# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_tw_Naibu_L-pro
_database_code_depnum_ccdc_archive 'CCDC 2530249'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2026-02-10 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            'ibuprofen L-proline sodium'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H30 N Na O6'
_chemical_formula_sum            'C18 H30 N Na O6'
_chemical_formula_weight         379.42

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'
Na Na 0.0362 0.0249 '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                   9.3842(6)
_cell_length_b                   6.1358(5)
_cell_length_c                   18.3975(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.437(7)
_cell_angle_gamma                90
_cell_volume                     1052.65(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4027
_cell_measurement_theta_min      3.2600
_cell_measurement_theta_max      26.3580

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.84157
_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       
;
'120 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10131
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.291
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4227
_reflns_number_gt                3777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.980

_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
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0666P)²+0.6195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(19)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4227
_refine_ls_number_parameters     341
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.105
_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
Na1 Na 0.75241(16) 0.5427(3) 0.48084(9) 0.0409(4) Uani 1 1 d . . . . .
O2 O 0.9790(4) 0.4982(6) 0.5496(2) 0.0577(8) Uani 1 1 d G . . . .
H2A H 1.013402 0.610907 0.567988 0.087 Uiso 1 1 d G U . . .
H2B H 1.002505 0.403685 0.580140 0.087 Uiso 1 1 d G U . . .
O3 O 0.7719(4) 0.9027(6) 0.5245(2) 0.0611(9) Uani 1 1 d G . . . .
H3A H 0.722481 1.008660 0.532244 0.092 Uiso 1 1 d G U . . .
H3B H 0.842836 0.954593 0.508723 0.092 Uiso 1 1 d G U . . .
N11 N 0.3599(3) 0.5012(7) 0.64928(19) 0.0441(8) Uani 1 1 d D U . . .
H11A H 0.294718 0.599455 0.632262 0.053 Uiso 1 1 calc R U . A 3
H11B H 0.321791 0.369139 0.641975 0.053 Uiso 1 1 calc R U . A 3
C12 C 0.4021(10) 0.537(2) 0.7287(4) 0.061(3) Uani 0.723(17) 1 d D . P B 3
H12A H 0.323954 0.600236 0.751977 0.073 Uiso 0.723(17) 1 calc R U P B 3
H12B H 0.431874 0.402146 0.753248 0.073 Uiso 0.723(17) 1 calc R U P B 3
C13 C 0.5223(9) 0.6899(17) 0.7293(4) 0.068(3) Uani 0.723(17) 1 d D . P B 3
H13A H 0.582120 0.684684 0.775850 0.081 Uiso 0.723(17) 1 calc R U P B 3
H13B H 0.487862 0.837810 0.720831 0.081 Uiso 0.723(17) 1 calc R U P B 3
C14 C 0.6055(15) 0.615(3) 0.6677(5) 0.061(4) Uani 0.723(17) 1 d D . P B 3
H14A H 0.675042 0.503751 0.684642 0.073 Uiso 0.723(17) 1 calc R U P B 3
H14B H 0.655334 0.735903 0.647928 0.073 Uiso 0.723(17) 1 calc R U P B 3
C12B C 0.420(2) 0.483(7) 0.7276(8) 0.061(8) Uani 0.277(17) 1 d D U P B 4
H12C H 0.371849 0.584013 0.756876 0.073 Uiso 0.277(17) 1 calc R U P B 4
H12D H 0.404678 0.336329 0.745051 0.073 Uiso 0.277(17) 1 calc R U P B 4
C13B C 0.575(2) 0.530(4) 0.7358(10) 0.065(6) Uani 0.277(17) 1 d D U P B 4
H13C H 0.630856 0.397073 0.740585 0.079 Uiso 0.277(17) 1 calc R U P B 4
H13D H 0.601464 0.621973 0.778036 0.079 Uiso 0.277(17) 1 calc R U P B 4
C14B C 0.595(4) 0.649(8) 0.6648(9) 0.048(8) Uani 0.277(17) 1 d D U P B 4
H14C H 0.693300 0.637856 0.653172 0.058 Uiso 0.277(17) 1 calc R U P B 4
H14D H 0.568706 0.801581 0.666984 0.058 Uiso 0.277(17) 1 calc R U P B 4
C15 C 0.4911(4) 0.5220(7) 0.6101(2) 0.0381(8) Uani 1 1 d D U . . .
H15 H 0.473230 0.622455 0.568676 0.046 Uiso 1 1 calc R U . B 3
C16 C 0.5343(4) 0.2987(7) 0.5840(2) 0.0359(8) Uani 1 1 d . . . . .
O17 O 0.6425(3) 0.2953(5) 0.55030(17) 0.0489(8) Uani 1 1 d . . . . .
O18 O 0.4602(3) 0.1387(5) 0.59789(19) 0.0503(8) Uani 1 1 d . . . . .
C21 C 1.1136(6) 0.6041(12) 0.2903(3) 0.0717(17) Uani 1 1 d . . . . .
H21A H 1.180280 0.558496 0.257382 0.108 Uiso 1 1 calc R U . . .
H21B H 1.164493 0.636409 0.337236 0.108 Uiso 1 1 calc R U . . .
H21C H 1.063721 0.732074 0.271190 0.108 Uiso 1 1 calc R U . . .
C22 C 1.0068(5) 0.4236(9) 0.2982(3) 0.0498(11) Uani 1 1 d D . . . .
H22 H 1.061131 0.296258 0.317814 0.060 Uiso 0.620(15) 1 calc R U P C 1
H22B H 1.059476 0.292608 0.315813 0.060 Uiso 0.380(15) 1 calc R U P C 2
C23 C 0.8992(4) 0.4822(7) 0.3529(2) 0.0381(9) Uani 1 1 d . . . . .
O24 O 0.8719(4) 0.6760(5) 0.3657(2) 0.0524(8) Uani 1 1 d . . . . .
O25 O 0.8460(3) 0.3243(5) 0.38420(17) 0.0459(7) Uani 1 1 d . . . . .
C26 C 0.9228(15) 0.354(2) 0.2249(5) 0.052(5) Uani 0.620(15) 1 d DG U P C 1
C27 C 0.9345(13) 0.1504(18) 0.1933(6) 0.063(3) Uani 0.620(15) 1 d DG U P C 1
H27 H 0.996842 0.047139 0.216120 0.076 Uiso 0.620(15) 1 calc R U P C 1
C28 C 0.8529(13) 0.1006(14) 0.1276(5) 0.069(3) Uani 0.620(15) 1 d DG U P C 1
H28 H 0.860743 -0.035885 0.106471 0.083 Uiso 0.620(15) 1 calc R U P C 1
C29 C 0.7597(11) 0.2549(17) 0.0935(4) 0.068(3) Uani 0.620(15) 1 d DG U P C 1
C30 C 0.7480(12) 0.4590(16) 0.1251(5) 0.071(3) Uani 0.620(15) 1 d DG U P C 1
H30 H 0.685624 0.562237 0.102339 0.085 Uiso 0.620(15) 1 calc R U P C 1
C31 C 0.8295(15) 0.5087(17) 0.1908(6) 0.062(3) Uani 0.620(15) 1 d DG U P C 1
H31 H 0.821722 0.645266 0.211988 0.074 Uiso 0.620(15) 1 calc R U P C 1
C32 C 0.6722(14) 0.195(3) 0.0201(5) 0.089(4) Uani 0.620(15) 1 d D U P C 1
H32A H 0.649787 0.040648 0.021154 0.106 Uiso 0.620(15) 1 calc R U P C 1
H32B H 0.582026 0.273545 0.016801 0.106 Uiso 0.620(15) 1 calc R U P C 1
C33 C 0.7418(14) 0.240(3) -0.0487(6) 0.099(4) Uani 0.620(15) 1 d D U P C 1
H33 H 0.828430 0.152441 -0.050983 0.119 Uiso 0.620(15) 1 calc R U P C 1
C34 C 0.770(3) 0.463(3) -0.0539(13) 0.201(11) Uani 0.620(15) 1 d D U P C 1
H34A H 0.858272 0.497300 -0.024606 0.302 Uiso 0.620(15) 1 calc R U P C 1
H34B H 0.693156 0.544690 -0.036694 0.302 Uiso 0.620(15) 1 calc R U P C 1
H34C H 0.777718 0.500261 -0.103999 0.302 Uiso 0.620(15) 1 calc R U P C 1
C35 C 0.644(2) 0.218(5) -0.1135(8) 0.165(9) Uani 0.620(15) 1 d D U P C 1
