# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_999359
_audit_creation_date             2013-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            'm-MPCPA '
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N2 O2'
_chemical_formula_sum            'C11 H10 N2 O2'
_chemical_formula_weight         202.21

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   P21/c

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                   15.6778(10)
_cell_length_b                   3.9598(3)
_cell_length_c                   17.4076(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.928(8)
_cell_angle_gamma                90.00
_cell_volume                     1022.26(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2074
#_exptl_absorpt_correction_T_min                   0.98258
#_exptl_absorpt_correction_T_max                   1.00000

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7686
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1796
_reflns_number_gt                1496
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 1990)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1990)'

_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)+(0.0371P)²+0.4052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1796
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38606(10) 0.4715(4) 0.24164(8) 0.0581(5) Uani 1 1 d . . .
O2 O 0.14133(11) 0.4535(5) 0.55633(9) 0.0642(5) Uani 1 1 d . . .
N1 N 0.48935(11) 0.7562(5) 0.34116(10) 0.0508(5) Uani 1 1 d . . .
H1A H 0.5246 0.7831 0.3127 0.061 Uiso 1 1 calc R . .
H1B H 0.5042 0.8357 0.3897 0.061 Uiso 1 1 calc R . .
N2 N 0.41351(13) 0.8423(5) 0.50450(11) 0.0601(6) Uani 1 1 d . . .
C1 C 0.41214(13) 0.5923(5) 0.31019(12) 0.0410(5) Uani 1 1 d . . .
C2 C 0.38630(13) 0.7111(5) 0.44273(12) 0.0414(5) Uani 1 1 d . . .
C3 C 0.35436(12) 0.5590(5) 0.36412(11) 0.0369(4) Uani 1 1 d . . .
C4 C 0.27515(13) 0.3959(5) 0.33592(11) 0.0401(5) Uani 1 1 d . . .
H4 H 0.2631 0.3072 0.2840 0.048 Uiso 1 1 calc R . .
C5 C 0.20479(12) 0.3330(5) 0.37196(12) 0.0394(5) Uani 1 1 d . . .
C6 C 0.21188(13) 0.4212(5) 0.45171(12) 0.0431(5) Uani 1 1 d . . .
H6 H 0.2653 0.5136 0.4859 0.052 Uiso 1 1 calc R . .
C7 C 0.12526(14) 0.1869(5) 0.32282(13) 0.0496(5) Uani 1 1 d . . .
H7 H 0.1199 0.1213 0.2702 0.059 Uiso 1 1 calc R . .
C8 C 0.06074(14) 0.2329(6) 0.42933(15) 0.0559(6) Uani 1 1 d . . .
H8 H 0.0120 0.2036 0.4481 0.067 Uiso 1 1 calc R . .
C9 C 0.14044(13) 0.3722(5) 0.47972(13) 0.0458(5) Uani 1 1 d . . .
C10 C 0.22056(17) 0.6074(7) 0.60995(14) 0.0662(7) Uani 1 1 d . . .
H10A H 0.2346 0.8067 0.5850 0.099 Uiso 1 1 calc R . .
H10B H 0.2700 0.4515 0.6212 0.099 Uiso 1 1 calc R . .
H10C H 0.2105 0.6675 0.6597 0.099 Uiso 1 1 calc R . .
C11 C 0.05402(14) 0.1387(6) 0.35199(15) 0.0593(6) Uani 1 1 d . . .
H11 H 0.0009 0.0412 0.3187 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0511(9) 0.0891(12) 0.0390(8) -0.0135(8) 0.0215(7) -0.0031(8)
O2 0.0559(10) 0.0891(12) 0.0585(10) 0.0001(9) 0.0337(8) -0.0013(9)
N1 0.0440(10) 0.0768(13) 0.0375(9) -0.0013(9) 0.0215(8) -0.0088(9)
N2 0.0550(11) 0.0845(15) 0.0456(11) -0.0104(11) 0.0229(9) -0.0208(11)
C1 0.0389(11) 0.0505(12) 0.0364(11) 0.0059(9) 0.0161(8) 0.0081(9)
C2 0.0368(10) 0.0529(12) 0.0386(11) 0.0031(10) 0.0179(9) -0.0046(9)
C3 0.0380(10) 0.0420(11) 0.0334(10) 0.0028(8) 0.0153(8) 0.0049(9)
C4 0.0412(11) 0.0455(11) 0.0339(10) -0.0010(9) 0.0127(8) 0.0046(9)
C5 0.0357(10) 0.0397(11) 0.0433(11) 0.0030(9) 0.0134(8) 0.0038(9)
C6 0.0353(10) 0.0496(12) 0.0458(11) 0.0014(9) 0.0151(9) -0.0009(9)
C7 0.0449(12) 0.0509(13) 0.0502(12) -0.0030(10) 0.0117(10) -0.0018(10)
C8 0.0382(12) 0.0629(15) 0.0715(16) 0.0085(12) 0.0247(11) -0.0016(10)
C9 0.0431(11) 0.0481(12) 0.0515(12) 0.0068(10) 0.0229(10) 0.0039(10)
C10 0.0748(17) 0.0792(18) 0.0482(13) -0.0020(12) 0.0248(12) -0.0007(14)
C11 0.0361(11) 0.0645(15) 0.0720(16) -0.0017(13) 0.0102(11) -0.0103(11)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.226(2) . ?
O2 C9 1.368(2) . ?
O2 C10 1.426(3) . ?
N1 C1 1.324(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C2 1.145(2) . ?
C1 C3 1.507(2) . ?
C2 C3 1.429(3) . ?
C3 C4 1.343(3) . ?
C4 C5 1.457(3) . ?
C4 H4 0.9300 . ?
C5 C7 1.389(3) . ?
C5 C6 1.401(3) . ?
C6 C9 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C11 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C11 1.368(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 C10 118.05(16) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
O1 C1 N1 124.03(18) . . ?
O1 C1 C3 119.61(18) . . ?
N1 C1 C3 116.36(17) . . ?
N2 C2 C3 177.3(2) . . ?
C4 C3 C2 123.22(17) . . ?
C4 C3 C1 119.05(17) . . ?
C2 C3 C1 117.72(17) . . ?
C3 C4 C5 131.63(18) . . ?
C3 C4 H4 114.2 . . ?
C5 C4 H4 114.2 . . ?
C7 C5 C6 118.77(18) . . ?
C7 C5 C4 117.39(18) . . ?
C6 C5 C4 123.81(17) . . ?
C9 C6 C5 120.34(19) . . ?
C9 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C11 C7 C5 120.2(2) . . ?
C11 C7 H7 119.9 . . ?
C5 C7 H7 119.9 . . ?
C11 C8 C9 119.79(19) . . ?
C11 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
O2 C9 C6 124.16(19) . . ?
O2 C9 C8 115.63(18) . . ?
C6 C9 C8 120.2(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 C7 120.7(2) . . ?
C8 C11 H11 119.6 . . ?
C7 C11 H11 119.6 . . ?

