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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_ks1136

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
Felodipine : 4,4'-bipyridine (1:1)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 Cl2 N O4, C10 H8 N2'
_chemical_formula_sum            'C28 H27 Cl2 N3 O4'
_chemical_formula_weight         540.42

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      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                   7.7589(10)
_cell_length_b                   9.2634(12)
_cell_length_c                   17.830(2)
_cell_angle_alpha                90.403(8)
_cell_angle_beta                 90.275(9)
_cell_angle_gamma                97.322(9)
_cell_volume                     1271.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2476
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.91

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker Nonius X8APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13673
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.664
_diffrn_reflns_theta_max         25.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.913
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.913
_reflns_number_total             4214
_reflns_number_gt                2594
_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 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2012)'
_computing_publication_material  SHELXL-2013

_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)+(0.0901P)²+5.3596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4214
_refine_ls_number_parameters     342
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.0957
_refine_ls_wR_factor_ref         0.2641
_refine_ls_wR_factor_gt          0.2379
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.091

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 -0.3585(3) 0.9119(2) 0.08844(14) 0.0636(7) Uani 1 1 d . . . . .
Cl2 Cl -0.4115(2) 0.6272(2) 0.18337(11) 0.0428(6) Uani 1 1 d . . . . .
O1 O -0.0070(7) 0.2549(6) 0.0731(3) 0.0479(14) Uani 1 1 d . . . . .
O2 O -0.2247(6) 0.3715(6) 0.1133(3) 0.0408(13) Uani 1 1 d . . . . .
O3 O -0.0292(6) 0.6465(6) 0.4292(3) 0.0388(13) Uani 1 1 d . . . . .
O4 O -0.2222(6) 0.6495(6) 0.3352(3) 0.0409(13) Uani 1 1 d . . . . .
N1 N 0.2496(7) 0.3979(6) 0.2810(3) 0.0320(14) Uani 1 1 d D . . . .
H1 H 0.353(4) 0.376(7) 0.295(4) 0.028(18) Uiso 1 1 d D . . . .
C1 C 0.1743(8) 0.3477(7) 0.2128(4) 0.0280(16) Uani 1 1 d . . . . .
C2 C 0.0226(8) 0.3892(7) 0.1902(4) 0.0264(15) Uani 1 1 d . . . . .
C3 C -0.0659(8) 0.5015(7) 0.2336(4) 0.0262(15) Uani 1 1 d . . . . .
H3 H -0.1911 0.4625 0.2401 0.031 Uiso 1 1 calc R U . . .
C4 C 0.0164(8) 0.5311(7) 0.3119(4) 0.0277(16) Uani 1 1 d . . . . .
C5 C 0.1676(8) 0.4782(7) 0.3306(4) 0.0282(16) Uani 1 1 d . . . . .
C6 C -0.0555(8) 0.6444(7) 0.1888(3) 0.0247(15) Uani 1 1 d . . . . .
C7 C 0.1059(8) 0.7131(7) 0.1709(3) 0.0275(16) Uani 1 1 d . . . . .
H7 H 0.2055 0.6723 0.1875 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1289(10) 0.8410(8) 0.1291(4) 0.0364(18) Uani 1 1 d . . . . .
H8 H 0.2423 0.8869 0.1179 0.044 Uiso 1 1 calc R U . . .
C9 C -0.0182(11) 0.9003(8) 0.1040(4) 0.0390(19) Uani 1 1 d . . . . .
H9 H -0.0055 0.9866 0.0750 0.047 Uiso 1 1 calc R U . . .
C10 C -0.1798(10) 0.8333(8) 0.1215(4) 0.0383(19) Uani 1 1 d . . . . .
C11 C -0.2027(9) 0.7056(7) 0.1636(4) 0.0313(17) Uani 1 1 d . . . . .
C12 C 0.2824(9) 0.2478(8) 0.1723(4) 0.0340(17) Uani 1 1 d . . . . .
H12A H 0.2388 0.2312 0.1209 0.051 Uiso 1 1 calc R U . . .
H12B H 0.2748 0.1547 0.1986 0.051 Uiso 1 1 calc R U . . .
H12C H 0.4038 0.2927 0.1712 0.051 Uiso 1 1 calc R U . . .
C13 C -0.0636(9) 0.3301(8) 0.1198(4) 0.0316(17) Uani 1 1 d . . . . .
C14 C -0.3168(10) 0.3363(9) 0.0419(4) 0.0412(19) Uani 1 1 d . . . . .
H14A H -0.2826 0.2454 0.0204 0.049 Uiso 1 1 calc R U . . .
H14B H -0.4439 0.3218 0.0503 0.049 Uiso 1 1 calc R U . . .
C15 C -0.2724(11) 0.4549(10) -0.0090(5) 0.059(3) Uani 1 1 d . . . . .
H15A H -0.3309 0.4320 -0.0573 0.088 Uiso 1 1 calc R U . . .
H15B H -0.1463 0.4695 -0.0165 0.088 Uiso 1 1 calc R U . . .
H15C H -0.3097 0.5438 0.0120 0.088 Uiso 1 1 calc R U . . .
C16 C -0.0720(8) 0.6119(8) 0.3653(4) 0.0287(16) Uani 1 1 d . . . . .
C17 C -0.3194(9) 0.7362(9) 0.3813(4) 0.044(2) Uani 1 1 d . . . . .
H17A H -0.4232 0.7571 0.3539 0.065 Uiso 1 1 calc R U . . .
H17B H -0.2474 0.8279 0.3942 0.065 Uiso 1 1 calc R U . . .
H17C H -0.3543 0.6833 0.4273 0.065 Uiso 1 1 calc R U . . .
C18 C 0.2590(9) 0.5023(8) 0.4071(4) 0.0390(19) Uani 1 1 d . . . . .
H18A H 0.3741 0.4695 0.4045 0.058 Uiso 1 1 calc R U . . .
H18B H 0.1896 0.4466 0.4454 0.058 Uiso 1 1 calc R U . . .
H18C H 0.2717 0.6060 0.4202 0.058 Uiso 1 1 calc R U . . .