H35A H 0.689370 0.262291 -0.155138 0.247 Uiso 0.620(15) 1 calc R U P C 1
H35B H 0.560969 0.307367 -0.109572 0.247 Uiso 0.620(15) 1 calc R U P C 1
H35C H 0.614422 0.068104 -0.119133 0.247 Uiso 0.620(15) 1 calc R U P C 1
C26B C 0.920(3) 0.371(4) 0.2252(10) 0.059(8) Uani 0.380(15) 1 d DG U P C 2
C27B C 0.972(2) 0.181(4) 0.1964(11) 0.074(7) Uani 0.380(15) 1 d DG U P C 2
H27B H 1.052938 0.113626 0.220079 0.089 Uiso 0.380(15) 1 calc R U P C 2
C28B C 0.904(2) 0.093(3) 0.1321(11) 0.082(7) Uani 0.380(15) 1 d DG U P C 2
H28B H 0.938773 -0.033265 0.112785 0.098 Uiso 0.380(15) 1 calc R U P C 2
C29B C 0.7828(18) 0.195(3) 0.0967(8) 0.074(5) Uani 0.380(15) 1 d DG U P C 2
C30B C 0.7303(18) 0.384(3) 0.1255(9) 0.071(5) Uani 0.380(15) 1 d DG U P C 2
H30B H 0.649436 0.451767 0.101809 0.085 Uiso 0.380(15) 1 calc R U P C 2
C31B C 0.799(2) 0.472(3) 0.1898(10) 0.071(6) Uani 0.380(15) 1 d DG U P C 2
H31B H 0.763599 0.598661 0.209103 0.085 Uiso 0.380(15) 1 calc R U P C 2
C32B C 0.703(2) 0.095(4) 0.0269(8) 0.087(6) Uani 0.380(15) 1 d D U P C 2
H32C H 0.654575 -0.034234 0.041804 0.105 Uiso 0.380(15) 1 calc R U P C 2
H32D H 0.629171 0.197930 0.008836 0.105 Uiso 0.380(15) 1 calc R U P C 2
C33B C 0.779(2) 0.031(5) -0.0367(10) 0.131(8) Uani 0.380(15) 1 d D U P C 2
H33B H 0.827322 -0.107298 -0.023504 0.157 Uiso 0.380(15) 1 calc R U P C 2
C34B C 0.884(2) 0.170(5) -0.0563(9) 0.112(8) Uani 0.380(15) 1 d D U P C 2
H34D H 0.933437 0.102200 -0.093197 0.168 Uiso 0.380(15) 1 calc R U P C 2
H34E H 0.950674 0.201611 -0.014202 0.168 Uiso 0.380(15) 1 calc R U P C 2
H34F H 0.840283 0.303020 -0.075162 0.168 Uiso 0.380(15) 1 calc R U P C 2
C35B C 0.690(3) -0.007(7) -0.1018(11) 0.146(11) Uani 0.380(15) 1 d D U P C 2
H35D H 0.655347 0.129777 -0.122327 0.220 Uiso 0.380(15) 1 calc R U P C 2
H35E H 0.610087 -0.095234 -0.091704 0.220 Uiso 0.380(15) 1 calc R U P C 2
H35F H 0.743046 -0.080852 -0.136026 0.220 Uiso 0.380(15) 1 calc R U P C 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
Na1 O17 2.302(3) . ?
Na1 O3 2.351(4) . ?
Na1 O2 2.365(3) . ?
Na1 O18 2.404(4) 2_656 ?
Na1 O25 2.466(3) . ?
Na1 O24 2.636(4) . ?
Na1 C23 2.882(4) . ?
O2 H2A 0.8200 . ?
O2 H2B 0.8201 . ?
O3 H3A 0.8200 . ?
O3 H3B 0.8200 . ?
N11 C12 1.487(8) . ?
N11 C12B 1.493(13) . ?
N11 C15 1.500(5) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
C12 C13 1.466(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.519(15) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.531(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C12B C13B 1.468(15) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B C14B 1.527(19) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15 1.536(13) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15 C16 1.522(6) . ?
C15 H15 0.9800 . ?
C16 O18 1.246(5) . ?
C16 O17 1.248(5) . ?
C21 C22 1.511(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C26B 1.526(10) . ?
C22 C26 1.543(7) . ?
C22 C23 1.545(6) . ?
C22 H22 0.9800 . ?
C22 H22B 0.9800 . ?
C23 O24 1.245(6) . ?
C23 O25 1.259(5) . ?
C26 C27 1.3900 . ?
C26 C31 1.3900 . ?
C27 C28 1.3900 . ?
C27 H27 0.9300 . ?
C28 C29 1.3900 . ?
C28 H28 0.9300 . ?
C29 C30 1.3900 . ?
C29 C32 1.545(9) . ?
C30 C31 1.3900 . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.515(14) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.397(16) . ?
C33 C35 1.429(14) . ?
C33 H33 0.9800 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C26B C27B 1.3900 . ?
C26B C31B 1.3900 . ?
C27B C28B 1.3900 . ?
C27B H27B 0.9300 . ?
C28B C29B 1.3900 . ?
C28B H28B 0.9300 . ?
C29B C30B 1.3900 . ?
C29B C32B 1.537(12) . ?
C30B C31B 1.3900 . ?
C30B H30B 0.9300 . ?
C31B H31B 0.9300 . ?
C32B C33B 1.490(16) . ?
C32B H32C 0.9700 . ?
C32B H32D 0.9700 . ?
C33B C34B 1.377(16) . ?
C33B C35B 1.404(16) . ?
C33B H33B 0.9800 . ?
C34B H34D 0.9600 . ?
C34B H34E 0.9600 . ?
C34B H34F 0.9600 . ?
C35B H35D 0.9600 . ?
C35B H35E 0.9600 . ?
C35B H35F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O17 Na1 O3 116.91(14) . . ?
O17 Na1 O2 93.38(14) . . ?
O3 Na1 O2 83.97(15) . . ?
O17 Na1 O18 95.89(13) . 2_656 ?
O3 Na1 O18 90.20(14) . 2_656 ?
O2 Na1 O18 170.56(14) . 2_656 ?
O17 Na1 O25 105.06(12) . . ?
O3 Na1 O25 137.47(13) . . ?
O2 Na1 O25 87.21(13) . . ?
O18 Na1 O25 92.13(12) 2_656 . ?
O17 Na1 O24 155.29(13) . . ?
O3 Na1 O24 87.68(13) . . ?
O2 Na1 O24 91.60(13) . . ?
O18 Na1 O24 80.72(12) 2_656 . ?
O25 Na1 O24 51.02(10) . . ?
O17 Na1 C23 130.81(13) . . ?
O3 Na1 C23 111.99(14) . . ?
O2 Na1 C23 86.49(13) . . ?
O18 Na1 C23 88.83(12) 2_656 . ?
O25 Na1 C23 25.75(12) . . ?
O24 Na1 C23 25.57(12) . . ?
Na1 O2 H2A 114.3 . . ?
Na1 O2 H2B 127.2 . . ?
H2A O2 H2B 104.5 . . ?
Na1 O3 H3A 141.3 . . ?
Na1 O3 H3B 106.2 . . ?
H3A O3 H3B 104.5 . . ?
C12 N11 C15 108.5(5) . . ?
C12B N11 C15 103.1(9) . . ?
C12 N11 H11A 110.0 . . ?
C15 N11 H11A 110.0 . . ?
C12 N11 H11B 110.0 . . ?
C15 N11 H11B 110.0 . . ?
H11A N11 H11B 108.4 . . ?
C13 C12 N11 102.9(6) . . ?
C13 C12 H12A 111.2 . . ?
N11 C12 H12A 111.2 . . ?
C13 C12 H12B 111.2 . . ?
N11 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C12 C13 C14 105.1(7) . . ?
C12 C13 H13A 110.7 . . ?
C14 C13 H13A 110.7 . . ?
C12 C13 H13B 110.7 . . ?
C14 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
C13 C14 C15 104.5(8) . . ?
C13 C14 H14A 110.9 . . ?
C15 C14 H14A 110.9 . . ?
C13 C14 H14B 110.9 . . ?
C15 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C13B C12B N11 110.4(12) . . ?
C13B C12B H12C 109.6 . . ?
N11 C12B H12C 109.6 . . ?
C13B C12B H12D 109.6 . . ?
N11 C12B H12D 109.6 . . ?
H12C C12B H12D 108.1 . . ?
C12B C13B C14B 103.0(15) . . ?
C12B C13B H13C 111.2 . . ?
C14B C13B H13C 111.2 . . ?
C12B C13B H13D 111.2 . . ?
C14B C13B H13D 111.2 . . ?
H13C C13B H13D 109.1 . . ?
C13B C14B C15 100.7(14) . . ?
C13B C14B H14C 111.6 . . ?
C15 C14B H14C 111.6 . . ?
C13B C14B H14D 111.6 . . ?
C15 C14B H14D 111.6 . . ?
H14C C14B H14D 109.4 . . ?
N11 C15 C16 109.7(3) . . ?
N11 C15 C14 104.4(5) . . ?
C16 C15 C14 111.2(9) . . ?
N11 C15 C14B 103.0(12) . . ?
C16 C15 C14B 119(2) . . ?
N11 C15 H15 110.5 . . ?
C16 C15 H15 110.5 . . ?
C14 C15 H15 110.5 . . ?
O18 C16 O17 126.3(4) . . ?
O18 C16 C15 118.0(3) . . ?
O17 C16 C15 115.6(4) . . ?
C16 O17 Na1 134.9(3) . . ?