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
N2 C2 C3 C4 -148(5) . . . . ?
N2 C2 C3 C1 31(5) . . . . ?
O1 C1 C3 C4 0.2(3) . . . . ?
N1 C1 C3 C4 179.85(18) . . . . ?
O1 C1 C3 C2 -178.43(19) . . . . ?
N1 C1 C3 C2 1.2(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C1 C3 C4 C5 -177.92(19) . . . . ?
C3 C4 C5 C7 172.8(2) . . . . ?
C3 C4 C5 C6 -5.0(3) . . . . ?
C7 C5 C6 C9 -1.8(3) . . . . ?
C4 C5 C6 C9 176.01(19) . . . . ?
C6 C5 C7 C11 1.7(3) . . . . ?
C4 C5 C7 C11 -176.3(2) . . . . ?
C10 O2 C9 C6 1.7(3) . . . . ?
C10 O2 C9 C8 -178.1(2) . . . . ?
C5 C6 C9 O2 -179.46(19) . . . . ?
C5 C6 C9 C8 0.4(3) . . . . ?
C11 C8 C9 O2 -179.0(2) . . . . ?
C11 C8 C9 C6 1.2(3) . . . . ?
C9 C8 C11 C7 -1.3(4) . . . . ?
C5 C7 C11 C8 -0.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B N2 0.86 2.27 3.068(3) 154.9 3_676
N1 H1A O1 0.86 2.07 2.906(2) 165.0 2_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 999359'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p
_audit_creation_date             2013-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            o-MPCPA
_chemical_name_systematic        
; 
 2-cyano-3-(2-methoxyphenyl)-2-propenamide 
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N2 O2'
_chemical_formula_sum            'C11 H10 N2 O2'
_chemical_formula_weight         202.21

