# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1044084'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(E)-2-methoxy-6-{[(3-nitrophenyl)imino]methyl}phenol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_formula_weight         272.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   12.8418(3)
_cell_length_b                   7.5487(2)
_cell_length_c                   26.4610(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2565.10(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3466
_cell_measurement_theta_min      3.3140
_cell_measurement_theta_max      67.4290

_exptl_crystal_description       plaquet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7327
_exptl_absorpt_correction_T_max  0.9656
_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     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6547
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         67.54
_reflns_number_total             2290
_reflns_number_gt                1948
_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
_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)+(0.0626P)²+0.3676P] 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       0.00088(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2290
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.33389(12) 0.7041(2) 0.63301(6) 0.0548(4) Uani 1 1 d . . .
H1 H 0.3025 0.8151 0.6323 0.066 Uiso 1 1 calc R . .
C2 C 0.37250(11) 0.62707(19) 0.58969(5) 0.0481(4) Uani 1 1 d . . .
C3 C 0.42001(11) 0.46361(19) 0.58884(5) 0.0484(4) Uani 1 1 d . . .
H3 H 0.4449 0.4158 0.5588 0.058 Uiso 1 1 calc R . .
C4 C 0.42979(10) 0.37180(18) 0.63423(5) 0.0449(3) Uani 1 1 d . . .
C5 C 0.39096(12) 0.4471(2) 0.67840(5) 0.0513(4) Uani 1 1 d . . .
H5 H 0.3971 0.3863 0.7088 0.062 Uiso 1 1 calc R . .
C6 C 0.34362(13) 0.6103(2) 0.67755(6) 0.0583(4) Uani 1 1 d . . .
H6 H 0.3178 0.6583 0.7074 0.070 Uiso 1 1 calc R . .
C7 C 0.52008(12) 0.1213(2) 0.60261(5) 0.0503(4) Uani 1 1 d . . .
C8 C 0.57044(11) -0.04836(19) 0.60942(5) 0.0467(3) Uani 1 1 d . . .
C9 C 0.61563(12) -0.1357(2) 0.56790(6) 0.0556(4) Uani 1 1 d . . .
H9 H 0.6126 -0.0843 0.5360 0.067 Uiso 1 1 calc R . .
C10 C 0.66388(13) -0.2955(2) 0.57408(6) 0.0594(4) Uani 1 1 d . . .
H10 H 0.6937 -0.3520 0.5464 0.071 Uiso 1 1 calc R . .
C11 C 0.66875(11) -0.3745(2) 0.62176(6) 0.0543(4) Uani 1 1 d . . .
H11 H 0.7013 -0.4837 0.6256 0.065 Uiso 1 1 calc R . .
C12 C 0.62543(10) -0.29120(19) 0.66317(5) 0.0477(3) Uani 1 1 d . . .
C13 C 0.57613(10) -0.12642(18) 0.65736(5) 0.0448(3) Uani 1 1 d . . .
C14 C 0.66827(14) -0.5256(2) 0.71961(7) 0.0637(4) Uani 1 1 d . . .
H14A H 0.6325 -0.6093 0.6986 0.096 Uiso 1 1 calc R . .
H14B H 0.6597 -0.5581 0.7544 0.096 Uiso 1 1 calc R . .
H14C H 0.7410 -0.5254 0.7113 0.096 Uiso 1 1 calc R . .
N1 N 0.47819(9) 0.20444(16) 0.63948(4) 0.0493(3) Uani 1 1 d . . .
N2 N 0.36428(11) 0.7262(2) 0.54202(5) 0.0611(4) Uani 1 1 d . . .
O1 O 0.39541(13) 0.65676(19) 0.50339(4) 0.0832(4) Uani 1 1 d . . .
O2 O 0.32788(14) 0.8753(2) 0.54325(5) 0.0940(5) Uani 1 1 d . . .
O3 O 0.53672(9) -0.04906(15) 0.69902(4) 0.0566(3) Uani 1 1 d . . .
O4 O 0.62651(9) -0.35445(14) 0.71163(4) 0.0588(3) Uani 1 1 d . . .
H7 H 0.5206(14) 0.170(3) 0.5668(8) 0.069(5) Uiso 1 1 d . . .
H3O H 0.5077(17) 0.055(3) 0.6880(8) 0.086(7) Uiso 1 1 d . . .


