# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_Fuli_RmanLprol_2
_database_code_depnum_ccdc_archive 'CCDC 2174324'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'R-mandelic acid , L-proline (1:1)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 O3, C5 H9 N O2'
_chemical_formula_sum            'C13 H17 N O5'
_chemical_formula_weight         267.27

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.8248(5)
_cell_length_b                   7.9556(4)
_cell_length_c                   20.9680(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1305.28(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3659
_cell_measurement_theta_min      3.2100
_cell_measurement_theta_max      25.6360

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_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_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'75 images, ΔΦ 2.5° '
;



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9519
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.214
_diffrn_reflns_theta_max         26.091
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2586
_reflns_number_gt                2249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       MAR
_computing_cell_refinement       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.5658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(9)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4144(4) 0.0645(3) 0.45956(13) 0.0414(6) Uani 1 1 d . . . . .
H1A H 0.327984 0.081073 0.486447 0.050 Uiso 1 1 calc R U . . .
H1B H 0.511542 0.069883 0.481538 0.050 Uiso 1 1 calc R U . . .
C2 C 0.3979(7) -0.1038(5) 0.4289(2) 0.0701(12) Uani 1 1 d . . . . .
H2A H 0.493444 -0.174931 0.440710 0.084 Uiso 1 1 calc R U . . .
H2B H 0.292918 -0.158033 0.442379 0.084 Uiso 1 1 calc R U . . .
C3 C 0.3962(7) -0.0758(6) 0.3599(2) 0.0739(13) Uani 1 1 d . . . . .
H3A H 0.311539 -0.147477 0.339815 0.089 Uiso 1 1 calc R U . . .
H3B H 0.507232 -0.101742 0.341812 0.089 Uiso 1 1 calc R U . . .
C4 C 0.3535(6) 0.1041(5) 0.34896(19) 0.0602(10) Uani 1 1 d . . . . .
H4A H 0.231509 0.118271 0.342813 0.072 Uiso 1 1 calc R U . . .
H4B H 0.412671 0.146693 0.311647 0.072 Uiso 1 1 calc R U . . .
C5 C 0.4130(4) 0.1962(4) 0.40920(16) 0.0418(7) Uani 1 1 d . . . . .
H5 H 0.529399 0.238423 0.402755 0.050 Uiso 1 1 calc R U . . .
C6 C 0.2965(4) 0.3412(4) 0.42741(16) 0.0418(7) Uani 1 1 d . . . . .
O7 O 0.2048(3) 0.3232(3) 0.47480(12) 0.0544(7) Uani 1 1 d . . . . .
O8 O 0.2977(3) 0.4657(3) 0.39017(12) 0.0522(6) Uani 1 1 d . . . . .
C11 C 0.8843(5) 0.9453(5) 0.39576(17) 0.0486(8) Uani 1 1 d . . . . .
H11 H 0.905772 0.918485 0.438186 0.058 Uiso 1 1 calc R U . . .
C12 C 0.8685(5) 1.1122(5) 0.3776(2) 0.0597(10) Uani 1 1 d . . . . .
H12 H 0.879990 1.197013 0.407841 0.072 Uiso 1 1 calc R U . . .
C13 C 0.8357(6) 1.1526(5) 0.3151(2) 0.0636(11) Uani 1 1 d . . . . .
H13 H 0.823468 1.264449 0.303133 0.076 Uiso 1 1 calc R U . . .
C14 C 0.8214(5) 1.0289(5) 0.27104(19) 0.0589(10) Uani 1 1 d . . . . .
H14 H 0.799694 1.056297 0.228693 0.071 Uiso 1 1 calc R U . . .
C15 C 0.8388(5) 0.8620(5) 0.28854(16) 0.0495(9) Uani 1 1 d . . . . .
H15 H 0.830285 0.778477 0.257663 0.059 Uiso 1 1 calc R U . . .
C16 C 0.8684(4) 0.8182(4) 0.35087(16) 0.0398(7) Uani 1 1 d . . . . .
C17 C 0.8810(5) 0.6354(5) 0.37085(18) 0.0492(9) Uani 1 1 d . . . . .
H17 H 0.921311 0.568709 0.334539 0.059 Uiso 1 1 calc R U . . .
O18 O 0.9948(3) 0.6138(4) 0.42225(14) 0.0684(8) Uani 1 1 d . . . . .
H18 H 1.081201 0.565804 0.409744 0.103 Uiso 1 1 calc R U . . .
C19 C 0.7056(5) 0.5700(4) 0.39153(18) 0.0473(8) Uani 1 1 d . . . . .
O20 O 0.5965(3) 0.5592(3) 0.34375(12) 0.0558(7) Uani 1 1 d . . . . .
H20 H 0.501804 0.534124 0.357517 0.084 Uiso 1 1 calc R U . . .
O21 O 0.6700(3) 0.5329(4) 0.44517(13) 0.0651(8) 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
N1 C5 1.488(4) . ?
N1 C2 1.491(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C2 C3 1.465(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.488(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.533(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.519(4) . ?
C5 H5 0.9800 . ?
C6 O7 1.234(4) . ?
C6 O8 1.262(4) . ?
C11 C12 1.387(6) . ?
C11 C16 1.387(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.355(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.517(5) . ?
C17 O18 1.408(4) . ?
C17 C19 1.530(5) . ?
C17 H17 0.9800 . ?
O18 H18 0.8200 . ?
C19 O21 1.196(4) . ?
C19 O20 1.319(4) . ?
O20 H20 0.8200 . ?

