# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_tai_17_3b_t
_database_code_depnum_ccdc_archive 'CCDC 1987225'
loop_
_audit_author_name
_audit_author_address
'Ian Scowen'
;University of Lincoln
United Kingdom
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (R, S)-2-hydroxysuccinic acid nicotinamide 
;
_chemical_name_common            
;
(DL)-malic acid nicotinamide
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N4 O12'
_chemical_formula_weight         512.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

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

_cell_length_a                   18.629(3)
_cell_length_b                   5.2842(8)
_cell_length_c                   22.841(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2248.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4167
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      22.51

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.078
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   'SADABS - Bruker AXS, Madison WI'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16447
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         24.66
_reflns_number_total             3047
_reflns_number_gt                2538
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0638P)²+1.3125P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.2(17)
_refine_ls_number_reflns         3047
_refine_ls_number_parameters     335
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.5074(2) 1.0130(7) 0.16534(19) 0.0249(10) Uani 1 1 d . . .
N2A N 0.5858(2) 0.4130(7) 0.06101(17) 0.0248(10) Uani 1 1 d . . .
O1A O 0.66443(17) 0.3191(6) 0.13339(14) 0.0263(8) Uani 1 1 d . . .
C1A C 0.5816(2) 0.6483(9) 0.1526(2) 0.0154(11) Uani 1 1 d . . .
C2A C 0.5953(3) 0.6464(9) 0.2121(2) 0.0240(12) Uani 1 1 d . . .
H2A H 0.6258 0.5204 0.2283 0.029 Uiso 1 1 calc R . .
C3A C 0.5649(2) 0.8269(9) 0.2479(2) 0.0270(12) Uani 1 1 d . . .
H3A H 0.5737 0.8272 0.2889 0.032 Uiso 1 1 calc R . .
C4A C 0.5211(3) 1.0079(9) 0.2224(2) 0.0267(12) Uani 1 1 d . . .
H4A H 0.4999 1.1333 0.2467 0.032 Uiso 1 1 calc R . .
C6A C 0.5366(2) 0.8345(9) 0.1309(2) 0.0205(11) Uani 1 1 d . . .
H6A H 0.5260 0.8362 0.0902 0.025 Uiso 1 1 calc R . .
C7A C 0.6137(3) 0.4479(9) 0.11418(19) 0.0190(11) Uani 1 1 d . . .
O1B O 0.60576(17) 0.3284(6) 0.82181(14) 0.0261(8) Uani 1 1 d . . .
N1B N 0.7637(2) 1.0239(7) 0.79436(17) 0.0211(9) Uani 1 1 d . . .
C1B C 0.6874(2) 0.6620(9) 0.8052(2) 0.0214(11) Uani 1 1 d . . .
C2B C 0.6646(3) 0.6907(9) 0.7478(2) 0.0270(12) Uani 1 1 d . . .
H2B H 0.6302 0.5777 0.7318 0.032 Uiso 1 1 calc R . .
C3B C 0.6921(3) 0.8833(10) 0.7144(2) 0.0340(14) Uani 1 1 d . . .
H3B H 0.6775 0.9043 0.6748 0.041 Uiso 1 1 calc R . .
C4B C 0.7418(3) 1.0470(10) 0.7395(2) 0.0286(13) Uani 1 1 d . . .
H4B H 0.7607 1.1807 0.7163 0.034 Uiso 1 1 calc R . .
C6B C 0.7379(3) 0.8351(9) 0.8267(2) 0.0252(12) Uani 1 1 d . . .
H6B H 0.7544 0.8170 0.8658 0.030 Uiso 1 1 calc R . .
C7B C 0.6573(3) 0.4521(9) 0.8423(2) 0.0223(11) Uani 1 1 d . . .
O12C O 0.55867(18) 1.0832(6) 0.95395(15) 0.0296(8) Uani 1 1 d . . .
O2C O 0.47859(16) 0.6895(6) 0.99794(13) 0.0230(8) Uani 1 1 d . . .
O42C O 0.38436(16) 0.9355(7) 0.90544(14) 0.0270(8) Uani 1 1 d . . .
N2B N 0.6862(2) 0.4094(7) 0.89411(17) 0.0247(10) Uani 1 1 d . . .
O11C O 0.54969(18) 0.9256(6) 0.86322(13) 0.0247(8) Uani 1 1 d . . .
O41C O 0.35636(17) 0.6512(6) 0.83608(15) 0.0251(8) Uani 1 1 d . . .
C1C C 0.5405(2) 0.9178(9) 0.9205(2) 0.0198(11) Uani 1 1 d . . .
C2C C 0.5070(2) 0.6704(9) 0.94055(19) 0.0184(11) Uani 1 1 d . . .
H2C H 0.5476 0.5473 0.9434 0.022 Uiso 1 1 calc R . .
C3C C 0.4547(3) 0.5555(8) 0.89716(19) 0.0192(11) Uani 1 1 d . . .
H3C1 H 0.4812 0.5057 0.8614 0.023 Uiso 1 1 calc R . .
H3C2 H 0.4336 0.4005 0.9144 0.023 Uiso 1 1 calc R . .
C4C C 0.3954(2) 0.7344(9) 0.8808(2) 0.0172(11) Uani 1 1 d . . .
O2D O 0.29875(16) 0.3245(5) -0.04230(13) 0.0226(8) Uani 1 1 d . . .
O11D O 0.22083(17) 0.0869(6) 0.08951(14) 0.0264(8) Uani 1 1 d . . .
O12D O 0.21828(19) -0.0736(6) -0.00077(15) 0.0323(9) Uani 1 1 d . . .
O41D O 0.39152(18) 0.0746(7) 0.04857(15) 0.0287(9) Uani 1 1 d . . .
O42D O 0.42114(16) 0.3558(6) 0.11821(14) 0.0240(8) Uani 1 1 d . . .
C1D C 0.2346(2) 0.0948(9) 0.0323(2) 0.0187(11) Uani 1 1 d . . .
C2D C 0.2688(2) 0.3422(9) 0.01518(19) 0.0188(11) Uani 1 1 d . . .
H2D H 0.2287 0.4673 0.0123 0.023 Uiso 1 1 calc R . .
C3D C 0.3213(2) 0.4514(8) 0.0590(2) 0.0176(11) Uani 1 1 d . . .
H3D1 H 0.3418 0.6092 0.0428 0.021 Uiso 1 1 calc R . .
H3D2 H 0.2949 0.4960 0.0952 0.021 Uiso 1 1 calc R . .
C4D C 0.3811(2) 0.2753(9) 0.0743(2) 0.0181(11) Uani 1 1 d . . .
H2AN H 0.5466 0.4994 0.0460 0.12(3) Uiso 1 1 d . . .
H3AN H 0.6019 0.2892 0.0325 0.023(12) Uiso 1 1 d . . .
H2BN H 0.6756 0.2680 0.9182 0.036(14) Uiso 1 1 d . . .
H3BN H 0.7268 0.4992 0.9106 0.034(14) Uiso 1 1 d . . .
H11C H 0.5766 1.0893 0.8503 0.046(16) Uiso 1 1 d . . .
H41C H 0.3237 0.7966 0.8206 0.054(17) Uiso 1 1 d . . .
H2CO H 0.4416 0.8294 1.0013 0.10(3) Uiso 1 1 d . . .
H2DO H 0.3278 0.1562 -0.0380 0.055(17) Uiso 1 1 d . . .
H11D H 0.2095 -0.0815 0.1051 0.12(3) Uiso 1 1 d . . .
H42D H 0.4670 0.2055 0.1365 0.10(3) 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
N1A C4A 1.329(7) . ?
N1A C6A 1.343(6) . ?
N2A C7A 1.334(6) . ?
N2A H2AN 0.927(4) . ?
N2A H3AN 0.970(4) . ?
O1A C7A 1.245(6) . ?
C1A C2A 1.383(7) . ?
C1A C6A 1.384(7) . ?
C1A C7A 1.500(7) . ?
C2A C3A 1.378(7) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.386(7) . ?
C3A H3A 0.9500 . ?
C4A H4A 0.9500 . ?
C6A H6A 0.9500 . ?
O1B C7B 1.251(6) . ?
N1B C4B 1.324(7) . ?
N1B C6B 1.331(6) . ?
C1B C6B 1.400(7) . ?
C1B C2B 1.387(7) . ?
C1B C7B 1.503(7) . ?
C2B C3B 1.372(7) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.391(7) . ?
C3B H3B 0.9500 . ?
C4B H4B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B N2B 1.321(6) . ?
O12C C1C 1.208(5) . ?
O2C C2C 1.417(5) . ?
O2C H2CO 1.014(3) . ?
O42C C4C 1.220(6) . ?
N2B H2BN 0.949(4) . ?
N2B H3BN 0.969(4) . ?
O11C C1C 1.321(6) . ?
O11C H11C 1.042(3) . ?
O41C C4C 1.329(6) . ?
O41C H41C 1.042(3) . ?
C1C C2C 1.520(7) . ?
C2C C3C 1.516(6) . ?
C2C H2C 1.0000 . ?
C3C C4C 1.502(7) . ?
C3C H3C1 0.9900 . ?
C3C H3C2 0.9900 . ?
O2D C2D 1.430(5) . ?
O2D H2DO 1.046(3) . ?
O11D C1D 1.333(6) . ?
O11D H11D 0.982(3) . ?
O12D C1D 1.206(5) . ?
O41D C4D 1.228(5) . ?
O42D C4D 1.319(6) . ?
O42D H42D 1.239(3) . ?
C1D C2D 1.506(7) . ?
C2D C3D 1.514(6) . ?
C2D H2D 1.0000 . ?
C3D C4D 1.494(6) . ?
C3D H3D1 0.9900 . ?
C3D H3D2 0.9900 . ?

