# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 892822' #TrackingRef 'web_deposit_cif_file_0_A.vanderLee_1342701706.kf137.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _cell_length_a 11.3990(4) _cell_length_b 15.5354(5) _cell_length_c 9.2351(3) _cell_angle_alpha 90 _cell_angle_beta 109.568(4) _cell_angle_gamma 90 _cell_volume 1540.97(10) _cell_oxdiff_length_a 9.2364(3) _cell_oxdiff_length_b 15.5326(6) _cell_oxdiff_length_c 11.4000(4) _cell_oxdiff_angle_alpha 89.989(3) _cell_oxdiff_angle_beta 109.579(3) _cell_oxdiff_angle_gamma 90.006(3) _cell_oxdiff_volume 1540.95(10) _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,-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' 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' 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' _cell_formula_units_Z 4 # Given Formula = C13.33 N1.33 O1.33 # Dc = 1.29 Fooo = 648.00 Mu = 0.87 M = 300.23 # Found Formula = C13.33 H9.33 N2.67 # Dc = 1.34 FOOO = 648.00 Mu = 0.82 M = 310.36 _chemical_formula_sum 'C20 H14 N4' _chemical_formula_moiety 'C20 H14 N4' _chemical_compound_source ? _chemical_formula_weight 310.35 _cell_measurement_temperature 173 _cell_measurement_reflns_used 6922 _cell_measurement_theta_min 2.7910 _cell_measurement_theta_max 26.4685 _exptl_crystal_description prism _exptl_crystal_colour transparent _exptl_crystal_size_min 0.150 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_max 0.300 _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_min 0.96207 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_detector_area_resol_mean 8.4205 _diffrn_reflns_av_sigmaI/netI 0.1447 #montpellier_reflns_maxres is minimum d (highest resolution) #where <= 2.0 #(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999) _montpellier_reflns_maxres 0.84 _montpellier_reflns_completeness_maxres 99.7 #montpellier_diffrn_reflns_class_completeness_shell is completeness in shell #montpellier_diffrn_class_reflns_cumul_completeness is cumulative #completeness to resolution of shell loop_ _montpellier_diffrn_reflns_class_number _montpellier_diffrn_reflns_class_d_res_high _montpellier_diffrn_reflns_class_d_res_low _montpellier_diffrn_reflns_class_completeness_shell _montpellier_diffrn_reflns_class_cumul_completeness 1 100.0 10.000 0.0 0.0 2 10.000 5.000 65.6 60.0 3 5.000 3.333 100.0 86.5 4 3.333 2.500 100.0 94.2 5 2.500 2.000 100.0 96.9 6 2.000 1.667 100.0 98.2 7 1.667 1.429 100.0 98.8 8 1.429 1.250 100.0 99.2 9 1.250 1.111 100.0 99.4 10 1.111 1.000 100.0 99.6 11 1.000 0.909 100.0 99.7 12 0.909 0.833 95.9 98.8 13 0.833 0.796 45.7 92.0 loop_ _diffrn_reflns_class_number _diffrn_reflns_class_d_res_high _diffrn_reflns_class_d_res_low _diffrn_reflns_class_av_R_eq _diffrn_reflns_class_av_uI/I 20 0.82 0.80 0.640 1.4 19 0.84 0.82 0.438 1.7 18 0.86 0.84 0.382 2.5 17 0.89 0.86 0.307 3.6 16 0.92 0.89 0.333 4.7 15 0.95 0.92 0.243 6.7 14 0.99 0.95 0.213 7.5 13 1.03 0.99 0.148 10.3 12 1.07 1.03 0.114 13.9 11 1.13 1.07 0.111 14.1 10 1.19 1.13 0.085 18.6 9 1.26 1.19 0.083 20.1 8 1.35 1.26 0.085 19.6 7 1.45 1.35 0.112 21.3 6 1.59 1.45 0.068 29.4 5 1.78 1.59 0.039 42.3 4 2.05 1.78 0.034 54.9 3 2.52 2.05 0.036 52.5 2 3.56 2.52 0.016 95.1 1 100.0 3.56 0.014 590 _diffrn_measurement_device Area _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 173 _diffrn_reflns_number 23653 _reflns_number_total 2940 _diffrn_reflns_av_R_equivalents 0.050 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 2940 # Theoretical number of reflections is about 6406 _diffrn_reflns_theta_min 2.797 _diffrn_reflns_theta_max 26.526 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 25.199 _diffrn_measured_fraction_theta_full 0.982 _diffrn_orient_matrix_UB_11 -0.0097055000 _diffrn_orient_matrix_UB_12 0.0435217000 _diffrn_orient_matrix_UB_13 -0.0243442000 _diffrn_orient_matrix_UB_21 -0.0486198000 _diffrn_orient_matrix_UB_22 -0.0129778000 _diffrn_orient_matrix_UB_23 -0.0672744000 _diffrn_orient_matrix_UB_31 -0.0436219000 _diffrn_orient_matrix_UB_32 0.0047696000 _diffrn_orient_matrix_UB_33 0.0390493000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -6.00 102.