_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
C1 C2 1.378(2) . ?
C1 C6 1.381(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(2) . ?
C2 N2 1.4705(19) . ?
C3 C4 1.3925(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.3921(19) . ?
C4 N1 1.4148(19) . ?
C5 C6 1.374(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.2787(19) . ?
C7 C8 1.446(2) . ?
C7 H7 1.02(2) . ?
C8 C13 1.4007(19) . ?
C8 C9 1.407(2) . ?
C9 C10 1.366(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.397(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C12 O4 1.3683(18) . ?
C12 C13 1.404(2) . ?
C13 O3 1.3461(16) . ?
C14 O4 1.4144(19) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N2 O1 1.2164(18) . ?
N2 O2 1.2190(19) . ?
O3 H3O 0.92(2) . ?

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
C2 C1 C6 117.47(14) . . ?
C2 C1 H1 121.3 . . ?
C6 C1 H1 121.3 . . ?
C3 C2 C1 123.46(13) . . ?
C3 C2 N2 118.30(13) . . ?
C1 C2 N2 118.23(13) . . ?
C2 C3 C4 118.16(13) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 119.26(13) . . ?
C5 C4 N1 116.08(12) . . ?
C3 C4 N1 124.66(12) . . ?
C6 C5 C4 120.71(13) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.93(14) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N1 C7 C8 121.87(13) . . ?
N1 C7 H7 122.4(11) . . ?
C8 C7 H7 115.7(11) . . ?
C13 C8 C9 119.25(13) . . ?
C13 C8 C7 120.58(12) . . ?
C9 C8 C7 120.16(13) . . ?
C10 C9 C8 120.50(14) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.36(14) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.31(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O4 C12 C11 125.52(13) . . ?
O4 C12 C13 114.59(12) . . ?
C11 C12 C13 119.89(13) . . ?
O3 C13 C8 122.65(13) . . ?
O3 C13 C12 117.66(12) . . ?
C8 C13 C12 119.69(12) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 N1 C4 123.27(12) . . ?
O1 N2 O2 123.12(14) . . ?
O1 N2 C2 118.54(13) . . ?
O2 N2 C2 118.33(13) . . ?
C13 O3 H3O 105.3(14) . . ?
C12 O4 C14 117.55(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(2) . . . . ?
C6 C1 C2 N2 -179.07(14) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
N2 C2 C3 C4 178.58(12) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C2 C3 C4 N1 -178.87(13) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
N1 C4 C5 C6 179.22(13) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
N1 C7 C8 C13 -0.9(2) . . . . ?
N1 C7 C8 C9 179.99(14) . . . . ?
C13 C8 C9 C10 0.5(2) . . . . ?
C7 C8 C9 C10 179.61(14) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 O4 -179.17(14) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C9 C8 C13 O3 178.55(13) . . . . ?
C7 C8 C13 O3 -0.6(2) . . . . ?
C9 C8 C13 C12 -0.8(2) . . . . ?
C7 C8 C13 C12 -179.96(12) . . . . ?
O4 C12 C13 O3 0.48(18) . . . . ?
C11 C12 C13 O3 -178.84(13) . . . . ?
O4 C12 C13 C8 179.88(12) . . . . ?
C11 C12 C13 C8 0.6(2) . . . . ?
C8 C7 N1 C4 178.97(12) . . . . ?
C5 C4 N1 C7 -177.96(14) . . . . ?
C3 C4 N1 C7 1.4(2) . . . . ?
C3 C2 N2 O1 3.3(2) . . . . ?
C1 C2 N2 O1 -177.85(16) . . . . ?
C3 C2 N2 O2 -175.68(16) . . . . ?
C1 C2 N2 O2 3.2(2) . . . . ?
C11 C12 O4 C14 -5.2(2) . . . . ?
C13 C12 O4 C14 175.56(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        67.54
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1044161'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(E)-2-methoxy-6-{[(3-nitrophenyl)imino]methyl}phenol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_formula_weight         272.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7895(3)
_cell_length_b                   11.3446(10)
_cell_length_c                   12.0610(9)
_cell_angle_alpha                93.472(7)
_cell_angle_beta                 100.357(6)
_cell_angle_gamma                94.022(6)
_cell_volume                     641.28(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1645
_cell_measurement_theta_min      3.7480
_cell_measurement_theta_max      67.0770

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_T_max  0.9656
_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     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3990
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         66.60
_reflns_number_total             2242
_reflns_number_gt                1863
_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
_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)+(0.0706P)²+0.0244P] 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         2242
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.6886(3) 1.21312(15) 0.82815(14) 0.0697(4) Uani 1 1 d . . .
