# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_COMPOUNDNAME #============================================================================== _exptl_special_details ; Crystals were grown by vapour diffusion of diethyl ether into the chloroform/ methanol reaction mixture. They were isolated and dried in vacuo, but retained their crystallinity. ; _refine_special_details ; ? ; _cell_length_a 8.86510(19) _cell_length_b 9.19185(19) _cell_length_c 11.5192(2) _cell_angle_alpha 76.6530(17) _cell_angle_beta 77.0659(18) _cell_angle_gamma 85.5043(17) _cell_volume 889.78(3) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 0.0181 0.0091 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 0.0311 0.0180 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' Fe -1.1336 3.1974 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805 1.0369 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Se -0.7943 1.1372 17.0006 2.4098 5.8196 0.2726 3.9731 15.2372 4.3543 43.8163 2.8409 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C38 H28 Fe1 N14 Se2 # Dc = 1.67 Fooo = 448.00 Mu = 61.65 M = 447.25 # Found Formula = C38 H28 Fe1 N14 Se2 # Dc = 1.67 FOOO = 448.00 Mu = 61.65 M = 447.25 _chemical_formula_sum 'C38 H28 Fe1 N14 Se2' _chemical_formula_moiety 'C38 H28 Fe1 N14 Se2' _chemical_compound_source synthesized _chemical_formula_weight 894.50 _cell_measurement_temperature 100.01(14) _cell_measurement_reflns_used 15913 _cell_measurement_theta_min 4.0360 _cell_measurement_theta_max 76.5565 _exptl_crystal_description block _exptl_crystal_colour orange-red _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 6.165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.576 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Agilent Supernova' _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w/2\q _computing_data_collection 'CrysAlisPro (Agilent, 2011)' _computing_cell_refinement 'CrysAlisPro (Agilent, 2011)' _computing_data_reduction 'CrysAlisPro (Agilent, 2011)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 100.01(14) _diffrn_reflns_number 21108 _reflns_number_total 3713 _diffrn_reflns_av_R_equivalents 0.0292 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3713 # Theoretical number of reflections is about 7484 _diffrn_reflns_theta_min 4.036 _diffrn_reflns_theta_max 76.557 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 73.495 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 11 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 1.76 _oxford_diffrn_Wilson_scale 0.03 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.89 _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>0.0\s(I) _refine_ls_number_reflns 3696 _refine_ls_number_restraints 0 _refine_ls_number_parameters 250 _oxford_refine_ls_R_factor_ref 0.0287 _refine_ls_wR_factor_ref 0.0735 _refine_ls_goodness_of_fit_ref 1.0059 _refine_ls_shift/su_max 0.0004333 _refine_ls_shift/su_mean 0.0000235 # The values computed with all filters except I/sigma _oxford_reflns_number_all 3696 _refine_ls_R_factor_all 0.0287 _refine_ls_wR_factor_all 0.0735 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3668 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_gt 0.0732 # 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 #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.33P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 _atom_site_attached_hydrogens N1 N 0.0139(2) 1.07395(18) 0.16397(15) 0.0167 1.0000 Uani . . . . . . C2 C -0.0911(2) 1.1613(2) 0.2198(2) 0.0220 1.0000 Uani . . . . . . C3 C -0.0787(3) 1.1979(3) 0.3276(2) 0.0270 1.0000 Uani . . . . . . C4 C 0.0443(3) 1.1404(2) 0.38029(19) 0.0233 1.0000 Uani . . . . . . C5 C 0.1532(2) 1.0489(2) 0.32403(18) 0.0197 1.0000 Uani . . . . . . C6 C 0.1363(2) 1.0191(2) 0.21501(17) 0.0151 1.0000 Uani . . . . . . C7 C 0.2466(2) 0.9333(2) 0.13888(17) 0.0139 1.0000 Uani . . . . . . N8 N 0.37382(18) 0.84822(17) 0.16279(14) 0.0137 1.0000 Uani . . . . . . C9 C 0.4330(2) 0.7957(2) 0.05831(17) 0.0140 1.0000 Uani . . . . . . N10 N 0.34718(19) 0.84521(18) -0.02338(14) 0.0152 1.0000 Uani . . . . . . N11 N 0.23040(19) 0.93185(18) 0.02816(15) 0.0151 1.0000 Uani . . . . . . C12 C 0.5681(2) 0.6927(2) 0.03710(17) 0.0146 1.0000 Uani . . . . . . C13 C 0.6170(3) 0.5927(2) 0.13085(19) 0.0213 1.0000 Uani . . . . . . N14 N 0.7312(2) 0.4916(2) 0.10794(19) 0.0295 1.0000 Uani . . . . . . C15 C 0.7977(2) 0.4947(2) -0.0087(2) 0.0225 1.0000 Uani . . . . . . C16 C 0.7502(3) 0.5971(3) -0.1026(2) 0.0279 1.0000 Uani . . . . . . N17 N 0.6349(2) 0.6982(2) -0.08113(17) 0.0271 1.0000 Uani . . . . . . C18 C 0.4272(2) 0.8145(2) 0.27630(16) 0.0136 1.0000 Uani . . . . . . C19 C 0.5454(2) 0.8956(2) 0.28904(18) 0.0179 1.0000 Uani . . . . . . C20 C 0.5919(3) 0.8624(2) 0.39992(19) 0.0216 1.0000 Uani . . . . . . C21 C 0.5230(2) 0.7493(2) 0.49645(18) 0.0183 1.0000 Uani . . . . . . C22 C 0.4055(2) 0.6693(2) 0.47949(17) 0.0161 1.0000 Uani . . . . . . C23 C 0.3557(2) 0.7018(2) 0.36991(18) 0.0156 1.0000 Uani . . . . . . C24 C 0.5754(3) 0.7133(3) 0.6157(2) 0.0295 1.0000 Uani . . . . . . N31 N -0.0732(2) 0.79258(19) 0.12058(16) 0.0209 1.0000 Uani . . . . . . C32 C -0.0683(2) 0.7147(2) 0.21509(19) 0.0201 1.0000 Uani . . . . . . Se33 Se -0.05694(3) 0.59633(3) 0.36025(2) 0.0274 1.0000 Uani . . . . . . H51 H 0.7988 0.5981 -0.1819 0.0342 1.0000 Uiso R . . . . . H41 H 0.8760 0.4252 -0.0274 0.0270 1.0000 Uiso R . . . . . H21 H 0.5738 0.5936 0.2079 0.0274 1.0000 Uiso R . . . . . H141 H 0.2760 0.6490 0.3595 0.0188 1.0000 Uiso R . . . . . H131 H 0.3587 0.5901 0.5428 0.0190 1.0000 Uiso R . . . . . H151 H 0.5780 0.8014 0.6442 0.0449 1.0000 Uiso R . . . . . H153 H 0.5098 0.6447 0.6761 0.0455 1.0000 Uiso R . . . . . H152 H 0.6778 0.6711 0.6038 0.0451 1.0000 Uiso R . . . . . H111 H 0.6712 0.9160 0.4101 0.0265 1.0000 Uiso R . . . . . H101 H 0.5907 0.9708 0.2257 0.0216 1.0000 Uiso R . . . . . H221 H 0.2373 1.0077 0.3582 0.0234 1.0000 Uiso R . . . . . H211 H 0.0546 1.1629 0.4512 0.0287 1.0000 Uiso R . . . . . H201 H -0.1508 1.2625 0.3635 0.0323 1.0000 Uiso R . . . . . H191 H -0.1755 1.1992 0.1836 0.0260 1.0000 Uiso R . . . . . Fe1 Fe 0.0000 1.0000 0.0000 0.0111 1.0000 Uani S . . . . . 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 0.0180(8) 0.0148(8) 0.0159(8) -0.0029(6) -0.0030(6) 0.0045(6) C2 0.0208(10) 0.0198(10) 0.0242(10) -0.0069(8) -0.0034(8) 0.0084(8) C3 0.0264(11) 0.0258(11) 0.0280(11) -0.0135(9) 0.0013(9) 0.0065(9) C4 0.0278(11) 0.0239(10) 0.0182(10) -0.0093(8) -0.0009(8) 0.0020(8) C5 0.0237(10) 0.0188(9) 0.0170(9) -0.0056(7) -0.0053(8) 0.0047(8) C6 0.0160(9) 0.0131(8) 0.0143(9) -0.0012(7) -0.0021(7) 0.0031(7) C7 0.0146(9) 0.0129(8) 0.0134(8) -0.0018(7) -0.0032(7) 0.0030(7) N8 0.0142(8) 0.0139(7) 0.0123(7) -0.0022(6) -0.0033(6) 0.0039(6) C9 0.0151(9) 0.0126(8) 0.0124(8) -0.0012(7) -0.0013(7) 0.0016(7) N10 0.0154(8) 0.0149(7) 0.0135(7) -0.0029(6) -0.0016(6) 0.0050(6) N11 0.0146(8) 0.0157(7) 0.0139(7) -0.0029(6) -0.0027(6) 0.0054(6) C12 0.0126(9) 0.0142(8) 0.0165(9) -0.0034(7) -0.0026(7) 0.0017(7) C13 0.0254(11) 0.0202(10) 0.0166(9) -0.0025(8) -0.0057(8) 0.0084(8) N14 0.0306(11) 0.0275(10) 0.0296(10) -0.0052(8) -0.0104(8) 0.0126(8) C15 0.0174(10) 0.0183(10) 0.0325(11) -0.0112(8) -0.0026(8) 0.0046(8) C16 0.0208(11) 0.0377(13) 0.0214(11) -0.0086(9) 0.0033(8) 0.0048(9) N17 0.0230(9) 0.0346(10) 0.0195(9) -0.0036(8) -0.0012(7) 0.0074(8) C18 0.0150(9) 0.0134(8) 0.0118(8) -0.0030(7) -0.0034(7) 0.0055(7) C19 0.0212(10) 0.0161(9) 0.0144(9) 0.0006(7) -0.0033(7) -0.0017(7) C20 0.0258(11) 0.0203(10) 0.0198(10) -0.0019(8) -0.0083(8) -0.0047(8) C21 0.0241(10) 0.0170(9) 0.0136(9) -0.0029(7) -0.0053(8) 0.0032(8) C22 0.0180(9) 0.0130(8) 0.0138(9) -0.0007(7) 0.0006(7) 0.0031(7) C23 0.0144(9) 0.0136(8) 0.0177(9) -0.0030(7) -0.0024(7) 0.0023(7) C24 0.0450(14) 0.0270(11) 0.0186(10) -0.0003(9) -0.0141(10) -0.0070(10) N31 0.0221(9) 0.0160(8) 0.0199(9) 0.0022(7) -0.0015(7) 0.0014(7) C32 0.0174(10) 0.0181(9) 0.0234(10) -0.0048(8) -0.0008(8) -0.0004(7) Se33 0.02603(14) 0.02941(14) 0.02235(13) 0.00764(9) -0.00763(9) -0.00613(9) Fe1 0.0117(2) 0.01007(19) 0.00983(19) -0.00013(14) -0.00254(15) 0.00398(14) _refine_ls_extinction_method None _oxford_refine_ls_scale 6.04(10) 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 . 1.334(3) yes N1 . C6 . 1.357(3) yes N1 . Fe1 . 2.1806(17) yes C2 . C3 . 1.388(3) yes C2 . H191 . 0.942 no C3 . C4 . 1.376(3) yes C3 . H201 . 0.932 no C4 . C5 . 1.380(3) yes C4 . H211 . 0.913 no C5 . C6 . 1.387(3) yes C5 . H221 . 0.933 no C6 . C7 . 1.470(2) yes C7 . N8 . 1.364(2) yes C7 . N11 . 1.318(2) yes N8 . C9 . 1.379(2) yes N8 . C18 . 