# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Snprx_etoh
_database_code_depnum_ccdc_archive 'CCDC 1861015'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid; ethanol'
_chemical_name_common            'S-naproxen ethanol solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O3, C2 H6 O'
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32

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

_cell_length_a                   5.9273(2)
_cell_length_b                   8.7713(5)
_cell_length_c                   28.0747(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1459.61(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5433
_cell_measurement_theta_min      3.5040
_cell_measurement_theta_max      25.4230

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_T_min  0.20783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '180 images, ΔΦ 1.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9659
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.183
_diffrn_reflns_theta_max         25.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             2620
_reflns_number_gt                2291
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.969

_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0386P)²+0.7851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_chemical_absolute_configuration rm
_refine_ls_number_reflns         2620
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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
O1 O 0.2613(4) 0.6461(3) 0.40264(8) 0.0375(6) Uani 1 1 d . . . . .
O2 O 0.7638(4) 0.4868(3) 0.67332(8) 0.0374(6) Uani 1 1 d . . . . .
H2 H 0.756(7) 0.563(5) 0.6961(14) 0.056 Uiso 1 1 d . U . . .
O3 O 0.4938(4) 0.3958(3) 0.71983(9) 0.0411(6) Uani 1 1 d . . . . .
C1 C 0.0712(6) 0.7444(4) 0.40605(13) 0.0400(9) Uani 1 1 d . . . . .
H1A H 0.098840 0.821535 0.430600 0.060 Uiso 1 1 calc R U . . .
H1B H -0.062581 0.684595 0.414557 0.060 Uiso 1 1 calc R U . . .
H1C H 0.046225 0.794657 0.375325 0.060 Uiso 1 1 calc R U . . .
C2 C 0.3232(5) 0.5720(4) 0.44286(11) 0.0306(7) Uani 1 1 d . . . . .
C3 C 0.5278(5) 0.4913(4) 0.43870(12) 0.0330(7) Uani 1 1 d . . . . .
H3 H 0.606305 0.491233 0.409204 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6133(5) 0.4140(4) 0.47607(12) 0.0316(8) Uani 1 1 d . . . . .
H4 H 0.751686 0.360549 0.472572 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5001(5) 0.4115(4) 0.52044(11) 0.0276(7) Uani 1 1 d . . . . .
C6 C 0.5890(5) 0.3377(4) 0.56046(11) 0.0288(7) Uani 1 1 d . . . . .
H6 H 0.729502 0.286268 0.557782 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4802(5) 0.3376(4) 0.60294(12) 0.0303(7) Uani 1 1 d . . . . .
C8 C 0.2679(5) 0.4113(4) 0.60625(11) 0.0314(7) Uani 1 1 d . . . . .
H8 H 0.187448 0.409335 0.635502 0.038 Uiso 1 1 calc R U . . .
C9 C 0.1786(5) 0.4845(4) 0.56823(11) 0.0303(7) Uani 1 1 d . . . . .
H9 H 0.036936 0.534193 0.571400 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2909(5) 0.4887(4) 0.52415(11) 0.0282(7) Uani 1 1 d . . . . .
C11 C 0.2067(5) 0.5713(4) 0.48468(11) 0.0298(7) Uani 1 1 d . . . . .
H11 H 0.069197 0.626267 0.487346 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6068(5) 0.3868(4) 0.68397(12) 0.0302(7) Uani 1 1 d . . . . .
C13 C 0.5840(6) 0.2649(4) 0.64695(12) 0.0330(8) Uani 1 1 d . . . . .
H13 H 0.738885 0.228800 0.638411 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4509(7) 0.1292(4) 0.66484(13) 0.0430(9) Uani 1 1 d . . . . .
H14A H 0.520040 0.090460 0.694143 0.064 Uiso 1 1 calc R U . . .
H14B H 0.451172 0.048934 0.640575 0.064 Uiso 1 1 calc R U . . .
H14C H 0.295218 0.160508 0.671398 0.064 Uiso 1 1 calc R U . . .
O4 O 0.2972(5) 0.7780(3) 0.27259(10) 0.0536(8) Uani 1 1 d . . . . .
H4O H 0.191(9) 0.731(6) 0.2537(17) 0.080 Uiso 1 1 d . U . . .
C15 C 0.4664(7) 0.6691(5) 0.28303(16) 0.0504(10) Uani 1 1 d . . . . .
H15A H 0.518934 0.620391 0.253217 0.060 Uiso 1 1 calc R U . . .
H15B H 0.403938 0.588696 0.303994 0.060 Uiso 1 1 calc R U . . .
C16 C 0.6572(6) 0.7453(6) 0.30694(15) 0.0516(11) Uani 1 1 d . . . . .
H16A H 0.606760 0.786785 0.337557 0.077 Uiso 1 1 calc R U . . .
H16B H 0.713065 0.828368 0.286795 0.077 Uiso 1 1 calc R U . . .
H16C H 0.778525 0.671410 0.312361 0.077 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
O1 C2 1.354(4) . ?
O1 C1 1.422(4) . ?
O2 C12 1.313(4) . ?
O2 H2 0.93(5) . ?
O3 C12 1.212(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C11 1.362(4) . ?
C2 C3 1.409(5) . ?
C3 C4 1.348(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(5) . ?
C5 C10 1.416(4) . ?
C6 C7 1.356(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.417(4) . ?
C7 C13 1.521(5) . ?
C8 C9 1.354(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.406(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.497(5) . ?
C13 C14 1.513(5) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O4 C15 1.416(5) . ?
O4 H4O 0.92(5) . ?
C15 C16 1.476(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 116.7(3) . . ?
C12 O2 H2 107(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C11 125.7(3) . . ?
O1 C2 C3 113.9(3) . . ?
C11 C2 C3 120.4(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 122.4(3) . . ?
C6 C5 C10 119.4(3) . . ?
C4 C5 C10 118.2(3) . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 118.7(3) . . ?
C6 C7 C13 121.5(3) . . ?
C8 C7 C13 119.8(3) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.4(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 122.4(3) . . ?
C9 C10 C5 117.9(3) . . ?
C11 C10 C5 119.7(3) . . ?
C2 C11 C10 119.9(3) . . ?
C2 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O3 C12 O2 122.5(3) . . ?
O3 C12 C13 125.0(3) . . ?
O2 C12 C13 112.5(3) . . ?
C12 C13 C14 112.2(3) . . ?
C12 C13 C7 107.5(3) . . ?
C14 C13 C7 112.8(3) . . ?
C12 C13 H13 108.0 . . ?
C14 C13 H13 108.0 . . ?
C7 C13 H13 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 O4 H4O 108(3) . . ?
O4 C15 C16 109.4(3) . . ?
O4 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
O4 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C1 O1 C2 C11 7.1(5) . . . . ?
C1 O1 C2 C3 -172.7(3) . . . . ?
O1 C2 C3 C4 178.8(3) . . . . ?
C11 C2 C3 C4 -1.0(5) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 -177.3(3) . . . . ?
C3 C4 C5 C10 1.8(5) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C10 C5 C6 C7 0.1(5) . . . . ?
C5 C6 C7 C8 1.6(5) . . . . ?
C5 C6 C7 C13 -176.5(3) . . . . ?
C6 C7 C8 C9 -2.0(5) . . . . ?
C13 C7 C8 C9 176.1(3) . . . . ?
C7 C8 C9 C10 0.8(5) . . . . ?
C8 C9 C10 C11 -176.5(3) . . . . ?
C8 C9 C10 C5 1.0(5) . . . . ?
C6 C5 C10 C9 -1.4(5) . . . . ?
C4 C5 C10 C9 179.5(3) . . . . ?
C6 C5 C10 C11 176.1(3) . . . . ?
C4 C5 C10 C11 -3.0(5) . . . . ?
O1 C2 C11 C10 180.0(3) . . . . ?
C3 C2 C11 C10 -0.2(5) . . . . ?
C9 C10 C11 C2 179.7(3) . . . . ?
C5 C10 C11 C2 2.2(5) . . . . ?
O3 C12 C13 C14 -15.9(5) . . . . ?
O2 C12 C13 C14 164.8(3) . . . . ?
O3 C12 C13 C7 108.8(4) . . . . ?
O2 C12 C13 C7 -70.5(3) . . . . ?
C6 C7 C13 C12 120.3(3) . . . . ?
C8 C7 C13 C12 -57.8(4) . . . . ?
C6 C7 C13 C14 -115.5(4) . . . . ?
C8 C7 C13 C14 66.5(4) . . . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043


# start Validation Reply Form
_vrf_PLAT340_Snprx_etoh          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00447 Ang.  
RESPONSE: Limited resolution.
;
_vrf_PLAT911_Snprx_etoh          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         71 Report
RESPONSE: These reflection are missing because of the instrument geometery 
limitations.

;
####################################################################### 
# 
# 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_RSnprx-Lpro-1-2
_database_code_depnum_ccdc_archive 'CCDC 1861023'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_chemical_name_systematic        
'(2R)-2-(6-methoxynaphthalen-2-yl)propanoic acid;(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid;tetrakis((2S)-pyrrolidine-2-carboxylic acid);'
_chemical_name_common            
;
RS-naproxen L-proline 1:2 cocrystal
;
_chemical_formula_moiety         'C14 H14 O3, 2(C5 H9 N O2)'
_chemical_formula_sum            'C24 H32 N2 O7'
_chemical_formula_weight         460.52
_exptl_crystal_density_diffrn    1.276
_chemical_melting_point          444(1)
_chemical_absolute_configuration rm


_cell_length_a                   5.84172(9)
_cell_length_b                   8.98394(13)
_cell_length_c                   45.6816(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2397.45(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    407
_cell_special_details            
; 
The powder pattern was indexed using FOX program
;
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'-x+1/2, -y, z+1/2 '
'-x, y+1/2, -z+1/2 '
'x+1/2, -y+1/2, -z '
_pd_spec_size_axial              4
_pd_spec_size_equat              0.5
_pd_spec_size_thick              0.5


_pd_spec_mounting                'Thin-wall 0.5 mm glass capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  colourless
_exptl_absorpt_correction_type   none

_pd_instr_location               
; 
X04SA beamline, Swiss Light Source (SLS), Villigen, Switzerland
;
_pd_calibration_special_details  
; 
using LaB₆ standard
;

_diffrn_ambient_temperature      407
_diffrn_source                   synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  'Mythen II'
_diffrn_detector                 'solid-state silicon microstrip detector'
_diffrn_detector_type            'Mythen II'
_diffrn_radiation_wavelength     0.708
_pd_meas_scan_method             step
_pd_meas_special_details         
;  ?
;

_pd_meas_number_of_points        8807
_pd_meas_2theta_range_min        1.2996
_pd_meas_2theta_range_max        33.00120
_pd_meas_2theta_range_inc        0.0036


_pd_proc_ls_prof_R_factor        1.865
_pd_proc_ls_prof_wR_factor       2.188
_pd_proc_ls_prof_wR_expected     0.531

_refine_ls_R_I_factor            4.228
_refine_ls_number_reflns         ?
_refine_ls_number_parameters     ?
_refine_ls_number_restraints     ?
_refine_ls_goodness_of_fit_all   4.12
_refine_ls_shift/su_max          0.001

_pd_proc_2theta_range_min        1.2996
_pd_proc_2theta_range_max        33.00120
_pd_proc_2theta_range_inc        0.0036
_pd_proc_wavelength              0.708

_computing_data_collection       ?
_computing_structure_solution    FOX
_computing_structure_refinement  'TOPAS V5'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
O1 O 4 0.788(4) 0.434(4) 0.62487(16) 1 10.02752
C14 C 4 0.584(4) 0.354(3) 0.54120(15) 1 4.137338
H14 H 4 0.719(5) 0.300(3) 0.54152(17) 1 4.974281
C13 C 4 0.516(4) 0.425(2) 0.51483(14) 1 3.93205
C12 C 4 0.646(4) 0.415(3) 0.48877(15) 1 4.761097
H12 H 4 0.780(4) 0.359(3) 0.48857(17) 1 5.684892
C11 C 4 0.577(3) 0.485(2) 0.46405(14) 1 5.076924
H11 H 4 0.663(3) 0.476(3) 0.44701(15) 1 6.079676
C10 C 4 0.1453(16) 0.7392(6) 0.43597(11) 1 6.190216
H00A H 4 0.1357(17) 0.7807(6) 0.41664(11) 1 9.316907
H00B H 4 0.1679(18) 0.8178(6) 0.44992(11) 1 9.316907
H00D H 4 0.0059(17) 0.6873(9) 0.44041(11) 1 9.316907
C1 C 4 0.600(4) 0.407(3) 0.61701(15) 1 4.721619
O2 O 4 0.423(3) 0.477(2) 0.62732(13) 1 6.600791
H2A H 4 0.465(3) 0.538(2) 0.63951(13) 1 7.895684
C2 C 4 0.539(5) 0.290(3) 0.59431(16) 1 4.911115
H2 H 4 0.679(5) 0.236(3) 0.58962(18) 0.5 5.921763
O3 O 4 0.3329(19) 0.6381(11) 0.43736(11) 1 6.332338
C3 C 4 0.369(6) 0.179(2) 0.60707(18) 0.5 7.161385
H00E H 4 0.224(5) 0.2271(15) 0.61036(17) 0.5 10.73813
H00G H 4 0.427(6) 0.141(2) 0.62528(18) 0.5 10.73813
H00H H 4 0.348(7) 0.0978(18) 0.59358(19) 0.5 10.73813
C4 C 4 0.455(4) 0.363(2) 0.56620(15) 1 4.232086
C5 C 4 0.247(3) 0.4433(13) 0.56525(13) 1 4.532122
H5 H 4 0.156(3) 0.4478(12) 0.58189(13) 1 5.448022
C7 C 4 0.311(3) 0.5084(13) 0.51432(12) 1 3.979424
C6 C 4 0.178(3) 0.5140(10) 0.54031(12) 1 4.50054
H6 H 4 0.041(2) 0.5670(9) 0.54035(12) 1 5.369065
C9 C 4 0.378(2) 0.5720(13) 0.46382(12) 1 4.595288
C8 C 4 0.246(2) 0.5846(9) 0.48841(12) 1 4.39
H8 H 4 0.1142(19) 0.6426(7) 0.48817(11) 1 5.290108
C3a C 4 0.759(6) 0.201(3) 0.59028(19) 0.5 7.161385
H2b H 4 0.423(5) 0.220(2) 0.60139(17) 0.5 10.73813
H00Ea H 4 0.806(6) 0.161(4) 0.6088(2) 0.5 10.73813
H00Ga H 4 0.877(5) 0.264(4) 0.58268(19) 0.5 10.73813
H00Ha H 4 0.732(6) 0.120(3) 0.5768(2) 0.5 10.73813
N1 N 4 0.003(3) 0.818(5) 0.68015(13) 1 3.69518
H00W H 4 -0.128(3) 0.768(9) 0.68161(19) 1 4.421583
H00X H 4 0.052(3) 0.835(4) 0.69832(12) 1 4.421583
C19 C 4 -0.024(11) 0.960(6) 0.6642(2) 1 5.155881
H00 H 4 0.094(16) 1.031(3) 0.6696(2) 1 6.158633
HB H 4 -0.171(14) 1.005(10) 0.6689(3) 1 6.158633
C17 C 4 0.1599(15) 0.7891(10) 0.63199(9) 1 5.02955
H00Z H 4 0.308(3) 0.824(4) 0.62532(13) 1 6.000719
H H 4 0.107(5) 0.7110(17) 0.61898(12) 1 6.000719
C16 C 4 0.177(5) 0.7291(12) 0.66357(11) 1 3.458309
H00Y H 4 0.135(12) 0.6235(16) 0.66422(18) 1 4.184712
C15 C 4 0.415(4) 0.750(7) 0.67633(18) 1 3.592536
O4 O 4 0.574(8) 0.677(12) 0.6645(3) 1 4.611079
O5 O 4 0.441(4) 0.837(7) 0.69746(19) 1 4.997968
C18 C 4 -0.009(9) 0.915(5) 0.63269(18) 1 6.419191
H0AA H 4 0.040(15) 0.998(4) 0.6206(2) 1 7.73777
HA H 4 -0.157(6) 0.881(9) 0.6256(2) 1 7.73777
N2 N 4 0.293(4) 0.7431(14) 0.75326(18) 1 3.868885
H00I H 4 0.216(6) 0.6673(17) 0.7455(3) 1 4.658453
H00L H 4 0.333(3) 0.8047(18) 0.73890(14) 1 4.658453
O6 O 4 0.012(4) 0.959(4) 0.7339(2) 1 5.069029
C24 C 4 0.500(5) 0.687(3) 0.7687(2) 1 5.669101
H00U H 4 0.499(8) 0.579(3) 0.7695(3) 1 6.790288
H00V H 4 0.638(4) 0.719(4) 0.7586(2) 1 6.790288
C23 C 4 0.495(4) 0.751(2) 0.79881(17) 1 5.724371
H00N H 4 0.643(3) 0.791(4) 0.8040(2) 1 6.869245
H00Q H 4 0.454(6) 0.6744(18) 0.8129(2) 1 6.869245
C22 C 4 0.3172(15) 0.8707(9) 0.79836(13) 1 6.063885
H00S H 4 0.385(3) 0.9659(13) 0.79339(17) 1 7.264029
H00T H 4 0.2427(16) 0.8792(15) 0.81727(13) 1 7.264029
C21 C 4 0.147(2) 0.823(2) 0.77501(18) 1 3.837302
H00M H 4 0.038(4) 0.752(3) 0.7836(3) 1 4.579496
C20 C 4 0.015(3) 0.949(4) 0.7609(2) 1 3.608327
O7 O 4 -0.083(5) 1.037(5) 0.7779(3) 1 5.882284

loop_
_pd_proc_2theta_corrected
_pd_calc_intensity_total
_pd_proc_intensity_total
1.29960 1161.68188 1147.07528
1.30320 1161.97284 1142.62530
1.30680 1162.26383 1145.97309
1.31040 1162.55485 1138.56605
1.31400 1162.84591 1141.81916
1.31760 1163.13699 1146.25194
1.32120 1163.42811 1151.50234
1.32480 1163.71927 1142.87381
1.32840 1164.01047 1141.61660
1.33200 1164.30170 1147.80014
1.33560 1164.59297 1148.42468
1.33920 1164.88428 1149.50978
1.34280 1165.17564 1148.57665
1.34640 1165.46704 1151.15370
1.35000 1165.75848 1155.27694
1.35360 1166.04997 1150.21872
1.35720 1166.34151 1148.36278
1.36080 1166.63310 1145.99630
1.36440 1166.92474 1157.69369
1.36800 1167.21643 1152.21201
1.37160 1167.50818 1152.04705
1.37520 1167.79998 1151.37173
1.37880 1168.09185 1155.57842
1.38240 1168.32081 1163.63979
1.38600 1168.54612 1164.17420
1.38960 1168.77151 1167.83269
1.39320 1168.99696 1161.99731
1.39680 1169.22249 1154.81951
1.40040 1169.44808 1165.43389
1.40400 1169.67376 1161.11961
1.40760 1169.89951 1174.33797
1.41120 1170.12535 1166.22289
1.41480 1170.35128 1165.77549
1.41840 1170.57729 1164.29583
1.42200 1170.80339 1157.55786
1.42560 1171.02960 1163.92724
1.42920 1171.25590 1167.14955
1.43280 1171.48231 1163.44438
1.43640 1171.70883 1172.18278
1.44000 1171.93547 1171.17408
1.44360 1172.16222 1166.21427
1.44720 1172.38910 1172.58108
1.45080 1172.61611 1167.90722
1.45440 1172.84325 1171.95285
1.45800 1173.07054 1166.43056
1.46160 1173.29797 1168.26825
1.46520 1173.52556 1174.30690
1.46880 1173.75332 1169.01952
1.47240 1173.98124 1172.66126
1.47600 1174.20934 1173.26224
1.47960 1174.43763 1173.87139
1.48320 1174.66612 1178.72295
1.48680 1174.89481 1178.81698
1.49040 1175.12372 1176.73390
1.49400 1175.35285 1178.69105
1.49760 1175.58223 1174.54908
1.50120 1175.81186 1170.82578
1.50480 1176.04175 1180.96679
1.50840 1176.27192 1173.83095
1.51200 1176.50239 1182.17338
1.51560 1176.73317 1186.03282
1.51920 1176.96428 1182.04595
1.52280 1177.19573 1182.74531
1.52640 1177.42755 1180.91000
1.53000 1177.65976 1178.89089
1.53360 1177.89238 1175.21282
1.53720 1178.12544 1183.32033
1.54080 1178.35896 1187.73999
1.54440 1178.59297 1184.83233
1.54800 1178.82750 1187.95768
1.55160 1179.06259 1189.91676
1.55520 1179.29827 1185.55760
1.55880 1179.53459 1194.63579
1.56240 1179.77157 1195.62711
1.56600 1180.00928 1199.02135
1.56960 1180.24776 1197.61490
1.57320 1180.48706 1196.08176
1.57680 1180.72724 1201.13862
1.58040 1180.96837 1203.56745
1.58400 1181.21052 1197.46201
1.58760 1181.45377 1192.69407
1.59120 1181.69821 1196.48057
1.59480 1181.94391 1192.29001
1.59840 1182.19100 1190.63863
1.60200 1182.43958 1191.96963
1.60560 1182.68978 1196.68700
1.60920 1182.94174 1198.40787
1.61280 1183.19561 1200.63974
1.61640 1183.45156 1189.49379
1.62000 1183.70979 1187.30367
1.62360 1183.97052 1193.56801
1.62720 1184.23397 1193.06466
1.63080 1184.50042 1195.22822
1.63440 1184.77018 1200.26815
1.63800 1185.04359 1201.05531
1.64160 1185.32103 1204.12347
1.64520 1185.60296 1201.43745
1.64880 1185.88987 1202.34537
1.65240 1186.18235 1196.79900
1.65600 1186.48105 1196.57317
1.65960 1186.78676 1202.31074
1.66320 1187.10035 1207.93655
1.66680 1187.42286 1204.83866
1.67040 1187.75551 1208.20301
1.67400 1188.09972 1212.07357
1.67760 1188.45718 1210.92272
1.68120 1188.82989 1211.88962
1.68480 1189.22025 1207.13884
1.68840 1189.63115 1212.19311
1.69200 1190.06613 1213.81830
1.69560 1190.52954 1213.34267
1.69920 1191.02698 1208.16442
1.70280 1191.56620 1218.47216
1.70640 1192.15949 1223.91819
1.71000 1192.83006 1225.78679
1.71360 1193.62755 1230.89298
1.71720 1194.66287 1234.55860
1.72080 1196.17730 1238.02792
1.72440 1198.66302 1236.33804
1.72800 1203.04562 1238.18410
1.73160 1210.92007 1251.13588
1.73520 1224.80682 1264.00172
1.73880 1248.38215 1270.16343
1.74240 1286.65292 1310.18909
1.74600 1346.06998 1350.99182
1.74960 1434.53392 1432.46134
1.75320 1561.05391 1542.59696
1.75680 1734.47027 1704.07650
1.76040 1960.38917 1924.38734
1.76400 2235.91669 2187.88880
1.76760 2543.39781 2554.18924
1.77120 2846.57542 2952.58404
1.77480 3093.56236 3270.34977
1.77840 3228.96632 3390.20803
1.78200 3212.85663 3334.64157
1.78560 3039.37266 3140.23321
1.78920 2743.55687 2807.80675
1.79280 2388.08903 2405.63630
1.79640 2038.44206 1967.59542
1.80000 1742.58846 1624.79312
1.80360 1522.47864 1435.99830
1.80720 1376.79329 1350.91177
1.81080 1290.31299 1315.28922
1.81440 1243.90978 1293.51659
1.81800 1221.15381 1279.14151
1.82160 1210.74930 1263.64334
1.82520 1206.13784 1254.71674
1.82880 1204.01646 1256.26854
1.83240 1202.91493 1247.97102
1.83600 1202.24283 1244.51451
1.83960 1201.77847 1240.54101
1.84320 1201.43818 1242.34651
1.84680 1201.18602 1228.14015
1.85040 1201.00252 1234.58930
1.85400 1200.87466 1240.31660
1.85760 1200.79269 1230.51206
1.86120 1200.74896 1234.98116
1.86480 1200.73738 1232.59805
1.86840 1200.75299 1230.77622
1.87200 1200.79177 1227.09308
1.87560 1200.85041 1229.27862
1.87920 1200.92615 1230.57804
1.88280 1201.01671 1232.66540
1.88640 1201.12017 1233.59954
1.89000 1201.23492 1232.30471
1.89360 1201.35958 1222.08726
1.89720 1201.49297 1218.25965
1.90080 1201.63410 1225.91823
1.90440 1201.78210 1226.51734
1.90800 1201.93622 1226.70328
1.91160 1202.09581 1227.04084
1.91520 1202.26032 1229.85273
1.91880 1202.42924 1231.58317
1.92240 1202.60215 1237.08565
1.92600 1202.77866 1235.11045
1.92960 1202.95843 1230.04622
1.93320 1203.14117 1230.73194
1.93680 1203.32661 1233.03570
1.94040 1203.51451 1229.43733
1.94400 1203.70467 1233.67519
1.94760 1203.89689 1234.81048
1.95120 1204.09100 1233.69236
1.95480 1204.28686 1227.16290
1.95840 1204.48432 1216.99493
1.96200 1204.68327 1233.02043
1.96560 1204.88358 1232.24218
1.96920 1205.08516 1231.01300
1.97280 1205.28791 1233.27727
1.97640 1205.49175 1233.35669
1.98000 1205.69660 1232.41843
1.98360 1205.90240 1230.41170
1.98720 1206.10907 1231.81291
1.99080 1206.31656 1234.20169
1.99440 1206.52482 1231.24313
1.99800 1206.73379 1234.24235
2.00160 1206.94344 1229.57959
2.00520 1207.15371 1235.74629
2.00880 1207.36457 1230.31088
2.01240 1207.57598 1231.41916
2.01600 1207.78791 1236.61293
2.01960 1208.00033 1236.24855
2.02320 1208.21321 1237.69281
2.02680 1208.42653 1240.00118
2.03040 1208.64025 1237.05000
2.03400 1208.85437 1237.54601
2.03760 1209.06884 1233.06852
2.04120 1209.28367 1236.95741
2.04480 1209.49881 1236.97372
2.04840 1209.71427 1235.33633
2.05200 1209.93003 1236.75638
2.05560 1210.14606 1230.31995
2.05920 1210.36235 1234.47635
2.06280 1210.57890 1230.84415
2.06640 1210.79568 1233.11613
2.07000 1211.01269 1239.89220
2.07360 1211.22992 1240.85740
2.07720 1211.44735 1231.53361
2.08080 1211.66498 1222.14587
2.08440 1211.88280 1239.66768
2.08800 1212.10079 1246.43093
2.09160 1212.31895 1241.36367
2.09520 1212.53728 1239.81141
2.09880 1212.75576 1241.50483
2.10240 1212.97438 1233.23264
2.10600 1213.19315 1236.36771
2.10960 1213.41206 1237.03461
2.11320 1213.63109 1239.65626
2.11680 1213.85025 1240.66179
2.12040 1214.06953 1249.43633
2.12400 1214.28892 1238.46248
2.12760 1214.50843 1240.46248
2.13120 1214.72803 1239.03868
2.13480 1214.94774 1244.69771
2.13840 1215.16754 1239.59260
2.14200 1215.38744 1234.97599
2.14560 1215.60743 1241.76285
2.14920 1215.82750 1247.71987
2.15280 1216.04766 1242.08296
2.15640 1216.26789 1242.44704
2.16000 1216.48820 1244.07728
2.16360 1216.70859 1244.62645
2.16720 1216.92904 1238.11507
2.17080 1217.14957 1249.38918
2.17440 1217.37016 1247.53796
2.17800 1217.59081 1245.08818
2.18160 1217.81153 1241.23345
2.18520 1218.03230 1244.16496
2.18880 1218.25313 1239.93926
2.19240 1218.47402 1230.08498
2.19600 1218.69496 1238.86600
2.19960 1218.91595 1245.63682
2.20320 1219.13699 1244.24681
2.20680 1219.35807 1234.53223
2.21040 1219.57921 1235.71721
2.21400 1219.80039 1241.85136
2.21760 1220.02161 1244.34501
2.22120 1220.24288 1244.11724
2.22480 1220.46418 1242.64322
2.22840 1220.68553 1244.21335
2.23200 1220.90691 1244.27542
2.23560 1221.12833 1245.50443
2.23920 1221.34978 1248.78399
2.24280 1221.57127 1238.24451
2.24640 1221.79280 1242.48914
2.25000 1222.01435 1241.07881
2.25360 1222.23594 1248.36169
2.25720 1222.45756 1241.77626
2.26080 1222.67921 1236.57144
2.26440 1222.90089 1233.47044
2.26800 1223.12259 1244.05398
2.27160 1223.34432 1246.02580
2.27520 1223.56608 1245.04859
2.27880 1223.78787 1241.48241
2.28240 1224.00968 1242.28493
2.28600 1224.23151 1244.87970
2.28960 1224.45337 1246.30678
2.29320 1224.67525 1256.12879
2.29680 1224.89715 1243.84166
2.30040 1225.11907 1233.25891
2.30400 1225.34102 1243.78143
2.30760 1225.56298 1243.30403
2.31120 1225.78497 1245.93958
2.31480 1226.00697 1241.31400
2.31840 1226.22900 1244.90082
2.32200 1226.45104 1243.26811
2.32560 1226.67310 1242.34469
2.32920 1226.89518 1243.73397
2.33280 1227.11727 1239.44032
2.33640 1227.33938 1239.45671
2.34000 1227.56151 1243.33505
2.34360 1227.78365 1244.82951
2.34720 1228.00581 1246.15433
2.35080 1228.22798 1247.22260
2.35440 1228.45017 1249.28350
2.35800 1228.67237 1242.11494
2.36160 1228.89459 1237.71448
2.36520 1229.11682 1246.89337
2.36880 1229.33906 1251.04199
2.37240 1229.56131 1242.21815
2.37600 1229.78358 1243.01464
2.37960 1230.00586 1248.14052
2.38320 1230.22815 1249.31770
2.38680 1230.45046 1239.90717
2.39040 1230.67277 1246.33440
2.39400 1230.89510 1245.49724
2.39760 1231.11744 1245.28170
2.40120 1231.33978 1245.99464
2.40480 1231.56214 1244.60355
2.40840 1231.78451 1243.42990
2.41200 1232.00689 1249.79044
2.41560 1232.22928 1251.47160
2.41920 1232.45167 1249.44398
2.42280 1232.67408 1242.68492
2.42640 1232.89650 1245.32236
2.43000 1233.11892 1244.02104
2.43360 1233.34135 1246.69935
2.43720 1233.56380 1249.81752
2.44080 1233.78625 1248.75065
2.44440 1234.00870 1246.98004
2.44800 1234.23117 1243.71000
2.45160 1234.45364 1247.78306
2.45520 1234.67612 1254.86372
2.45880 1234.89861 1252.91407
2.46240 1235.12111 1251.31440
2.46600 1235.34364 1249.24583
2.46960 1235.56672 1250.34305
2.47320 1235.79082 1246.63288
2.47680 1236.01660 1244.91381
2.48040 1236.24605 1252.94619
2.48400 1236.48826 1243.19857
2.48760 1236.71102 1240.98150
2.49120 1236.93379 1241.38634
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31.39920 384.43816 379.30711
31.40280 384.72337 380.71217
31.40640 385.00086 378.31668
31.41000 385.24103 381.55495
31.41360 385.41416 382.87604
31.41720 385.49846 378.78518
31.42080 385.48716 380.49921
31.42440 385.39028 383.89287
31.42800 385.23039 379.05536
31.43160 385.03452 376.85491
31.43520 384.82676 378.46281
31.43880 384.62407 377.46345
31.44240 384.43558 378.00763
31.44600 384.26422 376.66223
31.44960 384.10924 375.38011
31.45320 383.96782 379.88011
31.45680 383.83516 380.50441
31.46040 383.70346 378.06360
31.46400 383.56195 378.54823
31.46760 383.39855 376.60953
31.47120 383.20417 377.55149
31.47480 382.97629 378.38270
31.47840 382.71994 381.16515
31.48200 382.44539 381.10600
31.48560 382.16442 377.68174
31.48920 381.88763 373.72743
31.49280 381.62373 379.05671
31.49640 381.38023 373.99301
31.50000 381.16421 375.93368
31.50360 380.98227 372.77188
31.50720 380.83947 373.59901
31.51080 380.73881 375.26803
31.51440 380.68073 379.16766
31.51800 380.66282 375.14959
31.52160 380.67955 376.72781
31.52520 380.72137 375.85389
31.52880 380.77487 374.16460
31.53240 380.82357 376.08622
31.53600 380.85011 375.44616
31.53960 380.83965 374.91562
31.54320 380.78340 375.43749
31.54680 380.68070 375.03788
31.55040 380.53872 377.68444
31.55400 380.37001 379.60648
31.55760 380.18919 379.75219
31.56120 380.01021 379.42152
31.56480 379.84492 375.16992
31.56840 379.70278 377.03469
31.57200 379.59120 376.40199
31.57560 379.51543 377.17894
31.57920 379.47906 378.79065
31.58280 379.48241 371.15855
31.58640 379.52291 371.07506
31.59000 379.59462 381.56923
31.59360 379.68825 376.66303
31.59720 379.79189 373.91773
31.60080 379.89182 374.11811
31.60440 379.97624 375.93189
31.60800 380.03622 374.02096
31.61160 380.06776 375.48319
31.61520 380.07108 372.56679
31.61880 380.04817 374.51449
31.62240 380.00024 376.28208
31.62600 379.92650 376.04808
31.62960 379.82463 374.60031
31.63320 379.69292 378.79187
31.63680 379.53255 377.13794
31.64040 379.34893 374.39021
31.64400 379.15109 378.50156
31.64760 378.94965 370.96487
31.65120 378.75466 376.21443
31.65480 378.57405 373.09640
31.65840 378.41312 371.61498
31.66200 378.27463 373.84365
31.66560 378.15929 375.09787
31.66920 378.06722 374.58708
31.67280 377.99793 376.01270
31.67640 377.95213 373.53098
31.68000 377.93107 374.24688
31.68360 377.93645 373.54560
31.68720 377.96960 377.01730
31.69080 378.03070 376.37830
31.69440 378.11843 378.02646
31.69800 378.22969 373.63774
31.70160 378.35949 369.51880
31.70520 378.50092 372.69340
31.70880 378.64535 375.80057
31.71240 378.78334 377.24639
31.71600 378.90631 374.68950
31.71960 379.00892 376.65220
31.72320 379.09098 371.99552
31.72680 379.15783 377.29646
31.73040 379.21863 373.31954
31.73400 379.28388 376.04061
31.73760 379.36269 376.06333
31.74120 379.46112 372.87957
31.74480 379.58159 376.63239
31.74840 379.72299 376.69438
31.75200 379.88156 372.57895
31.75560 380.05208 374.58536
31.75920 380.22886 375.90735
31.76280 380.40605 378.76441
31.76640 380.57720 378.20545
31.77000 380.73481 378.43414
31.77360 380.87061 375.29353
31.77720 380.97680 375.06481
31.78080 381.04811 375.61451
31.78440 381.08391 371.85142
31.78800 381.08978 372.79823
31.79160 381.07736 378.65587
31.79520 381.06200 377.45439
31.79880 381.05948 372.59826
31.80240 381.08270 377.07260
31.80600 381.13989 372.05505
31.80960 381.23342 376.28727
31.81320 381.36035 377.92222
31.81680 381.51371 372.96975
31.82040 381.68472 373.99129
31.82400 381.86502 379.55622
31.82760 382.04807 380.37797
31.83120 382.22899 378.54711
31.83480 382.40383 377.98074
31.83840 382.56877 379.51385
31.84200 382.72078 376.42613
31.84560 382.85854 379.57131
31.84920 382.98311 377.51988
31.85280 383.09778 378.16868
31.85640 383.20705 378.83540
31.86000 383.31467 379.17470
31.86360 383.42148 379.03589
31.86720 383.52482 377.07102
31.87080 383.61964 377.79111
31.87440 383.69872 375.64618
31.87800 383.75535 379.33126
31.88160 383.78293 380.85283
31.88520 383.77375 376.88626
31.88880 383.71921 373.22629
31.89240 383.61227 376.16121
31.89600 383.45168 378.94800
31.89960 383.24525 380.39825
31.90320 383.00968 376.24274
31.90680 382.76679 377.79287
31.91040 382.53821 379.33230
31.91400 382.34104 373.21628
31.91760 382.18543 372.59743
31.92120 382.07399 375.30329
31.92480 382.00244 372.74563
31.92840 381.96062 375.02006
31.93200 381.93365 378.03935
31.93560 381.90304 375.72371
31.93920 381.84833 377.19340
31.94280 381.74970 377.42433
31.94640 381.59117 375.04063
31.95000 381.36373 374.13160
31.95360 381.06682 374.74260
31.95720 380.70826 376.75155
31.96080 380.30191 377.74212
31.96440 379.86519 376.26898
31.96800 379.41636 375.40448
31.97160 378.97234 370.20495
31.97520 378.54736 369.74810
31.97880 378.15244 374.57060
31.98240 377.79544 374.47189
31.98600 377.48126 378.34277
31.98960 377.21238 372.31523
31.99320 376.98962 377.88386
31.99680 376.81179 376.25899
32.00040 376.67660 376.89043
32.00400 376.58097 372.99394
32.00760 376.52115 369.40930
32.01120 376.49304 371.50699
32.01480 376.49214 370.96727
32.01840 376.51368 376.77395
32.02200 376.55307 374.63646
32.02560 376.60499 371.66446
32.02920 376.66429 370.40017
32.03280 376.72595 370.02972
32.03640 376.78527 370.36109
32.04000 376.83786 377.81028
32.04360 376.87960 379.41155
32.04720 376.90676 376.44914
32.05080 376.91663 373.87852
32.05440 376.90836 376.47058
32.05800 376.88362 374.38569
32.06160 376.84661 374.53508
32.06520 376.80303 375.16602
32.06880 376.75911 374.36512
32.07240 376.72077 375.84197
32.07600 376.69312 373.69063
32.07960 376.68047 373.37491
32.08320 376.68648 375.35181
32.08680 376.71457 369.66307
32.09040 376.76816 371.17428
32.09400 376.85076 374.97037
32.09760 376.96681 376.43922
32.10120 377.11937 377.84622
32.10480 377.31078 376.95989
32.10840 377.54181 377.70659
32.11200 377.81117 373.92518
32.11560 378.11505 374.44008
32.11920 378.44681 373.10494
32.12280 378.79649 373.48998
32.12640 379.15070 374.78054
32.13000 379.49299 372.16179
32.13360 379.80538 373.86939
32.13720 380.07103 373.02529
32.14080 380.27757 378.15733
32.14440 380.41943 377.39522
32.14800 380.49810 377.56536
32.15160 380.51999 372.04242
32.15520 380.49301 373.42356
32.15880 380.42334 377.04847
32.16240 380.31370 376.25616
32.16600 380.16360 377.08886
32.16960 379.97145 376.81051
32.17320 379.73752 376.33955
32.17680 379.46605 375.95851
32.18040 379.16540 377.98478
32.18400 378.84633 375.55770
32.18760 378.52059 376.12272
32.19120 378.19836 376.58581
32.19480 377.88848 375.04156
32.19840 377.59822 374.95461
32.20200 377.33330 374.09165
32.20560 377.09776 374.78766
32.20920 376.89395 371.51476
32.21280 376.72229 369.31061
32.21640 376.58234 375.02113
32.22000 376.47164 374.26433
32.22360 376.38675 373.93567
32.22720 376.32315 376.09224
32.23080 376.27543 375.15524
32.23440 376.23747 373.45525
32.23800 376.20295 370.39727
32.24160 376.16605 373.19524
32.24520 376.12230 375.41424
32.24880 376.06935 376.65384
32.25240 376.00718 376.48549
32.25600 375.93786 376.02709
32.25960 375.86449 376.87002
32.26320 375.79067 375.56157
32.26680 375.71986 372.59426
32.27040 375.65521 370.36458
32.27400 375.59953 374.22572
32.27760 375.55536 372.35508
32.28120 375.52495 379.95786
32.28480 375.51080 374.66295
32.28840 375.51505 373.85453
32.29200 375.53998 375.15691
32.29560 375.58765 373.30970
32.29920 375.66086 368.89834
32.30280 375.76149 369.88635
32.30640 375.89142 372.00355
32.31000 376.05202 374.82586
32.31360 376.24386 375.00594
32.31720 376.46642 374.50427
32.32080 376.71764 379.16120
32.32440 376.99400 375.08115
32.32800 377.28990 372.14245
32.33160 377.59717 374.90103
32.33520 377.90547 375.54845
32.33880 378.20240 376.22269
32.34240 378.47420 374.24484
32.34600 378.70690 373.61230
32.34960 378.88813 378.52815
32.35320 379.00940 378.15474
32.35680 379.06837 373.86174
32.36040 379.06992 374.32846
32.36400 379.02512 374.79764
32.36760 378.94831 377.04024
32.37120 378.85379 375.55732
32.37480 378.75318 371.54402
32.37840 378.65413 374.23311
32.38200 378.56457 378.13171
32.38560 378.48399 375.31918
32.38920 378.40694 377.12802
32.39280 378.32952 375.52131
32.39640 378.24632 372.10556
32.40000 378.15072 377.21562
32.40360 378.03590 376.83897
32.40720 377.89648 376.42701
32.41080 377.73029 373.93476
32.41440 377.53931 377.77563
32.41800 377.32925 376.76850
32.42160 377.10818 375.28195
32.42520 376.88494 375.13544
32.42880 376.66787 378.38000
32.43240 376.46405 379.24391
32.43600 376.27907 376.93983
32.43960 376.11702 375.69086
32.44320 375.98057 372.32678
32.44680 375.87119 374.17811
32.45040 375.78919 373.95931
32.45400 375.73393 374.82063
32.45760 375.70387 370.69183
32.46120 375.69683 374.64175
32.46480 375.70987 374.62622
32.46840 375.73951 372.69871
32.47200 375.78172 375.42120
32.47560 375.83197 377.62190
32.47920 375.88538 376.93744
32.48280 375.93702 372.97141
32.48640 375.98254 375.39972
32.49000 376.01889 376.10472
32.49360 376.04491 377.05821
32.49720 376.06139 372.69806
32.50080 376.07061 373.08588
32.50440 376.07558 372.65283
32.50800 376.07917 376.75983
32.51160 376.08361 375.52849
32.51520 376.09026 374.17674
32.51880 376.09977 373.68555
32.52240 376.11239 372.40781
32.52600 376.12849 376.02994
32.52960 376.14887 374.15483
32.53320 376.17474 370.86082
32.53680 376.20749 374.04011
32.54040 376.24836 375.37624
32.54400 376.29835 376.60573
32.54760 376.35826 376.03026
32.55120 376.42868 373.21743
32.55480 376.50968 371.82531
32.55840 376.60120 372.44029
32.56200 376.70170 371.23266
32.56560 376.80884 373.68066
32.56920 376.91981 372.63765
32.57280 377.03202 372.99922
32.57640 377.14395 374.26167
32.58000 377.25534 372.96634
32.58360 377.36665 375.82169
32.58720 377.47802 375.24913
32.59080 377.58813 372.41732
32.59440 377.69348 375.49756
32.59800 377.78819 379.66430
32.60160 377.86466 375.74746
32.60520 377.91457 376.59304
32.60880 377.93149 380.03271
32.61240 377.91206 376.28551
32.61600 377.85849 379.24170
32.61960 377.77852 379.93274
32.62320 377.68378 380.93343
32.62680 377.58766 376.42401
32.63040 377.50322 375.60762
32.63400 377.44210 378.54195
32.63760 377.41381 379.97059
32.64120 377.42564 372.87040
32.64480 377.48250 374.06437
32.64840 377.58689 374.10761
32.65200 377.73886 372.87608
32.65560 377.93609 371.45064
32.65920 378.17408 372.85978
32.66280 378.44633 379.39689
32.66640 378.74445 375.29725
32.67000 379.05782 376.19397
32.67360 379.37340 376.26912
32.67720 379.67582 377.85122
32.68080 379.94858 378.98678
32.68440 380.17637 372.13539
32.68800 380.34797 373.49421
32.69160 380.45832 378.47245
32.69520 380.50897 373.90528
32.69880 380.50660 379.02363
32.70240 380.46052 376.46389
32.70600 380.38050 375.02721
32.70960 380.27522 378.63140
32.71320 380.15191 376.71759
32.71680 380.01647 379.78543
32.72040 379.87430 377.67899
32.72400 379.73085 378.33067
32.72760 379.59204 379.52959
32.73120 379.46386 374.95730
32.73480 379.35176 378.27047
32.73840 379.26020 376.87550
32.74200 379.19271 376.11998
32.74560 379.15207 377.53133
32.74920 379.14025 381.25988
32.75280 379.15788 375.86940
32.75640 379.20356 373.07873
32.76000 379.27295 371.58134
32.76360 379.35893 374.74733
32.76720 379.45102 375.50689
32.77080 379.53717 378.29618
32.77440 379.60604 380.43425
32.77800 379.64998 379.80582
32.78160 379.66740 379.56854
32.78520 379.66316 376.91047
32.78880 379.64679 379.92940
32.79240 379.62952 377.95329
32.79600 379.62102 379.90732
32.79960 379.62772 379.34185
32.80320 379.65185 375.69752
32.80680 379.69115 377.45525
32.81040 379.73943 374.90886
32.81400 379.78774 374.85763
32.81760 379.82661 378.67333
32.82120 379.84867 374.80237
32.82480 379.85084 376.11899
32.82840 379.83482 375.06272
32.83200 379.80583 374.26088
32.83560 379.77035 375.88807
32.83920 379.73395 373.40255
32.84280 379.69999 370.27262
32.84640 379.66895 375.49943
32.85000 379.63844 375.31171
32.85360 379.60343 377.01544
32.85720 379.55714 374.90590
32.86080 379.49149 375.65059
32.86440 379.39909 376.48464
32.86800 379.27442 376.14462
32.87160 379.11578 376.76982
32.87520 378.92575 378.39820
32.87880 378.71067 376.64579
32.88240 378.47921 378.38069
32.88600 378.24086 375.44165
32.88960 378.00464 374.91715
32.89320 377.77914 371.84096
32.89680 377.57137 372.66602
32.90040 377.38714 372.74051
32.90400 377.23072 371.76905
32.90760 377.10461 376.35964
32.91120 377.00959 376.57135
32.91480 376.94457 371.17034
32.91840 376.90675 376.47734
32.92200 376.89175 372.20148
32.92560 376.89381 374.19570
32.92920 376.90627 375.16919
32.93280 376.92206 377.77419
32.93640 376.93484 373.25036
32.94000 376.94003 375.71557
32.94360 376.93576 377.84304
32.94720 376.92333 374.71314
32.95080 376.90631 372.31824
32.95440 376.88986 374.76137
32.95800 376.87976 377.22080
32.96160 376.88183 373.98408
32.96520 376.90162 373.10451
32.96880 376.94427 372.12574
32.97240 377.01436 372.59639
32.97600 377.11583 374.33424
32.97960 377.25181 373.34914
32.98320 377.42431 372.41176
32.98680 377.63397 375.00799
32.99040 377.87921 378.55749
32.99400 378.15591 377.02922
32.99760 378.45679 375.67442
33.00120 378.77108 381.78938