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
C5 N1 C2 109.0(3) . . ?
C5 N1 H1A 109.9 . . ?
C2 N1 H1A 109.9 . . ?
C5 N1 H1B 109.9 . . ?
C2 N1 H1B 109.9 . . ?
H1A N1 H1B 108.3 . . ?
C3 C2 N1 106.9(3) . . ?
C3 C2 H2A 110.3 . . ?
N1 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
N1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C2 C3 C4 107.5(4) . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 C5 105.4(3) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C6 111.1(3) . . ?
N1 C5 C4 104.5(3) . . ?
C6 C5 C4 112.8(3) . . ?
N1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
O7 C6 O8 126.4(3) . . ?
O7 C6 C5 117.6(3) . . ?
O8 C6 C5 115.9(3) . . ?
C12 C11 C16 120.3(4) . . ?
C12 C11 H11 119.9 . . ?
C16 C11 H11 119.9 . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.5(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 118.4(3) . . ?
C15 C16 C17 121.2(3) . . ?
C11 C16 C17 120.4(3) . . ?
O18 C17 C16 111.6(3) . . ?
O18 C17 C19 108.0(3) . . ?
C16 C17 C19 110.2(3) . . ?
O18 C17 H17 109.0 . . ?
C16 C17 H17 109.0 . . ?
C19 C17 H17 109.0 . . ?
C17 O18 H18 109.5 . . ?
O21 C19 O20 123.2(4) . . ?
O21 C19 C17 124.0(3) . . ?
O20 C19 C17 112.8(3) . . ?
C19 O20 H20 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 3.1(5) . . . . ?
N1 C2 C3 C4 -18.5(6) . . . . ?
C2 C3 C4 C5 26.3(6) . . . . ?
C2 N1 C5 C6 134.8(3) . . . . ?
C2 N1 C5 C4 12.8(4) . . . . ?
C3 C4 C5 N1 -23.7(5) . . . . ?
C3 C4 C5 C6 -144.5(4) . . . . ?
N1 C5 C6 O7 -9.1(4) . . . . ?
C4 C5 C6 O7 108.0(4) . . . . ?
N1 C5 C6 O8 174.3(3) . . . . ?
C4 C5 C6 O8 -68.7(4) . . . . ?
C16 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C14 -0.9(7) . . . . ?
C12 C13 C14 C15 0.3(6) . . . . ?
C13 C14 C15 C16 0.9(6) . . . . ?
C14 C15 C16 C11 -1.4(6) . . . . ?
C14 C15 C16 C17 177.7(3) . . . . ?
C12 C11 C16 C15 0.8(5) . . . . ?
C12 C11 C16 C17 -178.4(3) . . . . ?
C15 C16 C17 O18 148.1(3) . . . . ?
C11 C16 C17 O18 -32.8(4) . . . . ?
C15 C16 C17 C19 -91.8(4) . . . . ?
C11 C16 C17 C19 87.2(4) . . . . ?
O18 C17 C19 O21 10.5(5) . . . . ?
C16 C17 C19 O21 -111.7(4) . . . . ?
O18 C17 C19 O20 -169.7(3) . . . . ?
C16 C17 C19 O20 68.1(4) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.037



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_Alex_Sman_Lpro
_database_code_depnum_ccdc_archive 'CCDC 2174326'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'S-mandelic acid L-proline (1:2)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H9 N O2, C8 H8 O3'
_chemical_formula_sum            'C13 H17 N O5'
_chemical_formula_weight         267.27

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   14.6468(7)
_cell_length_b                   5.7771(2)
_cell_length_c                   16.2043(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.386(6)
_cell_angle_gamma                90
_cell_volume                     1308.50(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3717
_cell_measurement_theta_min      2.8070
_cell_measurement_theta_max      26.2150

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.90312
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_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_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'100 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9623
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.817
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4725
_reflns_number_gt                3740
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.986

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

_computing_data_collection       MAR
_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    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;