N2 N 0.5808(7) 0.2587(6) 0.3267(3) 0.0336(15) Uani 1 1 d . . . . .
N3 N 1.3563(8) -0.0584(7) 0.4054(3) 0.0378(15) Uani 1 1 d . . . . .
C22 C 0.6691(9) 0.2817(8) 0.3907(4) 0.0356(18) Uani 1 1 d . . . . .
H22 H 0.6244 0.3428 0.4268 0.043 Uiso 1 1 calc R U . . .
C23 C 0.8198(9) 0.2249(8) 0.4097(4) 0.0327(17) Uani 1 1 d . . . . .
H23 H 0.8745 0.2472 0.4569 0.039 Uiso 1 1 calc R U . . .
C24 C 0.8895(8) 0.1354(7) 0.3591(4) 0.0281(16) Uani 1 1 d . . . . .
C25 C 0.7989(10) 0.1088(9) 0.2907(4) 0.0413(19) Uani 1 1 d . . . . .
H25 H 0.8403 0.0479 0.2536 0.050 Uiso 1 1 calc R U . . .
C26 C 0.6500(10) 0.1715(9) 0.2782(4) 0.043(2) Uani 1 1 d . . . . .
H26 H 0.5918 0.1514 0.2315 0.052 Uiso 1 1 calc R U . . .
C32 C 1.2624(9) -0.0899(8) 0.3430(4) 0.0400(19) Uani 1 1 d . . . . .
H32 H 1.3001 -0.1580 0.3086 0.048 Uiso 1 1 calc R U . . .
C33 C 1.1141(9) -0.0295(8) 0.3257(4) 0.0345(17) Uani 1 1 d . . . . .
H33 H 1.0540 -0.0553 0.2801 0.041 Uiso 1 1 calc R U . . .
C34 C 1.0521(8) 0.0684(7) 0.3743(4) 0.0259(16) Uani 1 1 d . . . . .
C35 C 1.1488(9) 0.1013(8) 0.4395(4) 0.0320(17) Uani 1 1 d . . . . .
H35 H 1.1128 0.1673 0.4754 0.038 Uiso 1 1 calc R U . . .
C36 C 1.2994(9) 0.0363(8) 0.4517(4) 0.0363(18) Uani 1 1 d . . . . .
H36 H 1.3648 0.0620 0.4961 0.044 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 C10 1.748(7) . ?
Cl2 C11 1.728(7) . ?
O1 C13 1.202(8) . ?
O2 C13 1.358(8) . ?
O2 C14 1.472(8) . ?
O3 C16 1.214(8) . ?
O4 C16 1.367(8) . ?
O4 C17 1.428(9) . ?
N1 C5 1.362(9) . ?
N1 C1 1.398(8) . ?
N1 H1 0.882(10) . ?
C1 C2 1.344(9) . ?
C1 C12 1.508(10) . ?
C2 C13 1.487(9) . ?
C2 C3 1.526(10) . ?
C3 C4 1.539(9) . ?
C3 C6 1.545(9) . ?
C3 H3 1.0000 . ?
C4 C5 1.369(9) . ?
C4 C16 1.437(10) . ?
C5 C18 1.536(9) . ?
C6 C7 1.370(9) . ?
C6 C11 1.411(9) . ?
C7 C8 1.397(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.365(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(10) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.439(11) . ?
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 . ?
N2 C22 1.330(9) . ?
N2 C26 1.341(10) . ?
N3 C36 1.319(9) . ?
N3 C32 1.336(9) . ?
C22 C23 1.384(10) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.408(10) . ?
C24 C34 1.500(9) . ?
C25 C26 1.376(10) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C32 C33 1.376(10) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.390(9) . ?
C35 C36 1.397(9) . ?
C35 H35 0.9500 . ?
C36 H36 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 116.6(6) . . ?
C16 O4 C17 116.7(5) . . ?
C5 N1 C1 122.5(6) . . ?
C5 N1 H1 117(4) . . ?
C1 N1 H1 121(4) . . ?
C2 C1 N1 120.4(6) . . ?
C2 C1 C12 127.6(6) . . ?
N1 C1 C12 112.0(6) . . ?
C1 C2 C13 120.9(6) . . ?
C1 C2 C3 122.1(6) . . ?
C13 C2 C3 117.0(5) . . ?
C2 C3 C4 111.4(5) . . ?
C2 C3 C6 109.9(5) . . ?
C4 C3 C6 110.2(5) . . ?
C2 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C6 C3 H3 108.4 . . ?
C5 C4 C16 120.9(6) . . ?
C5 C4 C3 120.7(6) . . ?
C16 C4 C3 118.4(5) . . ?
N1 C5 C4 121.3(6) . . ?
N1 C5 C18 114.4(6) . . ?
C4 C5 C18 124.3(6) . . ?
C7 C6 C11 118.4(6) . . ?
C7 C6 C3 117.9(5) . . ?
C11 C6 C3 123.6(6) . . ?
C6 C7 C8 122.3(6) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C9 118.8(7) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 119.6(7) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.5(6) . . ?
C9 C10 Cl1 117.6(6) . . ?
C11 C10 Cl1 120.9(6) . . ?
C10 C11 C6 119.3(6) . . ?
C10 C11 Cl2 118.8(5) . . ?
C6 C11 Cl2 121.9(5) . . ?
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 121.6(6) . . ?
O1 C13 C2 127.8(6) . . ?
O2 C13 C2 110.6(6) . . ?
C15 C14 O2 108.5(6) . . ?
C15 C14 H14A 110.0 . . ?
O2 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
O2 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 . . ?
O3 C16 O4 120.7(6) . . ?
O3 C16 C4 128.6(6) . . ?
O4 C16 C4 110.7(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 . . ?
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 . . ?
C22 N2 C26 114.1(6) . . ?
C36 N3 C32 116.3(6) . . ?
N2 C22 C23 126.2(7) . . ?
N2 C22 H22 116.9 . . ?
C23 C22 H22 116.9 . . ?
C24 C23 C22 119.0(7) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 116.2(6) . . ?
C23 C24 C34 123.1(6) . . ?
C25 C24 C34 120.7(7) . . ?
C26 C25 C24 119.5(7) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
N2 C26 C25 124.9(7) . . ?
N2 C26 H26 117.5 . . ?
C25 C26 H26 117.5 . . ?
N3 C32 C33 123.8(8) . . ?
N3 C32 H32 118.1 . . ?
C33 C32 H32 118.1 . . ?
C32 C33 C34 120.5(7) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C33 C34 C35 116.0(6) . . ?
C33 C34 C24 122.7(6) . . ?
C35 C34 C24 121.3(6) . . ?
C34 C35 C36 119.5(7) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
N3 C36 C35 124.0(7) . . ?
N3 C36 H36 118.0 . . ?
C35 C36 H36 118.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.882(10) 2.27(2) 3.126(8) 165(6) .

