# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jurg Hulliger' _publ_contact_author_email JUERG.HULLIGER@IAC.UNIBE.CH _publ_section_title ; Polymorphism, polar morphology and absolute structure determination of 4-iodo-4'-nitrobiphenyl (INBP) ; loop_ _publ_author_name 'Jurg Hulliger' 'Athanasios Batagiannis' 'Norwid-Rasmus Behrnd' 'Ricarda Berger' 'Mariana Bertoni' ; M.Bonin ; 'Labat Gael' 'Couderc Gaetan' 'Anna Prodi-Schwab' 'Julius Tsuwi' # Attachment 'CIFS.txt' data_CCDC724433 _database_code_depnum_ccdc_archive 'CCDC 724433' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 I N O2' _chemical_formula_sum 'C12 H8 I N O2' _chemical_formula_weight 325.09 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' I I -0.4742 1.8119 '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 orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+3/4, -y+5/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+5/4, -y+3/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+5/4, -y+5/4, z+1/4' _cell_length_a 18.892(6) _cell_length_b 8.215(3) _cell_length_c 14.400(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2234.8(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3061 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 33.30 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.932 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 2.849 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5933 _exptl_absorpt_correction_T_max 0.8126 _exptl_absorpt_process_details ? _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 'STOE image plate 2' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5908 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 33.33 _reflns_number_total 1889 _reflns_number_gt 1120 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2005)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2005)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _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^)+(0.0308P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(3) _refine_ls_number_reflns 1889 _refine_ls_number_parameters 76 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0548 _refine_ls_goodness_of_fit_ref 0.897 _refine_ls_restrained_S_all 0.897 _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 I1 I 0.5000 -0.5000 0.0000 0.05505(12) Uani 1 2 d S . . O1 O 0.4433(2) -0.4874(6) -0.7777(3) 0.0866(13) Uani 1 1 d . . . N1 N 0.5000 -0.5000 -0.7374(4) 0.0605(13) Uani 1 2 d S . . C1 C 0.5000 -0.5000 -0.1463(4) 0.0461(12) Uani 1 2 d S . . C2 C 0.4514(3) -0.4076(6) -0.1934(3) 0.0499(10) Uani 1 1 d . . . H1 H 0.4185 -0.3458 -0.1608 0.060 Uiso 1 1 calc R . . C3 C 0.4513(3) -0.4062(5) -0.2900(3) 0.0488(10) Uani 1 1 d . . . H2 H 0.4186 -0.3423 -0.3215 0.059 Uiso 1 1 calc R . . C4 C 0.5000 -0.5000 -0.3406(7) 0.040(2) Uani 1 2 d S . . C5 C 0.5000 -0.5000 -0.4443(4) 0.0426(10) Uani 1 2 d S . . C6 C 0.43695(19) -0.4828(6) -0.4932(8) 0.0474(12) Uani 1 1 d . . . H3 H 0.3946 -0.4695 -0.4611 0.057 Uiso 1 1 calc R . . C7 C 0.4367(2) -0.4855(5) -0.5891(3) 0.0511(9) Uani 1 1 d . . . H4 H 0.3945 -0.4775 -0.6221 0.061 Uiso 1 1 calc R . . C8 C 0.5000 -0.5000 -0.6342(8) 0.050(3) Uani 1 2 d S . . 