_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+0.2468P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4725
_refine_ls_number_parameters     357
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.56419(19) 1.0248(5) 0.12525(18) 0.0348(7) Uani 1 1 d . . . . .
H1A H 0.505022 0.975267 0.119279 0.042 Uiso 1 1 calc R U . . .
H1B H 0.560610 1.152587 0.093765 0.042 Uiso 1 1 calc R U . . .
C2 C 0.6144(3) 1.0751(8) 0.2180(2) 0.0534(10) Uani 1 1 d . . . . .
H2A H 0.595486 0.966998 0.255687 0.064 Uiso 1 1 calc R U . . .
H2B H 0.601558 1.231658 0.233097 0.064 Uiso 1 1 calc R U . . .
C3 C 0.7180(3) 1.0448(7) 0.2232(3) 0.0542(11) Uani 1 1 d . . . . .
H3A H 0.756791 1.015496 0.282171 0.065 Uiso 1 1 calc R U . . .
H3B H 0.742374 1.180580 0.201550 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7169(3) 0.8357(8) 0.1658(3) 0.0537(11) Uani 1 1 d . . . . .
H4A H 0.723519 0.693630 0.199046 0.064 Uiso 1 1 calc R U . . .
H4B H 0.768679 0.844708 0.140165 0.064 Uiso 1 1 calc R U . . .
C5 C 0.6194(2) 0.8432(6) 0.0955(2) 0.0326(8) Uani 1 1 d . . . . .
H5 H 0.627927 0.887737 0.039884 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5680(2) 0.6113(6) 0.0869(2) 0.0323(8) Uani 1 1 d . . . . .
O7 O 0.49830(18) 0.5941(5) 0.11442(19) 0.0543(7) Uani 1 1 d . . . . .
O8 O 0.60125(16) 0.4497(4) 0.05249(17) 0.0404(6) Uani 1 1 d . . . . .
N11 N 0.36769(19) 0.5075(5) 0.20534(19) 0.0373(7) Uani 1 1 d D U . . .
H11A H 0.411179 0.462006 0.180391 0.045 Uiso 1 1 calc R U . A 1
H11B H 0.385990 0.642408 0.231607 0.045 Uiso 1 1 calc R U . A 1
C12 C 0.2723(6) 0.529(9) 0.1404(10) 0.0592(16) Uani 0.636(16) 1 d D U P B 1
H12A H 0.272001 0.454087 0.086685 0.071 Uiso 0.636(16) 1 calc R U P B 1
H12B H 0.255242 0.690205 0.128721 0.071 Uiso 0.636(16) 1 calc R U P B 1
C13 C 0.2027(6) 0.410(3) 0.1793(7) 0.069(3) Uani 0.636(16) 1 d D U P B 1
H13A H 0.183045 0.261824 0.151702 0.082 Uiso 0.636(16) 1 calc R U P B 1
H13B H 0.146289 0.505207 0.172301 0.082 Uiso 0.636(16) 1 calc R U P B 1
C14 C 0.2565(5) 0.377(3) 0.2752(7) 0.052(3) Uani 0.636(16) 1 d D U P B 1
H14A H 0.254544 0.515509 0.308718 0.062 Uiso 0.636(16) 1 calc R U P B 1
H14B H 0.232366 0.246419 0.299859 0.062 Uiso 0.636(16) 1 calc R U P B 1
C12B C 0.2772(9) 0.541(16) 0.1347(17) 0.0592(16) Uani 0.364(16) 1 d D U P B 2
H12C H 0.266510 0.416348 0.092611 0.071 Uiso 0.364(16) 1 calc R U P B 2
H12D H 0.276450 0.687706 0.105556 0.071 Uiso 0.364(16) 1 calc R U P B 2
C13B C 0.2043(12) 0.536(4) 0.1842(13) 0.069(3) Uani 0.364(16) 1 d D U P B 2
H13C H 0.142058 0.485592 0.147818 0.082 Uiso 0.364(16) 1 calc R U P B 2
H13D H 0.198159 0.685914 0.208765 0.082 Uiso 0.364(16) 1 calc R U P B 2
C14B C 0.2488(9) 0.358(6) 0.2544(16) 0.052(3) Uani 0.364(16) 1 d D U P B 2
H14C H 0.217680 0.209662 0.238175 0.062 Uiso 0.364(16) 1 calc R U P B 2
H14D H 0.238383 0.406148 0.308221 0.062 Uiso 0.364(16) 1 calc R U P B 2
C15 C 0.3561(2) 0.3322(6) 0.2678(2) 0.0353(8) Uani 1 1 d D U . . .
H15 H 0.403419 0.361382 0.323954 0.042 Uiso 1 1 calc R U . B 1
C16 C 0.3727(3) 0.0910(7) 0.2368(3) 0.0432(9) Uani 1 1 d . . . . .
O17 O 0.3931(2) 0.0720(5) 0.16910(19) 0.0582(8) Uani 1 1 d . . . . .
O18 O 0.3629(3) -0.0745(5) 0.2843(2) 0.0717(10) Uani 1 1 d . . . . .
C21 C 0.9612(3) 0.3287(8) 0.2177(3) 0.0522(11) Uani 1 1 d . . . . .
H21 H 0.928784 0.467265 0.200403 0.063 Uiso 1 1 calc R U . . .
C22 C 1.0057(3) 0.2898(9) 0.3042(3) 0.0606(12) Uani 1 1 d . . . . .
H22 H 1.002459 0.401990 0.344336 0.073 Uiso 1 1 calc R U . . .
C23 C 1.0542(3) 0.0910(8) 0.3319(3) 0.0539(11) Uani 1 1 d . . . . .
H23 H 1.084782 0.066734 0.390351 0.065 Uiso 1 1 calc R U . . .
C24 C 1.0574(3) -0.0725(9) 0.2723(3) 0.0630(12) Uani 1 1 d . . . . .
H24 H 1.090429 -0.209913 0.290259 0.076 Uiso 1 1 calc R U . . .
C25 C 1.0115(3) -0.0360(8) 0.1848(3) 0.0541(11) Uani 1 1 d . . . . .
H25 H 1.013274 -0.150386 0.144943 0.065 Uiso 1 1 calc R U . . .
C26 C 0.9637(2) 0.1668(6) 0.1567(2) 0.0352(8) Uani 1 1 d . . . . .
C27 C 0.9212(2) 0.2082(7) 0.0599(2) 0.0370(8) Uani 1 1 d . . . . .
H27 H 0.896864 0.061228 0.031605 0.044 Uiso 1 1 calc R U . . .
O28 O 0.99130(18) 0.2963(5) 0.02362(18) 0.0476(7) Uani 1 1 d . . . . .
H28 H 1.025727 0.190203 0.017134 0.071 Uiso 1 1 calc R U . . .
C29 C 0.8402(2) 0.3824(7) 0.0403(2) 0.0382(9) Uani 1 1 d . . . . .
O30 O 0.84546(18) 0.5778(5) 0.01735(19) 0.0550(7) Uani 1 1 d . . . . .
O31 O 0.76372(17) 0.2886(5) 0.05336(19) 0.0491(7) Uani 1 1 d . . . . .
H31 H 0.722690 0.388276 0.048939 0.074 Uiso 1 1 calc R U . . .
C41 C 0.2762(3) 0.4187(7) 0.5179(3) 0.0501(10) Uani 1 1 d . . . . .
H41 H 0.324900 0.471408 0.496752 0.060 Uiso 1 1 calc R U . . .
C42 C 0.1948(3) 0.5505(9) 0.5062(3) 0.0607(12) Uani 1 1 d . . . . .
H42 H 0.188663 0.691172 0.477179 0.073 Uiso 1 1 calc R U . . .
C43 C 0.1231(3) 0.4743(10) 0.5373(3) 0.0661(14) Uani 1 1 d . . . . .
H43 H 0.068128 0.563101 0.529209 0.079 Uiso 1 1 calc R U . . .
C44 C 0.1317(3) 0.2685(11) 0.5801(3) 0.0702(15) Uani 1 1 d . . . . .
H44 H 0.083090 0.218429 0.601863 0.084 Uiso 1 1 calc R U . . .
C45 C 0.2132(3) 0.1333(9) 0.5915(3) 0.0611(12) Uani 1 1 d . . . . .
H45 H 0.218273 -0.008344 0.619769 0.073 Uiso 1 1 calc R U . . .
C46 C 0.2862(3) 0.2084(7) 0.5610(2) 0.0452(10) Uani 1 1 d . . . . .
C47 C 0.3769(3) 0.0682(8) 0.5730(3) 0.0550(11) Uani 1 1 d . . . . .
H47 H 0.365855 -0.087208 0.592281 0.066 Uiso 1 1 calc R U . . .
O48 O 0.4553(3) 0.1664(7) 0.6370(2) 0.0947(13) Uani 1 1 d . . . . .
H48 H 0.463364 0.300041 0.623593 0.142 Uiso 1 1 calc R U . . .
C49 C 0.4001(3) 0.0445(7) 0.4884(3) 0.0532(11) Uani 1 1 d . . . . .
O50 O 0.4719(2) 0.1208(7) 0.4771(3) 0.0842(11) Uani 1 1 d . . . . .
O51 O 0.3331(2) -0.0635(6) 0.42993(19) 0.0572(8) Uani 1 1 d . . . . .
H51 H 0.343682 -0.054316 0.383108 0.086 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.490(4) . ?
N1 C2 1.491(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C2 C3 1.505(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.521(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.539(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.522(5) . ?
C5 H5 0.9800 . ?
C6 O7 1.234(4) . ?
C6 O8 1.258(4) . ?
N11 C15 1.476(5) . ?
N11 C12 1.482(7) . ?
N11 C12B 1.483(10) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
C12 C13 1.513(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.530(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.523(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12B C13B 1.516(18) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B C14B 1.526(14) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15 1.529(11) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15 C16 1.525(5) . ?
C15 H15 0.9800 . ?
C16 O17 1.225(4) . ?
C16 O18 1.262(5) . ?
C21 C26 1.369(5) . ?
C21 C22 1.376(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.354(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.361(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.392(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.371(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.525(5) . ?
C27 O28 1.420(4) . ?
C27 C29 1.515(5) . ?
C27 H27 0.9800 . ?
O28 H28 0.8200 . ?
C29 O30 1.198(5) . ?
C29 O31 1.318(4) . ?
O31 H31 0.8200 . ?
C41 C42 1.380(6) . ?
C41 C46 1.387(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.366(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.363(7) . ?
C43 H43 0.9300 . ?
C44 C45 1.392(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.376(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.517(5) . ?
C47 O48 1.415(5) . ?
C47 C49 1.514(6) . ?
C47 H47 0.9800 . ?
O48 H48 0.8200 . ?
C49 O50 1.205(5) . ?
C49 O51 1.301(5) . ?
O51 H51 0.8200 . ?