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
C4A N1A C6A 118.9(4) . . ?
C7A N2A H2AN 125.1(4) . . ?
C7A N2A H3AN 125.7(4) . . ?
H2AN N2A H3AN 109.1(4) . . ?
C2A C1A C6A 118.0(4) . . ?
C2A C1A C7A 119.7(4) . . ?
C6A C1A C7A 122.3(4) . . ?
C1A C2A C3A 120.2(5) . . ?
C1A C2A H2A 119.9 . . ?
C3A C2A H2A 119.9 . . ?
C2A C3A C4A 118.0(5) . . ?
C2A C3A H3A 121.0 . . ?
C4A C3A H3A 121.0 . . ?
N1A C4A C3A 122.6(5) . . ?
N1A C4A H4A 118.7 . . ?
C3A C4A H4A 118.7 . . ?
N1A C6A C1A 122.3(4) . . ?
N1A C6A H6A 118.9 . . ?
C1A C6A H6A 118.9 . . ?
O1A C7A N2A 122.8(4) . . ?
O1A C7A C1A 118.9(4) . . ?
N2A C7A C1A 118.4(4) . . ?
C4B N1B C6B 118.9(4) . . ?
C6B C1B C2B 117.7(5) . . ?
C6B C1B C7B 122.5(4) . . ?
C2B C1B C7B 119.8(4) . . ?
C3B C2B C1B 119.6(5) . . ?
C3B C2B H2B 120.2 . . ?
C1B C2B H2B 120.2 . . ?
C2B C3B C4B 118.7(5) . . ?
C2B C3B H3B 120.6 . . ?
C4B C3B H3B 120.6 . . ?
N1B C4B C3B 122.6(5) . . ?
N1B C4B H4B 118.7 . . ?
C3B C4B H4B 118.7 . . ?
N1B C6B C1B 122.6(5) . . ?
N1B C6B H6B 118.7 . . ?
C1B C6B H6B 118.7 . . ?
O1B C7B N2B 124.0(4) . . ?
O1B C7B C1B 117.5(5) . . ?
N2B C7B C1B 118.5(4) . . ?
C2C O2C H2CO 112.1(3) . . ?
C7B N2B H2BN 124.7(4) . . ?
C7B N2B H3BN 125.7(4) . . ?
H2BN N2B H3BN 108.9(4) . . ?
C1C O11C H11C 111.6(3) . . ?
C4C O41C H41C 109.7(3) . . ?
O12C C1C O11C 124.5(5) . . ?
O12C C1C C2C 123.2(5) . . ?
O11C C1C C2C 112.2(4) . . ?
O2C C2C C1C 111.8(4) . . ?
O2C C2C C3C 113.2(4) . . ?
C1C C2C C3C 114.3(4) . . ?
O2C C2C H2C 105.5 . . ?
C1C C2C H2C 105.5 . . ?
C3C C2C H2C 105.5 . . ?
C4C C3C C2C 112.5(4) . . ?
C4C C3C H3C1 109.1 . . ?
C2C C3C H3C1 109.1 . . ?
C4C C3C H3C2 109.1 . . ?
C2C C3C H3C2 109.1 . . ?
H3C1 C3C H3C2 107.8 . . ?
O42C C4C O41C 123.4(4) . . ?
O42C C4C C3C 123.9(4) . . ?
O41C C4C C3C 112.7(4) . . ?
C2D O2D H2DO 99.9(3) . . ?
C1D O11D H11D 115.2(4) . . ?
C4D O42D H42D 116.0(3) . . ?
O12D C1D O11D 122.9(4) . . ?
O12D C1D C2D 125.8(4) . . ?
O11D C1D C2D 111.3(4) . . ?
O2D C2D C1D 110.3(4) . . ?
O2D C2D C3D 112.4(4) . . ?
C1D C2D C3D 115.6(4) . . ?
O2D C2D H2D 105.9 . . ?
C1D C2D H2D 105.9 . . ?
C3D C2D H2D 105.9 . . ?
C4D C3D C2D 113.6(4) . . ?
C4D C3D H3D1 108.9 . . ?
C2D C3D H3D1 108.9 . . ?
C4D C3D H3D2 108.9 . . ?
C2D C3D H3D2 108.9 . . ?
H3D1 C3D H3D2 107.7 . . ?
O41D C4D O42D 123.6(4) . . ?
O41D C4D C3D 122.9(4) . . ?
O42D C4D C3D 113.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_theta_full        24.66
_diffrn_measured_fraction_theta_full 0.864
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.059