C16 O18 Na1 120.9(3) . 2_646 ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C21 C22 C26B 111.5(12) . . ?
C21 C22 C26 113.4(7) . . ?
C21 C22 C23 112.4(4) . . ?
C26B C22 C23 107.3(11) . . ?
C26 C22 C23 109.0(7) . . ?
C21 C22 H22 107.2 . . ?
C26 C22 H22 107.2 . . ?
C23 C22 H22 107.2 . . ?
C21 C22 H22B 108.5 . . ?
C26B C22 H22B 108.5 . . ?
C23 C22 H22B 108.5 . . ?
O24 C23 O25 123.2(4) . . ?
O24 C23 C22 120.6(4) . . ?
O25 C23 C22 116.1(4) . . ?
O24 C23 Na1 66.1(2) . . ?
O25 C23 Na1 58.3(2) . . ?
C22 C23 Na1 165.6(3) . . ?
C23 O24 Na1 88.3(3) . . ?
C23 O25 Na1 95.9(3) . . ?
C27 C26 C31 120.0 . . ?
C27 C26 C22 123.8(8) . . ?
C31 C26 C22 116.2(8) . . ?
C28 C27 C26 120.0 . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C27 120.0 . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.0 . . ?
C28 C29 C32 118.6(8) . . ?
C30 C29 C32 121.4(8) . . ?
C29 C30 C31 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C26 120.0 . . ?
C30 C31 H31 120.0 . . ?
C26 C31 H31 120.0 . . ?
C33 C32 C29 116.8(10) . . ?
C33 C32 H32A 108.1 . . ?
C29 C32 H32A 108.1 . . ?
C33 C32 H32B 108.1 . . ?
C29 C32 H32B 108.1 . . ?
H32A C32 H32B 107.3 . . ?
C34 C33 C35 98.5(17) . . ?
C34 C33 C32 109.9(14) . . ?
C35 C33 C32 112.3(12) . . ?
C34 C33 H33 111.8 . . ?
C35 C33 H33 111.8 . . ?
C32 C33 H33 111.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C27B C26B C31B 120.0 . . ?
C27B C26B C22 109.6(14) . . ?
C31B C26B C22 130.2(14) . . ?
C26B C27B C28B 120.0 . . ?
C26B C27B H27B 120.0 . . ?
C28B C27B H27B 120.0 . . ?
C29B C28B C27B 120.0 . . ?
C29B C28B H28B 120.0 . . ?
C27B C28B H28B 120.0 . . ?
C28B C29B C30B 120.0 . . ?
C28B C29B C32B 120.5(12) . . ?
C30B C29B C32B 119.4(12) . . ?
C29B C30B C31B 120.0 . . ?
C29B C30B H30B 120.0 . . ?
C31B C30B H30B 120.0 . . ?
C30B C31B C26B 120.0 . . ?
C30B C31B H31B 120.0 . . ?
C26B C31B H31B 120.0 . . ?
C33B C32B C29B 122.0(13) . . ?
C33B C32B H32C 106.8 . . ?
C29B C32B H32C 106.8 . . ?
C33B C32B H32D 106.8 . . ?
C29B C32B H32D 106.8 . . ?
H32C C32B H32D 106.7 . . ?
C34B C33B C35B 105(2) . . ?
C34B C33B C32B 117.5(18) . . ?
C35B C33B C32B 114.9(17) . . ?
C34B C33B H33B 106.3 . . ?
C35B C33B H33B 106.3 . . ?
C32B C33B H33B 106.3 . . ?
C33B C34B H34D 109.5 . . ?
C33B C34B H34E 109.5 . . ?
H34D C34B H34E 109.5 . . ?
C33B C34B H34F 109.5 . . ?
H34D C34B H34F 109.5 . . ?
H34E C34B H34F 109.5 . . ?
C33B C35B H35D 109.5 . . ?
C33B C35B H35E 109.5 . . ?
H35D C35B H35E 109.5 . . ?
C33B C35B H35F 109.5 . . ?
H35D C35B H35F 109.5 . . ?
H35E C35B H35F 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
C15 N11 C12 C13 30.9(10) . . . . ?
N11 C12 C13 C14 -38.8(13) . . . . ?
C12 C13 C14 C15 32.6(15) . . . . ?
C15 N11 C12B C13B 10(3) . . . . ?
N11 C12B C13B C14B 18(4) . . . . ?
C12B C13B C14B C15 -38(4) . . . . ?
C12 N11 C15 C16 108.7(7) . . . . ?
C12B N11 C15 C16 94.6(18) . . . . ?
C12 N11 C15 C14 -10.6(11) . . . . ?
C12B N11 C15 C14B -34(3) . . . . ?
C13 C14 C15 N11 -13.1(14) . . . . ?
C13 C14 C15 C16 -131.3(11) . . . . ?
C13B C14B C15 N11 45(3) . . . . ?
C13B C14B C15 C16 -77(3) . . . . ?
N11 C15 C16 O18 -0.2(5) . . . . ?
C14 C15 C16 O18 114.8(6) . . . . ?
C14B C15 C16 O18 118.3(9) . . . . ?
N11 C15 C16 O17 179.8(3) . . . . ?
C14 C15 C16 O17 -65.2(6) . . . . ?
C14B C15 C16 O17 -61.7(10) . . . . ?
O18 C16 O17 Na1 153.4(3) . . . . ?
C15 C16 O17 Na1 -26.6(5) . . . . ?
O17 C16 O18 Na1 -94.8(4) . . . 2_646 ?
C15 C16 O18 Na1 85.2(4) . . . 2_646 ?
C21 C22 C23 O24 24.7(6) . . . . ?
C26B C22 C23 O24 -98.2(12) . . . . ?
C26 C22 C23 O24 -101.8(7) . . . . ?
C21 C22 C23 O25 -153.3(4) . . . . ?
C26B C22 C23 O25 83.8(12) . . . . ?
C26 C22 C23 O25 80.1(7) . . . . ?
C21 C22 C23 Na1 -89.5(13) . . . . ?
C26B C22 C23 Na1 147.5(15) . . . . ?
C26 C22 C23 Na1 143.9(12) . . . . ?
O25 C23 O24 Na1 12.2(4) . . . . ?
C22 C23 O24 Na1 -165.7(4) . . . . ?
O24 C23 O25 Na1 -13.1(5) . . . . ?
C22 C23 O25 Na1 164.8(3) . . . . ?
C21 C22 C26 C27 114.4(9) . . . . ?
C23 C22 C26 C27 -119.6(9) . . . . ?
C21 C22 C26 C31 -66.6(9) . . . . ?
C23 C22 C26 C31 59.4(9) . . . . ?
C31 C26 C27 C28 0.0 . . . . ?
C22 C26 C27 C28 179.0(14) . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
C27 C28 C29 C32 179.3(11) . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C32 C29 C30 C31 -179.2(11) . . . . ?
C29 C30 C31 C26 0.0 . . . . ?
C27 C26 C31 C30 0.0 . . . . ?
C22 C26 C31 C30 -179.1(13) . . . . ?
C28 C29 C32 C33 -88.4(14) . . . . ?
C30 C29 C32 C33 90.8(15) . . . . ?
C29 C32 C33 C34 -61(2) . . . . ?
C29 C32 C33 C35 -169.1(16) . . . . ?
C21 C22 C26B C27B 102.2(12) . . . . ?
C23 C22 C26B C27B -134.3(11) . . . . ?
C21 C22 C26B C31B -82.3(19) . . . . ?
C23 C22 C26B C31B 41(2) . . . . ?
C31B C26B C27B C28B 0.0 . . . . ?
C22 C26B C27B C28B 176(2) . . . . ?
C26B C27B C28B C29B 0.0 . . . . ?
C27B C28B C29B C30B 0.0 . . . . ?
C27B C28B C29B C32B -178(2) . . . . ?
C28B C29B C30B C31B 0.0 . . . . ?
C32B C29B C30B C31B 178(2) . . . . ?
C29B C30B C31B C26B 0.0 . . . . ?
C27B C26B C31B C30B 0.0 . . . . ?
C22 C26B C31B C30B -175(3) . . . . ?
C28B C29B C32B C33B -51(3) . . . . ?
C30B C29B C32B C33B 131(2) . . . . ?
C29B C32B C33B C34B -41(3) . . . . ?
C29B C32B C33B C35B -165(3) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Isopropyl alcohol/hexane (30/70)'
####################################################################### 
# 
# 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_tw_sibuna_lpro_r_all2_tw
_database_code_depnum_ccdc_archive 'CCDC 2530250'
loop_
_audit_author_name
_audit_author_address
'Koen Robeyns'
;Universite catholique de Louvain
Belgium
;
_audit_update_record             
;
2026-02-10 deposited with the CCDC.	2026-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            'S-ibuprofen L-proline sodium'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H26 N Na O4'
_chemical_formula_sum            'C18 H26 N Na O4'
_chemical_formula_weight         343.39

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.7825(6)
_cell_length_b                   9.8484(10)
_cell_length_c                   17.0500(15)
_cell_angle_alpha                83.265(8)
_cell_angle_beta                 84.387(8)
_cell_angle_gamma                85.997(8)
_cell_volume                     957.97(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3083
_cell_measurement_theta_min      2.4050
_cell_measurement_theta_max      26.3520

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81047
_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       
;
'200 images, ΔΦ 1.2° '
'150 images, ΔΦ 1.2° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6539
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.416
_diffrn_reflns_theta_max         25.251
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             6539
_reflns_number_gt                5359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.896
_reflns_Friedel_fraction_full    0.895

_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
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0540P)²+0.2825P] 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 2019 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         6539
_refine_ls_number_parameters     618
_refine_ls_number_restraints     295
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.043
_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
Na1 Na 0.5995(3) 0.58278(19) 0.54540(11) 0.0454(5) Uani 1 1 d . . . . .