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
C5 N1 C2 108.2(3) . . ?
C5 N1 H1A 110.1 . . ?
C2 N1 H1A 110.1 . . ?
C5 N1 H1B 110.1 . . ?
C2 N1 H1B 110.1 . . ?
H1A N1 H1B 108.4 . . ?
N1 C2 C3 102.7(3) . . ?
N1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
N1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 103.4(3) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C3 C4 C5 105.6(3) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C6 110.4(3) . . ?
N1 C5 C4 104.6(3) . . ?
C6 C5 C4 111.5(3) . . ?
N1 C5 H5 110.1 . . ?
C6 C5 H5 110.1 . . ?
C4 C5 H5 110.1 . . ?
O7 C6 O8 124.9(3) . . ?
O7 C6 C5 118.6(3) . . ?
O8 C6 C5 116.5(3) . . ?
C15 N11 C12 105.4(12) . . ?
C15 N11 C12B 111(2) . . ?
C15 N11 H11A 110.7 . . ?
C12 N11 H11A 110.7 . . ?
C15 N11 H11B 110.7 . . ?
C12 N11 H11B 110.7 . . ?
H11A N11 H11B 108.8 . . ?
N11 C12 C13 106.0(10) . . ?
N11 C12 H12A 110.5 . . ?
C13 C12 H12A 110.5 . . ?
N11 C12 H12B 110.5 . . ?
C13 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C12 C13 C14 105.9(9) . . ?
C12 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C15 C14 C13 98.9(7) . . ?
C15 C14 H14A 112.0 . . ?
C13 C14 H14A 112.0 . . ?
C15 C14 H14B 112.0 . . ?
C13 C14 H14B 112.0 . . ?
H14A C14 H14B 109.7 . . ?
N11 C12B C13B 101.4(13) . . ?
N11 C12B H12C 111.5 . . ?
C13B C12B H12C 111.5 . . ?
N11 C12B H12D 111.5 . . ?
C13B C12B H12D 111.5 . . ?
H12C C12B H12D 109.3 . . ?
C12B C13B C14B 101(2) . . ?
C12B C13B H13C 111.5 . . ?
C14B C13B H13C 111.5 . . ?
C12B C13B H13D 111.5 . . ?
C14B C13B H13D 111.5 . . ?
H13C C13B H13D 109.3 . . ?
C13B C14B C15 111.3(13) . . ?
C13B C14B H14C 109.4 . . ?
C15 C14B H14C 109.4 . . ?
C13B C14B H14D 109.4 . . ?
C15 C14B H14D 109.4 . . ?
H14C C14B H14D 108.0 . . ?
N11 C15 C14 104.2(6) . . ?
N11 C15 C16 109.8(3) . . ?
C14 C15 C16 115.7(8) . . ?
N11 C15 C14B 99.2(9) . . ?
C16 C15 C14B 107.5(14) . . ?
N11 C15 H15 109.0 . . ?
C14 C15 H15 109.0 . . ?
C16 C15 H15 109.0 . . ?
O17 C16 O18 125.5(4) . . ?
O17 C16 C15 118.8(4) . . ?
O18 C16 C15 115.7(3) . . ?
C26 C21 C22 121.1(4) . . ?
C26 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 121.2(4) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 118.6(4) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C23 C24 C25 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 120.7(4) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C21 C26 C25 117.8(4) . . ?
C21 C26 C27 123.0(3) . . ?
C25 C26 C27 119.1(3) . . ?
O28 C27 C29 107.0(3) . . ?
O28 C27 C26 111.0(3) . . ?
C29 C27 C26 111.9(3) . . ?
O28 C27 H27 108.9 . . ?
C29 C27 H27 108.9 . . ?
C26 C27 H27 108.9 . . ?
C27 O28 H28 109.5 . . ?
O30 C29 O31 125.0(3) . . ?
O30 C29 C27 124.9(3) . . ?
O31 C29 C27 110.1(3) . . ?
C29 O31 H31 109.5 . . ?
C42 C41 C46 120.6(4) . . ?
C42 C41 H41 119.7 . . ?
C46 C41 H41 119.7 . . ?
C43 C42 C41 120.0(5) . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C44 C43 C42 120.3(5) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 120.2(5) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C46 C45 C44 120.2(5) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C45 C46 C41 118.7(4) . . ?
C45 C46 C47 122.0(4) . . ?
C41 C46 C47 119.3(4) . . ?
O48 C47 C49 110.3(4) . . ?
O48 C47 C46 111.6(3) . . ?
C49 C47 C46 110.9(3) . . ?
O48 C47 H47 108.0 . . ?
C49 C47 H47 108.0 . . ?
C46 C47 H47 108.0 . . ?
C47 O48 H48 109.5 . . ?
O50 C49 O51 124.6(5) . . ?
O50 C49 C47 123.2(4) . . ?
O51 C49 C47 112.3(4) . . ?
C49 O51 H51 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 34.1(4) . . . . ?
N1 C2 C3 C4 -39.4(4) . . . . ?
C2 C3 C4 C5 30.9(4) . . . . ?
C2 N1 C5 C6 105.4(3) . . . . ?
C2 N1 C5 C4 -14.7(4) . . . . ?
C3 C4 C5 N1 -10.3(4) . . . . ?
C3 C4 C5 C6 -129.6(3) . . . . ?
N1 C5 C6 O7 -8.8(4) . . . . ?
C4 C5 C6 O7 107.0(4) . . . . ?
N1 C5 C6 O8 171.8(3) . . . . ?
C4 C5 C6 O8 -72.4(4) . . . . ?
C15 N11 C12 C13 14(3) . . . . ?
N11 C12 C13 C14 14(3) . . . . ?
C12 C13 C14 C15 -35(2) . . . . ?
C15 N11 C12B C13B 41(6) . . . . ?
N11 C12B C13B C14B -35(5) . . . . ?
C12B C13B C14B C15 21(4) . . . . ?
C12 N11 C15 C14 -37.0(19) . . . . ?
C12 N11 C15 C16 87.5(18) . . . . ?
C12B N11 C15 C16 86(3) . . . . ?
C12B N11 C15 C14B -27(4) . . . . ?
C13 C14 C15 N11 43.9(13) . . . . ?
C13 C14 C15 C16 -76.8(12) . . . . ?
C13B C14B C15 N11 2(2) . . . . ?
C13B C14B C15 C16 -112(2) . . . . ?
N11 C15 C16 O17 0.6(5) . . . . ?
C14 C15 C16 O17 118.2(6) . . . . ?
C14B C15 C16 O17 107.6(9) . . . . ?
N11 C15 C16 O18 -178.6(3) . . . . ?
C14 C15 C16 O18 -61.0(6) . . . . ?
C14B C15 C16 O18 -71.7(9) . . . . ?
C26 C21 C22 C23 0.5(7) . . . . ?
C21 C22 C23 C24 -0.7(7) . . . . ?
C22 C23 C24 C25 -0.1(7) . . . . ?
C23 C24 C25 C26 1.1(7) . . . . ?
C22 C21 C26 C25 0.5(6) . . . . ?
C22 C21 C26 C27 -175.8(4) . . . . ?
C24 C25 C26 C21 -1.3(6) . . . . ?
C24 C25 C26 C27 175.1(4) . . . . ?
C21 C26 C27 O28 92.7(4) . . . . ?
C25 C26 C27 O28 -83.5(4) . . . . ?
C21 C26 C27 C29 -26.8(5) . . . . ?
C25 C26 C27 C29 156.9(3) . . . . ?
O28 C27 C29 O30 -15.8(5) . . . . ?
C26 C27 C29 O30 106.0(4) . . . . ?
O28 C27 C29 O31 165.0(3) . . . . ?
C26 C27 C29 O31 -73.1(4) . . . . ?
C46 C41 C42 C43 0.1(6) . . . . ?
C41 C42 C43 C44 0.2(7) . . . . ?
C42 C43 C44 C45 -0.9(7) . . . . ?
C43 C44 C45 C46 1.2(7) . . . . ?
C44 C45 C46 C41 -0.9(6) . . . . ?
C44 C45 C46 C47 179.1(4) . . . . ?
C42 C41 C46 C45 0.2(6) . . . . ?
C42 C41 C46 C47 -179.8(4) . . . . ?
C45 C46 C47 O48 -105.9(5) . . . . ?
C41 C46 C47 O48 74.1(5) . . . . ?
C45 C46 C47 C49 130.7(4) . . . . ?
C41 C46 C47 C49 -49.3(5) . . . . ?
O48 C47 C49 O50 -6.6(6) . . . . ?
C46 C47 C49 O50 117.5(5) . . . . ?
O48 C47 C49 O51 174.4(4) . . . . ?
C46 C47 C49 O51 -61.5(5) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.034



