# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_PA-NAM
_database_code_depnum_ccdc_archive 'CCDC 1473194'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Picolinic acid : Nicotinamide'
_chemical_name_common            ?
_chemical_melting_point          388
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N3 O3'
_chemical_formula_weight         245.24

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   'P 1 21/c 1'

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

_cell_length_a                   11.9096(10)
_cell_length_b                   5.5828(4)
_cell_length_c                   17.2361(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.291(9)
_cell_angle_gamma                90.00
_cell_volume                     1119.74(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3372
_cell_measurement_theta_min      3.4930
_cell_measurement_theta_max      29.6340

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62020
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_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            17368
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2193
_reflns_number_gt                1756
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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)+(0.0476P)²+2.9646P] 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       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2193
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1790
_refine_ls_wR_factor_gt          0.1707
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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 0.4859(3) 0.3134(6) 0.14571(19) 0.0169(7) Uani 1 1 d . . .
C2 C 0.5759(3) 0.1514(6) 0.12156(19) 0.0164(7) Uani 1 1 d . . .
C3 C 0.6978(3) -0.1818(6) 0.1576(2) 0.0203(8) Uani 1 1 d . . .
H3 H 0.7247 -0.3033 0.1937 0.024 Uiso 1 1 calc R . .
C4 C 0.7408(3) -0.1574(6) 0.0900(2) 0.0206(8) Uani 1 1 d . . .
H4 H 0.7972 -0.2611 0.0801 0.025 Uiso 1 1 calc R . .
C5 C 0.6985(3) 0.0250(6) 0.0365(2) 0.0207(8) Uani 1 1 d . . .
H5 H 0.7254 0.0416 -0.0101 0.025 Uiso 1 1 calc R . .
C6 C 0.6162(3) 0.1816(6) 0.05290(19) 0.0191(8) Uani 1 1 d . . .
H6 H 0.5885 0.3056 0.0180 0.023 Uiso 1 1 calc R . .
C7 C 0.7923(3) -0.7852(6) -0.18407(19) 0.0187(8) Uani 1 1 d . . .
C8 C 0.8643(3) -0.5793(6) -0.14576(19) 0.0182(8) Uani 1 1 d . . .
C9 C 0.8353(3) -0.4374(7) -0.0866(2) 0.0213(8) Uani 1 1 d . . .
H9 H 0.7669 -0.4712 -0.0711 0.026 Uiso 1 1 calc R . .
C10 C 0.9968(3) -0.2106(7) -0.0748(2) 0.0234(8) Uani 1 1 d . . .
H10 H 1.0425 -0.0846 -0.0509 0.028 Uiso 1 1 calc R . .
C11 C 1.0338(3) -0.3400(7) -0.1329(2) 0.0211(8) Uani 1 1 d . . .
H11 H 1.1024 -0.3017 -0.1475 0.025 Uiso 1 1 calc R . .
C12 C 0.9664(3) -0.5283(7) -0.1690(2) 0.0205(8) Uani 1 1 d . . .
H12 H 0.9892 -0.6190 -0.2082 0.025 Uiso 1 1 calc R . .
N1 N 0.6172(2) -0.0300(5) 0.17130(16) 0.0165(6) Uani 1 1 d . . .
N2 N 0.8989(3) -0.2557(6) -0.05066(18) 0.0246(7) Uani 1 1 d . . .
N3 N 0.6884(2) -0.8152(6) -0.16682(18) 0.0195(7) Uani 1 1 d . . .
O1 O 0.4516(2) 0.2506(4) 0.20675(13) 0.0182(6) Uani 1 1 d . . .
O2 O 0.4559(2) 0.4918(5) 0.10265(14) 0.0237(6) Uani 1 1 d . . .
O3 O 0.8298(2) -0.9216(5) -0.22903(15) 0.0255(6) Uani 1 1 d . . .
H1 H 0.580(3) -0.065(8) 0.217(2) 0.035(12) Uiso 1 1 d . . .
H3A H 0.653(3) -0.696(7) -0.147(2) 0.018(10) Uiso 1 1 d . . .
H3B H 0.634(4) -0.936(9) -0.194(3) 0.041(12) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0177(17) 0.0164(18) 0.0152(16) -0.0022(14) 0.0005(13) -0.0002(14)
C2 0.0181(17) 0.0150(17) 0.0152(16) 0.0011(13) 0.0017(13) -0.0039(14)
C3 0.0239(18) 0.0159(18) 0.0208(17) -0.0009(14) 0.0038(14) 0.0007(15)
C4 0.0209(18) 0.0189(18) 0.0230(18) -0.0034(15) 0.0071(14) 0.0014(15)
C5 0.0228(18) 0.0228(19) 0.0182(17) 0.0008(15) 0.0085(14) -0.0007(15)
C6 0.0218(18) 0.0197(18) 0.0157(16) 0.0023(14) 0.0038(14) -0.0002(15)
C7 0.0224(18) 0.0179(18) 0.0159(16) 0.0005(14) 0.0040(14) 0.0004(14)
C8 0.0216(17) 0.0162(18) 0.0165(16) 0.0013(14) 0.0030(14) 0.0030(14)
C9 0.0177(17) 0.025(2) 0.0223(17) -0.0023(15) 0.0063(14) -0.0012(15)
C10 0.0241(19) 0.022(2) 0.0243(18) -0.0041(15) 0.0053(15) -0.0023(16)
C11 0.0187(17) 0.024(2) 0.0216(18) -0.0004(15) 0.0072(14) -0.0031(15)
C12 0.0219(18) 0.0231(19) 0.0173(16) -0.0016(14) 0.0057(14) 0.0032(15)
N1 0.0181(14) 0.0183(15) 0.0142(13) 0.0003(12) 0.0061(11) 0.0002(12)
N2 0.0246(16) 0.0249(17) 0.0258(16) -0.0079(13) 0.0085(13) -0.0030(14)
N3 0.0176(15) 0.0179(16) 0.0242(16) -0.0048(13) 0.0071(13) -0.0022(13)
O1 0.0229(13) 0.0158(13) 0.0182(12) -0.0013(10) 0.0098(10) -0.0005(10)
O2 0.0283(14) 0.0224(14) 0.0220(13) 0.0056(11) 0.0086(11) 0.0072(11)
O3 0.0287(14) 0.0228(14) 0.0280(13) -0.0085(11) 0.0127(11) -0.0046(11)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.248(4) . ?
C1 O1 1.257(4) . ?
C1 C2 1.527(5) . ?
C2 N1 1.350(4) . ?
C2 C6 1.379(5) . ?
C3 N1 1.339(4) . ?
C3 C4 1.376(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.387(5) . ?
C7 O3 1.236(4) . ?
C7 N3 1.344(4) . ?
C7 C8 1.501(5) . ?
C8 C12 1.388(5) . ?
C8 C9 1.391(5) . ?
C9 N2 1.337(5) . ?
C10 N2 1.343(5) . ?
C10 C11 1.380(5) . ?
C11 C12 1.387(5) . ?

