# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_586
_audit_block_doi                 10.5517/ccwydy4
_database_code_depnum_ccdc_archive 'CCDC 832627'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1055/s-0031-1290449 2012
_audit_update_record             
;
2011-07-04 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(2E)-2-(ethoxycarbonyl)-3-[(2-ethoxyphenyl)amino]acrylic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N O6'
_chemical_formula_weight         307.30

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           -P2yn
_symmetry_space_group_name_H-M   P121/n1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9000(2)
_cell_length_b                   23.1582(7)
_cell_length_c                   8.7135(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.9040(10)
_cell_angle_gamma                90.00
_cell_volume                     1516.93(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4723
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.13

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18031
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         29.63
_reflns_number_total             4264
_reflns_number_gt                2519
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1047P)²+0.3661P] 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       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4264
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1918
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.007

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 0.90477(19) 0.10319(6) 0.52815(17) 0.0495(4) Uani 1 1 d . . .
C1 C 0.8351(2) 0.06409(7) 0.40030(19) 0.0463(4) Uani 1 1 d . . .
C2 C 0.7649(2) 0.01111(7) 0.42962(19) 0.0467(4) Uani 1 1 d . . .
C8 C 1.0551(2) 0.19194(8) 0.6381(2) 0.0526(4) Uani 1 1 d . . .
O6 O 0.7091(2) -0.05946(6) 0.59916(16) 0.0669(4) Uani 1 1 d . . .
C7 C 0.9743(2) 0.15457(7) 0.5146(2) 0.0503(4) Uani 1 1 d . . .
O4 O 1.0214(2) 0.13202(7) 0.84544(17) 0.0737(4) Uani 1 1 d . . .
O5 O 0.7768(2) 0.02834(6) 0.70390(17) 0.0733(4) Uani 1 1 d . . .
C5 C 0.7790(3) 0.03647(9) 0.1219(2) 0.0651(5) Uani 1 1 d . . .
H5 H 0.7839 0.0450 0.0191 0.078 Uiso 1 1 calc R . .
C3 C 0.7042(3) -0.02818(8) 0.3031(2) 0.0577(5) Uani 1 1 d . . .
H3 H 0.6582 -0.0635 0.3223 0.069 Uiso 1 1 calc R . .
C13 C 0.7519(2) -0.00415(8) 0.5915(2) 0.0521(4) Uani 1 1 d . . .
C6 C 0.8399(3) 0.07601(8) 0.2445(2) 0.0582(5) Uani 1 1 d . . .
H6 H 0.8848 0.1112 0.2233 0.070 Uiso 1 1 calc R . .
O1 O 1.1993(2) 0.28243(6) 0.70128(19) 0.0778(5) Uani 1 1 d . . .
C4 C 0.7109(3) -0.01577(9) 0.1509(2) 0.0646(5) Uani 1 1 d . . .
H4 H 0.6697 -0.0424 0.0679 0.078 Uiso 1 1 calc R . .
C9 C 1.1218(2) 0.24676(8) 0.6007(2) 0.0589(5) Uani 1 1 d . . .
O2 O 1.0913(2) 0.25621(7) 0.44454(18) 0.0773(5) Uani 1 1 d . . .
O3 O 1.1583(3) 0.21523(8) 0.91873(19) 0.0985(6) Uani 1 1 d . . .
C12 C 1.0755(3) 0.17701(9) 0.8060(2) 0.0633(5) Uani 1 1 d . . .
C14 C 0.6895(3) -0.07949(10) 0.7507(3) 0.0696(6) Uani 1 1 d . . .
H14A H 0.5981 -0.0575 0.7778 0.083 Uiso 1 1 calc R . .
H14B H 0.8005 -0.0751 0.8371 0.083 Uiso 1 1 calc R . .
C10 C 1.1483(4) 0.31227(13) 0.3987(4) 0.1051(10) Uani 1 1 d . . .
H10A H 1.0999 0.3433 0.4473 0.126 Uiso 1 1 calc R . .
H10B H 1.2770 0.3150 0.4372 0.126 Uiso 1 1 calc R . .
C15 C 0.6387(4) -0.14118(12) 0.7275(4) 0.1029(9) Uani 1 1 d . . .
H15A H 0.6242 -0.1564 0.8252 0.154 Uiso 1 1 calc R . .
H15B H 0.7302 -0.1624 0.7006 0.154 Uiso 1 1 calc R . .
H15C H 0.5288 -0.1448 0.6416 0.154 Uiso 1 1 calc R . .
C11 C 1.0862(4) 0.31770(14) 0.2257(4) 0.1122(11) Uani 1 1 d . . .
H11A H 1.1228 0.3543 0.1950 0.168 Uiso 1 1 calc R . .
H11B H 0.9588 0.3152 0.1884 0.168 Uiso 1 1 calc R . .
H11C H 1.1357 0.2872 0.1783 0.168 Uiso 1 1 calc R . .
H7 H 0.9679 0.1659 0.4053 0.061(5) Uiso 1 1 d R . .
H1N H 0.9056 0.0929 0.6232 0.077(7) Uiso 1 1 d R . .
H4A H 1.1989 0.2526 0.8514 0.188(16) Uiso 1 1 d R . .