# start Validation Reply Form
_vrf_PLAT029_tai_17_3b_t         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.864 Why?  
RESPONSE: only small, weakly diffracting crystal avaialable
;
# end Validation Reply Form

####################################################################### 
# 
# 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_tai_23_3b_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1987228'
loop_
_audit_author_name
_audit_author_address
'Ian Scowen'
;University of Lincoln
United Kingdom
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (R)-2-hydroxysuccinic acid nicotinamide 
;
_chemical_name_common            
;
L-malic acid nicotinamide
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N4 O7'
_chemical_formula_weight         378.34
_chemical_absolute_configuration syn

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   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   4.7631(2)
_cell_length_b                   8.8253(4)
_cell_length_c                   10.6620(5)
_cell_angle_alpha                96.829(3)
_cell_angle_beta                 95.279(3)
_cell_angle_gamma                105.603(3)
_cell_volume                     424.99(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2766
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      31.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             198
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_T_max  0.7630
_exptl_absorpt_process_details   'SADABS - Bruker AXS, Madison WI'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7290
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         32.00
_reflns_number_total             4822
_reflns_number_gt                3952
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0488P)²+0.0293P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(8)
_refine_ls_number_reflns         4822
_refine_ls_number_parameters     312
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
C1A C 0.1666(4) 0.4681(2) 0.72139(16) 0.0216(4) Uani 1 1 d . . .
C2A C -0.0768(4) 0.3865(2) 0.79272(18) 0.0230(4) Uani 1 1 d . . .
C3A C 0.0485(4) 0.3156(2) 0.90122(18) 0.0233(4) Uani 1 1 d . . .
C4A C -0.2008(4) 0.2188(2) 0.96529(17) 0.0197(3) Uani 1 1 d . . .
O3A O 0.2443(3) 0.43750(19) 0.99183(15) 0.0419(4) Uani 1 1 d . . .
O11A O 0.2789(3) 0.62058(15) 0.75973(13) 0.0276(3) Uani 1 1 d . . .
O12A O 0.2547(3) 0.39399(15) 0.63790(13) 0.0348(3) Uani 1 1 d . . .
O41A O -0.3719(3) 0.09341(15) 0.89882(12) 0.0280(3) Uani 1 1 d . . .
O42A O -0.2151(3) 0.26782(15) 1.07717(12) 0.0288(3) Uani 1 1 d . . .
H21A H -0.181(5) 0.465(3) 0.830(2) 0.027(6) Uiso 1 1 d . . .
H22A H -0.215(5) 0.300(3) 0.732(2) 0.041(7) Uiso 1 1 d . . .
H31A H 0.161(5) 0.245(2) 0.8654(19) 0.021(5) Uiso 1 1 d . . .
H3AO H 0.158(6) 0.431(3) 1.059(3) 0.059(8) Uiso 1 1 d . . .
C1B C 0.9067(4) 0.8875(2) 0.67159(19) 0.0260(4) Uani 1 1 d . . .
C2B C 1.1382(5) 0.9435(2) 0.6049(2) 0.0282(4) Uani 1 1 d . . .
C3B C 1.1739(4) 0.8483(2) 0.49756(18) 0.0234(4) Uani 1 1 d . . .
C4B C 0.9729(4) 0.7000(2) 0.46021(16) 0.0191(3) Uani 1 1 d . . .
C5B C 0.7496(4) 0.6506(2) 0.53478(17) 0.0209(4) Uani 1 1 d . . .
C6B C 0.9986(4) 0.5944(2) 0.34285(17) 0.0205(3) Uani 1 1 d . . .
O1B O 1.2391(3) 0.60440(17) 0.30486(13) 0.0301(3) Uani 1 1 d . . .
N1B N 0.7179(3) 0.74203(18) 0.63827(14) 0.0224(3) Uani 1 1 d . . .
N2B N 0.7487(4) 0.4922(2) 0.28407(16) 0.0262(4) Uani 1 1 d . . .
H1B H 0.874(5) 0.945(3) 0.744(2) 0.028(6) Uiso 1 1 d . . .
H2B H 1.276(5) 1.045(3) 0.630(2) 0.030(6) Uiso 1 1 d . . .
H3B H 1.342(5) 0.885(3) 0.448(2) 0.023(5) Uiso 1 1 d . . .
H5B H 0.614(5) 0.540(3) 0.516(2) 0.035(6) Uiso 1 1 d . . .
H21B H 0.573(5) 0.497(3) 0.301(2) 0.022(5) Uiso 1 1 d . . .
H22B H 0.763(5) 0.432(3) 0.216(2) 0.029(6) Uiso 1 1 d . . .
C1C C -0.9611(4) -0.1846(2) 0.99043(18) 0.0233(4) Uani 1 1 d . . .
C2C C -1.1894(4) -0.2457(2) 1.05709(18) 0.0252(4) Uani 1 1 d . . .
C3C C -1.2274(4) -0.1534(2) 1.16557(17) 0.0216(4) Uani 1 1 d . . .
C4C C -1.0306(3) -0.0041(2) 1.20742(16) 0.0176(3) Uani 1 1 d . . .
C5C C -0.8061(4) 0.0509(2) 1.13587(16) 0.0178(3) Uani 1 1 d . . .
C6C C -1.0697(4) 0.0983(2) 1.32357(16) 0.0195(3) Uani 1 1 d . . .
O1C O -1.3194(3) 0.08488(17) 1.35349(13) 0.0268(3) Uani 1 1 d . . .
N1C N -0.7768(3) -0.03842(17) 1.02970(14) 0.0198(3) Uani 1 1 d . . .
N2C N -0.8278(4) 0.20127(19) 1.38788(16) 0.0240(3) Uani 1 1 d . . .
H1C H -0.917(4) -0.244(3) 0.915(2) 0.023(5) Uiso 1 1 d . . .
H2C H -1.317(5) -0.349(3) 1.026(2) 0.037(7) Uiso 1 1 d . . .
H3C H 0.615(5) 0.803(3) 0.213(2) 0.026(6) Uiso 1 1 d . . .
H5C H -0.670(4) 0.148(2) 1.1575(18) 0.011(4) Uiso 1 1 d . . .
H21C H -0.668(5) 0.189(3) 1.373(2) 0.025(6) Uiso 1 1 d . . .
H22C H -0.841(6) 0.257(4) 1.461(3) 0.048(8) Uiso 1 1 d . . .
H11O H 0.4395 0.6676 0.7178 0.041(10) Uiso 0.70 1 d P A 1
H1BN H 0.5695 0.7129 0.6780 0.03(2) Uiso 0.30 1 d P B 2
H1CN H -0.6500 -0.0046 0.9895 0.018(7) Uiso 0.70 1 d P C 1
H41O H -0.5186 0.0292 0.9576 0.008(14) Uiso 0.30 1 d P D 2


