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C14 H17 N5 O1 # Dc = 1.22 Fooo = 1152.00 Mu = 0.82 M = 271.32 # Found Formula = C14 H17 N5 O1 # Dc = 1.22 FOOO = 1152.00 Mu = 0.82 M = 271.32 _chemical_formula_sum 'C14 H17 N5 O1' _chemical_formula_moiety 'C12 H14 N4 O, C2 H3 N' _chemical_compound_source ? _chemical_formula_weight 271.32 _cell_measurement_reflns_used 6426 _cell_measurement_theta_min 4.0784 _cell_measurement_theta_max 28.5629 _cell_measurement_temperature 175 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.70 _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.082 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; AbsPack - CrysAlis RED (Oxford Diffraction, 2002) ; _exptl_absorpt_correction_T_min 0.86786 _exptl_absorpt_correction_T_max 1.00000 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_number '4 frames' _diffrn_standards_interval_time 30 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 175 _diffrn_reflns_number 12019 _reflns_number_total 3766 _diffrn_reflns_av_R_equivalents 0.022 # Number of reflections with Friedels Law is 3373 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3766 _diffrn_reflns_theta_min 4.089 _diffrn_reflns_theta_max 28.593 _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 26.019 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _reflns_limit_h_min 0 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 35 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.22 _refine_diff_density_max 0.26 _refine_ls_number_reflns 2127 _refine_ls_number_restraints 0 _refine_ls_number_parameters 181 #_refine_ls_R_factor_ref 0.0453 _refine_ls_wR_factor_ref 0.0442 _refine_ls_goodness_of_fit_ref 1.0831 #_reflns_number_all 3373 _refine_ls_R_factor_all 0.0776 _refine_ls_wR_factor_all 0.0472 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 2127 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_gt 0.0442 _refine_ls_shift/su_max 0.010181 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 8.74 -10.6 -0.324 0.770 -6.26 ; _refine_special_details ; All atoms were refined anisotropically. Positional coordinated of the hydrogen atoms were refined independently ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens H21 H 0.6200 1.3144 0.0303 0.0500 1.0000 Uiso R . . . . . H22 H 0.4026 1.2756 0.0752 0.0500 1.0000 Uiso R . . . . . H23 H 0.4257 1.1322 0.1372 0.0500 1.0000 Uiso R . . . . . H24 H 0.8115 1.0563 0.1455 0.0500 1.0000 Uiso R . . . . . H25 H 0.6707 1.0043 0.1642 0.0500 1.0000 Uiso R . . . . . H26 H 0.6413 0.8909 0.0976 0.0500 1.0000 Uiso R . . . . . H27 H 0.7988 0.9384 0.0746 0.0500 1.0000 Uiso R . . . . . H28 H 0.9267 0.8228 0.1193 0.0500 1.0000 Uiso R . . . . . H29 H 0.9396 0.6812 0.1678 0.0500 1.0000 Uiso R . . . . . H30 H 0.9786 0.5437 0.2349 0.0391 1.0000 Uiso R . . . . . H31 H 0.9373 0.3562 0.2653 0.0492 1.0000 Uiso R . . . . . H32 H 0.7382 0.2501 0.2390 0.0493 1.0000 Uiso R . . . . . H33 H 0.5813 0.3325 0.1828 0.0439 1.0000 Uiso R . . . . . H34 H 0.6226 0.5197 0.1515 0.0359 1.0000 Uiso R . . . . . H35 H 0.8352 0.5040 0.0644 0.0925 1.0000 Uiso R . . . . . H36 H 0.8849 0.6265 0.0471 0.0925 1.0000 Uiso R . . . . . H37 H 0.8466 0.5311 0.0091 0.0925 1.0000 Uiso R . . . . . N1 N 0.70726(14) 1.18312(13) 0.07343(5) 0.0351 1.0000 Uani . . . . . . C2 C 0.60882(17) 1.25537(16) 0.05682(7) 0.0364 1.0000 Uani . . . . . . N3 N 0.48506(14) 1.24169(12) 0.07995(5) 0.0325 1.0000 Uani . . . . . . C4 C 0.50465(17) 1.15518(14) 0.11392(6) 0.0312 1.0000 Uani . . . . . . C5 C 0.64184(16) 1.11986(13) 0.10979(6) 0.0283 1.0000 Uani . . . . . . C6 C 0.71980(18) 1.02467(14) 0.13581(6) 0.0347 1.0000 Uani . . . . . . C7 C 0.74425(19) 0.92101(15) 0.10229(7) 0.0363 1.0000 Uani . . . . . . N8 N 0.82140(15) 0.82501(12) 0.12504(6) 0.0361 1.0000 Uani . . . . . . C9 C 0.75443(17) 0.73968(13) 0.14968(6) 0.0275 1.0000 Uani . . . . . . O10 O 0.62377(11) 0.73505(10) 0.15479(4) 0.0341 1.0000 Uani . . . . . . N11 N 0.84498(13) 0.65736(11) 0.16861(5) 0.0289 1.0000 Uani . . . . . . C12 C 0.80692(16) 0.54923(13) 0.18944(6) 0.0262 1.0000 Uani . . . . . . C13 C 0.68712(17) 0.48650(14) 0.17433(6) 0.0301 1.0000 Uani . . . . . . C14 C 0.66261(19) 0.37557(15) 0.19310(6) 0.0362 1.0000 Uani . . . . . . C15 C 0.7552(2) 0.32661(15) 0.22662(7) 0.0415 1.0000 Uani . . . . . . C16 C 0.8733(2) 0.38952(17) 0.24205(6) 0.0410 1.0000 Uani . . . . . . C17 C 0.89807(17) 0.50039(15) 0.22370(6) 0.0327 1.0000 Uani . . . . . . N18 N 0.5661(3) 0.6334(4) 0.04059(9) 0.1080 1.0000 Uani . . . . . . C19 C 0.6787(3) 0.6018(3) 0.04005(8) 0.0669 1.0000 Uani . . . . . . C20 C 0.8244(3) 0.5632(3) 0.04000(10) 0.0773 1.0000 Uani . . . . . . 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 N1 0.0226(6) 0.0367(7) 0.0460(8) 0.0063(6) 0.0018(6) -0.0005(6) C2 0.0267(8) 0.0352(8) 0.0474(9) 0.0080(8) 0.0007(7) -0.0001(7) N3 0.0211(6) 0.0305(7) 0.0460(8) -0.0004(6) -0.0009(6) 0.0014(5) C4 0.0264(7) 0.0287(7) 0.0384(8) -0.0003(7) 0.0024(7) -0.0038(7) C5 0.0248(7) 0.0252(7) 0.0348(8) -0.0034(6) -0.0006(6) -0.0039(6) C6 0.0330(8) 0.0328(8) 0.0384(8) 0.0041(7) -0.0032(7) 0.0018(7) C7 0.0333(8) 0.0302(7) 0.0453(10) 0.0054(7) -0.0010(7) 0.0048(7) N8 0.0232(6) 0.0319(7) 0.0531(8) 0.0071(6) -0.0003(6) 0.0029(6) C9 0.0206(7) 0.0266(7) 0.0354(7) -0.0064(7) -0.0021(6) 0.0016(6) O10 0.0169(5) 0.0324(6) 0.0528(7) -0.0029(5) -0.0019(5) 0.0032(5) N11 0.0164(5) 0.0248(6) 0.0455(8) 0.0005(6) -0.0008(5) -0.0001(5) C12 0.0228(7) 0.0245(7) 0.0314(7) -0.0054(6) 0.0049(6) 0.0025(6) C13 0.0239(7) 0.0293(8) 0.0370(8) -0.0039(7) 0.0010(6) -0.0013(6) C14 0.0347(8) 0.0301(8) 0.0438(9) -0.0073(7) 0.0077(7) -0.0074(7) C15 0.0529(10) 0.0316(8) 0.0400(9) 0.0043(7) 0.0113(9) -0.0027(9) C16 0.0458(10) 0.0438(10) 0.0333(9) 0.0054(8) 0.0002(7) 0.0059(9) C17 0.0310(8) 0.0362(8) 0.0309(8) -0.0039(7) 0.0009(6) 0.0003(7) N18 0.0687(16) 0.192(3) 0.0638(15) 0.0140(18) 0.0056(12) 0.026(2) C19 0.0691(16) 0.0929(19) 0.0387(11) 0.0066(11) -0.0046(11) 0.0045(15) C20 0.0829(19) 0.0890(19) 0.0602(15) 0.0073(13) -0.0160(14) 0.0251(16) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.018(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag H21 . C2 . 0.998 no H22 . N3 . 0.876 no H23 . C4 . 1.013 no H24 . C6 . 0.970 no H25 . C6 . 0.935 no H26 . C7 . 1.034 no H27 . C7 . 0.937 no H28 . N8 . 1.001 no H29 . N11 . 0.929 no H30 . C17 . 0.955 no H31 . C16 . 0.955 no H32 . C15 . 0.952 no H33 . C14 . 0.952 no H34 . C13 . 0.950 no H35 . C20 . 0.957 no H36 . C20 . 0.941 no H37 . C20 . 0.947 no N1 . C2 . 1.321(2) yes N1 . C5 . 1.377(2) yes C2 . N3 . 1.333(2) yes N3 . C4 . 1.371(2) yes C4 . C5 . 1.354(2) yes C5 . C6 . 1.493(2) yes C6 . C7 . 1.518(2) yes C7 . N8 . 1.456(2) yes N8 . C9 . 1.343(2) yes C9 . O10 . 1.2355(19) yes C9 . N11 . 1.371(2) yes N11 . C12 . 1.409(2) yes C12 . C13 . 1.397(2) yes C12 . C17 . 1.388(2) yes C13 . C14 . 1.389(2) yes C14 . C15 . 1.383(3) yes C15 . C16 . 1.388(3) yes C16 . C17 . 1.384(3) yes N18 . C19 . 1.117(4) yes C19 . C20 . 