# 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 
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data_mo_023ub122_0ma_aa
_database_code_depnum_ccdc_archive 'CCDC 1821371'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        'Sildenafil anisole solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H30 N6 O4 S), C7 H8 O'
_chemical_formula_sum            'C51 H68 N12 O9 S2'
_chemical_formula_weight         1057.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.8822(7)
_cell_length_b                   14.2697(7)
_cell_length_c                   12.8142(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.409(2)
_cell_angle_gamma                90
_cell_volume                     2610.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9578
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      30.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             1124
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7218
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 We have eliminated all potential causes of this alert, but the minimum and maximum
 residual electron density still remains more negative and positive than normally expected,
 the names of the nearest atoms to this minimum and their distances from the minimum are :
Highest peak    2.30  at  0.4842  0.6393  0.3799  [  0.08 A from C24 ]
 Deepest hole   -2.52  at  0.4526  0.4292  0.4383  [  0.17 A from O5 ]
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            95257
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.018
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8010
_reflns_number_gt                6939
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'XT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0874P)²+4.4294P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8010
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1704
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
S1 S 0.17342(3) 0.46860(3) 0.11969(3) 0.00912(10) Uani 1 1 d . . . . .
O1 O 0.09337(9) 0.42249(9) 0.04883(10) 0.0133(2) Uani 1 1 d . . . . .
O2 O 0.25894(9) 0.41783(9) 0.16347(10) 0.0129(2) Uani 1 1 d . . . . .
O3 O 0.06470(9) 0.61753(10) 0.49634(10) 0.0151(3) Uani 1 1 d . . . . .
O4 O 0.40956(9) 0.71372(9) 0.67239(11) 0.0156(3) Uani 1 1 d . . . . .
N1 N 0.19808(10) 0.55593(11) 0.05079(12) 0.0120(3) Uani 1 1 d . . . . .
N2 N 0.23483(11) 0.70624(11) -0.07609(12) 0.0135(3) Uani 1 1 d . . . . .
N3 N 0.29101(10) 0.62716(10) 0.56100(11) 0.0102(3) Uani 1 1 d . . . . .
H3N H 0.2718 0.6763 0.5192 0.012 Uiso 1 1 calc R U . . .
N4 N 0.26007(10) 0.46660(10) 0.58541(12) 0.0119(3) Uani 1 1 d . . . . .
N5 N 0.44882(10) 0.53388(11) 0.81040(12) 0.0126(3) Uani 1 1 d . . . . .
N6 N 0.44131(11) 0.44343(11) 0.83924(12) 0.0144(3) Uani 1 1 d . . . . .
C1 C 0.12393(12) 0.62353(13) 0.00223(14) 0.0135(3) Uani 1 1 d . . . . .
H1A H 0.1241 0.6749 0.0542 0.016 Uiso 1 1 calc R U . . .
H1B H 0.0620 0.5924 -0.0160 0.016 Uiso 1 1 calc R U . . .
C2 C 0.14217(13) 0.66245(12) -0.09996(14) 0.0139(3) Uani 1 1 d . . . . .
H2A H 0.1380 0.6111 -0.1531 0.017 Uiso 1 1 calc R U . . .
H2B H 0.0935 0.7094 -0.1331 0.017 Uiso 1 1 calc R U . . .
C3 C 0.30775(13) 0.63798(13) -0.02306(17) 0.0178(4) Uani 1 1 d . . . . .
H3A H 0.3699 0.6686 -0.0054 0.021 Uiso 1 1 calc R U . . .
H3B H 0.3078 0.5857 -0.0738 0.021 Uiso 1 1 calc R U . . .
C4 C 0.29114(12) 0.59954(13) 0.08040(16) 0.0156(3) Uani 1 1 d . . . . .
H4A H 0.3397 0.5526 0.1140 0.019 Uiso 1 1 calc R U . . .
H4B H 0.2940 0.6508 0.1333 0.019 Uiso 1 1 calc R U . . .
C5 C 0.24924(16) 0.73993(14) -0.17837(17) 0.0225(4) Uani 1 1 d . . . . .
H5A H 0.2458 0.6870 -0.2281 0.034 Uiso 1 1 calc R U . . .
H5B H 0.3110 0.7695 -0.1635 0.034 Uiso 1 1 calc R U . . .
H5C H 0.2006 0.7858 -0.2118 0.034 Uiso 1 1 calc R U . . .
C6 C 0.13736(11) 0.51306(12) 0.22971(13) 0.0102(3) Uani 1 1 d . . . . .
C7 C 0.04777(12) 0.55070(13) 0.21373(13) 0.0123(3) Uani 1 1 d . . . . .
H7 H 0.0051 0.5518 0.1429 0.015 Uiso 1 1 calc R U . . .
C8 C 0.02104(12) 0.58650(12) 0.30140(14) 0.0126(3) Uani 1 1 d . . . . .
H8 H -0.0399 0.6121 0.2904 0.015 Uiso 1 1 calc R U . . .
C9 C 0.08389(11) 0.58484(12) 0.40574(13) 0.0108(3) Uani 1 1 d . . . . .
C10 C 0.17360(11) 0.54630(12) 0.42156(13) 0.0102(3) Uani 1 1 d . . . . .
C11 C 0.19991(11) 0.51091(12) 0.33358(13) 0.0105(3) Uani 1 1 d . . . . .
H11 H 0.2607 0.4852 0.3443 0.013 Uiso 1 1 calc R U . . .
C12 C 0.24354(11) 0.54396(12) 0.53055(13) 0.0106(3) Uani 1 1 d . . . . .
C13 C 0.36709(11) 0.63928(12) 0.65282(13) 0.0104(3) Uani 1 1 d . . . . .
C14 C 0.38403(11) 0.55413(12) 0.71508(13) 0.0112(3) Uani 1 1 d . . . . .
C15 C 0.33202(12) 0.47324(12) 0.68129(13) 0.0113(3) Uani 1 1 d . . . . .
C16 C 0.37084(12) 0.40547(12) 0.76160(14) 0.0132(3) Uani 1 1 d . . . . .
C17 C 0.34212(14) 0.30562(13) 0.76676(15) 0.0171(3) Uani 1 1 d . . . . .
H17A H 0.3911 0.2723 0.8231 0.021 Uiso 1 1 calc R U . . .
H17B H 0.3370 0.2750 0.6960 0.021 Uiso 1 1 calc R U . . .
C18 C 0.24786(16) 0.29694(16) 0.79347(19) 0.0268(4) Uani 1 1 d . . . . .
H18A H 0.1991 0.3300 0.7368 0.032 Uiso 1 1 calc R U . . .
H18B H 0.2301 0.2300 0.7912 0.032 Uiso 1 1 calc R U . . .
C19 C 0.2500(2) 0.3367(2) 0.9038(3) 0.0509(9) Uani 1 1 d . . . . .
H19A H 0.2665 0.4033 0.9063 0.076 Uiso 1 1 calc R U . . .
H19B H 0.2967 0.3029 0.9607 0.076 Uiso 1 1 calc R U . . .
H19C H 0.1882 0.3295 0.9157 0.076 Uiso 1 1 calc R U . . .
C20 C -0.02942(12) 0.64978(14) 0.48699(15) 0.0159(3) Uani 1 1 d . . . . .
H20A H -0.0755 0.6001 0.4552 0.019 Uiso 1 1 calc R U . . .
