# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Isakov, D.' . ; Departamento de F\'isica Universidade do Minho P-4710-057 Braga Portugal ; 'de Matos Gomes, E.' . ; Departamento de F\'isica Universidade do Minho P-4710-057 Braga Portugal ; 'Rodrigues, V. H.' 'Correspondence author' ; CEMDRX, Department of Physics University of Coimbra P-3004-516 Coimbra Portugal ; 'Costa, M.M.R.R.' . ; CEMDRX, Department of Physics University of Coimbra P-3004-516 Coimbra Portugal ; 'Belsley, M. S.' . ; Departamento de F\'isica Universidade do Minho P-4710-057 Braga Portugal ; _publ_section_title ; Synthesis, structure and nonlinear optical p roperties of L-argininium perrhenate crystal ; _publ_contact_author_email vhugo@fis.uc.pt _publ_contact_author_name V.H.Rodrigues data_LARe _database_code_depnum_ccdc_archive 'CCDC 857125' #TrackingRef 'LARe.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; l-argininium perrhenate ; _chemical_name_common 'l-argininium perrhenate' _chemical_melting_point ? _chemical_formula_moiety 'C6 H15 N4 O2 1+, Re O4 1-' _chemical_formula_sum 'C6 H15 N4 O6 Re' _chemical_formula_weight 425.42 _chemical_absolute_configuration rmad 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' Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.0901(3) _cell_length_b 13.9239(6) _cell_length_c 16.8234(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1192.34(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7498 _cell_measurement_theta_min 2.8291 _cell_measurement_theta_max 32.1874 _exptl_crystal_description block _exptl_crystal_colour 'translucent colourless' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.370 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 10.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.605369 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 36430 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 36.63 _reflns_number_total 5840 _reflns_number_gt 4917 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX-II software (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0709P)^2^+4.5869P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(19) _refine_ls_number_reflns 5840 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.008 _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 Re1 Re 0.18935(6) 0.14011(2) 0.866915(16) 0.03713(8) Uani 1 1 d . . . O1 O 0.372(2) 0.0671(8) 0.9289(5) 0.084(3) Uani 1 1 d . . . O2 O 0.3640(17) 0.1729(7) 0.7855(4) 0.066(2) Uani 1 1 d . . . O3 O -0.0700(18) 0.0695(7) 0.8374(8) 0.093(4) Uani 1 1 d . . . O4 O 0.067(3) 0.2354(6) 0.9172(7) 0.098(4) Uani 1 1 d . . . O5 O 0.8621(10) 0.5372(4) 0.8944(4) 0.0404(11) Uani 1 1 d . . . O6 O 0.5258(14) 0.5849(5) 0.9685(4) 0.0546(16) Uani 1 1 d . . . C1 C 0.6402(12) 0.5269(4) 0.9245(4) 0.0306(11) Uani 1 1 d . . . C2 C 0.4987(10) 0.4327(4) 0.9050(3) 0.0226(8) Uani 1 1 d . . . H2 H 0.6148 0.3790 0.9183 0.027 Uiso 1 1 calc R . . N1 N 0.2584(11) 0.4263(5) 0.9548(3) 0.0341(11) Uani 1 1 d . . . H1A H 0.2992 0.4390 1.0052 0.051 Uiso 1 1 calc R . . H1B H 0.1918 0.3673 0.9514 0.051 Uiso 1 1 calc R . . H1C H 0.1403 0.4686 0.9377 0.051 Uiso 1 1 calc R . . C3 C 0.4193(11) 0.4244(4) 0.8186(3) 0.0264(9) Uani 1 1 d . . . H3A H 0.3464 0.4854 0.8016 0.032 Uiso 1 1 calc R . . H3B H 0.2814 0.3766 0.8143 0.032 Uiso 1 1 calc R . . C4 C 0.6407(11) 0.3971(5) 0.7622(3) 0.0279(10) Uani 1 1 d . . . H4A H 0.7595 0.4510 0.7560 0.034 Uiso 1 1 calc R . . H4B H 0.7393 0.3438 0.7843 0.034 Uiso 1 1 calc R . . C5 C 0.5304(13) 0.3690(5) 0.6821(3) 0.0320(11) Uani 1 1 d . . . H5A H 0.4117 0.3152 0.6892 0.038 Uiso 1 1 calc R . . H5B H 0.4286 0.4223 0.6614 0.038 Uiso 1 1 calc R . . N2 N 0.7328(12) 0.3421(3) 0.6223(3) 0.0314(11) Uani 1 1 d . . . H2A H 0.7657 0.3829 0.5853 0.038 Uiso 1 1 calc R . . C6 C 0.8621(11) 0.2632(4) 0.6215(3) 0.0248(9) Uani 1 1 d . . . N3 N 1.0482(14) 0.2510(4) 0.5665(3) 0.0369(12) Uani 1 1 d . . . H3C H 1.0794 0.2957 0.5325 0.044 Uiso 1 1 calc R . . H3D H 1.1369 0.1985 0.5651 0.044 Uiso 1 1 calc R . . N4 N 0.8198(15) 0.1945(4) 0.6744(3) 0.0357(11) Uani 1 1 