# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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#######################################################################

data_dlnw
_database_code_depnum_ccdc_archive 'CCDC 1854201'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2019-01-17 downloaded from the CCDC.
;
_audit_creation_date             2018-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'darunavir dihydrate'
_chemical_name_systematic        
;
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl((2S,3R)-4-
((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-
phenylbutan-2-yl)carbamate dihydrate
;
_chemical_formula_moiety         'C27 H37 N3 O7 S, 2(H2 O)'
_chemical_formula_sum            'C27 H41 N3 O9 S'
_chemical_formula_weight         583.69
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   9.9965(5)
_cell_length_b                   16.5620(10)
_cell_length_c                   18.7532(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3104.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22461
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      58.814
_cell_measurement_theta_min      6.446
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.9398
_exptl_absorpt_correction_T_min  0.9284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22461
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.407
_diffrn_reflns_theta_min         3.223
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.863
_reflns_number_gt                5472
_reflns_number_total             7509
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    
'Ortep3 for windows (Farrugia,1997) and Diamond (Brandengurg & Putz, 2005)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1921 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         7509
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+0.6587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1225
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 N2(H2A), N3(H3A,H3B), O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C10(H10), C19(H19)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C18(H18A,
 H18B)
2.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C23(H23), C24(H24),
 C26(H26), C27(H27)
2.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1 C 0.6862(3) 0.67881(19) 0.22959(18) 0.0415(7) Uani 1 1 d . . . . .
H1A H 0.755102 0.658155 0.198087 0.050 Uiso 1 1 calc R . . . .
H1B H 0.724639 0.683669 0.276882 0.050 Uiso 1 1 calc R . . . .
C2 C 0.6439(3) 0.76245(19) 0.20382(17) 0.0392(7) Uani 1 1 d . . . . .
H2 H 0.600413 0.755891 0.157335 0.047 Uiso 1 1 calc R . . . .
C3 C 0.7641(3) 0.81810(18) 0.19355(16) 0.0372(7) Uani 1 1 d . . . . .
H3 H 0.808320 0.825192 0.239768 0.045 Uiso 1 1 calc R . . . .
C4 C 0.9784(3) 0.75365(18) 0.16495(16) 0.0359(6) Uani 1 1 d . . . . .
C5 C 1.1835(3) 0.7003(2) 0.12055(17) 0.0446(8) Uani 1 1 d . . . . .
H5 H 1.183645 0.666817 0.163631 0.054 Uiso 1 1 calc R . . . .
C6 C 1.2174(4) 0.6513(3) 0.0549(2) 0.0571(9) Uani 1 1 d . . . . .
H6A H 1.279027 0.608113 0.066722 0.068 Uiso 1 1 calc R . . . .
H6B H 1.137254 0.628066 0.034283 0.068 Uiso 1 1 calc R . . . .
C7 C 1.3578(3) 0.7625(2) 0.04733(18) 0.0520(9) Uani 1 1 d . . . . .
H7 H 1.451067 0.744420 0.049467 0.062 Uiso 1 1 calc R . . . .
C8 C 1.2418(4) 0.8804(3) 0.0533(2) 0.0634(10) Uani 1 1 d . . . . .
H8A H 1.155832 0.865433 0.033174 0.076 Uiso 1 1 calc R . . . .
H8B H 1.252657 0.938439 0.049803 0.076 Uiso 1 1 calc R . . . .
C9 C 1.2538(4) 0.8521(2) 0.13014(19) 0.0556(9) Uani 1 1 d . . . . .
H9A H 1.321280 0.882787 0.155584 0.067 Uiso 1 1 calc R . . . .
H9B H 1.169087 0.857054 0.154981 0.067 Uiso 1 1 calc R . . . .
C10 C 1.2947(3) 0.7642(2) 0.12273(17) 0.0471(8) Uani 1 1 d . . . . .
H10 H 1.361634 0.750068 0.158840 0.057 Uiso 1 1 calc R . . . .
C11 C 0.7203(3) 0.9013(2) 0.1663(2) 0.0525(8) Uani 1 1 d . . . . .
H11A H 0.673526 0.894602 0.121360 0.063 Uiso 1 1 calc R . . . .
H11B H 0.658046 0.924724 0.200139 0.063 Uiso 1 1 calc R . . . .
C12 C 0.8358(3) 0.95903(19) 0.1555(2) 0.0500(8) Uani 1 1 d . . . . .
C13 C 0.8849(4) 0.9756(3) 0.0885(2) 0.0663(11) Uani 1 1 d . . . . .
H13 H 0.847242 0.950161 0.049049 0.080 Uiso 1 1 calc R . . . .
C14 C 0.9898(5) 1.0297(3) 0.0786(3) 0.0813(14) Uani 1 1 d . . . . .
H14 H 1.021308 1.040477 0.032959 0.098 Uiso 1 1 calc R . . . .
C15 C 1.0461(5) 1.0668(3) 0.1358(3) 0.0891(15) Uani 1 1 d . . . . .
H15 H 1.115352 1.103655 0.129408 0.107 Uiso 1 1 calc R . . . .
C16 C 1.0000(5) 1.0496(3) 0.2033(3) 0.0943(17) Uani 1 1 d . . . . .
H16 H 1.039710 1.074023 0.242577 0.113 Uiso 1 1 calc R . . . .
C17 C 0.8958(5) 0.9965(3) 0.2132(2) 0.0752(12) Uani 1 1 d . . . . .
H17 H 0.865373 0.985655 0.259053 0.090 Uiso 1 1 calc R . . . .
C18 C 0.5587(4) 0.5771(2) 0.30092(18) 0.0531(8) Uani 1 1 d . . . . .
H18A H 0.645481 0.557660 0.316438 0.064 Uiso 1 1 calc R . . . .
H18B H 0.501085 0.530605 0.294153 0.064 Uiso 1 1 calc R . . . .
C19 C 0.4996(4) 0.6309(3) 0.35870(19) 0.0609(10) Uani 1 1 d . . . . .
H19 H 0.557136 0.678442 0.364288 0.073 Uiso 1 1 calc R . . . .
C20 C 0.4992(7) 0.5839(4) 0.4289(2) 0.1002(18) Uani 1 1 d . . . . .
H20A H 0.449940 0.534570 0.422876 0.150 Uiso 1 1 calc GR . . . .
H20B H 0.457741 0.615914 0.465419 0.150 Uiso 1 1 calc GR . . . .
H20C H 0.589484 0.571603 0.442507 0.150 Uiso 1 1 calc GR . . . .
C21 C 0.3600(5) 0.6591(3) 0.3399(3) 0.0894(15) Uani 1 1 d . . . . .
H21A H 0.360678 0.682968 0.293244 0.134 Uiso 1 1 calc GR . . . .
H21B H 0.330762 0.698303 0.374179 0.134 Uiso 1 1 calc GR . . . .
H21C H 0.300096 0.613784 0.340277 0.134 Uiso 1 1 calc GR . . . .
C22 C 0.6909(3) 0.4995(2) 0.15201(17) 0.0424(7) Uani 1 1 d . . . . .
C23 C 0.6853(3) 0.4235(2) 0.18453(17) 0.0463(8) Uani 1 1 d . . . . .
H23 H 0.609506 0.408435 0.210001 0.056 Uiso 1 1 calc R . . . .
C24 C 0.7914(4) 0.3712(2) 0.17897(18) 0.0506(8) Uani 1 1 d . . . . .
H24 H 0.786452 0.320833 0.200665 0.061 Uiso 1 1 calc R . . . .
C25 C 0.9068(4) 0.3926(2) 0.14119(17) 0.0497(8) Uani 1 1 d . . . . .
C26 C 0.9118(3) 0.4687(2) 0.10966(17) 0.0493(8) Uani 1 1 d . . . . .
H26 H 0.988205 0.484096 0.084806 0.059 Uiso 1 1 calc R . . . .
C27 C 0.8054(3) 0.5219(2) 0.11463(17) 0.0478(8) Uani 1 1 d . . . . .
H27 H 0.810315 0.572402 0.093085 0.057 Uiso 1 1 calc R . . . .
N1 N 0.5740(3) 0.61989(16) 0.23215(14) 0.0421(6) Uani 1 1 d . . . . .
N2 N 0.8600(2) 0.78303(16) 0.14398(13) 0.0376(6) Uani 1 1 d . . . . .
H2A H 0.833730 0.785185 0.093385 0.045 Uiso 1 1 d R . . . .
N3 N 1.0095(3) 0.3372(2) 0.13327(18) 0.0664(9) Uani 1 1 d . . . . .
H3A H 1.084562 0.354774 0.125396 0.080 Uiso 1 1 d R . . . .
H3B H 1.014522 0.301234 0.166276 0.080 Uiso 1 1 d R . . . .
O1 O 0.4360(2) 0.51874(15) 0.16960(14) 0.0574(6) Uani 1 1 d . . . . .
O2 O 0.5616(3) 0.62112(15) 0.10136(12) 0.0550(6) Uani 1 1 d . . . . .
O1W O 0.6743(4) 0.8631(2) 0.37940(19) 0.1023(12) Uani 1 1 d . . . . .
H1WA H 0.649662 0.910788 0.378607 0.153 Uiso 1 1 d R . . . .
H1WB H 0.648102 0.842918 0.417087 0.153 Uiso 1 1 d R . . . .
O3 O 0.5498(2) 0.79793(15) 0.25064(13) 0.0549(6) Uani 1 1 d . . . . .
H3C H 0.587674 0.812013 0.287387 0.082 Uiso 1 1 calc GR . . . .
O2W O 0.5989(13) 0.7852(4) 0.5112(3) 0.282(6) Uani 1 1 d . . . . .
H2WA H 0.661889 0.753653 0.503529 0.422 Uiso 1 1 d R . . . .
H2WB H 0.526799 0.797633 0.493319 0.422 Uiso 1 1 d R . . . .
O4 O 1.0146(2) 0.74417(15) 0.22605(11) 0.0457(5) Uani 1 1 d . . . . .
O5 O 1.05338(19) 0.73494(14) 0.10744(10) 0.0441(5) Uani 1 1 d . . . . .
O6 O 1.2778(3) 0.70701(18) 0.00672(13) 0.0621(7) Uani 1 1 d . . . . .
O7 O 1.3492(3) 0.83879(18) 0.01784(14) 0.0663(8) Uani 1 1 d . . . . .
S1 S 0.55557(8) 0.56597(5) 0.15967(4) 0.0438(2) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0371(16) 0.0413(19) 0.0462(17) 0.0002(14) -0.0002(13) 0.0016(13)
C2 0.0309(14) 0.0379(17) 0.0488(17) -0.0035(14) 0.0007(11) 0.0038(12)
C3 0.0338(15) 0.0364(17) 0.0414(16) -0.0038(13) -0.0007(12) 0.0020(12)
C4 0.0331(14) 0.0351(16) 0.0394(16) 0.0008(14) 0.0037(11) -0.0020(11)
C5 0.0373(16) 0.055(2) 0.0419(17) 0.0059(16) 0.0029(13) 0.0105(14)
C6 0.055(2) 0.059(2) 0.057(2) -0.0016(18) 0.0106(16) 0.0107(18)
C7 0.0398(17) 0.069(3) 0.0474(19) 0.0050(18) 0.0051(13) 0.0058(17)
C8 0.072(3) 0.056(2) 0.061(2) 0.0033(19) 0.0079(19) 0.010(2)
C9 0.059(2) 0.063(2) 0.0439(19) -0.0060(17) 0.0077(15) -0.0101(18)
C10 0.0379(16) 0.066(2) 0.0379(17) 0.0083(16) 0.0016(12) 0.0045(16)
C11 0.0454(18) 0.0365(17) 0.076(2) 0.0040(18) -0.0010(17) 0.0030(14)
C12 0.0516(19) 0.0314(17) 0.067(2) 0.0016(17) -0.0062(17) 0.0000(13)
C13 0.073(3) 0.051(2) 0.074(3) 0.000(2) -0.007(2) -0.016(2)
C14 0.086(3) 0.069(3) 0.088(3) 0.011(3) 0.000(2) -0.022(3)
C15 0.075(3) 0.066(3) 0.125(4) 0.020(3) -0.022(3) -0.028(3)
C16 0.106(4) 0.073(4) 0.104(4) -0.006(3) -0.039(3) -0.034(3)
C17 0.094(3) 0.061(3) 0.071(3) -0.002(2) -0.012(2) -0.014(2)
C18 0.062(2) 0.045(2) 0.052(2) 0.0074(16) 0.0038(16) -0.0039(18)
C19 0.081(3) 0.055(2) 0.047(2) 0.0033(17) 0.0097(17) -0.008(2)
C20 0.146(5) 0.102(4) 0.053(3) 0.011(3) 0.010(3) 0.001(4)
C21 0.086(3) 0.080(3) 0.102(4) 0.014(3) 0.042(3) 0.009(3)
C22 0.0465(17) 0.0405(18) 0.0403(17) 0.0014(14) 0.0003(13) -0.0013(14)
C23 0.0498(18) 0.043(2) 0.0466(18) 0.0038(15) 0.0031(13) -0.0052(15)
C24 0.062(2) 0.0404(19) 0.050(2) 0.0088(15) 0.0008(15) -0.0005(16)
C25 0.059(2) 0.049(2) 0.0405(18) -0.0025(15) -0.0018(14) 0.0089(16)
C26 0.052(2) 0.054(2) 0.0416(18) 0.0047(16) 0.0079(14) 0.0015(16)
C27 0.061(2) 0.044(2) 0.0389(18) 0.0052(15) 0.0063(14) -0.0027(16)
N1 0.0434(14) 0.0388(15) 0.0442(14) 0.0034(12) 0.0028(11) -0.0030(12)
N2 0.0324(12) 0.0447(16) 0.0357(13) -0.0014(11) -0.0016(9) 0.0022(10)
N3 0.067(2) 0.067(2) 0.065(2) 0.0083(17) 0.0086(15) 0.0198(17)
O1 0.0448(13) 0.0539(15) 0.0735(16) -0.0034(13) -0.0044(12) -0.0087(11)
O2 0.0638(15) 0.0523(15) 0.0491(13) 0.0058(11) -0.0054(12) 0.0053(12)
O1W 0.110(3) 0.105(3) 0.092(2) 0.003(2) 0.011(2) 0.030(2)
O3 0.0427(12) 0.0512(15) 0.0708(17) -0.0062(13) 0.0144(11) 0.0074(11)
O2W 0.519(18) 0.168(7) 0.158(6) 0.010(5) 0.002(8) -0.043(9)
O4 0.0428(11) 0.0583(15) 0.0362(12) 0.0026(11) -0.0014(8) 0.0094(10)
O5 0.0314(10) 0.0644(15) 0.0364(11) -0.0007(10) 0.0015(8) 0.0078(10)
O6 0.0643(16) 0.0776(19) 0.0444(14) -0.0032(13) 0.0124(11) 0.0057(14)
O7 0.0734(18) 0.0697(19) 0.0559(16) 0.0172(14) 0.0210(13) 0.0103(14)
S1 0.0431(4) 0.0416(4) 0.0467(4) 0.0022(4) -0.0027(3) -0.0013(3)

