# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 _publ_contact_author_phone '91 40 23011338' _publ_contact_author_fax '91 40 23011338' _publ_contact_author_email ansc@uohyd.ernet.in _publ_contact_author_name 'Prof Ashwini Nangia' _publ_contact_author_address ; Chemistry University of Hyderabad School of Chemistry, University of Hyderabad 500046 INDIA ; loop_ _publ_author_name _publ_author_address 'Sumod George' ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; 'Ashwini Nangia' ; School of Chemistry University of Hyderabad Hyderabad 500 046 India ; T.C.W.Mak ; Department of Chemistry The Chinese University of Hong Kong China ; 'C.-K. Lam' ; Department of Chemistry The Chinese University of Hong Kong China ; 'J.-F. Nicoud' ; Groupe de Materiaux Organiques Institut de Physique et Chimie des Materiaux de Strasbourg CNRS et Universite Louis Pasteur (UMR 7504) 23 rue du Loess, 67037 Strasbourg cedex, FRANCE ; _publ_requested_journal 'Chemical Communications' _publ_section_title ; Crystal engineering of urea a-network via I***O2N synthon and design of SHG active crystal N-4-iodophenyl-N'-4'-nitrophenylurea ; data_BromoNitro _database_code_depnum_ccdc_archive 'CCDC 231521' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-4-bromophenyl-N'-4'-nitrophenylurea ; _chemical_name_common ; ? ; _chemical_melting_point 'above 523k' _chemical_formula_moiety 'C13 H10 Br N3 O3' _chemical_formula_sum 'C13 H10 Br N3 O3' _chemical_formula_weight 336 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9974(8) _cell_length_b 13.4826(13) _cell_length_c 12.0227(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.671(2) _cell_angle_gamma 90.00 _cell_volume 1292.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2564 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.527 _exptl_crystal_size_mid 0.292 _exptl_crystal_size_min 0.150 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 3.192 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.581643 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _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 CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8669 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.02 _reflns_number_total 3120 _reflns_number_gt 1919 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART CCD DIFFRACTOMETER' _computing_cell_refinement 'BRUKER SMART CCD DIFFRACTOMETER' _computing_data_reduction 'BRUKER SMART CCD DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.0861P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3120 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1489 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 Br1 Br 0.11031(6) -0.01332(3) 0.64995(4) 0.0578(2) Uani 1 1 d . . . C1 C 0.3978(5) 0.8259(3) 0.3369(3) 0.0369(8) Uani 1 1 d . . . C2 C 0.4181(5) 0.7330(3) 0.2925(3) 0.0406(9) Uani 1 1 d . . . H2A H 0.4648 0.7261 0.2245 0.049 Uiso 1 1 calc R . . C3 C 0.3692(5) 0.6498(3) 0.3489(3) 0.0409(9) Uani 1 1 d . . . H3A H 0.3812 0.5869 0.3187 0.049 Uiso 1 1 calc R . . C4 C 0.3019(4) 0.6612(3) 0.4513(3) 0.0337(8) Uani 1 1 d . . . C5 C 0.2844(5) 0.7556(3) 0.4960(3) 0.0427(9) Uani 1 1 d . . . H5A H 0.2410 0.7626 0.5650 0.051 Uiso 1 1 calc R . . C6 C 0.3304(5) 0.8387(3) 0.4394(3) 0.0443(9) Uani 1 1 d . . . H6A H 0.3170 0.9017 0.4688 0.053 Uiso 1 1 calc R . . C11 C 0.1353(5) 0.1240(3) 0.6231(3) 0.0374(8) Uani 1 1 d . . . C12 C 0.0783(5) 0.1917(3) 0.6991(3) 0.0423(9) Uani 1 1 d . . . H12A H 0.0282 0.1701 0.7619 0.051 Uiso 1 1 calc R . . C13 C 0.0979(5) 0.2920(3) 0.6789(3) 0.0387(9) Uani 1 1 d . . . H13A H 0.0610 0.3379 0.7292 0.046 Uiso 1 1 calc R . . C14 C 0.1712(5) 0.3256(3) 0.5855(3) 0.0342(8) Uani 1 1 d . . . C15 C 0.2280(5) 0.2571(3) 0.5104(3) 