# start Validation Reply Form
_vrf_GEOM001_RSnprx-Lpro-1-2     
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM003_RSnprx-Lpro-1-2     
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM006_RSnprx-Lpro-1-2     
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM007_RSnprx-Lpro-1-2     
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_exptl_crystal_colour            colourless
_exptl_crystal_description       powder
####################################################################### 
# 
# 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_nt0025_RSnprxDproMeOHb4
_database_code_depnum_ccdc_archive 'CCDC 1861019'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
(2R)-2-(6-methoxynaphthalen-2-yl)propanoic acid;
 bis((2R)-pyrrolidine-2-carboxylic acid); 
(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid; methanol
;
_chemical_name_common            
;
1:1 RS-naproxen D-proline cocrystal methanol solvate 
;
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H14 O3), 2(C5 H9 N O2), C H4 O'
_chemical_formula_sum            'C39 H50 N2 O11'
_chemical_formula_weight         722.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.9532(4)
_cell_length_b                   5.76337(15)
_cell_length_c                   25.2764(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.984(3)
_cell_angle_gamma                90
_cell_volume                     1882.42(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5523
_cell_measurement_theta_min      3.4980
_cell_measurement_theta_max      66.9150

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.768
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            11648
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.420
_diffrn_reflns_theta_max         67.194
_diffrn_reflns_theta_full        67.194
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.836
_reflns_number_total             5615
_reflns_number_gt                4791
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.523
_reflns_Friedel_fraction_max     0.645
_reflns_Friedel_fraction_full    0.645

_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0892P)²+0.2271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_chemical_absolute_configuration rm
_refine_ls_number_reflns         5615
_refine_ls_number_parameters     493
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.150
_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
O1 O 0.8211(2) 1.2924(6) 0.29572(10) 0.0736(8) Uani 1 1 d . . . . .
H1 H 0.837539 1.291733 0.327634 0.088 Uiso 1 1 calc R U . . .
O2 O 0.7192(2) 1.0064(7) 0.31789(12) 0.0883(9) Uani 1 1 d . . . . .
O3 O 1.1595(2) 0.8245(6) 0.04306(11) 0.0786(9) Uani 1 1 d . . . . .
C1 C 0.7493(3) 1.1373(8) 0.28501(14) 0.0639(9) Uani 1 1 d . . . . .
C2 C 0.7099(3) 1.1367(8) 0.22737(14) 0.0681(10) Uani 1 1 d . . . . .
H2 H 0.698758 1.297734 0.215862 0.082 Uiso 1 1 calc R U . . .
C3 C 0.6087(3) 1.0083(11) 0.21940(19) 0.0872(14) Uani 1 1 d . . . . .
H3A H 0.557656 1.083428 0.239186 0.131 Uiso 1 1 calc R U . . .
H3B H 0.617924 0.851309 0.231526 0.131 Uiso 1 1 calc R U . . .
H3C H 0.586195 1.008263 0.182409 0.131 Uiso 1 1 calc R U . . .
C4 C 0.7933(3) 1.0307(8) 0.19530(13) 0.0613(9) Uani 1 1 d . . . . .
C5 C 0.8397(3) 0.8173(8) 0.21007(15) 0.0681(10) Uani 1 1 d . . . . .
H5 H 0.815803 0.736286 0.238619 0.082 Uiso 1 1 calc R U . . .
C6 C 0.9186(3) 0.7258(8) 0.18369(14) 0.0677(10) Uani 1 1 d . . . . .
H6 H 0.948425 0.585896 0.195003 0.081 Uiso 1 1 calc R U . . .
C7 C 0.9557(3) 0.8405(7) 0.13953(13) 0.0589(9) Uani 1 1 d . . . . .
C8 C 1.0419(3) 0.7586(8) 0.11280(13) 0.0626(9) Uani 1 1 d . . . . .
H8 H 1.075276 0.622541 0.123974 0.075 Uiso 1 1 calc R U . . .
C9 C 1.0756(3) 0.8795(8) 0.07078(13) 0.0647(9) Uani 1 1 d . . . . .
C10 C 1.2135(4) 0.6160(11) 0.05756(19) 0.0889(14) Uani 1 1 d . . . . .
H10A H 1.237054 0.622544 0.094395 0.133 Uiso 1 1 calc R U . . .
H10B H 1.271906 0.599302 0.036466 0.133 Uiso 1 1 calc R U . . .
H10C H 1.168004 0.485729 0.051596 0.133 Uiso 1 1 calc R U . . .
C11 C 1.0230(3) 1.0806(9) 0.05251(14) 0.0717(11) Uani 1 1 d . . . . .
H11 H 1.044490 1.157634 0.022867 0.086 Uiso 1 1 calc R U . . .
C12 C 0.9411(3) 1.1640(8) 0.07766(14) 0.0702(10) Uani 1 1 d . . . . .
H12 H 0.907972 1.298419 0.065212 0.084 Uiso 1 1 calc R U . . .
C13 C 0.9057(3) 1.0489(7) 0.12253(13) 0.0590(9) Uani 1 1 d . . . . .
C14 C 0.8255(3) 1.1390(7) 0.15109(13) 0.0630(9) Uani 1 1 d . . . . .
H14 H 0.793388 1.276114 0.139654 0.076 Uiso 1 1 calc R U . . .
O7 O -0.0201(4) 1.1282(6) 0.46412(11) 0.1116(13) Uani 1 1 d . . . . .
O8 O -0.1018(2) 1.2850(5) 0.39357(10) 0.0755(8) Uani 1 1 d . . . . .
N1 N -0.0136(3) 0.7013(6) 0.42650(11) 0.0702(8) Uani 1 1 d D U . . .
H1A H -0.047014 0.566898 0.422488 0.084 Uiso 1 1 calc R U . A 1
H1B H -0.012399 0.744041 0.460370 0.084 Uiso 1 1 calc R U . A 1
C29 C -0.0628(3) 1.1167(7) 0.41944(13) 0.0627(9) Uani 1 1 d . . . . .
C30 C -0.0629(3) 0.8833(7) 0.39120(12) 0.0573(8) Uani 1 1 d D U . . .
H30 H -0.133729 0.838005 0.379422 0.069 Uiso 1 1 calc R U . B 1
C31A C 0.0028(8) 0.913(3) 0.3433(4) 0.069(3) Uani 0.567(14) 1 d D U P C 1
H31A H -0.039436 0.910417 0.310037 0.082 Uiso 0.567(14) 1 calc R U P C 1
H31B H 0.043284 1.054384 0.345617 0.082 Uiso 0.567(14) 1 calc R U P C 1
C32A C 0.0704(8) 0.699(2) 0.3500(4) 0.098(3) Uani 0.567(14) 1 d D U P C 1
H32A H 0.033655 0.561623 0.336692 0.118 Uiso 0.567(14) 1 calc R U P C 1
H32B H 0.133086 0.716202 0.331454 0.118 Uiso 0.567(14) 1 calc R U P C 1
C33A C 0.0947(8) 0.683(3) 0.4083(6) 0.089(5) Uani 0.567(14) 1 d D U P C 1
H33A H 0.138322 0.809955 0.421472 0.106 Uiso 0.567(14) 1 calc R U P C 1
H33B H 0.127009 0.536297 0.418426 0.106 Uiso 0.567(14) 1 calc R U P C 1
C31B C 0.0000(13) 0.843(4) 0.3427(5) 0.095(8) Uani 0.433(14) 1 d D U P C 2
H31C H -0.024138 0.706151 0.323048 0.114 Uiso 0.433(14) 1 calc R U P C 2
H31D H -0.003682 0.975831 0.319171 0.114 Uiso 0.433(14) 1 calc R U P C 2
C32B C 0.1087(10) 0.808(4) 0.3675(7) 0.114 Uiso 0.433(14) 1 d D U P C 2
H32C H 0.156040 0.764153 0.341109 0.114 Uiso 0.433(14) 1 calc R U P C 2
H32D H 0.134284 0.947217 0.385583 0.114 Uiso 0.433(14) 1 calc R U P C 2
C33B C 0.0946(11) 0.615(4) 0.4059(8) 0.089(6) Uani 0.433(14) 1 d D U P C 2
H33C H 0.149402 0.610466 0.434027 0.107 Uiso 0.433(14) 1 calc R U P C 2
H33D H 0.088688 0.464912 0.388484 0.107 Uiso 0.433(14) 1 calc R U P C 2
O10 O 0.4001(2) 0.9588(5) 0.39437(10) 0.0742(8) Uani 1 1 d . . . . .
O11 O 0.4737(3) 0.7921(5) 0.46574(10) 0.0986(12) Uani 1 1 d . . . . .
N2 N 0.4932(2) 0.3773(5) 0.42431(10) 0.0602(7) Uani 1 1 d . . . . .
H2A H 0.494646 0.421715 0.458076 0.072 Uiso 1 1 calc R U . . .
H2B H 0.457084 0.246178 0.420824 0.072 Uiso 1 1 calc R U . . .
C34 C 0.4384(3) 0.7866(6) 0.41963(12) 0.0589(8) Uani 1 1 d . . . . .
C35 C 0.4431(3) 0.5631(6) 0.38902(12) 0.0574(8) Uani 1 1 d . . . . .
H35 H 0.373658 0.515004 0.375471 0.069 Uiso 1 1 calc R U . . .
C36 C 0.5151(4) 0.5788(10) 0.34416(15) 0.0908(15) Uani 1 1 d . . . . .
H36A H 0.512522 0.731519 0.328017 0.109 Uiso 1 1 calc R U . . .
H36B H 0.497989 0.463000 0.317109 0.109 Uiso 1 1 calc R U . . .
C37 C 0.6207(5) 0.5319(12) 0.3723(3) 0.1109(19) Uani 1 1 d . . . . .
H37A H 0.670603 0.487959 0.347254 0.133 Uiso 1 1 calc R U . . .
H37B H 0.646128 0.667319 0.391939 0.133 Uiso 1 1 calc R U . . .
C38 C 0.6012(4) 0.3387(10) 0.4084(2) 0.0904(13) Uani 1 1 d . . . . .
H38A H 0.650256 0.341345 0.439229 0.109 Uiso 1 1 calc R U . . .
H38B H 0.606637 0.190770 0.390551 0.109 Uiso 1 1 calc R U . . .
O4 O 0.3205(2) -0.0370(6) 0.29699(10) 0.0824(9) Uani 1 1 d . . . . .
H4 H 0.344086 -0.032015 0.327921 0.099 Uiso 1 1 calc R U . . .
O5 O 0.2341(2) 0.2732(7) 0.32131(11) 0.0864(9) Uani 1 1 d . . . . .
O6 O 0.6569(2) 0.4502(6) 0.04234(11) 0.0795(9) Uani 1 1 d . . . . .
C15 C 0.2560(3) 0.1336(8) 0.28795(14) 0.0634(9) Uani 1 1 d . . . . .
C16 C 0.2132(3) 0.1430(8) 0.23034(14) 0.0686(10) Uani 1 1 d . . . . .
H16 H 0.200087 -0.016456 0.218176 0.082 Uiso 1 1 calc R U . . .
C17 C 0.1128(3) 0.2752(11) 0.22394(18) 0.0846(13) Uani 1 1 d . . . . .
H17A H 0.087597 0.274212 0.187313 0.127 Uiso 1 1 calc R U . . .
H17B H 0.123960 0.432355 0.235521 0.127 Uiso 1 1 calc R U . . .
H17C H 0.062717 0.203113 0.244926 0.127 Uiso 1 1 calc R U . . .
C18 C 0.2952(3) 0.2477(8) 0.19705(13) 0.0605(9) Uani 1 1 d . . . . .
C19 C 0.3251(3) 0.1390(7) 0.15314(13) 0.0622(9) Uani 1 1 d . . . . .
H19 H 0.292306 0.001709 0.142350 0.075 Uiso 1 1 calc R U . . .
C20 C 0.4046(3) 0.2278(7) 0.12306(13) 0.0588(8) Uani 1 1 d . . . . .
C21 C 0.4389(3) 0.1143(8) 0.07810(14) 0.0715(11) Uani 1 1 d . . . . .
H21 H 0.404438 -0.018413 0.065571 0.086 Uiso 1 1 calc R U . . .
C22 C 0.5207(3) 0.1934(9) 0.05258(14) 0.0709(11) Uani 1 1 d . . . . .
H22 H 0.542001 0.114162 0.023189 0.085 Uiso 1 1 calc R U . . .
C23 C 0.7113(3) 0.6574(10) 0.05600(18) 0.0831(13) Uani 1 1 d . . . . .
H23A H 0.741502 0.645717 0.091682 0.125 Uiso 1 1 calc R U . . .
H23B H 0.664353 0.786358 0.053400 0.125 Uiso 1 1 calc R U . . .
H23C H 0.765004 0.680358 0.032187 0.125 Uiso 1 1 calc R U . . .
C24 C 0.5732(3) 0.3945(8) 0.07051(13) 0.0640(9) Uani 1 1 d . . . . .
C25 C 0.5404(3) 0.5175(8) 0.11249(13) 0.0646(9) Uani 1 1 d . . . . .
H25 H 0.573710 0.654413 0.123136 0.078 Uiso 1 1 calc R U . . .
C26 C 0.4554(3) 0.4355(7) 0.13978(12) 0.0566(8) Uani 1 1 d . . . . .
C27 C 0.4195(3) 0.5530(8) 0.18424(14) 0.0672(10) Uani 1 1 d . . . . .
H27 H 0.448823 0.694612 0.194610 0.081 Uiso 1 1 calc R U . . .
C28 C 0.3426(3) 0.4613(8) 0.21208(14) 0.0654(10) Uani 1 1 d . . . . .
H28 H 0.320914 0.540506 0.241390 0.078 Uiso 1 1 calc R U . . .
C39 C 0.2415(9) 0.189(2) 0.4951(5) 0.189(4) Uiso 1 1 d D . . . .
H39A H 0.213714 0.035969 0.489563 0.283 Uiso 0.5 1 calc R U P D 1
H39B H 0.193495 0.282039 0.513169 0.283 Uiso 0.5 1 calc R U P D 1
H39C H 0.305965 0.180159 0.516120 0.283 Uiso 0.5 1 calc R U P D 1
H39D H 0.216593 0.119289 0.526224 0.283 Uiso 0.5 1 calc R U P E 2
H39E H 0.299890 0.103182 0.484247 0.283 Uiso 0.5 1 calc R U P E 2
H39F H 0.187535 0.187893 0.467041 0.283 Uiso 0.5 1 calc R U P E 2
O12A O 0.257(2) 0.286(6) 0.4481(8) 0.317(12) Uiso 0.5 1 d D . P F 1
H12A H 0.256371 0.185143 0.425190 0.381 Uiso 0.5 1 calc DR U P F 1
O12B O 0.2706(19) 0.413(4) 0.5061(9) 0.275(10) Uiso 0.5 1 d D . P F 2
H12B H 0.220015 0.498679 0.502066 0.330 Uiso 0.5 1 calc . U P G 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
O1 C1 1.304(5) . ?
O1 H1 0.8200 . ?
O2 C1 1.207(5) . ?
O3 C9 1.370(5) . ?
O3 C10 1.426(7) . ?
C1 C2 1.510(5) . ?
C2 C3 1.506(6) . ?
C2 C4 1.523(5) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C14 1.370(5) . ?
C4 C5 1.408(6) . ?
C5 C6 1.365(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(5) . ?
C6 H6 0.9300 . ?
C7 C13 1.417(6) . ?
C7 C8 1.425(5) . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C11 1.405(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.362(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.418(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.404(5) . ?
C14 H14 0.9300 . ?
O7 C29 1.224(4) . ?
O8 C29 1.256(5) . ?
N1 C30 1.491(5) . ?
N1 C33A 1.510(9) . ?
N1 C33B 1.608(10) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C29 C30 1.523(5) . ?
C30 C31B 1.537(10) . ?
C30 C31A 1.537(8) . ?
C30 H30 0.9800 . ?
C31A C32A 1.516(13) . ?
C31A H31A 0.9700 . ?
C31A H31B 0.9700 . ?
C32A C33A 1.488(15) . ?
C32A H32A 0.9700 . ?
C32A H32B 0.9700 . ?
C33A H33A 0.9700 . ?
C33A H33B 0.9700 . ?
C31B C32B 1.515(15) . ?
C31B H31C 0.9700 . ?
C31B H31D 0.9700 . ?
C32B C33B 1.496(16) . ?
C32B H32C 0.9700 . ?
C32B H32D 0.9700 . ?
C33B H33C 0.9700 . ?
C33B H33D 0.9700 . ?
O10 C34 1.263(4) . ?
O11 C34 1.222(4) . ?
N2 C38 1.498(6) . ?
N2 C35 1.511(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
C34 C35 1.506(5) . ?
C35 C36 1.520(6) . ?
C35 H35 0.9800 . ?
C36 C37 1.521(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.472(8) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
O4 C15 1.300(5) . ?
O4 H4 0.8200 . ?
O5 C15 1.213(5) . ?
O6 C24 1.375(5) . ?
O6 C23 1.417(6) . ?
C15 C16 1.523(5) . ?
C16 C17 1.507(6) . ?
C16 C18 1.525(5) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.354(5) . ?
C18 C28 1.416(6) . ?
C19 C20 1.418(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.409(5) . ?
C20 C26 1.417(5) . ?
C21 C22 1.357(6) . ?
C21 H21 0.9300 . ?
C22 C24 1.403(6) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.368(5) . ?
C25 C26 1.420(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.418(5) . ?
C27 C28 1.366(6) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C39 O12A 1.341(19) . ?
C39 O12B 1.37(2) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C39 H39D 0.9600 . ?
C39 H39E 0.9600 . ?
C39 H39F 0.9600 . ?
O12A H12A 0.8200 . ?
O12B H12B 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
C1 O1 H1 109.5 . . ?
C9 O3 C10 117.2(4) . . ?
O2 C1 O1 123.0(3) . . ?
O2 C1 C2 124.0(4) . . ?
O1 C1 C2 113.0(4) . . ?
C3 C2 C1 111.3(4) . . ?
C3 C2 C4 112.0(4) . . ?
C1 C2 C4 108.0(3) . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C4 C2 H2 108.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C14 C4 C5 117.8(4) . . ?
C14 C4 C2 121.3(4) . . ?
C5 C4 C2 121.0(4) . . ?
C6 C5 C4 121.9(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 120.9(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C13 117.7(3) . . ?
C6 C7 C8 122.7(4) . . ?
C13 C7 C8 119.6(4) . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 O3 125.9(4) . . ?
C8 C9 C11 120.1(4) . . ?
O3 C9 C11 114.0(3) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 120.9(4) . . ?
C12 C11 H11 119.6 . . ?
C9 C11 H11 119.6 . . ?
C11 C12 C13 121.0(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C7 119.7(3) . . ?
C14 C13 C12 122.0(4) . . ?
C7 C13 C12 118.2(4) . . ?
C4 C14 C13 121.9(4) . . ?
C4 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C30 N1 C33A 103.6(5) . . ?
C30 N1 C33B 111.7(6) . . ?
C30 N1 H1A 111.0 . . ?
C33A N1 H1A 111.0 . . ?
C30 N1 H1B 111.0 . . ?
C33A N1 H1B 111.0 . . ?
H1A N1 H1B 109.0 . . ?
O7 C29 O8 125.3(3) . . ?
O7 C29 C30 117.7(3) . . ?
O8 C29 C30 116.8(3) . . ?
N1 C30 C29 110.8(3) . . ?
N1 C30 C31B 98.1(7) . . ?
C29 C30 C31B 121.7(9) . . ?
N1 C30 C31A 108.2(5) . . ?
C29 C30 C31A 106.8(8) . . ?
N1 C30 H30 110.3 . . ?
C29 C30 H30 110.3 . . ?
C31A C30 H30 110.3 . . ?
C32A C31A C30 99.7(7) . . ?
C32A C31A H31A 111.8 . . ?
C30 C31A H31A 111.8 . . ?
C32A C31A H31B 111.8 . . ?
C30 C31A H31B 111.8 . . ?
H31A C31A H31B 109.5 . . ?
C33A C32A C31A 103.9(9) . . ?
C33A C32A H32A 111.0 . . ?
C31A C32A H32A 111.0 . . ?
C33A C32A H32B 111.0 . . ?
C31A C32A H32B 111.0 . . ?
H32A C32A H32B 109.0 . . ?
C32A C33A N1 99.3(8) . . ?
C32A C33A H33A 111.9 . . ?
N1 C33A H33A 111.9 . . ?
C32A C33A H33B 111.9 . . ?
N1 C33A H33B 111.9 . . ?
H33A C33A H33B 109.6 . . ?
C32B C31B C30 102.6(10) . . ?
C32B C31B H31C 111.2 . . ?
C30 C31B H31C 111.2 . . ?
C32B C31B H31D 111.2 . . ?
C30 C31B H31D 111.2 . . ?
H31C C31B H31D 109.2 . . ?
C33B C32B C31B 102.4(13) . . ?
C33B C32B H32C 111.3 . . ?
C31B C32B H32C 111.3 . . ?
C33B C32B H32D 111.3 . . ?
C31B C32B H32D 111.3 . . ?
H32C C32B H32D 109.2 . . ?
C32B C33B N1 97.4(10) . . ?
C32B C33B H33C 112.3 . . ?
N1 C33B H33C 112.3 . . ?
C32B C33B H33D 112.3 . . ?
N1 C33B H33D 112.3 . . ?
H33C C33B H33D 109.9 . . ?
C38 N2 C35 108.5(3) . . ?
C38 N2 H2A 110.0 . . ?
C35 N2 H2A 110.0 . . ?
C38 N2 H2B 110.0 . . ?
C35 N2 H2B 110.0 . . ?
H2A N2 H2B 108.4 . . ?
O11 C34 O10 124.7(3) . . ?
O11 C34 C35 119.1(3) . . ?
O10 C34 C35 116.2(3) . . ?
C34 C35 N2 109.5(2) . . ?
C34 C35 C36 112.4(4) . . ?
N2 C35 C36 102.8(3) . . ?
C34 C35 H35 110.6 . . ?
N2 C35 H35 110.6 . . ?
C36 C35 H35 110.6 . . ?
C35 C36 C37 102.6(3) . . ?
C35 C36 H36A 111.2 . . ?
C37 C36 H36A 111.2 . . ?
C35 C36 H36B 111.2 . . ?
C37 C36 H36B 111.2 . . ?
H36A C36 H36B 109.2 . . ?
C38 C37 C36 103.7(5) . . ?
C38 C37 H37A 111.0 . . ?
C36 C37 H37A 111.0 . . ?
C38 C37 H37B 111.0 . . ?
C36 C37 H37B 111.0 . . ?
H37A C37 H37B 109.0 . . ?
C37 C38 N2 104.9(4) . . ?
C37 C38 H38A 110.8 . . ?
N2 C38 H38A 110.8 . . ?
C37 C38 H38B 110.8 . . ?
N2 C38 H38B 110.8 . . ?
H38A C38 H38B 108.8 . . ?
C15 O4 H4 109.5 . . ?
C24 O6 C23 117.9(4) . . ?
O5 C15 O4 123.9(3) . . ?
O5 C15 C16 123.6(4) . . ?
O4 C15 C16 112.4(4) . . ?
C17 C16 C15 112.0(4) . . ?
C17 C16 C18 111.7(4) . . ?
C15 C16 C18 108.7(3) . . ?
C17 C16 H16 108.1 . . ?
C15 C16 H16 108.1 . . ?
C18 C16 H16 108.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C28 118.6(3) . . ?
C19 C18 C16 121.3(4) . . ?
C28 C18 C16 120.1(4) . . ?
C18 C19 C20 122.2(4) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C26 117.8(4) . . ?
C21 C20 C19 123.1(4) . . ?
C26 C20 C19 119.0(3) . . ?
C22 C21 C20 121.8(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C24 120.1(4) . . ?
C21 C22 H22 120.0 . . ?
C24 C22 H22 120.0 . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 O6 125.4(4) . . ?
C25 C24 C22 120.6(4) . . ?
O6 C24 C22 114.0(4) . . ?
C24 C25 C26 119.8(4) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C20 C26 C27 118.0(3) . . ?
C20 C26 C25 119.7(3) . . ?
C27 C26 C25 122.3(4) . . ?
C28 C27 C26 121.0(4) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C18 121.1(4) . . ?
C27 C28 H28 119.5 . . ?
C18 C28 H28 119.5 . . ?
O12A C39 H39A 109.5 . . ?
O12A C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O12A C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O12B C39 H39D 109.5 . . ?
O12B C39 H39E 109.5 . . ?
H39D C39 H39E 109.5 . . ?
O12B C39 H39F 109.5 . . ?
H39D C39 H39F 109.5 . . ?
H39E C39 H39F 109.5 . . ?
C39 O12A H12A 109.5 . . ?
C39 O12B H12B 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
O2 C1 C2 C3 17.3(6) . . . . ?
O1 C1 C2 C3 -163.8(4) . . . . ?
O2 C1 C2 C4 -106.0(5) . . . . ?
O1 C1 C2 C4 72.9(5) . . . . ?
C3 C2 C4 C14 107.0(5) . . . . ?
C1 C2 C4 C14 -130.1(4) . . . . ?
C3 C2 C4 C5 -72.8(5) . . . . ?
C1 C2 C4 C5 50.1(5) . . . . ?
C14 C4 C5 C6 4.0(6) . . . . ?
C2 C4 C5 C6 -176.2(4) . . . . ?
C4 C5 C6 C7 -1.3(6) . . . . ?
C5 C6 C7 C13 -2.2(6) . . . . ?
C5 C6 C7 C8 176.1(4) . . . . ?
C6 C7 C8 C9 -178.7(4) . . . . ?
C13 C7 C8 C9 -0.5(5) . . . . ?
C7 C8 C9 O3 177.5(3) . . . . ?
C7 C8 C9 C11 -2.4(6) . . . . ?
C10 O3 C9 C8 3.3(6) . . . . ?
C10 O3 C9 C11 -176.9(4) . . . . ?
C8 C9 C11 C12 3.1(6) . . . . ?
O3 C9 C11 C12 -176.8(4) . . . . ?
C9 C11 C12 C13 -0.8(6) . . . . ?
C6 C7 C13 C14 2.9(5) . . . . ?
C8 C7 C13 C14 -175.4(3) . . . . ?
C6 C7 C13 C12 -179.0(4) . . . . ?
C8 C7 C13 C12 2.6(5) . . . . ?
C11 C12 C13 C14 176.0(4) . . . . ?
C11 C12 C13 C7 -2.0(6) . . . . ?
C5 C4 C14 C13 -3.2(5) . . . . ?
C2 C4 C14 C13 177.0(3) . . . . ?
C7 C13 C14 C4 -0.2(5) . . . . ?
C12 C13 C14 C4 -178.2(3) . . . . ?
C33A N1 C30 C29 -99.6(9) . . . . ?
C33B N1 C30 C29 -111.8(12) . . . . ?
C33B N1 C30 C31B 16.7(15) . . . . ?
C33A N1 C30 C31A 17.1(11) . . . . ?
O7 C29 C30 N1 3.4(5) . . . . ?
O8 C29 C30 N1 179.5(3) . . . . ?
O7 C29 C30 C31B -110.9(8) . . . . ?
O8 C29 C30 C31B 65.2(8) . . . . ?
O7 C29 C30 C31A -114.2(6) . . . . ?
O8 C29 C30 C31A 61.9(6) . . . . ?
N1 C30 C31A C32A 13.1(12) . . . . ?
C29 C30 C31A C32A 132.4(9) . . . . ?
C30 C31A C32A C33A -39.6(14) . . . . ?
C31A C32A C33A N1 50.9(14) . . . . ?
C30 N1 C33A C32A -40.9(12) . . . . ?
N1 C30 C31B C32B -41.9(14) . . . . ?
C29 C30 C31B C32B 78.7(13) . . . . ?
C30 C31B C32B C33B 55(2) . . . . ?
C31B C32B C33B N1 -40(2) . . . . ?
C30 N1 C33B C32B 14(2) . . . . ?
O11 C34 C35 N2 0.6(5) . . . . ?
O10 C34 C35 N2 178.5(3) . . . . ?
O11 C34 C35 C36 -113.0(4) . . . . ?
O10 C34 C35 C36 64.9(5) . . . . ?
C38 N2 C35 C34 -104.9(4) . . . . ?
C38 N2 C35 C36 14.7(4) . . . . ?
C34 C35 C36 C37 83.3(5) . . . . ?
N2 C35 C36 C37 -34.3(5) . . . . ?
C35 C36 C37 C38 42.4(5) . . . . ?
C36 C37 C38 N2 -33.0(5) . . . . ?
C35 N2 C38 C37 11.3(5) . . . . ?
O5 C15 C16 C17 -23.0(6) . . . . ?
O4 C15 C16 C17 158.6(4) . . . . ?
O5 C15 C16 C18 100.9(5) . . . . ?
O4 C15 C16 C18 -77.5(5) . . . . ?
C17 C16 C18 C19 -108.2(5) . . . . ?
C15 C16 C18 C19 127.7(4) . . . . ?
C17 C16 C18 C28 72.5(4) . . . . ?
C15 C16 C18 C28 -51.6(5) . . . . ?
C28 C18 C19 C20 2.4(5) . . . . ?
C16 C18 C19 C20 -176.9(3) . . . . ?
C18 C19 C20 C21 178.2(3) . . . . ?
C18 C19 C20 C26 0.7(5) . . . . ?
C26 C20 C21 C22 2.9(6) . . . . ?
C19 C20 C21 C22 -174.6(4) . . . . ?
C20 C21 C22 C24 -0.6(6) . . . . ?
C23 O6 C24 C25 -3.1(5) . . . . ?
C23 O6 C24 C22 176.9(3) . . . . ?
C21 C22 C24 C25 -2.4(6) . . . . ?
C21 C22 C24 O6 177.7(4) . . . . ?
O6 C24 C25 C26 -177.2(3) . . . . ?
C22 C24 C25 C26 2.9(5) . . . . ?
C21 C20 C26 C27 178.5(3) . . . . ?
C19 C20 C26 C27 -3.9(5) . . . . ?
C21 C20 C26 C25 -2.3(5) . . . . ?
C19 C20 C26 C25 175.3(3) . . . . ?
C24 C25 C26 C20 -0.5(5) . . . . ?
C24 C25 C26 C27 178.6(3) . . . . ?
C20 C26 C27 C28 4.0(5) . . . . ?
C25 C26 C27 C28 -175.2(4) . . . . ?
C26 C27 C28 C18 -0.8(6) . . . . ?
C19 C18 C28 C27 -2.4(5) . . . . ?
C16 C18 C28 C27 177.0(4) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.035


# start Validation Reply Form
_vrf_PLAT420_nt0025_RSnprxDproMeOHb4 
;
PROBLEM: D-H Without Acceptor       O12B     --H12B           Please Check 
RESPONSE: Second componend of disordered methanol molecule.
;
_vrf_PLAT202_nt0025_RSnprxDproMeOHb4 
;
PROBLEM: Isotropic non-H Atoms in Anion/Solvent .........          1 Check 
RESPONSE: Carbon atom of the disordered methanol molecule.
;
_vrf_PLAT242_nt0025_RSnprxDproMeOHb4 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        C15 Check 
RESPONSE: Carbon atom in the wobbling COOH-group.
;
_vrf_PLAT243_nt0025_RSnprxDproMeOHb4 
;
PROBLEM: High   'Solvent' Ueq as Compared to Neighbors of        C37 Check 
RESPONSE: Probably because of minor disorder of the proline molecule.
;
_vrf_PLAT244_nt0025_RSnprxDproMeOHb4 
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of        C29 Check 
RESPONSE: Carbon atom in the wobbling COO^-^-group.
;
_vrf_PLAT340_nt0025_RSnprxDproMeOHb4 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00564 Ang.  
RESPONSE: Limited resolution - crystal diffracts poorly on Mo radiation, 
and we had to use Cu radiation. 
;
_vrf_PLAT911_nt0025_RSnprxDproMeOHb4 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.598         36 Report
RESPONSE: 9 reflections are missing because of overflow, the rest is missing
 in the highest and lowest resolution shells because of the instrument 
geometry limitation.
;
_vrf_PLAT913_nt0025_RSnprxDproMeOHb4 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          9 Note  
RESPONSE: These reflections are missing because of overflow.
;
_vrf_PLAT915_nt0025_RSnprxDproMeOHb4 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         64 %     
RESPONSE: Absolute configuration established by
 the structure determination of a compound containing a chiral reference
 molecule of known absolute configuration (S-naproxen). Signal-to-noise ratio
of the data was not sufficient enough for direct determination of the absolute
 configuration by anomalous-dispersion effects, so we did not collect all 
Friedel pairs.
;
####################################################################### 
# 
# 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_RSnprx_DLpro_1_1_pol_II
_database_code_depnum_ccdc_archive 'CCDC 1861024'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_chemical_name_systematic        
'(2R)-2-(6-methoxynaphthalen-2-yl)propanoic acid (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid (2R)-pyrrolidin-1-ium-2-carboxylate (2S)-pyrrolidin-1-ium-2-carboxylate, polymorph II'
_chemical_name_common            
;
RS-naproxen DL-proline 1:1 cocrystal, polymorph II
;
_chemical_formula_moiety         'C14 H14 O3, C5 H9 N O2'
_chemical_formula_sum            'C19 H23 N O5'
_chemical_formula_weight         345.38
_exptl_crystal_density_diffrn    1.290
_chemical_melting_point          ?
_chemical_absolute_configuration rm


_cell_length_a                   34.537(4)
_cell_length_b                   9.0077(8)
_cell_length_c                   5.7183(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1779.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    428
_cell_special_details            
; 
The powder pattern was indexed using FOX program
;
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'

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

_pd_spec_size_axial              4
_pd_spec_size_equat              0.5
_pd_spec_size_thick              0.5


_pd_spec_mounting                'Thin-wall 0.5 mm glass capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  colourless
_exptl_absorpt_correction_type   none

_pd_instr_location               
; 
BM1 beamline, The Swiss-Norwegian Beamlines (SNBL) at 
European Synchrotron Radiation Facility (ESRF), Grenoble, France
;
_pd_calibration_special_details  
; 
using LaB₆ standard
;

_diffrn_ambient_temperature      428
_diffrn_source                   synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  PILATUS@SNBL
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_type            'PILATUS 2M'
_diffrn_radiation_wavelength     0.78487
_pd_meas_scan_method             fixed
_pd_meas_special_details         
;  ?
;

_pd_meas_number_of_points        2056
_pd_meas_2theta_range_min        2.13192
_pd_meas_2theta_range_max        33.99443
_pd_meas_2theta_range_inc        0.00155


_pd_proc_ls_prof_R_factor        5.13
_pd_proc_ls_prof_wR_factor       7.78
_pd_proc_ls_prof_wR_expected     0.11

_refine_ls_R_I_factor            8.76
_refine_ls_number_reflns         ?
_refine_ls_number_parameters     ?
_refine_ls_number_restraints     ?
_refine_ls_goodness_of_fit_all   72.47
_refine_ls_shift/su_max          0.001

_pd_proc_2theta_range_min        2.13192
_pd_proc_2theta_range_max        33.99443
_pd_proc_2theta_range_inc        0.00155
_pd_proc_wavelength              0.78487

_computing_data_collection       ?
_computing_structure_solution    FOX
_computing_structure_refinement  'TOPAS V5'
_computing_molecular_graphics    ?
_computing_publication_material  ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C1 C 4 0.2673793 0.6833727 0.6750669 1 15
O2 O 4 0.2494537 0.7995153 0.7500287 1 15
O3 O 4 0.285514 0.6709187 0.4858962 1 15
N4 N 4 0.3032161 0.5341866 0.9634741 1 15
H5 H 4 0.2989188 0.483772 1.094788 1 15
H6 H 4 0.3123681 0.6220444 1.008359 1 15
C7 C 4 0.2664594 0.5447303 0.8349292 1 15
H8 H 4 0.2450449 0.5494801 0.9471187 1 15
C9 C 4 0.2648 0.39595 0.69097 1 15
H10 H 4 0.2449757 0.3305012 0.7526885 1 15
H11 H 4 0.259179 0.4162685 0.527883 1 15
C12 C 4 0.3055741 0.3271819 0.7138596 1 15
H13 H 4 0.315303 0.2949783 0.5630342 1 15
H14 H 4 0.3041355 0.2406055 0.814357 1 15
C15 C 4 0.3300779 0.4481923 0.8162226 1 15
H16 H 4 0.35158 0.4095088 0.9067527 1 15
H17 H 4 0.3408284 0.5077797 0.690732 1 15
C1a C 4 0.5772(4) 0.5062(6) -0.095(3) 1 7.3(3)
O2a O 4 0.5799(4) 0.6397(6) 0.049(3) 1 7.3(3)
C3a C 4 0.5469(4) 0.7019(6) 0.133(3) 1 7.3(3)
C4a C 4 0.5470(4) 0.7837(6) 0.341(3) 1 7.3(3)
C5a C 4 0.5142(4) 0.8488(6) 0.423(3) 1 7.3(3)
C6a C 4 0.4793(4) 0.8347(6) 0.297(3) 1 7.3(3)
C7a C 4 0.4462(4) 0.9146(6) 0.369(3) 1 7.3(3)
C8a C 4 0.4130(4) 0.9068(6) 0.241(3) 1 7.3(3)
C9a C 4 0.4114(4) 0.8172(6) 0.044(3) 1 7.3(3)
C10a C 4 0.4437(4) 0.7411(6) -0.027(3) 1 7.3(3)
C11a C 4 0.4782(4) 0.7516(6) 0.102(3) 1 7.3(3)
C12a C 4 0.5127(4) 0.6816(6) 0.018(3) 1 7.3(3)
C13a C 4 0.3781(4) 1.0005(6) 0.310(3) 1 7.3(3)
C14a C 4 0.3582(4) 1.0756(6) 0.091(3) 1 7.3(3)
C15a C 4 0.3511(4) 0.8938(6) 0.417(3) 1 7.3(3)
O16a O 4 0.3222(4) 0.9561(6) 0.525(3) 1 7.3(3)
O17a O 4 0.3541(4) 0.7611(6) 0.411(3) 1 7.3(3)
H18a H 4 0.5705(4) 0.8006(6) 0.416(3) 1 8.8(3)
H19a H 4 0.5145(4) 0.8990(6) 0.565(3) 1 8.8(3)
H20a H 4 0.4467(4) 0.9697(6) 0.506(3) 1 8.8(3)
H21a H 4 0.3886(4) 0.8107(6) -0.042(3) 1 8.8(3)
H22a H 4 0.4424(4) 0.6791(6) -0.157(3) 1 8.8(3)
H23a H 4 0.5123(4) 0.6301(6) -0.123(3) 1 8.8(3)
H24a H 4 0.3854(4) 1.0762(6) 0.425(3) 1 8.8(3)
H25a H 4 0.5799(4) 0.4198(6) 0.001(3) 1 8.8(3)
H26a H 4 0.5974(4) 0.5072(6) -0.211(3) 1 8.8(3)
H27a H 4 0.5525(4) 0.5037(6) -0.172(3) 1 8.8(3)
H28a H 4 0.3651(4) 1.0225(6) -0.048(3) 1 8.8(3)
H29a H 4 0.3667(4) 1.1768(6) 0.078(3) 1 8.8(3)
H30a H 4 0.3305(4) 1.0733(6) 0.110(3) 1 8.8(3)
H31a H 4 0.3022(4) 0.9080(6) 0.515(3) 1 8.8(3)

