# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Charles Devillers' 'Dominique Lucas' 'Yves Mugnier' 'Yoann Rousselin' _publ_contact_author_name 'Charles Devillers' _publ_contact_author_email CHARLES.DEVILLERS@U-BOURGOGNE.FR _publ_section_title ; Exploring the redox reactivity of magnesium porphine. Insight into the origins of electropolymerization ; # Attachment 'crystal_structure_of_2_DEVILLERS1.cif' #============================================================================== data_08cde47b _database_code_depnum_ccdc_archive 'CCDC 741386' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N2 O' _chemical_formula_sum 'C10 H10 N2 O' _chemical_formula_weight 174.20 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8435(5) _cell_length_b 6.9555(2) _cell_length_c 11.1256(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.4700(10) _cell_angle_gamma 90.00 _cell_volume 878.89(6) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3796 _cell_measurement_theta_min 0.985 _cell_measurement_theta_max 27.498 _exptl_crystal_description Prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3559 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1985 _reflns_number_gt 1453 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia,1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0549P)^2^+0.1140P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.049(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1985 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.38252(12) 0.8982(2) 0.21621(13) 0.0250(3) Uani 1 1 d . . . H1 H 0.3806 0.9977 0.1572 0.030 Uiso 1 1 calc R . . C2 C 0.44284(12) 0.9021(2) 0.34040(13) 0.0260(3) Uani 1 1 d . . . H2 H 0.4905 1.0045 0.3836 0.031 Uiso 1 1 calc R . . C3 C 0.42121(11) 0.7253(2) 0.39306(12) 0.0235(3) Uani 1 1 d . . . H3 H 0.4515 0.6877 0.4782 0.028 Uiso 1 1 calc R . . C4 C 0.34864(11) 0.6182(2) 0.29899(12) 0.0214(3) Uani 1 1 d . . . C5 C 0.29928(12) 0.4198(2) 0.30005(14) 0.0267(4) Uani 1 1 d . . . H5A H 0.3473 0.3511 0.3751 0.032 Uiso 1 1 calc R . . H5B H 0.3069 0.3495 0.2254 0.032 Uiso 1 1 calc R . . C6 C 0.17264(12) 0.41410(19) 0.30055(12) 0.0220(3) Uani 1 1 d . . . C7 C 0.12525(13) 0.3971(2) 0.40057(13) 0.0260(3) Uani 1 1 d . . . H7 H 0.1683 0.3867 0.4865 0.031 Uiso 1 1 calc R . . C8 C 0.00283(12) 0.3981(2) 0.35229(12) 0.0247(3) Uani 1 1 d . . . H8 H -0.0525 0.3875 0.3993 0.030 Uiso 1 1 calc R . . C9 C -0.02333(12) 0.41739(19) 0.22360(12) 0.0207(3) Uani 1 1 d . . . C10 C -0.13449(12) 0.42063(19) 0.13218(12) 0.0217(3) Uani 1 1 d . . . H10 H -0.2026 0.4132 0.1610 0.026 Uiso 1 1 calc R . . N1 N 0.32526(9) 0.72529(17) 0.19176(10) 0.0226(3) Uani 1 1 d . . . H1A H 0.2802 0.6886 0.1180 0.027 Uiso 1 1 d R . . N2 N 0.08226(9) 0.42641(15) 0.19445(10) 0.0206(3) Uani 1 1 d . . . H2A H 0.0897 0.4384 0.1183 0.025 Uiso 1 1 d R . . O1 O -0.14980(8) 0.43235(14) 0.01748(8) 0.0264(3) Uani 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 C1 0.0234(7) 0.0267(8) 0.0276(7) -0.0005(6) 0.0116(6) -0.0029(6) C2 0.0200(7) 0.0296(8) 0.0287(7) -0.0090(6) 0.0075(6) -0.0060(6) C3 0.0173(7) 0.0304(8) 0.0221(7) -0.0015(6) 0.0045(5) 0.0014(6) C4 0.0136(7) 0.0256(8) 