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'

_space_group_crystal_system      Monoclinic
_space_group_name_H-M            I2/a
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.7381(9)
_cell_length_b                   8.8770(4)
_cell_length_c                   17.5640(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.368(6)
_cell_angle_gamma                90.00
_cell_volume                     2083.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1670
_cell_measurement_theta_min      3.7610
_cell_measurement_theta_max      26.5640

_exptl_crystal_description       bolck
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22






_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0395
_diffrn_standards_number         5283
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4389
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1839
_reflns_number_gt                1357
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0556P)²+0.3409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1839
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07945(10) 0.65094(13) 0.29288(7) 0.0532(4) Uani 1 1 d . . .
O2 O 0.15108(13) 0.76188(16) 0.54529(9) 0.0758(5) Uani 1 1 d . . .
N1 N 0.02799(12) 0.42670(16) 0.23912(8) 0.0496(4) Uani 1 1 d . . .
H1A H 0.0124 0.4642 0.1927 0.059 Uiso 1 1 calc R . .
H1B H 0.0192 0.3322 0.2461 0.059 Uiso 1 1 calc R . .
N2 N 0.08869(16) 0.15365(19) 0.38274(10) 0.0768(6) Uani 1 1 d . . .
C1 C 0.06565(12) 0.51488(19) 0.30014(10) 0.0394(4) Uani 1 1 d . . .
C2 C 0.08956(14) 0.2830(2) 0.38293(10) 0.0486(5) Uani 1 1 d . . .
C3 C 0.09079(12) 0.44348(18) 0.37968(10) 0.0369(4) Uani 1 1 d . . .
C4 C 0.11126(12) 0.53343(19) 0.44279(10) 0.0387(4) Uani 1 1 d . . .
H4 H 0.1110 0.6355 0.4309 0.046 Uiso 1 1 calc R . .
C5 C 0.13371(12) 0.50151(19) 0.52619(10) 0.0404(4) Uani 1 1 d . . .
C6 C 0.13567(15) 0.3575(2) 0.55823(11) 0.0521(5) Uani 1 1 d . . .
H6 H 0.1222 0.2749 0.5249 0.062 Uiso 1 1 calc R . .
C7 C 0.15694(16) 0.3342(3) 0.63795(12) 0.0631(6) Uani 1 1 d . . .
H7 H 0.1592 0.2369 0.6579 0.076 Uiso 1 1 calc R . .
C8 C 0.17471(16) 0.4552(3) 0.68768(12) 0.0650(6) Uani 1 1 d . . .
H8 H 0.1877 0.4396 0.7414 0.078 Uiso 1 1 calc R . .
C9 C 0.17355(15) 0.5992(3) 0.65906(12) 0.0618(6) Uani 1 1 d . . .
H9 H 0.1861 0.6805 0.6933 0.074 Uiso 1 1 calc R . .
C10 C 0.15346(14) 0.6233(2) 0.57854(11) 0.0490(5) Uani 1 1 d . . .
C11 C 0.1879(3) 0.8885(3) 0.59412(18) 0.1093(11) Uani 1 1 d . . .
H11A H 0.1867 0.9766 0.5622 0.164 Uiso 1 1 calc R . .
H11B H 0.2552 0.8690 0.6225 0.164 Uiso 1 1 calc R . .
H11C H 0.1463 0.9048 0.6304 0.164 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0632(9) 0.0384(8) 0.0542(8) 0.0077(6) 0.0055(7) -0.0028(6)
O2 0.1098(13) 0.0505(9) 0.0680(10) -0.0218(8) 0.0224(9) -0.0156(8)
N1 0.0716(11) 0.0396(8) 0.0358(8) 0.0015(7) 0.0089(8) -0.0010(8)
N2 0.1254(18) 0.0384(11) 0.0537(11) -0.0015(8) -0.0054(11) -0.0001(10)
C1 0.0394(10) 0.0361(10) 0.0431(10) 0.0021(8) 0.0102(8) 0.0026(8)