H1 H 0.8123 1.2814 0.8366 0.084 Uiso 1 1 calc R . .
C2 C 0.6554(3) 1.13584(13) 0.73289(12) 0.0599(4) Uani 1 1 d . . .
C3 C 0.4749(3) 1.03391(13) 0.71622(13) 0.0589(4) Uani 1 1 d . . .
H3 H 0.4578 0.9840 0.6509 0.071 Uiso 1 1 calc R . .
C4 C 0.3187(3) 1.00740(13) 0.79949(13) 0.0587(4) Uani 1 1 d . . .
C5 C 0.3516(3) 1.08430(14) 0.89616(13) 0.0656(4) Uani 1 1 d . . .
H5 H 0.2491 1.0667 0.9525 0.079 Uiso 1 1 calc R . .
C6 C 0.5334(4) 1.18618(16) 0.91012(15) 0.0721(4) Uani 1 1 d . . .
H6 H 0.5510 1.2367 0.9751 0.087 Uiso 1 1 calc R . .
C7 C -0.0039(3) 0.85684(14) 0.69686(13) 0.0622(4) Uani 1 1 d . . .
H7 H 0.0436 0.8846 0.6311 0.075 Uiso 1 1 calc R . .
C8 C -0.2195(3) 0.75931(13) 0.68769(13) 0.0611(4) Uani 1 1 d . . .
C9 C -0.3667(4) 0.71415(16) 0.58048(15) 0.0755(5) Uani 1 1 d . . .
H9 H -0.3189 0.7448 0.5159 0.091 Uiso 1 1 calc R . .
C10 C -0.5802(4) 0.62534(17) 0.57053(16) 0.0836(5) Uani 1 1 d . . .
H10 H -0.6777 0.5964 0.4993 0.100 Uiso 1 1 calc R . .
C11 C -0.6521(4) 0.57819(16) 0.66615(16) 0.0763(5) Uani 1 1 d . . .
H11 H -0.7967 0.5175 0.6585 0.092 Uiso 1 1 calc R . .
C12 C -0.5110(3) 0.62059(14) 0.77220(15) 0.0677(4) Uani 1 1 d . . .
C13 C -0.2946(3) 0.71256(14) 0.78400(13) 0.0620(4) Uani 1 1 d . . .
C14 C -0.7790(4) 0.48631(19) 0.8663(2) 0.0922(6) Uani 1 1 d . . .
H14A H -0.9593 0.5116 0.8317 0.138 Uiso 1 1 calc R . .
H14B H -0.7885 0.4645 0.9413 0.138 Uiso 1 1 calc R . .
H14C H -0.7345 0.4193 0.8222 0.138 Uiso 1 1 calc R . .
N1 N 0.1240(3) 0.90634(11) 0.79252(11) 0.0623(3) Uani 1 1 d . . .
N2 N 0.8249(3) 1.16284(13) 0.64593(12) 0.0690(4) Uani 1 1 d . . .
O1 O 0.8092(3) 1.09042(12) 0.56525(11) 0.0857(4) Uani 1 1 d . . .
O2 O 0.9771(3) 1.25487(13) 0.65822(12) 0.0957(4) Uani 1 1 d . . .
O3 O -0.1630(3) 0.75239(12) 0.88938(10) 0.0816(4) Uani 1 1 d . . .
O4 O -0.5633(3) 0.58056(12) 0.87172(11) 0.0900(4) Uani 1 1 d . . .
H3O H -0.036(5) 0.811(2) 0.880(2) 0.110(7) Uiso 1 1 d . . .


_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
C1 C6 1.376(2) . ?
C1 C2 1.381(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(2) . ?
C2 N2 1.471(2) . ?
C3 C4 1.391(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(2) . ?
C4 N1 1.4147(19) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.281(2) . ?
C7 C8 1.445(2) . ?
C7 H7 0.9300 . ?
C8 C13 1.399(2) . ?
C8 C9 1.405(2) . ?
C9 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 O4 1.367(2) . ?
