# 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_Compound1 #TrackingRef 'Compound1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 Mg N2 O8' _chemical_formula_weight 288.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mg Mg 0.0486 0.0363 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.5673(5) _cell_length_b 9.3773(5) _cell_length_c 7.7862(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.734(7) _cell_angle_gamma 90.00 _cell_volume 523.25(5) _cell_formula_units_Z 2 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 1305 _cell_measurement_theta_min 3.5079 _cell_measurement_theta_max 29.0071 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9582 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 301(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _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 2354 _diffrn_reflns_av_R_equivalents 0.0127 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1021 _reflns_number_gt 927 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.3314P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1021 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_restrained_S_all 1.192 _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 Mg1 Mg 1.0000 1.0000 0.0000 0.0163(3) Uani 1 2 d S . . O2 O 0.9704(2) 1.40101(15) 0.24897(19) 0.0246(4) Uani 1 1 d . . . O1 O 0.5107(2) 1.21512(16) 0.0016(2) 0.0312(4) Uani 1 1 d . . . O1W O 1.2823(2) 1.00534(18) 0.0627(2) 0.0281(4) Uani 1 1 d . . . O3 O 1.02140(19) 1.19382(14) 0.1334(2) 0.0244(4) Uani 1 1 d . . . C2 C 0.5103(3) 1.3475(2) -0.0018(3) 0.0197(5) Uani 1 1 d . . . N1 N 0.6411(2) 1.42296(17) -0.0327(2) 0.0190(4) Uani 1 1 d . . . C1 C 0.6488(3) 1.5783(2) -0.0283(3) 0.0223(5) Uani 1 1 d . . . H1A H 0.6600 1.6113 -0.1425 0.027 Uiso 1 1 calc R . . H1B H 0.7615 1.6068 0.0668 0.027 Uiso 1 1 calc R . . C4 C 0.9409(3) 1.3102(2) 0.1227(3) 0.0172(4) Uani 1 1 d . . . C3 C 0.7948(3) 1.3488(2) -0.0616(3) 0.0194(4) Uani 1 1 d . . . H3A H 0.8521 1.4085 -0.1307 0.023 Uiso 1 1 calc R . . H3B H 0.7503 1.2625 -0.1306 0.023 Uiso 1 1 calc R . . H1WA H 1.336(5) 1.080(4) 0.043(4) 0.054(10) Uiso 1 1 d . . . H1WB H 1.346(3) 0.929(3) 0.042(3) 0.026(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mg1 0.0157(5) 0.0126(5) 0.0205(5) 0.0011(3) 0.0059(4) 0.0016(3) O2 0.0282(8) 0.0200(8) 0.0244(8) -0.0087(6) 0.0068(6) -0.0001(6) O1 0.0257(8) 0.0139(8) 0.0586(11) 0.0010(7) 0.0201(8) 0.0020(6) O1W 0.0190(8) 0.0186(8) 0.0489(10) 0.0012(7) 0.0141(7) -0.0008(6) O3 0.0237(7) 0.0163(7) 0.0291(8) -0.0026(6) 0.0026(6) 0.0052(6) C2 0.0174(9) 0.0151(10) 0.0257(10) 0.0014(8) 0.0058(8) 0.0012(7) N1 0.0153(8) 0.0141(9) 0.0279(9) -0.0002(7) 0.0074(7) 0.0024(6) C1 0.0173(9) 0.0159(11) 0.0349(12) 0.0020(8) 0.0100(8) 0.0008(7) C4 0.0162(9) 0.0153(9) 0.0226(10) -0.0007(8) 0.0097(8) -0.0011(7) C3 0.0176(9) 0.0176(10) 0.0251(10) -0.0011(8) 0.0098(8) 0.0027(8) _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 Mg1 O1W 2.0336(15) . ? Mg1 O1W 2.0336(15) 3_775 ? Mg1 O3 2.0738(14) 3_775 ? Mg1 O3 2.0738(14) . ? Mg1 O2 2.1097(14) 4_585 ? Mg1 O2 2.1097(14) 2_745 ? O2 C4 1.265(2) . ? O2 Mg1 2.1097(14) 2_755 ? O1 C2 1.242(3) . ? O3 C4 1.240(2) . ? C2 N1 1.300(3) . ? C2 C1 1.473(3) 3_685 ? N1 C3 1.434(2) . ? N1 C1 1.458(3) . ? C1 C2 1.473(3) 3_685 ? C4 C3 1.547(3) . ? 