#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/32/2013209.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013209 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _publ_section_title ; A chain of edge-fused rings generated by the combination of an N---H···O hydrogen bond and an iodo--nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o98 _journal_page_last o101 _journal_paper_doi 10.1107/S0108270103001379 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C13 H10 I N3 O2' _chemical_formula_moiety 'C13 H10 I N3 O2' _chemical_formula_sum 'C13 H10 I N3 O2' _chemical_formula_weight 367.14 _chemical_name_systematic ; 2-Iodobenzaldehyse-4-nitrophenylhydrazone ; _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 24.0858(11) _cell_length_b 5.0699(2) _cell_length_c 10.5080(4) _cell_measurement_reflns_used 2800 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.42 _cell_measurement_theta_min 3.38 _cell_volume 1283.16(9) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Software (Nonius, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8490 _diffrn_reflns_theta_full 27.42 _diffrn_reflns_theta_max 27.42 _diffrn_reflns_theta_min 3.38 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 2.497 _exptl_absorpt_correction_T_max 0.865 _exptl_absorpt_correction_T_min 0.502 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.900 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _refine_diff_density_max 1.198 _refine_diff_density_min -0.471 _refine_ls_abs_structure_details 'Flack (1983), 1259 Friedel pairs' _refine_ls_abs_structure_Flack -0.08(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2800 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0356 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0298P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0714 _refine_ls_wR_factor_ref 0.0804 _reflns_number_gt 2082 _reflns_number_total 2800 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1609.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2013209 _cod_database_fobs_code 2013209 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol I22 0.876111(14) 0.80511(6) 0.99980(7) 0.02451(12) Uani d . 1 . . I O41 0.75761(18) -0.9173(10) 0.3440(4) 0.0298(10) Uani d . 1 . . O O42 0.8286(2) -0.7960(8) 0.2309(4) 0.0342(11) Uani d . 1 . . O N1 0.8383(2) 0.0228(9) 0.6790(5) 0.0238(12) Uani d . 1 . . N N2 0.88431(19) 0.1797(8) 0.6758(5) 0.0181(11) Uani d . 1 . . N N4 0.7976(2) -0.7716(10) 0.3259(5) 0.0252(12) Uani d . 1 . . N C11 0.8295(2) -0.1731(11) 0.5902(5) 0.0169(13) Uani d . 1 . . C C12 0.7819(3) -0.3277(11) 0.6028(6) 0.0203(14) Uani d . 1 . . C C13 0.7719(2) -0.5242(10) 0.5156(7) 0.0217(14) Uani d . 1 . . C C14 0.8089(2) -0.5666(12) 0.4170(5) 0.0190(12) Uani d . 1 . . C C15 0.8567(2) -0.4147(13) 0.4038(5) 0.0211(13) Uani d . 1 . . C C16 0.8674(2) -0.2158(9) 0.4942(19) 0.0216(14) Uani d . 1 . . C C21 0.9338(2) 0.5366(11) 0.7712(5) 0.0209(13) Uani d . 1 . . C C22 0.9396(2) 0.7336(11) 0.8643(6) 0.0206(13) Uani d . 1 . . C C23 0.9849(2) 0.8953(13) 0.8680(6) 0.0217(9) Uani d . 1 . . C C24 1.0273(2) 0.8620(11) 0.7729(6) 0.0217(9) Uani d . 1 . . C C25 1.0228(3) 0.6848(11) 0.6870(6) 0.0259(10) Uani d . 1 . . C C26 0.9777(2) 0.5148(11) 0.6803(6) 0.0259(10) Uani d . 1 . . C C27 0.8866(2) 0.3589(12) 0.7629(6) 0.0224(15) Uani d . 