H20B H -0.0441 0.7058 0.4396 0.019 Uiso 1 1 calc R U . . .
C21 C -0.03304(15) 0.67354(15) 0.60069(16) 0.0205(4) Uani 1 1 d . . . . .
H21A H -0.0967 0.6931 0.5985 0.031 Uiso 1 1 calc R U . . .
H21B H 0.0109 0.7246 0.6299 0.031 Uiso 1 1 calc R U . . .
H21C H -0.0157 0.6183 0.6474 0.031 Uiso 1 1 calc R U . . .
C22 C 0.52045(13) 0.59451(14) 0.87753(14) 0.0170(3) Uani 1 1 d . . . . .
H22A H 0.5760 0.5933 0.8508 0.026 Uiso 1 1 calc R U . . .
H22B H 0.5373 0.5724 0.9530 0.026 Uiso 1 1 calc R U . . .
H22C H 0.4964 0.6587 0.8741 0.026 Uiso 1 1 calc R U . . .
C23 C 0.53502(19) 0.6520(3) 0.4814(2) 0.0432(4) Uani 1 1 d . . . . .
H23 H 0.5632 0.7115 0.5014 0.052 Uiso 0.5 1 calc R U P A 1
H23A H 0.5600 0.7159 0.4927 0.052 Uiso 0.5 1 calc R U P A 2
H23B H 0.5870 0.6072 0.4957 0.052 Uiso 0.5 1 calc R U P A 2
H23C H 0.4969 0.6399 0.5310 0.052 Uiso 0.5 1 calc R U P A 2
C24 C 0.5148(4) 0.3570(5) 0.6153(4) 0.0432(4) Uani 0.5 1 d . . P . .
H24 H 0.5263 0.3086 0.6683 0.052 Uiso 0.5 1 calc R U P . .
C25 C 0.54884(19) 0.4427(3) 0.6330(2) 0.0432(4) Uani 1 1 d . . . . .
H25 H 0.5883 0.4601 0.7024 0.052 Uiso 1 1 calc R U . . .
C26 C 0.5262(4) 0.5059(5) 0.5496(4) 0.0432(4) Uani 0.5 1 d . . P . .
C27 C 0.55386(16) 0.5807(2) 0.56538(18) 0.0432(4) Uani 0.5 1 d . . P B 1
H27 H 0.5907 0.5970 0.6365 0.052 Uiso 0.5 1 calc R U P B 1
O5 O 0.55386(16) 0.5807(2) 0.56538(18) 0.0432(4) Uani 0.5 1 d . . P B 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
S1 O2 1.4338(13) . ?
S1 O1 1.4372(13) . ?
S1 N1 1.6279(15) . ?
S1 C6 1.7622(17) . ?
O3 C9 1.354(2) . ?
O3 C20 1.447(2) . ?
O4 C13 1.225(2) . ?
N1 C1 1.466(2) . ?
N1 C4 1.467(2) . ?
N2 C2 1.465(2) . ?
N2 C5 1.468(2) . ?
N2 C3 1.474(2) . ?
N3 C12 1.380(2) . ?
N3 C13 1.394(2) . ?
N3 H3N 0.8800 . ?
N4 C12 1.294(2) . ?
N4 C15 1.386(2) . ?
N5 N6 1.356(2) . ?
N5 C14 1.356(2) . ?
N5 C22 1.451(2) . ?
N6 C16 1.339(2) . ?
C1 C2 1.516(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.392(2) . ?
C6 C7 1.398(2) . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(2) . ?
C10 C11 1.389(2) . ?
C10 C12 1.488(2) . ?
C11 H11 0.9500 . ?
C13 C14 1.436(2) . ?
C14 C15 1.389(2) . ?
C15 C16 1.411(2) . ?
C16 C17 1.494(3) . ?
C17 C18 1.540(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.515(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.512(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.258(6) 3_666 ?
C23 C27 1.449(3) . ?
C23 H23 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C23 1.258(6) 3_666 ?
C24 C25 1.319(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.366(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.142(8) . ?
C26 C26 1.302(12) 3_666 ?
C26 C27 2.032(8) 3_666 ?
C27 C26 2.032(8) 3_666 ?
C27 H27 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
O2 S1 O1 120.11(8) . . ?
O2 S1 N1 106.73(8) . . ?
O1 S1 N1 106.34(8) . . ?
O2 S1 C6 107.83(8) . . ?
O1 S1 C6 106.55(8) . . ?
N1 S1 C6 108.94(8) . . ?
C9 O3 C20 118.18(13) . . ?
C1 N1 C4 111.91(14) . . ?
C1 N1 S1 118.44(11) . . ?
C4 N1 S1 121.69(12) . . ?
C2 N2 C5 108.64(15) . . ?
C2 N2 C3 109.97(14) . . ?
C5 N2 C3 110.74(15) . . ?
C12 N3 C13 125.04(14) . . ?
C12 N3 H3N 117.5 . . ?
C13 N3 H3N 117.5 . . ?
C12 N4 C15 113.82(14) . . ?
N6 N5 C14 110.85(14) . . ?
N6 N5 C22 120.62(14) . . ?
C14 N5 C22 128.53(15) . . ?
C16 N6 N5 106.87(14) . . ?
N1 C1 C2 108.11(14) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N2 C2 C1 111.32(14) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 111.17(14) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C3 107.59(15) . . ?
N1 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
N1 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 120.05(15) . . ?
C11 C6 S1 118.97(13) . . ?
C7 C6 S1 120.97(12) . . ?
C8 C7 C6 120.10(15) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.96(15) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
O3 C9 C8 124.58(15) . . ?
O3 C9 C10 115.67(14) . . ?
C8 C9 C10 119.75(15) . . ?
C11 C10 C9 119.98(15) . . ?
C11 C10 C12 118.09(14) . . ?
C9 C10 C12 121.91(15) . . ?
C10 C11 C6 120.16(15) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
N4 C12 N3 125.20(15) . . ?
N4 C12 C10 120.27(15) . . ?
N3 C12 C10 114.37(14) . . ?
O4 C13 N3 121.96(15) . . ?
O4 C13 C14 128.34(15) . . ?
N3 C13 C14 109.70(14) . . ?
N5 C14 C15 107.18(15) . . ?
N5 C14 C13 130.47(16) . . ?
C15 C14 C13 122.34(15) . . ?
N4 C15 C14 123.77(15) . . ?
N4 C15 C16 130.84(16) . . ?
C14 C15 C16 105.36(15) . . ?
N6 C16 C15 109.74(15) . . ?
N6 C16 C17 121.78(16) . . ?
C15 C16 C17 128.48(16) . . ?
C16 C17 C18 112.11(16) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 113.4(2) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 106.79(15) . . ?
O3 C20 H20A 110.4 . . ?
C21 C20 H20A 110.4 . . ?
O3 C20 H20B 110.4 . . ?
C21 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C27 126.7(5) 3_666 . ?
C24 C23 H23 116.7 3_666 . ?
C27 C23 H23 116.7 . . ?
C24 C23 H23A 109.5 3_666 . ?
C24 C23 H23B 109.5 3_666 . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 3_666 . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C23 C24 C25 110.8(5) 3_666 . ?
C23 C24 H24 124.6 3_666 . ?
C25 C24 H24 124.6 . . ?
C24 C25 C26 118.7(5) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C27 C26 C26 112.4(7) . 3_666 ?
C27 C26 C25 118.9(5) . . ?
C26 C26 C25 128.7(10) 3_666 . ?
C27 C26 C27 143.7(4) . 3_666 ?
C26 C26 C27 31.3(5) 3_666 3_666 ?
C25 C26 C27 97.4(5) . 3_666 ?
C26 C27 C23 122.7(4) . . ?
C26 C27 C26 36.3(4) . 3_666 ?
C23 C27 C26 86.4(2) . 3_666 ?
C26 C27 H27 118.6 . . ?
C23 C27 H27 118.6 . . ?
C26 C27 H27 154.9 3_666 . ?

