#------------------------------------------------------------------------------
#$Date: 2019-11-14 14:41:25 +0200 (Thu, 14 Nov 2019) $
#$Revision: 227795 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/50/7235098.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7235098
loop_
_publ_author_name
'Tumanova, Natalia'
'Tumanov, Nikolay'
'Fischer, Franziska'
'Morelle, Fabrice'
'Ban, Voraksmy'
'Robeyns, Koen'
'Filinchuk, Yaroslav'
'Wouters, Johan'
'Emmerling, Franziska'
'Leyssens, Tom'
_publ_section_title
;
 Exploring polymorphism and stoichiometric diversity in naproxen/proline
 cocrystals
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7308
_journal_paper_doi               10.1039/C8CE01338A
_journal_volume                  20
_journal_year                    2018
_chemical_absolute_configuration rm
_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
_chemical_name_common
;
1:1 S-naproxen DL-proline cocrystal hydrate
;
_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'
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_update_record
;
2018-08-08 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.06468(13)
_cell_length_b                   12.2629(3)
_cell_length_c                   50.6290(15)
_cell_measurement_temperature    295
_cell_volume                     3765.31(17)
_computing_structure_refinement  'TOPAS V5'
_computing_structure_solution    FOX
_diffrn_ambient_temperature      295
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_type            'PILATUS 2M'
_diffrn_measurement_device_type  PILATUS@SNBL
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.798
_diffrn_source                   synchrotron
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       powder
_pd_char_colour                  colourless
_pd_instr_location
; 
BM1 beamline, The Swiss-Norwegian Beamlines (SNBL) at 
European Synchrotron Radiation Facility (ESRF), Grenoble, France
;
_pd_meas_2theta_range_inc        0.01
_pd_meas_2theta_range_max        34.99581
_pd_meas_2theta_range_min        1.37503
_pd_meas_number_of_points        3363
_pd_meas_scan_method             fixed
_pd_proc_2theta_range_inc        0.01
_pd_proc_2theta_range_max        34.99581
_pd_proc_2theta_range_min        1.37503
_pd_proc_ls_prof_R_factor        2.45
_pd_proc_ls_prof_wR_expected     0.16
_pd_proc_ls_prof_wR_factor       3.63
_pd_proc_wavelength              0.798
_pd_spec_mounting                'Thin-wall 0.5 mm glass capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_spec_size_axial              4
_pd_spec_size_equat              0.5
_pd_spec_size_thick              0.5
_refine_ls_goodness_of_fit_all   22.67
_refine_ls_R_I_factor            2.59
_refine_ls_shift/su_max          0.001
_cod_data_source_file            c8ce01338a2.cif
_cod_data_source_block           S-nprx-DL-pro-1-1-H2O
_cod_original_cell_volume        3765.29(17)
_cod_database_code               7235098
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 -0.0502(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
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