0.0379(8) Uani 1 1 d . . . H15A H 0.2777 0.2786 0.4473 0.045 Uiso 1 1 calc R . . C16 C 0.2098(5) 0.1575(3) 0.5306(3) 0.0400(9) Uani 1 1 d . . . H16A H 0.2485 0.1117 0.4808 0.048 Uiso 1 1 calc R . . C21 C 0.2628(5) 0.4817(3) 0.4949(3) 0.0362(8) Uani 1 1 d . . . N1 N 0.4523(4) 0.9138(3) 0.2783(3) 0.0468(8) Uani 1 1 d . . . N2 N 0.2470(4) 0.5817(2) 0.5137(3) 0.0409(8) Uani 1 1 d . . . H2B H 0.1965 0.5976 0.5716 0.049 Uiso 1 1 calc R . . N3 N 0.1836(4) 0.4285(2) 0.5734(2) 0.0403(8) Uani 1 1 d . . . H3B H 0.1353 0.4634 0.6214 0.048 Uiso 1 1 calc R . . O1 O 0.5204(4) 0.9005(2) 0.1929(3) 0.0583(8) Uani 1 1 d . . . O2 O 0.4294(5) 0.9944(2) 0.3171(3) 0.0706(10) Uani 1 1 d . . . O3 O 0.3366(4) 0.4448(2) 0.4204(2) 0.0467(7) 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 Br1 0.0826(4) 0.0324(3) 0.0599(3) 0.00405(19) 0.0152(2) -0.0069(2) C1 0.037(2) 0.035(2) 0.039(2) 0.0079(15) 0.0078(16) 0.0002(16) C2 0.047(2) 0.044(2) 0.033(2) 0.0025(16) 0.0141(16) -0.0017(17) C3 0.052(2) 0.032(2) 0.041(2) -0.0034(15) 0.0161(18) -0.0017(17) C4 0.034(2) 0.0313(19) 0.037(2) 0.0013(14) 0.0086(15) 0.0004(15) C5 0.054(2) 0.036(2) 0.042(2) -0.0016(16) 0.0214(18) 0.0008(17) C6 0.058(3) 0.029(2) 0.048(2) -0.0013(16) 0.0153(19) 0.0017(18) C11 0.042(2) 0.030(2) 0.040(2) 0.0037(15) 0.0008(16) -0.0045(15) C12 0.052(2) 0.040(2) 0.035(2) 0.0021(16) 0.0111(18) -0.0052(18) C13 0.049(2) 0.034(2) 0.035(2) -0.0042(15) 0.0116(17) 0.0006(17) C14 0.038(2) 0.0293(19) 0.0349(19) -0.0012(14) 0.0001(16) -0.0009(15) C15 0.046(2) 0.033(2) 0.035(2) -0.0003(15) 0.0075(16) -0.0033(16) C16 0.048(2) 0.036(2) 0.037(2) -0.0047(16) 0.0112(17) -0.0012(17) C21 0.038(2) 0.0300(19) 0.040(2) 0.0004(15) 0.0035(16) -0.0029(16) N1 0.042(2) 0.049(2) 0.049(2) 0.0086(16) 0.0071(16) -0.0018(16) N2 0.052(2) 0.0302(17) 0.0439(18) -0.0001(13) 0.0234(15) 0.0001(14) N3 0.056(2) 0.0287(18) 0.0386(18) -0.0004(13) 0.0157(15) -0.0004(14) O1 0.0589(19) 0.063(2) 0.0549(19) 0.0180(16) 0.0185(15) -0.0068(16) O2 0.097(3) 0.036(2) 0.083(2) 0.0131(16) 0.030(2) -0.0061(17) O3 0.0584(18) 0.0367(16) 0.0481(17) -0.0011(12) 0.0221(14) -0.0009(13) _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 Br1 C11 1.892(4) . ? C1 C2 1.376(6) . ? C1 C6 1.396(5) . ? C1 N1 1.463(5) . ? C2 C3 1.384(5) . ? C2 H2A 0.9300 . ? C3 C4 1.392(5) . ? C3 H3A 0.9300 . ? C4 C5 1.393(5) . ? C4 N2 1.399(5) . ? C5 C6 1.376(6) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C11 C16 1.380(5) . ? C11 C12 1.394(6) . ? C12 C13 1.385(5) . ? C12 H12A 0.9300 . ? C13 C14 1.384(5) . ? C13 H13A 0.9300 . ? C14 C15 1.393(5) . ? C14 N3 1.400(5) . ? C15 C16 1.375(6) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C21 O3 1.218(5) . ? C21 N2 1.375(5) . ? C21 N3 1.379(5) . ? N1 O2 1.203(5) . ? N1 O1 1.213(4) . ? N2 H2B 0.8600 . ? N3 H3B 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 C2 C1 C6 121.4(4) . . ? C2 C1 N1 120.0(3) . . ? C6 C1 N1 118.5(4) . . ? C1 C2 C3 120.0(4) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 N2 123.4(3) . . ? C5 C4 N2 116.6(3) . . ? C6 C5 C4 121.0(4) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? C5 C6 C1 118.3(4) . . ? C5 C6 H6A 120.9 . . ? C1 C6 H6A 120.9 . . ? C16 C11 C12 120.0(4) . . ? C16 C11 Br1 121.1(3) . . ? C12 C11 Br1 119.0(3) . . ? C13 C12 C11 118.5(4) . . ? C13 C12 H12A 120.8 . . ? C11 C12 H12A 120.8 . . ? C14 C13 C12 121.5(4) . . ? C14 C13 H13A 119.2 . . ? C12 C13 H13A 119.2 . . ? C13 C14 C15 119.4(4) . . ? C13 C14 N3 116.5(3) . . ? C15 C14 N3 124.0(3) . . ? C16 C15 C14 119.2(4) . . ? C16 C15 H15A 120.4 . . ? C14 C15 H15A 120.4 . . ? C15 C16 C11 121.4(4) . . ? C15 C16 H16A 119.3 . . ? C11 C16 H16A 119.3 . . ? O3 C21 N2 125.3(3) . . ? O3 C21 N3 124.6(3) . . ? N2 C21 N3 110.1(3) . . ? O2 N1 O1 123.7(4) . . ? O2 