C12 C13 1.400(2) . ?
C13 O3 1.349(2) . ?
C14 O4 1.423(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N2 O2 1.2161(18) . ?
N2 O1 1.2230(19) . ?
O3 H3O 0.89(3) . ?

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
C6 C1 C2 118.03(15) . . ?
C6 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
C3 C2 C1 123.22(14) . . ?
C3 C2 N2 118.45(13) . . ?
C1 C2 N2 118.33(14) . . ?
C2 C3 C4 118.36(14) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C5 118.94(14) . . ?
C3 C4 N1 124.11(13) . . ?
C5 C4 N1 116.95(13) . . ?
C6 C5 C4 121.31(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C1 C6 C5 120.14(15) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C8 122.19(14) . . ?
N1 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C13 C8 C9 119.15(14) . . ?
C13 C8 C7 121.18(14) . . ?
C9 C8 C7 119.59(15) . . ?
C10 C9 C8 120.33(16) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.40(16) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.49(16) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O4 C12 C11 125.40(15) . . ?
O4 C12 C13 114.74(14) . . ?
C11 C12 C13 119.86(16) . . ?
O3 C13 C8 122.15(14) . . ?
O3 C13 C12 118.10(14) . . ?
C8 C13 C12 119.75(14) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 N1 C4 121.26(13) . . ?
O2 N2 O1 123.04(14) . . ?
O2 N2 C2 118.75(14) . . ?
O1 N2 C2 118.20(13) . . ?
C13 O3 H3O 105.5(16) . . ?
C12 O4 C14 117.89(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(2) . . . . ?
C6 C1 C2 N2 -178.79(14) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
N2 C2 C3 C4 178.82(13) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 N1 179.36(13) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
N1 C4 C5 C6 -179.05(14) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
N1 C7 C8 C13 -1.3(2) . . . . ?
N1 C7 C8 C9 175.48(15) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C7 C8 C9 C10 -177.10(16) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 O4 -179.75(17) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C9 C8 C13 O3 -179.60(15) . . . . ?
C7 C8 C13 O3 -2.8(2) . . . . ?
C9 C8 C13 C12 1.1(2) . . . . ?
C7 C8 C13 C12 177.92(13) . . . . ?
O4 C12 C13 O3 -0.4(2) . . . . ?
C11 C12 C13 O3 179.43(16) . . . . ?
O4 C12 C13 C8 178.99(14) . . . . ?
C11 C12 C13 C8 -1.2(2) . . . . ?
C8 C7 N1 C4 -175.14(13) . . . . ?
C3 C4 N1 C7 -26.9(2) . . . . ?
C5 C4 N1 C7 152.69(15) . . . . ?
C3 C2 N2 O2 177.40(14) . . . . ?
C1 C2 N2 O2 -3.6(2) . . . . ?
C3 C2 N2 O1 -3.7(2) . . . . ?
C1 C2 N2 O1 175.26(14) . . . . ?
C11 C12 O4 C14 0.8(3) . . . . ?
C13 C12 O4 C14 -179.45(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.033
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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/access/V1 
# 
# Audit and citation data items may have 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_p3_lt
_database_code_depnum_ccdc_archive 'CCDC 1052602'

_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        P3-PolymorphI-Pbca
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 N2 O4'
_chemical_formula_sum            'C14 H12 N2 O4'
_chemical_formula_weight         272.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   12.4915(15)
_cell_length_b                   7.5972(14)
_cell_length_c                   26.1737(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2483.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      29.3

_exptl_crystal_description       plaquet
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.988
_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  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, 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            9181
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         29.27
_reflns_number_total             3027
_reflns_number_gt                2561
_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
_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)+(0.0437P)²+0.7710P] 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         3388
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H2O H 0.4922 0.5449 0.6886 0.039 Uiso 0.60 1 d P A 1
H1N H 0.5201 0.6616 0.6709 0.050 Uiso 0.40 1 d P B 2
O1 O 0.37427(7) 0.14115(12) 0.71150(3) 0.0185(2) Uani 1 1 d . . .
O2 O 0.46486(7) 0.44672(11) 0.69871(3) 0.0180(2) Uani 1 1 d . . .
C3 C 0.58091(10) 0.96012(16) 0.58830(5) 0.0159(3) Uani 1 1 d . . .
H3 H 0.5571 0.9126 0.5576 0.019 Uiso 1 1 calc R . .