loop_
_pd_proc_2theta_corrected
_pd_calc_intensity_total
_pd_proc_intensity_total
2.13192 2374.98951 2376.24900
2.14743 2382.82026 2377.91800
2.16293 2390.65143 2382.85200
2.17843 2398.48307 2405.82600
2.19394 2406.31526 2415.52600
2.20945 2414.14809 2423.34400
2.22495 2421.98115 2424.72800
2.24045 2428.62470 2435.37900
2.25596 2434.69389 2438.00200
2.27146 2440.76431 2448.11000
2.28697 2446.83622 2445.82200
2.30247 2452.90993 2449.72500
2.31798 2458.98586 2461.35800
2.33348 2465.06414 2467.42500
2.34899 2471.14684 2477.07200
2.36449 2477.24065 2474.77600
2.38000 2483.34801 2479.26500
2.39550 2489.44801 2486.94200
2.41101 2495.55942 2491.46800
2.42651 2500.49224 2498.86300
2.44202 2503.83674 2497.64000
2.45752 2507.43885 2508.16900
2.47303 2511.92775 2509.78900
2.48853 2519.05232 2510.26400
2.50404 2532.60587 2530.47100
2.51954 2559.12894 2586.34400
2.53505 2606.90350 2743.43000
2.55055 2678.60056 3020.89900
2.56606 2762.56734 3381.14400
2.58156 2830.37307 3696.41800
2.59707 2850.44197 3871.94400
2.61257 2811.82200 3809.68000
2.62808 2735.08202 3539.04400
2.64358 2655.58741 3159.90400
2.65909 2598.14839 2843.76300
2.67459 2567.48276 2663.15300
2.69009 2555.71536 2582.50700
2.70560 2553.39510 2564.39700
2.72111 2554.63950 2561.38800
2.73661 2556.93817 2562.17700
2.75211 2559.49557 2576.32200
2.76762 2562.11512 2578.16200
2.78313 2564.75577 2587.26000
2.79863 2567.40823 2589.20000
2.81413 2570.06889 2586.51800
2.82964 2572.73600 2590.32100
2.84514 2575.40797 2590.83000
2.86065 2578.08374 2591.58700
2.87615 2580.76253 2595.73500
2.89166 2583.77461 2592.52700
2.90716 2586.89782 2602.39800
2.92267 2590.02267 2607.39800
2.93817 2593.14887 2604.09500
2.95368 2596.27601 2611.33700
2.96918 2599.40432 2613.83500
2.98469 2602.53345 2622.58300
3.00019 2605.66330 2631.55600
3.01570 2608.79376 2627.88100
3.03120 2611.92476 2633.80600
3.04671 2615.05625 2631.06200
3.06221 2618.18825 2628.40400
3.07772 2621.32135 2633.70600
3.09322 2624.45376 2634.43400
3.10873 2627.58669 2643.10100
3.12423 2630.71989 2648.02600
3.13974 2633.85335 2647.60500
3.15524 2636.98704 2644.72900
3.17075 2640.12095 2642.60100
3.18625 2643.25486 2646.69400
3.20176 2646.38917 2651.13500
3.21726 2649.52365 2652.94200
3.23277 2652.65830 2662.87300
3.24827 2655.79311 2670.40900
3.26378 2658.92809 2667.09400
3.27928 2662.06321 2669.04000
3.29479 2665.19827 2663.68500
3.31029 2668.33388 2668.55300
3.32579 2671.46923 2675.06200
3.34130 2674.60492 2670.74300
3.35681 2677.74074 2675.98900
3.37231 2680.59037 2675.98900
3.38781 2681.80465 2678.18800
3.40332 2683.01906 2686.08100
3.41882 2684.23353 2686.59900
3.43433 2685.44828 2697.95800
3.44983 2686.66302 2701.54700
3.46534 2687.87796 2703.80200
3.48084 2689.09305 2706.04500
3.49635 2690.30828 2703.31400
3.51185 2691.52364 2700.26400
3.52736 2692.73916 2706.14000
3.54286 2693.95482 2706.66200
3.55837 2695.17055 2708.01800
3.57387 2696.38652 2706.20400
3.58938 2697.60264 2705.77900
3.60488 2698.81893 2710.37800
3.62039 2700.03539 2712.02400
3.63589 2701.25194 2718.88300
3.65140 2702.46875 2722.56200
3.66690 2703.68574 2720.03000
3.68241 2704.90292 2720.98600
3.69791 2706.12030 2722.26700
3.71342 2707.33789 2721.93700
3.72892 2708.55568 2725.95700
3.74443 2709.77370 2722.69600
3.75993 2710.99194 2725.76700
3.77544 2712.21042 2726.34500
3.79094 2713.42907 2721.57400
3.80645 2714.64805 2723.80100
3.82195 2715.86730 2722.52300
3.83746 2717.08683 2727.71400
3.85296 2718.30664 2732.27500
3.86847 2719.52668 2730.43700
3.88397 2720.74712 2734.07500
3.89947 2721.96788 2738.65200
3.91498 2723.18944 2737.05000
3.93049 2724.41424 2742.19400
3.94599 2725.63613 2736.43800
3.96150 2726.85841 2738.60400
3.97700 2728.08111 2739.92500
3.99251 2729.30425 2739.58900
4.00801 2730.52785 2750.19700
4.02351 2731.75186 2755.72600
4.03902 2732.97645 2763.40500
4.05452 2734.20158 2771.19800
4.07003 2735.42727 2767.21100
4.08553 2736.65356 2770.97300
4.10104 2737.88039 2769.57600
4.11654 2739.10805 2761.01300
4.13205 2740.33633 2753.17700
4.14755 2741.56527 2743.80500
4.16306 2742.79508 2741.20600
4.17856 2744.02572 2744.84900
4.19407 2745.25725 2742.38600
4.20957 2746.48971 2745.94800
4.22508 2746.43066 2748.96600
4.24058 2746.13282 2755.53300
4.25609 2745.83612 2756.18600
4.27159 2745.54061 2753.09200
4.28710 2745.24639 2752.84600
4.30260 2744.95354 2754.09600
4.31811 2744.66217 2751.21600
4.33361 2744.37237 2754.42600
4.34912 2744.08426 2755.83800
4.36462 2743.79798 2754.47000
4.38013 2743.51367 2759.42900
4.39563 2743.23144 2753.36100
4.41114 2742.95147 2754.78700
4.42664 2742.67400 2753.87300
4.44215 2742.39916 2753.65000
4.45765 2742.12720 2761.38000
4.47316 2741.85838 2758.91400
4.48866 2741.59296 2759.82700
4.50417 2741.33199 2762.32100
4.51967 2741.07593 2760.22600
4.53517 2740.82274 2762.44600
4.55068 2740.57441 2762.86300
4.56618 2740.33144 2760.73800
4.58169 2740.09436 2768.92900
4.59720 2739.86380 2764.73000
4.61270 2739.64047 2770.07800
4.62820 2739.42516 2769.39500
4.64371 2739.21877 2769.57800
4.65921 2739.02240 2773.76900
4.67472 2738.83721 2769.84300
4.69022 2738.66464 2768.08000
4.70573 2738.50632 2771.96200
4.72123 2738.36415 2770.55200
4.73674 2738.24041 2777.09700
4.75224 2738.13771 2777.78700
4.76775 2738.05924 2776.23400
4.78325 2738.00876 2775.83100
4.79876 2737.99083 2775.92900
4.81426 2738.01096 2780.02100
4.82977 2738.07590 2790.67800
4.84527 2738.19399 2797.70900
4.86078 2738.37556 2804.57100
4.87628 2738.63476 2803.67200
4.89179 2739.01461 2793.10700
4.90729 2739.48066 2789.48200
4.92280 2740.08913 2781.78200
4.93830 2740.87698 2778.75400
4.95381 2741.89981 2777.27700
4.96931 2743.24144 2775.18200
4.98482 2744.96225 2779.44300
5.00032 2747.30213 2782.71300
5.01583 2750.95031 2785.16500
5.03133 2758.66060 2792.25700
5.04684 2780.61151 2796.72000
5.06234 2847.33785 2811.82400
5.07785 3028.78851 2872.84900
5.09335 3439.50662 3038.26000
5.10886 4194.08817 3418.56400
5.12436 5311.27481 4102.90600
5.13987 6646.62363 5122.91000
5.15537 7940.56319 6617.91200
5.17087 8938.92091 8071.57900
5.18638 9429.84849 9281.38100
5.20188 9190.92285 9731.72900
5.21739 8137.01872 9116.28400
5.23289 6561.55443 7544.26900
5.24840 4998.59992 5800.06400
5.26391 3848.02949 4407.05300
5.27941 3194.55354 3523.62300
5.29491 2901.49718 3073.76500
5.31042 2794.73265 2896.83100
5.32592 2760.92555 2825.38800
5.34143 2749.83272 2796.90900
5.35693 2744.90325 2779.93900
5.37244 2741.82941 2769.82200
5.38794 2739.61697 2764.95500
5.40345 2737.99935 2767.43800
5.41895 2736.87104 2762.64200
5.43446 2736.18617 2765.16900
5.44996 2735.94397 2763.02500
5.46547 2736.21150 2762.33600
5.48097 2737.28266 2761.76700
5.49648 2740.47582 2763.87100
5.51198 2751.24083 2768.16900
5.52749 2788.05330 2800.53100
5.54299 2899.03117 2888.61500
5.55850 3174.15775 3209.81700
5.57400 3715.65100 3844.05000
5.58951 4534.81300 4889.52000
5.60501 5432.14811 6091.44400
5.62052 6018.30021 6817.29500
5.63602 5963.70850 6647.33200
5.65153 5298.03030 5790.62000
5.66703 4384.21045 4715.30200
5.68254 3597.62061 3761.50600
5.69804 3102.42860 3172.43600
5.71354 2862.28785 2915.46900
5.72905 2769.47325 2817.98500
5.74456 2739.28013 2782.49100
5.76006 2729.75357 2765.36400
5.77557 2725.89627 2757.71400
5.79107 2723.56709 2751.79200
5.80657 2721.79843 2749.95500
5.82208 2720.34724 2741.29500
5.83758 2719.11852 2739.47200
5.85309 2718.05630 2738.03600
5.86859 2717.12211 2733.85300
5.88410 2716.28752 2735.63000
5.89960 2715.53188 2733.16100
5.91511 2714.83978 2735.59000
5.93061 2714.19960 2737.84400
5.94612 2713.60264 2735.87400
5.96162 2713.09905 2734.74500
5.97713 2712.57041 2727.88600
5.99263 2712.06406 2725.89200
6.00814 2711.57968 2725.22500
6.02364 2711.11465 2725.25700
6.03915 2710.72924 2724.70500
6.05465 2710.35306 2725.34100
6.07016 2709.96181 2719.54300
6.08566 2709.55707 2725.39600
6.10117 2709.16481 2724.76000
6.11667 2708.78494 2723.52500
6.13218 2708.41787 2721.35400
6.14768 2708.06465 2717.17800
6.16319 2707.72736 2715.29100
6.17869 2707.41074 2716.88300
6.19420 2707.13067 2717.41800
6.20970 2706.95412 2722.10100
6.22521 2707.14557 2722.02500
6.24071 2708.55510 2718.82500
6.25622 2713.25710 2717.06300
6.27172 2724.80141 2711.72600
6.28723 2746.57311 2709.61200
6.30273 2777.68715 2713.50500
6.31824 2808.99577 2712.30300
6.33374 2825.51639 2716.81600
6.34925 2817.57978 2713.89900
6.36475 2789.78223 2709.37800
6.38026 2756.54864 2707.64300
6.39576 2730.09056 2702.36400
6.41127 2714.36284 2703.20400
6.42677 2707.02617 2705.22600
6.44228 2704.18730 2706.43300
6.45778 2703.15208 2708.40100
6.47328 2702.68808 2705.75900
6.48879 2702.38034 2700.19000
6.50429 2702.11865 2701.86000
6.51980 2701.87707 2698.01700
6.53530 2701.64830 2701.17400
6.55081 2701.42905 2696.43700
6.56631 2701.21722 2694.60300
6.58182 2701.01133 2694.27600
6.59732 2700.81044 2692.05600
6.61283 2700.61814 2689.93200
6.62833 2700.42494 2689.50500
6.64384 2700.23489 2688.54600
6.65934 2700.04769 2690.42600
6.67485 2699.86402 2686.41800
6.69035 2699.70203 2684.87300
6.70586 2699.52584 2688.99300
6.72136 2699.37518 2691.03800
6.73687 2699.20054 2689.22100
6.75237 2699.02823 2685.29100
6.76788 2698.85835 2673.65700
6.78338 2698.69099 2670.57600
6.79889 2698.52634 2667.80700
6.81439 2698.36458 2669.48500
6.82990 2698.20602 2672.68700
6.84540 2698.05097 2668.33300
6.86091 2697.89989 2671.91800
6.87641 2697.75331 2671.67500
6.89192 2697.61192 2672.18200
6.90742 2697.47659 2672.38200
6.92293 2697.34995 2669.30800
6.93843 2697.26099 2670.05700
6.95394 2697.15208 2673.17600
6.96944 2697.05596 2668.79600
6.98494 2696.97667 2675.81200
7.00045 2696.99398 2675.69500
7.01595 2696.96176 2673.95600
7.03146 2696.96503 2672.79100
7.04697 2697.01574 2668.53900
7.06247 2697.14522 2670.11700
7.07797 2697.45847 2669.54100
7.09348 2698.38399 2664.75200
7.10898 2701.48134 2661.91800
7.12449 2711.25255 2662.89600
7.13999 2737.32292 2680.77000
7.15550 2793.33296 2716.78900
7.17100 2887.17966 2762.57800
7.18651 3004.52615 2821.48100
7.20201 3102.10836 2866.26300
7.21752 3128.77914 2876.85500
7.23302 3068.07287 2847.53800
7.24853 2955.30719 2787.45500
7.26403 2843.24649 2732.48500
7.27954 2764.33249 2694.20200
7.29504 2721.95484 2669.93300
7.31055 2703.92115 2662.25300
7.32605 2697.53500 2658.80300
7.34156 2695.39841 2658.34200
7.35706 2694.53769 2659.21100
7.37257 2694.03170 2654.52000
7.38807 2693.64765 2657.85100
7.40358 2693.32785 2659.30500
7.41908 2693.05257 2660.63200
7.43459 2692.81124 2664.35100
7.45009 2692.59704 2659.29600
7.46560 2692.40521 2659.11500
7.48110 2692.23258 2658.80100
7.49661 2692.07699 2654.88700
7.51211 2691.93714 2655.62900
7.52762 2691.81242 2654.46800
7.54312 2691.70282 2653.66000
7.55863 2691.60894 2658.31100
7.57413 2691.53200 2653.98800
7.58964 2691.47397 2654.62500
7.60514 2691.43780 2661.33200
7.62065 2691.42776 2660.61200
7.63615 2691.45016 2663.93100
7.65165 2691.51590 2659.03100
7.66716 2691.68997 2657.91300
7.68266 2692.00204 2662.45800
7.69817 2692.87299 2666.67500
7.71367 2695.63192 2678.16600
7.72918 2703.73355 2699.32800
7.74468 2723.67785 2738.91800
7.76019 2762.96639 2808.37600
7.77569 2822.77434 2890.66700
7.79120 2889.19686 2972.32500
7.80670 2933.99190 3043.40900
7.82221 2932.03814 3049.58700
7.83771 2884.51686 2997.64600
7.85322 2817.81893 2906.40100
7.86872 2759.55837 2816.86200
7.88423 2722.32920 2743.66900
7.89973 2704.04829 2698.05300
7.91524 2697.04315 2679.90700
7.93074 2695.04243 2677.54800
7.94625 2694.83548 2676.98800
7.96175 2695.23077 2676.29200
7.97726 2695.93223 2673.93800
7.99276 2696.89775 2673.53600
8.00827 2698.16312 2672.75300
8.02377 2699.80135 2667.49800
8.03928 2701.93389 2671.09200
8.05478 2704.81499 2675.05700
8.07029 2709.25502 2679.33700
8.08579 2718.40718 2689.83100
8.10130 2743.47360 2701.73900
8.11680 2816.33783 2765.60600
8.13231 3004.50994 2891.06200
8.14781 3402.95925 3154.55600
8.16332 4067.90366 3619.40300
8.17882 4908.59266 4156.49500
8.19432 5653.83596 4571.72700
8.20983 6011.88729 4826.07600
8.22533 5964.19037 4834.98300
8.24084 5827.44507 4772.75200
8.25634 5894.91666 4746.70300
8.27185 6108.26956 4741.59200
8.28735 6112.03084 4600.70700
8.30286 5641.25653 4267.94500
8.31836 4810.82616 3784.48900
8.33387 3952.77041 3308.94300
8.34937 3317.16839 2983.37500
8.36488 2956.98424 2810.70500
8.38038 2795.55685 2727.53200
8.39589 2736.22316 2699.13300
8.41139 2716.65778 2693.38500
8.42690 2709.78161 2693.34900
8.44240 2706.64266 2697.10000
8.45791 2704.80677 2694.25800
8.47341 2703.63118 2693.48900
8.48892 2702.93887 2698.79500
8.50442 2702.58997 2693.91400
8.51993 2702.50628 2693.49500
8.53543 2702.63164 2693.44200
8.55094 2702.92477 2691.08300
8.56644 2703.35471 2696.35400
8.58195 2703.89809 2699.81400
8.59745 2704.53709 2703.74700
8.61296 2705.25777 2707.21200
8.62846 2706.04942 2704.51100
8.64397 2706.90372 2707.09700
8.65947 2707.81419 2708.24900
8.67498 2708.77616 2707.50100
8.69048 2709.83424 2712.35300
8.70599 2710.88848 2708.66600
8.72149 2711.98553 2713.41400
8.73700 2713.12434 2715.23300
8.75250 2714.30421 2714.81400
8.76801 2715.52545 2719.86400
8.78351 2716.78893 2721.42200
8.79902 2718.09592 2723.03500
8.81452 2719.44850 2728.29800
8.83002 2720.84902 2726.88300
8.84553 2722.30106 2730.21800
8.86103 2723.80863 2727.15700
8.87654 2725.37534 2725.61100
8.89204 2726.99790 2729.54300
8.90755 2728.69694 2728.20900
8.92305 2730.48757 2727.84800
8.93856 2732.37099 2729.96400
8.95406 2734.35908 2732.99700
8.96957 2736.46710 2743.88800
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32.52147 921.48435 906.73110
32.53698 919.11010 907.04570
32.55248 917.07514 907.63870
32.56799 915.52457 907.98200
32.58349 914.51382 909.32870
32.59900 914.02143 909.08050
32.61450 913.99486 908.60940
32.63000 914.35480 911.88460
32.64551 914.97578 914.44940
32.66101 915.67777 915.18730
32.67652 916.25342 914.81180
32.69202 916.51261 913.27590
32.70753 916.32973 911.94280
32.72303 915.67836 912.21090
32.73854 914.64792 909.86770
32.75404 913.41924 908.70750
32.76955 912.19076 906.35550
32.78506 911.12288 904.93810
32.80056 910.30967 905.24630
32.81606 909.77972 908.10770
32.83157 909.50986 909.25840
32.84707 909.45172 909.13240
32.86258 909.55815 906.73020
32.87808 909.80766 906.51060
32.89359 910.20677 909.58830
32.90909 910.77107 910.38850
32.92460 911.50917 910.29140
32.94011 912.41837 910.13070
32.95561 913.49971 908.38690
32.97111 914.79366 906.87880
32.98662 916.41685 907.56440
33.00212 918.55797 910.73430
33.01763 921.42092 914.57160
33.03313 925.10352 918.21110
33.04864 929.50524 919.33110
33.06414 934.26107 922.79710
33.07965 938.81577 928.69270
33.09515 942.50906 933.54350
33.11066 944.69371 932.47780
33.12616 944.90659 931.92170
33.14167 943.19177 931.29070
33.15717 940.19208 930.88130
33.17268 936.82347 929.47080
33.18818 933.87931 930.97360
33.20369 931.78770 932.06010
33.21919 930.57464 933.03250
33.23470 929.92468 934.10230
33.25020 929.33274 934.31990
33.26571 928.33102 932.01820
33.28121 926.75738 930.55080
33.29671 924.82149 928.19500
33.31222 922.92209 923.00950
33.32772 921.43143 918.29820
33.34323 921.01063 918.79830
33.35873 921.62409 918.14560
33.37424 922.71324 915.28060
33.38974 924.01461 915.56820
33.40525 925.30073 917.07780
33.42075 926.51559 918.82900
33.43626 927.80282 920.22520
33.45176 929.37393 921.78250
33.46727 931.37411 922.30270
33.48277 933.79724 920.70650
33.49828 936.49166 921.86400
33.51378 939.19337 923.69150
33.52929 941.59560 922.34680
33.54480 943.39230 920.60490
33.56030 944.35396 921.40270
33.57580 944.36615 923.53040
33.59131 943.46324 923.08760
33.60681 941.87903 918.16670
33.62232 940.01260 915.11880
33.63782 938.30318 912.26260
33.65332 937.09009 912.06370
33.66883 936.54191 911.02120
33.68433 936.64303 910.07300
33.69984 937.22671 908.96800
33.71535 938.04501 908.59860
33.73085 938.86107 907.14840
33.74636 939.54914 909.07570
33.76186 940.14828 911.84530
33.77737 940.83358 914.03250
33.79287 941.80819 915.60660
33.80838 943.20576 918.39180
33.82388 945.02292 922.31250
33.83938 947.10598 924.60820
33.85489 949.17514 926.93240
33.87040 950.89894 926.63280
33.88590 952.02405 923.88420
33.90141 952.48862 918.29860
33.91691 952.42392 914.56670
33.93242 952.06775 912.96120
33.94792 951.65662 911.54090
33.96342 951.35212 908.89820
33.97893 951.22830 909.02010
33.99443 951.30739 911.91540

# start Validation Reply Form
_vrf_GEOM001_RSnprx_DLpro_1_1_pol_II 
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM003_RSnprx_DLpro_1_1_pol_II 
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM006_RSnprx_DLpro_1_1_pol_II 
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM007_RSnprx_DLpro_1_1_pol_II 
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_exptl_crystal_colour            colourless
_exptl_crystal_description       powder
####################################################################### 
# 
# 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_nt0023_SprxDLpro_MeOH_b6
_database_code_depnum_ccdc_archive 'CCDC 1861018'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
bis((2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid) 
2R)-pyrrolidin-1-ium-2-carboxylate
2S)-pyrrolidin-1-ium-2-carboxylate
;
_chemical_name_common            'S-naproxen DL-proline 1:1 cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H14 O3), 2(C5 H9 N O2)'
_chemical_formula_sum            'C38 H46 N2 O10'
_chemical_formula_weight         690.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.84337(19)
_cell_length_b                   5.83510(15)
_cell_length_c                   33.6766(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.9839(19)
_cell_angle_gamma                90
_cell_volume                     1736.74(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4502
_cell_measurement_theta_min      4.0000
_cell_measurement_theta_max      67.0620

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.787
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            10460
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.626
_diffrn_reflns_theta_max         67.145
_diffrn_reflns_theta_full        67.145
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_point_group_measured_fraction_full 0.785
_reflns_number_total             4868
_reflns_number_gt                4427
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.428
_reflns_Friedel_fraction_max     0.527
_reflns_Friedel_fraction_full    0.527

_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0780P)²+0.2562P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_chemical_absolute_configuration rm
_refine_ls_number_reflns         4868
_refine_ls_number_parameters     457
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O9 O 0.7029(2) 0.2078(5) 0.25418(8) 0.0637(7) Uani 1 1 d . . . . .
O10 O 0.8526(2) 0.4988(5) 0.27331(8) 0.0639(7) Uani 1 1 d . . . . .
N2 N 0.4463(2) 0.4296(5) 0.26397(7) 0.0441(6) Uani 1 1 d . . . . .
H2A H 0.375123 0.516464 0.252223 0.053 Uiso 1 1 calc R U . . .
H2B H 0.462495 0.308747 0.248571 0.053 Uiso 1 1 calc R U . . .
C34 C 0.7261(3) 0.4075(7) 0.26533(9) 0.0473(8) Uani 1 1 d . . . . .
C35 C 0.5891(3) 0.5638(6) 0.27037(10) 0.0482(8) Uani 1 1 d . . . . .
H35 H 0.591738 0.691307 0.251472 0.058 Uiso 1 1 calc R U . . .
C36 C 0.5762(5) 0.6555(8) 0.31270(13) 0.0736(12) Uani 1 1 d . . . . .
H36A H 0.675394 0.670010 0.325687 0.088 Uiso 1 1 calc R U . . .
H36B H 0.526963 0.804069 0.312545 0.088 Uiso 1 1 calc R U . . .
C37 C 0.4839(5) 0.4831(14) 0.33305(12) 0.100(2) Uani 1 1 d . . . . .
H37A H 0.549197 0.380995 0.348576 0.120 Uiso 1 1 calc R U . . .
H37B H 0.416249 0.558856 0.350926 0.120 Uiso 1 1 calc R U . . .
C38 C 0.3974(4) 0.3538(8) 0.30375(11) 0.0672(11) Uani 1 1 d . . . . .
H38A H 0.290140 0.382094 0.306368 0.081 Uiso 1 1 calc R U . . .
H38B H 0.415991 0.191065 0.307229 0.081 Uiso 1 1 calc R U . . .
O1 O 0.2868(3) 0.6534(8) 0.14840(10) 0.0972(13) Uani 1 1 d . . . . .
O2 O 0.5025(2) 0.7613(6) 0.17642(8) 0.0732(9) Uani 1 1 d . . . . .
H2O H 0.446419 0.835792 0.190385 0.088 Uiso 1 1 calc R U . . .
O3 O 0.1006(3) 0.2023(7) -0.08206(7) 0.0760(9) Uani 1 1 d . . . . .
C1 C 0.4211(3) 0.6444(6) 0.15015(9) 0.0479(8) Uani 1 1 d . . . . .
C2 C 0.5180(4) 0.5118(8) 0.12229(10) 0.0588(10) Uani 1 1 d . . . . .
H2 H 0.590212 0.620356 0.111377 0.071 Uiso 1 1 calc R U . . .
C3 C 0.6096(7) 0.3350(12) 0.14621(16) 0.118(3) Uani 1 1 d . . . . .
H3A H 0.672253 0.411679 0.165900 0.176 Uiso 1 1 calc R U . . .
H3B H 0.672105 0.249876 0.128737 0.176 Uiso 1 1 calc R U . . .
H3C H 0.542014 0.232245 0.159051 0.176 Uiso 1 1 calc R U . . .
C4 C 0.4255(4) 0.4139(7) 0.08745(9) 0.0508(8) Uani 1 1 d . . . . .
C5 C 0.4211(3) 0.5274(7) 0.05191(10) 0.0484(8) Uani 1 1 d . . . . .
H5 H 0.474512 0.663901 0.049695 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3376(3) 0.4431(6) 0.01840(9) 0.0450(7) Uani 1 1 d . . . . .
C7 C 0.3340(4) 0.5592(7) -0.01853(10) 0.0535(8) Uani 1 1 d . . . . .
H7 H 0.386300 0.696392 -0.021070 0.064 Uiso 1 1 calc R U . . .
C8 C 0.2547(4) 0.4717(8) -0.05024(11) 0.0596(10) Uani 1 1 d . . . . .
H8 H 0.254650 0.549064 -0.074387 0.071 Uiso 1 1 calc R U . . .
C9 C 0.1735(4) 0.2682(7) -0.04732(10) 0.0531(9) Uani 1 1 d . . . . .
C10 C 0.0011(5) 0.0131(9) -0.08078(13) 0.0747(12) Uani 1 1 d . . . . .
H10A H -0.047649 -0.007930 -0.106437 0.112 Uiso 1 1 calc R U . . .
H10B H -0.073944 0.041162 -0.061432 0.112 Uiso 1 1 calc R U . . .
H10C H 0.057280 -0.122303 -0.073609 0.112 Uiso 1 1 calc R U . . .
C11 C 0.1726(4) 0.1496(7) -0.01220(9) 0.0504(8) Uani 1 1 d . . . . .
H11 H 0.117652 0.014431 -0.010329 0.060 Uiso 1 1 calc R U . . .
C12 C 0.2569(3) 0.2359(6) 0.02142(9) 0.0454(7) Uani 1 1 d . . . . .
C13 C 0.2634(4) 0.1203(7) 0.05852(10) 0.0560(9) Uani 1 1 d . . . . .
H13 H 0.211340 -0.017023 0.061256 0.067 Uiso 1 1 calc R U . . .
C14 C 0.3445(4) 0.2071(8) 0.09016(10) 0.0579(9) Uani 1 1 d . . . . .
H14 H 0.346386 0.127869 0.114133 0.069 Uiso 1 1 calc R U . . .
O7 O 0.3475(2) -0.0087(5) 0.22693(8) 0.0646(8) Uani 1 1 d . . . . .
O8 O 0.1989(2) -0.2979(5) 0.24522(8) 0.0632(7) Uani 1 1 d . . . . .
N1 N -0.0575(3) -0.0671(5) 0.23393(8) 0.0475(6) Uani 1 1 d . . . . .
H1A H -0.127497 0.018590 0.245153 0.057 Uiso 1 1 calc R U . . .
H1B H -0.041576 -0.191563 0.248760 0.057 Uiso 1 1 calc R U . . .
C29 C 0.2220(3) -0.0975(7) 0.23472(9) 0.0482(8) Uani 1 1 d . . . . .
C30 C 0.0863(3) 0.0657(6) 0.23043(10) 0.0462(8) Uani 1 1 d . . . . .
H30 H 0.093217 0.184473 0.250985 0.055 Uiso 1 1 calc R U . . .
C31 C 0.0687(5) 0.1739(9) 0.19013(13) 0.0751(12) Uani 1 1 d . . . . .
H31A H 0.014666 0.318191 0.191675 0.090 Uiso 1 1 calc R U . . .
H31B H 0.166740 0.202103 0.179054 0.090 Uiso 1 1 calc R U . . .
C32 C -0.0170(5) 0.0103(13) 0.16604(13) 0.0961(19) Uani 1 1 d . . . . .
H32A H 0.051361 -0.085674 0.151446 0.115 Uiso 1 1 calc R U . . .
H32B H -0.082852 0.090433 0.147064 0.115 Uiso 1 1 calc R U . . .
C33 C -0.1083(4) -0.1330(8) 0.19260(13) 0.0743(12) Uani 1 1 d . . . . .
H33A H -0.090043 -0.294564 0.187956 0.089 Uiso 1 1 calc R U . . .
H33B H -0.215382 -0.102290 0.188234 0.089 Uiso 1 1 calc R U . . .
O4 O 0.0059(2) 0.2295(6) 0.32244(7) 0.0637(7) Uani 1 1 d . . . . .
H4 H -0.050161 0.301751 0.307106 0.076 Uiso 1 1 calc R U . . .
O5 O -0.1984(3) 0.2061(9) 0.35749(10) 0.1099(15) Uani 1 1 d . . . . .
O6 O 0.3969(3) 0.2472(6) 0.58449(7) 0.0667(8) Uani 1 1 d . . . . .
C15 C -0.0730(4) 0.1447(8) 0.35112(9) 0.0565(9) Uani 1 1 d . . . . .
C16 C 0.0087(4) -0.0412(7) 0.37518(10) 0.0588(9) Uani 1 1 d . . . . .
H16 H -0.067593 -0.150168 0.383952 0.071 Uiso 1 1 calc R U . . .
C17 C 0.1206(6) -0.1733(9) 0.35016(13) 0.0837(14) Uani 1 1 d . . . . .
H17A H 0.192641 -0.068534 0.339599 0.125 Uiso 1 1 calc R U . . .
H17B H 0.066761 -0.249259 0.328706 0.125 Uiso 1 1 calc R U . . .
H17C H 0.172696 -0.284996 0.366489 0.125 Uiso 1 1 calc R U . . .
C18 C 0.0883(3) 0.0585(6) 0.41217(9) 0.0467(8) Uani 1 1 d . . . . .
C19 C 0.1740(4) 0.2613(7) 0.41082(10) 0.0564(9) Uani 1 1 d . . . . .
H19 H 0.177732 0.341277 0.386982 0.068 Uiso 1 1 calc R U . . .
C20 C 0.2516(4) 0.3440(7) 0.44331(10) 0.0541(9) Uani 1 1 d . . . . .
H20 H 0.305758 0.479875 0.441332 0.065 Uiso 1 1 calc R U . . .
C21 C 0.2513(3) 0.2268(6) 0.48002(9) 0.0439(7) Uani 1 1 d . . . . .
C22 C 0.3326(3) 0.3064(7) 0.51443(9) 0.0487(8) Uani 1 1 d . . . . .
H22 H 0.390437 0.439169 0.513258 0.058 Uiso 1 1 calc R U . . .
C23 C 0.3257(3) 0.1871(7) 0.54933(9) 0.0503(8) Uani 1 1 d . . . . .
C24 C 0.4850(5) 0.4497(9) 0.58499(11) 0.0687(11) Uani 1 1 d . . . . .
H24A H 0.564217 0.435350 0.566355 0.103 Uiso 1 1 calc R U . . .
H24B H 0.528685 0.473057 0.611169 0.103 Uiso 1 1 calc R U . . .
H24C H 0.421932 0.578010 0.577773 0.103 Uiso 1 1 calc R U . . .
C25 C 0.2407(4) -0.0166(7) 0.55121(10) 0.0530(9) Uani 1 1 d . . . . .
H25 H 0.236865 -0.095937 0.575107 0.064 Uiso 1 1 calc R U . . .
C26 C 0.1647(4) -0.0981(7) 0.51870(9) 0.0505(8) Uani 1 1 d . . . . .
H26 H 0.110280 -0.233925 0.520417 0.061 Uiso 1 1 calc R U . . .
C27 C 0.1669(3) 0.0211(6) 0.48190(9) 0.0419(7) Uani 1 1 d . . . . .
C28 C 0.0854(3) -0.0578(6) 0.44761(9) 0.0453(7) Uani 1 1 d . . . . .
H28 H 0.028612 -0.191523 0.449129 0.054 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
O9 C34 1.240(5) . ?
O10 C34 1.260(4) . ?
N2 C38 1.489(5) . ?
N2 C35 1.495(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
C34 C35 1.531(4) . ?
C35 C36 1.531(5) . ?
C35 H35 0.9800 . ?
C36 C37 1.479(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.441(6) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
O1 C1 1.188(4) . ?
O2 C1 1.312(4) . ?
O2 H2O 0.8200 . ?
O3 C9 1.371(4) . ?
O3 C10 1.413(6) . ?
C1 C2 1.506(5) . ?
C2 C4 1.518(5) . ?
C2 C3 1.525(7) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.367(5) . ?
C4 C14 1.408(6) . ?
C5 C6 1.415(5) . ?
C5 H5 0.9300 . ?
C6 C12 1.409(5) . ?
C6 C7 1.416(5) . ?
C7 C8 1.357(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(6) . ?
C8 H8 0.9300 . ?
C9 C11 1.370(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.426(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.419(5) . ?
C13 C14 1.361(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
O7 C29 1.261(4) . ?
O8 C29 1.241(5) . ?
N1 C30 1.497(4) . ?
N1 C33 1.498(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C29 C30 1.534(4) . ?
C30 C31 1.500(5) . ?
C30 H30 0.9800 . ?
C31 C32 1.449(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.484(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
O4 C15 1.308(4) . ?
O4 H4 0.8200 . ?
O5 C15 1.192(4) . ?
O6 C23 1.367(4) . ?
O6 C24 1.415(5) . ?
C15 C16 1.521(6) . ?
C16 C18 1.525(5) . ?
C16 C17 1.530(6) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C28 1.374(5) . ?
C18 C19 1.407(5) . ?
C19 C20 1.359(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.413(5) . ?
C20 H20 0.9300 . ?
C21 C27 1.416(5) . ?
C21 C22 1.420(4) . ?
C22 C23 1.369(5) . ?
C22 H22 0.9300 . ?
C23 C25 1.409(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.351(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.422(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.417(4) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C38 N2 C35 107.2(3) . . ?
C38 N2 H2A 110.3 . . ?
C35 N2 H2A 110.3 . . ?
C38 N2 H2B 110.3 . . ?
C35 N2 H2B 110.3 . . ?
H2A N2 H2B 108.5 . . ?
O9 C34 O10 126.8(3) . . ?
O9 C34 C35 118.1(3) . . ?
O10 C34 C35 115.2(3) . . ?
N2 C35 C34 109.9(3) . . ?
N2 C35 C36 103.2(3) . . ?
C34 C35 C36 113.3(3) . . ?
N2 C35 H35 110.1 . . ?
C34 C35 H35 110.1 . . ?
C36 C35 H35 110.1 . . ?
C37 C36 C35 104.7(4) . . ?
C37 C36 H36A 110.8 . . ?
C35 C36 H36A 110.8 . . ?
C37 C36 H36B 110.8 . . ?
C35 C36 H36B 110.8 . . ?
H36A C36 H36B 108.9 . . ?
C38 C37 C36 109.1(4) . . ?
C38 C37 H37A 109.9 . . ?
C36 C37 H37A 109.9 . . ?
C38 C37 H37B 109.9 . . ?
C36 C37 H37B 109.9 . . ?
H37A C37 H37B 108.3 . . ?
C37 C38 N2 107.3(4) . . ?
C37 C38 H38A 110.3 . . ?
N2 C38 H38A 110.3 . . ?
C37 C38 H38B 110.3 . . ?
N2 C38 H38B 110.3 . . ?
H38A C38 H38B 108.5 . . ?
C1 O2 H2O 109.5 . . ?
C9 O3 C10 117.9(3) . . ?
O1 C1 O2 122.3(3) . . ?
O1 C1 C2 125.5(3) . . ?
O2 C1 C2 112.1(3) . . ?
C1 C2 C4 111.9(3) . . ?
C1 C2 C3 108.8(3) . . ?
C4 C2 C3 114.5(4) . . ?
C1 C2 H2 107.1 . . ?
C4 C2 H2 107.1 . . ?
C3 C2 H2 107.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C14 118.2(3) . . ?
C5 C4 C2 119.5(4) . . ?
C14 C4 C2 122.3(3) . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C12 C6 C5 119.5(3) . . ?
C12 C6 C7 118.5(3) . . ?
C5 C6 C7 122.0(3) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C11 C9 O3 125.3(4) . . ?
C11 C9 C8 120.6(3) . . ?
O3 C9 C8 114.0(3) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 119.3(3) . . ?
C9 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C6 C12 C13 117.8(3) . . ?
C6 C12 C11 119.8(3) . . ?
C13 C12 C11 122.4(3) . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C4 121.6(3) . . ?
C13 C14 H14 119.2 . . ?
C4 C14 H14 119.2 . . ?
C30 N1 C33 106.7(3) . . ?
C30 N1 H1A 110.4 . . ?
C33 N1 H1A 110.4 . . ?
C30 N1 H1B 110.4 . . ?
C33 N1 H1B 110.4 . . ?
H1A N1 H1B 108.6 . . ?
O8 C29 O7 126.9(3) . . ?
O8 C29 C30 118.4(3) . . ?
O7 C29 C30 114.6(4) . . ?
N1 C30 C31 103.1(3) . . ?
N1 C30 C29 109.6(3) . . ?
C31 C30 C29 113.8(3) . . ?
N1 C30 H30 110.1 . . ?
C31 C30 H30 110.1 . . ?
C29 C30 H30 110.1 . . ?
C32 C31 C30 105.4(4) . . ?
C32 C31 H31A 110.7 . . ?
C30 C31 H31A 110.7 . . ?
C32 C31 H31B 110.7 . . ?
C30 C31 H31B 110.7 . . ?
H31A C31 H31B 108.8 . . ?
C31 C32 C33 108.6(4) . . ?
C31 C32 H32A 110.0 . . ?
C33 C32 H32A 110.0 . . ?
C31 C32 H32B 110.0 . . ?
C33 C32 H32B 110.0 . . ?
H32A C32 H32B 108.4 . . ?
C32 C33 N1 105.3(3) . . ?
C32 C33 H33A 110.7 . . ?
N1 C33 H33A 110.7 . . ?
C32 C33 H33B 110.7 . . ?
N1 C33 H33B 110.7 . . ?
H33A C33 H33B 108.8 . . ?
C15 O4 H4 109.5 . . ?
C23 O6 C24 117.5(3) . . ?
O5 C15 O4 122.9(4) . . ?
O5 C15 C16 123.1(4) . . ?
O4 C15 C16 114.1(3) . . ?
C15 C16 C18 111.1(3) . . ?
C15 C16 C17 111.7(3) . . ?
C18 C16 C17 110.7(3) . . ?
C15 C16 H16 107.7 . . ?
C18 C16 H16 107.7 . . ?
C17 C16 H16 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C28 C18 C19 118.0(3) . . ?
C28 C18 C16 119.9(3) . . ?
C19 C18 C16 121.9(3) . . ?
C20 C19 C18 122.0(3) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 121.1(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C27 117.8(3) . . ?
C20 C21 C22 122.7(3) . . ?
C27 C21 C22 119.6(3) . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
O6 C23 C22 125.5(4) . . ?
O6 C23 C25 114.1(3) . . ?
C22 C23 C25 120.5(3) . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C23 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C23 C25 H25 119.6 . . ?
C25 C26 C27 120.8(3) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C21 C27 C28 119.6(3) . . ?
C21 C27 C26 118.5(3) . . ?
C28 C27 C26 122.0(3) . . ?
C18 C28 C27 121.5(3) . . ?
C18 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?

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
C38 N2 C35 C34 95.0(3) . . . . ?
C38 N2 C35 C36 -26.2(4) . . . . ?
O9 C34 C35 N2 5.4(4) . . . . ?
O10 C34 C35 N2 -174.4(3) . . . . ?
O9 C34 C35 C36 120.2(4) . . . . ?
O10 C34 C35 C36 -59.6(4) . . . . ?
N2 C35 C36 C37 28.9(4) . . . . ?
C34 C35 C36 C37 -89.9(4) . . . . ?
C35 C36 C37 C38 -21.7(6) . . . . ?
C36 C37 C38 N2 5.4(6) . . . . ?
C35 N2 C38 C37 13.6(5) . . . . ?
O1 C1 C2 C4 7.9(6) . . . . ?
O2 C1 C2 C4 -169.2(4) . . . . ?
O1 C1 C2 C3 -119.6(5) . . . . ?
O2 C1 C2 C3 63.2(5) . . . . ?
C1 C2 C4 C5 98.1(4) . . . . ?
C3 C2 C4 C5 -137.6(4) . . . . ?
C1 C2 C4 C14 -82.6(4) . . . . ?
C3 C2 C4 C14 41.7(5) . . . . ?
C14 C4 C5 C6 0.2(5) . . . . ?
C2 C4 C5 C6 179.6(3) . . . . ?
C4 C5 C6 C12 -0.3(5) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
C12 C6 C7 C8 -0.2(5) . . . . ?
C5 C6 C7 C8 178.9(3) . . . . ?
C6 C7 C8 C9 0.9(6) . . . . ?
C10 O3 C9 C11 8.4(6) . . . . ?
C10 O3 C9 C8 -172.7(3) . . . . ?
C7 C8 C9 C11 -0.5(6) . . . . ?
C7 C8 C9 O3 -179.5(3) . . . . ?
O3 C9 C11 C12 178.4(3) . . . . ?
C8 C9 C11 C12 -0.5(5) . . . . ?
C5 C6 C12 C13 0.0(5) . . . . ?
C7 C6 C12 C13 179.2(3) . . . . ?
C5 C6 C12 C11 -179.9(3) . . . . ?
C7 C6 C12 C11 -0.8(5) . . . . ?
C9 C11 C12 C6 1.1(5) . . . . ?
C9 C11 C12 C13 -178.9(3) . . . . ?
C6 C12 C13 C14 0.2(5) . . . . ?
C11 C12 C13 C14 -179.8(3) . . . . ?
C12 C13 C14 C4 -0.2(6) . . . . ?
C5 C4 C14 C13 0.0(5) . . . . ?
C2 C4 C14 C13 -179.3(3) . . . . ?
C33 N1 C30 C31 28.9(4) . . . . ?
C33 N1 C30 C29 -92.5(3) . . . . ?
O8 C29 C30 N1 -9.2(4) . . . . ?
O7 C29 C30 N1 170.9(3) . . . . ?
O8 C29 C30 C31 -124.0(4) . . . . ?
O7 C29 C30 C31 56.1(4) . . . . ?
N1 C30 C31 C32 -33.2(4) . . . . ?
C29 C30 C31 C32 85.4(4) . . . . ?
C30 C31 C32 C33 25.5(5) . . . . ?
C31 C32 C33 N1 -7.2(5) . . . . ?
C30 N1 C33 C32 -14.0(4) . . . . ?
O5 C15 C16 C18 -86.2(5) . . . . ?
O4 C15 C16 C18 94.7(4) . . . . ?
O5 C15 C16 C17 149.7(5) . . . . ?
O4 C15 C16 C17 -29.5(5) . . . . ?
C15 C16 C18 C28 139.2(3) . . . . ?
C17 C16 C18 C28 -96.0(4) . . . . ?
C15 C16 C18 C19 -44.9(5) . . . . ?
C17 C16 C18 C19 79.8(5) . . . . ?
C28 C18 C19 C20 -0.5(6) . . . . ?
C16 C18 C19 C20 -176.5(4) . . . . ?
C18 C19 C20 C21 1.0(6) . . . . ?
C19 C20 C21 C27 -0.3(5) . . . . ?
C19 C20 C21 C22 179.1(3) . . . . ?
C20 C21 C22 C23 178.9(3) . . . . ?
C27 C21 C22 C23 -1.7(5) . . . . ?
C24 O6 C23 C22 0.1(5) . . . . ?
C24 O6 C23 C25 179.8(3) . . . . ?
C21 C22 C23 O6 -179.1(3) . . . . ?
C21 C22 C23 C25 1.2(5) . . . . ?
O6 C23 C25 C26 -179.7(3) . . . . ?
C22 C23 C25 C26 0.1(5) . . . . ?
C23 C25 C26 C27 -0.8(5) . . . . ?
C20 C21 C27 C28 -0.7(4) . . . . ?
C22 C21 C27 C28 179.8(3) . . . . ?
C20 C21 C27 C26 -179.6(3) . . . . ?
C22 C21 C27 C26 0.9(5) . . . . ?
C25 C26 C27 C21 0.3(5) . . . . ?
C25 C26 C27 C28 -178.5(3) . . . . ?
C19 C18 C28 C27 -0.6(5) . . . . ?
C16 C18 C28 C27 175.5(3) . . . . ?
C21 C27 C28 C18 1.2(5) . . . . ?
C26 C27 C28 C18 -180.0(3) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.036


# start Validation Reply Form
_vrf_PLAT242_nt0023_SprxDLpro_MeOH_b6 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check 
RESPONSE: Carbon atom in the wobbling COOH-group.

;
_vrf_PLAT243_nt0023_SprxDLpro_MeOH_b6 
;
PROBLEM: High   'Solvent' Ueq as Compared to Neighbors of        C32 Check 
RESPONSE: Probably because of minor disorder of the proline molecule.