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
O2 C1 O1 128.2(3) . . ?
O2 C1 C2 116.0(3) . . ?
O1 C1 C2 115.8(3) . . ?
N1 C2 C6 119.4(3) . . ?
N1 C2 C1 116.9(3) . . ?
C6 C2 C1 123.7(3) . . ?
N1 C3 C4 119.8(3) . . ?
C3 C4 C5 119.1(3) . . ?
C6 C5 C4 119.8(3) . . ?
C2 C6 C5 119.2(3) . . ?
O3 C7 N3 122.4(3) . . ?
O3 C7 C8 120.0(3) . . ?
N3 C7 C8 117.7(3) . . ?
C12 C8 C9 117.6(3) . . ?
C12 C8 C7 118.9(3) . . ?
C9 C8 C7 123.4(3) . . ?
N2 C9 C8 124.6(3) . . ?
N2 C10 C11 123.9(3) . . ?
C10 C11 C12 118.6(3) . . ?
C11 C12 C8 119.0(3) . . ?
C3 N1 C2 122.7(3) . . ?
C9 N2 C10 116.3(3) . . ?

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
O2 C1 C2 N1 174.1(3) . . . . ?
O1 C1 C2 N1 -5.6(4) . . . . ?
O2 C1 C2 C6 -5.7(5) . . . . ?
O1 C1 C2 C6 174.6(3) . . . . ?
N1 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 1.5(5) . . . . ?
N1 C2 C6 C5 -0.1(5) . . . . ?
C1 C2 C6 C5 179.8(3) . . . . ?
C4 C5 C6 C2 -1.2(5) . . . . ?
O3 C7 C8 C12 7.7(5) . . . . ?
N3 C7 C8 C12 -173.1(3) . . . . ?
O3 C7 C8 C9 -171.1(3) . . . . ?
N3 C7 C8 C9 8.1(5) . . . . ?
C12 C8 C9 N2 -0.1(5) . . . . ?
C7 C8 C9 N2 178.8(3) . . . . ?
N2 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 C8 0.2(5) . . . . ?
C9 C8 C12 C11 -0.2(5) . . . . ?
C7 C8 C12 C11 -179.1(3) . . . . ?
C4 C3 N1 C2 -0.8(5) . . . . ?
C6 C2 N1 C3 1.1(5) . . . . ?
C1 C2 N1 C3 -178.8(3) . . . . ?
C8 C9 N2 C10 0.4(5) . . . . ?
C11 C10 N2 C9 -0.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.074
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'Isopropyl alcohol'
####################################################################### 
# 
# 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_PA-INAM
_database_code_depnum_ccdc_archive 'CCDC 1473195'
_audit_update_record             
;
2016-04-09 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Picolinic acid : Isonicotinamide'
_chemical_name_common            ?
_chemical_melting_point          393
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N3 O3'
_chemical_formula_weight         245.24

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   6.9822(4)
_cell_length_b                   7.1747(5)
_cell_length_c                   12.7208(9)
_cell_angle_alpha                76.298(6)
_cell_angle_beta                 83.080(5)
_cell_angle_gamma                69.036(6)
_cell_volume                     577.68(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3183
_cell_measurement_theta_min      3.1020
_cell_measurement_theta_max      29.9120

_exptl_crystal_description       needle-shape
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_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            8598
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         30.35
_reflns_number_total             3065
_reflns_number_gt                2279
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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)+(0.0511P)²+0.1280P] 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         3065
