# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_fel_acetone
_database_code_depnum_ccdc_archive 'CCDC 1048180'
_audit_update_record             
;
2015-02-08 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'felodipine:acetone (1:1)'
_chemical_name_common            'felodipine:acetone (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 Cl2 N O4, C3 H6 O'
_chemical_formula_sum            'C21 H25 Cl2 N O5'
_chemical_formula_weight         442.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.1774(8)
_cell_length_b                   16.6983(15)
_cell_length_c                   14.3375(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.865(4)
_cell_angle_gamma                90
_cell_volume                     2113.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8516
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.29

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.340
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6952
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33416
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.832
_diffrn_reflns_theta_max         25.707
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4003
_reflns_number_gt                3130
_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       'APEX2 v2010.1-2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0332P)²+1.7889P] 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         4003
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.049

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
Cl1 Cl 0.83302(6) 0.09985(3) 0.92891(4) 0.02795(15) Uani 1 1 d . . . . .
Cl2 Cl 0.74131(7) 0.22496(4) 1.06233(4) 0.03425(17) Uani 1 1 d . . . . .
O1 O 0.37488(18) -0.10352(9) 0.74719(11) 0.0313(4) Uani 1 1 d . . . . .
O2 O 0.56745(16) -0.03663(8) 0.84664(10) 0.0230(3) Uani 1 1 d . . . . .
O3 O 0.8006(2) 0.20038(11) 0.57810(11) 0.0399(4) Uani 1 1 d . . . . .
O4 O 0.85948(17) 0.15362(9) 0.72997(11) 0.0301(4) Uani 1 1 d . . . . .
N1 N 0.3784(2) 0.07973(10) 0.53926(12) 0.0236(4) Uani 1 1 d . . . . .
H1A H 0.3011 0.0881 0.4882 0.028 Uiso 1 1 calc R U . . .
C1 C 0.3629(2) 0.02279(12) 0.60545(15) 0.0208(5) Uani 1 1 d . . . . .
C2 C 0.4707(2) 0.01608(12) 0.69119(14) 0.0194(4) Uani 1 1 d . . . . .
C3 C 0.5997(2) 0.07658(12) 0.72101(14) 0.0180(4) Uani 1 1 d . . . . .
H3A H 0.6954 0.0473 0.7528 0.022 Uiso 1 1 calc R U . . .
C4 C 0.6208(2) 0.12085(12) 0.63196(14) 0.0202(5) Uani 1 1 d . . . . .
C5 C 0.5079(2) 0.12433(12) 0.54842(14) 0.0219(5) Uani 1 1 d . . . . .
C6 C 0.5675(2) 0.13726(11) 0.79360(13) 0.0166(4) Uani 1 1 d . . . . .
C7 C 0.4340(2) 0.18130(12) 0.76569(14) 0.0202(4) Uani 1 1 d . . . . .
H7A H 0.3653 0.1711 0.7041 0.024 Uiso 1 1 calc R U . . .
C8 C 0.3977(3) 0.23949(13) 0.82459(15) 0.0240(5) Uani 1 1 d . . . . .
H8A H 0.3072 0.2697 0.8023 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4935(3) 0.25334(13) 0.91578(15) 0.0257(5) Uani 1 1 d . . . . .
H9A H 0.4693 0.2927 0.9570 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6252(2) 0.20907(13) 0.94595(14) 0.0231(5) Uani 1 1 d . . . . .
C11 C 0.6641(2) 0.15184(12) 0.88578(14) 0.0190(4) Uani 1 1 d . . . . .
C12 C 0.2187(3) -0.02422(14) 0.57172(16) 0.0286(5) Uani 1 1 d . . . . .
H12A H 0.1936 -0.0481 0.6278 0.043 Uiso 1 1 calc R U . . .
H12B H 0.2319 -0.0667 0.5276 0.043 Uiso 1 1 calc R U . . .
H12C H 0.1365 0.0115 0.5378 0.043 Uiso 1 1 calc R U . . .
C13 C 0.4615(2) -0.04719(12) 0.76071(14) 0.0205(5) Uani 1 1 d . . . . .
C14 C 0.5636(3) -0.09454(13) 0.92157(15) 0.0286(5) Uani 1 1 d . . . . .
H14A H 0.5754 -0.1494 0.8986 0.034 Uiso 1 1 calc R U . . .
H14B H 0.4655 -0.0913 0.9376 0.034 Uiso 1 1 calc R U . . .
C15 C 0.6909(3) -0.07575(17) 1.00942(18) 0.0481(7) Uani 1 1 d . . . . .
H15A H 0.6874 -0.1126 1.0620 0.072 Uiso 1 1 calc R U . . .
H15B H 0.6808 -0.0205 1.0300 0.072 Uiso 1 1 calc R U . . .
H15C H 0.7878 -0.0819 0.9938 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7640(3) 0.16246(13) 0.64037(15) 0.0243(5) Uani 1 1 d . . . . .
C17 C 1.0069(3) 0.18942(16) 0.74574(18) 0.0369(6) Uani 1 1 d . . . . .
H17A H 1.0658 0.1805 0.8130 0.055 Uiso 1 1 calc R U . . .
H17B H 0.9957 0.2471 0.7331 0.055 Uiso 1 1 calc R U . . .
H17C H 1.0594 0.1651 0.7018 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5046(3) 0.17357(14) 0.46008(15) 0.0294(5) Uani 1 1 d . . . . .
H18A H 0.5465 0.2268 0.4801 0.044 Uiso 1 1 calc R U . . .
H18B H 0.3998 0.1789 0.4201 0.044 Uiso 1 1 calc R U . . .
H18C H 0.5653 0.1471 0.4225 0.044 Uiso 1 1 calc R U . . .
O5 O 0.1454(2) 0.06764(11) 0.35135(12) 0.0473(5) Uani 1 1 d . . . . .