_refine_diff_density_max         2.299
_refine_diff_density_min         -2.520
_refine_diff_density_rms         0.095

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_mo_023WB33_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1832573'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        'Sildenafil dioxane solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 N6 O4 S, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C24 H34 N6 O5 S'
_chemical_formula_weight         518.63

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.6055(5)
_cell_length_b                   13.5523(4)
_cell_length_c                   12.5064(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.3620(10)
_cell_angle_gamma                90
_cell_volume                     2537.86(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6895
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.71

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27836
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         26.780
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5382
_reflns_number_gt                4067
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'XT-2014 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0491P)²+3.1869P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5382
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
S1 S 0.66750(3) 0.44675(4) 0.11555(4) 0.01198(12) Uani 1 1 d . . . . .
H1N H 0.7681(18) 0.692(2) 0.513(2) 0.030(7) Uiso 1 1 d . . . . .
O1 O 0.58735(9) 0.40214(11) 0.04592(12) 0.0168(3) Uani 1 1 d . . . . .
O2 O 0.74624(9) 0.38822(11) 0.15740(12) 0.0159(3) Uani 1 1 d . . . . .
O3 O 0.90181(9) 0.73492(11) 0.66317(12) 0.0174(3) Uani 1 1 d . . . . .
O4 O 0.57469(9) 0.62117(11) 0.50117(11) 0.0152(3) Uani 1 1 d . . . . .
N1 N 0.69311(11) 0.53521(13) 0.04220(14) 0.0144(4) Uani 1 1 d . . . . .
N2 N 0.73243(12) 0.69379(13) -0.08438(14) 0.0155(4) Uani 1 1 d . . . . .
N3 N 0.78949(11) 0.63686(13) 0.55873(14) 0.0112(3) Uani 1 1 d . . . . .
N4 N 0.76786(11) 0.46718(13) 0.59346(14) 0.0130(4) Uani 1 1 d . . . . .
N5 N 0.95118(11) 0.55215(13) 0.81195(13) 0.0128(3) Uani 1 1 d . . . . .
N6 N 0.94942(11) 0.45744(13) 0.84697(14) 0.0148(4) Uani 1 1 d . . . . .
C1 C 0.62604(13) 0.61210(15) -0.00138(17) 0.0145(4) Uani 1 1 d . . . . .
H1A H 0.6314 0.6651 0.0546 0.017 Uiso 1 1 calc R U . . .
H1B H 0.5652 0.5837 -0.0180 0.017 Uiso 1 1 calc R U . . .
C2 C 0.64183(13) 0.65342(16) -0.10622(17) 0.0151(4) Uani 1 1 d . . . . .
H2A H 0.6332 0.6006 -0.1630 0.018 Uiso 1 1 calc R U . . .
H2B H 0.5977 0.7061 -0.1363 0.018 Uiso 1 1 calc R U . . .
C3 C 0.79921(14) 0.61673(16) -0.03614(18) 0.0178(4) Uani 1 1 d . . . . .
H3A H 0.8599 0.6453 -0.0193 0.021 Uiso 1 1 calc R U . . .
H3B H 0.7949 0.5631 -0.0912 0.021 Uiso 1 1 calc R U . . .
C4 C 0.78448(13) 0.57471(16) 0.06956(18) 0.0164(4) Uani 1 1 d . . . . .
H4A H 0.8282 0.5216 0.0993 0.020 Uiso 1 1 calc R U . . .
H4B H 0.7924 0.6270 0.1268 0.020 Uiso 1 1 calc R U . . .
C5 C 0.74495(16) 0.73157(17) -0.18860(19) 0.0227(5) Uani 1 1 d . . . . .
H5A H 0.7323 0.6790 -0.2447 0.034 Uiso 1 1 calc R U . . .
H5B H 0.8067 0.7540 -0.1757 0.034 Uiso 1 1 calc R U . . .
H5C H 0.7041 0.7870 -0.2152 0.034 Uiso 1 1 calc R U . . .
C6 C 0.63837(13) 0.49954(15) 0.22935(16) 0.0117(4) Uani 1 1 d . . . . .
C7 C 0.55407(13) 0.54099(15) 0.21397(16) 0.0129(4) Uani 1 1 d . . . . .
H7 H 0.5123 0.5405 0.1421 0.015 Uiso 1 1 calc R U . . .
C8 C 0.53087(13) 0.58291(15) 0.30293(16) 0.0138(4) Uani 1 1 d . . . . .
H8 H 0.4734 0.6114 0.2920 0.017 Uiso 1 1 calc R U . . .
C9 C 0.59218(13) 0.58331(15) 0.40895(16) 0.0131(4) Uani 1 1 d . . . . .
C10 C 0.67770(13) 0.54296(15) 0.42401(16) 0.0120(4) Uani 1 1 d . . . . .
C11 C 0.69992(13) 0.50050(14) 0.33413(16) 0.0120(4) Uani 1 1 d . . . . .
H11 H 0.7573 0.4721 0.3444 0.014 Uiso 1 1 calc R U . . .
C12 C 0.74752(13) 0.54663(15) 0.53381(16) 0.0115(4) Uani 1 1 d . . . . .
C13 C 0.86385(13) 0.65474(15) 0.64837(16) 0.0127(4) Uani 1 1 d . . . . .
C14 C 0.88569(12) 0.56796(15) 0.71582(16) 0.0120(4) Uani 1 1 d . . . . .
C15 C 0.83893(13) 0.47980(15) 0.68824(16) 0.0124(4) Uani 1 1 d . . . . .
C16 C 0.88146(13) 0.41254(15) 0.77287(17) 0.0140(4) Uani 1 1 d . . . . .
C17 C 0.85956(14) 0.30698(16) 0.78770(18) 0.0185(5) Uani 1 1 d . . . . .
H17A H 0.9156 0.2705 0.8214 0.022 Uiso 1 1 calc R U . . .
H17B H 0.8312 0.2776 0.7137 0.022 Uiso 1 1 calc R U . . .
C18 C 0.79681(15) 0.29458(18) 0.86149(19) 0.0231(5) Uani 1 1 d . . . . .
H18A H 0.7913 0.2235 0.8765 0.028 Uiso 1 1 calc R U . . .
H18B H 0.8234 0.3277 0.9338 0.028 Uiso 1 1 calc R U . . .
C19 C 0.70414(15) 0.33686(19) 0.8092(2) 0.0276(5) Uani 1 1 d . . . . .
H19A H 0.7093 0.4063 0.7898 0.041 Uiso 1 1 calc R U . . .
H19B H 0.6686 0.3320 0.8623 0.041 Uiso 1 1 calc R U . . .
H19C H 0.6748 0.2996 0.7416 0.041 Uiso 1 1 calc R U . . .
C20 C 0.48400(13) 0.65318(17) 0.49017(17) 0.0169(4) Uani 1 1 d . . . . .
H20A H 0.4415 0.5991 0.4597 0.020 Uiso 1 1 calc R U . . .
H20B H 0.4688 0.7103 0.4390 0.020 Uiso 1 1 calc R U . . .
C21 C 0.47859(15) 0.68170(17) 0.60411(18) 0.0209(5) Uani 1 1 d . . . . .
H21A H 0.4174 0.7019 0.5997 0.031 Uiso 1 1 calc R U . . .
H21B H 0.5195 0.7367 0.6324 0.031 Uiso 1 1 calc R U . . .
H21C H 0.4954 0.6252 0.6545 0.031 Uiso 1 1 calc R U . . .
C22 C 1.01865(14) 0.62061(16) 0.87452(18) 0.0188(5) Uani 1 1 d . . . . .
H22A H 1.0724 0.6152 0.8490 0.028 Uiso 1 1 calc R U . . .
H22B H 1.0336 0.6046 0.9541 0.028 Uiso 1 1 calc R U . . .
H22C H 0.9955 0.6881 0.8626 0.028 Uiso 1 1 calc R U . . .
O1W O 0.90741(10) 0.49088(14) 0.45324(14) 0.0299(4) Uani 1 1 d . . . . .
C1W C 1.04111(16) 0.4433(2) 0.5930(2) 0.0323(6) Uani 1 1 d . . . . .
H1WA H 1.0220 0.4774 0.6524 0.039 Uiso 1 1 calc R U . . .
H1WB H 1.0781 0.3859 0.6266 0.039 Uiso 1 1 calc R U . . .
C2W C 0.96050(17) 0.4087(2) 0.5039(2) 0.0327(6) Uani 1 1 d . . . . .
H2WA H 0.9797 0.3713 0.4467 0.039 Uiso 1 1 calc R U . . .
H2WB H 0.9246 0.3642 0.5370 0.039 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
S1 O2 1.4320(14) . ?
S1 O1 1.4404(15) . ?
S1 N1 1.6264(18) . ?
S1 C6 1.763(2) . ?
O3 C13 1.226(2) . ?
O4 C9 1.358(2) . ?
O4 C20 1.449(2) . ?
N1 C1 1.469(2) . ?
N1 C4 1.470(3) . ?
N2 C5 1.464(3) . ?
N2 C2 1.468(3) . ?
N2 C3 1.479(3) . ?
N3 C12 1.381(3) . ?
N3 C13 1.389(2) . ?
N3 H1N 0.94(3) . ?
N4 C12 1.297(3) . ?
N4 C15 1.387(2) . ?
N5 C14 1.358(2) . ?
N5 N6 1.359(2) . ?
N5 C22 1.455(3) . ?
N6 C16 1.342(3) . ?
C1 C2 1.508(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.515(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.390(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(3) . ?
C10 C11 1.391(3) . ?
C10 C12 1.494(3) . ?
C11 H11 0.9500 . ?
C13 C14 1.431(3) . ?
C14 C15 1.392(3) . ?
C15 C16 1.413(3) . ?
C16 C17 1.494(3) . ?
C17 C18 1.532(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.521(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.502(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O1W C2W 1.425(3) . ?
O1W C1W 1.427(3) 3_766 ?
C1W O1W 1.427(3) 3_766 ?
C1W C2W 1.501(4) . ?
C1W H1WA 0.9900 . ?
C1W H1WB 0.9900 . ?
C2W H2WA 0.9900 . ?
C2W H2WB 0.9900 . ?