1.448(2) yes C9 . N10 . 1.319(2) yes C9 . C12 . 1.479(3) yes N10 . N11 . 1.368(2) yes N11 . Fe1 . 2.1614(16) yes C12 . C13 . 1.374(3) yes C12 . N17 . 1.349(3) yes C13 . N14 . 1.343(3) yes C13 . H21 . 0.887 no N14 . C15 . 1.336(3) yes C15 . C16 . 1.380(3) yes C15 . H41 . 0.929 no C16 . N17 . 1.347(3) yes C16 . H51 . 0.917 no C18 . C19 . 1.385(3) yes C18 . C23 . 1.385(3) yes C19 . C20 . 1.389(3) yes C19 . H101 . 0.922 no C20 . C21 . 1.397(3) yes C20 . H111 . 0.932 no C21 . C22 . 1.393(3) yes C21 . C24 . 1.505(3) yes C22 . C23 . 1.390(3) yes C22 . H131 . 0.949 no C23 . H141 . 0.932 no C24 . H151 . 0.945 no C24 . H153 . 0.945 no C24 . H152 . 0.952 no N31 . C32 . 1.165(3) yes N31 . Fe1 . 2.1338(17) yes C32 . Se33 . 1.791(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 C2 . N1 . C6 . 118.52(17) yes C2 . N1 . Fe1 . 125.28(14) yes C6 . N1 . Fe1 . 116.11(12) yes N1 . C2 . C3 . 122.2(2) yes N1 . C2 . H191 . 118.0 no C3 . C2 . H191 . 119.8 no C2 . C3 . C4 . 119.25(19) yes C2 . C3 . H201 . 121.0 no C4 . C3 . H201 . 119.8 no C3 . C4 . C5 . 119.2(2) yes C3 . C4 . H211 . 120.7 no C5 . C4 . H211 . 120.1 no C4 . C5 . C6 . 118.83(19) yes C4 . C5 . H221 . 120.9 no C6 . C5 . H221 . 120.2 no C5 . C6 . N1 . 121.97(17) yes C5 . C6 . C7 . 125.96(18) yes N1 . C6 . C7 . 112.02(16) yes C6 . C7 . N8 . 130.23(17) yes C6 . C7 . N11 . 120.41(17) yes N8 . C7 . N11 . 109.36(16) yes C7 . N8 . C9 . 104.71(15) yes C7 . N8 . C18 . 126.80(16) yes C9 . N8 . C18 . 128.39(16) yes N8 . C9 . N10 . 110.42(16) yes N8 . C9 . C12 . 127.20(17) yes N10 . C9 . C12 . 122.33(17) yes C9 . N10 . N11 . 106.52(15) yes N10 . N11 . C7 . 109.00(15) yes N10 . N11 . Fe1 . 134.49(13) yes C7 . N11 . Fe1 . 112.79(12) yes C9 . C12 . C13 . 122.38(18) yes C9 . C12 . N17 . 115.29(17) yes C13 . C12 . N17 . 122.24(18) yes C12 . C13 . N14 . 120.87(19) yes C12 . C13 . H21 . 120.6 no N14 . C13 . H21 . 118.5 no C13 . N14 . C15 . 117.62(19) yes N14 . C15 . C16 . 121.33(19) yes N14 . C15 . H41 . 119.5 no C16 . C15 . H41 . 119.1 no C15 . C16 . N17 . 121.7(2) yes C15 . C16 . H51 . 119.7 no N17 . C16 . H51 . 118.5 no C12 . N17 . C16 . 116.18(19) yes N8 . C18 . C19 . 119.77(17) yes N8 . C18 . C23 . 118.19(17) yes C19 . C18 . C23 . 122.03(18) yes C18 . C19 . C20 . 118.33(18) yes C18 . C19 . H101 . 120.5 no C20 . C19 . H101 . 121.1 no C19 . C20 . C21 . 121.35(19) yes C19 . C20 . H111 . 119.5 no C21 . C20 . H111 . 119.2 no C20 . C21 . C22 . 118.53(18) yes C20 . C21 . C24 . 120.86(19) yes C22 . C21 . C24 . 120.61(18) yes C21 . C22 . C23 . 121.16(18) yes C21 . C22 . H131 . 120.2 no C23 . C22 . H131 . 118.6 no C22 . C23 . C18 . 118.60(18) yes C22 . C23 . H141 . 120.8 no C18 . C23 . H141 . 120.6 no C21 . C24 . H151 . 110.4 no C21 . C24 . H153 . 111.7 no H151 . C24 . H153 . 109.0 no C21 . C24 . H152 . 109.4 no H151 . C24 . H152 . 107.5 no H153 . C24 . H152 . 108.7 no C32 . N31 . Fe1 . 144.60(17) yes N31 . C32 . Se33 . 178.82(19) yes N1 . Fe1 . N1 2_575 179.995 yes N1 . Fe1 . N11 . 75.36(6) yes N1 2_575 Fe1 . N11 . 104.64(6) yes N1 . Fe1 . N11 2_575 104.64(6) yes N1 2_575 Fe1 . N11 2_575 75.36(6) yes N11 . Fe1 . N11 2_575 179.995 yes N1 . Fe1 . N31 2_575 94.25(7) yes N1 2_575 Fe1 . N31 2_575 85.75(7) yes N11 . Fe1 . N31 2_575 93.61(6) yes N11 2_575 Fe1 . N31 2_575 86.39(6) yes N1 . Fe1 . N31 . 85.75(7) yes N1 2_575 Fe1 . N31 . 94.25(7) yes N11 . Fe1 . N31 . 86.39(6) yes N11 2_575 Fe1 . N31 . 93.61(6) yes N31 2_575 Fe1 . N31 . 179.995 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 C13 . H21 . C18 . 124 0.887 2.509 3.094(3) yes C19 . H101 . N10 2_675 163 0.922 2.519 3.410(3) yes C5 . H221 . C18 . 124 0.933 2.544 3.158(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 27/02/13 at 10:41:04 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 2,X'S) H ( 191,X'S) RIDE C ( 3,X'S) H ( 201,X'S) RIDE C ( 4,X'S) H ( 211,X'S) RIDE C ( 5,X'S) H ( 221,X'S) RIDE C ( 13,X'S) H ( 21,X'S) RIDE C ( 15,X'S) H ( 41,X'S) RIDE C ( 16,X'S) H ( 51,X'S) RIDE C ( 19,X'S) H ( 101,X'S) RIDE C ( 20,X'S) H ( 111,X'S) RIDE C ( 22,X'S) H ( 131,X'S) RIDE C ( 23,X'S) H ( 141,X'S) RIDE C ( 24,X'S) H ( 151,X'S) H ( 153,X'S) H ( 152,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 27/02/13 at 10:41:04 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details -10 1 0 x . 