C2 0.0625(12) 0.0413(12) 0.0363(10) 0.0001(8) -0.0001(8) 0.0006(9)
C3 0.0371(9) 0.0321(9) 0.0416(9) 0.0007(7) 0.0091(7) 0.0021(7)
C4 0.0371(10) 0.0345(9) 0.0453(10) -0.0012(8) 0.0112(8) -0.0004(8)
C5 0.0339(9) 0.0469(11) 0.0414(10) -0.0039(9) 0.0108(7) -0.0018(8)
C6 0.0581(12) 0.0523(12) 0.0464(11) 0.0008(9) 0.0132(9) 0.0005(10)
C7 0.0660(14) 0.0766(15) 0.0474(12) 0.0110(11) 0.0148(10) 0.0048(11)
C8 0.0536(12) 0.1008(18) 0.0412(11) 0.0009(13) 0.0120(9) 0.0025(13)
C9 0.0498(12) 0.0872(17) 0.0489(13) -0.0247(12) 0.0121(9) -0.0071(12)
C10 0.0439(10) 0.0533(12) 0.0507(12) -0.0122(9) 0.0131(9) -0.0045(9)
C11 0.159(3) 0.0653(17) 0.111(2) -0.0459(16) 0.047(2) -0.0371(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
O1 C1 1.2338(19) . ?
O2 C10 1.359(2) . ?
O2 C11 1.433(3) . ?
N1 C1 1.331(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C2 1.148(2) . ?
C1 C3 1.500(2) . ?
C2 C3 1.426(2) . ?
C3 C4 1.342(2) . ?
C4 C5 1.453(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(2) . ?
C5 C10 1.405(2) . ?
C6 C7 1.378(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C10 O2 C11 118.86(19) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
O1 C1 N1 122.20(15) . . ?
O1 C1 C3 120.14(15) . . ?
N1 C1 C3 117.66(15) . . ?
N2 C2 C3 177.53(19) . . ?
C4 C3 C2 124.30(15) . . ?
C4 C3 C1 118.49(15) . . ?
C2 C3 C1 117.20(14) . . ?
C3 C4 C5 132.19(16) . . ?
C3 C4 H4 113.9 . . ?
C5 C4 H4 113.9 . . ?
C6 C5 C10 117.32(17) . . ?
C6 C5 C4 124.41(16) . . ?
C10 C5 C4 118.26(16) . . ?
C7 C6 C5 121.81(19) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.76(19) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 119.86(19) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
O2 C10 C9 123.71(17) . . ?
O2 C10 C5 115.70(16) . . ?
C9 C10 C5 120.58(18) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
N2 C2 C3 C4 -164(5) . . . . ?
N2 C2 C3 C1 17(5) . . . . ?
O1 C1 C3 C4 11.6(2) . . . . ?
N1 C1 C3 C4 -167.99(15) . . . . ?
O1 C1 C3 C2 -169.45(16) . . . . ?
N1 C1 C3 C2 11.0(2) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C1 C3 C4 C5 177.03(17) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C3 C4 C5 C10 179.17(17) . . . . ?
C10 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 -179.63(18) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C11 O2 C10 C9 11.4(3) . . . . ?
C11 O2 C10 C5 -168.83(19) . . . . ?
C8 C9 C10 O2 -179.83(18) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C6 C5 C10 O2 179.90(17) . . . . ?
C4 C5 C10 O2 -1.0(2) . . . . ?
C6 C5 C10 C9 -0.3(3) . . . . ?
C4 C5 C10 C9 178.79(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O1 0.86 2.11 2.8466(19) 142.8 4_445
N1 H1A N2 0.86 2.38 3.102(2) 141.9 4_455

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 999360'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
2-cyano-3-(4-methoxyphenyl)-2-propenamide
;
_chemical_name_common            p-MPCPA
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N2 O2'
_chemical_formula_sum            'C11 H10 N2 O2'
_chemical_formula_weight         202.21

