# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Keiichiro Ogawa' _publ_contact_author_email OGAWA@RAMIE.C.U-TOKYO.AC.JP _publ_section_title ; Crystalline-state conformational change of beta-nitrostyrenes and its freezing at low temperature ; loop_ _publ_author_name 'Keiichiro Ogawa' 'Jun Harada' 'Mayuko Harakawa' # Attachment 'nitrostyrenes.cif' data_no2300k _database_code_depnum_ccdc_archive 'CCDC 701892' _audit_creation_method SHELXL-97 _chemical_name_systematic ; \b-Nitrostyrene ; _chemical_name_common beta-Nitrostyrene _chemical_melting_point 54_C _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 N O2' _chemical_formula_weight 149.15 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_1_21/c_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0602(7) _cell_length_b 5.7898(5) _cell_length_c 18.0494(15) _cell_angle_alpha 90.00 _cell_angle_beta 114.606(2) _cell_angle_gamma 90.00 _cell_volume 765.82(11) _cell_formula_units_Z 4 _cell_measurement_temperature 300 _cell_measurement_reflns_used 2468 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 24.5 _exptl_crystal_description plate _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9282 _exptl_absorpt_correction_T_max 0.9906 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 5s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 300 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11365 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 30.07 _reflns_number_total 2229 _reflns_number_gt 1356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K, the structure of which is free from disorder, were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. For the same reason as above, the atomic distance C(7)...N(1) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction in order to restrain the bond angle C(7)---C(8)---N(1) of the two conformers to be equal. ; _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^)+(0.0596P)^2^+0.1587P] 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 2229 _refine_ls_number_parameters 132 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1624 _refine_ls_wR_factor_gt 0.1349 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.035 _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 N1A N 0.8374(3) 0.8175(8) 0.5417(3) 0.0659(12) Uani 0.69 1 d PD A 1 O1A O 0.7632(4) 0.9804(6) 0.55464(19) 0.0850(8) Uani 0.69 1 d PD A 1 O2A O 0.9911(3) 0.7442(5) 0.58275(16) 0.1023(8) Uani 0.69 1 d PD A 1 C1A C 0.4626(4) 0.4912(5) 0.37369(14) 0.0489(6) Uani 0.69 1 d PD A 1 C2A C 0.2836(4) 0.5427(5) 0.32234(19) 0.0571(7) Uani 0.69 1 d P A 1 H2A H 0.2313 0.6784 0.3302 0.069 Uiso 0.69 1 calc PR A 1 C3A C 0.1820(4) 0.3970(7) 0.2600(2) 0.0676(9) Uani 0.69 1 d P A 1 H3A H 0.0628 0.4352 0.2251 0.081 Uiso 0.69 1 calc PR A 1 C4A C 0.2601(5) 0.1888(7) 0.2496(2) 0.0651(9) Uani 0.69 1 d P A 1 H4A H 0.1922 0.0881 0.2078 0.078 Uiso 0.69 1 calc PR A 1 C5A C 0.4346(6) 0.1353(5) 0.3005(2) 0.0604(8) Uani 0.69 1 d P A 1 H5A H 0.4853 -0.0029 0.2936 0.072 Uiso 0.69 1 calc PR A 1 C6A C 0.5368(4) 0.2829(6) 0.36196(19) 0.0577(7) Uani 0.69 1 d P A 1 H6A H 0.6565 0.2444 0.3962 0.069 Uiso 0.69 1 calc PR A 1 C7A C 0.5698(3) 0.6553(4) 0.43686(12) 0.0514(5) Uani 0.69 1 d PD A 1 H7A H 0.5086 0.7797 0.4466 0.062 Uiso 0.69 1 calc PR A 1 C8A C 0.7465(3) 0.6403(4) 0.48108(15) 0.0669(6) Uani 0.69 1 d PD A 1 H8A H 0.8128 0.5179 0.4737 0.080 Uiso 0.69 1 calc PR A 1 N1B N 0.8345(12) 0.833(2) 0.5384(10) 0.119(6) Uiso 0.31 1 d PD B 2 O1B O 0.8110(13) 1.0340(16) 0.5557(7) 0.114(4) Uiso 0.31 1 d PD B 2 O2B O 1.0049(10) 0.8366(11) 0.5606(4) 0.097(2) Uiso 0.31 1 d PD B 2 C1B C 0.5043(8) 0.4374(12) 0.3778(3) 0.055(2) Uiso 0.31 1 d PGD B 2 C2B C 0.3385(9) 0.5521(9) 0.3401(4) 0.062(2) Uiso 0.31 1 d PG B 2 H2B H 0.3211 0.6935 0.3603 0.074 Uiso 0.31 1 calc PR B 2 C3B C 0.1987(7) 0.4554(12) 0.2723(4) 0.071(3) Uiso 0.31 1 d PG B 2 H3B H 0.0878 0.5322 0.2471 0.085 Uiso 0.31 1 calc PR B 2 C4B C 0.2247(10) 0.2440(12) 0.2422(3) 0.059(2) Uiso 0.31 1 d PG B 2 H4B H 0.1312 0.1793 0.1969 0.071 Uiso 0.31 1 calc PR B 2 C5B C 0.3905(11) 0.1294(10) 0.2799(4) 0.065(3) Uiso 0.31 1 d PG B 2 H5B H 0.4079 -0.0121 0.2598 0.078 Uiso 0.31 1 calc PR B 2 C6B C 0.5303(8) 0.2261(12) 0.3477(4) 0.061(3) Uiso 0.31 1 d PG B 2 H6B H 0.6412 0.1493 0.3729 0.074 Uiso 0.31 1 calc PR B 2 C7B C 0.6559(8) 0.5476(10) 0.4438(3) 0.0640(12) Uiso 0.31 1 d PD B 2 H7B H 0.7642 0.4639 0.4644 0.077 Uiso 0.31 1 calc PR B 2 C8B C 0.6618(8) 0.7439(10) 0.4776(3) 0.0643(12) Uiso 0.31 1 d PD B 2 H8B H 0.5555 0.8300 0.4634 0.077 Uiso 0.31 1 calc PR B 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 N1A 0.0469(12) 0.090(2) 0.0516(13) -0.0228(12) 0.0112(8) -0.0019(10) O1A 0.0772(16) 0.0822(16) 0.0985(17) -0.0212(13) 0.0393(14) 0.0113(15) O2A 0.0757(14) 0.119(2) 0.1010(18) 0.0003(16) 0.0260(13) 0.0278(14) C1A 0.0559(14) 0.0478(12) 0.0471(12) 0.0056(9) 0.0255(10) 0.0042(12) C2A 0.0461(14) 0.0603(15) 0.0618(16) -0.0055(11) 0.0193(14) 0.0008(11) C3A 0.0543(15) 0.0701(19) 0.0743(18) -0.0082(17) 0.0225(11) -0.0078(13) C4A 0.074(2) 0.0574(16) 0.0675(17) -0.0108(14) 0.0326(14) -0.0136(18) C5A 0.0722(19) 0.0527(15) 0.0612(17) -0.0003(12) 0.0327(18) 0.0014(12) C6A 0.0674(17) 0.0535(16) 0.0555(13) 0.0043(14) 0.0289(11) 0.0085(11) C7A 0.0513(11) 0.0522(11) 0.0533(11) 0.0018(9) 0.0242(9) 0.0115(9) C8A 0.0575(13) 0.0729(15) 0.0674(14) -0.0177(12) 0.0232(11) 0.0128(12) _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 N1A O1A 1.191(3) . ? N1A O2A 1.224(4) . ? N1A C8A 1.456(3) . ? C1A C2A 1.384(4) . ? C1A C6A 1.401(4) . ? C1A C7A 1.459(3) . ? C2A C3A 1.371(5) . ? C3A C4A 1.409(5) . ? C4A C5A 1.358(5) . ? C5A C6A 1.370(5) . ? C7A C8A 1.314(3) . ? N1B O1B 1.237(9) . ? N1B O2B 1.261(8) . ? N1B C8B 1.462(7) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.451(6) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.282(8) . ? 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 O2A 128.3(3) . . ? O1A N1A C8A 124.7(3) . . ? O2A N1A C8A 106.0(3) . . ? C2A C1A C6A 118.4(2) . . ? C2A C1A C7A 119.8(3) . . ? C6A C1A C7A 121.8(3) . . ? C3A C2A C1A 121.1(2) . . ? C2A C3A C4A 119.3(2) . . ? C5A C4A C3A 119.9(2) . . ? C4A C5A C6A 120.7(2) . . ? C5A C6A C1A 120.6(2) . . ? C8A C7A C1A 124.9(2) . . ? C7A C8A N1A 119.3(2) . . ? O1B N1B O2B 99.6(9) . . ? O1B N1B C8B 108.9(9) . . ? O2B N1B C8B 144.5(11) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 120.1(6) . . ? C6B C1B C7B 119.7(6) . . ? C3B C2B C1B 120.0 . . ? C2B C3B C4B 120.0 . . ? C5B C4B C3B 120.0 . . ? C4B C5B C6B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 129.2(6) . . ? C7B C8B N1B 120.4(7) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -1.7(3) . . . . ? C7A C1A C2A C3A 177.0(2) . . . . ? C1A C2A C3A C4A 1.6(3) . . . . ? C2A C3A C4A C5A -0.5(4) . . . . ? C3A C4A C5A C6A -0.5(3) . . . . ? C4A C5A C6A C1A 0.4(3) . . . . ? C2A C1A C6A C5A 0.6(3) . . . . ? C7A C1A C6A C5A -178.0(2) . . . . ? C2A C1A C7A C8A -169.9(2) . . . . ? C6A C1A C7A C8A 8.7(3) . . . . ? C1A C7A C8A N1A 179.4(3) . . . . ? O1A N1A C8A C7A -0.5(7) . . . . ? O2A N1A C8A C7A 169.0(3) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 174.2(6) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C2B C3B C4B C5B 0.0 . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -174.3(6) . . . . ? C2B C1B C7B C8B 2.9(8) . . . . ? C6B C1B C7B C8B 177.1(5) . . . . ? C1B C7B C8B N1B -174.0(11) . . . . ? O1B N1B C8B C7B 172.7(11) . . . . ? O2B N1B C8B C7B 31(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.07 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.146 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.041 #===END data_no2250k _database_code_depnum_ccdc_archive 'CCDC 701893' _audit_creation_method SHELXL-97 _chemical_name_systematic ; \b-Nitrostyrene ; _chemical_name_common beta-Nitrostyrene _chemical_melting_point 54_C _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 N O2' _chemical_formula_weight 149.15 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_1_21/c_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0411(6) _cell_length_b 5.7561(4) _cell_length_c 17.8760(14) _cell_angle_alpha 90.00 _cell_angle_beta 114.040(1) _cell_angle_gamma 90.00 _cell_volume 755.63(10) _cell_formula_units_Z 4 _cell_measurement_temperature 250 _cell_measurement_reflns_used 3117 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 28.9 _exptl_crystal_description plate _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9273 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 5s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 250 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11217 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2190 _reflns_number_gt 1574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K, the structure of which is free from disorder, were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. For the same reason as above, the atomic distance C(7)...N(1) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction in order to restrain the bond angle C(7)---C(8)---N(1) of the two conformers to be equal. ; _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^)+(0.0633P)^2^+0.1288P] 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 2190 _refine_ls_number_parameters 132 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.045 _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 N1A N 0.8398(3) 0.8167(5) 0.54086(17) 0.0520(7) Uani 0.75 1 d PD A 1 O1A O 0.7633(3) 0.9819(4) 0.55265(13) 0.0686(5) Uani 0.75 1 d PD A 1 O2A O 1.0065(3) 0.7893(6) 0.57585(18) 0.1020(10) Uani 0.75 1 d PD A 1 C1A C 0.4619(3) 0.4903(3) 0.37387(9) 0.0383(4) Uani 0.75 1 d PD A 1 C2A C 0.2822(3) 0.5447(3) 0.32241(13) 0.0450(4) Uani 0.75 1 d P A 1 H2A H 0.2300 0.6830 0.3308 0.054 Uiso 0.75 1 calc PR A 1 C3A C 0.1806(3) 0.3984(5) 0.25961(16) 0.0527(6) Uani 0.75 1 d P A 1 H3A H 0.0606 0.4384 0.2245 0.063 Uiso 0.75 1 calc PR A 1 C4A C 0.2564(4) 0.1896(5) 0.24811(14) 0.0513(6) Uani 0.75 1 d P A 1 H4A H 0.1872 0.0890 0.2053 0.062 Uiso 0.75 1 calc PR A 1 C5A C 0.4316(4) 0.1319(3) 0.29921(18) 0.0473(5) Uani 0.75 1 d P A 1 H5A H 0.4813 -0.0094 0.2917 0.057 Uiso 0.75 1 calc PR A 1 C6A C 0.5351(3) 0.2794(4) 0.36150(13) 0.0442(4) Uani 0.75 1 d P A 1 H6A H 0.6554 0.2387 0.3959 0.053 Uiso 0.75 1 calc PR A 1 C7A C 0.56967(19) 0.6552(3) 0.43681(8) 0.0395(3) Uani 0.75 1 d PD A 1 H7A H 0.5084 0.7823 0.4470 0.047 Uiso 0.75 1 calc PR A 1 C8A C 0.7468(2) 0.6396(3) 0.48060(10) 0.0521(4) Uani 0.75 1 d PD A 1 H8A H 0.8126 0.5139 0.4727 0.062 Uiso 0.75 1 calc PR A 1 N1B N 0.8335(15) 0.841(2) 0.5353(9) 0.107(6) Uiso 0.25 1 d PD B 2 O1B O 0.8105(12) 1.0375(15) 0.5586(6) 0.093(3) Uiso 0.25 1 d PD B 2 O2B O 0.9702(13) 0.7204(17) 0.5752(6) 0.090(3) Uiso 0.25 1 d PD B 2 C1B C 0.5032(7) 0.4342(10) 0.3775(3) 0.0446(19) Uiso 0.25 1 d PGD B 2 C2B C 0.3382(8) 0.5506(8) 0.3407(4) 0.0462(19) Uiso 0.25 1 d PG B 2 H2B H 0.3216 0.6948 0.3614 0.055 Uiso 0.25 1 calc PR B 2 C3B C 0.1976(7) 0.4539(11) 0.2732(4) 0.063(3) Uiso 0.25 1 d PG B 2 H3B H 0.0860 0.5326 0.2483 0.075 Uiso 0.25 1 calc PR B 2 C4B C 0.2221(9) 0.2407(11) 0.2426(3) 0.051(3) Uiso 0.25 1 d PG B 2 H4B H 0.1270 0.1753 0.1969 0.062 Uiso 0.25 1 calc PR B 2 C5B C 0.3871(10) 0.1242(9) 0.2794(4) 0.058(3) Uiso 0.25 1 d PG B 2 H5B H 0.4037 -0.0199 0.2587 0.069 Uiso 0.25 1 calc PR B 2 C6B C 0.5277(7) 0.2210(10) 0.3469(4) 0.056(3) Uiso 0.25 1 d PG B 2 H6B H 0.6393 0.1423 0.3718 0.067 Uiso 0.25 1 calc PR B 2 C7B C 0.6553(8) 0.5466(10) 0.4439(3) 0.0553(12) Uiso 0.25 1 d PD B 2 H7B H 0.7640 0.4605 0.4655 0.066 Uiso 0.25 1 calc PR B 2 C8B C 0.6610(8) 0.7457(11) 0.4765(3) 0.0561(12) Uiso 0.25 1 d PD B 2 H8B H 0.5531 0.8318 0.4626 0.067 Uiso 0.25 1 calc PR B 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 N1A 0.0384(8) 0.0678(12) 0.0418(8) -0.0163(8) 0.0081(5) 0.0028(7) O1A 0.0596(10) 0.0655(11) 0.0776(11) -0.0223(9) 0.0247(8) 0.0087(9) O2A 0.0438(9) 0.124(2) 0.1141(17) -0.0544(16) 0.0073(9) 0.0129(12) C1A 0.0417(9) 0.0378(8) 0.0386(8) 0.0046(6) 0.0197(6) 0.0048(8) C2A 0.0353(9) 0.0461(9) 0.0494(10) -0.0025(7) 0.0130(8) 0.0012(7) C3A 0.0409(9) 0.0554(12) 0.0579(11) -0.0049(11) 0.0160(7) -0.0049(8) C4A 0.0565(13) 0.0469(11) 0.0542(12) -0.0087(9) 0.0262(9) -0.0111(12) C5A 0.0584(12) 0.0401(10) 0.0495(11) -0.0012(7) 0.0284(12) 0.0002(8) C6A 0.0513(10) 0.0398(10) 0.0436(8) 0.0033(8) 0.0216(7) 0.0059(7) C7A 0.0405(7) 0.0396(7) 0.0408(7) 0.0006(6) 0.0190(6) 0.0082(6) C8A 0.0438(8) 0.0573(10) 0.0519(9) -0.0152(7) 0.0163(7) 0.0104(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 N1A O1A 1.197(2) . ? N1A O2A 1.237(3) . ? N1A C8A 1.450(2) . ? C1A C2A 1.396(3) . ? C1A C6A 1.406(3) . ? C1A C7A 1.457(2) . ? C2A C3A 1.375(3) . ? C3A C4A 1.400(4) . ? C4A C5A 1.371(4) . ? C5A C6A 1.378(4) . ? C7A C8A 1.320(2) . ? N1B O1B 1.244(8) . ? N1B O2B 1.249(9) . ? N1B C8B 1.464(8) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.463(6) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.279(8) . ? 