N1 C1 118.9(4) . . ? O1 N1 C1 117.4(4) . . ? C21 N2 C4 128.7(3) . . ? C21 N2 H2B 115.6 . . ? C4 N2 H2B 115.6 . . ? C21 N3 C14 128.8(3) . . ? C21 N3 H3B 115.6 . . ? C14 N3 H3B 115.6 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.852 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.098 data_chloronitrourea _database_code_depnum_ccdc_archive 'CCDC 231522' _audit_creation_method SHELXL-97 # CHEMICAL DATA _chemical_name_systematic ; N-4-chlorophenyl-N'-4'-nitrophenylurea ; _chemical_name_common ; ? ; _chemical_melting_point 'above 523k' _chemical_formula_moiety 'C13 H10 Cl N3 O3' _chemical_formula_sum 'C13 H10 Cl N3 O3' _chemical_formula_weight 291.69 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.0360(5) _cell_length_b 13.3397(8) _cell_length_c 11.8513(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.8820(10) _cell_angle_gamma 90.00 _cell_volume 1265.82(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2610 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.427 _exptl_crystal_size_mid 0.292 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.313 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.819560 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _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 CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8434 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 28.02 _reflns_number_total 3067 _reflns_number_gt 2200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART CCD DIFFRACTOMETER' _computing_cell_refinement 'BRUKER SMART CCD DIFFRACTOMETER' _computing_data_reduction 'BRUKER SMART CCD DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.0861P)^2^+0.1740P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3067 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1357 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 Cl1 Cl 0.11250(8) -0.01371(4) 0.64766(5) 0.0642(2) Uani 1 1 d . . . C1 C 0.3987(2) 0.82588(15) 0.33778(15) 0.0397(4) Uani 1 1 d . . . C2 C 0.4203(2) 0.73195(15) 0.29178(16) 0.0440(5) Uani 1 1 d . . . H2A H 0.4670 0.7256 0.2230 0.053 Uiso 1 1 calc R . . C3 C 0.3722(2) 0.64752(15) 0.34817(16) 0.0423(4) Uani 1 1 d . . . H3A H 0.3864 0.5842 0.3176 0.051 Uiso 1 1 calc R . . C4 C 0.3021(2) 0.65800(14) 0.45127(16) 0.0375(4) Uani 1 1 d . . . C5 C 0.2823(2) 0.75360(15) 0.49633(17) 0.0448(5) Uani 1 1 d . . . H5A H 0.2362 0.7603 0.5653 0.054 Uiso 1 1 calc R . . C6 C 0.3298(3) 0.83791(15) 0.44058(18) 0.0465(5) Uani 1 1 d . . . H6A H 0.3162 0.9014 0.4709 0.056 Uiso 1 1 calc R . . C11 C 0.1341(2) 0.11484(15) 0.62336(17) 0.0426(4) Uani 1 1 d . . . C12 C 0.0770(2) 0.18274(15) 0.69969(16) 0.0443(5) Uani 1 1 d . . . H12A H 0.0263 0.1604 0.7627 0.053 Uiso 1 1 calc R . . C13 C 0.0964(2) 0.28382(15) 0.68084(17) 0.0436(4) Uani 1 1 d . . . H13A H 0.0588 0.3298 0.7319 0.052 Uiso 1 1 calc R . . C14 C 0.1718(2) 0.31829(14) 0.58615(15) 0.0372(4) Uani 1 1 d . . . C15 C 0.2278(2) 0.24907(15) 0.51009(16) 0.0418(4) Uani 1 1 d . . . H15A H 0.2778 0.2710 0.4466 0.050 Uiso 1 1 calc R . . C16 C 0.2088(3) 0.14744(15) 0.52930(17) 0.0444(5) Uani 1 1 d . . . H16A H 0.2464 0.1011 0.4787 0.053 Uiso 1 1 calc R . . C21 C 0.2630(2) 0.47631(14) 0.49486(16) 0.0383(4) Uani 1 1 d . . . N1 N 0.4538(2) 0.91442(14) 0.28024(16) 0.0502(4) Uani 1 1 d . . . N2 N 0.2469(2) 0.57807(12) 0.51330(14) 0.0455(4) Uani 1 1 d . . . H2B H 0.1954 0.5942 0.5714 0.055 Uiso 1 1 calc R . . N3 N 0.1845(2) 0.42258(11) 0.57408(14) 0.0429(4) Uani 1 1 d . . . H3B H 0.1367 0.4577 0.6229 0.052 Uiso 1 1 calc R . . O1 O 0.52260(19) 0.90261(13) 0.19265(14) 0.0627(5) Uani 1 1 d . . . O2 O 0.4321(2) 0.99742(13) 0.32073(17) 0.0748(5) Uani 1 1 d . . . O3 O 0.33630(18) 0.43981(10) 0.41904(12) 0.0498(4) 