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 O1W Mg1 O1W 180.00(9) . 3_775 ? O1W Mg1 O3 92.80(6) . 3_775 ? O1W Mg1 O3 87.20(6) 3_775 3_775 ? O1W Mg1 O3 87.20(6) . . ? O1W Mg1 O3 92.80(6) 3_775 . ? O3 Mg1 O3 180.00(7) 3_775 . ? O1W Mg1 O2 90.13(6) . 4_585 ? O1W Mg1 O2 89.87(6) 3_775 4_585 ? O3 Mg1 O2 87.34(6) 3_775 4_585 ? O3 Mg1 O2 92.66(6) . 4_585 ? O1W Mg1 O2 89.87(6) . 2_745 ? O1W Mg1 O2 90.13(6) 3_775 2_745 ? O3 Mg1 O2 92.66(6) 3_775 2_745 ? O3 Mg1 O2 87.34(6) . 2_745 ? O2 Mg1 O2 180.00(7) 4_585 2_745 ? C4 O2 Mg1 162.92(14) . 2_755 ? C4 O3 Mg1 141.29(13) . . ? O1 C2 N1 123.41(18) . . ? O1 C2 C1 117.73(18) . 3_685 ? N1 C2 C1 118.86(18) . 3_685 ? C2 N1 C3 118.01(17) . . ? C2 N1 C1 124.50(17) . . ? C3 N1 C1 117.36(16) . . ? N1 C1 C2 116.52(17) . 3_685 ? O3 C4 O2 125.44(19) . . ? O3 C4 C3 117.24(17) . . ? O2 C4 C3 117.31(16) . . ? N1 C3 C4 110.01(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O1 0.85(4) 1.93(4) 2.759(2) 165(3) 1_655 O1W H1WB O1 0.90(3) 1.84(3) 2.735(2) 175(2) 3_775 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.371 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 932217' ####################################################################### # # 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_compound2 #TrackingRef 'Compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 Ca N2 O8' _chemical_formula_weight 304.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ca Ca 0.2262 0.3064 '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 7.5941(4) _cell_length_b 5.6569(3) _cell_length_c 13.1056(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.284(4) _cell_angle_gamma 90.00 _cell_volume 560.61(5) _cell_formula_units_Z 2 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 1519 _cell_measurement_theta_min 3.1157 _cell_measurement_theta_max 28.9633 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.803 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.602 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8399 _exptl_absorpt_correction_T_max 0.8640 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 301(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _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 2586 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1100 _reflns_number_gt 990 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro ' _computing_cell_refinement 'CrysAlisPro ' _computing_data_reduction 'CrysAlisPro ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0269P)^2^+0.2526P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1100 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _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 Ca1 Ca 0.5000 0.0000 1.0000 0.01412(15) Uani 1 2 d S . . O3 O 0.22362(16) 0.1637(2) 0.94807(9) 0.0246(3) Uani 1 1 d . . . N1 N 0.05625(18) 0.4810(2) 0.90177(10) 0.0166(3) Uani 1 1 d . . . C4 C 0.0580(2) 0.3232(3) 1.07469(12) 0.0187(4) Uani 1 1 d . . . H4A H -0.0047 0.1766 1.0842 0.022 Uiso 1 1 calc R . . H4B H 0.1614 0.3247 1.1240 0.022 Uiso 1 1 calc R . . O2 O -0.12520(17) 0.1545(2) 0.77940(9) 0.0262(3) Uani 1 1 d . . . C3 C 0.1192(2) 0.3223(3) 0.96949(12) 0.0167(4) Uani 1 1 d . . . O1 O 0.01086(17) 0.2518(2) 0.64232(8) 0.0225(3) Uani 1 1 d . . . C2 C 0.0953(2) 0.4601(3) 0.79545(12) 0.0202(4) Uani 1 1 d . . . H2A H 0.2192 0.4202 0.7937 0.024 Uiso 1 1 calc R . . H2B H 0.0755 0.6119 0.7619 0.024 Uiso 1 1 calc R . . C1 C -0.0175(2) 0.2731(3) 0.73610(12) 0.0169(4) Uani 1 1 d . . . O1W O 0.3729(2) -0.2937(3) 1.09368(11) 0.0310(4) Uani 1 1 d . . . H1WA H 0.301(3) -0.259(4) 1.1320(18) 0.039(7) Uiso 1 1 d . . . H1WB H 0.414(4) -0.423(6) 1.1106(19) 0.049(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ca1 0.0161(3) 0.0148(3) 0.0119(2) 0.00071(17) 0.00348(17) 0.00273(18) O3 0.0219(6) 0.0248(7) 0.0265(7) -0.0053(5) -0.0003(5) 0.0102(5) N1 0.0182(7) 0.0181(8) 0.0133(6) -0.0017(5) 0.0007(5) 0.0026(6) C4 0.0207(9) 0.0156(9) 0.0191(8) 0.0013(7) -0.0013(7) 0.0030(7) O2 0.0305(7) 0.0275(7) 0.0214(6) -0.0008(5) 0.0069(5) -0.0087(6) C3 0.0137(8) 0.0164(9) 0.0195(8) -0.0041(7) -0.0020(6) -0.0011(7) O1 0.0336(7) 0.0221(7) 0.0122(6) -0.0007(5) 0.0047(5) -0.0015(6) C2 0.0235(9) 0.0225(9) 0.0152(8) -0.0014(7) 0.0049(7) -0.0032(7) C1 0.0198(8) 0.0163(8) 0.0146(8) 0.0018(6) 0.0008(6) 0.0044(7) O1W 0.0374(9) 0.0242(8) 0.0340(8) 0.0090(6) 0.0165(7) 0.0003(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 Ca1 O1W 2.3273(14) . ? Ca1 O1W 2.3273(14) 3_657 ? Ca1 O1 2.3300(11) 2_546 ? Ca1 O1 2.3300(11) 4_666 ? Ca1 O3 2.3373(12) . ? Ca1 O3 2.3373(12) 3_657 ? O3 C3 1.246(2) . ? N1 C3 1.320(2) . ? N1 C2 1.456(2) . ? N1 C4 1.458(2) 3_567 ? C4 N1 1.458(2) 3_567 ? C4 C3 1.495(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O2 C1 1.236(2) . ? O1 C1 1.2729(19) . ? O1 Ca1 2.3300(11) 2_556 ? C2 C1 1.528(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? O1W H1WA 0.80(3) . ? O1W H1WB 0.82(3) . ? 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 O1W Ca1 O1W 180.0 . 3_657 ? O1W Ca1 O1 90.36(5) . 2_546 ? O1W Ca1 O1 89.64(5) 3_657 2_546 ? O1W Ca1 O1 89.64(5) . 4_666 ? O1W Ca1 O1 90.36(5) 3_657 4_666 ? O1 Ca1 O1 180.0 2_546 4_666 ? O1W Ca1 O3 91.81(5) . . ? O1W Ca1 O3 88.19(5) 3_657 . ? O1 Ca1 O3 92.35(4) 2_546 . ? O1 Ca1 O3 87.65(4) 4_666 . ? O1W Ca1 O3 88.19(5) . 3_657 ? O1W Ca1 O3 91.81(5) 3_657 3_657 ? O1 Ca1 O3 87.65(4) 2_546 3_657 ? O1 Ca1 O3 92.35(4) 4_666 3_657 ? O3 Ca1 O3 180.0 . 