2 2 1 x . _database_code_depnum_ccdc_archive 'CCDC 937363' ####################################################################### # # 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_COMPOUNDNAME #============================================================================== _exptl_special_details ; Crystals were grown by vapour diffusion of diethyl ether into the chloroform/ methanol reaction mixture. They were isolated and dried in vacuo, but retained their crystallinity. ; _refine_special_details ; ? ; _cell_length_a 8.9760(3) _cell_length_b 9.2721(6) _cell_length_c 11.5674(7) _cell_angle_alpha 76.218(5) _cell_angle_beta 77.043(4) _cell_angle_gamma 84.919(4) _cell_volume 910.57(9) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 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 0.0181 0.0091 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 0.0311 0.0180 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' Fe -1.1336 3.1974 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805 1.0369 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Se -0.7943 1.1372 17.0006 2.4098 5.8196 0.2726 3.9731 15.2372 4.3543 43.8163 2.8409 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C38 H28 Fe1 N14 Se2 # Dc = 1.63 Fooo = 448.00 Mu = 60.24 M = 447.25 # Found Formula = C38 H28 Fe1 N14 Se2 # Dc = 1.63 FOOO = 448.00 Mu = 60.24 M = 447.25 _chemical_formula_sum 'C38 H28 Fe1 N14 Se2' _chemical_formula_moiety 'C38 H28 Fe1 N14 Se2' _chemical_compound_source synthesized _chemical_formula_weight 894.50 _cell_measurement_temperature 260.01(10) _cell_measurement_reflns_used 4729 _cell_measurement_theta_min 4.0247 _cell_measurement_theta_max 76.5304 _exptl_crystal_description block _exptl_crystal_colour orange-red _exptl_crystal_size_min 0.080 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_max 0.220 _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 6.024 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.604 _exptl_absorpt_correction_T_max 1.00 _diffrn_measurement_device_type 'Agilent Supernova' _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w/2\q _computing_data_collection 'CrysAlisPro (Agilent, 2011)' _computing_cell_refinement 'CrysAlisPro (Agilent, 2011)' _computing_data_reduction 'CrysAlisPro (Agilent, 2011)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 260.01(10) _diffrn_reflns_number 7500 _reflns_number_total 3730 _diffrn_reflns_av_R_equivalents 0.0234 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3730 # Theoretical number of reflections is about 7657 _diffrn_reflns_theta_min 4.025 _diffrn_reflns_theta_max 76.531 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 74.338 _diffrn_measured_fraction_theta_full 0.983 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -10 _reflns_limit_h_max 11 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _oxford_diffrn_Wilson_B_factor 3.46 _oxford_diffrn_Wilson_scale 0.03 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.74 _refine_diff_density_max 0.51 # 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 3715 _refine_ls_number_restraints 0 _refine_ls_number_parameters 250 _oxford_refine_ls_R_factor_ref 0.0389 _refine_ls_wR_factor_ref 0.1012 _refine_ls_goodness_of_fit_ref 0.9956 _refine_ls_shift/su_max 0.0003529 _refine_ls_shift/su_mean 0.0000137 # The values computed with all filters except I/sigma _oxford_reflns_number_all 3715 _refine_ls_R_factor_all 0.0389 _refine_ls_wR_factor_all 0.1012 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3529 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_gt 0.0984 # 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 #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.65P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 _atom_site_attached_hydrogens C12 C 0.5634(3) 0.1934(3) 0.0382(2) 0.0323 1.0000 Uani . . . . . . C13 C 0.6127(3) 0.0948(3) 0.1315(2) 0.0460 1.0000 Uani . . . . . . N14 N 0.7276(3) -0.0047(3) 0.1085(3) 0.0611 1.0000 Uani . . . . . . C15 C 0.7932(3) -0.0013(3) -0.0072(3) 0.0498 1.0000 Uani . . . . . . C16 C 0.7453(4) 0.0994(4) -0.1004(3) 0.0592 1.0000 Uani . . . . . . N17 N 0.6303(3) 0.1995(3) -0.0789(2) 0.0572 1.0000 Uani . . . . . . C18 C 0.4242(2) 0.3143(2) 0.27575(19) 0.0293 1.0000 Uani . . . . . . C19 C 0.3545(3) 0.2042(3) 0.3705(2) 0.0342 1.0000 Uani . . . . . . C20 C 0.4047(3) 0.1718(3) 0.4788(2) 0.0361 1.0000 Uani . . . . . . C21 C 0.5226(3) 0.2497(3) 0.4935(2) 0.0387 1.0000 Uani . . . . . . C22 C 0.5892(3) 0.3599(3) 0.3963(3) 0.0459 1.0000 Uani . . . . . . C23 C 0.5419(3) 0.3932(3) 0.2869(2) 0.0396 1.0000 Uani . . . . . . C24 C 0.5762(5) 0.2138(4) 0.6119(3) 0.0608 1.0000 Uani . . . . . . N31 N 0.0710(3) 0.7069(3) -0.1196(2) 0.0466 1.0000 Uani . . . . . . C32 C 0.0654(3) 0.7851(3) -0.2128(2) 0.0396 1.0000 Uani . . . . . . Se33 Se 0.05330(4) 0.90501(4) -0.35656(3) 0.0614 1.0000 Uani . . . . . . N1 N 0.0133(2) 0.5723(2) 0.16386(18) 0.0349 1.0000 Uani . . . . . . C2 C -0.0916(3) 0.6585(3) 0.2196(3) 0.0459 1.0000 Uani . . . . . . C3 C -0.0783(4) 0.6953(4) 0.3259(3) 0.0555 1.0000 Uani . . . . . . C4 C 0.0440(4) 0.6398(3) 0.3773(3) 0.0504 1.0000 Uani . . . . . . C5 C 0.1528(3) 0.5498(3) 0.3214(2) 0.0425 1.0000 Uani . . . . . . C6 C 0.1353(3) 0.5188(2) 0.2143(2) 0.0326 1.0000 Uani . . . . . . C7 C 0.2445(2) 0.4332(2) 0.1385(2) 0.0308 1.0000 Uani . . . . . . N8 N 0.3706(2) 0.3480(2) 0.16289(17) 0.0301 1.0000 Uani . . . . . . C9 C 0.4291(2) 0.2954(2) 0.0594(2) 0.0306 1.0000 Uani . . . . . . N10 N 0.3442(2) 0.3448(2) -0.02178(17) 0.0338 1.0000 Uani . . . . . . N11 N 0.2283(2) 0.4314(2) 0.02902(18) 0.0334 1.0000 Uani . . . . . . Fe1 Fe 0.0000 0.5000 0.0000 0.0285 1.0000 Uani S . . . . . H201 H 0.7931 0.0990 -0.1783 0.0715 1.0000 Uiso R . . . . . H191 H 0.8730 -0.0675 -0.0245 0.0596 1.0000 Uiso R . . . . . H171 H 0.5714 0.0939 0.2078 0.0559 1.0000 Uiso R . . . . . H271 H 0.2760 0.1529 0.3612 0.0419 1.0000 Uiso R . . . . . H261 H 0.3583 0.0973 0.5421 0.0425 1.0000 Uiso R . . . . . H282 H 0.5105 0.1479 0.6742 0.0917 1.0000 Uiso R . . . . . H281 H 0.5798 0.3006 0.6389 0.0914 1.0000 Uiso R . . . . . H283 H 0.6770 0.1688 0.6018 0.0912 1.0000 Uiso R . . . . . H241 H 0.6675 0.4135 0.4051 0.0553 1.0000 Uiso R . . . . . H231 H 0.5870 0.4659 0.2233 0.0487 1.0000 Uiso R . . . . . H51 H 0.2367 0.5102 0.3550 0.0505 1.0000 Uiso R . . . . . H41 H 0.0550 0.6623 0.4485 0.0604 1.0000 Uiso R . . . . . H31 H -0.1494 0.7591 0.3613 0.0674 1.0000 Uiso R . . . . . H21 H -0.1758 0.6960 0.1842 0.0550 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 C12 0.0276(10) 0.0335(11) 0.0355(11) -0.0091(9) -0.0074(8) 0.0053(8) C13 0.0481(14) 0.0493(14) 0.0382(13) -0.0097(11) -0.0135(11) 0.0221(12) N14 0.0591(15) 0.0591(15) 0.0662(17) -0.0177(13) -0.0240(13) 0.0289(13) C15 0.0356(12) 0.0450(14) 0.0711(19) -0.0247(13) -0.0095(12) 0.0135(11) C16 0.0455(15) 0.073(2) 0.0507(17) -0.0174(15) 0.0041(13) 0.0170(14) N17 0.0486(13) 0.0692(16) 0.0439(13) -0.0087(11) -0.0023(10) 0.0201(12) C18 0.0273(10) 0.0319(10) 0.0290(10) -0.0075(8) -0.0089(8) 0.0075(8) C19 0.0285(10) 0.0349(11) 0.0381(12) -0.0064(9) -0.0083(9) 0.0020(8) C20 0.0372(12) 0.0349(11) 0.0314(11) -0.0035(9) -0.0037(9) 0.0045(9) C21 0.0443(13) 0.0403(12) 0.0329(12) -0.0072(9) -0.0140(10) 0.0036(10) C22 0.0491(15) 0.0487(14) 0.0432(14) -0.0048(11) -0.0191(11) -0.0101(11) C23 0.0391(12) 0.0423(13) 0.0358(12) -0.0008(10) -0.0109(10) -0.0065(10) C24 0.085(2) 0.0613(18) 0.0419(15) -0.0039(13) -0.0312(16) -0.0084(16) N31 0.0485(12) 0.0382(11) 0.0473(13) -0.0007(9) -0.0090(10) 0.0020(9) C32 0.0364(12) 0.0353(12) 0.0438(14) -0.0049(10) -0.0064(10) -0.0003(9) Se33 0.0580(2) 0.0660(2) 0.0522(2) 0.01306(15) -0.01952(15) -0.01181(15) N1 0.0322(9) 0.0355(10) 0.0366(10) -0.0092(8) -0.0096(8) 0.0098(8) C2 0.0392(13) 0.0470(14) 0.0506(15) -0.0168(12) -0.0088(11) 0.0166(11) C3 0.0500(16) 0.0587(17) 0.0576(17) -0.0278(14) -0.0020(13) 0.0157(13) C4 0.0561(16) 0.0555(16) 0.0424(14) -0.0242(12) -0.0053(12) 0.0061(13) C5 0.0452(14) 0.0463(13) 0.0394(13) -0.0161(11) -0.0132(11) 0.0091(11) C6 0.0317(11) 0.0323(10) 0.0324(11) -0.0068(8) -0.0079(9) 0.0068(8) C7 0.0280(10) 0.0324(10) 0.0314(11) -0.0059(8) -0.0090(8) 0.0066(8) N8 0.0267(9) 0.0336(9) 0.0301(9) -0.0072(7) -0.0097(7) 0.0082(7) C9 0.0273(10) 0.0330(10) 0.0303(10) -0.0058(8) -0.0076(8) 0.0053(8) N10 0.0302(9) 0.0398(10) 0.0306(9) -0.0091(8) -0.0082(7) 0.0110(7) N11 0.0295(9) 0.0384(10) 0.0319(9) -0.0084(8) -0.0102(7) 0.0125(7) Fe1 0.0260(2) 0.0302(2) 0.0279(2) -0.00399(18) -0.00934(18) 0.00876(17) _refine_ls_extinction_method None _oxford_refine_ls_scale 6.30(15) 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 C12 . C13 . 