1.438(4) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C5 . 105.48(13) yes H21 . C2 . N1 . 127.0 no H21 . C2 . N3 . 121.2 no N1 . C2 . N3 . 111.84(15) yes C2 . N3 . H22 . 130.4 no C2 . N3 . C4 . 106.92(13) yes H22 . N3 . C4 . 122.6 no H23 . C4 . N3 . 121.2 no H23 . C4 . C5 . 132.1 no N3 . C4 . C5 . 106.63(14) yes N1 . C5 . C4 . 109.13(14) yes N1 . C5 . C6 . 120.72(14) yes C4 . C5 . C6 . 130.05(15) yes C5 . C6 . H24 . 107.1 no C5 . C6 . H25 . 109.8 no H24 . C6 . H25 . 107.6 no C5 . C6 . C7 . 110.77(13) yes H24 . C6 . C7 . 108.8 no H25 . C6 . C7 . 112.6 no C6 . C7 . H26 . 101.3 no C6 . C7 . H27 . 114.1 no H26 . C7 . H27 . 118.7 no C6 . C7 . N8 . 113.90(14) yes H26 . C7 . N8 . 105.5 no H27 . C7 . N8 . 103.6 no C7 . N8 . H28 . 116.2 no C7 . N8 . C9 . 122.07(14) yes H28 . N8 . C9 . 121.6 no N8 . C9 . O10 . 123.55(15) yes N8 . C9 . N11 . 113.55(14) yes O10 . C9 . N11 . 122.90(15) yes H29 . N11 . C9 . 112.4 no H29 . N11 . C12 . 120.7 no C9 . N11 . C12 . 126.85(13) yes N11 . C12 . C13 . 122.35(14) yes N11 . C12 . C17 . 118.14(14) yes C13 . C12 . C17 . 119.35(15) yes H34 . C13 . C12 . 120.2 no H34 . C13 . C14 . 120.3 no C12 . C13 . C14 . 119.53(16) yes H33 . C14 . C13 . 119.7 no H33 . C14 . C15 . 119.4 no C13 . C14 . C15 . 120.83(16) yes H32 . C15 . C14 . 120.2 no H32 . C15 . C16 . 120.2 no C14 . C15 . C16 . 119.62(16) yes H31 . C16 . C15 . 119.9 no H31 . C16 . C17 . 120.2 no C15 . C16 . C17 . 119.89(17) yes H30 . C17 . C12 . 119.8 no H30 . C17 . C16 . 119.4 no C12 . C17 . C16 . 120.76(16) yes N18 . C19 . C20 . 178.8(4) yes C19 . C20 . H35 . 108.5 no C19 . C20 . H37 . 109.2 no H35 . C20 . H37 . 109.1 no C19 . C20 . H36 . 109.7 no H35 . C20 . H36 . 109.7 no H37 . C20 . H36 . 110.6 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N3 . H22 . N1 5_475 166 0.88 1.89 2.751(2) yes N8 . H28 . O10 5_565 140 1.00 2.19 3.032(2) yes N11 . H29 . O10 5_565 165 0.93 2.01 2.916(2) yes # Attachment 'mdbm17_p21c.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 676075' _audit_creation_date 07-05-31 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'mdbm17 in P 21/n' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.6630(18) _cell_length_b 6.0080(10) _cell_length_c 17.365(2) _cell_angle_alpha 90 _cell_angle_beta 129.922(8) _cell_angle_gamma 90 _cell_volume 933.2(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0010 0.0007 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 ; International Tables Vol C 4.2.6.8 and 6.1.1.4, dispersion factors from Interpolated values from CXRO/LLNL data ; H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 ; International Tables Vol C 4.2.6.8 and 6.1.1.4, dispersion factors from Interpolated values from CXRO/LLNL data ; N 0.0028 0.0016 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 ; International Tables Vol C 4.2.6.8 and 6.1.1.4, dispersion factors from Interpolated values from CXRO/LLNL data ; O 0.0046 0.0029 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 ; International Tables Vol C 4.2.6.8 and 6.1.1.4, dispersion factors from Interpolated values from CXRO/LLNL data ; _cell_formula_units_Z 4 # Given Formula = C13 H25 N2 O1 # Dc = 1.60 Fooo = 424.00 Mu = 1.01 M = 225.35 # Found Formula = C10 H10 N4 O1 # Dc = 1.44 FOOO = 424.00 Mu = 1.00 M = 202.22 _chemical_formula_sum 'C10 H10 N4 O1' _chemical_formula_moiety 'C10 H10 N4 O1' _chemical_compound_source ? _chemical_formula_weight 202.22 _cell_measurement_reflns_used 8192 _cell_measurement_theta_min 2 _cell_measurement_theta_max 13 _cell_measurement_temperature 120 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_min 0.1 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.100 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_radiation_monochromator graphite _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.51091 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SMART (Siemens, 1993)' _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 8098 _reflns_number_total 2532 _diffrn_reflns_av_R_equivalents 0.079 # Number of reflections with Friedels Law is 2532 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2678 _diffrn_reflns_theta_min 2.674 _diffrn_reflns_theta_max 20.945 _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 20.526 _diffrn_measured_fraction_theta_full 0.954 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -16 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.38 _refine_diff_density_max 0.46 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 2365 _refine_ls_number_restraints 0 _refine_ls_number_parameters 136 _oxford_refine_ls_R_factor_ref 0.0552 _refine_ls_wR_factor_ref 0.0560 _refine_ls_goodness_of_fit_ref 0.9396 _refine_ls_shift/su_max 0.000233 # The values computed from all data _oxford_reflns_number_all 2532 _refine_ls_R_factor_all 0.0576 _refine_ls_wR_factor_all 0.0569 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2365 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_gt 0.0560 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.07 1.90 1.79 0.620 0.428 ; _refine_special_details ; All atoms were refined anisotropically. Positional coordinated of the hydrogen atoms were initially refined with soft restraints on their angles and distances in order to optimise their geometries. After that they were treated as riding on their parent atoms. ; _publ_section_references ; Burla, M. C., Camalli, M. B., Carrozzini, G. L. , Cascarano, R., Giacovazzo, C., Polidori, G., \& Spagna, R. J. Appl. Crystallogr., 2003, 36, 1103. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Siemens Industrial Automation, Inc (1993). SMART: Area-Detector Software Package; Madison, WI. Siemens Industrial Automation, Inc (1995). SAINT: Area-Detector Integration Software.; Madison, WI. Siemens Industrial Automation, Inc (1996). SADABS: Area-Detector Absorption Correction;: Madison, WI. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N 0.12935(8) 0.81676(12) 0.10627(5) 0.0123 1.0000 Uani . . . . . . . C2 C 0.11889(10) 1.01916(14) 0.13957(7) 0.0133 1.0000 Uani . . . . . . . C3 C 0.26150(10) 1.08441(14) 0.21406(7) 0.0135 1.0000 Uani . . . . . . . N4 N 0.36156(8) 0.92838(12) 0.22787(5) 0.0124 1.0000 Uani . . . . . . . C5 C 0.27558(9) 0.77155(14) 0.16067(6) 0.0098 1.0000 Uani . . . . . . . N6 N 0.33311(8) 0.58418(12) 0.15044(5) 0.0116 1.0000 Uani . . . . . . . C7 C 0.25618(9) 0.45858(14) 0.06386(6) 0.0107 1.0000 Uani . . . . . . . O8 O 0.12292(7) 0.48309(12) -0.00621(5) 0.0155 1.0000 Uani . . . . . . . N9 N 0.34666(8) 0.30784(12) 0.06685(5) 0.0128 1.0000 Uani . . . . . . . C10 C 0.30017(10) 0.15227(14) -0.00906(6) 0.0121 1.0000 Uani . . . . . . . C11 C 0.19056(11) 0.20175(15) -0.11063(7) 0.0159 1.0000 Uani . . . . . . . C12 C 0.15299(12) 0.04460(18) -0.18238(7) 0.0196 1.0000 Uani . . . . . . . C13 C 0.22440(13) -0.16012(17) -0.15406(8) 0.0222 1.0000 Uani . . . . . . . C14 C 0.33537(13) -0.20734(16) -0.05278(9) 0.0218 1.0000 Uani . . . . . . . C15 C 0.37320(11) -0.05255(15) 0.01961(7) 0.0167 1.0000 Uani . . . . . . . H16 H 0.1430 0.3432 -0.1294 0.0500 1.0000 Uiso R . . . . . . H17 H 0.0774 0.0748 -0.2504 0.0500 1.0000 Uiso R . . . . . . H18 H 0.1990 -0.2677 -0.2018 0.0500 1.0000 Uiso R . . . . . . H19 H 0.3878 -0.3433 -0.0325 0.0500 1.0000 Uiso R . . . . . . H20 H 0.4500 -0.0790 0.0871 0.0500 1.0000 Uiso R . . . . . . H21 H 0.4414 0.3023 0.1234 0.0500 1.0000 Uiso R . . . . . . H22 H 0.4258 0.5473 0.1984 0.0500 1.0000 Uiso R . . . . . . H23 H 0.0518 0.7348 0.0593 0.0500 1.0000 Uiso R . . . . . . H24 H 0.0249 1.0878 0.1125 0.0500 1.0000 Uiso R . . . . . . H25 H 0.2901 1.2189 0.2505 0.0500 1.0000 Uiso 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 N1 0.0076(3) 0.0126(3) 0.0112(3) -0.0026(2) 0.0035(3) -0.0007(2) C2 0.0125(4) 0.0120(4) 0.0139(4) -0.0002(3) 0.0078(3) 0.0014(3) C3 0.0140(4) 0.0110(4) 0.0156(4) -0.0023(3) 0.0095(3) -0.0022(3) N4 0.0093(3) 0.0119(3) 0.0124(3) -0.0031(2) 0.0054(3) -0.0032(2) C5 0.0085(3) 0.0100(4) 0.0085(3) -0.0002(3) 0.0043(3) -0.0013(3) N6 0.0075(3) 0.0114(3) 0.0097(3) -0.0016(2) 0.0026(3) 0.0006(2) C7 0.0095(4) 0.0103(3) 0.0113(3) -0.0016(3) 0.0063(3) -0.0020(3) O8 0.0074(3) 0.0186(3) 0.0142(3) -0.0056(2) 0.0041(3) -0.0021(2) N9 0.0098(3) 0.0126(3) 0.0113(3) -0.0021(2) 0.0046(3) 0.0011(2) C10 0.0125(4) 0.0109(4) 0.0148(4) -0.0019(3) 0.0097(3) -0.0022(3) C11 0.0152(4) 0.0155(4) 0.0145(4) -0.0023(3) 0.0083(3) -0.0017(3) C12 0.0200(5) 0.0233(5) 0.0168(4) -0.0073(3) 0.0125(4) -0.0076(3) C13 0.0312(5) 0.0177(4) 0.0292(5) -0.0110(4) 0.0247(5) -0.0097(4) C14 0.0314(5) 0.0119(4) 0.0334(5) -0.0016(4) 0.0260(5) -0.0001(3) C15 0.0212(5) 0.0126(4) 0.0219(4) 0.0021(3) 0.0163(4) 0.0012(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.079(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C2 . 1.3850(11) yes N1 . C5 . 1.3443(11) yes N1 . H23 . 0.883 no C2 . C3 . 1.3535(12) yes C2 . H24 . 0.966 no C3 . N4 . 1.3924(12) yes C3 . H25 . 0.945 no N4 . C5 . 1.3241(10) yes C5 . N6 . 1.3791(11) yes N6 . C7 . 1.3798(10) yes N6 . H22 . 0.869 no C7 . O8 . 1.2208(11) yes C7 . N9 . 1.3661(11) yes N9 . C10 . 1.4099(11) yes N9 . H21 . 0.891 no C10 . C11 . 1.3927(12) yes C10 . C15 . 1.3940(12) yes C11 . C12 . 1.3910(13) yes C11 . H16 . 0.951 no C12 . C13 . 1.3866(16) yes C12 . H17 . 0.932 no C13 . C14 . 1.3882(16) yes C13 . H18 . 0.937 no C14 . C15 . 1.3885(14) yes C14 . H19 . 0.943 no C15 . H20 . 0.923 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C5 . 107.21(7) yes C2 . N1 . H23 . 124.3 no C5 . N1 . H23 . 128.5 no N1 . C2 . C3 . 105.66(8) yes N1 . C2 . H24 . 123.3 no C3 . C2 . H24 . 131.1 no C2 . C3 . N4 . 110.47(8) yes C2 . C3 . H25 . 125.2 no N4 . C3 . H25 . 124.3 no C3 . N4 . C5 . 104.49(7) yes N1 . C5 . N4 . 112.16(8) yes N1 . C5 . N6 . 125.25(7) yes N4 . C5 . N6 . 122.58(8) yes C5 . N6 . C7 . 123.84(7) yes C5 . N6 . H22 . 119.6 no C7 . N6 . H22 . 116.3 no N6 . C7 . O8 . 122.80(8) yes N6 . C7 . N9 . 112.02(7) yes O8 . C7 . N9 . 125.18(8) yes C7 . N9 . C10 . 125.43(7) yes C7 . N9 . H21 . 116.6 no C10 . N9 . H21 . 117.8 no N9 . C10 . C11 . 122.16(8) yes N9 . C10 . C15 . 118.10(8) yes C11 . C10 . C15 . 119.64(8) yes C10 . C11 . C12 . 119.67(9) yes C10 . C11 . H16 . 118.9 no C12 . C11 . H16 . 121.4 no C11 . C12 . C13 . 120.81(10) yes C11 . C12 . H17 . 120.1 no C13 . C12 . H17 . 119.1 no C12 . C13 . C14 . 119.34(9) yes C12 . C13 . H18 . 121.4 no C14 . C13 . H18 . 119.2 no C13 . C14 . C15 . 120.42(9) yes C13 . C14 . H19 . 120.3 no C15 . C14 . H19 . 119.3 no C10 . C15 . C14 . 120.10(9) yes C10 . C15 . H20 . 