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 O2A 122.7(2) . . ? O1A N1A C8A 122.91(18) . . ? O2A N1A C8A 114.2(2) . . ? C2A C1A C6A 118.52(15) . . ? C2A C1A C7A 119.55(19) . . ? C6A C1A C7A 121.90(19) . . ? C3A C2A C1A 120.81(16) . . ? C2A C3A C4A 119.74(17) . . ? C5A C4A C3A 120.06(18) . . ? C4A C5A C6A 120.50(17) . . ? C5A C6A C1A 120.35(16) . . ? C8A C7A C1A 124.90(15) . . ? C7A C8A N1A 119.84(15) . . ? O1B N1B O2B 122.1(10) . . ? O1B N1B C8B 110.8(9) . . ? O2B N1B C8B 123.8(9) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 119.5(5) . . ? C6B C1B C7B 120.3(5) . . ? C3B C2B C1B 120.0 . . ? C4B C3B C2B 120.0 . . ? C3B C4B C5B 120.0 . . ? C6B C5B C4B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 129.0(6) . . ? C7B C8B N1B 120.7(7) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -1.8(2) . . . . ? C7A C1A C2A C3A 176.34(16) . . . . ? C1A C2A C3A C4A 1.5(3) . . . . ? C2A C3A C4A C5A -0.2(3) . . . . ? C3A C4A C5A C6A -0.8(2) . . . . ? C4A C5A C6A C1A 0.5(2) . . . . ? C2A C1A C6A C5A 0.8(2) . . . . ? C7A C1A C6A C5A -177.31(15) . . . . ? C2A C1A C7A C8A -169.43(16) . . . . ? C6A C1A C7A C8A 8.6(2) . . . . ? C1A C7A C8A N1A 179.1(2) . . . . ? O1A N1A C8A C7A -1.0(5) . . . . ? O2A N1A C8A C7A -177.2(3) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 174.7(5) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C2B C3B C4B C5B 0.0 . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -174.6(5) . . . . ? C2B C1B C7B C8B 1.3(8) . . . . ? C6B C1B C7B C8B 176.0(5) . . . . ? C1B C7B C8B N1B -171.9(11) . . . . ? O1B N1B C8B C7B 178.7(11) . . . . ? O2B N1B C8B C7B -22(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.173 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.040 #===END data_no2200k _database_code_depnum_ccdc_archive 'CCDC 701894' _audit_creation_method SHELXL-97 _chemical_name_systematic ; \b-Nitrostyrene ; _chemical_name_common beta-Nitrostyrene _chemical_melting_point 54_C _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 N O2' _chemical_formula_weight 149.15 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_1_21/c_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0279(6) _cell_length_b 5.7186(4) _cell_length_c 17.6994(13) _cell_angle_alpha 90.00 _cell_angle_beta 113.470(1) _cell_angle_gamma 90.00 _cell_volume 745.33(9) _cell_formula_units_Z 4 _cell_measurement_temperature 200 _cell_measurement_reflns_used 3874 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 29.8 _exptl_crystal_description plate _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9263 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 5s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 200 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 11008 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2157 _reflns_number_gt 1745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K, the structure of which is free from disorder, were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. For the same reason as above, the atomic distance C(7)...N(1) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction in order to restrain the bond angle C(7)---C(8)---N(1) of the two conformers to be equal. ; _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^)+(0.0568P)^2^+0.2089P] 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 2157 _refine_ls_number_parameters 132 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.028 _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 N1A N 0.8421(2) 0.8162(5) 0.54002(18) 0.0413(5) Uani 0.82 1 d PD A 1 O1A O 0.7641(2) 0.9839(3) 0.55176(11) 0.0522(4) Uani 0.82 1 d PD A 1 O2A O 1.0032(2) 0.7692(4) 0.57906(12) 0.0712(6) Uani 0.82 1 d PD A 1 C1A C 0.4607(2) 0.4903(3) 0.37389(8) 0.0289(3) Uani 0.82 1 d PD A 1 C2A C 0.2816(3) 0.5461(3) 0.32283(11) 0.0343(3) Uani 0.82 1 d P A 1 H2A H 0.2295 0.6870 0.3318 0.041 Uiso 0.82 1 calc PR A 1 C3A C 0.1794(2) 0.3988(4) 0.25949(13) 0.0404(4) Uani 0.82 1 d P A 1 H3A H 0.0587 0.4404 0.2243 0.048 Uiso 0.82 1 calc PR A 1 C4A C 0.2537(3) 0.1887(4) 0.24719(11) 0.0395(4) Uani 0.82 1 d P A 1 H4A H 0.1836 0.0870 0.2037 0.047 Uiso 0.82 1 calc PR A 1 C5A C 0.4294(3) 0.1289(3) 0.29843(14) 0.0362(4) Uani 0.82 1 d P A 1 H5A H 0.4791 -0.0151 0.2905 0.043 Uiso 0.82 1 calc PR A 1 C6A C 0.5334(2) 0.2774(3) 0.36125(11) 0.0337(3) Uani 0.82 1 d P A 1 H6A H 0.6544 0.2354 0.3959 0.040 Uiso 0.82 1 calc PR A 1 C7A C 0.56918(17) 0.6561(2) 0.43688(7) 0.0297(3) Uani 0.82 1 d PD A 1 H7A H 0.5081 0.7853 0.4480 0.036 Uiso 0.82 1 calc PR A 1 C8A C 0.74700(19) 0.6395(3) 0.47976(9) 0.0394(3) Uani 0.82 1 d PD A 1 H8A H 0.8121 0.5111 0.4709 0.047 Uiso 0.82 1 calc PR A 1 N1B N 0.8384(14) 0.841(3) 0.5342(14) 0.086(7) Uiso 0.18 1 d PD B 2 O1B O 0.8083(16) 1.037(2) 0.5571(8) 0.078(4) Uiso 0.18 1 d PD B 2 O2B O 1.0092(13) 0.8381(16) 0.5576(6) 0.056(2) Uiso 0.18 1 d PD B 2 C1B C 0.5010(8) 0.4336(12) 0.3773(4) 0.036(2) Uiso 0.18 1 d PGD B 2 C2B C 0.3366(10) 0.5513(10) 0.3410(4) 0.038(2) Uiso 0.18 1 d PG B 2 H2B H 0.3203 0.6981 0.3623 0.045 Uiso 0.18 1 calc PR B 2 C3B C 0.1960(8) 0.4541(13) 0.2737(5) 0.051(4) Uiso 0.18 1 d PG B 2 H3B H 0.0836 0.5345 0.2489 0.062 Uiso 0.18 1 calc PR B 2 C4B C 0.2198(10) 0.2393(14) 0.2426(4) 0.042(3) Uiso 0.18 1 d PG B 2 H4B H 0.1237 0.1729 0.1966 0.050 Uiso 0.18 1 calc PR B 2 C5B C 0.3842(12) 0.1217(11) 0.2789(5) 0.048(4) Uiso 0.18 1 d PG B 2 H5B H 0.4005 -0.0251 0.2576 0.057 Uiso 0.18 1 calc PR B 2 C6B C 0.5249(9) 0.2188(13) 0.3462(5) 0.044(3) Uiso 0.18 1 d PG B 2 H6B H 0.6372 0.1384 0.3710 0.053 Uiso 0.18 1 calc PR B 2 C7B C 0.6499(12) 0.5519(17) 0.4430(5) 0.060(2) Uiso 0.18 1 d PD B 2 H7B H 0.7584 0.4622 0.4643 0.072 Uiso 0.18 1 calc PR B 2 C8B C 0.6638(12) 0.7409(18) 0.4761(5) 0.059(2) Uiso 0.18 1 d PD B 2 H8B H 0.5565 0.8303 0.4641 0.071 Uiso 0.18 1 calc PR B 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 N1A 0.0312(7) 0.0531(9) 0.0343(7) -0.0138(7) 0.0075(5) 0.0015(5) O1A 0.0444(8) 0.0509(8) 0.0579(8) -0.0183(7) 0.0169(6) 0.0075(7) O2A 0.0426(7) 0.0899(15) 0.0672(12) -0.0192(11) 0.0073(7) 0.0179(9) C1A 0.0309(7) 0.0279(6) 0.0301(6) 0.0031(5) 0.0143(5) 0.0043(6) C2A 0.0268(7) 0.0345(7) 0.0384(8) -0.0013(5) 0.0097(7) 0.0011(5) C3A 0.0316(7) 0.0430(9) 0.0433(8) -0.0046(8) 0.0115(6) -0.0044(6) C4A 0.0431(9) 0.0366(8) 0.0412(9) -0.0060(7) 0.0194(7) -0.0082(9) C5A 0.0448(9) 0.0300(8) 0.0379(8) -0.0009(6) 0.0208(9) -0.0002(6) C6A 0.0392(8) 0.0300(7) 0.0333(7) 0.0010(7) 0.0157(5) 0.0043(5) C7A 0.0308(6) 0.0297(6) 0.0302(6) 0.0003(5) 0.0137(5) 0.0061(5) C8A 0.0327(6) 0.0437(7) 0.0388(7) -0.0127(6) 0.0109(5) 0.0078(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 N1A O1A 1.208(2) . ? N1A O2A 1.229(2) . ? N1A C8A 1.447(2) . ? C1A C2A 1.397(2) . ? C1A C6A 1.406(2) . ? C1A C7A 1.4582(18) . ? C2A C3A 1.381(3) . ? C3A C4A 1.397(3) . ? C4A C5A 1.382(3) . ? C5A C6A 1.384(3) . ? C7A C8A 1.3266(18) . ? N1B O1B 1.250(9) . ? N1B O2B 1.264(9) . ? N1B C8B 1.483(8) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.460(7) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.213(12) . ? 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 O2A 125.35(17) . . ? O1A N1A C8A 121.59(16) . . ? O2A N1A C8A 112.96(18) . . ? C2A C1A C6A 118.72(13) . . ? C2A C1A C7A 119.58(15) . . ? C6A C1A C7A 121.67(15) . . ? C3A C2A C1A 120.79(13) . . ? C2A C3A C4A 119.90(14) . . ? C5A C4A C3A 119.88(15) . . ? C4A C5A C6A 120.48(14) . . ? C5A C6A C1A 120.20(14) . . ? C8A C7A C1A 124.75(13) . . ? C7A C8A N1A 120.24(13) . . ? O1B N1B O2B 103.3(10) . . ? O1B N1B C8B 108.6(11) . . ? O2B N1B C8B 145.5(13) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 118.0(6) . . ? C6B C1B C7B 121.8(6) . . ? C3B C2B C1B 120.0 . . ? C2B C3B C4B 120.0 . . ? C3B C4B C5B 120.0 . . ? C6B C5B C4B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 133.3(10) . . ? C7B C8B N1B 123.9(10) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -2.0(2) . . . . ? C7A C1A C2A C3A 176.05(13) . . . . ? C1A C2A C3A C4A 1.5(2) . . . . ? C2A C3A C4A C5A -0.1(2) . . . . ? C3A C4A C5A C6A -0.9(2) . . . . ? C4A C5A C6A C1A 0.4(2) . . . . ? C2A C1A C6A C5A 1.01(19) . . . . ? C7A C1A C6A C5A -176.98(13) . . . . ? C2A C1A C7A C8A -168.83(14) . . . . ? C6A C1A C7A C8A 9.1(2) . . . . ? C1A C7A C8A N1A 179.0(2) . . . . ? O1A N1A C8A C7A -1.4(5) . . . . ? O2A N1A C8A C7A 175.0(2) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 174.6(7) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C2B C3B C4B C5B 0.0 . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -174.4(7) . . . . ? C2B C1B C7B C8B 0.9(14) . . . . ? C6B C1B C7B C8B 175.4(10) . . . . ? C1B C7B C8B N1B -170.6(16) . . . . ? O1B N1B C8B C7B 179.6(15) . . . . ? O2B N1B C8B C7B 23(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.258 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.044 #===END data_no2150k _database_code_depnum_ccdc_archive 'CCDC 701895' _audit_creation_method SHELXL-97 _chemical_name_systematic ; \b-Nitrostyrene ; _chemical_name_common beta-Nitrostyrene _chemical_melting_point 54_C _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 N O2' _chemical_formula_weight 149.15 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_1_21/c_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0185(6) _cell_length_b 5.6848(4) _cell_length_c 17.5444(12) _cell_angle_alpha 90.00 _cell_angle_beta 112.991(1) _cell_angle_gamma 90.00 _cell_volume 736.21(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 5044 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.0 _exptl_crystal_description plate _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9255 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 5s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 150 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10868 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0128 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2134 _reflns_number_gt 1831 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K, the structure of which is free from disorder, were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. For the same reason as above, the atomic distance C(7)...N(1) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction in order to restrain the bond angle C(7)---C(8)---N(1) of the two conformers to be equal. ; _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^)+(0.0689P)^2^+0.1398P] 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 2134 _refine_ls_number_parameters 124 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1243 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.077 _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 N1A N 0.84376(18) 0.8167(3) 0.53905(10) 0.0318(3) Uani 0.88 1 d PD A 1 O1A O 0.76531(17) 0.9868(2) 0.55136(8) 0.0385(3) Uani 0.88 1 d PD A 1 O2A O 1.00880(18) 0.7872(4) 0.57486(12) 0.0581(5) Uani 0.88 1 d PD A 1 C1A C 0.46109(14) 0.48816(18) 0.37415(6) 0.0209(2) Uani 0.88 1 d PD A 1 C2A C 0.28256(15) 0.54713(19) 0.32382(7) 0.0247(2) Uani 0.88 1 d P A 1 H2A H 0.2318 0.6894 0.3335 0.030 Uiso 0.88 1 calc PR A 1 C3A C 0.17859(15) 0.3996(2) 0.25973(7) 0.0295(3) Uani 0.88 1 d P A 1 H3A H 0.0583 0.4427 0.2251 0.035 Uiso 0.88 1 calc PR A 1 C4A C 0.25096(17) 0.1888(2) 0.24640(7) 0.0284(3) Uani 0.88 1 d P A 1 H4A H 0.1803 0.0880 0.2025 0.034 Uiso 0.88 1 calc PR A 1 C5A C 0.42672(16) 0.12581(19) 0.29742(7) 0.0264(2) Uani 0.88 1 d P A 1 H5A H 0.4750 -0.0197 0.2889 0.032 Uiso 0.88 1 calc PR A 1 C6A C 0.53216(14) 0.2738(2) 0.36078(7) 0.0244(2) Uani 0.88 1 d P A 1 H6A H 0.6525 0.2300 0.3951 0.029 Uiso 0.88 1 calc PR A 1 C7A C 0.56865(13) 0.65674(18) 0.43698(6) 0.0224(2) Uani 0.88 1 d PD A 1 H7A H 0.5076 0.7863 0.4487 0.027 Uiso 0.88 1 calc PR A 1 C8A C 0.74742(15) 0.6397(2) 0.47896(7) 0.0295(3) Uani 0.88 1 d PD A 1 H8A H 0.8116 0.5104 0.4693 0.035 Uiso 0.88 1 calc PR A 1 N1B N 0.840(2) 0.843(4) 0.5324(15) 0.073(2) Uiso 0.12 1 d PD B 2 O1B O 0.803(3) 1.035(3) 0.5550(14) 0.102(6) Uiso 0.12 1 d PD B 2 O2B