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
O2 S1 O1 119.87(9) . . ?
O2 S1 N1 107.02(9) . . ?
O1 S1 N1 106.13(9) . . ?
O2 S1 C6 108.64(9) . . ?
O1 S1 C6 106.32(9) . . ?
N1 S1 C6 108.45(9) . . ?
C9 O4 C20 117.18(15) . . ?
C1 N1 C4 111.78(16) . . ?
C1 N1 S1 118.02(14) . . ?
C4 N1 S1 120.89(13) . . ?
C5 N2 C2 109.14(16) . . ?
C5 N2 C3 110.78(17) . . ?
C2 N2 C3 110.11(16) . . ?
C12 N3 C13 124.89(17) . . ?
C12 N3 H1N 120.2(16) . . ?
C13 N3 H1N 114.9(16) . . ?
C12 N4 C15 113.35(17) . . ?
C14 N5 N6 110.85(16) . . ?
C14 N5 C22 128.73(18) . . ?
N6 N5 C22 120.40(16) . . ?
C16 N6 N5 106.83(16) . . ?
N1 C1 C2 108.19(16) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N2 C2 C1 111.17(16) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 111.02(17) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C3 108.02(16) . . ?
N1 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
N1 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 120.10(18) . . ?
C11 C6 S1 119.87(15) . . ?
C7 C6 S1 120.03(15) . . ?
C8 C7 C6 120.32(18) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.93(18) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
O4 C9 C8 123.96(18) . . ?
O4 C9 C10 116.34(17) . . ?
C8 C9 C10 119.70(18) . . ?
C11 C10 C9 119.76(18) . . ?
C11 C10 C12 118.25(17) . . ?
C9 C10 C12 121.97(18) . . ?
C6 C11 C10 120.17(18) . . ?
C6 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
N4 C12 N3 125.56(17) . . ?
N4 C12 C10 119.85(18) . . ?
N3 C12 C10 114.44(17) . . ?
O3 C13 N3 122.32(18) . . ?
O3 C13 C14 127.90(18) . . ?
N3 C13 C14 109.78(17) . . ?
N5 C14 C15 107.18(17) . . ?
N5 C14 C13 130.27(18) . . ?
C15 C14 C13 122.55(17) . . ?
N4 C15 C14 123.70(18) . . ?
N4 C15 C16 130.88(19) . . ?
C14 C15 C16 105.39(17) . . ?
N6 C16 C15 109.75(18) . . ?
N6 C16 C17 120.82(18) . . ?
C15 C16 C17 129.42(18) . . ?
C16 C17 C18 112.78(19) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 113.02(18) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 C21 107.54(17) . . ?
O4 C20 H20A 110.2 . . ?
C21 C20 H20A 110.2 . . ?
O4 C20 H20B 110.2 . . ?
C21 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2W O1W C1W 110.18(18) . 3_766 ?
O1W C1W C2W 110.2(2) 3_766 . ?
O1W C1W H1WA 109.6 3_766 . ?
C2W C1W H1WA 109.6 . . ?
O1W C1W H1WB 109.6 3_766 . ?
C2W C1W H1WB 109.6 . . ?
H1WA C1W H1WB 108.1 . . ?
O1W C2W C1W 110.3(2) . . ?
O1W C2W H2WA 109.6 . . ?
C1W C2W H2WA 109.6 . . ?
O1W C2W H2WB 109.6 . . ?
C1W C2W H2WB 109.6 . . ?
H2WA C2W H2WB 108.1 . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.073