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - 12.8809 77.0000 -150.0000 108 #__ type_ start__ end____ width___ exp.time_ 2 omega -7.00 100.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - 12.8809 77.0000 90.0000 107 #__ type_ start__ end____ width___ exp.time_ 3 omega -3.00 105.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - 12.8809 77.0000 -30.0000 108 #__ type_ start__ end____ width___ exp.time_ 4 omega -54.00 27.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - -16.1622 77.0000 120.0000 81 #__ type_ start__ end____ width___ exp.time_ 5 omega -54.00 27.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - -16.1622 77.0000 0.0000 81 #__ type_ start__ end____ width___ exp.time_ 6 omega -53.00 28.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - -16.1622 77.0000 -120.0000 81 #__ type_ start__ end____ width___ exp.time_ 7 omega 34.00 112.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - 12.8809 179.0000 120.0000 78 #__ type_ start__ end____ width___ exp.time_ 8 omega -106.00 20.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - -16.1622 -38.0000 -30.0000 126 #__ type_ start__ end____ width___ exp.time_ 9 omega -106.00 -7.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - -16.1622 -38.0000 90.0000 99 #__ type_ start__ end____ width___ exp.time_ 10 omega -113.00 -32.00 1.0000 70.0000 omega____ theta____ kappa____ phi______ frames - -16.1622 179.0000 120.0000 81 ; _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _reflns_limit_h_min -14 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _oxford_diffrn_Wilson_B_factor 1.98 _oxford_diffrn_Wilson_scale 0.69 _atom_sites_solution_primary other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.50 _refine_diff_density_max 0.45 # 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>-3.0\s(I) _refine_ls_number_reflns 2939 _refine_ls_number_restraints 0 _refine_ls_number_parameters 217 _oxford_refine_ls_R_factor_ref 0.0800 _refine_ls_wR_factor_ref 0.1136 _refine_ls_goodness_of_fit_ref 0.9700 _refine_ls_shift/su_max 0.0002795 _refine_ls_shift/su_mean 0.0000291 # The values computed from all data _oxford_reflns_number_all 2940 _refine_ls_R_factor_all 0.0802 _refine_ls_wR_factor_all 0.1142 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2065 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_gt 0.0885 # 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 Fsqd _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: 162. 256. 157. 64.9 15.2 ; # Insert your own references if required - in alphabetical order 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 1.02106(17) 0.64692(12) 0.4768(2) 0.0257 1.0000 Uani . . . . . . C2 C 1.0971(2) 0.63584(13) 0.6277(2) 0.0249 1.0000 Uani . . . . . . C3 C 1.0283(2) 0.58360(14) 0.6938(2) 0.0278 1.0000 Uani . . . . . . N4 N 0.91337(19) 0.56333(13) 0.5853(2) 0.0360 1.0000 Uani . . . . . . C5 C 0.9143(2) 0.60290(16) 0.4606(3) 0.0330 1.0000 Uani . . . . . . C6 C 1.0787(2) 0.55965(15) 0.8475(3) 0.0363 1.0000 Uani . . . . . . C7 C 1.1956(2) 0.59016(16) 0.9306(3) 0.0386 1.0000 Uani . . . . . . C8 C 1.2623(2) 0.64320(16) 0.8638(3) 0.0369 1.0000 Uani . . . . . . C9 C 1.2149(2) 0.66690(15) 0.7097(3) 0.0292 1.0000 Uani . . . . . . C10 C 1.0481(2) 0.70173(15) 0.3629(2) 0.0278 1.0000 Uani . . . . . . C11 C 0.9624(2) 0.68406(14) 0.2080(3) 0.0296 1.0000 Uani . . . . . . C12 C 0.8908(2) 0.66786(15) 0.0836(3) 