C21 C 0.0922(3) 0.08466(14) 0.26650(16) 0.0326(6) Uani 1 1 d . . . . .
C22 C 0.1545(3) 0.15073(17) 0.2193(2) 0.0470(7) Uani 1 1 d . . . . .
H22A H 0.2156 0.1864 0.2691 0.070 Uiso 1 1 calc R U . . .
H22B H 0.0709 0.1811 0.1769 0.070 Uiso 1 1 calc R U . . .
H22C H 0.2179 0.1282 0.1808 0.070 Uiso 1 1 calc R U . . .
C23 C -0.0405(3) 0.03972(17) 0.20556(19) 0.0458(7) Uani 1 1 d . . . . .
H23A H -0.0588 -0.0078 0.2408 0.069 Uiso 1 1 calc R U . . .
H23B H -0.0195 0.0233 0.1449 0.069 Uiso 1 1 calc R U . . .
H23C H -0.1303 0.0742 0.1910 0.069 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
Cl1 C11 1.736(2) . ?
Cl2 C10 1.737(2) . ?
O1 C13 1.212(2) . ?
O2 C13 1.356(2) . ?
O2 C14 1.453(2) . ?
O3 C16 1.214(3) . ?
O4 C16 1.351(3) . ?
O4 C17 1.439(3) . ?
N1 C1 1.378(3) . ?
N1 C5 1.378(3) . ?
N1 H1A 0.8800 . ?
C1 C2 1.356(3) . ?
C1 C12 1.500(3) . ?
C2 C13 1.471(3) . ?
C2 C3 1.526(3) . ?
C3 C4 1.532(3) . ?
C3 C6 1.538(3) . ?
C3 H3A 1.0000 . ?
C4 C5 1.354(3) . ?
C4 C16 1.462(3) . ?
C5 C18 1.503(3) . ?
C6 C7 1.390(3) . ?
C6 C11 1.397(3) . ?
C7 C8 1.386(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.398(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.498(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O5 C21 1.214(3) . ?
C21 C22 1.488(4) . ?
C21 C23 1.492(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C13 O2 C14 115.40(16) . . ?
C16 O4 C17 116.19(17) . . ?
C1 N1 C5 123.76(18) . . ?
C1 N1 H1A 118.1 . . ?
C5 N1 H1A 118.1 . . ?
C2 C1 N1 119.64(19) . . ?
C2 C1 C12 127.58(19) . . ?
N1 C1 C12 112.75(18) . . ?
C1 C2 C13 120.71(19) . . ?
C1 C2 C3 121.17(18) . . ?
C13 C2 C3 118.02(17) . . ?
C2 C3 C4 110.54(16) . . ?
C2 C3 C6 110.34(16) . . ?
C4 C3 C6 109.72(16) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C6 C3 H3A 108.7 . . ?
C5 C4 C16 120.39(18) . . ?
C5 C4 C3 121.15(19) . . ?
C16 C4 C3 118.41(18) . . ?
C4 C5 N1 119.52(18) . . ?
C4 C5 C18 127.1(2) . . ?
N1 C5 C18 113.39(18) . . ?
C7 C6 C11 117.49(18) . . ?
C7 C6 C3 118.10(17) . . ?
C11 C6 C3 124.41(18) . . ?
C8 C7 C6 122.33(19) . . ?
C8 C7 H7A 118.8 . . ?
C6 C7 H7A 118.8 . . ?
C9 C8 C7 119.8(2) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 H9A 120.6 . . ?
C10 C9 H9A 120.6 . . ?
C9 C10 C11 121.46(19) . . ?
C9 C10 Cl2 118.26(16) . . ?
C11 C10 Cl2 120.28(17) . . ?
C6 C11 C10 119.99(19) . . ?
C6 C11 Cl1 121.59(16) . . ?
C10 C11 Cl1 118.42(15) . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 O2 121.47(18) . . ?
O1 C13 C2 127.28(19) . . ?
O2 C13 C2 111.24(17) . . ?
O2 C14 C15 108.15(18) . . ?
O2 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O2 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 O4 121.2(2) . . ?
O3 C16 C4 127.6(2) . . ?
O4 C16 C4 111.17(17) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C21 C22 122.0(2) . . ?
O5 C21 C23 120.6(2) . . ?
C22 C21 C23 117.4(2) . . ?
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 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 9.2(3) . . . . ?
C5 N1 C1 C12 -172.53(19) . . . . ?
N1 C1 C2 C13 -176.45(18) . . . . ?
C12 C1 C2 C13 5.5(3) . . . . ?
N1 C1 C2 C3 7.2(3) . . . . ?
C12 C1 C2 C3 -170.83(19) . . . . ?
C1 C2 C3 C4 -20.7(3) . . . . ?
C13 C2 C3 C4 162.89(17) . . . . ?
C1 C2 C3 C6 100.9(2) . . . . ?
C13 C2 C3 C6 -75.6(2) . . . . ?
C2 C3 C4 C5 20.9(3) . . . . ?
C6 C3 C4 C5 -101.0(2) . . . . ?
C2 C3 C4 C16 -161.67(17) . . . . ?
C6 C3 C4 C16 76.4(2) . . . . ?
C16 C4 C5 N1 174.98(18) . . . . ?
C3 C4 C5 N1 -7.7(3) . . . . ?
C16 C4 C5 C18 -5.6(3) . . . . ?
C3 C4 C5 C18 171.72(19) . . . . ?
C1 N1 C5 C4 -8.9(3) . . . . ?
C1 N1 C5 C18 171.64(18) . . . . ?
C2 C3 C6 C7 -57.1(2) . . . . ?
C4 C3 C6 C7 64.9(2) . . . . ?
C2 C3 C6 C11 123.5(2) . . . . ?
C4 C3 C6 C11 -114.4(2) . . . . ?
C11 C6 C7 C8 1.9(3) . . . . ?