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 Cl1 0.0927(5) 0.0361(3) 0.0664(4) 0.0047(2) 0.0221(3) -0.0087(3) C1 0.0424(9) 0.0367(10) 0.0412(10) 0.0079(7) 0.0113(8) -0.0005(7) C2 0.0503(10) 0.0468(11) 0.0367(10) 0.0010(8) 0.0145(8) 0.0007(8) C3 0.0515(11) 0.0368(10) 0.0404(10) -0.0040(7) 0.0152(8) 0.0002(8) C4 0.0408(9) 0.0336(9) 0.0397(10) 0.0013(7) 0.0122(7) 0.0012(7) C5 0.0594(12) 0.0374(10) 0.0408(10) -0.0003(8) 0.0229(8) 0.0022(8) C6 0.0608(12) 0.0322(9) 0.0489(11) 0.0004(8) 0.0185(9) 0.0030(8) C11 0.0509(11) 0.0349(10) 0.0420(10) 0.0033(8) 0.0047(8) -0.0052(8) C12 0.0545(11) 0.0409(11) 0.0389(10) 0.0032(8) 0.0120(8) -0.0045(8) C13 0.0547(11) 0.0381(10) 0.0398(10) -0.0019(8) 0.0144(8) 0.0008(8) C14 0.0410(9) 0.0339(9) 0.0373(9) 0.0006(7) 0.0058(7) -0.0014(7) C15 0.0533(11) 0.0369(10) 0.0366(10) -0.0014(7) 0.0124(8) -0.0035(8) C16 0.0569(11) 0.0355(10) 0.0421(11) -0.0046(8) 0.0117(8) -0.0009(8) C21 0.0425(9) 0.0337(9) 0.0395(10) -0.0011(7) 0.0087(8) -0.0001(7) N1 0.0506(9) 0.0501(11) 0.0515(10) 0.0118(8) 0.0127(8) -0.0021(8) N2 0.0582(10) 0.0342(9) 0.0476(10) 0.0005(7) 0.0255(8) -0.0003(7) N3 0.0591(10) 0.0309(8) 0.0416(9) -0.0008(6) 0.0203(7) 0.0005(7) O1 0.0679(10) 0.0673(11) 0.0566(10) 0.0183(8) 0.0259(8) -0.0067(8) O2 0.1059(14) 0.0393(9) 0.0835(13) 0.0098(8) 0.0333(11) -0.0067(9) O3 0.0640(9) 0.0382(8) 0.0508(8) -0.0024(6) 0.0251(7) 0.0006(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 Cl1 C11 1.750(2) . ? C1 C2 1.383(3) . ? C1 C6 1.390(3) . ? C1 N1 1.452(2) . ? C2 C3 1.381(3) . ? C2 H2A 0.9300 . ? C3 C4 1.395(2) . ? C3 H3A 0.9300 . ? C4 N2 1.389(2) . ? C4 C5 1.397(3) . ? C5 C6 1.375(3) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C11 C16 1.380(3) . ? C11 C12 1.386(3) . ? C12 C13 1.378(3) . ? C12 H12A 0.9300 . ? C13 C14 1.398(3) . ? C13 H13A 0.9300 . ? C14 C15 1.392(3) . ? C14 N3 1.403(2) . ? C15 C16 1.385(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C21 O3 1.217(2) . ? C21 N3 1.376(2) . ? C21 N2 1.383(2) . ? N1 O2 1.225(3) . ? N1 O1 1.227(2) . ? N2 H2B 0.8600 . ? N3 H3B 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 C2 C1 C6 121.51(17) . . ? C2 C1 N1 119.90(17) . . ? C6 C1 N1 118.56(17) . . ? C3 C2 C1 119.89(17) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 119.50(18) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? N2 C4 C3 123.88(17) . . ? N2 C4 C5 116.52(16) . . ? C3 C4 C5 119.59(17) . . ? C6 C5 C4 121.19(18) . . ? C6 C5 H5A 119.4 . . ? C4 C5 H5A 119.4 . . ? C5 C6 C1 118.33(18) . . ? C5 C6 H6A 120.8 . . ? C1 C6 H6A 120.8 . . ? C16 C11 C12 120.80(19) . . ? C16 C11 Cl1 119.85(16) . . ? C12 C11 Cl1 119.34(15) . . ? C13 C12 C11 119.05(19) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 120.99(18) . . ? C12 C13 H13A 119.5 . . ? C14 C13 H13A 119.5 . . ? C15 C14 C13 119.21(18) . . ? C15 C14 N3 124.16(17) . . ? C13 C14 N3 116.63(16) . . ? C16 C15 C14 119.77(18) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C11 C16 C15 120.18(19) . . ? C11 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? O3 C21 N3 125.03(18) . . ? O3 C21 N2 124.54(17) . . ? N3 C21 N2 110.44(16) . . ? O2 N1 O1 122.47(18) . . ? O2 N1 C1 119.47(18) . . ? O1 N1 C1 118.05(19) . . ? C21 N2 C4 129.16(16) . . ? C21 N2 H2B 115.4 . . ? C4 N2 H2B 115.4 . . ? C21 N3 C14 128.87(16) . . ? C21 N3 H3B 115.6 . . ? C14 N3 H3B 115.6 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.231 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.067 data_EthynylNitro _database_code_depnum_ccdc_archive 'CCDC 231523' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-4-ethynyl-N'-4'-nitrophenylurea ; _chemical_name_common ; ? ; _chemical_melting_point 'above 523k' _chemical_formula_moiety 'C15 H11 N3 O3' _chemical_formula_sum 'C15 H11 N3 O3' _chemical_formula_weight 281.27 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 Cc _symmetry_space_group_name_Hall C-2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.422(3) _cell_length_b 4.6511(9) _cell_length_c 21.261(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.97(3) _cell_angle_gamma 90.00 _cell_volume 1322.