_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
C1A O12A 1.214(2) . ?
C1A O11A 1.306(2) . ?
C1A C2A 1.511(3) . ?
C2A C3A 1.527(2) . ?
C2A H21A 1.02(2) . ?
C2A H22A 0.98(3) . ?
C3A O3A 1.417(2) . ?
C3A C4A 1.532(2) . ?
C3A H31A 0.99(2) . ?
C4A O42A 1.234(2) . ?
C4A O41A 1.270(2) . ?
O3A H3AO 0.86(3) . ?
O11A H11O 0.9453(13) . ?
O41A H41O 1.0742(12) . ?
C1B N1B 1.340(2) . ?
C1B C2B 1.379(3) . ?
C1B H1B 0.92(2) . ?
C2B C3B 1.388(3) . ?
C2B H2B 0.95(2) . ?
C3B C4B 1.386(2) . ?
C3B H3B 1.00(2) . ?
C4B C5B 1.394(2) . ?
C4B C6B 1.503(2) . ?
C5B N1B 1.333(2) . ?
C5B H5B 1.00(3) . ?
C6B O1B 1.235(2) . ?
C6B N2B 1.332(3) . ?
N1B H1BN 0.8534(15) . ?
N2B H21B 0.89(2) . ?
N2B H22B 0.86(3) . ?
C1C N1C 1.344(2) . ?
C1C C2C 1.377(3) . ?
C1C H1C 0.98(2) . ?
C2C C3C 1.389(3) . ?
C2C H2C 0.95(3) . ?
C3C C4C 1.390(2) . ?
C4C C5C 1.385(2) . ?
C4C C6C 1.500(2) . ?
C5C N1C 1.341(2) . ?
C5C H5C 0.92(2) . ?
C6C O1C 1.239(2) . ?
C6C N2C 1.329(2) . ?
N1C H1CN 0.7866(14) . ?
N2C H21C 0.83(2) . ?
N2C H22C 0.88(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
O12A C1A O11A 123.50(17) . . ?
O12A C1A C2A 121.43(16) . . ?
O11A C1A C2A 115.02(15) . . ?
C1A C2A C3A 110.18(14) . . ?
C1A C2A H21A 110.7(13) . . ?
C3A C2A H21A 108.9(12) . . ?
C1A C2A H22A 107.2(14) . . ?
C3A C2A H22A 109.2(14) . . ?
H21A C2A H22A 110.7(18) . . ?
O3A C3A C2A 110.44(14) . . ?
O3A C3A C4A 110.23(15) . . ?
C2A C3A C4A 110.28(13) . . ?
O3A C3A H31A 107.9(12) . . ?
C2A C3A H31A 108.5(11) . . ?
C4A C3A H31A 109.4(12) . . ?
O42A C4A O41A 125.75(16) . . ?
O42A C4A C3A 117.37(15) . . ?
O41A C4A C3A 116.88(15) . . ?
C3A O3A H3AO 103.0(19) . . ?
C1A O11A H11O 113.52(14) . . ?
C4A O41A H41O 109.54(13) . . ?
N1B C1B C2B 122.17(19) . . ?
N1B C1B H1B 114.5(14) . . ?
C2B C1B H1B 123.2(14) . . ?
C1B C2B C3B 119.28(19) . . ?
C1B C2B H2B 122.2(14) . . ?
C3B C2B H2B 118.6(14) . . ?
C4B C3B C2B 118.71(18) . . ?
C4B C3B H3B 120.1(13) . . ?
C2B C3B H3B 121.2(13) . . ?
C3B C4B C5B 118.42(16) . . ?
C3B C4B C6B 120.57(16) . . ?
C5B C4B C6B 121.01(16) . . ?
N1B C5B C4B 122.56(17) . . ?
N1B C5B H5B 116.6(14) . . ?
C4B C5B H5B 120.7(14) . . ?
O1B C6B N2B 123.11(18) . . ?
O1B C6B C4B 120.91(16) . . ?
N2B C6B C4B 115.98(16) . . ?
C5B N1B C1B 118.80(16) . . ?
C5B N1B H1BN 120.69(17) . . ?
C1B N1B H1BN 120.17(17) . . ?
C6B N2B H21B 123.2(14) . . ?
C6B N2B H22B 115.9(16) . . ?
H21B N2B H22B 120(2) . . ?
N1C C1C C2C 120.73(17) . . ?
N1C C1C H1C 115.7(13) . . ?
C2C C1C H1C 123.5(13) . . ?
C1C C2C C3C 118.92(17) . . ?
C1C C2C H2C 118.2(15) . . ?
C3C C2C H2C 122.8(15) . . ?
C4C C3C C2C 119.88(17) . . ?
C3C C4C C5C 118.38(16) . . ?
C3C C4C C6C 120.71(15) . . ?
C5C C4C C6C 120.84(15) . . ?
N1C C5C C4C 120.90(16) . . ?
N1C C5C H5C 116.2(12) . . ?
C4C C5C H5C 122.9(12) . . ?
O1C C6C N2C 123.78(18) . . ?
O1C C6C C4C 119.57(17) . . ?
N2C C6C C4C 116.64(16) . . ?
C5C N1C C1C 121.14(16) . . ?
C5C N1C H1CN 119.51(17) . . ?
C1C N1C H1CN 119.35(17) . . ?
C6C N2C H21C 117.8(15) . . ?
C6C N2C H22C 118.8(19) . . ?
H21C N2C H22C 120(2) . . ?