118.6 no C14 . C15 . H20 . 121.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N9 . H21 . N4 3_645 154 0.89 2.22 3.0401(16) yes N6 . H22 . N4 3_645 161 0.87 2.06 2.8921(16) yes N1 . H23 . O8 2_565 153 0.88 2.07 2.8913(16) yes _vrf_DIFF020_CRYSTALS_cif ; PROBLEM: _diffrn_standards_interval_count and RESPONSE: synchrotron measurement; monitor counts are used to correct for decay ; _vrf_DIFF022_CRYSTALS_cif ; PROBLEM: _diffrn_standards_decay_% is missing RESPONSE: synchrotron measurement; monitor counts are used to correct for decay ; # Attachment 'yml59_pbca.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 676076' _audit_creation_date 07-05-29 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title yml59 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 11.4412(4) _cell_length_b 9.3860(10) _cell_length_c 27.4207(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2944.6(3) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 x+1/2,y,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C14 H17 N5 O1 # Dc = 1.22 Fooo = 1152.00 Mu = 0.82 M = 271.32 # Found Formula = C14 H17 N5 O1 # Dc = 1.22 FOOO = 1152.00 Mu = 0.82 M = 271.32 _chemical_formula_sum 'C14 H17 N5 O1' _chemical_formula_moiety 'C12 H14 N4 O, C2 H3 N' _chemical_compound_source ? _chemical_formula_weight 271.32 _cell_measurement_reflns_used 6426 _cell_measurement_theta_min 4.0784 _cell_measurement_theta_max 28.5629 _cell_measurement_temperature 175 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.70 _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.082 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; AbsPack - CrysAlis RED (Oxford Diffraction, 2002) ; _exptl_absorpt_correction_T_min 0.86786 _exptl_absorpt_correction_T_max 1.00000 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_number '4 frames' _diffrn_standards_interval_time 30 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 175 _diffrn_reflns_number 12019 _reflns_number_total 3766 _diffrn_reflns_av_R_equivalents 0.022 # Number of reflections with Friedels Law is 3373 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3766 _diffrn_reflns_theta_min 4.089 _diffrn_reflns_theta_max 28.593 _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 26.019 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _reflns_limit_h_min 0 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 35 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.28 _refine_diff_density_max 0.27 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 2708 _refine_ls_number_restraints 0 _refine_ls_number_parameters 181 _oxford_refine_ls_R_factor_ref 0.0607 _refine_ls_wR_factor_ref 0.0506 _refine_ls_goodness_of_fit_ref 1.0708 _refine_ls_shift/su_max 0.000287 # The values computed from all data _oxford_reflns_number_all 3373 _refine_ls_R_factor_all 0.0772 _refine_ls_wR_factor_all 0.0519 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2708 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_gt 0.0506 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 12.8 5.92 10.1 4.69 ; _refine_special_details ; All atoms were refined anisotropically. Positional coordinated of the hydrogen atoms were initially refined with soft restraints on their angles and distances in order to optimise their geometries. After that they were treated as riding on their parent atoms. ; _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. M. C. Burla, M. B. Camalli, G. L. Carrozzini, R. Cascarano, C. Giacovazzo, G. Polidori