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.41 _cell_measurement_theta_max 10.71 _exptl_crystal_description plates _exptl_crystal_colour brown _exptl_crystal_size_max .16 _exptl_crystal_size_mid .11 _exptl_crystal_size_min .09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.102 _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 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 CAD4 _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% none _diffrn_reflns_number 3017 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3017 _reflns_number_gt 1912 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 Software' _computing_data_reduction 'XTAL 3.5 (Hall et al., 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLUTON-(C) (Spek, 1979-1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0926P)^2^+0.4289P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 3(3) _refine_ls_number_reflns 3017 _refine_ls_number_parameters 190 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1729 _refine_ls_wR_factor_gt 0.1232 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.006 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 O1 O 0.5777(3) 0.0997(4) 0.2400(2) 0.0444(5) Uani 1 1 d . . . N2 N 0.6367(3) 0.5220(7) 0.20528(17) 0.0450(11) Uani 1 1 d . . . H2A H 0.6319 0.7060 0.2076 0.054 Uiso 1 1 calc R . . C11 C 0.8739(3) 0.4213(13) 0.1353(2) 0.0561(15) Uani 1 1 d . . . H11A H 0.9380 0.4992 0.1391 0.067 Uiso 1 1 calc R . . C5 C 0.8042(3) 0.5214(12) 0.1730(2) 0.0516(14) Uani 1 1 d . . . H5A H 0.8211 0.6634 0.2028 0.062 Uiso 1 1 calc R . . C9 C 0.4439(3) 0.4063(10) 0.3112(2) 0.0355(11) Uani 1 1 d . . . N1 N 0.5144(2) 0.5222(8) 0.27270(18) 0.0471(11) Uani 1 1 d . . . H1A H 0.5185 0.7063 0.2702 0.057 Uiso 1 1 calc R . . N3 N 0.2273(3) 0.1006(11) 0.4255(2) 0.0644(14) Uani 1 1 d . . . C2 C 0.8509(3) 0.2044(14) 0.0913(2) 0.0524(15) Uani 1 1 d . . . C12 C 0.7069(3) 0.4087(10) 0.1663(2) 0.0383(11) Uani 1 1 d . . . C1 C 0.3976(3) 0.0957(11) 0.3931(2) 0.0517(13) Uani 1 1 d . . . H1B H 0.4142 -0.0459 0.4231 0.062 Uiso 1 1 calc R . . C6 C 0.6832(3) 0.1938(10) 0.1224(2) 0.0453(12) Uani 1 1 d . . . H6A H 0.6188 0.1182 0.1177 0.054 Uiso 1 1 calc R . . C4 C 0.5766(4) 0.3625(5) 0.2392(3) 0.0351(6) Uani 1 1 d . . . C8 C 0.4686(3) 0.1961(11) 0.3548(2) 0.0473(13) Uani 1 1 d . . . H8A H 0.5330 0.1204 0.3587 0.057 Uiso 1 1 calc R . . C13 C 0.3030(3) 0.2076(12) 0.3863(2) 0.0433(12) Uani 1 1 d . . . C15 C 0.9270(4) 0.1011(14) 0.0530(3) 0.0645(17) Uani 1 1 d . . . C3 C 0.2774(3) 0.4155(13) 0.3436(2) 0.0539(15) Uani 1 1 d . . . H3A H 0.2127 0.4891 0.3396 0.065 Uiso 1 1 calc R . . C10 C 0.7550(3) 0.0931(12) 0.0857(2) 0.0524(13) Uani 1 1 d . . . H10A H 0.7389 -0.0526 0.0567 0.063 Uiso 1 1 calc R . . C7 C 0.3488(3) 0.5180(12) 0.3057(2) 0.0484(13) Uani 1 1 d . . . H7A H 0.3322 0.6627 0.2765 0.058 Uiso 1 1 calc R . . O2 O 0.2492(3) -0.0957(10) 0.4614(2) 0.1071(15) Uani 1 1 d . . . O3 O 0.1463(3) 0.2186(11) 0.4218(2) 0.1048(14) Uani 1 1 d . . . C14 C 0.9911(4) 0.0191(15) 0.0239(3) 0.0954(19) Uani 1 1 d . . . H14 H 1.0421 -0.0463 0.0006 0.114 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 O1 0.0535(11) 0.0225(8) 0.0612(12) -0.001(2) 0.0278(9) -0.001(2) N2 0.060(3) 0.0180(19) 0.063(3) -0.0021(19) 0.038(2) 0.001(2) C11 0.036(3) 0.072(4) 0.061(4) 0.008(3) 0.012(2) -0.005(3) C5 0.053(3) 0.051(3) 0.054(3) -0.010(3) 