_diffrn_measured_fraction_theta_max 0.930
_diffrn_reflns_theta_full        32.00
_diffrn_measured_fraction_theta_full 0.930
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044

# start Validation Reply Form
_vrf_PLAT029_tai_23_3b_2_0m      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.930 Why?  
RESPONSE: weakly diffracting crytal
;
# end Validation Reply Form

####################################################################### 
# 
# 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_tai_31_3c_0m
_database_code_depnum_ccdc_archive 'CCDC 1987227'
loop_
_audit_author_name
_audit_author_address
'Ian Scowen'
;University of Lincoln
United Kingdom
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (R,S)-2-hydroxy-3-phenylpropionic acid isonicotinamide 
;
_chemical_name_common            
;
 DL-phenyllactic acid isonicotinamide
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O4'
_chemical_formula_weight         288.30

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.3395(5)
_cell_length_b                   11.3914(15)
_cell_length_c                   11.6131(13)
_cell_angle_alpha                78.849(9)
_cell_angle_beta                 82.062(8)
_cell_angle_gamma                81.076(9)
_cell_volume                     680.36(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1347
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      21.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6817
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   'SADABS - Bruker AXS, Madison WI'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17283
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3114
_reflns_number_gt                1870
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.3233P] 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         3114
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_restrained_S_all      0.790
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.004

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
C3A C 0.5568(4) 0.91605(19) 0.30732(17) 0.0195(4) Uani 1 1 d . . .
C4A C 0.7409(4) 0.9456(2) 0.36602(19) 0.0235(5) Uani 1 1 d . . .
H4A H 0.8535 1.0015 0.3271 0.028 Uiso 1 1 calc R . .
C6A C 0.5230(4) 0.96609(19) 0.17923(18) 0.0226(5) Uani 1 1 d . . .
C2A C 0.3954(4) 0.8351(2) 0.36814(19) 0.0236(5) Uani 1 1 d . . .
H2A H 0.2670 0.8136 0.3301 0.028 Uiso 1 1 calc R . .
C1A C 0.4237(4) 0.7858(2) 0.48528(19) 0.0244(5) Uani 1 1 d . . .
H1A H 0.3118 0.7306 0.5265 0.029 Uiso 1 1 calc R . .
C5A C 0.7566(4) 0.8913(2) 0.48343(19) 0.0247(5) Uani 1 1 d . . .
H5A H 0.8837 0.9109 0.5236 0.030 Uiso 1 1 calc R . .
N1A N 0.6015(3) 0.81280(17) 0.54253(16) 0.0246(4) Uani 1 1 d . . .
N2A N 0.7176(4) 1.01270(19) 0.11262(18) 0.0292(5) Uani 1 1 d . . .
O1A O 0.3217(3) 0.95971(15) 0.14091(14) 0.0309(4) Uani 1 1 d . . .
C2B C 0.0748(4) 0.3314(2) 1.08198(19) 0.0245(5) Uani 1 1 d . . .
H2B H 0.1041 0.4175 1.0732 0.029 Uiso 1 1 calc R . .
C3B C 0.2572(4) 0.2722(2) 0.99022(19) 0.0252(5) Uani 1 1 d . . .
H3B1 H 0.4341 0.2670 1.0092 0.030 Uiso 1 1 calc R . .
H3B2 H 0.2196 0.1889 0.9948 0.030 Uiso 1 1 calc R . .
C1B C 0.1221(4) 0.2668(2) 1.20597(19) 0.0232(5) Uani 1 1 d . . .
C31B C 0.2383(4) 0.3400(2) 0.86577(19) 0.0233(5) Uani 1 1 d . . .
C32B C 0.0605(4) 0.3194(2) 0.79738(19) 0.0263(5) Uani 1 1 d . . .
H32B H -0.0533 0.2619 0.8293 0.032 Uiso 1 1 calc R . .
C36B C 0.4008(4) 0.4253(2) 0.8171(2) 0.0283(5) Uani 1 1 d . . .
H36B H 0.5217 0.4412 0.8630 0.034 Uiso 1 1 calc R . .
C34B C 0.2126(4) 0.4662(2) 0.6350(2) 0.0311(6) Uani 1 1 d . . .
H34B H 0.2039 0.5086 0.5564 0.037 Uiso 1 1 calc R . .
C33B C 0.0484(4) 0.3822(2) 0.6830(2) 0.0301(6) Uani 1 1 d . . .
H33B H -0.0739 0.3675 0.6372 0.036 Uiso 1 1 calc R . .
C35B C 0.3890(4) 0.4880(2) 0.7020(2) 0.0315(6) Uani 1 1 d . . .
H35B H 0.5023 0.5456 0.6696 0.038 Uiso 1 1 calc R . .
O2B O 0.3489(3) 0.27587(16) 1.23314(14) 0.0318(4) Uani 1 1 d . . .
O1B O -0.0353(3) 0.21338(16) 1.27253(14) 0.0345(4) Uani 1 1 d . . .
O3B O -0.1788(3) 0.32847(18) 1.06132(15) 0.0375(5) Uani 1 1 d . . .
H2BO H 0.367(5) 0.242(3) 1.315(3) 0.062(9) Uiso 1 1 d . . .
H1BN H 0.706(6) 1.033(3) 0.031(3) 0.066(10) Uiso 1 1 d . . .
H2BN H 0.859(5) 1.015(3) 0.139(3) 0.046(8) Uiso 1 1 d . . .
H3BO H -0.274(7) 0.312(4) 1.133(4) 0.094(13) 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
C3A C2A 1.386(3) . ?
C3A C4A 1.386(3) . ?
C3A C6A 1.511(3) . ?
C4A C5A 1.392(3) . ?
C4A H4A 0.9500 . ?
C6A O1A 1.236(2) . ?
C6A N2A 1.323(3) . ?
C2A C1A 1.387(3) . ?
C2A H2A 0.9500 . ?
C1A N1A 1.335(3) . ?
C1A H1A 0.9500 . ?
C5A N1A 1.338(3) . ?
C5A H5A 0.9500 . ?
N2A H1BN 0.94(3) . ?
N2A H2BN 0.86(3) . ?
C2B O3B 1.414(2) . ?
C2B C1B 1.521(3) . ?
C2B C3B 1.526(3) . ?
C2B H2B 1.0000 . ?
C3B C31B 1.510(3) . ?
C3B H3B1 0.9900 . ?
C3B H3B2 0.9900 . ?
C1B O1B 1.213(3) . ?
C1B O2B 1.317(2) . ?
C31B C36B 1.389(3) . ?
C31B C32B 1.392(3) . ?
C32B C33B 1.386(3) . ?
C32B H32B 0.9500 . ?
C36B C35B 1.393(3) . ?
C36B H36B 0.9500 . ?
C34B C35B 1.380(3) . ?
C34B C33B 1.383(3) . ?
C34B H34B 0.9500 . ?
C33B H33B 0.9500 . ?
C35B H35B 0.9500 . ?
O2B H2BO 0.97(3) . ?
O3B H3BO 0.92(4) . ?