3_657 ? C3 O3 Ca1 142.43(11) . . ? C3 N1 C2 119.69(14) . . ? C3 N1 C4 124.06(14) . 3_567 ? C2 N1 C4 116.21(13) . 3_567 ? N1 C4 C3 116.06(14) 3_567 . ? N1 C4 H4A 108.3 3_567 . ? C3 C4 H4A 108.3 . . ? N1 C4 H4B 108.3 3_567 . ? C3 C4 H4B 108.3 . . ? H4A C4 H4B 107.4 . . ? O3 C3 N1 122.43(15) . . ? O3 C3 C4 117.92(15) . . ? N1 C3 C4 119.58(15) . . ? C1 O1 Ca1 135.97(11) . 2_556 ? N1 C2 C1 112.91(13) . . ? N1 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? O2 C1 O1 124.73(16) . . ? O2 C1 C2 120.38(14) . . ? O1 C1 C2 114.88(14) . . ? Ca1 O1W H1WA 119.6(17) . . ? Ca1 O1W H1WB 128.0(19) . . ? H1WA O1W H1WB 108(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O2 0.80(3) 1.94(3) 2.739(2) 176(2) 3_557 O1W H1WB O1 0.82(3) 2.03(3) 2.845(2) 176(3) 4_656 O1W H1WB O2 0.82(3) 2.61(3) 3.1757(19) 128(2) 4_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.237 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.048 _database_code_depnum_ccdc_archive 'CCDC 932218' ####################################################################### # # 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_compound3 #TrackingRef 'Compound3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N2 O9 Sr' _chemical_formula_weight 369.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sr Sr -1.5307 3.2498 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.6213(16) _cell_length_b 6.9431(5) _cell_length_c 8.0865(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.072(9) _cell_angle_gamma 90.00 _cell_volume 1286.43(14) _cell_formula_units_Z 4 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 2818 _cell_measurement_theta_min 3.4794 _cell_measurement_theta_max 29.1262 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.910 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 4.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3628 _exptl_absorpt_correction_T_max 0.4844 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 301(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _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 5462 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1258 _reflns_number_gt 1200 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXS-97 (Sheldrick, 1990)' _computing_publication_material 'SHELXS-97 (Sheldrick, 1990)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.0653P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1258 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0211 _refine_ls_R_factor_gt 0.0196 _refine_ls_wR_factor_ref 0.0501 _refine_ls_wR_factor_gt 0.0494 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sr1 Sr 1.0000 -0.11982(3) 0.2500 0.01692(10) Uani 1 2 d S . . O2 O 0.90034(7) 0.11711(19) 0.18874(18) 0.0324(3) Uani 1 1 d . . . O10 O 0.95857(5) 0.16294(19) 0.01514(17) 0.0232(3) Uani 1 1 d . . . O2W O 0.91782(8) -0.2664(3) 0.0122(2) 0.0416(4) Uani 