# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm #TrackingRef '- 1.cif' _journal_coden_Cambridge 1350 _publ_contact_author_name 'Edward RT Tiekink' _publ_contact_author_address ; Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia ; _publ_contact_author_phone ' +60 3 7967 6775 ' _publ_contact_author_fax ' +60 3 7967 4193 ' _publ_contact_author_email Edward.Tiekink@gmail.com loop_ _publ_author_footnote _publ_author_address ; Correspondence e-mail: Edward.Tiekink@gmail.com ; ; Department of Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia ; #TrackingRef '- 1.cif' _publ_section_title ; Structure of (1) ; _publ_author_name E.R.T.Tiekink data_h _database_code_depnum_ccdc_archive 'CCDC 882592' # TEXT _publ_section_abstract ; The structure of (1) is described. ; # start Validation Reply Form _vrf_PLAT910_h ; PROBLEM: Missing # of FCF Reflections Below Th(Min) ..... 1 RESPONSE: Theta min = 3.0 deg. The missing reflection is (0 0 2) which has a theta value of 2.0 deg. and therefore was excluded. ; _vrf_PLAT911_h ; PROBLEM: Missing # FCF Refl Between THmin & STh/L= 0.600 3 RESPONSE: These reflections were probably affected by unexpected deviations in their intensities for symmetry equivalent measurements and omitted during initial data reduction. ; _vrf_PLAT912_h ; PROBLEM: Missing # of FCF Reflections Above STh/L= 0.600 6 RESPONSE: Theta max for the refinement = 27.5 deg. If the refinement is truncated at theta max = 25.0, this alert does not persist. Hence, the reflections are probably reflections at or just beyond the requested theta(max) for the measurement. ; _vrf_PLAT913_h ; PROBLEM: Missing # of Very Strong Reflections in FCF .... 1 RESPONSE: This is most likely a low angle reflection, i.e. (0 0 2), outside of the limits 3.0 to 27.5 deg. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 N4 O' _chemical_formula_sum 'C10 H12 N4 O' _chemical_formula_weight 204.24 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' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.7842(19) _cell_length_b 7.258(2) _cell_length_c 21.155(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.751(8) _cell_angle_gamma 90.00 _cell_volume 1034.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4218 _cell_measurement_theta_min 2.8062 _cell_measurement_theta_max 30.6670 _exptl_crystal_description prism _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1312 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC12\K/SATURN724 _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1' _diffrn_reflns_number 25445 _diffrn_reflns_av_R_equivalents 0.0897 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2363 _reflns_number_gt 2320 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'CrystalClear (Rigaku Americas Corporation, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) & Brandenburg (Crystal Impact, 2006)' _computing_publication_material SHELXL97 _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^ > 2\s(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^)+(0.0739P)^2^+0.2983P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2363 _refine_ls_number_parameters 143 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1454 _refine_ls_wR_factor_gt 0.1449 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 0.78303(15) 0.40823(14) 0.54326(5) 0.0302(3) Uani 1 1 d D . . H1O H 0.707(3) 0.500(2) 0.5460(10) 0.045 Uiso 1 1 d D . . N1 N 0.43738(19) 0.27380(17) 0.44557(6) 0.0311(3) Uani 1 1 d . . . N2 N 0.33629(18) 0.13230(17) 0.41977(6) 0.0315(3) Uani 1 1 d . . . N3 N 0.47378(17) 0.00611(16) 0.40802(5) 0.0264(3) Uani 1 1 d . . . N4 N 0.41952(18) -0.16249(16) 0.37950(6) 0.0283(3) Uani 1 1 d D . . H4N H 0.347(2) -0.229(2) 0.4037(7) 0.034 Uiso 1 1 d D . . C1 C 0.7868(2) 0.3769(2) 0.47668(7) 0.0311(3) Uani 1 1 d . . . H1A H 0.9208 0.3339 0.4694 0.037 Uiso 1 1 calc R . . H1B H 0.7614 0.4948 0.4536 0.037 Uiso 1 1 calc R . . C2 C 0.6363(2) 0.23763(19) 0.45014(6) 0.0271(3) Uani 1 1 d . . . C3 C 0.6620(2) 0.06440(19) 0.42602(6) 0.0260(3) Uani 1 1 d . . . C4 C 0.8391(2) -0.0499(2) 0.41737(8) 0.0355(4) Uani 1 1 d . . . H4A H 0.8407 -0.1594 0.4445 0.053 Uiso 1 1 calc R . . H4B H 0.9599 0.0223 0.4292 0.053 Uiso 1 1 calc R . . H4C H 0.8333 -0.0877 0.3727 0.053 Uiso 1 1 calc R . . C5 C 0.3297(2) -0.15004(18) 0.31516(6) 0.0267(3) Uani 1 1 d . . . C6 C 0.4006(2) -0.0283(2) 0.27220(7) 0.0329(3) Uani 1 1 d . . . H6 H 0.5075 0.0525 0.2856 0.039 Uiso 1 1 calc R . . C7 C 0.3127(2) -0.0267(2) 0.20914(7) 0.0357(4) Uani 1 1 d . . . H7 H 0.3597 0.0563 0.1796 0.043 Uiso 1 1 calc R . . C8 C 0.1571(2) -0.1453(2) 0.18921(7) 0.0346(4) Uani 1 1 d . . . H8 H 0.0972 -0.1425 0.1463 0.042 Uiso 1 1 calc R . . C9 C 0.0894(2) -0.2681(2) 0.23221(7) 0.0359(4) Uani 1 1 d . . . H9 H -0.0158 -0.3506 0.2186 0.043 Uiso 1 1 calc R . . C10 C 0.1754(2) -0.2704(2) 0.29521(7) 0.0322(3) Uani 1 1 d . . . H10 H 0.1287 -0.3541 0.3246 0.039 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 O1 0.0365(6) 0.0289(5) 0.0249(5) -0.0022(4) 0.0024(4) -0.0029(4) N1 0.0329(6) 0.0292(6) 0.0314(6) -0.0044(5) 0.0041(5) -0.0032(5) N2 0.0297(6) 0.0296(6) 0.0356(7) -0.0060(5) 0.0048(5) -0.0005(5) N3 0.0280(6) 0.0244(6) 0.0267(6) -0.0020(4) 0.0030(5) -0.0027(4) N4 0.0337(6) 0.0238(6) 0.0274(6) -0.0021(4) 0.0031(5) -0.0059(4) C1 0.0366(8) 0.0312(7) 0.0258(7) -0.0015(5) 0.0047(6) -0.0091(6) C2 0.0312(7) 0.0280(7) 0.0222(6) 0.0007(5) 0.0035(5) -0.0044(5) C3 0.0273(7) 0.0278(7) 0.0227(6) 0.0023(5) 0.0021(5) -0.0036(5) C4 0.0299(7) 0.0344(8) 0.0416(9) -0.0028(6) 0.0014(6) 0.0004(6) C5 0.0284(7) 0.0254(6) 0.0267(7) -0.0032(5) 0.0044(5) 0.0000(5) C6 0.0339(7) 0.0316(7) 0.0332(8) 0.0004(6) 0.0047(6) -0.0059(6) C7 0.0418(8) 0.0367(8) 0.0300(8) 0.0033(6) 0.0098(6) -0.0013(6) C8 0.0380(8) 0.0400(8) 0.0259(7) -0.0044(6) 0.0041(6) 0.0036(6) C9 0.0357(8) 0.0397(8) 0.0319(8) -0.0081(6) 