1.367(3) yes C12 . N17 . 1.343(3) yes C12 . C9 . 1.478(3) yes C13 . N14 . 1.346(3) yes C13 . H171 . 0.876 no N14 . C15 . 1.330(4) yes C15 . C16 . 1.370(5) yes C15 . H191 . 0.920 no C16 . N17 . 1.347(4) yes C16 . H201 . 0.908 no C18 . C19 . 1.381(3) yes C18 . C23 . 1.382(3) yes C18 . N8 . 1.447(3) yes C19 . C20 . 1.383(3) yes C19 . H271 . 0.923 no C20 . C21 . 1.395(4) yes C20 . H261 . 0.928 no C21 . C22 . 1.387(4) yes C21 . C24 . 1.506(4) yes C22 . C23 . 1.382(4) yes C22 . H241 . 0.932 no C23 . H231 . 0.916 no C24 . H282 . 0.951 no C24 . H281 . 0.936 no C24 . H283 . 0.957 no N31 . C32 . 1.155(4) yes N31 . Fe1 . 2.135(2) yes C32 . Se33 . 1.787(3) yes N1 . C2 . 1.334(3) yes N1 . C6 . 1.356(3) yes N1 . Fe1 . 2.186(2) yes C2 . C3 . 1.385(4) yes C2 . H21 . 0.940 no C3 . C4 . 1.368(5) yes C3 . H31 . 0.925 no C4 . C5 . 1.378(4) yes C4 . H41 . 0.924 no C5 . C6 . 1.380(3) yes C5 . H51 . 0.932 no C6 . C7 . 1.473(3) yes C7 . N8 . 1.365(3) yes C7 . N11 . 1.311(3) yes N8 . C9 . 1.377(3) yes C9 . N10 . 1.314(3) yes N10 . N11 . 1.369(3) yes N11 . Fe1 . 2.1663(18) 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 C13 . C12 . N17 . 122.0(2) yes C13 . C12 . C9 . 122.2(2) yes N17 . C12 . C9 . 115.7(2) yes C12 . C13 . N14 . 120.6(3) yes C12 . C13 . H171 . 121.7 no N14 . C13 . H171 . 117.6 no C13 . N14 . C15 . 117.8(3) yes N14 . C15 . C16 . 121.4(2) yes N14 . C15 . H191 . 119.0 no C16 . C15 . H191 . 119.7 no C15 . C16 . N17 . 121.5(3) yes C15 . C16 . H201 . 119.0 no N17 . C16 . H201 . 119.5 no C16 . N17 . C12 . 116.6(3) yes C19 . C18 . C23 . 121.6(2) yes C19 . C18 . N8 . 118.6(2) yes C23 . C18 . N8 . 119.7(2) yes C18 . C19 . C20 . 119.0(2) yes C18 . C19 . H271 . 120.3 no C20 . C19 . H271 . 120.7 no C19 . C20 . C21 . 120.9(2) yes C19 . C20 . H261 . 118.9 no C21 . C20 . H261 . 120.2 no C20 . C21 . C22 . 118.3(2) yes C20 . C21 . C24 . 120.5(2) yes C22 . C21 . C24 . 121.2(3) yes C21 . C22 . C23 . 121.7(2) yes C21 . C22 . H241 . 119.3 no C23 . C22 . H241 . 119.0 no C18 . C23 . C22 . 118.4(2) yes C18 . C23 . H231 . 120.7 no C22 . C23 . H231 . 120.9 no C21 . C24 . H282 . 112.1 no C21 . C24 . H281 . 110.4 no H282 . C24 . H281 . 107.9 no C21 . C24 . H283 . 110.7 no H282 . C24 . H283 . 108.1 no H281 . C24 . H283 . 107.5 no C32 . N31 . Fe1 . 144.7(2) yes N31 . C32 . Se33 . 178.9(2) yes C2 . N1 . C6 . 118.5(2) yes C2 . N1 . Fe1 . 125.13(17) yes C6 . N1 . Fe1 . 116.32(15) yes N1 . C2 . C3 . 121.9(2) yes N1 . C2 . H21 . 118.4 no C3 . C2 . H21 . 119.7 no C2 . C3 . C4 . 119.4(2) yes C2 . C3 . H31 . 120.9 no C4 . C3 . H31 . 119.6 no C3 . C4 . C5 . 119.3(3) yes C3 . C4 . H41 . 121.0 no C5 . C4 . H41 . 119.7 no C4 . C5 . C6 . 118.8(2) yes C4 . C5 . H51 . 120.8 no C6 . C5 . H51 . 120.4 no C5 . C6 . N1 . 122.0(2) yes C5 . C6 . C7 . 126.1(2) yes N1 . C6 . C7 . 111.84(19) yes C6 . C7 . N8 . 130.0(2) yes C6 . C7 . N11 . 120.59(19) yes N8 . C7 . N11 . 109.36(19) yes C18 . N8 . C7 . 126.99(18) yes C18 . N8 . C9 . 128.16(17) yes C7 . N8 . C9 . 104.76(17) yes C12 . C9 . N8 . 127.45(19) yes C12 . C9 . N10 . 122.2(2) yes N8 . C9 . N10 . 110.27(18) yes C9 . N10 . N11 . 106.65(18) yes N10 . N11 . C7 . 108.96(17) yes N10 . N11 . Fe1 . 134.38(15) yes C7 . N11 . Fe1 . 113.01(14) yes N1 2_565 Fe1 . N1 . 179.995 yes N1 2_565 Fe1 . N11 . 104.87(7) yes N1 . Fe1 . N11 . 75.13(7) yes N1 2_565 Fe1 . N11 2_565 75.13(7) yes N1 . Fe1 . N11 2_565 104.87(7) yes N11 . Fe1 . N11 2_565 179.995 yes N1 2_565 Fe1 . N31 . 86.03(9) yes N1 . Fe1 . N31 . 93.97(9) yes N11 . Fe1 . N31 . 93.62(8) yes N11 2_565 Fe1 . N31 . 86.38(8) yes N1 2_565 Fe1 . N31 2_565 93.97(9) yes N1 . Fe1 . N31 2_565 86.03(9) yes N11 . Fe1 . N31 2_565 86.38(8) yes N11 2_565 Fe1 . N31 2_565 93.62(8) yes N31 . Fe1 . N31 2_565 179.995 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 C13 . H171 . C18 . 123 0.876 2.523 3.088(4) yes C23 . H231 . N10 2_665 165 0.916 2.548 3.440(4) yes C5 . H51 . C18 . 