data_new _audit_update_record ; 2014-06-04 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C9 H14 N), Cr2 O7' _chemical_formula_sum 'C18 H28 Cr2 N2 O7' _chemical_formula_weight 488.42 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' 'Cr' 'Cr' 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 7.9379(2) _cell_length_b 36.2439(16) _cell_length_c 7.5753(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.069(2) _cell_angle_gamma 90.00 _cell_volume 2167.20(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 4345 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.43 _cell_measurement_wavelength 0.71073 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 1.043 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.722 _exptl_absorpt_correction_T_max 0.910 _exptl_special_details ? _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_unetI/netI 0.0522 _diffrn_reflns_number 18139 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4959 _reflns_number_gt 4147 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (Bruker, 2006)' _computing_cell_refinement 'Bruker APEX2 (Bruker, 2006)' _computing_data_reduction 'Bruker APEX2 (Bruker, 2006)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX publication routines (Farrugia, 2012), CRYSCAL (T. Roisnel, local program) ; _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^)+(0.0376P)^2^+2.0169P] 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 4959 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 Cr1 Cr -0.12326(5) -0.048947(11) -0.75152(5) 0.01454(11) Uani 1 1 d . . . Cr2 Cr -0.31447(5) 0.023990(11) -0.65700(5) 0.01360(11) Uani 1 1 d . . . O7 O -0.2026(2) 0.05022(5) -0.7742(2) 0.0228(4) Uani 1 1 d . . . O3 O 0.0302(2) -0.03192(5) -0.8490(3) 0.0248(4) Uani 1 1 d . . . O6 O -0.3515(3) 0.04440(5) -0.4767(2) 0.0278(5) Uani 1 1 d . . . O5 O -0.4887(2) 0.01377(5) -0.7760(3) 0.0235(4) Uani 1 1 d . . . O4 O -0.1961(2) -0.01688(5) -0.5948(2) 0.0191(4) Uani 1 1 d . . . O1 O -0.2801(2) -0.05802(6) -0.8992(3) 0.0324(5) Uani 1 1 d . . . O2 O -0.0628(3) -0.08513(5) -0.6416(3) 0.0364(5) Uani 1 1 d . . . N2 N -0.1630(3) -0.04253(6) -0.2398(3) 0.0174(4) Uani 1 1 d . . . H2A H -0.1710 -0.0327 -0.3481 0.026 Uiso 1 1 calc R . . H2B H -0.0673 -0.0350 -0.1785 0.026 Uiso 1 1 calc R . . H2C H -0.2509 -0.0353 -0.1846 0.026 Uiso 1 1 calc R . . N1 N -0.6275(3) -0.06407(6) 0.1151(3) 0.0193(5) Uani 1 1 d . . . H1A H -0.6951 -0.0565 0.0208 0.029 Uiso 1 1 calc R . . H1B H -0.5245 -0.0546 0.1113 0.029 Uiso 1 1 calc R . . H1C H -0.6691 -0.0566 0.2136 0.029 Uiso 1 1 calc R . . C11 C -0.3349(3) -0.09772(7) -0.3277(3) 0.0174(5) Uani 1 1 d . . . H11A H -0.3697 -0.0854 -0.4394 0.021 Uiso 1 1 calc R . . H11B H -0.4171 -0.0919 -0.2458 0.021 Uiso 1 1 calc R . . C13 C -0.5032(3) -0.15756(7) -0.3983(3) 0.0203(5) Uani 1 1 d . . . C10 C -0.1627(3) -0.08370(7) -0.2537(3) 0.0174(5) Uani 1 1 d . . . H10A H -0.1322 -0.0943 -0.1371 0.021 Uiso 1 1 calc R . . H10B H -0.0787 -0.0914 -0.3303 0.021 Uiso 1 1 calc R . . C1 C -0.6171(3) -0.10520(7) 0.1143(4) 0.0205(5) Uani 1 1 d . . . H1D H -0.5606 -0.1137 0.2267 0.025 Uiso 1 1 calc R . . H1E H -0.5509 -0.1132 0.0207 0.025 Uiso 1 1 calc R . . C3 C -0.7901(3) -0.16394(7) 0.0822(4) 0.0243(6) Uani 1 1 d . . . H3A H -0.7264 -0.1722 -0.0129 0.029 Uiso 1 1 calc R . . H3B H -0.7321 -0.1728 0.1932 0.029 Uiso 1 1 calc R . . C2 C -0.7920(3) -0.12188(7) 0.0851(4) 0.0234(6) Uani 1 1 d . . . H2D H -0.8481 -0.1130 -0.0268 0.028 Uiso 1 1 calc R . . H2E H -0.8574 -0.1136 0.1788 0.028 Uiso 1 1 calc R . . C4 C -0.9654(3) -0.18082(7) 0.0563(4) 0.0232(6) Uani 1 1 d . . . C14 C -0.6564(3) -0.13852(7) -0.4077(4) 0.0220(6) Uani 1 1 d . . . H14 H -0.6561 -0.1131 -0.3924 0.026 Uiso 1 1 calc R . . C12 C -0.3313(3) -0.13934(7) -0.3574(4) 0.0242(6) Uani 1 1 d . . . H12A H -0.2645 -0.1443 -0.4548 0.029 Uiso 1 1 calc R . . H12B H -0.2740 -0.1508 -0.2520 0.029 Uiso 1 1 calc R . . C15 C -0.8096(3) -0.15720(8) -0.4397(4) 0.0272(6) Uani 1 1 d . . . H15 H -0.9108 -0.1441 -0.4461 0.033 Uiso 1 1 calc R . . C17 C -0.6612(4) -0.21414(8) -0.4546(5) 0.0377(8) Uani 1 1 d . . . H17 H -0.6622 -0.2396 -0.4706 0.045 Uiso 1 1 calc R . . C9 C -0.9996(4) -0.21069(8) -0.0579(4) 0.0314(7) Uani 1 1 d . . . H9 H -0.9139 -0.2202 -0.1192 0.038 Uiso 1 1 calc R . . C6 C -1.2574(4) -0.18343(8) 0.1207(4) 0.0338(7) Uani 1 1 d . . . H6 H -1.3440 -0.1742 0.1817 0.041 Uiso 1 1 calc R . . C8 C -1.1599(5) -0.22642(8) -0.0812(5) 0.0402(9) Uani 1 1 d . . . H8 H -1.1799 -0.2464 -0.1573 0.048 Uiso 1 1 calc R . . C5 C -1.0975(4) -0.16747(8) 0.1459(4) 0.0278(6) Uani 1 1 d . . . H5 H -1.0784 -0.1476 0.2233 0.033 Uiso 1 1 calc R . . C18 C -0.5087(4) -0.19569(8) -0.4238(4) 0.0325(7) Uani 1 1 d . . . H18 H -0.4079 -0.2089 -0.4200 0.039 Uiso 1 1 calc R . . C7 C -1.2892(4) -0.21282(9) 0.0064(5) 0.0376(8) Uani 1 1 d . . . H7 H -1.3967 -0.2233 -0.0110 0.045 Uiso 1 1 calc R . . C16 C -0.8129(4) -0.19489(8) -0.4619(4) 0.0301(7) Uani 1 1 d . . . H16 H -0.9157 -0.2073 -0.4815 0.036 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 Cr1 0.0154(2) 0.0156(2) 0.0129(2) -0.00036(16) 0.00280(15) 0.00109(15) Cr2 0.01384(19) 0.0147(2) 0.0122(2) 0.00057(15) 0.00154(15) 0.00190(15) O7 0.0194(9) 0.0250(10) 0.0241(10) 0.0070(8) 0.0031(8) -0.0033(7) O3 0.0188(9) 0.0256(10) 0.0316(11) -0.0028(9) 0.0107(8) -0.0031(8) O6 0.0407(12) 0.0268(11) 0.0164(9) -0.0027(8) 0.0049(9) 0.0116(9) O5 0.0145(9) 0.0238(10) 0.0312(11) -0.0024(8) -0.0032(8) 0.0011(7) O4 0.0239(9) 0.0193(9) 0.0138(9) -0.0003(7) 0.0003(7) 0.0070(7) O1 0.0171(9) 0.0546(14) 0.0256(11) -0.0191(10) 0.0039(8) -0.0046(9) O2 0.0632(15) 0.0227(11) 0.0263(11) 0.0073(9) 0.0181(10) 0.0194(10) N2 0.0161(10) 0.0214(11) 0.0143(10) 0.0003(9) -0.0002(8) -0.0023(8) N1 0.0170(10) 0.0247(12) 0.0164(11) -0.0015(9) 0.0030(8) -0.0022(9) C11 0.0156(12) 0.0175(13) 0.0192(13) -0.0006(10) 0.0011(10) 0.0000(10) C13 0.0210(13) 0.0186(13) 0.0209(13) -0.0006(11) 0.0004(10) -0.0007(10) C10 0.0190(12) 0.0186(13) 0.0144(12) 0.0002(10) 0.0011(10) 0.0014(10) C1 0.0188(12) 0.0213(13) 0.0215(13) 0.0007(11) 0.0021(10) 0.0022(10) C3 0.0238(14) 0.0223(14) 0.0273(15) 0.0003(12) 0.0053(11) 0.0037(11) C2 0.0191(13) 