_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 C7 1.331(2) . ?
N1 C1 1.410(2) . ?
N1 H1N 0.8595 . ?
C1 C6 1.397(2) . ?
C1 C2 1.402(2) . ?
C2 C3 1.395(2) . ?
C2 C13 1.488(2) . ?
C8 C7 1.376(2) . ?
C8 C9 1.450(3) . ?
C8 C12 1.464(3) . ?
O6 C13 1.332(2) . ?
O6 C14 1.452(2) . ?
C7 H7 0.9743 . ?
O4 C12 1.215(3) . ?
O5 C13 1.203(2) . ?
C5 C4 1.379(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
O1 C9 1.223(2) . ?
C4 H4 0.9300 . ?
C9 O2 1.325(2) . ?
O2 C10 1.469(3) . ?
O3 C12 1.334(2) . ?
O3 H4A 1.1453 . ?
C14 C15 1.481(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C10 C11 1.440(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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
C7 N1 C1 125.13(15) . . ?
C7 N1 H1N 116.9 . . ?
C1 N1 H1N 117.9 . . ?
C6 C1 C2 118.70(15) . . ?
C6 C1 N1 121.37(16) . . ?
C2 C1 N1 119.89(14) . . ?
C3 C2 C1 119.07(15) . . ?
C3 C2 C13 119.12(16) . . ?
C1 C2 C13 121.81(15) . . ?
C7 C8 C9 119.22(17) . . ?
C7 C8 C12 121.04(17) . . ?
C9 C8 C12 119.74(17) . . ?
C13 O6 C14 116.92(15) . . ?
N1 C7 C8 126.71(17) . . ?
N1 C7 H7 115.4 . . ?
C8 C7 H7 117.9 . . ?
C4 C5 C6 120.32(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C4 C3 C2 121.35(18) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
O5 C13 O6 122.78(17) . . ?
O5 C13 C2 125.58(17) . . ?
O6 C13 C2 111.63(15) . . ?
C5 C6 C1 121.01(18) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C3 C4 C5 119.54(18) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
O1 C9 O2 121.17(19) . . ?
O1 C9 C8 124.52(19) . . ?
O2 C9 C8 114.31(16) . . ?
C9 O2 C10 116.81(17) . . ?
C12 O3 H4A 106.0 . . ?
O4 C12 O3 119.8(2) . . ?
O4 C12 C8 123.03(18) . . ?
O3 C12 C8 117.22(19) . . ?
O6 C14 C15 106.51(19) . . ?
O6 C14 H14A 110.4 . . ?
C15 C14 H14A 110.4 . . ?
O6 C14 H14B 110.4 . . ?
C15 C14 H14B 110.4 . . ?
H14A C14 H14B 108.6 . . ?
C11 C10 O2 109.1(2) . . ?
C11 C10 H10A 109.9 . . ?
O2 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
O2 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 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
C7 N1 C1 C6 2.4(3) . . . . ?
C7 N1 C1 C2 -179.87(15) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
N1 C1 C2 C3 -177.03(15) . . . . ?
C6 C1 C2 C13 -178.69(16) . . . . ?
N1 C1 C2 C13 3.5(2) . . . . ?
C1 N1 C7 C8 -174.86(16) . . . . ?
C9 C8 C7 N1 -179.27(16) . . . . ?
C12 C8 C7 N1 1.1(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C13 C2 C3 C4 179.04(17) . . . . ?
C14 O6 C13 O5 1.2(3) . . . . ?
C14 O6 C13 C2 -179.02(16) . . . . ?
C3 C2 C13 O5 -169.51(19) . . . . ?
C1 C2 C13 O5 10.0(3) . . . . ?
C3 C2 C13 O6 10.8(2) . . . . ?
C1 C2 C13 O6 -169.76(15) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
N1 C1 C6 C5 176.99(17) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C7 C8 C9 O1 -178.18(18) . . . . ?
C12 C8 C9 O1 1.4(3) . . . . ?
C7 C8 C9 O2 2.2(3) . . . . ?
C12 C8 C9 O2 -178.17(17) . . . . ?
O1 C9 O2 C10 -2.4(3) . . . . ?
C8 C9 O2 C10 177.2(2) . . . . ?
C7 C8 C12 O4 -1.0(3) . . . . ?
C9 C8 C12 O4 179.40(18) . . . . ?
C7 C8 C12 O3 178.81(18) . . . . ?
C9 C8 C12 O3 -0.8(3) . . . . ?
C13 O6 C14 C15 178.8(2) . . . . ?
C9 O2 C10 C11 -173.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.63
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.035



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MHE-1
_database_code_depnum_ccdc_archive 'CCDC 957106'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 (2E)-2-(ethoxycarbonyl)-3-(phenylamino)prop-2-enoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 N O4'
_chemical_formula_weight         235.23

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0418(13)
_cell_length_b                   7.5275(14)
_cell_length_c                   11.444(2)
_cell_angle_alpha                84.212(9)
_cell_angle_beta                 75.935(9)
_cell_angle_gamma                82.835(9)
_cell_volume                     582.28(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4539
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      31.67
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
__exptl_crystal_density_meas     ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   ?






