# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_dil
_database_code_depnum_ccdc_archive 'CCDC 1056494'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            Diltiazem
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 N2 O4 S'
_chemical_formula_sum            'C22 H26 N2 O4 S'
_chemical_formula_weight         414.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_chemical_absolute_configuration rmad

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

_cell_length_a                   9.3387(2)
_cell_length_b                   13.9027(4)
_cell_length_c                   16.5550(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2149.39(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11053
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      30.034

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.181
_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      173(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  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6221
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1012
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         30.02
_reflns_number_total             6221
_reflns_number_gt                4230
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;

_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)+(0.0306P)²+0.8701P] 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 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_number_reflns         6221
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71501(6) 0.95805(5) 0.23643(4) 0.03024(17) Uani 1 1 d . . .
O1 O 1.34556(18) 0.81089(14) 0.31629(11) 0.0345(5) Uani 1 1 d . . .
O2 O 0.99524(17) 1.15822(12) 0.16226(10) 0.0242(4) Uani 1 1 d . . .
O3 O 0.91513(17) 1.24068(13) 0.05476(11) 0.0301(4) Uani 1 1 d . . .
O4 O 0.98707(16) 1.02234(13) 0.04735(10) 0.0289(4) Uani 1 1 d . . .
N1 N 0.74633(19) 1.00398(15) 0.05307(12) 0.0240(5) Uani 1 1 d . . .
N2 N 0.8079(2) 0.78148(17) -0.07143(14) 0.0368(6) Uani 1 1 d . . .
C1 C 0.8655(2) 1.04356(19) 0.23681(15) 0.0233(5) Uani 1 1 d . . .
H1 H 0.8497 1.0894 0.2809 0.028 Uiso 1 1 calc R . .
C2 C 0.8682(2) 1.10006(18) 0.15756(15) 0.0218(5) Uani 1 1 d . . .
H2 H 0.7841 1.1421 0.1551 0.026 Uiso 1 1 calc R . .
C3 C 0.8741(2) 1.03863(19) 0.08140(14) 0.0225(5) Uani 1 1 d . . .
C4 C 0.6101(2) 1.02384(19) 0.08957(16) 0.0240(6) Uani 1 1 d . . .
C5 C 0.4971(2) 1.05478(19) 0.04098(16) 0.0268(6) Uani 1 1 d . . .
H5 H 0.5119 1.0644 -0.0140 0.032 Uiso 1 1 calc R . .
C6 C 0.3630(3) 1.07121(19) 0.07397(17) 0.0294(6) Uani 1 1 d . . .
H6 H 0.2878 1.0901 0.0407 0.035 Uiso 1 1 calc R . .
C7 C 0.3402(2) 1.0598(2) 0.15528(17) 0.0315(7) Uani 1 1 d . . .
H7 H 0.2498 1.0708 0.1770 0.038 Uiso 1 1 calc R . .
C8 C 0.4524(2) 1.0318(2) 0.20496(16) 0.0288(6) Uani 1 1 d . . .
H8 H 0.4378 1.0264 0.2603 0.035 Uiso 1 1 calc R . .
C9 C 0.5868(2) 1.01190(18) 0.17233(15) 0.0231(6) Uani 1 1 d . . .
C10 C 0.9975(2) 0.98499(18) 0.25692(15) 0.0232(5) Uani 1 1 d . . .
C11 C 1.0831(2) 1.00980(19) 0.32222(15) 0.0249(6) Uani 1 1 d . . .
H11 H 1.0618 1.0650 0.3516 0.030 Uiso 1 1 calc R . .
C12 C 1.2004(2) 0.9539(2) 0.34470(14) 0.0261(6) Uani 1 1 d . . .
H12 H 1.2563 0.9714 0.3888 0.031 Uiso 1 1 calc R . .
C13 C 1.2331(2) 0.8718(2) 0.30077(15) 0.0255(6) Uani 1 1 d . . .
C14 C 1.1491(2) 0.84633(19) 0.23458(16) 0.0275(6) Uani 1 1 d . . .
H14 H 1.1714 0.7917 0.2048 0.033 Uiso 1 1 calc R . .
C15 C 1.0334(3) 0.9018(2) 0.21329(15) 0.0267(6) Uani 1 1 d . . .
H15 H 0.9778 0.8840 0.1692 0.032 Uiso 1 1 calc R . .
C16 C 1.4270(3) 0.8271(2) 0.38831(18) 0.0419(8) Uani 1 1 d . . .
H16A H 1.4759 0.8876 0.3843 0.063 Uiso 1 1 calc R . .
H16B H 1.4958 0.7763 0.3948 0.063 Uiso 1 1 calc R . .
H16C H 1.3639 0.8281 0.4341 0.063 Uiso 1 1 calc R . .
C17 C 1.0063(3) 1.22698(18) 0.10483(15) 0.0236(5) Uani 1 1 d . . .
C18 C 1.1421(3) 1.2825(2) 0.11326(18) 0.0330(7) Uani 1 1 d . . .
H18A H 1.1928 1.2819 0.0628 0.049 Uiso 1 1 calc R . .
H18C H 1.2005 1.2537 0.1544 0.049 Uiso 1 1 calc R . .
H18B H 1.1205 1.3477 0.1280 0.049 Uiso 1 1 calc R . .
C19 C 0.7529(3) 0.94411(19) -0.01998(16) 0.0291(6) Uani 1 1 d . . .
H19A H 0.8202 0.9721 -0.0579 0.035 Uiso 1 1 calc R . .
H19B H 0.6594 0.9427 -0.0455 0.035 Uiso 1 1 calc R . .
C20 C 0.7987(3) 0.8429(2) 0.00015(17) 0.0344(7) Uani 1 1 d . . .
H20B H 0.8915 0.8448 0.0264 0.041 Uiso 1 1 calc R . .
H20A H 0.7308 0.8152 0.0379 0.041 Uiso 1 1 calc R . .
C21 C 0.8236(4) 0.6807(2) -0.0463(2) 0.0617(10) Uani 1 1 d . . .
H21A H 0.9081 0.6741 -0.0138 0.093 Uiso 1 1 calc R . .
H21B H 0.8315 0.6405 -0.0932 0.093 Uiso 1 1 calc R . .
H21C H 0.7413 0.6618 -0.0154 0.093 Uiso 1 1 calc R . .
C22 C 0.9290(3) 0.8087(3) -0.1222(2) 0.0512(9) Uani 1 1 d . . .
H22A H 0.9164 0.8735 -0.1409 0.077 Uiso 1 1 calc R . .
H22C H 0.9345 0.7661 -0.1677 0.077 Uiso 1 1 calc R . .