_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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.527(4) . ?
C1 N1 1.487(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.527(4) . ?
C2 O3 1.414(4) . ?
C3 H3 0.9800 . ?
C3 C11 1.534(4) . ?
C3 N2 1.456(4) . ?
C4 N2 1.339(4) . ?
C4 O4 1.212(3) . ?
C4 O5 1.349(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.512(5) . ?
C5 C10 1.535(5) . ?
C5 O5 1.443(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 O6 1.425(5) . ?
C7 H7 0.9800 . ?
C7 C10 1.549(4) . ?
C7 O6 1.438(5) . ?
C7 O7 1.381(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.521(5) . ?
C8 O7 1.439(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.519(5) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.513(5) . ?
C12 C13 1.377(6) . ?
C12 C17 1.383(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.358(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(6) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.522(5) . ?
C18 N1 1.479(4) . ?
C19 H19 0.9800 . ?
C19 C20 1.530(6) . ?
C19 C21 1.513(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.399(5) . ?
C22 C27 1.392(4) . ?
C22 S1 1.750(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.373(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.399(5) . ?
C25 C26 1.394(5) . ?
C25 N3 1.385(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.385(5) . ?
C27 H27 0.9300 . ?
N1 S1 1.637(3) . ?
N2 H2A 0.9850 . ?
N3 H3A 0.8181 . ?
N3 H3B 0.8606 . ?
O1 S1 1.440(2) . ?
O2 S1 1.426(2) . ?
O1W H1WA 0.8279 . ?
O1W H1WB 0.8242 . ?
O3 H3C 0.8200 . ?
O2W H2WA 0.8302 . ?
O2W H2WB 0.8210 . ?