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_Alex_S-Man_L-Proline_twin1_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2174325'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_Alex_S-Man_L-Proline_twin1_hklf5 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: A resolution cut-off was imposed beyond which refinement statistics were poor.
;
_vrf_PLAT089_Alex_S-Man_L-Proline_twin1_hklf5 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.29 Note
RESPONSE: A result of the data cut-off (see above)
;
# Added during the CSD deposition process: Monday 23 May 2022 12:22 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'S-mandelic acid L-proline (1:1)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C5 H9 N O2), C8 H8 O3'
_chemical_formula_sum            'C18 H26 N2 O7'
_chemical_formula_weight         382.41

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   5.9617(14)
_cell_length_b                   9.3791(15)
_cell_length_c                   16.778(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.189(19)
_cell_angle_gamma                90
_cell_volume                     938.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    928
_cell_measurement_theta_min      3.2390
_cell_measurement_theta_max      22.7760

_exptl_crystal_description       colourless
_exptl_crystal_colour            plate
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.70450
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus source'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'100 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4164
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.258
_diffrn_reflns_theta_max         21.961
_diffrn_reflns_theta_full        21.961
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4164
_reflns_number_gt                2418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.970

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       MAR
_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    'SHELXT (Sheldrick, 2015)'
_atom_sites_solution_primary     'dual space'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;