H22B H 1.0159 0.8044 -0.0914 0.077 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
S1 C9 1.766(2) . ?
S1 C1 1.841(2) . ?
O1 C13 1.373(3) . ?
O1 C16 1.432(3) . ?
O2 C17 1.352(3) . ?
O2 C2 1.438(3) . ?
O3 C17 1.203(3) . ?
O4 C3 1.217(3) . ?
N1 C3 1.370(3) . ?
N1 C4 1.435(3) . ?
N1 C19 1.469(3) . ?
N2 C22 1.459(4) . ?
N2 C20 1.463(3) . ?
N2 C21 1.468(4) . ?
C1 C10 1.515(3) . ?
C1 C2 1.529(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.524(4) . ?
C2 H2 0.9800 . ?
C4 C5 1.395(3) . ?
C4 C9 1.397(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.395(3) . ?
C8 H8 0.9300 . ?
C10 C11 1.388(3) . ?
C10 C15 1.404(4) . ?
C11 C12 1.394(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(3) . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.492(3) . ?
C18 H18A 0.9600 . ?
C18 H18C 0.9600 . ?
C18 H18B 0.9600 . ?
C19 C20 1.508(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20A 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22C 0.9600 . ?
C22 H22B 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
C9 S1 C1 104.21(11) . . ?
C13 O1 C16 117.7(2) . . ?
C17 O2 C2 114.97(18) . . ?
C3 N1 C4 124.1(2) . . ?
C3 N1 C19 116.41(18) . . ?
C4 N1 C19 119.50(18) . . ?
C22 N2 C20 111.1(2) . . ?
C22 N2 C21 109.5(3) . . ?
C20 N2 C21 109.4(2) . . ?
C10 C1 C2 116.79(19) . . ?
C10 C1 S1 105.96(17) . . ?
C2 C1 S1 109.98(16) . . ?
C10 C1 H1 107.9 . . ?
C2 C1 H1 107.9 . . ?
S1 C1 H1 107.9 . . ?
O2 C2 C3 109.29(19) . . ?
O2 C2 C1 104.85(18) . . ?
C3 C2 C1 115.0(2) . . ?
O2 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
O4 C3 N1 122.1(2) . . ?
O4 C3 C2 121.2(2) . . ?
N1 C3 C2 116.68(19) . . ?
C5 C4 C9 119.0(2) . . ?
C5 C4 N1 119.2(2) . . ?
C9 C4 N1 121.9(2) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 119.7(2) . . ?
C8 C9 S1 117.50(19) . . ?
C4 C9 S1 122.29(17) . . ?
C11 C10 C15 117.9(2) . . ?
C11 C10 C1 120.4(2) . . ?
C15 C10 C1 121.6(2) . . ?
C10 C11 C12 121.5(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
O1 C13 C12 125.3(2) . . ?
O1 C13 C14 114.9(2) . . ?
C12 C13 C14 119.8(2) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 122.9(2) . . ?
O3 C17 C18 125.7(2) . . ?
O2 C17 C18 111.4(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
N1 C19 C20 111.0(2) . . ?
N1 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
N1 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
N2 C20 C19 112.5(2) . . ?
N2 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
N2 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
H20B C20 H20A 107.8 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22C C22 H22B 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
C9 S1 C1 C10 -154.91(17) . . . . ?
C9 S1 C1 C2 -27.8(2) . . . . ?
C17 O2 C2 C3 67.5(2) . . . . ?
C17 O2 C2 C1 -168.75(19) . . . . ?
C10 C1 C2 O2 -54.8(3) . . . . ?
S1 C1 C2 O2 -175.60(15) . . . . ?
C10 C1 C2 C3 65.2(3) . . . . ?
S1 C1 C2 C3 -55.6(2) . . . . ?
C4 N1 C3 O4 -177.9(2) . . . . ?
C19 N1 C3 O4 1.2(4) . . . . ?
C4 N1 C3 C2 1.4(3) . . . . ?
C19 N1 C3 C2 -179.5(2) . . . . ?
O2 C2 C3 O4 20.4(3) . . . . ?
C1 C2 C3 O4 -97.2(3) . . . . ?
O2 C2 C3 N1 -158.9(2) . . . . ?
C1 C2 C3 N1 83.5(3) . . . . ?
C3 N1 C4 C5 131.1(3) . . . . ?
C19 N1 C4 C5 -48.0(3) . . . . ?
C3 N1 C4 C9 -49.8(4) . . . . ?
C19 N1 C4 C9 131.1(3) . . . . ?
C9 C4 C5 C6 -1.5(4) . . . . ?
N1 C4 C5 C6 177.7(2) . . . . ?
C4 C5 C6 C7 1.8(4) . . . . ?
C5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 -2.3(4) . . . . ?
C7 C8 C9 C4 2.5(4) . . . . ?
C7 C8 C9 S1 -169.8(2) . . . . ?
C5 C4 C9 C8 -0.6(4) . . . . ?
N1 C4 C9 C8 -179.8(2) . . . . ?
C5 C4 C9 S1 171.35(19) . . . . ?
N1 C4 C9 S1 -7.8(4) . . . . ?
C1 S1 C9 C8 -121.1(2) . . . . ?
C1 S1 C9 C4 66.8(2) . . . . ?
C2 C1 C10 C11 113.1(3) . . . . ?
S1 C1 C10 C11 -124.0(2) . . . . ?
C2 C1 C10 C15 -70.1(3) . . . . ?
S1 C1 C10 C15 52.7(3) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C1 C10 C11 C12 176.3(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C16 O1 C13 C12 7.0(4) . . . . ?
C16 O1 C13 C14 -173.5(2) . . . . ?
C11 C12 C13 O1 179.7(2) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
O1 C13 C14 C15 179.9(2) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 C10 0.3(4) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C1 C10 C15 C14 -176.5(2) . . . . ?
C2 O2 C17 O3 2.0(3) . . . . ?
C2 O2 C17 C18 -178.9(2) . . . . ?
C3 N1 C19 C20 79.4(3) . . . . ?
C4 N1 C19 C20 -101.5(3) . . . . ?
C22 N2 C20 C19 70.6(3) . . . . ?
C21 N2 C20 C19 -168.4(3) . . . . ?
N1 C19 C20 N2 -179.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_dil-asa
_database_code_depnum_ccdc_archive 'CCDC 1056495'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Dilteazem  acetylsalicylate hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 N2 O4 S, C9 H7 O4, H2 O'
_chemical_formula_sum            'C31 H36 N2 O9 S'
_chemical_formula_weight         612.68