;
_vrf_PLAT340_nt0023_SprxDLpro_MeOH_b6 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00533 Ang.  
RESPONSE: Limited resolution - crystal diffracts poorly on Mo radiation, 
and we had to use Cu radiation.
;
_vrf_PLAT911_nt0023_SprxDLpro_MeOH_b6 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.598         27 Report
RESPONSE: 8 reflections are missing because of overflow, the rest is missing
in the highest resolution shell because of the instrument geometry limitation.
;
_vrf_PLAT913_nt0023_SprxDLpro_MeOH_b6 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          8 Note  
RESPONSE: These reflections are missing because of overflow.
;
_vrf_PLAT915_nt0023_SprxDLpro_MeOH_b6 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         53 %     
RESPONSE: Absolute configuration established by
 the structure determination of a compound containing a chiral reference
 molecule of known absolute configuration (S-naproxen). Signal-to-noise ratio
of the data was not sufficient enough for direct determination of the absolute
 configuration by anomalous-dispersion effects, so we did not collect all 
Friedel pairs.
;
_vrf_PLAT978_nt0023_SprxDLpro_MeOH_b6 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: Limited resolution - crystal diffracts poorly on Mo radiation, 
and we had to use Cu radiation.
;
####################################################################### 
# 
# 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_nt0017_Natalia_Snprx_DLpro_EtOHb6
_database_code_depnum_ccdc_archive 'CCDC 1861016'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid (2R)-pyrrolidin-1-ium-2-carboxylate (2S)-pyrrolidin-1-ium-2-carboxylate'
_chemical_name_common            'S-naproxen DL-proline 1:2 cocrystal'
_chemical_melting_point          455(1)
_chemical_formula_moiety         'C14 H14 O3, 2(C5 H9 N O2)'
_chemical_formula_sum            'C24 H32 N2 O7'
_chemical_formula_weight         460.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.8836(7)
_cell_length_b                   9.0952(18)
_cell_length_c                   44.047(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2357.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    954
_cell_measurement_theta_min      4.0240
_cell_measurement_theta_max      53.8150

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    0.790
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            5139
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         4.014
_diffrn_reflns_theta_max         62.649
_diffrn_reflns_theta_full        62.649
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_point_group_measured_fraction_full 0.825
_reflns_number_total             3125
_reflns_number_gt                1899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.445
_reflns_Friedel_fraction_max     0.625
_reflns_Friedel_fraction_full    0.625

_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0416P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_chemical_absolute_configuration rm
_refine_ls_number_reflns         3125
_refine_ls_number_parameters     356
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O1 O -0.3995(10) 0.4509(10) 0.38034(17) 0.163(4) Uani 1 1 d . . . . .
N1 N 0.4873(8) 0.7653(6) 0.32159(11) 0.0609(14) Uani 1 1 d D U . . .
H1A H 0.448565 0.780659 0.302323 0.073 Uiso 0.56(2) 1 calc R U P A 1
H1B H 0.613055 0.710869 0.321857 0.073 Uiso 0.56(2) 1 calc R U P A 1
H1C H 0.435670 0.802789 0.304256 0.073 Uiso 0.44(2) 1 calc R U P A 2
H1D H 0.599300 0.702893 0.317268 0.073 Uiso 0.44(2) 1 calc R U P A 2
C1 C -0.2235(14) 0.3874(10) 0.38302(18) 0.084(2) Uani 1 1 d . . . . .
O2 O -0.0503(9) 0.4207(7) 0.36668(15) 0.1053(19) Uani 1 1 d . . . . .
H2O H -0.082028 0.490531 0.355685 0.126 Uiso 1 1 calc R U . . .
N2 N 0.7970(8) 0.6967(6) 0.24931(13) 0.0622(14) Uani 1 1 d D U . . .
H2A H 0.846317 0.759398 0.263351 0.075 Uiso 1 1 calc R U . A 1
H2B H 0.712108 0.628729 0.258400 0.075 Uiso 1 1 calc R U . A 1
C2 C -0.1723(13) 0.2746(9) 0.40669(17) 0.078(2) Uani 1 1 d . . . . .
H2 H -0.318330 0.232969 0.413060 0.094 Uiso 1 1 calc R U . . .
O3 O 0.1522(10) 0.6463(7) 0.56282(13) 0.0999(18) Uani 1 1 d . . . . .
C3 C -0.0292(15) 0.1466(8) 0.39456(19) 0.103(3) Uani 1 1 d . . . . .
H3A H 0.120976 0.181057 0.389854 0.154 Uiso 1 1 calc R U . . .
H3B H -0.098707 0.107851 0.376545 0.154 Uiso 1 1 calc R U . . .
H3C H -0.020214 0.070874 0.409689 0.154 Uiso 1 1 calc R U . . .
O4 O -0.0895(7) 0.6364(5) 0.32904(12) 0.0807(15) Uani 1 1 d . . . . .
C4 C -0.0692(12) 0.3462(8) 0.43436(18) 0.0679(19) Uani 1 1 d . . . . .
O5 O 0.0749(8) 0.7962(6) 0.29869(11) 0.0787(14) Uani 1 1 d . . . . .
C5 C 0.1448(11) 0.4170(9) 0.43253(18) 0.074(2) Uani 1 1 d . . . . .
H5 H 0.225996 0.414140 0.414429 0.088 Uiso 1 1 calc R U . . .
O6 O 0.5398(8) 0.9252(5) 0.26751(12) 0.0752(13) Uani 1 1 d . . . . .
C6 C 0.2333(11) 0.4891(9) 0.45690(19) 0.078(2) Uani 1 1 d . . . . .
H6 H 0.371375 0.537740 0.454699 0.094 Uiso 1 1 calc R U . . .
O7 O 0.4666(9) 1.0017(6) 0.22054(12) 0.0962(17) Uani 1 1 d . . . . .
C7 C 0.1240(11) 0.4928(8) 0.48521(17) 0.0668(19) Uani 1 1 d . . . . .
C8 C 0.2074(12) 0.5727(9) 0.51013(19) 0.075(2) Uani 1 1 d . . . . .
H8 H 0.341556 0.625894 0.508067 0.091 Uiso 1 1 calc R U . . .
C9 C 0.0963(14) 0.5740(8) 0.53722(19) 0.076(2) Uani 1 1 d . . . . .
C10 C 0.3419(14) 0.7455(9) 0.56123(18) 0.097(3) Uani 1 1 d . . . . .
H10A H 0.324236 0.809151 0.544006 0.145 Uiso 1 1 calc R U . . .
H10B H 0.480022 0.690203 0.559186 0.145 Uiso 1 1 calc R U . . .
H10C H 0.348077 0.803375 0.579434 0.145 Uiso 1 1 calc R U . . .
C11 C -0.1120(13) 0.4914(9) 0.54001(19) 0.079(2) Uani 1 1 d . . . . .
H11 H -0.190775 0.490173 0.558313 0.095 Uiso 1 1 calc R U . . .
C12 C -0.1916(12) 0.4161(8) 0.51590(18) 0.073(2) Uani 1 1 d . . . . .
H12 H -0.323750 0.361243 0.518326 0.088 Uiso 1 1 calc R U . . .
C13 C -0.0867(11) 0.4161(7) 0.48752(17) 0.0606(17) Uani 1 1 d . . . . .
C14 C -0.1732(12) 0.3452(8) 0.46173(18) 0.0683(19) Uani 1 1 d . . . . .
H14 H -0.309965 0.294659 0.463544 0.082 Uiso 1 1 calc R U . . .
C15 C 0.0778(12) 0.7093(8) 0.32003(17) 0.0621(17) Uani 1 1 d . . . . .
C16 C 0.3009(10) 0.6863(8) 0.33757(15) 0.0602(17) Uani 1 1 d D U . . .
H16 H 0.335841 0.581674 0.340111 0.072 Uiso 1 1 calc R U . A 1
C17A C 0.2892(19) 0.7662(19) 0.3683(3) 0.073(6) Uani 0.56(2) 1 d D U P A 1
H17A H 0.151807 0.824815 0.369500 0.088 Uiso 0.56(2) 1 calc R U P A 1
H17B H 0.288555 0.695613 0.384770 0.088 Uiso 0.56(2) 1 calc R U P A 1
C18A C 0.497(4) 0.864(3) 0.3703(3) 0.107(8) Uani 0.56(2) 1 d D U P A 1
H18A H 0.627195 0.809919 0.377892 0.128 Uiso 0.56(2) 1 calc R U P A 1
H18B H 0.469049 0.948105 0.383238 0.128 Uiso 0.56(2) 1 calc R U P A 1
C19A C 0.531(6) 0.910(3) 0.3371(5) 0.077(8) Uani 0.56(2) 1 d D U P A 1
H19A H 0.422534 0.984817 0.330956 0.093 Uiso 0.56(2) 1 calc R U P A 1
H19B H 0.684300 0.945500 0.333444 0.093 Uiso 0.56(2) 1 calc R U P A 1
C17B C 0.296(5) 0.753(3) 0.3696(3) 0.126(14) Uani 0.44(2) 1 d D U P A 2
H17C H 0.144380 0.751076 0.378188 0.151 Uiso 0.44(2) 1 calc R U P A 2
H17D H 0.399929 0.702296 0.383180 0.151 Uiso 0.44(2) 1 calc R U P A 2
C18B C 0.374(3) 0.908(2) 0.3632(4) 0.070(6) Uani 0.44(2) 1 d D U P A 2
H18C H 0.420934 0.956854 0.381763 0.084 Uiso 0.44(2) 1 calc R U P A 2
H18D H 0.254153 0.964754 0.353702 0.084 Uiso 0.44(2) 1 calc R U P A 2
C19B C 0.575(7) 0.887(3) 0.3417(7) 0.072(11) Uani 0.44(2) 1 d D U P A 2
H19C H 0.606348 0.975283 0.330139 0.087 Uiso 0.44(2) 1 calc R U P A 2
H19D H 0.711049 0.857008 0.352490 0.087 Uiso 0.44(2) 1 calc R U P A 2
C20 C 0.5450(11) 0.9122(7) 0.2391(2) 0.0616(18) Uani 1 1 d . . . . .
C21 C 0.6600(11) 0.7762(8) 0.22613(16) 0.0659(18) Uani 1 1 d D U . . .
H21 H 0.545012 0.709896 0.217658 0.079 Uiso 1 1 calc R U . A 1
C22A C 0.834(4) 0.811(3) 0.2023(6) 0.093(8) Uani 0.56(2) 1 d D U P A 1
H22A H 0.766072 0.805585 0.182326 0.111 Uiso 0.56(2) 1 calc R U P A 1
H22B H 0.891652 0.910095 0.205289 0.111 Uiso 0.56(2) 1 calc R U P A 1
C23A C 1.018(6) 0.707(4) 0.2046(5) 0.112(15) Uani 0.56(2) 1 d D U P A 1
H23A H 1.162930 0.758044 0.204058 0.134 Uiso 0.56(2) 1 calc R U P A 1
H23B H 1.012795 0.638744 0.187700 0.134 Uiso 0.56(2) 1 calc R U P A 1
C24A C 0.993(2) 0.6262(17) 0.2339(3) 0.064(6) Uani 0.56(2) 1 d D U P A 1
H24A H 0.963107 0.522798 0.230253 0.077 Uiso 0.56(2) 1 calc R U P A 1
H24B H 1.129539 0.635227 0.246053 0.077 Uiso 0.56(2) 1 calc R U P A 1
C22B C 0.813(5) 0.789(5) 0.1990(7) 0.112(15) Uani 0.44(2) 1 d D U P A 2
H22C H 0.725751 0.780310 0.180352 0.135 Uiso 0.44(2) 1 calc R U P A 2
H22D H 0.891230 0.882466 0.198967 0.135 Uiso 0.44(2) 1 calc R U P A 2
C23B C 0.974(7) 0.670(5) 0.2012(6) 0.083(10) Uani 0.44(2) 1 d D U P A 2
H23C H 1.120946 0.700928 0.193658 0.099 Uiso 0.44(2) 1 calc R U P A 2
H23D H 0.922847 0.586726 0.189225 0.099 Uiso 0.44(2) 1 calc R U P A 2
C24B C 0.993(5) 0.627(4) 0.2338(5) 0.134(17) Uani 0.44(2) 1 d D U P A 2
H24C H 0.985724 0.520479 0.235895 0.161 Uiso 0.44(2) 1 calc R U P A 2
H24D H 1.134855 0.661095 0.242327 0.161 Uiso 0.44(2) 1 calc R U P A 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
O1 C1 1.192(9) . ?
N1 C16 1.488(7) . ?
N1 C19B 1.506(14) . ?
N1 C19A 1.508(14) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
C1 O2 1.284(8) . ?
C1 C2 1.494(10) . ?
O2 H2O 0.8200 . ?
N2 C24B 1.483(11) . ?
N2 C24A 1.484(9) . ?
N2 C21 1.488(8) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
C2 C4 1.509(10) . ?
C2 C3 1.532(10) . ?
C2 H2 0.9800 . ?
O3 C9 1.346(9) . ?
O3 C10 1.437(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
O4 C15 1.252(8) . ?
C4 C14 1.352(9) . ?
C4 C5 1.416(9) . ?
O5 C15 1.229(8) . ?
C5 C6 1.361(10) . ?
C5 H5 0.9300 . ?
O6 C20 1.257(8) . ?
C6 C7 1.403(9) . ?
C6 H6 0.9300 . ?
O7 C20 1.243(8) . ?
C7 C8 1.405(10) . ?
C7 C13 1.426(9) . ?
C8 C9 1.361(10) . ?
C8 H8 0.9300 . ?
C9 C11 1.443(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.348(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.402(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.537(8) . ?
C16 C17A 1.536(11) . ?
C16 C17B 1.536(13) . ?
C16 H16 0.9800 . ?
C17A C18A 1.512(14) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A C19A 1.54(2) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C17B C18B 1.508(16) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B C19B 1.53(2) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20 C21 1.521(9) . ?
C21 C22A 1.501(12) . ?
C21 C22B 1.502(13) . ?
C21 H21 0.9800 . ?
C22A C23A 1.440(14) . ?
C22A H22A 0.9700 . ?
C22A H22B 0.9700 . ?
C23A C24A 1.492(15) . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C24A H24A 0.9700 . ?
C24A H24B 0.9700 . ?
C22B C23B 1.440(15) . ?
C22B H22C 0.9700 . ?
C22B H22D 0.9700 . ?
C23B C24B 1.490(16) . ?
C23B H23C 0.9700 . ?
C23B H23D 0.9700 . ?
C24B H24C 0.9700 . ?
C24B H24D 0.9700 . ?

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
C16 N1 C19B 109.2(8) . . ?
C16 N1 C19A 109.5(8) . . ?
C16 N1 H1A 109.8 . . ?
C19A N1 H1A 109.8 . . ?
C16 N1 H1B 109.8 . . ?
C19A N1 H1B 109.8 . . ?
H1A N1 H1B 108.2 . . ?
C16 N1 H1C 109.8 . . ?
C19B N1 H1C 109.8 . . ?
C16 N1 H1D 109.8 . . ?
C19B N1 H1D 109.9 . . ?
H1C N1 H1D 108.3 . . ?
O1 C1 O2 121.3(7) . . ?
O1 C1 C2 125.2(8) . . ?
O2 C1 C2 113.2(7) . . ?
C1 O2 H2O 109.5 . . ?
C24B N2 C21 108.2(10) . . ?
C24A N2 C21 108.4(7) . . ?
C24A N2 H2A 110.0 . . ?
C21 N2 H2A 110.0 . . ?
C24A N2 H2B 110.0 . . ?
C21 N2 H2B 110.0 . . ?
H2A N2 H2B 108.4 . . ?
C1 C2 C4 110.4(7) . . ?
C1 C2 C3 112.9(7) . . ?
C4 C2 C3 112.9(6) . . ?
C1 C2 H2 106.7 . . ?
C4 C2 H2 106.7 . . ?
C3 C2 H2 106.7 . . ?
C9 O3 C10 117.1(6) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C14 C4 C5 117.1(7) . . ?
C14 C4 C2 122.4(6) . . ?
C5 C4 C2 120.5(7) . . ?
C6 C5 C4 121.0(7) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 122.5(7) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C8 123.1(7) . . ?
C6 C7 C13 116.7(7) . . ?
C8 C7 C13 120.1(7) . . ?
C9 C8 C7 121.4(7) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
O3 C9 C8 128.4(7) . . ?
O3 C9 C11 113.0(7) . . ?
C8 C9 C11 118.6(8) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 119.5(8) . . ?
C12 C11 H11 120.2 . . ?
C9 C11 H11 120.2 . . ?
C11 C12 C13 123.6(7) . . ?
C11 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C12 C13 C14 124.5(7) . . ?
C12 C13 C7 116.7(7) . . ?
C14 C13 C7 118.9(7) . . ?
C4 C14 C13 123.7(7) . . ?
C4 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
O5 C15 O4 124.9(6) . . ?
O5 C15 C16 119.0(7) . . ?
O4 C15 C16 116.1(6) . . ?
N1 C16 C17A 102.8(7) . . ?
N1 C16 C17B 104.9(9) . . ?
N1 C16 C15 109.0(5) . . ?
C17A C16 C15 109.9(7) . . ?
C17B C16 C15 113.1(14) . . ?
N1 C16 H16 111.6 . . ?
C17A C16 H16 111.6 . . ?
C15 C16 H16 111.6 . . ?
C18A C17A C16 107.1(9) . . ?
C18A C17A H17A 110.3 . . ?
C16 C17A H17A 110.3 . . ?
C18A C17A H17B 110.3 . . ?
C16 C17A H17B 110.3 . . ?
H17A C17A H17B 108.6 . . ?
C17A C18A C19A 102.2(14) . . ?
C17A C18A H18A 111.3 . . ?
C19A C18A H18A 111.3 . . ?
C17A C18A H18B 111.3 . . ?
C19A C18A H18B 111.3 . . ?
H18A C18A H18B 109.2 . . ?
N1 C19A C18A 99.6(16) . . ?
N1 C19A H19A 111.8 . . ?
C18A C19A H19A 111.8 . . ?
N1 C19A H19B 111.8 . . ?
C18A C19A H19B 111.8 . . ?
H19A C19A H19B 109.6 . . ?
C18B C17B C16 101.1(12) . . ?
C18B C17B H17C 111.6 . . ?
C16 C17B H17C 111.6 . . ?
C18B C17B H17D 111.6 . . ?
C16 C17B H17D 111.6 . . ?
H17C C17B H17D 109.4 . . ?
C17B C18B C19B 103.4(15) . . ?
C17B C18B H18C 111.1 . . ?
C19B C18B H18C 111.1 . . ?
C17B C18B H18D 111.1 . . ?
C19B C18B H18D 111.1 . . ?
H18C C18B H18D 109.0 . . ?
N1 C19B C18B 101.1(16) . . ?
N1 C19B H19C 111.6 . . ?
C18B C19B H19C 111.6 . . ?
N1 C19B H19D 111.5 . . ?
C18B C19B H19D 111.5 . . ?
H19C C19B H19D 109.4 . . ?
O7 C20 O6 125.7(7) . . ?
O7 C20 C21 116.8(7) . . ?
O6 C20 C21 117.5(7) . . ?
N2 C21 C22A 102.2(11) . . ?
N2 C21 C22B 105.0(11) . . ?
N2 C21 C20 112.2(6) . . ?
C22A C21 C20 113.2(12) . . ?
C22B C21 C20 120.4(17) . . ?
N2 C21 H21 109.7 . . ?
C22A C21 H21 109.6 . . ?
C20 C21 H21 109.7 . . ?
C23A C22A C21 109.0(13) . . ?
C23A C22A H22A 109.9 . . ?
C21 C22A H22A 109.9 . . ?
C23A C22A H22B 109.8 . . ?
C21 C22A H22B 109.9 . . ?
H22A C22A H22B 108.3 . . ?
C22A C23A C24A 108.0(12) . . ?
C22A C23A H23A 110.1 . . ?
C24A C23A H23A 110.1 . . ?
C22A C23A H23B 110.1 . . ?
C24A C23A H23B 110.1 . . ?
H23A C23A H23B 108.4 . . ?
N2 C24A C23A 105.1(8) . . ?
N2 C24A H24A 110.7 . . ?
C23A C24A H24A 110.7 . . ?
N2 C24A H24B 110.7 . . ?
C23A C24A H24B 110.7 . . ?
H24A C24A H24B 108.8 . . ?
C23B C22B C21 106.4(15) . . ?
C23B C22B H22C 110.4 . . ?
C21 C22B H22C 110.4 . . ?
C23B C22B H22D 110.5 . . ?
C21 C22B H22D 110.5 . . ?
H22C C22B H22D 108.6 . . ?
C22B C23B C24B 108.3(15) . . ?
C22B C23B H23C 110.0 . . ?
C24B C23B H23C 110.0 . . ?
C22B C23B H23D 110.1 . . ?
C24B C23B H23D 110.0 . . ?
H23C C23B H23D 108.4 . . ?
N2 C24B C23B 105.8(10) . . ?
N2 C24B H24C 110.6 . . ?
C23B C24B H24C 110.6 . . ?
N2 C24B H24D 110.6 . . ?
C23B C24B H24D 110.6 . . ?
H24C C24B H24D 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C4 -91.4(11) . . . . ?
O2 C1 C2 C4 83.0(9) . . . . ?
O1 C1 C2 C3 141.2(10) . . . . ?
O2 C1 C2 C3 -44.4(10) . . . . ?
C1 C2 C4 C14 116.2(8) . . . . ?
C3 C2 C4 C14 -116.4(8) . . . . ?
C1 C2 C4 C5 -64.4(9) . . . . ?
C3 C2 C4 C5 63.0(9) . . . . ?
C14 C4 C5 C6 -4.3(10) . . . . ?
C2 C4 C5 C6 176.2(7) . . . . ?
C4 C5 C6 C7 2.5(12) . . . . ?
C5 C6 C7 C8 -176.7(7) . . . . ?
C5 C6 C7 C13 0.3(11) . . . . ?
C6 C7 C8 C9 179.8(7) . . . . ?
C13 C7 C8 C9 2.9(11) . . . . ?
C10 O3 C9 C8 5.9(11) . . . . ?
C10 O3 C9 C11 -172.8(6) . . . . ?
C7 C8 C9 O3 -178.9(7) . . . . ?
C7 C8 C9 C11 -0.2(11) . . . . ?
O3 C9 C11 C12 178.5(7) . . . . ?
C8 C9 C11 C12 -0.3(11) . . . . ?
C9 C11 C12 C13 -1.9(11) . . . . ?
C11 C12 C13 C14 -176.3(7) . . . . ?
C11 C12 C13 C7 4.3(10) . . . . ?
C6 C7 C13 C12 178.1(7) . . . . ?
C8 C7 C13 C12 -4.7(9) . . . . ?
C6 C7 C13 C14 -1.3(9) . . . . ?
C8 C7 C13 C14 175.9(7) . . . . ?
C5 C4 C14 C13 3.4(10) . . . . ?
C2 C4 C14 C13 -177.2(6) . . . . ?
C12 C13 C14 C4 -180.0(7) . . . . ?
C7 C13 C14 C4 -0.7(10) . . . . ?
C19A N1 C16 C17A -17(2) . . . . ?
C19B N1 C16 C17B -6(3) . . . . ?
C19B N1 C16 C15 115(2) . . . . ?
C19A N1 C16 C15 99.4(19) . . . . ?
O5 C15 C16 N1 -7.6(9) . . . . ?
O4 C15 C16 N1 172.7(6) . . . . ?
O5 C15 C16 C17A 104.3(10) . . . . ?
O4 C15 C16 C17A -75.4(10) . . . . ?
O5 C15 C16 C17B 108.8(11) . . . . ?
O4 C15 C16 C17B -70.9(11) . . . . ?
N1 C16 C17A C18A -11.0(16) . . . . ?
C15 C16 C17A C18A -126.9(14) . . . . ?
C16 C17A C18A C19A 34(3) . . . . ?
C16 N1 C19A C18A 38(3) . . . . ?
C17A C18A C19A N1 -42(3) . . . . ?
N1 C16 C17B C18B 31(2) . . . . ?
C15 C16 C17B C18B -87.6(18) . . . . ?
C16 C17B C18B C19B -45(3) . . . . ?
C16 N1 C19B C18B -21(3) . . . . ?
C17B C18B C19B N1 41(3) . . . . ?
C24A N2 C21 C22A -26.9(17) . . . . ?
C24B N2 C21 C22B -16(3) . . . . ?
C24B N2 C21 C20 -149(2) . . . . ?
C24A N2 C21 C20 -148.6(9) . . . . ?
O7 C20 C21 N2 165.6(6) . . . . ?
O6 C20 C21 N2 -13.6(8) . . . . ?
O7 C20 C21 C22A 50.5(17) . . . . ?
O6 C20 C21 C22A -128.7(16) . . . . ?
O7 C20 C21 C22B 41(2) . . . . ?
O6 C20 C21 C22B -138(2) . . . . ?
N2 C21 C22A C23A 24(3) . . . . ?
C20 C21 C22A C23A 145(3) . . . . ?
C21 C22A C23A C24A -13(4) . . . . ?
C21 N2 C24A C23A 20(2) . . . . ?
C22A C23A C24A N2 -4(4) . . . . ?
N2 C21 C22B C23B 25(4) . . . . ?
C20 C21 C22B C23B 152(3) . . . . ?
C21 C22B C23B C24B -24(5) . . . . ?
C21 N2 C24B C23B 2(4) . . . . ?
C22B C23B C24B N2 14(5) . . . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038


# start Validation Reply Form
_vrf_PLAT340_nt0017_Natalia_Snprx_DLpro_EtOHb6 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01069 Ang.  
RESPONSE: Crystals were small and weakly diffracting, even for the best 
selected crystals diffraction limit was not higher than 0.9 \%A. 
In addition, both proline molecules are disordered.  
;
_vrf_THETM01_nt0017_Natalia_Snprx_DLpro_EtOHb6 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.590
RESPONSE: Crystals were small and weakly diffracting, even for the best 
selected crystals diffraction limit was not higher than 0.9 \%A, so
we changed the data collection strategy accordingly.  
;
_vrf_PLAT029_nt0017_Natalia_Snprx_DLpro_EtOHb6 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.963 Why?  
RESPONSE: Crystals were small and weakly diffracting, even for the best 
selected crystals diffraction limit was not higher than 0.9 \%A, so
we changed the data collection strategy accordingly.  
;
_vrf_PLAT089_nt0017_Natalia_Snprx_DLpro_EtOHb6 
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.08 Note  
RESPONSE: Crystals were small and weakly diffracting, even for the best 
selected crystals diffraction limit was not higher than 0.9 \%A. All hydrogen 
atoms not involved in hydrogen bonding were refined in riding mode to 
minimize the number of parameters. Additionally, disorder of proline increases 
the number of parameters.  
;
_vrf_PLAT242_nt0017_Natalia_Snprx_DLpro_EtOHb6 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check 
RESPONSE: Carbon atom in the wobbling COOH-group.
;
_vrf_PLAT244_nt0017_Natalia_Snprx_DLpro_EtOHb6 
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of        C16 Check 
RESPONSE: Neighboring atoms are disordered.
;
_vrf_PLAT911_nt0017_Natalia_Snprx_DLpro_EtOHb6 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.576         75 Report
RESPONSE: These reflections are missing in the highest resolution 
shells because of the instrument geometry limitation.
;
_vrf_PLAT915_nt0017_Natalia_Snprx_DLpro_EtOHb6 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         63 %     
RESPONSE: ... Absolute configuration established by
 the structure determination of a compound containing a chiral reference
 molecule of known absolute configuration (S-naproxen). Signal-to-noise ratio
of the data was not sufficient enough for direct determination of the absolute
 configuration by anomalous-dispersion effects 
;
_vrf_PLAT978_nt0017_Natalia_Snprx_DLpro_EtOHb6 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: Crystals were small and weakly diffracting, even for the best 
selected crystals diffraction limit was not higher than 0.9 \%A.
;
####################################################################### 
# 
# 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_Snprx-L_2-3
_database_code_depnum_ccdc_archive 'CCDC 1861028'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'bis((2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid) tris((2S)-pyrrolidin-1-ium-2-carboxylate)'
_chemical_name_common            'S-naproxen L-proline 2:3 cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H14 O3), 3(C5 H9 N O2)'
_chemical_formula_sum            'C43 H55 N3 O12'
_chemical_formula_weight         805.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0090 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0160 0.0090 '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                   5.70180(10)
_cell_length_b                   18.8609(3)
_cell_length_c                   37.2392(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4004.74(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8552
_cell_measurement_theta_min      1.7820
_cell_measurement_theta_max      28.1600

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             1720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.82656
_diffrn_radiation_type           synchrotron
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  'Pilatus 6M'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18663
_diffrn_reflns_av_unetI/netI     0.1120
_diffrn_reflns_av_R_equivalents  0.1298
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         1.787
_diffrn_reflns_theta_max         28.657
_diffrn_reflns_theta_full        28.657
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measured_fraction_theta_full 0.865
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_Laue_measured_fraction_full 0.865
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_point_group_measured_fraction_full 0.825
_reflns_number_total             5419
_reflns_number_gt                3761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_max     0.769
_reflns_Friedel_fraction_full    0.769

_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       ?
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0853P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_chemical_absolute_configuration rm
_refine_ls_number_reflns         5419
_refine_ls_number_parameters     529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1443
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_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
O1 O 0.1291(8) 0.3816(2) 0.64453(12) 0.0452(12) Uani 1 1 d . . . . .
H1 H 0.158235 0.350115 0.659826 0.068 Uiso 1 1 calc R U . . .
O2 O 0.4341(9) 0.4352(2) 0.67015(13) 0.0483(13) Uani 1 1 d . . . . .
O3 O 0.5003(8) 0.2932(2) 0.43083(12) 0.0441(12) Uani 1 1 d . . . . .
C1 C 0.2871(12) 0.4330(3) 0.64711(19) 0.0384(17) Uani 1 1 d . . . . .
C2 C 0.2701(13) 0.4858(3) 0.61637(18) 0.0428(18) Uani 1 1 d . . . . .
H2 H 0.100469 0.497214 0.612733 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3971(14) 0.5546(3) 0.6253(2) 0.052(2) Uani 1 1 d . . . . .
H3A H 0.566730 0.546196 0.625531 0.078 Uiso 1 1 calc R U . . .
H3B H 0.346803 0.571459 0.648965 0.078 Uiso 1 1 calc R U . . .
H3C H 0.359585 0.590437 0.607125 0.078 Uiso 1 1 calc R U . . .
C4 C 0.3580(12) 0.4505(3) 0.58276(18) 0.0383(17) Uani 1 1 d . . . . .
C5 C 0.5760(12) 0.4141(3) 0.58298(19) 0.0407(17) Uani 1 1 d . . . . .
H5 H 0.669807 0.414940 0.604054 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6537(13) 0.3777(3) 0.55352(19) 0.0435(18) Uani 1 1 d . . . . .
H6 H 0.798879 0.353092 0.554870 0.052 Uiso 1 1 calc R U . . .
C7 C 0.5249(12) 0.3755(3) 0.52122(18) 0.0367(17) Uani 1 1 d . . . . .
C8 C 0.5910(12) 0.3343(3) 0.49118(17) 0.0397(17) Uani 1 1 d . . . . .
H8 H 0.731985 0.307540 0.492192 0.048 Uiso 1 1 calc R U . . .
C9 C 0.4578(12) 0.3319(3) 0.46076(18) 0.0367(17) Uani 1 1 d . . . . .
C10 C 0.6961(12) 0.2460(3) 0.4321(2) 0.0482(19) Uani 1 1 d . . . . .
H10A H 0.698330 0.216807 0.410314 0.072 Uiso 1 1 calc R U . . .
H10B H 0.682584 0.215274 0.453213 0.072 Uiso 1 1 calc R U . . .
H10C H 0.841577 0.273481 0.433591 0.072 Uiso 1 1 calc R U . . .
C11 C 0.2442(12) 0.3722(3) 0.45972(19) 0.0413(18) Uani 1 1 d . . . . .
H11 H 0.148659 0.370633 0.438833 0.050 Uiso 1 1 calc R U . . .
C12 C 0.1772(12) 0.4121(3) 0.48790(19) 0.0398(17) Uani 1 1 d . . . . .
H12 H 0.037580 0.439313 0.486128 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3086(11) 0.4146(3) 0.51997(18) 0.0364(17) Uani 1 1 d . . . . .
C14 C 0.2336(13) 0.4510(3) 0.55103(18) 0.0404(17) Uani 1 1 d . . . . .
H14 H 0.091109 0.477018 0.550008 0.048 Uiso 1 1 calc R U . . .
O7 O -0.3612(8) 0.2129(2) 0.30579(12) 0.0436(12) Uani 1 1 d . . . . .
O8 O -0.2238(8) 0.2951(2) 0.26829(12) 0.0415(12) Uani 1 1 d . . . . .
N1 N 0.2214(9) 0.2788(3) 0.28663(15) 0.0394(14) Uani 1 1 d . . . . .
H11N H 0.164246 0.292289 0.264857 0.047 Uiso 1 1 calc R U . . .
H12N H 0.359120 0.255405 0.283228 0.047 Uiso 1 1 calc R U . . .
C29 C -0.1987(11) 0.2492(3) 0.29174(19) 0.0367(16) Uani 1 1 d . . . . .
C30 C 0.0506(11) 0.2330(3) 0.30550(17) 0.0354(16) Uani 1 1 d . . . . .
H30 H 0.089380 0.181953 0.301295 0.042 Uiso 1 1 calc R U . . .
C31 C 0.0776(13) 0.2510(4) 0.34555(18) 0.0467(18) Uani 1 1 d . . . . .
H31A H -0.073421 0.267339 0.355732 0.056 Uiso 1 1 calc R U . . .
H31B H 0.131538 0.209043 0.359217 0.056 Uiso 1 1 calc R U . . .
C32 C 0.2612(13) 0.3103(3) 0.34702(18) 0.0466(18) Uani 1 1 d . . . . .
H32A H 0.218528 0.346347 0.365226 0.056 Uiso 1 1 calc R U . . .
H32B H 0.418216 0.291078 0.352803 0.056 Uiso 1 1 calc R U . . .
C33 C 0.2572(12) 0.3415(3) 0.30999(17) 0.0418(17) Uani 1 1 d . . . . .
H33A H 0.127156 0.375853 0.307320 0.050 Uiso 1 1 calc R U . . .
H33B H 0.407235 0.365484 0.304382 0.050 Uiso 1 1 calc R U . . .
O9 O 1.2165(8) 0.5213(2) 0.28992(12) 0.0470(12) Uani 1 1 d . . . . .
O10 O 1.0682(8) 0.6189(2) 0.26386(13) 0.0448(12) Uani 1 1 d . . . . .
N2 N 0.6312(9) 0.5675(3) 0.26067(14) 0.0390(14) Uani 1 1 d . . . . .
H21N H 0.502580 0.559141 0.274502 0.047 Uiso 1 1 calc R U . . .
H22N H 0.679310 0.612883 0.264554 0.047 Uiso 1 1 calc R U . . .
C34 C 1.0551(12) 0.5577(4) 0.27524(18) 0.0365(16) Uani 1 1 d . . . . .
C35 C 0.8239(11) 0.5165(3) 0.27021(18) 0.0369(16) Uani 1 1 d . . . . .
H35 H 0.783315 0.490245 0.292698 0.044 Uiso 1 1 calc R U . . .
C36 C 0.8387(12) 0.4652(3) 0.23858(18) 0.0411(18) Uani 1 1 d . . . . .
H36A H 0.844811 0.415525 0.247043 0.049 Uiso 1 1 calc R U . . .
H36B H 0.979375 0.474989 0.223804 0.049 Uiso 1 1 calc R U . . .
C37 C 0.6122(13) 0.4791(3) 0.21696(19) 0.0423(18) Uani 1 1 d . . . . .
H37A H 0.634033 0.467380 0.191265 0.051 Uiso 1 1 calc R U . . .
H37B H 0.479311 0.451233 0.226592 0.051 Uiso 1 1 calc R U . . .
C38 C 0.5729(12) 0.5572(3) 0.22207(17) 0.0395(17) Uani 1 1 d . . . . .
H38A H 0.677810 0.585416 0.206440 0.047 Uiso 1 1 calc R U . . .
H38B H 0.408007 0.570284 0.217032 0.047 Uiso 1 1 calc R U . . .
O11 O 0.5935(8) 0.7070(2) 0.28022(13) 0.0453(12) Uani 1 1 d . . . . .
O12 O 0.7546(7) 0.8119(2) 0.29228(12) 0.0427(12) Uani 1 1 d . . . . .
N3 N 0.1714(9) 0.7397(3) 0.30525(14) 0.0380(14) Uani 1 1 d . . . . .
H31N H 0.039179 0.761916 0.297484 0.046 Uiso 1 1 calc R U . . .
H32N H 0.215957 0.707743 0.288257 0.046 Uiso 1 1 calc R U . . .
C39 C 0.5870(11) 0.7676(4) 0.29312(18) 0.0368(16) Uani 1 1 d . . . . .
C40 C 0.3629(11) 0.7929(3) 0.31116(17) 0.0350(16) Uani 1 1 d . . . . .
H40 H 0.315458 0.840177 0.301460 0.042 Uiso 1 1 calc R U . . .
C41 C 0.3910(13) 0.7965(4) 0.35219(18) 0.0484(19) Uani 1 1 d . . . . .
H41A H 0.537937 0.773092 0.359901 0.058 Uiso 1 1 calc R U . . .
H41B H 0.392772 0.846366 0.360547 0.058 Uiso 1 1 calc R U . . .
C42 C 0.1768(14) 0.7573(4) 0.3668(2) 0.059(2) Uani 1 1 d . . . . .
H42A H 0.212266 0.735401 0.390344 0.071 Uiso 1 1 calc R U . . .
H42B H 0.042457 0.790025 0.369653 0.071 Uiso 1 1 calc R U . . .
C43 C 0.1244(13) 0.7027(4) 0.33990(17) 0.0448(18) Uani 1 1 d . . . . .
H43A H -0.041159 0.687161 0.341476 0.054 Uiso 1 1 calc R U . . .
H43B H 0.227938 0.660927 0.342845 0.054 Uiso 1 1 calc R U . . .
O4 O 0.6107(10) 0.5801(3) 0.35615(16) 0.0736(18) Uani 1 1 d . . . . .
O5 O 0.3610(9) 0.4895(2) 0.35283(13) 0.0501(13) Uani 1 1 d . . . . .
H5O H 0.314010 0.511160 0.334491 0.075 Uiso 1 1 calc R U . . .
O6 O 1.0947(9) 0.6988(2) 0.56633(12) 0.0532(14) Uani 1 1 d . . . . .
C15 C 0.5388(13) 0.5254(4) 0.3678(2) 0.0444(18) Uani 1 1 d . . . . .
C16 C 0.6406(13) 0.4827(3) 0.39864(18) 0.0436(18) Uani 1 1 d . . . . .
H16 H 0.506410 0.459027 0.411100 0.052 Uiso 1 1 calc R U . . .
C17 C 0.7945(14) 0.4238(4) 0.3825(2) 0.056(2) Uani 1 1 d . . . . .
H17A H 0.934618 0.444940 0.371624 0.084 Uiso 1 1 calc R U . . .
H17B H 0.705516 0.398235 0.364091 0.084 Uiso 1 1 calc R U . . .
H17C H 0.841594 0.390792 0.401487 0.084 Uiso 1 1 calc R U . . .
C18 C 0.7665(12) 0.5267(3) 0.42617(19) 0.0398(17) Uani 1 1 d . . . . .
C19 C 0.9797(13) 0.5623(3) 0.41847(19) 0.0434(18) Uani 1 1 d . . . . .
H19 H 1.043391 0.559355 0.394949 0.052 Uiso 1 1 calc R U . . .
C20 C 1.0954(12) 0.6006(3) 0.44377(19) 0.0432(18) Uani 1 1 d . . . . .
H20 H 1.239416 0.622845 0.437682 0.052 Uiso 1 1 calc R U . . .
C21 C 1.0057(12) 0.6080(3) 0.47912(18) 0.0384(17) Uani 1 1 d . . . . .
C22 C 1.1124(13) 0.6505(3) 0.50579(18) 0.0437(18) Uani 1 1 d . . . . .
H22 H 1.253981 0.674887 0.500471 0.052 Uiso 1 1 calc R U . . .
C23 C 1.0146(14) 0.6570(4) 0.53907(19) 0.0441(18) Uani 1 1 d . . . . .
C24 C 1.2601(14) 0.7525(4) 0.5570(2) 0.056(2) Uani 1 1 d . . . . .
H24A H 1.199492 0.780265 0.536772 0.084 Uiso 1 1 calc R U . . .
H24B H 1.408956 0.730317 0.550122 0.084 Uiso 1 1 calc R U . . .
H24C H 1.285549 0.783759 0.577638 0.084 Uiso 1 1 calc R U . . .
C25 C 0.8092(13) 0.6187(4) 0.54776(19) 0.0456(19) Uani 1 1 d . . . . .
H25 H 0.744616 0.622048 0.571211 0.055 Uiso 1 1 calc R U . . .
C26 C 0.7039(12) 0.5772(3) 0.52280(18) 0.0413(18) Uani 1 1 d . . . . .
H26 H 0.567302 0.551265 0.529176 0.050 Uiso 1 1 calc R U . . .
C27 C 0.7923(12) 0.5718(3) 0.48779(18) 0.0369(17) Uani 1 1 d . . . . .
C28 C 0.6813(12) 0.5313(3) 0.46041(19) 0.0423(18) Uani 1 1 d . . . . .
H28 H 0.541626 0.506311 0.466171 0.051 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
O1 C1 1.327(8) . ?
O1 H1 0.8400 . ?
O2 C1 1.200(8) . ?
O3 C9 1.353(8) . ?
O3 C10 1.429(8) . ?
C1 C2 1.519(9) . ?
C2 C4 1.503(9) . ?
C2 C3 1.524(9) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C14 1.378(9) . ?
C4 C5 1.420(9) . ?
C5 C6 1.368(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.410(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(9) . ?
C7 C13 1.437(9) . ?
C8 C9 1.365(9) . ?
C8 H8 0.9500 . ?
C9 C11 1.436(9) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.347(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.411(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.412(9) . ?
C14 H14 0.9500 . ?
O7 C29 1.264(8) . ?
O8 C29 1.239(7) . ?
N1 C30 1.480(8) . ?
N1 C33 1.481(8) . ?
N1 H11N 0.9100 . ?
N1 H12N 0.9100 . ?
C29 C30 1.541(9) . ?
C30 C31 1.537(9) . ?
C30 H30 1.0000 . ?
C31 C32 1.533(9) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.499(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
O9 C34 1.272(8) . ?
O10 C34 1.232(7) . ?
N2 C38 1.488(8) . ?
N2 C35 1.503(8) . ?
N2 H21N 0.9100 . ?
N2 H22N 0.9100 . ?
C34 C35 1.542(9) . ?
C35 C36 1.526(9) . ?
C35 H35 1.0000 . ?
C36 C37 1.544(10) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.501(8) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
O11 C39 1.242(7) . ?
O12 C39 1.270(7) . ?
N3 C43 1.491(8) . ?
N3 C40 1.499(8) . ?
N3 H31N 0.9100 . ?
N3 H32N 0.9100 . ?
C39 C40 1.520(9) . ?
C40 C41 1.538(9) . ?
C40 H40 1.0000 . ?
C41 C42 1.528(10) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.467(9) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
O4 C15 1.191(8) . ?
O5 C15 1.342(9) . ?
O5 H5O 0.8400 . ?
O6 C23 1.364(8) . ?
O6 C24 1.426(8) . ?
C15 C16 1.517(10) . ?
C16 C18 1.503(10) . ?
C16 C17 1.538(9) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C28 1.367(10) . ?
C18 C19 1.418(10) . ?
C19 C20 1.357(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.419(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.414(9) . ?
C21 C27 1.432(9) . ?
C22 C23 1.364(9) . ?
C22 H22 0.9500 . ?
C23 C25 1.413(10) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.355(9) . ?
C25 H25 0.9500 . ?
C26 C27 1.402(9) . ?
C26 H26 0.9500 . ?
C27 C28 1.422(9) . ?
C28 H28 0.9500 . ?

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
C1 O1 H1 109.5 . . ?
C9 O3 C10 116.7(5) . . ?
O2 C1 O1 123.5(6) . . ?
O2 C1 C2 124.1(6) . . ?
O1 C1 C2 112.3(6) . . ?
C4 C2 C1 108.5(5) . . ?
C4 C2 C3 113.5(6) . . ?
C1 C2 C3 111.3(6) . . ?
C4 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C3 C2 H2 107.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C14 C4 C5 117.3(6) . . ?
C14 C4 C2 122.6(6) . . ?
C5 C4 C2 120.1(6) . . ?
C6 C5 C4 121.5(7) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 122.0(7) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 123.5(6) . . ?
C6 C7 C13 117.4(6) . . ?
C8 C7 C13 119.0(6) . . ?
C9 C8 C7 121.8(6) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
O3 C9 C8 127.0(6) . . ?
O3 C9 C11 114.5(6) . . ?
C8 C9 C11 118.5(6) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 121.0(7) . . ?
C12 C11 H11 119.5 . . ?
C9 C11 H11 119.5 . . ?
C11 C12 C13 121.9(6) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 123.3(6) . . ?
C12 C13 C7 117.8(6) . . ?
C14 C13 C7 118.9(6) . . ?
C4 C14 C13 122.9(7) . . ?
C4 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C30 N1 C33 106.2(5) . . ?
C30 N1 H11N 110.5 . . ?
C33 N1 H11N 110.5 . . ?
C30 N1 H12N 110.5 . . ?
C33 N1 H12N 110.5 . . ?
H11N N1 H12N 108.7 . . ?
O8 C29 O7 125.8(6) . . ?
O8 C29 C30 118.6(6) . . ?
O7 C29 C30 115.5(6) . . ?
N1 C30 C31 105.4(5) . . ?
N1 C30 C29 109.5(5) . . ?
C31 C30 C29 111.8(5) . . ?
N1 C30 H30 110.0 . . ?
C31 C30 H30 110.0 . . ?
C29 C30 H30 110.0 . . ?
C32 C31 C30 105.3(5) . . ?
C32 C31 H31A 110.7 . . ?
C30 C31 H31A 110.7 . . ?
C32 C31 H31B 110.7 . . ?
C30 C31 H31B 110.7 . . ?
H31A C31 H31B 108.8 . . ?
C33 C32 C31 104.1(6) . . ?
C33 C32 H32A 110.9 . . ?
C31 C32 H32A 110.9 . . ?
C33 C32 H32B 110.9 . . ?
C31 C32 H32B 110.9 . . ?
H32A C32 H32B 109.0 . . ?
N1 C33 C32 103.3(5) . . ?
N1 C33 H33A 111.1 . . ?
C32 C33 H33A 111.1 . . ?
N1 C33 H33B 111.1 . . ?
C32 C33 H33B 111.1 . . ?
H33A C33 H33B 109.1 . . ?
C38 N2 C35 107.9(5) . . ?
C38 N2 H21N 110.1 . . ?
C35 N2 H21N 110.1 . . ?
C38 N2 H22N 110.1 . . ?
C35 N2 H22N 110.1 . . ?
H21N N2 H22N 108.4 . . ?
O10 C34 O9 127.6(6) . . ?
O10 C34 C35 118.8(6) . . ?
O9 C34 C35 113.5(5) . . ?
N2 C35 C36 105.3(5) . . ?
N2 C35 C34 109.3(5) . . ?
C36 C35 C34 111.5(5) . . ?
N2 C35 H35 110.2 . . ?
C36 C35 H35 110.2 . . ?
C34 C35 H35 110.2 . . ?
C35 C36 C37 104.4(5) . . ?
C35 C36 H36A 110.9 . . ?
C37 C36 H36A 110.9 . . ?
C35 C36 H36B 110.9 . . ?
C37 C36 H36B 110.9 . . ?
H36A C36 H36B 108.9 . . ?
C38 C37 C36 103.0(5) . . ?
C38 C37 H37A 111.2 . . ?
C36 C37 H37A 111.2 . . ?
C38 C37 H37B 111.2 . . ?
C36 C37 H37B 111.2 . . ?
H37A C37 H37B 109.1 . . ?
N2 C38 C37 102.6(5) . . ?
N2 C38 H38A 111.3 . . ?
C37 C38 H38A 111.3 . . ?
N2 C38 H38B 111.3 . . ?
C37 C38 H38B 111.3 . . ?
H38A C38 H38B 109.2 . . ?
C43 N3 C40 108.5(5) . . ?
C43 N3 H31N 110.0 . . ?
C40 N3 H31N 110.0 . . ?
C43 N3 H32N 110.0 . . ?
C40 N3 H32N 110.0 . . ?
H31N N3 H32N 108.4 . . ?
O11 C39 O12 125.1(6) . . ?
O11 C39 C40 119.0(6) . . ?
O12 C39 C40 115.9(6) . . ?
N3 C40 C39 109.8(5) . . ?
N3 C40 C41 104.6(5) . . ?
C39 C40 C41 111.4(5) . . ?
N3 C40 H40 110.3 . . ?
C39 C40 H40 110.3 . . ?
C41 C40 H40 110.3 . . ?
C42 C41 C40 104.4(6) . . ?
C42 C41 H41A 110.9 . . ?
C40 C41 H41A 110.9 . . ?
C42 C41 H41B 110.9 . . ?
C40 C41 H41B 110.9 . . ?
H41A C41 H41B 108.9 . . ?
C43 C42 C41 105.1(6) . . ?
C43 C42 H42A 110.7 . . ?
C41 C42 H42A 110.7 . . ?
C43 C42 H42B 110.7 . . ?
C41 C42 H42B 110.7 . . ?
H42A C42 H42B 108.8 . . ?
C42 C43 N3 103.0(5) . . ?
C42 C43 H43A 111.2 . . ?
N3 C43 H43A 111.2 . . ?
C42 C43 H43B 111.2 . . ?
N3 C43 H43B 111.2 . . ?
H43A C43 H43B 109.1 . . ?
C15 O5 H5O 109.5 . . ?
C23 O6 C24 116.8(5) . . ?
O4 C15 O5 123.0(7) . . ?
O4 C15 C16 127.2(7) . . ?
O5 C15 C16 109.6(6) . . ?
C18 C16 C15 113.9(6) . . ?
C18 C16 C17 113.2(6) . . ?
C15 C16 C17 107.8(6) . . ?
C18 C16 H16 107.2 . . ?
C15 C16 H16 107.2 . . ?
C17 C16 H16 107.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C28 C18 C19 117.6(7) . . ?
C28 C18 C16 120.1(6) . . ?
C19 C18 C16 122.2(7) . . ?
C20 C19 C18 121.8(7) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 121.4(7) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 123.5(6) . . ?
C22 C21 C27 118.5(6) . . ?
C20 C21 C27 117.9(6) . . ?
C23 C22 C21 120.9(7) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 O6 126.2(7) . . ?
C22 C23 C25 120.0(7) . . ?
O6 C23 C25 113.8(7) . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C23 120.3(7) . . ?
C26 C25 H25 119.8 . . ?
C23 C25 H25 119.8 . . ?
C25 C26 C27 121.4(7) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C26 C27 C28 123.1(6) . . ?
C26 C27 C21 118.7(6) . . ?
C28 C27 C21 118.2(6) . . ?
C18 C28 C27 123.0(7) . . ?
C18 C28 H28 118.5 . . ?
C27 C28 H28 118.5 . . ?