and R. Spagna, J. Appl. Crystallogr., 2003, 36, 1103. Oxford Diffraction, (2002) CrysAlis RED. Oxford Diffraction, (2002) Xcalibur User Manual Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N -0.18312(12) 0.70717(13) 0.07342(5) 0.0352 1.0000 Uani . . . . . . . C2 C -0.25543(14) 0.60869(16) 0.05687(6) 0.0362 1.0000 Uani . . . . . . . N3 N -0.24171(11) 0.48506(13) 0.07997(5) 0.0324 1.0000 Uani . . . . . . . C4 C -0.15522(13) 0.50467(16) 0.11389(6) 0.0314 1.0000 Uani . . . . . . . C5 C -0.11998(12) 0.64186(15) 0.10985(5) 0.0280 1.0000 Uani . . . . . . . C6 C -0.02460(13) 0.71982(17) 0.13594(6) 0.0347 1.0000 Uani . . . . . . . C7 C 0.07904(13) 0.74461(18) 0.10228(6) 0.0362 1.0000 Uani . . . . . . . N8 N 0.17495(11) 0.82147(13) 0.12504(5) 0.0359 1.0000 Uani . . . . . . . C9 C 0.26035(12) 0.75440(15) 0.14968(5) 0.0273 1.0000 Uani . . . . . . . O10 O 0.26491(9) 0.62373(10) 0.15477(4) 0.0339 1.0000 Uani . . . . . . . N11 N 0.34257(10) 0.84491(12) 0.16859(5) 0.0291 1.0000 Uani . . . . . . . C12 C 0.45066(12) 0.80675(14) 0.18943(5) 0.0259 1.0000 Uani . . . . . . . C13 C 0.51360(13) 0.68697(15) 0.17431(5) 0.0302 1.0000 Uani . . . . . . . C14 C 0.62446(13) 0.66280(17) 0.19308(6) 0.0358 1.0000 Uani . . . . . . . C15 C 0.67348(14) 0.7552(2) 0.22666(6) 0.0415 1.0000 Uani . . . . . . . C16 C 0.61069(15) 0.87307(19) 0.24199(6) 0.0407 1.0000 Uani . . . . . . . C17 C 0.49956(14) 0.89807(16) 0.22369(5) 0.0326 1.0000 Uani . . . . . . . N18 N 0.3665(3) 0.5661(3) 0.04060(8) 0.1075 1.0000 Uani . . . . . . . C19 C 0.3979(3) 0.6790(3) 0.04007(7) 0.0668 1.0000 Uani . . . . . . . C20 C 0.4370(3) 0.8239(3) 0.04011(9) 0.0754 1.0000 Uani . . . . . . . H21 H -0.3108 0.6213 0.0317 0.0500 1.0000 Uiso R . . . . . . H22 H -0.2756 0.4026 0.0752 0.0500 1.0000 Uiso R . . . . . . H23 H -0.1297 0.4331 0.1352 0.0500 1.0000 Uiso R . . . . . . H24 H -0.0550 0.8125 0.1465 0.0500 1.0000 Uiso R . . . . . . H25 H -0.0016 0.6660 0.1648 0.0500 1.0000 Uiso R . . . . . . H26 H 0.1081 0.6515 0.0925 0.0500 1.0000 Uiso R . . . . . . H27 H 0.0552 0.7972 0.0737 0.0500 1.0000 Uiso R . . . . . . H28 H 0.1772 0.9268 0.1193 0.0500 1.0000 Uiso R . . . . . . H29 H 0.3187 0.9395 0.1678 0.0500 1.0000 Uiso R . . . . . . H30 H 0.4556 0.9782 0.2341 0.0500 1.0000 Uiso R . . . . . . H31 H 0.6422 0.9375 0.2655 0.0500 1.0000 Uiso R . . . . . . H32 H 0.7500 0.7390 0.2394 0.0500 1.0000 Uiso R . . . . . . H33 H 0.6678 0.5800 0.1834 0.0500 1.0000 Uiso R . . . . . . H34 H 0.4807 0.6238 0.1514 0.0500 1.0000 Uiso R . . . . . . H35 H 0.4892 0.8394 0.0667 0.0500 1.0000 Uiso R . . . . . . H36 H 0.3710 0.8838 0.0440 0.0500 1.0000 Uiso R . . . . . . H37 H 0.4742 0.8460 0.0107 0.0500 1.0000 Uiso 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 N1 0.0366(7) 0.0224(6) 0.0466(8) 0.0020(5) -0.0064(6) 0.0008(5) C2 0.0354(8) 0.0260(7) 0.0471(8) 0.0010(6) -0.0084(7) -0.0003(6) N3 0.0304(6) 0.0211(6) 0.0457(7) -0.0007(5) 0.0004(6) -0.0015(5) C4 0.0292(7) 0.0265(7) 0.0384(7) 0.0025(6) 0.0000(6) 0.0034(6) C5 0.0247(6) 0.0250(7) 0.0343(7) -0.0002(5) 0.0030(6) 0.0039(5) C6 0.0325(8) 0.0328(8) 0.0387(8) -0.0037(6) -0.0036(6) -0.0022(6) C7 0.0302(7) 0.0336(8) 0.0448(9) -0.0030(7) -0.0055(7) -0.0045(7) N8 0.0314(6) 0.0235(6) 0.0528(8) 0.0003(6) -0.0072(6) -0.0032(5) C9 0.0261(6) 0.0207(6) 0.0350(7) -0.0023(5) 0.0066(6) -0.0008(5) O10 0.0324(6) 0.0173(5) 0.0520(6) -0.0018(4) 0.0028(5) -0.0031(4) N11 0.0247(6) 0.0160(5) 0.0465(7) -0.0005(5) -0.0005(5) 0.0001(5) C12 0.0249(6) 0.0221(6) 