0.0299 1.0000 Uani . . . . . . C13 C 0.8090(2) 0.64486(15) -0.0589(3) 0.0296 1.0000 Uani . . . . . . C14 C 0.7384(2) 0.62223(15) -0.1804(3) 0.0301 1.0000 Uani . . . . . . C15 C 0.6540(2) 0.59504(15) -0.3318(3) 0.0312 1.0000 Uani . . . . . . N16 N 0.63024(17) 0.50238(12) -0.3404(2) 0.0279 1.0000 Uani . . . . . . C17 C 0.5492(2) 0.45837(14) -0.2840(2) 0.0274 1.0000 Uani . . . . . . C18 C 0.5599(2) 0.37163(15) -0.3214(3) 0.0284 1.0000 Uani . . . . . . N19 N 0.64488(19) 0.36370(13) -0.3996(2) 0.0366 1.0000 Uani . . . . . . C20 C 0.6831(2) 0.44253(15) -0.4066(3) 0.0328 1.0000 Uani . . . . . . C21 C 0.4878(2) 0.30895(16) -0.2818(3) 0.0357 1.0000 Uani . . . . . . C22 C 0.4090(2) 0.33594(17) -0.2049(3) 0.0373 1.0000 Uani . . . . . . C23 C 0.4003(2) 0.42229(16) -0.1689(3) 0.0370 1.0000 Uani . . . . . . C24 C 0.4696(2) 0.48508(16) -0.2077(3) 0.0336 1.0000 Uani . . . . . . H51 H 0.8493 0.6006 0.3675 0.0495 1.0000 Uiso R . . . . . H61 H 1.0340 0.5246 0.8919 0.0559 1.0000 Uiso R . . . . . H71 H 1.2317 0.5760 1.0349 0.0583 1.0000 Uiso R . . . . . H81 H 1.3405 0.6627 0.9226 0.0535 1.0000 Uiso R . . . . . H91 H 1.2580 0.7025 0.6620 0.0448 1.0000 Uiso R . . . . . H101 H 1.0403 0.7625 0.3871 0.0442 1.0000 Uiso R . . . . . H102 H 1.1331 0.6915 0.3650 0.0442 1.0000 Uiso R . . . . . H151 H 0.6911 0.6107 -0.4096 0.0473 1.0000 Uiso R . . . . . H152 H 0.5741 0.6249 -0.3528 0.0473 1.0000 Uiso R . . . . . H201 H 0.7427 0.4577 -0.4515 0.0512 1.0000 Uiso R . . . . . H211 H 0.4930 0.2515 -0.3083 0.0537 1.0000 Uiso R . . . . . H221 H 0.3603 0.2957 -0.1768 0.0571 1.0000 Uiso R . . . . . H231 H 0.3455 0.4382 -0.1172 0.0570 1.0000 Uiso R . . . . . H241 H 0.4635 0.5433 -0.1866 0.0509 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 0.0259(9) 0.0291(10) 0.0223(9) -0.0012(8) 0.0084(7) -0.0048(8) C2 0.0276(11) 0.0250(11) 0.0219(10) -0.0011(9) 0.0079(9) 0.0024(9) C3 0.0323(12) 0.0264(11) 0.0261(11) -0.0010(9) 0.0116(10) 0.0002(10) N4 0.0336(11) 0.0420(12) 0.0327(11) -0.0011(9) 0.0116(9) -0.0122(9) C5 0.0271(11) 0.0407(13) 0.0283(12) -0.0016(10) 0.0051(10) -0.0091(11) C6 0.0486(15) 0.0297(12) 0.0330(13) 0.0047(10) 0.0170(12) 0.0056(11) C7 0.0443(14) 0.0383(14) 0.0278(12) 0.0040(11) 0.0048(11) 0.0132(12) C8 0.0275(12) 0.0416(14) 0.0355(13) -0.0062(11) 0.0025(10) 0.0059(11) C9 0.0245(11) 0.0312(12) 0.0320(12) -0.0057(10) 0.0094(9) 0.0003(9) C10 0.0282(11) 0.0319(12) 0.0238(11) 0.0007(10) 0.0093(9) -0.0044(10) C11 0.0352(13) 0.0281(12) 0.0273(12) 0.0009(9) 0.0128(10) -0.0040(10) C12 0.0343(13) 0.0311(12) 0.0266(12) 0.0024(10) 0.0132(10) -0.0035(10) C13 0.0337(12) 0.0282(12) 0.0254(12) 0.0026(9) 0.0078(10) -0.0018(10) C14 0.0318(12) 0.0267(12) 0.0318(13) 0.0036(9) 0.0107(10) 0.0006(10) C15 0.0344(12) 0.0285(12) 0.0284(12) 0.0011(10) 0.0073(10) -0.0037(10) N16 0.0270(10) 0.0289(10) 0.0262(10) -0.0015(8) 0.0067(8) -0.0032(8) C17 0.0231(11) 0.0307(12) 0.0246(11) 0.0010(9) 0.0032(9) -0.0010(9) C18 0.0236(11) 0.0314(12) 0.0273(12) -0.0017(9) 0.0047(9) -0.0009(9) N19 0.0348(11) 0.0328(11) 0.0458(12) -0.0047(9) 0.0184(10) -0.0022(9) C20 0.0300(12) 0.0363(13) 0.0359(13) -0.0043(10) 0.0159(10) -0.0026(10) C21 0.0305(12) 0.0334(13) 0.0406(14) 0.0018(11) 0.0084(11) -0.0036(10) C22 0.0285(12) 0.0429(14) 0.0407(14) 0.0040(11) 0.0119(11) -0.0068(11) C23 0.0276(12) 0.0460(15) 0.0394(14) -0.0044(11) 0.0137(11) -0.0008(11) C24 0.0309(12) 0.0346(13) 0.0351(13) -0.0028(10) 0.0110(10) 0.0021(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.304(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 . 1.383(3) yes N1 . C5 . 1.360(3) yes N1 . C10 . 1.464(3) yes C2 . C3 . 1.402(3) yes C2 . C9 . 1.389(3) yes C3 . N4 . 1.393(3) yes C3 . C6 . 1.392(3) yes N4 . C5 . 1.308(3) yes C5 . H51 . 0.929 no C6 . C7 . 1.380(4) yes C6 . H61 . 