C3 C6 C7 C8 -177.52(18) . . . . ?
C6 C7 C8 C9 -2.2(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C8 C9 C10 Cl2 -177.93(16) . . . . ?
C7 C6 C11 C10 -0.2(3) . . . . ?
C3 C6 C11 C10 179.22(18) . . . . ?
C7 C6 C11 Cl1 179.40(15) . . . . ?
C3 C6 C11 Cl1 -1.2(3) . . . . ?
C9 C10 C11 C6 -1.3(3) . . . . ?
Cl2 C10 C11 C6 177.64(15) . . . . ?
C9 C10 C11 Cl1 179.13(16) . . . . ?
Cl2 C10 C11 Cl1 -1.9(2) . . . . ?
C14 O2 C13 O1 -3.2(3) . . . . ?
C14 O2 C13 C2 177.73(17) . . . . ?
C1 C2 C13 O1 9.6(3) . . . . ?
C3 C2 C13 O1 -173.9(2) . . . . ?
C1 C2 C13 O2 -171.38(18) . . . . ?
C3 C2 C13 O2 5.1(2) . . . . ?
C13 O2 C14 C15 177.9(2) . . . . ?
C17 O4 C16 O3 -1.8(3) . . . . ?
C17 O4 C16 C4 177.60(18) . . . . ?
C5 C4 C16 O3 -2.5(3) . . . . ?
C3 C4 C16 O3 -179.9(2) . . . . ?
C5 C4 C16 O4 178.11(19) . . . . ?
C3 C4 C16 O4 0.7(3) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_exptl_crystal_preparation       pharmaceutical
####################################################################### 
# 
# 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_fel_apn
_database_code_depnum_ccdc_archive 'CCDC 1048181'
_audit_update_record             
;
2015-02-08 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            'felodipine:acetophenone (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 Cl2 N O4, C8 H8 O'
_chemical_formula_sum            'C26 H27 Cl2 N O5'
_chemical_formula_weight         504.39
_chemical_absolute_configuration unk

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.3940(7)
_cell_length_b                   11.4991(10)
_cell_length_c                   29.003(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2466.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3496
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      23.70

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11352
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         25.09
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_reflns_number_total             4368
_reflns_number_gt                3570
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 v2010.1-2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL v.6.12 (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0513P)²+1.1024P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
1849 Friedel pairs measured
Refined as a racemic twin: essentially 50:50 ratio
Starting compound was a racemate
;
_refine_ls_abs_structure_Flack   0.47(9)
_refine_ls_number_reflns         4368
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.051

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.75357(16) 0.70389(8) 0.03568(3) 0.0421(3) Uani 1 1 d . . .
Cl2 Cl 0.35606(13) 0.71137(9) 0.07068(3) 0.0358(2) Uani 1 1 d . . .
O1 O 0.2158(5) 1.0391(2) 0.19577(10) 0.0571(9) Uani 1 1 d . . .
O2 O 0.1931(4) 0.9204(2) 0.13533(9) 0.0465(8) Uani 1 1 d . . .
O3 O 0.2372(5) 0.5060(2) 0.14233(8) 0.0477(8) Uani 1 1 d . . .
O4 O 0.2212(4) 0.41523(18) 0.20987(8) 0.0411(7) Uani 1 1 d . . .
N1 N 0.3153(4) 0.7344(2) 0.27496(9) 0.0287(7) Uani 1 1 d . . .
H1A H 0.3488 0.7384 0.3040 0.034 Uiso 1 1 calc R . .
C1 C 0.2873(5) 0.8372(3) 0.25120(12) 0.0271(9) Uani 1 1 d . . .
C2 C 0.2718(5) 0.8347(3) 0.20485(12) 0.0249(8) Uani 1 1 d . . .
C3 C 0.3062(4) 0.7231(3) 0.17830(11) 0.0221(7) Uani 1 1 d . . .
H3A H 0.2169 0.7187 0.1525 0.027 Uiso 1 1 calc R . .
C4 C 0.2787(5) 0.6177(3) 0.20915(11) 0.0216(7) Uani 1 1 d . . .
C5 C 0.2935(5) 0.6259(3) 0.25551(11) 0.0240(8) Uani 1 1 d . . .
C6 C 0.4963(4) 0.7229(3) 0.15755(10) 0.0199(7) Uani 1 1 d . . .
C7 C 0.6446(5) 0.7274(3) 0.18699(11) 0.0243(8) Uani 1 1 d . . .
H7A H 0.6242 0.7332 0.2192 0.029 Uiso 1 1 calc R . .
C8 C 0.8198(5) 0.7239(3) 0.17113(12) 0.0293(8) Uani 1 1 d . . .
H8A H 0.9180 0.7269 0.1922 0.035 Uiso 1 1 calc R . .
C9 C 0.8518(5) 0.7161(3) 0.12406(12) 0.0322(8) Uani 1 1 d . . .
H9A H 0.9720 0.7129 0.1126 0.039 Uiso 1 1 calc R . .
C10 C 0.7072(5) 0.7130(3) 0.09441(11) 0.0262(8) Uani 1 1 d . . .
C11 C 0.5315(5) 0.7168(3) 0.11055(11) 0.0242(7) Uani 1 1 d . . .
C12 C 0.2730(6) 0.9413(3) 0.28205(13) 0.0408(10) Uani 1 1 d . . .
H12A H 0.1532 0.9767 0.2785 0.061 Uiso 1 1 calc R . .
H12B H 0.3663 0.9980 0.2737 0.061 Uiso 1 1 calc R . .
H12C H 0.2900 0.9173 0.3142 0.061 Uiso 1 1 calc R . .
C13 C 0.2268(5) 0.9418(3) 0.18016(13) 0.0317(9) Uani 1 1 d . . .
C14 C 0.1297(9) 1.0203(4) 0.10898(17) 0.0688(15) Uani 1 1 d . . .