O 0.986(3) 0.740(4) 0.5698(15) 0.102(6) Uiso 0.12 1 d PD B 2 C1B C 0.5049(16) 0.423(3) 0.3767(7) 0.073(2) Uiso 0.12 1 d PGD B 2 C2B C 0.346(2) 0.5526(19) 0.3442(9) 0.073(2) Uiso 0.12 1 d PG B 2 H2B H 0.3374 0.7004 0.3677 0.087 Uiso 0.12 1 calc PR B 2 C3B C 0.1985(16) 0.466(2) 0.2772(9) 0.073(2) Uiso 0.12 1 d PG B 2 H3B H 0.0896 0.5548 0.2549 0.087 Uiso 0.12 1 calc PR B 2 C4B C 0.2106(16) 0.250(3) 0.2427(7) 0.073(2) Uiso 0.12 1 d PG B 2 H4B H 0.1100 0.1907 0.1970 0.087 Uiso 0.12 1 calc PR B 2 C5B C 0.370(2) 0.1200(19) 0.2753(8) 0.073(2) Uiso 0.12 1 d PG B 2 H5B H 0.3781 -0.0278 0.2518 0.087 Uiso 0.12 1 calc PR B 2 C6B C 0.5170(14) 0.207(2) 0.3423(8) 0.073(2) Uiso 0.12 1 d PG B 2 H6B H 0.6259 0.1178 0.3645 0.087 Uiso 0.12 1 calc PR B 2 C7B C 0.630(2) 0.570(3) 0.4413(9) 0.073(2) Uiso 0.12 1 d PD B 2 H7B H 0.7269 0.4661 0.4702 0.087 Uiso 0.12 1 calc PR B 2 C8B C 0.673(2) 0.733(3) 0.4741(9) 0.073(2) Uiso 0.12 1 d PD B 2 H8B H 0.5736 0.8367 0.4619 0.087 Uiso 0.12 1 calc PR B 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 N1A 0.0238(5) 0.0401(6) 0.0279(5) -0.0098(5) 0.0061(4) 0.0032(4) O1A 0.0332(5) 0.0383(6) 0.0411(5) -0.0140(4) 0.0114(4) 0.0062(4) O2A 0.0236(5) 0.0745(10) 0.0605(7) -0.0339(7) -0.0006(4) 0.0098(5) C1A 0.0220(4) 0.0213(5) 0.0206(4) 0.0018(3) 0.0096(3) 0.0013(3) C2A 0.0214(5) 0.0242(5) 0.0279(5) -0.0005(4) 0.0091(4) 0.0010(4) C3A 0.0232(5) 0.0315(6) 0.0314(5) -0.0026(4) 0.0079(4) -0.0032(4) C4A 0.0305(6) 0.0279(5) 0.0285(5) -0.0042(4) 0.0133(4) -0.0071(4) C5A 0.0333(6) 0.0211(5) 0.0285(5) -0.0007(4) 0.0160(4) -0.0005(4) C6A 0.0275(5) 0.0219(5) 0.0245(5) 0.0016(4) 0.0111(4) 0.0036(4) C7A 0.0230(5) 0.0230(5) 0.0219(4) 0.0001(3) 0.0096(4) 0.0046(4) C8A 0.0244(5) 0.0325(5) 0.0289(5) -0.0100(4) 0.0076(4) 0.0059(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 N1A O1A 1.2179(14) . ? N1A O2A 1.2349(15) . ? N1A C8A 1.4438(15) . ? C1A C2A 1.3979(14) . ? C1A C6A 1.4034(14) . ? C1A C7A 1.4610(13) . ? C2A C3A 1.3893(15) . ? C3A C4A 1.3905(16) . ? C4A C5A 1.3893(16) . ? C5A C6A 1.3871(15) . ? C7A C8A 1.3349(14) . ? N1B O1B 1.237(10) . ? N1B O2B 1.245(10) . ? N1B C8B 1.469(9) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.452(9) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.070(19) . ? 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 O2A 122.89(12) . . ? O1A N1A C8A 121.12(12) . . ? O2A N1A C8A 115.98(13) . . ? C2A C1A C6A 119.03(9) . . ? C2A C1A C7A 118.45(10) . . ? C6A C1A C7A 122.49(10) . . ? C3A C2A C1A 120.61(10) . . ? C2A C3A C4A 119.89(10) . . ? C5A C4A C3A 119.92(10) . . ? C6A C5A C4A 120.49(10) . . ? C5A C6A C1A 120.02(9) . . ? C8A C7A C1A 123.99(10) . . ? C7A C8A N1A 120.35(11) . . ? O1B N1B O2B 122.9(19) . . ? O1B N1B C8B 109.4(19) . . ? O2B N1B C8B 125.4(18) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 105.0(13) . . ? C6B C1B C7B 134.9(12) . . ? C3B C2B C1B 120.0 . . ? C2B C3B C4B 120.0 . . ? C3B C4B C5B 120.0 . . ? C6B C5B C4B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 154(2) . . ? C7B C8B N1B 139(2) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -2.07(15) . . . . ? C7A C1A C2A C3A 175.83(9) . . . . ? C1A C2A C3A C4A 1.37(16) . . . . ? C2A C3A C4A C5A 0.28(16) . . . . ? C3A C4A C5A C6A -1.20(16) . . . . ? C4A C5A C6A C1A 0.48(15) . . . . ? C2A C1A C6A C5A 1.15(14) . . . . ? C7A C1A C6A C5A -176.67(9) . . . . ? C2A C1A C7A C8A -168.23(10) . . . . ? C6A C1A C7A C8A 9.59(16) . . . . ? C1A C7A C8A N1A 178.89(13) . . . . ? O1A N1A C8A C7A -1.6(3) . . . . ? O2A N1A C8A C7A -179.88(19) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 176.6(13) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C2B C3B C4B C5B 0.0 . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -175.4(18) . . . . ? C2B C1B C7B C8B -12(5) . . . . ? C6B C1B C7B C8B 164(4) . . . . ? C1B C7B C8B N1B -162(3) . . . . ? O1B N1B C8B C7B -175(3) . . . . ? O2B N1B C8B C7B -12(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.287 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.059 #===END data_no290k _database_code_depnum_ccdc_archive 'CCDC 701896' _audit_creation_method SHELXL-97 _chemical_name_systematic ; \b-Nitrostyrene ; _chemical_name_common beta-Nitrostyrene _chemical_melting_point 54_C _chemical_formula_moiety ? _chemical_formula_sum 'C8 H7 N O2' _chemical_formula_weight 149.15 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_1_21/c_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.9963(6) _cell_length_b 5.6699(4) _cell_length_c 17.4179(13) _cell_angle_alpha 90.00 _cell_angle_beta 112.752(1) _cell_angle_gamma 90.00 _cell_volume 728.25(9) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 5843 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.0 _exptl_crystal_description plate _exptl_crystal_colour pale_yellow _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9247 _exptl_absorpt_correction_T_max 0.9901 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 5s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 90 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 10648 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0131 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2112 _reflns_number_gt 1871 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K, the structure of which is free from disorder, were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. For the same reason as above, the atomic distance C(7)...N(1) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction in order to restrain the bond angle C(7)---C(8)---N(1) of the two conformers to be equal. ; _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^)+(0.0565P)^2^+0.1876P] 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 2112 _refine_ls_number_parameters 124 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1066 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.078 _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 N1A N 0.84470(15) 0.8181(2) 0.53842(10) 0.0214(2) Uani 0.91 1 d PD A 1 O1A O 0.76450(13) 0.98826(18) 0.55127(6) 0.0255(2) Uani 0.91 1 d PD A 1 O2A O 1.01045(14) 0.7896(3) 0.57421(8) 0.0380(3) Uani 0.91 1 d PD A 1 C1A C 0.46068(13) 0.48573(17) 0.37415(5) 0.01428(18) Uani 0.91 1 d PD A 1 C2A C 0.28160(13) 0.54455(17) 0.32359(6) 0.01687(19) Uani 0.91 1 d P A 1 H2A H 0.2306 0.6872 0.3333 0.020 Uiso 0.91 1 calc PR A 1 C3A C 0.17781(13) 0.39575(19) 0.25926(6) 0.0195(2) Uani 0.91 1 d P A 1 H3A H 0.0574 0.4388 0.2244 0.023 Uiso 0.91 1 calc PR A 1 C4A C 0.25048(15) 0.18392(18) 0.24603(6) 0.0190(2) Uani 0.91 1 d P A 1 H4A H 0.1799 0.0825 0.2020 0.023 Uiso 0.91 1 calc PR A 1 C5A C 0.42687(14) 0.12081(17) 0.29744(6) 0.0178(2) Uani 0.91 1 d P A 1 H5A H 0.4755 -0.0252 0.2889 0.021 Uiso 0.91 1 calc PR A 1 C6A C 0.53202(12) 0.26998(18) 0.36102(6) 0.01666(19) Uani 0.91 1 d P A 1 H6A H 0.6523 0.2261 0.3957 0.020 Uiso 0.91 1 calc PR A 1 C7A C 0.56824(12) 0.65553(16) 0.43704(5) 0.01538(19) Uani 0.91 1 d PD A 1 H7A H 0.5069 0.7848 0.4491 0.018 Uiso 0.91 1 calc PR A 1 C8A C 0.74766(13) 0.63988(18) 0.47855(6) 0.0201(2) Uani 0.91 1 d PD A 1 H8A H 0.8119 0.5103 0.4686 0.024 Uiso 0.91 1 calc PR A 1 N1B N 0.827(3) 0.847(4) 0.5359(17) 0.0500(17) Uiso 0.09 1 d PD B 2 O1B O 0.805(2) 1.046(3) 0.5592(12) 0.066(5) Uiso 0.09 1 d PD B 2 O2B O 0.976(3) 0.742(4) 0.5675(14) 0.066(5) Uiso 0.09 1 d PD B 2 C1B C 0.5058(15) 0.415(2) 0.3770(7) 0.0500(17) Uiso 0.09 1 d PGD B 2 C2B C 0.348(2) 0.5485(18) 0.3450(8) 0.0500(17) Uiso 0.09 1 d PG B 2 H2B H 0.3419 0.6972 0.3689 0.060 Uiso 0.09 1 calc PR B 2 C3B C 0.1992(15) 0.465(2) 0.2779(9) 0.0500(17) Uiso 0.09 1 d PG B 2 H3B H 0.0914 0.5558 0.2560 0.060 Uiso 0.09 1 calc PR B 2 C4B C 0.2082(15) 0.247(3) 0.2429(7) 0.0500(17) Uiso 0.09 1 d PG B 2 H4B H 0.1065 0.1896 0.1970 0.060 Uiso 0.09 1 calc PR B 2 C5B C 0.3660(18) 0.1134(18) 0.2749(8) 0.0500(17) Uiso 0.09 1 d PG B 2 H5B H 0.3721 -0.0352 0.2510 0.060 Uiso 0.09 1 calc PR B 2 C6B C 0.5148(14) 0.197(2) 0.3420(8) 0.0500(17) Uiso 0.09 1 d PG B 2 H6B H 0.6226 0.1062 0.3639 0.060 Uiso 0.09 1 calc PR B 2 C7B C 0.639(2) 0.559(3) 0.4416(9) 0.0500(17) Uiso 0.09 1 d PD B 2 H7B H 0.7458 0.4672 0.4655 0.060 Uiso 0.09 1 calc PR B 2 C8B C 0.666(2) 0.734(3) 0.4747(9) 0.0500(17) Uiso 0.09 1 d PD B 2 H8B H 0.5604 0.8298 0.4595 0.060 Uiso 0.09 1 calc PR B 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 N1A 0.0159(4) 0.0269(5) 0.0190(4) -0.0060(4) 0.0041(3) 0.0029(4) O1A 0.0225(4) 0.0251(5) 0.0273(4) -0.0090(3) 0.0080(3) 0.0044(3) O2A 0.0156(4) 0.0487(7) 0.0400(5) -0.0213(5) 0.0000(4) 0.0061(4) C1A 0.0150(4) 0.0147(4) 0.0139(4) 0.0011(3) 0.0064(3) 0.0008(3) C2A 0.0148(4) 0.0168(4) 0.0187(4) -0.0004(3) 0.0062(3) 0.0006(3) C3A 0.0158(4) 0.0209(5) 0.0206(4) -0.0016(3) 0.0056(3) -0.0022(3) C4A 0.0204(5) 0.0186(5) 0.0190(4) -0.0025(3) 0.0088(3) -0.0043(3) C5A 0.0220(5) 0.0149(4) 0.0187(4) -0.0002(3) 0.0105(4) -0.0003(3) C6A 0.0186(4) 0.0152(4) 0.0166(4) 0.0008(3) 0.0072(3) 0.0021(3) C7A 0.0163(4) 0.0157(4) 0.0148(4) -0.0001(3) 0.0067(3) 0.0030(3) C8A 0.0174(4) 0.0221(4) 0.0193(4) -0.0067(3) 0.0054(3) 0.0035(3) _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 N1A O1A 1.2260(12) . ? N1A O2A 1.2379(12) . ? N1A C8A 1.4439(13) . ? C1A C2A 1.4006(12) . ? C1A C6A 1.4053(12) . ? C1A C7A 1.4621(12) . ? C2A C3A 1.3917(13) . ? C3A C4A 1.3918(14) . ? C4A C5A 1.3937(14) . ? C5A C6A 1.3887(13) . ? C7A C8A 1.3366(13) . ? N1B O1B 1.232(10) . ? N1B O2B 1.250(10) . ? N1B C8B 1.469(9) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.461(9) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.125(19) . ? 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 O2A 123.00(10) . . ? O1A N1A C8A 120.64(9) . . ? O2A N1A C8A 116.35(10) . . ? C2A C1A C6A 119.05(8) . . ? C2A C1A C7A 118.45(9) . . ? C6A C1A C7A 122.47(9) . . ? C3A C2A C1A 120.54(8) . . ? C2A C3A C4A 119.95(9) . . ? C3A C4A C5A 119.92(9) . . ? C6A C5A C4A 120.41(9) . . ? C5A C6A C1A 120.08(8) . . ? C8A C7A C1A 123.98(9) . . ? C7A C8A N1A 120.59(9) . . ? O1B N1B O2B 121.7(17) . . ? O1B N1B C8B 116.0(18) . . ? O2B N1B C8B 122.0(16) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 106.3(12) . . ? C6B C1B C7B 133.5(12) . . ? C3B C2B C1B 120.0 . . ? C2B C3B C4B 120.0 . . ? C5B C4B C3B 120.0 . . ? C4B C5B C6B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 146(2) . . ? C7B C8B N1B 134.3(19) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -2.36(13) . . . . ? C7A C1A C2A C3A 175.71(8) . . . . ? C1A C2A C3A C4A 1.52(14) . . . . ? C2A C3A C4A C5A 0.24(14) . . . . ? C3A C4A C5A C6A -1.13(14) . . . . ? C4A C5A C6A C1A 0.27(13) . . . . ? C2A C1A C6A C5A 1.46(13) . . . . ? C7A C1A C6A C5A -176.53(8) . . . . ? C2A C1A C7A C8A -167.62(9) . . . . ? C6A C1A C7A C8A 10.38(14) . . . . ? C1A C7A C8A N1A 178.55(12) . . . . ? O1A N1A C8A C7A -1.0(3) . . . . ? O2A N1A C8A C7A 179.80(16) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 175.7(12) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C2B C3B C4B C5B 0.0 . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -174.3(16) . . . . ? C2B C1B C7B C8B -2(3) . . . . ? C6B C1B C7B C8B 173(2) . . . . ? C1B C7B C8B N1B -173(3) . . . . ? O1B N1B C8B C7B -180(2) . . . . ? O2B N1B C8B C7B -5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.298 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.063 #===END data_nme2300k _database_code_depnum_ccdc_archive 'CCDC 701897' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Dimethylamino-\b-nitrostyrene ; _chemical_name_common 4-Dimethylamino-beta-nitrostyrene _chemical_melting_point 180_C _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 orthorhombic _symmetry_space_group_name_H-M P_b_c_a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.3129(6) _cell_length_b 7.4611(5) _cell_length_c 25.3216(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1948.