123 0.932 2.556 3.164(4) yes _iucr_refine_instruction_details_constraints ; # # Punched on 27/02/13 at 10:47:08 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 13,X'S) H ( 171,X'S) RIDE C ( 15,X'S) H ( 191,X'S) RIDE C ( 16,X'S) H ( 201,X'S) RIDE C ( 19,X'S) H ( 271,X'S) RIDE C ( 20,X'S) H ( 261,X'S) RIDE C ( 22,X'S) H ( 241,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 282,X'S) H ( 281,X'S) H ( 283,X'S) RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 5,X'S) H ( 51,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 27/02/13 at 10:47:08 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 937364' ####################################################################### # # 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_rwh2_35 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 N6' _chemical_formula_weight 314.35 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.2509(13) _cell_length_b 6.8857(9) _cell_length_c 17.815(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.229(5) _cell_angle_gamma 90.00 _cell_volume 1500.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5351 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 26.06 _exptl_crystal_description 'irregular chunk' _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9404 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details 'SCALE (Bruker AXS Inc.)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX II area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19001 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3057 _reflns_number_gt 2593 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The pyridine and pyrazine rings were distingushed, and the position of the nitrogen atoms determined, by looking for Q peaks representing hydrogen atoms. The pyridine ring presented four carbon atoms with Q peaks at appropriate distances and angles to be sp3 bound hydrogen atoms. In contrast, the pyrazine ring present three carbons atoms with Q peaks meeting such requirements. At the pyrazine ring was a fourth Q peak that could have possibly been a hydrogen atom, but the C-H angle was longer than all the other hydrogen atoms and the Q peak was the smallest of the Q list. The ring atom was also para to the other nitrogen atom of the heterocyclic, confirming that is the other nitrogen atom. ; _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^)+(0.0472P)^2^+0.6447P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3057 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.43000(12) 0.2426(2) 0.51198(8) 0.0228(3) Uani 1 1 d . . . N1 N 0.49602(11) 0.25667(18) 0.45622(7) 0.0275(3) Uani 1 1 d . . . N2 N 0.60103(11) 0.27214(19) 0.48746(7) 0.0271(3) Uani 1 1 d . . . C2 C 0.59548(12) 0.2668(2) 0.56100(8) 0.0222(3) Uani 1 1 d . . . C3 C 0.69239(12) 0.2755(2) 0.61337(9) 0.0237(3) Uani 1 1 d . . . C4 C 0.79007(12) 0.3472(2) 0.58831(10) 0.0318(4) Uani 1 1 d . . . H4 H 0.7920 0.3931 0.5381 0.038 Uiso 1 1 calc R . . N3 N 0.88164(12) 0.3530(2) 0.63321(10) 0.0471(4) Uani 1 1 d . . . C5 C 0.87296(14) 0.2873(3) 0.70443(12) 0.0391(4) Uani 1 1 d . . . H5 H 0.9350 0.2924 0.7389 0.047 Uiso 1 1 calc R . . C6 C 0.77580(13) 0.2133(3) 0.72791(10) 0.0325(4) Uani 1 1 d . . . H6 H 0.7737 0.1655 0.7778 0.039 Uiso 1 1 calc R . . N4 N 0.68464(10) 0.20611(19) 0.68319(7) 0.0265(3) Uani 1 1 d . . . N5 N 0.48891(10) 0.24840(17) 0.57973(6) 0.0199(3) Uani 1 1 d . . . C7 C 0.44779(11) 0.2434(2) 0.65408(8) 0.0194(3) Uani 1 1 d . . . C8 C 0.44353(11) 0.4137(2) 0.69457(8) 0.0223(3) Uani 1 1 d . . . H8 H 0.4685 0.5322 0.6743 0.027 Uiso 1 1 calc R . . C9 C 0.40210(12) 0.4086(2) 0.76542(8) 0.0250(3) Uani 1 1 d . . . H9 H 0.3995 0.5249 0.7940 0.030 Uiso 1 1 calc R . . C10 C 0.36424(11) 0.2362(2) 0.79545(8) 0.0230(3) Uani 1 1 d . . . C11 C 0.31609(13) 0.2309(3) 0.87150(9) 0.0312(4) Uani 1 1 d . . . H11A H 0.3094 0.3636 0.8906 0.037 Uiso 1 1 calc R . . H11B H 0.3639 0.1554 0.9064 0.037 Uiso 1 1 calc R . . H11C H 0.2437 0.1702 0.8669 0.037 Uiso 1 1 calc R . . C12 C 0.37007(11) 0.0671(2) 0.75293(8) 0.0234(3) Uani 1 1 d . . . H12 H 0.3447 -0.0518 0.7727 0.028 Uiso 1 1 calc R . . C13 C 0.41223(11) 0.0690(2) 0.68230(8) 0.0223(3) Uani 1 1 d . . . H13 H 0.4166 -0.0472 0.6539 0.027 Uiso 1 1 calc R . . C14 C 0.31049(13) 0.2256(2) 0.49977(9) 0.0253(3) Uani 1 1 d . . . N6 N 0.24633(11) 0.2648(2) 0.55682(8) 0.0327(3) Uani 1 1 d . . . C15 C 0.13790(14) 0.2493(3) 0.54252(11) 0.0390(4) Uani 1 1 d . . . H15 H 0.0908 0.2768 0.5818 0.047 Uiso 1 1 calc R . . C16 C 0.09237(16) 0.1955(3) 0.47366(13) 0.0501(6) Uani 1 1 d . . . H16 H 0.0153 0.1838 0.4660 0.060 Uiso 1 1 calc R . . C17 C 0.15929(17) 0.1583(3) 0.41552(12) 0.0469(5) Uani 1 1 