d . . . H4C H 0.7027 0.2022 0.7107 0.043 Uiso 1 1 calc R . . H4D H 0.9094 0.1422 0.6725 0.043 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 Re1 0.04129(13) 0.03727(12) 0.03283(11) 0.00597(10) 0.00464(11) -0.00405(11) O1 0.107(8) 0.096(7) 0.049(4) 0.025(4) -0.029(5) -0.006(6) O2 0.068(5) 0.080(5) 0.051(3) 0.030(3) 0.025(3) 0.005(4) O3 0.051(4) 0.068(5) 0.159(11) -0.028(6) 0.002(6) -0.023(4) O4 0.139(10) 0.055(5) 0.099(7) -0.033(5) 0.052(8) -0.017(6) O5 0.031(2) 0.040(3) 0.050(3) 0.008(2) -0.003(2) -0.0092(18) O6 0.058(4) 0.041(3) 0.065(4) -0.027(3) -0.007(3) 0.007(3) C1 0.030(3) 0.027(2) 0.035(3) -0.003(2) -0.010(2) 0.0023(19) C2 0.025(2) 0.0200(19) 0.0229(19) -0.0034(16) 0.0042(16) -0.0008(15) N1 0.033(2) 0.037(3) 0.032(2) -0.003(2) 0.0068(18) 0.000(2) C3 0.0194(19) 0.029(2) 0.031(2) -0.0053(19) -0.0020(18) 0.0013(19) C4 0.028(2) 0.032(3) 0.024(2) -0.0068(18) 0.0015(17) -0.0003(18) C5 0.038(3) 0.034(3) 0.024(2) -0.001(2) -0.0020(19) 0.008(2) N2 0.041(3) 0.025(2) 0.028(2) 0.0114(15) -0.0023(18) 0.0011(17) C6 0.032(2) 0.022(2) 0.0205(19) -0.0003(15) -0.0024(15) 0.0025(16) N3 0.048(3) 0.033(3) 0.030(2) 0.0025(19) 0.011(2) 0.008(2) N4 0.047(3) 0.025(2) 0.035(2) 0.0055(17) 0.006(3) 0.006(2) _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 Re1 O4 1.692(9) . ? Re1 O2 1.696(6) . ? Re1 O3 1.719(8) . ? Re1 O1 1.729(9) . ? O5 C1 1.246(8) . ? O6 C1 1.241(9) . ? C1 C2 1.532(8) . ? C2 N1 1.486(7) . ? C2 C3 1.512(8) . ? C2 H2 0.9800 . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 H1C 0.8900 . ? C3 C4 1.521(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.513(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N2 1.487(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? N2 C6 1.281(7) . ? N2 H2A 0.8600 . ? C6 N4 1.324(7) . ? C6 N3 1.334(8) . ? N3 H3C 0.8600 . ? N3 H3D 0.8600 . ? N4 H4C 0.8600 . ? N4 H4D 0.8600 . ? 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 O4 Re1 O2 112.7(5) . . ? O4 Re1 O3 108.1(6) . . ? O2 Re1 O3 108.8(5) . . ? O4 Re1 O1 110.9(6) . . ? O2 Re1 O1 111.3(5) . . ? O3 Re1 O1 104.6(6) . . ? O6 C1 O5 126.3(7) . . ? O6 C1 C2 117.7(6) . . ? O5 C1 C2 116.0(6) . . ? N1 C2 C3 108.5(4) . . ? N1 C2 C1 108.5(5) . . ? C3 C2 C1 113.5(5) . . ? N1 C2 H2 108.7 . . ? C3 C2 H2 108.7 . . ? C1 C2 H2 108.7 . . ? C2 N1 H1A 109.5 . . ? C2 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C2 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? C2 C3 C4 114.9(4) . . ? C2 C3 H3A 108.6 . . ? C4 C3 H3A 108.6 . . ? C2 C3 H3B 108.6 . . ? C4 C3 H3B 108.6 . . ? H3A C3 H3B 107.5 . . ? C5 C4 C3 110.2(5) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? N2 C5 C4 114.3(5) . . ? N2 C5 H5A 108.7 . . ? C4 C5 H5A 108.7 . . ? N2 C5 H5B 108.7 . . ? C4 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C6 N2 C5 125.4(5) . . ? C6 N2 H2A 117.3 . . ? C5 N2 H2A 117.3 . . ? N2 C6 N4 121.9(6) . . ? N2 C6 N3 118.8(5) . . ? N4 C6 N3 119.3(5) . . ? C6 N3 H3C 120.0 . . ? C6 N3 H3D 120.0 . . ? H3C N3 H3D 120.0 . . ? C6 N4 H4C 120.0 . . ? C6 N4 H4D 120.0 . . ? H4C N4 H4D 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O6 C1 C2 N1 -8.1(8) . . . . ? O5 C1 C2 N1 171.6(6) . . . . ? O6 C1 C2 C3 112.6(7) . . . . ? O5 C1 C2 C3 -67.6(7) . . . . ? N1 C2 C3 C4 -160.9(5) . . . . ? C1 C2 C3 C4 78.4(6) . . . . ? C2 C3 C4 C5 167.3(5) . . . . ? C3 C4 C5 N2 179.3(5) . . . . ? C4 C5 N2 C6 74.6(8) . . . . ? C5 N2 C6 N4 2.2(10) . . . . ? C5 N2 C6 N3 -176.4(6) . . . . ? 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 O1 0.89 2.44 2.774(10) 102.6 4_457 N1 H1B O4 0.89 2.03 2.900(11) 166.8 . N1 H1C O5 0.89 1.86 2.737(8) 169.3 1_455 N2 H2A O6 0.86 2.28 3.039(8) 147.8 2_664 N3 H3C O6 0.86 2.05 2.842(8) 152.5 2_664 N3 H3D O5 0.86 2.35 3.082(8) 143.8 3_746 N3 H3D O6 0.86 2.40 3.225(10) 160.4 3_746 N4 H4C O2 0.86 2.17 2.994(10) 159.6 . N4 H4D O5 0.86 2.18 2.959(8) 150.4 3_746 C5 H5A O2 0.97 2.57 3.347(10) 137.1 . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 36.63 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 6.534 _refine_diff_density_min -3.687 _refine_diff_density_rms 0.243