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 300 _cell_measurement_reflns_used 7072 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 29.9 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9637 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 10s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 300 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 28459 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0140 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 30.05 _reflns_number_total 2847 _reflns_number_gt 1910 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. The following target values were taken from the corresponding bond lengths of 4-dimethylamino-\b-ethyl-\b-nitrostyrene at 100 K reported in reference 13 and used for SHELXL DFIX instructions. The length of the N---Ph bond (N(2)---C(4)) of the two conformers was restrained to be 1.37 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---Me bonds (N(2)---C(9) and N(2)---C(10)) of the two conformers were restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C\\dbC bond (C(7)\\dbC(8)) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction. DFIX was not applied to the length because the observed length of the C\\dbC bond would change with temperature and there is no proper target length required for DFIX. ; _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^)+(0.0532P)^2^+0.5447P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0051(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2847 _refine_ls_number_parameters 176 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1556 _refine_ls_wR_factor_gt 0.1294 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.048 _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 N1A N 0.3740(4) 0.1234(6) 0.36397(10) 0.0694(9) Uani 0.72 1 d PD A 1 N2A N 0.3956(8) 0.2261(11) 0.67705(17) 0.064(2) Uani 0.72 1 d PD A 1 O1A O 0.4587(7) 0.2175(11) 0.3450(3) 0.1043(16) Uani 0.72 1 d PD A 1 O2A O 0.3026(3) 0.0378(5) 0.33524(11) 0.1070(11) Uani 0.72 1 d PD A 1 C1A C 0.4176(2) 0.1998(3) 0.51041(7) 0.0428(4) Uani 0.72 1 d PD A 1 C2A C 0.5031(3) 0.2998(4) 0.54105(9) 0.0488(6) Uani 0.72 1 d P A 1 H2A H 0.5676 0.3654 0.5241 0.059 Uiso 0.72 1 calc PR A 1 C3A C 0.4964(3) 0.3057(4) 0.59495(11) 0.0452(11) Uani 0.72 1 d P A 1 H3A H 0.5566 0.3740 0.6134 0.054 Uiso 0.72 1 calc PR A 1 C4A C 0.4012(5) 0.2116(8) 0.62316(13) 0.0528(19) Uani 0.72 1 d PD A 1 C5A C 0.3157(3) 0.1061(4) 0.59215(13) 0.0506(6) Uani 0.72 1 d P A 1 H5A H 0.2520 0.0385 0.6089 0.061 Uiso 0.72 1 calc PR A 1 C6A C 0.3243(2) 0.1012(3) 0.53840(10) 0.0473(5) Uani 0.72 1 d P A 1 H6A H 0.2663 0.0299 0.5197 0.057 Uiso 0.72 1 calc PR A 1 C7A C 0.4269(2) 0.1989(3) 0.45397(8) 0.0485(4) Uani 0.72 1 d PD A 1 H7A H 0.4932 0.2680 0.4396 0.058 Uiso 0.72 1 calc PR A 1 C8A C 0.3529(2) 0.1118(3) 0.41959(7) 0.0554(5) Uani 0.72 1 d PD A 1 H8A H 0.2853 0.0411 0.4321 0.066 Uiso 0.72 1 calc PR A 1 C9A C 0.4987(7) 0.3195(10) 0.7049(3) 0.090(2) Uani 0.72 1 d PD A 1 H91A H 0.4737 0.3376 0.7411 0.135 Uiso 0.72 1 calc PR A 1 H92A H 0.5139 0.4335 0.6885 0.135 Uiso 0.72 1 calc PR A 1 H93A H 0.5766 0.2492 0.7036 0.135 Uiso 0.72 1 calc PR A 1 C10A C 0.3030(7) 0.1198(11) 0.7074(3) 0.099(2) Uani 0.72 1 d PD A 1 H101 H 0.3066 0.1549 0.7439 0.149 Uiso 0.72 1 calc PR A 1 H102 H 0.3245 -0.0050 0.7044 0.149 Uiso 0.72 1 calc PR A 1 H103 H 0.2172 0.1396 0.6940 0.149 Uiso 0.72 1 calc PR A 1 N1B N 0.3975(13) 0.163(2) 0.3678(4) 0.085(4) Uiso 0.28 1 d PD B 2 N2B N 0.3991(16) 0.222(2) 0.6787(4) 0.045(4) Uiso 0.28 1 d PD B 2 O1B O 0.4866(18) 0.232(3) 0.3431(9) 0.089(3) Uiso 0.28 1 d PD B 2 O2B O 0.3139(12) 0.0549(17) 0.3541(5) 0.122(5) Uiso 0.28 1 d PD B 2 C1B C 0.3786(5) 0.1619(7) 0.51707(15) 0.0398(15) Uiso 0.28 1 d PGD B 2 C2B C 0.4749(6) 0.2728(10) 0.5372(2) 0.056(3) Uiso 0.28 1 d PG B 2 H2B H 0.5320 0.3306 0.5144 0.067 Uiso 0.28 1 calc PR B 2 C3B C 0.4860(8) 0.2974(13) 0.5915(3) 0.073(6) Uiso 0.28 1 d PG B 2 H3B H 0.5504 0.3716 0.6050 0.088 Uiso 0.28 1 calc PR B 2 C4B C 0.4007(9) 0.2111(14) 0.62552(17) 0.031(3) Uiso 0.28 1 d PGD B 2 C5B C 0.3044(7) 0.1002(10) 0.6054(2) 0.047(2) Uiso 0.28 1 d PG B 2 H5B H 0.2474 0.0424 0.6281 0.057 Uiso 0.28 1 calc PR B 2 C6B C 0.2934(5) 0.0756(7) 0.5511(2) 0.052(2) Uiso 0.28 1 d PG B 2 H6B H 0.2289 0.0014 0.5376 0.063 Uiso 0.28 1 calc PR B 2 C7B C 0.3617(6) 0.1339(8) 0.4613(2) 0.0600(13) Uiso 0.28 1 d PD B 2 H7B H 0.2949 0.0572 0.4514 0.072 Uiso 0.28 1 calc PR B 2 C8B C 0.4297(7) 0.2040(9) 0.4227(3) 0.0681(16) Uiso 0.28 1 d PD B 2 H8B H 0.4986 0.2801 0.4303 0.082 Uiso 0.28 1 calc PR B 2 C9B C 0.4916(12) 0.3242(14) 0.7092(6) 0.048(2) Uiso 0.28 1 d PD B 2 H91B H 0.5777 0.2984 0.6970 0.073 Uiso 0.28 1 calc PR B 2 H92B H 0.4842 0.2923 0.7458 0.073 Uiso 0.28 1 calc PR B 2 H93B H 0.4742 0.4498 0.7051 0.073 Uiso 0.28 1 calc PR B 2 C10B C 0.3059(11) 0.1241(16) 0.7090(5) 0.051(3) Uiso 0.28 1 d PD B 2 H104 H 0.2201 0.1577 0.6982 0.077 Uiso 0.28 1 calc PR B 2 H105 H 0.3172 0.1509 0.7458 0.077 Uiso 0.28 1 calc PR B 2 H106 H 0.3181 -0.0020 0.7034 0.077 Uiso 0.28 1 calc PR B 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 N1A 0.088(3) 0.079(2) 0.0420(12) -0.0054(12) -0.0054(13) 0.034(2) N2A 0.066(3) 0.077(3) 0.050(2) 0.0040(10) 0.0066(10) -0.0060(11) O1A 0.119(5) 0.126(3) 0.0680(17) 0.0056(16) 0.002(3) -0.003(3) O2A 0.1023(17) 0.146(2) 0.0729(15) -0.0346(16) -0.0297(13) 0.0235(15) C1A 0.0392(9) 0.0406(9) 0.0486(10) 0.0023(8) -0.0017(8) 0.0023(8) C2A 0.0478(12) 0.0510(12) 0.0475(13) 0.0006(9) -0.0022(9) -0.0059(11) C3A 0.0444(13) 0.0487(16) 0.0427(14) -0.0012(7) -0.0027(7) -0.0070(8) C4A 0.051(2) 0.049(2) 0.058(2) 0.0016(9) -0.0021(9) 0.0064(9) C5A 0.0443(11) 0.0526(13) 0.0548(15) 0.0018(12) 0.0013(11) -0.0062(9) C6A 0.0396(9) 0.0454(10) 0.0569(11) -0.0024(10) -0.0080(10) -0.0044(9) C7A 0.0519(11) 0.0469(10) 0.0465(11) 0.0009(8) -0.0024(8) 0.0101(9) C8A 0.0537(11) 0.0684(13) 0.0440(10) -0.0057(9) -0.0067(8) 0.0151(10) C9A 0.101(3) 0.124(4) 0.0452(19) -0.0133(16) -0.0093(17) -0.0098(19) C10A 0.101(3) 0.109(3) 0.088(3) 0.033(2) 0.0363(19) -0.0037(18) _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 N1A O2A 1.216(5) . ? N1A O1A 1.218(6) . ? N1A C8A 1.428(3) . ? N2A C4A 1.370(5) . ? N2A C9A 1.454(5) . ? N2A C10A 1.460(5) . ? C1A C2A 1.392(4) . ? C1A C6A 1.403(3) . ? C1A C7A 1.433(3) . ? C2A C3A 1.367(3) . ? C3A C4A 1.403(4) . ? C4A C5A 1.419(3) . ? C5A C6A 1.364(4) . ? C7A C8A 1.328(3) . ? N1B O1B 1.225(9) . ? N1B O2B 1.231(9) . ? N1B C8B 1.461(8) . ? N2B C4B 1.349(9) . ? N2B C10B 1.431(9) . ? N2B C9B 1.445(9) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.439(6) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.311(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 O2A N1A O1A 120.1(5) . . ? O2A N1A C8A 117.8(4) . . ? O1A N1A C8A 122.2(5) . . ? C4A N2A C9A 119.4(5) . . ? C4A N2A C10A 120.6(6) . . ? C9A N2A C10A 118.9(5) . . ? C2A C1A C6A 115.73(17) . . ? C2A C1A C7A 121.1(2) . . ? C6A C1A C7A 123.2(2) . . ? C3A C2A C1A 122.8(3) . . ? C2A C3A C4A 121.9(3) . . ? N2A C4A C3A 119.8(4) . . ? N2A C4A C5A 124.7(4) . . ? C3A C4A C5A 115.5(3) . . ? C6A C5A C4A 121.8(2) . . ? C5A C6A C1A 122.30(18) . . ? C8A C7A C1A 128.2(2) . . ? C7A C8A N1A 122.0(3) . . ? O1B N1B O2B 131.0(16) . . ? O1B N1B C8B 103.2(15) . . ? O2B N1B C8B 124.3(12) . . ? C4B N2B C10B 120.9(11) . . ? C4B N2B C9B 123.9(11) . . ? C10B N2B C9B 115.2(9) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 122.3(5) . . ? C6B C1B C7B 117.7(5) . . ? C1B C2B C3B 120.0 . . ? C4B C3B C2B 120.0 . . ? N2B C4B C3B 126.8(7) . . ? N2B C4B C5B 113.2(7) . . ? C3B C4B C5B 120.0 . . ? C6B C5B C4B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 127.5(7) . . ? C7B C8B N1B 120.2(8) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -1.2(3) . . . . ? C7A C1A C2A C3A 179.3(2) . . . . ? C1A C2A C3A C4A -0.6(3) . . . . ? C9A N2A C4A C3A -8.1(11) . . . . ? C10A N2A C4A C3A -175.8(6) . . . . ? C9A N2A C4A C5A 172.0(6) . . . . ? C10A N2A C4A C5A 4.4(11) . . . . ? C2A C3A C4A N2A -177.9(6) . . . . ? C2A C3A C4A C5A 2.0(4) . . . . ? N2A C4A C5A C6A 178.2(6) . . . . ? C3A C4A C5A C6A -1.6(4) . . . . ? C4A C5A C6A C1A -0.1(3) . . . . ? C2A C1A C6A C5A 1.6(3) . . . . ? C7A C1A C6A C5A -178.9(2) . . . . ? C2A C1A C7A C8A -179.7(2) . . . . ? C6A C1A C7A C8A 0.8(3) . . . . ? C1A C7A C8A N1A -179.9(2) . . . . ? O2A N1A C8A C7A 179.2(3) . . . . ? O1A N1A C8A C7A -2.1(7) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 179.1(6) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C10B N2B C4B C3B -179.5(10) . . . . ? C9B N2B C4B C3B -2(2) . . . . ? C10B N2B C4B C5B 1(2) . . . . ? C9B N2B C4B C5B 178.0(13) . . . . ? C2B C3B C4B N2B -179.8(14) . . . . ? C2B C3B C4B C5B 0.0 . . . . ? N2B C4B C5B C6B 179.8(12) . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -179.1(6) . . . . ? C2B C1B C7B C8B -0.2(9) . . . . ? C6B C1B C7B C8B 178.9(6) . . . . ? C1B C7B C8B N1B -178.9(9) . . . . ? O1B N1B C8B C7B -172.8(14) . . . . ? O2B N1B C8B C7B -5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.166 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.031 #===END data_nme2250k _database_code_depnum_ccdc_archive 'CCDC 701898' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Dimethylamino-\b-nitrostyrene ; _chemical_name_common 4-Dimethylamino-beta-nitrostyrene _chemical_melting_point 180_C _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 orthorhombic _symmetry_space_group_name_H-M P_b_c_a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.2801(8) _cell_length_b 7.4110(5) _cell_length_c 25.2458(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1923.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 250 _cell_measurement_reflns_used 4376 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.0 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9633 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 10s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 250 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 28081 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2816 _reflns_number_gt 2159 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. The following target values were taken from the corresponding bond lengths of 4-dimethylamino-\b-ethyl-\b-nitrostyrene at 100 K reported in reference 13 and used for SHELXL DFIX instructions. The length of the N---Ph bond (N(2)---C(4)) of the two conformers was restrained to be 1.37 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---Me bonds (N(2)---C(9) and N(2)---C(10)) of the two conformers were restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C\\dbC bond (C(7)\\dbC(8)) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction. DFIX was not applied to the length because the observed length of the C\\dbC bond would change with temperature and there is no proper target length required for DFIX. ; _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^)+(0.0769P)^2^+0.6363P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0063(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2816 _refine_ls_number_parameters 163 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1697 _refine_ls_wR_factor_gt 0.1497 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.033 _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 N1A N 0.3734(3) 0.1184(3) 0.36429(8) 0.0543(6) Uani 0.80 1 d PD A 1 N2A N 0.3968(5) 0.2256(5) 0.67819(10) 0.0425(6) Uani 0.80 1 d PD A 1 O1A O 0.4592(3) 0.2128(7) 0.34582(18) 0.0814(9) Uani 0.80 1 d PD A 1 O2A O 0.3018(2) 0.0301(4) 0.33470(7) 0.0875(8) Uani 0.80 1 d PD A 1 C1A C 0.41603(15) 0.1986(2) 0.51124(6) 0.0342(3) Uani 0.80 1 d PD A 1 C2A C 0.50333(17) 0.3017(3) 0.54120(7) 0.0374(4) Uani 0.80 1 d P A 1 H2A H 0.5683 0.3675 0.5235 0.045 Uiso 0.80 1 calc PR A 1 C3A C 0.4976(2) 0.3106(4) 0.59571(9) 0.0367(3) Uani 0.80 1 d P A 1 H3A H 0.5586 0.3812 0.6141 0.044 Uiso 0.80 1 calc PR A 1 C4A C 0.4014(3) 0.2151(4) 0.62437(7) 0.0324(3) Uani 0.80 1 d PD A 1 C5A C 0.3150(2) 0.1074(3) 0.59402(7) 0.0386(4) Uani 0.80 1 d P A 1 H5A H 0.2506 0.0395 0.6114 0.046 Uiso 0.80 1 calc PR A 1 C6A C 0.32332(16) 0.1000(2) 0.53972(7) 0.0378(4) Uani 0.80 1 d P A 1 H6A H 0.2647 0.0263 0.5211 0.045 Uiso 0.80 1 calc PR A 1 C7A C 0.42719(16) 0.1976(2) 0.45437(6) 0.0386(4) Uani 0.80 1 d PD A 1 H7A H 0.4945 0.2676 0.4398 0.046 Uiso 0.80 1 calc PR A 1 C8A C 0.35231(17) 0.1081(3) 0.42007(6) 0.0445(4) Uani 0.80 1 d PD A 1 H8A H 0.2839 0.0363 0.4330 0.053 Uiso 0.80 1 calc PR A 1 C9A C 0.4957(8) 0.3269(12) 0.7068(2) 0.0584(7) Uani 0.80 1 d PD A 1 H91A H 0.4783 0.3207 0.7445 0.088 Uiso 0.80 1 calc PR A 1 H92A H 0.4940 0.4519 0.6954 0.088 Uiso 0.80 1 calc PR A 1 H93A H 0.5806 0.2757 0.6995 0.088 Uiso 0.80 1 calc PR A 1 C10A C 0.3006(9) 0.1238(13) 0.7082(3) 0.0641(10) Uani 0.80 1 d PD A 1 H101 H 0.3026 0.1617 0.7450 0.096 Uiso 0.80 1 calc PR A 1 H102 H 0.3205 -0.0040 0.7060 0.096 Uiso 0.80 1 calc PR A 1 H103 H 0.2148 0.1457 0.6936 0.096 Uiso 0.80 1 calc PR A 1 N1B N 0.3995(13) 0.156(2) 0.3684(4) 0.0603(10) Uiso 0.20 1 d PD B 2 N2B N 0.392(3) 0.248(3) 0.6784(5) 0.0603(10) Uiso 0.20 1 d PD B 2 O1B O 0.4890(14) 