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_chemical_absolute_configuration rm

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

_cell_length_a                   9.9411(4)
_cell_length_b                   10.7606(3)
_cell_length_c                   28.5926(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3058.61(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    152796
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      30.034

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.163
_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      173(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  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8725
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.2030
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         30.03
_reflns_number_total             8725
_reflns_number_gt                4302
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;

_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)+(0.0000P)²+3.5075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(13)
_refine_ls_number_reflns         8725
_refine_ls_number_parameters     405
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2268
_refine_ls_R_factor_gt           0.0984
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.67793(11) 0.01126(11) 0.05627(4) 0.0300(3) Uani 1 1 d . . .
O1 O 0.0718(3) -0.1265(3) -0.01069(12) 0.0446(10) Uani 1 1 d . . .
O2 O 0.4258(3) 0.3039(3) 0.06456(10) 0.0283(7) Uani 1 1 d . . .
O3 O 0.4905(3) 0.4460(3) 0.11794(10) 0.0317(8) Uani 1 1 d . . .
O4 O 0.4073(3) 0.1709(3) 0.14379(11) 0.0298(8) Uani 1 1 d . . .
O5 O 1.1952(3) -0.3070(3) 0.21687(11) 0.0372(8) Uani 1 1 d . . .
O6 O 1.1840(3) -0.5056(3) 0.19347(10) 0.0348(8) Uani 1 1 d . . .
O7 O 1.0657(3) -0.1726(3) 0.14757(11) 0.0311(8) Uani 1 1 d . . .
O8 O 0.9865(3) -0.0835(3) 0.21294(13) 0.0495(10) Uani 1 1 d . . .
O9 O 1.4462(4) -0.3067(4) 0.17232(17) 0.0622(13) Uani 1 1 d . . .
N1 N 0.6334(3) 0.1429(3) 0.15044(13) 0.0268(9) Uani 1 1 d . . .
N2 N 0.6465(3) -0.0981(4) 0.24646(13) 0.0238(9) Uani 1 1 d D . .
C1 C 0.5501(4) 0.1279(4) 0.03993(15) 0.0272(11) Uani 1 1 d . . .
H1 H 0.5807 0.1681 0.0111 0.033 Uiso 1 1 calc R . .
C2 C 0.5396(4) 0.2286(4) 0.07758(14) 0.0219(10) Uani 1 1 d . . .
H2 H 0.6210 0.2799 0.0769 0.026 Uiso 1 1 calc R . .
C3 C 0.5203(5) 0.1774(4) 0.12671(15) 0.0258(10) Uani 1 1 d . . .
C4 C 0.7667(4) 0.1517(4) 0.13080(17) 0.0261(11) Uani 1 1 d . . .
C5 C 0.8660(5) 0.2112(4) 0.15664(18) 0.0349(12) Uani 1 1 d . . .
H5 H 0.8453 0.2451 0.1857 0.042 Uiso 1 1 calc R . .
C6 C 0.9957(5) 0.2202(5) 0.13937(19) 0.0428(14) Uani 1 1 d . . .
H6 H 1.0618 0.2602 0.1568 0.051 Uiso 1 1 calc R . .
C7 C 1.0270(5) 0.1699(5) 0.0964(2) 0.0406(14) Uani 1 1 d . . .
H7 H 1.1143 0.1760 0.0849 0.049 Uiso 1 1 calc R . .
C8 C 0.9295(4) 0.1104(5) 0.07024(18) 0.0354(12) Uani 1 1 d . . .
H8 H 0.9510 0.0766 0.0413 0.042 Uiso 1 1 calc R . .
C9 C 0.7986(4) 0.1013(4) 0.08747(16) 0.0271(11) Uani 1 1 d . . .
C10 C 0.4223(4) 0.0574(4) 0.02850(15) 0.0250(10) Uani 1 1 d . . .
C11 C 0.3628(5) 0.0760(5) -0.01511(16) 0.0341(12) Uani 1 1 d . . .
H11 H 0.4012 0.1310 -0.0363 0.041 Uiso 1 1 calc R . .
C12 C 0.2452(4) 0.0115(5) -0.02681(17) 0.0362(12) Uani 1 1 d . . .
H12 H 0.2059 0.0238 -0.0560 0.043 Uiso 1 1 calc R . .
C13 C 0.1867(5) -0.0707(5) 0.00466(17) 0.0343(12) Uani 1 1 d . . .
C14 C 0.2468(4) -0.0888(5) 0.04774(16) 0.0326(12) Uani 1 1 d . . .
H14 H 0.2079 -0.1430 0.0692 0.039 Uiso 1 1 calc R . .
C15 C 0.3647(4) -0.0268(4) 0.05924(16) 0.0319(11) Uani 1 1 d . . .
H15 H 0.4056 -0.0419 0.0879 0.038 Uiso 1 1 calc R . .
C16 C 0.0176(5) -0.2223(6) 0.0180(2) 0.0607(18) Uani 1 1 d . . .
H16A H 0.0837 -0.2863 0.0223 0.091 Uiso 1 1 calc R . .
H16B H -0.0607 -0.2567 0.0032 0.091 Uiso 1 1 calc R . .
H16C H -0.0068 -0.1883 0.0479 0.091 Uiso 1 1 calc R . .
C17 C 0.4108(4) 0.4099(4) 0.08858(16) 0.0262(10) Uani 1 1 d . . .
C18 C 0.2841(4) 0.4776(5) 0.07566(18) 0.0420(14) Uani 1 1 d . . .
H18A H 0.2133 0.4541 0.0967 0.063 Uiso 1 1 calc R . .
H18B H 0.2591 0.4566 0.0442 0.063 Uiso 1 1 calc R . .
H18C H 0.2990 0.5656 0.0778 0.063 Uiso 1 1 calc R . .
C19 C 0.6188(4) 0.0920(4) 0.19789(15) 0.0280(11) Uani 1 1 d . . .
H19A H 0.5272 0.1042 0.2086 0.034 Uiso 1 1 calc R . .
H19B H 0.6785 0.1358 0.2191 0.034 Uiso 1 1 calc R . .
C20 C 0.6522(4) -0.0459(4) 0.19836(15) 0.0255(11) Uani 1 1 d . . .
H20A H 0.5889 -0.0899 0.1786 0.031 Uiso 1 1 calc R . .
H20B H 0.7416 -0.0582 0.1856 0.031 Uiso 1 1 calc R . .
C21 C 0.5082(4) -0.0962(5) 0.26700(15) 0.0311(12) Uani 1 1 d . . .
H21A H 0.4763 -0.0121 0.2684 0.047 Uiso 1 1 calc R . .
H21B H 0.5106 -0.1306 0.2980 0.047 Uiso 1 1 calc R . .
H21C H 0.4488 -0.1447 0.2478 0.047 Uiso 1 1 calc R . .
C22 C 0.7014(5) -0.2276(4) 0.24799(16) 0.0315(12) Uani 1 1 d . . .
H22A H 0.6967 -0.2586 0.2794 0.047 Uiso 1 1 calc R . .
H22B H 0.7934 -0.2271 0.2378 0.047 Uiso 1 1 calc R . .
H22C H 0.6494 -0.2801 0.2278 0.047 Uiso 1 1 calc R . .
C23 C 1.1382(4) -0.3968(5) 0.19702(16) 0.0303(12) Uani 1 1 d . . .
C24 C 1.0013(4) -0.3744(4) 0.17485(15) 0.0255(11) Uani 1 1 d . . .
C25 C 0.9053(4) -0.4687(5) 0.17678(16) 0.0319(12) Uani 1 1 d . . .
H25 H 0.9244 -0.5421 0.1926 0.038 Uiso 1 1 calc R . .
C26 C 0.7805(5) -0.4537(5) 0.15502(18) 0.0386(13) Uani 1 1 d . . .
H26 H 0.7160 -0.5160 0.1570 0.046 Uiso 1 1 calc R . .
C27 C 0.7533(4) -0.3457(5) 0.13057(17) 0.0341(13) Uani 1 1 d . . .
H27 H 0.6714 -0.3365 0.1152 0.041 Uiso 1 1 calc R . .
C28 C 0.8467(4) -0.2526(5) 0.12889(15) 0.0316(12) Uani 1 1 d . . .
H28 H 0.8277 -0.1795 0.1129 0.038 Uiso 1 1 calc R . .
C29 C 0.9688(4) -0.2671(4) 0.15087(16) 0.0270(11) Uani 1 1 d . . .
C30 C 1.0744(5) -0.0938(5) 0.18449(19) 0.0353(12) Uani 1 1 d . . .
C31 C 1.2030(4) -0.0218(5) 0.18423(18) 0.0452(14) Uani 1 1 d . . .
H31A H 1.2095 0.0264 0.2124 0.068 Uiso 1 1 calc R . .
H31B H 1.2045 0.0327 0.1576 0.068 Uiso 1 1 calc R . .
H31C H 1.2777 -0.0782 0.1825 0.068 Uiso 1 1 calc R . .
H9A H 1.438(6) -0.379(6) 0.153(2) 0.08(2) Uiso 1 1 d . . .
H2A H 0.696(5) -0.051(4) 0.2655(16) 0.07(2) Uiso 1 1 d D . .
H9B H 1.369(6) -0.309(6) 0.184(2) 0.08(2) Uiso 1 1 d . . .