_shelxl_version_number           2012-9


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dioxane'
####################################################################### 
# 
# 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_mo_023ub111_0ma_aa
_database_code_depnum_ccdc_archive 'CCDC 1821374'
_audit_update_record             
;
2018-05-08 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Sildenafil toluene solvate'
_chemical_name_common            
'5-[2-ethoxy-5-(4-methylpiperazin-1-yl) sulfonyl-phenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C22 H30 N6 O4 S), C7 H8'
_chemical_formula_sum            'C51 H68 N12 O8 S2'
_chemical_formula_weight         1041.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.8287(6)
_cell_length_b                   14.3781(6)
_cell_length_c                   12.7277(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.4830(10)
_cell_angle_gamma                90
_cell_volume                     2602.13(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9833
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.71

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.666
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.092
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59166
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.189
_diffrn_reflns_theta_max         28.728
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6727
_reflns_number_gt                5757
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'XT-2014/5 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0549P)²+0.9411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6727
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
S1 S 0.17283(2) 0.46767(2) 0.12333(2) 0.01122(8) Uani 1 1 d . . . . .
N1 N 0.19890(7) 0.55303(7) 0.05328(8) 0.01294(19) Uani 1 1 d . . . . .
O1 O 0.09236(6) 0.42186(6) 0.05209(7) 0.01562(17) Uani 1 1 d . . . . .
C1 C 0.12523(8) 0.62072(8) 0.00347(9) 0.0155(2) Uani 1 1 d . . . . .
H1A H 0.124537 0.671134 0.056213 0.019 Uiso 1 1 calc R U . . .
H1B H 0.062914 0.590006 -0.016870 0.019 Uiso 1 1 calc R U . . .
O2 O 0.25800(6) 0.41662(6) 0.16922(7) 0.01481(17) Uani 1 1 d . . . . .
N2 N 0.23914(7) 0.70351(7) -0.07056(8) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.14559(8) 0.66048(8) -0.09761(9) 0.0163(2) Uani 1 1 d . . . . .
H2A H 0.141994 0.610199 -0.151788 0.020 Uiso 1 1 calc R U . . .
H2B H 0.097356 0.707596 -0.131233 0.020 Uiso 1 1 calc R U . . .
C3 C 0.31167(8) 0.63534(8) -0.01699(10) 0.0173(2) Uani 1 1 d . . . . .
H3A H 0.374185 0.665638 0.002757 0.021 Uiso 1 1 calc R U . . .
H3B H 0.312450 0.584054 -0.068626 0.021 Uiso 1 1 calc R U . . .
O3 O 0.06323(6) 0.62284(6) 0.49896(7) 0.01725(18) Uani 1 1 d . . . . .
N3 N 0.29018(7) 0.63342(7) 0.56600(8) 0.01236(19) Uani 1 1 d . . . . .
H3N H 0.2693(11) 0.6857(12) 0.5205(14) 0.028(4) Uiso 1 1 d . . . . .
O4 O 0.40840(6) 0.72049(6) 0.67833(7) 0.01799(18) Uani 1 1 d . . . . .
N4 N 0.26260(7) 0.47266(7) 0.58882(8) 0.01334(19) Uani 1 1 d . . . . .
C4 C 0.29271(8) 0.59597(8) 0.08581(9) 0.0146(2) Uani 1 1 d . . . . .
H4A H 0.340910 0.548977 0.119969 0.018 Uiso 1 1 calc R U . . .
H4B H 0.294922 0.646268 0.139605 0.018 Uiso 1 1 calc R U . . .
C5 C 0.25622(10) 0.73894(9) -0.17121(10) 0.0235(3) Uani 1 1 d . . . . .
H5A H 0.252289 0.687585 -0.222952 0.035 Uiso 1 1 calc R U . . .
H5B H 0.318980 0.766944 -0.153776 0.035 Uiso 1 1 calc R U . . .
H5C H 0.208801 0.785967 -0.204203 0.035 Uiso 1 1 calc R U . . .
N5 N 0.45373(7) 0.54079(7) 0.81286(8) 0.01393(19) Uani 1 1 d . . . . .
C6 C 0.13622(8) 0.51445(8) 0.23275(9) 0.0121(2) Uani 1 1 d . . . . .
N6 N 0.44909(7) 0.44993(7) 0.84054(8) 0.0163(2) Uani 1 1 d . . . . .
C7 C 0.04627(8) 0.55201(8) 0.21538(9) 0.0144(2) Uani 1 1 d . . . . .
H7 H 0.003416 0.552166 0.143949 0.017 Uiso 1 1 calc R U . . .
C8 C 0.01964(8) 0.58924(8) 0.30313(9) 0.0156(2) Uani 1 1 d . . . . .
H8 H -0.041472 0.614835 0.291496 0.019 Uiso 1 1 calc R U . . .
C9 C 0.08274(8) 0.58904(8) 0.40845(9) 0.0137(2) Uani 1 1 d . . . . .
C10 C 0.17300(8) 0.55119(8) 0.42515(9) 0.0122(2) Uani 1 1 d . . . . .
C11 C 0.19903(8) 0.51366(8) 0.33735(9) 0.0128(2) Uani 1 1 d . . . . .
H11 H 0.259849 0.487409 0.348811 0.015 Uiso 1 1 calc R U . . .
C12 C 0.24399(8) 0.55024(8) 0.53482(9) 0.0120(2) Uani 1 1 d . . . . .
C13 C 0.36705(8) 0.64583(8) 0.65756(9) 0.0129(2) Uani 1 1 d . . . . .
C14 C 0.38669(8) 0.56076(8) 0.71911(9) 0.0123(2) Uani 1 1 d . . . . .
C15 C 0.33577(8) 0.47986(8) 0.68444(9) 0.0129(2) Uani 1 1 d . . . . .
C16 C 0.37798(8) 0.41218(8) 0.76334(9) 0.0149(2) Uani 1 1 d . . . . .
C17 C 0.35044(9) 0.31220(8) 0.76806(10) 0.0186(2) Uani 1 1 d . . . . .
H17A H 0.398790 0.280222 0.826784 0.022 Uiso 1 1 calc R U . . .
H17B H 0.348332 0.281642 0.697702 0.022 Uiso 1 1 calc R U . . .
C18 C 0.25442(9) 0.30176(9) 0.78995(11) 0.0216(3) Uani 1 1 d . . . . .
H18A H 0.206192 0.333453 0.730818 0.026 Uiso 1 1 calc R U . . .
H18B H 0.237889 0.234928 0.787634 0.026 Uiso 1 1 calc R U . . .
C19 C 0.25208(12) 0.34170(11) 0.89955(13) 0.0347(4) Uani 1 1 d . . . . .
H19A H 0.268882 0.407767 0.902773 0.052 Uiso 1 1 calc R U . . .
H19B H 0.297145 0.308275 0.958809 0.052 Uiso 1 1 calc R U . . .
H19C H 0.188693 0.334834 0.907820 0.052 Uiso 1 1 calc R U . . .
C20 C -0.03201(8) 0.65248(9) 0.48933(10) 0.0183(2) Uani 1 1 d . . . . .
H20A H -0.077020 0.602211 0.457219 0.022 Uiso 1 1 calc R U . . .
H20B H -0.048013 0.707947 0.441563 0.022 Uiso 1 1 calc R U . . .
C21 C -0.03648(10) 0.67528(10) 0.60333(11) 0.0229(3) Uani 1 1 d . . . . .
H21A H -0.100920 0.692825 0.600814 0.034 Uiso 1 1 calc R U . . .
H21B H 0.006100 0.727137 0.632716 0.034 Uiso 1 1 calc R U . . .
H21C H -0.017524 0.620714 0.650585 0.034 Uiso 1 1 calc R U . . .
C22 C 0.52473(8) 0.60209(9) 0.88099(10) 0.0178(2) Uani 1 1 d . . . . .
H22A H 0.584188 0.593855 0.862830 0.027 Uiso 1 1 calc R U . . .
H22B H 0.533834 0.586855 0.958355 0.027 Uiso 1 1 calc R U . . .
H22C H 0.503970 0.666830 0.867648 0.027 Uiso 1 1 calc R U . . .
C23 C 0.51232(18) 0.55313(12) 0.49284(19) 0.0337(2) Uani 0.5 1 d G . P A -1
C24 C 0.45761(16) 0.50377(15) 0.40347(16) 0.0337(2) Uani 0.5 1 d G . P A -1
H24 H 0.434203 0.533699 0.334541 0.040 Uiso 0.5 1 calc R U P A -1
C25 C 0.43713(14) 0.41064(15) 0.41496(16) 0.0337(2) Uani 0.5 1 d G . P A -1
H25 H 0.399732 0.376904 0.353874 0.040 Uiso 0.5 1 calc R U P A -1
C27 C 0.47137(16) 0.36685(12) 0.51581(18) 0.0337(2) Uani 0.5 1 d G . P A -1
H27 H 0.457376 0.303194 0.523660 0.040 Uiso 0.5 1 calc R U P A -1
C26 C 0.52609(15) 0.41620(15) 0.60518(15) 0.0337(2) Uani 0.5 1 d G . P A -1
H26 H 0.549492 0.386277 0.674115 0.040 Uiso 0.5 1 calc R U P A -1
C28 C 0.54657(15) 0.50934(15) 0.59370(17) 0.0337(2) Uani 0.5 1 d G . P A -1
H28 H 0.583965 0.543071 0.654785 0.040 Uiso 0.5 1 calc R U P A -1
C29 C 0.5362(3) 0.6526(2) 0.4775(3) 0.0337(2) Uani 0.5 1 d . . P A -1
H29C H 0.511160 0.669639 0.400102 0.040 Uiso 0.5 1 calc R U P A -1
H29B H 0.604637 0.660400 0.500245 0.040 Uiso 0.5 1 calc R U P A -1
H29A H 0.508292 0.692812 0.522093 0.040 Uiso 0.5 1 calc R U P A -1