H14A H 0.0297 1.0590 0.1257 0.083 Uiso 1 1 calc R . .
H14B H 0.2293 1.0771 0.1053 0.083 Uiso 1 1 calc R . .
C15 C 0.0694(10) 0.9836(5) 0.0656(2) 0.098(2) Uani 1 1 d . . .
H15A H 0.0186 1.0500 0.0489 0.147 Uiso 1 1 calc R . .
H15B H -0.0239 0.9239 0.0695 0.147 Uiso 1 1 calc R . .
H15C H 0.1712 0.9513 0.0482 0.147 Uiso 1 1 calc R . .
C16 C 0.2460(6) 0.5106(3) 0.18372(12) 0.0284(8) Uani 1 1 d . . .
C17 C 0.1873(7) 0.3072(3) 0.18512(14) 0.0508(13) Uani 1 1 d . . .
H17A H 0.1712 0.2437 0.2073 0.076 Uiso 1 1 calc R . .
H17B H 0.2904 0.2899 0.1650 0.076 Uiso 1 1 calc R . .
H17C H 0.0777 0.3154 0.1664 0.076 Uiso 1 1 calc R . .
C18 C 0.2867(6) 0.5299(3) 0.29082(11) 0.0312(9) Uani 1 1 d . . .
H18A H 0.3697 0.4675 0.2818 0.047 Uiso 1 1 calc R . .
H18B H 0.1634 0.4991 0.2927 0.047 Uiso 1 1 calc R . .
H18C H 0.3227 0.5607 0.3210 0.047 Uiso 1 1 calc R . .
O5 O 0.3580(6) 0.7389(2) 0.37571(9) 0.0707(11) Uani 1 1 d . . .
C19 C 0.3418(7) 0.9111(3) 0.41962(14) 0.0510(12) Uani 1 1 d . . .
H19A H 0.3604 0.9480 0.3895 0.076 Uiso 1 1 calc R . .
H19B H 0.4368 0.9364 0.4409 0.076 Uiso 1 1 calc R . .
H19C H 0.2234 0.9337 0.4319 0.076 Uiso 1 1 calc R . .
C20 C 0.3494(6) 0.7800(3) 0.41421(13) 0.0415(10) Uani 1 1 d . . .
C21 C 0.3506(5) 0.7050(3) 0.45526(11) 0.0335(8) Uani 1 1 d . . .
C22 C 0.3091(6) 0.7445(3) 0.49869(13) 0.0452(11) Uani 1 1 d . . .
H22A H 0.2752 0.8235 0.5029 0.054 Uiso 1 1 calc R . .
C23 C 0.3161(7) 0.6706(4) 0.53643(15) 0.0561(13) Uani 1 1 d . . .
H23A H 0.2883 0.6994 0.5663 0.067 Uiso 1 1 calc R . .
C24 C 0.3626(7) 0.5566(4) 0.53081(16) 0.0561(13) Uani 1 1 d . . .
H24A H 0.3656 0.5059 0.5567 0.067 Uiso 1 1 calc R . .
C25 C 0.4048(7) 0.5156(4) 0.48817(16) 0.0498(12) Uani 1 1 d . . .
H25A H 0.4404 0.4368 0.4845 0.060 Uiso 1 1 calc R . .
C26 C 0.3963(6) 0.5876(3) 0.45022(14) 0.0423(11) Uani 1 1 d . . .
H26A H 0.4216 0.5572 0.4204 0.051 Uiso 1 1 calc R . .


_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
Cl1 C10 1.741(3) . ?
Cl2 C11 1.739(3) . ?
O1 C13 1.210(4) . ?
O2 C13 1.346(4) . ?
O2 C14 1.457(5) . ?
O3 C16 1.204(4) . ?
O4 C16 1.346(4) . ?
O4 C17 1.456(4) . ?
N1 C5 1.379(4) . ?
N1 C1 1.384(4) . ?
N1 H1A 0.8800 . ?
C1 C2 1.349(5) . ?
C1 C12 1.498(5) . ?
C2 C13 1.462(5) . ?
C2 C3 1.518(4) . ?
C3 C4 1.520(4) . ?
C3 C6 1.529(5) . ?
C3 H3A 1.0000 . ?
C4 C5 1.352(4) . ?
C4 C16 1.455(5) . ?
C5 C18 1.506(4) . ?
C6 C11 1.390(4) . ?
C6 C7 1.391(5) . ?
C7 C8 1.375(5) . ?
C7 H7A 0.9500 . ?
C8 C9 1.388(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.373(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.381(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.399(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O5 C20 1.215(4) . ?
C19 C20 1.516(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.470(5) . ?
C21 C22 1.374(5) . ?
C21 C26 1.400(5) . ?
C22 C23 1.387(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.365(6) . ?
C23 H23A 0.9500 . ?
C24 C25 1.360(6) . ?
C24 H24A 0.9500 . ?
C25 C26 1.378(6) . ?
C25 H25A 0.9500 . ?
C26 H26A 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
C13 O2 C14 115.0(3) . . ?
C16 O4 C17 116.2(3) . . ?
C5 N1 C1 123.5(3) . . ?
C5 N1 H1A 118.3 . . ?
C1 N1 H1A 118.3 . . ?
C2 C1 N1 119.4(3) . . ?
C2 C1 C12 127.3(3) . . ?
N1 C1 C12 113.3(3) . . ?
C1 C2 C13 119.3(3) . . ?
C1 C2 C3 120.6(3) . . ?
C13 C2 C3 120.1(3) . . ?
C2 C3 C4 110.7(3) . . ?
C2 C3 C6 110.8(3) . . ?
C4 C3 C6 110.7(3) . . ?
C2 C3 H3A 108.2 . . ?
C4 C3 H3A 108.2 . . ?
C6 C3 H3A 108.2 . . ?
C5 C4 C16 125.2(3) . . ?