0.930 no C7 . C8 . 1.398(4) yes C7 . H71 . 0.938 no C8 . C9 . 1.392(3) yes C8 . H81 . 0.926 no C9 . H91 . 0.941 no C10 . C11 . 1.463(3) yes C10 . H101 . 0.980 no C10 . H102 . 0.976 no C11 . C12 . 1.192(3) yes C12 . C13 . 1.381(3) yes C13 . C14 . 1.195(3) yes C14 . C15 . 1.469(3) yes C15 . N16 . 1.462(3) yes C15 . H151 . 0.979 no C15 . H152 . 0.981 no N16 . C17 . 1.383(3) yes N16 . C20 . 1.360(3) yes C17 . C18 . 1.406(3) yes C17 . C24 . 1.386(3) yes C18 . N19 . 1.395(3) yes C18 . C21 . 1.399(3) yes N19 . C20 . 1.309(3) yes C20 . H201 . 0.937 no C21 . C22 . 1.383(4) yes C21 . H211 . 0.933 no C22 . C23 . 1.394(4) yes C22 . H221 . 0.929 no C23 . C24 . 1.376(3) yes C23 . H231 . 0.938 no C24 . H241 . 0.933 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 . 106.50(18) yes C2 . N1 . C10 . 125.78(18) yes C5 . N1 . C10 . 127.53(18) yes N1 . C2 . C3 . 104.93(18) yes N1 . C2 . C9 . 132.1(2) yes C3 . C2 . C9 . 122.9(2) yes C2 . C3 . N4 . 110.22(19) yes C2 . C3 . C6 . 119.9(2) yes N4 . C3 . C6 . 129.9(2) yes C3 . N4 . C5 . 104.15(19) yes N1 . C5 . N4 . 114.2(2) yes N1 . C5 . H51 . 121.9 no N4 . C5 . H51 . 123.9 no C3 . C6 . C7 . 117.9(2) yes C3 . C6 . H61 . 120.5 no C7 . C6 . H61 . 121.7 no C6 . C7 . C8 . 121.6(2) yes C6 . C7 . H71 . 120.0 no C8 . C7 . H71 . 118.4 no C7 . C8 . C9 . 121.7(2) yes C7 . C8 . H81 . 119.5 no C9 . C8 . H81 . 118.8 no C8 . C9 . C2 . 116.0(2) yes C8 . C9 . H91 . 123.3 no C2 . C9 . H91 . 120.7 no N1 . C10 . C11 . 111.17(18) yes N1 . C10 . H101 . 109.8 no C11 . C10 . H101 . 108.8 no N1 . C10 . H102 . 109.8 no C11 . C10 . H102 . 108.8 no H101 . C10 . H102 . 108.5 no C10 . C11 . C12 . 178.0(2) yes C11 . C12 . C13 . 177.2(3) yes C12 . C13 . C14 . 177.8(2) yes C13 . C14 . C15 . 178.5(2) yes C14 . C15 . N16 . 112.64(18) yes C14 . C15 . H151 . 108.7 no N16 . C15 . H151 . 108.8 no C14 . C15 . H152 . 108.7 no N16 . C15 . H152 . 108.2 no H151 . C15 . H152 . 109.8 no C15 . N16 . C17 . 126.96(19) yes C15 . N16 . C20 . 126.6(2) yes C17 . N16 . C20 . 106.49(19) yes N16 . C17 . C18 . 104.94(19) yes N16 . C17 . C24 . 132.6(2) yes C18 . C17 . C24 . 122.5(2) yes C17 . C18 . N19 . 110.1(2) yes C17 . C18 . C21 . 119.8(2) yes N19 . C18 . C21 . 130.1(2) yes C18 . N19 . C20 . 104.1(2) yes N16 . C20 . N19 . 114.3(2) yes N16 . C20 . H201 . 121.6 no N19 . C20 . H201 . 124.1 no C18 . C21 . C22 . 117.5(2) yes C18 . C21 . H211 . 120.2 no C22 . C21 . H211 . 122.3 no C21 . C22 . C23 . 121.6(2) yes C21 . C22 . H221 . 119.4 no C23 . C22 . H221 . 118.9 no C22 . C23 . C24 . 121.8(2) yes C22 . C23 . H231 . 119.2 no C24 . C23 . H231 . 119.0 no C17 . C24 . C23 . 116.8(2) yes C17 . C24 . H241 . 120.3 no C23 . C24 . H241 . 122.9 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 C10 . H102 . N19 2_765 168 0.98 2.59 3.550(3) yes C20 . H201 . N4 1_554 139 0.94 2.48 3.248(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 02/02/11 at 17:19:11 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) H ( 102,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 02/02/11 at 17:19:11 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; data_2 _database_code_depnum_ccdc_archive 'CCDC 892823' #TrackingRef '12706_web_deposit_cif_file_2_A.vanderLee_1342701706.kf129fonce.