0.230(2) 0.3444(8) 0.0603(10) Uiso 0.20 1 d PD B 2 O2B O 0.3130(9) 0.0524(12) 0.3524(4) 0.0603(10) Uiso 0.20 1 d PD B 2 C1B C 0.3781(8) 0.1604(12) 0.5173(3) 0.0603(10) Uiso 0.20 1 d PGD B 2 C2B C 0.4748(9) 0.2740(14) 0.5365(4) 0.0603(10) Uiso 0.20 1 d PG B 2 H2B H 0.5317 0.3319 0.5128 0.072 Uiso 0.20 1 calc PR B 2 C3B C 0.4875(12) 0.3019(19) 0.5907(4) 0.0603(10) Uiso 0.20 1 d PG B 2 H3B H 0.5529 0.3787 0.6036 0.072 Uiso 0.20 1 calc PR B 2 C4B C 0.4034(14) 0.216(2) 0.6257(3) 0.0603(10) Uiso 0.20 1 d PGD B 2 C5B C 0.3066(11) 0.1028(18) 0.6065(3) 0.0603(10) Uiso 0.20 1 d PG B 2 H5B H 0.2497 0.0449 0.6302 0.072 Uiso 0.20 1 calc PR B 2 C6B C 0.2940(8) 0.0748(12) 0.5523(4) 0.0603(10) Uiso 0.20 1 d PG B 2 H6B H 0.2285 -0.0020 0.5394 0.072 Uiso 0.20 1 calc PR B 2 C7B C 0.3609(9) 0.1326(12) 0.4617(3) 0.0603(10) Uiso 0.20 1 d PD B 2 H7B H 0.2924 0.0557 0.4518 0.072 Uiso 0.20 1 calc PR B 2 C8B C 0.4290(9) 0.2012(12) 0.4230(3) 0.0603(10) Uiso 0.20 1 d PD B 2 H8B H 0.4978 0.2805 0.4307 0.072 Uiso 0.20 1 calc PR B 2 C9B C 0.494(3) 0.328(5) 0.7104(11) 0.0603(10) Uiso 0.20 1 d PD B 2 H91B H 0.5571 0.2365 0.7196 0.090 Uiso 0.20 1 calc PR B 2 H92B H 0.4560 0.3777 0.7425 0.090 Uiso 0.20 1 calc PR B 2 H93B H 0.5358 0.4236 0.6905 0.090 Uiso 0.20 1 calc PR B 2 C10B C 0.312(4) 0.126(5) 0.7084(13) 0.0603(10) Uiso 0.20 1 d PD B 2 H104 H 0.2206 0.1544 0.7025 0.090 Uiso 0.20 1 calc PR B 2 H105 H 0.3316 0.1370 0.7458 0.090 Uiso 0.20 1 calc PR B 2 H106 H 0.3283 0.0027 0.6970 0.090 Uiso 0.20 1 calc PR B 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 N1A 0.0624(15) 0.0634(16) 0.0372(8) -0.0083(8) -0.0103(8) 0.0213(12) N2A 0.0449(9) 0.0477(15) 0.0347(7) 0.0018(6) 0.0056(5) -0.0029(10) O1A 0.093(3) 0.0968(19) 0.0548(10) 0.0045(12) 0.0009(19) -0.0042(19) O2A 0.0884(14) 0.1221(18) 0.0519(10) -0.0359(11) -0.0279(9) 0.0184(12) C1A 0.0356(7) 0.0324(7) 0.0346(7) -0.0011(6) -0.0051(6) 0.0061(6) C2A 0.0391(9) 0.0385(8) 0.0347(8) 0.0004(6) -0.0014(6) -0.0036(6) C3A 0.0374(8) 0.0395(8) 0.0331(8) -0.0008(6) -0.0019(6) -0.0056(6) C4A 0.0318(7) 0.0301(6) 0.0353(7) 0.0010(5) -0.0010(5) 0.0036(5) C5A 0.0344(7) 0.0384(8) 0.0432(10) 0.0001(8) -0.0017(7) -0.0042(6) C6A 0.0338(7) 0.0360(8) 0.0436(9) -0.0021(7) -0.0075(7) -0.0011(6) C7A 0.0427(8) 0.0386(8) 0.0346(8) 0.0004(6) -0.0028(6) 0.0085(6) C8A 0.0435(8) 0.0552(10) 0.0346(8) -0.0056(7) -0.0056(6) 0.0115(7) C9A 0.0654(12) 0.0766(14) 0.0333(12) -0.0064(11) -0.0060(10) -0.0064(11) C10A 0.065(3) 0.0698(14) 0.0578(12) 0.0200(11) 0.0206(14) -0.0029(15) _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 N1A O1A 1.219(3) . ? N1A O2A 1.236(3) . ? N1A C8A 1.427(3) . ? N2A C4A 1.362(3) . ? N2A C9A 1.455(4) . ? N2A C10A 1.456(3) . ? C1A C6A 1.399(2) . ? C1A C2A 1.401(2) . ? C1A C7A 1.440(2) . ? C2A C3A 1.379(2) . ? C3A C4A 1.415(2) . ? C4A C5A 1.419(2) . ? C5A C6A 1.375(2) . ? C7A C8A 1.335(2) . ? N1B O1B 1.228(9) . ? N1B O2B 1.243(8) . ? N1B C8B 1.451(9) . ? N2B C4B 1.356(10) . ? N2B C10B 1.443(10) . ? N2B C9B 1.447(10) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.431(8) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.303(8) . ? 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 O2A 120.2(3) . . ? O1A N1A C8A 121.2(3) . . ? O2A N1A C8A 118.5(3) . . ? C4A N2A C9A 120.0(4) . . ? C4A N2A C10A 120.9(5) . . ? C9A N2A C10A 118.9(5) . . ? C6A C1A C2A 116.34(14) . . ? C6A C1A C7A 124.31(15) . . ? C2A C1A C7A 119.35(15) . . ? C3A C2A C1A 122.51(14) . . ? C2A C3A C4A 121.09(14) . . ? N2A C4A C3A 120.4(3) . . ? N2A C4A C5A 123.3(3) . . ? C3A C4A C5A 116.27(14) . . ? C6A C5A C4A 121.46(15) . . ? C5A C6A C1A 122.29(14) . . ? C8A C7A C1A 127.10(18) . . ? C7A C8A N1A 121.73(19) . . ? O1B N1B O2B 130.5(13) . . ? O1B N1B C8B 102.2(13) . . ? O2B N1B C8B 126.8(12) . . ? C4B N2B C10B 117(2) . . ? C4B N2B C9B 124(2) . . ? C10B N2B C9B 112(2) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 121.1(7) . . ? C6B C1B C7B 118.8(7) . . ? C3B C2B C1B 120.0 . . ? C4B C3B C2B 120.0 . . ? N2B C4B C3B 126.8(14) . . ? N2B C4B C5B 112.6(14) . . ? C3B C4B C5B 120.0 . . ? C6B C5B C4B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 127.8(9) . . ? C7B C8B N1B 120.7(9) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -1.5(2) . . . . ? C7A C1A C2A C3A 179.32(18) . . . . ? C1A C2A C3A C4A -0.3(2) . . . . ? C9A N2A C4A C3A -3.6(6) . . . . ? C10A N2A C4A C3A -178.2(6) . . . . ? C9A N2A C4A C5A 174.8(5) . . . . ? C10A N2A C4A C5A 0.2(7) . . . . ? C2A C3A C4A N2A -179.8(3) . . . . ? C2A C3A C4A C5A 1.7(2) . . . . ? N2A C4A C5A C6A -179.7(3) . . . . ? C3A C4A C5A C6A -1.3(2) . . . . ? C4A C5A C6A C1A -0.5(2) . . . . ? C2A C1A C6A C5A 1.9(2) . . . . ? C7A C1A C6A C5A -178.94(17) . . . . ? C6A C1A C7A C8A 1.2(3) . . . . ? C2A C1A C7A C8A -179.69(16) . . . . ? C1A C7A C8A N1A 179.91(18) . . . . ? O1A N1A C8A C7A -1.6(4) . . . . ? O2A N1A C8A C7A 178.9(2) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 178.5(10) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C10B N2B C4B C3B -171(2) . . . . ? C9B N2B C4B C3B -23(3) . . . . ? C10B N2B C4B C5B 18(3) . . . . ? C9B N2B C4B C5B 166(2) . . . . ? C2B C3B C4B N2B -170(2) . . . . ? C2B C3B C4B C5B 0.0 . . . . ? N2B C4B C5B C6B 171.7(17) . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -178.5(9) . . . . ? C2B C1B C7B C8B 1.2(14) . . . . ? C6B C1B C7B C8B 179.7(9) . . . . ? C1B C7B C8B N1B 179.0(11) . . . . ? O1B N1B C8B C7B -173.8(13) . . . . ? O2B N1B C8B C7B -1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.264 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.043 #===END data_nme2200k _database_code_depnum_ccdc_archive 'CCDC 701899' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Dimethylamino-\b-nitrostyrene ; _chemical_name_common 4-Dimethylamino-beta-nitrostyrene _chemical_melting_point 180_C _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 orthorhombic _symmetry_space_group_name_H-M P_b_c_a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.2466(6) _cell_length_b 7.3631(4) _cell_length_c 25.1655(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1898.65(19) _cell_formula_units_Z 8 _cell_measurement_temperature 200 _cell_measurement_reflns_used 5133 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.0 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9628 _exptl_absorpt_correction_T_max 0.9811 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 10s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 200 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 26498 _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_sigmaI/netI 0.0114 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 30.02 _reflns_number_total 2776 _reflns_number_gt 2341 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. The following target values were taken from the corresponding bond lengths of 4-dimethylamino-\b-ethyl-\b-nitrostyrene at 100 K reported in reference 13 and used for SHELXL DFIX instructions. The length of the N---Ph bond (N(2)---C(4)) of the two conformers was restrained to be 1.37 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---Me bonds (N(2)---C(9) and N(2)---C(10)) of the two conformers were restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C\\dbC bond (C(7)\\dbC(8)) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction. DFIX was not applied to the length because the observed length of the C\\dbC bond would change with temperature and there is no proper target length required for DFIX. ; _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^)+(0.0748P)^2^+0.4763P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0057(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2776 _refine_ls_number_parameters 163 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.1467 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.075 _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 N1A N 0.37426(18) 0.1153(2) 0.36448(6) 0.0429(4) Uani 0.86 1 d PD A 1 N2A N 0.3956(3) 0.2323(4) 0.67881(6) 0.0331(3) Uani 0.86 1 d PD A 1 O1A O 0.4636(3) 0.2109(5) 0.34707(8) 0.0618(5) Uani 0.86 1 d PD A 1 O2A O 0.30149(17) 0.0257(3) 0.33524(5) 0.0662(5) Uani 0.86 1 d PD A 1 C1A C 0.41616(12) 0.19894(16) 0.51170(4) 0.0268(3) Uani 0.86 1 d PD A 1 C2A C 0.50376(12) 0.30405(18) 0.54143(5) 0.0288(3) Uani 0.86 1 d P A 1 H2A H 0.5694 0.3706 0.5232 0.035 Uiso 0.86 1 calc PR A 1 C3A C 0.49847(15) 0.3146(2) 0.59623(5) 0.0280(3) Uani 0.86 1 d P A 1 H3A H 0.5601 0.3873 0.6148 0.034 Uiso 0.86 1 calc PR A 1 C4A C 0.40210(15) 0.2184(2) 0.62500(5) 0.0250(2) Uani 0.86 1 d PD A 1 C5A C 0.31515(14) 0.1087(2) 0.59515(5) 0.0297(3) Uani 0.86 1 d P A 1 H5A H 0.2502 0.0402 0.6131 0.036 Uiso 0.86 1 calc PR A 1 C6A C 0.32300(12) 0.09977(17) 0.54058(5) 0.0293(3) Uani 0.86 1 d P A 1 H6A H 0.2635 0.0241 0.5219 0.035 Uiso 0.86 1 calc PR A 1 C7A C 0.42742(12) 0.19628(16) 0.45469(5) 0.0297(3) Uani 0.86 1 d PD A 1 H7A H 0.4956 0.2671 0.4397 0.036 Uiso 0.86 1 calc PR A 1 C8A C 0.35172(13) 0.10427(19) 0.42050(5) 0.0343(3) Uani 0.86 1 d PD A 1 H8A H 0.2825 0.0311 0.4336 0.041 Uiso 0.86 1 calc PR A 1 C9A C 0.4934(3) 0.3344(5) 0.70831(11) 0.0412(5) Uani 0.86 1 d PD A 1 H91A H 0.4710 0.3342 0.7462 0.062 Uiso 0.86 1 calc PR A 1 H92A H 0.4958 0.4598 0.6953 0.062 Uiso 0.86 1 calc PR A 1 H93A H 0.5792 0.2781 0.7033 0.062 Uiso 0.86 1 calc PR A 1 C10A C 0.3017(5) 0.1257(7) 0.70860(17) 0.0453(4) Uani 0.86 1 d PD A 1 H101 H 0.3051 0.1604 0.7462 0.068 Uiso 0.86 1 calc PR A 1 H102 H 0.3226 -0.0036 0.7051 0.068 Uiso 0.86 1 calc PR A 1 H103 H 0.2138 0.1483 0.6947 0.068 Uiso 0.86 1 calc PR A 1 N1B N 0.3959(19) 0.150(3) 0.3690(6) 0.0726(19) Uiso 0.14 1 d PD B 2 N2B N 0.393(3) 0.245(4) 0.6796(6) 0.0726(19) Uiso 0.14 1 d PD B 2 O1B O 0.477(2) 0.223(4) 0.3392(8) 0.0726(19) Uiso 0.14 1 d PD B 2 O2B O 0.3133(16) 0.048(2) 0.3500(6) 0.0726(19) Uiso 0.14 1 d PD B 2 C1B C 0.3799(14) 0.161(2) 0.5178(4) 0.0726(19) Uiso 0.14 1 d PGD B 2 C2B C 0.4772(13) 0.278(2) 0.5356(5) 0.0726(19) Uiso 0.14 1 d PG B 2 H2B H 0.5339 0.3346 0.5108 0.087 Uiso 0.14 1 calc PR B 2 C3B C 0.4915(16) 0.311(2) 0.5896(6) 0.0726(19) Uiso 0.14 1 d PG B 2 H3B H 0.5579 0.3908 0.6018 0.087 Uiso 0.14 1 calc PR B 2 C4B C 0.4085(19) 0.228(3) 0.6259(4) 0.0726(19) Uiso 0.14 1 d PGD B 2 C5B C 0.3112(16) 0.111(2) 0.6081(5) 0.0726(19) Uiso 0.14 1 d PG B 2 H5B H 0.2545 0.0540 0.6329 0.087 Uiso 0.14 1 calc PR B 2 C6B C 0.2970(12) 0.0776(19) 0.5540(6) 0.0726(19) Uiso 0.14 1 d PG B 2 H6B H 0.2305 -0.0022 0.5419 0.087 Uiso 0.14 1 calc PR B 2 C7B C 0.3629(15) 0.132(2) 0.4621(4) 0.0726(19) Uiso 0.14 1 d PD B 2 H7B H 0.2938 0.0525 0.4524 0.087 Uiso 0.14 1 calc PR B 2 C8B C 0.4296(14) 0.200(2) 0.4227(5) 0.0726(19) Uiso 0.14 1 d PD B 2 H8B H 0.4997 0.2812 0.4294 0.087 Uiso 0.14 1 calc PR B 2 C9B C 0.505(3) 0.315(6) 0.7086(14) 0.0726(19) Uiso 0.14 1 d PD B 2 H91B H 0.5476 0.4107 0.6876 0.109 Uiso 0.14 1 calc PR B 2 H92B H 0.5673 0.2168 0.7151 0.109 Uiso 0.14 1 calc PR B 2 H93B H 0.4760 0.3662 0.7425 0.109 Uiso 0.14 1 calc PR B 2 C10B C 0.305(4) 0.134(6) 0.7102(17) 0.0726(19) Uiso 0.14 1 d PD B 2 H104 H 0.2164 0.1828 0.7075 0.109 Uiso 0.14 1 calc PR B 2 H105 H 0.3324 0.1331 0.7475 0.109 Uiso 0.14 1 calc PR B 2 H106 H 0.3064 0.0093 0.6963 0.109 Uiso 0.14 1 calc PR B 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 N1A 0.0507(9) 0.0509(10) 0.0271(6) -0.0063(5) -0.0079(5) 0.0193(7) N2A 0.0345(5) 0.0388(7) 0.0261(5) 0.0004(4) 0.0047(4) -0.0044(5) O1A 0.0819(13) 0.0696(10) 0.0338(8) 0.0051(7) 0.0040(7) 0.0014(9) O2A 0.0651(8) 0.0928(11) 0.0405(7) -0.0270(7) -0.0204(6) 0.0155(7) C1A 0.0282(5) 0.0260(5) 0.0264(5) -0.0008(4) -0.0038(4) 0.0044(4) C2A 0.0306(6) 0.0300(6) 0.0259(5) 0.0008(4) -0.0003(4) -0.0029(4) C3A 0.0291(5) 0.0302(5) 0.0248(5) -0.0006(4) -0.0004(4) -0.0048(4) C4A 0.0245(5) 0.0236(5) 0.0269(5) 0.0006(4) 0.0002(4) 0.0023(4) C5A 0.0268(5) 0.0296(5) 0.0328(6) 0.0000(5) -0.0012(5) -0.0041(4) C6A 0.0274(5) 0.0284(5) 0.0322(6) -0.0014(4) -0.0054(5) -0.0009(4) C7A 0.0331(6) 0.0295(6) 0.0266(5) 0.0007(4) -0.0024(4) 0.0061(4) C8A 0.0345(6) 0.0426(7) 0.0257(5) -0.0047(5) -0.0044(4) 0.0088(5) C9A 0.0444(9) 0.0532(12) 0.0261(6) -0.0048(6) -0.0027(5) -0.0031(8) C10A 0.0473(8) 0.0494(9) 0.0394(8) 0.0116(7) 0.0133(6) -0.0039(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 N1A O1A 1.235(3) . ? N1A O2A 1.2380(19) . ? N1A C8A 1.4309(18) . ? N2A C4A 1.3598(16) . ? N2A C10A 1.4510(19) . ? N2A C9A 1.456(2) . ? C1A C2A 1.4016(16) . ? C1A C6A 1.4045(16) . ? C1A C7A 1.4395(16) . ? C2A C3A 1.3824(16) . ? C3A C4A 1.4148(15) . ? C4A C5A 1.4176(15) . ? C5A C6A 1.3771(17) . ? C7A C8A 1.3420(17) . ? N1B O2B 1.232(9) . ? N1B O1B 1.238(10) . ? N1B C8B 1.443(10) . ? N2B C4B 1.366(10) . ? N2B C10B 1.446(10) . ? N2B C9B 1.453(10) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.429(9) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.302(9) . ? 