_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+1.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 508 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4164
_refine_ls_number_parameters     373
_refine_ls_number_restraints     373
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0769
_refine_ls_wR_factor_ref         0.2162
_refine_ls_wR_factor_gt          0.1903
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.421(2) 0.2171(14) 0.7008(7) 0.060(3) Uani 1 1 d D U . . .
H1A H -0.535584 0.277224 0.705027 0.071 Uiso 1 1 calc R U . A 1
H1B H -0.384725 0.208861 0.649610 0.071 Uiso 1 1 calc R U . A 1
C2 C -0.480(5) 0.078(2) 0.7340(16) 0.070(8) Uani 0.80(4) 1 d D U P B 1
H2A H -0.637730 0.058010 0.725719 0.084 Uiso 0.80(4) 1 calc R U P B 1
H2B H -0.392234 0.003060 0.709187 0.084 Uiso 0.80(4) 1 calc R U P B 1
C3 C -0.429(5) 0.087(3) 0.8172(16) 0.083(9) Uani 0.80(4) 1 d D U P B 1
H3A H -0.401334 -0.006457 0.839402 0.099 Uiso 0.80(4) 1 calc R U P B 1
H3B H -0.552543 0.131066 0.845918 0.099 Uiso 0.80(4) 1 calc R U P B 1
C4 C -0.229(5) 0.176(3) 0.8221(13) 0.078(9) Uani 0.80(4) 1 d D U P B 1
H4A H -0.096005 0.116310 0.824114 0.093 Uiso 0.80(4) 1 calc R U P B 1
H4B H -0.233095 0.234257 0.869719 0.093 Uiso 0.80(4) 1 calc R U P B 1
C2B C -0.440(18) 0.063(4) 0.709(6) 0.061(17) Uani 0.20(4) 1 d D U P B 2
H2C H -0.596237 0.035851 0.714498 0.073 Uiso 0.20(4) 1 calc R U P B 2
H2D H -0.379240 0.015712 0.662705 0.073 Uiso 0.20(4) 1 calc R U P B 2
C3B C -0.318(17) 0.018(6) 0.779(5) 0.068(18) Uani 0.20(4) 1 d D U P B 2
H3C H -0.216340 -0.059162 0.766402 0.081 Uiso 0.20(4) 1 calc R U P B 2
H3D H -0.420001 -0.013182 0.820404 0.081 Uiso 0.20(4) 1 calc R U P B 2
C4B C -0.195(18) 0.143(6) 0.805(5) 0.059(15) Uani 0.20(4) 1 d D U P B 2
H4C H -0.036196 0.120084 0.807953 0.070 Uiso 0.20(4) 1 calc R U P B 2
H4D H -0.244220 0.170740 0.857443 0.070 Uiso 0.20(4) 1 calc R U P B 2
C5 C -0.227(2) 0.2696(17) 0.7473(9) 0.053(4) Uani 1 1 d D U . . .
H5 H -0.249277 0.369727 0.761978 0.064 Uiso 1 1 calc R U . B 1
C6 C -0.016(3) 0.2537(18) 0.6996(11) 0.055(4) Uani 1 1 d . U . . .
O7 O -0.0244(19) 0.1936(13) 0.6352(7) 0.066(3) Uani 1 1 d . U . . .
O8 O 0.153(2) 0.3106(13) 0.7309(7) 0.077(4) Uani 1 1 d . U . . .
N11 N 0.7657(18) 0.5441(12) 0.4757(7) 0.043(3) Uani 1 1 d . U . . .
H11A H 0.663787 0.485011 0.455311 0.051 Uiso 1 1 calc R U . . .
H11B H 0.799586 0.608990 0.438952 0.051 Uiso 1 1 calc R U . . .
C12 C 0.967(3) 0.4648(16) 0.4987(10) 0.056(4) Uani 1 1 d . U . . .
H12A H 1.065447 0.450180 0.453537 0.068 Uiso 1 1 calc R U . . .
H12B H 0.928915 0.373059 0.521732 0.068 Uiso 1 1 calc R U . . .
C13 C 1.073(3) 0.5625(18) 0.5600(10) 0.065(4) Uani 1 1 d . U . . .
H13A H 1.172595 0.509581 0.595002 0.078 Uiso 1 1 calc R U . . .
H13B H 1.157751 0.637707 0.534283 0.078 Uiso 1 1 calc R U . . .
C14 C 0.878(3) 0.6238(17) 0.6062(9) 0.058(4) Uani 1 1 d . U . . .
H14A H 0.908164 0.721812 0.621373 0.070 Uiso 1 1 calc R U . . .
H14B H 0.850466 0.568426 0.654025 0.070 Uiso 1 1 calc R U . . .
C15 C 0.675(3) 0.6153(15) 0.5482(8) 0.044(4) Uani 1 1 d . U . . .
H15 H 0.561536 0.552680 0.571897 0.053 Uiso 1 1 calc R U . . .
C16 C 0.565(2) 0.7559(15) 0.5286(10) 0.043(3) Uani 1 1 d . U . . .
O17 O 0.5357(16) 0.7841(10) 0.4581(6) 0.050(3) Uani 1 1 d . U . . .
O18 O 0.5070(17) 0.8285(11) 0.5869(6) 0.054(3) Uani 1 1 d . U . . .
C21 C 0.018(5) 0.811(4) 0.897(2) 0.084(10) Uani 0.75(7) 1 d D U P C 3
H21 H -0.106911 0.802987 0.863796 0.101 Uiso 0.75(7) 1 calc R U P C 3
C22 C 0.022(7) 0.913(3) 0.958(2) 0.088(10) Uani 0.75(7) 1 d D U P C 3
H22 H -0.104787 0.968589 0.967558 0.106 Uiso 0.75(7) 1 calc R U P C 3
C23 C 0.204(8) 0.934(4) 1.004(2) 0.089(11) Uani 0.75(7) 1 d D U P C 3
H23 H 0.205719 1.002541 1.043835 0.107 Uiso 0.75(7) 1 calc R U P C 3
C24 C 0.386(7) 0.851(4) 0.9904(18) 0.083(9) Uani 0.75(7) 1 d D U P C 3
H24 H 0.515150 0.867012 1.020288 0.099 Uiso 0.75(7) 1 calc R U P C 3