d . . . H17 H 0.1290 0.1233 0.3671 0.056 Uiso 1 1 calc R . . C18 C 0.26909(14) 0.1725(2) 0.42875(9) 0.0332(4) Uani 1 1 d . . . H18 H 0.3170 0.1464 0.3898 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0305(8) 0.0171(7) 0.0207(7) -0.0001(6) 0.0023(6) 0.0033(6) N1 0.0360(8) 0.0238(7) 0.0234(7) 0.0000(5) 0.0062(6) 0.0050(6) N2 0.0316(7) 0.0259(7) 0.0249(7) 0.0019(5) 0.0104(5) 0.0044(5) C2 0.0242(7) 0.0175(7) 0.0259(8) 0.0017(6) 0.0100(6) 0.0024(6) C3 0.0224(7) 0.0191(7) 0.0304(8) 0.0008(6) 0.0077(6) 0.0031(6) C4 0.0242(8) 0.0294(9) 0.0427(10) 0.0096(7) 0.0092(7) 0.0039(7) N3 0.0297(8) 0.0359(9) 0.0759(12) 0.0125(8) 0.0039(8) 0.0002(7) C5 0.0250(8) 0.0292(9) 0.0619(12) 0.0039(9) -0.0075(8) 0.0002(7) C6 0.0292(9) 0.0325(9) 0.0354(9) -0.0018(7) -0.0017(7) 0.0026(7) N4 0.0229(6) 0.0296(7) 0.0272(7) -0.0004(6) 0.0029(5) 0.0014(5) N5 0.0218(6) 0.0193(6) 0.0192(6) 0.0006(5) 0.0047(5) 0.0013(5) C7 0.0160(7) 0.0240(8) 0.0182(7) 0.0014(6) 0.0021(5) 0.0018(5) C8 0.0196(7) 0.0217(8) 0.0260(8) 0.0007(6) 0.0033(6) -0.0021(6) C9 0.0241(7) 0.0256(8) 0.0258(8) -0.0047(6) 0.0048(6) 0.0001(6) C10 0.0168(7) 0.0300(8) 0.0226(7) 0.0002(6) 0.0035(6) 0.0005(6) C11 0.0320(9) 0.0362(10) 0.0264(8) -0.0019(7) 0.0091(7) -0.0028(7) C12 0.0212(7) 0.0238(8) 0.0256(8) 0.0044(6) 0.0031(6) -0.0010(6) C13 0.0223(7) 0.0211(8) 0.0236(7) -0.0002(6) 0.0021(6) 0.0007(6) C14 0.0308(8) 0.0169(7) 0.0276(8) 0.0027(6) -0.0028(6) 0.0005(6) N6 0.0285(7) 0.0332(8) 0.0363(8) 0.0090(6) 0.0020(6) -0.0010(6) C15 0.0257(9) 0.0385(10) 0.0524(11) 0.0172(8) -0.0010(8) -0.0036(7) C16 0.0346(10) 0.0362(11) 0.0766(15) 0.0203(10) -0.0230(10) -0.0120(8) C17 0.0567(12) 0.0274(10) 0.0531(12) -0.0001(9) -0.0279(10) -0.0055(9) C18 0.0440(10) 0.0225(8) 0.0319(9) -0.0030(7) -0.0092(7) 0.0032(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.3194(19) . ? C1 N5 1.3715(19) . ? C1 C14 1.473(2) . ? N1 N2 1.3767(19) . ? N2 C2 1.3162(19) . ? C2 N5 1.3716(18) . ? C2 C3 1.469(2) . ? C3 N4 1.341(2) . ? C3 C4 1.391(2) . ? C4 N3 1.341(2) . ? C4 H4 0.9500 . ? N3 C5 1.357(3) . ? C5 C6 1.381(2) . ? C5 H5 0.9500 . ? C6 N4 1.336(2) . ? C6 H6 0.9500 . ? N5 C7 1.4438(17) . ? C7 C8 1.379(2) . ? C7 C13 1.382(2) . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 C10 1.393(2) . ? C9 H9 0.9500 . ? C10 C12 1.393(2) . ? C10 C11 1.508(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 N6 1.347(2) . ? C14 C18 1.385(2) . ? N6 C15 1.343(2) . ? C15 C16 1.370(3) . ? C15 H15 0.9500 . ? C16 C17 1.381(3) . ? C16 H16 0.9500 . ? C17 C18 1.356(3) . ? C17 H17 0.9500 . ? C18 H18 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 N1 C1 N5 110.24(13) . . ? N1 C1 C14 122.77(14) . . ? N5 C1 C14 126.99(13) . . ? C1 N1 N2 107.44(12) . . ? C2 N2 N1 107.51(12) . . ? N2 C2 N5 110.36(13) . . ? N2 C2 C3 123.07(13) . . ? N5 C2 C3 126.56(13) . . ? N4 C3 C4 122.09(15) . . ? N4 C3 C2 118.53(13) . . ? C4 C3 C2 119.32(14) . . ? N3 C4 C3 121.67(16) . . ? N3 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 N3 C5 116.15(15) . . ? N3 C5 C6 121.36(16) . . ? N3 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? N4 C6 C5 122.61(17) . . ? N4 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? C6 N4 C3 116.08(14) . . ? C1 N5 C2 104.45(12) . . ? C1 N5 C7 127.82(12) . . ? C2 N5 C7 127.69(12) . . ? C8 C7 C13 121.78(13) . . ? C8 C7 N5 119.02(12) . . ? C13 C7 N5 119.19(12) . . ? C7 C8 C9 118.77(14) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C8 C9 C10 121.18(14) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C9 C10 C12 118.39(13) . . ? C9 C10 C11 121.42(14) . . ? C12 C10 C11 120.17(14) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C10 121.22(14) . . ? C13 C12 H12 119.4 . . ? C10 C12 H12 119.4 . . ? C7 C13 C12 118.65(14) . . ? C7 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? N6 C14 C18 122.89(16) . . ? N6 C14 C1 119.35(14) . . ? C18 C14 C1 117.75(15) . . ? C15 N6 C14 117.01(16) . . ? N6 C15 C16 122.69(19) . . ? N6 C15 H15 118.7 . . ? C16 C15 H15 118.7 . . ? C15 C16 C17 119.54(17) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 118.77(17) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C17 C18 C14 119.10(18) . . ? C17 C18 H18 120.5 . . ? C14 C18 H18 120.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.247 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 937365'