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
O2 C1 C2 C4 104.7(7) . . . . ?
O1 C1 C2 C4 -71.6(7) . . . . ?
O2 C1 C2 C3 -20.9(9) . . . . ?
O1 C1 C2 C3 162.8(6) . . . . ?
C1 C2 C4 C14 129.9(7) . . . . ?
C3 C2 C4 C14 -105.8(8) . . . . ?
C1 C2 C4 C5 -49.2(8) . . . . ?
C3 C2 C4 C5 75.1(8) . . . . ?
C14 C4 C5 C6 -3.4(9) . . . . ?
C2 C4 C5 C6 175.8(6) . . . . ?
C4 C5 C6 C7 1.3(10) . . . . ?
C5 C6 C7 C8 -175.2(6) . . . . ?
C5 C6 C7 C13 1.3(9) . . . . ?
C6 C7 C8 C9 177.9(6) . . . . ?
C13 C7 C8 C9 1.5(9) . . . . ?
C10 O3 C9 C8 4.9(9) . . . . ?
C10 O3 C9 C11 -173.1(5) . . . . ?
C7 C8 C9 O3 -178.3(6) . . . . ?
C7 C8 C9 C11 -0.5(9) . . . . ?
O3 C9 C11 C12 178.8(6) . . . . ?
C8 C9 C11 C12 0.7(9) . . . . ?
C9 C11 C12 C13 -2.0(10) . . . . ?
C11 C12 C13 C14 -174.5(6) . . . . ?
C11 C12 C13 C7 3.0(9) . . . . ?
C6 C7 C13 C12 -179.3(6) . . . . ?
C8 C7 C13 C12 -2.7(9) . . . . ?
C6 C7 C13 C14 -1.7(9) . . . . ?
C8 C7 C13 C14 174.9(6) . . . . ?
C5 C4 C14 C13 2.9(9) . . . . ?
C2 C4 C14 C13 -176.2(6) . . . . ?
C12 C13 C14 C4 177.0(6) . . . . ?
C7 C13 C14 C4 -0.4(9) . . . . ?
C33 N1 C30 C31 -25.8(6) . . . . ?
C33 N1 C30 C29 94.5(6) . . . . ?
O8 C29 C30 N1 0.0(8) . . . . ?
O7 C29 C30 N1 179.7(5) . . . . ?
O8 C29 C30 C31 116.4(6) . . . . ?
O7 C29 C30 C31 -63.9(7) . . . . ?
N1 C30 C31 C32 2.4(7) . . . . ?
C29 C30 C31 C32 -116.4(6) . . . . ?
C30 C31 C32 C33 21.3(7) . . . . ?
C30 N1 C33 C32 39.7(6) . . . . ?
C31 C32 C33 N1 -37.1(7) . . . . ?
C38 N2 C35 C36 -12.2(6) . . . . ?
C38 N2 C35 C34 107.7(6) . . . . ?
O10 C34 C35 N2 -15.5(8) . . . . ?
O9 C34 C35 N2 167.3(5) . . . . ?
O10 C34 C35 C36 100.5(7) . . . . ?
O9 C34 C35 C36 -76.7(7) . . . . ?
N2 C35 C36 C37 -13.5(6) . . . . ?
C34 C35 C36 C37 -131.9(6) . . . . ?
C35 C36 C37 C38 33.9(7) . . . . ?
C35 N2 C38 C37 33.5(6) . . . . ?
C36 C37 C38 N2 -41.0(6) . . . . ?
C43 N3 C40 C39 108.3(6) . . . . ?
C43 N3 C40 C41 -11.4(6) . . . . ?
O11 C39 C40 N3 -7.8(8) . . . . ?
O12 C39 C40 N3 171.5(5) . . . . ?
O11 C39 C40 C41 107.6(7) . . . . ?
O12 C39 C40 C41 -73.1(7) . . . . ?
N3 C40 C41 C42 -12.0(7) . . . . ?
C39 C40 C41 C42 -130.6(6) . . . . ?
C40 C41 C42 C43 31.7(7) . . . . ?
C41 C42 C43 N3 -38.4(7) . . . . ?
C40 N3 C43 C42 31.3(7) . . . . ?
O4 C15 C16 C18 28.8(11) . . . . ?
O5 C15 C16 C18 -156.3(6) . . . . ?
O4 C15 C16 C17 -97.6(9) . . . . ?
O5 C15 C16 C17 77.2(7) . . . . ?
C15 C16 C18 C28 114.9(7) . . . . ?
C17 C16 C18 C28 -121.5(7) . . . . ?
C15 C16 C18 C19 -67.8(8) . . . . ?
C17 C16 C18 C19 55.9(8) . . . . ?
C28 C18 C19 C20 -0.9(9) . . . . ?
C16 C18 C19 C20 -178.3(6) . . . . ?
C18 C19 C20 C21 -1.3(10) . . . . ?
C19 C20 C21 C22 -176.2(6) . . . . ?
C19 C20 C21 C27 2.1(9) . . . . ?
C20 C21 C22 C23 178.3(7) . . . . ?
C27 C21 C22 C23 0.0(9) . . . . ?
C21 C22 C23 O6 -176.7(6) . . . . ?
C21 C22 C23 C25 2.6(10) . . . . ?
C24 O6 C23 C22 15.5(10) . . . . ?
C24 O6 C23 C25 -163.8(6) . . . . ?
C22 C23 C25 C26 -2.2(10) . . . . ?
O6 C23 C25 C26 177.2(6) . . . . ?
C23 C25 C26 C27 -0.9(10) . . . . ?
C25 C26 C27 C28 -177.2(6) . . . . ?
C25 C26 C27 C21 3.5(9) . . . . ?
C22 C21 C27 C26 -3.0(9) . . . . ?
C20 C21 C27 C26 178.6(6) . . . . ?
C22 C21 C27 C28 177.6(6) . . . . ?
C20 C21 C27 C28 -0.8(9) . . . . ?
C19 C18 C28 C27 2.2(10) . . . . ?
C16 C18 C28 C27 179.7(6) . . . . ?
C26 C27 C28 C18 179.2(6) . . . . ?
C21 C27 C28 C18 -1.4(9) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.064


# start Validation Reply Form
_vrf_RINTA01_pos_d               
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: Weak data, see comments below.
;
_vrf_THETM01_pos_d               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.590
RESPONSE: All crystals are very thin needles (diameter approximately 0.01 mm) 
and they were very weakly diffracting even when we used synchrotron beamline
 with insertion device as source. Diffraction limit for the best selected 
crystal, which was used in the refinement, is around 0.9.
;
_vrf_PLAT029_pos_d               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.865 Why?  
RESPONSE: A cusp of data is missing due to the instrument geometry 
limitation (one rotation axis).
;
_vrf_PLAT911_pos_d               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.580        488 Report
RESPONSE: A cusp of data is missing due to the instrument geometry 
limitation (one rotation axis).
;
_vrf_PLAT089_pos_d               
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.23 Note  
RESPONSE: See comments above.
;
_vrf_PLAT250_pos_d               
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.1 Note  
RESPONSE: ...
;
_vrf_PLAT340_pos_d               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00945 Ang.  
RESPONSE: See comments above.
;
_vrf_PLAT915_pos_d               
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         77 %     
RESPONSE: Absolute configuration established by
 the structure determination of a compound containing a chiral reference
 molecules of known absolute configuration (S-naproxen and L-proline). 
Signal-to-noise ratio of the data was not sufficient enough for direct
 determination of the absolute configuration by anomalous-dispersion effects. 
;
_vrf_PLAT978_pos_d               
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: Limited resilution if the data, see comments above.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_S-nprx-DL-pro-1-1-H2O
_database_code_depnum_ccdc_archive 'CCDC 1861022'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_chemical_name_systematic        
'bis((2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid); (2R)-pyrrolidin-1-ium-2-carboxylate; (2S)-pyrrolidin-1-ium-2-carboxylate; water'
_chemical_name_common            
;
1:1 S-naproxen DL-proline cocrystal hydrate
;

_chemical_formula_moiety         '2(C14 H14 O3), 2(C5 H9 N O2), 2(H2 O1)'
_chemical_formula_sum            'C38 H50 N2 O12'
_chemical_formula_weight         726.8
_exptl_crystal_density_diffrn    1.282
_chemical_melting_point          ?
_chemical_absolute_configuration rm

_cell_length_a                   6.06468(13)
_cell_length_b                   12.2629(3)
_cell_length_c                   50.6290(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3765.29(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_special_details            
; 
The powder pattern was indexed using FOX program
;
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'-x+1/2, -y, z+1/2 '
'-x, y+1/2, -z+1/2 '
'x+1/2, -y+1/2, -z '
_pd_spec_size_axial              4
_pd_spec_size_equat              0.5
_pd_spec_size_thick              0.5


_pd_spec_mounting                'Thin-wall 0.5 mm glass capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  colourless
_exptl_absorpt_correction_type   none

_pd_instr_location               
; 
BM1 beamline, The Swiss-Norwegian Beamlines (SNBL) at 
European Synchrotron Radiation Facility (ESRF), Grenoble, France
;
_pd_calibration_special_details  
; 
using LaB₆ standard
;

_diffrn_ambient_temperature      295
_diffrn_source                   synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  PILATUS@SNBL
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_type            'PILATUS 2M'
_diffrn_radiation_wavelength     0.798
_pd_meas_scan_method             fixed
_pd_meas_special_details         
;  ?
;

_pd_meas_number_of_points        3363
_pd_meas_2theta_range_min        1.37503
_pd_meas_2theta_range_max        34.99581
_pd_meas_2theta_range_inc        0.01


_pd_proc_ls_prof_R_factor        2.45
_pd_proc_ls_prof_wR_factor       3.63
_pd_proc_ls_prof_wR_expected     0.16

_refine_ls_R_I_factor            2.59
_refine_ls_number_reflns         ?
_refine_ls_number_parameters     ?
_refine_ls_number_restraints     ?
_refine_ls_goodness_of_fit_all   22.67
_refine_ls_shift/su_max          0.001

_pd_proc_2theta_range_min        1.37503
_pd_proc_2theta_range_max        34.99581
_pd_proc_2theta_range_inc        0.01
_pd_proc_wavelength              0.798

_computing_data_collection       ?
_computing_structure_solution    FOX
_computing_structure_refinement  'TOPAS V5'
_computing_molecular_graphics    ?
_computing_publication_material  ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C1a C 4 -0.0502(14) 0.3601(10) 0.2850(2) 1 5.1(4)
C2a C 4 0.0917(14) 0.2826(10) 0.3008(2) 1 5.1(4)
O1a O 4 -0.0608(14) 0.3478(10) 0.2608(2) 1 5.1(4)
O2a O 4 -0.1508(14) 0.4325(10) 0.2978(2) 1 5.1(4)
H2a H 4 -0.0053(14) 0.2347(10) 0.3110(2) 1 5.1(4)
C3a C 4 0.2589(14) 0.3331(10) 0.3195(2) 1 5.1(4)
N1a N 4 0.2307(14) 0.2132(10) 0.2830(2) 1 5.1(4)
H3Aa H 4 0.3269(14) 0.3971(10) 0.3117(2) 1 5.1(4)
H3Ba H 4 0.1904(14) 0.3536(10) 0.3360(2) 1 5.1(4)
C4a C 4 0.4259(14) 0.2433(10) 0.3234(2) 1 5.1(4)
H4Aa H 4 0.5683(14) 0.2734(10) 0.3283(2) 1 5.1(4)
H4Ba H 4 0.3781(14) 0.1937(10) 0.3372(2) 1 5.1(4)
C5a C 4 0.4391(14) 0.1857(10) 0.2976(2) 1 5.1(4)
H5Aa H 4 0.4506(14) 0.1075(10) 0.3002(2) 1 5.1(4)
H5Ba H 4 0.5669(14) 0.2102(10) 0.2877(2) 1 5.1(4)
H1Aa H 4 0.2625(14) 0.2496(10) 0.2681(2) 1 5.1(4)
H1Ba H 4 0.1578(14) 0.1518(10) 0.2787(2) 1 5.1(4)
C11b C 4 0.7002(11) 0.5277(5) 0.35057(12) 1 5.1(3)
C12b C 4 0.7019(11) 0.5690(5) 0.37899(12) 1 5.1(3)
O5b O 4 0.8638(11) 0.4627(5) 0.34561(12) 1 5.1(3)
O6b O 4 0.5635(11) 0.5520(5) 0.33443(12) 1 5.1(3)
H12b H 4 0.8544(11) 0.5704(5) 0.38535(12) 1 5.1(3)
C13b C 4 0.6088(11) 0.6809(5) 0.38028(12) 1 5.1(3)
C14b C 4 0.5718(11) 0.4886(5) 0.39584(12) 1 5.1(3)
H13Ab H 4 0.7209(11) 0.7357(5) 0.37545(12) 1 5.1(3)
H13Bb H 4 0.5611(11) 0.6956(5) 0.39800(12) 1 5.1(3)
H13Cb H 4 0.4855(11) 0.6863(5) 0.36872(12) 1 5.1(3)
C15b C 4 0.6524(11) 0.4519(5) 0.41937(12) 1 5.1(3)
C19b C 4 0.3655(11) 0.4502(5) 0.38769(12) 1 5.1(3)
H15b H 4 0.7859(11) 0.4792(5) 0.42556(12) 1 5.1(3)
C16b C 4 0.5386(11) 0.3734(5) 0.43473(12) 1 5.1(3)
C17b C 4 0.3355(11) 0.3314(5) 0.42567(12) 1 5.1(3)
C20b C 4 0.6252(11) 0.3322(5) 0.45864(12) 1 5.1(3)
C18b C 4 0.2497(11) 0.3748(5) 0.40181(12) 1 5.1(3)
C23b C 4 0.2282(11) 0.2478(5) 0.44022(12) 1 5.1(3)
H18b H 4 0.1128(11) 0.3514(5) 0.39570(12) 1 5.1(3)
H19b H 4 0.3053(11) 0.4769(5) 0.37210(12) 1 5.1(3)
H20b H 4 0.7566(11) 0.3606(5) 0.46520(12) 1 5.1(3)
C21b C 4 0.5206(11) 0.2524(5) 0.47215(12) 1 5.1(3)
H21b H 4 0.5809(11) 0.2262(5) 0.48782(12) 1 5.1(3)
C22b C 4 0.3201(11) 0.2082(5) 0.46267(12) 1 5.1(3)
O7b O 4 0.2378(11) 0.1258(5) 0.47795(12) 1 5.1(3)
H23b H 4 0.0943(11) 0.2200(5) 0.43428(12) 1 5.1(3)
H5Cb H 4 0.8502(11) 0.4465(5) 0.32920(12) 1 5.1(3)
C24b C 4 0.0800(11) 0.0570(5) 0.46551(12) 1 5.1(3)
H24Ab H 4 0.0717(11) -0.0123(5) 0.47498(12) 1 5.1(3)
H24Bb H 4 0.1200(11) 0.0427(5) 0.44687(12) 1 5.1(3)
H24Cb H 4 -0.0662(11) 0.0914(5) 0.46630(12) 1 5.1(3)
C1c C 4 0.4554(18) 0.3597(10) 0.2172(2) 1 6.0(5)
C2c C 4 0.5974(18) 0.2821(10) 0.2014(2) 1 6.0(5)
O1c O 4 0.4448(18) 0.3474(10) 0.2414(2) 1 6.0(5)
O2c O 4 0.3549(18) 0.4321(10) 0.2043(2) 1 6.0(5)
H2c H 4 0.5004(18) 0.2342(10) 0.1912(2) 1 6.0(5)
C3c C 4 0.7646(18) 0.3327(10) 0.1827(2) 1 6.0(5)
N1c N 4 0.7364(18) 0.2128(10) 0.2191(2) 1 6.0(5)
H3Ac H 4 0.8326(18) 0.3967(10) 0.1905(2) 1 6.0(5)
H3Bc H 4 0.6961(18) 0.3531(10) 0.1661(2) 1 6.0(5)
C4c C 4 0.9315(18) 0.2429(10) 0.1787(2) 1 6.0(5)
H4Ac H 4 1.0740(18) 0.2729(10) 0.1739(2) 1 6.0(5)
H4Bc H 4 0.8838(18) 0.1933(10) 0.1650(2) 1 6.0(5)
C5c C 4 0.9447(18) 0.1853(10) 0.2046(2) 1 6.0(5)
H5Ac H 4 0.9562(18) 0.1071(10) 0.2020(2) 1 6.0(5)
H5Bc H 4 1.0726(18) 0.2098(10) 0.2145(2) 1 6.0(5)
H1Ac H 4 0.7681(18) 0.2492(10) 0.2341(2) 1 6.0(5)
H1Bc H 4 0.6635(18) 0.1514(10) 0.2234(2) 1 6.0(5)
O8d O 4 0.042(3) 0.5445(16) 0.2300(3) 1 4.3(4)
H8Ad H 4 -0.024(3) 0.4932(16) 0.2378(3) 1 4.3(4)
H8Bd H 4 0.121(3) 0.5146(16) 0.2180(3) 1 4.3(4)
O8e O 4 0.535(4) 0.5372(16) 0.2638(4) 1 4.3(4)
H8Ae H 4 0.469(4) 0.4859(16) 0.2559(4) 1 4.3(4)
H8Be H 4 0.614(4) 0.5073(16) 0.2757(4) 1 4.3(4)
C11f C 4 0.8240(13) 1.0597(5) 0.35441(13) 1 5.8(3)
C12f C 4 0.8360(13) 1.0898(5) 0.38360(13) 1 5.8(3)
O5f O 4 0.6713(13) 0.9884(5) 0.34952(13) 1 5.8(3)
O6f O 4 0.9412(13) 1.0975(5) 0.33762(13) 1 5.8(3)
H12f H 4 0.9539(13) 1.1422(5) 0.38611(13) 1 5.8(3)
C13f C 4 0.6293(13) 1.1396(5) 0.39213(13) 1 5.8(3)
C14f C 4 0.8869(13) 0.9880(5) 0.39977(13) 1 5.8(3)
H13Af H 4 0.6395(13) 1.2186(5) 0.39145(13) 1 5.8(3)
H13Bf H 4 0.5984(13) 1.1177(5) 0.41000(13) 1 5.8(3)
H13Cf H 4 0.5147(13) 1.1161(5) 0.38119(13) 1 5.8(3)
C15f C 4 0.7428(13) 0.9504(5) 0.41835(13) 1 5.8(3)
C19f C 4 1.0829(13) 0.9298(5) 0.39596(13) 1 5.8(3)
H15f H 4 0.6083(13) 0.9858(5) 0.42055(13) 1 5.8(3)
C16f C 4 0.7916(13) 0.8589(5) 0.43440(13) 1 5.8(3)
C17f C 4 0.9945(13) 0.8041(5) 0.43123(13) 1 5.8(3)
C20f C 4 0.6464(13) 0.8221(5) 0.45432(13) 1 5.8(3)
C18f C 4 1.1369(13) 0.8412(5) 0.41089(13) 1 5.8(3)
C23f C 4 1.0495(13) 0.7166(5) 0.44841(13) 1 5.8(3)
H18f H 4 1.2690(13) 0.8048(5) 0.40772(13) 1 5.8(3)
H19f H 4 1.1796(13) 0.9524(5) 0.38282(13) 1 5.8(3)
H20f H 4 0.5099(13) 0.8558(5) 0.45634(13) 1 5.8(3)
C21f C 4 0.7022(13) 0.7389(5) 0.47050(13) 1 5.8(3)
H21f H 4 0.6043(13) 0.7162(5) 0.48356(13) 1 5.8(3)
C22f C 4 0.9082(13) 0.6860(5) 0.46779(13) 1 5.8(3)
O7f O 4 0.9443(13) 0.6059(5) 0.48609(13) 1 5.8(3)
H23f H 4 1.1832(13) 0.6804(5) 0.44636(13) 1 5.8(3)
H5Cf H 4 0.6817(13) 0.9757(5) 0.33290(13) 1 5.8(3)
C24f C 4 1.0438(13) 0.5115(5) 0.47742(13) 1 5.8(3)
H24Af H 4 1.0131(13) 0.5020(5) 0.45866(13) 1 5.8(3)
H24Bf H 4 0.9830(13) 0.4493(5) 0.48712(13) 1 5.8(3)
H24Cf H 4 1.2023(13) 0.5157(5) 0.48025(13) 1 5.8(3)

loop_
_pd_proc_2theta_corrected
_pd_calc_intensity_total
_pd_proc_intensity_total
1.37503 714.33940 730.17271
1.38503 716.69554 727.67926
1.39503 719.05517 720.54628
1.40503 721.41863 717.14510
1.41503 723.78633 715.57095
1.42503 726.15870 719.23170
1.43503 728.53627 721.91175
1.44503 730.92239 725.87127
1.45503 733.31658 725.02670
1.46503 735.71365 726.89079
1.47503 738.11881 730.91857
1.48503 740.53309 733.91417
1.49503 742.95768 737.75222
1.50503 745.39396 738.84036
1.51503 747.84357 744.59879
1.52503 750.30844 746.37482
1.53503 752.79084 750.66670
1.54503 755.29351 752.46454
1.55503 757.81973 755.95058
1.56503 760.37346 757.76090
1.57504 763.57406 761.45143
1.58504 767.41893 765.15986
1.59504 771.30945 766.17020
1.60504 775.25483 770.04094
1.61504 779.26671 771.73106
1.62504 783.35998 778.04804
1.63504 787.55391 782.19077
1.64504 791.87377 788.10256
1.65504 796.35402 791.23636
1.66504 801.03933 792.66324
1.67504 804.71561 799.03934
1.68504 807.49174 808.30678
1.69504 810.76137 818.38213
1.70504 814.79599 830.76969
1.71504 820.49230 845.40083
1.72504 831.79607 868.26841
1.73504 864.88189 915.48788
1.74504 972.54269 1028.07492
1.75504 1282.23579 1274.44659
1.76504 2000.76839 1870.06641
1.77504 3289.23962 3033.26499
1.78504 4995.97592 4844.00055
1.79504 6495.60610 6414.33213
1.80504 6979.92033 6729.22890
1.81504 6140.42639 5698.78304
1.82504 4493.08905 4081.61792
1.83504 2859.81178 2657.33614
1.84504 1739.67230 1727.34975
1.85504 1165.68905 1274.54778
1.86504 937.55439 1025.96271
1.87504 864.25322 922.60736
1.88504 843.32761 873.98128
1.89504 836.68685 855.39879
1.90504 833.70150 845.32975
1.91504 831.93915 840.10235
1.92504 830.82774 836.13826
1.93504 830.16113 833.87347
1.94504 829.82181 832.01814
1.95504 829.72940 827.26720
1.96504 829.71647 824.86785
1.97504 829.74338 826.07680
1.98504 829.88798 827.65752
1.99504 830.12701 827.91730
2.00505 830.44263 831.01986
2.01505 830.82102 832.79672
2.02505 831.25132 833.54482
2.03505 831.72493 834.64119
2.04505 832.23493 834.52402
2.05505 832.77576 837.74566
2.06505 833.34284 834.60936
2.07505 833.93244 834.55924
2.08505 834.54145 832.11883
2.09505 835.16729 835.73606
2.10505 835.80778 837.76744
2.11505 836.46109 840.02102
2.12505 837.12567 838.77928
2.13505 837.80019 838.09527
2.14505 838.48352 840.51441
2.15505 839.17467 842.95654
2.16505 839.87280 842.99387
2.17505 840.57717 842.65240
2.18505 841.28714 842.51074
2.19505 842.00216 844.31431
2.20505 842.72172 847.35969
2.21505 843.44540 847.83150
2.22505 844.17281 848.25510
2.23505 844.90361 851.18466
2.24505 845.63750 852.64490
2.25505 846.37422 855.54477
2.26505 847.11352 854.45579
2.27505 847.85518 853.44465
2.28505 848.59902 852.43113
2.29505 849.34486 852.36882
2.30505 850.09254 854.57629
2.31505 850.84193 859.41090
2.32505 851.59289 862.25463
2.33505 852.34531 860.73167
2.34505 853.09908 857.52600
2.35505 853.85410 857.97444
2.36505 854.61030 860.69253
2.37505 855.36764 861.18670
2.38505 856.12679 859.42656
2.39505 856.88605 860.35314
2.40505 857.64620 861.63534
2.41505 858.40718 861.48880
2.42505 859.16894 861.79404
2.43506 859.93142 861.28943
2.44506 860.69460 864.64150
2.45506 861.45842 868.74261
2.46506 862.22286 870.58720
2.47506 862.98786 870.19969
2.48506 863.75341 870.12069
2.49506 864.51947 870.31044
2.50506 865.28602 870.22089
2.51506 866.05302 869.90849
2.52506 866.82046 871.75747
2.53506 867.52765 871.22875
2.54506 867.72217 872.34596
2.55506 867.91706 871.57829
2.56506 868.11231 874.84920
2.57506 868.30790 877.19695
2.58506 868.50381 878.37717
2.59506 868.70003 878.23038
2.60506 868.89654 876.85624
2.61506 869.09334 876.94353
2.62506 869.29041 876.52805
2.63506 869.48773 877.18707
2.64506 869.68531 878.94726
2.65506 869.88313 878.47700
2.66506 870.08118 878.15541
2.67506 870.27945 878.57103
2.68506 870.47794 879.23439
2.69506 870.67663 879.87428
2.70506 870.87553 881.70733
2.71506 871.07462 884.14825
2.72506 871.27390 883.92959
2.73506 871.47337 883.56311
2.74506 871.67302 884.47985
2.75506 871.87284 886.29529
2.76506 872.07284 884.98626
2.77506 872.27301 885.25122
2.78506 872.47334 884.21755
2.79506 872.67383 883.09151
2.80506 872.87448 882.49376
2.81506 873.07530 882.65646
2.82506 873.27627 884.63205
2.83506 873.47739 884.16077
2.84506 873.67867 885.83228
2.85506 873.88011 885.71460
2.86507 874.08170 887.10741
2.87507 874.28344 885.34703
2.88507 874.48534 887.50208
2.89507 874.68740 885.34769
2.90507 874.88961 888.38738
2.91507 875.09199 887.99286
2.92507 875.29455 888.62011
2.93507 875.49805 889.52398
2.94507 875.70093 888.49704
2.95507 875.90398 889.73493
2.96507 876.10721 889.96694
2.97507 876.31061 893.78624
2.98507 876.51421 892.63499
2.99507 876.71800 892.47116
3.00507 876.92199 890.01147
3.01507 877.12619 891.20108
3.02507 877.33060 893.83584
3.03507 877.53525 894.26724
3.04507 877.74013 892.91550
3.05507 877.94527 890.75503
3.06507 878.15067 892.29990
3.07507 878.35635 895.04526
3.08507 878.56232 896.47616
3.09507 878.76861 896.33726
3.10507 878.97523 897.32776
3.11507 879.18221 893.73965
3.12507 879.38957 892.16813
3.13507 879.59734 891.20798
3.14507 879.80938 892.42468
3.15507 880.01810 892.41619
3.16507 880.22732 895.87944
3.17507 880.43710 897.82466
3.18507 880.64749 895.84414
3.19507 880.85852 895.31725
3.20507 881.07027 894.60141
3.21507 881.28281 896.67644
3.22507 881.49620 898.42291
3.23507 881.71055 900.05276
3.24507 881.92593 900.10851
3.25507 882.14248 897.54964
3.26507 882.36031 896.84431
3.27507 882.57957 895.86083
3.28507 882.80044 896.24122
3.29508 883.02312 895.45581
3.30508 883.24782 897.89414
3.31508 883.47484 900.43205
3.32508 883.70446 901.46482
3.33508 883.93708 900.23538
3.34508 884.17314 900.94559
3.35508 884.41315 901.18586
3.36508 884.65776 902.76549
3.37508 884.90773 904.80751
3.38508 885.16400 906.03157
3.39508 885.42773 910.44817
3.40508 885.70033 921.09772
3.41508 885.98360 942.54053
3.42508 886.27980 963.54320
3.43508 886.59182 976.21521
3.44508 886.92340 969.67631
3.45508 887.27947 950.43326
3.46508 887.66658 931.63441
3.47508 888.09361 917.26264
3.48508 888.57285 908.93259
3.49508 889.12188 904.71023
3.50508 889.76850 902.44134
3.51508 890.57113 902.31882
3.52508 891.71535 904.74440
3.53508 893.90052 908.28818
3.54508 899.51056 915.87852
3.55508 915.01178 933.49668
3.56508 953.30780 980.25064
3.57508 1030.98515 1079.27241
3.58508 1154.65024 1238.98273
3.59508 1301.36120 1429.67198
3.60508 1413.91044 1557.45472
3.61508 1430.53572 1549.40685
3.62508 1340.79559 1422.54123
3.63508 1197.30688 1238.29207
3.64508 1063.41807 1094.15926
3.65508 972.70418 997.49581
3.66508 925.19806 946.64824
3.67508 905.24469 921.78767
3.68508 898.18189 907.21314
3.69508 895.82482 901.31313
3.70508 894.76371 898.53017
3.71508 894.17240 896.15205
3.72509 893.78663 894.25216
3.73509 893.53762 893.98043
3.74509 893.41717 895.10330
3.75509 893.49461 894.94708
3.76509 894.07389 893.00968
3.77509 896.08470 891.14936
3.78509 901.63682 889.83488
3.79509 914.02748 889.48282
3.80509 935.89704 890.63529
3.81509 965.37792 891.73837
3.82509 993.31015 892.34526
3.83509 1006.09596 893.95822
3.84509 995.88400 896.16531
3.85509 968.92771 899.10982
3.86509 938.86165 897.06988
3.87509 915.67757 897.19938
3.88509 902.06963 896.70358
3.89509 895.71573 896.55816
3.90509 893.23873 895.31590
3.91509 892.34845 896.20984
3.92509 891.98946 897.77896
3.93509 891.79504 898.58943
3.94509 891.66077 901.57091
3.95509 891.55803 900.54888
3.96509 891.47666 901.31357
3.97509 891.41130 900.61886
3.98509 891.35844 901.39122
3.99509 891.31568 900.21283
4.00509 891.28135 898.75093
4.01509 891.25436 898.00452
4.02509 891.23412 897.82728
4.03509 891.22052 898.73786
4.04509 891.21445 899.37691
4.05509 891.21999 900.70416
4.06509 891.25342 901.11316
4.07509 891.36993 901.60540
4.08509 891.71819 902.12727
4.09509 892.59532 902.86187
4.10509 894.39139 902.34512
4.11509 897.29028 903.28365
4.12509 900.81862 904.90578
4.13509 903.68478 906.34579
4.14509 904.37109 908.01226
4.15510 902.44356 905.34707
4.16510 899.03729 902.44958
4.17510 895.69151 900.00698
4.18510 893.31409 901.84294
4.19510 892.00309 900.44416
4.20510 891.41872 900.43179
4.21510 891.19595 900.59825
4.22510 891.11409 902.73009
4.23510 891.07862 902.36248
4.24510 891.05832 903.07743
4.25510 891.04418 901.96222
4.26510 891.03374 902.11897
4.27510 891.02598 902.22655
4.28510 891.02032 901.49284
4.29510 891.01637 901.69325
4.30510 891.01386 900.72464
4.31510 891.01260 901.97601
4.32510 891.01248 902.01059
4.33510 891.01341 902.96894
4.34510 891.01536 903.98152
4.35510 891.01832 902.20410
4.36510 891.02231 900.88723
4.37510 891.02740 899.18263
4.38510 891.03366 900.28737
4.39510 891.04124 899.78171
4.40510 891.05029 899.58552
4.41510 891.06105 899.17364
4.42510 891.07382 899.49552
4.43510 891.08899 900.26567
4.44510 891.10708 901.38344
4.45510 891.12877 902.54056
4.46510 891.15501 900.91009
4.47510 891.18706 901.50165
4.48510 891.22670 899.85976
4.49510 891.27652 899.63819
4.50510 891.34092 898.56482
4.51510 891.43021 900.67207
4.52510 891.57814 900.09779
4.53510 891.90245 898.76482
4.54510 892.75878 898.24514
4.55510 894.98955 900.22272
4.56510 900.03370 902.03198
4.57510 909.35022 902.29158
4.58511 922.85247 905.14407
4.59511 937.29354 906.34251
4.60511 946.55561 909.32735
4.61511 945.32802 907.44738
4.62511 934.38247 903.41411
4.63511 919.69506 900.08782
4.64511 906.94807 899.50653
4.65511 898.63576 900.03703
4.66511 894.34694 899.07983
4.67511 892.52324 897.69144
4.68511 891.83822 895.50254
4.69511 891.57558 896.14481
4.70511 891.45052 897.97669
4.71511 891.37271 900.56009
4.72511 891.31653 901.98343
4.73511 891.27370 900.70876
4.74511 891.24041 899.13881
4.75511 891.21427 896.49177
4.76511 891.19364 896.00425
4.77511 891.17733 896.68769
4.78511 891.16448 897.53792
4.79511 891.15442 897.78923
4.80511 891.14667 899.09428
4.81511 891.14086 899.66285
4.82511 891.13671 899.84017
4.83511 891.13398 898.67518
4.84511 891.13251 896.73568
4.85511 891.10810 896.07636
4.86511 890.93780 895.93317
4.87511 890.76847 896.68857
4.88511 890.60005 895.60329
4.89511 890.43252 895.24493
4.90511 890.26588 897.46104
4.91511 890.10012 899.10351
4.92511 889.93527 897.67834
4.93511 889.77139 895.28376
4.94511 889.60853 894.70176
4.95511 889.44690 894.56486
4.96511 889.28637 894.39305
4.97511 889.12721 893.97683
4.98511 888.96961 892.33918
4.99511 888.81380 891.84959
5.00511 888.66007 891.78176
5.01512 888.50880 890.67109
5.02512 888.36050 889.12750
5.03512 888.21580 889.94513
5.04512 888.07554 891.57331
5.05512 887.94088 892.20017
5.06512 887.81338 891.30102
5.07512 887.69582 891.82625
5.08512 887.59065 891.80292
5.09512 887.50579 892.21860
5.10512 887.46303 891.59926
5.11512 887.53612 892.31374
5.12512 887.96359 894.16201
5.13512 889.28287 896.08894
5.14512 892.54123 895.01066
5.15512 898.97456 892.73809
5.16512 908.98950 891.98967
5.17512 920.79487 891.64594
5.18512 930.03613 892.26221
5.19512 931.77703 892.25713
5.20512 924.84697 892.68507
5.21512 913.18388 891.01477
5.22512 901.79338 887.85305
5.23512 893.58265 886.75681
5.24512 888.90384 888.70514
5.25512 886.69713 890.61378
5.26512 885.77513 890.10449
5.27512 885.39072 890.27688
5.28512 885.21094 890.04854
5.29512 885.12512 890.59331
5.30512 885.10770 890.20442
5.31512 885.16739 889.74125
5.32512 885.34419 890.74764
5.33512 885.77543 893.69800
5.34512 886.92377 896.83502
5.35512 890.13305 899.52175
5.36512 898.47230 906.24833
5.37512 916.98297 921.96376
5.38512 950.69050 955.03516
5.39512 999.23259 1006.30220
5.40512 1051.43632 1070.56491
5.41512 1085.95264 1110.08059
5.42512 1083.32203 1097.03395
5.43512 1045.07474 1045.76037
5.44513 991.96710 987.51026
5.45513 944.50311 941.57030
5.46513 912.41533 915.07706
5.47513 895.07985 902.82210
5.48513 887.25075 897.58716
5.49513 884.05310 897.69211
5.50513 882.67300 896.05242
5.51513 881.91667 895.75458
5.52513 881.38049 897.77866
5.53513 880.94369 900.47457
5.54513 880.56688 902.44453
5.55513 880.23232 902.94631
5.56513 879.92927 904.18390
5.57513 879.65031 905.31008
5.58513 879.39008 904.24348
5.59513 879.14465 902.03743
5.60513 878.91107 899.35453
5.61513 878.68708 899.35242
5.62513 878.47095 900.10585
5.63513 878.26134 900.18851
5.64513 878.05720 897.69199
5.65513 877.85769 894.56360
5.66513 877.66214 891.87553
5.67513 877.47003 889.95578
5.68513 877.28096 887.73587
5.69513 877.09460 885.88175
5.70513 876.91072 883.86762
5.71513 876.73014 883.61399
5.72513 876.55200 881.69200
5.73513 876.37504 880.99025
5.74513 876.20053 878.87729
5.75513 876.02895 878.93050
5.76513 875.86165 879.44547
5.77513 875.70264 879.27118
5.78513 875.56180 879.30602
5.79513 875.49194 878.92987
5.80513 875.57186 879.26083
5.81513 875.92846 878.80516
5.82513 876.66293 878.96736
5.83513 877.71614 876.96719
5.84513 878.76127 879.23066
5.85513 879.26496 878.34269
5.86513 878.88816 878.31285
5.87514 877.68691 877.36679
5.88514 876.23488 878.18853
5.89514 874.98342 877.53876
5.90514 874.11078 877.25506
5.91514 873.57239 876.39969
5.92514 873.23984 878.03262
5.93514 873.00492 878.08164
5.94514 872.80933 874.53065
5.95514 872.62571 873.89770
5.96514 872.44715 874.76059
5.97514 872.27111 876.73564
5.98514 872.09675 877.41838
5.99514 871.92357 876.49798
6.00514 871.75133 876.76690
6.01514 871.55959 876.73787
6.02514 871.32947 876.77601
6.03514 871.10295 875.19144
6.04514 870.86955 873.49370
6.05514 870.63653 872.84714
6.06514 870.40383 873.34157
6.07514 870.17142 874.43000
6.08514 869.93928 873.69320
6.09514 869.70737 873.72927
6.10514 869.47568 872.40894
6.11514 869.24419 873.05464
6.12514 869.01289 870.55802
6.13514 868.78177 869.79246
6.14514 868.55083 869.59215
6.15514 868.32004 870.37806
6.16514 868.09076 870.02335
6.17514 867.86641 869.65701
6.18514 867.63616 869.04138
6.19514 867.40606 868.60636
6.20514 867.17611 868.49909
6.21514 866.94631 868.28929
6.22514 866.71667 869.29454
6.23514 866.48717 870.81642
6.24514 866.25783 870.91617
6.25514 866.02864 869.72176
6.26514 865.79962 869.70151
6.27514 865.57076 868.89815
6.28514 865.35741 868.83646
6.29514 865.13480 866.91505
6.30515 864.90666 866.46628
6.31515 864.67871 867.31452
6.32515 864.45097 868.20385
6.33515 864.22346 869.42034
6.34515 863.99691 867.16726
6.35515 863.77043 865.90624
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33.66578 279.07018 278.57730
33.67578 278.04118 279.41915
33.68578 276.96217 276.64528
33.69578 276.02973 275.55342
33.70578 275.29710 276.00910
33.71578 274.89829 275.84659
33.72578 274.88851 276.23377
33.73578 275.14217 276.64820
33.74578 275.38277 277.91085
33.75578 275.42245 278.66490
33.76578 275.35622 278.29866
33.77578 275.32608 279.69051
33.78578 275.30176 280.39457
33.79578 275.25504 280.21977
33.80578 275.25138 280.14659
33.81578 275.24641 278.92248
33.82579 275.17229 277.47307
33.83579 275.13244 277.58545
33.84579 274.94362 277.84684
33.85579 274.93776 276.91363
33.86579 275.09837 277.17264
33.87579 275.44651 276.00038
33.88579 276.09642 276.44286
33.89579 277.08219 277.79713
33.90579 278.31152 279.02701
33.91579 279.72537 278.89175
33.92579 281.07225 278.54906
33.93579 281.70869 281.60283
33.94579 281.28616 283.88825
33.95579 280.20583 284.66017
33.96579 278.90652 283.51342
33.97579 277.68404 280.47442
33.98579 276.93061 280.43708
33.99579 276.76577 284.58390
34.00579 276.84845 285.47229
34.01579 276.74359 284.34782
34.02579 276.33567 284.08157
34.03579 275.73530 284.59433
34.04579 275.02617 285.26792
34.05579 274.34309 283.52537
34.06579 273.78212 281.73916
34.07579 273.38354 280.02398
34.08579 273.20914 278.66820
34.09579 273.26859 278.67260
34.10579 273.32508 279.08817
34.11579 273.04890 281.46329
34.12579 272.57996 281.93180
34.13579 272.33683 280.82180
34.14579 272.37461 280.77571
34.15579 272.20633 280.92486
34.16579 271.25739 283.49398
34.17579 269.65128 282.98503
34.18579 268.03268 281.34406
34.19579 266.79791 283.31097
34.20579 265.91270 282.51018
34.21579 265.22582 280.88913
34.22579 264.74140 280.70026
34.23579 264.46697 280.85744
34.24579 264.20672 280.70203
34.25580 263.66515 279.34986
34.26580 262.71611 278.02573
34.27580 261.48470 276.06547
34.28580 260.23682 276.51183
34.29580 259.21512 276.91209
34.30580 258.54201 274.44462
34.31580 258.25066 272.53262
34.32580 258.32984 273.80585
34.33580 258.72394 274.41027
34.34580 259.31955 271.94342
34.35580 259.97728 272.63794
34.36580 260.55639 274.57682
34.37580 260.91864 274.53008
34.38580 261.11993 276.05839
34.39580 261.33534 279.93127
34.40580 261.50731 279.43548
34.41580 261.50082 279.65370
34.42580 261.34396 279.41929
34.43580 261.13897 277.98437
34.44580 260.92216 277.26156
34.45580 260.40101 275.99502
34.46580 259.20096 277.54112
34.47580 257.48612 276.67880
34.48580 255.75157 276.10094
34.49580 254.29645 274.69187
34.50580 253.15506 270.95670
34.51580 252.24054 271.52509
34.52580 251.51495 271.71465
34.53580 251.00375 270.23796
34.54580 250.70294 269.44003
34.55580 250.53871 268.91109
34.56580 250.35248 270.54837
34.57580 250.02412 273.02922
34.58580 249.60164 273.22332
34.59580 249.15169 272.40702
34.60580 248.67398 273.21755
34.61580 248.23931 273.76526
34.62580 247.98491 273.24242
34.63580 247.97863 274.67487
34.64580 248.15976 277.18726
34.65580 248.32873 275.73505
34.66580 248.28145 273.44893
34.67580 248.06893 271.41079
34.68581 247.95269 273.00820
34.69581 248.13743 276.10594
34.70581 248.67463 274.82643
34.71581 249.43279 275.60333
34.72581 250.08447 276.30087
34.73581 250.42910 274.25802
34.74581 250.65246 276.95256
34.75581 250.88173 280.28176
34.76581 250.79002 279.31922
34.77581 249.93299 278.86567
34.78581 248.32562 279.41357
34.79581 246.35810 278.80736
34.80581 244.41213 279.60450
34.81581 242.74463 278.09378
34.82581 241.46096 279.80201
34.83581 240.55057 282.69829
34.84581 239.94637 275.46018
34.85581 239.57042 269.38879
34.86581 239.37249 275.58408
34.87581 239.37465 277.24717
34.88581 239.65836 268.51366
34.89581 240.30201 272.09134
34.90581 241.32571 286.87604
34.91581 242.63689 261.91416
34.92581 244.00275 229.00161
34.93581 245.08073 240.19272
34.94581 245.48483 249.78743
34.95581 245.08967 265.30846
34.96581 244.26659 265.56572
34.97581 243.47779 258.92900
34.98581 242.88062 273.74962
34.99581 242.28012 245.03678

# start Validation Reply Form
_vrf_GEOM001_S-nprx-DL-pro-1-1-H2O 
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM003_S-nprx-DL-pro-1-1-H2O 
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM006_S-nprx-DL-pro-1-1-H2O 
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM007_S-nprx-DL-pro-1-1-H2O 
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_exptl_crystal_colour            colourless
_exptl_crystal_description       powder
####################################################################### 
# 
# 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_nt0022_SnprxLpro_EtOH_b6
_database_code_depnum_ccdc_archive 'CCDC 1861017'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid 
bis((2S)-pyrrolidin-1-ium-2-carboxylate)
;
_chemical_name_common            'S-naproxen L-proline 1:2 cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O3, 2(C5 H9 N O2)'
_chemical_formula_sum            'C24 H32 N2 O7'
_chemical_formula_weight         460.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.88160(7)
_cell_length_b                   8.79809(10)
_cell_length_c                   45.4679(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2352.82(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    13404
_cell_measurement_theta_min      3.8590
_cell_measurement_theta_max      67.0330