_exptl_special_details           
;
 ?
;
_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  MoKα
_diffrn_measurement_method       'phi and omega scans'

_diffrn_reflns_number            14267
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.839
_diffrn_reflns_theta_max         33.583
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4021
_reflns_number_gt                2736
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0799P)²+0.0408P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4021
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1314
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16215(14) 0.77158(14) 0.35014(7) 0.0567(2) Uani 1 1 d . . . . .
H1O H 0.041(3) 0.828(3) 0.373(2) 0.097(6) Uiso 1 1 d . . . . .
O2 O 0.35226(13) 0.59892(14) 0.45174(8) 0.0613(3) Uani 1 1 d . . . . .
O3 O -0.18255(12) 0.88075(13) 0.46094(7) 0.0556(2) Uani 1 1 d . . . . .
O4 O -0.28878(11) 0.79954(11) 0.65709(7) 0.0480(2) Uani 1 1 d . . . . .
N1 N 0.21075(14) 0.49672(12) 0.68747(8) 0.0418(2) Uani 1 1 d . . . . .
H1N H 0.317(2) 0.490(2) 0.6299(15) 0.063(4) Uiso 1 1 d . . . . .
C1 C 0.21656(16) 0.40020(14) 0.80002(9) 0.0411(2) Uani 1 1 d . . . . .
C2 C 0.39249(18) 0.37616(18) 0.83629(11) 0.0528(3) Uani 1 1 d . . . . .
H2 H 0.5048 0.4200 0.7868 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3993(2) 0.2859(2) 0.94725(12) 0.0659(4) Uani 1 1 d . . . . .
H3 H 0.5169 0.2699 0.9721 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2346(2) 0.2201(2) 1.02078(11) 0.0671(4) Uani 1 1 d . . . . .
H4 H 0.2404 0.1609 1.0954 0.081 Uiso 1 1 calc R U . . .
C5 C 0.0611(2) 0.24207(19) 0.98360(12) 0.0632(4) Uani 1 1 d . . . . .
H5 H -0.0503 0.1968 1.0332 0.076 Uiso 1 1 calc R U . . .
C6 C 0.05068(19) 0.33138(17) 0.87263(11) 0.0516(3) Uani 1 1 d . . . . .
H6 H -0.0666 0.3448 0.8474 0.062 Uiso 1 1 calc R U . . .
C7 C 0.05327(15) 0.59813(13) 0.66675(9) 0.0392(2) Uani 1 1 d . . . . .
H7 H -0.0561 0.6067 0.7314 0.047 Uiso 1 1 calc R U . . .
C8 C 0.03299(15) 0.69258(13) 0.56002(9) 0.0386(2) Uani 1 1 d . . . . .
C9 C 0.19307(16) 0.68385(15) 0.45223(10) 0.0434(2) Uani 1 1 d . . . . .
C10 C -0.15200(15) 0.79802(14) 0.55394(9) 0.0412(2) Uani 1 1 d . . . . .
C11 C -0.47893(16) 0.89578(18) 0.64901(11) 0.0510(3) Uani 1 1 d . . . . .
H11A H -0.5345 0.8406 0.5937 0.061 Uiso 1 1 calc R U . . .
H11B H -0.4633 1.0197 0.6194 0.061 Uiso 1 1 calc R U . . .
C12 C -0.6109(2) 0.88752(19) 0.77213(12) 0.0593(3) Uani 1 1 d . . . . .
H12A H -0.6194 0.7644 0.8024 0.089 Uiso 1 1 calc R U . . .
H12B H -0.7397 0.9436 0.7686 0.089 Uiso 1 1 calc R U . . .
H12C H -0.5588 0.9492 0.8249 0.089 Uiso 1 1 calc R U . . .