N2 N 1.1618(7) 0.8578(4) 0.4578(2) 0.0454(10) Uani 1 1 d . . . . .
H2A H 1.282518 0.900457 0.469605 0.055 Uiso 1 1 calc R U . . .
H2AB H 1.113895 0.801378 0.500040 0.055 Uiso 1 1 calc R U . . .
C3 C 1.2304(11) 0.7794(6) 0.3884(4) 0.0632(15) Uani 1 1 d . . . . .
H3A H 1.390402 0.742617 0.388532 0.076 Uiso 1 1 calc R U . . .
H3AB H 1.129179 0.705082 0.387764 0.076 Uiso 1 1 calc R U . . .
C4 C 1.2005(13) 0.8867(8) 0.3200(4) 0.079(2) Uani 1 1 d . . . . .
H4A H 1.180408 0.845126 0.272489 0.095 Uiso 1 1 calc R U . . .
H4AB H 1.334802 0.942016 0.309926 0.095 Uiso 1 1 calc R U . . .
C5 C 0.9848(10) 0.9727(7) 0.3445(3) 0.0666(16) Uani 1 1 d . . . . .
H5A H 0.848243 0.938692 0.326369 0.080 Uiso 1 1 calc R U . . .
H5AB H 0.998482 1.067302 0.322174 0.080 Uiso 1 1 calc R U . . .
C6 C 0.9662(8) 0.9613(5) 0.4350(3) 0.0413(10) Uani 1 1 d . . . . .
H6 H 0.989993 1.049995 0.452789 0.050 Uiso 1 1 calc R U . . .
C7 C 0.7319(8) 0.9083(5) 0.4723(3) 0.0440(11) Uani 1 1 d . . . . .
O8 O 0.7299(6) 0.7899(4) 0.5059(3) 0.0656(11) Uani 1 1 d . . . . .
O9 O 0.5599(6) 0.9915(4) 0.4636(2) 0.0564(9) Uani 1 1 d . . . . .
C11 C 0.6260(10) 0.3834(6) 0.3284(3) 0.0544(13) Uani 1 1 d D . . . .
H11 H 0.776171 0.338554 0.311347 0.065 Uiso 1 1 calc R U . A 1
C12 C 0.6499(9) 0.4320(5) 0.4095(3) 0.0483(12) Uani 1 1 d . . . . .
O13 O 0.8398(7) 0.4750(5) 0.4219(2) 0.0719(12) Uani 1 1 d . . . . .
O14 O 0.4816(7) 0.4271(6) 0.4605(3) 0.0788(13) Uani 1 1 d . . . . .
C15 C 0.4429(15) 0.2764(7) 0.3337(4) 0.085(2) Uani 1 1 d . . . . .
H15A H 0.291863 0.317986 0.347965 0.127 Uiso 1 1 calc R U . . .
H15B H 0.478830 0.202169 0.373121 0.127 Uiso 1 1 calc R U . . .
H15C H 0.443429 0.242233 0.283176 0.127 Uiso 1 1 calc R U . . .
C16 C 0.574(5) 0.500(3) 0.264(2) 0.043(5) Uani 0.576(18) 1 d D . P B 1
C17 C 0.741(5) 0.596(2) 0.2454(14) 0.065(7) Uani 0.576(18) 1 d D . P B 1
H17 H 0.878510 0.583665 0.270051 0.078 Uiso 0.576(18) 1 calc R U P B 1
C18 C 0.707(6) 0.711(3) 0.190(2) 0.073(7) Uani 0.576(18) 1 d D . P B 1
H18 H 0.812222 0.779682 0.183597 0.088 Uiso 0.576(18) 1 calc R U P B 1
C19 C 0.522(4) 0.723(2) 0.1438(10) 0.060(6) Uani 0.576(18) 1 d D . P B 1
C20 C 0.370(4) 0.621(3) 0.1570(17) 0.065(7) Uani 0.576(18) 1 d D . P B 1
H20 H 0.245427 0.625125 0.126116 0.078 Uiso 0.576(18) 1 calc R U P B 1
C21 C 0.396(4) 0.510(2) 0.2154(12) 0.058(6) Uani 0.576(18) 1 d D . P B 1
H21 H 0.290933 0.441476 0.221344 0.070 Uiso 0.576(18) 1 calc R U P B 1
C22 C 0.500(4) 0.8389(18) 0.0778(7) 0.071(6) Uani 0.576(18) 1 d D U P B 1
H22A H 0.337036 0.870842 0.077581 0.085 Uiso 0.576(18) 1 calc R U P B 1
H22B H 0.585803 0.914447 0.088899 0.085 Uiso 0.576(18) 1 calc R U P B 1
C23 C 0.585(3) 0.8009(16) -0.0035(7) 0.089(5) Uani 0.576(18) 1 d D U P B 1
H23 H 0.502924 0.720968 -0.011853 0.107 Uiso 0.576(18) 1 calc R U P B 1
C24 C 0.528(4) 0.914(2) -0.0688(8) 0.133(8) Uani 0.576(18) 1 d D U P B 1
H24A H 0.585580 0.885406 -0.119408 0.200 Uiso 0.576(18) 1 calc R U P B 1
H24B H 0.362222 0.931518 -0.067099 0.200 Uiso 0.576(18) 1 calc R U P B 1
H24C H 0.599577 0.995654 -0.061031 0.200 Uiso 0.576(18) 1 calc R U P B 1
C25 C 0.845(3) 0.759(2) -0.0105(9) 0.128(8) Uani 0.576(18) 1 d D U P B 1
H25A H 0.891669 0.735456 -0.063128 0.192 Uiso 0.576(18) 1 calc R U P B 1
H25B H 0.931581 0.833265 -0.000117 0.192 Uiso 0.576(18) 1 calc R U P B 1
H25C H 0.874817 0.680694 0.027244 0.192 Uiso 0.576(18) 1 calc R U P B 1
C16B C 0.607(8) 0.513(4) 0.269(3) 0.045(7) Uani 0.424(18) 1 d D U P B 2
C17B C 0.753(5) 0.621(3) 0.2584(17) 0.044(5) Uani 0.424(18) 1 d D U P B 2
H17B H 0.863564 0.623735 0.294205 0.053 Uiso 0.424(18) 1 calc R U P B 2
C18B C 0.740(7) 0.726(4) 0.195(3) 0.060(7) Uani 0.424(18) 1 d D U P B 2
H18B H 0.854911 0.789111 0.186184 0.072 Uiso 0.424(18) 1 calc R U P B 2
C19B C 0.562(5) 0.738(3) 0.1468(14) 0.054(6) Uani 0.424(18) 1 d D U P B 2
C20B C 0.392(6) 0.646(4) 0.167(2) 0.062(7) Uani 0.424(18) 1 d D U P B 2
H20B H 0.259907 0.655550 0.139479 0.075 Uiso 0.424(18) 1 calc R U P B 2
C21B C 0.409(5) 0.539(2) 0.2287(16) 0.050(6) Uani 0.424(18) 1 d D U P B 2
H21B H 0.284126 0.483852 0.242704 0.060 Uiso 0.424(18) 1 calc R U P B 2
C22B C 0.548(6) 0.850(2) 0.0789(11) 0.075(7) Uani 0.424(18) 1 d D U P B 2
H22C H 0.387496 0.862641 0.065611 0.090 Uiso 0.424(18) 1 calc R U P B 2
H22D H 0.587499 0.934718 0.096729 0.090 Uiso 0.424(18) 1 calc R U P B 2
C23B C 0.701(4) 0.8264(17) 0.0047(10) 0.081(6) Uani 0.424(18) 1 d D U P B 2
H23B H 0.861531 0.817806 0.019499 0.097 Uiso 0.424(18) 1 calc R U P B 2
C24B C 0.688(5) 0.947(2) -0.0595(12) 0.108(8) Uani 0.424(18) 1 d D U P B 2
H24D H 0.789084 0.927099 -0.105366 0.162 Uiso 0.424(18) 1 calc R U P B 2
H24E H 0.531239 0.963293 -0.073532 0.162 Uiso 0.424(18) 1 calc R U P B 2
H24F H 0.736695 1.027360 -0.040038 0.162 Uiso 0.424(18) 1 calc R U P B 2
C25B C 0.659(5) 0.6932(18) -0.0276(11) 0.123(9) Uani 0.424(18) 1 d D U P B 2
H25D H 0.761870 0.683640 -0.074702 0.185 Uiso 0.424(18) 1 calc R U P B 2
H25E H 0.689349 0.617358 0.011561 0.185 Uiso 0.424(18) 1 calc R U P B 2
H25F H 0.500831 0.694780 -0.040027 0.185 Uiso 0.424(18) 1 calc R U P B 2
Na31 Na 0.1091(3) 0.41801(19) 0.50786(11) 0.0448(5) Uani 1 1 d . . . . .