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
C2A C3A C4A 118.74(19) . . ?
C2A C3A C6A 117.54(18) . . ?
C4A C3A C6A 123.71(19) . . ?
C3A C4A C5A 118.26(19) . . ?
C3A C4A H4A 120.9 . . ?
C5A C4A H4A 120.9 . . ?
O1A C6A N2A 123.2(2) . . ?
O1A C6A C3A 119.71(19) . . ?
N2A C6A C3A 117.08(19) . . ?
C3A C2A C1A 119.1(2) . . ?
C3A C2A H2A 120.4 . . ?
C1A C2A H2A 120.4 . . ?
N1A C1A C2A 122.7(2) . . ?
N1A C1A H1A 118.6 . . ?
C2A C1A H1A 118.6 . . ?
N1A C5A C4A 123.25(19) . . ?
N1A C5A H5A 118.4 . . ?
C4A C5A H5A 118.4 . . ?
C1A N1A C5A 117.91(19) . . ?
C6A N2A H1BN 117.0(19) . . ?
C6A N2A H2BN 122.8(19) . . ?
H1BN N2A H2BN 120(3) . . ?
O3B C2B C1B 110.76(18) . . ?
O3B C2B C3B 108.88(18) . . ?
C1B C2B C3B 110.41(18) . . ?
O3B C2B H2B 108.9 . . ?
C1B C2B H2B 108.9 . . ?
C3B C2B H2B 108.9 . . ?
C31B C3B C2B 112.94(18) . . ?
C31B C3B H3B1 109.0 . . ?
C2B C3B H3B1 109.0 . . ?
C31B C3B H3B2 109.0 . . ?
C2B C3B H3B2 109.0 . . ?
H3B1 C3B H3B2 107.8 . . ?
O1B C1B O2B 124.0(2) . . ?
O1B C1B C2B 122.89(19) . . ?
O2B C1B C2B 113.10(18) . . ?
C36B C31B C32B 118.5(2) . . ?
C36B C31B C3B 119.98(19) . . ?
C32B C31B C3B 121.5(2) . . ?
C33B C32B C31B 120.4(2) . . ?
C33B C32B H32B 119.8 . . ?
C31B C32B H32B 119.8 . . ?
C31B C36B C35B 121.0(2) . . ?
C31B C36B H36B 119.5 . . ?
C35B C36B H36B 119.5 . . ?
C35B C34B C33B 119.6(2) . . ?
C35B C34B H34B 120.2 . . ?
C33B C34B H34B 120.2 . . ?
C34B C33B C32B 120.6(2) . . ?
C34B C33B H33B 119.7 . . ?
C32B C33B H33B 119.7 . . ?
C34B C35B C36B 119.9(2) . . ?
C34B C35B H35B 120.1 . . ?
C36B C35B H35B 120.1 . . ?
C1B O2B H2BO 111.5(17) . . ?
C2B O3B H3BO 108(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_tai_52_1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1987226'
loop_
_audit_author_name
_audit_author_address
'Ian Scowen'
;University of Lincoln
United Kingdom
;
_audit_update_record             
;
2020-02-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (S)-2hyrdoxy-3-phenylpropionic acid nicotinamide
;
_chemical_name_common            
;
(L)-phenyllactic acid nictonamide
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H10 O3; C6 H6 N2 O1'
_chemical_formula_sum            'C15 H16 N2 O4'
_chemical_formula_weight         288.30
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.3040(2)
_cell_length_b                   11.4994(4)
_cell_length_c                   11.7480(5)
_cell_angle_alpha                80.398(3)
_cell_angle_beta                 81.767(3)
_cell_angle_gamma                82.135(3)
_cell_volume                     694.52(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1976
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      63.22

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6817
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   'SADABS - Bruker AXS, Madison WI'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14779
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         66.62
_reflns_number_total             3555
_reflns_number_gt                2910
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0788P)²+0.0121P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_number_reflns         3555
_refine_ls_number_parameters     411
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002