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ? #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 10.3530(3) _cell_length_b 12.3146(3) _cell_length_c 9.4233(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1201.41(5) _cell_oxdiff_length_a 9.4245(3) _cell_oxdiff_length_b 10.3524(3) _cell_oxdiff_length_c 12.3138(4) _cell_oxdiff_angle_alpha 90.010(3) _cell_oxdiff_angle_beta 90.014(2) _cell_oxdiff_angle_gamma 89.998(2) _cell_oxdiff_volume 1201.41(6) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n ' _symmetry_space_group_name_Hall ' -P 2n 2ab ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x,-y,z+1/2 -x,y,-z+1/2 -x+1/2,-y+1/2,z+1/2 x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,-z -x+1/2,y+1/2,z 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 4 _chemical_formula_sum 'C12 H12 N4 O' _chemical_formula_moiety 'C12 H10 N4, H2 O' _chemical_compound_source ? _chemical_formula_weight 228.26 _cell_measurement_reflns_used 8739 _cell_measurement_theta_min 2.9171 _cell_measurement_theta_max 29.0981 _cell_measurement_temperature 173.1 _exptl_crystal_description prism _exptl_crystal_colour transparent _exptl_crystal_size_min 0.250 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_max 0.450 _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_min 0.89516 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_detector_area_resol_mean 8.4205 _diffrn_reflns_av_sigmaI/netI 0.0827 #montpellier_reflns_maxres is minimum d (highest resolution) #where <= 2.0 #(Z. Dauter, Acta Cryst. D55, 1703-1717, 1999) _montpellier_reflns_maxres 0.73 _montpellier_reflns_completeness_maxres 99.8 #montpellier_diffrn_reflns_class_completeness_shell is completeness in shell #montpellier_diffrn_class_reflns_cumul_completeness is cumulative #completeness to resolution of shell loop_ _montpellier_diffrn_reflns_class_number _montpellier_diffrn_reflns_class_d_res_high _montpellier_diffrn_reflns_class_d_res_low _montpellier_diffrn_reflns_class_completeness_shell _montpellier_diffrn_reflns_class_cumul_completeness 1 100.0 10.000 0.0 0.0 2 10.000 5.000 65.2 57.7 3 5.000 3.333 100.0 86.7 4 3.333 2.500 100.0 94.2 5 2.500 2.000 100.0 97.0 6 2.000 1.667 100.0 98.2 7 1.667 1.429 100.0 98.8 8 1.429 1.250 100.0 99.2 9 1.250 1.111 100.0 99.4 10 1.111 1.000 100.0 99.6 11 1.000 0.909 100.0 99.7 12 0.909 0.833 100.0 99.8 13 0.833 0.769 99.8 99.8 14 0.769 0.729 68.1 95.2 loop_ _diffrn_reflns_class_number _diffrn_reflns_class_d_res_high _diffrn_reflns_class_d_res_low _diffrn_reflns_class_av_R_eq _diffrn_reflns_class_av_uI/I 20 0.75 0.73 0.348 2.4 19 0.77 0.75 0.257 4.2 18 0.79 0.77 0.274 6.2 17 0.82 0.79 0.205 9.4 16 0.84 0.82 0.213 10.5 15 0.87 0.84 0.158 13.9 14 0.90 0.87 0.125 16.6 13 0.94 0.90 0.107 20.2 12 0.98 0.94 0.084 26.4 11 1.03 0.98 0.072 28.7 10 1.09 1.03 0.049 33.8 9 1.15 1.09 0.059 37.0 8 1.23 1.15 0.039 56.8 7 1.33 1.23 0.041 58.7 6 1.46 1.33 0.044 53.9 5 1.63 1.46 0.033 67.4 4 1.88 1.63 0.021 1382 3 2.31 1.88 0.025 89.8 2 3.26 2.31 0.014 1051 1 100.0 3.26 0.014 675 _diffrn_measurement_device Area _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _diffrn_orient_matrix_UB_11 -0.0473473000 _diffrn_orient_matrix_UB_12 -0.0394200000 _diffrn_orient_matrix_UB_13 0.0175250000 _diffrn_orient_matrix_UB_21 -0.0327926000 _diffrn_orient_matrix_UB_22 0.0388599000 _diffrn_orient_matrix_UB_23 0.0423000000 _diffrn_orient_matrix_UB_31 -0.0371117000 _diffrn_orient_matrix_UB_32 0.0159365000 _diffrn_orient_matrix_UB_33 -0.0597310000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 2.00 100.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 19.2538 77.0000 90.0000 98 #__ type_ start__ end____ width___ exp.time_ 2 omega -15.00 101.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 19.2538 77.0000 -150.0000 116 #__ type_ start__ end____ width___ exp.time_ 3 omega -19.00 84.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 19.2538 77.0000 0.0000 103 #__ type_ start__ end____ width___ exp.time_ 4 omega -58.00 66.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -22.5351 77.0000 90.0000 124 #__ type_ start__ end____ width___ exp.time_ 5 omega -60.00 46.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -22.5351 77.0000 -150.0000 106 #__ type_ start__ end____ width___ exp.time_ 6 omega -61.00 49.