1 1 d . . . H2WA H 0.9105(14) -0.219(5) -0.091(5) 0.076(10) Uiso 1 1 d . . . H2WB H 0.8898(13) -0.315(5) 0.015(4) 0.049(8) Uiso 1 1 d . . . O1 O 0.81395(7) 0.5712(2) 0.0358(2) 0.0450(4) Uani 1 1 d . . . O1W O 1.0000 -0.4943(3) 0.2500 0.0698(10) Uani 1 2 d S . . H1WA H 1.0092(15) -0.567(5) 0.336(4) 0.072(10) Uiso 1 1 d . . . N1 N 0.80384(6) 0.2590(2) -0.04488(19) 0.0236(3) Uani 1 1 d . . . C4 C 0.78635(8) 0.4197(3) 0.0170(2) 0.0257(4) Uani 1 1 d . . . C2 C 0.86018(7) 0.2511(3) -0.0890(2) 0.0246(4) Uani 1 1 d . . . H2A H 0.8705 0.3800 -0.1176 0.029 Uiso 1 1 calc R . . H2B H 0.8563 0.1717 -0.1899 0.029 Uiso 1 1 calc R . . C1 C 0.90954(7) 0.1719(2) 0.0512(2) 0.0182(4) Uani 1 1 d . . . C3 C 0.77136(9) 0.0793(3) -0.0643(3) 0.0348(5) Uani 1 1 d . . . H3A H 0.7959 -0.0178 0.0044 0.042 Uiso 1 1 calc R . . H3B H 0.7646 0.0392 -0.1823 0.042 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 Sr1 0.01423(14) 0.01996(14) 0.01792(14) 0.000 0.00653(9) 0.000 O2 0.0271(8) 0.0502(9) 0.0221(7) 0.0051(6) 0.0102(6) 0.0046(6) O10 0.0141(6) 0.0295(6) 0.0276(7) -0.0008(5) 0.0084(5) 0.0019(5) O2W 0.0375(10) 0.0534(10) 0.0311(8) 0.0041(7) 0.0029(7) -0.0253(8) O1 0.0331(9) 0.0395(8) 0.0678(11) -0.0145(8) 0.0228(8) -0.0119(7) O1W 0.112(3) 0.0223(12) 0.0538(17) 0.000 -0.0212(17) 0.000 N1 0.0117(7) 0.0321(8) 0.0279(8) 0.0006(7) 0.0061(6) 0.0020(6) C4 0.0167(9) 0.0324(10) 0.0276(10) -0.0041(8) 0.0044(8) -0.0023(7) C2 0.0148(9) 0.0350(10) 0.0258(9) 0.0032(8) 0.0086(7) 0.0037(8) C1 0.0152(9) 0.0186(8) 0.0214(9) -0.0037(7) 0.0060(7) 0.0003(7) C3 0.0235(11) 0.0359(11) 0.0485(13) -0.0158(10) 0.0155(10) -0.0036(8) _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 Sr1 O10 2.5816(13) 5_755 ? Sr1 O10 2.5816(13) 6_556 ? Sr1 O2W 2.5857(16) . ? Sr1 O2W 2.5857(16) 2_755 ? Sr1 O1W 2.600(2) . ? Sr1 O10 2.7413(13) 2_755 ? Sr1 O10 2.7413(13) . ? Sr1 O2 2.8153(14) 2_755 ? Sr1 O2 2.8153(14) . ? Sr1 C1 3.0952(17) 2_755 ? Sr1 C1 3.0952(17) . ? Sr1 Sr1 4.3722(2) 5_756 ? O2 C1 1.243(2) . ? O10 C1 1.263(2) . ? O10 Sr1 2.5816(13) 5_755 ? O1 C4 1.227(2) . ? N1 C4 1.330(3) . ? N1 C3 1.453(3) . ? N1 C2 1.460(2) . ? C4 C3 1.503(3) 7_655 ? C2 C1 1.518(2) . ? C3 C4 1.503(3) 7_655 ? 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 O10 Sr1 O10 166.68(6) 5_755 6_556 ? O10 Sr1 O2W 72.81(5) 5_755 . ? O10 Sr1 O2W 101.79(5) 6_556 . ? O10 Sr1 O2W 101.79(5) 5_755 2_755 ? O10 Sr1 O2W 72.81(5) 6_556 2_755 ? O2W Sr1 O2W 133.64(8) . 2_755 ? O10 Sr1 O1W 83.34(3) 5_755 . ? O10 Sr1 O1W 83.34(3) 6_556 . ? O2W Sr1 O1W 66.82(4) . . ? O2W Sr1 O1W 66.82(4) 2_755 . ? O10 Sr1 O10 120.99(4) 5_755 2_755 ? O10 Sr1 O10 69.59(4) 6_556 2_755 ? O2W Sr1 O10 150.93(5) . 2_755 ? O2W Sr1 O10 71.92(5) 2_755 2_755 ? O1W Sr1 O10 135.74(3) . 2_755 ? O10 Sr1 O10 69.59(4) 5_755 . ? O10 Sr1 O10 120.99(4) 6_556 . ? O2W Sr1 O10 71.92(5) . . ? O2W Sr1 O10 150.93(5) 2_755 . ? O1W Sr1 O10 135.74(3) . . ? O10 Sr1 O10 88.52(6) 2_755 . ? O10 Sr1 O2 75.19(4) 5_755 2_755 ? O10 Sr1 O2 113.03(4) 6_556 2_755 ? O2W Sr1 O2 143.64(5) . 