0.0217(14) 0.0295(15) 0.0030(12) 0.0029(11) 0.0021(10) C4 0.0288(14) 0.0164(13) 0.0233(14) 0.0036(11) -0.0022(11) -0.0004(11) C14 0.0231(13) 0.0165(13) 0.0259(14) -0.0014(11) 0.0006(11) -0.0001(10) C12 0.0204(13) 0.0182(13) 0.0333(16) -0.0014(12) -0.0005(11) 0.0018(10) C15 0.0220(14) 0.0258(15) 0.0339(16) -0.0007(13) 0.0031(12) 0.0008(11) C17 0.0373(17) 0.0179(15) 0.055(2) -0.0030(14) -0.0101(15) -0.0038(13) C9 0.0459(18) 0.0200(14) 0.0273(16) 0.0000(12) -0.0017(13) 0.0041(13) C6 0.0289(15) 0.0301(16) 0.0423(18) 0.0102(14) 0.0028(14) -0.0041(13) C8 0.059(2) 0.0178(15) 0.0387(19) 0.0008(14) -0.0172(17) -0.0077(14) C5 0.0284(15) 0.0231(14) 0.0313(16) -0.0011(12) 0.0003(12) -0.0043(12) C18 0.0262(15) 0.0198(14) 0.0491(19) -0.0026(14) -0.0066(14) 0.0036(11) C7 0.0339(17) 0.0280(17) 0.047(2) 0.0143(15) -0.0119(15) -0.0114(14) C16 0.0273(15) 0.0257(15) 0.0363(17) -0.0010(13) -0.0016(13) -0.0073(12) _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 Cr1 O2 1.5994(19) . ? Cr1 O3 1.6125(18) . ? Cr1 O1 1.6171(19) . ? Cr1 O4 1.8002(17) . ? Cr2 O6 1.6074(19) . ? Cr2 O5 1.6121(17) . ? Cr2 O7 1.6272(18) . ? Cr2 O4 1.7902(17) . ? N2 C10 1.496(3) . ? N1 C1 1.493(3) . ? C11 C10 1.510(3) . ? C11 C12 1.526(3) . ? C13 C14 1.393(4) . ? C13 C18 1.395(4) . ? C13 C12 1.518(3) . ? C1 C2 1.509(3) . ? C3 C4 1.514(4) . ? C3 C2 1.525(4) . ? C4 C9 1.394(4) . ? C4 C5 1.395(4) . ? C14 C15 1.391(4) . ? C15 C16 1.377(4) . ? C17 C18 1.381(4) . ? C17 C16 1.388(4) . ? C9 C8 1.388(5) . ? C6 C7 1.379(5) . ? C6 C5 1.389(4) . ? C8 C7 1.371(5) . ? 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 O2 Cr1 O3 110.65(11) . . ? O2 Cr1 O1 111.10(12) . . ? O3 Cr1 O1 108.93(10) . . ? O2 Cr1 O4 106.60(9) . . ? O3 Cr1 O4 111.46(9) . . ? O1 Cr1 O4 108.06(9) . . ? O6 Cr2 O5 110.98(10) . . ? O6 Cr2 O7 110.73(10) . . ? O5 Cr2 O7 108.33(10) . . ? O6 Cr2 O4 107.16(9) . . ? O5 Cr2 O4 110.64(9) . . ? O7 Cr2 O4 108.99(9) . . ? Cr2 O4 Cr1 123.83(10) . . ? C10 C11 C12 110.9(2) . . ? C14 C13 C18 118.0(2) . . ? C14 C13 C12 123.7(2) . . ? C18 C13 C12 118.3(2) . . ? N2 C10 C11 110.70(19) . . ? N1 C1 C2 110.5(2) . . ? C4 C3 C2 113.3(2) . . ? C1 C2 C3 113.1(2) . . ? C9 C4 C5 117.7(3) . . ? C9 C4 C3 120.7(3) . . ? C5 C4 C3 121.7(2) . . ? C15 C14 C13 120.7(2) . . ? C13 C12 C11 115.5(2) . . ? C16 C15 C14 120.6(3) . . ? C18 C17 C16 120.3(3) . . ? C8 C9 C4 120.9(3) . . ? C7 C6 C5 120.8(3) . . ? C7 C8 C9 120.9(3) . . ? C6 C5 C4 120.8(3) . . ? C17 C18 C13 121.1(3) . . ? C8 C7 C6 119.0(3) . . ? C15 C16 C17 119.2(3) . . ? 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 N1 H1A O7 0.89 1.97 2.829(3) 161.8 3_454 N1 H1B O1 0.89 1.95 2.780(3) 153.7 1_556 N1 H1C O6 0.89 2.03 2.853(3) 153.0 3_455 N2 H2A O4 0.89 1.94 2.831(3) 173.5 . N2 H2B O7 0.89 2.28 2.906(3) 127.6 3_554 N2 H2B O3 0.89 2.54 3.210(3) 133.0 1_556 N2 H2C O5 0.89 2.20 2.969(3) 144.3 3_454 C2 H2E O2 0.97 2.46 3.409(3) 166.4 1_456 C5 H5 O2 0.93 2.48 3.388(4) 164.2 1_456 C10 H10B O2 0.97 2.39 3.124(3) 132.5 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.451 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.078