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
H1AO H 0.384(16) 0.527(8) 0.786(7) 0.12(3) Uiso 1 1 d . . .
H3AO H 0.983(14) 0.720(7) 0.787(7) 0.10(2) Uiso 1 1 d . . .
H1CO H 1.145(10) 1.162(5) 0.245(4) 0.048(15) Uiso 1 1 d . . .
H3CO H 0.488(11) 0.978(6) 0.303(5) 0.064(17) Uiso 1 1 d . . .
H21D H 0.052(8) 0.808(4) -0.006(4) 0.029(12) Uiso 1 1 d . . .
H22D H -0.120(11) 0.703(5) 0.021(5) 0.057(16) Uiso 1 1 d . . .
H21B H 0.636(12) -0.019(6) 1.014(6) 0.08(2) Uiso 1 1 d . . .
H22B H 0.476(12) -0.134(7) 1.037(6) 0.08(2) Uiso 1 1 d . . .
O1A O 0.3736(6) 0.6191(3) 0.7794(3) 0.0368(7) Uani 1 1 d . . .
O2A O 0.7782(6) 0.5717(3) 0.8173(3) 0.0402(8) Uani 1 1 d . . .
O3A O 0.8885(7) 0.7928(3) 0.7645(4) 0.0640(12) Uani 1 1 d . . .
C1A C 0.5204(7) 0.9698(3) 0.6234(4) 0.0286(9) Uani 1 1 d . . .
C2A C 0.3395(9) 1.0313(4) 0.5544(4) 0.0368(10) Uani 1 1 d . . .
H2A H 0.2247 0.9886 0.5274 0.044 Uiso 1 1 calc R . .
C3A C 0.3222(9) 1.1535(4) 0.5238(4) 0.0422(11) Uani 1 1 d . . .
H3A H 0.1963 1.1934 0.4765 0.051 Uiso 1 1 calc R . .
C4A C 0.4862(9) 1.2171(4) 0.5616(4) 0.0392(11) Uani 1 1 d . . .
H4A H 0.4768 1.3007 0.5397 0.047 Uiso 1 1 calc R . .
C5A C 0.6634(10) 1.1585(4) 0.6313(4) 0.0433(12) Uani 1 1 d . . .
H5A H 0.7752 1.2025 0.6588 0.052 Uiso 1 1 calc R . .
C6A C 0.6829(8) 1.0358(4) 0.6626(4) 0.0351(10) Uani 1 1 d . . .
H6A H 0.8077 0.9969 0.7110 0.042 Uiso 1 1 calc R . .
C7A C 0.5407(8) 0.8353(3) 0.6473(4) 0.0322(9) Uani 1 1 d . . .
H7A1 H 0.3699 0.8112 0.6441 0.039 Uiso 1 1 calc R . .
H7A2 H 0.6596 0.8039 0.5837 0.039 Uiso 1 1 calc R . .
C8A C 0.6306(7) 0.7770(3) 0.7610(4) 0.0297(9) Uani 1 1 d . . .
H8A H 0.5229 0.8162 0.8242 0.036 Uiso 1 1 calc R . .
C9A C 0.6047(8) 0.6447(4) 0.7879(4) 0.0285(9) Uani 1 1 d . . .
N1B N 0.3491(7) 0.3871(3) 0.8364(3) 0.0301(8) Uani 1 1 d . . .
N2B N 0.4920(7) -0.0453(3) 1.0139(4) 0.0376(9) Uani 1 1 d . . .
O1B O 0.0836(5) -0.0176(3) 0.9748(3) 0.0415(8) Uani 1 1 d . . .
C1B C 0.1710(8) 0.3281(4) 0.8083(4) 0.0326(10) Uani 1 1 d . . .
H1B H 0.0544 0.3691 0.7568 0.039 Uiso 1 1 calc R . .
C2B C 0.1512(8) 0.2099(4) 0.8514(4) 0.0312(10) Uani 1 1 d . . .
H2B H 0.0247 0.1703 0.8288 0.037 Uiso 1 1 calc R . .
C3B C 0.3178(7) 0.1496(4) 0.9280(3) 0.0260(9) Uani 1 1 d . . .
C4B C 0.4993(8) 0.2106(4) 0.9574(4) 0.0287(9) Uani 1 1 d . . .
H4B H 0.6164 0.1719 1.0096 0.034 Uiso 1 1 calc R . .
C5B C 0.5093(8) 0.3280(4) 0.9104(4) 0.0321(10) Uani 1 1 d . . .
H5B H 0.6354 0.3690 0.9313 0.038 Uiso 1 1 calc R . .
C6B C 0.2904(7) 0.0211(4) 0.9751(3) 0.0280(9) Uani 1 1 d . . .
O1C O 1.1133(5) 1.0770(3) 0.2813(3) 0.0375(7) Uani 1 1 d . . .
O2C O 0.7276(6) 1.1179(3) 0.2188(3) 0.0430(8) Uani 1 1 d . . .
O3C O 0.5801(6) 0.9083(3) 0.3254(3) 0.0458(9) Uani 1 1 d . . .
C1C C 0.9887(7) 0.7111(3) 0.3604(3) 0.0265(8) Uani 1 1 d . . .
C2C C 0.8135(8) 0.6391(4) 0.3416(4) 0.0323(9) Uani 1 1 d . . .
H2C H 0.7093 0.6645 0.2807 0.039 Uiso 1 1 calc R . .
C3C C 0.7901(9) 0.5305(4) 0.4113(4) 0.0388(11) Uani 1 1 d . . .
H3C H 0.6688 0.4822 0.3978 0.047 Uiso 1 1 calc R . .
C4C C 0.9398(9) 0.4913(4) 0.4995(4) 0.0433(11) Uani 1 1 d . . .
H4C H 0.9246 0.4162 0.5461 0.052 Uiso 1 1 calc R . .
C5C C 1.1128(9) 0.5632(4) 0.5193(4) 0.0472(12) Uani 1 1 d . . .
H5C H 1.2146 0.5380 0.5811 0.057 Uiso 1 1 calc R . .
C6C C 1.1388(8) 0.6717(4) 0.4496(4) 0.0384(11) Uani 1 1 d . . .
H6C H 1.2608 0.7195 0.4632 0.046 Uiso 1 1 calc R . .
C7C C 1.0182(7) 0.8308(3) 0.2870(4) 0.0301(9) Uani 1 1 d . . .
H7C1 H 0.9897 0.8271 0.2063 0.036 Uiso 1 1 calc R . .
H7C2 H 1.1955 0.8496 0.2851 0.036 Uiso 1 1 calc R . .
C8C C 0.8291(7) 0.9296(3) 0.3341(4) 0.0272(8) Uani 1 1 d . . .
H8C H 0.8465 0.9263 0.4183 0.033 Uiso 1 1 calc R . .
C9C C 0.8835(8) 1.0513(4) 0.2711(4) 0.0283(9) Uani 1 1 d . . .
N1D N 0.1608(7) 0.3000(3) 0.2045(3) 0.0312(8) Uani 1 1 d . . .
N2D N 0.0410(7) 0.7286(3) 0.0177(3) 0.0323(8) Uani 1 1 d . . .
O1D O 0.4502(5) 0.6985(3) 0.0603(3) 0.0356(7) Uani 1 1 d . . .
C1D C 0.0062(8) 0.3580(4) 0.1273(4) 0.0305(9) Uani 1 1 d . . .
H1D H -0.1201 0.3171 0.1064 0.037 Uiso 1 1 calc R . .
C2D C 0.0225(8) 0.4744(4) 0.0770(4) 0.0294(9) Uani 1 1 d . . .
H2D H -0.0895 0.5127 0.0223 0.035 Uiso 1 1 calc R . .
C3D C 0.2065(7) 0.5343(3) 0.1080(3) 0.0238(9) Uani 1 1 d . . .
C4D C 0.3658(8) 0.4750(4) 0.1877(4) 0.0289(9) Uani 1 1 d . . .
H4D H 0.4943 0.5137 0.2099 0.035 Uiso 1 1 calc R . .
C5D C 0.3350(8) 0.3587(4) 0.2344(4) 0.0318(10) Uani 1 1 d . . .
H5D H 0.4426 0.3188 0.2903 0.038 Uiso 1 1 calc R . .
C6D C 0.2406(7) 0.6619(3) 0.0593(3) 0.0251(9) Uani 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
O1A C9A 1.320(5) . ?
O2A C9A 1.206(5) . ?
O3A C8A 1.411(5) . ?
C1A C2A 1.387(6) . ?
C1A C6A 1.393(6) . ?
C1A C7A 1.517(5) . ?
C2A C3A 1.385(7) . ?
C3A C4A 1.372(7) . ?
C4A C5A 1.367(7) . ?
C5A C6A 1.391(7) . ?
C7A C8A 1.502(6) . ?
C8A C9A 1.522(6) . ?
N1B C5B 1.340(6) . ?
N1B C1B 1.342(5) . ?
N2B C6B 1.317(6) . ?
O1B C6B 1.240(5) . ?
C1B C2B 1.382(6) . ?
C2B C3B 1.387(6) . ?
C3B C4B 1.378(6) . ?
C3B C6B 1.508(6) . ?
C4B C5B 1.376(6) . ?
O1C C9C 1.319(5) . ?
O2C C9C 1.209(5) . ?
O3C C8C 1.397(5) . ?
C1C C6C 1.385(6) . ?
C1C C2C 1.388(5) . ?
C1C C7C 1.512(5) . ?
C2C C3C 1.385(6) . ?
C3C C4C 1.375(7) . ?
C4C C5C 1.383(7) . ?
C5C C6C 1.385(7) . ?
C7C C8C 1.531(5) . ?
C8C C9C 1.514(6) . ?
N1D C5D 1.333(6) . ?
N1D C1D 1.342(6) . ?
N2D C6D 1.322(5) . ?
O1D C6D 1.244(5) . ?
C1D C2D 1.379(6) . ?
C2D C3D 1.389(6) . ?
C3D C4D 1.382(6) . ?
C3D C6D 1.509(6) . ?
C4D C5D 1.381(6) . ?