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
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
N1 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
N1 C1 C2 113.4(2) . . ?
C1 C2 H2 107.7 . . ?
C3 C2 C1 111.7(2) . . ?
C3 C2 H2 107.7 . . ?
O3 C2 C1 111.4(3) . . ?
O3 C2 H2 107.7 . . ?
O3 C2 C3 110.5(2) . . ?
C2 C3 H3 108.4 . . ?
C2 C3 C11 111.1(2) . . ?
C11 C3 H3 108.4 . . ?
N2 C3 C2 111.0(2) . . ?
N2 C3 H3 108.4 . . ?
N2 C3 C11 109.5(3) . . ?
N2 C4 O5 109.9(2) . . ?
O4 C4 N2 126.1(3) . . ?
O4 C4 O5 124.1(2) . . ?
C6 C5 H5 111.5 . . ?
C6 C5 C10 103.2(3) . . ?
C10 C5 H5 111.5 . . ?
O5 C5 H5 111.5 . . ?
O5 C5 C6 106.1(3) . . ?
O5 C5 C10 112.6(3) . . ?
C5 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
O6 C6 C5 105.3(3) . . ?
O6 C6 H6A 110.7 . . ?
O6 C6 H6B 110.7 . . ?
C10 C7 H7 110.8 . . ?
O6 C7 H7 110.8 . . ?
O6 C7 C10 105.5(3) . . ?
O7 C7 H7 110.8 . . ?
O7 C7 C10 108.9(3) . . ?
O7 C7 O6 109.8(3) . . ?
H8A C8 H8B 109.1 . . ?
C9 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
O7 C8 H8A 111.1 . . ?
O7 C8 H8B 111.1 . . ?
O7 C8 C9 103.4(3) . . ?
C8 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 C8 103.3(3) . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
C5 C10 C7 105.0(3) . . ?
C5 C10 H10 110.4 . . ?
C7 C10 H10 110.4 . . ?
C9 C10 C5 117.9(3) . . ?
C9 C10 C7 102.1(3) . . ?
C9 C10 H10 110.4 . . ?
C3 C11 H11A 108.9 . . ?
C3 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C3 113.2(3) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 C17 118.0(4) . . ?
C17 C12 C11 120.7(4) . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.1(4) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(5) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.5(4) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.7(5) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
N1 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
N1 C18 C19 112.3(3) . . ?
C18 C19 H19 108.6 . . ?
C18 C19 C20 108.4(4) . . ?
C20 C19 H19 108.6 . . ?
C21 C19 C18 111.8(4) . . ?
C21 C19 H19 108.6 . . ?
C21 C19 C20 110.8(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 S1 119.9(2) . . ?
C27 C22 C23 119.5(3) . . ?
C27 C22 S1 120.6(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 121.1(3) . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 118.2(3) . . ?
N3 C25 C24 119.9(3) . . ?
N3 C25 C26 121.8(3) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.3(3) . . ?
C27 C26 H26 119.4 . . ?
C22 C27 H27 120.1 . . ?
C26 C27 C22 119.7(3) . . ?
C26 C27 H27 120.1 . . ?
C1 N1 S1 114.6(2) . . ?
C18 N1 C1 114.9(3) . . ?
C18 N1 S1 116.8(2) . . ?
C3 N2 H2A 115.2 . . ?
C4 N2 C3 122.6(3) . . ?
C4 N2 H2A 122.1 . . ?
C25 N3 H3A 117.6 . . ?
C25 N3 H3B 115.1 . . ?
H3A N3 H3B 108.8 . . ?
H1WA O1W H1WB 107.9 . . ?
C2 O3 H3C 109.5 . . ?
H2WA O2W H2WB 138.9 . . ?
C4 O5 C5 117.1(2) . . ?
C6 O6 C7 108.2(3) . . ?
C7 O7 C8 107.4(3) . . ?
N1 S1 C22 108.91(15) . . ?
O1 S1 C22 108.07(15) . . ?
O1 S1 N1 106.41(14) . . ?
O2 S1 C22 107.91(15) . . ?
O2 S1 N1 106.41(14) . . ?
O2 S1 O1 118.82(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A O6 0.98 1.96 2.948(3) 178.0 3_465 yes
N3 H3A O1W 0.82 2.42 3.199(5) 160.4 4_745 yes
N3 H3B O4 0.86 2.25 3.065(4) 158.4 4_745 yes
O1W H1WA O1 0.83 2.18 2.951(5) 155.2 4_655 yes
O1W H1WB O2W 0.82 2.07 2.888(8) 174.4 . yes
O3 H3C O1W 0.82 2.11 2.923(5) 172.6 . yes

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 C2 C3 C11 178.9(3) . . . . ?
C1 C2 C3 N2 56.9(3) . . . . ?
C1 N1 S1 C22 69.1(2) . . . . ?
C1 N1 S1 O1 -174.7(2) . . . . ?
C1 N1 S1 O2 -47.0(2) . . . . ?
C2 C1 N1 C18 -128.2(3) . . . . ?
C2 C1 N1 S1 92.4(3) . . . . ?
C2 C3 C11 C12 179.7(3) . . . . ?
C2 C3 N2 C4 -108.3(3) . . . . ?
C3 C11 C12 C13 103.0(4) . . . . ?
C3 C11 C12 C17 -76.6(4) . . . . ?
C5 C6 O6 C7 36.9(4) . . . . ?
C6 C5 C10 C7 16.2(3) . . . . ?
C6 C5 C10 C9 129.0(3) . . . . ?
C6 C5 O5 C4 154.5(3) . . . . ?
C8 C9 C10 C5 -91.5(3) . . . . ?
C8 C9 C10 C7 22.9(3) . . . . ?
C9 C8 O7 C7 37.6(4) . . . . ?
C10 C5 C6 O6 -32.1(3) . . . . ?
C10 C5 O5 C4 -93.3(3) . . . . ?
C10 C7 O6 C6 -25.7(4) . . . . ?
C10 C7 O7 C8 -22.9(4) . . . . ?
C11 C3 N2 C4 128.8(3) . . . . ?
C11 C12 C13 C14 179.0(4) . . . . ?
C11 C12 C17 C16 -179.4(4) . . . . ?
C12 C13 C14 C15 0.4(7) . . . . ?
C13 C12 C17 C16 1.0(6) . . . . ?
C13 C14 C15 C16 1.0(8) . . . . ?
C14 C15 C16 C17 -1.4(8) . . . . ?
C15 C16 C17 C12 0.4(8) . . . . ?
C17 C12 C13 C14 -1.4(6) . . . . ?
C18 N1 S1 C22 -69.5(3) . . . . ?
C18 N1 S1 O1 46.8(3) . . . . ?
C18 N1 S1 O2 174.4(2) . . . . ?
C19 C18 N1 C1 74.2(4) . . . . ?
C19 C18 N1 S1 -147.4(3) . . . . ?
C22 C23 C24 C25 0.2(5) . . . . ?
C23 C22 C27 C26 0.4(5) . . . . ?
C23 C22 S1 N1 88.0(3) . . . . ?
C23 C22 S1 O1 -27.2(3) . . . . ?
C23 C22 S1 O2 -156.9(3) . . . . ?
C23 C24 C25 C26 0.5(5) . . . . ?
C23 C24 C25 N3 -176.7(3) . . . . ?
C24 C25 C26 C27 -0.7(5) . . . . ?
C25 C26 C27 C22 0.3(5) . . . . ?
C27 C22 C23 C24 -0.7(5) . . . . ?
C27 C22 S1 N1 -91.1(3) . . . . ?
C27 C22 S1 O1 153.7(3) . . . . ?
C27 C22 S1 O2 24.1(3) . . . . ?
N1 C1 C2 C3 -173.3(2) . . . . ?
N1 C1 C2 O3 62.6(3) . . . . ?
N1 C18 C19 C20 -175.1(4) . . . . ?
N1 C18 C19 C21 62.5(4) . . . . ?
N2 C3 C11 C12 -57.4(4) . . . . ?
N2 C4 O5 C5 -178.4(3) . . . . ?
N3 C25 C26 C27 176.4(3) . . . . ?
O3 C2 C3 C11 -56.5(4) . . . . ?
O3 C2 C3 N2 -178.5(2) . . . . ?
O4 C4 N2 C3 8.5(5) . . . . ?
O4 C4 O5 C5 1.1(4) . . . . ?
O5 C4 N2 C3 -172.0(3) . . . . ?
O5 C5 C6 O6 86.5(3) . . . . ?
O5 C5 C10 C7 -97.7(3) . . . . ?
O5 C5 C10 C9 15.1(4) . . . . ?
O6 C7 C10 C5 4.6(3) . . . . ?
O6 C7 C10 C9 -118.9(3) . . . . ?
O6 C7 O7 C8 92.2(3) . . . . ?
O7 C7 C10 C5 122.4(3) . . . . ?
O7 C7 C10 C9 -1.1(4) . . . . ?
O7 C7 O6 C6 -142.9(3) . . . . ?
O7 C8 C9 C10 -37.1(4) . . . . ?
S1 C22 C23 C24 -179.7(3) . . . . ?
S1 C22 C27 C26 179.5(3) . . . . ?

_shelx_res_file                  
;
TITL dlnw in P 21 21 21
    dlnw.res
    created by SHELXL-2018/3 at 16:25:16 on 26-Jul-2018
CELL 0.71073 9.9965 16.562 18.7532 90 90 90
ZERR 4 0.0005 0.001 0.0011 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 108 164 12 36 4
EQIV $1 -0.5+X,1.5-Y,-Z
EQIV $2 2-X,-0.5+Y,0.5-Z
EQIV $3 1-X,0.5+Y,0.5-Z

L.S. 10
PLAN  3
SIZE 0.4 0.46 0.48
TEMP 23
HTAB N2 O6_$1
HTAB N3 O1W_$2
HTAB N3 O4_$2
HTAB O1W O1_$3
HTAB O1W O2W
HTAB O3 O1W
BOND $H
CONF
fmap 2
acta
MERG 2
REM <olex2.extras>
REM <HklSrc "%.\\DLNW.hkl">
REM </olex2.extras>