2_755 ? O2W Sr1 O2 69.80(5) 2_755 2_755 ? O1W Sr1 O2 125.76(3) . 2_755 ? O10 Sr1 O2 46.94(4) 2_755 2_755 ? O10 Sr1 O2 81.13(4) . 2_755 ? O10 Sr1 O2 113.03(4) 5_755 . ? O10 Sr1 O2 75.19(4) 6_556 . ? O2W Sr1 O2 69.80(5) . . ? O2W Sr1 O2 143.64(5) 2_755 . ? O1W Sr1 O2 125.75(3) . . ? O10 Sr1 O2 81.13(4) 2_755 . ? O10 Sr1 O2 46.94(4) . . ? O2 Sr1 O2 108.49(6) 2_755 . ? O10 Sr1 C1 98.86(4) 5_755 2_755 ? O10 Sr1 C1 89.87(4) 6_556 2_755 ? O2W Sr1 C1 160.45(5) . 2_755 ? O2W Sr1 C1 64.70(5) 2_755 2_755 ? O1W Sr1 C1 130.86(3) . 2_755 ? O10 Sr1 C1 24.02(4) 2_755 2_755 ? O10 Sr1 C1 88.64(4) . 2_755 ? O2 Sr1 C1 23.68(4) 2_755 2_755 ? O2 Sr1 C1 98.70(4) . 2_755 ? O10 Sr1 C1 89.87(4) 5_755 . ? O10 Sr1 C1 98.86(4) 6_556 . ? O2W Sr1 C1 64.70(5) . . ? O2W Sr1 C1 160.45(5) 2_755 . ? O1W Sr1 C1 130.86(3) . . ? O10 Sr1 C1 88.64(4) 2_755 . ? O10 Sr1 C1 24.02(4) . . ? O2 Sr1 C1 98.70(4) 2_755 . ? O2 Sr1 C1 23.68(4) . . ? C1 Sr1 C1 98.27(6) 2_755 . ? O10 Sr1 Sr1 153.82(3) 5_755 5_756 ? O10 Sr1 Sr1 35.99(3) 6_556 5_756 ? O2W Sr1 Sr1 131.96(4) . 5_756 ? O2W Sr1 Sr1 68.34(4) 2_755 5_756 ? O1W Sr1 Sr1 112.367(5) . 5_756 ? O10 Sr1 Sr1 33.60(3) 2_755 5_756 ? O10 Sr1 Sr1 106.73(3) . 5_756 ? O2 Sr1 Sr1 78.63(3) 2_755 5_756 ? O2 Sr1 Sr1 75.66(3) . 5_756 ? C1 Sr1 Sr1 54.97(3) 2_755 5_756 ? C1 Sr1 Sr1 94.36(3) . 5_756 ? C1 O2 Sr1 90.89(11) . . ? C1 O10 Sr1 138.73(12) . 5_755 ? C1 O10 Sr1 93.90(10) . . ? Sr1 O10 Sr1 110.41(4) 5_755 . ? C4 N1 C3 123.86(16) . . ? C4 N1 C2 120.56(16) . . ? C3 N1 C2 115.49(15) . . ? O1 C4 N1 124.17(18) . . ? O1 C4 C3 116.89(18) . 7_655 ? N1 C4 C3 118.93(17) . 7_655 ? N1 C2 C1 114.26(14) . . ? O2 C1 O10 124.14(17) . . ? O2 C1 C2 120.62(15) . . ? O10 C1 C2 115.22(15) . . ? O2 C1 Sr1 65.43(10) . . ? O10 C1 Sr1 62.08(9) . . ? C2 C1 Sr1 158.88(12) . . ? N1 C3 C4 117.17(17) . 7_655 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.289 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.068 _database_code_depnum_ccdc_archive 'CCDC 932219' ####################################################################### # # 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_compound4 #TrackingRef 'Compound4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Ba N2 O7' _chemical_formula_weight 383.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ba Ba -0.3244 2.2819 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 4.6423(2) _cell_length_b 13.5308(6) _cell_length_c 17.7254(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.474(4) _cell_angle_gamma 90.00 _cell_volume 1111.36(9) _cell_formula_units_Z 4 _cell_measurement_temperature 301(2) _cell_measurement_reflns_used 1819 _cell_measurement_theta_min 3.2173 _cell_measurement_theta_max 29.0382 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 3.605 