_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 C9 1.781(5) . ?
S1 C1 1.846(4) . ?
O1 C13 1.363(5) . ?
O1 C16 1.423(6) . ?
O2 C17 1.340(5) . ?
O2 C2 1.440(5) . ?
O3 C17 1.218(5) . ?
O4 C3 1.227(5) . ?
O5 C23 1.256(5) . ?
O6 C23 1.261(6) . ?
O7 C30 1.356(6) . ?
O7 C29 1.405(5) . ?
O8 C30 1.199(5) . ?
O9 H9A 0.96(6) . ?
O9 H9B 0.84(6) . ?
N1 C3 1.365(5) . ?
N1 C4 1.443(5) . ?
N1 C19 1.470(5) . ?
N2 C20 1.487(5) . ?
N2 C21 1.495(5) . ?
N2 C22 1.497(6) . ?
N2 H2A 0.894(19) . ?
C1 C10 1.515(6) . ?
C1 C2 1.531(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.521(6) . ?
C2 H2 0.9800 . ?
C4 C5 1.389(6) . ?
C4 C9 1.389(6) . ?
C5 C6 1.384(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.395(6) . ?
C8 H8 0.9300 . ?
C10 C15 1.386(6) . ?
C10 C11 1.394(6) . ?
C11 C12 1.400(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(6) . ?
C14 C15 1.389(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.501(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.520(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.521(6) . ?
C24 C29 1.381(6) . ?
C24 C25 1.395(6) . ?
C25 C26 1.397(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.382(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.367(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.376(6) . ?
C28 H28 0.9300 . ?
C30 C31 1.495(6) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 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
C9 S1 C1 102.7(2) . . ?
C13 O1 C16 116.8(4) . . ?
C17 O2 C2 115.7(3) . . ?
C30 O7 C29 116.4(4) . . ?
H9A O9 H9B 97(5) . . ?
C3 N1 C4 123.0(4) . . ?
C3 N1 C19 118.6(3) . . ?
C4 N1 C19 118.3(3) . . ?
C20 N2 C21 113.1(3) . . ?
C20 N2 C22 111.4(3) . . ?
C21 N2 C22 109.7(4) . . ?
C20 N2 H2A 109(4) . . ?
C21 N2 H2A 105(4) . . ?
C22 N2 H2A 108(4) . . ?
C10 C1 C2 116.6(3) . . ?
C10 C1 S1 106.9(3) . . ?
C2 C1 S1 110.5(3) . . ?
C10 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
S1 C1 H1 107.5 . . ?
O2 C2 C3 110.1(3) . . ?
O2 C2 C1 105.7(3) . . ?
C3 C2 C1 113.7(4) . . ?
O2 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
O4 C3 N1 122.7(4) . . ?
O4 C3 C2 120.3(4) . . ?
N1 C3 C2 117.0(4) . . ?
C5 C4 C9 119.5(4) . . ?
C5 C4 N1 118.4(4) . . ?
C9 C4 N1 122.1(4) . . ?
C6 C5 C4 120.3(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.1(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.4(5) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 120.0(4) . . ?
C4 C9 S1 120.4(3) . . ?
C8 C9 S1 119.3(4) . . ?
C15 C10 C11 119.1(4) . . ?
C15 C10 C1 122.5(4) . . ?
C11 C10 C1 118.5(4) . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 C14 125.9(5) . . ?
O1 C13 C12 115.0(4) . . ?
C14 C13 C12 119.1(4) . . ?
C13 C14 C15 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.8(4) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 123.5(4) . . ?
O3 C17 C18 124.1(4) . . ?
O2 C17 C18 112.4(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 110.5(4) . . ?
N1 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
N2 C20 C19 111.6(4) . . ?
N2 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
N2 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 O6 126.1(4) . . ?
O5 C23 C24 118.0(4) . . ?
O6 C23 C24 115.9(4) . . ?
C29 C24 C25 117.9(4) . . ?
C29 C24 C23 123.3(4) . . ?
C25 C24 C23 118.7(4) . . ?
C24 C25 C26 120.4(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 119.7(4) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C28 C27 C26 120.1(4) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.0(5) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C24 121.9(4) . . ?
C28 C29 O7 119.5(4) . . ?
C24 C29 O7 118.6(4) . . ?
O8 C30 O7 122.6(4) . . ?
O8 C30 C31 125.4(5) . . ?
O7 C30 C31 112.0(4) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C9 S1 C1 C10 -160.7(3) . . . . ?
C9 S1 C1 C2 -32.8(3) . . . . ?
C17 O2 C2 C3 67.2(4) . . . . ?
C17 O2 C2 C1 -169.7(3) . . . . ?
C10 C1 C2 O2 -49.9(5) . . . . ?
S1 C1 C2 O2 -172.3(3) . . . . ?
C10 C1 C2 C3 70.9(5) . . . . ?
S1 C1 C2 C3 -51.5(4) . . . . ?
C4 N1 C3 O4 -179.2(4) . . . . ?
C19 N1 C3 O4 2.0(7) . . . . ?
C4 N1 C3 C2 -0.7(6) . . . . ?
C19 N1 C3 C2 -179.5(4) . . . . ?
O2 C2 C3 O4 21.1(6) . . . . ?
C1 C2 C3 O4 -97.2(5) . . . . ?
O2 C2 C3 N1 -157.4(4) . . . . ?
C1 C2 C3 N1 84.2(5) . . . . ?
C3 N1 C4 C5 129.1(5) . . . . ?
C19 N1 C4 C5 -52.1(6) . . . . ?
C3 N1 C4 C9 -51.9(7) . . . . ?
C19 N1 C4 C9 126.9(4) . . . . ?
C9 C4 C5 C6 0.0(7) . . . . ?
N1 C4 C5 C6 179.1(4) . . . . ?
C4 C5 C6 C7 -0.1(7) . . . . ?
C5 C6 C7 C8 0.1(8) . . . . ?
C6 C7 C8 C9 0.0(7) . . . . ?
C5 C4 C9 C8 0.1(7) . . . . ?
N1 C4 C9 C8 -179.0(4) . . . . ?
C5 C4 C9 S1 173.7(4) . . . . ?
N1 C4 C9 S1 -5.3(6) . . . . ?
C7 C8 C9 C4 -0.1(7) . . . . ?
C7 C8 C9 S1 -173.8(4) . . . . ?
C1 S1 C9 C4 68.5(4) . . . . ?
C1 S1 C9 C8 -117.8(4) . . . . ?
C2 C1 C10 C15 -70.4(5) . . . . ?
S1 C1 C10 C15 53.8(5) . . . . ?
C2 C1 C10 C11 111.2(5) . . . . ?
S1 C1 C10 C11 -124.6(4) . . . . ?
C15 C10 C11 C12 1.1(7) . . . . ?
C1 C10 C11 C12 179.6(4) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C16 O1 C13 C14 -7.6(7) . . . . ?
C16 O1 C13 C12 172.6(4) . . . . ?
C11 C12 C13 O1 179.3(4) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
O1 C13 C14 C15 179.6(4) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C11 C10 C15 C14 -2.3(6) . . . . ?
C1 C10 C15 C14 179.4(4) . . . . ?
C13 C14 C15 C10 2.0(7) . . . . ?
C2 O2 C17 O3 3.8(6) . . . . ?
C2 O2 C17 C18 -175.3(3) . . . . ?
C3 N1 C19 C20 110.1(4) . . . . ?
C4 N1 C19 C20 -68.7(5) . . . . ?
C21 N2 C20 C19 65.4(5) . . . . ?
C22 N2 C20 C19 -170.5(3) . . . . ?
N1 C19 C20 N2 176.4(3) . . . . ?
O5 C23 C24 C29 39.2(6) . . . . ?
O6 C23 C24 C29 -140.6(4) . . . . ?
O5 C23 C24 C25 -143.9(4) . . . . ?
O6 C23 C24 C25 36.3(6) . . . . ?
C29 C24 C25 C26 -0.1(7) . . . . ?
C23 C24 C25 C26 -177.2(4) . . . . ?
C24 C25 C26 C27 1.4(7) . . . . ?
C25 C26 C27 C28 -2.0(7) . . . . ?
C26 C27 C28 C29 1.1(7) . . . . ?
C27 C28 C29 C24 0.3(7) . . . . ?
C27 C28 C29 O7 177.8(4) . . . . ?
C25 C24 C29 C28 -0.8(7) . . . . ?
C23 C24 C29 C28 176.2(4) . . . . ?
C25 C24 C29 O7 -178.4(4) . . . . ?
C23 C24 C29 O7 -1.4(6) . . . . ?
C30 O7 C29 C28 99.0(5) . . . . ?
C30 O7 C29 C24 -83.3(5) . . . . ?
C29 O7 C30 O8 -17.9(7) . . . . ?
C29 O7 C30 C31 163.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.071


####################################################################### 
# 
# 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_dil_nia
_database_code_depnum_ccdc_archive 'CCDC 1056496'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Diltiazem nicotinate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H27 N2 O4 S, C6 H4 N O2'
_chemical_formula_sum            'C28 H31 N3 O6 S'
_chemical_formula_weight         537.62

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_chemical_absolute_configuration rmad

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

_cell_length_a                   8.7897(2)
_cell_length_b                   6.17260(10)
_cell_length_c                   25.1531(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.5255(11)
_cell_angle_gamma                90.00
_cell_volume                     1364.21(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15036
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      30.034