WGHT    0.053300    0.658700
FVAR       0.53328
C1    1    0.686167    0.678805    0.229591    11.00000    0.03712    0.04134 =
         0.04619    0.00024   -0.00016    0.00161
AFIX  23
H1A   2    0.755102    0.658155    0.198087    11.00000   -1.20000
H1B   2    0.724639    0.683669    0.276882    11.00000   -1.20000
AFIX   0
C2    1    0.643868    0.762453    0.203818    11.00000    0.03090    0.03791 =
         0.04876   -0.00348    0.00072    0.00379
AFIX  13
H2    2    0.600413    0.755891    0.157335    11.00000   -1.20000
AFIX   0
C3    1    0.764116    0.818096    0.193548    11.00000    0.03384    0.03638 =
         0.04140   -0.00376   -0.00067    0.00200
AFIX  13
H3    2    0.808320    0.825192    0.239768    11.00000   -1.20000
AFIX   0
C4    1    0.978391    0.753652    0.164948    11.00000    0.03311    0.03511 =
         0.03938    0.00083    0.00366   -0.00202
C5    1    1.183496    0.700309    0.120551    11.00000    0.03730    0.05460 =
         0.04188    0.00587    0.00289    0.01054
AFIX  13
H5    2    1.183645    0.666817    0.163631    11.00000   -1.20000
AFIX   0
C6    1    1.217407    0.651348    0.054950    11.00000    0.05522    0.05911 =
         0.05685   -0.00161    0.01058    0.01071
AFIX  23
H6A   2    1.279027    0.608113    0.066722    11.00000   -1.20000
H6B   2    1.137254    0.628066    0.034283    11.00000   -1.20000
AFIX   0
C7    1    1.357825    0.762534    0.047332    11.00000    0.03979    0.06872 =
         0.04742    0.00501    0.00512    0.00584
AFIX  13
H7    2    1.451067    0.744420    0.049467    11.00000   -1.20000
AFIX   0
C8    1    1.241755    0.880374    0.053263    11.00000    0.07234    0.05647 =
         0.06129    0.00329    0.00787    0.01014
AFIX  23
H8A   2    1.155832    0.865433    0.033174    11.00000   -1.20000
H8B   2    1.252657    0.938439    0.049803    11.00000   -1.20000
AFIX   0
C9    1    1.253804    0.852101    0.130143    11.00000    0.05948    0.06332 =
         0.04391   -0.00603    0.00772   -0.01012
AFIX  23
H9A   2    1.321280    0.882787    0.155584    11.00000   -1.20000
H9B   2    1.169087    0.857054    0.154981    11.00000   -1.20000
AFIX   0
C10   1    1.294723    0.764155    0.122730    11.00000    0.03794    0.06564 =
         0.03785    0.00834    0.00160    0.00446
AFIX  13
H10   2    1.361634    0.750068    0.158840    11.00000   -1.20000
AFIX   0
C11   1    0.720310    0.901301    0.166287    11.00000    0.04538    0.03646 =
         0.07553    0.00399   -0.00095    0.00297
AFIX  23
H11A  2    0.673526    0.894602    0.121360    11.00000   -1.20000
H11B  2    0.658046    0.924724    0.200139    11.00000   -1.20000
AFIX   0
C12   1    0.835823    0.959027    0.155522    11.00000    0.05155    0.03138 =
         0.06717    0.00157   -0.00625   -0.00001
C13   1    0.884871    0.975587    0.088455    11.00000    0.07332    0.05134 =
         0.07425   -0.00043   -0.00713   -0.01555
AFIX  43
H13   2    0.847242    0.950161    0.049049    11.00000   -1.20000
AFIX   0
C14   1    0.989805    1.029731    0.078646    11.00000    0.08627    0.06939 =
         0.08836    0.01062    0.00029   -0.02249
AFIX  43
H14   2    1.021308    1.040477    0.032959    11.00000   -1.20000
AFIX   0
C15   1    1.046133    1.066839    0.135792    11.00000    0.07524    0.06650 =
         0.12542    0.01985   -0.02152   -0.02779
AFIX  43
H15   2    1.115352    1.103655    0.129408    11.00000   -1.20000
AFIX   0
C16   1    1.000004    1.049555    0.203278    11.00000    0.10583    0.07267 =
         0.10435   -0.00645   -0.03875   -0.03424
AFIX  43
H16   2    1.039710    1.074023    0.242577    11.00000   -1.20000
AFIX   0
C17   1    0.895784    0.996466    0.213169    11.00000    0.09424    0.06094 =
         0.07055   -0.00184   -0.01243   -0.01448
AFIX  43
H17   2    0.865373    0.985655    0.259053    11.00000   -1.20000
AFIX   0
C18   1    0.558702    0.577103    0.300921    11.00000    0.06205    0.04539 =
         0.05184    0.00740    0.00379   -0.00385
AFIX  23
H18A  2    0.645481    0.557660    0.316438    11.00000   -1.20000
H18B  2    0.501085    0.530605    0.294153    11.00000   -1.20000
AFIX   0
C19   1    0.499631    0.630939    0.358699    11.00000    0.08081    0.05518 =
         0.04678    0.00326    0.00965   -0.00836
AFIX  13
H19   2    0.557136    0.678442    0.364288    11.00000   -1.20000
AFIX   0
C20   1    0.499155    0.583871    0.428917    11.00000    0.14569    0.10244 =
         0.05262    0.01138    0.00965    0.00065
AFIX 137
H20A  2    0.449940    0.534570    0.422876    11.00000   -1.50000
H20B  2    0.457741    0.615914    0.465419    11.00000   -1.50000
H20C  2    0.589484    0.571603    0.442507    11.00000   -1.50000
AFIX   0
C21   1    0.360038    0.659069    0.339881    11.00000    0.08586    0.08046 =
         0.10180    0.01409    0.04176    0.00862
AFIX 137
H21A  2    0.360678    0.682968    0.293244    11.00000   -1.50000
H21B  2    0.330762    0.698303    0.374179    11.00000   -1.50000
H21C  2    0.300096    0.613784    0.340277    11.00000   -1.50000
AFIX   0
C22   1    0.690900    0.499496    0.152013    11.00000    0.04650    0.04051 =
         0.04026    0.00138    0.00033   -0.00131
C23   1    0.685306    0.423548    0.184535    11.00000    0.04977    0.04263 =
         0.04663    0.00383    0.00312   -0.00517
AFIX  43
H23   2    0.609506    0.408435    0.210001    11.00000   -1.20000
AFIX   0
C24   1    0.791394    0.371241    0.178972    11.00000    0.06163    0.04040 =
         0.04979    0.00883    0.00078   -0.00052
AFIX  43
H24   2    0.786452    0.320833    0.200665    11.00000   -1.20000
AFIX   0
C25   1    0.906795    0.392577    0.141189    11.00000    0.05935    0.04922 =
         0.04050   -0.00255   -0.00184    0.00894
C26   1    0.911844    0.468714    0.109664    11.00000    0.05206    0.05423 =
         0.04159    0.00465    0.00786    0.00146
AFIX  43
H26   2    0.988205    0.484096    0.084806    11.00000   -1.20000
AFIX   0
C27   1    0.805377    0.521913    0.114629    11.00000    0.06061    0.04399 =
         0.03888    0.00520    0.00631   -0.00274
AFIX  43
H27   2    0.810315    0.572402    0.093085    11.00000   -1.20000
AFIX   0
N1    3    0.574047    0.619892    0.232153    11.00000    0.04337    0.03881 =
         0.04415    0.00337    0.00282   -0.00301
N2    3    0.859980    0.783035    0.143975    11.00000    0.03236    0.04467 =
         0.03575   -0.00140   -0.00156    0.00222
AFIX   3
H2A   2    0.833730    0.785185    0.093385    11.00000   -1.20000
AFIX   0
N3    3    1.009512    0.337204    0.133266    11.00000    0.06693    0.06714 =
         0.06506    0.00826    0.00855    0.01983
AFIX   3
H3A   2    1.084562    0.354774    0.125396    11.00000   -1.20000
H3B   2    1.014522    0.301234    0.166276    11.00000   -1.20000
AFIX   0
O1    4    0.436033    0.518739    0.169601    11.00000    0.04477    0.05386 =
         0.07348   -0.00337   -0.00439   -0.00874
O2    4    0.561581    0.621117    0.101365    11.00000    0.06378    0.05230 =
         0.04906    0.00576   -0.00535    0.00525

O1W   4    0.674272    0.863068    0.379397    11.00000    0.10965    0.10524 =
         0.09204    0.00311    0.01059    0.03029
AFIX   3
H1WA  2    0.649662    0.910788    0.378607    11.00000   -1.50000
H1WB  2    0.648102    0.842918    0.417087    11.00000   -1.50000
AFIX   0