0.0022(6) -0.0067(6) C10 0.0352(8) 0.0320(7) 0.0299(7) -0.0026(5) 0.0062(6) -0.0069(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.4301(17) . ? O1 H1O 0.850(9) . ? N1 N2 1.3172(17) . ? N1 C2 1.3668(19) . ? N2 N3 1.3510(17) . ? N3 C3 1.3565(17) . ? N3 N4 1.3946(16) . ? N4 C5 1.4273(18) . ? N4 H4N 0.893(9) . ? C1 C2 1.4986(19) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.376(2) . ? C3 C4 1.489(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C10 1.3903(19) . ? C5 C6 1.393(2) . ? C6 C7 1.396(2) . ? C6 H6 0.9500 . ? C7 C8 1.388(2) . ? C7 H7 0.9500 . ? C8 C9 1.390(2) . ? C8 H8 0.9500 . ? C9 C10 1.391(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? 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 C1 O1 H1O 105.9(14) . . ? N2 N1 C2 109.95(12) . . ? N1 N2 N3 105.53(11) . . ? N2 N3 C3 112.60(12) . . ? N2 N3 N4 121.45(11) . . ? C3 N3 N4 125.94(12) . . ? N3 N4 C5 114.74(11) . . ? N3 N4 H4N 111.1(12) . . ? C5 N4 H4N 112.2(12) . . ? O1 C1 C2 112.70(11) . . ? O1 C1 H1A 109.1 . . ? C2 C1 H1A 109.1 . . ? O1 C1 H1B 109.1 . . ? C2 C1 H1B 109.1 . . ? H1A C1 H1B 107.8 . . ? N1 C2 C3 108.45(12) . . ? N1 C2 C1 121.37(13) . . ? C3 C2 C1 130.16(13) . . ? N3 C3 C2 103.47(12) . . ? N3 C3 C4 122.57(13) . . ? C2 C3 C4 133.96(13) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C10 C5 C6 120.38(13) . . ? C10 C5 N4 118.14(12) . . ? C6 C5 N4 121.38(12) . . ? C5 C6 C7 119.16(14) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? C8 C7 C6 120.62(14) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 119.78(14) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C8 120.07(14) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C5 119.97(14) . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? 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 C2 N1 N2 N3 -0.04(15) . . . . ? N1 N2 N3 C3 0.11(16) . . . . ? N1 N2 N3 N4 -179.01(11) . . . . ? N2 N3 N4 C5 66.22(16) . . . . ? C3 N3 N4 C5 -112.78(15) . . . . ? N2 N1 C2 C3 -0.04(16) . . . . ? N2 N1 C2 C1 178.79(12) . . . . ? O1 C1 C2 N1 68.12(17) . . . . ? O1 C1 C2 C3 -113.35(16) . . . . ? N2 N3 C3 C2 -0.13(15) . . . . ? N4 N3 C3 C2 178.94(12) . . . . ? N2 N3 C3 C4 -179.43(13) . . . . ? N4 N3 C3 C4 -0.4(2) . . . . ? N1 C2 C3 N3 0.10(15) . . . . ? C1 C2 C3 N3 -178.59(14) . . . . ? N1 C2 C3 C4 179.28(15) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? N3 N4 C5 C10 -142.60(13) . . . . ? N3 N4 C5 C6 40.93(18) . . . . ? C10 C5 C6 C7 1.0(2) . . . . ? N4 C5 C6 C7 177.42(13) . . . . ? C5 C6 C7 C8 -0.3(2) . . . . ? C6 C7 C8 C9 -0.6(2) . . . . ? C7 C8 C9 C10 0.9(2) . . . . ? C8 C9 C10 C5 -0.2(2) . . . . ? C6 C5 C10 C9 -0.8(2) . . . . ? N4 C5 C10 C9 -177.29(13) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.199 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.054 data_f _database_code_depnum_ccdc_archive 'CCDC 882593' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H11 F N4 O' _chemical_formula_sum 'C10 H11 F N4 O' _chemical_formula_weight 222.