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.791
_shelx_estimated_absorpt_T_min   0.727
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            23068
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         3.889
_diffrn_reflns_theta_max         67.225
_diffrn_reflns_theta_full        67.225
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4165
_reflns_number_gt                4025
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_max     0.985
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0657P)²+0.3973P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1595 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4165
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O1 O 0.8790(4) 0.4382(5) 0.62159(7) 0.1232(14) Uani 1 1 d . . . . .
N1 N 0.0052(3) 0.8084(2) 0.67898(4) 0.0432(4) Uani 1 1 d . . . . .
H1A H -0.133(3) 0.7490(12) 0.67956(4) 0.052 Uiso 1 1 calc R U . . .
H1B H 0.0539(10) 0.8281(4) 0.6990(4) 0.052 Uiso 1 1 calc R U . . .
C1 C 0.6912(5) 0.4069(3) 0.61489(6) 0.0547(6) Uani 1 1 d . . . . .
O2 O 0.5165(4) 0.4731(3) 0.62659(5) 0.0790(7) Uani 1 1 d . . . . .
H2O H 0.568(2) 0.551(5) 0.6403(9) 0.095 Uiso 1 1 calc R U . . .
N2 N 0.3033(3) 0.7369(2) 0.75389(5) 0.0446(5) Uani 1 1 d . . . . .
H2A H 0.2207(17) 0.6478(18) 0.74515(19) 0.054 Uiso 1 1 calc R U . . .
H2B H 0.3428(9) 0.8095(15) 0.7376(3) 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6288(5) 0.2858(3) 0.59254(6) 0.0587(7) Uani 1 1 d . . . . .
H2 H 0.769369 0.234051 0.586744 0.070 Uiso 1 1 calc R U . . .
O3 O 0.3280(5) 0.6343(3) 0.43701(5) 0.0758(7) Uani 1 1 d . . . . .
C3 C 0.4726(8) 0.1674(4) 0.60663(8) 0.0861(11) Uani 1 1 d . . . . .
H3A H 0.328882 0.213363 0.611229 0.129 Uiso 1 1 calc R U . . .
H3B H 0.541338 0.129805 0.624346 0.129 Uiso 1 1 calc R U . . .
H3C H 0.449571 0.084799 0.593169 0.129 Uiso 1 1 calc R U . . .
O4 O 0.5846(3) 0.6880(2) 0.66394(4) 0.0545(4) Uani 1 1 d . . . . .
C4 C 0.5274(5) 0.3577(3) 0.56503(6) 0.0493(6) Uani 1 1 d . . . . .
C5 C 0.3148(5) 0.4342(3) 0.56573(6) 0.0528(6) Uani 1 1 d . . . . .
H5 H 0.231633 0.436515 0.583126 0.063 Uiso 1 1 calc R U . . .
O5 O 0.4355(3) 0.8423(2) 0.69717(4) 0.0586(5) Uani 1 1 d . . . . .
C7 C 0.3502(4) 0.5022(3) 0.51425(5) 0.0457(5) Uani 1 1 d . . . . .
O7 O -0.0827(4) 1.0276(2) 0.77949(4) 0.0705(6) Uani 1 1 d . . . . .
C6 C 0.2309(4) 0.5040(3) 0.54133(6) 0.0527(6) Uani 1 1 d . . . . .
H6 H 0.092040 0.554224 0.542452 0.063 Uiso 1 1 calc R U . . .
O6 O 0.0099(4) 0.9501(2) 0.73509(4) 0.0600(5) Uani 1 1 d . . . . .
C9 C 0.3882(5) 0.5681(3) 0.46312(6) 0.0551(6) Uani 1 1 d . . . . .
C8 C 0.2689(5) 0.5768(3) 0.48881(6) 0.0521(6) Uani 1 1 d . . . . .
H8 H 0.134030 0.631800 0.489572 0.063 Uiso 1 1 calc R U . . .
C18 C -0.0115(7) 0.9083(4) 0.63137(7) 0.0769(9) Uani 1 1 d . . . . .
H18A H 0.033845 0.994569 0.619453 0.092 Uiso 1 1 calc R U . . .
H18B H -0.154699 0.869188 0.623972 0.092 Uiso 1 1 calc R U . . .
C24 C 0.5141(5) 0.6846(4) 0.76901(7) 0.0685(8) Uani 1 1 d . . . . .
H24A H 0.518376 0.574441 0.769803 0.082 Uiso 1 1 calc R U . . .
H24B H 0.647594 0.720054 0.758539 0.082 Uiso 1 1 calc R U . . .
C23 C 0.5088(6) 0.7491(4) 0.79923(7) 0.0679(8) Uani 1 1 d . . . . .
H23A H 0.654574 0.793990 0.804145 0.082 Uiso 1 1 calc R U . . .
H23B H 0.474531 0.670419 0.813500 0.082 Uiso 1 1 calc R U . . .
C22 C 0.3267(6) 0.8675(4) 0.79914(7) 0.0726(9) Uani 1 1 d . . . . .
H22A H 0.388666 0.966061 0.793930 0.087 Uiso 1 1 calc R U . . .
H22B H 0.255248 0.874822 0.818318 0.087 Uiso 1 1 calc R U . . .
C21 C 0.1567(4) 0.8140(3) 0.77609(5) 0.0444(5) Uani 1 1 d . . . . .
H21 H 0.053933 0.739257 0.784947 0.053 Uiso 1 1 calc R U . . .
C20 C 0.0172(4) 0.9408(2) 0.76222(5) 0.0416(5) Uani 1 1 d . . . . .
C19 C -0.0329(5) 0.9532(3) 0.66306(7) 0.0617(7) Uani 1 1 d . . . . .
H19A H 0.080663 1.028300 0.668349 0.074 Uiso 1 1 calc R U . . .
H19B H -0.182841 0.993898 0.667193 0.074 Uiso 1 1 calc R U . . .
C17 C 0.1684(5) 0.7870(4) 0.63089(5) 0.0599(7) Uani 1 1 d . . . . .
H17A H 0.312796 0.829211 0.624628 0.072 Uiso 1 1 calc R U . . .
H17B H 0.126121 0.706324 0.617402 0.072 Uiso 1 1 calc R U . . .
C16 C 0.1865(4) 0.7252(3) 0.66239(5) 0.0404(5) Uani 1 1 d . . . . .
H16 H 0.153807 0.615973 0.662483 0.049 Uiso 1 1 calc R U . . .
C15 C 0.4198(4) 0.7541(3) 0.67599(5) 0.0402(5) Uani 1 1 d . . . . .
C14 C 0.6426(4) 0.3516(3) 0.53898(6) 0.0489(6) Uani 1 1 d . . . . .
H14 H 0.780353 0.299877 0.538227 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5593(4) 0.4212(3) 0.51314(5) 0.0452(5) Uani 1 1 d . . . . .
C12 C 0.6763(5) 0.4149(3) 0.48598(6) 0.0566(6) Uani 1 1 d . . . . .
H12 H 0.813036 0.362289 0.484725 0.068 Uiso 1 1 calc R U . . .
C11 C 0.5917(5) 0.4846(3) 0.46178(6) 0.0605(7) Uani 1 1 d . . . . .
H11 H 0.669279 0.477058 0.444024 0.073 Uiso 1 1 calc R U . . .
C10 C 0.1362(7) 0.7322(4) 0.43709(7) 0.0729(9) Uani 1 1 d . . . . .
H10A H 0.114645 0.773633 0.417764 0.109 Uiso 1 1 calc R U . . .
H10B H 0.160764 0.813316 0.450843 0.109 Uiso 1 1 calc R U . . .
H10C H 0.003450 0.675733 0.442724 0.109 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
O1 C1 1.179(4) . ?
N1 C19 1.482(4) . ?
N1 C16 1.497(3) . ?
N1 H1A 0.97(2) . ?
N1 H1B 0.968(19) . ?
C1 O2 1.295(4) . ?
C1 C2 1.517(4) . ?
O2 H2O 0.98(4) . ?
N2 C24 1.490(3) . ?
N2 C21 1.491(3) . ?
N2 H2A 1.00(2) . ?
N2 H2B 1.00(2) . ?
C2 C4 1.523(4) . ?
C2 C3 1.530(5) . ?
C2 H2 0.9800 . ?
O3 C9 1.369(3) . ?
O3 C10 1.419(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
O4 C15 1.256(3) . ?
C4 C14 1.365(4) . ?
C4 C5 1.420(4) . ?
C5 C6 1.361(4) . ?
C5 H5 0.9300 . ?
O5 C15 1.240(3) . ?
C7 C8 1.413(4) . ?
C7 C6 1.417(4) . ?
C7 C13 1.422(3) . ?
O7 C20 1.243(3) . ?
C6 H6 0.9300 . ?
O6 C20 1.237(3) . ?
C9 C8 1.364(4) . ?
C9 C11 1.406(4) . ?
C8 H8 0.9300 . ?
C18 C19 1.499(4) . ?
C18 C17 1.503(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C24 C23 1.487(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C23 C22 1.494(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C22 C21 1.523(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C21 C20 1.522(3) . ?
C21 H21 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C17 C16 1.536(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 C15 1.526(3) . ?
C16 H16 0.9800 . ?
C14 C13 1.413(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.415(4) . ?
C12 C11 1.354(4) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C19 N1 C16 106.36(19) . . ?
C19 N1 H1A 110.5 . . ?
C16 N1 H1A 110.5 . . ?
C19 N1 H1B 110.5 . . ?
C16 N1 H1B 110.5 . . ?
H1A N1 H1B 108.6 . . ?
O1 C1 O2 122.1(3) . . ?
O1 C1 C2 124.3(3) . . ?
O2 C1 C2 113.5(2) . . ?
C1 O2 H2O 109.5 . . ?
C24 N2 C21 108.0(2) . . ?
C24 N2 H2A 110.1 . . ?
C21 N2 H2A 110.1 . . ?
C24 N2 H2B 110.1 . . ?
C21 N2 H2B 110.1 . . ?
H2A N2 H2B 108.4 . . ?
C1 C2 C4 110.7(2) . . ?
C1 C2 C3 110.0(3) . . ?
C4 C2 C3 113.0(3) . . ?
C1 C2 H2 107.6 . . ?
C4 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
C9 O3 C10 117.5(2) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C14 C4 C5 118.4(2) . . ?
C14 C4 C2 120.1(2) . . ?
C5 C4 C2 121.5(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C8 C7 C6 122.6(2) . . ?
C8 C7 C13 119.7(2) . . ?
C6 C7 C13 117.7(2) . . ?
C5 C6 C7 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C9 O3 125.9(3) . . ?
C8 C9 C11 120.3(2) . . ?
O3 C9 C11 113.9(2) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C19 C18 C17 105.1(2) . . ?
C19 C18 H18A 110.7 . . ?
C17 C18 H18A 110.7 . . ?
C19 C18 H18B 110.7 . . ?
C17 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?
C23 C24 N2 106.9(2) . . ?
C23 C24 H24A 110.3 . . ?
N2 C24 H24A 110.3 . . ?
C23 C24 H24B 110.3 . . ?
N2 C24 H24B 110.3 . . ?
H24A C24 H24B 108.6 . . ?
C24 C23 C22 106.2(2) . . ?
C24 C23 H23A 110.5 . . ?
C22 C23 H23A 110.5 . . ?
C24 C23 H23B 110.5 . . ?
C22 C23 H23B 110.5 . . ?
H23A C23 H23B 108.7 . . ?
C23 C22 C21 104.9(2) . . ?
C23 C22 H22A 110.8 . . ?
C21 C22 H22A 110.8 . . ?
C23 C22 H22B 110.8 . . ?
C21 C22 H22B 110.8 . . ?
H22A C22 H22B 108.8 . . ?
N2 C21 C20 111.39(19) . . ?
N2 C21 C22 103.1(2) . . ?
C20 C21 C22 114.4(2) . . ?
N2 C21 H21 109.2 . . ?
C20 C21 H21 109.2 . . ?
C22 C21 H21 109.2 . . ?
O6 C20 O7 125.0(2) . . ?
O6 C20 C21 118.7(2) . . ?
O7 C20 C21 116.3(2) . . ?
N1 C19 C18 103.3(2) . . ?
N1 C19 H19A 111.1 . . ?
C18 C19 H19A 111.1 . . ?
N1 C19 H19B 111.1 . . ?
C18 C19 H19B 111.1 . . ?
H19A C19 H19B 109.1 . . ?
C18 C17 C16 106.6(2) . . ?
C18 C17 H17A 110.4 . . ?
C16 C17 H17A 110.4 . . ?
C18 C17 H17B 110.4 . . ?
C16 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
N1 C16 C15 110.77(17) . . ?
N1 C16 C17 104.34(19) . . ?
C15 C16 C17 112.4(2) . . ?
N1 C16 H16 109.7 . . ?
C15 C16 H16 109.7 . . ?
C17 C16 H16 109.7 . . ?
O5 C15 O4 124.8(2) . . ?
O5 C15 C16 119.1(2) . . ?
O4 C15 C16 116.11(19) . . ?
C4 C14 C13 122.1(2) . . ?
C4 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C13 C12 122.7(2) . . ?
C14 C13 C7 119.2(2) . . ?
C12 C13 C7 118.1(2) . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C11 C9 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C9 C11 H11 119.5 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O1 C1 C2 C4 -111.5(4) . . . . ?
O2 C1 C2 C4 69.4(3) . . . . ?
O1 C1 C2 C3 122.8(4) . . . . ?
O2 C1 C2 C3 -56.2(3) . . . . ?
C1 C2 C4 C14 112.7(3) . . . . ?
C3 C2 C4 C14 -123.4(3) . . . . ?
C1 C2 C4 C5 -66.4(3) . . . . ?
C3 C2 C4 C5 57.6(3) . . . . ?
C14 C4 C5 C6 -2.1(4) . . . . ?
C2 C4 C5 C6 176.9(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C8 C7 C6 C5 -178.6(3) . . . . ?
C13 C7 C6 C5 1.5(4) . . . . ?
C10 O3 C9 C8 6.2(4) . . . . ?
C10 O3 C9 C11 -174.3(3) . . . . ?
O3 C9 C8 C7 179.7(3) . . . . ?
C11 C9 C8 C7 0.3(4) . . . . ?
C6 C7 C8 C9 -178.4(3) . . . . ?
C13 C7 C8 C9 1.5(4) . . . . ?
C21 N2 C24 C23 -7.8(3) . . . . ?
N2 C24 C23 C22 -13.4(4) . . . . ?
C24 C23 C22 C21 29.0(4) . . . . ?
C24 N2 C21 C20 148.3(2) . . . . ?
C24 N2 C21 C22 25.2(3) . . . . ?
C23 C22 C21 N2 -33.1(3) . . . . ?
C23 C22 C21 C20 -154.2(2) . . . . ?
N2 C21 C20 O6 11.4(3) . . . . ?
C22 C21 C20 O6 127.9(3) . . . . ?
N2 C21 C20 O7 -168.9(2) . . . . ?
C22 C21 C20 O7 -52.4(3) . . . . ?
C16 N1 C19 C18 37.8(3) . . . . ?
C17 C18 C19 N1 -35.0(3) . . . . ?
C19 C18 C17 C16 19.5(4) . . . . ?
C19 N1 C16 C15 95.8(2) . . . . ?
C19 N1 C16 C17 -25.4(3) . . . . ?
C18 C17 C16 N1 3.3(3) . . . . ?
C18 C17 C16 C15 -116.8(3) . . . . ?
N1 C16 C15 O5 -2.7(3) . . . . ?
C17 C16 C15 O5 113.6(3) . . . . ?
N1 C16 C15 O4 179.2(2) . . . . ?
C17 C16 C15 O4 -64.5(3) . . . . ?
C5 C4 C14 C13 1.4(4) . . . . ?
C2 C4 C14 C13 -177.7(2) . . . . ?
C4 C14 C13 C12 -179.6(2) . . . . ?
C4 C14 C13 C7 0.8(4) . . . . ?
C8 C7 C13 C14 177.8(2) . . . . ?
C6 C7 C13 C14 -2.2(3) . . . . ?
C8 C7 C13 C12 -1.8(4) . . . . ?
C6 C7 C13 C12 178.2(2) . . . . ?
C14 C13 C12 C11 -179.3(3) . . . . ?
C7 C13 C12 C11 0.2(4) . . . . ?
C13 C12 C11 C9 1.5(4) . . . . ?
C8 C9 C11 C12 -1.8(4) . . . . ?
O3 C9 C11 C12 178.7(3) . . . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039


# start Validation Reply Form
_vrf_PLAT242_nt0022_SnprxLpro_EtOH_b6 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check 
RESPONSE: Carbon atom in the wobbling COOH-group.
;
_vrf_PLAT243_nt0022_SnprxLpro_EtOH_b6 
;
PROBLEM: High   'Solvent' Ueq as Compared to Neighbors of        C18 Check 
RESPONSE: Probably because of minor disorder of the proline molecule.
;
_vrf_PLAT244_nt0022_SnprxLpro_EtOH_b6 
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of        C20 Check 
RESPONSE:  Carbon atom in the wobbling COO^-^-group.
;
_vrf_PLAT911_nt0022_SnprxLpro_EtOH_b6 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.598          9 Report
RESPONSE: These reflections are missing in the highest resolution 
shells because of the instrument geometry limitation.
;
_vrf_PLAT978_nt0022_SnprxLpro_EtOH_b6 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: Limited resolution - crystal diffracts poorly on Mo radiation, 
and we had to use Cu radiation.
;
####################################################################### 
# 
# 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_S-nprx-L-pro-pol-II
_database_code_depnum_ccdc_archive 'CCDC 1861026'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_chemical_name_systematic        
'(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid; (2S)-pyrrolidin-1-ium-2-carboxylate, polymorph II'
_chemical_name_common            
;
S-naproxen L-proline 1:1 cocrystal, polymorph II
;
_chemical_formula_moiety         '2(C14 H14 O3), 2(C5 H9 N O2)'
_chemical_formula_sum            'C38 H46 N2 O10'
_chemical_formula_weight         690.77
_exptl_crystal_density_diffrn    1.304
_chemical_melting_point          ?
_chemical_absolute_configuration rm

_cell_length_a                   16.2991(7)
_cell_length_b                   5.8654(3)
_cell_length_c                   18.6876(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.052(4)
_cell_angle_gamma                90
_cell_volume                     1759.12(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_cell_special_details            
; 
The powder pattern was indexed using FOX program
;

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_space_group_name_Hall           'P 2yb'

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

_pd_spec_size_axial              4
_pd_spec_size_equat              0.5
_pd_spec_size_thick              0.5


_pd_spec_mounting                'Thin-wall 0.5 mm glass capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  colourless
_exptl_absorpt_correction_type   none

_pd_instr_location               
; 
X04SA beamline, Swiss Light Source (SLS), Villigen, Switzerland
;
_pd_calibration_special_details  
; 
using LaB₆ standard
;

_diffrn_ambient_temperature      295
_diffrn_source                   synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  'Mythen II'
_diffrn_detector                 'solid-state silicon microstrip detector'
_diffrn_detector_type            'Mythen II'
_diffrn_radiation_wavelength     0.776188
_pd_meas_scan_method             step
_pd_meas_special_details         
;  ?
;

_pd_meas_number_of_points        8571
_pd_meas_2theta_range_min        2.1492
_pd_meas_2theta_range_max        33.0012
_pd_meas_2theta_range_inc        0.0036


_pd_proc_ls_prof_R_factor        7.433
_pd_proc_ls_prof_wR_factor       8.797
_pd_proc_ls_prof_wR_expected     0.394

_refine_ls_R_I_factor            16.66
_refine_ls_number_reflns         ?
_refine_ls_number_parameters     ?
_refine_ls_number_restraints     ?
_refine_ls_goodness_of_fit_all   22.30
_refine_ls_shift/su_max          0.001

_pd_proc_2theta_range_min        2.1492
_pd_proc_2theta_range_max        33.0012
_pd_proc_2theta_range_inc        0.0036
_pd_proc_wavelength              0.776188

_computing_data_collection       ?
_computing_structure_solution    FOX
_computing_structure_refinement  'TOPAS V5'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C1 C 0.4132253 0.8815808 0.3264186 1 5.2(9)
O2 O 0.3815322 0.7681073 0.2725972 1 5.2(9)
O3 O 0.426872 1.09572527 0.3285084 1 5.2(9)
N4 N 0.4306089 0.4947677 0.3836366 1 5.2(9)
H5 H 0.4314883 0.4230187 0.4257283 1 6.3(11)
H6 H 0.3825784 0.459298 0.355283 1 6.3(11)
C7 C 0.4387236 0.7503615 0.3981061 1 5.2(9)
H8 H 0.4055678 0.7977525 0.4345082 1 6.3(11)
C9 C 0.53352 0.77109 0.42433 1 5.2(9)
H10 H 0.5428686 0.7072262 0.4729548 1 6.3(11)
H11 H 0.5536838 0.92655786 0.4237532 1 6.3(11)
C12 C 0.5701461 0.6138374 0.3722727 1 5.2(9)
H13 H 0.6250754 0.5496052 0.3885385 1 6.3(11)
H14 H 0.5744445 0.7044736 0.3296679 1 6.3(11)
C15 C 0.5041637 0.4246145 0.351945 1 5.2(9)
H16 H 0.4878187 0.3876927 0.300847 1 6.3(11)
H17 H 0.5290842 0.2905682 0.3773278 1 6.3(11)
C1a C 0.4169247 0.7046517 0.08520564 1 5.9(8)
O2a O 0.4605275 0.8184751 0.1363002 1 5.9(8)
O3a O 0.3648913 0.7815361 0.03449704 1 5.9(8)
N4a N 0.4059701 0.3457807 0.1554064 1 5.9(8)
H5a H 0.4415798 0.2349025 0.1718639 1 7.0(10)
H6a H 0.4108739 0.44758211 0.1912169 1 7.0(10)
C7a C 0.4302503 0.44499206 0.0866116 1 5.9(8)
H8a H 0.4902547 0.42993547 0.08724841 1 7.0(10)
C9a C 0.38418 0.32184 0.02694 1 5.9(8)
H10a H 0.4132756 0.1878027 0.01404872 1 7.0(10)
H11a H 0.375999 0.41021058 -0.01761318 1 7.0(10)
C12a C 0.3018637 0.2530446 0.05023065 1 5.9(8)
H13a H 0.2869596 0.103846 0.02959076 1 7.0(10)
H14a H 0.2548376 0.3536792 0.03497672 1 7.0(10)
C15a C 0.3220084 0.2428774 0.134134 1 5.9(8)
H16a H 0.2802501 0.3343764 0.1519306 1 7.0(10)
H17a H 0.3227415 0.0890429 0.153286 1 7.0(10)
C1b C 1.096738 0.3217831 0.01142655 1 3.7(6)
O2b O 1.10121 0.1833438 0.07705142 1 3.7(6)
C3b C 1.029418 0.1180806 0.09867653 1 3.7(6)
C4b C 1.021105 -0.0988843 0.1274233 1 3.7(6)
C5b C 0.9500231 -0.1624172 0.1506106 1 3.7(6)
C6b C 0.8831824 -0.0080585 0.1463015 1 3.7(6)
C7b C 0.8126864 -0.0654109 0.1770386 1 3.7(6)
C8b C 0.7498079 0.0877478 0.175797 1 3.7(6)
C9b C 0.7540465 0.2983122 0.1428622 1 3.7(6)
C10b C 0.8226778 0.3546087 0.1134572 1 3.7(6)
C11b C 0.8884529 0.1980583 0.1160271 1 3.7(6)
C12b C 0.9629871 0.2635 0.09081751 1 3.7(6)
C13b C 0.6764387 0.0316794 0.2132286 1 3.7(6)
C14b C 0.7024876 -0.1245599 0.2821946 1 3.7(6)
C15b C 0.6174159 -0.0892784 0.157315 1 3.7(6)
O16b O 0.5971448 -0.2908183 0.1773545 1 3.7(6)
O17b O 0.5887986 -0.0171334 0.09812566 1 3.7(6)
H18b H 1.067204 -0.1949545 0.1346553 1 4.5(7)
H19b H 0.9447374 -0.309725 0.1676478 1 4.5(7)
H20b H 0.8083437 -0.2099026 0.1965264 1 4.5(7)
H21b H 0.7106856 0.40220544 0.1414178 1 4.5(7)
H22b H 0.8247506 0.493948109 0.09009197 1 4.5(7)
H23b H 0.9682466 0.41024572 0.07332017 1 4.5(7)
H24b H 0.6498681 0.1714858 0.2266156 1 4.5(7)
H25b H 1.03993 0.3648293 -0.005954015 1 4.5(7)
H26b H 1.130021 0.45645786 0.02242726 1 4.5(7)
H27b H 1.117371 0.2353328 -0.02529161 1 4.5(7)
H28b H 0.7484471 -0.056131 0.3140868 1 4.5(7)
H29b H 0.6560784 -0.1415596 0.3070982 1 4.5(7)
H30b H 0.7197056 -0.2710515 0.2673152 1 4.5(7)
H31b H 0.550604 -0.2942984 0.1883433 1 4.5(7)
C1c C 0.702701 0.4223105 0.5082918 1 2.9(5)
O2c O 0.7324021 0.5582845 0.4524103 1 2.9(5)
C3c C 0.7986271 0.4828179 0.4239559 1 2.9(5)
C4c C 0.7951211 0.2775901 0.3855527 1 2.9(5)
C5c C 0.8606705 0.2044571 0.3557215 1 2.9(5)
C6c C 0.93390327 0.3361255 0.3632094 1 2.9(5)
C7c C 0.998744208 0.2723121 0.3261014 1 2.9(5)
C8c C 1.06769977 0.4056434 0.3304272 1 2.9(5)
C9c C 1.07535939 0.601004 0.3728919 1 2.9(5)
C10c C 1.01202514 0.6645555 0.4081743 1 2.9(5)
C11c C 0.93998333 0.5292233 0.4025479 1 2.9(5)
C12c C 0.8712187 0.6044099 0.434637 1 2.9(5)
C13c C 1.1353174 0.3441513 0.2868943 1 2.9(5)
C14c C 1.19691 0.1568614 0.3258804 1 2.9(5)
C15c C 1.1809955 0.5590115 0.2826112 1 2.9(5)
O16c O 1.1738209 0.6926089 0.2263553 1 2.9(5)
O17c O 1.2283549 0.6058973 0.3380038 1 2.9(5)
H18c H 0.7449574 0.1982993 0.3767675 1 3.5(6)
H19c H 0.8580197 0.0644069 0.3320972 1 3.5(6)
H20c H 0.991916067 0.1468536 0.2952012 1 3.5(6)
H21c H 1.1229375 0.6907687 0.3764905 1 3.5(6)
H22c H 1.01775237 0.7935721 0.4375533 1 3.5(6)
H23c H 0.873917 0.7435725 0.4587845 1 3.5(6)
H24c H 1.1106503 0.2941532 0.2378065 1 3.5(6)
H25c H 0.6635458 0.3106728 0.485584 1 3.5(6)
H26c H 0.7490107 0.3467848 0.5375975 1 3.5(6)
H27c H 0.6760027 0.5201179 0.5384454 1 3.5(6)
H28c H 1.1655957 0.0274402 0.3374132 1 3.5(6)
H29c H 1.2344904 0.1110607 0.2943089 1 3.5(6)
H30c H 1.2276504 0.2177852 0.3702636 1 3.5(6)
H31c H 1.2189076 0.7379938 0.2182788 1 3.5(6)

loop_
_pd_proc_2theta_corrected
_pd_calc_intensity_total
_pd_proc_intensity_total
2.14920 93.93468 93.93729
2.15280 93.97622 94.11651
2.15640 94.01779 93.92063
2.16000 94.05941 94.36558
2.16360 94.10105 94.25272
2.16720 94.14274 94.66208
2.17080 94.18448 94.53873
2.17440 94.22625 94.82017
2.17800 94.26808 94.45862
2.18160 94.30995 94.70284
2.18520 94.35188 94.92171
2.18880 94.39386 95.07130
2.19240 94.43590 95.25528
2.19600 94.47801 95.08488
2.19960 94.52018 95.41411
2.20320 94.56243 95.50292
2.20680 94.60475 94.86716
2.21040 94.64716 95.04506
2.21400 94.68965 95.20842
2.21760 94.73224 95.06178
2.22120 94.77493 95.54975
2.22480 94.81772 95.35902
2.22840 94.86064 95.32242
2.23200 94.90367 95.77154
2.23560 94.94684 96.14916
2.23920 94.99016 96.27677
2.24280 95.03363 95.38384
2.24640 95.07727 95.81181
2.25000 95.12109 95.87866
2.25360 95.16511 95.96834
2.25720 95.20934 96.03878
2.26080 95.25381 96.07764
2.26440 95.29853 96.42713
2.26800 95.34354 96.64081
2.27160 95.38884 96.16544
2.27520 95.43448 96.31566
2.27880 95.48049 96.78487
2.28240 95.52691 97.14048
2.28600 95.57377 97.06704
2.28960 95.62112 96.92226
2.29320 95.66902 97.05229
2.29680 95.71754 96.93647
2.30040 95.76673 97.20945
2.30400 95.81669 97.30676
2.30760 95.86751 97.61296
2.31120 95.91930 97.50042
2.31480 95.97220 97.69338
2.31840 96.02638 97.97003
2.32200 96.08209 97.88461
2.32560 96.13967 97.94898
2.32920 96.19967 97.77020
2.33280 96.26300 98.28081
2.33640 96.33119 98.67147
2.34000 96.40695 98.86512
2.34360 96.49486 98.53526
2.34720 96.60267 98.79823
2.35080 96.74309 99.43511
2.35440 96.93632 99.69577
2.35800 97.21338 99.81683
2.36160 97.62018 100.49162
2.36520 98.22189 101.10821
2.36880 99.10702 101.36432
2.37240 100.38985 101.27639
2.37600 102.20963 102.34825
2.37960 104.72440 103.25576
2.38320 108.09735 104.64452
2.38680 112.47453 106.93815
2.39040 117.95404 109.67307
2.39400 124.54955 113.29374
2.39760 132.15398 118.73428
2.40120 140.51172 125.78174
2.40480 149.20896 135.29810
2.40840 157.68981 145.91094
2.41200 165.30180 157.24863
2.41560 171.36840 167.64100
2.41920 175.28101 174.43989
2.42280 176.59830 175.84159
2.42640 175.13563 172.43393
2.43000 171.01778 163.61048
2.43360 164.66613 152.78520
2.43720 156.71630 139.99177
2.44080 147.89872 127.90502
2.44440 138.92382 117.90309
2.44800 130.39485 111.23413
2.45160 122.75454 106.42575
2.45520 116.26558 104.25139
2.45880 111.02100 102.29508
2.46240 106.97674 101.82660
2.46600 103.99554 101.09825
2.46960 101.89174 100.50929
2.47320 100.46879 100.48494
2.47680 99.54557 100.37272
2.48040 98.97081 100.35204
2.48400 98.62780 99.94027
2.48760 98.43235 100.31683
2.49120 98.32728 100.34652
2.49480 98.27579 100.00067
2.49840 98.25537 99.97058
2.50200 98.25283 99.94096
2.50560 98.26074 99.91592
2.50920 98.27501 99.82126
2.51280 98.29345 100.00470
2.51640 98.31485 100.03524
2.52000 98.33852 99.93662
2.52360 98.36403 100.63936
2.52720 98.39110 100.45375
2.53080 98.41953 99.89427
2.53440 98.44914 100.07543
2.53800 98.47979 100.32175
2.54160 98.51137 100.79863
2.54520 98.54379 100.61435
2.54880 98.57695 100.58580
2.55240 98.61078 100.36677
2.55600 98.64522 100.44330
2.55960 98.68021 100.36463
2.56320 98.71571 100.51924
2.56680 98.75167 100.73292
2.57040 98.78806 100.66137
2.57400 98.82486 100.76394
2.57760 98.86200 101.08535
2.58120 98.89948 101.03992
2.58480 98.93727 101.56685
2.58840 98.97536 101.14286
2.59200 99.01374 100.86170
2.59560 99.05239 101.22794
2.59920 99.09130 100.83350
2.60280 99.13045 101.03691
2.60640 99.16986 100.93779
2.61000 99.20950 101.13843
2.61360 99.24937 101.06921
2.61720 99.28948 101.04755
2.62080 99.32982 101.18309
2.62440 99.37040 101.77000
2.62800 99.41122 101.91694
2.63160 99.45229 101.63653
2.63520 99.49361 101.48690
2.63880 99.53520 101.82196
2.64240 99.57707 102.19549
2.64600 99.61924 102.11807
2.64960 99.66173 101.91269
2.65320 99.70456 102.33237
2.65680 99.74776 102.51036
2.66040 99.79137 102.22181
2.66400 99.83542 102.80465
2.66760 99.87996 102.53169
2.67120 99.92506 102.55896
2.67480 99.97077 102.67539
2.67840 100.01718 102.87645
2.68200 100.06441 102.94681
2.68560 100.11263 103.33087
2.68920 100.16207 103.27345
2.69280 100.21314 103.69746
2.69640 100.26656 103.51686
2.70000 100.32357 103.85442
2.70360 100.38639 104.59442
2.70720 100.45886 104.47877
2.71080 100.54750 104.58137
2.71440 100.66296 104.87815
2.71800 100.82202 105.33299
2.72160 101.04988 106.21365
2.72520 101.38270 106.50724
2.72880 101.86950 107.17592
2.73240 102.57281 108.68080
2.73600 103.56656 110.03196
2.73960 104.93011 111.98506
2.74320 106.73732 114.15850
2.74680 109.04064 118.21374
2.75040 111.85165 123.90210
2.75400 115.12130 133.94832
2.75760 118.72493 148.27419
2.76120 122.45769 167.57803
2.76480 126.04485 191.08071
2.76840 129.16855 216.49560
2.77200 131.50906 241.57160
2.77560 132.79578 255.83206
2.77920 132.86081 259.50847
2.78280 131.68209 249.08339
2.78640 129.39710 228.99831
2.79000 126.27374 201.45983
2.79360 122.65014 172.98861
2.79720 118.87013 149.18188
2.80080 115.23295 131.49962
2.80440 111.96205 121.33960
2.80800 109.19239 114.93602
2.81160 106.97429 111.40318
2.81520 105.28949 109.67328
2.81880 104.07376 108.59715
2.82240 103.23985 107.43271
2.82600 102.69656 106.80960
2.82960 102.36146 106.41007
2.83320 102.16752 105.66106
2.83680 102.06454 105.45495
2.84040 102.01760 105.43536
2.84400 102.00385 104.76195
2.84760 102.00921 105.14994
2.85120 102.02542 105.39640
2.85480 102.04786 105.18571
2.85840 102.07400 105.11354
2.86200 102.10253 105.20828
2.86560 102.13270 104.76210
2.86920 102.16413 104.23860
2.87280 102.19657 104.33741
2.87640 102.22985 104.53432
2.88000 102.26386 104.79335
2.88360 102.29849 104.36763
2.88720 102.33368 104.16863
2.89080 102.36935 104.21606
2.89440 102.40546 104.28109
2.89800 102.44194 104.65557
2.90160 102.47876 104.94946
2.90520 102.51589 104.93352
2.90880 102.55329 105.00811
2.91240 102.59094 104.65680
2.91600 102.62881 104.46718
2.91960 102.66688 104.64439
2.92320 102.70513 104.74163
2.92680 102.74354 104.92183
2.93040 102.78211 104.88453
2.93400 102.82081 104.68790
2.93760 102.85963 105.29527
2.94120 102.89858 105.04879
2.94480 102.93762 104.94280
2.94840 102.97677 105.21371
2.95200 103.01600 105.11403
2.95560 103.05532 104.95392
2.95920 103.09471 105.12024
2.96280 103.13418 104.66663
2.96640 103.17371 105.06957
2.97000 103.21330 105.23816
2.97360 103.25295 105.53777
2.97720 103.29265 105.62385
2.98080 103.33240 105.52406
2.98440 103.37220 105.57899
2.98800 103.41204 105.97067
2.99160 103.45192 105.86716
2.99520 103.49184 105.71859
2.99880 103.53179 105.38851
3.00240 103.57178 105.44325
3.00600 103.61180 105.33334
3.00960 103.65185 105.28935
3.01320 103.69193 105.11754
3.01680 103.73204 105.17769
3.02040 103.77217 105.65058
3.02400 103.81232 105.91661
3.02760 103.85250 105.95772
3.03120 103.89270 106.24171
3.03480 103.93292 105.50381
3.03840 103.97316 106.04873
3.04200 104.01341 105.80486
3.04560 104.05369 106.56234
3.04920 104.09398 105.79692
3.05280 104.13429 105.76316
3.05640 104.17462 106.62100
3.06000 104.21496 106.28417
3.06360 104.25531 106.16359
3.06720 104.29568 106.23245
3.07080 104.33606 106.30884
3.07440 104.37645 106.62174
3.07800 104.41686 106.41688
3.08160 104.45728 106.38724
3.08520 104.49771 106.66831
3.08880 104.53815 106.65948
3.09240 104.57861 106.62055
3.09600 104.61907 106.44892
3.09960 104.65955 107.11983
3.10320 104.70003 107.07007
3.10680 104.74053 106.98141
3.11040 104.78103 106.20200
3.11400 104.82155 106.58195
3.11760 104.86208 106.29384
3.12120 104.90261 106.84647
3.12480 104.94316 106.64529
3.12840 104.98371 106.90086
3.13200 105.02428 107.06294
3.13560 105.06485 107.08368
3.13920 105.10544 106.82228
3.14280 105.14603 107.11558
3.14640 105.18664 107.27797
3.15000 105.22725 107.54238
3.15360 105.26788 107.75008
3.15720 105.30852 107.36368
3.16080 105.34917 107.62911
3.16440 105.38983 107.80670
3.16800 105.43050 107.50253
3.17160 105.47118 107.87525
3.17520 105.51188 108.00327
3.17880 105.55260 108.60827
3.18240 105.59332 107.97492
3.18600 105.63407 107.62979
3.18960 105.67482 107.77682
3.19320 105.71560 107.68269
3.19680 105.75640 108.23694
3.20040 105.79721 108.62928
3.20400 105.83805 108.07944
3.20760 105.87891 108.85822
3.21120 105.91980 108.53749
3.21480 105.96071 109.28256
3.21840 106.00166 108.98794
3.22200 106.04263 109.11698
3.22560 106.08365 108.85604
3.22920 106.12471 108.82278
3.23280 106.16581 108.79910
3.23640 106.20696 109.21080
3.24000 106.24817 109.83211
3.24360 106.28944 110.21943
3.24720 106.33079 109.91991
3.25080 106.37222 110.31332
3.25440 106.41374 110.77413
3.25800 106.45537 111.05163
3.26160 106.49712 110.92941
3.26520 106.53902 110.95885
3.26880 106.58110 111.67185
3.27240 106.62341 112.34352
3.27600 106.66602 112.37911
3.27960 106.70909 113.33726
3.28320 106.75285 113.37353
3.28680 106.79781 114.26374
3.29040 106.84481 115.27377
3.29400 106.89537 116.90079
3.29760 106.95200 117.99619
3.30120 107.01867 119.25033
3.30480 107.10129 121.45044
3.30840 107.20806 124.46549
3.31200 107.34954 127.93192
3.31560 107.53795 133.99334
3.31920 107.78564 142.08014
3.32280 108.10246 156.61312
3.32640 108.49223 178.03952
3.33000 108.94892 209.22100
3.33360 109.45362 248.60275
3.33720 109.97356 293.94879
3.34080 110.46417 339.44841
3.34440 110.87450 378.51165
3.34800 111.15562 402.96278
3.35160 111.27089 408.09934
3.35520 111.20616 391.79133
3.35880 110.97556 357.89159
3.36240 110.61819 313.49580
3.36600 110.18680 263.94302
3.36960 109.73510 217.69767
3.37320 109.30847 181.19959
3.37680 108.93876 156.29843
3.38040 108.64289 140.15156
3.38400 108.42430 130.84586
3.38760 108.27651 125.28657
3.39120 108.18739 122.03074
3.39480 108.14296 119.64904
3.39840 108.13016 117.56138
3.40200 108.13832 115.95748
3.40560 108.13258 114.86486
3.40920 108.13461 114.07022
3.41280 108.14105 113.10622
3.41640 108.14994 112.31525
3.42000 108.16019 111.99566
3.42360 108.17122 111.92761
3.42720 108.18273 111.49258
3.43080 108.19457 111.37163
3.43440 108.20665 111.33274
3.43800 108.21893 110.85878
3.44160 108.23136 110.67688
3.44520 108.24393 110.75437
3.44880 108.25661 110.47050
3.45240 108.26939 109.90328
3.45600 108.28226 110.47253
3.45960 108.29521 110.38820
3.46320 108.30823 109.82999
3.46680 108.32130 109.38441
3.47040 108.33443 109.51348
3.47400 108.34760 109.03549
3.47760 108.36082 109.50010
3.48120 108.37407 109.40191
3.48480 108.38736 109.85538
3.48840 108.40067 110.00758
3.49200 108.41402 109.58726
3.49560 108.42739 109.48947
3.49920 108.44078 109.88159
3.50280 108.45419 109.41359
3.50640 108.46762 109.43950
3.51000 108.48107 109.52565
3.51360 108.49453 108.96776
3.51720 108.50801 108.75290
3.52080 108.52150 109.30352
3.52440 108.53501 109.18077
3.52800 108.54852 108.95201
3.53160 108.56205 108.92887
3.53520 108.57559 109.91817
3.53880 108.58913 109.64614
3.54240 108.60268 109.35296
3.54600 108.61624 109.13674
3.54960 108.62981 109.30640
3.55320 108.64339 109.77276
3.55680 108.65697 109.82962
3.56040 108.67055 109.63933
3.56400 108.68415 109.55487
3.56760 108.69774 109.48038
3.57120 108.71135 110.08024
3.57480 108.72496 109.76096
3.57840 108.73857 109.19209
3.58200 108.75218 109.39224
3.58560 108.76580 109.61545
3.58920 108.77943 109.23547
3.59280 108.79306 109.92184
3.59640 108.80669 109.76793
3.60000 108.82032 109.65498
3.60360 108.83396 109.86676
3.60720 108.84760 109.74521
3.61080 108.86124 109.76126
3.61440 108.87489 109.46782
3.61800 108.88854 109.53075
3.62160 108.90219 109.69534
3.62520 108.91584 109.10211
3.62880 108.92950 109.73349
3.63240 108.94315 110.13815
3.63600 108.95681 109.70566
3.63960 108.97048 109.47348
3.64320 108.98414 109.39652
3.64680 108.99782 109.55637
3.65040 109.01152 109.87705
3.65400 109.02526 109.59605
3.65760 109.03909 109.58567
3.66120 109.05321 109.56923
3.66480 109.06689 110.32441
3.66840 109.08057 110.11085
3.67200 109.09425 109.69822
3.67560 109.10794 109.95852
3.67920 109.12163 110.21161
3.68280 109.13531 109.43808
3.68640 109.14900 109.65648
3.69000 109.16270 110.07053
3.69360 109.17639 110.04075
3.69720 109.19009 110.00114
3.70080 109.20378 109.93422
3.70440 109.21748 109.88934
3.70800 109.23118 110.17718
3.71160 109.24488 109.77212
3.71520 109.25859 110.26636
3.71880 109.27229 110.00929
3.72240 109.28600 110.20157
3.72600 109.29971 109.78979
3.72960 109.31342 110.43625
3.73320 109.32714 109.95310
3.73680 109.34085 110.29396
3.74040 109.35457 110.27549
3.74400 109.36829 110.33583
3.74760 109.38201 110.15661
3.75120 109.39573 109.98887
3.75480 109.40946 109.94000
3.75840 109.42319 109.86882
3.76200 109.43692 110.24521
3.76560 109.45066 110.36970
3.76920 109.46439 109.97737
3.77280 109.47813 110.02794
3.77640 109.49188 110.24773
3.78000 109.50562 110.01641
3.78360 109.51937 110.27902
3.78720 109.53312 110.42386
3.79080 109.54688 110.04256
3.79440 109.56064 109.96771
3.79800 109.57441 110.44062
3.80160 109.58818 109.64699
3.80520 109.60195 110.44400
3.80880 109.61573 110.05941
3.81240 109.62952 110.11944
3.81600 109.64331 110.47813
3.81960 109.65711 110.42519
3.82320 109.67092 110.99059
3.82680 109.68473 110.84338
3.83040 109.69855 110.28975
3.83400 109.71238 111.07917
3.83760 109.72623 110.85432
3.84120 109.74008 111.41703
3.84480 109.75394 111.50206
3.84840 109.76782 111.59132
3.85200 109.78171 111.30385
3.85560 109.79562 111.57336
3.85920 109.80954 111.32514
3.86280 109.82348 111.37749
3.86640 109.83745 111.11296
3.87000 109.85144 111.08055
3.87360 109.86545 110.69157
3.87720 109.87950 110.78968
3.88080 109.89358 111.07634
3.88440 109.90770 110.91070
3.88800 109.92186 111.22267
3.89160 109.93608 110.70893
3.89520 109.95035 110.96972
3.89880 109.96469 111.33669
3.90240 109.97910 110.38695
3.90600 109.99361 110.21278
3.90960 110.00822 110.78639
3.91320 110.02296 111.69872
3.91680 110.03785 111.10323
3.92040 110.05293 111.20711
3.92400 110.06828 111.00086
3.92760 110.08401 111.30057
3.93120 110.10036 111.23212
3.93480 110.11777 111.29482
3.93840 110.13712 111.07159
3.94200 110.15998 111.48477
3.94560 110.18900 111.38003
3.94920 110.22847 111.35044
3.95280 110.28461 111.17921
3.95640 110.36564 111.22618
3.96000 110.48109 111.74694
3.96360 110.64008 111.82486
3.96720 110.84841 111.74623
3.97080 111.10500 111.65064
3.97440 111.39844 111.70068
3.97800 111.70537 112.61115
3.98160 111.99171 113.05135
3.98520 112.21766 113.49995
3.98880 112.34600 113.96860
3.99240 112.35290 113.78594
3.99600 112.23773 114.23625
3.99960 112.02488 114.00598
4.00320 111.75427 113.40768
4.00680 111.46799 112.52593
4.01040 111.20070 112.16663
4.01400 110.97507 112.20826
4.01760 110.80109 112.03360
4.02120 110.67823 111.55467
4.02480 110.59914 111.66040
4.02840 110.55354 111.90346
4.03200 110.53123 111.52872
4.03560 110.52386 111.53793
4.03920 110.52538 111.34508
4.04280 110.53192 111.36561
4.04640 110.54120 111.50475
4.05000 110.55202 112.09721
4.05360 110.56410 111.74678
4.05720 110.57604 111.02076
4.06080 110.58823 111.37639
4.06440 110.60064 111.24801
4.06800 110.61323 111.69169
4.07160 110.62595 111.35594
4.07520 110.63880 111.78400
4.07880 110.65175 111.44441
4.08240 110.66478 111.47862
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32.92560 34.90731 35.03214
32.92920 34.92445 35.08042
32.93280 34.94056 34.83017
32.93640 34.95559 34.74639
32.94000 34.96952 35.05640
32.94360 34.98234 34.97229
32.94720 34.99401 35.15967
32.95080 35.00451 35.20394
32.95440 35.01380 35.22133
32.95800 35.02187 34.67862
32.96160 35.02869 34.79860
32.96520 35.03422 34.80818
32.96880 35.03844 34.84747
32.97240 35.04131 35.03209
32.97600 35.04283 34.84761
32.97960 35.04297 34.81825
32.98320 35.04172 34.72066
32.98680 35.03911 34.59133
32.99040 35.03514 34.61565
32.99400 35.02988 34.50261
32.99760 35.02339 34.56370
33.00120 35.01577 34.19148