_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 C9 1.3344(13) . ?
O1 H1O 0.90(2) . ?
O2 C9 1.2183(14) . ?
O3 C10 1.2293(12) . ?
O4 C10 1.3299(14) . ?
O4 C11 1.4598(13) . ?
N1 C7 1.3224(13) . ?
N1 C1 1.4205(12) . ?
N1 H1N 0.870(17) . ?
C1 C6 1.3841(17) . ?
C1 C2 1.3852(16) . ?
C2 C3 1.3870(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3896(16) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.3791(13) . ?
C7 H7 0.9300 . ?
C8 C10 1.4514(14) . ?
C8 C9 1.4556(15) . ?
C11 C12 1.4877(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C9 O1 H1O 103.1(14) . . ?
C10 O4 C11 115.10(8) . . ?
C7 N1 C1 123.40(9) . . ?
C7 N1 H1N 118.8(10) . . ?
C1 N1 H1N 117.8(10) . . ?
C6 C1 C2 120.27(10) . . ?
C6 C1 N1 121.14(10) . . ?
C2 C1 N1 118.59(10) . . ?
C1 C2 C3 119.26(12) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.84(13) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.66(11) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.60(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.35(12) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N1 C7 C8 127.30(9) . . ?
N1 C7 H7 116.4 . . ?
C8 C7 H7 116.4 . . ?
C7 C8 C10 119.70(9) . . ?
C7 C8 C9 120.81(9) . . ?
C10 C8 C9 119.47(9) . . ?
O2 C9 O1 119.20(10) . . ?
O2 C9 C8 122.60(9) . . ?
O1 C9 C8 118.20(9) . . ?
O3 C10 O4 121.61(9) . . ?
O3 C10 C8 123.20(10) . . ?
O4 C10 C8 115.19(9) . . ?
O4 C11 C12 107.73(9) . . ?
O4 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C7 N1 C1 C6 32.44(16) . . . . ?
C7 N1 C1 C2 -147.45(11) . . . . ?
C6 C1 C2 C3 -1.43(19) . . . . ?
N1 C1 C2 C3 178.47(11) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C2 C1 C6 C5 1.66(19) . . . . ?
N1 C1 C6 C5 -178.22(11) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C1 N1 C7 C8 -178.30(10) . . . . ?
N1 C7 C8 C10 -179.82(10) . . . . ?
N1 C7 C8 C9 1.94(17) . . . . ?
C7 C8 C9 O2 -2.36(18) . . . . ?
C10 C8 C9 O2 179.40(11) . . . . ?
C7 C8 C9 O1 177.06(10) . . . . ?
C10 C8 C9 O1 -1.18(16) . . . . ?
C11 O4 C10 O3 3.87(17) . . . . ?
C11 O4 C10 C8 -176.13(9) . . . . ?
C7 C8 C10 O3 -177.59(10) . . . . ?
C9 C8 C10 O3 0.68(18) . . . . ?
C7 C8 C10 O4 2.41(16) . . . . ?
C9 C8 C10 O4 -179.33(9) . . . . ?
C10 O4 C11 C12 -178.63(10) . . . . ?

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 H1N O2 0.870(17) 2.089(16) 2.7072(13) 127.4(13) .
O1 H1O O3 0.90(2) 1.67(2) 2.5281(13) 159(2) .
N1 H1N O2 0.870(17) 2.326(17) 3.1340(14) 154.5(13) 2_666
C2 H2 O2 0.93 2.68 3.3483(16) 129.2 2_666
C12 H12A C2 0.96 2.90 3.843(2) 166.9 1_455
C5 H5 C12 0.93 2.93 3.838(2) 166.7 2_467

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-3


_diffrn_ambient_temperature      296
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MHE-2
_database_code_depnum_ccdc_archive 'CCDC 957107'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
  (2E)-2-(ethoxycarbonyl)-3-[(4-methylphenyl)amino]prop-2-enoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N O4'
_chemical_formula_weight         249.26

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8768(2)
_cell_length_b                   7.5092(3)
_cell_length_c                   12.8653(4)
_cell_angle_alpha                93.415(2)
_cell_angle_beta                 104.473(2)
_cell_angle_gamma                95.382(2)
_cell_volume                     638.06(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2013
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      22.10


_exptl_crystal_description       PRISM
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9589
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.641
_diffrn_reflns_theta_max         24.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.9000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_reflns_number_total             2078
_reflns_number_gt                1479
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.0895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2078
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.005
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03080(18) 0.23504(18) 0.36411(10) 0.0623(4) Uani 1 1 d . . . . .
H1O H -0.0790 0.1740 0.3842 0.093 Uiso 1 1 d R U . . .
O2 O 0.31030(19) 0.40102(19) 0.45504(10) 0.0653(4) Uani 1 1 d . . . . .
O3 O -0.22138(18) 0.12301(18) 0.46605(11) 0.0627(4) Uani 1 1 d . . . . .
O4 O -0.15944(17) 0.19693(16) 0.64333(10) 0.0546(4) Uani 1 1 d . . . . .
N1 N 0.3703(2) 0.49314(19) 0.66885(11) 0.0482(4) Uani 1 1 d . . . . .
H1N H 0.4269 0.4999 0.6127 0.058 Uiso 1 1 d R U . . .
C1 C 0.4748(3) 0.5801(2) 0.77127(14) 0.0466(5) Uani 1 1 d . . . . .
C2 C 0.6836(3) 0.5967(3) 0.80064(15) 0.0567(5) Uani 1 1 d . . . . .
H2 H 0.7539 0.5534 0.7532 0.068 Uiso 1 1 calc R U . . .
C3 C 0.7872(3) 0.6777(3) 0.90052(16) 0.0645(6) Uani 1 1 d . . . . .
H3 H 0.9277 0.6886 0.9192 0.077 Uiso 1 1 calc R U . . .
C4 C 0.6897(3) 0.7432(3) 0.97373(15) 0.0613(6) Uani 1 1 d . . . . .
C5 C 0.4808(3) 0.7265(3) 0.94198(16) 0.0666(6) Uani 1 1 d . . . . .
H5 H 0.4104 0.7697 0.9893 0.080 Uiso 1 1 calc R U . . .
C6 C 0.3742(3) 0.6474(3) 0.84199(16) 0.0597(5) Uani 1 1 d . . . . .
H6 H 0.2338 0.6395 0.8224 0.072 Uiso 1 1 calc R U . . .
C7 C 0.1923(2) 0.3946(2) 0.64955(14) 0.0456(5) Uani 1 1 d . . . . .
H7 H 0.1367 0.3839 0.7081 0.055 Uiso 1 1 calc R U . . .
C8 C 0.0804(2) 0.3065(2) 0.55357(14) 0.0435(4) Uani 1 1 d . . . . .
C9 C 0.1495(3) 0.3182(2) 0.45621(15) 0.0485(5) Uani 1 1 d . . . . .
C10 C -0.1114(3) 0.2017(2) 0.54916(15) 0.0474(5) Uani 1 1 d . . . . .
C11 C -0.3549(3) 0.0971(3) 0.63912(16) 0.0584(5) Uani 1 1 d . . . . .
H11A H -0.3629 -0.0233 0.6055 0.070 Uiso 1 1 calc R U . . .
H11B H -0.4637 0.1568 0.5972 0.070 Uiso 1 1 calc R U . . .
C12 C -0.3732(3) 0.0896(3) 0.75214(17) 0.0730(6) Uani 1 1 d . . . . .
H12A H -0.2693 0.0246 0.7918 0.109 Uiso 1 1 calc R U . . .
H12B H -0.5033 0.0300 0.7514 0.109 Uiso 1 1 calc R U . . .
H12C H -0.3586 0.2094 0.7858 0.109 Uiso 1 1 calc R U . . .
C13 C 0.8069(4) 0.8327(4) 1.08290(18) 0.0931(8) Uani 1 1 d . . . . .
H13A H 0.9151 0.7642 1.1134 0.140 Uiso 1 1 calc R U . . .
H13B H 0.7183 0.8388 1.1297 0.140 Uiso 1 1 calc R U . . .
H13C H 0.8618 0.9519 1.0747 0.140 Uiso 1 1 calc R U . . .