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.165
_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      173(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  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7311
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1053
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         29.97
_reflns_number_total             7311
_reflns_number_gt                4922
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_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)+(0.0272P)²+0.4688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(9)
_refine_ls_number_reflns         7311
_refine_ls_number_parameters     351
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.60388(9) 0.14628(12) 0.64639(3) 0.03146(18) Uani 1 1 d . . .
O1 O 0.1642(2) -0.0403(3) 0.43849(7) 0.0311(5) Uani 1 1 d . . .
O2 O 0.2423(2) 0.5449(3) 0.63662(7) 0.0272(4) Uani 1 1 d . . .
O3 O 0.1788(2) 0.6368(3) 0.71945(7) 0.0315(5) Uani 1 1 d . . .
O4 O 0.1859(2) 0.1691(3) 0.68960(7) 0.0274(4) Uani 1 1 d . . .
O5 O 0.4101(3) 0.9115(3) 0.90313(8) 0.0380(5) Uani 1 1 d . . .
O6 O 0.3269(3) 0.5710(4) 0.90070(11) 0.0537(7) Uani 1 1 d . . .
N1 N 0.3993(3) 0.2086(3) 0.74148(8) 0.0248(5) Uani 1 1 d . . .
N2 N 0.1617(3) 0.0359(4) 0.85708(9) 0.0259(5) Uani 1 1 d . . .
N3 N 0.8416(3) 0.7267(4) 0.95240(11) 0.0431(7) Uani 1 1 d . . .
C1 C 0.4690(3) 0.3433(4) 0.61687(10) 0.0257(6) Uani 1 1 d . . .
H1 H 0.5280 0.4646 0.6029 0.031 Uiso 1 1 calc R . .
C2 C 0.3685(3) 0.4313(4) 0.66105(10) 0.0243(6) Uani 1 1 d . . .
H2 H 0.4285 0.5346 0.6825 0.029 Uiso 1 1 calc R . .
C3 C 0.3089(3) 0.2546(4) 0.69805(10) 0.0238(6) Uani 1 1 d . . .
C4 C 0.5499(3) 0.2890(4) 0.74869(11) 0.0264(6) Uani 1 1 d . . .
C5 C 0.5961(4) 0.3810(5) 0.79683(11) 0.0343(7) Uani 1 1 d . . .
H5 H 0.5272 0.3926 0.8241 0.041 Uiso 1 1 calc R . .
C6 C 0.7432(4) 0.4555(5) 0.80477(12) 0.0385(8) Uani 1 1 d . . .
H6 H 0.7730 0.5157 0.8373 0.046 Uiso 1 1 calc R . .
C7 C 0.8452(4) 0.4404(5) 0.76452(12) 0.0370(8) Uani 1 1 d . . .
H7 H 0.9439 0.4920 0.7697 0.044 Uiso 1 1 calc R . .
C8 C 0.8019(4) 0.3492(5) 0.71655(12) 0.0334(7) Uani 1 1 d . . .
H8 H 0.8719 0.3382 0.6896 0.040 Uiso 1 1 calc R . .
C9 C 0.6548(3) 0.2737(4) 0.70798(11) 0.0280(6) Uani 1 1 d . . .
C10 C 0.3869(3) 0.2336(4) 0.57018(10) 0.0242(6) Uani 1 1 d . . .
C11 C 0.3219(3) 0.0300(4) 0.57440(11) 0.0266(6) Uani 1 1 d . . .
H11 H 0.3289 -0.0428 0.6067 0.032 Uiso 1 1 calc R . .
C12 C 0.2465(3) -0.0679(4) 0.53155(11) 0.0260(6) Uani 1 1 d . . .
H12 H 0.2036 -0.2046 0.5353 0.031 Uiso 1 1 calc R . .
C13 C 0.2357(3) 0.0391(4) 0.48323(11) 0.0234(6) Uani 1 1 d . . .
C14 C 0.3039(3) 0.2422(4) 0.47790(11) 0.0253(6) Uani 1 1 d . . .
H14 H 0.2992 0.3134 0.4453 0.030 Uiso 1 1 calc R . .
C15 C 0.3783(3) 0.3375(4) 0.52104(10) 0.0230(6) Uani 1 1 d . . .
H15 H 0.4231 0.4728 0.5172 0.028 Uiso 1 1 calc R . .
C16 C 0.0681(4) -0.2251(5) 0.44398(12) 0.0361(7) Uani 1 1 d . . .
H16A H 0.1295 -0.3510 0.4510 0.054 Uiso 1 1 calc R . .
H16B H 0.0093 -0.2463 0.4117 0.054 Uiso 1 1 calc R . .
H16C H 0.0009 -0.2022 0.4729 0.054 Uiso 1 1 calc R . .
C17 C 0.1518(3) 0.6443(5) 0.67249(10) 0.0263(6) Uani 1 1 d . . .
C18 C 0.0205(3) 0.7603(5) 0.64652(12) 0.0326(7) Uani 1 1 d . . .
H18A H -0.0590 0.7777 0.6716 0.049 Uiso 1 1 calc R . .
H18B H -0.0171 0.6777 0.6166 0.049 Uiso 1 1 calc R . .
H18C H 0.0532 0.9002 0.6346 0.049 Uiso 1 1 calc R . .
C19 C 0.3382(3) 0.0600(4) 0.78179(11) 0.0262(6) Uani 1 1 d . . .
H19A H 0.4205 0.0087 0.8050 0.031 Uiso 1 1 calc R . .
H19B H 0.2918 -0.0645 0.7643 0.031 Uiso 1 1 calc R . .
C20 C 0.2208(3) 0.1759(5) 0.81445(10) 0.0280(6) Uani 1 1 d . . .
H20A H 0.2663 0.3046 0.8303 0.034 Uiso 1 1 calc R . .
H20B H 0.1368 0.2216 0.7913 0.034 Uiso 1 1 calc R . .
C21 C 0.0682(4) -0.1463(5) 0.83605(12) 0.0392(8) Uani 1 1 d . . .
H21A H -0.0171 -0.0902 0.8158 0.059 Uiso 1 1 calc R . .
H21B H 0.0322 -0.2312 0.8651 0.059 Uiso 1 1 calc R . .
H21C H 0.1288 -0.2356 0.8136 0.059 Uiso 1 1 calc R . .
C22 C 0.0739(4) 0.1663(6) 0.89522(11) 0.0366(7) Uani 1 1 d . . .
H22A H 0.1394 0.2728 0.9117 0.055 Uiso 1 1 calc R . .
H22B H 0.0342 0.0729 0.9220 0.055 Uiso 1 1 calc R . .
H22C H -0.0087 0.2376 0.8766 0.055 Uiso 1 1 calc R . .
C23 C 0.4260(4) 0.7074(5) 0.91086(11) 0.0318(7) Uani 1 1 d . . .
C24 C 0.5792(3) 0.6370(5) 0.93273(10) 0.0300(6) Uani 1 1 d . . .
C25 C 0.7012(4) 0.7789(5) 0.93482(12) 0.0368(8) Uani 1 1 d . . .
H25 H 0.6845 0.9202 0.9232 0.044 Uiso 1 1 calc R . .
C26 C 0.8614(4) 0.5236(6) 0.96975(12) 0.0398(8) Uani 1 1 d . . .
H26 H 0.9578 0.4834 0.9824 0.048 Uiso 1 1 calc R . .
C27 C 0.7475(4) 0.3704(5) 0.97002(12) 0.0390(8) Uani 1 1 d . . .
H27 H 0.7668 0.2317 0.9829 0.047 Uiso 1 1 calc R . .
C28 C 0.6038(4) 0.4265(5) 0.95074(12) 0.0370(7) Uani 1 1 d . . .
H28 H 0.5254 0.3254 0.9498 0.044 Uiso 1 1 calc R . .
H2A H 0.256(5) -0.023(6) 0.8791(15) 0.070(12) Uiso 1 1 d . . .