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4110 _exptl_absorpt_correction_T_max 0.4660 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 301(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini ultra' _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 2835 _diffrn_reflns_av_R_equivalents 0.0137 _diffrn_reflns_av_sigmaI/netI 0.0159 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1093 _reflns_number_gt 1088 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0119P)^2^+1.9387P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1093 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0151 _refine_ls_R_factor_gt 0.0150 _refine_ls_wR_factor_ref 0.0353 _refine_ls_wR_factor_gt 0.0352 _refine_ls_goodness_of_fit_ref 1.200 _refine_ls_restrained_S_all 1.200 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ba1 Ba 0.0000 0.429602(13) 0.2500 0.01673(7) Uani 1 2 d S . . C1 C -0.0708(5) 0.06784(17) 0.35609(14) 0.0215(5) Uani 1 1 d . . . O1 O 0.0377(4) -0.01147(12) 0.33447(10) 0.0273(4) Uani 1 1 d . . . N1 N -0.0598(4) 0.19426(14) 0.45857(11) 0.0212(4) Uani 1 1 d . . . O1W O -0.5000 0.2766(2) 0.2500 0.0454(8) Uani 1 2 d S . . O2 O -0.3133(4) 0.10048(14) 0.33354(11) 0.0324(4) Uani 1 1 d . . . C2 C 0.1111(5) 0.12776(19) 0.41458(15) 0.0262(5) Uani 1 1 d . . . H2A H 0.2160 0.0826 0.4487 0.031 Uiso 1 1 calc R . . H2B H 0.2516 0.1662 0.3888 0.031 Uiso 1 1 calc R . . O3 O 0.0307(4) 0.32597(15) 0.38561(11) 0.0374(5) Uani 1 1 d . . . C3 C -0.2028(5) 0.14816(18) 0.52016(14) 0.0233(5) Uani 1 1 d . . . H3A H -0.0552 0.1231 0.5562 0.028 Uiso 1 1 calc R . . H3B H -0.3107 0.0917 0.4999 0.028 Uiso 1 1 calc R . . C4 C -0.0953(5) 0.28840(18) 0.43774(13) 0.0218(5) Uani 1 1 d . . . H1WA H -0.420(8) 0.241(3) 0.287(2) 0.067(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ba1 0.02018(11) 0.01708(11) 0.01321(11) 0.000 0.00324(7) 0.000 C1 0.0242(13) 0.0225(12) 0.0184(12) -0.0008(9) 0.0061(10) -0.0002(9) O1 0.0323(10) 0.0239(9) 0.0259(9) -0.0063(8) 0.0048(8) 0.0058(7) N1 0.0246(10) 0.0210(10) 0.0184(10) -0.0033(8) 0.0043(8) 0.0001(8) O1W 0.075(2) 0.0265(15) 0.0351(18) 0.000 0.0035(16) 0.000 O2 0.0259(10) 0.0326(10) 0.0375(11) -0.0100(9) -0.0074(8) 0.0060(8) C2 0.0202(12) 0.0310(13) 0.0273(13) -0.0103(11) 0.0017(10) 0.0032(10) O3 0.0389(11) 0.0454(12) 0.0295(10) 0.0167(9) 0.0157(9) 0.0042(9) C3 0.0255(13) 0.0212(11) 0.0233(13) 0.0036(10) 0.0033(10) 0.0014(10) C4 0.0218(12) 0.0269(12) 0.0164(11) 0.0015(10) -0.0005(9) -0.0008(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ba1 O3 2.7790(18) 2 ? Ba1 O3 2.7790(18) . ? Ba1 O1 2.8060(17) 4 ? Ba1 O1 2.8060(17) 3_455 ? Ba1 O2 2.8521(18) 3 ? Ba1 O2 2.8520(18) 4_455 ? Ba1 O1 2.9419(18) 3 ? Ba1 O1 2.9419(18) 4_455 ? Ba1 O1W 3.110(2) . ? Ba1 O1W 3.110(2) 1_655 ? Ba1 C1 3.248(2) 3 ? Ba1 C1 3.248(2) 4_455 ? C1 O2 1.252(3) . ? C1 O1 1.255(3) . ? C1 C2 1.530(3) . ? C1 Ba1 3.248(2) 3_445 ? O1 Ba1 2.8060(17) 3_545 ? O1 Ba1 2.9419(18) 3_445 ? N1 C4 1.334(3) . ? N1 C3 1.452(3) . ? N1 C2 1.457(3) . ? O1W Ba1 3.110(2) 1_455 ? O2 Ba1 2.8520(18) 3_445 ? O3 C4 1.233(3) . ? C3 C4 1.502(3) 7_456 ? C4 C3 1.502(3) 7_456 ? 