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   'P21/c   '

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                   3.920(2)
_cell_length_b                   10.792(6)
_cell_length_c                   23.124(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.463(8)
_cell_angle_gamma                90.00
_cell_volume                     976.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2260
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      28.66

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4626
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1698
_reflns_number_gt                1453
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0010P)²+6.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.039(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1698
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.2367
_refine_ls_wR_factor_gt          0.2333
_refine_ls_goodness_of_fit_ref   1.035
_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
N1 N 0.2620(17) 0.9857(4) 0.0718(2) 0.0576(16) Uani 1 1 d . . .
N2 N 0.7011(17) 0.8411(5) 0.1877(2) 0.0688(18) Uani 1 1 d . . .
O1 O 0.0355(12) 0.8388(4) 0.01268(17) 0.0585(13) Uani 1 1 d . . .
O2 O 0.7348(12) 0.1775(3) 0.15425(17) 0.0542(12) Uani 1 1 d . . .
C1 C 0.2088(14) 0.8671(5) 0.0557(2) 0.0399(13) Uani 1 1 d . . .
C2 C 0.3694(14) 0.7693(5) 0.0942(2) 0.0361(12) Uani 1 1 d . . .
C3 C 0.5535(15) 0.8068(5) 0.1465(2) 0.0433(14) Uani 1 1 d . . .
C4 C 0.3345(14) 0.6498(5) 0.0769(2) 0.0398(13) Uani 1 1 d . . .
H4A H 0.2084 0.6411 0.0418 0.048 Uiso 1 1 calc R . .
C5 C 0.4510(13) 0.5330(5) 0.1012(2) 0.0365(12) Uani 1 1 d . . .
C6 C 0.6282(15) 0.5159(5) 0.1548(2) 0.0429(14) Uani 1 1 d . . .
H6A H 0.6823 0.5844 0.1780 0.051 Uiso 1 1 calc R . .
C7 C 0.7250(14) 0.3991(5) 0.1742(2) 0.0399(13) Uani 1 1 d . . .
H7A H 0.8393 0.3895 0.2104 0.048 Uiso 1 1 calc R . .
C8 C 0.6516(14) 0.2964(5) 0.1398(2) 0.0401(13) Uani 1 1 d . . .
C9 C 0.4766(16) 0.3115(5) 0.0861(2) 0.0472(15) Uani 1 1 d . . .
H9A H 0.4256 0.2430 0.0628 0.057 Uiso 1 1 calc R . .
C10 C 0.3804(15) 0.4269(5) 0.0680(2) 0.0415(13) Uani 1 1 d . . .
H10A H 0.2628 0.4356 0.0321 0.050 Uiso 1 1 calc R . .
C11 C 0.9134(18) 0.1557(5) 0.2091(3) 0.0571(17) Uani 1 1 d . . .
H11A H 0.9553 0.0686 0.2139 0.086 Uiso 1 1 calc R . .
H11B H 0.7774 0.1846 0.2396 0.086 Uiso 1 1 calc R . .
H11C H 1.1271 0.1994 0.2108 0.086 Uiso 1 1 calc R . .
H2 H 0.169(16) 1.044(6) 0.044(3) 0.055(17) Uiso 1 1 d . . .
H1 H 0.41(2) 1.018(9) 0.101(4) 0.12(3) 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 0.088(4) 0.029(3) 0.053(3) 0.006(2) -0.022(3) 0.006(3)
N2 0.102(5) 0.045(3) 0.055(3) 0.004(3) -0.027(3) -0.002(3)
O1 0.081(3) 0.036(2) 0.055(3) 0.0056(18) -0.026(2) 0.003(2)