0.022(2) -0.010(3) C9 0.042(3) 0.027(2) 0.041(3) -0.001(2) 0.025(2) 0.002(2) N1 0.050(2) 0.027(2) 0.069(3) -0.003(2) 0.036(2) -0.002(2) N3 0.063(3) 0.076(4) 0.060(3) -0.002(3) 0.036(3) -0.020(3) C2 0.055(3) 0.066(4) 0.039(3) 0.013(3) 0.018(2) 0.011(3) C12 0.039(3) 0.032(3) 0.045(3) 0.006(2) 0.015(2) 0.007(2) C1 0.059(3) 0.047(3) 0.052(3) 0.010(3) 0.024(2) -0.004(3) C6 0.044(2) 0.042(3) 0.053(3) -0.005(2) 0.017(2) -0.003(2) C4 0.0373(12) 0.0262(12) 0.0444(14) 0.011(3) 0.0185(11) 0.011(3) C8 0.040(2) 0.052(3) 0.052(3) 0.006(3) 0.016(2) 0.005(2) C13 0.037(2) 0.053(3) 0.043(3) -0.002(2) 0.020(2) -0.016(2) C15 0.057(3) 0.084(5) 0.055(3) 0.016(3) 0.021(3) 0.022(3) C3 0.041(3) 0.068(4) 0.056(3) 0.004(3) 0.025(3) 0.001(3) C10 0.058(3) 0.055(3) 0.046(3) -0.015(3) 0.015(2) -0.002(3) C7 0.043(3) 0.055(3) 0.049(3) 0.006(3) 0.016(2) 0.006(3) O2 0.122(3) 0.100(3) 0.110(3) 0.046(3) 0.073(3) -0.002(2) O3 0.0524(18) 0.158(4) 0.110(3) 0.039(3) 0.0404(18) 0.006(2) C14 0.072(3) 0.146(5) 0.073(3) 0.009(4) 0.032(3) 0.037(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 O1 C4 1.223(3) . ? N2 C4 1.349(5) . ? N2 C12 1.409(5) . ? N2 H2A 0.8600 . ? C11 C5 1.365(6) . ? C11 C2 1.392(7) . ? C11 H11A 0.9300 . ? C5 C12 1.403(6) . ? C5 H5A 0.9300 . ? C9 C8 1.368(6) . ? C9 C7 1.373(6) . ? C9 N1 1.412(5) . ? N1 C4 1.364(5) . ? N1 H1A 0.8600 . ? N3 O2 1.209(6) . ? N3 O3 1.215(6) . ? N3 C13 1.457(5) . ? C2 C10 1.383(7) . ? C2 C15 1.443(6) . ? C12 C6 1.386(7) . ? C1 C13 1.368(6) . ? C1 C8 1.387(5) . ? C1 H1B 0.9300 . ? C6 C10 1.374(6) . ? C6 H6A 0.9300 . ? C8 H8A 0.9300 . ? C13 C3 1.350(7) . ? C15 C14 1.167(6) . ? C3 C7 1.389(6) . ? C3 H3A 0.9300 . ? C10 H10A 0.9300 . ? C7 H7A 0.9300 . ? C14 H14 0.9300 . ? 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 C4 N2 C12 124.7(3) . . ? C4 N2 H2A 117.7 . . ? C12 N2 H2A 117.7 . . ? C5 C11 C2 121.2(5) . . ? C5 C11 H11A 119.4 . . ? C2 C11 H11A 119.4 . . ? C11 C5 C12 119.5(5) . . ? C11 C5 H5A 120.2 . . ? C12 C5 H5A 120.2 . . ? C8 C9 C7 119.9(4) . . ? C8 C9 N1 122.0(4) . . ? C7 C9 N1 118.1(4) . . ? C4 N1 C9 124.6(3) . . ? C4 N1 H1A 117.7 . . ? C9 N1 H1A 117.7 . . ? O2 N3 O3 123.3(4) . . ? O2 N3 C13 118.4(5) . . ? O3 N3 C13 118.3(5) . . ? C10 C2 C11 118.7(4) . . ? C10 C2 C15 121.8(5) . . ? C11 C2 C15 119.6(5) . . ? C6 C12 C5 119.6(4) . . ? C6 C12 N2 122.7(4) . . ? C5 C12 N2 117.7(4) . . ? C13 C1 C8 119.2(5) . . ? C13 C1 H1B 120.4 . . ? C8 C1 H1B 120.4 . . ? C10 C6 C12 119.8(4) . . ? C10 C6 H6A 120.1 . . ? C12 C6 H6A 120.1 . . ? O1 C4 N2 123.4(4) . . ? O1 C4 N1 122.9(4) . . ? N2 C4 N1 113.65(19) . . ? C9 C8 C1 120.0(4) . . ? C9 C8 H8A 120.0 . . ? C1 C8 H8A 120.0 . . ? C3 C13 C1 121.6(4) . . ? C3 C13 N3 118.7(4) . . ? C1 C13 N3 119.8(5) . . ? C14 C15 C2 177.6(6) . . ? C13 C3 C7 119.2(4) . . ? C13 C3 H3A 120.4 . . ? C7 C3 H3A 120.4 . . ? C6 C10 C2 121.2(5) . . ? C6 C10 H10A 119.4 . . ? C2 C10 H10A 119.4 . . ? C9 C7 C3 120.2(5) . . ? C9 C7 H7A 119.9 . . ? C3 C7 H7A 119.9 . . ? C15 C14 H14 180.0 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.207 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.040 data_iodonitro _database_code_depnum_ccdc_archive 'CCDC 231524' _audit_creation_method SHELXL-97 # CHEMICAL DATA _chemical_name_systematic ; N-4-iodophenyl-N'-4'-nitrophenylurea ; _chemical_name_common ? _chemical_melting_point 'above 523k' _chemical_formula_moiety 'C13 H10 I N3 O3' _chemical_formula_sum 'C13 H10 I N3 O3' _chemical_formula_weight 383 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' O O 0.0106 0.0060 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc _symmetry_space_group_name_Hall C-2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.552(3) _cell_length_b 4.6722(9) _cell_length_c 21.377(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.40(3) _cell_angle_gamma 90.00 _cell_volume 1353.