# 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        
;
β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 5s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with
an e.s.d. of 0.01 Å. The length of the C---NO2 bond (C(8)---N(1)) of the
two conformers was restrained to be 1.44 Å with an e.s.d. of 0.01 Å.
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 Å with an e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0596P)²+0.1587P] where P=(Fo²+2Fc²)/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        
;
β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 5s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with
an e.s.d. of 0.01 Å. The length of the C---NO2 bond (C(8)---N(1)) of the
two conformers was restrained to be 1.44 Å with an e.s.d. of 0.01 Å.
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 Å with an e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0633P)²+0.1288P] where P=(Fo²+2Fc²)/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        
;
β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 5s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with
an e.s.d. of 0.01 Å. The length of the C---NO2 bond (C(8)---N(1)) of the
two conformers was restrained to be 1.44 Å with an e.s.d. of 0.01 Å.
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 Å with an e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0568P)²+0.2089P] where P=(Fo²+2Fc²)/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        
;
β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 5s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with
an e.s.d. of 0.01 Å. The length of the C---NO2 bond (C(8)---N(1)) of the
two conformers was restrained to be 1.44 Å with an e.s.d. of 0.01 Å.
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 Å with an e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0689P)²+0.1398P] where P=(Fo²+2Fc²)/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        
;
β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 5s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with
an e.s.d. of 0.01 Å. The length of the C---NO2 bond (C(8)---N(1)) of the
two conformers was restrained to be 1.44 Å with an e.s.d. of 0.01 Å.
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 Å with an e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0565P)²+0.1876P] where P=(Fo²+2Fc²)/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-β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 10s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with an e.s.d. of 0.01 Å. The
length of the C---NO2 bond (C(8)---N(1)) of the two conformers was
restrained to be 1.44 Å with an e.s.d. of 0.01 Å. 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 Å with an e.s.d. of 0.01 Å.

The following target values were taken from the corresponding bond lengths
of 4-dimethylamino-β-ethyl-β-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 Å with an
e.s.d. of 0.01 Å. 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 Å with an
e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0532P)²+0.5447P] where P=(Fo²+2Fc²)/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+0.001xFc²λ³/sin(2θ)]^-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-β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 10s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with an e.s.d. of 0.01 Å. The
length of the C---NO2 bond (C(8)---N(1)) of the two conformers was
restrained to be 1.44 Å with an e.s.d. of 0.01 Å. 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 Å with an e.s.d. of 0.01 Å.

The following target values were taken from the corresponding bond lengths
of 4-dimethylamino-β-ethyl-β-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 Å with an
e.s.d. of 0.01 Å. 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 Å with an
e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0769P)²+0.6363P] where P=(Fo²+2Fc²)/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+0.001xFc²λ³/sin(2θ)]^-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-β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 10s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with an e.s.d. of 0.01 Å. The
length of the C---NO2 bond (C(8)---N(1)) of the two conformers was
restrained to be 1.44 Å with an e.s.d. of 0.01 Å. 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 Å with an e.s.d. of 0.01 Å.

The following target values were taken from the corresponding bond lengths
of 4-dimethylamino-β-ethyl-β-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 Å with an
e.s.d. of 0.01 Å. 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 Å with an
e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0748P)²+0.4763P] where P=(Fo²+2Fc²)/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+0.001xFc²λ³/sin(2θ)]^-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-β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 5s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with an e.s.d. of 0.01 Å. The
length of the C---NO2 bond (C(8)---N(1)) of the two conformers was
restrained to be 1.44 Å with an e.s.d. of 0.01 Å. 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 Å with an e.s.d. of 0.01 Å.

The following target values were taken from the corresponding bond lengths
of 4-dimethylamino-β-ethyl-β-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 Å with an
e.s.d. of 0.01 Å. 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 Å with an
e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0706P)²+0.5275P] where P=(Fo²+2Fc²)/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-β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 5s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with an e.s.d. of 0.01 Å. The
length of the C---NO2 bond (C(8)---N(1)) of the two conformers was
restrained to be 1.44 Å with an e.s.d. of 0.01 Å. 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 Å with an e.s.d. of 0.01 Å.

The following target values were taken from the corresponding bond lengths
of 4-dimethylamino-β-ethyl-β-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 Å with an
e.s.d. of 0.01 Å. 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 Å with an
e.s.d. of 0.01 Å.

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 Å 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/[σ²(Fo²)+(0.0669P)²+0.5440P] where P=(Fo²+2Fc²)/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-β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 10s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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-
β-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 Å with an e.s.d. of 0.01 Å. The
length of the C---NO2 bond (C(8)---N(1)) of the two conformers was
restrained to be 1.44 Å with an e.s.d. of 0.01 Å. 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 Å with an e.s.d. of 0.01 Å. The length of the
O---Ph bond (O(3)---C(4)) of the two conformers was restrained to be 1.36
Å with an e.s.d. of 0.01 Å. The length of the O---Me bond (O(3)---C(9))
of the two conformers was restrained to be 1.43 Å with an e.s.d. of
0.01 Å.

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 Å 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/[σ²(Fo²)+(0.1074P)²+0.0493P] where P=(Fo²+2Fc²)/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+0.001xFc²λ³/sin(2θ)]^-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-β-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 φ angle (0,
90, 180 and 270°) for the crystal and each exposure of 10s covered 0.3° in
ω. 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       ω_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 F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0731P)²+0.0678P] where P=(Fo²+2Fc²)/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