_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 C9 1.339(2) . ?
O1 H1O 0.9452 . ?
O2 C9 1.2210(19) . ?
O3 C10 1.225(2) . ?
O4 C10 1.335(2) . ?
O4 C11 1.4634(19) . ?
N1 C7 1.3279(19) . ?
N1 C1 1.420(2) . ?
N1 H1N 0.9039 . ?
C1 C6 1.374(3) . ?
C1 C2 1.382(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 C13 1.515(3) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.373(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.451(2) . ?
C8 C10 1.458(2) . ?
C11 C12 1.494(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C9 O1 H1O 104.8 . . ?
C10 O4 C11 115.28(14) . . ?
C7 N1 C1 123.85(15) . . ?
C7 N1 H1N 116.2 . . ?
C1 N1 H1N 119.9 . . ?
C6 C1 C2 119.21(17) . . ?
C6 C1 N1 121.84(16) . . ?
C2 C1 N1 118.95(16) . . ?
C3 C2 C1 119.65(19) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 122.27(19) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 116.92(18) . . ?
C3 C4 C13 121.3(2) . . ?
C5 C4 C13 121.8(2) . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C1 C6 C5 120.15(18) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C8 127.84(17) . . ?
N1 C7 H7 116.1 . . ?
C8 C7 H7 116.1 . . ?
C7 C8 C9 120.85(15) . . ?
C7 C8 C10 119.59(16) . . ?
C9 C8 C10 119.55(15) . . ?
O2 C9 O1 119.01(17) . . ?
O2 C9 C8 122.67(16) . . ?
O1 C9 C8 118.31(15) . . ?
O3 C10 O4 121.91(16) . . ?
O3 C10 C8 123.24(17) . . ?
O4 C10 C8 114.86(15) . . ?
O4 C11 C12 107.78(15) . . ?
O4 C11 H11A 110.2 . . ?
C12 C11 H11A 110.1 . . ?
O4 C11 H11B 110.1 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C7 N1 C1 C6 -33.3(3) . . . . ?
C7 N1 C1 C2 146.45(18) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
N1 C1 C2 C3 -178.77(17) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C13 -179.7(2) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C13 C4 C5 C6 179.0(2) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
N1 C1 C6 C5 178.15(17) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C1 N1 C7 C8 179.75(17) . . . . ?
N1 C7 C8 C9 -1.8(3) . . . . ?
N1 C7 C8 C10 178.91(16) . . . . ?
C7 C8 C9 O2 2.1(3) . . . . ?
C10 C8 C9 O2 -178.64(17) . . . . ?
C7 C8 C9 O1 -177.58(16) . . . . ?
C10 C8 C9 O1 1.7(3) . . . . ?
C11 O4 C10 O3 -2.2(3) . . . . ?
C11 O4 C10 C8 178.02(15) . . . . ?
C7 C8 C10 O3 178.33(17) . . . . ?
C9 C8 C10 O3 -1.0(3) . . . . ?
C7 C8 C10 O4 -1.9(2) . . . . ?
C9 C8 C10 O4 178.84(16) . . . . ?
C10 O4 C11 C12 174.12(17) . . . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MHE-3
_database_code_depnum_ccdc_archive 'CCDC 957109'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 2E)-3-[(4-chlorophenyl)amino]-2-(ethoxycarbonyl)prop-2-enoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cl N O4'
_chemical_formula_weight         269.68

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0837(2)
_cell_length_b                   7.4404(2)
_cell_length_c                   12.4791(4)
_cell_angle_alpha                92.127(2)
_cell_angle_beta                 105.123(2)
_cell_angle_gamma                97.607(2)
_cell_volume                     627.58(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5878
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      29.99