O3    4    0.5







####################################################################### 
# 
# 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_dl-ethy
_database_code_depnum_ccdc_archive 'CCDC 1863702'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;
_audit_creation_date             2018-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'darunavir ethanol solvate'
_chemical_name_systematic        
'(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl((2S,3R)-4-((4-amino-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate ethanol solvate'
_chemical_formula_moiety         'C27 H37 N3 O7 S, C2 H6 O'
_chemical_formula_sum            'C29 H43 N3 O8 S'
_chemical_formula_weight         593.72
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   9.9846(5)
_cell_length_b                   16.6017(10)
_cell_length_c                   19.0274(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3154.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26982
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      51.992
_cell_measurement_theta_min      6.382
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_correction_T_min  0.9313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T. (1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.191
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  R-AXIS-RAPID
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3911
_reflns_number_total             6191
_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.
;
_reflns_threshold_expression     'I > 2\s(I)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    
'Ortep3 for windows (Farrugia,1997) and Diamond (Brandengurg & Putz, 2005)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6191
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.0923
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+1.4336P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1592
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C28-C29
 1.54 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.0005 and sigma for
terminal atoms of 0.001
4.a Riding coordinates:
 N3(H3A,H3B)
4.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C10(H10), C19(H19)
4.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C18(H18A,
 H18B), C28(H28A,H28B)
4.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C23(H23), C24(H24),
 C26(H26), C27(H27), N2(H2A)
4.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C29(H29A,H29B,H29C)
4.f Idealised tetrahedral OH refined as rotating group:
 O3(H3C), O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1 C 0.3168(6) 0.3306(4) 0.2260(4) 0.0412(16) Uani 1 1 d . . . . .
H1A H 0.249049 0.351161 0.194225 0.049 Uiso 1 1 calc R . . . .
H1B H 0.277250 0.327283 0.272509 0.049 Uiso 1 1 calc R . . . .
C2 C 0.3571(6) 0.2463(4) 0.2025(3) 0.0386(15) Uani 1 1 d . . . . .
H2 H 0.401127 0.251201 0.156651 0.046 Uiso 1 1 calc R . . . .
C3 C 0.2357(6) 0.1927(4) 0.1933(3) 0.0372(15) Uani 1 1 d . . . . .
H3 H 0.191042 0.187567 0.238940 0.045 Uiso 1 1 calc R . . . .
C4 C 0.0216(6) 0.2543(4) 0.1641(3) 0.0372(15) Uani 1 1 d . . . . .
C5 C -0.1849(6) 0.3043(4) 0.1176(4) 0.0457(17) Uani 1 1 d . . . . .
H5 H -0.185862 0.338533 0.159491 0.055 Uiso 1 1 calc R . . . .
C6 C -0.2172(8) 0.3526(5) 0.0516(4) 0.060(2) Uani 1 1 d . . . . .
H6A H -0.278822 0.396187 0.062082 0.071 Uiso 1 1 calc R . . . .
H6B H -0.136436 0.375020 0.031051 0.071 Uiso 1 1 calc R . . . .
C7 C -0.3573(7) 0.2413(5) 0.0467(4) 0.059(2) Uani 1 1 d . . . . .
H7 H -0.450353 0.259899 0.048604 0.070 Uiso 1 1 calc R . . . .
C8 C -0.2420(8) 0.1243(5) 0.0547(4) 0.065(2) Uani 1 1 d . . . . .
H8A H -0.156427 0.139307 0.034470 0.078 Uiso 1 1 calc R . . . .
H8B H -0.251725 0.066222 0.052535 0.078 Uiso 1 1 calc R . . . .
C9 C -0.2541(7) 0.1542(5) 0.1295(4) 0.058(2) Uani 1 1 d . . . . .
H9A H -0.321615 0.124264 0.155108 0.070 Uiso 1 1 calc R . . . .
H9B H -0.169247 0.149914 0.154042 0.070 Uiso 1 1 calc R . . . .
C10 C -0.2948(6) 0.2412(4) 0.1206(3) 0.0496(18) Uani 1 1 d . . . . .
H10 H -0.361932 0.256049 0.155849 0.060 Uiso 1 1 calc R . . . .
C11 C 0.2778(7) 0.1076(4) 0.1688(4) 0.0513(18) Uani 1 1 d . . . . .
H11A H 0.323834 0.112068 0.124091 0.062 Uiso 1 1 calc R . . . .
H11B H 0.340460 0.085374 0.202597 0.062 Uiso 1 1 calc R . . . .
C12 C 0.1607(7) 0.0502(4) 0.1608(4) 0.0488(17) Uani 1 1 d . . . . .
C13 C 0.1055(8) 0.0341(4) 0.0962(4) 0.061(2) Uani 1 1 d . . . . .
H13 H 0.138822 0.059922 0.056512 0.074 Uiso 1 1 calc R . . . .
C14 C 0.0005(8) -0.0203(5) 0.0892(5) 0.071(2) Uani 1 1 d . . . . .
H14 H -0.035759 -0.031248 0.045171 0.086 Uiso 1 1 calc R . . . .
C15 C -0.0489(9) -0.0576(5) 0.1480(6) 0.090(3) Uani 1 1 d . . . . .
H15 H -0.118368 -0.094556 0.143810 0.108 Uiso 1 1 calc R . . . .
C16 C 0.0028(10) -0.0409(6) 0.2123(6) 0.091(3) Uani 1 1 d . . . . .
H16 H -0.032749 -0.065522 0.252082 0.110 Uiso 1 1 calc R . . . .
C17 C 0.1081(9) 0.0125(5) 0.2189(5) 0.074(2) Uani 1 1 d . . . . .
H17 H 0.143742 0.023156 0.263096 0.088 Uiso 1 1 calc R . . . .
C18 C 0.4480(7) 0.4316(4) 0.2953(3) 0.0532(18) Uani 1 1 d . . . . .
H18A H 0.361685 0.451848 0.310560 0.064 Uiso 1 1 calc R . . . .
H18B H 0.506645 0.477394 0.288026 0.064 Uiso 1 1 calc R . . . .
C19 C 0.5061(7) 0.3785(5) 0.3524(4) 0.0572(19) Uani 1 1 d . . . . .
H19 H 0.448251 0.331213 0.357667 0.069 Uiso 1 1 calc R . . . .
C20 C 0.5056(10) 0.4251(6) 0.4217(4) 0.094(3) Uani 1 1 d . . . . .
H20A H 0.533662 0.390134 0.459103 0.141 Uiso 1 1 calc GR . . . .
H20B H 0.416801 0.444437 0.431125 0.141 Uiso 1 1 calc GR . . . .
H20C H 0.566040 0.469889 0.418396 0.141 Uiso 1 1 calc GR . . . .
C21 C 0.6459(8) 0.3499(5) 0.3349(5) 0.082(3) Uani 1 1 d . . . . .
H21A H 0.645324 0.323647 0.289964 0.123 Uiso 1 1 calc GR . . . .
H21B H 0.675453 0.312625 0.370249 0.123 Uiso 1 1 calc GR . . . .
H21C H 0.705565 0.395171 0.333489 0.123 Uiso 1 1 calc GR . . . .
C22 C 0.3160(6) 0.5089(4) 0.1488(3) 0.0393(15) Uani 1 1 d . . . . .
C23 C 0.3193(7) 0.5830(4) 0.1836(3) 0.0441(17) Uani 1 1 d . . . . .
H23 H 0.394650 0.597571 0.209441 0.053 Uiso 1 1 calc R . . . .
C24 C 0.2130(7) 0.6338(4) 0.1800(4) 0.0516(19) Uani 1 1 d . . . . .
H24 H 0.217511 0.683332 0.202605 0.062 Uiso 1 1 calc R . . . .
C25 C 0.0980(7) 0.6136(4) 0.1434(3) 0.0475(17) Uani 1 1 d . . . . .
C26 C 0.0938(7) 0.5392(4) 0.1092(4) 0.0537(19) Uani 1 1 d . . . . .
H26 H 0.017200 0.524273 0.084647 0.064 Uiso 1 1 calc R . . . .
C27 C 0.2011(7) 0.4881(4) 0.1115(3) 0.0489(18) Uani 1 1 d . . . . .
H27 H 0.197383 0.439137 0.087876 0.059 Uiso 1 1 calc R . . . .
C28 C 0.6236(14) 0.6566(8) 0.0556(7) 0.152(5) Uani 1 1 d D U . . .
H28A H 0.529227 0.669753 0.059246 0.182 Uiso 1 1 calc R . . . .
H28B H 0.633476 0.610291 0.024948 0.182 Uiso 1 1 calc R . . . .
C29 C 0.7028(16) 0.7287(9) 0.0267(9) 0.214(7) Uani 1 1 d D U . . .
H29A H 0.706539 0.770319 0.061682 0.322 Uiso 1 1 calc GR . . . .
H29B H 0.659257 0.748926 -0.014635 0.322 Uiso 1 1 calc GR . . . .
H29C H 0.792059 0.711829 0.015100 0.322 Uiso 1 1 calc GR . . . .
N1 N 0.4312(5) 0.3882(3) 0.2281(3) 0.0415(13) Uani 1 1 d . . . . .
N2 N 0.1408(4) 0.2262(3) 0.1438(2) 0.0370(12) Uani 1 1 d . . . . .
H2A H 0.161828 0.228025 0.099996 0.044 Uiso 1 1 calc R . . . .
N3 N -0.0073(6) 0.6669(4) 0.1400(3) 0.0660(18) Uani 1 1 d . . . . .
H3A H -0.002774 0.707718 0.167777 0.079 Uiso 1 1 d R . . . .
H3B H -0.087024 0.650528 0.130547 0.079 Uiso 1 1 d R . . . .
O1 O 0.5708(4) 0.4879(3) 0.1656(3) 0.0571(13) Uani 1 1 d . . . . .
O2 O 0.4421(5) 0.3863(3) 0.0983(2) 0.0532(12) Uani 1 1 d . . . . .
O3 O 0.4507(4) 0.2112(3) 0.2501(2) 0.0539(12) Uani 1 1 d . . . . .
H3C H 0.412049 0.198327 0.286439 0.081 Uiso 1 1 calc GR . . . .
O4 O -0.0168(4) 0.2638(3) 0.2230(2) 0.0467(11) Uani 1 1 d . . . . .
O5 O -0.0534(4) 0.2702(3) 0.1058(2) 0.0451(11) Uani 1 1 d . . . . .
O6 O -0.2777(5) 0.2948(3) 0.0052(2) 0.0647(15) Uani 1 1 d . . . . .
O7 O -0.3505(5) 0.1639(3) 0.0192(3) 0.0686(15) Uani 1 1 d . . . . .
O8 O 0.6789(7) 0.6394(4) 0.1246(3) 0.0917(19) Uani 1 1 d . . . . .
H8 H 0.650898 0.595784 0.138407 0.138 Uiso 1 1 calc GR . . . .
S1 S 0.44914(17) 0.44147(10) 0.15586(9) 0.0446(4) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.038(4) 0.040(4) 0.045(4) -0.001(3) -0.001(3) -0.003(3)
C2 0.031(3) 0.039(4) 0.046(4) 0.006(3) -0.003(3) 0.006(3)
C3 0.036(3) 0.034(4) 0.042(4) 0.005(3) 0.000(3) 0.001(3)
C4 0.034(3) 0.035(4) 0.043(4) -0.005(3) -0.003(3) -0.004(3)
C5 0.033(3) 0.059(5) 0.045(4) -0.001(4) 0.002(3) 0.015(3)
C6 0.060(5) 0.052(5) 0.067(5) 0.002(4) -0.007(4) 0.007(4)
C7 0.045(4) 0.076(6) 0.054(5) -0.006(5) -0.005(4) 0.011(4)
C8 0.073(5) 0.059(5) 0.063(5) -0.004(4) -0.011(4) 0.008(4)
C9 0.055(4) 0.067(5) 0.052(5) 0.003(4) -0.004(4) -0.011(4)
C10 0.032(3) 0.072(5) 0.045(4) -0.002(4) 0.002(3) 0.002(4)
C11 0.049(4) 0.036(4) 0.069(5) 0.000(4) -0.001(4) -0.001(3)
C12 0.055(4) 0.027(3) 0.064(5) 0.004(4) 0.014(4) 0.005(3)
C13 0.066(5) 0.049(5) 0.069(5) 0.000(4) 0.013(4) -0.009(4)
C14 0.064(5) 0.067(6) 0.084(6) -0.020(5) 0.006(5) -0.012(5)
C15 0.072(5) 0.063(5) 0.134(9) -0.021(6) 0.032(7) -0.023(5)
C16 0.104(7) 0.077(7) 0.093(8) 0.005(6) 0.029(6) -0.037(6)
C17 0.097(6) 0.052(5) 0.072(6) 0.001(5) 0.004(5) -0.008(5)
C18 0.056(4) 0.049(4) 0.054(4) -0.008(4) 0.000(4) -0.006(4)
C19 0.073(5) 0.053(5) 0.046(4) -0.001(4) -0.004(4) -0.002(4)
C20 0.131(8) 0.097(8) 0.054(5) -0.020(5) -0.009(5) 0.003(6)
C21 0.076(6) 0.080(6) 0.089(6) -0.005(5) -0.027(5) 0.010(5)
C22 0.036(3) 0.040(4) 0.042(4) 0.004(3) 0.003(3) 0.002(3)
C23 0.046(4) 0.039(4) 0.048(4) -0.001(3) 0.004(3) -0.005(3)
C24 0.065(5) 0.033(4) 0.057(5) -0.008(3) 0.003(4) -0.005(4)
C25 0.054(4) 0.048(4) 0.041(4) 0.007(4) 0.002(3) 0.005(4)
C26 0.054(4) 0.062(5) 0.046(4) 0.002(4) -0.011(4) -0.002(4)
C27 0.060(5) 0.044(4) 0.043(4) -0.008(3) -0.009(4) 0.007(4)
C28 0.152(5) 0.152(5) 0.152(5) -0.0002(7) -0.0002(7) -0.0002(7)
C29 0.215(7) 0.215(7) 0.214(7) 0.0002(14) 0.0002(14) 0.0007(14)
N1 0.041(3) 0.041(3) 0.042(3) 0.003(3) -0.004(3) -0.004(3)
N2 0.032(3) 0.045(3) 0.035(3) 0.001(3) 0.004(2) 0.003(2)
N3 0.062(4) 0.068(4) 0.068(4) -0.004(4) -0.004(3) 0.014(3)
O1 0.042(3) 0.048(3) 0.081(3) 0.006(3) 0.007(3) -0.008(2)
O2 0.063(3) 0.049(3) 0.048(3) -0.007(2) 0.008(2) 0.004(3)
O3 0.040(2) 0.048(3) 0.074(3) 0.004(3) -0.016(2) 0.006(2)
O4 0.041(2) 0.061(3) 0.039(3) -0.003(2) 0.001(2) 0.011(2)
O5 0.032(2) 0.065(3) 0.038(2) -0.004(2) 0.001(2) 0.011(2)
O6 0.063(3) 0.081(4) 0.049(3) 0.000(3) -0.010(3) 0.012(3)
O7 0.072(3) 0.072(4) 0.061(3) -0.014(3) -0.020(3) 0.006(3)
O8 0.103(5) 0.089(5) 0.082(4) 0.011(4) -0.024(4) -0.028(4)
S1 0.0417(9) 0.0399(9) 0.0523(10) -0.0006(9) 0.0012(8) -0.0007(8)