# start Validation Reply Form
_vrf_GEOM001_S-nprx-L-pro-pol-II 
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM003_S-nprx-L-pro-pol-II 
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM006_S-nprx-L-pro-pol-II 
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM007_S-nprx-L-pro-pol-II 
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_PLAT413_S-nprx-L-pro-pol-II 
;
PROBLEM: Short Inter XH3 .. XHn H14 ..H29B 1.72 Ang.
RESPONSE: A possible reason of this alert is a disorder of the 
proline molecules. Proline is highly flexible in terms of conformations, 
which may cause its disorder that was observed in almost all the structures
 found from single-crystal X-ray diffraction. We tried to introduce disorder
 for proline in the refinement of powder X-ray diffraction data but it did not
 significantly improve the structural models and only made fit less stable, 
so we decided to omit it.
;
_vrf_PLAT430_S-nprx-L-pro-pol-II 
;
PROBLEM: Short Inter D...A Contact O2A ..O17B 2.52 Ang.
RESPONSE: A possible reason of this alert is a disorder of the 
proline molecules. Proline is highly flexible in terms of conformations, 
which may cause its disorder that was observed in almost all the structures
 found from single-crystal X-ray diffraction. We tried to introduce disorder
 for proline in the refinement of powder X-ray diffraction data but it did not
 significantly improve the structural models and only made fit less stable, 
so we decided to omit it.
;
_exptl_crystal_colour            colourless
_exptl_crystal_description       powder
####################################################################### 
# 
# 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_RS-nprx-D-pro-pol-II
_database_code_depnum_ccdc_archive 'CCDC 1861025'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_chemical_name_systematic        
'(2R)-2-(6-methoxynaphthalen-2-yl)propanoic acid (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid bis((2R)-pyrrolidin-1-ium-2-carboxylate), polymorph II'
_chemical_name_common            
;
RS-naproxen D-proline 1:1 cocrystal, polymorph II
;
_chemical_formula_moiety         '2(C14 H14 O3), 2(C5 H9 N O2)'
_chemical_formula_sum            'C38 H46 N2 O10'
_chemical_formula_weight         690.76
_exptl_crystal_density_diffrn    1.231
_chemical_melting_point          432(1)
_chemical_absolute_configuration rm


_cell_length_a                   12.5901(6)
_cell_length_b                   5.7587(3)
_cell_length_c                   51.425(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3728.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_special_details            
; 
The powder pattern was indexed using FOX program
;
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'

_pd_spec_size_axial              4
_pd_spec_size_equat              0.5
_pd_spec_size_thick              0.5


_pd_spec_mounting                'Thin-wall 0.5 mm glass capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  colourless
_exptl_absorpt_correction_type   none

_pd_instr_location               
; 
X04SA beamline, Swiss Light Source (SLS), Villigen, Switzerland
;
_pd_calibration_special_details  
; 
using LaB₆ standard
;

_diffrn_ambient_temperature      295
_diffrn_source                   synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  'Mythen II'
_diffrn_detector                 'solid-state silicon microstrip detector'
_diffrn_detector_type            'Mythen II'
_diffrn_radiation_wavelength     1.0007
_pd_meas_scan_method             step
_pd_meas_special_details         
;  ?
;

_pd_meas_number_of_points        9223
_pd_meas_2theta_range_min        1.800
_pd_meas_2theta_range_max        34.99920
_pd_meas_2theta_range_inc        0.0036


_pd_proc_ls_prof_R_factor        5.720
_pd_proc_ls_prof_wR_factor       6.275
_pd_proc_ls_prof_wR_expected     0.170

_refine_ls_R_I_factor            12.489
_refine_ls_number_reflns         ?
_refine_ls_number_parameters     ?
_refine_ls_number_restraints     ?
_refine_ls_goodness_of_fit_all   36.98
_refine_ls_shift/su_max          0.001

_pd_proc_2theta_range_min        1.800
_pd_proc_2theta_range_max        34.99920
_pd_proc_2theta_range_inc        0.0036
_pd_proc_wavelength              1.0007

_computing_data_collection       ?
_computing_structure_solution    FOX
_computing_structure_refinement  'TOPAS V5'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'-x+1/2, -y, z+1/2 '
'-x, y+1/2, -z+1/2 '
'x+1/2, -y+1/2, -z '
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C1a C 4 0.7620(11) -0.144(3) 0.9449(3) 1 7.76136
O2a O 4 0.7066(11) -0.153(3) 0.9240(3) 1 7.76136
O3a O 4 0.8257(11) -0.294(3) 0.9529(3) 1 7.76136
N4a N 4 0.6949(11) 0.265(3) 0.9462(3) 1 7.76136
H5a H 4 0.7094(11) 0.243(3) 0.9295(3) 1 9.313632
H6a H 4 0.7186(11) 0.405(3) 0.9505(3) 1 9.313632
C7a C 4 0.7487(11) 0.074(3) 0.9620(3) 1 7.76136
H8a H 4 0.8187(11) 0.123(3) 0.9682(3) 1 9.313632
C9a C 4 0.6735(11) 0.034(3) 0.9848(3) 1 7.76136
H10a H 4 0.6830(11) -0.119(3) 0.9924(3) 1 9.313632
H11a H 4 0.6832(11) 0.151(3) 0.9981(3) 1 9.313632
C12a C 4 0.5649(11) 0.050(3) 0.9713(3) 1 7.76136
H13a H 4 0.5445(11) -0.097(3) 0.9636(3) 1 9.313632
H14a H 4 0.5107(11) 0.097(3) 0.9837(3) 1 9.313632
C15a C 4 0.5787(11) 0.240(3) 0.9503(3) 1 7.76136
H16a H 4 0.5438(11) 0.195(3) 0.9343(3) 1 9.313632
H17a H 4 0.5500(11) 0.386(3) 0.9565(3) 1 9.313632
C1 C 4 0.3413(12) 0.530(4) 0.4601(2) 1 11.95527
O2 O 4 0.2474(12) 0.615(4) 0.4615(2) 1 11.95527
O3 O 4 0.4264(12) 0.641(4) 0.4593(2) 1 11.95527
N4 N 4 0.2578(12) 0.157(4) 0.4743(2) 1 11.95527
H5 H 4 0.2733(12) 0.009(4) 0.4778(2) 1 14.34632
H6 H 4 0.2464(12) 0.228(4) 0.4894(2) 1 14.34632
C7 C 4 0.3502(12) 0.264(4) 0.4594(2) 1 11.95527
H8 H 4 0.4186(12) 0.213(4) 0.4665(2) 1 14.34632
C9 C 4 0.3280(12) 0.160(4) 0.4316(2) 1 11.95527
H10 H 4 0.3624(12) 0.011(4) 0.4298(2) 1 14.34632
H11 H 4 0.3583(12) 0.262(4) 0.4185(2) 1 14.34632
C12 C 4 0.2072(12) 0.134(4) 0.4289(2) 1 11.95527
H13 H 4 0.1898(12) -0.018(4) 0.4220(2) 1 14.34632
H14 H 4 0.1782(12) 0.254(4) 0.4178(2) 1 14.34632
C15 C 4 0.1639(12) 0.164(4) 0.4569(2) 1 11.95527
H16 H 4 0.1143(12) 0.041(4) 0.4612(2) 1 14.34632
H17 H 4 0.1283(12) 0.312(4) 0.4589(2) 1 14.34632
O1c O 4 0.8498(8) 0.877(2) 0.2691(2) 1 2.7926
O2c O 4 0.5212(8) 0.578(2) 0.4023(2) 1 2.7926
O3c O 4 0.4697(8) 0.936(2) 0.4081(2) 1 2.7926
C4c C 4 0.6236(8) 0.666(2) 0.3226(2) 1 2.7926
C5c C 4 0.5533(8) 0.604(2) 0.3429(2) 1 2.7926
C6c C 4 0.7104(8) 0.521(2) 0.3167(2) 1 2.7926
C7c C 4 0.6112(8) 0.868(2) 0.3100(2) 1 2.7926
C8c C 4 0.4724(8) 0.749(2) 0.3495(2) 1 2.7926
C9c C 4 0.7839(8) 0.591(2) 0.2990(2) 1 2.7926
C10c C 4 0.6879(8) 0.940(2) 0.2911(2) 1 2.7926
C11c C 4 0.5263(8) 1.015(2) 0.3164(2) 1 2.7926
C12c C 4 0.4573(8) 0.955(2) 0.3359(2) 1 2.7926
C13c C 4 0.4009(8) 0.690(2) 0.3725(2) 1 2.7926
C14c C 4 0.7751(8) 0.805(2) 0.2863(2) 1 2.7926
C15c C 4 0.4668(8) 0.740(2) 0.3955(2) 1 2.7926
C16c C 4 0.3067(8) 0.869(2) 0.3757(2) 1 2.7926
C17c C 4 0.8791(8) 1.122(2) 0.2683(2) 1 2.7926
H18c H 4 0.5604(8) 0.462(2) 0.3512(2) 1 3.35112
H19c H 4 0.7160(8) 0.375(2) 0.3243(2) 1 3.35112
H20c H 4 0.8447(8) 0.501(2) 0.2969(2) 1 3.35112
H21c H 4 0.6835(8) 1.088(2) 0.2840(2) 1 3.35112
H22c H 4 0.5151(8) 1.151(2) 0.3070(2) 1 3.35112
H23c H 4 0.4014(8) 1.053(2) 0.3403(2) 1 3.35112
H24c H 4 0.3729(8) 0.532(2) 0.3709(2) 1 3.35112
H25c H 4 0.2569(8) 0.849(2) 0.3617(2) 1 3.35112
H26c H 4 0.2717(8) 0.843(2) 0.3920(2) 1 3.35112
H27c H 4 0.3343(8) 1.024(2) 0.3752(2) 1 3.35112
H28c H 4 0.4625(8) 0.919(2) 0.4238(2) 1 3.35112
H29c H 4 0.8285(8) 1.206(2) 0.2580(2) 1 3.35112
H30c H 4 0.8809(8) 1.183(2) 0.2857(2) 1 3.35112
H31c H 4 0.9485(8) 1.138(2) 0.2608(2) 1 3.35112
C1b C 4 0.1002(9) -0.335(2) 0.7581(2) 1 8.13096
O2b O 4 0.1111(9) -0.280(2) 0.7858(2) 1 8.13096
C3b C 4 0.1999(9) -0.169(2) 0.7941(2) 1 8.13096
C4b C 4 0.2457(9) 0.010(2) 0.7796(2) 1 8.13096
C5b C 4 0.3332(9) 0.125(2) 0.7882(2) 1 8.13096
C6b C 4 0.3793(9) 0.064(2) 0.8122(2) 1 8.13096
C7b C 4 0.4634(9) 0.199(2) 0.8224(2) 1 8.13096
C8b C 4 0.5044(9) 0.147(2) 0.8462(2) 1 8.13096
C9b C 4 0.4657(9) -0.041(2) 0.8601(2) 1 8.13096
C10b C 4 0.3832(9) -0.170(2) 0.8503(2) 1 8.13096
C11b C 4 0.3392(9) -0.113(2) 0.8260(2) 1 8.13096
C12b C 4 0.2479(9) -0.236(2) 0.8167(2) 1 8.13096
C13b C 4 0.5903(9) 0.301(2) 0.8579(2) 1 8.13096
C14b C 4 0.5888(9) 0.555(2) 0.8463(2) 1 8.13096
C15b C 4 0.5638(9) 0.310(2) 0.8858(2) 1 8.13096
O16b O 4 0.5905(9) 0.504(2) 0.8969(2) 1 8.13096
O17b O 4 0.5218(9) 0.159(2) 0.8980(2) 1 8.13096
H18b H 4 0.2113(9) 0.060(2) 0.7645(2) 1 9.757152
H19b H 4 0.3643(9) 0.239(2) 0.7779(2) 1 9.757152
H20b H 4 0.4924(9) 0.319(2) 0.8126(2) 1 9.757152
H21b H 4 0.4945(9) -0.077(2) 0.8762(2) 1 9.757152
H22b H 4 0.3584(9) -0.298(2) 0.8595(2) 1 9.757152
H23b H 4 0.2172(9) -0.351(2) 0.8269(2) 1 9.757152
H24b H 4 0.6606(9) 0.231(2) 0.8557(2) 1 9.757152
H25b H 4 0.0619(9) -0.213(2) 0.7496(2) 1 9.757152
H26b H 4 0.0621(9) -0.478(2) 0.7562(2) 1 9.757152
H27b H 4 0.1693(9) -0.350(2) 0.7505(2) 1 9.757152
H28b H 4 0.5438(9) 0.652(2) 0.8567(2) 1 9.757152
H29b H 4 0.5623(9) 0.550(2) 0.8288(2) 1 9.757152
H30b H 4 0.6596(9) 0.617(2) 0.8462(2) 1 9.757152
H31b H 4 0.6209(9) 0.485(2) 0.9109(2) 1 9.757152

loop_
_pd_proc_2theta_corrected
_pd_calc_intensity_total
_pd_proc_intensity_total
1.80000 1244.26245 1250.45333
1.80360 1244.26244 1249.69614
1.80720 1244.26250 1251.04362
1.81080 1244.26262 1250.44738
1.81440 1244.26280 1251.18145
1.81800 1244.26306 1251.30804
1.82160 1244.26339 1250.09349
1.82520 1244.26379 1247.79152
1.82880 1244.26428 1247.44791
1.83240 1244.26484 1248.66331
1.83600 1244.26549 1244.98971
1.83960 1244.26623 1247.61191
1.84320 1244.26706 1248.20267
1.84680 1244.26799 1249.08296
1.85040 1244.26901 1247.84074
1.85400 1244.27015 1244.65918
1.85760 1244.27139 1246.95382
1.86120 1244.27274 1246.81534
1.86480 1244.27421 1245.83081
1.86840 1244.27580 1247.19932
1.87200 1244.27753 1247.17959
1.87560 1244.27939 1246.84112
1.87920 1244.28138 1249.42946
1.88280 1244.28353 1248.47290
1.88640 1244.28583 1246.98366
1.89000 1244.28829 1249.13052
1.89360 1244.29093 1245.06162
1.89720 1244.29373 1246.16449
1.90080 1244.29673 1244.94555
1.90440 1244.29992 1245.12186
1.90800 1244.30331 1245.92370
1.91160 1244.30692 1244.48895
1.91520 1244.31076 1245.67348
1.91880 1244.31484 1247.28839
1.92240 1244.31916 1245.64818
1.92600 1244.32375 1244.93282
1.92960 1244.32862 1246.40259
1.93320 1244.33379 1247.68366
1.93680 1244.33926 1245.84601
1.94040 1244.34506 1244.91088
1.94400 1244.35121 1245.83690
1.94760 1244.35773 1245.23146
1.95120 1244.36463 1247.61179
1.95480 1244.37194 1244.70681
1.95840 1244.37970 1245.06458
1.96200 1244.38791 1241.37469
1.96560 1244.39662 1242.32949
1.96920 1244.40585 1245.45754
1.97280 1244.41564 1245.29711
1.97640 1244.42602 1244.21847
1.98000 1244.43704 1246.49678
1.98360 1244.44873 1246.03523
1.98720 1244.46115 1246.79724
1.99080 1244.47434 1245.68017
1.99440 1244.48837 1244.66285
1.99800 1244.50328 1244.24604
2.00160 1244.51915 1244.20063
2.00520 1244.53605 1241.55452
2.00880 1244.55406 1244.47764
2.01240 1244.57326 1245.13738
2.01600 1244.59375 1246.49597
2.01960 1244.61564 1247.53963
2.02320 1244.63904 1245.52897
2.02680 1244.66408 1247.49627
2.03040 1244.69091 1246.58082
2.03400 1244.71967 1244.20476
2.03760 1244.75056 1244.41930
2.04120 1244.78376 1247.84580
2.04480 1244.81949 1244.73871
2.04840 1244.85801 1248.07541
2.05200 1244.89959 1247.61223
2.05560 1244.94454 1245.36770
2.05920 1244.99322 1247.16184
2.06280 1245.04603 1245.26817
2.06640 1245.10342 1248.87496
2.07000 1245.16592 1245.98288
2.07360 1245.23413 1244.92031
2.07720 1245.30872 1245.72928
2.08080 1245.39050 1247.20594
2.08440 1245.48039 1250.29180
2.08800 1245.57945 1252.70950
2.09160 1245.68894 1251.90788
2.09520 1245.81034 1249.35740
2.09880 1245.94537 1249.92204
2.10240 1246.09612 1250.41325
2.10600 1246.26506 1251.17310
2.10960 1246.45515 1251.20277
2.11320 1246.67001 1252.60809
2.11680 1246.91403 1247.21020
2.12040 1247.19262 1253.27171
2.12400 1247.51249 1253.95196
2.12760 1247.88211 1255.81862
2.13120 1248.31236 1255.12925
2.13480 1248.81794 1256.32165
2.13840 1249.42041 1259.32153
2.14200 1250.15583 1261.32093
2.14560 1251.09318 1267.41632
2.14920 1252.37646 1273.55645
2.15280 1254.31107 1278.70463
2.15640 1257.51965 1287.73170
2.16000 1263.17832 1303.54374
2.16360 1273.29339 1323.71599
2.16720 1290.87976 1344.60293
2.17080 1319.78659 1376.21243
2.17440 1363.87681 1417.99531
2.17800 1425.42937 1467.00314
2.18160 1503.04158 1527.65868
2.18520 1589.81633 1592.12326
2.18880 1672.92473 1651.77705
2.19240 1735.49038 1696.41113
2.19600 1761.31799 1715.57795
2.19960 1742.13143 1704.29092
2.20320 1683.15899 1656.18799
2.20680 1600.36482 1590.59002
2.21040 1511.84169 1513.07694
2.21400 1431.60351 1440.03107
2.21760 1367.47392 1374.35228
2.22120 1321.43322 1328.38841
2.22480 1291.36345 1298.23286
2.22840 1273.25462 1283.47982
2.23200 1262.99967 1272.69635
2.23560 1257.36413 1265.87015
2.23920 1254.21371 1262.76831
2.24280 1252.32195 1258.67573
2.24640 1251.05838 1254.99719
2.25000 1250.12454 1253.94823
2.25360 1249.38446 1250.22759
2.25720 1248.77421 1250.59632
2.26080 1248.26019 1248.69944
2.26440 1247.82173 1250.81932
2.26800 1247.44438 1246.83011
2.27160 1247.11724 1246.95869
2.27520 1246.83180 1248.17231
2.27880 1246.58128 1246.13604
2.28240 1246.36020 1246.66273
2.28600 1246.16412 1246.03000
2.28960 1245.98940 1246.04082
2.29320 1245.83303 1248.53457
2.29680 1245.69252 1244.96799
2.30040 1245.56576 1248.47879
2.30400 1245.45101 1246.28918
2.30760 1245.34677 1246.85066
2.31120 1245.25179 1249.07106
2.31480 1245.16497 1245.79707
2.31840 1245.08539 1244.11908
2.32200 1245.01226 1243.36236
2.32560 1244.94487 1243.15210
2.32920 1244.88262 1244.89760
2.33280 1244.82500 1245.14138
2.33640 1244.77153 1242.63275
2.34000 1244.72181 1241.40839
2.34360 1244.67549 1240.75539
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34.09920 479.56968 480.12665
34.10280 479.60314 478.30711
34.10640 479.45922 479.02024
34.11000 479.13635 477.91499
34.11360 478.64609 476.93753
34.11720 478.01430 475.64935
34.12080 477.26866 474.53713
34.12440 476.43923 473.48295
34.12800 475.55351 471.83581
34.13160 474.62887 470.14667
34.13520 473.69473 469.23261
34.13880 472.75927 467.39172
34.14240 471.83311 465.43179
34.14600 470.92407 467.52292
34.14960 470.03778 464.39119
34.15320 469.17769 462.32460
34.15680 468.34522 462.68081
34.16040 467.54017 463.32486
34.16400 466.76149 461.27937
34.16760 466.00832 457.02942
34.17120 465.28093 457.40406
34.17480 464.58134 455.73619
34.17840 463.91341 455.54425
34.18200 463.28244 453.60384
34.18560 462.69466 454.02246
34.18920 462.15610 455.74482
34.19280 461.67220 454.64056
34.19640 461.24727 453.54848
34.20000 460.88415 451.82108
34.20360 460.58404 452.28830
34.20720 460.34623 451.96241
34.21080 460.16796 450.37967
34.21440 460.04410 450.59670
34.21800 459.96712 451.04155
34.22160 459.92715 450.11257
34.22520 459.91233 451.27170
34.22880 459.90956 452.60029
34.23240 459.90560 449.59442
34.23600 459.88833 451.85336
34.23960 459.84810 449.11192
34.24320 459.77888 451.24104
34.24680 459.67897 450.44674
34.25040 459.55113 450.56419
34.25400 459.40220 449.89957
34.25760 459.24216 450.49363
34.26120 459.08284 450.97163
34.26480 458.93659 449.94917
34.26840 458.81488 450.29998
34.27200 458.72727 450.81140
34.27560 458.68056 449.70301
34.27920 458.67758 450.47403
34.28280 458.71985 451.57041
34.28640 458.80326 452.42611
34.29000 458.92120 452.16011
34.29360 459.06441 453.57276
34.29720 459.22185 453.96441
34.30080 459.38188 453.08184
34.30440 459.53373 453.92607
34.30800 459.66887 454.26512
34.31160 459.78203 454.06971
34.31520 459.87165 455.30697
34.31880 459.93943 455.81321
34.32240 459.98927 456.27363
34.32600 460.02570 456.33172
34.32960 460.05249 455.38778
34.33320 460.07144 456.00594
34.33680 460.08143 456.68820
34.34040 460.07988 455.99541
34.34400 460.06086 456.59326
34.34760 460.01727 455.95250
34.35120 459.94121 457.12949
34.35480 459.82489 456.64196
34.35840 459.66154 456.33957
34.36200 459.44642 455.60816
34.36560 459.17778 455.36952
34.36920 458.85756 456.09513
34.37280 458.49163 455.96620
34.37640 458.08944 454.65008
34.38000 457.66317 453.77686
34.38360 457.22660 454.08862
34.38720 456.79384 453.51560
34.39080 456.37834 453.22966
34.39440 455.99170 454.28751
34.39800 455.64569 451.53437
34.40160 455.34819 451.62421
34.40520 455.10628 450.23002
34.40880 454.92510 451.11017
34.41240 454.80846 452.71742
34.41600 454.75885 448.94982
34.41960 454.77764 450.15085
34.42320 454.86503 452.91825
34.42680 455.02008 451.74588
34.43040 455.24056 451.82928
34.43400 455.52279 450.24241
34.43760 455.85310 451.50696
34.44120 456.22965 451.78492
34.44480 456.64706 451.22224
34.44840 457.09538 452.06772
34.45200 457.56402 453.41995
34.45560 458.04261 454.32473
34.45920 458.52198 455.22609
34.46280 458.99486 455.87343
34.46640 459.45787 457.17682
34.47000 459.90896 456.80684
34.47360 460.34818 457.93048
34.47720 460.77526 459.63109
34.48080 461.18901 462.00388
34.48440 461.58599 462.60003
34.48800 461.96024 463.13164
34.49160 462.30339 465.54440
34.49520 462.60573 465.49523
34.49880 462.85725 466.53264
34.50240 463.04869 468.79809
34.50600 463.17194 472.22358
34.50960 463.22015 471.70655
34.51320 463.18756 470.70516
34.51680 463.06951 474.50041
34.52040 462.86283 472.78717
34.52400 462.56668 472.51260
34.52760 462.18332 472.42432
34.53120 461.71868 473.41224
34.53480 461.18215 472.39353
34.53840 460.58584 471.37430
34.54200 459.94335 472.14892
34.54560 459.26861 471.55385
34.54920 458.57520 469.67281
34.55280 457.87565 469.89074
34.55640 457.18154 468.67940
34.56000 456.50339 467.04732
34.56360 455.85075 466.04056
34.56720 455.23204 466.96826
34.57080 454.65419 467.12068
34.57440 454.12343 466.05635
34.57800 453.64376 465.04547
34.58160 453.21791 463.60989
34.58520 452.84714 462.75206
34.58880 452.53142 463.45945
34.59240 452.26957 461.23971
34.59600 452.05931 461.42916
34.59960 451.89743 463.25981
34.60320 451.77963 462.76758
34.60680 451.70047 460.26015
34.61040 451.65319 462.61355
34.61400 451.62959 462.59930
34.61760 451.62006 460.62612
34.62120 451.61394 460.54706
34.62480 451.60006 460.35072
34.62840 451.56772 459.30850
34.63200 451.50779 458.80878
34.63560 451.41376 458.55338
34.63920 451.28260 458.18085
34.64280 451.11517 458.28821
34.64640 450.91596 457.10763
34.65000 450.69256 456.03693
34.65360 450.45454 453.26210
34.65720 450.21242 454.31066
34.66080 449.97651 454.88241
34.66440 449.75693 451.34408
34.66800 449.56201 451.44386
34.67160 449.39882 452.42236
34.67520 449.27298 453.40807
34.67880 449.18876 451.11377
34.68240 449.14922 448.45244
34.68600 449.15630 448.19615
34.68960 449.21096 448.86056
34.69320 449.31311 451.16778
34.69680 449.46160 451.94349
34.70040 449.65407 450.50958
34.70400 449.88671 451.81344
34.70760 450.15412 451.61658
34.71120 450.44913 452.20974
34.71480 450.76287 452.86364
34.71840 451.08501 452.10166
34.72200 451.40440 451.26885
34.72560 451.71004 451.53801
34.72920 451.99224 452.01443
34.73280 452.24390 452.14153
34.73640 452.46143 451.94284
34.74000 452.64523 451.47791
34.74360 452.79940 450.57537
34.74720 452.93097 451.25022
34.75080 453.04860 451.53432
34.75440 453.16120 450.97407
34.75800 453.27676 450.23297
34.76160 453.40135 451.78353
34.76520 453.53838 448.73900
34.76880 453.68849 450.50133
34.77240 453.84875 450.14767
34.77600 454.01291 451.21152
34.77960 454.17144 451.25425
34.78320 454.31200 449.15878
34.78680 454.41906 451.02708
34.79040 454.48067 451.13697
34.79400 454.48222 450.33969
34.79760 454.41391 450.09710
34.80120 454.27042 450.05724
34.80480 454.05202 449.20189
34.80840 453.76439 447.91698
34.81200 453.41770 448.22085
34.81560 453.02518 450.53535
34.81920 452.60143 450.72476
34.82280 452.16091 448.81031
34.82640 451.71631 448.03551
34.83000 451.27741 447.60098
34.83360 450.85568 448.10941
34.83720 450.45510 446.78445
34.84080 450.07938 446.07966
34.84440 449.73078 447.23946
34.84800 449.41082 447.80814
34.85160 449.12098 445.89878
34.85520 448.86308 446.65993
34.85880 448.63661 447.84623
34.86240 448.45034 445.55656
34.86600 448.30465 444.33147
34.86960 448.20292 445.97460
34.87320 448.14835 444.39722
34.87680 448.14377 444.19264
34.88040 448.19148 444.84797
34.88400 448.29317 444.94326
34.88760 448.44982 444.82088
34.89120 448.66155 445.42825
34.89480 448.92752 446.78259
34.89840 449.24464 447.42069
34.90200 449.61126 447.63304
34.90560 450.02092 446.92359
34.90920 450.46598 446.85113
34.91280 450.93649 447.76669
34.91640 451.42022 445.93595
34.92000 451.90310 447.74500
34.92360 452.36958 449.03344
34.92720 452.80624 447.48189
34.93080 453.20000 448.88874
34.93440 453.54199 450.44403
34.93800 453.82814 447.22001
34.94160 454.05949 448.34968
34.94520 454.24156 447.26540
34.94880 454.38286 447.16490
34.95240 454.49300 448.25849
34.95600 454.58085 447.77754
34.95960 454.65238 447.73126
34.96320 454.71325 448.10991
34.96680 454.76447 447.42523
34.97040 454.80660 447.01983
34.97400 454.84015 448.12075
34.97760 454.86687 449.26456
34.98120 454.89436 448.79476
34.98480 454.92973 449.36745
34.98840 454.98410 450.31421
34.99200 455.07024 450.53140
34.99560 455.20118 450.29127
34.99920 455.38863 452.29939
# start Validation Reply Form
_vrf_GEOM001_RS-nprx-D-pro-pol-II 
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM003_RS-nprx-D-pro-pol-II 
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM006_RS-nprx-D-pro-pol-II 
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM007_RS-nprx-D-pro-pol-II 
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_PLAT415_RS-nprx-D-pro-pol-II 
;
PROBLEM: Short Inter D-H..H-X H6 ..H10A 1.56 Ang.
RESPONSE:  A possible reason of this alert is a disorder of the 
proline molecules. Proline is highly flexible in terms of conformations, 
which may cause its disorder that was observed in almost all the structures
 found from single-crystal X-ray diffraction. We tried to introduce disorder
 for proline in the refinement of powder X-ray diffraction data but it did not
 significantly improve the structural models and only made fit less stable, 
so we decided to omit it.
;
_exptl_crystal_colour            colourless
_exptl_crystal_description       powder
####################################################################### 
# 
# 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_nt0026_RSnprxDproEtOHb2_polI
_database_code_depnum_ccdc_archive 'CCDC 1861020'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
(2R)-2-(6-methoxynaphthalen-2-yl)propanoic acid 
(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid 
bis((2R)-pyrrolidin-1-ium-2-carboxylate), polymorph I
;
_chemical_name_common            
'RS-naproxen D-proline 1:1 cocrystal, polymorph I'
_chemical_melting_point          435(1)
_chemical_formula_moiety         '2(C14 H14 O3), 2(C5 H9 N O2)'
_chemical_formula_sum            'C38 H46 N2 O10'
_chemical_formula_weight         690.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.1578(5)
_cell_length_b                   5.8278(2)
_cell_length_c                   25.6828(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.762(5)
_cell_angle_gamma                90
_cell_volume                     1798.45(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3642
_cell_measurement_theta_min      3.4710
_cell_measurement_theta_max      66.6840

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.760
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            11150
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         67.220
_diffrn_reflns_theta_full        67.220
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.788
_diffrn_reflns_point_group_measured_fraction_full 0.788
_reflns_number_total             5055
_reflns_number_gt                4166
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.434
_reflns_Friedel_fraction_max     0.534
_reflns_Friedel_fraction_full    0.534

_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0998P)²+0.7181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_chemical_absolute_configuration rm
_refine_ls_number_reflns         5055
_refine_ls_number_parameters     458
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1964
_refine_ls_wR_factor_gt          0.1847
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.3712(5) 0.5184(15) 0.3030(2) 0.135(3) Uani 1 1 d . . . . .
N1 N 0.5540(5) 0.6733(9) 0.4343(2) 0.0862(17) Uani 1 1 d . . . . .
H1A H 0.513891 0.546822 0.426448 0.103 Uiso 1 1 calc R U . . .
H1B H 0.551304 0.709025 0.467816 0.103 Uiso 1 1 calc R U . . .
C1 C 0.3152(5) 0.3519(17) 0.2903(3) 0.087(2) Uani 1 1 d . . . . .
O2 O 0.3088(5) 0.1850(10) 0.3237(2) 0.1139(18) Uani 1 1 d . . . . .
H2O H 0.350582 0.211743 0.351227 0.137 Uiso 1 1 calc R U . . .
N2 N 0.0516(4) 0.4951(8) 0.43741(16) 0.0618(11) Uani 1 1 d . . . . .
H2A H 0.020584 0.363102 0.425500 0.074 Uiso 1 1 calc R U . . .
H2B H 0.026383 0.531561 0.467100 0.074 Uiso 1 1 calc R U . . .
C2 C 0.2506(4) 0.3078(12) 0.2368(2) 0.0747(16) Uani 1 1 d . . . . .
H2 H 0.228936 0.457651 0.221136 0.090 Uiso 1 1 calc R U . . .
O3 O 0.6672(3) -0.0275(10) 0.04154(17) 0.0856(13) Uani 1 1 d . . . . .
C3 C 0.1451(5) 0.1717(16) 0.2368(3) 0.095(2) Uani 1 1 d . . . . .
H3A H 0.104027 0.167583 0.201822 0.142 Uiso 1 1 calc R U . . .
H3B H 0.100661 0.242891 0.260158 0.142 Uiso 1 1 calc R U . . .
H3C H 0.163504 0.018130 0.248555 0.142 Uiso 1 1 calc R U . . .
C38 C 0.1755(6) 0.4726(14) 0.4472(3) 0.108(3) Uani 1 1 d . . . . .
H38A H 0.205034 0.517551 0.483022 0.130 Uiso 1 1 calc R U . . .
H38B H 0.197808 0.315821 0.441673 0.130 Uiso 1 1 calc R U . . .
C37 C 0.2159(5) 0.6301(16) 0.4085(4) 0.114(3) Uani 1 1 d . . . . .
H37A H 0.276933 0.560905 0.393866 0.137 Uiso 1 1 calc R U . . .
H37B H 0.241062 0.774063 0.425189 0.137 Uiso 1 1 calc R U . . .
O4 O 0.7956(4) 0.3659(9) 0.33213(16) 0.0889(13) Uani 1 1 d . . . . .
C4 C 0.3270(4) 0.1971(10) 0.2027(2) 0.0650(14) Uani 1 1 d . . . . .
O5 O 0.8796(3) 0.0721(8) 0.30041(15) 0.0786(11) Uani 1 1 d . . . . .
H5A H 0.916843 0.075136 0.329845 0.094 Uiso 1 1 calc R U . . .
C5 C 0.3499(4) 0.3022(10) 0.1578(2) 0.0650(14) Uani 1 1 d . . . . .
H5 H 0.314141 0.439275 0.147289 0.078 Uiso 1 1 calc R U . . .
O6 O 1.1575(3) 0.6360(9) 0.04520(16) 0.0836(13) Uani 1 1 d . . . . .
C6 C 0.4259(4) 0.2095(10) 0.1271(2) 0.0609(13) Uani 1 1 d . . . . .
O7 O 0.5579(4) 1.0885(8) 0.47692(14) 0.0850(12) Uani 1 1 d . . . . .
C7 C 0.4510(5) 0.3192(12) 0.0809(2) 0.0744(16) Uani 1 1 d . . . . .
H7 H 0.413573 0.452907 0.068936 0.089 Uiso 1 1 calc R U . . .
O8 O 0.4563(4) 1.2508(9) 0.40875(19) 0.1018(16) Uani 1 1 d . . . . .
C8 C 0.5290(5) 0.2306(13) 0.0540(2) 0.0757(16) Uani 1 1 d . . . . .
H8 H 0.543087 0.303176 0.023431 0.091 Uiso 1 1 calc R U . . .
O9 O 0.0474(4) 0.9211(7) 0.47289(14) 0.0857(13) Uani 1 1 d . . . . .
C9 C 0.5885(4) 0.0332(11) 0.0711(2) 0.0674(14) Uani 1 1 d . . . . .
O10 O -0.0076(4) 1.0783(7) 0.39526(15) 0.0786(11) Uani 1 1 d . . . . .
C10 C 0.7280(5) -0.2303(15) 0.0549(3) 0.094(2) Uani 1 1 d . . . . .
H10A H 0.776503 -0.258892 0.029442 0.141 Uiso 1 1 calc R U . . .
H10B H 0.677518 -0.356707 0.055297 0.141 Uiso 1 1 calc R U . . .
H10C H 0.771490 -0.213406 0.089195 0.141 Uiso 1 1 calc R U . . .
C11 C 0.5641(4) -0.0828(12) 0.1145(2) 0.0691(14) Uani 1 1 d . . . . .
H11 H 0.601417 -0.218212 0.125167 0.083 Uiso 1 1 calc R U . . .
C12 C 0.4821(4) 0.0041(10) 0.1431(2) 0.0630(13) Uani 1 1 d . . . . .
C13 C 0.4546(5) -0.1056(12) 0.1888(2) 0.0736(15) Uani 1 1 d . . . . .
H13 H 0.488957 -0.243757 0.199649 0.088 Uiso 1 1 calc R U . . .
C14 C 0.3796(5) -0.0141(12) 0.2171(2) 0.0727(15) Uani 1 1 d . . . . .
H14 H 0.362755 -0.091966 0.246499 0.087 Uiso 1 1 calc R U . . .
C15 C 0.8075(4) 0.2420(10) 0.2958(2) 0.0581(12) Uani 1 1 d . . . . .
C16 C 0.7458(4) 0.2648(10) 0.2407(2) 0.0617(13) Uani 1 1 d . . . . .
H16 H 0.726247 0.110876 0.227013 0.074 Uiso 1 1 calc R U . . .
C17 C 0.6394(4) 0.4026(15) 0.2396(3) 0.0884(19) Uani 1 1 d . . . . .
H17A H 0.657158 0.553738 0.253159 0.133 Uiso 1 1 calc R U . . .
H17B H 0.591753 0.327486 0.260843 0.133 Uiso 1 1 calc R U . . .
H17C H 0.601896 0.413587 0.203941 0.133 Uiso 1 1 calc R U . . .
C18 C 0.8238(4) 0.3755(10) 0.20649(19) 0.0604(12) Uani 1 1 d . . . . .
C19 C 0.8777(5) 0.5846(11) 0.2229(2) 0.0693(14) Uani 1 1 d . . . . .
H19 H 0.863174 0.654601 0.253627 0.083 Uiso 1 1 calc R U . . .
C20 C 0.9507(5) 0.6855(11) 0.1944(2) 0.0714(15) Uani 1 1 d . . . . .
H20 H 0.984205 0.823627 0.205910 0.086 Uiso 1 1 calc R U . . .
C21 C 0.9762(4) 0.5845(11) 0.14779(19) 0.0633(13) Uani 1 1 d . . . . .
C22 C 1.0577(5) 0.6751(11) 0.1191(2) 0.0691(14) Uani 1 1 d . . . . .
H22 H 1.096414 0.807604 0.130848 0.083 Uiso 1 1 calc R U . . .
C23 C 1.0792(4) 0.5685(13) 0.0747(2) 0.0705(15) Uani 1 1 d . . . . .
C24 C 1.2209(5) 0.8371(14) 0.0607(3) 0.090(2) Uani 1 1 d . . . . .
H24A H 1.274168 0.861147 0.037189 0.134 Uiso 1 1 calc R U . . .
H24B H 1.259125 0.818372 0.095955 0.134 Uiso 1 1 calc R U . . .
H24C H 1.172037 0.967093 0.059231 0.134 Uiso 1 1 calc R U . . .
C25 C 1.0197(5) 0.3726(13) 0.0559(2) 0.0732(15) Uani 1 1 d . . . . .
H25 H 1.033200 0.305507 0.024682 0.088 Uiso 1 1 calc R U . . .
C26 C 0.9423(5) 0.2783(12) 0.0825(2) 0.0723(15) Uani 1 1 d . . . . .
H26 H 0.904090 0.147090 0.069471 0.087 Uiso 1 1 calc R U . . .
C27 C 0.9193(4) 0.3787(10) 0.13015(19) 0.0596(12) Uani 1 1 d . . . . .
C28 C 0.8444(4) 0.2803(10) 0.16052(19) 0.0614(13) Uani 1 1 d . . . . .
H28 H 0.807719 0.145589 0.148774 0.074 Uiso 1 1 calc R U . . .
C29 C 0.5081(4) 1.0823(11) 0.4319(2) 0.0622(12) Uani 1 1 d . . . . .
C30 C 0.5073(4) 0.8671(10) 0.3990(2) 0.0614(13) Uani 1 1 d . . . . .
H30 H 0.431835 0.831496 0.381506 0.074 Uiso 1 1 calc R U . . .
C31 C 0.5871(5) 0.8825(12) 0.3597(2) 0.0725(15) Uani 1 1 d . . . . .
H31A H 0.566432 0.776348 0.330763 0.087 Uiso 1 1 calc R U . . .
H31B H 0.588939 1.036800 0.345685 0.087 Uiso 1 1 calc R U . . .
C32 C 0.6973(6) 0.8189(14) 0.3909(3) 0.096(2) Uani 1 1 d . . . . .
H32A H 0.748246 0.766384 0.367858 0.115 Uiso 1 1 calc R U . . .
H32B H 0.730181 0.949437 0.410989 0.115 Uiso 1 1 calc R U . . .
C33 C 0.6729(6) 0.6318(16) 0.4267(3) 0.110(3) Uani 1 1 d . . . . .
H33A H 0.722423 0.639520 0.460047 0.132 Uiso 1 1 calc R U . . .
H33B H 0.680777 0.482759 0.410863 0.132 Uiso 1 1 calc R U . . .
C34 C 0.0191(4) 0.9094(9) 0.42487(18) 0.0538(11) Uani 1 1 d . . . . .
C35 C 0.0239(4) 0.6774(8) 0.39785(19) 0.0530(11) Uani 1 1 d . . . . .
H35 H -0.046813 0.644273 0.375315 0.064 Uiso 1 1 calc R U . . .
C36 C 0.1184(6) 0.6679(13) 0.3667(3) 0.090(2) Uani 1 1 d . . . . .
H36A H 0.109415 0.542296 0.341636 0.108 Uiso 1 1 calc R U . . .
H36B H 0.125390 0.810674 0.348038 0.108 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
O1 C1 1.201(10) . ?
N1 C30 1.505(8) . ?
N1 C33 1.507(9) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C1 O2 1.307(10) . ?
C1 C2 1.499(9) . ?
O2 H2O 0.8200 . ?
N2 C35 1.473(6) . ?
N2 C38 1.495(8) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
C2 C3 1.508(9) . ?
C2 C4 1.514(8) . ?
C2 H2 0.9800 . ?
O3 C9 1.357(7) . ?
O3 C10 1.409(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C38 C37 1.489(12) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C37 C36 1.490(11) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
O4 C15 1.206(7) . ?
C4 C5 1.370(8) . ?
C4 C14 1.410(9) . ?
O5 C15 1.316(7) . ?
O5 H5A 0.8200 . ?
C5 C6 1.412(8) . ?
C5 H5 0.9300 . ?
O6 C23 1.362(7) . ?
O6 C24 1.425(9) . ?
C6 C12 1.408(8) . ?
C6 C7 1.422(8) . ?
O7 C29 1.221(6) . ?
C7 C8 1.357(9) . ?
C7 H7 0.9300 . ?
O8 C29 1.265(8) . ?
C8 C9 1.394(10) . ?
C8 H8 0.9300 . ?
O9 C34 1.231(6) . ?
C9 C11 1.374(8) . ?
O10 C34 1.256(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.419(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.420(8) . ?
C13 C14 1.359(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.502(7) . ?
C16 C17 1.520(8) . ?
C16 C18 1.531(7) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C28 1.362(7) . ?
C18 C19 1.417(8) . ?
C19 C20 1.366(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.409(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.422(8) . ?
C21 C27 1.424(8) . ?
C22 C23 1.358(8) . ?
C22 H22 0.9300 . ?
C23 C25 1.398(10) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.360(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.421(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.409(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.511(8) . ?
C30 C31 1.506(7) . ?
C30 H30 0.9800 . ?
C31 C32 1.500(9) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.485(11) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.525(7) . ?
C35 C36 1.498(7) . ?
C35 H35 0.9800 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?