_exptl_crystal_description       prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.310
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_T_max  0.9756
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14717
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.695
_diffrn_reflns_theta_max         32.037
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4157
_reflns_number_gt                2843
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0899P)²+0.0677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4157
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1639
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.82109(7) 0.87344(7) 1.10795(4) 0.07555(19) Uani 1 1 d . . . . .
O1 O 0.03003(16) 0.23136(17) 0.36033(9) 0.0580(3) Uani 1 1 d . . . . .
H1O H -0.0680 0.1750 0.3804 0.087 Uiso 1 1 d R U . . .
O2 O 0.30707(16) 0.40125(17) 0.45396(9) 0.0602(3) Uani 1 1 d . . . . .
O3 O -0.22080(16) 0.11924(17) 0.46415(9) 0.0579(3) Uani 1 1 d . . . . .
O4 O -0.16017(14) 0.20082(14) 0.64599(9) 0.0490(3) Uani 1 1 d . . . . .
N1 N 0.36697(16) 0.49751(16) 0.67278(10) 0.0430(3) Uani 1 1 d . . . . .
H1N H 0.4280 0.5020 0.6156 0.052 Uiso 1 1 d R U . . .
C1 C 0.47209(19) 0.58899(18) 0.77761(11) 0.0411(3) Uani 1 1 d . . . . .
C2 C 0.6773(2) 0.6165(2) 0.80537(13) 0.0514(4) Uani 1 1 d . . . . .
H2 H 0.7430 0.5763 0.7556 0.062 Uiso 1 1 calc R U . . .
C3 C 0.7836(2) 0.7036(2) 0.90701(14) 0.0558(4) Uani 1 1 d . . . . .
H3 H 0.9211 0.7226 0.9257 0.067 Uiso 1 1 calc R U . . .
C4 C 0.6857(2) 0.7623(2) 0.98070(12) 0.0503(3) Uani 1 1 d . . . . .
C5 C 0.4826(2) 0.7379(2) 0.95353(13) 0.0563(4) Uani 1 1 d . . . . .
H5 H 0.4175 0.7790 1.0033 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3755(2) 0.6514(2) 0.85128(13) 0.0518(4) Uani 1 1 d . . . . .
H6 H 0.2381 0.6353 0.8322 0.062 Uiso 1 1 calc R U . . .
C7 C 0.19032(19) 0.39709(18) 0.65399(11) 0.0405(3) Uani 1 1 d . . . . .
H7 H 0.1361 0.3870 0.7142 0.049 Uiso 1 1 calc R U . . .
C8 C 0.07928(18) 0.30660(17) 0.55509(11) 0.0391(3) Uani 1 1 d . . . . .
C9 C 0.1478(2) 0.3168(2) 0.45472(12) 0.0445(3) Uani 1 1 d . . . . .
C10 C -0.11189(19) 0.20145(18) 0.55024(12) 0.0419(3) Uani 1 1 d . . . . .
C11 C -0.3542(2) 0.1006(2) 0.64181(14) 0.0542(4) Uani 1 1 d . . . . .
H11A H -0.3632 -0.0249 0.6145 0.065 Uiso 1 1 calc R U . . .
H11B H -0.4576 0.1549 0.5925 0.065 Uiso 1 1 calc R U . . .
C12 C -0.3764(3) 0.1095(2) 0.75794(15) 0.0619(4) Uani 1 1 d . . . . .
H12A H -0.2737 0.0548 0.8058 0.093 Uiso 1 1 calc R U . . .
H12B H -0.5030 0.0453 0.7583 0.093 Uiso 1 1 calc R U . . .
H12C H -0.3668 0.2343 0.7841 0.093 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.7389(15) . ?
O1 C9 1.3335(17) . ?
O1 H1O 0.8621 . ?
O2 C9 1.2193(17) . ?
O3 C10 1.2318(16) . ?
O4 C10 1.3259(17) . ?
O4 C11 1.4618(16) . ?
N1 C7 1.3287(16) . ?
N1 C1 1.4214(16) . ?
N1 H1N 0.9250 . ?
C1 C6 1.382(2) . ?
C1 C2 1.3888(19) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(2) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.3736(17) . ?
C7 H7 0.9300 . ?
C8 C10 1.4570(17) . ?
C8 C9 1.4576(19) . ?
C11 C12 1.498(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C9 O1 H1O 103.8 . . ?
C10 O4 C11 115.47(11) . . ?
C7 N1 C1 123.63(12) . . ?
C7 N1 H1N 118.0 . . ?
C1 N1 H1N 118.3 . . ?
C6 C1 C2 119.73(13) . . ?
C6 C1 N1 121.77(12) . . ?
C2 C1 N1 118.49(13) . . ?
C3 C2 C1 119.86(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 119.88(14) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.76(14) . . ?
C5 C4 Cl1 119.75(13) . . ?
C3 C4 Cl1 119.47(12) . . ?
C4 C5 C6 119.45(15) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.30(14) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C8 126.92(12) . . ?
N1 C7 H7 116.5 . . ?
C8 C7 H7 116.5 . . ?
C7 C8 C10 119.28(12) . . ?
C7 C8 C9 121.15(11) . . ?
C10 C8 C9 119.56(12) . . ?
O2 C9 O1 119.20(13) . . ?
O2 C9 C8 122.48(13) . . ?
O1 C9 C8 118.32(12) . . ?
O3 C10 O4 122.34(12) . . ?
O3 C10 C8 122.89(13) . . ?
O4 C10 C8 114.78(11) . . ?
O4 C11 C12 107.14(13) . . ?
O4 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O4 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C7 N1 C1 C6 -30.0(2) . . . . ?
C7 N1 C1 C2 150.45(14) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
N1 C1 C2 C3 -179.46(13) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C2 C3 C4 Cl1 -179.47(12) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
Cl1 C4 C5 C6 179.10(12) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
N1 C1 C6 C5 179.11(14) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C1 N1 C7 C8 179.27(13) . . . . ?
N1 C7 C8 C10 179.60(13) . . . . ?
N1 C7 C8 C9 -1.5(2) . . . . ?
C7 C8 C9 O2 1.8(2) . . . . ?
C10 C8 C9 O2 -179.33(14) . . . . ?
C7 C8 C9 O1 -177.56(13) . . . . ?
C10 C8 C9 O1 1.3(2) . . . . ?
C11 O4 C10 O3 -1.8(2) . . . . ?
C11 O4 C10 C8 178.20(12) . . . . ?
C7 C8 C10 O3 178.83(13) . . . . ?
C9 C8 C10 O3 -0.1(2) . . . . ?
C7 C8 C10 O4 -1.18(19) . . . . ?
C9 C8 C10 O4 179.93(12) . . . . ?
C10 O4 C11 C12 177.62(13) . . . . ?