_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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.523(8) . ?
C1 N1 1.491(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.515(8) . ?
C2 O3 1.427(7) . ?
C3 H3 0.9800 . ?
C3 C11 1.544(8) . ?
C3 N2 1.447(7) . ?
C4 N2 1.336(7) . ?
C4 O4 1.195(7) . ?
C4 O5 1.364(7) . ?
C5 H5 0.9800 . ?
C5 C6 1.525(9) . ?
C5 C10 1.517(9) . ?
C5 O5 1.447(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 O6 1.437(8) . ?
C7 H7 0.9800 . ?
C7 C10 1.538(9) . ?
C7 O6 1.430(8) . ?
C7 O7 1.389(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.511(10) . ?
C8 O7 1.436(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.510(10) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.516(9) . ?
C12 C13 1.374(10) . ?
C12 C17 1.375(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.357(12) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(11) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.514(9) . ?
C18 N1 1.477(8) . ?
C19 H19 0.9800 . ?
C19 C20 1.529(10) . ?
C19 C21 1.511(11) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.398(8) . ?
C22 C27 1.392(8) . ?
C22 S1 1.744(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.357(9) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(9) . ?
C25 C26 1.396(9) . ?
C25 N3 1.376(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.367(9) . ?
C27 H27 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.536(3) . ?
C28 O8 1.452(13) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N1 S1 1.643(5) . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8602 . ?
O1 S1 1.450(5) . ?
O2 S1 1.430(4) . ?
O3 H3C 0.8200 . ?
O8 H8 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
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
N1 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
N1 C1 C2 113.3(5) . . ?
C1 C2 H2 107.7 . . ?
C3 C2 C1 111.3(5) . . ?
C3 C2 H2 107.7 . . ?
O3 C2 C1 111.2(5) . . ?
O3 C2 H2 107.7 . . ?
O3 C2 C3 110.9(5) . . ?
C2 C3 H3 108.2 . . ?
C2 C3 C11 110.8(5) . . ?
C11 C3 H3 108.2 . . ?
N2 C3 C2 111.9(5) . . ?
N2 C3 H3 108.2 . . ?
N2 C3 C11 109.5(5) . . ?
N2 C4 O5 108.8(5) . . ?
O4 C4 N2 127.0(6) . . ?
O4 C4 O5 124.1(5) . . ?
C6 C5 H5 111.2 . . ?
C10 C5 H5 111.2 . . ?
C10 C5 C6 104.0(6) . . ?
O5 C5 H5 111.2 . . ?
O5 C5 C6 105.7(5) . . ?
O5 C5 C10 113.1(5) . . ?
C5 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 109.0 . . ?
O6 C6 C5 104.0(6) . . ?
O6 C6 H6A 110.9 . . ?
O6 C6 H6B 110.9 . . ?
C10 C7 H7 110.6 . . ?
O6 C7 H7 110.6 . . ?
O6 C7 C10 106.2(6) . . ?
O7 C7 H7 110.6 . . ?
O7 C7 C10 108.9(6) . . ?
O7 C7 O6 109.8(6) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
O7 C8 H8A 111.1 . . ?
O7 C8 H8B 111.1 . . ?
O7 C8 C9 103.5(6) . . ?
C8 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 C8 103.3(6) . . ?
C10 C9 H9A 111.1 . . ?
C10 C9 H9B 111.1 . . ?
C5 C10 C7 105.0(6) . . ?
C5 C10 H10 110.4 . . ?
C7 C10 H10 110.4 . . ?
C9 C10 C5 118.0(5) . . ?
C9 C10 C7 102.3(6) . . ?
C9 C10 H10 110.4 . . ?
C3 C11 H11A 108.9 . . ?
C3 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C3 113.3(5) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C13 C12 C11 121.5(7) . . ?
C13 C12 C17 118.5(7) . . ?
C17 C12 C11 120.0(7) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(8) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.1(8) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(8) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(9) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.7(8) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
N1 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
N1 C18 C19 112.4(6) . . ?
C18 C19 H19 108.3 . . ?
C18 C19 C20 108.9(6) . . ?
C20 C19 H19 108.3 . . ?
C21 C19 C18 112.3(7) . . ?
C21 C19 H19 108.3 . . ?
C21 C19 C20 110.6(7) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 S1 120.7(5) . . ?
C27 C22 C23 118.7(6) . . ?
C27 C22 S1 120.6(5) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(6) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.2 . . ?
C23 C24 C25 121.7(6) . . ?
C25 C24 H24 119.2 . . ?
C24 C25 C26 118.2(6) . . ?
N3 C25 C24 120.1(6) . . ?
N3 C25 C26 121.6(7) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.7(6) . . ?
C27 C26 H26 119.7 . . ?
C22 C27 H27 119.7 . . ?
C26 C27 C22 120.5(6) . . ?
C26 C27 H27 119.7 . . ?
H28A C28 H28B 108.7 . . ?
C29 C28 H28A 110.5 . . ?
C29 C28 H28B 110.5 . . ?
O8 C28 H28A 110.5 . . ?
O8 C28 H28B 110.5 . . ?
O8 C28 C29 106.3(11) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C1 N1 S1 114.0(4) . . ?
C18 N1 C1 115.0(5) . . ?
C18 N1 S1 116.7(4) . . ?
C3 N2 H2A 119.0 . . ?
C4 N2 C3 122.0(5) . . ?
C4 N2 H2A 119.0 . . ?
C25 N3 H3A 116.0 . . ?
C25 N3 H3B 120.8 . . ?
H3A N3 H3B 115.3 . . ?
C2 O3 H3C 109.5 . . ?
C4 O5 C5 116.6(4) . . ?
C7 O6 C6 108.0(5) . . ?
C7 O7 C8 106.4(5) . . ?
C28 O8 H8 109.5 . . ?
N1 S1 C22 109.1(3) . . ?
O1 S1 C22 107.9(3) . . ?
O1 S1 N1 105.7(3) . . ?
O2 S1 C22 108.4(3) . . ?
O2 S1 N1 106.9(3) . . ?
O2 S1 O1 118.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A O6 0.86 2.13 2.970(7) 167.4 3 yes
N3 H3A O4 0.86 2.29 3.073(8) 152.1 4 yes
N3 H3B O8 0.86 2.35 3.179(9) 163.0 1_455 yes
O3 H3C O8 0.82 2.16 2.963(9) 168.1 4_645 yes
O8 H8 O1 0.82 2.03 2.847(7) 175.2 . yes