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.2213(2) 0.6373(2) 0.90142(12) 0.0181(3) Uani 1 1 d . . .
C2 C 0.1609(2) 0.8371(2) 0.82096(11) 0.0171(3) Uani 1 1 d . . .
C3 C 0.0982(2) 0.9995(2) 0.64525(12) 0.0243(4) Uani 1 1 d . . .
H3 H 0.0888 0.9945 0.5737 0.029 Uiso 1 1 calc R . .
C4 C 0.0579(2) 1.1889(2) 0.66982(13) 0.0236(3) Uani 1 1 d . . .
H4 H 0.0223 1.3070 0.6159 0.028 Uiso 1 1 calc R . .
C5 C 0.0715(2) 1.1987(2) 0.77540(13) 0.0217(3) Uani 1 1 d . . .
H5 H 0.0466 1.3232 0.7941 0.026 Uiso 1 1 calc R . .
C6 C 0.1230(2) 1.0190(2) 0.85305(12) 0.0180(3) Uani 1 1 d . . .
H6 H 0.1319 1.0204 0.9252 0.022 Uiso 1 1 calc R . .
C7 C 0.5446(2) 0.2445(2) 0.62276(12) 0.0179(3) Uani 1 1 d . . .
C8 C 0.5928(2) 0.0531(2) 0.71000(12) 0.0162(3) Uani 1 1 d . . .
C9 C 0.6220(2) -0.1292(2) 0.67953(12) 0.0188(3) Uani 1 1 d . . .
H9 H 0.6089 -0.1309 0.6079 0.023 Uiso 1 1 calc R . .
C10 C 0.6704(2) -0.3069(2) 0.75723(12) 0.0196(3) Uani 1 1 d . . .
H10 H 0.6872 -0.4281 0.7368 0.024 Uiso 1 1 calc R . .
C11 C 0.6666(2) -0.1370(2) 0.88994(12) 0.0188(3) Uani 1 1 d . . .
H11 H 0.6823 -0.1398 0.9619 0.023 Uiso 1 1 calc R . .
C12 C 0.6154(2) 0.0486(2) 0.81753(12) 0.0178(3) Uani 1 1 d . . .
H12 H 0.5966 0.1681 0.8404 0.021 Uiso 1 1 calc R . .
N1 N 0.14976(18) 0.82436(19) 0.71857(10) 0.0214(3) Uani 1 1 d . . .
N2 N 0.69449(18) -0.31288(18) 0.86121(10) 0.0186(3) Uani 1 1 d . . .
N3 N 0.4452(2) 0.4219(2) 0.65206(12) 0.0212(3) Uani 1 1 d . . .
O1 O 0.28113(16) 0.47273(15) 0.87433(8) 0.0239(3) Uani 1 1 d . . .
O2 O 0.20414(17) 0.65747(17) 1.00193(9) 0.0253(3) Uani 1 1 d . . .
O3 O 0.60021(17) 0.22934(16) 0.52818(8) 0.0264(3) Uani 1 1 d . . .
H2 H 0.246(4) 0.513(4) 1.055(2) 0.089(9) Uiso 1 1 d . . .
H3A H 0.417(3) 0.534(3) 0.5993(16) 0.035(5) Uiso 1 1 d . . .
H3B H 0.390(3) 0.437(3) 0.7218(16) 0.037(5) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0159(6) 0.0197(7) 0.0180(7) -0.0047(6) 0.0011(6) -0.0051(5)
C2 0.0131(6) 0.0205(7) 0.0174(7) -0.0049(6) 0.0003(5) -0.0049(5)
C3 0.0210(7) 0.0332(9) 0.0160(8) -0.0048(7) -0.0028(6) -0.0057(6)
C4 0.0183(7) 0.0242(8) 0.0228(8) 0.0021(6) -0.0027(6) -0.0047(6)
C5 0.0167(7) 0.0190(7) 0.0290(9) -0.0058(6) 0.0005(6) -0.0055(5)
C6 0.0167(7) 0.0204(7) 0.0174(7) -0.0056(6) 0.0010(6) -0.0064(5)
C7 0.0191(7) 0.0182(7) 0.0169(7) -0.0037(6) 0.0003(6) -0.0071(5)
C8 0.0138(6) 0.0172(7) 0.0163(7) -0.0025(6) 0.0016(5) -0.0049(5)
C9 0.0176(7) 0.0204(7) 0.0173(7) -0.0047(6) -0.0004(6) -0.0049(5)
C10 0.0213(7) 0.0173(7) 0.0206(8) -0.0045(6) -0.0020(6) -0.0062(5)
C11 0.0178(7) 0.0218(8) 0.0153(7) -0.0036(6) -0.0011(6) -0.0050(5)
C12 0.0171(6) 0.0175(7) 0.0188(8) -0.0061(6) 0.0018(6) -0.0055(5)
N1 0.0193(6) 0.0253(7) 0.0183(7) -0.0062(5) -0.0011(5) -0.0048(5)
N2 0.0174(6) 0.0185(6) 0.0181(6) -0.0014(5) -0.0012(5) -0.0054(5)
N3 0.0285(7) 0.0163(7) 0.0164(7) -0.0018(5) 0.0009(6) -0.0064(5)
O1 0.0310(6) 0.0183(6) 0.0212(6) -0.0071(4) 0.0001(5) -0.0055(4)
O2 0.0382(6) 0.0189(6) 0.0152(6) -0.0040(4) 0.0004(5) -0.0055(5)
O3 0.0380(6) 0.0205(6) 0.0160(6) -0.0034(4) 0.0035(5) -0.0063(5)