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MHE-4
_database_code_depnum_ccdc_archive 'CCDC 957110'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 (2E)-2-(ethoxycarbonyl)-3-[(3-nitrophenyl)amino]prop-2-enoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N2 O6'
_chemical_formula_weight         280.24

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                   11.4230(7)
_cell_length_b                   8.6148(5)
_cell_length_c                   13.9893(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.165(4)
_cell_angle_gamma                90.00
_cell_volume                     1274.91(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2476
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      23.54

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_T_max  0.9789
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         23.72
_reflns_number_total             1932
_reflns_number_gt                1490
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0422P)²+0.4489P] 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       0.0055(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1932
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.033
_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
O1 O 0.16307(18) 0.5836(2) 0.63846(15) 0.0726(5) Uani 1 1 d . . .
H1O H 0.133(3) 0.631(3) 0.578(2) 0.095(10) Uiso 1 1 d . . .
O2 O 0.24730(17) 0.3531(2) 0.68444(12) 0.0732(5) Uani 1 1 d . . .
O3 O 0.09001(15) 0.66272(17) 0.44889(12) 0.0639(5) Uani 1 1 d . . .
O4 O 0.12124(13) 0.49969(16) 0.33658(11) 0.0576(4) Uani 1 1 d . . .
O5 O 0.49179(16) -0.2922(2) 0.74392(13) 0.0721(5) Uani 1 1 d . . .
O6 O 0.5597(2) -0.4210(2) 0.64508(15) 0.1080(8) Uani 1 1 d . . .
N1 N 0.28271(16) 0.16836(19) 0.54384(14) 0.0465(4) Uani 1 1 d . . .
H1N H 0.295(2) 0.182(3) 0.6081(18) 0.060(7) Uiso 1 1 d . . .
N2 N 0.49581(17) -0.3175(2) 0.65984(15) 0.0570(5) Uani 1 1 d . . .
C1 C 0.32302(17) 0.0260(2) 0.51772(14) 0.0394(5) Uani 1 1 d . . .
C2 C 0.38287(17) -0.0764(2) 0.59700(14) 0.0411(5) Uani 1 1 d . . .
H2 H 0.3933 -0.0526 0.6646 0.049 Uiso 1 1 calc R . .
C3 C 0.42686(17) -0.2143(2) 0.57394(14) 0.0423(5) Uani 1 1 d . . .
C4 C 0.41162(19) -0.2564(2) 0.47504(16) 0.0507(5) Uani 1 1 d . . .
H4 H 0.4425 -0.3503 0.4615 0.061 Uiso 1 1 calc R . .
C5 C 0.3492(2) -0.1544(3) 0.39719(16) 0.0525(6) Uani 1 1 d . . .
H5 H 0.3360 -0.1809 0.3294 0.063 Uiso 1 1 calc R . .
C6 C 0.30569(19) -0.0141(2) 0.41689(15) 0.0473(5) Uani 1 1 d . . .
H6 H 0.2648 0.0540 0.3630 0.057 Uiso 1 1 calc R . .
C7 C 0.23002(17) 0.2855(2) 0.48121(15) 0.0439(5) Uani 1 1 d . . .
H7 H 0.2191 0.2741 0.4122 0.053 Uiso 1 1 calc R . .
C8 C 0.19013(18) 0.4223(2) 0.50920(15) 0.0456(5) Uani 1 1 d . . .
C9 C 0.2030(2) 0.4484(3) 0.61598(17) 0.0546(6) Uani 1 1 d . . .
C10 C 0.13023(19) 0.5390(2) 0.43101(16) 0.0482(5) Uani 1 1 d . . .
C11 C 0.0562(2) 0.6066(3) 0.25311(18) 0.0634(6) Uani 1 1 d . . .
H11A H 0.0975 0.7071 0.2666 0.076 Uiso 1 1 calc R . .
H11B H -0.0308 0.6201 0.2467 0.076 Uiso 1 1 calc R . .
C12 C 0.0604(3) 0.5390(3) 0.15686(19) 0.0766(8) Uani 1 1 d . . .
H12A H 0.1468 0.5230 0.1650 0.115 Uiso 1 1 calc R . .
H12B H 0.0207 0.6089 0.1004 0.115 Uiso 1 1 calc R . .
H12C H 0.0165 0.4415 0.1430 0.115 Uiso 1 1 calc R . .