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 C2 C3 C11 179.5(5) . . . . ?
C1 C2 C3 N2 57.1(7) . . . . ?
C1 N1 S1 C22 69.2(5) . . . . ?
C1 N1 S1 O1 -175.1(4) . . . . ?
C1 N1 S1 O2 -47.8(5) . . . . ?
C2 C1 N1 C18 -127.3(6) . . . . ?
C2 C1 N1 S1 94.0(6) . . . . ?
C2 C3 C11 C12 178.3(6) . . . . ?
C2 C3 N2 C4 -110.6(6) . . . . ?
C3 C11 C12 C13 99.7(8) . . . . ?
C3 C11 C12 C17 -80.7(8) . . . . ?
C5 C6 O6 C7 36.7(7) . . . . ?
C6 C5 C10 C7 16.0(7) . . . . ?
C6 C5 C10 C9 129.0(6) . . . . ?
C6 C5 O5 C4 152.9(5) . . . . ?
C8 C9 C10 C5 -91.7(7) . . . . ?
C8 C9 C10 C7 22.8(7) . . . . ?
C9 C8 O7 C7 38.6(7) . . . . ?
C10 C5 C6 O6 -31.8(7) . . . . ?
C10 C5 O5 C4 -93.9(6) . . . . ?
C10 C7 O6 C6 -26.4(7) . . . . ?
C10 C7 O7 C8 -24.1(8) . . . . ?
C11 C3 N2 C4 126.2(6) . . . . ?
C11 C12 C13 C14 178.3(6) . . . . ?
C11 C12 C17 C16 -179.0(7) . . . . ?
C12 C13 C14 C15 0.6(12) . . . . ?
C13 C12 C17 C16 0.6(11) . . . . ?
C13 C14 C15 C16 0.8(14) . . . . ?
C14 C15 C16 C17 -1.5(15) . . . . ?
C15 C16 C17 C12 0.8(14) . . . . ?
C17 C12 C13 C14 -1.3(11) . . . . ?
C18 N1 S1 C22 -68.8(5) . . . . ?
C18 N1 S1 O1 47.0(5) . . . . ?
C18 N1 S1 O2 174.3(5) . . . . ?
C19 C18 N1 C1 74.6(7) . . . . ?
C19 C18 N1 S1 -147.9(5) . . . . ?
C22 C23 C24 C25 1.4(10) . . . . ?
C23 C22 C27 C26 -0.2(10) . . . . ?
C23 C22 S1 N1 83.8(5) . . . . ?
C23 C22 S1 O1 -30.5(6) . . . . ?
C23 C22 S1 O2 -160.2(5) . . . . ?
C23 C24 C25 C26 -0.6(10) . . . . ?
C23 C24 C25 N3 -179.2(6) . . . . ?
C24 C25 C26 C27 -0.5(10) . . . . ?
C25 C26 C27 C22 0.9(10) . . . . ?
C27 C22 C23 C24 -1.0(9) . . . . ?
C27 C22 S1 N1 -92.6(6) . . . . ?
C27 C22 S1 O1 153.1(5) . . . . ?
C27 C22 S1 O2 23.4(6) . . . . ?
N1 C1 C2 C3 -173.5(5) . . . . ?
N1 C1 C2 O3 62.2(7) . . . . ?
N1 C18 C19 C20 -173.8(7) . . . . ?
N1 C18 C19 C21 63.4(8) . . . . ?
N2 C3 C11 C12 -57.9(7) . . . . ?
N2 C4 O5 C5 -177.7(5) . . . . ?
N3 C25 C26 C27 178.0(6) . . . . ?
O3 C2 C3 C11 -56.1(7) . . . . ?
O3 C2 C3 N2 -178.5(5) . . . . ?
O4 C4 N2 C3 8.5(9) . . . . ?
O4 C4 O5 C5 3.0(9) . . . . ?
O5 C4 N2 C3 -170.7(5) . . . . ?
O5 C5 C6 O6 87.5(6) . . . . ?
O5 C5 C10 C7 -98.1(6) . . . . ?
O5 C5 C10 C9 14.9(8) . . . . ?
O6 C7 C10 C5 5.3(7) . . . . ?
O6 C7 C10 C9 -118.5(6) . . . . ?
O6 C7 O7 C8 91.9(6) . . . . ?
O7 C7 C10 C5 123.5(6) . . . . ?
O7 C7 C10 C9 -0.2(7) . . . . ?
O7 C7 O6 C6 -144.0(5) . . . . ?
O7 C8 C9 C10 -37.8(7) . . . . ?
S1 C22 C23 C24 -177.5(5) . . . . ?
S1 C22 C27 C26 176.3(5) . . . . ?

_iucr_refine_instructions_details 
;
TITL dalunav in P 21 21 21
    dl-ethy.res
    created by SHELXL-2018/3 at 13:36:02 on 24-Aug-2018
CELL 0.71073 9.9846 16.6017 19.0274 90 90 90
ZERR 4 0.0005 0.001 0.001 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O S
UNIT 116 172 12 32 4
EQIV $1 0.5+X,0.5-Y,-Z
EQIV $2 -X,0.5+Y,0.5-Z
EQIV $3 -1+X,+Y,+Z
EQIV $4 1-X,-0.5+Y,0.5-Z
DFIX 1.54 0.002 C28 C29
ISOR 0.0005 0.001 C28 C29

L.S. 30
PLAN  3
SIZE 0.16 0.2 0.47
TEMP 23
HTAB N2 O6_$1
HTAB N3 O4_$2
HTAB N3 O8_$3
HTAB O3 O8_$4
HTAB O8 O1
BOND $H
CONF
fmap 2
acta
MERG 2
OMIT -3 52
REM <olex2.extras>
REM <HklSrc "%.\\dalunav.hkl">
REM </olex2.extras>