N32 N 0.5390(7) 0.1433(4) 0.6086(3) 0.0480(10) Uani 1 1 d . . . . .
H32A H 0.677537 0.098515 0.602522 0.058 Uiso 1 1 calc R U . . .
H32B H 0.504926 0.185274 0.561718 0.058 Uiso 1 1 calc R U . . .
C33 C 0.5425(11) 0.2454(6) 0.6668(4) 0.0633(15) Uani 1 1 d . . . . .
H33A H 0.692371 0.285516 0.662442 0.076 Uiso 1 1 calc R U . . .
H33B H 0.421652 0.317819 0.659075 0.076 Uiso 1 1 calc R U . . .
C34 C 0.4980(16) 0.1607(9) 0.7447(4) 0.090(2) Uani 1 1 d . . . . .
H34A H 0.428164 0.217268 0.784643 0.107 Uiso 1 1 calc R U . . .
H34B H 0.642099 0.116516 0.762233 0.107 Uiso 1 1 calc R U . . .
C35 C 0.3326(11) 0.0549(8) 0.7307(3) 0.0705(17) Uani 1 1 d . . . . .
H35A H 0.173974 0.082920 0.748635 0.085 Uiso 1 1 calc R U . . .
H35B H 0.373815 -0.033091 0.759389 0.085 Uiso 1 1 calc R U . . .
C36 C 0.3555(8) 0.0448(5) 0.6414(3) 0.0445(11) Uani 1 1 d . . . . .
H36 H 0.408427 -0.048495 0.630714 0.053 Uiso 1 1 calc R U . . .
C37 C 0.1279(8) 0.0882(5) 0.6030(3) 0.0436(11) Uani 1 1 d . . . . .
O38 O 0.1189(6) 0.1958(4) 0.5568(2) 0.0597(10) Uani 1 1 d . . . . .
O39 O -0.0326(6) 0.0084(4) 0.6222(3) 0.0643(11) Uani 1 1 d . . . . .
C41 C 0.0182(10) 0.6433(5) 0.7172(3) 0.0533(13) Uani 1 1 d D . . . .
H41 H 0.137701 0.709818 0.714951 0.064 Uiso 1 1 calc R U . C 3
C42 C 0.0477(8) 0.5796(5) 0.6387(3) 0.0435(12) Uani 1 1 d . . . . .
O43 O -0.1083(6) 0.5069(4) 0.6227(2) 0.0512(9) Uani 1 1 d . . . . .
O44 O 0.2228(7) 0.6067(5) 0.5914(2) 0.0688(12) Uani 1 1 d . . . . .
C45 C -0.2207(13) 0.7220(7) 0.7254(4) 0.080(2) Uani 1 1 d . . . . .
H45A H -0.238232 0.762778 0.774276 0.120 Uiso 1 1 calc R U . . .
H45B H -0.341452 0.659893 0.725387 0.120 Uiso 1 1 calc R U . . .
H45C H -0.231398 0.792410 0.681737 0.120 Uiso 1 1 calc R U . . .
C46 C 0.060(4) 0.534(2) 0.7864(12) 0.050(5) Uani 0.683(16) 1 d D . P D 3
C47 C -0.078(3) 0.423(2) 0.8046(11) 0.059(5) Uani 0.683(16) 1 d D . P D 3
H47 H -0.191298 0.409275 0.771657 0.070 Uiso 0.683(16) 1 calc R U P D 3
C48 C -0.047(4) 0.330(2) 0.8730(14) 0.078(6) Uani 0.683(16) 1 d D . P D 3
H48 H -0.144185 0.257717 0.884952 0.093 Uiso 0.683(16) 1 calc R U P D 3
C49 C 0.123(3) 0.3434(19) 0.9224(7) 0.061(5) Uani 0.683(16) 1 d D . P D 3
C50 C 0.254(3) 0.4575(19) 0.9058(10) 0.074(6) Uani 0.683(16) 1 d D . P D 3
H50 H 0.366162 0.471199 0.939327 0.089 Uiso 0.683(16) 1 calc R U P D 3
C51 C 0.222(3) 0.5528(18) 0.8391(9) 0.065(5) Uani 0.683(16) 1 d D . P D 3
H51 H 0.309919 0.629518 0.829852 0.078 Uiso 0.683(16) 1 calc R U P D 3
C52 C 0.154(3) 0.2422(16) 0.9949(6) 0.077(5) Uani 0.683(16) 1 d D U P D 3
H52A H 0.089237 0.157057 0.987135 0.092 Uiso 0.683(16) 1 calc R U P D 3
H52B H 0.319241 0.223396 0.999458 0.092 Uiso 0.683(16) 1 calc R U P D 3
C53 C 0.044(2) 0.2878(13) 1.0714(6) 0.081(4) Uani 0.683(16) 1 d D U P D 3
H53 H 0.110323 0.374426 1.077341 0.097 Uiso 0.683(16) 1 calc R U P D 3
C54 C -0.217(2) 0.3164(17) 1.0729(7) 0.116(5) Uani 0.683(16) 1 d D U P D 3
H54A H -0.276731 0.344999 1.123305 0.174 Uiso 0.683(16) 1 calc R U P D 3
H54B H -0.251904 0.387560 1.031487 0.174 Uiso 0.683(16) 1 calc R U P D 3
H54C H -0.289101 0.234667 1.064858 0.174 Uiso 0.683(16) 1 calc R U P D 3
C55 C 0.102(3) 0.1881(16) 1.1430(6) 0.111(5) Uani 0.683(16) 1 d D U P D 3
H55A H 0.027647 0.221477 1.190409 0.166 Uiso 0.683(16) 1 calc R U P D 3
H55B H 0.046993 0.099992 1.137924 0.166 Uiso 0.683(16) 1 calc R U P D 3
H55C H 0.267312 0.179944 1.145647 0.166 Uiso 0.683(16) 1 calc R U P D 3
C46B C 0.031(9) 0.535(5) 0.789(3) 0.047(9) Uani 0.317(16) 1 d D U P D 4
C47B C -0.135(7) 0.438(5) 0.811(3) 0.054(9) Uani 0.317(16) 1 d D U P D 4
H47B H -0.271340 0.445922 0.785584 0.064 Uiso 0.317(16) 1 calc R U P D 4
C48B C -0.099(7) 0.329(4) 0.871(2) 0.049(7) Uani 0.317(16) 1 d D U P D 4
H48B H -0.200394 0.258359 0.877959 0.059 Uiso 0.317(16) 1 calc R U P D 4
C49B C 0.081(6) 0.323(3) 0.9182(15) 0.050(7) Uani 0.317(16) 1 d D U P D 4
C50B C 0.249(6) 0.418(3) 0.8967(19) 0.054(7) Uani 0.317(16) 1 d D U P D 4
H50B H 0.374932 0.417259 0.926914 0.065 Uiso 0.317(16) 1 calc R U P D 4
C51B C 0.231(7) 0.515(3) 0.830(2) 0.058(9) Uani 0.317(16) 1 d D U P D 4
H51B H 0.357060 0.568118 0.812084 0.070 Uiso 0.317(16) 1 calc R U P D 4
C52B C 0.100(6) 0.219(3) 0.9902(11) 0.063(7) Uani 0.317(16) 1 d D U P D 4
H52C H 0.065056 0.130243 0.976101 0.076 Uiso 0.317(16) 1 calc R U P D 4
H52D H 0.260240 0.211416 1.003343 0.076 Uiso 0.317(16) 1 calc R U P D 4
C53B C -0.054(4) 0.248(2) 1.0625(11) 0.077(7) Uani 0.317(16) 1 d D U P D 4
H53B H -0.214010 0.251410 1.048069 0.092 Uiso 0.317(16) 1 calc R U P D 4
C54B C -0.022(7) 0.384(2) 1.0928(17) 0.133(12) Uani 0.317(16) 1 d D U P D 4
H54D H -0.127665 0.393997 1.139215 0.200 Uiso 0.317(16) 1 calc R U P D 4
H54E H 0.134891 0.386710 1.105961 0.200 Uiso 0.317(16) 1 calc R U P D 4
H54F H -0.054424 0.457576 1.052439 0.200 Uiso 0.317(16) 1 calc R U P D 4
C55B C -0.034(6) 0.133(2) 1.1301(13) 0.104(9) Uani 0.317(16) 1 d D U P D 4
H55D H -0.135074 0.155366 1.175400 0.156 Uiso 0.317(16) 1 calc R U P D 4
H55E H -0.078107 0.049077 1.113589 0.156 Uiso 0.317(16) 1 calc R U P D 4
H55F H 0.123864 0.121307 1.143910 0.156 Uiso 0.317(16) 1 calc R U P D 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
Na1 O8 2.231(4) . ?