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 O3 Ba1 O3 119.39(9) 2 . ? O3 Ba1 O1 71.50(5) 2 4 ? O3 Ba1 O1 127.17(5) . 4 ? O3 Ba1 O1 127.17(5) 2 3_455 ? O3 Ba1 O1 71.50(5) . 3_455 ? O1 Ba1 O1 146.98(7) 4 3_455 ? O3 Ba1 O2 148.89(6) 2 3 ? O3 Ba1 O2 87.82(6) . 3 ? O1 Ba1 O2 80.12(5) 4 3 ? O1 Ba1 O2 73.19(5) 3_455 3 ? O3 Ba1 O2 87.82(6) 2 4_455 ? O3 Ba1 O2 148.89(6) . 4_455 ? O1 Ba1 O2 73.19(5) 4 4_455 ? O1 Ba1 O2 80.12(5) 3_455 4_455 ? O2 Ba1 O2 71.67(8) 3 4_455 ? O3 Ba1 O1 125.06(5) 2 3 ? O3 Ba1 O1 72.49(6) . 3 ? O1 Ba1 O1 62.73(6) 4 3 ? O1 Ba1 O1 107.71(6) 3_455 3 ? O2 Ba1 O1 45.11(5) 3 3 ? O2 Ba1 O1 105.45(5) 4_455 3 ? O3 Ba1 O1 72.49(6) 2 4_455 ? O3 Ba1 O1 125.06(5) . 4_455 ? O1 Ba1 O1 107.71(6) 4 4_455 ? O1 Ba1 O1 62.73(6) 3_455 4_455 ? O2 Ba1 O1 105.45(5) 3 4_455 ? O2 Ba1 O1 45.11(5) 4_455 4_455 ? O1 Ba1 O1 148.55(7) 3 4_455 ? O3 Ba1 O1W 70.43(4) 2 . ? O3 Ba1 O1W 70.33(5) . . ? O1 Ba1 O1W 141.64(4) 4 . ? O1 Ba1 O1W 66.06(5) 3_455 . ? O2 Ba1 O1W 137.98(5) 3 . ? O2 Ba1 O1W 109.65(5) 4_455 . ? O1 Ba1 O1W 142.24(4) 3 . ? O1 Ba1 O1W 64.55(5) 4_455 . ? O3 Ba1 O1W 70.33(5) 2 1_655 ? O3 Ba1 O1W 70.43(4) . 1_655 ? O1 Ba1 O1W 66.06(5) 4 1_655 ? O1 Ba1 O1W 141.64(4) 3_455 1_655 ? O2 Ba1 O1W 109.65(5) 3 1_655 ? O2 Ba1 O1W 137.98(5) 4_455 1_655 ? O1 Ba1 O1W 64.55(5) 3 1_655 ? O1 Ba1 O1W 142.24(4) 4_455 1_655 ? O1W Ba1 O1W 96.54(8) . 1_655 ? O3 Ba1 C1 142.08(6) 2 3 ? O3 Ba1 C1 78.01(6) . 3 ? O1 Ba1 C1 71.53(6) 4 3 ? O1 Ba1 C1 89.40(6) 3_455 3 ? O2 Ba1 C1 22.50(5) 3 3 ? O2 Ba1 C1 89.44(6) 4_455 3 ? O1 Ba1 C1 22.71(5) 3 3 ? O1 Ba1 C1 127.61(5) 4_455 3 ? O1W Ba1 C1 144.58(4) . 3 ? O1W Ba1 C1 87.23(5) 1_655 3 ? O3 Ba1 C1 78.01(6) 2 4_455 ? O3 Ba1 C1 142.08(6) . 4_455 ? O1 Ba1 C1 89.40(6) 4 4_455 ? O1 Ba1 C1 71.53(6) 3_455 4_455 ? O2 Ba1 C1 89.44(6) 3 4_455 ? O2 Ba1 C1 22.50(5) 4_455 4_455 ? O1 Ba1 C1 127.61(5) 3 4_455 ? O1 Ba1 C1 22.71(5) 4_455 4_455 ? O1W Ba1 C1 87.23(5) . 4_455 ? O1W Ba1 C1 144.58(4) 1_655 4_455 ? C1 Ba1 C1 109.68(8) 3 4_455 ? O2 C1 O1 125.0(2) . . ? O2 C1 C2 118.6(2) . . ? O1 C1 C2 116.4(2) . . ? O2 C1 Ba1 60.68(13) . 3_445 ? O1 C1 Ba1 64.81(13) . 3_445 ? C2 C1 Ba1 172.66(17) . 3_445 ? C1 O1 Ba1 137.72(16) . 3_545 ? C1 O1 Ba1 92.48(15) . 3_445 ? Ba1 O1 Ba1 107.71(6) 3_545 3_445 ? C4 N1 C3 124.3(2) . . ? C4 N1 C2 120.3(2) . . ? C3 N1 C2 115.2(2) . . ? Ba1 O1W Ba1 96.54(8) . 1_455 ? C1 O2 Ba1 96.83(14) . 3_445 ? N1 C2 C1 113.2(2) . . ? C4 O3 Ba1 148.71(17) . . ? N1 C3 C4 117.1(2) . 7_456 ? O3 C4 N1 123.0(2) . . ? O3 C4 C3 118.4(2) . 7_456 ? N1 C4 C3 118.6(2) . 7_456 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.564 _refine_diff_density_min -0.648 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 932220'