_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 C9 1.784(3) . ?
S1 C1 1.841(3) . ?
O1 C13 1.365(3) . ?
O1 C16 1.429(3) . ?
O2 C17 1.364(3) . ?
O2 C2 1.437(3) . ?
O3 C17 1.199(3) . ?
O4 C3 1.217(3) . ?
O5 C23 1.281(3) . ?
O6 C23 1.233(4) . ?
N1 C3 1.363(3) . ?
N1 C4 1.421(4) . ?
N1 C19 1.479(3) . ?
N2 C20 1.482(3) . ?
N2 C21 1.483(4) . ?
N2 C22 1.485(4) . ?
N2 H2A 1.05(4) . ?
N3 C26 1.338(4) . ?
N3 C25 1.339(4) . ?
C1 C10 1.521(4) . ?
C1 C2 1.537(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.535(4) . ?
C2 H2 0.9800 . ?
C4 C5 1.389(4) . ?
C4 C9 1.399(4) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C10 C11 1.386(4) . ?
C10 C15 1.393(4) . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(4) . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.494(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.516(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.505(4) . ?
C24 C25 1.384(4) . ?
C24 C28 1.391(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.377(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(5) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C1 101.71(13) . . ?
C13 O1 C16 117.9(2) . . ?
C17 O2 C2 113.2(2) . . ?
C3 N1 C4 123.4(2) . . ?
C3 N1 C19 117.7(2) . . ?
C4 N1 C19 118.9(2) . . ?
C20 N2 C21 112.7(2) . . ?
C20 N2 C22 110.5(2) . . ?
C21 N2 C22 110.4(2) . . ?
C20 N2 H2A 107(2) . . ?
C21 N2 H2A 110(2) . . ?
C22 N2 H2A 105(2) . . ?
C26 N3 C25 116.4(3) . . ?
C10 C1 C2 116.4(2) . . ?
C10 C1 S1 107.73(19) . . ?
C2 C1 S1 108.55(17) . . ?
C10 C1 H1 107.9 . . ?
C2 C1 H1 107.9 . . ?
S1 C1 H1 107.9 . . ?
O2 C2 C3 109.5(2) . . ?
O2 C2 C1 108.4(2) . . ?
C3 C2 C1 113.5(2) . . ?
O2 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
O4 C3 N1 123.1(2) . . ?
O4 C3 C2 121.2(2) . . ?
N1 C3 C2 115.6(2) . . ?
C5 C4 C9 118.9(3) . . ?
C5 C4 N1 120.3(3) . . ?
C9 C4 N1 120.9(2) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 119.6(3) . . ?
C8 C9 S1 119.7(2) . . ?
C4 C9 S1 120.7(2) . . ?
C11 C10 C15 118.2(3) . . ?
C11 C10 C1 122.2(3) . . ?
C15 C10 C1 119.6(2) . . ?
C10 C11 C12 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
O1 C13 C12 124.9(2) . . ?
O1 C13 C14 115.6(2) . . ?
C12 C13 C14 119.5(3) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.9(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 122.0(3) . . ?
O3 C17 C18 125.4(3) . . ?
O2 C17 C18 112.6(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 110.1(2) . . ?
N1 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
N1 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.2 . . ?
N2 C20 C19 111.9(2) . . ?
N2 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O6 C23 O5 124.5(3) . . ?
O6 C23 C24 119.9(3) . . ?
O5 C23 C24 115.6(3) . . ?
C25 C24 C28 117.7(3) . . ?
C25 C24 C23 121.1(3) . . ?
C28 C24 C23 121.3(3) . . ?
N3 C25 C24 124.5(3) . . ?
N3 C25 H25 117.7 . . ?
C24 C25 H25 117.7 . . ?
N3 C26 C27 123.8(3) . . ?
N3 C26 H26 118.1 . . ?
C27 C26 H26 118.1 . . ?
C26 C27 C28 118.9(3) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C27 C28 C24 118.7(3) . . ?
C27 C28 H28 120.6 . . ?
C24 C28 H28 120.6 . . ?

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
C9 S1 C1 C10 -166.78(19) . . . . ?
C9 S1 C1 C2 -39.9(2) . . . . ?
C17 O2 C2 C3 60.4(3) . . . . ?
C17 O2 C2 C1 -175.2(2) . . . . ?
C10 C1 C2 O2 -45.2(3) . . . . ?
S1 C1 C2 O2 -166.91(17) . . . . ?
C10 C1 C2 C3 76.7(3) . . . . ?
S1 C1 C2 C3 -45.0(3) . . . . ?
C4 N1 C3 O4 172.7(2) . . . . ?
C19 N1 C3 O4 -4.7(4) . . . . ?
C4 N1 C3 C2 -10.1(4) . . . . ?
C19 N1 C3 C2 172.5(2) . . . . ?
O2 C2 C3 O4 28.4(3) . . . . ?
C1 C2 C3 O4 -92.8(3) . . . . ?
O2 C2 C3 N1 -148.8(2) . . . . ?
C1 C2 C3 N1 89.9(3) . . . . ?
C3 N1 C4 C5 132.5(3) . . . . ?
C19 N1 C4 C5 -50.1(4) . . . . ?
C3 N1 C4 C9 -48.6(4) . . . . ?
C19 N1 C4 C9 128.8(3) . . . . ?
C9 C4 C5 C6 -0.3(5) . . . . ?
N1 C4 C5 C6 178.6(3) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C7 C8 C9 C4 -0.5(4) . . . . ?
C7 C8 C9 S1 -177.5(2) . . . . ?
C5 C4 C9 C8 0.3(4) . . . . ?
N1 C4 C9 C8 -178.6(3) . . . . ?
C5 C4 C9 S1 177.2(2) . . . . ?
N1 C4 C9 S1 -1.7(4) . . . . ?
C1 S1 C9 C8 -112.7(3) . . . . ?
C1 S1 C9 C4 70.4(2) . . . . ?
C2 C1 C10 C11 -73.2(3) . . . . ?
S1 C1 C10 C11 48.9(3) . . . . ?
C2 C1 C10 C15 108.0(3) . . . . ?
S1 C1 C10 C15 -129.9(2) . . . . ?
C15 C10 C11 C12 -1.5(4) . . . . ?
C1 C10 C11 C12 179.7(3) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C16 O1 C13 C12 13.1(4) . . . . ?
C16 O1 C13 C14 -168.0(2) . . . . ?
C11 C12 C13 O1 -179.7(3) . . . . ?
C11 C12 C13 C14 1.5(4) . . . . ?
O1 C13 C14 C15 179.5(3) . . . . ?
C12 C13 C14 C15 -1.6(4) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C11 C10 C15 C14 1.4(4) . . . . ?
C1 C10 C15 C14 -179.8(3) . . . . ?
C2 O2 C17 O3 0.8(4) . . . . ?
C2 O2 C17 C18 -179.6(2) . . . . ?
C3 N1 C19 C20 -75.1(3) . . . . ?
C4 N1 C19 C20 107.4(3) . . . . ?
C21 N2 C20 C19 -68.3(3) . . . . ?
C22 N2 C20 C19 167.7(2) . . . . ?
N1 C19 C20 N2 -177.3(2) . . . . ?
O6 C23 C24 C25 167.4(3) . . . . ?
O5 C23 C24 C25 -11.3(4) . . . . ?
O6 C23 C24 C28 -11.6(4) . . . . ?
O5 C23 C24 C28 169.7(3) . . . . ?
C26 N3 C25 C24 -1.2(5) . . . . ?
C28 C24 C25 N3 0.8(5) . . . . ?
C23 C24 C25 N3 -178.2(3) . . . . ?
C25 N3 C26 C27 0.4(5) . . . . ?
N3 C26 C27 C28 0.8(5) . . . . ?
C26 C27 C28 C24 -1.2(4) . . . . ?
C25 C24 C28 C27 0.5(4) . . . . ?
C23 C24 C28 C27 179.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        29.97
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_dil-mal
_database_code_depnum_ccdc_archive 'CCDC 1056497'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Diltiazem L-Malate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H32 N2 O9 S'
_chemical_formula_weight         548.60

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'
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'
H H 0.0000 0.0000 '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'
_chemical_absolute_configuration rmad

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                   5.89620(10)
_cell_length_b                   9.0320(2)
_cell_length_c                   50.5074(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2689.75(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    30417
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    0.176
_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      173(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  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5177
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_sigmaI/netI    0.1519
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3184
_reflns_number_gt                1853
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;