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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' _symmetry_space_group_name_Hall '-P 2yn ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.4975(6) _cell_length_b 6.6420(2) _cell_length_c 13.5534(6) _cell_angle_alpha 90.00 _cell_angle_beta 118.641(2) _cell_angle_gamma 90.00 _cell_volume 1066.39(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2595 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.858198 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on a \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_reflns_number 9414 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2434 _reflns_number_gt 2012 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0214P)^2^+1.0457P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2434 _refine_ls_number_parameters 152 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 F1 F 1.00646(13) 0.2349(2) 0.36412(14) 0.0617(5) Uani 1 1 d . . . O1 O 0.27601(11) 0.7972(2) 0.30373(11) 0.0304(3) Uani 1 1 d D . . H1O H 0.2176(14) 0.862(3) 0.2614(17) 0.046 Uiso 1 1 d D . . N1 N 0.42929(12) 0.4832(2) 0.32359(12) 0.0237(3) Uani 1 1 d . . . N2 N 0.51891(12) 0.3734(2) 0.38505(12) 0.0240(3) Uani 1 1 d . . . N3 N 0.60236(12) 0.5060(2) 0.44350(12) 0.0207(3) Uani 1 1 d . . . N4 N 0.71027(12) 0.4445(2) 0.51965(12) 0.0214(3) Uani 1 1 d D . . H4N H 0.7107(17) 0.361(3) 0.5711(13) 0.026 Uiso 1 1 d D . . C1 C 0.36802(14) 0.8401(3) 0.28354(15) 0.0246(4) Uani 1 1 d . . . H1A H 0.3992 0.9752 0.3130 0.030 Uiso 1 1 calc R . . H1B H 0.3427 0.8378 0.2018 0.030 Uiso 1 1 calc R . . C2 C 0.45549(14) 0.6824(3) 0.34223(14) 0.0211(4) Uani 1 1 d . . . C3 C 0.56741(14) 0.7006(3) 0.42033(14) 0.0210(4) Uani 1 1 d . . . C4 C 0.64307(16) 0.8736(3) 0.47539(17) 0.0313(4) Uani 1 1 d . . . H4A H 0.7092 0.8647 0.4637 0.047 Uiso 1 1 calc R . . H4B H 0.6676 0.8714 0.5561 0.047 Uiso 1 1 calc R . . H4C H 0.6025 0.9994 0.4428 0.047 Uiso 1 1 calc R . . C5 C 0.78066(15) 0.3848(3) 0.47435(15) 0.0226(4) Uani 1 1 d . . . C6 C 0.75570(17) 0.4285(3) 0.36475(16) 0.0309(4) Uani 1 1 d . . . H6 H 0.6865 0.4925 0.3152 0.037 Uiso 1 1 calc R . . C7 C 0.8326(2) 0.3782(3) 0.32763(19) 0.0411(5) Uani 1 1 d . . . H7 H 0.8168 0.4081 0.2529 0.049 Uiso 1 1 calc R . . C8 C 0.93106(19) 0.2851(3) 0.4004(2) 0.0396(5) Uani 1 1 d . . . C9 C 0.95756(18) 0.2402(3) 0.50926(19) 0.0364(5) Uani 1 1 d . . . H9 H 1.0268 0.1757 0.5580 0.044 Uiso 1 1 calc R . . C10 C 0.88172(16) 0.2904(3) 0.54668(16) 0.0283(4) Uani 1 1 d . . . H10 H 0.8987 0.2604 0.6217 0.034 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 F1 0.0663(10) 0.0659(10) 0.0858(11) -0.0138(8) 0.0628(9) 0.0011(8) O1 0.0208(6) 0.0347(8) 0.0344(7) 0.0151(6) 0.0121(6) 0.0093(5) N1 0.0196(7) 0.0237(8) 0.0239(7) 0.0007(6) 0.0073(6) 0.0005(6) N2 0.0206(7) 0.0209(7) 0.0252(7) -0.0013(6) 0.0068(6) -0.0007(6) N3 0.0177(7) 