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -22.5351 77.0000 -30.0000 110 #__ type_ start__ end____ width___ exp.time_ 7 omega 34.00 118.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 19.2538 179.0000 0.0000 84 #__ type_ start__ end____ width___ exp.time_ 8 omega -27.00 21.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 19.2538 104.0000 6.0000 48 #__ type_ start__ end____ width___ exp.time_ 9 omega -113.00 14.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -22.5351 -38.0000 -180.0000 127 #__ type_ start__ end____ width___ exp.time_ 10 omega -59.00 67.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -22.5351 38.0000 -180.0000 126 #__ type_ start__ end____ width___ exp.time_ 11 omega -119.00 -32.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -22.5351 179.0000 -150.0000 87 ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 173.1 _diffrn_reflns_number 24150 _reflns_number_total 1546 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 1546 # Theoretical number of reflections is about 3244 _diffrn_reflns_theta_min 3.309 _diffrn_reflns_theta_max 29.162 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.704 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 2.53 _oxford_diffrn_Wilson_scale 0.07 _atom_sites_solution_primary other #heavy,direct,difmap,geom _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.29 _refine_diff_density_max 0.28 # 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>-3.0\s(I) _refine_ls_number_reflns 1546 _refine_ls_number_restraints 1 _refine_ls_number_parameters 96 _oxford_refine_ls_R_factor_ref 0.0540 _refine_ls_wR_factor_ref 0.1093 _refine_ls_goodness_of_fit_ref 0.9727 _refine_ls_shift/su_max 0.0002088 _refine_ls_shift/su_mean 0.0000261 # The values computed from all data _oxford_reflns_number_all 1546 _refine_ls_R_factor_all 0.0540 _refine_ls_wR_factor_all 0.1093 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1262 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_gt 0.0947 # 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 Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment refxyz # 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: 462. 756. 465. 192. 40.6 ; # Insert your own references if required - in alphabetical order 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 O1 O 1.0000 0.15762(11) 0.7500 0.0317 1.0000 Uani DS T . . . . H11 H 0.9390(15) 0.1162(9) 0.717(2) 0.0500 1.0000 Uiso D . . . . . N2 N 0.75252(10) 0.35690(8) 0.55295(11) 0.0228 1.0000 Uani . . . . . . C3 C 0.66275(13) 0.43617(10) 0.55922(15) 0.0296 1.0000 Uani . . . . . . H31 H 0.584(2) 0.4329(15) 0.501(2) 0.0500 1.0000 Uiso . . . . . . N4 N 0.69487(12) 0.51258(9) 0.65040(14) 0.0351 1.0000 Uani . . . . . . C5 C 0.81184(15) 0.47956(11) 0.70599(17) 0.0371 1.0000 Uani . . . . . . H51 H 0.8583(19) 0.5226(15) 0.780(2) 0.0500 1.0000 Uiso . . . . . . C6 C 0.84831(14) 0.38372(11) 0.64688(16) 0.0324 1.0000 Uani . . . . . . H61 H 0.9242(19) 0.3382(16) 0.659(2) 0.0500 1.0000 Uiso . . . . . . C7 C 0.74499(13) 0.25766(10) 0.46793(13) 0.0257 1.0000 Uani . . . . . . H71 H 0.7421(18) 0.1948(16) 0.5318(19) 0.0500 1.0000 Uiso . . . . . . H72 H 0.664(2) 0.2629(15) 0.411(2) 0.0500 1.0000 Uiso . . . . . . C8 C 0.85575(12) 0.24889(10) 0.37185(12) 0.0251 1.0000 Uani . . . . . . C9 C 0.94768(12) 0.24572(9) 0.29524(13) 0.0253 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 O1 0.0256(6) 0.0226(6) 0.0467(8) 0.0000 -0.0030(6) 0.0000 N2 0.0218(5) 0.0218(5) 0.0247(5) 0.0014(4) 0.0017(4) 0.0034(4) C3 0.0280(6) 0.0263(6) 0.0344(6) 0.0031(5) 0.0012(5) 0.0079(5) N4 0.0377(6) 0.0245(5) 0.0433(7) -0.0019(5) 0.0053(5) 0.0061(5) C5 0.0365(7) 0.0316(7) 0.0430(8) -0.0090(6) -0.0009(6) -0.0005(6) C6 0.0276(7) 0.0323(7) 0.0374(7) -0.0047(5) -0.0042(5) 0.0045(5) C7 0.0260(6) 0.0234(6) 0.0278(6) -0.0010(5) 0.0041(5) 0.0010(4) C8 0.0273(6) 0.0241(6) 0.0240(6) 0.0003(4) -0.0006(5) 0.0033(4) C9 0.0279(6) 0.0236(5) 0.0243(5) -0.0002(4) -0.0012(5) 0.0009(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.23(5) 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 O1 . H11 4_756 0.869(18) no O1 . H11 . 