_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)+(0.0492P)²+0.0000P] 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_number_reflns         3184
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.1156(2) 0.16250(15) 0.92614(3) 0.0298(4) Uani 1 1 d . . .
O1 O 0.2909(6) 0.5799(4) 1.03014(7) 0.0302(10) Uani 1 1 d . . .
O2 O -0.2900(5) 0.5189(4) 0.93079(7) 0.0233(9) Uani 1 1 d . . .
O3 O -0.3716(5) 0.5951(4) 0.88937(8) 0.0288(9) Uani 1 1 d . . .
O4 O 0.1051(5) 0.5690(4) 0.90418(7) 0.0250(9) Uani 1 1 d . . .
O5 O 0.7257(6) 0.2688(4) 0.77889(8) 0.0350(11) Uani 1 1 d . . .
O6 O 0.5669(5) 0.4424(4) 0.80400(8) 0.0279(10) Uani 1 1 d . . .
O7 O 0.1526(5) 0.3475(4) 0.79576(7) 0.0254(9) Uani 1 1 d . . .
H7A H 0.0271 0.3229 0.7903 0.038 Uiso 1 1 calc R . .
O8 O 0.4151(9) 0.4085(5) 0.71535(10) 0.0643(15) Uani 1 1 d . . .
O9 O 0.2450(7) 0.5283(4) 0.74691(8) 0.0416(11) Uani 1 1 d . . .
H9 H 0.2881 0.5343 0.7623 0.062 Uiso 1 1 calc R . .
N1 N 0.0515(6) 0.3672(4) 0.87819(9) 0.0211(10) Uani 1 1 d . . .
N2 N 0.2215(6) 0.6196(4) 0.82193(8) 0.0215(10) Uani 1 1 d . . .
H2A H 0.3027 0.5480 0.8135 0.026 Uiso 1 1 calc R . .
C1 C -0.0907(8) 0.2917(5) 0.94062(11) 0.0234(13) Uani 1 1 d . . .
H1 H -0.2193 0.2333 0.9471 0.028 Uiso 1 1 calc R . .
C2 C -0.1794(8) 0.3949(5) 0.91864(11) 0.0231(13) Uani 1 1 d . . .
H2 H -0.2913 0.3406 0.9081 0.028 Uiso 1 1 calc R . .
C3 C 0.0089(8) 0.4510(6) 0.90004(11) 0.0221(13) Uani 1 1 d . . .
C4 C -0.0331(8) 0.2191(5) 0.87509(12) 0.0267(14) Uani 1 1 d . . .
C5 C -0.1283(9) 0.1775(6) 0.85089(12) 0.0310(14) Uani 1 1 d . . .
H5 H -0.1408 0.2466 0.8373 0.037 Uiso 1 1 calc R . .
C6 C -0.2037(9) 0.0346(6) 0.84696(13) 0.0346(15) Uani 1 1 d . . .
H6 H -0.2674 0.0073 0.8308 0.042 Uiso 1 1 calc R . .
C7 C -0.1838(9) -0.0684(6) 0.86733(12) 0.0309(15) Uani 1 1 d . . .
H7 H -0.2341 -0.1650 0.8648 0.037 Uiso 1 1 calc R . .
C8 C -0.0891(9) -0.0269(6) 0.89131(13) 0.0341(15) Uani 1 1 d . . .
H8 H -0.0735 -0.0966 0.9047 0.041 Uiso 1 1 calc R . .
C9 C -0.0175(8) 0.1169(5) 0.89549(11) 0.0268(14) Uani 1 1 d . . .
C10 C 0.0176(8) 0.3667(5) 0.96432(11) 0.0234(13) Uani 1 1 d . . .
C11 C -0.0903(8) 0.3690(5) 0.98855(11) 0.0225(12) Uani 1 1 d . . .
H11 H -0.2301 0.3224 0.9904 0.027 Uiso 1 1 calc R . .
C12 C 0.0060(8) 0.4399(5) 1.01031(11) 0.0237(13) Uani 1 1 d . . .
H12 H -0.0680 0.4389 1.0266 0.028 Uiso 1 1 calc R . .
C13 C 0.2133(9) 0.5122(5) 1.00766(11) 0.0227(13) Uani 1 1 d . . .
C14 C 0.3266(8) 0.5076(5) 0.98375(12) 0.0243(13) Uani 1 1 d . . .
H14 H 0.4678 0.5524 0.9821 0.029 Uiso 1 1 calc R . .
C15 C 0.2298(8) 0.4362(6) 0.96234(11) 0.0267(14) Uani 1 1 d . . .
H15 H 0.3069 0.4343 0.9463 0.032 Uiso 1 1 calc R . .
C16 C 0.4776(8) 0.6793(6) 1.02738(13) 0.0378(16) Uani 1 1 d . . .
H16A H 0.5164 0.7194 1.0444 0.057 Uiso 1 1 calc R . .
H16B H 0.4364 0.7584 1.0156 0.057 Uiso 1 1 calc R . .
H16C H 0.6055 0.6271 1.0203 0.057 Uiso 1 1 calc R . .
C17 C -0.3840(8) 0.6149(6) 0.91286(13) 0.0268(14) Uani 1 1 d . . .
C18 C -0.5005(8) 0.7406(5) 0.92618(12) 0.0309(14) Uani 1 1 d . . .
H18A H -0.5557 0.8086 0.9131 0.046 Uiso 1 1 calc R . .
H18B H -0.3956 0.7905 0.9376 0.046 Uiso 1 1 calc R . .
H18C H -0.6256 0.7037 0.9364 0.046 Uiso 1 1 calc R . .
C19 C 0.1996(8) 0.4291(5) 0.85745(10) 0.0210(13) Uani 1 1 d . . .
H19A H 0.2491 0.3507 0.8457 0.025 Uiso 1 1 calc R . .
H19B H 0.3328 0.4731 0.8655 0.025 Uiso 1 1 calc R . .
C20 C 0.0726(8) 0.5452(5) 0.84184(10) 0.0212(13) Uani 1 1 d . . .
H20A H -0.0543 0.4991 0.8328 0.025 Uiso 1 1 calc R . .
H20B H 0.0124 0.6189 0.8539 0.025 Uiso 1 1 calc R . .
C21 C 0.3862(9) 0.7235(6) 0.83446(11) 0.0308(14) Uani 1 1 d . . .
H21C H 0.4803 0.7669 0.8210 0.046 Uiso 1 1 calc R . .
H21A H 0.4792 0.6703 0.8468 0.046 Uiso 1 1 calc R . .
H21B H 0.3050 0.8002 0.8436 0.046 Uiso 1 1 calc R . .
C22 C 0.0825(8) 0.6974(6) 0.80160(11) 0.0315(15) Uani 1 1 d . . .
H22C H -0.0202 0.6283 0.7935 0.047 Uiso 1 1 calc R . .
H22B H 0.1803 0.7384 0.7883 0.047 Uiso 1 1 calc R . .
H22A H -0.0023 0.7755 0.8099 0.047 Uiso 1 1 calc R . .
C23 C 0.5561(8) 0.3329(6) 0.78905(12) 0.0243(14) Uani 1 1 d . . .
C24 C 0.3232(7) 0.2684(6) 0.78167(11) 0.0216(13) Uani 1 1 d . . .
H24 H 0.3196 0.1656 0.7879 0.026 Uiso 1 1 calc R . .
C25 C 0.2819(8) 0.2666(5) 0.75135(10) 0.0249(13) Uani 1 1 d . . .
H25A H 0.3779 0.1904 0.7437 0.030 Uiso 1 1 calc R . .
H25B H 0.1259 0.2369 0.7483 0.030 Uiso 1 1 calc R . .
C26 C 0.3225(8) 0.4068(6) 0.73640(12) 0.0254(14) Uani 1 1 d . . .