N2 N 0.63621(8) 1.22511(15) 0.54214(4) 0.0185(2) Uani 1 1 d . . .
N1 N 0.52251(8) 0.69899(14) 0.63877(4) 0.0163(2) Uani 1 1 d . . .
C7 C 0.48075(10) 0.61646(17) 0.60086(5) 0.0166(3) Uani 1 1 d . . .
O4 O 0.67160(9) 1.37603(13) 0.54416(4) 0.0287(3) Uani 1 1 d . . .
O3 O 0.60670(8) 1.15462(13) 0.50228(3) 0.0259(2) Uani 1 1 d . . .
C12 C 0.37504(9) 0.20327(16) 0.66237(5) 0.0148(3) Uani 1 1 d . . .
C2 C 0.62746(10) 1.12470(17) 0.59003(5) 0.0158(3) Uani 1 1 d . . .
C11 C 0.33102(10) 0.11958(17) 0.62041(5) 0.0171(3) Uani 1 1 d . . .
H11 H 0.2981 0.0106 0.6244 0.021 Uiso 1 1 calc R . .
C13 C 0.42477(9) 0.36836(16) 0.65650(5) 0.0143(3) Uani 1 1 d . . .
C4 C 0.57070(10) 0.86710(16) 0.63408(5) 0.0148(3) Uani 1 1 d . . .
C5 C 0.60872(10) 0.94145(17) 0.67946(5) 0.0165(3) Uani 1 1 d . . .
H5 H 0.6024 0.8794 0.7099 0.020 Uiso 1 1 calc R . .
C9 C 0.38464(10) 0.35795(17) 0.56561(5) 0.0180(3) Uani 1 1 d . . .
H9 H 0.3877 0.4089 0.5333 0.022 Uiso 1 1 calc R . .
C14 C 0.33080(11) -0.03055(17) 0.71927(5) 0.0200(3) Uani 1 1 d . . .
H14A H 0.2560 -0.0300 0.7109 0.030 Uiso 1 1 calc R . .
H14B H 0.3397 -0.0638 0.7544 0.030 Uiso 1 1 calc R . .
H14C H 0.3675 -0.1133 0.6978 0.030 Uiso 1 1 calc R . .
C8 C 0.43051(10) 0.44592(16) 0.60787(5) 0.0150(3) Uani 1 1 d . . .
C10 C 0.33561(10) 0.19795(17) 0.57188(5) 0.0188(3) Uani 1 1 d . . .
H10 H 0.3053 0.1412 0.5439 0.023 Uiso 1 1 calc R . .
C1 C 0.66525(10) 1.20165(17) 0.63449(5) 0.0174(3) Uani 1 1 d . . .
H1 H 0.6960 1.3131 0.6342 0.021 Uiso 1 1 calc R . .
C6 C 0.65558(11) 1.10620(17) 0.67951(5) 0.0196(3) Uani 1 1 d . . .
H6 H 0.6809 1.1536 0.7100 0.023 Uiso 1 1 calc R . .
H7 H 0.4798(12) 0.662(2) 0.5666(6) 0.024(4) Uiso 1 1 d . . .


_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 C12 1.3698(14) . ?
O1 C14 1.4275(15) . ?
O2 C13 1.3513(14) . ?
O2 H2O 0.8618 . ?
C3 C2 1.3796(18) . ?
C3 C4 1.3968(17) . ?
C3 H3 0.9300 . ?
N2 O3 1.2293(14) . ?
N2 O4 1.2300(14) . ?
N2 C2 1.4714(16) . ?
N1 C7 1.2845(17) . ?
N1 C4 1.4172(16) . ?
N1 H1N 0.8881 . ?
C7 C8 1.4513(18) . ?
C7 H7 0.960(16) . ?
C12 C11 1.3830(17) . ?
C12 C13 1.4081(18) . ?
C2 C1 1.3853(18) . ?
C11 C10 1.4042(18) . ?
C11 H11 0.9300 . ?
C13 C8 1.4044(17) . ?
C4 C5 1.3986(17) . ?
C5 C6 1.3818(19) . ?
C5 H5 0.9300 . ?
C9 C10 1.3710(19) . ?
C9 C8 1.4136(17) . ?
C9 H9 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C10 H10 0.9300 . ?
C1 C6 1.3887(18) . ?