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 O2A 122.64(19) . . ? O1A N1A C8A 120.09(18) . . ? O2A N1A C8A 117.27(17) . . ? C4A N2A C10A 120.4(3) . . ? C4A N2A C9A 120.9(2) . . ? C10A N2A C9A 118.2(3) . . ? C2A C1A C6A 116.50(10) . . ? C2A C1A C7A 119.22(11) . . ? C6A C1A C7A 124.28(11) . . ? C3A C2A C1A 122.58(11) . . ? C2A C3A C4A 120.63(10) . . ? N2A C4A C3A 120.39(15) . . ? N2A C4A C5A 122.68(15) . . ? C3A C4A C5A 116.93(10) . . ? C6A C5A C4A 121.26(11) . . ? C5A C6A C1A 122.06(10) . . ? C8A C7A C1A 126.84(13) . . ? C7A C8A N1A 120.65(13) . . ? O2B N1B O1B 119(2) . . ? O2B N1B C8B 133.2(18) . . ? O1B N1B C8B 107.4(16) . . ? C4B N2B C10B 123(3) . . ? C4B N2B C9B 116(2) . . ? C10B N2B C9B 115(3) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 119.7(11) . . ? C6B C1B C7B 120.2(11) . . ? C3B C2B C1B 120.0 . . ? C2B C3B C4B 120.0 . . ? N2B C4B C5B 107.2(17) . . ? N2B C4B C3B 132.6(17) . . ? C5B C4B C3B 120.0 . . ? C6B C5B C4B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 128.6(14) . . ? C7B C8B N1B 119.3(14) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -1.44(17) . . . . ? C7A C1A C2A C3A 179.46(12) . . . . ? C1A C2A C3A C4A -0.26(18) . . . . ? C10A N2A C4A C3A -176.5(3) . . . . ? C9A N2A C4A C3A -4.9(4) . . . . ? C10A N2A C4A C5A 3.3(4) . . . . ? C9A N2A C4A C5A 174.9(2) . . . . ? C2A C3A C4A N2A -178.6(2) . . . . ? C2A C3A C4A C5A 1.60(16) . . . . ? N2A C4A C5A C6A 179.0(2) . . . . ? C3A C4A C5A C6A -1.24(16) . . . . ? C4A C5A C6A C1A -0.49(18) . . . . ? C2A C1A C6A C5A 1.81(17) . . . . ? C7A C1A C6A C5A -179.15(12) . . . . ? C2A C1A C7A C8A -179.67(12) . . . . ? C6A C1A C7A C8A 1.31(19) . . . . ? C1A C7A C8A N1A 179.73(13) . . . . ? O1A N1A C8A C7A -0.4(3) . . . . ? O2A N1A C8A C7A 179.39(16) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 177.9(14) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C10B N2B C4B C5B 10(4) . . . . ? C9B N2B C4B C5B 162(3) . . . . ? C10B N2B C4B C3B -176(3) . . . . ? C9B N2B C4B C3B -23(4) . . . . ? C2B C3B C4B N2B -174(3) . . . . ? C2B C3B C4B C5B 0.0 . . . . ? N2B C4B C5B C6B 176(2) . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -177.9(14) . . . . ? C2B C1B C7B C8B 1(2) . . . . ? C6B C1B C7B C8B 179.1(14) . . . . ? C1B C7B C8B N1B 179.4(17) . . . . ? O2B N1B C8B C7B -2(4) . . . . ? O1B N1B C8B C7B -176(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.315 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.042 #===END data_nme2150k _database_code_depnum_ccdc_archive 'CCDC 701900' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Dimethylamino-\b-nitrostyrene ; _chemical_name_common 4-Dimethylamino-beta-nitrostyrene _chemical_melting_point 180_C _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 orthorhombic _symmetry_space_group_name_H-M P_b_c_a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.2078(6) _cell_length_b 7.3313(4) _cell_length_c 25.1387(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1881.29(18) _cell_formula_units_Z 8 _cell_measurement_temperature 150 _cell_measurement_reflns_used 5003 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.0 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9625 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 5s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 150 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 27378 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0119 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2760 _reflns_number_gt 2353 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. The following target values were taken from the corresponding bond lengths of 4-dimethylamino-\b-ethyl-\b-nitrostyrene at 100 K reported in reference 13 and used for SHELXL DFIX instructions. The length of the N---Ph bond (N(2)---C(4)) of the two conformers was restrained to be 1.37 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---Me bonds (N(2)---C(9) and N(2)---C(10)) of the two conformers were restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C\\dbC bond (C(7)\\dbC(8)) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction. DFIX was not applied to the length because the observed length of the C\\dbC bond would change with temperature and there is no proper target length required for DFIX. ; _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^)+(0.0706P)^2^+0.5275P] 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 2760 _refine_ls_number_parameters 162 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.057 _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 N1A N 0.37420(15) 0.1134(2) 0.36447(5) 0.0339(3) Uani 0.88 1 d PD A 1 N2A N 0.3961(3) 0.2347(4) 0.67915(6) 0.0265(3) Uani 0.88 1 d PD A 1 O1A O 0.4642(3) 0.2101(4) 0.34714(6) 0.0483(4) Uani 0.88 1 d PD A 1 O2A O 0.30121(14) 0.0229(2) 0.33525(5) 0.0514(4) Uani 0.88 1 d PD A 1 C1A C 0.41642(11) 0.19885(15) 0.51191(4) 0.0216(2) Uani 0.88 1 d PD A 1 C2A C 0.50462(11) 0.30496(17) 0.54152(4) 0.0230(2) Uani 0.88 1 d P A 1 H2A H 0.5704 0.3716 0.5232 0.028 Uiso 0.88 1 calc PR A 1 C3A C 0.49948(14) 0.3162(2) 0.59646(5) 0.0225(2) Uani 0.88 1 d P A 1 H3A H 0.5614 0.3892 0.6150 0.027 Uiso 0.88 1 calc PR A 1 C4A C 0.40255(15) 0.2196(2) 0.62528(5) 0.0204(2) Uani 0.88 1 d PD A 1 C5A C 0.31518(13) 0.10869(18) 0.59556(5) 0.0240(2) Uani 0.88 1 d P A 1 H5A H 0.2501 0.0399 0.6137 0.029 Uiso 0.88 1 calc PR A 1 C6A C 0.32301(11) 0.09896(16) 0.54092(5) 0.0236(2) Uani 0.88 1 d P A 1 H6A H 0.2635 0.0225 0.5223 0.028 Uiso 0.88 1 calc PR A 1 C7A C 0.42763(11) 0.19576(15) 0.45478(4) 0.0240(2) Uani 0.88 1 d PD A 1 H7A H 0.4959 0.2671 0.4397 0.029 Uiso 0.88 1 calc PR A 1 C8A C 0.35169(11) 0.10262(17) 0.42063(4) 0.0274(2) Uani 0.88 1 d PD A 1 H8A H 0.2824 0.0289 0.4338 0.033 Uiso 0.88 1 calc PR A 1 C9A C 0.4952(4) 0.3364(7) 0.70852(13) 0.0329(3) Uani 0.88 1 d PD A 1 H91A H 0.4706 0.3421 0.7462 0.049 Uiso 0.88 1 calc PR A 1 H92A H 0.5015 0.4603 0.6941 0.049 Uiso 0.88 1 calc PR A 1 H93A H 0.5801 0.2751 0.7050 0.049 Uiso 0.88 1 calc PR A 1 C10A C 0.3014(3) 0.1263(5) 0.70859(8) 0.0349(4) Uani 0.88 1 d PD A 1 H101 H 0.3056 0.1584 0.7464 0.052 Uiso 0.88 1 calc PR A 1 H102 H 0.3215 -0.0035 0.7042 0.052 Uiso 0.88 1 calc PR A 1 H103 H 0.2131 0.1511 0.6950 0.052 Uiso 0.88 1 calc PR A 1 N1B N 0.3964(19) 0.147(3) 0.3696(6) 0.0579(16) Uiso 0.12 1 d PD B 2 N2B N 0.390(3) 0.239(5) 0.6797(6) 0.0579(16) Uiso 0.12 1 d PD B 2 O1B O 0.474(2) 0.216(4) 0.3380(7) 0.0579(16) Uiso 0.12 1 d PD B 2 O2B O 0.3122(15) 0.045(2) 0.3510(6) 0.0579(16) Uiso 0.12 1 d PD B 2 C1B C 0.3780(13) 0.1591(19) 0.5181(4) 0.0579(16) Uiso 0.12 1 d PGD B 2 C2B C 0.4763(13) 0.276(2) 0.5353(5) 0.0579(16) Uiso 0.12 1 d PG B 2 H2B H 0.5327 0.3328 0.5101 0.069 Uiso 0.12 1 calc PR B 2 C3B C 0.4921(16) 0.311(3) 0.5893(6) 0.0579(16) Uiso 0.12 1 d PG B 2 H3B H 0.5593 0.3909 0.6010 0.069 Uiso 0.12 1 calc PR B 2 C4B C 0.4096(19) 0.228(3) 0.6261(4) 0.0579(16) Uiso 0.12 1 d PGD B 2 C5B C 0.3113(16) 0.111(2) 0.6088(5) 0.0579(16) Uiso 0.12 1 d PG B 2 H5B H 0.2549 0.0544 0.6340 0.069 Uiso 0.12 1 calc PR B 2 C6B C 0.2955(12) 0.0764(18) 0.5549(5) 0.0579(16) Uiso 0.12 1 d PG B 2 H6B H 0.2283 -0.0037 0.5431 0.069 Uiso 0.12 1 calc PR B 2 C7B C 0.3621(14) 0.129(2) 0.4622(4) 0.0579(16) Uiso 0.12 1 d PD B 2 H7B H 0.2942 0.0474 0.4522 0.069 Uiso 0.12 1 calc PR B 2 C8B C 0.4294(14) 0.2009(19) 0.4231(5) 0.0579(16) Uiso 0.12 1 d PD B 2 H8B H 0.4979 0.2857 0.4298 0.069 Uiso 0.12 1 calc PR B 2 C9B C 0.495(4) 0.329(7) 0.7087(16) 0.0579(16) Uiso 0.12 1 d PD B 2 H91B H 0.5787 0.3018 0.6916 0.087 Uiso 0.12 1 calc PR B 2 H92B H 0.4959 0.2842 0.7454 0.087 Uiso 0.12 1 calc PR B 2 H93B H 0.4798 0.4609 0.7086 0.087 Uiso 0.12 1 calc PR B 2 C10B C 0.307(4) 0.138(6) 0.7160(12) 0.0579(16) Uiso 0.12 1 d PD B 2 H104 H 0.2152 0.1670 0.7089 0.087 Uiso 0.12 1 calc PR B 2 H105 H 0.3289 0.1719 0.7527 0.087 Uiso 0.12 1 calc PR B 2 H106 H 0.3218 0.0071 0.7110 0.087 Uiso 0.12 1 calc PR B 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 N1A 0.0400(8) 0.0403(9) 0.0216(5) -0.0050(4) -0.0065(4) 0.0155(6) N2A 0.0273(5) 0.0314(5) 0.0210(4) 0.0003(4) 0.0038(3) -0.0037(4) O1A 0.0646(9) 0.0538(7) 0.0267(7) 0.0031(6) 0.0024(6) 0.0023(6) O2A 0.0507(7) 0.0716(9) 0.0319(6) -0.0211(6) -0.0160(5) 0.0118(6) C1A 0.0228(5) 0.0208(5) 0.0210(5) -0.0007(4) -0.0030(4) 0.0036(4) C2A 0.0244(5) 0.0241(5) 0.0206(5) 0.0007(4) -0.0006(4) -0.0021(4) C3A 0.0231(5) 0.0245(5) 0.0199(5) -0.0007(4) -0.0005(4) -0.0030(4) C4A 0.0200(5) 0.0192(5) 0.0220(5) 0.0004(3) -0.0002(3) 0.0019(4) C5A 0.0219(5) 0.0241(5) 0.0261(6) -0.0004(5) -0.0013(4) -0.0025(4) C6A 0.0221(5) 0.0233(5) 0.0254(5) -0.0011(4) -0.0041(4) -0.0004(4) C7A 0.0270(5) 0.0235(5) 0.0216(5) 0.0006(4) -0.0019(4) 0.0050(4) C8A 0.0278(5) 0.0340(6) 0.0204(5) -0.0036(4) -0.0033(4) 0.0069(4) C9A 0.0356(6) 0.0424(9) 0.0208(5) -0.0038(5) -0.0022(4) -0.0037(5) C10A 0.0367(7) 0.0386(9) 0.0294(9) 0.0080(8) 0.0096(7) -0.0029(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 N1A O2A 1.2389(17) . ? N1A O1A 1.239(2) . ? N1A C8A 1.4325(17) . ? N2A C4A 1.3603(15) . ? N2A C10A 1.4541(17) . ? N2A C9A 1.4574(18) . ? C1A C2A 1.4035(14) . ? C1A C6A 1.4063(15) . ? C1A C7A 1.4409(15) . ? C2A C3A 1.3846(15) . ? C3A C4A 1.4162(14) . ? C4A C5A 1.4193(14) . ? C5A C6A 1.3775(16) . ? C7A C8A 1.3432(15) . ? N1B O2B 1.231(9) . ? N1B O1B 1.234(10) . ? N1B C8B 1.443(9) . ? N2B C4B 1.365(10) . ? N2B C10B 1.448(10) . ? N2B C9B 1.451(10) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.431(9) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.309(9) . ? 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 O2A N1A O1A 122.95(16) . . ? O2A N1A C8A 117.27(15) . . ? O1A N1A C8A 119.79(15) . . ? C4A N2A C10A 119.6(2) . . ? C4A N2A C9A 120.8(2) . . ? C10A N2A C9A 118.9(2) . . ? C2A C1A C6A 116.65(9) . . ? C2A C1A C7A 119.11(10) . . ? C6A C1A C7A 124.24(10) . . ? C3A C2A C1A 122.52(10) . . ? C2A C3A C4A 120.47(10) . . ? N2A C4A C3A 120.15(15) . . ? N2A C4A C5A 122.71(15) . . ? C3A C4A C5A 117.14(10) . . ? C6A C5A C4A 121.20(10) . . ? C5A C6A C1A 121.97(10) . . ? C8A C7A C1A 126.82(11) . . ? C7A C8A N1A 120.61(12) . . ? O2B N1B O1B 117.2(19) . . ? O2B N1B C8B 133.1(17) . . ? O1B N1B C8B 109.6(16) . . ? C4B N2B C10B 133(3) . . ? C4B N2B C9B 115(3) . . ? C10B N2B C9B 110(3) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 118.8(11) . . ? C6B C1B C7B 121.2(11) . . ? C1B C2B C3B 120.0 . . ? C4B C3B C2B 120.0 . . ? N2B C4B C3B 136.0(18) . . ? N2B C4B C5B 103.8(18) . . ? C3B C4B C5B 120.0 . . ? C4B C5B C6B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 128.0(13) . . ? C7B C8B N1B 117.8(13) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -1.58(16) . . . . ? C7A C1A C2A C3A 179.44(11) . . . . ? C1A C2A C3A C4A -0.31(17) . . . . ? C10A N2A C4A C3A -176.3(2) . . . . ? C9A N2A C4A C3A -5.6(4) . . . . ? C10A N2A C4A C5A 3.5(4) . . . . ? C9A N2A C4A C5A 174.2(3) . . . . ? C2A C3A C4A N2A -178.4(2) . . . . ? C2A C3A C4A C5A 1.76(15) . . . . ? N2A C4A C5A C6A 178.9(2) . . . . ? C3A C4A C5A C6A -1.33(15) . . . . ? C4A C5A C6A C1A -0.60(16) . . . . ? C2A C1A C6A C5A 2.03(15) . . . . ? C7A C1A C6A C5A -179.05(11) . . . . ? C2A C1A C7A C8A -179.83(11) . . . . ? C6A C1A C7A C8A 1.28(18) . . . . ? C1A C7A C8A N1A 179.69(12) . . . . ? O2A N1A C8A C7A 179.43(14) . . . . ? O1A N1A C8A C7A -0.3(3) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 178.6(14) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C10B N2B C4B C3B -175(3) . . . . ? C9B N2B C4B C3B -16(5) . . . . ? C10B N2B C4B C5B 10(5) . . . . ? C9B N2B C4B C5B 170(3) . . . . ? C2B C3B C4B N2B -174(3) . . . . ? C2B C3B C4B C5B 0.0 . . . . ? N2B C4B C5B C6B 176(2) . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -178.6(14) . . . . ? C2B C1B C7B C8B 0(2) . . . . ? C6B C1B C7B C8B 178.1(13) . . . . ? C1B C7B C8B N1B 178.8(16) . . . . ? O2B N1B C8B C7B 2(4) . . . . ? O1B N1B C8B C7B -175(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.336 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.044 #===END data_nme290k _database_code_depnum_ccdc_archive 'CCDC 701901' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Dimethylamino-\b-nitrostyrene ; _chemical_name_common 4-Dimethylamino-beta-nitrostyrene _chemical_melting_point 180_C _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 N2 O2' _chemical_formula_weight 192.22 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 orthorhombic _symmetry_space_group_name_H-M P_b_c_a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.1607(5) _cell_length_b 7.2960(4) _cell_length_c 25.1132(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1861.70(17) _cell_formula_units_Z 8 _cell_measurement_temperature 90 _cell_measurement_reflns_used 5826 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 30.0 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9621 _exptl_absorpt_correction_T_max 0.9808 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 5s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 90 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 27117 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0108 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 30.01 _reflns_number_total 2721 _reflns_number_gt 2426 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. The following target values were taken from the corresponding bond lengths of 4-dimethylamino-\b-ethyl-\b-nitrostyrene at 100 K reported in reference 13 and used for SHELXL DFIX instructions. The length of the N---Ph bond (N(2)---C(4)) of the two conformers was restrained to be 1.37 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---Me bonds (N(2)---C(9) and N(2)---C(10)) of the two conformers were restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C\\dbC bond (C(7)\\dbC(8)) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction. DFIX was not applied to the length because the observed length of the C\\dbC bond would change with temperature and there is no proper target length required for DFIX. ; _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^)+(0.0669P)^2^+0.5440P] 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 2721 _refine_ls_number_parameters 162 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0442 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1197 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 N1A N 0.37431(12) 0.11179(16) 0.36453(4) 0.0230(2) Uani 0.90 1 d PD A 1 N2A N 0.3968(2) 0.2358(3) 0.67940(5) 0.0186(3) Uani 0.90 1 d PD A 1 O1A O 0.46434(16) 0.2086(2) 0.34705(4) 0.0319(3) Uani 0.90 1 d PD A 1 O2A O 0.30072(10) 0.02029(15) 0.33530(4) 0.0341(3) Uani 0.90 1 d PD A 1 C1A C 0.41678(9) 0.19851(13) 0.51205(4) 0.01544(19) Uani 0.90 1 d PD A 1 C2A C 0.50561(10) 0.30578(14) 0.54152(4) 0.0164(2) Uani 0.90 1 d P A 1 H2A H 0.5714 0.3728 0.5230 0.020 Uiso 0.90 1 calc PR A 1 C3A C 0.50096(13) 0.3176(2) 0.59652(5) 0.0162(2) Uani 0.90 1 d P A 1 H3A H 0.5634 0.3909 0.6149 0.019 Uiso 0.90 1 calc PR A 1 C4A C 0.40341(15) 0.2207(2) 0.62548(4) 0.01519(19) Uani 0.90 1 d PD A 1 C5A C 0.31541(11) 0.10845(16) 0.59588(4) 0.0170(2) Uani 0.90 1 d P A 1 H5A H 0.2503 0.0393 0.6141 0.020 Uiso 0.90 1 calc PR A 1 C6A C 0.32290(10) 0.09820(14) 0.54122(4) 0.0167(2) Uani 0.90 1 d P A 1 H6A H 0.2630 0.0212 0.5227 0.020 Uiso 0.90 1 calc PR A 1 C7A C 0.42795(9) 0.19531(13) 0.45484(4) 0.0171(2) Uani 0.90 1 d PD A 1 H7A H 0.4962 0.2673 0.4397 0.021 Uiso 0.90 1 calc PR A 1 C8A C 0.35163(10) 0.10093(14) 0.42073(4) 0.0194(2) Uani 0.90 1 d PD A 1 H8A H 0.2822 0.0266 0.4340 0.023 Uiso 0.90 1 calc PR A 1 C9A C 0.4963(4) 0.3391(8) 0.70868(17) 0.0231(3) Uani 0.90 1 d PD A 1 H91A H 0.4739 0.3401 0.7466 0.035 Uiso 0.90 1 calc PR A 1 H92A H 0.4992 0.4652 0.6953 0.035 Uiso 0.90 1 calc PR A 1 H93A H 0.5825 0.2813 0.7038 0.035 Uiso 0.90 1 calc PR A 1 C10A C 0.3012(2) 0.1266(3) 0.70884(5) 0.0237(3) Uani 0.90 1 d PD A 1 H101 H 0.3058 0.1578 0.7467 0.035 Uiso 0.90 1 calc PR A 1 H102 H 0.3209 -0.0039 0.7041 0.035 Uiso 0.90 1 calc PR A 1 H103 H 0.2125 0.1524 0.6954 0.035 Uiso 0.90 1 calc PR A 1 N1B N 0.4028(15) 0.149(2) 0.3688(5) 0.0361(11) Uiso 0.10 1 d PD B 2 N2B N 0.384(3) 0.247(5) 0.6810(6) 0.0361(11) Uiso 0.10 1 d PD B 2 O1B O 0.4802(17) 0.219(3) 0.3370(6) 0.0361(11) Uiso 0.10 1 d PD B 2 O2B O 0.3150(12) 0.0469(15) 0.3526(5) 0.0361(11) Uiso 0.10 1 d PD B 2 C1B C 0.3765(11) 0.1562(15) 0.5193(3) 0.0361(11) Uiso 0.10 1 d PGD B 2 C2B C 0.4739(11) 0.2747(17) 0.5373(5) 0.0361(11) Uiso 0.10 1 d PG B 2 H2B H 0.5312 0.3327 0.5126 0.043 Uiso 0.10 1 calc PR B 2 C3B C 0.4874(15) 0.308(2) 0.5915(5) 0.0361(11) Uiso 0.10 1 d PG B 2 H3B H 0.5539 0.3895 0.6039 0.043 Uiso 0.10 1 calc PR B 2 C4B C 0.4035(18) 0.224(3) 0.6277(3) 0.0361(11) Uiso 0.10 1 d PGD B 2 C5B C 0.3061(14) 0.105(2) 0.6096(4) 0.0361(11) Uiso 0.10 1 d PG B 2 H5B H 0.2488 0.0473 0.6343 0.043 Uiso 0.10 1 calc PR B 2 C6B C 0.2927(10) 0.0714(14) 0.5554(4) 0.0361(11) Uiso 0.10 1 d PG B 2 H6B H 0.2261 -0.0096 0.5430 0.043 Uiso 0.10 1 calc PR B 2 C7B C 0.3618(12) 0.1288(16) 0.4629(3) 0.0361(11) Uiso 0.10 1 d PD B 2 H7B H 0.2923 0.0493 0.4525 0.043 Uiso 0.10 1 calc PR B 2 C8B C 0.4318(11) 0.1992(16) 0.4235(4) 0.0361(11) Uiso 0.10 1 d PD B 2 H8B H 0.5012 0.2825 0.4310 0.043 Uiso 0.10 1 calc PR B 2 C9B C 0.491(5) 0.334(9) 0.710(2) 0.0361(11) Uiso 0.10 1 d PD B 2 H91B H 0.5654 0.2479 0.7125 0.054 Uiso 0.10 1 calc PR B 2 H92B H 0.4616 0.3686 0.7452 0.054 Uiso 0.10 1 calc PR B 2 H93B H 0.5199 0.4434 0.6902 0.054 Uiso 0.10 1 calc PR B 2 C10B C 0.308(3) 0.143(4) 0.7189(8) 0.0361(11) Uiso 0.10 1 d PD B 2 H104 H 0.2136 0.1606 0.7116 0.054 Uiso 0.10 1 calc PR B 2 H105 H 0.3276 0.1847 0.7550 0.054 Uiso 0.10 1 calc PR B 2 H106 H 0.3293 0.0123 0.7156 0.054 Uiso 0.10 1 calc PR B 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 N1A 0.0265(6) 0.0264(6) 0.0159(4) -0.0035(3) -0.0046(4) 0.0092(4) N2A 0.0182(6) 0.0220(5) 0.0156(4) 0.0003(3) 0.0030(3) -0.0024(5) O1A 0.0413(7) 0.0348(5) 0.0196(6) 0.0027(5) 0.0026(4) 0.0015(5) O2A 0.0329(5) 0.0470(6) 0.0225(4) -0.0146(4) -0.0111(4) 0.0076(4) C1A 0.0162(4) 0.0151(4) 0.0150(4) -0.0003(3) -0.0019(3) 0.0025(3) C2A 0.0169(4) 0.0170(5) 0.0154(4) 0.0004(3) -0.0010(3) -0.0012(3) C3A 0.0162(4) 0.0176(4) 0.0148(4) -0.0008(3) -0.0007(3) -0.0016(3) C4A 0.0148(4) 0.0142(4) 0.0165(4) 0.0001(3) -0.0007(3) 0.0018(3) C5A 0.0157(4) 0.0169(4) 0.0183(5) 0.0004(4) -0.0006(4) -0.0014(3) C6A 0.0157(4) 0.0164(4) 0.0180(5) -0.0005(3) -0.0028(3) -0.0005(3) C7A 0.0193(4) 0.0166(4) 0.0156(4) 0.0005(3) -0.0017(3) 0.0041(3) C8A 0.0199(4) 0.0236(5) 0.0146(4) -0.0020(3) -0.0020(3) 0.0048(4) C9A 0.0245(6) 0.0295(7) 0.0152(5) -0.0024(4) -0.0018(4) -0.0030(5) C10A 0.0251(6) 0.0261(7) 0.0198(7) 0.0045(5) 0.0065(6) -0.0018(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 N1A O1A 1.2362(17) . ? N1A O2A 1.2426(13) . ? N1A C8A 1.4322(13) . ? N2A C4A 1.3603(14) . ? N2A C10A 1.4583(15) . ? N2A C9A 1.4591(17) . ? C1A C2A 1.4055(12) . ? C1A C6A 1.4080(13) . ? C1A C7A 1.4413(13) . ? C2A C3A 1.3845(13) . ? C3A C4A 1.4183(13) . ? C4A C5A 1.4221(13) . ? C5A C6A 1.3768(13) . ? C7A C8A 1.3450(13) . ? N1B O1B 1.231(9) . ? N1B O2B 1.234(9) . ? N1B C8B 1.451(9) . ? N2B C4B 1.363(10) . ? N2B C10B 1.446(10) . ? N2B C9B 1.450(10) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.438(8) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.323(9) . ? 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 O2A 122.84(12) . . ? O1A N1A C8A 120.05(12) . . ? O2A N1A C8A 117.11(12) . . ? C4A N2A C10A 119.54(17) . . ? C4A N2A C9A 120.6(2) . . ? C10A N2A C9A 119.2(2) . . ? C2A C1A C6A 116.77(8) . . ? C2A C1A C7A 118.91(9) . . ? C6A C1A C7A 124.31(9) . . ? C3A C2A C1A 122.56(9) . . ? C2A C3A C4A 120.28(9) . . ? N2A C4A C3A 120.29(14) . . ? N2A C4A C5A 122.43(15) . . ? C3A C4A C5A 117.29(9) . . ? C6A C5A C4A 121.17(9) . . ? C5A C6A C1A 121.87(8) . . ? C8A C7A C1A 126.70(10) . . ? C7A C8A N1A 120.43(10) . . ? O1B N1B O2B 120.0(15) . . ? O1B N1B C8B 112.4(13) . . ? O2B N1B C8B 127.6(14) . . ? C4B N2B C10B 131(2) . . ? C4B N2B C9B 116(3) . . ? C10B N2B C9B 108(3) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 118.8(9) . . ? C6B C1B C7B 121.1(9) . . ? C3B C2B C1B 120.0 . . ? C2B C3B C4B 120.0 . . ? N2B C4B C3B 132.4(16) . . ? N2B C4B C5B 107.2(16) . . ? C3B C4B C5B 120.0 . . ? C4B C5B C6B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 128.8(11) . . ? C7B C8B N1B 120.1(11) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -1.44(14) . . . . ? C7A C1A C2A C3A 179.46(10) . . . . ? C1A C2A C3A C4A -0.52(14) . . . . ? C10A N2A C4A C3A -176.25(17) . . . . ? C9A N2A C4A C3A -5.2(4) . . . . ? C10A N2A C4A C5A 3.3(3) . . . . ? C9A N2A C4A C5A 174.4(3) . . . . ? C2A C3A C4A N2A -178.40(19) . . . . ? C2A C3A C4A C5A 2.01(13) . . . . ? N2A C4A C5A C6A 178.87(18) . . . . ? C3A C4A C5A C6A -1.55(13) . . . . ? C4A C5A C6A C1A -0.44(14) . . . . ? C2A C1A C6A C5A 1.92(13) . . . . ? C7A C1A C6A C5A -179.03(9) . . . . ? C2A C1A C7A C8A -179.95(9) . . . . ? C6A C1A C7A C8A 1.03(15) . . . . ? C1A C7A C8A N1A 179.74(9) . . . . ? O1A N1A C8A C7A -0.11(18) . . . . ? O2A N1A C8A C7A 179.58(10) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B 177.8(12) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C10B N2B C4B C3B -172(3) . . . . ? C9B N2B C4B C3B -21(5) . . . . ? C10B N2B C4B C5B 16(4) . . . . ? C9B N2B C4B C5B 167(4) . . . . ? C2B C3B C4B N2B -171(3) . . . . ? C2B C3B C4B C5B 0.0 . . . . ? N2B C4B C5B C6B 173(2) . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B -177.8(12) . . . . ? C2B C1B C7B C8B 1.7(17) . . . . ? C6B C1B C7B C8B 179.5(11) . . . . ? C1B C7B C8B N1B 178.2(13) . . . . ? O1B N1B C8B C7B -176.9(16) . . . . ? O2B N1B C8B C7B 2(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.396 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.051 #===END data_omert _database_code_depnum_ccdc_archive 'CCDC 701902' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Methoxy-\b-nitrostyrene ; _chemical_name_common 4-Methoxy-beta-nitrostyrene _chemical_melting_point 89_C _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N O3' _chemical_formula_weight 179.17 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 triclinic _symmetry_space_group_name_H-M P_-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8529(6) _cell_length_b 8.6855(8) _cell_length_c 9.0724(9) _cell_angle_alpha 103.447(2) _cell_angle_beta 90.696(2) _cell_angle_gamma 95.572(2) _cell_volume 446.15(8) _cell_formula_units_Z 2 _cell_measurement_temperature 300 _cell_measurement_reflns_used 2231 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 29.9 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9663 _exptl_absorpt_correction_T_max 0.9702 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 10s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 300 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6964 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 30.02 _reflns_number_total 2597 _reflns_number_gt 1634 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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. In order to avoid the distortion of the structures, especially that of the minor conformer, the following lengths were restrained using SHELXL DFIX instructions. The observed lengths of the corresponding bonds of 4-methoxy- \b-nitrostyrene (3) at 90 K were used as the target values of the restraints. The length of the C---Ph bond (C(1)---C(7)) of the two conformers was restrained to be 1.45 \%A with an e.s.d. of 0.01 \%A. The length of the C---NO2 bond (C(8)---N(1)) of the two conformers was restrained to be 1.44 \%A with an e.s.d. of 0.01 \%A. The lengths of the N---O bonds (N(1)---O(1) and N(1)---O(2)) of the two conformers were restrained to be 1.23 \%A with an e.s.d. of 0.01 \%A. The length of the O---Ph bond (O(3)---C(4)) of the two conformers was restrained to be 1.36 \%A with an e.s.d. of 0.01 \%A. The length of the O---Me bond (O(3)---C(9)) of the two conformers was restrained to be 1.43 \%A with an e.s.d. of 0.01 \%A. The length of the C\\dbC bond (C(7)\\dbC(8)) of the two conformers was restrained to be equal with an e.s.d. of 0.01 \%A using SHELXL SADI instruction. ; _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^)+(0.1074P)^2^+0.0493P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.20(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2597 _refine_ls_number_parameters 149 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0600 _refine_ls_wR_factor_ref 0.2189 _refine_ls_wR_factor_gt 0.1898 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 N1A N 