O2 0.084(3) 0.0275(19) 0.049(2) 0.0017(17) -0.015(2) 0.002(2)
C1 0.048(3) 0.035(3) 0.036(3) 0.002(2) -0.004(2) -0.001(2)
C2 0.042(3) 0.033(3) 0.033(3) 0.003(2) 0.000(2) 0.004(2)
C3 0.057(3) 0.026(3) 0.046(3) 0.004(2) -0.004(3) 0.004(2)
C4 0.049(3) 0.037(3) 0.034(3) 0.003(2) -0.001(2) 0.002(2)
C5 0.041(3) 0.033(3) 0.035(3) 0.003(2) -0.001(2) 0.001(2)
C6 0.059(4) 0.032(3) 0.038(3) -0.006(2) -0.004(2) -0.001(3)
C7 0.052(3) 0.036(3) 0.030(3) 0.002(2) -0.007(2) 0.002(2)
C8 0.049(3) 0.030(3) 0.041(3) 0.003(2) 0.002(2) -0.002(2)
C9 0.065(4) 0.029(3) 0.045(3) -0.005(2) -0.012(3) -0.003(3)
C10 0.054(3) 0.035(3) 0.034(3) 0.004(2) -0.007(2) -0.004(2)
C11 0.076(5) 0.040(3) 0.053(4) 0.006(3) -0.013(3) 0.010(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 C1 1.345(7) . ?
N1 H2 0.95(7) . ?
N1 H1 0.93(10) . ?
N2 C3 1.146(7) . ?
O1 C1 1.209(6) . ?
O2 C8 1.360(6) . ?
O2 C11 1.431(7) . ?
C1 C2 1.496(7) . ?
C2 C4 1.355(7) . ?
C2 C3 1.429(7) . ?
C4 C5 1.443(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.396(7) . ?
C5 C10 1.397(7) . ?
C6 C7 1.383(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.385(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.390(7) . ?
C9 C10 1.361(7) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C1 N1 H2 114(4) . . ?
C1 N1 H1 130(6) . . ?
H2 N1 H1 116(7) . . ?
C8 O2 C11 118.1(4) . . ?
O1 C1 N1 122.6(5) . . ?
O1 C1 C2 120.4(5) . . ?
N1 C1 C2 117.0(5) . . ?
C4 C2 C3 123.8(5) . . ?
C4 C2 C1 117.7(5) . . ?
C3 C2 C1 118.5(4) . . ?
N2 C3 C2 177.6(6) . . ?
C2 C4 C5 133.8(5) . . ?
C2 C4 H4A 113.1 . . ?
C5 C4 H4A 113.1 . . ?
C6 C5 C10 116.8(5) . . ?
C6 C5 C4 126.2(5) . . ?
C10 C5 C4 117.0(4) . . ?
C7 C6 C5 121.4(5) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C8 119.9(5) . . ?
C6 C7 H7A 120.0 . . ?
C8 C7 H7A 120.0 . . ?
O2 C8 C7 125.1(5) . . ?
O2 C8 C9 115.3(5) . . ?
C7 C8 C9 119.6(5) . . ?
C10 C9 C8 119.7(5) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
C9 C10 C5 122.6(5) . . ?
C9 C10 H10A 118.7 . . ?
C5 C10 H10A 118.7 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
O1 C1 C2 C4 4.8(9) . . . . ?
N1 C1 C2 C4 -176.3(6) . . . . ?
O1 C1 C2 C3 -176.0(6) . . . . ?
N1 C1 C2 C3 2.9(8) . . . . ?
C4 C2 C3 N2 165(16) . . . . ?
C1 C2 C3 N2 -14(17) . . . . ?
C3 C2 C4 C5 0.4(10) . . . . ?
C1 C2 C4 C5 179.5(6) . . . . ?
C2 C4 C5 C6 3.9(10) . . . . ?
C2 C4 C5 C10 -176.0(6) . . . . ?
C10 C5 C6 C7 -0.8(8) . . . . ?
C4 C5 C6 C7 179.3(6) . . . . ?
C5 C6 C7 C8 1.2(9) . . . . ?
C11 O2 C8 C7 -0.3(9) . . . . ?
C11 O2 C8 C9 -179.6(6) . . . . ?
C6 C7 C8 O2 179.8(6) . . . . ?
C6 C7 C8 C9 -0.9(9) . . . . ?
O2 C8 C9 C10 179.6(6) . . . . ?
C7 C8 C9 C10 0.2(9) . . . . ?
C8 C9 C10 C5 0.2(10) . . . . ?
C6 C5 C10 C9 0.1(9) . . . . ?
C4 C5 C10 C9 180.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 999361'