C1 H1 0.9300 . ?
C6 H6 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
C12 O1 C14 116.83(10) . . ?
C13 O2 H2O 106.1 . . ?
C2 C3 C4 117.97(11) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
O3 N2 O4 123.38(11) . . ?
O3 N2 C2 118.35(11) . . ?
O4 N2 C2 118.27(10) . . ?
C7 N1 C4 123.05(11) . . ?
C7 N1 H1N 124.2 . . ?
C4 N1 H1N 112.6 . . ?
N1 C7 C8 120.91(11) . . ?
N1 C7 H7 123.4(9) . . ?
C8 C7 H7 115.7(9) . . ?
O1 C12 C11 125.75(11) . . ?
O1 C12 C13 114.36(10) . . ?
C11 C12 C13 119.89(11) . . ?
C3 C2 C1 123.61(12) . . ?
C3 C2 N2 118.25(11) . . ?
C1 C2 N2 118.13(11) . . ?
C12 C11 C10 120.48(12) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
O2 C13 C8 122.50(11) . . ?
O2 C13 C12 117.82(11) . . ?
C8 C13 C12 119.68(11) . . ?
C3 C4 C5 119.55(12) . . ?
C3 C4 N1 124.69(11) . . ?
C5 C4 N1 115.76(11) . . ?
C6 C5 C4 120.69(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C10 C9 C8 120.44(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C8 C9 119.35(11) . . ?
C13 C8 C7 120.74(11) . . ?
C9 C8 C7 119.90(11) . . ?
C9 C10 C11 120.16(12) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C2 C1 C6 117.56(12) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
C5 C6 C1 120.61(12) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C7 C8 -178.80(11) . . . . ?
C14 O1 C12 C11 4.66(18) . . . . ?
C14 O1 C12 C13 -176.25(10) . . . . ?
C4 C3 C2 C1 0.56(19) . . . . ?
C4 C3 C2 N2 -178.61(10) . . . . ?
O3 N2 C2 C3 -3.63(17) . . . . ?
O4 N2 C2 C3 175.58(11) . . . . ?
O3 N2 C2 C1 177.15(11) . . . . ?
O4 N2 C2 C1 -3.64(17) . . . . ?
O1 C12 C11 C10 179.12(12) . . . . ?
C13 C12 C11 C10 0.07(18) . . . . ?
O1 C12 C13 O2 -0.38(16) . . . . ?
C11 C12 C13 O2 178.77(11) . . . . ?
O1 C12 C13 C8 -179.96(11) . . . . ?
C11 C12 C13 C8 -0.81(18) . . . . ?
C2 C3 C4 C5 -0.87(18) . . . . ?
C2 C3 C4 N1 178.42(11) . . . . ?
C7 N1 C4 C3 -1.64(19) . . . . ?
C7 N1 C4 C5 177.67(12) . . . . ?
C3 C4 C5 C6 0.41(19) . . . . ?
N1 C4 C5 C6 -178.93(11) . . . . ?
O2 C13 C8 C9 -178.58(11) . . . . ?
C12 C13 C8 C9 0.98(18) . . . . ?
O2 C13 C8 C7 0.06(18) . . . . ?
C12 C13 C8 C7 179.61(11) . . . . ?
C10 C9 C8 C13 -0.43(19) . . . . ?
C10 C9 C8 C7 -179.07(11) . . . . ?
N1 C7 C8 C13 1.08(19) . . . . ?
N1 C7 C8 C9 179.70(12) . . . . ?
C8 C9 C10 C11 -0.31(19) . . . . ?
C12 C11 C10 C9 0.49(19) . . . . ?
C3 C2 C1 C6 0.22(19) . . . . ?
N2 C2 C1 C6 179.39(11) . . . . ?
C4 C5 C6 C1 0.39(19) . . . . ?