0.869(18) no N2 . C3 . 1.3492(15) yes N2 . C6 . 1.3697(17) yes N2 . C7 . 1.4633(16) yes C3 . H31 . 0.98(2) no C3 . N4 . 1.3168(18) yes N4 . C5 . 1.381(2) yes C5 . H51 . 1.00(2) no C5 . C6 . 1.3586(19) yes C6 . H61 . 0.971(19) no C7 . H71 . 0.981(19) no C7 . H72 . 0.99(2) no C7 . C8 . 1.4651(17) yes C8 . C9 . 1.1952(17) yes C9 . C9 4_755 1.379(2) 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 H11 4_756 O1 . H11 . 107.99(10) no C3 . N2 . C6 . 107.21(11) yes C3 . N2 . C7 . 126.27(11) yes C6 . N2 . C7 . 126.43(11) yes N2 . C3 . H31 . 121.3(11) no N2 . C3 . N4 . 111.82(12) yes H31 . C3 . N4 . 126.9(11) no C3 . N4 . C5 . 104.99(11) yes N4 . C5 . H51 . 122.1(11) no N4 . C5 . C6 . 110.12(13) yes H51 . C5 . C6 . 127.8(11) no N2 . C6 . C5 . 105.86(12) yes N2 . C6 . H61 . 121.4(12) no C5 . C6 . H61 . 132.7(12) no N2 . C7 . H71 . 108.9(11) no N2 . C7 . H72 . 106.5(11) no H71 . C7 . H72 . 110.9(15) no N2 . C7 . C8 . 110.99(11) yes H71 . C7 . C8 . 110.2(11) no H72 . C7 . C8 . 109.3(11) no C7 . C8 . C9 . 177.40(13) yes C9 4_755 C9 . C8 . 177.87(11) yes 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 O1 . H11 . N4 8_645 175.9(5) 0.869(18) 1.986(18) 2.8534(19) yes C6 . H61 . O1 . 143.4(15) 0.971(19) 2.511(19) 3.3411(19) yes C7 . H71 . N4 8_645 160.2(15) 0.981(19) 2.59(2) 3.5289(19) yes C7 . H72 . O1 5_654 158.6(15) 0.99(2) 2.48(2) 3.4262(19) yes _iucr_refine_instruction_details_constraints ; # # Punched on 05/01/11 at 11:04:19 # #LIST 12 BLOCK CONT SCALE CONT O ( 1 ,X'S,U'S) CONT H ( 11 ,X'S) CONT N ( 2 ,X'S,U'S) UNTIL C ( 3 ) CONT H ( 31 ,X'S) CONT N ( 4 ,X'S,U'S) UNTIL C ( 5 ) CONT H ( 51 ,X'S) CONT C ( 6 ,X'S,U'S) CONT H ( 61 ,X'S) CONT C ( 7 ,X'S,U'S) CONT H ( 71 ,X'S) UNTIL H ( 72 ) CONT C ( 8 ,X'S,U'S) UNTIL C ( 9 ) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 05/01/11 at 11:04:19 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) ANGLE 108 , .1 = H(11) TO O(1) TO H(11,-2,1,2,0,1) REM HREST END (DO NOT REMOVE THIS LINE) END ; data_3 _database_code_depnum_ccdc_archive 'CCDC 892824' #TrackingRef '12707_web_deposit_cif_file_4_A.vanderLee_1342701706.kf184_refO6O12_sylvain.cif' _chemical_name_mineral ?? _chemical_formula_moiety 'C20 H14 N4, H2 O' _chemical_formula_sum 'C20 H16 N4 O' _cell_formula_units_Z 4 _chemical_formula_weight 328.37 _cell_length_a 4.537803 _cell_length_b 19.75839 _cell_length_c 19.85653 _cell_angle_alpha 90 _cell_angle_beta 95.38883 _cell_angle_gamma 90 _cell_volume 1772.462 _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz '-x, y+1/2, -z' 'x, y, z' _diffrn_ambient_temperature 293(2) _diffrn_radiation_type X-rays _diffrn_radiation_wavelength 1.541 _diffrn_source 'sealed tube' _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ; PANAlytical Xpert-Pro diffractometer ; _pd_proc_ls_prof_wR_factor 0.06921 _pd_proc_ls_prof_wR_expected 0.03524 _pd_proc_2theta_range_min 5.015 _pd_proc_2theta_range_max 62.526 _pd_proc_2theta_range_inc 0.017 _pd_proc_number_of_points 3384 loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv N1 N 0 0.3201839 -0.09555402 -0.6002763 1 1.931971 C2 C 0 0.5402468 -0.09104001 -0.547345 1 1.931971 C3 C 0 0.5267484 -0.1524808 -0.5124481 1 1.931971 N4 N 0 0.3035123 -0.1933036 -0.5435399 1 1.931971 C5 C 0 0.1903095 -0.1570936 -0.5947981 1 1.931971 C6 C 0 0.722097 -0.1648389 -0.4552556 1 1.931971 C7 C 0 0.9308765 -0.116063 -0.4327858 1 1.931971 C8 C 0 0.9443074 -0.05492893 -0.4675084 