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
C2A C1A C6A 117.5(4) . . ?
C2A C1A C7A 119.0(4) . . ?
C6A C1A C7A 123.5(3) . . ?
C3A C2A C1A 121.7(4) . . ?
C4A C3A C2A 120.2(4) . . ?
C5A C4A C3A 119.2(4) . . ?
C4A C5A C6A 121.2(5) . . ?
C5A C6A C1A 120.3(4) . . ?
C8A C7A C1A 116.4(3) . . ?
O3A C8A C7A 111.4(4) . . ?
O3A C8A C9A 108.4(3) . . ?
C7A C8A C9A 113.5(3) . . ?
O2A C9A O1A 123.9(4) . . ?
O2A C9A C8A 122.6(4) . . ?
O1A C9A C8A 113.5(3) . . ?
C5B N1B C1B 117.8(4) . . ?
N1B C1B C2B 122.4(4) . . ?
C1B C2B C3B 119.3(4) . . ?
C4B C3B C2B 118.1(4) . . ?
C4B C3B C6B 123.5(4) . . ?
C2B C3B C6B 118.4(4) . . ?
C5B C4B C3B 119.4(4) . . ?
N1B C5B C4B 123.0(4) . . ?
O1B C6B N2B 123.1(4) . . ?
O1B C6B C3B 119.4(3) . . ?
N2B C6B C3B 117.5(4) . . ?
C6C C1C C2C 118.7(4) . . ?
C6C C1C C7C 119.5(4) . . ?
C2C C1C C7C 121.8(3) . . ?
C3C C2C C1C 120.3(4) . . ?
C4C C3C C2C 121.0(4) . . ?
C3C C4C C5C 118.9(5) . . ?
C4C C5C C6C 120.5(4) . . ?
C5C C6C C1C 120.6(4) . . ?
C1C C7C C8C 112.0(3) . . ?
O3C C8C C9C 111.3(3) . . ?
O3C C8C C7C 108.7(3) . . ?
C9C C8C C7C 111.8(3) . . ?
O2C C9C O1C 124.2(4) . . ?
O2C C9C C8C 122.5(4) . . ?
O1C C9C C8C 113.2(3) . . ?
C5D N1D C1D 118.1(4) . . ?
N1D C1D C2D 122.9(4) . . ?
C1D C2D C3D 118.5(4) . . ?
C4D C3D C2D 118.8(4) . . ?
C4D C3D C6D 118.1(3) . . ?
C2D C3D C6D 123.1(4) . . ?
C5D C4D C3D 118.9(4) . . ?
N1D C5D C4D 122.8(4) . . ?
O1D C6D N2D 123.9(4) . . ?
O1D C6D C3D 119.3(3) . . ?
N2D C6D C3D 116.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        66.62
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.065

# start Validation Reply Form
_vrf_PLAT915_tai_52_1a_0m        
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         48 %     
RESPONSE: Mo-Ka radiation - absolute config from synthesis
;
# end Validation Reply Form