0.3231(4) 0.4019(4) 0.6261(3) 0.0675(7) Uani 0.85 1 d PD A 1 O1A O 0.4970(4) 0.3760(3) 0.6850(2) 0.0981(7) Uani 0.85 1 d PD A 1 O2A O 0.2694(4) 0.3388(3) 0.4941(2) 0.1095(8) Uani 0.85 1 d PD A 1 O3A O -0.3272(2) 1.00345(18) 1.21624(16) 0.0741(4) Uani 0.85 1 d PD A 1 C1A C 0.0698(3) 0.6893(2) 0.94514(19) 0.0519(5) Uani 0.85 1 d PD A 1 C2A C 0.1381(4) 0.7539(3) 1.0946(2) 0.0622(5) Uani 0.85 1 d P A 1 H2A H 0.2730 0.7265 1.1324 0.075 Uiso 0.85 1 calc PR A 1 C3A C 0.0091(4) 0.8593(3) 1.1898(2) 0.0632(5) Uani 0.85 1 d P A 1 H3A H 0.0572 0.9015 1.2905 0.076 Uiso 0.85 1 calc PR A 1 C4A C -0.1907(3) 0.9011(2) 1.1341(2) 0.0545(4) Uani 0.85 1 d PD A 1 C5A C -0.2616(3) 0.8372(2) 0.9838(2) 0.0620(5) Uani 0.85 1 d P A 1 H5A H -0.3960 0.8652 0.9460 0.074 Uiso 0.85 1 calc PR A 1 C6A C -0.1332(3) 0.7327(2) 0.8911(2) 0.0604(5) Uani 0.85 1 d P A 1 H6A H -0.1823 0.6901 0.7907 0.072 Uiso 0.85 1 calc PR A 1 C7A C 0.2122(3) 0.5806(2) 0.8506(2) 0.0589(5) Uani 0.85 1 d PD A 1 H7A H 0.3444 0.5585 0.8962 0.071 Uiso 0.85 1 calc PR A 1 C8A C 0.1711(3) 0.5106(2) 0.7067(2) 0.0662(5) Uani 0.85 1 d PD A 1 H8A H 0.0426 0.5316 0.6563 0.079 Uiso 0.85 1 calc PR A 1 C9A C -0.2650(5) 1.0719(3) 1.3734(3) 0.0871(8) Uani 0.85 1 d PD A 1 H91A H -0.2604 0.9886 1.4265 0.131 Uiso 0.85 1 calc PR A 1 H92A H -0.3765 1.1415 1.4174 0.131 Uiso 0.85 1 calc PR A 1 H93A H -0.1164 1.1313 1.3813 0.131 Uiso 0.85 1 calc PR A 1 N1B N 0.345(3) 0.421(4) 0.625(2) 0.0939(14) Uiso 0.15 1 d PD B 2 O1B O 0.543(2) 0.3846(18) 0.6323(15) 0.0939(14) Uiso 0.15 1 d PD B 2 O2B O 0.202(2) 0.3583(17) 0.5226(17) 0.0939(14) Uiso 0.15 1 d PD B 2 O3B O -0.1367(16) 0.9900(11) 1.3312(9) 0.0939(14) Uiso 0.15 1 d PD B 2 C1B C 0.025(3) 0.6908(18) 0.9263(14) 0.0939(14) Uiso 0.15 1 d PGD B 2 C2B C 0.163(2) 0.7198(17) 1.0574(19) 0.0939(14) Uiso 0.15 1 d PG B 2 H2B H 0.2984 0.6718 1.0567 0.113 Uiso 0.15 1 calc PR B 2 C3B C 0.099(2) 0.8204(16) 1.1897(13) 0.0939(14) Uiso 0.15 1 d PG B 2 H3B H 0.1912 0.8398 1.2775 0.113 Uiso 0.15 1 calc PR B 2 C4B C -0.104(3) 0.8920(13) 1.1908(12) 0.0939(14) Uiso 0.15 1 d PGD B 2 C5B C -0.2420(19) 0.8631(16) 1.0597(17) 0.0939(14) Uiso 0.15 1 d PG B 2 H5B H -0.3775 0.9110 1.0604 0.113 Uiso 0.15 1 calc PR B 2 C6B C -0.178(3) 0.762(2) 0.9274(12) 0.0939(14) Uiso 0.15 1 d PG B 2 H6B H -0.2703 0.7431 0.8396 0.113 Uiso 0.15 1 calc PR B 2 C7B C 0.099(3) 0.5782(16) 0.7943(15) 0.0939(14) Uiso 0.15 1 d PD B 2 H7B H -0.0059 0.5484 0.7125 0.113 Uiso 0.15 1 calc PR B 2 C8B C 0.294(2) 0.5125(18) 0.7739(17) 0.0939(14) Uiso 0.15 1 d PD B 2 H8B H 0.3980 0.5247 0.8550 0.113 Uiso 0.15 1 calc PR B 2 C9B C -0.342(3) 1.065(3) 1.332(3) 0.0939(14) Uiso 0.15 1 d PD B 2 H91B H -0.3057 1.1784 1.3607 0.141 Uiso 0.15 1 calc PR B 2 H92B H -0.4443 1.0319 1.4030 0.141 Uiso 0.15 1 calc PR B 2 H93B H -0.4139 1.0353 1.2323 0.141 Uiso 0.15 1 calc PR B 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 N1A 0.0754(12) 0.0636(13) 0.0650(9) 0.0121(8) 0.0073(8) 0.0214(11) O1A 0.0901(13) 0.1220(15) 0.0891(14) 0.0233(12) 0.0022(9) 0.0495(11) O2A 0.1167(18) 0.1341(17) 0.0696(11) -0.0090(10) -0.0060(10) 0.0548(13) O3A 0.0722(9) 0.0752(9) 0.0717(9) 0.0042(7) 0.0109(6) 0.0225(7) C1A 0.0509(9) 0.0511(8) 0.0568(9) 0.0181(7) 0.0043(7) 0.0064(7) C2A 0.0567(9) 0.0730(12) 0.0598(12) 0.0185(9) -0.0022(7) 0.0140(8) C3A 0.0637(11) 0.0698(11) 0.0557(9) 0.0133(8) -0.0027(7) 0.0095(8) C4A 0.0520(8) 0.0537(9) 0.0582(9) 0.0131(7) 0.0055(7) 0.0070(7) C5A 0.0538(9) 0.0683(11) 0.0623(10) 0.0089(8) -0.0016(7) 0.0140(8) C6A 0.0562(10) 0.0655(11) 0.0580(10) 0.0107(8) -0.0034(7) 0.0095(8) C7A 0.0547(9) 0.0614(10) 0.0637(10) 0.0191(8) 0.0027(7) 0.0105(7) C8A 0.0654(11) 0.0688(11) 0.0661(11) 0.0132(8) 0.0009(8) 0.0219(8) C9A 0.1012(19) 0.0822(15) 0.0710(16) -0.0027(12) 0.0156(12) 0.0237(15) _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 N1A O1A 1.208(3) . ? N1A O2A 1.219(3) . ? N1A C8A 1.440(3) . ? O3A C4A 1.352(2) . ? O3A C9A 1.439(3) . ? C1A C2A 1.379(2) . ? C1A C6A 1.397(2) . ? C1A C7A 1.454(2) . ? C2A C3A 1.392(3) . ? C3A C4A 1.381(3) . ? C4A C5A 1.388(3) . ? C5A C6A 1.375(2) . ? C7A C8A 1.314(2) . ? N1B O2B 1.233(10) . ? N1B O1B 1.233(10) . ? N1B C8B 1.447(10) . ? O3B C4B 1.384(8) . ? O3B C9B 1.419(9) . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C1B C7B 1.460(9) . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C7B C8B 1.318(9) . ? 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 O2A 121.4(2) . . ? O1A N1A C8A 122.0(2) . . ? O2A N1A C8A 116.6(2) . . ? C4A O3A C9A 118.48(17) . . ? C2A C1A C6A 118.22(16) . . ? C2A C1A C7A 118.84(15) . . ? C6A C1A C7A 122.94(16) . . ? C1A C2A C3A 121.24(17) . . ? C4A C3A C2A 119.64(17) . . ? O3A C4A C3A 124.4(2) . . ? O3A C4A C5A 115.76(18) . . ? C3A C4A C5A 119.82(16) . . ? C6A C5A C4A 119.99(16) . . ? C5A C6A C1A 121.11(16) . . ? C8A C7A C1A 125.99(17) . . ? C7A C8A N1A 120.7(2) . . ? O2B N1B O1B 124.5(17) . . ? O2B N1B C8B 125.5(17) . . ? O1B N1B C8B 107.7(13) . . ? C4B O3B C9B 111.8(13) . . ? C2B C1B C6B 120.0 . . ? C2B C1B C7B 116.5(14) . . ? C6B C1B C7B 123.5(14) . . ? C1B C2B C3B 120.0 . . ? C4B C3B C2B 120.0 . . ? O3B C4B C5B 128.2(13) . . ? O3B C4B C3B 111.7(13) . . ? C5B C4B C3B 120.0 . . ? C6B C5B C4B 120.0 . . ? C5B C6B C1B 120.0 . . ? C8B C7B C1B 129.6(16) . . ? C7B C8B N1B 120.0(14) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A 0.1(3) . . . . ? C7A C1A C2A C3A 179.59(19) . . . . ? C1A C2A C3A C4A -0.3(3) . . . . ? C9A O3A C4A C3A -1.4(3) . . . . ? C9A O3A C4A C5A 179.08(19) . . . . ? C2A C3A C4A O3A -179.29(18) . . . . ? C2A C3A C4A C5A 0.2(3) . . . . ? O3A C4A C5A C6A 179.62(17) . . . . ? C3A C4A C5A C6A 0.1(3) . . . . ? C4A C5A C6A C1A -0.3(3) . . . . ? C2A C1A C6A C5A 0.1(3) . . . . ? C7A C1A C6A C5A -179.28(19) . . . . ? C2A C1A C7A C8A -179.47(18) . . . . ? C6A C1A C7A C8A 0.0(3) . . . . ? C1A C7A C8A N1A -178.5(3) . . . . ? O1A N1A C8A C7A -3.1(5) . . . . ? O2A N1A C8A C7A 178.0(3) . . . . ? C6B C1B C2B C3B 0.0 . . . . ? C7B C1B C2B C3B -177.3(16) . . . . ? C1B C2B C3B C4B 0.0 . . . . ? C9B O3B C4B C5B 0.4(18) . . . . ? C9B O3B C4B C3B 179.2(12) . . . . ? C2B C3B C4B O3B -178.9(12) . . . . ? C2B C3B C4B C5B 0.0 . . . . ? O3B C4B C5B C6B 178.7(14) . . . . ? C3B C4B C5B C6B 0.0 . . . . ? C4B C5B C6B C1B 0.0 . . . . ? C2B C1B C6B C5B 0.0 . . . . ? C7B C1B C6B C5B 177.1(17) . . . . ? C2B C1B C7B C8B -9(2) . . . . ? C6B C1B C7B C8B 173.7(14) . . . . ? C1B C7B C8B N1B -171(2) . . . . ? O2B N1B C8B C7B -22(5) . . . . ? O1B N1B C8B C7B 174(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.159 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.042 #===END data_ome90k _database_code_depnum_ccdc_archive 'CCDC 701903' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-Methoxy-\b-nitrostyrene ; _chemical_name_common 4-Methoxy-beta-nitrostyrene _chemical_melting_point 89_C _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 N O3' _chemical_formula_weight 179.17 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 triclinic _symmetry_space_group_name_H-M P_-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7014(3) _cell_length_b 8.4321(5) _cell_length_c 9.1812(5) _cell_angle_alpha 103.481(1) _cell_angle_beta 90.271(1) _cell_angle_gamma 97.265(1) _cell_volume 425.51(4) _cell_formula_units_Z 2 _cell_measurement_temperature 90 _cell_measurement_reflns_used 4466 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 30.0 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9647 _exptl_absorpt_correction_T_max 0.9688 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 10s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 90 _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 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6600 _diffrn_reflns_av_R_equivalents 0.0111 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 30.02 _reflns_number_total 2462 _reflns_number_gt 2220 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.0731P)^2^+0.0678P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2462 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.32582(12) 0.40766(8) 0.62177(7) 0.01896(16) Uani 1 1 d . . . O1 O 0.50036(11) 0.37618(8) 0.68318(7) 0.02732(17) Uani 1 1 d . . . O2 O 0.27092(12) 0.34703(8) 0.48748(7) 0.02836(17) Uani 1 1 d . . . O3 O -0.33201(11) 1.00654(7) 1.22304(7) 0.02236(16) Uani 1 1 d . . . C1 C 0.07022(13) 0.69019(9) 0.94630(8) 0.01638(17) Uani 1 1 d . . . C2 C 0.14090(13) 0.75247(9) 1.09677(8) 0.01856(17) Uani 1 1 d . . . C3 C 0.01180(14) 0.85828(10) 1.19409(8) 0.01920(17) Uani 1 1 d . . . C4 C -0.19263(13) 0.90319(9) 1.13982(9) 0.01773(17) Uani 1 1 d . . . C5 C -0.26647(14) 0.84137(10) 0.98907(9) 0.01923(17) Uani 1 1 d . . . C6 C -0.13759(13) 0.73625(9) 0.89403(8) 0.01848(17) Uani 1 1 d . . . C7 C 0.21366(14) 0.58120(9) 0.85060(8) 0.01761(17) Uani 1 1 d . . . C8 C 0.17307(14) 0.51705(10) 0.70395(9) 0.01961(17) Uani 1 1 d . . . C9 C -0.26523(17) 1.07255(11) 1.37768(10) 0.02580(19) Uani 1 1 d . . . H2 H 0.283(2) 0.7208(15) 1.1346(13) 0.028(3) Uiso 1 1 d . . . H3 H 0.068(2) 0.8968(15) 1.2953(14) 0.031(3) Uiso 1 1 d . . . H5 H -0.413(2) 0.8746(16) 0.9532(15) 0.036(3) Uiso 1 1 d . . . H6 H -0.195(2) 0.6970(14) 0.7903(13) 0.025(3) Uiso 1 1 d . . . H7 H 0.343(2) 0.5538(17) 0.8987(14) 0.036(3) Uiso 1 1 d . . . H8 H 0.046(2) 0.5304(15) 0.6394(14) 0.031(3) Uiso 1 1 d . . . H91 H -0.271(2) 0.9879(15) 1.4301(13) 0.027(3) Uiso 1 1 d . . . H92 H -0.111(2) 1.1343(15) 1.3873(13) 0.031(3) Uiso 1 1 d . . . H93 H -0.381(3) 1.1434(18) 1.4161(16) 0.049(4) Uiso 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 N1 0.0209(3) 0.0189(3) 0.0173(3) 0.0030(2) 0.0008(2) 0.0056(2) O1 0.0268(3) 0.0342(3) 0.0228(3) 0.0038(2) -0.0015(2) 0.0164(3) O2 0.0324(3) 0.0331(3) 0.0171(3) -0.0033(2) -0.0023(2) 0.0125(3) O3 0.0225(3) 0.0226(3) 0.0209(3) -0.0001(2) 0.0034(2) 0.0086(2) C1 0.0163(3) 0.0162(3) 0.0168(3) 0.0038(3) 0.0012(2) 0.0032(2) C2 0.0180(3) 0.0206(3) 0.0178(3) 0.0049(3) -0.0001(3) 0.0048(3) C3 0.0208(4) 0.0208(3) 0.0154(3) 0.0026(3) 0.0001(3) 0.0039(3) C4 0.0174(3) 0.0159(3) 0.0200(3) 0.0034(3) 0.0039(3) 0.0040(2) C5 0.0169(3) 0.0205(3) 0.0204(4) 0.0038(3) 0.0001(3) 0.0050(3) C6 0.0183(3) 0.0200(3) 0.0167(3) 0.0027(3) -0.0005(2) 0.0037(3) C7 0.0177(3) 0.0174(3) 0.0180(3) 0.0038(3) 0.0013(2) 0.0041(3) C8 0.0200(4) 0.0199(3) 0.0192(4) 0.0025(3) 0.0010(3) 0.0079(3) C9 0.0294(4) 0.0244(4) 0.0215(4) -0.0006(3) 0.0051(3) 0.0068(3) _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 1.2287(9) . ? N1 O2 1.2416(9) . ? N1 C8 1.4365(10) . ? O3 C4 1.3583(9) . ? O3 C9 1.4294(10) . ? C1 C2 1.3963(10) . ? C1 C6 1.4081(10) . ? C1 C7 1.4511(10) . ? C2 C3 1.3917(10) . ? C2 H2 0.972(12) . ? C3 C4 1.3943(11) . ? C3 H3 0.949(12) . ? C4 C5 1.4026(11) . ? C5 C6 1.3774(10) . ? C5 H5 0.990(13) . ? C6 H6 0.973(12) . ? C7 C8 1.3360(10) . ? C7 H7 0.938(13) . ? C8 H8 0.965(13) . ? C9 H91 0.946(12) . ? C9 H92 0.958(13) . ? C9 H93 0.957(16) . ? 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 122.49(7) . . ? O1 N1 C8 120.93(7) . . ? O2 N1 C8 116.58(7) . . ? C4 O3 C9 117.54(7) . . ? C2 C1 C6 118.40(7) . . ? C2 C1 C7 118.75(7) . . ? C6 C1 C7 122.85(7) . . ? C3 C2 C1 121.53(7) . . ? C3 C2 H2 119.2(7) . . ? C1 C2 H2 119.3(7) . . ? C2 C3 C4 119.15(7) . . ? C2 C3 H3 118.0(7) . . ? C4 C3 H3 122.8(7) . . ? O3 C4 C3 124.70(7) . . ? O3 C4 C5 115.26(7) . . ? C3 C4 C5 120.05(7) . . ? C6 C5 C4 120.23(7) . . ? C6 C5 H5 121.2(8) . . ? C4 C5 H5 118.6(8) . . ? C5 C6 C1 120.63(7) . . ? C5 C6 H6 117.4(7) . . ? C1 C6 H6 122.0(7) . . ? C8 C7 C1 125.47(7) . . ? C8 C7 H7 119.0(8) . . ? C1 C7 H7 115.5(8) . . ? C7 C8 N1 120.22(7) . . ? C7 C8 H8 129.1(8) . . ? N1 C8 H8 110.7(8) . . ? O3 C9 H91 110.9(7) . . ? O3 C9 H92 110.3(7) . . ? H91 C9 H92 110.9(10) . . ? O3 C9 H93 105.3(9) . . ? H91 C9 H93 109.1(11) . . ? H92 C9 H93 110.2(11) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.31(11) . . . . ? C7 C1 C2 C3 179.62(7) . . . . ? C1 C2 C3 C4 -0.09(12) . . . . ? C9 O3 C4 C3 -0.65(12) . . . . ? C9 O3 C4 C5 179.75(7) . . . . ? C2 C3 C4 O3 -179.32(7) . . . . ? C2 C3 C4 C5 0.27(12) . . . . ? O3 C4 C5 C6 179.59(7) . . . . ? C3 C4 C5 C6 -0.03(12) . . . . ? C4 C5 C6 C1 -0.39(12) . . . . ? C2 C1 C6 C5 0.55(11) . . . . ? C7 C1 C6 C5 -179.38(7) . . . . ? C2 C1 C7 C8 -177.51(7) . . . . ? C6 C1 C7 C8 2.42(13) . . . . ? C1 C7 C8 N1 -178.72(7) . . . . ? O1 N1 C8 C7 -2.73(12) . . . . ? O2 N1 C8 C7 176.83(7) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.421 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.063