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2163 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _exptl_crystal_description BLOCK _exptl_crystal_colour YELLOW _exptl_crystal_size_max 0.577 _exptl_crystal_size_mid 0.527 _exptl_crystal_size_min 0.336 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.880 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 2.377 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.519112 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; Iodo group and Nitro group are disordered with site occupancy 0.9 and 0.1 ; _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 CCD DIFFRACTOMETER' _diffrn_measurement_method 'OMEGA SCAN' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4355 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.01 _reflns_number_total 2212 _reflns_number_gt 2036 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART CCD DIFFRACTOMETER' _computing_cell_refinement 'BRUKER SMART CCD DIFFRACTOMETER' _computing_data_reduction 'BRUKER SMART CCD DIFFRACTOMETER' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SIEMENS SHELXTL' _computing_publication_material 'SIEMENS 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^)+(0.0679P)^2^+1.9588P] 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 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 _refine_ls_number_reflns 2212 _refine_ls_number_parameters 201 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0739 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.041 _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 O1 O 0.0855(4) 0.0756(7) 0.4493(2) 0.0455(11) Uani 1 1 d . . . N1 N 0.0166(5) 0.4993(12) 0.4799(4) 0.0470(16) Uani 1 1 d . . . H2A H 0.0192 0.6823 0.4760 0.056 Uiso 1 1 calc R . . N3 N 0.1495(5) 0.4979(9) 0.4149(3) 0.0457(14) Uani 1 1 d . . . H3A H 0.1451 0.6812 0.4175 0.055 Uiso 1 1 calc R . . C1 C -0.2050(4) 0.1891(14) 0.5952(3) 0.0473(14) Uani 1 1 d D . . C2 C -0.1123(6) 0.0730(14) 0.6014(4) 0.0507(15) Uani 1 1 d . A . H2B H -0.0994 -0.0679 0.6311 0.061 Uiso 1 1 calc R . . C3 C -0.0378(4) 0.1713(13) 0.5621(3) 0.0451(13) Uani 1 1 d . . . H3B H 0.0251 0.0932 0.5650 0.054 Uiso 1 1 calc R A . C4 C -0.0573(5) 0.3837(14) 0.5190(3) 0.0384(14) Uani 1 1 d . A . C5 C -0.1515(6) 0.4989(14) 0.5144(4) 0.0508(16) Uani 1 1 d . . . H5A H -0.1644 0.6432 0.4855 0.061 Uiso 1 1 calc R A . C6 C -0.2263(5) 0.3995(16) 0.5526(4) 0.0523(16) Uani 1 1 d . A . H6A H -0.2898 0.4743 0.5494 0.063 Uiso 1 1 calc R . . C11 C 0.3752(4) 0.1895(13) 0.3003(3) 0.0445(13) Uani 1 1 d D . . C12 C 0.3936(5) 0.3986(14) 0.3439(3) 0.0485(14) Uani 1 1 d D A . H12A H 0.4568 0.4747 0.3479 0.058 Uiso 1 1 calc R . . C13 C 0.3186(5) 0.4972(13) 0.3821(4) 0.0471(15) Uani 1 1 d . . . H13A H 0.3315 0.6396 0.4114 0.057 Uiso 1 1 calc R A . C14 C 0.2243(4) 0.3839(11) 0.3766(3) 0.0361(11) Uani 1 1 d . A . C15 C 0.2057(5) 0.1727(14) 0.3323(3) 0.0440(14) Uani 1 1 d . . . H15A H 0.1425 0.0969 0.3281 0.053 Uiso 1 1 calc R A . C16 C 0.2811(6) 0.0743(14) 0.2942(4) 0.0483(16) Uani 1 1 d D A . H16A H 0.2686 -0.0680 0.2648 0.058 Uiso 1 1 calc R . . C21 C 0.0839(4) 0.3385(11) 0.4482(3) 0.0354(11) Uani 1 1 d . . . I1 I 0.48973(6) 0.05005(11) 0.24275(5) 0.0645(2) Uani 0.908(4) 1 d PD A 1 N2 N -0.2843(6) 0.0838(18) 0.6354(5) 0.069(3) Uani 0.908(4) 1 d PD A 1 O2 O -0.2658(8) -0.107(2) 0.6730(6) 0.110(4) Uani 0.908(4) 1 d PD A 1 O3 O -0.3663(6) 0.195(3) 0.6306(6) 0.117(4) Uani 0.908(4) 1 d PD A 1 I1A I -0.3200(9) 0.066(3) 0.6507(6) 0.096(5) Uani 0.092(4) 1 d PD A 2 N2A N 0.4573(16) 0.073(7) 0.2633(17) 0.090(15) Uiso 0.092(4) 1 d PD A 2 O2A O 0.523(3) 0.238(12) 0.247(3) 0.090(15) Uiso 0.092(4) 