C25 C 0.386(5) 0.745(4) 0.934(2) 0.075(9) Uani 0.75(7) 1 d D U P C 3
H25 H 0.512274 0.687758 0.927349 0.090 Uiso 0.75(7) 1 calc R U P C 3
C26 C 0.198(5) 0.723(4) 0.8871(18) 0.065(8) Uani 0.75(7) 1 d D U P C 3
C27 C 0.191(5) 0.610(3) 0.8235(13) 0.057(7) Uani 0.75(7) 1 d D U P C 3
H27 H 0.041793 0.606013 0.798788 0.068 Uiso 0.75(7) 1 calc R U P C 3
O28 O 0.246(6) 0.476(3) 0.8596(19) 0.069(9) Uani 0.75(7) 1 d D U P C 3
H28 H 0.236791 0.412785 0.826127 0.104 Uiso 0.75(7) 1 calc R U P C 3
C29 C 0.370(7) 0.641(3) 0.7607(18) 0.058(9) Uani 0.75(7) 1 d D U P C 3
O30 O 0.523(6) 0.570(4) 0.744(2) 0.101(12) Uani 0.75(7) 1 d D U P C 3
O31 O 0.311(5) 0.757(3) 0.7203(16) 0.056(7) Uani 0.75(7) 1 d D U P C 3
H31 H 0.390469 0.765117 0.680770 0.084 Uiso 0.75(7) 1 calc R U P C 3
C21B C 0.055(12) 0.814(10) 0.920(6) 0.07(2) Uani 0.25(7) 1 d D U P C 4
H21B H -0.093647 0.807625 0.903093 0.082 Uiso 0.25(7) 1 calc R U P C 4
C22B C 0.118(17) 0.910(10) 0.981(6) 0.07(2) Uani 0.25(7) 1 d D U P C 4
H22B H 0.018132 0.980763 0.996751 0.084 Uiso 0.25(7) 1 calc R U P C 4
C23B C 0.318(18) 0.900(10) 1.016(5) 0.07(2) Uani 0.25(7) 1 d D U P C 4
H23B H 0.355951 0.959210 1.058708 0.086 Uiso 0.25(7) 1 calc R U P C 4
C24B C 0.465(13) 0.801(10) 0.990(4) 0.07(2) Uani 0.25(7) 1 d D U P C 4
H24B H 0.597072 0.785664 1.018035 0.082 Uiso 0.25(7) 1 calc R U P C 4
C25B C 0.424(12) 0.723(13) 0.922(7) 0.07(2) Uani 0.25(7) 1 d D U P C 4
H25B H 0.535842 0.665169 0.900617 0.085 Uiso 0.25(7) 1 calc R U P C 4
C26B C 0.217(11) 0.731(11) 0.885(5) 0.06(2) Uani 0.25(7) 1 d D U P C 4
C27B C 0.148(11) 0.629(7) 0.820(3) 0.058(16) Uani 0.25(7) 1 d D U P C 4
H27B H -0.007567 0.647443 0.804390 0.070 Uiso 0.25(7) 1 calc R U P C 4
O28B O 0.169(16) 0.487(8) 0.849(5) 0.06(2) Uani 0.25(7) 1 d D U P C 4
H28B H 0.157245 0.430762 0.812122 0.090 Uiso 0.25(7) 1 calc R U P C 4
C29B C 0.301(14) 0.645(7) 0.748(4) 0.040(17) Uani 0.25(7) 1 d D U P C 4
O30B O 0.439(13) 0.567(8) 0.726(4) 0.06(2) Uani 0.25(7) 1 d D U P C 4
O31B O 0.232(14) 0.758(7) 0.706(5) 0.05(2) Uani 0.25(7) 1 d D U P C 4
H31B H 0.310235 0.767304 0.666107 0.072 Uiso 0.25(7) 1 calc R U P C 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2B 1.46(3) . ?
N1 C2 1.46(2) . ?
N1 C5 1.477(19) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C2 C3 1.43(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.45(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.53(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C2B C3B 1.43(3) . ?
C2B H2C 0.9700 . ?
C2B H2D 0.9700 . ?
C3B C4B 1.45(3) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4B C5 1.54(3) . ?
C4B H4C 0.9700 . ?
C4B H4D 0.9700 . ?
C5 C6 1.50(2) . ?
C5 H5 0.9800 . ?
C6 O7 1.22(2) . ?
C6 O8 1.253(19) . ?
N11 C12 1.463(18) . ?
N11 C15 1.492(16) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
C12 C13 1.51(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.51(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.55(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.508(19) . ?
C15 H15 0.9800 . ?
C16 O17 1.224(15) . ?
C16 O18 1.243(16) . ?
C21 C26 1.37(3) . ?
C21 C22 1.41(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.34(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.35(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.38(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.38(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.51(2) . ?
C27 O28 1.43(2) . ?
C27 C29 1.53(3) . ?
C27 H27 0.9800 . ?
O28 H28 0.8200 . ?
C29 O30 1.16(2) . ?
C29 O31 1.33(2) . ?
O31 H31 0.8200 . ?
C21B C26B 1.37(3) . ?
C21B C22B 1.41(4) . ?
C21B H21B 0.9300 . ?
C22B C23B 1.34(4) . ?
C22B H22B 0.9300 . ?
C23B C24B 1.35(4) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.38(3) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.38(3) . ?
C25B H25B 0.9300 . ?
C26B C27B 1.51(3) . ?
C27B O28B 1.43(3) . ?
C27B C29B 1.53(3) . ?
C27B H27B 0.9800 . ?
O28B H28B 0.8200 . ?
C29B O30B 1.16(3) . ?
C29B O31B 1.33(3) . ?
O31B H31B 0.8200 . ?