0.0248(6) -0.0023(6) 0.0050(5) 0.0023(5) C5 0.0194(7) 0.0223(8) 0.0353(8) -0.0013(6) 0.0027(6) 0.0020(6) C6 0.0214(7) 0.0163(7) 0.0252(7) -0.0001(5) 0.0018(6) -0.0021(5) C7 0.0286(8) 0.0254(8) 0.0203(6) 0.0011(6) 0.0008(6) -0.0046(6) C8 0.0256(8) 0.0264(8) 0.0229(7) -0.0014(6) 0.0079(6) -0.0053(6) C9 0.0200(7) 0.0211(7) 0.0220(7) -0.0010(5) 0.0075(5) -0.0030(5) C10 0.0204(7) 0.0231(7) 0.0226(7) -0.0030(5) 0.0077(5) -0.0053(6) N1 0.0194(6) 0.0277(7) 0.0200(5) -0.0050(5) 0.0042(4) -0.0021(5) N2 0.0190(6) 0.0225(6) 0.0207(6) -0.0007(4) 0.0061(5) -0.0021(5) O1 0.0236(5) 0.0354(6) 0.0194(5) -0.0021(4) 0.0047(4) -0.0057(4) _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 C2 1.3640(19) . ? C1 N1 1.3693(18) . ? C1 H1 0.9500 . ? C2 C3 1.417(2) . ? C2 H2 0.9500 . ? C3 C4 1.3706(18) . ? C3 H3 0.9500 . ? C4 N1 1.3664(17) . ? C4 C5 1.500(2) . ? C5 C6 1.502(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N2 1.3528(16) . ? C6 C7 1.386(2) . ? C7 C8 1.396(2) . ? C7 H7 0.9500 . ? C8 C9 1.3828(18) . ? C8 H8 0.9500 . ? C9 N2 1.3794(17) . ? C9 C10 1.4174(19) . ? C10 O1 1.2396(15) . ? C10 H10 0.9500 . ? N1 H1A 0.8800 . ? N2 H2A 0.8800 . ? 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 C2 C1 N1 107.86(12) . . ? C2 C1 H1 126.1 . . ? N1 C1 H1 126.1 . . ? C1 C2 C3 107.29(12) . . ? C1 C2 H2 126.4 . . ? C3 C2 H2 126.4 . . ? C4 C3 C2 107.68(11) . . ? C4 C3 H3 126.2 . . ? C2 C3 H3 126.2 . . ? N1 C4 C3 107.37(12) . . ? N1 C4 C5 121.68(12) . . ? C3 C4 C5 130.94(13) . . ? C4 C5 C6 114.60(11) . . ? C4 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? C4 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? N2 C6 C7 107.79(12) . . ? N2 C6 C5 122.62(12) . . ? C7 C6 C5 129.59(13) . . ? C6 C7 C8 107.67(12) . . ? C6 C7 H7 126.2 . . ? C8 C7 H7 126.2 . . ? C9 C8 C7 107.58(12) . . ? C9 C8 H8 126.2 . . ? C7 C8 H8 126.2 . . ? N2 C9 C8 107.21(12) . . ? N2 C9 C10 123.37(12) . . ? C8 C9 C10 129.37(13) . . ? O1 C10 C9 125.09(13) . . ? O1 C10 H10 117.5 . . ? C9 C10 H10 117.5 . . ? C4 N1 C1 109.80(11) . . ? C4 N1 H1A 125.1 . . ? C1 N1 H1A 125.1 . . ? C6 N2 C9 109.74(11) . . ? C6 N2 H2A 125.1 . . ? C9 N2 H2A 125.1 . . ? 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 N1 C1 C2 C3 -0.05(15) . . . . ? C1 C2 C3 C4 0.29(15) . . . . ? C2 C3 C4 N1 -0.41(15) . . . . ? C2 C3 C4 C5 178.77(13) . . . . ? N1 C4 C5 C6 -78.35(16) . . . . ? C3 C4 C5 C6 102.57(17) . . . . ? C4 C5 C6 N2 84.33(16) . . . . ? C4 C5 C6 C7 -95.47(17) . . . . ? N2 C6 C7 C8 0.40(15) . . . . ? C5 C6 C7 C8 -179.78(13) . . . . ? C6 C7 C8 C9 -0.53(16) . . . . ? C7 C8 C9 N2 0.46(15) . . . . ? C7 C8 C9 C10 178.08(13) . . . . ? N2 C9 C10 O1 -0.2(2) . . . . ? C8 C9 C10 O1 -177.52(14) . . . . ? C3 C4 N1 C1 0.39(15) . . . . ? C5 C4 N1 C1 -178.88(12) . . . . ? C2 C1 N1 C4 -0.20(15) . . . . ? C7 C6 N2 C9 -0.11(15) . . . . ? C5 C6 N2 C9 -179.95(12) . . . . ? C8 C9 N2 C6 -0.22(15) . . . . ? C10 C9 N2 C6 -178.02(12) . . . . ? 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 0.88 2.01 2.8630(14) 162.5 3_565 N2 H2A O1 0.88 2.05 2.8696(14) 154.3 3_565 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.214 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.043