C5 C4 C3 121.3(3) . . ?
C16 C4 C3 113.5(3) . . ?
C4 C5 N1 118.6(3) . . ?
C4 C5 C18 128.5(3) . . ?
N1 C5 C18 112.9(3) . . ?
C11 C6 C7 117.1(3) . . ?
C11 C6 C3 123.9(3) . . ?
C7 C6 C3 118.9(3) . . ?
C8 C7 C6 122.4(3) . . ?
C8 C7 H7A 118.8 . . ?
C6 C7 H7A 118.8 . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 120.3 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 Cl1 117.5(3) . . ?
C11 C10 Cl1 121.2(3) . . ?
C10 C11 C6 120.7(3) . . ?
C10 C11 Cl2 118.4(2) . . ?
C6 C11 Cl2 120.9(3) . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 O2 121.2(3) . . ?
O1 C13 C2 127.6(4) . . ?
O2 C13 C2 111.2(3) . . ?
C15 C14 O2 109.6(4) . . ?
C15 C14 H14A 109.7 . . ?
O2 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
O2 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 O4 121.2(3) . . ?
O3 C16 C4 123.5(3) . . ?
O4 C16 C4 115.3(3) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 C21 121.0(3) . . ?
O5 C20 C19 119.0(3) . . ?
C21 C20 C19 120.0(3) . . ?
C22 C21 C26 117.9(4) . . ?
C22 C21 C20 123.2(3) . . ?
C26 C21 C20 118.9(3) . . ?
C21 C22 C23 120.8(4) . . ?
C21 C22 H22A 119.6 . . ?
C23 C22 H22A 119.6 . . ?
C24 C23 C22 120.3(4) . . ?
C24 C23 H23A 119.9 . . ?
C22 C23 H23A 119.9 . . ?
C25 C24 C23 119.9(4) . . ?
C25 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C24 C25 C26 120.5(4) . . ?
C24 C25 H25A 119.7 . . ?
C26 C25 H25A 119.7 . . ?
C25 C26 C21 120.4(4) . . ?
C25 C26 H26A 119.8 . . ?
C21 C26 H26A 119.8 . . ?

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
C5 N1 C1 C2 -13.2(5) . . . . ?
C5 N1 C1 C12 165.3(3) . . . . ?
N1 C1 C2 C13 174.8(3) . . . . ?
C12 C1 C2 C13 -3.5(6) . . . . ?
N1 C1 C2 C3 -7.1(5) . . . . ?
C12 C1 C2 C3 174.7(4) . . . . ?
C1 C2 C3 C4 23.6(5) . . . . ?
C13 C2 C3 C4 -158.2(3) . . . . ?
C1 C2 C3 C6 -99.5(4) . . . . ?
C13 C2 C3 C6 78.6(4) . . . . ?
C2 C3 C4 C5 -23.6(4) . . . . ?
C6 C3 C4 C5 99.7(4) . . . . ?
C2 C3 C4 C16 159.5(3) . . . . ?
C6 C3 C4 C16 -77.3(4) . . . . ?
C16 C4 C5 N1 -176.7(3) . . . . ?
C3 C4 C5 N1 6.7(5) . . . . ?
C16 C4 C5 C18 2.3(6) . . . . ?
C3 C4 C5 C18 -174.3(4) . . . . ?
C1 N1 C5 C4 13.3(5) . . . . ?
C1 N1 C5 C18 -165.8(3) . . . . ?
C2 C3 C6 C11 -118.7(4) . . . . ?
C4 C3 C6 C11 118.1(3) . . . . ?
C2 C3 C6 C7 62.1(4) . . . . ?
C4 C3 C6 C7 -61.1(4) . . . . ?
C11 C6 C7 C8 -1.3(5) . . . . ?
C3 C6 C7 C8 178.0(3) . . . . ?
C6 C7 C8 C9 0.3(6) . . . . ?
C7 C8 C9 C10 0.6(6) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C8 C9 C10 Cl1 179.7(3) . . . . ?
C9 C10 C11 C6 -0.6(5) . . . . ?
Cl1 C10 C11 C6 179.3(3) . . . . ?
C9 C10 C11 Cl2 -179.5(3) . . . . ?
Cl1 C10 C11 Cl2 0.4(4) . . . . ?
C7 C6 C11 C10 1.4(5) . . . . ?
C3 C6 C11 C10 -177.8(3) . . . . ?
C7 C6 C11 Cl2 -179.7(2) . . . . ?
C3 C6 C11 Cl2 1.1(5) . . . . ?
C14 O2 C13 O1 -4.7(6) . . . . ?
C14 O2 C13 C2 174.2(4) . . . . ?
C1 C2 C13 O1 7.1(6) . . . . ?
C3 C2 C13 O1 -171.0(4) . . . . ?
C1 C2 C13 O2 -171.7(3) . . . . ?
C3 C2 C13 O2 10.1(5) . . . . ?
C13 O2 C14 C15 -169.6(5) . . . . ?
C17 O4 C16 O3 1.3(6) . . . . ?
C17 O4 C16 C4 179.7(4) . . . . ?
C5 C4 C16 O3 -178.5(4) . . . . ?
C3 C4 C16 O3 -1.7(6) . . . . ?
C5 C4 C16 O4 3.1(6) . . . . ?
C3 C4 C16 O4 179.9(3) . . . . ?
O5 C20 C21 C22 -168.0(5) . . . . ?
C19 C20 C21 C22 13.5(7) . . . . ?
O5 C20 C21 C26 12.1(7) . . . . ?
C19 C20 C21 C26 -166.4(4) . . . . ?
C26 C21 C22 C23 1.3(6) . . . . ?
C20 C21 C22 C23 -178.6(4) . . . . ?
C21 C22 C23 C24 -0.7(7) . . . . ?
C22 C23 C24 C25 0.9(8) . . . . ?