_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
S1 O2 1.4341(8) . ?
S1 O1 1.4372(8) . ?
S1 N1 1.6267(10) . ?
S1 C6 1.7652(11) . ?
N1 C1 1.4662(14) . ?
N1 C4 1.4700(14) . ?
C1 C2 1.5144(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N2 C5 1.4659(15) . ?
N2 C2 1.4678(15) . ?
N2 C3 1.4718(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5233(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O3 C9 1.3551(13) . ?
O3 C20 1.4467(14) . ?
N3 C12 1.3793(14) . ?
N3 C13 1.3912(14) . ?
N3 H3N 0.945(17) . ?
O4 C13 1.2274(14) . ?
N4 C12 1.2982(15) . ?
N4 C15 1.3855(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
N5 C14 1.3496(14) . ?
N5 N6 1.3599(14) . ?
N5 C22 1.4558(15) . ?
C6 C11 1.3915(15) . ?
C6 C7 1.3972(16) . ?
N6 C16 1.3357(15) . ?
C7 C8 1.3928(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4002(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.4040(15) . ?
C10 C11 1.3905(15) . ?
C10 C12 1.4910(15) . ?
C11 H11 0.9500 . ?
C13 C14 1.4370(15) . ?
C14 C15 1.3888(15) . ?
C15 C16 1.4109(15) . ?
C16 C17 1.5002(16) . ?
C17 C18 1.5338(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5181(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5073(17) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.3900 . ?
C23 C28 1.3900 . ?
C23 C29 1.499(4) . ?
C24 C25 1.3900 . ?
C24 H24 0.9500 . ?
C25 C27 1.3900 . ?
C25 H25 0.9500 . ?
C27 C26 1.3900 . ?
C27 H27 0.9500 . ?
C26 C28 1.3900 . ?
C26 H26 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29C 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29A 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
O2 S1 O1 120.00(5) . . ?
O2 S1 N1 106.89(5) . . ?
O1 S1 N1 106.49(5) . . ?
O2 S1 C6 107.83(5) . . ?
O1 S1 C6 106.63(5) . . ?
N1 S1 C6 108.61(5) . . ?
C1 N1 C4 111.86(9) . . ?
C1 N1 S1 118.30(8) . . ?
C4 N1 S1 121.04(8) . . ?
N1 C1 C2 108.31(9) . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
C5 N2 C2 109.13(10) . . ?
C5 N2 C3 110.58(10) . . ?
C2 N2 C3 110.23(9) . . ?
N2 C2 C1 111.28(9) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 110.89(9) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
C9 O3 C20 118.19(9) . . ?
C12 N3 C13 125.04(10) . . ?
C12 N3 H3N 117.6(10) . . ?
C13 N3 H3N 117.4(10) . . ?
C12 N4 C15 113.37(10) . . ?
N1 C4 C3 107.74(9) . . ?
N1 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
N1 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C14 N5 N6 110.78(9) . . ?
C14 N5 C22 128.65(10) . . ?
N6 N5 C22 120.57(9) . . ?
C11 C6 C7 120.29(10) . . ?
C11 C6 S1 118.66(8) . . ?
C7 C6 S1 121.06(8) . . ?
C16 N6 N5 106.69(9) . . ?
C8 C7 C6 119.78(10) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.16(10) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
O3 C9 C8 124.56(10) . . ?
O3 C9 C10 115.76(10) . . ?
C8 C9 C10 119.68(10) . . ?
C11 C10 C9 119.92(10) . . ?
C11 C10 C12 117.74(10) . . ?
C9 C10 C12 122.33(10) . . ?
C10 C11 C6 120.17(10) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
N4 C12 N3 125.39(10) . . ?
N4 C12 C10 119.41(10) . . ?
N3 C12 C10 114.99(9) . . ?
O4 C13 N3 122.22(10) . . ?
O4 C13 C14 127.99(10) . . ?
N3 C13 C14 109.79(10) . . ?
N5 C14 C15 107.48(10) . . ?
N5 C14 C13 130.36(10) . . ?
C15 C14 C13 122.13(10) . . ?
N4 C15 C14 124.14(10) . . ?
N4 C15 C16 130.72(11) . . ?
C14 C15 C16 105.08(10) . . ?
N6 C16 C15 109.97(10) . . ?
N6 C16 C17 121.81(10) . . ?
C15 C16 C17 128.21(11) . . ?
C16 C17 C18 112.23(10) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 113.22(11) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 106.92(10) . . ?
O3 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O3 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 120.0 . . ?
C24 C23 C29 119.0(2) . . ?
C28 C23 C29 121.0(2) . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C27 120.0 . . ?
C24 C25 H25 120.0 . . ?
C27 C25 H25 120.0 . . ?
C26 C27 C25 120.0 . . ?
C26 C27 H27 120.0 . . ?
C25 C27 H27 120.0 . . ?
C27 C26 C28 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C26 H26 120.0 . . ?
C26 C28 C23 120.0 . . ?
C26 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C23 C29 H29C 109.5 . . ?
C23 C29 H29B 109.5 . . ?
H29C C29 H29B 109.5 . . ?
C23 C29 H29A 109.5 . . ?
H29C C29 H29A 109.5 . . ?
H29B C29 H29A 109.5 . . ?