Na1 O44 2.248(4) . ?
Na1 O43 2.276(4) 1_655 ?
Na1 O14 2.402(5) . ?
Na1 O13 2.691(5) . ?
Na1 C12 2.877(6) . ?
Na1 Na31 3.306(2) 1_655 ?
Na1 Na31 3.511(2) . ?
N2 C3 1.495(7) . ?
N2 C6 1.517(6) . ?
N2 H2A 0.8900 . ?
N2 H2AB 0.8900 . ?
C3 C4 1.494(8) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 C5 1.510(9) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.528(7) . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C6 C7 1.538(6) . ?
C6 H6 0.9800 . ?
C7 O8 1.238(6) . ?
C7 O9 1.253(6) . ?
C11 C16 1.525(9) . ?
C11 C15 1.534(9) . ?
C11 C12 1.537(8) . ?
C11 C16B 1.537(11) . ?
C11 H11 0.9800 . ?
C12 O14 1.240(7) . ?
C12 O13 1.249(7) . ?
O13 Na31 2.241(4) 1_655 ?
O14 Na31 2.229(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C21 1.380(14) . ?
C16 C17 1.383(14) . ?
C17 C18 1.407(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(14) . ?
C19 C22 1.512(11) . ?
C20 C21 1.399(11) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.507(13) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.522(10) . ?
C23 C25 1.526(11) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C16B C21B 1.386(16) . ?
C16B C17B 1.389(16) . ?
C17B C18B 1.406(14) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.375(16) . ?
C18B H18B 0.9300 . ?
C19B C20B 1.372(16) . ?
C19B C22B 1.510(12) . ?
C20B C21B 1.401(13) . ?
C20B H20B 0.9300 . ?
C21B H21B 0.9300 . ?
C22B C23B 1.504(15) . ?
C22B H22C 0.9700 . ?
C22B H22D 0.9700 . ?
C23B C24B 1.522(11) . ?
C23B C25B 1.524(11) . ?
C23B H23B 0.9800 . ?
C24B H24D 0.9600 . ?
C24B H24E 0.9600 . ?
C24B H24F 0.9600 . ?
C25B H25D 0.9600 . ?
C25B H25E 0.9600 . ?
C25B H25F 0.9600 . ?
Na31 O38 2.247(4) . ?
Na31 O43 2.439(4) . ?
Na31 O44 2.624(5) . ?
Na31 C42 2.869(6) . ?
N32 C33 1.495(7) . ?
N32 C36 1.509(6) . ?
N32 H32A 0.8900 . ?
N32 H32B 0.8900 . ?
C33 C34 1.493(10) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.517(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.531(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C37 1.538(6) . ?
C36 H36 0.9800 . ?
C37 O38 1.246(6) . ?
C37 O39 1.251(6) . ?
C41 C46 1.527(9) . ?
C41 C42 1.535(7) . ?
C41 C46B 1.535(11) . ?
C41 C45 1.538(9) . ?
C41 H41 0.9800 . ?
C42 O44 1.254(6) . ?
C42 O43 1.258(6) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 C47 1.386(12) . ?
C46 C51 1.397(13) . ?
C47 C48 1.411(11) . ?
C47 H47 0.9300 . ?
C48 C49 1.377(14) . ?
C48 H48 0.9300 . ?
C49 C50 1.389(14) . ?
C49 C52 1.511(10) . ?
C50 C51 1.406(11) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 C53 1.496(12) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C53 C54 1.515(10) . ?
C53 C55 1.523(9) . ?
C53 H53 0.9800 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C46B C47B 1.389(15) . ?
C46B C51B 1.399(17) . ?
C47B C48B 1.413(14) . ?
C47B H47B 0.9300 . ?
C48B C49B 1.375(17) . ?
C48B H48B 0.9300 . ?
C49B C50B 1.391(17) . ?
C49B C52B 1.510(13) . ?
C50B C51B 1.408(14) . ?
C50B H50B 0.9300 . ?
C51B H51B 0.9300 . ?
C52B C53B 1.493(15) . ?
C52B H52C 0.9700 . ?
C52B H52D 0.9700 . ?
C53B C54B 1.521(12) . ?
C53B C55B 1.526(12) . ?
C53B H53B 0.9800 . ?
C54B H54D 0.9600 . ?
C54B H54E 0.9600 . ?
C54B H54F 0.9600 . ?
C55B H55D 0.9600 . ?
C55B H55E 0.9600 . ?
C55B H55F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Na1 O44 108.83(16) . . ?
O8 Na1 O43 96.53(16) . 1_655 ?
O44 Na1 O43 124.05(16) . 1_655 ?
O8 Na1 O14 125.7(2) . . ?
O44 Na1 O14 86.95(16) . . ?
O43 Na1 O14 117.20(17) 1_655 . ?
O8 Na1 O13 92.12(16) . . ?
O44 Na1 O13 135.90(16) . . ?
O43 Na1 O13 89.85(13) 1_655 . ?
O14 Na1 O13 50.25(13) . . ?
O8 Na1 C12 107.32(17) . . ?
O44 Na1 C12 110.41(17) . . ?
O43 Na1 C12 107.95(15) 1_655 . ?
O14 Na1 C12 25.17(15) . . ?
O13 Na1 C12 25.65(14) . . ?
O8 Na1 Na31 94.58(11) . 1_655 ?
O44 Na1 Na31 156.42(14) . 1_655 ?
O43 Na1 Na31 47.53(10) 1_655 1_655 ?
O14 Na1 Na31 81.44(12) . 1_655 ?
O13 Na1 Na31 42.35(9) . 1_655 ?
C12 Na1 Na31 63.26(11) . 1_655 ?
O8 Na1 Na31 133.50(12) . . ?
O44 Na1 Na31 48.33(12) . . ?
O43 Na1 Na31 129.97(11) 1_655 . ?
O14 Na1 Na31 38.90(10) . . ?
O13 Na1 Na31 89.03(10) . . ?
C12 Na1 Na31 63.51(12) . . ?
Na31 Na1 Na31 116.00(7) 1_655 . ?
C3 N2 C6 107.4(4) . . ?
C3 N2 H2A 110.2 . . ?
C6 N2 H2A 110.2 . . ?
C3 N2 H2AB 110.2 . . ?
C6 N2 H2AB 110.2 . . ?
H2A N2 H2AB 108.5 . . ?
C4 C3 N2 102.1(4) . . ?
C4 C3 H3A 111.4 . . ?
N2 C3 H3A 111.4 . . ?
C4 C3 H3AB 111.4 . . ?
N2 C3 H3AB 111.4 . . ?
H3A C3 H3AB 109.2 . . ?
C3 C4 C5 105.2(5) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4AB 110.7 . . ?
C5 C4 H4AB 110.7 . . ?
H4A C4 H4AB 108.8 . . ?
C4 C5 C6 106.2(4) . . ?
C4 C5 H5A 110.5 . . ?
C6 C5 H5A 110.5 . . ?
C4 C5 H5AB 110.5 . . ?
C6 C5 H5AB 110.5 . . ?
H5A C5 H5AB 108.7 . . ?
N2 C6 C5 104.2(4) . . ?
N2 C6 C7 109.5(4) . . ?
C5 C6 C7 112.1(4) . . ?
N2 C6 H6 110.3 . . ?
C5 C6 H6 110.3 . . ?
C7 C6 H6 110.3 . . ?
O8 C7 O9 126.8(4) . . ?
O8 C7 C6 118.2(4) . . ?
O9 C7 C6 114.9(4) . . ?
C7 O8 Na1 158.2(4) . . ?
C16 C11 C15 110.0(10) . . ?
C16 C11 C12 113.3(17) . . ?
C15 C11 C12 111.9(5) . . ?
C15 C11 C16B 119.5(13) . . ?
C12 C11 C16B 107(2) . . ?
C16 C11 H11 107.1 . . ?
C15 C11 H11 107.1 . . ?
C12 C11 H11 107.1 . . ?
O14 C12 O13 122.1(5) . . ?
O14 C12 C11 119.3(5) . . ?
O13 C12 C11 118.6(5) . . ?
O14 C12 Na1 55.5(3) . . ?
O13 C12 Na1 68.8(3) . . ?
C11 C12 Na1 163.7(3) . . ?
C12 O13 Na31 136.6(4) . 1_655 ?
C12 O13 Na1 85.5(3) . . ?
Na31 O13 Na1 83.67(14) 1_655 . ?
C12 O14 Na31 156.9(4) . . ?
C12 O14 Na1 99.3(4) . . ?
Na31 O14 Na1 98.52(16) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 115.9(11) . . ?
C21 C16 C11 126.6(15) . . ?
C17 C16 C11 116.7(14) . . ?
C16 C17 C18 121.7(12) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 121.1(12) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 116.8(10) . . ?
C20 C19 C22 121.7(12) . . ?
C18 C19 C22 121.3(12) . . ?