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
C2B N1 C5 110(3) . . ?
C2 N1 C5 106.6(14) . . ?
C2 N1 H1A 110.4 . . ?
C5 N1 H1A 110.4 . . ?
C2 N1 H1B 110.4 . . ?
C5 N1 H1B 110.4 . . ?
H1A N1 H1B 108.6 . . ?
C3 C2 N1 105.5(17) . . ?
C3 C2 H2A 110.6 . . ?
N1 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
N1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
C2 C3 C4 105.1(19) . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C3 C4 C5 106.9(17) . . ?
C3 C4 H4A 110.3 . . ?
C5 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
C5 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
C3B C2B N1 109(3) . . ?
C3B C2B H2C 109.8 . . ?
N1 C2B H2C 109.8 . . ?
C3B C2B H2D 109.8 . . ?
N1 C2B H2D 109.8 . . ?
H2C C2B H2D 108.3 . . ?
C2B C3B C4B 105(3) . . ?
C2B C3B H3C 110.7 . . ?
C4B C3B H3C 110.7 . . ?
C2B C3B H3D 110.7 . . ?
C4B C3B H3D 110.7 . . ?
H3C C3B H3D 108.8 . . ?
C3B C4B C5 112(3) . . ?
C3B C4B H4C 109.2 . . ?
C5 C4B H4C 109.2 . . ?
C3B C4B H4D 109.2 . . ?
C5 C4B H4D 109.2 . . ?
H4C C4B H4D 107.9 . . ?
N1 C5 C6 109.9(14) . . ?
N1 C5 C4 103.4(14) . . ?
C6 C5 C4 112.9(16) . . ?
N1 C5 C4B 100(3) . . ?
C6 C5 C4B 99(5) . . ?
N1 C5 H5 110.1 . . ?
C6 C5 H5 110.1 . . ?
C4 C5 H5 110.1 . . ?
O7 C6 O8 126.9(15) . . ?
O7 C6 C5 119.0(17) . . ?
O8 C6 C5 114.0(17) . . ?
C12 N11 C15 108.2(11) . . ?
C12 N11 H11A 110.1 . . ?
C15 N11 H11A 110.1 . . ?
C12 N11 H11B 110.1 . . ?
C15 N11 H11B 110.1 . . ?
H11A N11 H11B 108.4 . . ?
N11 C12 C13 102.2(12) . . ?
N11 C12 H12A 111.3 . . ?
C13 C12 H12A 111.3 . . ?
N11 C12 H12B 111.3 . . ?
C13 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
C14 C13 C12 105.0(12) . . ?
C14 C13 H13A 110.7 . . ?
C12 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
C12 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
C13 C14 C15 105.0(13) . . ?
C13 C14 H14A 110.8 . . ?
C15 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
C15 C14 H14B 110.8 . . ?
H14A C14 H14B 108.8 . . ?
N11 C15 C16 111.8(12) . . ?
N11 C15 C14 104.4(11) . . ?
C16 C15 C14 115.4(12) . . ?
N11 C15 H15 108.3 . . ?
C16 C15 H15 108.3 . . ?
C14 C15 H15 108.3 . . ?
O17 C16 O18 127.0(14) . . ?
O17 C16 C15 117.5(14) . . ?
O18 C16 C15 115.4(14) . . ?
C26 C21 C22 119(2) . . ?
C26 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 122(3) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 118(3) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C23 C24 C25 122(3) . . ?
C23 C24 H24 118.9 . . ?
C25 C24 H24 118.9 . . ?
C24 C25 C26 120(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C21 C26 C25 119(2) . . ?
C21 C26 C27 119(2) . . ?
C25 C26 C27 121.9(19) . . ?
O28 C27 C26 108.1(16) . . ?
O28 C27 C29 107.2(18) . . ?
C26 C27 C29 109.8(18) . . ?
O28 C27 H27 110.5 . . ?
C26 C27 H27 110.5 . . ?
C29 C27 H27 110.5 . . ?
C27 O28 H28 109.5 . . ?
O30 C29 O31 123.8(19) . . ?
O30 C29 C27 127(2) . . ?
O31 C29 C27 109(2) . . ?
C29 O31 H31 109.5 . . ?
C26B C21B C22B 119(3) . . ?
C26B C21B H21B 120.5 . . ?
C22B C21B H21B 120.5 . . ?
C23B C22B C21B 121(4) . . ?
C23B C22B H22B 119.6 . . ?
C21B C22B H22B 119.6 . . ?
C22B C23B C24B 119(4) . . ?
C22B C23B H23B 120.6 . . ?
C24B C23B H23B 120.6 . . ?
C23B C24B C25B 122(4) . . ?
C23B C24B H24B 119.1 . . ?
C25B C24B H24B 119.1 . . ?
C24B C25B C26B 120(3) . . ?
C24B C25B H25B 120.2 . . ?
C26B C25B H25B 120.2 . . ?
C21B C26B C25B 118(3) . . ?
C21B C26B C27B 119(3) . . ?
C25B C26B C27B 122(3) . . ?
O28B C27B C26B 109(3) . . ?
O28B C27B C29B 108(3) . . ?
C26B C27B C29B 111(3) . . ?
O28B C27B H27B 109.7 . . ?
C26B C27B H27B 109.7 . . ?
C29B C27B H27B 109.7 . . ?
C27B O28B H28B 109.5 . . ?
O30B C29B O31B 124(3) . . ?
O30B C29B C27B 127(3) . . ?
O31B C29B C27B 108(3) . . ?
C29B O31B H31B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 33(2) . . . . ?
N1 C2 C3 C4 -36(3) . . . . ?
C2 C3 C4 C5 25(3) . . . . ?
C5 N1 C2B C3B 19(10) . . . . ?
N1 C2B C3B C4B -9(12) . . . . ?
C2B C3B C4B C5 -3(13) . . . . ?
C2B N1 C5 C6 84(6) . . . . ?
C2 N1 C5 C6 104.2(18) . . . . ?
C2 N1 C5 C4 -16.7(19) . . . . ?
C2B N1 C5 C4B -19(7) . . . . ?
C3 C4 C5 N1 -5(2) . . . . ?
C3 C4 C5 C6 -124(2) . . . . ?
C3B C4B C5 N1 14(10) . . . . ?
C3B C4B C5 C6 -98(9) . . . . ?
N1 C5 C6 O7 -5(2) . . . . ?
C4 C5 C6 O7 109(2) . . . . ?
C4B C5 C6 O7 98(3) . . . . ?
N1 C5 C6 O8 172.3(13) . . . . ?
C4 C5 C6 O8 -73(2) . . . . ?
C4B C5 C6 O8 -84(3) . . . . ?
C15 N11 C12 C13 -37.2(14) . . . . ?
N11 C12 C13 C14 38.0(15) . . . . ?
C12 C13 C14 C15 -24.9(16) . . . . ?
C12 N11 C15 C16 147.1(12) . . . . ?
C12 N11 C15 C14 21.8(14) . . . . ?
C13 C14 C15 N11 2.6(15) . . . . ?
C13 C14 C15 C16 -120.4(14) . . . . ?
N11 C15 C16 O17 10.1(18) . . . . ?
C14 C15 C16 O17 129.2(14) . . . . ?
N11 C15 C16 O18 -172.7(11) . . . . ?
C14 C15 C16 O18 -53.6(17) . . . . ?
C26 C21 C22 C23 4(6) . . . . ?
C21 C22 C23 C24 -1(5) . . . . ?
C22 C23 C24 C25 -3(5) . . . . ?
C23 C24 C25 C26 2(6) . . . . ?
C22 C21 C26 C25 -5(6) . . . . ?
C22 C21 C26 C27 178(3) . . . . ?
C24 C25 C26 C21 1(6) . . . . ?
C24 C25 C26 C27 179(3) . . . . ?
C21 C26 C27 O28 -127(4) . . . . ?
C25 C26 C27 O28 55(4) . . . . ?
C21 C26 C27 C29 116(4) . . . . ?
C25 C26 C27 C29 -61(4) . . . . ?
O28 C27 C29 O30 0(4) . . . . ?
C26 C27 C29 O30 117(4) . . . . ?
O28 C27 C29 O31 174(3) . . . . ?
C26 C27 C29 O31 -69(3) . . . . ?
C26B C21B C22B C23B -14(18) . . . . ?
C21B C22B C23B C24B 4(17) . . . . ?
C22B C23B C24B C25B 8(17) . . . . ?
C23B C24B C25B C26B -9(19) . . . . ?
C22B C21B C26B C25B 13(18) . . . . ?
C22B C21B C26B C27B 180(9) . . . . ?
C24B C25B C26B C21B -2(19) . . . . ?
C24B C25B C26B C27B -169(10) . . . . ?
C21B C26B C27B O28B -111(10) . . . . ?
C25B C26B C27B O28B 56(11) . . . . ?
C21B C26B C27B C29B 131(10) . . . . ?
C25B C26B C27B C29B -63(11) . . . . ?
O28B C27B C29B O30B -12(10) . . . . ?
C26B C27B C29B O30B 107(9) . . . . ?
O28B C27B C29B O31B 161(8) . . . . ?
C26B C27B C29B O31B -80(8) . . . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.059



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