0.0202(7) 0.0187(7) -0.0005(6) 0.0044(6) 0.0002(6) N4 0.0165(7) 0.0248(8) 0.0183(7) 0.0029(6) 0.0046(6) 0.0046(6) C1 0.0201(8) 0.0270(9) 0.0233(9) 0.0049(7) 0.0077(7) 0.0031(7) C2 0.0206(8) 0.0212(8) 0.0199(8) 0.0008(7) 0.0085(7) 0.0005(7) C3 0.0221(8) 0.0193(8) 0.0192(8) -0.0006(7) 0.0080(7) 0.0014(7) C4 0.0267(10) 0.0213(9) 0.0345(10) -0.0045(8) 0.0056(8) -0.0030(7) C5 0.0227(9) 0.0190(8) 0.0261(9) -0.0026(7) 0.0116(7) -0.0007(7) C6 0.0329(10) 0.0312(10) 0.0288(10) -0.0020(8) 0.0149(8) -0.0012(8) C7 0.0525(14) 0.0416(12) 0.0398(12) -0.0057(10) 0.0307(11) -0.0042(11) C8 0.0430(12) 0.0366(11) 0.0560(14) -0.0120(10) 0.0372(11) -0.0041(10) C9 0.0299(10) 0.0305(10) 0.0513(13) -0.0047(9) 0.0214(10) 0.0038(8) C10 0.0274(9) 0.0258(9) 0.0311(10) -0.0014(8) 0.0136(8) 0.0026(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 F1 C8 1.367(2) . ? O1 C1 1.423(2) . ? O1 H1O 0.839(10) . ? N1 N2 1.313(2) . ? N1 C2 1.361(2) . ? N2 N3 1.348(2) . ? N3 C3 1.360(2) . ? N3 N4 1.3828(19) . ? N4 C5 1.413(2) . ? N4 H4N 0.888(9) . ? C1 C2 1.492(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.373(2) . ? C3 C4 1.480(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.387(3) . ? C5 C10 1.390(3) . ? C6 C7 1.394(3) . ? C6 H6 0.9500 . ? C7 C8 1.365(3) . ? C7 H7 0.9500 . ? C8 C9 1.373(3) . ? C9 C10 1.383(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? 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 C1 O1 H1O 112.7(17) . . ? N2 N1 C2 110.10(14) . . ? N1 N2 N3 105.45(14) . . ? N2 N3 C3 112.67(14) . . ? N2 N3 N4 122.03(14) . . ? C3 N3 N4 125.29(14) . . ? N3 N4 C5 116.46(13) . . ? N3 N4 H4N 112.2(13) . . ? C5 N4 H4N 114.4(13) . . ? O1 C1 C2 107.30(14) . . ? O1 C1 H1A 110.3 . . ? C2 C1 H1A 110.3 . . ? O1 C1 H1B 110.3 . . ? C2 C1 H1B 110.3 . . ? H1A C1 H1B 108.5 . . ? N1 C2 C3 108.70(15) . . ? N1 C2 C1 121.00(15) . . ? C3 C2 C1 130.29(16) . . ? N3 C3 C2 103.07(15) . . ? N3 C3 C4 122.86(15) . . ? C2 C3 C4 134.07(16) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C10 120.13(17) . . ? C6 C5 N4 122.55(16) . . ? C10 C5 N4 117.19(16) . . ? C5 C6 C7 119.70(19) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 118.9(2) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C7 C8 F1 119.0(2) . . ? C7 C8 C9 122.47(19) . . ? F1 C8 C9 118.6(2) . . ? C8 C9 C10 118.9(2) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 C5 119.90(18) . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? 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 C2 N1 N2 N3 0.30(19) . . . . ? N1 N2 N3 C3 0.01(19) . . . . ? N1 N2 N3 N4 178.86(14) . . . . ? N2 N3 N4 C5 80.3(2) . . . . ? C3 N3 N4 C5 -101.03(19) . . . . ? N2 N1 C2 C3 -0.5(2) . . . . ? N2 N1 C2 C1 -179.32(15) . . . . ? O1 C1 C2 N1 53.6(2) . . . . ? O1 C1 C2 C3 -124.89(19) . . . . ? N2 N3 C3 C2 -0.31(19) . . . . ? N4 N3 C3 C2 -179.11(15) . . . . ? N2 N3 C3 C4 178.91(16) . . . . ? N4 N3 C3 C4 0.1(3) . . . . ? N1 C2 C3 N3 0.48(19) . . . . ? C1 