1 1.931971 C9 C 0 0.7433847 -0.04015895 -0.5276171 1 1.931971 C10 C 0 0.2461708 -0.0434573 -0.6515143 1 1.931971 C11 C 0 0.04943466 -0.0701699 -0.7078752 1 1.931971 C12 C 0 -0.103943 -0.09300836 -0.7531516 1 1.931971 C13 C 0 -0.2919305 -0.1129955 -0.8082883 1 1.931971 C14 C 0 -0.4534386 -0.12818 -0.8568714 1 1.931971 C15 C 0 -0.6588028 -0.1471732 -0.9154782 1 1.931971 N16 N 0 -0.5499441 -0.1282002 -0.979804 1 1.931971 C17 C 0 -0.3403939 -0.1619999 -1.013344 1 1.931971 C18 C 0 -0.3137438 -0.1237524 -1.072234 1 1.931971 N19 N 0 -0.5033183 -0.06813236 -1.074042 1 1.931971 C20 C 0 -0.6354303 -0.07360194 -1.018516 1 1.931971 C21 C 0 -0.1171917 -0.1440993 -1.118273 1 1.931971 C22 C 0 0.05293769 -0.2023675 -1.105926 1 1.931971 C23 C 0 0.02651486 -0.2402887 -1.047538 1 1.931971 C24 C 0 -0.1700373 -0.2199418 -1.001498 1 1.931971 H51 H 0 0.03118048 -0.1745444 -0.6242258 1 2.318365 H61 H 0 0.7129504 -0.2064714 -0.4316094 1 2.318365 H71 H 0 1.06391 -0.1244789 -0.3938375 1 2.318365 H81 H 0 1.086487 -0.02171234 -0.4522064 1 2.318365 H91 H 0 0.7568907 0.001851014 -0.5503945 1 2.318365 H101 H 0 0.4227668 -0.02723269 -0.6680706 1 2.318365 H102 H 0 0.1350538 -0.0086287 -0.6327152 1 2.318365 H151 H 0 -0.6874096 -0.1947768 -0.9144025 1 2.318365 H152 H 0 -0.8423009 -0.1251876 -0.9112093 1 2.318365 H201 H 0 -0.7778873 -0.04087654 -1.00823 1 2.318365 H211 H 0 -0.09919761 -0.1182747 -1.158035 1 2.318365 H221 H 0 0.1867904 -0.2162238 -1.137279 1 2.318365 H231 H 0 0.1423736 -0.2799696 -1.039129 1 2.318365 H241 H 0 -0.1880313 -0.2457664 -0.9617364 1 2.318365 N25 N 0 0.3589474 0.1287668 -0.8442984 1 1.931971 C26 C 0 0.5523561 0.1188021 -0.7870778 1 1.931971 C27 C 0 0.4783271 0.1684957 -0.7416898 1 1.931971 N28 N 0 0.2450722 0.2078365 -0.7706253 1 1.931971 C29 C 0 0.1849777 0.1818844 -0.8310083 1 1.931971 C30 C 0 0.6332823 0.1728495 -0.6777513 1 1.931971 C31 C 0 0.8622664 0.1275095 -0.6592009 1 1.931971 C32 C 0 0.9362954 0.07781581 -0.7045888 1 1.931971 C33 C 0 0.7786526 0.07192633 -0.771778 1 1.931971 C34 C 0 0.3487174 0.088875 -0.9066055 1 1.931971 C35 C 0 0.07956923 0.1030197 -0.9508596 1 1.931971 C36 C 0 -0.1392633 0.1128219 -0.9859353 1 1.931971 C37 C 0 -0.3787188 0.1277621 -1.03166 1 1.931971 C38 C 0 -0.5793944 0.140891 -1.072829 1 1.931971 C39 C 0 -0.8282159 0.1587008 -1.122429 1 1.931971 N40 N 0 -0.7795852 0.1380868 -1.191174 1 1.931971 C41 C 0 -0.8127618 0.07382551 -1.218444 1 1.931971 C42 C 0 -0.7402714 0.08052409 -1.285477 1 1.931971 N43 N 0 -0.6651066 0.1474126 -1.298221 1 1.931971 C44 C 0 -0.6924718 0.1785665 -1.241021 1 1.931971 C45 C 0 -0.750915 0.02421819 -1.328022 1 1.931971 C46 C 0 -0.8334308 -0.03872915 -1.304105 1 1.931971 C47 C 0 -0.9053029 -0.0453706 -1.237644 1 1.931971 C48 C 0 -0.8946592 0.01093529 -1.195099 1 1.931971 H291 H 0 0.03549755 0.197042 -0.8642969 1 2.318365 H301 H 0 0.5828684 0.206691 -0.646842 1 2.318365 H311 H 0 0.9677915 0.1304744 -0.6156585 1 2.318365 H321 H 0 1.092234 0.04693914 -0.6919559 1 2.318365 H331 H 0 0.8325805 0.0377174 -0.801921 1 2.318365 H341 H 0 0.3528377 0.04204309 -0.8957239 1 2.318365 H342 H 0 0.5433009 0.08387252 -0.9198714 1 2.318365 H391 H 0 -1.001648 0.1373343 -1.10942 1 2.318365 H392 H 0 -0.8540744 0.2063801 -1.121123 1 2.318365 H481 H 0 -0.9436044 0.006412442 -1.149838 1 2.318365 H471 H 0 -0.9614964 -0.08823798 -1.221356 1 2.318365 H461 H 0 -0.8406792 -0.07707367 -1.333078 1 2.318365 H451 H 0 -0.7019699 0.02874105 -1.373282 1 2.318365 H441 H 0 -0.6523428 0.2256598 -1.237045 1 2.318365 H63 H 0 0.395373 0.7270881 0.3074492 1 1.2 H64 H 0 0.3806889 0.7534521 0.3713868 1 1.2 O6 O 0 0.3055297 0.7552813 0.3305727 1 1 H121 H 0 0.689283 0.7801527 0.4191098 1 1.2 H122 H 0 0.9644479 0.7525011 0.4127161 1 1.2 O12 O 0 0.7841341 0.7432474 0.4168845 1 1