C2 C1 C6 C5 -0.70(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.893
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.046
_iucr_refine_instruction_details 
;
TITL bn_p3-PBCA-LT in Pbca
CELL  0.71073  12.4915   7.5972  26.1737   90.000   90.000   90.000
ZERR     8.00   0.0015   0.0014   0.0018    0.000    0.000    0.000
LATT   1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  - X, 1/2 + Y, 1/2 - Z
SYMM  1/2 + X, 1/2 - Y, - Z
SFAC  C        2.31000 20.84392  1.02000 10.20751   1.58860   0.56870 =
         0.86500  51.65125   0.21560   0.003   0.002    11.500   0.770  12.011
SFAC  H        0.49300 10.51091  0.32291 26.12573   0.14019   3.14236 =
         0.04081  57.79977   0.00304   0.000   0.000     0.620   0.320   1.008
SFAC  N       12.21261  0.00570  3.13220  9.89331   2.01250  28.99754 =
         1.16630   0.58260 -11.52901   0.006   0.003    19.600   0.700  14.007
SFAC  O        3.04850 13.27711  2.28680  5.70111   1.54630   0.32390 =
         0.86700  32.90894   0.25080   0.011   0.006    32.500   0.660  15.999
UNIT  98   84   16   32
MERG   2
FMAP   2
PLAN   10
ACTA    50.00
HTAB    2.00000
BOND   $H
CONF
L.S.  10
WGHT    0.043700    0.771000
FVAR       5.71669
PART    1
H2O   2    0.492206    0.544856    0.688587    10.60000    0.03877
PART    2
H1N   2    0.520100    0.661600    0.670900    10.40000    0.05000
PART 0
AFIX   0
O1    4    0.374269    0.141149    0.711496    11.00000    0.02316    0.01750 =
         0.01474    0.00275   -0.00110   -0.00480
O2    4    0.464862    0.446723    0.698711    11.00000    0.02268    0.01843 =
         0.01294   -0.00073   -0.00236   -0.00482
C3    1    0.580911    0.960118    0.588304    11.00000    0.01482    0.01886 =
         0.01407   -0.00220   -0.00042    0.00016
AFIX  43
H3    2    0.557066    0.912568    0.557603    11.00000   -1.20000
AFIX   0
N2    3    0.636212    1.225108    0.542143    11.00000    0.01666    0.02146 =
         0.01744    0.00185    0.00020   -0.00252
N1    3    0.522509    0.698994    0.638771    11.00000    0.01609    0.01717 =
         0.01571    0.00048    0.00073   -0.00018
C7    1    0.480753    0.616458    0.600859    11.00000    0.01683    0.01822 =
         0.01465    0.00280    0.00040    0.00265
O4    4    0.671600    1.376028    0.544155    11.00000    0.03704    0.02337 =
         0.02563    0.00528   -0.00123   -0.01333
O3    4    0.606699    1.154617    0.502282    11.00000    0.03370    0.02921 =
         0.01491    0.00139   -0.00247   -0.00668
C12   1    0.375038    0.203272    0.662369    11.00000    0.01226    0.01814 =
         0.01394    0.00091    0.00071    0.00278
C2    1    0.627456    1.124696    0.590030    11.00000    0.01327    0.01957 =
         0.01451    0.00238    0.00057    0.00130
C11   1    0.331017    0.119578    0.620412    11.00000    0.01472    0.01637 =
         0.02018   -0.00149   -0.00070    0.00029
AFIX  43
H11   2    0.298132    0.010604    0.624373    11.00000   -1.20000
AFIX   0
C13   1    0.424771    0.368362    0.656497    11.00000    0.01158    0.01747 =
         0.01384   -0.00266   -0.00077    0.00237
C4    1    0.570695    0.867098    0.634077    11.00000    0.01237    0.01670 =
         0.01527   -0.00049    0.00103    0.00274
C5    1    0.608716    0.941452    0.679464    11.00000    0.01813    0.01829 =
         0.01320    0.00065    0.00027    0.00528
AFIX  43
H5    2    0.602391    0.879360    0.709937    11.00000   -1.20000
AFIX   0
C9    1    0.384643    0.357947    0.565610    11.00000    0.01902    0.02195 =
         0.01292    0.00102   -0.00101    0.00259
AFIX  43
H9    2    0.387749    0.408950    0.533343    11.00000   -1.20000
AFIX   0
C14   1    0.330803   -0.030546    0.719273    11.00000    0.02187    0.01721 =
         0.02101    0.00269    0.00090   -0.00383
AFIX 137
H14A  2    0.255995   -0.029959    0.710870    11.00000   -1.50000
H14B  2    0.339702   -0.063848    0.754398    11.00000   -1.50000
H14C  2    0.367479   -0.113297    0.697780    11.00000   -1.50000
AFIX   0
;

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH/EtOH'