C2 C3 N3 179.14(17) . . . . ? N1 C2 C3 C4 -178.61(19) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? N3 N4 C5 C6 15.0(2) . . . . ? N3 N4 C5 C10 -169.20(15) . . . . ? C10 C5 C6 C7 -0.3(3) . . . . ? N4 C5 C6 C7 175.39(18) . . . . ? C5 C6 C7 C8 0.4(3) . . . . ? C6 C7 C8 F1 179.78(19) . . . . ? C6 C7 C8 C9 -0.4(3) . . . . ? C7 C8 C9 C10 0.2(3) . . . . ? F1 C8 C9 C10 -179.98(18) . . . . ? C8 C9 C10 C5 0.0(3) . . . . ? C6 C5 C10 C9 0.1(3) . . . . ? N4 C5 C10 C9 -175.83(17) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.235 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.051 # Attachment '- 3.cif' data_cl _database_code_depnum_ccdc_archive 'CCDC 882594' #TrackingRef '- 3.cif' # TEXT _publ_section_abstract ; The structure of (3) is described. ; # start Validation Reply Form _vrf_PLAT029_cl ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.969 RESPONSE: Evidently, a cusp of data was not collected. Given the high redundancy in the data collection (ca. 6) and acceptable data/parameter ratio (>15), this does not present a problem. ; _vrf_PLAT910_cl ; PROBLEM: Missing # of FCF Reflections Below Th(Min) ..... 1 RESPONSE: Theta min = 3.0 deg. The missing reflection is (1 0 0) which has a theta value of 1.7 deg. and therefore was excluded. ; _vrf_PLAT911_cl ; PROBLEM: Missing # FCF Refl Between THmin & STh/L= 0.600 5 RESPONSE: These reflections were probably affected by unexpected deviations in their intensities for symmetry equivalent measurements and omitted during initial data reduction. ; _vrf_PLAT912_cl ; PROBLEM: Missing # of FCF Reflections Above STh/L= 0.600 63 RESPONSE: Theta max for the refinement = 27.5 deg. If the refinement is truncated at theta max = 25.0, this alert reduces down to 3 missing reflections. Accoridngly, the missing cusp of reflections lies between 25.0 and 27.5 deg. The three remaining reflections are probably reflections at or just beyond the requested theta(max) for the measurement. ; _vrf_PLAT913_cl ; PROBLEM: Missing # of Very Strong Reflections in FCF .... 1 RESPONSE: This is most likely a low angle reflection, i.e. (1 0 0), outside of the limits 3.0 to 27.5 deg. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H11 Cl N4 O' _chemical_formula_sum 'C10 H11 Cl N4 O' _chemical_formula_weight 238.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.4984(8) _cell_length_b 6.6361(4) _cell_length_c 14.0835(5) _cell_angle_alpha 90.00 _cell_angle_beta 118.380(3) _cell_angle_gamma 90.00 _cell_volume 1109.93(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2670 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.769027 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker-Nonius Roper CCD camera on a \k-goniostat ; _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_number 15735 _diffrn_reflns_av_R_equivalents 0.0800 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2479 _reflns_number_gt 1694 