# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author # name and address of author for correspondence ; Dr F. Millange ILV, UMR CNRS 8180 Universit\'e de Versailles Saint-Quentin-en-Yvelines 45 Avenue des Etats Unis 78035 Versailles Cedex France ; _publ_contact_author_phone '(33) 1 39 25 43 30' _publ_contact_author_fax '(33) 1 39 25 43 58' _publ_contact_author_email franck.millange@uvsq.fr _publ_requested_coeditor_name ? _publ_contact_letter ; ; #==================================================================== # 2. processing summary (iucr office use only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ; _journal_techeditor_code ? _journal_techeditor_notes ; ; _journal_coden_astm ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #==================================================================== # 3. title and author list _publ_section_title ; Regular Charge Order in Metal-Organic Framework: a First Example ; # the loop structure below should contain the names and addresses of all # authors, in the required order of publication. repeat as necessary. loop_ _publ_author_name _publ_author_address 'Medina, Manuela Elo sa' ; Instituto de Ciencia de Materiales de Madrid, Departamento de Nuevas Arquitecturas en Qu mica de Materiales Madrid Spain ; 'Dumont, Yves' ; GEMac, UMR CNRS 8180 Universit\'e de Versailles Saint-Quentin-en-Yvelines 45 Avenue des Etats Unis 78035 Versailles Cedex France ; 'Greneche, Jean-Marc' ; LPEC, UMR CNRS 6087 Universit\'e du Maine 72085 Le Mans Cedex France ; 'Millange, Franck' ; ILV, UMR CNRS 8180 Universit\'e de Versailles Saint-Quentin-en-Yvelines 45 Avenue des Etats Unis 78035 Versailles Cedex France ; #==================================================================== # 4. text _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; sheldrick, g.m. (1993). shelxl-93. program for crystal structure determination. univ. of g\"ottingen, federal republic of germany. sheldrick, g.m. (1997). shelxs-86. program for the solution of crystal structures. univ. of g\"ottingen, federal republic of germany. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #==================================================================== data_shelxl _database_code_depnum_ccdc_archive 'CCDC 793569' #TrackingRef 'mm125final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 Fe2 N O10' _chemical_formula_weight 518.02 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9004(14) _cell_length_b 8.554(3) _cell_length_c 10.380(3) _cell_angle_alpha 107.15(2) _cell_angle_beta 100.155(17) _cell_angle_gamma 102.095(17) _cell_volume 553.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour 'ligth orange' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 263 _exptl_absorpt_coefficient_mu 1.