_refine_diff_density_max         1.364
_refine_diff_density_min         -1.000
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_mo_023WB13A_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1832572'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        'Sildenafil chloroform solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H30 N6 O4 S, C H Cl3'
_chemical_formula_sum            'C23 H31 Cl3 N6 O4 S'
_chemical_formula_weight         593.95

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'
Cl Cl 0.1484 0.1585 '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'

_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                   16.3399(7)
_cell_length_b                   8.5767(3)
_cell_length_c                   40.1148(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5621.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      23.81

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             2480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.441
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan'
_exptl_absorpt_correction_T_min  0.6894
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35024
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         2.383
_diffrn_reflns_theta_max         26.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5787
_reflns_number_gt                3563
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'XT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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+5.4288P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5787
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1981
_refine_ls_wR_factor_gt          0.1718
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
S1 S 0.62154(5) 0.44480(11) 0.60020(2) 0.0545(3) Uani 1 1 d . . . . .
O1 O 0.58894(16) 0.3046(3) 0.61380(7) 0.0694(7) Uani 1 1 d . . . . .
N1 N 0.63266(16) 0.5650(3) 0.63099(7) 0.0507(7) Uani 1 1 d . . . . .
N2 N 0.6437(2) 0.7884(4) 0.68264(8) 0.0650(8) Uani 1 1 d . . . . .
O2 O 0.69751(15) 0.4418(3) 0.58274(7) 0.0689(7) Uani 1 1 d . . . . .
N3 N 0.25812(17) 0.5976(3) 0.54712(6) 0.0514(7) Uani 1 1 d . . . . .
H3N H 0.2744 0.6529 0.5305 0.062 Uiso 1 1 calc R U . . .
N4 N 0.30211(16) 0.4415(3) 0.59190(6) 0.0486(7) Uani 1 1 d . . . . .
O4 O 0.12617(15) 0.6513(3) 0.53284(6) 0.0675(7) Uani 1 1 d . . . . .
N5 N 0.09864(18) 0.3571(3) 0.62129(7) 0.0563(7) Uani 1 1 d . . . . .
O3 O 0.37407(15) 0.7185(3) 0.51077(6) 0.0654(7) Uani 1 1 d . . . . .
N6 N 0.08573(17) 0.4484(3) 0.59429(7) 0.0532(7) Uani 1 1 d . . . . .
C1 C 0.5639(2) 0.5874(4) 0.65407(8) 0.0545(9) Uani 1 1 d . . . . .
H1A H 0.5350 0.4898 0.6573 0.065 Uiso 1 1 calc R U . . .
H1B H 0.5259 0.6633 0.6451 0.065 Uiso 1 1 calc R U . . .
C2 C 0.5978(2) 0.6438(5) 0.68669(9) 0.0622(9) Uani 1 1 d . . . . .
H2A H 0.5532 0.6608 0.7022 0.075 Uiso 1 1 calc R U . . .
H2B H 0.6335 0.5645 0.6960 0.075 Uiso 1 1 calc R U . . .
C3 C 0.7098(2) 0.7655(5) 0.65881(10) 0.0670(10) Uani 1 1 d . . . . .
H3A H 0.7481 0.6893 0.6676 0.080 Uiso 1 1 calc R U . . .
H3B H 0.7391 0.8630 0.6558 0.080 Uiso 1 1 calc R U . . .
C4 C 0.6780(2) 0.7103(4) 0.62556(10) 0.0625(10) Uani 1 1 d . . . . .
H4A H 0.6424 0.7886 0.6159 0.075 Uiso 1 1 calc R U . . .
H4B H 0.7232 0.6923 0.6104 0.075 Uiso 1 1 calc R U . . .
C5 C 0.6776(3) 0.8370(6) 0.71491(11) 0.0965(16) Uani 1 1 d . . . . .
H5A H 0.7159 0.7601 0.7226 0.145 Uiso 1 1 calc R U . . .
H5B H 0.6341 0.8473 0.7308 0.145 Uiso 1 1 calc R U . . .
H5C H 0.7049 0.9354 0.7124 0.145 Uiso 1 1 calc R U . . .
C6 C 0.5476(2) 0.5227(4) 0.57276(8) 0.0512(8) Uani 1 1 d . . . . .
C7 C 0.5729(2) 0.6104(5) 0.54578(9) 0.0577(9) Uani 1 1 d . . . . .
H7 H 0.6283 0.6263 0.5418 0.069 Uiso 1 1 calc R U . . .
C8 C 0.5151(2) 0.6740(5) 0.52473(9) 0.0584(9) Uani 1 1 d . . . . .
H8 H 0.5318 0.7317 0.5063 0.070 Uiso 1 1 calc R U . . .
C9 C 0.4321(2) 0.6524(4) 0.53087(8) 0.0511(8) Uani 1 1 d . . . . .
C10 C 0.4055(2) 0.5622(4) 0.55796(8) 0.0474(8) Uani 1 1 d . . . . .
C11 C 0.4651(2) 0.4978(4) 0.57864(8) 0.0495(8) Uani 1 1 d . . . . .
H11 H 0.4492 0.4370 0.5967 0.059 Uiso 1 1 calc R U . . .
C12 C 0.3183(2) 0.5298(4) 0.56665(8) 0.0459(8) Uani 1 1 d . . . . .
C13 C 0.1740(2) 0.5853(4) 0.55175(8) 0.0519(8) Uani 1 1 d . . . . .
C14 C 0.1574(2) 0.4908(4) 0.58012(8) 0.0470(8) Uani 1 1 d . . . . .
C15 C 0.2197(2) 0.4222(4) 0.59840(8) 0.0470(8) Uani 1 1 d . . . . .
C16 C 0.1798(2) 0.3396(4) 0.62426(8) 0.0510(8) Uani 1 1 d . . . . .
C17 C 0.2167(2) 0.2494(5) 0.65211(9) 0.0634(10) Uani 1 1 d . . . . .
H17A H 0.2551 0.1750 0.6427 0.076 Uiso 1 1 calc R U . . .
H17B H 0.2478 0.3208 0.6659 0.076 Uiso 1 1 calc R U . . .
C18 C 0.1589(3) 0.1636(6) 0.67370(11) 0.0886(14) Uani 1 1 d . . . . .
H18A H 0.1379 0.0749 0.6614 0.106 Uiso 1 1 calc R U . . .
H18B H 0.1129 0.2314 0.6787 0.106 Uiso 1 1 calc R U . . .