C23 C24 C25 C26 -1.8(8) . . . . ?
C24 C25 C26 C21 2.4(7) . . . . ?
C22 C21 C26 C25 -2.1(6) . . . . ?
C20 C21 C26 C25 177.8(4) . . . . ?

_exptl_crystal_preparation       pharmaceutical
####################################################################### 
# 
# 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_fel_dmso
_database_code_depnum_ccdc_archive 'CCDC 1048182'
_audit_update_record             
;
2015-02-08 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
#==============================================================================

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            'felodipine:dimethylsulfoxide (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 Cl2 N O4, C2 H6 O S'
_chemical_formula_sum            'C20 H25 Cl2 N O5 S'
_chemical_formula_weight         462.37

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.660(3)
_cell_length_b                   9.816(3)
_cell_length_c                   13.782(4)
_cell_angle_alpha                87.37(2)
_cell_angle_beta                 79.17(3)
_cell_angle_gamma                77.79(3)
_cell_volume                     1124.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    30
_cell_measurement_theta_min      5
_cell_measurement_theta_max      15

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.412
_shelx_estimated_absorpt_T_min   0.859
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Bruker-P4
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4671
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.123
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3924
_reflns_number_gt                2045
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Site occupancy factors were refined for the C atoms of the disordered
ethyl/methyl esters. The refined value was 0.521(14). Since this does
not differ signficantly from 0.5, the disordered atoms were subsequently
constrained to site occupancy 0.5.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1189P)²+0.4842P] 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         3924
_refine_ls_number_parameters     281
# SAME restraints applied to two components of the DMSO molecule
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1603
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2420
_refine_ls_wR_factor_gt          0.1971
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.053
_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
Cl1 Cl 0.1615(2) 0.92074(18) 1.06885(12) 0.0828(6) Uani 1 1 d . . . . .
Cl2 Cl 0.1277(2) 0.68422(18) 0.93712(11) 0.0754(6) Uani 1 1 d . . . . .
N1 N 0.5187(5) 0.7063(5) 0.5344(3) 0.0605(13) Uani 1 1 d . . . . .
H1A H 0.5838 0.7342 0.4864 0.073 Uiso 1 1 calc R U . . .
O1 O 0.0076(5) 0.8246(6) 0.5713(4) 0.0913(16) Uani 1 1 d . . . . .
O2 O 0.0055(4) 0.7607(5) 0.7272(3) 0.0752(13) Uani 1 1 d . . . . .
O3 O 0.6801(5) 0.3954(5) 0.7423(4) 0.0917(16) Uani 1 1 d . . . . .
O4 O 0.4421(5) 0.4691(4) 0.8364(3) 0.0671(12) Uani 1 1 d . . . . .
C1 C 0.3558(7) 0.7622(6) 0.5430(4) 0.0572(15) Uani 1 1 d . . . . .
C2 C 0.2550(6) 0.7390(6) 0.6274(4) 0.0485(13) Uani 1 1 d . . . . .
C3 C 0.3219(6) 0.6757(5) 0.7172(4) 0.0476(13) Uani 1 1 d . . . . .
H3A H 0.2507 0.6164 0.7516 0.057 Uiso 1 1 calc R U . . .
C4 C 0.4913(6) 0.5840(5) 0.6866(4) 0.0501(14) Uani 1 1 d . . . . .
C5 C 0.5804(6) 0.6098(6) 0.5980(4) 0.0536(14) Uani 1 1 d . . . . .
C6 C 0.3272(6) 0.7876(5) 0.7884(4) 0.0456(13) Uani 1 1 d . . . . .
C7 C 0.4170(6) 0.8881(6) 0.7540(4) 0.0573(16) Uani 1 1 d . . . . .
H7A H 0.4694 0.8845 0.6885 0.069 Uiso 1 1 calc R U . . .
C8 C 0.4312(7) 0.9926(7) 0.8132(5) 0.0694(18) Uani 1 1 d . . . . .
H8A H 0.4930 1.0573 0.7879 0.083 Uiso 1 1 calc R U . . .
C9 C 0.3532(8) 1.0003(6) 0.9103(5) 0.0687(18) Uani 1 1 d . . . . .
H9A H 0.3634 1.0695 0.9511 0.082 Uiso 1 1 calc R U . . .
C10 C 0.2612(7) 0.9065(6) 0.9463(4) 0.0581(16) Uani 1 1 d . . . . .
C11 C 0.2469(6) 0.7995(5) 0.8873(4) 0.0502(14) Uani 1 1 d . . . . .
C12 C 0.3112(7) 0.8420(8) 0.4537(5) 0.076(2) Uani 1 1 d . . . . .
H12A H 0.1973 0.8777 0.4647 0.115 Uiso 1 1 calc R U . . .
H12B H 0.3416 0.7814 0.3975 0.115 Uiso 1 1 calc R U . . .
H12C H 0.3662 0.9181 0.4416 0.115 Uiso 1 1 calc R U . . .
C13 C 0.0809(7) 0.7806(6) 0.6352(4) 0.0571(15) Uani 1 1 d . . . . .