1 d PD A 2 O3A O 0.454(4) -0.179(9) 0.246(3) 0.090(15) Uiso 0.092(4) 1 d PD A 2 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 O1 0.052(2) 0.0246(16) 0.060(3) -0.0006(18) 0.020(2) 0.0000(15) N1 0.051(3) 0.025(2) 0.065(4) 0.001(2) 0.026(3) 0.003(2) N3 0.051(3) 0.025(2) 0.060(4) -0.001(2) 0.025(3) -0.0001(19) C1 0.042(3) 0.055(3) 0.045(3) -0.002(3) 0.013(3) -0.009(3) C2 0.055(4) 0.052(3) 0.046(4) 0.008(3) 0.008(3) -0.003(3) C3 0.038(3) 0.049(3) 0.049(3) 0.008(3) 0.009(2) 0.003(2) C4 0.041(3) 0.031(2) 0.043(3) -0.006(3) 0.010(3) -0.005(3) C5 0.048(4) 0.052(4) 0.052(4) 0.013(3) 0.008(3) 0.011(3) C6 0.034(3) 0.063(4) 0.059(4) 0.007(3) 0.008(3) 0.004(3) C11 0.042(3) 0.050(3) 0.042(3) 0.006(3) 0.013(2) 0.016(2) C12 0.036(3) 0.057(4) 0.052(4) 0.004(3) 0.006(3) -0.005(2) C13 0.046(3) 0.043(3) 0.053(4) -0.005(2) 0.012(3) -0.008(2) C14 0.039(3) 0.028(2) 0.041(3) 0.002(2) 0.013(2) 0.0015(19) C15 0.036(3) 0.044(3) 0.052(4) -0.004(3) 0.004(3) 0.002(2) C16 0.052(4) 0.051(3) 0.042(4) -0.011(3) 0.009(3) 0.006(3) C21 0.034(3) 0.030(2) 0.043(3) 0.001(2) 0.008(2) 0.000(2) I1 0.0534(3) 0.0784(3) 0.0620(3) 0.0060(4) 0.0253(2) 0.0225(3) N2 0.058(6) 0.087(6) 0.061(6) 0.004(4) 0.030(5) -0.006(5) O2 0.092(7) 0.133(8) 0.106(8) 0.064(7) 0.046(6) 0.009(6) O3 0.049(4) 0.168(10) 0.134(9) 0.054(9) 0.040(5) 0.005(5) I1A 0.073(8) 0.138(10) 0.078(7) -0.012(6) 0.037(6) -0.035(7) _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 O1 C21 1.229(6) . ? N1 C21 1.367(8) . ? N1 C4 1.416(11) . ? N1 H2A 0.8600 . ? N3 C21 1.364(8) . ? N3 C14 1.412(7) . ? N3 H3A 0.8600 . ? C1 C6 1.370(10) . ? C1 C2 1.375(10) . ? C1 N2 1.466(9) . ? C1 I1A 2.046(10) . ? C2 C3 1.395(9) . ? C2 H2B 0.9300 . ? C3 C4 1.378(9) . ? C3 H3B 0.9300 . ? C4 C5 1.388(10) . ? C5 C6 1.388(10) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C11 C12 1.372(10) . ? C11 C16 1.389(10) . ? C11 N2A 1.475(13) . ? C11 I1 2.092(5) . ? C12 C13 1.387(10) . ? C12 H12A 0.9300 . ? C13 C14 1.387(9) . ? C13 H13A 0.9300 . ? C14 C15 1.390(9) . ? C15 C16 1.390(10) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? N2 O2 1.224(7) . ? N2 O3 1.230(7) . ? N2A O2A 1.229(7) . ? N2A O3A 1.229(7) . ? 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 C21 N1 C4 124.1(6) . . ? C21 N1 H2A 117.9 . . ? C4 N1 H2A 117.9 . . ? C21 N3 C14 124.7(4) . . ? C21 N3 H3A 117.6 . . ? C14 N3 H3A 117.6 . . ? C6 C1 C2 122.4(5) . . ? C6 C1 N2 118.6(6) . . ? C2 C1 N2 119.0(6) . . ? C6 C1 I1A 115.4(7) . . ? C2 C1 I1A 122.2(7) . . ? N2 C1 I1A 3.6(5) . . ? C1 C2 C3 118.5(6) . . ? C1 C2 H2B 120.8 . . ? C3 C2 H2B 120.8 . . ? C4 C3 C2 120.2(6) . . ? C4 C3 H3B 119.9 . . ? C2 C3 H3B 119.9 . . ? C3 C4 C5 119.9(7) . . ? C3 C4 N1 122.4(6) . . ? C5 C4 N1 117.6(7) . . ? C6 C5 C4 120.2(7) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C1 C6 C5 118.7(6) . . ? C1 C6 H6A 120.6 . . ? C5 C6 H6A 120.6 . . ? C12 C11 C16 120.2(6) . . ? C12 C11 N2A 119.5(11) . . ? C16 C11 N2A 120.2(11) . . ? C12 C11 I1 119.3(5) . . ? C16 C11 I1 120.6(5) . . ? N2A C11 I1 4.5(18) . . ? C11 C12 C13 120.3(6) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C14 C13 C12 120.2(6) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C13 C14 C15 119.4(5) . . ? C13 C14 N3 118.1(6) . . ? C15 C14 N3 122.4(6) . . ? C16 C15 C14 120.2(6) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C11 C16 C15 119.7(6) . . ? C11 C16 H16A 120.2 . . ? C15 C16 H16A 120.2 . . ? O1 C21 N3 123.1(5) . . ? O1 C21 N1 123.4(6) . . ? N3 C21 N1 113.5(5) . . ? O2 N2 O3 122.9(11) . . ? O2 N2 C1 118.7(8) . . ? O3 N2 C1 118.3(7) . . ? O2A N2A O3A 122(2) . . ? O2A N2A C11 118.1(17) . . ? O3A N2A C11 119.2(17) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.730 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.070