1 . . C H1 0.8136 0.0473 0.7395 0.029 Uiso calc R 1 . . H H2 0.8570 0.3748 0.8224 0.027 Uiso calc R 1 . . H H12 0.7567 -0.2975 0.6708 0.024 Uiso calc R 1 . . H H13 0.7396 -0.6307 0.5229 0.026 Uiso calc R 1 . . H H15 0.8816 -0.4445 0.3352 0.025 Uiso calc R 1 . . H H16 0.9003 -0.1126 0.4890 0.026 Uiso calc R 1 . . H H23 0.9883 1.0269 0.9318 0.026 Uiso calc R 1 . . H H24 1.0590 0.9732 0.7740 0.026 Uiso calc R 1 . . H H25 1.0514 0.6689 0.6253 0.031 Uiso calc R 1 . . H H26 0.9761 0.3843 0.6155 0.031 Uiso calc R 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I22 0.02463(18) 0.02820(19) 0.02070(17) 0.00047(14) 0.0017(3) -0.0016(4) O41 0.030(3) 0.027(2) 0.032(3) -0.010(2) -0.006(2) -0.003(2) O42 0.036(3) 0.045(3) 0.021(2) -0.004(2) 0.002(2) -0.012(2) N1 0.026(3) 0.029(3) 0.016(2) 0.000(2) 0.005(2) -0.003(2) N2 0.021(3) 0.014(3) 0.020(3) 0.000(2) -0.001(2) 0.003(2) N4 0.023(3) 0.027(3) 0.025(3) 0.007(2) -0.010(2) -0.001(2) C11 0.016(3) 0.017(3) 0.017(3) 0.000(2) -0.006(2) 0.006(3) C12 0.019(3) 0.022(4) 0.019(3) 0.002(3) 0.005(3) -0.003(3) C13 0.017(3) 0.023(3) 0.026(4) 0.0011(19) -0.006(3) 0.004(4) C14 0.022(3) 0.016(3) 0.018(3) 0.001(3) -0.005(3) 0.003(3) C15 0.022(3) 0.028(3) 0.013(3) 0.005(3) 0.001(3) 0.003(3) C16 0.016(3) 0.025(2) 0.023(4) -0.002(2) 0.008(5) 0.006(6) C21 0.022(3) 0.018(3) 0.023(3) 0.003(2) -0.005(3) 0.003(3) C22 0.019(3) 0.018(3) 0.024(3) 0.007(2) 0.000(3) -0.002(3) C23 0.013(2) 0.019(2) 0.034(2) -0.0023(17) -0.0059(18) 0.008(2) C24 0.013(2) 0.019(2) 0.034(2) -0.0023(17) -0.0059(18) 0.008(2) C25 0.021(2) 0.030(3) 0.027(2) 0.0056(17) 0.002(2) 0.012(2) C26 0.021(2) 0.030(3) 0.027(2) 0.0056(17) 0.002(2) 0.012(2) C27 0.021(3) 0.023(3) 0.023(3) 0.003(2) -0.003(3) 0.002(3) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C16 C11 N1 120.4(6) no C16 C11 C12 121.7(6) no N1 C11 C12 117.8(5) no C13 C12 C11 119.2(5) no C13 C12 H12 120.4 no C11 C12 H12 120.4 no C12 C13 C14 119.9(5) no C12 C13 H13 120.0 no C14 C13 H13 120.0 no C13 C14 C15 121.5(6) no C13 C14 N4 119.2(5) no C15 C14 N4 119.3(5) no O41 N4 O42 122.1(5) no O41 N4 C14 118.6(5) no O42 N4 C14 119.3(5) no C14 C15 C16 118.7(7) no C14 C15 H15 120.7 no C16 C15 H15 120.7 no C11 C16 C15 119.0(5) no C11 C16 H16 120.5 no C15 C16 H16 120.5 no N2 N1 C11 121.9(5) no N2 N1 H1 119.0 no C11 N1 H1 119.0 no C27 N2 N1 115.3(5) no N2 C27 C21 120.8(5) no N2 C27 H2 119.6 no C21 C27 H2 119.6 no C22 C21 C26 116.5(5) no C22 C21 C27 124.0(5) no C26 C21 C27 119.4(5) no C23 C22 C21 121.7(6) no C23 C22 I22 117.0(4) no C21 C22 I22 121.2(4) no C22 C23 C24 118.5(5) no C22 C23 H23 120.7 no C24 C23 H23 120.7 no C25 C24 C23 120.8(6) no C25 C24 H24 119.6 no C23 C24 H24 119.6 no C24 C25 C26 122.6(6) no C24 C25 H25 118.7 no C26 C25 H25 118.7 no C25 C26 C21 119.8(6) no C25 C26 H26 120.1 no C21 C26 H26 120.1 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C11 C16 . 1.377(16) no C11 N1 . 1.380(7) no C11 C12 . 1.396(8) no C12 C13 . 1.375(8) no C12 H12 . 0.95 no C13 C14 . 1.384(8) no C13 H13 . 0.95 no C14 C15 . 1.391(8) no C14 N4 . 1.440(8) no N4 O41 . 1.229(7) no N4 O42 . 1.252(7) no C15 C16 . 1.409(16) no C15 H15 . 0.95 no C16 H16 . 0.95 no N1 N2 . 1.364(6) no N1 H1 . 0.88 no N2 C27 . 1.291(8) no C27 C21 . 1.454(8) no C27 H2 . 0.95 no C21 C22 . 1.405(8) no C21 C26 . 1.430(8) no C22 C23 . 1.364(8) no C22 I22 . 2.121(6) no C23 C24 . 1.439(8) no C23 H23 . 0.95 no C24 C25 . 1.278(8) no C24 H24 . 0.95 no C25 C26 . 1.387(8) no C25 H25 . 0.95 no C26 H26 . 0.95 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O41 4_665 0.88 2.04 2.905(6) 166 y 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_publ_flag C16 C11 C12 C13 -1.4(10) no N1 C11 C12 C13 179.9(5) no C11 C12 C13 C14 0.1(8) no C12 C13 C14 C15 0.2(9) no C12 C13 C14 N4 -179.5(5) no C13 C14 C15 C16 0.7(10) no N4 C14 C15 C16 -179.6(7) no N1 C11 C16 C15 -179.0(7) no C12 C11 C16 C15 2.3(13) no C14 C15 C16 C11 -1.9(13) no C16 C11 N1 N2 -0.2(9) no C11 N1 N2 C27 178.4(5) y N1 N2 C27 C21 179.1(5) y C12 C11 N1 N2 178.6(5) y C22 C21 C27 N2 -179.0(5) y C13 C14 N4 O41 -5.8(8) y C15 C14 N4 O41 174.6(5) no C13 C14 N4 O42 174.1(5) y C15 C14 N4 O42 -5.6(8) no N2 C27 C21 C26 1.0(8) no C26 C21 C22 C23 -0.1(8) no C27 C21 C22 C23 179.9(6) no C26 C21 C22 I22 176.7(4) no C27 C21 C22 I22 -3.3(8) no C21 C22 C23 C24 0.4(8) no I22 C22 C23 C24 -176.5(4) no C22 C23 C24 C25 -0.1(8) no C23 C24 C25 C26 -0.4(9) no C24 C25 C26 C21 0.7(9) no C22 C21 C26 C25 -0.4(8) no C27 C21 C26 C25 179.6(5) no