_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 C9 1.783(6) . ?
S1 C1 1.837(5) . ?
O1 C13 1.369(6) . ?
O1 C16 1.427(6) . ?
O2 C17 1.371(6) . ?
O2 C2 1.434(6) . ?
O3 C17 1.202(6) . ?
O4 C3 1.226(6) . ?
O5 C23 1.264(6) . ?
O6 C23 1.246(6) . ?
O7 C24 1.424(6) . ?
O7 H7A 0.8200 . ?
O8 C26 1.195(6) . ?
O9 C26 1.302(6) . ?
O9 H9 0.8200 . ?
N1 C3 1.362(6) . ?
N1 C4 1.436(6) . ?
N1 C19 1.474(6) . ?
N2 C22 1.490(6) . ?
N2 C21 1.491(6) . ?
N2 C20 1.495(6) . ?
N2 H2A 0.9100 . ?
C1 C10 1.516(7) . ?
C1 C2 1.541(7) . ?
C1 H1 0.9800 . ?
C2 C3 1.540(7) . ?
C2 H2 0.9800 . ?
C4 C9 1.386(7) . ?
C4 C5 1.397(7) . ?
C5 C6 1.379(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(7) . ?
C8 H8 0.9300 . ?
C10 C11 1.380(7) . ?
C10 C15 1.404(7) . ?
C11 C12 1.393(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(7) . ?
C14 C15 1.382(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.488(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.510(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22A 0.9600 . ?
C23 C24 1.538(7) . ?
C24 C25 1.551(7) . ?
C24 H24 0.9800 . ?
C25 C26 1.494(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C1 101.6(2) . . ?
C13 O1 C16 117.3(4) . . ?
C17 O2 C2 113.3(4) . . ?
C24 O7 H7A 109.5 . . ?
C26 O9 H9 109.5 . . ?
C3 N1 C4 122.8(4) . . ?
C3 N1 C19 118.3(4) . . ?
C4 N1 C19 118.8(4) . . ?
C22 N2 C21 110.8(4) . . ?
C22 N2 C20 110.6(4) . . ?
C21 N2 C20 112.3(4) . . ?
C22 N2 H2A 107.6 . . ?
C21 N2 H2A 107.6 . . ?
C20 N2 H2A 107.6 . . ?
C10 C1 C2 116.2(4) . . ?
C10 C1 S1 108.6(3) . . ?
C2 C1 S1 108.8(4) . . ?
C10 C1 H1 107.6 . . ?
C2 C1 H1 107.6 . . ?
S1 C1 H1 107.6 . . ?
O2 C2 C3 109.4(4) . . ?
O2 C2 C1 108.6(4) . . ?
C3 C2 C1 113.2(4) . . ?
O2 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
O4 C3 N1 122.4(5) . . ?
O4 C3 C2 121.0(5) . . ?
N1 C3 C2 116.4(4) . . ?
C9 C4 C5 119.9(5) . . ?
C9 C4 N1 121.1(5) . . ?
C5 C4 N1 119.0(5) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 119.9(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.7(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C4 119.4(5) . . ?
C8 C9 S1 118.9(4) . . ?
C4 C9 S1 121.4(4) . . ?
C11 C10 C15 117.9(5) . . ?
C11 C10 C1 120.9(5) . . ?
C15 C10 C1 121.3(5) . . ?
C10 C11 C12 121.3(5) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.8(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O1 C13 C14 125.2(5) . . ?
O1 C13 C12 115.1(5) . . ?
C14 C13 C12 119.7(5) . . ?
C13 C14 C15 119.9(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 121.4(5) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O2 122.3(5) . . ?
O3 C17 C18 126.0(5) . . ?
O2 C17 C18 111.7(6) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C20 109.9(4) . . ?
N1 C19 H19A 109.7 . . ?
C20 C19 H19A 109.7 . . ?
N1 C19 H19B 109.7 . . ?
C20 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
N2 C20 C19 111.8(4) . . ?
N2 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
N2 C21 H21C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
H21C C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22C C22 H22B 109.5 . . ?
N2 C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?
O6 C23 O5 124.7(4) . . ?
O6 C23 C24 119.5(4) . . ?
O5 C23 C24 115.8(5) . . ?
O7 C24 C23 108.7(4) . . ?
O7 C24 C25 112.8(4) . . ?
C23 C24 C25 112.6(4) . . ?
O7 C24 H24 107.5 . . ?
C23 C24 H24 107.5 . . ?
C25 C24 H24 107.5 . . ?
C26 C25 C24 117.7(4) . . ?
C26 C25 H25A 107.9 . . ?
C24 C25 H25A 107.9 . . ?
C26 C25 H25B 107.9 . . ?
C24 C25 H25B 107.9 . . ?
H25A C25 H25B 107.2 . . ?
O8 C26 O9 120.8(6) . . ?
O8 C26 C25 122.3(5) . . ?
O9 C26 C25 116.9(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
C9 S1 C1 C10 -168.4(4) . . . . ?
C9 S1 C1 C2 -41.0(4) . . . . ?
C17 O2 C2 C3 58.7(5) . . . . ?
C17 O2 C2 C1 -177.4(4) . . . . ?
C10 C1 C2 O2 -41.6(6) . . . . ?
S1 C1 C2 O2 -164.5(3) . . . . ?
C10 C1 C2 C3 80.0(6) . . . . ?
S1 C1 C2 C3 -42.9(5) . . . . ?
C4 N1 C3 O4 170.2(4) . . . . ?
C19 N1 C3 O4 -6.9(7) . . . . ?
C4 N1 C3 C2 -13.8(7) . . . . ?
C19 N1 C3 C2 169.1(4) . . . . ?
O2 C2 C3 O4 28.0(6) . . . . ?
C1 C2 C3 O4 -93.2(6) . . . . ?
O2 C2 C3 N1 -148.1(4) . . . . ?
C1 C2 C3 N1 90.7(5) . . . . ?
C3 N1 C4 C9 -46.0(7) . . . . ?
C19 N1 C4 C9 131.1(5) . . . . ?
C3 N1 C4 C5 135.3(5) . . . . ?
C19 N1 C4 C5 -47.6(7) . . . . ?
C9 C4 C5 C6 -1.0(8) . . . . ?
N1 C4 C5 C6 177.7(5) . . . . ?
C4 C5 C6 C7 -0.2(8) . . . . ?
C5 C6 C7 C8 0.1(9) . . . . ?
C6 C7 C8 C9 1.2(9) . . . . ?
C7 C8 C9 C4 -2.4(8) . . . . ?
C7 C8 C9 S1 -177.1(4) . . . . ?
C5 C4 C9 C8 2.3(8) . . . . ?
N1 C4 C9 C8 -176.4(5) . . . . ?
C5 C4 C9 S1 176.8(4) . . . . ?
N1 C4 C9 S1 -1.9(7) . . . . ?
C1 S1 C9 C8 -114.7(5) . . . . ?
C1 S1 C9 C4 70.8(5) . . . . ?
C2 C1 C10 C11 108.7(5) . . . . ?
S1 C1 C10 C11 -128.3(4) . . . . ?
C2 C1 C10 C15 -71.1(6) . . . . ?
S1 C1 C10 C15 51.9(5) . . . . ?
C15 C10 C11 C12 0.9(7) . . . . ?
C1 C10 C11 C12 -178.9(4) . . . . ?
C10 C11 C12 C13 1.1(7) . . . . ?
C16 O1 C13 C14 14.1(7) . . . . ?
C16 O1 C13 C12 -167.9(4) . . . . ?
C11 C12 C13 O1 179.1(4) . . . . ?
C11 C12 C13 C14 -2.8(7) . . . . ?
O1 C13 C14 C15 -179.6(5) . . . . ?
C12 C13 C14 C15 2.5(7) . . . . ?
C13 C14 C15 C10 -0.4(8) . . . . ?
C11 C10 C15 C14 -1.3(7) . . . . ?
C1 C10 C15 C14 178.5(5) . . . . ?
C2 O2 C17 O3 -0.4(7) . . . . ?
C2 O2 C17 C18 179.0(4) . . . . ?
C3 N1 C19 C20 -74.9(6) . . . . ?
C4 N1 C19 C20 107.9(5) . . . . ?
C22 N2 C20 C19 162.5(4) . . . . ?
C21 N2 C20 C19 -73.2(5) . . . . ?
N1 C19 C20 N2 175.6(4) . . . . ?
O6 C23 C24 O7 -3.7(7) . . . . ?
O5 C23 C24 O7 176.9(5) . . . . ?
O6 C23 C24 C25 122.0(6) . . . . ?
O5 C23 C24 C25 -57.4(6) . . . . ?
O7 C24 C25 C26 72.9(6) . . . . ?
C23 C24 C25 C26 -50.5(6) . . . . ?
C24 C25 C26 O8 138.2(6) . . . . ?
C24 C25 C26 O9 -44.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.885
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.885
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.065