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)' _computing_publication_material 'publCIF (Westrip, 2010)' _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^ > 2\s(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^)+(0.0620P)^2^+0.5670P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2479 _refine_ls_number_parameters 152 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 Cl1 Cl 1.14784(5) 0.24514(10) 1.00428(5) 0.0382(2) Uani 1 1 d . . . H1O H 0.458(2) 0.862(4) 0.2206(17) 0.057 Uiso 1 1 d D . . N1 N 0.59589(15) 0.4869(3) 0.42524(16) 0.0247(5) Uani 1 1 d . . . N2 N 0.62840(15) 0.3751(3) 0.51553(16) 0.0246(4) Uani 1 1 d . . . N3 N 0.65590(14) 0.5044(3) 0.60132(15) 0.0210(4) Uani 1 1 d . . . N4 N 0.68918(14) 0.4387(3) 0.70965(15) 0.0226(4) Uani 1 1 d D . . H4N H 0.6418(17) 0.355(3) 0.715(2) 0.027 Uiso 1 1 d D . . O1 O 0.47079(13) 0.7927(3) 0.27541(13) 0.0295(4) Uani 1 1 d D . . C1 C 0.57142(18) 0.8463(4) 0.36755(18) 0.0253(5) Uani 1 1 d . . . H1A H 0.5616 0.9773 0.3957 0.030 Uiso 1 1 calc R . . H1B H 0.6326 0.8608 0.3482 0.030 Uiso 1 1 calc R . . C2 C 0.60284(17) 0.6853(3) 0.45394(19) 0.0218(5) Uani 1 1 d . . . C3 C 0.64120(17) 0.6991(3) 0.56737(19) 0.0223(5) Uani 1 1 d . . . C4 C 0.6663(2) 0.8697(4) 0.6468(2) 0.0331(6) Uani 1 1 d . . . H4A H 0.6177 0.8578 0.6806 0.050 Uiso 1 1 calc R . . H4B H 0.6520 0.9988 0.6087 0.050 Uiso 1 1 calc R . . H4C H 0.7453 0.8630 0.7024 0.050 Uiso 1 1 calc R . . C5 C 0.79868(17) 0.3821(3) 0.77371(18) 0.0219(5) Uani 1 1 d . . . C6 C 0.87582(19) 0.4390(4) 0.7433(2) 0.0279(6) Uani 1 1 d . . . H6 H 0.8554 0.5044 0.6765 0.033 Uiso 1 1 calc R . . C7 C 0.98349(19) 0.3961(4) 0.8145(2) 0.0320(6) Uani 1 1 d . . . H7 H 1.0416 0.4329 0.7980 0.038 Uiso 1 1 calc R . . C8 C 1.01247(18) 0.2966(4) 0.9144(2) 0.0284(6) Uani 1 1 d . . . C9 C 0.93546(19) 0.2384(4) 0.9445(2) 0.0267(5) Uani 1 1 d . . . H9 H 0.9558 0.1727 1.0111 0.032 Uiso 1 1 calc R . . C10 C 0.82839(18) 0.2801(3) 0.87336(19) 0.0247(5) Uani 1 1 d . . . H10 H 0.7703 0.2409 0.8895 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0201(3) 0.0411(4) 0.0402(4) -0.0054(3) 0.0035(3) 0.0057(2) N1 0.0220(9) 0.0251(11) 0.0229(11) 0.0011(9) 0.0073(8) 0.0011(8) N2 0.0247(9) 0.0214(10) 0.0236(11) 0.0000(9) 0.0083(8) 0.0017(8) N3 0.0176(8) 0.0229(10) 0.0205(11) 0.0013(8) 0.0073(8) 0.0015(7) N4 0.0190(9) 0.0262(11) 0.0210(11) 0.0057(9) 0.0082(8) 0.0025(7) O1 0.0228(8) 0.0355(11) 0.0212(9) 0.0066(8) 0.0030(7) -0.0046(7) C1 0.0206(11) 0.0276(13) 0.0228(13) 0.0031(10) 0.0065(9) -0.0021(9) C2 0.0149(10) 0.0242(12) 0.0243(13) 0.0001(10) 0.0078(9) -0.0007(8) C3 0.0150(10) 0.0227(12) 0.0265(13) 0.0020(10) 0.0077(9) 0.0025(8) C4 0.0415(14) 0.0213(13) 0.0306(15) -0.0011(11) 0.0124(12) 0.0032(10) C5 0.0210(10) 0.0193(12) 0.0227(13) -0.0009(10) 0.0083(9) 0.0021(8) C6 0.0272(12) 0.0304(14) 0.0268(14) 0.0050(11) 0.0135(10) 0.0015(10) C7 0.0227(11) 0.0364(15) 0.0367(16) 0.0000(12) 0.0139(11) 