0.0307(7) 0.0047(5) 0.0050(5) -0.0022(5) C13 0.0295(7) 0.0241(7) 0.0369(7) 0.0016(6) 0.0040(6) 0.0016(6) C14 0.0295(7) 0.0345(8) 0.0435(8) 0.0077(7) 0.0067(6) 0.0069(6) C15 0.0318(8) 0.0527(10) 0.0398(8) 0.0114(8) -0.0039(7) 0.0022(8) C16 0.0431(9) 0.0455(9) 0.0334(8) 0.0004(7) -0.0056(7) -0.0053(8) C17 0.0359(8) 0.0309(7) 0.0310(7) 0.0010(6) 0.0038(6) -0.0002(6) N18 0.191(3) 0.0688(15) 0.0626(14) 0.0053(11) -0.0135(16) -0.0259(18) C19 0.0923(17) 0.0679(15) 0.0401(10) -0.0037(10) -0.0065(10) -0.0049(14) C20 0.0856(17) 0.0840(17) 0.0567(13) -0.0155(12) -0.0065(12) -0.0233(15) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.010(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C2 . 1.321(2) yes N1 . C5 . 1.3768(19) yes C2 . N3 . 1.3312(19) yes C2 . H21 . 0.944 no N3 . C4 . 1.371(2) yes N3 . H22 . 0.876 no C4 . C5 . 1.354(2) yes C4 . H23 . 0.937 no C5 . C6 . 1.496(2) yes C6 . C7 . 1.521(2) yes C6 . H24 . 0.980 no C6 . H25 . 0.976 no C7 . N8 . 1.4538(19) yes C7 . H26 . 0.973 no C7 . H27 . 0.966 no N8 . C9 . 1.3445(19) yes N8 . H28 . 1.001 no C9 . O10 . 1.2354(17) yes C9 . N11 . 1.3695(18) yes N11 . C12 . 1.4087(18) yes N11 . H29 . 0.929 no C12 . C13 . 1.398(2) yes C12 . C17 . 1.389(2) yes C13 . C14 . 1.387(2) yes C13 . H34 . 0.943 no C14 . C15 . 1.383(2) yes C14 . H33 . 0.959 no C15 . C16 . 1.385(3) yes C15 . H32 . 0.955 no C16 . C17 . 1.387(2) yes C16 . H31 . 0.954 no C17 . H30 . 0.949 no N18 . C19 . 1.118(3) yes C19 . C20 . 1.432(4) yes C20 . H35 . 0.954 no C20 . H36 . 0.947 no C20 . H37 . 0.936 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C5 . 105.44(12) yes N1 . C2 . N3 . 111.88(14) yes N1 . C2 . H21 . 125.7 no N3 . C2 . H21 . 122.4 no C2 . N3 . C4 . 106.91(12) yes C2 . N3 . H22 . 130.4 no C4 . N3 . H22 . 122.7 no N3 . C4 . C5 . 106.69(13) yes N3 . C4 . H23 . 123.5 no C5 . C4 . H23 . 129.8 no N1 . C5 . C4 . 109.06(13) yes N1 . C5 . C6 . 120.79(13) yes C4 . C5 . C6 . 130.04(14) yes C5 . C6 . C7 . 110.70(12) yes C5 . C6 . H24 . 108.4 no C7 . C6 . H24 . 108.7 no C5 . C6 . H25 . 109.3 no C7 . C6 . H25 . 111.2 no H24 . C6 . H25 . 108.4 no C6 . C7 . N8 . 113.83(13) yes C6 . C7 . H26 . 107.2 no N8 . C7 . H26 . 107.9 no C6 . C7 . H27 . 110.5 no N8 . C7 . H27 . 107.9 no H26 . C7 . H27 . 109.4 no C7 . N8 . C9 . 122.13(13) yes C7 . N8 . H28 . 116.2 no C9 . N8 . H28 . 121.5 no N8 . C9 . O10 . 123.53(13) yes N8 . C9 . N11 . 113.52(12) yes O10 . C9 . N11 . 122.96(13) yes C9 . N11 . C12 . 126.79(12) yes C9 . N11 . H29 . 112.5 no C12 . N11 . H29 . 120.7 no N11 . C12 . C13 . 122.44(13) yes N11 . C12 . C17 . 118.10(13) yes C13 . C12 . C17 . 119.30(14) yes C12 . C13 . C14 . 119.49(14) yes C12 . C13 . H34 . 119.8 no C14 . C13 . H34 . 120.7 no C13 . C14 . C15 . 121.00(15) yes C13 . C14 . H33 . 120.1 no C15 . C14 . H33 . 118.9 no C14 . C15 . C16 . 119.51(15) yes C14 . C15 . H32 . 121.0 no C16 . C15 . H32 . 119.5 no C15 . C16 . C17 . 120.06(16) yes C15 . C16 . H31 . 121.0 no C17 . C16 . H31 . 118.9 no C12 . C17 . C16 . 120.63(15) yes C12 . C17 . H30 . 118.6 no C16 . C17 . H30 . 120.8 no N18 . C19 . C20 . 179.1(3) yes C19 . C20 . H35 . 109.9 no C19 . C20 . H36 . 108.4 no H35 . C20 . H36 . 108.8 no C19 . C20 . H37 . 110.6 no H35 . C20 . H37 . 110.0 no H36 . C20 . H37 . 109.2 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N3 . H22 . N1 3_445 166 0.88 1.89 2.752(2) yes N8 . H28 . O10 3_555 140 1.00 2.19 3.031(2) yes N8 . H28 . N18 3_555 129 1.00 2.57 3.295(2) yes N11 . H29 . O10 3_555 165 0.93 2.01 2.916(2) yes