C14 C -0.1684(7) 0.7946(9) 0.7459(5) 0.086(2) Uani 0.5 1 d . . P A 1
H14A H -0.2086 0.7636 0.6915 0.103 Uiso 0.5 1 calc R U P A 1
H14B H -0.2064 0.8947 0.7524 0.103 Uiso 0.5 1 calc R U P A 1
C15 C -0.2298(15) 0.7204(15) 0.8430(11) 0.087(4) Uani 0.5 1 d . . P A 1
H15A H -0.3451 0.7418 0.8567 0.130 Uiso 0.5 1 calc R U P A 1
H15B H -0.1899 0.7520 0.8965 0.130 Uiso 0.5 1 calc R U P A 1
H15C H -0.1922 0.6215 0.8359 0.130 Uiso 0.5 1 calc R U P A 1
C17 C 0.4891(9) 0.3595(7) 0.9066(6) 0.086(2) Uani 0.5 1 d . . P B 1
H17A H 0.4041 0.3637 0.9629 0.128 Uiso 0.5 1 calc R U P B 1
H17B H 0.5847 0.3724 0.9275 0.128 Uiso 0.5 1 calc R U P B 1
H17C H 0.5095 0.2703 0.8756 0.128 Uiso 0.5 1 calc R U P B 1
C14' C 0.4891(9) 0.3595(7) 0.9066(6) 0.086(2) Uani 0.5 1 d . . P B 2
H14C H 0.5855 0.3723 0.9281 0.103 Uiso 0.5 1 calc R U P B 2
H14D H 0.5124 0.2693 0.8751 0.103 Uiso 0.5 1 calc R U P B 2
C15' C 0.3538(17) 0.3645(15) 0.9953(11) 0.089(4) Uani 0.5 1 d . . P B 2
H15D H 0.3857 0.2932 1.0419 0.134 Uiso 0.5 1 calc R U P B 2
H15E H 0.2595 0.3495 0.9740 0.134 Uiso 0.5 1 calc R U P B 2
H15F H 0.3309 0.4541 1.0262 0.134 Uiso 0.5 1 calc R U P B 2
C17' C -0.1684(7) 0.7946(9) 0.7459(5) 0.086(2) Uani 0.5 1 d . . P A 2
H17D H -0.2081 0.7771 0.8142 0.129 Uiso 0.5 1 calc R U P A 2
H17E H -0.2078 0.7380 0.7052 0.129 Uiso 0.5 1 calc R U P A 2
H17F H -0.2047 0.8913 0.7309 0.129 Uiso 0.5 1 calc R U P A 2
C16 C 0.5495(7) 0.4760(6) 0.7528(4) 0.0588(16) Uani 1 1 d . . . . .
C18 C 0.7552(7) 0.5384(7) 0.5598(5) 0.074(2) Uani 1 1 d . . . . .
H18A H 0.7906 0.5743 0.4954 0.112 Uiso 1 1 calc R U . . .
H18B H 0.7629 0.4397 0.5560 0.112 Uiso 1 1 calc R U . . .
H18C H 0.8217 0.5565 0.6041 0.112 Uiso 1 1 calc R U . . .
S1 S 0.8856(2) 0.6943(3) 0.32192(16) 0.0898(11) Uani 0.857(6) 1 d D . P C 1
O21 O 0.7025(6) 0.7365(7) 0.3439(4) 0.118(2) Uani 0.857(6) 1 d D . P C 1
C22 C 0.9333(10) 0.6528(9) 0.1984(6) 0.110(3) Uani 0.857(6) 1 d D . P C 1
H22A H 0.8971 0.5694 0.1883 0.165 Uiso 0.857(6) 1 calc R U P C 1
H22B H 1.0476 0.6379 0.1769 0.165 Uiso 0.857(6) 1 calc R U P C 1
H22C H 0.8817 0.7279 0.1610 0.165 Uiso 0.857(6) 1 calc R U P C 1
C23 C 0.9609(9) 0.8442(9) 0.3208(6) 0.100(3) Uani 0.857(6) 1 d D . P C 1
H23A H 0.9452 0.8774 0.3871 0.151 Uiso 0.857(6) 1 calc R U P C 1
H23B H 0.9058 0.9143 0.2814 0.151 Uiso 0.857(6) 1 calc R U P C 1
H23C H 1.0737 0.8240 0.2934 0.151 Uiso 0.857(6) 1 calc R U P C 1
S1' S 0.8267(9) 0.7848(10) 0.2657(6) 0.082(6) Uani 0.143(6) 1 d D . P C 2
O21' O 0.7025(6) 0.7365(7) 0.3439(4) 0.118(2) Uani 0.143(6) 1 d D . P C 2
C22' C 0.9333(10) 0.6528(9) 0.1984(6) 0.110(3) Uani 0.143(6) 1 d D . P C 2
H22D H 0.8653 0.6166 0.1630 0.165 Uiso 0.143(6) 1 calc R U P C 2
H22E H 0.9798 0.5813 0.2404 0.165 Uiso 0.143(6) 1 calc R U P C 2
H22F H 1.0172 0.6830 0.1522 0.165 Uiso 0.143(6) 1 calc R U P C 2
C23' C 0.9609(9) 0.8442(9) 0.3208(6) 0.100(3) Uani 0.143(6) 1 d D . P C 2
H23D H 0.9051 0.9206 0.3634 0.151 Uiso 0.143(6) 1 calc R U P C 2
H23E H 1.0399 0.8749 0.2710 0.151 Uiso 0.143(6) 1 calc R U P C 2
H23F H 1.0131 0.7703 0.3590 0.151 Uiso 0.143(6) 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.744(6) . ?
Cl2 C11 1.724(6) . ?
N1 C5 1.355(7) . ?
N1 C1 1.386(7) . ?
N1 H1A 0.8600 . ?
O1 C13 1.193(7) . ?
O2 C13 1.339(7) . ?
O2 C14 1.448(7) . ?
O3 C16 1.224(6) . ?
O4 C16 1.347(7) . ?
O4 C17 1.459(7) . ?
C1 C2 1.358(7) . ?
C1 C12 1.497(8) . ?
C2 C13 1.461(8) . ?
C2 C3 1.516(8) . ?
C3 C6 1.519(7) . ?
C3 C4 1.544(7) . ?
C3 H3A 0.9800 . ?
C4 C5 1.360(7) . ?
C4 C16 1.438(8) . ?
C5 C18 1.532(7) . ?
C6 C7 1.395(8) . ?
C6 C11 1.407(7) . ?
C7 C8 1.379(8) . ?
C7 H7A 0.9300 . ?
C8 C9 1.379(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.360(9) . ?