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7723 _exptl_absorpt_correction_T_max 0.9227 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; 'Blessing, Acta Cryst. (1995) A51, 33-38' ; _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 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 512x512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3051 _diffrn_reflns_av_R_equivalents 0.0736 _diffrn_reflns_av_sigmaI/netI 0.0887 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1944 _reflns_number_gt 1329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0841P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.0037(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1944 _refine_ls_number_parameters 160 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1507 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.004 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 Fe1 Fe 1.0000 0.5000 0.5000 0.02238(11) Uani 1 2 d S . . Fe2 Fe 0.5000 0.5000 0.5000 0.02451(11) Uani 1 2 d S . . C1 C 0.6389(3) 0.2418(2) 0.28260(19) 0.0283(6) Uani 1 1 d . . . C2 C 0.5684(3) 0.1158(2) 0.1363(2) 0.0304(6) Uani 1 1 d . . . C3 C 0.3604(3) 0.0411(3) 0.0736(2) 0.0458(8) Uani 1 1 d . . . H3 H 0.2654 0.0698 0.1230 0.055 Uiso 1 1 calc R . . C4 C 0.7071(3) 0.0740(3) 0.0598(2) 0.0457(8) Uani 1 1 d . . . H4 H 0.8468 0.1243 0.0992 0.055 Uiso 1 1 calc R . . C5 C 0.7989(3) 0.4294(2) 0.71214(19) 0.0292(6) Uani 1 1 d . . . C6 C 0.8999(3) 0.4625(2) 0.8613(2) 0.0322(6) Uani 1 1 d . . . C7 C 0.7989(3) 0.5048(3) 0.9642(2) 0.0434(7) Uani 1 1 d . . . H7 H 0.6644 0.5098 0.9407 0.052 Uiso 1 1 calc R . . C8 C 1.1037(3) 0.4602(3) 0.8977(2) 0.0440(7) Uani 1 1 d . . . H8 H 1.1742 0.4352 0.8292 0.053 Uiso 1 1 calc R . . C9 C 0.7417(10) 0.9449(9) 0.4411(9) 0.193(5) Uani 0.50 1 d PD . . H9A H 0.7428 1.0608 0.4856 0.289 Uiso 0.50 1 calc PR . . H9B H 0.6706 0.8737 0.4841 0.289 Uiso 0.50 1 calc PR . . H9C H 0.6733 0.9077 0.3439 0.289 Uiso 0.50 1 calc PR . . C10 C 1.0485(11) 0.9863(8) 0.3580(7) 0.137(4) Uani 0.50 1 d PD . . H10A H 0.9678 0.9211 0.2646 0.206 Uiso 0.50 1 calc PR . . H10B H 1.1820 0.9677 0.3695 0.206 Uiso 0.50 1 calc PR . . H10C H 1.0618 1.1051 0.3751 0.206 Uiso 0.50 1 calc PR . . N1 N 0.9490(13) 0.9335(7) 0.4559(9) 0.163(4) Uani 0.50 1 d P . . H1A H 0.9487 0.8250 0.4448 0.196 Uiso 0.50 1 calc PR . . H1B H 1.0229 0.9986 0.5431 0.196 Uiso 0.50 1 calc PR . . O1 O 0.78883(16) 0.61684(13) 0.50255(11) 0.0138(3) Uani 1 1 d . . . O2 O 0.8336(2) 0.30948(17) 0.32713(13) 0.0329(4) Uani 1 1 d . . . O3 O 0.8984(2) 0.38196(16) 0.62280(13) 0.0304(4) Uani 1 1 d . . . O4 O 0.6244(2) 0.44946(19) 0.68387(14) 0.0442(5) Uani 1 1 d . . . O5 O 0.5104(2) 0.27314(18) 0.34913(14) 0.0368(5) 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 Fe1 0.01916(17) 0.02748(17) 0.01465(16) 0.00065(13) 0.00030(14) 0.00724(14) Fe2 0.01879(16) 0.03548(19) 0.01379(17) 0.00101(14) -0.00028(14) 0.01069(14) C1 0.0305(10) 0.0232(9) 0.0241(9) 0.0012(7) 0.0034(8) 0.0059(8) C2 0.0280(9) 0.0287(9) 0.0212(9) -0.0060(8) -0.0023(8) 0.0083(8) C3 0.0279(10) 0.0593(14) 0.0298(11) -0.0146(10) 0.0114(9) 0.0101(10) C4 0.0224(10) 0.0559(14) 0.0342(12) -0.0093(11) -0.0018(10) 0.0031(10) C5 0.0267(9) 0.0322(9) 0.0225(9) 0.0076(7) -0.0009(8) 0.0041(8) C6 0.0312(10) 0.0396(10) 0.0236(9) 0.0102(7) 0.0031(8) 0.0096(8) C7 0.0309(9) 0.0758(13) 0.0286(10) 0.0179(9) 0.0067(8) 0.0267(9) C8 0.0349(10) 0.0789(13) 0.0252(10) 0.0209(9) 0.0085(8) 0.0253(10) C9 0.143(9) 0.117(3) 0.362(9) 0.172(4) 0.034(8) 0.024(5) C10 0.254(10) 0.058(3) 0.097(5) 0.033(3) 0.012(6) 0.055(5) N1 0.206(5) 0.058(4) 0.249(7) 0.026(4) 0.143(4) 0.051(4) O1 0.0104(5) 0.0152(5) 0.0131(5) 