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 I1 0.05781(19) 0.0709(2) 0.03646(15) 0.000 0.000 -0.0151(3) O1 0.083(3) 0.135(4) 0.0428(19) -0.004(2) -0.0151(19) 0.024(3) N1 0.075(4) 0.063(3) 0.043(3) 0.000 0.000 0.009(3) C1 0.052(3) 0.052(3) 0.034(3) 0.000 0.000 -0.009(5) C2 0.050(3) 0.060(3) 0.040(2) -0.0044(19) 0.0011(19) 0.007(2) C3 0.051(2) 0.051(2) 0.044(2) -0.0010(18) -0.0021(19) 0.0066(19) C4 0.045(4) 0.038(3) 0.038(6) 0.000 0.000 -0.006(4) C5 0.045(3) 0.041(2) 0.042(3) 0.000 0.000 0.001(2) C6 0.0474(15) 0.050(2) 0.044(3) 0.001(3) 0.000(3) 0.0051(18) C7 0.055(2) 0.057(2) 0.041(2) 0.0032(18) -0.0017(17) 0.003(2) C8 0.064(5) 0.051(4) 0.034(6) 0.000 0.000 0.005(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 I1 C1 2.107(5) . ? O1 N1 1.223(5) . ? N1 O1 1.223(5) 2_645 ? N1 C8 1.487(13) . ? C1 C2 1.371(6) . ? C1 C2 1.371(6) 2_645 ? C2 C3 1.391(6) . ? C2 H1 0.9300 . ? C3 C4 1.404(7) . ? C3 H2 0.9300 . ? C4 C3 1.404(7) 2_645 ? C4 C5 1.493(12) . ? C5 C6 1.391(7) . ? C5 C6 1.391(7) 2_645 ? C6 C7 1.381(13) . ? C6 H3 0.9300 . ? C7 C8 1.367(7) . ? C7 H4 0.9300 . ? C8 C7 1.367(7) 2_645 ? 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 N1 O1 123.4(6) . 2_645 ? O1 N1 C8 118.3(3) . . ? O1 N1 C8 118.3(3) 2_645 . ? C2 C1 C2 120.7(6) . 2_645 ? C2 C1 I1 119.6(3) . . ? C2 C1 I1 119.6(3) 2_645 . ? C1 C2 C3 120.0(5) . . ? C1 C2 H1 120.0 . . ? C3 C2 H1 120.0 . . ? C2 C3 C4 120.9(6) . . ? C2 C3 H2 119.5 . . ? C4 C3 H2 119.5 . . ? C3 C4 C3 117.5(8) . 2_645 ? C3 C4 C5 121.3(4) . . ? C3 C4 C5 121.3(4) 2_645 . ? C6 C5 C6 119.2(10) . 2_645 ? C6 C5 C4 120.4(5) . . ? C6 C5 C4 120.4(5) 2_645 . ? C7 C6 C5 120.5(6) . . ? C7 C6 H3 119.7 . . ? C5 C6 H3 119.7 . . ? C8 C7 C6 118.2(6) . . ? C8 C7 H4 120.9 . . ? C6 C7 H4 120.9 . . ? C7 C8 C7 123.3(9) . 2_645 ? C7 C8 N1 118.4(5) . . ? C7 C8 N1 118.4(5) 2_645 . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 33.33 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.299 _refine_diff_density_min -0.902 _refine_diff_density_rms 0.076 #==================================================================== data_CCDC724434 _database_code_depnum_ccdc_archive 'CCDC 724434' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 I N O2' _chemical_formula_sum 'C12 H8 I N O2' _chemical_formula_weight 325.11 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' I I -0.4742 1.8119 '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 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.405(3) _cell_length_b 14.441(5) _cell_length_c 8.194(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.074(18) _cell_angle_gamma 90.00 _cell_volume 1141.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3101 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 21.99 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.846 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 2.788 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.758742 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'refined from Sadabs (Bruker)' _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 SMART 1K' _diffrn_measurement_method 'omega scan method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12315 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2340 _reflns_number_gt 1624 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'SMART (Bruker, 1997)' _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_reduction 'SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL-97 _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^)+(0.0215P)^2^+0.3692P] 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 2340 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0576 _refine_ls_wR_factor_gt 0.0511 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 I1A I 0.5000 -0.02031(2) 0.2500 0.06917(13) Uani 1 2 d S . . O1A O 0.3922(3) 0.75566(18) 0.1671(4) 0.0910(8) Uani 1 1 d . . . N1A N 0.5000 0.7160(3) 0.2500 0.0661(11) Uani 1 2 d S . . C4A C 0.5000 0.3194(3) 0.2500 0.0536(11) Uani 1 2 d S . . C3A C 0.4077(3) 0.2683(2) 0.1099(4) 0.0659(9) Uani 1 1 d . . . H3A H 0.3448 0.2999 0.0143 0.079 Uiso 1 1 calc R . . C2A C 0.4067(4) 0.1729(2) 0.1086(4) 0.0665(9) Uani 1 1 d . . . H2A H 0.3440 0.1408 0.0136 0.080 Uiso 1 1 calc R . . C1A C 0.5000 0.1254(3) 0.2500 0.0577(12) Uani 1 2 d S . . C14A C 0.5000 0.4223(3) 0.2500 0.0558(12) Uani 1 2 d S . . C13A C 0.6209(3) 0.4723(2) 0.3367(5) 0.0722(10) Uani 1 1 d . . . H13A H 0.7033 0.4408 0.3961 0.087 Uiso 1 1 calc R . . C12A C 0.6209(4) 0.5680(2) 0.3363(5) 0.0726(10) Uani 1 1 d . . . H12A H 0.7024 0.6007 0.3943 0.087 Uiso 1 1 calc R . . C11A C 0.5000 0.6135(4) 0.2500 0.0622(12) Uani 1 2 d S . . I2A I 1.0000 -0.35694(2) 0.2500 0.08179(15) Uani 1 2 d S . . O2A O 1.1089(3) 0.41869(19) 0.2833(4) 0.1075(10) Uani 1 1 d . . . N2A N 1.0000 0.3803(4) 0.2500 0.0788(13) Uani 1 2 d S . . C24A C 1.0000 -0.0170(3) 0.2500 0.0556(12) Uani 1 2 d S . . C23A C 1.0932(3) -0.0680(2) 0.1998(4) 0.0604(8) Uani 1 1 d . . . H23A H 1.1568 -0.0367 0.1650 0.072 Uiso 1 1 calc R . . C22A C 1.0934(3) -0.1636(2) 0.2003(4) 0.0655(9) Uani 1 1 d . . . H22A H 1.1571 -0.1957 0.1670 0.079 Uiso 1 1 calc R . . C21A C 1.0000 -0.2116(4) 0.2500 0.0629(13) Uani 1 2 d S . . C34A C 1.0000 0.0847(3) 0.2500 0.0537(11) Uani 1 2 d S . . C33A C 0.8791(4) 0.1354(2) 0.2200(4) 0.0658(9) Uani 1 1 d . . . H33A H 0.7967 0.1037 0.1994 0.079 Uiso 1 1 calc R . . C32A C 0.8773(4) 0.2308(3) 0.2198(4) 0.0682(9) Uani 1 1 d . . . H32A H 0.7958 0.2635 0.1998 0.082 Uiso 1 1 calc R . . C31A C 1.0000 0.2759(4) 0.2500 0.0639(13) Uani 1 2 d S . . 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 I1A 0.0807(3) 0.0621(2) 0.0729(2) 0.000 0.03817(19) 0.000 O1A 0.0744(19) 0.0670(17) 0.119(2) 0.0040(16) 0.0226(16) 0.0131(15) N1A 0.066(3) 0.060(3) 0.074(3) 0.000 0.030(2) 0.000 C4A 0.048(3) 0.056(3) 0.058(3) 0.000 0.022(2) 0.000 C3A 0.062(2) 0.067(2) 0.058(2) -0.0008(17) 0.0109(17) 0.0043(18) C2A 0.068(2) 0.065(2) 0.057(2) -0.0098(17) 0.0127(17) 0.0007(18) C1A 0.057(3) 0.061(3) 0.058(3) 0.000 0.026(2) 0.000 C14A 0.050(3) 0.068(3) 0.047(2) 0.000 0.015(2) 0.000 C13A 0.046(2) 0.069(3) 0.086(3) 0.005(2) 0.0068(18) 0.0039(18) C12A 0.053(2) 0.065(2) 0.089(3) -0.003(2) 0.0139(19) -0.0075(18) C11A 0.057(3) 0.062(3) 0.068(3) 0.000 0.024(3) 0.000 I2A 0.0829(3) 0.0705(3) 0.0771(2) 0.000 0.01315(19) 0.000 O2A 0.101(2) 0.073(2) 0.133(3) 0.0008(17) 0.027(2) -0.0143(18) N2A 0.074(4) 0.089(4) 0.063(3) 0.000 0.014(3) 