C19 C 0.1943(4) 0.1057(7) 0.70614(11) 0.1037(17) Uani 1 1 d . . . . .
H19A H 0.2417 0.0429 0.7017 0.156 Uiso 1 1 calc R U . . .
H19B H 0.1541 0.0443 0.7177 0.156 Uiso 1 1 calc R U . . .
H19C H 0.2097 0.1930 0.7197 0.156 Uiso 1 1 calc R U . . .
C20 C 0.0033(2) 0.4936(5) 0.58533(11) 0.0679(10) Uani 1 1 d . . . . .
H20A H 0.0050 0.5620 0.5664 0.102 Uiso 1 1 calc R U . . .
H20B H -0.0218 0.5465 0.6038 0.102 Uiso 1 1 calc R U . . .
H20C H -0.0280 0.4024 0.5799 0.102 Uiso 1 1 calc R U . . .
C21 C 0.3975(2) 0.8199(5) 0.48411(9) 0.0630(10) Uani 1 1 d . . . . .
H21A H 0.4303 0.7639 0.4679 0.076 Uiso 1 1 calc R U . . .
H21B H 0.4295 0.9066 0.4926 0.076 Uiso 1 1 calc R U . . .
C22 C 0.3202(3) 0.8780(6) 0.46838(10) 0.0760(12) Uani 1 1 d . . . . .
H22A H 0.3334 0.9492 0.4507 0.114 Uiso 1 1 calc R U . . .
H22B H 0.2877 0.9305 0.4848 0.114 Uiso 1 1 calc R U . . .
H22C H 0.2900 0.7915 0.4595 0.114 Uiso 1 1 calc R U . . .
Cl1 Cl 0.07083(9) 0.6994(2) 0.66887(5) 0.1269(6) Uani 1 1 d . . . . .
Cl2 Cl 0.04371(14) 0.4907(2) 0.72444(5) 0.1552(8) Uani 1 1 d . . . . .
Cl3 Cl -0.07690(11) 0.71704(19) 0.70683(5) 0.1331(7) Uani 1 1 d . . . . .
C23 C -0.0002(3) 0.5940(5) 0.69198(12) 0.0835(13) Uani 1 1 d . . . . .
H23 H -0.0259 0.5184 0.6769 0.100 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
S1 O1 1.424(3) . ?
S1 O2 1.426(3) . ?
S1 N1 1.619(3) . ?
S1 C6 1.766(4) . ?
N1 C4 1.466(4) . ?
N1 C1 1.468(4) . ?
N2 C3 1.456(5) . ?
N2 C2 1.458(5) . ?
N2 C5 1.468(5) . ?
N3 C12 1.386(4) . ?
N3 C13 1.391(4) . ?
N3 H3N 0.8600 . ?
N4 C12 1.292(4) . ?
N4 C15 1.382(4) . ?
O4 C13 1.227(4) . ?
N5 C16 1.339(4) . ?
N5 N6 1.353(4) . ?
O3 C9 1.368(4) . ?
O3 C21 1.431(4) . ?
N6 C14 1.352(4) . ?
N6 C20 1.447(5) . ?
C1 C2 1.501(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.508(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.381(5) . ?
C6 C11 1.384(5) . ?
C7 C8 1.379(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.404(5) . ?
C10 C11 1.394(5) . ?
C10 C12 1.492(5) . ?
C11 H11 0.9300 . ?
C13 C14 1.423(5) . ?
C14 C15 1.385(5) . ?
C15 C16 1.415(5) . ?
C16 C17 1.487(5) . ?
C17 C18 1.478(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.508(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.498(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Cl1 C23 1.739(5) . ?
Cl2 C23 1.730(5) . ?
Cl3 C23 1.744(5) . ?
C23 H23 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
O1 S1 O2 119.93(17) . . ?
O1 S1 N1 106.72(16) . . ?
O2 S1 N1 106.77(16) . . ?
O1 S1 C6 107.59(16) . . ?
O2 S1 C6 107.24(17) . . ?
N1 S1 C6 108.14(15) . . ?
C4 N1 C1 111.7(3) . . ?
C4 N1 S1 119.0(2) . . ?
C1 N1 S1 118.6(2) . . ?
C3 N2 C2 109.9(3) . . ?
C3 N2 C5 109.7(3) . . ?
C2 N2 C5 109.7(3) . . ?
C12 N3 C13 126.4(3) . . ?
C12 N3 H3N 116.8 . . ?
C13 N3 H3N 116.8 . . ?
C12 N4 C15 114.7(3) . . ?
C16 N5 N6 106.9(3) . . ?
C9 O3 C21 120.5(3) . . ?
C14 N6 N5 110.9(3) . . ?
C14 N6 C20 129.1(3) . . ?
N5 N6 C20 119.9(3) . . ?
N1 C1 C2 108.0(3) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N2 C2 C1 111.5(3) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 111.6(3) . . ?
N2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C3 108.1(3) . . ?
N1 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
N1 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 120.6(3) . . ?
C7 C6 S1 119.3(3) . . ?
C11 C6 S1 120.1(3) . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O3 C9 C8 121.1(3) . . ?
O3 C9 C10 118.0(3) . . ?
C8 C9 C10 120.9(3) . . ?
C11 C10 C9 117.5(3) . . ?
C11 C10 C12 117.0(3) . . ?
C9 C10 C12 125.4(3) . . ?
C6 C11 C10 121.2(3) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
N4 C12 N3 123.0(3) . . ?
N4 C12 C10 119.2(3) . . ?
N3 C12 C10 117.8(3) . . ?
O4 C13 N3 120.8(3) . . ?
O4 C13 C14 129.5(3) . . ?
N3 C13 C14 109.7(3) . . ?
N6 C14 C15 107.4(3) . . ?
N6 C14 C13 130.8(3) . . ?
C15 C14 C13 121.7(3) . . ?
N4 C15 C14 124.4(3) . . ?
N4 C15 C16 130.4(3) . . ?
C14 C15 C16 105.2(3) . . ?
N5 C16 C15 109.6(3) . . ?
N5 C16 C17 121.8(3) . . ?
C15 C16 C17 128.6(3) . . ?
C18 C17 C16 116.1(3) . . ?
C18 C17 H17A 108.3 . . ?
C16 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C16 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C17 C18 C19 115.1(4) . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18B 108.5 . . ?
C19 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 C22 106.9(3) . . ?
O3 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 . . ?
O3 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 . . ?
H21A C21 H21B 108.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl2 C23 Cl1 113.0(3) . . ?
Cl2 C23 Cl3 110.5(3) . . ?
Cl1 C23 Cl3 110.3(3) . . ?
Cl2 C23 H23 107.6 . . ?
Cl1 C23 H23 107.6 . . ?
Cl3 C23 H23 107.6 . . ?

_refine_diff_density_max         0.678
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.054

_shelxl_version_number           2012-9


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