0.0014(4) 0.0007(4) 0.0050(4) O2 0.0269(7) 0.0374(7) 0.0208(7) -0.0051(6) 0.0004(5) 0.0071(6) O3 0.0372(7) 0.0371(6) 0.0183(6) 0.0095(5) 0.0062(5) 0.0142(6) O4 0.0362(7) 0.0736(8) 0.0285(7) 0.0220(6) 0.0041(6) 0.0239(7) O5 0.0280(7) 0.0406(8) 0.0253(7) -0.0079(6) 0.0040(6) 0.0055(6) _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 Fe1 O1 1.9317(12) 2_766 ? Fe1 O1 1.9317(12) . ? Fe1 O3 1.9784(15) 2_766 ? Fe1 O3 1.9784(15) . ? Fe1 O2 1.9896(13) 2_766 ? Fe1 O2 1.9896(13) . ? Fe2 O1 2.0256(12) 2_666 ? Fe2 O1 2.0256(12) . ? Fe2 O5 2.1281(16) . ? Fe2 O5 2.1281(16) 2_666 ? Fe2 O4 2.1520(16) . ? Fe2 O4 2.1520(16) 2_666 ? C1 O5 1.241(3) . ? C1 O2 1.285(2) . ? C1 C2 1.503(2) . ? C2 C4 1.385(3) . ? C2 C3 1.390(3) . ? C3 C4 1.372(3) 2_655 ? C3 H3 0.9300 . ? C4 C3 1.372(3) 2_655 ? C4 H4 0.9300 . ? C5 O4 1.248(3) . ? C5 O3 1.271(3) . ? C5 C6 1.497(3) . ? C6 C7 1.377(3) . ? C6 C8 1.396(3) . ? C7 C8 1.385(3) 2_767 ? C7 H7 0.9300 . ? C8 C7 1.385(3) 2_767 ? C8 H8 0.9300 . ? C9 N1 1.439(11) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N1 1.447(12) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? 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 O1 Fe1 O1 180.000(1) 2_766 . ? O1 Fe1 O3 92.28(6) 2_766 2_766 ? O1 Fe1 O3 87.72(6) . 2_766 ? O1 Fe1 O3 87.72(6) 2_766 . ? O1 Fe1 O3 92.28(6) . . ? O3 Fe1 O3 180.0 2_766 . ? O1 Fe1 O2 92.59(6) 2_766 2_766 ? O1 Fe1 O2 87.41(6) . 2_766 ? O3 Fe1 O2 92.97(6) 2_766 2_766 ? O3 Fe1 O2 87.03(6) . 2_766 ? O1 Fe1 O2 87.41(6) 2_766 . ? O1 Fe1 O2 92.59(6) . . ? O3 Fe1 O2 87.03(6) 2_766 . ? O3 Fe1 O2 92.97(6) . . ? O2 Fe1 O2 180.000(1) 2_766 . ? O1 Fe2 O1 180.0 2_666 . ? O1 Fe2 O5 89.79(5) 2_666 . ? O1 Fe2 O5 90.21(5) . . ? O1 Fe2 O5 90.21(5) 2_666 2_666 ? O1 Fe2 O5 89.79(5) . 2_666 ? O5 Fe2 O5 180.000(1) . 2_666 ? O1 Fe2 O4 91.26(6) 2_666 . ? O1 Fe2 O4 88.74(6) . . ? O5 Fe2 O4 97.87(6) . . ? O5 Fe2 O4 82.13(6) 2_666 . ? O1 Fe2 O4 88.74(6) 2_666 2_666 ? O1 Fe2 O4 91.26(6) . 2_666 ? O5 Fe2 O4 82.13(6) . 2_666 ? O5 Fe2 O4 97.87(6) 2_666 2_666 ? O4 Fe2 O4 180.0 . 2_666 ? O5 C1 O2 125.69(16) . . ? O5 C1 C2 119.47(16) . . ? O2 C1 C2 114.84(18) . . ? C4 C2 C3 118.49(17) . . ? C4 C2 C1 121.26(17) . . ? C3 C2 C1 120.2(2) . . ? C4 C3 C2 121.1(2) 2_655 . ? C4 C3 H3 119.4 2_655 . ? C2 C3 H3 119.4 . . ? C3 C4 C2 120.36(18) 2_655 . ? C3 C4 H4 119.8 2_655 . ? C2 C4 H4 119.8 . . ? O4 C5 O3 124.61(18) . . ? O4 C5 C6 118.36(19) . . ? O3 C5 C6 117.03(18) . . ? C7 C6 C8 119.48(19) . . ? C7 C6 C5 121.0(2) . . ? C8 C6 C5 119.4(2) . . ? C6 C7 C8 120.4(2) . 2_767 ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 2_767 . ? C7 C8 C6 120.1(2) 2_767 . ? C7 C8 H8 119.9 2_767 . ? C6 C8 H8 119.9 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 N1 C10 114.1(8) . . ? C9 N1 H1A 108.7 . . ? C10 N1 H1A 108.7 . . ? C9 N1 H1B 108.7 . . ? C10 N1 H1B 108.7 . . ? H1A N1 H1B 107.6 . . ? Fe1 O1 Fe2 121.33(6) . . ? C1 O2 Fe1 130.80(13) . . ? C5 O3 Fe1 128.36(14) . . ? C5 O4 Fe2 123.75(14) . . ? C1 O5 Fe2 131.89(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 0.90 2.19 2.915(7) 137.5 . N1 H1A O3 0.90 2.25 3.042(7) 146.9 2_766 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.800 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.125