C19 C20 C21 122.3(11) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C16 C21 C20 121.4(11) . . ?
C16 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C19 114.4(12) . . ?
C23 C22 H22A 108.7 . . ?
C19 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C19 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 112.2(9) . . ?
C22 C23 C25 112.4(11) . . ?
C24 C23 C25 110.8(12) . . ?
C22 C23 H23 107.0 . . ?
C24 C23 H23 107.0 . . ?
C25 C23 H23 107.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C21B C16B C17B 113.5(14) . . ?
C21B C16B C11 119(2) . . ?
C17B C16B C11 127(2) . . ?
C16B C17B C18B 122.3(15) . . ?
C16B C17B H17B 118.8 . . ?
C18B C17B H17B 118.8 . . ?
C19B C18B C17B 121.4(15) . . ?
C19B C18B H18B 119.3 . . ?
C17B C18B H18B 119.3 . . ?
C20B C19B C18B 115.6(12) . . ?
C20B C19B C22B 122.6(16) . . ?
C18B C19B C22B 121.6(16) . . ?
C19B C20B C21B 122.5(14) . . ?
C19B C20B H20B 118.8 . . ?
C21B C20B H20B 118.8 . . ?
C16B C21B C20B 121.9(14) . . ?
C16B C21B H21B 119.0 . . ?
C20B C21B H21B 119.0 . . ?
C23B C22B C19B 115.6(14) . . ?
C23B C22B H22C 108.4 . . ?
C19B C22B H22C 108.4 . . ?
C23B C22B H22D 108.4 . . ?
C19B C22B H22D 108.4 . . ?
H22C C22B H22D 107.4 . . ?
C22B C23B C24B 112.7(13) . . ?
C22B C23B C25B 113.2(17) . . ?
C24B C23B C25B 111.0(14) . . ?
C22B C23B H23B 106.5 . . ?
C24B C23B H23B 106.5 . . ?
C25B C23B H23B 106.5 . . ?
C23B C24B H24D 109.5 . . ?
C23B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C23B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C23B C25B H25D 109.5 . . ?
C23B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
C23B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
O14 Na31 O13 117.40(18) . 1_455 ?
O14 Na31 O38 97.92(19) . . ?
O13 Na31 O38 113.45(18) 1_455 . ?
O14 Na31 O43 131.99(16) . . ?
O13 Na31 O43 97.42(15) 1_455 . ?
O38 Na31 O43 96.98(14) . . ?
O14 Na31 O44 82.11(15) . . ?
O13 Na31 O44 118.23(17) 1_455 . ?
O38 Na31 O44 121.20(16) . . ?
O43 Na31 O44 51.43(12) . . ?
O14 Na31 C42 106.49(16) . . ?
O13 Na31 C42 112.17(16) 1_455 . ?
O38 Na31 C42 108.20(15) . . ?
O43 Na31 C42 25.83(13) . . ?
O44 Na31 C42 25.91(13) . . ?
O14 Na31 Na1 148.30(16) . 1_455 ?
O13 Na31 Na1 53.97(13) 1_455 1_455 ?
O38 Na31 Na1 113.55(12) . 1_455 ?
O43 Na31 Na1 43.48(9) . 1_455 ?
O44 Na31 Na1 78.55(10) . 1_455 ?
C42 Na31 Na1 61.22(10) . 1_455 ?
O14 Na31 Na1 42.58(12) . . ?
O13 Na31 Na1 131.85(14) 1_455 . ?
O38 Na31 Na1 112.77(11) . . ?
O43 Na31 Na1 89.71(10) . . ?
O44 Na31 Na1 39.79(9) . . ?
C42 Na31 Na1 63.99(11) . . ?
Na1 Na31 Na1 116.00(7) 1_455 . ?
C33 N32 C36 107.2(4) . . ?
C33 N32 H32A 110.3 . . ?
C36 N32 H32A 110.3 . . ?
C33 N32 H32B 110.3 . . ?
C36 N32 H32B 110.3 . . ?
H32A N32 H32B 108.5 . . ?
C34 C33 N32 102.7(5) . . ?
C34 C33 H33A 111.2 . . ?
N32 C33 H33A 111.2 . . ?
C34 C33 H33B 111.2 . . ?
N32 C33 H33B 111.2 . . ?
H33A C33 H33B 109.1 . . ?
C33 C34 C35 105.8(5) . . ?
C33 C34 H34A 110.6 . . ?
C35 C34 H34A 110.6 . . ?
C33 C34 H34B 110.6 . . ?
C35 C34 H34B 110.6 . . ?
H34A C34 H34B 108.7 . . ?
C34 C35 C36 106.6(5) . . ?
C34 C35 H35A 110.4 . . ?
C36 C35 H35A 110.4 . . ?
C34 C35 H35B 110.4 . . ?
C36 C35 H35B 110.4 . . ?
H35A C35 H35B 108.6 . . ?
N32 C36 C35 104.1(4) . . ?
N32 C36 C37 109.5(4) . . ?
C35 C36 C37 112.8(4) . . ?
N32 C36 H36 110.1 . . ?
C35 C36 H36 110.1 . . ?
C37 C36 H36 110.1 . . ?
O38 C37 O39 126.3(5) . . ?
O38 C37 C36 118.7(4) . . ?
O39 C37 C36 114.9(4) . . ?
C37 O38 Na31 162.5(4) . . ?
C46 C41 C42 110.3(13) . . ?
C42 C41 C46B 112(3) . . ?
C46 C41 C45 113.9(12) . . ?
C42 C41 C45 109.5(5) . . ?
C46B C41 C45 108(2) . . ?
C46 C41 H41 107.6 . . ?
C42 C41 H41 107.6 . . ?
C45 C41 H41 107.6 . . ?
O44 C42 O43 122.6(5) . . ?
O44 C42 C41 118.4(5) . . ?
O43 C42 C41 119.0(4) . . ?
O44 C42 Na31 66.1(3) . . ?
O43 C42 Na31 57.7(3) . . ?
C41 C42 Na31 170.5(3) . . ?
C42 O43 Na1 124.8(3) . 1_455 ?
C42 O43 Na31 96.5(3) . . ?
Na1 O43 Na31 88.98(13) 1_455 . ?
C42 O44 Na1 154.6(4) . . ?
C42 O44 Na31 88.0(3) . . ?
Na1 O44 Na31 91.87(15) . . ?
C41 C45 H45A 109.5 . . ?
C41 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C41 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C47 C46 C51 117.8(8) . . ?
C47 C46 C41 122.0(11) . . ?
C51 C46 C41 119.7(13) . . ?
C46 C47 C48 120.3(10) . . ?
C46 C47 H47 119.8 . . ?
C48 C47 H47 119.8 . . ?
C49 C48 C47 122.1(10) . . ?
C49 C48 H48 119.0 . . ?
C47 C48 H48 119.0 . . ?
C48 C49 C50 117.5(8) . . ?
C48 C49 C52 121.2(11) . . ?
C50 C49 C52 121.2(11) . . ?
C49 C50 C51 121.1(10) . . ?
C49 C50 H50 119.4 . . ?
C51 C50 H50 119.4 . . ?
C46 C51 C50 121.0(10) . . ?
C46 C51 H51 119.5 . . ?
C50 C51 H51 119.5 . . ?
C53 C52 C49 115.1(9) . . ?
C53 C52 H52A 108.5 . . ?
C49 C52 H52A 108.5 . . ?
C53 C52 H52B 108.5 . . ?
C49 C52 H52B 108.5 . . ?
H52A C52 H52B 107.5 . . ?
C52 C53 C54 113.7(9) . . ?
C52 C53 C55 112.5(8) . . ?
C54 C53 C55 109.8(10) . . ?
C52 C53 H53 106.8 . . ?
C54 C53 H53 106.8 . . ?
C55 C53 H53 106.8 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C53 C55 H55A 109.5 . . ?
C53 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C53 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C47B C46B C51B 115.8(13) . . ?
C47B C46B C41 123(2) . . ?
C51B C46B C41 120(3) . . ?
C46B C47B C48B 120.9(16) . . ?
C46B C47B H47B 119.5 . . ?
C48B C47B H47B 119.5 . . ?
C49B C48B C47B 122.4(16) . . ?
C49B C48B H48B 118.8 . . ?
C47B C48B H48B 118.8 . . ?
C48B C49B C50B 116.4(13) . . ?
C48B C49B C52B 122.8(17) . . ?
C50B C49B C52B 120.8(17) . . ?
C49B C50B C51B 120.8(15) . . ?
C49B C50B H50B 119.6 . . ?
C51B C50B H50B 119.6 . . ?
C46B C51B C50B 122.1(17) . . ?
C46B C51B H51B 118.9 . . ?
C50B C51B H51B 118.9 . . ?
C53B C52B C49B 116.0(16) . . ?
C53B C52B H52C 108.3 . . ?
C49B C52B H52C 108.3 . . ?
C53B C52B H52D 108.3 . . ?
C49B C52B H52D 108.3 . . ?
H52C C52B H52D 107.4 . . ?
C52B C53B C54B 115.3(18) . . ?