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
C30 N1 C33 108.9(5) . . ?
C30 N1 H1A 109.9 . . ?
C33 N1 H1A 109.9 . . ?
C30 N1 H1B 109.9 . . ?
C33 N1 H1B 109.9 . . ?
H1A N1 H1B 108.3 . . ?
O1 C1 O2 120.7(7) . . ?
O1 C1 C2 125.7(8) . . ?
O2 C1 C2 113.5(7) . . ?
C1 O2 H2O 109.5 . . ?
C35 N2 C38 107.3(5) . . ?
C35 N2 H2A 110.2 . . ?
C38 N2 H2A 110.2 . . ?
C35 N2 H2B 110.2 . . ?
C38 N2 H2B 110.2 . . ?
H2A N2 H2B 108.5 . . ?
C1 C2 C3 114.6(6) . . ?
C1 C2 C4 108.8(4) . . ?
C3 C2 C4 111.9(6) . . ?
C1 C2 H2 107.1 . . ?
C3 C2 H2 107.1 . . ?
C4 C2 H2 107.1 . . ?
C9 O3 C10 118.1(6) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C37 C38 N2 105.0(5) . . ?
C37 C38 H38A 110.7 . . ?
N2 C38 H38A 110.7 . . ?
C37 C38 H38B 110.7 . . ?
N2 C38 H38B 110.7 . . ?
H38A C38 H38B 108.8 . . ?
C38 C37 C36 105.4(5) . . ?
C38 C37 H37A 110.7 . . ?
C36 C37 H37A 110.7 . . ?
C38 C37 H37B 110.7 . . ?
C36 C37 H37B 110.7 . . ?
H37A C37 H37B 108.8 . . ?
C5 C4 C14 117.9(5) . . ?
C5 C4 C2 121.1(5) . . ?
C14 C4 C2 120.9(5) . . ?
C15 O5 H5A 109.5 . . ?
C4 C5 C6 122.3(5) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C23 O6 C24 118.4(5) . . ?
C12 C6 C5 119.4(5) . . ?
C12 C6 C7 118.1(5) . . ?
C5 C6 C7 122.5(5) . . ?
C8 C7 C6 120.6(6) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.5(6) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
O3 C9 C11 125.7(6) . . ?
O3 C9 C8 114.5(6) . . ?
C11 C9 C8 119.8(5) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 119.9(6) . . ?
C9 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C6 C12 C11 120.0(5) . . ?
C6 C12 C13 117.4(5) . . ?
C11 C12 C13 122.6(5) . . ?
C14 C13 C12 121.8(6) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C4 121.1(6) . . ?
C13 C14 H14 119.5 . . ?
C4 C14 H14 119.5 . . ?
O4 C15 O5 122.5(5) . . ?
O4 C15 C16 125.0(5) . . ?
O5 C15 C16 112.4(5) . . ?
C15 C16 C17 111.5(5) . . ?
C15 C16 C18 108.3(4) . . ?
C17 C16 C18 111.5(5) . . ?
C15 C16 H16 108.5 . . ?
C17 C16 H16 108.5 . . ?
C18 C16 H16 108.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C28 C18 C19 118.0(5) . . ?
C28 C18 C16 122.6(5) . . ?
C19 C18 C16 119.4(5) . . ?
C20 C19 C18 121.3(5) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 121.3(6) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C22 123.0(6) . . ?
C20 C21 C27 117.6(5) . . ?
C22 C21 C27 119.4(5) . . ?
C23 C22 C21 120.2(6) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 O6 125.1(6) . . ?
C22 C23 C25 120.5(6) . . ?
O6 C23 C25 114.4(5) . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C23 121.2(5) . . ?
C26 C25 H25 119.4 . . ?
C23 C25 H25 119.4 . . ?
C25 C26 C27 120.5(6) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 122.5(5) . . ?
C28 C27 C21 119.4(5) . . ?
C26 C27 C21 118.1(5) . . ?
C18 C28 C27 122.3(5) . . ?
C18 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
O7 C29 O8 124.2(5) . . ?
O7 C29 C30 120.9(5) . . ?
O8 C29 C30 114.9(5) . . ?
N1 C30 C31 103.1(5) . . ?
N1 C30 C29 108.4(4) . . ?
C31 C30 C29 112.1(5) . . ?
N1 C30 H30 111.0 . . ?
C31 C30 H30 111.0 . . ?
C29 C30 H30 111.0 . . ?
C32 C31 C30 103.9(5) . . ?
C32 C31 H31A 111.0 . . ?
C30 C31 H31A 111.0 . . ?
C32 C31 H31B 111.0 . . ?
C30 C31 H31B 111.0 . . ?
H31A C31 H31B 109.0 . . ?
C33 C32 C31 105.4(6) . . ?
C33 C32 H32A 110.7 . . ?
C31 C32 H32A 110.7 . . ?
C33 C32 H32B 110.7 . . ?
C31 C32 H32B 110.7 . . ?
H32A C32 H32B 108.8 . . ?
C32 C33 N1 104.4(6) . . ?
C32 C33 H33A 110.9 . . ?
N1 C33 H33A 110.9 . . ?
C32 C33 H33B 110.9 . . ?
N1 C33 H33B 110.9 . . ?
H33A C33 H33B 108.9 . . ?
O9 C34 O10 124.8(5) . . ?
O9 C34 C35 118.8(4) . . ?
O10 C34 C35 116.3(4) . . ?
N2 C35 C36 103.2(4) . . ?
N2 C35 C34 110.3(4) . . ?
C36 C35 C34 111.2(5) . . ?
N2 C35 H35 110.7 . . ?
C36 C35 H35 110.7 . . ?
C34 C35 H35 110.7 . . ?
C37 C36 C35 102.1(5) . . ?
C37 C36 H36A 111.3 . . ?
C35 C36 H36A 111.3 . . ?
C37 C36 H36B 111.3 . . ?
C35 C36 H36B 111.3 . . ?
H36A C36 H36B 109.2 . . ?

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
O1 C1 C2 C3 -148.3(8) . . . . ?
O2 C1 C2 C3 33.6(9) . . . . ?
O1 C1 C2 C4 85.6(9) . . . . ?
O2 C1 C2 C4 -92.4(7) . . . . ?
C35 N2 C38 C37 -5.4(7) . . . . ?
N2 C38 C37 C36 -20.1(8) . . . . ?
C1 C2 C4 C5 -118.2(7) . . . . ?
C3 C2 C4 C5 114.2(7) . . . . ?
C1 C2 C4 C14 59.6(8) . . . . ?
C3 C2 C4 C14 -68.0(7) . . . . ?
C14 C4 C5 C6 -1.8(8) . . . . ?
C2 C4 C5 C6 176.1(5) . . . . ?
C4 C5 C6 C12 -1.1(8) . . . . ?
C4 C5 C6 C7 -179.2(5) . . . . ?
C12 C6 C7 C8 -1.7(8) . . . . ?
C5 C6 C7 C8 176.5(5) . . . . ?
C6 C7 C8 C9 -1.3(9) . . . . ?
C10 O3 C9 C11 1.9(8) . . . . ?
C10 O3 C9 C8 -177.5(5) . . . . ?
C7 C8 C9 O3 -177.0(6) . . . . ?
C7 C8 C9 C11 3.6(9) . . . . ?
O3 C9 C11 C12 177.9(5) . . . . ?
C8 C9 C11 C12 -2.8(8) . . . . ?
C5 C6 C12 C11 -175.8(5) . . . . ?
C7 C6 C12 C11 2.5(7) . . . . ?
C5 C6 C12 C13 2.9(7) . . . . ?
C7 C6 C12 C13 -178.9(5) . . . . ?
C9 C11 C12 C6 -0.2(8) . . . . ?
C9 C11 C12 C13 -178.8(5) . . . . ?
C6 C12 C13 C14 -1.8(8) . . . . ?
C11 C12 C13 C14 176.8(6) . . . . ?
C12 C13 C14 C4 -1.1(9) . . . . ?
C5 C4 C14 C13 2.9(8) . . . . ?
C2 C4 C14 C13 -175.0(6) . . . . ?
O4 C15 C16 C17 -20.4(9) . . . . ?
O5 C15 C16 C17 161.0(6) . . . . ?
O4 C15 C16 C18 102.6(7) . . . . ?
O5 C15 C16 C18 -75.9(6) . . . . ?
C15 C16 C18 C28 126.8(5) . . . . ?
C17 C16 C18 C28 -110.1(6) . . . . ?
C15 C16 C18 C19 -52.8(7) . . . . ?
C17 C16 C18 C19 70.2(6) . . . . ?
C28 C18 C19 C20 -1.8(8) . . . . ?
C16 C18 C19 C20 177.9(5) . . . . ?
C18 C19 C20 C21 -0.7(9) . . . . ?
C19 C20 C21 C22 -175.2(5) . . . . ?
C19 C20 C21 C27 2.8(9) . . . . ?
C20 C21 C22 C23 179.4(6) . . . . ?
C27 C21 C22 C23 1.4(8) . . . . ?
C21 C22 C23 O6 -178.0(5) . . . . ?
C21 C22 C23 C25 1.7(9) . . . . ?
C24 O6 C23 C22 -1.6(9) . . . . ?
C24 O6 C23 C25 178.7(5) . . . . ?
C22 C23 C25 C26 -2.7(9) . . . . ?
O6 C23 C25 C26 177.0(6) . . . . ?
C23 C25 C26 C27 0.6(9) . . . . ?
C25 C26 C27 C28 -176.5(5) . . . . ?
C25 C26 C27 C21 2.5(8) . . . . ?
C20 C21 C27 C28 -2.6(7) . . . . ?
C22 C21 C27 C28 175.5(5) . . . . ?
C20 C21 C27 C26 178.5(5) . . . . ?
C22 C21 C27 C26 -3.4(7) . . . . ?
C19 C18 C28 C27 2.0(8) . . . . ?
C16 C18 C28 C27 -177.6(5) . . . . ?
C26 C27 C28 C18 179.1(5) . . . . ?
C21 C27 C28 C18 0.2(8) . . . . ?
C33 N1 C30 C31 17.4(7) . . . . ?
C33 N1 C30 C29 -101.5(6) . . . . ?
O7 C29 C30 N1 11.3(7) . . . . ?
O8 C29 C30 N1 -170.3(5) . . . . ?
O7 C29 C30 C31 -101.8(6) . . . . ?
O8 C29 C30 C31 76.7(7) . . . . ?
N1 C30 C31 C32 -33.6(6) . . . . ?
C29 C30 C31 C32 82.7(7) . . . . ?
C30 C31 C32 C33 38.5(7) . . . . ?
C31 C32 C33 N1 -26.9(8) . . . . ?
C30 N1 C33 C32 5.7(8) . . . . ?
C38 N2 C35 C36 28.5(6) . . . . ?
C38 N2 C35 C34 -90.3(5) . . . . ?
O9 C34 C35 N2 6.5(6) . . . . ?
O10 C34 C35 N2 -177.6(5) . . . . ?
O9 C34 C35 C36 -107.3(6) . . . . ?
O10 C34 C35 C36 68.5(6) . . . . ?
C38 C37 C36 C35 37.5(7) . . . . ?
N2 C35 C36 C37 -40.3(6) . . . . ?
C34 C35 C36 C37 77.9(6) . . . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.043



# start Validation Reply Form
_vrf_PLAT242_nt0026_RSnprxDproEtOHb2_polI 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check 
RESPONSE: Carbon atom in the wobbling COOH-group.
;
_vrf_PLAT243_nt0026_RSnprxDproEtOHb2_polI 
;
PROBLEM: High   'Solvent' Ueq as Compared to Neighbors of        C33 Check 
RESPONSE: Probably because of minor disorder of the proline molecule.
;
_vrf_PLAT244_nt0026_RSnprxDproEtOHb2_polI 
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of        C29 Check 
RESPONSE: Carbon atom in the wobbling COO^-^-group.
;
_vrf_PLAT340_nt0026_RSnprxDproEtOHb2_polI 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00833 Ang.  
RESPONSE: Limited resolution - crystal diffracts poorly on Mo radiation, 
and we had to use Cu radiation. 
;
_vrf_PLAT911_nt0026_RSnprxDproEtOHb2_polI 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.598         28 Report
RESPONSE: These reflections are missing in the highest and lowest resolution 
shells because of the instrument geometry limitation.

;
_vrf_PLAT915_nt0026_RSnprxDproEtOHb2_polI 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         53 %     
RESPONSE: Absolute configuration established by
 the structure determination of a compound containing a chiral reference
 molecule of known absolute configuration (S-naproxen). Signal-to-noise ratio
of the data was not sufficient enough for direct determination of the absolute
 configuration by anomalous-dispersion effects, so we did not collect all 
Friedel pairs.

;
_vrf_PLAT978_nt0026_RSnprxDproEtOHb2_polI 
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: Limited resolution - crystal diffracts poorly on Mo radiation, 
and we had to use Cu radiation.
;
####################################################################### 
# 
# 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_RSnprxDLpro_polI
_database_code_depnum_ccdc_archive 'CCDC 1861021'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
'(2R)-2-(6-methoxynaphthalen-2-yl)propanoic acid (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid (2R)-pyrrolidin-1-ium-2-carboxylate (2S)-pyrrolidin-1-ium-2-carboxylatepolymorph I'
_chemical_name_common            
'RS-naproxen DL-proline 1:1 cocrystal, polymorph I'
_chemical_melting_point          425(1)
_chemical_formula_moiety         'C14 H14 O3, C5 H9 N O2'
_chemical_formula_sum            'C19 H23 N O5'
_chemical_formula_weight         345.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   9.9964(3)
_cell_length_b                   9.0958(4)
_cell_length_c                   39.9654(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3633.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3687
_cell_measurement_theta_min      6.6550
_cell_measurement_theta_max      64.7370

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            18470
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         6.263
_diffrn_reflns_theta_max         67.253
_diffrn_reflns_theta_full        67.253
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3224
_reflns_number_gt                2429
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0494P)²+0.3417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3224
_refine_ls_number_parameters     257
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O1 O 0.25560(12) 0.59555(15) 0.67353(3) 0.0666(3) Uani 1 1 d . . . . .
H4 H 0.261421 0.548702 0.690995 0.080 Uiso 1 1 calc R U . . .
N1 N 0.01027(12) 0.26029(14) 0.77877(3) 0.0480(3) Uani 1 1 d D U . . .
H1A H -0.044190 0.329177 0.770737 0.058 Uiso 1 1 calc R U . A 1
H1B H -0.027949 0.172912 0.775756 0.058 Uiso 1 1 calc R U . A 1
C1 C 0.36970(16) 0.66100(19) 0.66741(4) 0.0540(4) Uani 1 1 d . . . . .
O2 O 0.46650(13) 0.64895(17) 0.68508(3) 0.0764(4) Uani 1 1 d . . . . .
C2 C 0.36782(18) 0.7477(2) 0.63508(4) 0.0590(4) Uani 1 1 d . . . . .
H2 H 0.280014 0.794693 0.632963 0.071 Uiso 1 1 calc R U . . .
O3 O 0.04955(11) 0.47725(13) 0.73555(3) 0.0617(3) Uani 1 1 d . . . . .
C3 C 0.4743(2) 0.8678(2) 0.63490(6) 0.0823(6) Uani 1 1 d . . . . .
H3A H 0.461906 0.930765 0.653929 0.123 Uiso 1 1 calc R U . . .
H3B H 0.466616 0.924586 0.614746 0.123 Uiso 1 1 calc R U . . .
H3C H 0.561447 0.823644 0.635918 0.123 Uiso 1 1 calc R U . . .
O4 O 0.25927(11) 0.41636(14) 0.72331(3) 0.0620(3) Uani 1 1 d . . . . .
C4 C 0.38424(17) 0.63992(19) 0.60625(4) 0.0544(4) Uani 1 1 d . . . . .
O5 O 0.57139(15) 0.16187(15) 0.49752(3) 0.0778(4) Uani 1 1 d . . . . .
C5 C 0.29021(18) 0.6343(2) 0.58018(4) 0.0614(4) Uani 1 1 d . . . . .
H5 H 0.215357 0.694869 0.581089 0.074 Uiso 1 1 calc R U . . .
C6 C 0.30602(19) 0.5420(2) 0.55350(4) 0.0634(5) Uani 1 1 d . . . . .
H6 H 0.242749 0.542392 0.536444 0.076 Uiso 1 1 calc R U . . .
C7 C 0.41648(17) 0.44611(19) 0.55137(4) 0.0545(4) Uani 1 1 d . . . . .
C8 C 0.43517(19) 0.3491(2) 0.52389(4) 0.0603(4) Uani 1 1 d . . . . .
H8 H 0.373619 0.348378 0.506438 0.072 Uiso 1 1 calc R U . . .
C9 C 0.5421(2) 0.2576(2) 0.52295(4) 0.0636(5) Uani 1 1 d . . . . .
C10 C 0.4796(3) 0.1555(2) 0.47030(5) 0.0822(6) Uani 1 1 d . . . . .
H10A H 0.510980 0.085895 0.454039 0.123 Uiso 1 1 calc R U . . .
H10B H 0.472614 0.250847 0.460138 0.123 Uiso 1 1 calc R U . . .
H10C H 0.393372 0.125532 0.478369 0.123 Uiso 1 1 calc R U . . .
C11 C 0.6340(2) 0.2558(3) 0.54955(5) 0.0782(6) Uani 1 1 d . . . . .
H11 H 0.705375 0.190267 0.549124 0.094 Uiso 1 1 calc R U . . .
C12 C 0.6196(2) 0.3488(3) 0.57589(5) 0.0775(6) Uani 1 1 d . . . . .
H12 H 0.682351 0.347192 0.593065 0.093 Uiso 1 1 calc R U . . .
C13 C 0.51065(17) 0.4484(2) 0.57772(4) 0.0588(4) Uani 1 1 d . . . . .
C14 C 0.49222(18) 0.5478(2) 0.60457(4) 0.0621(4) Uani 1 1 d . . . . .
H14 H 0.555500 0.550541 0.621618 0.074 Uiso 1 1 calc R U . . .
C15 C 0.14997(15) 0.39861(16) 0.73806(4) 0.0451(4) Uani 1 1 d . . . . .
C16 C 0.14246(14) 0.26595(17) 0.76114(4) 0.0471(4) Uani 1 1 d D U . . .
H16 H 0.154536 0.175942 0.748001 0.057 Uiso 1 1 calc R U . B 1
C17A C 0.2468(5) 0.2712(11) 0.78887(9) 0.074(2) Uani 0.685(8) 1 d D U P C 1
H17A H 0.280030 0.370471 0.792013 0.089 Uiso 0.685(8) 1 calc R U P C 1
H17B H 0.321555 0.206856 0.783846 0.089 Uiso 0.685(8) 1 calc R U P C 1
C18A C 0.1713(3) 0.2182(5) 0.81984(7) 0.0678(12) Uani 0.685(8) 1 d D U P C 1
H18A H 0.166128 0.111784 0.820516 0.081 Uiso 0.685(8) 1 calc R U P C 1
H18B H 0.213052 0.253462 0.840231 0.081 Uiso 0.685(8) 1 calc R U P C 1
C19A C 0.0357(5) 0.2859(13) 0.81485(9) 0.064(2) Uani 0.685(8) 1 d D U P C 1
H19A H -0.031133 0.237732 0.828611 0.077 Uiso 0.685(8) 1 calc R U P C 1
H19B H 0.036816 0.390055 0.820017 0.077 Uiso 0.685(8) 1 calc R U P C 1
C17B C 0.2434(9) 0.257(2) 0.7897(2) 0.072(4) Uani 0.315(8) 1 d D U P C 2
H17C H 0.324734 0.310156 0.784245 0.086 Uiso 0.315(8) 1 calc R U P C 2
H17D H 0.265583 0.155926 0.794876 0.086 Uiso 0.315(8) 1 calc R U P C 2
C18B C 0.1690(7) 0.3303(13) 0.81869(17) 0.080(3) Uani 0.315(8) 1 d D U P C 2
H18C H 0.209624 0.306045 0.840033 0.096 Uiso 0.315(8) 1 calc R U P C 2
H18D H 0.166458 0.436266 0.816127 0.096 Uiso 0.315(8) 1 calc R U P C 2
C19B C 0.0317(10) 0.264(3) 0.81558(19) 0.064(4) Uani 0.315(8) 1 d D U P C 2
H19C H 0.028900 0.166216 0.825098 0.076 Uiso 0.315(8) 1 calc R U P C 2
H19D H -0.034861 0.325099 0.826534 0.076 Uiso 0.315(8) 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
O1 C1 1.310(2) . ?
O1 H4 0.8200 . ?
N1 C19A 1.483(4) . ?
N1 C19B 1.487(8) . ?
N1 C16 1.4985(19) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
C1 O2 1.203(2) . ?
C1 C2 1.514(2) . ?
C2 C4 1.522(3) . ?
C2 C3 1.525(3) . ?
C2 H2 0.9800 . ?
O3 C15 1.2367(18) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
O4 C15 1.2518(18) . ?
C4 C14 1.368(3) . ?
C4 C5 1.404(2) . ?
O5 C9 1.370(2) . ?
O5 C10 1.424(3) . ?
C5 C6 1.366(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(3) . ?
C6 H6 0.9300 . ?
C7 C13 1.413(2) . ?
C7 C8 1.421(3) . ?
C8 C9 1.355(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.405(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.358(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.418(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.415(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.521(2) . ?
C16 C17A 1.523(4) . ?
C16 C17B 1.525(7) . ?
C16 H16 0.9800 . ?
C17A C18A 1.528(5) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A C19A 1.502(7) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C17B C18B 1.530(9) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B C19B 1.503(10) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?

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
C1 O1 H4 109.5 . . ?
C19A N1 C16 107.5(2) . . ?
C19B N1 C16 109.7(4) . . ?
C19A N1 H1A 110.2 . . ?
C16 N1 H1A 110.2 . . ?
C19A N1 H1B 110.2 . . ?
C16 N1 H1B 110.2 . . ?
H1A N1 H1B 108.5 . . ?
O2 C1 O1 123.34(16) . . ?
O2 C1 C2 123.95(16) . . ?
O1 C1 C2 112.66(14) . . ?
C1 C2 C4 108.03(14) . . ?
C1 C2 C3 111.62(16) . . ?
C4 C2 C3 112.49(16) . . ?
C1 C2 H2 108.2 . . ?
C4 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C14 C4 C5 117.99(16) . . ?
C14 C4 C2 121.12(15) . . ?
C5 C4 C2 120.88(15) . . ?
C9 O5 C10 117.04(16) . . ?
C6 C5 C4 121.60(16) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 121.20(16) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C13 117.88(16) . . ?
C6 C7 C8 122.27(16) . . ?
C13 C7 C8 119.85(16) . . ?
C9 C8 C7 120.43(17) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 O5 125.42(18) . . ?
C8 C9 C11 120.11(17) . . ?
O5 C9 C11 114.47(17) . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 120.66(19) . . ?
C12 C11 H11 119.7 . . ?
C9 C11 H11 119.7 . . ?
C11 C12 C13 121.27(19) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C7 C13 C14 119.22(16) . . ?
C7 C13 C12 117.63(16) . . ?
C14 C13 C12 123.15(17) . . ?
C4 C14 C13 122.07(16) . . ?
C4 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
O3 C15 O4 126.57(14) . . ?
O3 C15 C16 117.90(13) . . ?
O4 C15 C16 115.53(13) . . ?
N1 C16 C15 110.86(12) . . ?
N1 C16 C17A 105.2(2) . . ?
C15 C16 C17A 112.5(4) . . ?
N1 C16 C17B 103.3(4) . . ?
C15 C16 C17B 117.6(8) . . ?
N1 C16 H16 109.4 . . ?
C15 C16 H16 109.4 . . ?
C17A C16 H16 109.4 . . ?
C16 C17A C18A 104.0(3) . . ?
C16 C17A H17A 111.0 . . ?
C18A C17A H17A 111.0 . . ?
C16 C17A H17B 111.0 . . ?
C18A C17A H17B 111.0 . . ?
H17A C17A H17B 109.0 . . ?
C19A C18A C17A 102.1(4) . . ?
C19A C18A H18A 111.4 . . ?
C17A C18A H18A 111.4 . . ?
C19A C18A H18B 111.4 . . ?
C17A C18A H18B 111.4 . . ?
H18A C18A H18B 109.2 . . ?
N1 C19A C18A 102.7(4) . . ?
N1 C19A H19A 111.2 . . ?
C18A C19A H19A 111.2 . . ?
N1 C19A H19B 111.2 . . ?
C18A C19A H19B 111.2 . . ?
H19A C19A H19B 109.1 . . ?
C16 C17B C18B 102.9(6) . . ?
C16 C17B H17C 111.2 . . ?
C18B C17B H17C 111.2 . . ?
C16 C17B H17D 111.2 . . ?
C18B C17B H17D 111.2 . . ?
H17C C17B H17D 109.1 . . ?
C19B C18B C17B 102.0(9) . . ?
C19B C18B H18C 111.4 . . ?
C17B C18B H18C 111.4 . . ?
C19B C18B H18D 111.4 . . ?
C17B C18B H18D 111.4 . . ?
H18C C18B H18D 109.2 . . ?
N1 C19B C18B 102.9(7) . . ?
N1 C19B H19C 111.2 . . ?
C18B C19B H19C 111.2 . . ?
N1 C19B H19D 111.2 . . ?
C18B C19B H19D 111.2 . . ?
H19C C19B H19D 109.1 . . ?

_refine_diff_density_max         0.098
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.029





# start Validation Reply Form
_vrf_PLAT911_RSnprxDLpro_EtOH    
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.598         24 Report
RESPONSE: These reflections are missing in the highest resolution 
shells because of the instrument geometry limitation.
;
_vrf_PLAT978_RSnprxDLpro_EtOH    
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Note  
RESPONSE: Limited resolution because data were collected using Cu radiation
 (small crystals, diffraction is too weak on Mo radiation).
;
####################################################################### 
# 
# 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_RS-L-1-1-pol-III
_database_code_depnum_ccdc_archive 'CCDC 1861027'
_audit_update_record             
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_chemical_name_systematic        
'(2R)-2-(6-methoxynaphthalen-2-yl)propanoic acid (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid bis((2S)-pyrrolidin-1-ium-2-carboxylate), polymorph III'
_chemical_name_common            
;
RS-naproxen L-proline 1:1 cocrystal, polymorph III
;
_chemical_formula_moiety         '2(C14 H14 O3), 2(C5 H9 NO2)'
_chemical_formula_sum            'C38 H46 N2 O10'
_chemical_formula_weight         690.77
_exptl_crystal_density_diffrn    1.259
_chemical_melting_point          ?
_chemical_absolute_configuration rm


_cell_length_a                   12.705(2)
_cell_length_b                   5.7631(8)
_cell_length_c                   25.000(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.041(11)
_cell_angle_gamma                90
_cell_volume                     1823.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    402
_cell_special_details            
; 
The powder pattern was indexed using FOX program
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'

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


_pd_spec_size_axial              4
_pd_spec_size_equat              0.5
_pd_spec_size_thick              0.5


_pd_spec_mounting                'Thin-wall 0.5 mm glass capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_colour                  colourless
_exptl_absorpt_correction_type   none

_pd_instr_location               
; 
BM1 beamline, The Swiss-Norwegian Beamlines (SNBL) at 
European Synchrotron Radiation Facility (ESRF), Grenoble, France
;
_pd_calibration_special_details  
; 
using LaB₆ standard
;

_diffrn_ambient_temperature      402
_diffrn_source                   synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  PILATUS@SNBL
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_type            'PILATUS 2M'
_diffrn_radiation_wavelength     0.78487
_pd_meas_scan_method             fixed
_pd_meas_special_details         
;  ?
;

_pd_meas_number_of_points        2304
_pd_meas_2theta_range_min        1.29466
_pd_meas_2theta_range_max        37.00238
_pd_meas_2theta_range_inc        0.0155


_pd_proc_ls_prof_R_factor        4.939
_pd_proc_ls_prof_wR_factor       6.851
_pd_proc_ls_prof_wR_expected     0.110

_refine_ls_R_I_factor            7.117
_refine_ls_number_reflns         ?
_refine_ls_number_parameters     ?
_refine_ls_number_restraints     ?
_refine_ls_goodness_of_fit_all   62.48
_refine_ls_shift/su_max          0.001

_pd_proc_2theta_range_min        1.29466
_pd_proc_2theta_range_max        37.00238
_pd_proc_2theta_range_inc        0.0155
_pd_proc_wavelength              0.78487

_computing_data_collection       ?
_computing_structure_solution    FOX
_computing_structure_refinement  'TOPAS V5'
_computing_molecular_graphics    ?
_computing_publication_material  ?



loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C1a C 2 0.021349 0.4819493 0.1742777 1 15
O2a O 2 0.1073453 0.5430457 0.1980794 1 15
O3a O 2 -0.03255204 0.3010969 0.1839931 1 15
N4a N 2 0.00148578 0.8924034 0.1422364 1 15
H5a H 2 0.05041581 0.8957703 0.1699797 1 18
H6a H 2 -0.05595587 0.9747548 0.1475069 1 18
C7a C 2 -0.02485316 0.6399956 0.1285079 1 15
H8a H 2 -0.1014018 0.6163987 0.1227648 1 18
C9a C 2 0.0303 0.58173 0.07274 1 15
H10a H 2 0.06985159 0.4382699 0.07780022 1 18
H11a H 2 -0.026491 0.581765 0.04414764 1 18
C12a C 2 0.1059795 0.7877712 0.0693237 1 15
H13a H 2 0.172446 0.7485313 0.08936472 1 18
H14a H 2 0.115933 0.825497 0.03229263 1 18
C15a C 2 0.05097665 0.9919808 0.09572556 1 15
H16a H 2 0.09895052 1.116783 0.1072447 1 18
H17a H 2 -0.003800839 1.054938 0.07034766 1 18
C1 C 2 1.072192 0.9775339 0.600451 1 15
O2 O 2 1.094561 1.13596 0.5672795 1 15
O3 O 2 1.132103 0.8966944 0.6381252 1 15
N4 N 2 0.9623312 0.6406397 0.5655419 1 15
H5 H 2 0.9499794 0.6610822 0.530262 1 18
H6 H 2 1.027282 0.5816884 0.567186 1 18
C7 C 2 0.9598197 0.8764356 0.5930831 1 15
H8 H 2 0.9066572 0.9782285 0.5745312 1 18
C9 C 2 0.93105 0.78215 0.65171 1 15
H10 H 2 0.9049642 0.9186773 0.6689979 1 18
H11 H 2 0.9946414 0.7003052 0.6651874 1 18
C12 C 2 0.8393141 0.6179699 0.6341632 1 15
H13 H 2 0.7740655 0.7053948 0.6283782 1 18
H14 H 2 0.8353148 0.4988403 0.6613188 1 18
C15 C 2 0.8699357 0.5074364 0.5813586 1 15
H16 H 2 0.8101627 0.5252194 0.5547509 1 18
H17 H 2 0.8881658 0.3440952 0.583731 1 18
O1c O 2 0.7650036 1.21266 0.5003272 1 8.64745
O2c O 2 0.3758212 0.919505 0.2179819 1 8.64745
O3c O 2 0.3114791 0.5711961 0.2250735 1 8.64745
C4c C 2 0.5228934 0.9265726 0.3994708 1 8.64745
C5c C 2 0.4330173 0.8411474 0.368399 1 8.64745
C6c C 2 0.5616204 0.8097562 0.4466142 1 8.64745
C7c C 2 0.5682055 1.126209 0.3857563 1 8.64745
C8c C 2 0.3925408 0.9601012 0.324312 1 8.64745
C9c C 2 0.641426 0.9039027 0.4792898 1 8.64745
C10c C 2 0.6531387 1.223457 0.4198915 1 8.64745
C11c C 2 0.5276068 1.246585 0.3395529 1 8.64745
C12c C 2 0.4411818 1.162084 0.3090578 1 8.64745
C13c C 2 0.2916134 0.8761222 0.2928595 1 8.64745
C14c C 2 0.6867759 1.11616 0.4670421 1 8.64745
C15c C 2 0.3275683 0.7813137 0.2428648 1 8.64745
C16c C 2 0.2431431 0.6566954 0.3193895 1 8.64745
C17c C 2 0.81839 1.07122 0.54304 1 8.64745
H18c H 2 0.4032895 0.7002503 0.3771903 1 10.37694
H19c H 2 0.53458 0.6651185 0.4546114 1 10.37694
H20c H 2 0.6600356 0.8331393 0.5121987 1 10.37694
H21c H 2 0.6780438 1.370642 0.412422 1 10.37694
H22c H 2 0.5612412 1.379873 0.3288145 1 10.37694
H23c H 2 0.4140607 1.242214 0.2786211 1 10.37694
H24c H 2 0.2429628 1.005712 0.2845519 1 10.37694
H25c H 2 0.2041656 0.7051025 0.3486441 1 10.37694
H26c H 2 0.1966953 0.577218 0.2931076 1 10.37694
H27c H 2 0.2990389 0.5540844 0.3325798 1 10.37694
H28c H 2 0.2676261 0.5650515 0.1990109 1 10.37694
H29c H 2 0.7770051 1.068804 0.5733685 1 10.37694
H30c H 2 0.82784 0.9165694 0.53002 1 10.37694
H31c H 2 0.8866688 1.136064 0.5535991 1 10.37694
C1b C 2 0.70933 -0.54224 1.01123 1 15
O2b O 2 0.6996009 -0.3223137 0.9820673 1 15
C3b C 2 0.6150112 -0.287843 0.9458271 1 15
C4b C 2 0.5316348 -0.4466676 0.9403795 1 15
C5b C 2 0.4459548 -0.409794 0.9049758 1 15
C6b C 2 0.4398446 -0.208264 0.8730161 1 15
C7b C 2 0.3463661 -0.1579466 0.8402737 1 15
C8b C 2 0.3385935 0.04229099 0.8114108 1 15
C9b C 2 0.4234968 0.1941797 0.813031 1 15
C10b C 2 0.5137365 0.1468576 0.8452957 1 15
C11b C 2 0.5210284 -0.05784436 0.8759942 1 15
C12b C 2 0.6117547 -0.09861395 0.9128194 1 15
C13b C 2 0.2353504 0.1037185 0.7788871 1 15
C14b C 2 0.2033908 0.3657147 0.7860975 1 15
C15b C 2 0.2551517 0.04987845 0.7230524 1 15
O16b O 2 0.2039681 0.1832777 0.6877975 1 15
O17b O 2 0.3121524 -0.1003908 0.7091244 1 15
H18b H 2 0.5327795 -0.5720117 0.9638525 1 18
H19b H 2 0.3927215 -0.5207583 0.9007842 1 18
H20b H 2 0.2911535 -0.2644223 0.8374154 1 18
H21b H 2 0.4185063 0.3300462 0.7928965 1 18
H22b H 2 0.5712704 0.2467973 0.8456787 1 18
H23b H 2 0.6655968 0.01101079 0.9167371 1 18
H24b H 2 0.1779943 0.002602922 0.7885833 1 18
H25b H 2 0.6787339 -0.5269693 1.044825 1 18
H26b H 2 0.7826361 -0.5825382 1.017841 1 18
H27b H 2 0.6730174 -0.6618289 0.9902012 1 18
H28b H 2 0.2621794 0.463854 0.7799454 1 18
H29b H 2 0.1839258 0.3896053 0.8219316 1 18
H30b H 2 0.1445965 0.4033004 0.7608085 1 18
H31b H 2 0.1822116 0.1135496 0.660441 1 18

loop_
_pd_proc_2theta_corrected
_pd_calc_intensity_total
_pd_proc_intensity_total
1.29466 1985.82037 1907.61400
1.31016 1991.71405 1936.45300
1.32567 1997.63076 1945.06700
1.34117 2003.57368 1972.59300
1.35668 2009.54617 1980.85900
1.37218 2016.14094 2005.23300
1.38769 2026.36453 2031.58200
1.40319 2036.63416 2050.68100
1.41870 2046.96423 2077.92300
1.43420 2057.35067 2098.69600
1.44971 2067.81158 2108.17400
1.46521 2078.36109 2095.70200
1.48072 2089.01614 2095.13000
1.49622 2099.80032 2095.89800
1.51173 2110.75387 2104.83000
1.52723 2121.88804 2114.29800
1.54274 2132.88799 2114.52300
1.55824 2142.44101 2127.77200
1.57374 2152.38254 2129.16300
1.58925 2162.82859 2138.14300
1.60475 2173.95028 2147.98700
1.62026 2186.02813 2154.54000
1.63576 2198.95439 2186.41300
1.65127 2216.51785 2219.32800
1.66677 2249.83983 2279.82100
1.68228 2335.71825 2412.24900
1.69778 2571.01405 2630.38800
1.71329 3147.28982 3113.38900
1.72879 4320.26843 4146.40800
1.74430 6233.18155 6110.52500
1.75980 8635.28006 8670.03600
1.77531 10758.42706 11518.22000
1.79081 11629.66590 13196.85000
1.80632 10775.98724 12835.60000
1.82182 8668.32633 10780.61000
1.83733 6279.51990 7955.39600
1.85283 4378.46087 5436.29600
1.86834 3217.27876 3621.10100
1.88384 2653.48667 2807.26000
1.89935 2431.25227 2430.29000
1.91485 2358.77214 2339.37200
1.93036 2338.99007 2307.03600
1.94586 2335.01256 2298.67100
1.96137 2331.87358 2303.70000
1.97687 2329.09945 2300.68300
1.99238 2327.29765 2301.43400
2.00788 2326.17142 2304.31300
2.02339 2325.55080 2302.10900
2.03889 2325.31901 2304.95600
2.05440 2325.39121 2305.11900
2.06990 2325.70437 2308.31400
2.08541 2326.21089 2313.70800
2.10091 2326.87427 2312.06200
2.11641 2327.66631 2313.99800
2.13192 2328.56475 2309.28600
2.14743 2329.55196 2314.37300
2.16293 2331.06896 2321.16200
2.17843 2334.60253 2332.67500
2.19394 2338.18998 2342.58600
2.20945 2341.82367 2348.87700
2.22495 2345.49700 2357.26400
2.24045 2349.20691 2365.11300
2.25596 2352.94643 2369.95600
2.27146 2356.71120 2378.38300
2.28697 2360.49922 2379.59100
2.30247 2364.30779 2383.74100
2.31798 2368.13460 2388.21000
2.33348 2371.97740 2390.27300
2.34899 2375.83498 2395.90400
2.36449 2379.70560 2389.02600
2.38000 2383.58796 2391.82000
2.39550 2387.48093 2395.17400
2.41101 2391.38353 2404.38400
2.42651 2395.29489 2416.77600
2.44202 2399.21424 2414.26900
2.45752 2403.14066 2419.98700
2.47303 2407.07406 2423.59600
2.48853 2411.01366 2429.38600
2.50404 2414.95900 2439.67400
2.51954 2418.90966 2434.76300
2.53505 2422.86528 2437.56400
2.55055 2426.82555 2441.59500
2.56606 2430.79016 2437.69200
2.58156 2434.75861 2446.30000
2.59707 2438.73119 2450.78600
2.61257 2442.70746 2453.10600
2.62808 2446.68723 2461.70200
2.64358 2450.67036 2461.22800
2.65909 2454.65673 2467.38600
2.67459 2458.64623 2477.03900
2.69009 2462.63851 2477.00600
2.70560 2466.63427 2484.10300
2.72111 2470.65514 2483.10900
2.73661 2474.65662 2480.80600
2.75211 2478.66097 2482.07200
2.76762 2482.66817 2480.40100
2.78313 2486.67825 2485.36500
2.79863 2490.69124 2493.19900
2.81413 2494.70692 2496.40100
2.82964 2498.72587 2505.14000
2.84514 2502.74793 2512.04700
2.86065 2506.77320 2516.57300
2.87615 2510.80181 2521.61300
2.89166 2514.83391 2518.86300
2.90716 2518.86969 2520.05900
2.92267 2522.90936 2521.79700
2.93817 2526.95315 2525.55800
2.95368 2531.00110 2531.14800
2.96918 2535.05405 2531.93800
2.98469 2539.11213 2535.14600
3.00019 2543.17576 2537.79300
3.01570 2547.24544 2536.01000
3.03120 2551.32176 2542.73700
3.04671 2555.43147 2541.29200
3.06221 2559.52310 2545.41200
3.07772 2563.62423 2555.47400
3.09322 2567.10343 2559.00900
3.10873 2568.09199 2567.09200
3.12423 2569.12085 2568.92100
3.13974 2570.13790 2565.59500
3.15524 2571.17028 2570.95000
3.17075 2572.22156 2574.35000
3.18625 2573.29461 2577.87900
3.20176 2574.39315 2580.38500
3.21726 2575.52144 2576.43900
3.23277 2576.68488 2577.87100
3.24827 2577.89015 2579.96900
3.26378 2579.14566 2585.05000
3.27928 2580.46210 2590.97200
3.29479 2581.85316 2591.56200
3.31029 2583.33711 2592.17500
3.32579 2584.93742 2593.87000
3.34130 2586.68686 2591.23100
3.35681 2588.63238 2598.78800
3.37231 2590.85525 2601.29200
3.38781 2593.56675 2606.28800
3.40332 2597.33690 2622.59600
3.41882 2604.08322 2648.44300
3.43433 2619.02900 2685.56200
3.44983 2653.71223 2717.74700
3.46534 2727.43090 2759.05600
3.48084 2861.81511 2800.53800
3.49635 3065.90511 2852.77400
3.51185 3319.89861 2918.30500
3.52736 3573.45540 3009.59800
3.54286 3767.79683 3120.74300
3.55837 3875.90704 3258.62100
3.57387 3905.70216 3370.01900
3.58938 3853.49382 3433.50200
3.60488 3698.76778 3403.89900
3.62039 3455.45807 3274.97500
3.63589 3184.93774 3083.10800
3.65140 2951.22822 2909.04400
3.66690 2788.44425 2767.40300
3.68241 2695.87049 2693.77000
3.69791 2653.57413 2662.59300
3.71342 2641.87763 2652.28800
3.72892 2652.58014 2659.55500
3.74443 2691.29728 2667.07000
3.75993 2772.98076 2708.96100
3.77544 2909.42510 2772.89500
3.79094 3090.37810 2868.62200
3.80645 3270.55055 2970.19400
3.82195 3378.86668 3028.98200
3.83746 3359.82945 3033.57800
3.85296 3224.36682 2986.43300
3.86847 3038.32862 2892.70200
3.88397 2868.05789 2801.34000
3.89947 2748.33829 2738.22400
3.91498 2680.74078 2696.98800
3.93049 2649.52503 2677.64600
3.94599 2637.84569 2665.22800
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35.31235 919.64071 923.75230
35.32785 919.66619 921.77440
35.34336 919.66744 922.13320
35.35886 919.66396 924.53900
35.37437 919.67220 924.90140
35.38987 919.69763 923.31300
35.40538 919.73582 922.23970
35.42088 919.77654 922.11570
35.43639 919.81026 922.43390
35.45189 919.83010 924.46090
35.46740 919.83103 927.13470
35.48290 919.81091 928.18160
35.49841 919.77361 929.25240
35.51391 919.72750 927.20530
35.52942 919.68246 923.66050
35.54492 919.64855 922.51110
35.56043 919.63586 923.96460
35.57593 919.65535 927.05960
35.59144 919.71496 927.43620
35.60694 919.81948 925.45760
35.62244 919.97005 924.84030
35.63795 920.16606 925.50260
35.65345 920.40743 924.81580
35.66896 920.69356 926.96950
35.68446 921.02000 926.44130
35.69997 921.37678 925.85020
35.71548 921.74898 928.01040
35.73098 922.12153 931.92510
35.74649 922.48390 932.06040
35.76199 922.82822 932.15420
35.77749 923.14688 933.29600
35.79300 923.43062 933.88280
35.80850 923.67314 931.90720
35.82401 923.87835 931.98460
35.83951 924.05894 930.92030
35.85502 924.22982 928.60830
35.87053 924.39996 928.93230
35.88603 924.56837 927.83800
35.90154 924.72662 924.12540
35.91704 924.86337 923.06660
35.93254 924.97340 924.19260
35.94805 925.06609 924.37940
35.96355 925.16502 921.84590
35.97906 925.29980 919.31450
35.99456 925.49512 919.60510
36.01007 925.76387 920.04440
36.02557 926.10235 919.79710
36.04108 926.49132 919.31360
36.05658 926.89501 920.65730
36.07209 927.26983 922.82930
36.08759 927.57366 923.30390
36.10310 927.78119 920.08970
36.11860 927.88943 918.59040
36.13411 927.91140 919.57590
36.14961 927.86233 919.72600
36.16512 927.75266 919.10160
36.18062 927.59488 915.46290
36.19613 927.40713 913.79890
36.21163 927.21025 914.91460
36.22713 927.02507 915.62020
36.24264 926.86637 917.19060
36.25814 926.74426 921.12020
36.27365 926.66136 921.99690
36.28915 926.61450 921.41580
36.30466 926.59719 923.81770
36.32017 926.59080 924.87150
36.33567 926.52367 922.55040
36.35118 926.47860 923.16920
36.36668 926.46061 925.71010
36.38218 926.47337 925.43670
36.39769 926.51592 923.30760
36.41319 926.58208 925.45480
36.42870 926.66163 927.25850
36.44420 926.73767 925.41160
36.45971 926.78975 927.21470
36.47522 926.79848 931.22800
36.49072 926.75464 929.52620
36.50623 926.66372 927.83890
36.52173 926.54185 930.50790
36.53724 926.40767 931.79820
36.55274 926.28009 931.91220
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36.59925 926.10112 933.38270
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36.66127 926.33104 935.35080
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36.72329 926.13866 939.00880
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36.81632 925.61132 941.07900
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36.97137 925.59265 939.68430
36.98687 925.60825 940.62610
37.00238 925.58780 940.33430
# start Validation Reply Form
_vrf_GEOM001_RS-L-1-1-pol-III    
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM003_RS-L-1-1-pol-III    
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM006_RS-L-1-1-pol-III    
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_GEOM007_RS-L-1-1-pol-III    
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: The molecules in the refinement were treated as rigid bodies, 
thus providing the values of the bond lengths and bond angles is meaningless;
only torsion angles were refined.
;
_vrf_PLAT351_RS-L-1-1-pol-III    
;
PROBLEM: Long   C-H (X0.96,N1.08A)  C17C     - H8       ..       1.41 Ang. 
RESPONSE: A possible reason of this alert is a disorder of the 
proline molecules. Proline is highly flexible in terms of conformations, 
which may cause its disorder that was observed in almost all the structures
 found from single-crystal X-ray diffraction. We tried to introduce disorder
 for proline in the refinement of powder X-ray diffraction data but it did not
 significantly improve the structural models and only made fit less stable, 
so we decided to omit it.
;
_vrf_PLAT411_RS-L-1-1-pol-III    
;
PROBLEM: Short Inter H...H Contact  H14      ..H24C             1.77 Ang.  
RESPONSE: A possible reason of this alert is a disorder of the 
proline molecules. Proline is highly flexible in terms of conformations, 
which may cause its disorder that was observed in almost all the structures
 found from single-crystal X-ray diffraction. We tried to introduce disorder
 for proline in the refinement of powder X-ray diffraction data but it did not
 significantly improve the structural models and only made fit less stable, 
so we decided to omit it.
;
_vrf_PLAT413_RS-L-1-1-pol-III    
;
PROBLEM: Short Inter XH3 .. XHn     H14      ..H25C             1.77 Ang.  
RESPONSE: A possible reason of this alert is a disorder of the 
proline molecules. Proline is highly flexible in terms of conformations, 
which may cause its disorder that was observed in almost all the structures
 found from single-crystal X-ray diffraction. We tried to introduce disorder
 for proline in the refinement of powder X-ray diffraction data but it did not
 significantly improve the structural models and only made fit less stable, 
so we decided to omit it.
;
_exptl_crystal_colour            colourless
_exptl_crystal_description       powder