0.0011(10) C8 0.0177(11) 0.0280(13) 0.0331(15) -0.0057(11) 0.0068(10) 0.0019(9) C9 0.0276(11) 0.0252(13) 0.0217(13) 0.0023(10) 0.0072(10) 0.0044(9) C10 0.0226(11) 0.0242(13) 0.0260(14) 0.0043(10) 0.0105(10) 0.0034(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C8 1.691(2) . ? N1 N2 1.352(3) . ? N1 C2 1.367(3) . ? N2 N3 1.381(3) . ? N3 C3 1.359(3) . ? N3 N4 1.438(3) . ? N4 C5 1.368(3) . ? N4 H4N 0.876(10) . ? O1 C1 1.407(3) . ? O1 H1O 0.843(10) . ? C1 C2 1.520(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.429(3) . ? C3 C4 1.512(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.354(3) . ? C5 C10 1.433(3) . ? C6 C7 1.347(3) . ? C6 H6 0.9500 . ? C7 C8 1.430(4) . ? C7 H7 0.9500 . ? C8 C9 1.352(3) . ? C9 C10 1.339(3) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? 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 N2 N1 C2 107.71(19) . . ? N1 N2 N3 108.30(18) . . ? C3 N3 N2 110.44(18) . . ? C3 N3 N4 125.56(19) . . ? N2 N3 N4 123.92(18) . . ? C5 N4 N3 118.52(17) . . ? C5 N4 H4N 111.9(17) . . ? N3 N4 H4N 114.1(17) . . ? C1 O1 H1O 113(2) . . ? O1 C1 C2 109.90(18) . . ? O1 C1 H1A 109.7 . . ? C2 C1 H1A 109.7 . . ? O1 C1 H1B 109.7 . . ? C2 C1 H1B 109.7 . . ? H1A C1 H1B 108.2 . . ? N1 C2 C3 109.3(2) . . ? N1 C2 C1 119.1(2) . . ? C3 C2 C1 131.6(2) . . ? N3 C3 C2 104.3(2) . . ? N3 C3 C4 120.5(2) . . ? C2 C3 C4 135.2(2) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 N4 117.8(2) . . ? C6 C5 C10 122.8(2) . . ? N4 C5 C10 119.15(19) . . ? C7 C6 C5 115.2(2) . . ? C7 C6 H6 122.4 . . ? C5 C6 H6 122.4 . . ? C6 C7 C8 121.6(2) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C9 C8 C7 123.3(2) . . ? C9 C8 Cl1 115.2(2) . . ? C7 C8 Cl1 121.51(17) . . ? C10 C9 C8 115.1(2) . . ? C10 C9 H9 122.4 . . ? C8 C9 H9 122.4 . . ? C9 C10 C5 122.0(2) . . ? C9 C10 H10 119.0 . . ? C5 C10 H10 119.0 . . ? 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 C2 N1 N2 N3 0.0(2) . . . . ? N1 N2 N3 C3 0.2(2) . . . . ? N1 N2 N3 N4 176.96(16) . . . . ? C3 N3 N4 C5 -101.8(2) . . . . ? N2 N3 N4 C5 81.9(2) . . . . ? N2 N1 C2 C3 -0.1(2) . . . . ? N2 N1 C2 C1 179.73(17) . . . . ? O1 C1 C2 N1 44.9(3) . . . . ? O1 C1 C2 C3 -135.3(2) . . . . ? N2 N3 C3 C2 -0.2(2) . . . . ? N4 N3 C3 C2 -176.97(16) . . . . ? N2 N3 C3 C4 -179.77(18) . . . . ? N4 N3 C3 C4 3.5(3) . . . . ? N1 C2 C3 N3 0.2(2) . . . . ? C1 C2 C3 N3 -179.6(2) . . . . ? N1 C2 C3 C4 179.7(2) . . . . ? C1 C2 C3 C4 -0.2(4) . . . . ? N3 N4 C5 C6 16.8(3) . . . . ? N3 N4 C5 C10 -167.99(19) . . . . ? N4 C5 C6 C7 173.8(2) . . . . ? C10 C5 C6 C7 -1.2(4) . . . . ? C5 C6 C7 C8 0.3(4) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C6 C7 C8 Cl1 -179.3(2) . . . . ? C7 C8 C9 C10 0.2(4) . . . . ? Cl1 C8 C9 C10 179.72(18) . . . . ? C8 C9 C10 C5 -1.0(4) . . . . ? C6 C5 C10 C9 1.6(4) . . . . ? N4 C5 C10 C9 -173.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.234 _refine_diff_density_min -0.351 _refine_diff_density_rms 0.064