C52B C53B C55B 112.1(15) . . ?
C54B C53B C55B 109.4(16) . . ?
C52B C53B H53B 106.5 . . ?
C54B C53B H53B 106.5 . . ?
C55B C53B H53B 106.5 . . ?
C53B C54B H54D 109.5 . . ?
C53B C54B H54E 109.5 . . ?
H54D C54B H54E 109.5 . . ?
C53B C54B H54F 109.5 . . ?
H54D C54B H54F 109.5 . . ?
H54E C54B H54F 109.5 . . ?
C53B C55B H55D 109.5 . . ?
C53B C55B H55E 109.5 . . ?
H55D C55B H55E 109.5 . . ?
C53B C55B H55F 109.5 . . ?
H55D C55B H55F 109.5 . . ?
H55E C55B H55F 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
C6 N2 C3 C4 35.6(6) . . . . ?
N2 C3 C4 C5 -38.3(7) . . . . ?
C3 C4 C5 C6 27.3(7) . . . . ?
C3 N2 C6 C5 -18.9(5) . . . . ?
C3 N2 C6 C7 101.2(5) . . . . ?
C4 C5 C6 N2 -5.1(6) . . . . ?
C4 C5 C6 C7 -123.5(5) . . . . ?
N2 C6 C7 O8 -7.8(6) . . . . ?
C5 C6 C7 O8 107.4(6) . . . . ?
N2 C6 C7 O9 173.5(4) . . . . ?
C5 C6 C7 O9 -71.3(6) . . . . ?
O9 C7 O8 Na1 35.3(14) . . . . ?
C6 C7 O8 Na1 -143.3(8) . . . . ?
C16 C11 C12 O14 98.4(13) . . . . ?
C15 C11 C12 O14 -26.6(7) . . . . ?
C16B C11 C12 O14 105.7(19) . . . . ?
C16 C11 C12 O13 -81.8(13) . . . . ?
C15 C11 C12 O13 153.2(6) . . . . ?
C16B C11 C12 O13 -74.5(19) . . . . ?
C16 C11 C12 Na1 32(2) . . . . ?
C15 C11 C12 Na1 -93.4(14) . . . . ?
C16B C11 C12 Na1 39(2) . . . . ?
O14 C12 O13 Na31 59.6(8) . . . 1_655 ?
C11 C12 O13 Na31 -120.2(5) . . . 1_655 ?
Na1 C12 O13 Na31 75.9(5) . . . 1_655 ?
O14 C12 O13 Na1 -16.3(6) . . . . ?
C11 C12 O13 Na1 163.9(4) . . . . ?
O13 C12 O14 Na31 158.8(9) . . . . ?
C11 C12 O14 Na31 -21.4(14) . . . . ?
Na1 C12 O14 Na31 140.3(13) . . . . ?
O13 C12 O14 Na1 18.5(6) . . . . ?
C11 C12 O14 Na1 -161.7(4) . . . . ?
C15 C11 C16 C21 -2(5) . . . . ?
C12 C11 C16 C21 -128(4) . . . . ?
C15 C11 C16 C17 -172(3) . . . . ?
C12 C11 C16 C17 62(4) . . . . ?
C21 C16 C17 C18 12(6) . . . . ?
C11 C16 C17 C18 -177(3) . . . . ?
C16 C17 C18 C19 -9(7) . . . . ?
C17 C18 C19 C20 2(6) . . . . ?
C17 C18 C19 C22 -173(3) . . . . ?
C18 C19 C20 C21 2(5) . . . . ?
C22 C19 C20 C21 177(3) . . . . ?
C17 C16 C21 C20 -8(5) . . . . ?
C11 C16 C21 C20 -178(3) . . . . ?
C19 C20 C21 C16 2(5) . . . . ?
C20 C19 C22 C23 -77(3) . . . . ?
C18 C19 C22 C23 98(3) . . . . ?
C19 C22 C23 C24 172.0(16) . . . . ?
C19 C22 C23 C25 -62(2) . . . . ?
C15 C11 C16B C21B 8(6) . . . . ?
C12 C11 C16B C21B -120(5) . . . . ?
C15 C11 C16B C17B 178(5) . . . . ?
C12 C11 C16B C17B 50(6) . . . . ?
C21B C16B C17B C18B -18(8) . . . . ?
C11 C16B C17B C18B 171(5) . . . . ?
C16B C17B C18B C19B 9(8) . . . . ?
C17B C18B C19B C20B 4(8) . . . . ?
C17B C18B C19B C22B -180(4) . . . . ?
C18B C19B C20B C21B -6(7) . . . . ?
C22B C19B C20B C21B 178(3) . . . . ?
C17B C16B C21B C20B 16(7) . . . . ?
C11 C16B C21B C20B -173(4) . . . . ?
C19B C20B C21B C16B -5(7) . . . . ?
C20B C19B C22B C23B -104(4) . . . . ?
C18B C19B C22B C23B 80(5) . . . . ?
C19B C22B C23B C24B -177(2) . . . . ?
C19B C22B C23B C25B 56(3) . . . . ?
C36 N32 C33 C34 36.4(6) . . . . ?
N32 C33 C34 C35 -34.6(7) . . . . ?
C33 C34 C35 C36 20.7(8) . . . . ?
C33 N32 C36 C35 -23.5(5) . . . . ?
C33 N32 C36 C37 97.4(5) . . . . ?
C34 C35 C36 N32 1.5(7) . . . . ?
C34 C35 C36 C37 -117.1(6) . . . . ?
N32 C36 C37 O38 -4.0(6) . . . . ?
C35 C36 C37 O38 111.4(5) . . . . ?
N32 C36 C37 O39 175.7(4) . . . . ?
C35 C36 C37 O39 -68.9(6) . . . . ?
O39 C37 O38 Na31 111.8(11) . . . . ?
C36 C37 O38 Na31 -68.6(12) . . . . ?
C46 C41 C42 O44 -109.0(10) . . . . ?
C46B C41 C42 O44 -116(2) . . . . ?
C45 C41 C42 O44 124.9(5) . . . . ?
C46 C41 C42 O43 73.8(10) . . . . ?
C46B C41 C42 O43 67(2) . . . . ?
C45 C41 C42 O43 -52.3(6) . . . . ?
O44 C42 O43 Na1 -80.1(6) . . . 1_455 ?
C41 C42 O43 Na1 97.0(5) . . . 1_455 ?
Na31 C42 O43 Na1 -93.3(3) . . . 1_455 ?
O44 C42 O43 Na31 13.2(5) . . . . ?
C41 C42 O43 Na31 -169.7(4) . . . . ?
O43 C42 O44 Na1 -102.4(9) . . . . ?
C41 C42 O44 Na1 80.6(10) . . . . ?
Na31 C42 O44 Na1 -90.1(9) . . . . ?
O43 C42 O44 Na31 -12.2(5) . . . . ?
C41 C42 O44 Na31 170.7(4) . . . . ?
C42 C41 C46 C47 -62(3) . . . . ?
C45 C41 C46 C47 62(3) . . . . ?
C42 C41 C46 C51 126(2) . . . . ?
C45 C41 C46 C51 -110(2) . . . . ?
C51 C46 C47 C48 -2(4) . . . . ?
C41 C46 C47 C48 -175(3) . . . . ?
C46 C47 C48 C49 -2(5) . . . . ?
C47 C48 C49 C50 4(4) . . . . ?
C47 C48 C49 C52 -180(2) . . . . ?
C48 C49 C50 C51 -3(3) . . . . ?
C52 C49 C50 C51 -178.8(17) . . . . ?
C47 C46 C51 C50 4(4) . . . . ?
C41 C46 C51 C50 176(2) . . . . ?
C49 C50 C51 C46 -1(3) . . . . ?
C48 C49 C52 C53 -99(2) . . . . ?
C50 C49 C52 C53 77(2) . . . . ?
C49 C52 C53 C54 60.1(16) . . . . ?
C49 C52 C53 C55 -174.3(12) . . . . ?
C42 C41 C46B C47B -66(6) . . . . ?
C45 C41 C46B C47B 54(6) . . . . ?
C42 C41 C46B C51B 104(5) . . . . ?
C45 C41 C46B C51B -135(5) . . . . ?
C51B C46B C47B C48B 0(9) . . . . ?
C41 C46B C47B C48B 171(5) . . . . ?
C46B C47B C48B C49B 10(9) . . . . ?
C47B C48B C49B C50B -10(7) . . . . ?
C47B C48B C49B C52B 170(4) . . . . ?
C48B C49B C50B C51B 0(7) . . . . ?
C52B C49B C50B C51B -180(3) . . . . ?
C47B C46B C51B C50B -10(8) . . . . ?
C41 C46B C51B C50B 179(4) . . . . ?
C49B C50B C51B C46B 10(7) . . . . ?
C48B C49B C52B C53B -78(5) . . . . ?
C50B C49B C52B C53B 102(4) . . . . ?
C49B C52B C53B C54B -58(3) . . . . ?
C49B C52B C53B C55B 176(2) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Isopropyl alcohol/hexane (30/70)'