_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 C9 1.331(3) . ?
O1 H1O 0.89(3) . ?
O2 C9 1.217(3) . ?
O3 C10 1.223(2) . ?
O4 C10 1.330(2) . ?
O4 C11 1.453(2) . ?
O5 N2 1.214(2) . ?
O6 N2 1.218(2) . ?
N1 C7 1.323(2) . ?
N1 C1 1.406(2) . ?
N1 H1N 0.86(2) . ?
N2 C3 1.463(3) . ?
C1 C2 1.379(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(3) . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.373(3) . ?
C7 H7 0.9300 . ?
C8 C10 1.453(3) . ?
C8 C9 1.462(3) . ?
C11 C12 1.485(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C9 O1 H1O 102.8(18) . . ?
C10 O4 C11 117.47(17) . . ?
C7 N1 C1 127.23(18) . . ?
C7 N1 H1N 116.0(15) . . ?
C1 N1 H1N 116.7(15) . . ?
O5 N2 O6 122.67(19) . . ?
O5 N2 C3 118.77(18) . . ?
O6 N2 C3 118.5(2) . . ?
C2 C1 C6 119.63(18) . . ?
C2 C1 N1 117.40(17) . . ?
C6 C1 N1 122.97(18) . . ?
C3 C2 C1 118.54(17) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 123.00(18) . . ?
C2 C3 N2 117.62(18) . . ?
C4 C3 N2 119.36(18) . . ?
C5 C4 C3 117.41(19) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C4 C5 C6 121.56(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 119.83(19) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N1 C7 C8 125.65(19) . . ?
N1 C7 H7 117.2 . . ?
C8 C7 H7 117.2 . . ?
C7 C8 C10 119.49(18) . . ?
C7 C8 C9 120.47(19) . . ?
C10 C8 C9 120.00(18) . . ?
O2 C9 O1 118.8(2) . . ?
O2 C9 C8 123.52(19) . . ?
O1 C9 C8 117.7(2) . . ?
O3 C10 O4 122.07(19) . . ?
O3 C10 C8 123.8(2) . . ?
O4 C10 C8 114.16(18) . . ?
O4 C11 C12 107.36(19) . . ?
O4 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C7 N1 C1 C2 176.09(18) . . . . ?
C7 N1 C1 C6 -3.5(3) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
N1 C1 C2 C3 -177.93(17) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C1 C2 C3 N2 176.89(17) . . . . ?
O5 N2 C3 C2 13.2(3) . . . . ?
O6 N2 C3 C2 -163.4(2) . . . . ?
O5 N2 C3 C4 -168.5(2) . . . . ?
O6 N2 C3 C4 14.9(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
N2 C3 C4 C5 -178.38(18) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
N1 C1 C6 C5 179.05(19) . . . . ?
C1 N1 C7 C8 179.03(19) . . . . ?
N1 C7 C8 C10 -178.14(19) . . . . ?
N1 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 O2 -0.8(3) . . . . ?
C10 C8 C9 O2 176.8(2) . . . . ?
C7 C8 C9 O1 179.75(19) . . . . ?
C10 C8 C9 O1 -2.7(3) . . . . ?
C11 O4 C10 O3 -2.7(3) . . . . ?
C11 O4 C10 C8 176.67(17) . . . . ?
C7 C8 C10 O3 178.7(2) . . . . ?
C9 C8 C10 O3 1.1(3) . . . . ?
C7 C8 C10 O4 -0.7(3) . . . . ?
C9 C8 C10 O4 -178.29(18) . . . . ?
C10 O4 C11 C12 179.07(19) . . . . ?

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
O1 H1O O3 0.89(3) 1.70(3) 2.554(2) 160(3) .
N1 H1N O2 0.86(2) 2.01(2) 2.677(2) 133(2) .
C7 H7 O4 0.93 2.29 2.673(2) 104.0 .
N1 H1N O5 0.86(2) 2.54(2) 3.130(2) 126.4(17) 2_656
C2 H2 O6 0.93 2.75 3.668(3) 167.7 2_656
C4 H4 O6 0.93 2.47 3.328(3) 154.2 3_646
C5 H5 O5 0.93 2.50 3.178(3) 129.7 4
C6 H6 O2 0.93 2.56 3.362(2) 145.0 4_565

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        23.72
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.030