WGHT    0.052300    1.433600
FVAR       0.35334
C1    1    0.316806    0.330570    0.226036    11.00000    0.03782    0.04028 =
         0.04537   -0.00078   -0.00064   -0.00305
AFIX  23
H1A   2    0.249049    0.351161    0.194225    11.00000   -1.20000
H1B   2    0.277250    0.327283    0.272509    11.00000   -1.20000
AFIX   0
C2    1    0.357079    0.246338    0.202482    11.00000    0.03095    0.03850 =
         0.04647    0.00632   -0.00255    0.00637
AFIX  13
H2    2    0.401127    0.251201    0.156651    11.00000   -1.20000
AFIX   0
C3    1    0.235680    0.192655    0.193285    11.00000    0.03599    0.03403 =
         0.04173    0.00459   -0.00048    0.00056
AFIX  13
H3    2    0.191042    0.187567    0.238940    11.00000   -1.20000
AFIX   0
C4    1    0.021562    0.254293    0.164052    11.00000    0.03441    0.03450 =
         0.04266   -0.00463   -0.00282   -0.00448
C5    1   -0.184875    0.304262    0.117558    11.00000    0.03302    0.05867 =
         0.04542   -0.00074    0.00235    0.01546
AFIX  13
H5    2   -0.185862    0.338533    0.159491    11.00000   -1.20000
AFIX   0
C6    1   -0.217193    0.352649    0.051596    11.00000    0.06007    0.05189 =
         0.06670    0.00183   -0.00713    0.00656
AFIX  23
H6A   2   -0.278822    0.396187    0.062082    11.00000   -1.20000
H6B   2   -0.136436    0.375020    0.031051    11.00000   -1.20000
AFIX   0
C7    1   -0.357267    0.241306    0.046716    11.00000    0.04508    0.07612 =
         0.05442   -0.00582   -0.00514    0.01112
AFIX  13
H7    2   -0.450353    0.259899    0.048604    11.00000   -1.20000
AFIX   0
C8    1   -0.242016    0.124303    0.054727    11.00000    0.07328    0.05893 =
         0.06270   -0.00408   -0.01063    0.00782
AFIX  23
H8A   2   -0.156427    0.139307    0.034470    11.00000   -1.20000
H8B   2   -0.251725    0.066222    0.052535    11.00000   -1.20000
AFIX   0
C9    1   -0.254054    0.154246    0.129463    11.00000    0.05547    0.06665 =
         0.05243    0.00341   -0.00428   -0.01093
AFIX  23
H9A   2   -0.321615    0.124264    0.155108    11.00000   -1.20000
H9B   2   -0.169247    0.149914    0.154042    11.00000   -1.20000
AFIX   0
C10   1   -0.294762    0.241232    0.120589    11.00000    0.03189    0.07241 =
         0.04462   -0.00230    0.00210    0.00200
AFIX  13
H10   2   -0.361932    0.256049    0.155849    11.00000   -1.20000
AFIX   0
C11   1    0.277818    0.107646    0.168823    11.00000    0.04872    0.03638 =
         0.06884   -0.00005   -0.00142   -0.00106
AFIX  23
H11A  2    0.323834    0.112068    0.124091    11.00000   -1.20000
H11B  2    0.340460    0.085374    0.202597    11.00000   -1.20000
AFIX   0
C12   1    0.160741    0.050230    0.160787    11.00000    0.05475    0.02733 =
         0.06442    0.00384    0.01407    0.00528
C13   1    0.105456    0.034066    0.096179    11.00000    0.06609    0.04906 =
         0.06921   -0.00020    0.01331   -0.00878
AFIX  43
H13   2    0.138822    0.059922    0.056512    11.00000   -1.20000
AFIX   0
C14   1    0.000493   -0.020295    0.089168    11.00000    0.06362    0.06696 =
         0.08386   -0.01997    0.00609   -0.01229
AFIX  43
H14   2   -0.035759   -0.031248    0.045171    11.00000   -1.20000
AFIX   0
C15   1   -0.048887   -0.057561    0.148018    11.00000    0.07221    0.06312 =
         0.13393   -0.02083    0.03230   -0.02281
AFIX  43
H15   2   -0.118368   -0.094556    0.143810    11.00000   -1.20000
AFIX   0
C16   1    0.002783   -0.040908    0.212332    11.00000    0.10390    0.07677 =
         0.09329    0.00545    0.02924   -0.03732
AFIX  43
H16   2   -0.032749   -0.065522    0.252082    11.00000   -1.20000
AFIX   0
C17   1    0.108091    0.012548    0.218900    11.00000    0.09712    0.05203 =
         0.07167    0.00055    0.00357   -0.00775
AFIX  43
H17   2    0.143742    0.023156    0.263096    11.00000   -1.20000
AFIX   0
C18   1    0.448013    0.431556    0.295286    11.00000    0.05631    0.04927 =
         0.05398   -0.00786   -0.00045   -0.00566
AFIX  23
H18A  2    0.361685    0.451848    0.310560    11.00000   -1.20000
H18B  2    0.506645    0.477394    0.288026    11.00000   -1.20000
AFIX   0
C19   1    0.506074    0.378523    0.352364    11.00000    0.07252    0.05302 =
         0.04595   -0.00104   -0.00359   -0.00167
AFIX  13
H19   2    0.448251    0.331213    0.357667    11.00000   -1.20000
AFIX   0
C20   1    0.505600    0.425077    0.421697    11.00000    0.13063    0.09689 =
         0.05381   -0.01951   -0.00905    0.00257
AFIX 137
H20A  2    0.533662    0.390134    0.459103    11.00000   -1.50000
H20B  2    0.416801    0.444437    0.431125    11.00000   -1.50000
H20C  2    0.566040    0.469889    0.418396    11.00000   -1.50000
AFIX   0
C21   1    0.645851    0.349879    0.334926    11.00000    0.07621    0.07972 =
         0.08931   -0.00526   -0.02748    0.00977
AFIX 137
H21A  2    0.645324    0.323647    0.289964    11.00000   -1.50000
H21B  2    0.675453    0.312625    0.370249    11.00000   -1.50000
H21C  2    0.705565    0.395171    0.333489    11.00000   -1.50000
AFIX   0
C22   1    0.315956    0.508917    0.148773    11.00000    0.03601    0.03993 =
         0.04196    0.00355    0.00311    0.00229
C23   1    0.319326    0.583014    0.183648    11.00000    0.04557    0.03858 =
         0.04804   -0.00133    0.00441   -0.00524
AFIX  43
H23   2    0.394650    0.597571    0.209441    11.00000   -1.20000
AFIX   0
C24   1    0.212982    0.633758    0.179968    11.00000    0.06492    0.03252 =
         0.05726   -0.00835    0.00275   -0.00530
AFIX  43
H24   2    0.217511    0.683332    0.202605    11.00000   -1.20000
AFIX   0
C25   1    0.097966    0.613596    0.143377    11.00000    0.05378    0.04820 =
         0.04063    0.00664    0.00247    0.00489
C26   1    0.093795    0.539230    0.109206    11.00000    0.05380    0.06158 =
         0.04567    0.00165   -0.01114   -0.00192
AFIX  43
H26   2    0.017200    0.524273    0.084647    11.00000   -1.20000
AFIX   0
C27   1    0.201130    0.488150    0.111461    11.00000    0.05966    0.04422 =
         0.04288   -0.00814   -0.00853    0.00748
AFIX  43
H27   2    0.197383    0.439137    0.087876    11.00000   -1.20000
AFIX   0

C28   1    0.623623    0.656579    0.055624    11.00000    0.15208    0.15197 =
         0.15182   -0.00024   -0.00024   -0.00024
AFIX  23
H28A  2    0.529227    0.669753    0.059246    11.00000   -1.20000
H28B  2    0.633476    0.610291    0.024948    11.00000   -1.20000
AFIX   0
C29   1    0.702792    0.728673    0.026734    11.00000    0.21457    0.21469 =
         0.21382    0.00019    0.00024    0.00070
AFIX 137
H29A  2    0.706539    0.770319    0.061682    11.00000   -1.50000
H29B  2    0.659257    0.748926   -0.014635    11.00000   -1.50000
H29C  2    0.792059    0.711829    0.015100    11.00000   -1.50000
AFIX   0

N1    3    0.431175    0.388250    0.228084    11.00000    0.04117    0.04137 =
         0.04198    0.00260   -0.00391   -0.00391
N2    3    0.140801    0.226164    0.143796    11.00000    0.03153    0.04465 =
         0.03494    0.00076    0.00446    0.00265
AFIX  43
H2A   2    0.161828    0.228025    0.099996    11.00000   -1.20000
AFIX   0
N3    3   -0.007324    0.666938    0.140007    11.00000    0.06225    0.06754 =
         0.06825   -0.00356   -0.00383    0.01415
AFIX   3
H3A   2   -0.002774    0.707718    0.167777    11.00000   -1.20000
H3B   2   -0.087024    0.650528    0.130547    11.00000   -1.20000
AFIX   0
O1    4    0.570778    0.487897    0.165630    11.00000    0.04237    0.04790 =
         0.08103    0.00638    0.00653   -0.00833
O2    4    0.442133    0.386293    0.098293    11.00000    0.06312    0.04870 =
         0.04789   -0.00734    0.00797    0.00441
O3    4    0.450717    0.211183    0.250111    11.00000    0.04036    0.04756 =
         0.07368    0.00387   -0.01598    0.00594
AFIX 147
H3C   2    0.412049    0.198327    0.286439    11.00000   -1.50000
AFIX   0
O4    4   -0.016782    0.263795    0.222963    11.00000    0.04071    0.06072 =
         0.03863   -0.00282    0.00091    0.01103
O5    4   -0.053413    0.270211    0.105775    11.00000    0.03214    0.06524 =
         0.03798   -0.00419    0.00097    0.01062
O6    4   -0.277670    0.294828    0.005208    11.00000    0.06345    0.08136 =
         0.04927   -0.00020   -0.01007    0.01163
O7    4   -0.350451    0.163903    0.019178    11.00000    0.07226    0.07205 =
         0.06140   -0.01427   -0.01986    0.00564

O8    4    0.678949    0.639417    0.124581    11.00000    0.10347    0.08943 =
         0.08226    0.01124   -0.02388   -0.02759
AFIX 147
H8    2    0.650898    0.595784    0.138407    11.00000   -1.50000
AFIX   0

S1    5    0.449140    0.441466    0.155864    11.00000    0.04175    0.03987 =
         0.05232   -0.00058    0.00124   -0.00069
HKLF 4




REM  dalunav in P 21 21 21
REM wR2 = 0.1592, GooF = S = 1.103, Restrained GooF = 1.102 for all data
REM R1 = 0.0923 for 3911 Fo > 4sig(Fo) and 0.1451 for all 6191 data
REM 375 parameters refined using 13 restraints

END  
     
WGHT      0.0549      1.4350 

REM Highest difference peak  0.290,  deepest hole -0.306,  1-sigma level  0.050
Q1    1   0.5402  0.6970  0.0209  11.00000  0.05    0.29
Q2    1   0.3739  0.4814  0.1505  11.00000  0.05    0.23
Q3    1   0.6782  0.6473  0.0372  11.00000  0.05    0.22

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0923 for 3911 Fo > 4sig(Fo) and 0.1451 for all 30521 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.29, deepest hole -0.31
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1451
  REM R1_gt = 0.0923
  REM wR_ref = 0.1592
  REM GOOF = 1.103
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 30521
  REM Reflections_gt = 3911
  REM Parameters = n/a
  REM Hole = -0.31
  REM Peak = 0.29
  REM Flack = 0.01(5)

  
;
_olex2_submission_original_sample_id DLNW-C2H5OH
_olex2_submission_special_instructions 'No special instructions were received'