C9 H9A 0.9300 . ?
C10 C11 1.396(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.553(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
S1 O21 1.527(5) . ?
S1 C22 1.722(8) . ?
S1 C23 1.730(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 123.2(5) . . ?
C5 N1 H1A 118.4 . . ?
C1 N1 H1A 118.4 . . ?
C13 O2 C14 117.3(5) . . ?
C16 O4 C17 116.4(5) . . ?
C2 C1 N1 118.9(5) . . ?
C2 C1 C12 127.2(5) . . ?
N1 C1 C12 113.9(5) . . ?
C1 C2 C13 120.8(5) . . ?
C1 C2 C3 120.4(5) . . ?
C13 C2 C3 118.8(4) . . ?
C2 C3 C6 111.4(4) . . ?
C2 C3 C4 111.0(4) . . ?
C6 C3 C4 109.9(4) . . ?
C2 C3 H3A 108.2 . . ?
C6 C3 H3A 108.2 . . ?
C4 C3 H3A 108.2 . . ?
C5 C4 C16 122.6(5) . . ?
C5 C4 C3 118.4(5) . . ?
C16 C4 C3 119.0(5) . . ?
N1 C5 C4 121.3(5) . . ?
N1 C5 C18 113.2(5) . . ?
C4 C5 C18 125.5(5) . . ?
C7 C6 C11 116.6(5) . . ?
C7 C6 C3 118.3(5) . . ?
C11 C6 C3 125.1(5) . . ?
C8 C7 C6 122.7(5) . . ?
C8 C7 H7A 118.7 . . ?
C6 C7 H7A 118.7 . . ?
C7 C8 C9 119.5(6) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 120.3 . . ?
C10 C9 C8 119.8(6) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 121.2(5) . . ?
C9 C10 Cl1 118.7(5) . . ?
C11 C10 Cl1 120.0(5) . . ?
C10 C11 C6 120.2(5) . . ?
C10 C11 Cl2 119.0(4) . . ?
C6 C11 Cl2 120.8(4) . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 O2 121.3(5) . . ?
O1 C13 C2 127.8(5) . . ?
O2 C13 C2 110.8(5) . . ?
O2 C14 C15 108.3(7) . . ?
O2 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
O2 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H15D C15' H15E 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
O3 C16 O4 118.9(5) . . ?
O3 C16 C4 128.4(5) . . ?
O4 C16 C4 112.7(5) . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O21 S1 C22 104.8(4) . . ?
O21 S1 C23 107.7(4) . . ?
C22 S1 C23 100.8(4) . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 11.8(9) . . . . ?
C5 N1 C1 C12 -167.2(6) . . . . ?
N1 C1 C2 C13 -172.3(5) . . . . ?
C12 C1 C2 C13 6.7(10) . . . . ?
N1 C1 C2 C3 10.8(8) . . . . ?
C12 C1 C2 C3 -170.2(6) . . . . ?
C1 C2 C3 C6 95.6(6) . . . . ?
C13 C2 C3 C6 -81.3(6) . . . . ?
C1 C2 C3 C4 -27.2(7) . . . . ?
C13 C2 C3 C4 155.9(5) . . . . ?
C2 C3 C4 C5 24.0(7) . . . . ?
C6 C3 C4 C5 -99.6(6) . . . . ?
C2 C3 C4 C16 -156.6(5) . . . . ?
C6 C3 C4 C16 79.7(6) . . . . ?
C1 N1 C5 C4 -14.8(9) . . . . ?
C1 N1 C5 C18 165.9(5) . . . . ?
C16 C4 C5 N1 175.7(5) . . . . ?
C3 C4 C5 N1 -4.9(8) . . . . ?
C16 C4 C5 C18 -5.0(9) . . . . ?
C3 C4 C5 C18 174.3(5) . . . . ?
C2 C3 C6 C7 -58.9(6) . . . . ?
C4 C3 C6 C7 64.5(6) . . . . ?
C2 C3 C6 C11 120.5(5) . . . . ?
C4 C3 C6 C11 -116.1(5) . . . . ?
C11 C6 C7 C8 1.5(8) . . . . ?
C3 C6 C7 C8 -179.0(5) . . . . ?
C6 C7 C8 C9 -0.6(9) . . . . ?
C7 C8 C9 C10 -1.0(10) . . . . ?
C8 C9 C10 C11 1.6(9) . . . . ?
C8 C9 C10 Cl1 -179.0(5) . . . . ?
C9 C10 C11 C6 -0.5(8) . . . . ?
Cl1 C10 C11 C6 -180.0(4) . . . . ?
C9 C10 C11 Cl2 -179.7(5) . . . . ?
Cl1 C10 C11 Cl2 0.8(6) . . . . ?
C7 C6 C11 C10 -1.0(7) . . . . ?
C3 C6 C11 C10 179.6(5) . . . . ?
C7 C6 C11 Cl2 178.2(4) . . . . ?
C3 C6 C11 Cl2 -1.2(7) . . . . ?
C14 O2 C13 O1 0.0(9) . . . . ?
C14 O2 C13 C2 -178.8(5) . . . . ?
C1 C2 C13 O1 7.5(10) . . . . ?
C3 C2 C13 O1 -175.6(6) . . . . ?
C1 C2 C13 O2 -173.9(5) . . . . ?
C3 C2 C13 O2 3.1(7) . . . . ?
C13 O2 C14 C15 161.6(8) . . . . ?
C17 O4 C16 O3 -2.8(8) . . . . ?
C17 O4 C16 C4 178.2(5) . . . . ?
C5 C4 C16 O3 0.8(10) . . . . ?
C3 C4 C16 O3 -178.5(6) . . . . ?
C5 C4 C16 O4 179.7(5) . . . . ?
C3 C4 C16 O4 0.3(7) . . . . ?

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.085

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylsulfoxide'
_exptl_crystal_preparation       pharmaceutical