_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 O1 1.2220(17) . ?
C1 O2 1.3070(17) . ?
C1 C2 1.502(2) . ?
C2 N1 1.3404(18) . ?
C2 C6 1.3855(19) . ?
C3 N1 1.334(2) . ?
C3 C4 1.389(2) . ?
C4 C5 1.377(2) . ?
C5 C6 1.385(2) . ?
C7 O3 1.2366(17) . ?
C7 N3 1.3307(18) . ?
C7 C8 1.506(2) . ?
C8 C12 1.3873(19) . ?
C8 C9 1.3900(19) . ?
C9 C10 1.375(2) . ?
C10 N2 1.3420(18) . ?
C11 N2 1.3379(18) . ?
C11 C12 1.381(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
O1 C1 O2 123.83(14) . . ?
O1 C1 C2 122.58(13) . . ?
O2 C1 C2 113.59(12) . . ?
N1 C2 C6 123.74(14) . . ?
N1 C2 C1 115.45(12) . . ?
C6 C2 C1 120.80(13) . . ?
N1 C3 C4 123.63(14) . . ?
C5 C4 C3 118.82(15) . . ?
C4 C5 C6 118.55(14) . . ?
C5 C6 C2 118.58(14) . . ?
O3 C7 N3 123.45(14) . . ?
O3 C7 C8 118.65(12) . . ?
N3 C7 C8 117.89(13) . . ?
C12 C8 C9 118.71(13) . . ?
C12 C8 C7 123.63(13) . . ?
C9 C8 C7 117.62(13) . . ?
C10 C9 C8 118.80(13) . . ?
N2 C10 C9 122.87(13) . . ?
N2 C11 C12 122.95(13) . . ?
C11 C12 C8 118.65(13) . . ?
C3 N1 C2 116.67(13) . . ?
C11 N2 C10 118.01(12) . . ?

_diffrn_measured_fraction_theta_max 0.879
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.055
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'Ethyl acetate'
