# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Ivan Halasz' ; Department of Chemistry Faculty of Science University of Zagreb Horvatovac 102a 10000 Zagreb Croatia ; H.Vancik ; Department of Chemistry Faculty of Science University of Zagreb Horvatovac 102a 10000 Zagreb Croatia ; _publ_contact_author_address ; Department of Chemistry Faculty of Science University of Zagreb Horvatovac 102a 10000 Zagreb Croatia ; _publ_contact_author_email vancik@chem.pmf.hr _publ_contact_author_fax '+385 1 460 6401' _publ_contact_author_phone '+385 1 460 6416' #TrackingRef '- p-no2_p-Cl_ccdc.cif' # 1. SUBMISSION DETAILS _publ_contact_author_name 'Ivan Halasz' _publ_section_title ; ; data_p-no2 _database_code_depnum_ccdc_archive 'CCDC 642711' _publ_section_abstract ; ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-nitronitrosobenzene ; _chemical_name_common 4-nitronitrosobenzene _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 N2 O3' _chemical_formula_sum 'C6 H4 N2 O3' _chemical_formula_weight 152.11 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 5.8638(12) _cell_length_b 5.0832(11) _cell_length_c 10.708(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.124(16) _cell_angle_gamma 90.00 _cell_volume 318.97(11) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 156 _exptl_absorpt_coefficient_mu 0.131 _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 100(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 Xcalibur' _diffrn_measurement_method '\o scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2889 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.44 _diffrn_reflns_theta_max 27.06 _reflns_number_total 697 _reflns_number_gt 594 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2003) ; _computing_cell_refinement ; CrysAlis RED (Oxford Diffraction, 2003) ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2003) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 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^)+(0.0549P)^2^+0.0077P] 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 697 _refine_ls_number_parameters 93 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1161 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.295 _refine_ls_restrained_S_all 1.308 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean <0.001 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 N1 N 0.6868(11) 0.3953(14) 0.3599(5) 0.0246(14) Uani 0.50 1 d PDU A 1 O1 O 0.560(2) 0.495(3) 0.2800(12) 0.046(3) Uani 0.50 1 d PD A 1 O2 O 0.8855(10) 0.4544(13) 0.3814(7) 0.0451(13) Uani 0.50 1 d PD A 1 N2A N 0.6223(18) 0.4289(19) 0.3339(9) 0.028(2) Uani 0.287(6) 1 d PDU A 2 O3A O 0.8176(18) 0.5241(19) 0.3590(11) 0.047(3) Uani 0.287(6) 1 d PDU A 2 N2B N 0.733(4) 0.420(4) 0.3741(17) 0.037(5) Uani 0.212(6) 1 d PDU A 3 O3B O 0.607(5) 0.508(8) 0.285(2) 0.039(5) Uani 0.212(6) 1 d PDU A 3 C1 C 0.5863(2) 0.1956(3) 0.43091(14) 0.0379(5) Uani 1 1 d DU . . C3 C 0.7142(3) 0.1046(3) 0.53284(15) 0.0402(5) Uani 1 1 d . . . H3 H 0.8564 0.1770 0.5535 0.048 Uiso 1 1 calc R . . C2 C 0.3732(3) 0.0954(3) 0.39685(15) 0.0397(5) Uani 1 1 d . . . H2 