0.000 C24A 0.050(3) 0.066(3) 0.045(2) 0.000 0.012(2) 0.000 C23A 0.0470(19) 0.078(2) 0.0580(19) 0.0049(17) 0.0222(16) -0.0002(17) C22A 0.059(2) 0.073(2) 0.062(2) -0.0009(18) 0.0193(17) 0.0076(18) C21A 0.051(3) 0.079(4) 0.047(3) 0.000 0.005(2) 0.000 C34A 0.049(3) 0.060(3) 0.047(2) 0.000 0.013(2) 0.000 C33A 0.054(2) 0.076(3) 0.064(2) -0.0032(18) 0.0192(17) -0.0032(18) C32A 0.055(2) 0.076(3) 0.068(2) -0.0016(19) 0.0177(18) 0.0063(19) C31A 0.069(4) 0.064(3) 0.049(3) 0.000 0.012(2) 0.000 _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 I1A C1A 2.104(5) . ? O1A N1A 1.214(3) . ? N1A O1A 1.214(3) 2_655 ? N1A C11A 1.481(6) . ? C4A C3A 1.398(4) . ? C4A C3A 1.398(4) 2_655 ? C4A C14A 1.486(6) . ? C3A C2A 1.378(4) . ? C3A H3A 0.9300 . ? C2A C1A 1.382(4) . ? C2A H2A 0.9300 . ? C1A C2A 1.382(4) 2_655 ? C14A C13A 1.392(4) 2_655 ? C14A C13A 1.392(4) . ? C13A C12A 1.381(4) . ? C13A H13A 0.9300 . ? C12A C11A 1.359(4) . ? C12A H12A 0.9300 . ? C11A C12A 1.359(4) 2_655 ? I2A C21A 2.099(5) . ? O2A N2A 1.197(3) . ? N2A O2A 1.197(3) 2_755 ? N2A C31A 1.508(7) . ? C24A C23A 1.397(4) 2_755 ? C24A C23A 1.397(4) . ? C24A C34A 1.469(6) . ? C23A C22A 1.381(4) . ? C23A H23A 0.9300 . ? C22A C21A 1.374(4) . ? C22A H22A 0.9300 . ? C21A C22A 1.374(4) 2_755 ? C34A C33A 1.396(4) 2_755 ? C34A C33A 1.396(4) . ? C33A C32A 1.378(4) . ? C33A H33A 0.9300 . ? C32A C31A 1.370(4) . ? C32A H32A 0.9300 . ? C31A C32A 1.370(4) 2_755 ? 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 O1A N1A O1A 123.8(5) 2_655 . ? O1A N1A C11A 118.1(2) 2_655 . ? O1A N1A C11A 118.1(2) . . ? C3A C4A C3A 116.3(4) . 2_655 ? C3A C4A C14A 121.8(2) . . ? C3A C4A C14A 121.8(2) 2_655 . ? C2A C3A C4A 122.3(3) . . ? C2A C3A H3A 118.8 . . ? C4A C3A H3A 118.8 . . ? C3A C2A C1A 119.3(3) . . ? C3A C2A H2A 120.4 . . ? C1A C2A H2A 120.4 . . ? C2A C1A C2A 120.5(4) 2_655 . ? C2A C1A I1A 119.8(2) 2_655 . ? C2A C1A I1A 119.8(2) . . ? C13A C14A C13A 117.5(4) 2_655 . ? C13A C14A C4A 121.2(2) 2_655 . ? C13A C14A C4A 121.2(2) . . ? C12A C13A C14A 121.2(3) . . ? C12A C13A H13A 119.4 . . ? C14A C13A H13A 119.4 . . ? C11A C12A C13A 119.0(3) . . ? C11A C12A H12A 120.5 . . ? C13A C12A H12A 120.5 . . ? C12A C11A C12A 122.1(5) 2_655 . ? C12A C11A N1A 118.9(2) 2_655 . ? C12A C11A N1A 118.9(2) . . ? O2A N2A O2A 124.8(6) . 2_755 ? O2A N2A C31A 117.6(3) . . ? O2A N2A C31A 117.6(3) 2_755 . ? C23A C24A C23A 116.3(4) 2_755 . ? C23A C24A C34A 121.8(2) 2_755 . ? C23A C24A C34A 121.8(2) . . ? C22A C23A C24A 121.8(3) . . ? C22A C23A H23A 119.1 . . ? C24A C23A H23A 119.1 . . ? C21A C22A C23A 120.3(4) . . ? C21A C22A H22A 119.9 . . ? C23A C22A H22A 119.9 . . ? C22A C21A C22A 119.5(5) 2_755 . ? C22A C21A I2A 120.3(2) 2_755 . ? C22A C21A I2A 120.3(2) . . ? C33A C34A C33A 116.7(4) 2_755 . ? C33A C34A C24A 121.7(2) 2_755 . ? C33A C34A C24A 121.7(2) . . ? C32A C33A C34A 122.4(3) . . ? C32A C33A H33A 118.8 . . ? C34A C33A H33A 118.8 . . ? C31A C32A C33A 117.6(4) . . ? C31A C32A H32A 121.2 . . ? C33A C32A H32A 121.2 . . ? C32A C31A C32A 123.3(5) . 2_755 ? C32A C31A N2A 118.4(2) . . ? C32A C31A N2A 118.4(2) 2_755 . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.302 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.055 #===END