H 0.2911 0.1619 0.3279 0.048 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 N1 0.023(4) 0.031(3) 0.019(2) -0.0064(18) 0.000(2) 0.003(2) O1 0.049(5) 0.040(3) 0.048(3) 0.015(2) 0.003(2) 0.012(4) O2 0.044(3) 0.046(3) 0.046(2) 0.0037(19) 0.0079(19) -0.0169(19) N2A 0.028(3) 0.028(3) 0.028(3) -0.0002(10) 0.0012(11) -0.0004(10) O3A 0.048(6) 0.037(5) 0.058(6) -0.005(4) 0.016(4) -0.028(4) N2B 0.037(5) 0.037(5) 0.037(5) 0.0004(11) 0.0013(11) -0.0002(11) O3B 0.044(9) 0.042(6) 0.032(6) 0.007(5) 0.010(5) 0.006(6) C1 0.0434(9) 0.0335(9) 0.0382(9) -0.0112(7) 0.0209(7) -0.0077(7) C3 0.0380(9) 0.0422(10) 0.0414(9) -0.0128(8) 0.0134(7) -0.0086(7) C2 0.0442(9) 0.0401(9) 0.0354(9) -0.0076(7) 0.0112(7) -0.0020(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 N1 O2 1.217(8) . ? N1 O1 1.223(8) . ? N1 C1 1.411(6) . ? N2A O3A 1.263(12) . ? N2A C1 1.596(10) . ? N2B O3B 1.266(15) . ? N2B C1 1.567(15) . ? C1 C3 1.381(2) . ? C1 C2 1.386(2) . ? C3 C2 1.376(2) 3_656 ? C2 C3 1.376(2) 3_656 ? C2 H2 0.9300 . ? C3 H3 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 O2 N1 O1 125.9(9) . . ? O2 N1 C1 119.4(5) . . ? O1 N1 C1 114.7(9) . . ? O3A N2A C1 106.7(8) . . ? O3B N2B C1 103(2) . . ? C3 C1 C2 122.88(16) . . ? C3 C1 N1 116.2(3) . . ? C2 C1 N1 120.9(3) . . ? C3 C1 N2B 105.1(8) . . ? C2 C1 N2B 132.1(8) . . ? C3 C1 N2A 133.0(4) . . ? C2 C1 N2A 104.0(4) . . ? C2 C3 C1 118.52(14) 3_656 . ? C3 C2 C1 118.59(15) 3_656 . ? C3 C2 H2 120.7 3_656 . ? C1 C2 H2 120.7 . . ? C2 C3 H3 120.7 3_656 . ? C1 C3 H3 120.7 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.144 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.036 ############################################################3 data_p-cl _database_code_depnum_ccdc_archive 'CCDC 801871' #TrackingRef '- p-no2_p-Cl_ccdc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-chloronitrosobenzene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H4 Cl N O' _chemical_formula_sum 'C6 H4 Cl N O' _chemical_formula_weight 141.55 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 P21/n 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 3.735(2) _cell_length_b 6.533(6) _cell_length_c 13.510(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.38(6) _cell_angle_gamma 90.00 _cell_volume 326.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 144 _exptl_absorpt_coefficient_mu 0.492 _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 'CCD Xcalibur' _diffrn_measurement_method '\o scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1470 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.36 _diffrn_reflns_theta_max 26.07 _reflns_number_total 644 _reflns_number_gt 393 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2003) ; _computing_cell_refinement ; CrysAlis RED (Oxford Diffraction, 2003) ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2003) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 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^)+(0.0725P)^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_number_reflns 644 _refine_ls_number_parameters 93 _refine_ls_number_restraints 56 _refine_ls_R_factor_all 0.1377 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.1989 _refine_ls_wR_factor_gt 0.1634 _refine_ls_goodness_of_fit_ref 1.272 _refine_ls_restrained_S_all 1.266 _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 N1 N 0.171(4) 0.227(2) 0.3621(9) 0.058(4) Uani 0.25 1 d PDU A 1 O1 O 0.110(2) 0.2888(15) 0.2771(7) 0.059(4) Uani 0.172(6) 1 d PD A 1 O2 O 0.305(3) 0.0727(18) 0.4043(17) 0.074(6) Uani 0.131(7) 1 d PD A 1 C1 C 0.088(8) 0.391(3) 0.4383(16) 0.056(5) Uani 0.25 1 d PDU . 1 C2 C 0.136(6) 0.339(4) 0.5387(18) 0.064(7) Uani 0.25 1 d PDU . 1 H2 H 0.2389 0.2116 0.5562 0.076 Uiso 0.25 1 calc PR . 1 C3 C -0.070(8) 0.573(3) 0.4059(17) 0.049(4) Uani 0.25 1 d PDU . 1 H3 H -0.1114 0.6113 0.3389 0.059 Uiso 0.25 1 calc PR . 1 Cl Cl 0.2003(18) 0.1532(11) 0.3417(4) 0.086(2) Uani 0.25 1 d PD B 2 C1A C 0.079(6) 0.337(2) 0.4253(11) 0.040(4) Uani 0.25 1 d PDU B 2 C2A C 0.156(5) 0.290(4) 0.5255(14) 0.048(5) Uani 0.25 1 d PDU . 2 H2A H 0.2518 0.1637 0.5476 0.057 Uiso 0.25 1 calc PR . 2 C3A C -0.063(8) 0.517(3) 0.3903(17) 0.051(5) Uani 0.25 1 d PDU . 2 H3A H -0.1113 0.5402 0.3217 0.061 Uiso 0.25 1 calc PR . 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 N1 0.033(5) 0.076(8) 0.068(8) -0.033(6) 0.013(5) -0.019(5) O1 0.069(6) 0.068(7) 0.044(6) -0.016(5) 0.020(4) -0.003(4) O2 0.064(8) 0.050(8) 0.100(15) -0.001(8) -0.009(8) 0.023(5) C1 0.040(6) 0.065(9) 0.062(8) -0.016(6) 0.006(5) -0.015(7) C2 0.054(9) 0.062(12) 0.071(11) -0.003(8) -0.006(7) 0.009(6) C3 0.037(5) 0.067(10) 0.041(7) -0.007(7) -0.004(5) -0.010(8) Cl 0.054(2) 0.126(5) 0.083(3) -0.050(4) 0.026(2) -0.026(3) C1A 0.028(5) 0.054(9) 0.040(7) 0.005(7) 0.007(5) -0.019(7) C2A 0.029(5) 0.054(9) 0.064(9) 0.014(8) 0.019(5) -0.011(6) C3A 0.038(5) 0.068(10) 0.047(7) 0.005(8) 0.008(6) -0.012(8) _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 N1 O1 1.208(14) . ? N1 O2 1.228(15) . ? N1 C1 1.549(15) . ? C1 C3 1.369(14) . ? C1 C2 1.386(14) . ? C1 C2 2.00(3) 3_566 ? C2 C3 1.00(3) 3_566 ? C2 C1 2.00(3) 3_566 ? C2 H2 0.9300 . ? C3 C2 1.00(3) 3_566 ? C3 H3 0.9300 . ? Cl C1A 1.751(13) . ? C1A C3A 1.351(13) . ? C1A C2A 1.376(12) . ? C2A C3A 1.77(3) 3_566 ? C2A H2A 0.9300 . ? C3A C2A 1.77(3) 3_566 ? C3A H3A 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 O1 N1 O2 136.4(17) . . ? O1 N1 C1 111.8(13) . . ? O2 N1 C1 111.6(15) . . ? C3 C1 C2 121.1(15) . . ? C3 C1 N1 120.5(17) . . ? C2 C1 N1 117.9(18) . . ? C3 C1 C2 27.4(13) . 3_566 ? C2 C1 C2 93.7(14) . 3_566 ? N1 C1 C2 148(2) . 3_566 ? C3 C2 C1 125(3) 3_566 . ? C3 C2 C1 38.9(15) 3_566 3_566 ? C1 C2 C1 86.3(14) . 3_566 ? C3 C2 H2 117.4 3_566 . ? C1 C2 H2 117.4 . . ? C1 C2 H2 156.3 3_566 . ? C2 C3 C1 114(2) 3_566 . ? C2 C3 H3 123.1 3_566 . ? C1 C3 H3 123.1 . . ? C3A C1A C2A 123.6(15) . . ? C3A C1A Cl 119.8(12) . . ? C2A C1A Cl 116.5(14) . . ? C1A C2A C3A 116.3(18) . 3_566 ? C1A C2A H2A 121.9 . . ? C3A C2A H2A 121.9 3_566 . ? C1A C3A C2A 120.1(18) . 3_566 ? C1A C3A H3A 119.9 . . ? C2A C3A H3A 119.9 3_566 . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.068 _refine_diff_density_min -0.066 _refine_diff_density_rms 0.020