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 994273'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ks1137

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            
;
Felodipine : 4,4'-bipyridine (2:1)
;
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H19 Cl2 N O4), C10 H8 N2'
_chemical_formula_sum            'C46 H46 Cl4 N4 O8'
_chemical_formula_weight         924.67

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      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                   10.4207(9)
_cell_length_b                   10.6061(9)
_cell_length_c                   11.2328(9)
_cell_angle_alpha                67.167(4)
_cell_angle_beta                 73.749(4)
_cell_angle_gamma                81.109(5)
_cell_volume                     1097.00(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8313
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.55

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             482
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.329
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6387
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker Nonius X8APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23260
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.762
_diffrn_reflns_theta_max         25.748
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             4000
_reflns_number_gt                2771
_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 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2012)'
_computing_publication_material  SHELXL-2013

_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)+(0.0979P)²+2.5733P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4000
_refine_ls_number_parameters     288
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2191
_refine_ls_wR_factor_gt          0.1928
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.198
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.081

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 0.19805(15) 0.21842(17) 1.15662(13) 0.0655(5) Uani 1 1 d . . . . .
Cl2 Cl 0.31462(12) 0.43571(13) 0.87868(12) 0.0475(4) Uani 1 1 d . . . . .
O1 O 0.2449(3) 0.3364(4) 0.4599(3) 0.0517(9) Uani 1 1 d . . . . .
O2 O 0.2394(3) 0.4097(3) 0.6236(3) 0.0349(7) Uani 1 1 d . . . . .
O3 O 0.8125(3) 0.2891(3) 0.7398(3) 0.0403(8) Uani 1 1 d . . . . .
O4 O 0.6164(3) 0.4018(3) 0.7833(3) 0.0401(8) Uani 1 1 d . . . . .
N1 N 0.6438(4) 0.1845(4) 0.4851(3) 0.0358(9) Uani 1 1 d D . . . .
H1 H 0.689(4) 0.144(4) 0.430(3) 0.024(11) Uiso 1 1 d D . . . .
C1 C 0.7051(4) 0.2145(4) 0.5643(4) 0.0302(9) Uani 1 1 d . . . . .
C2 C 0.6350(4) 0.2831(4) 0.6438(4) 0.0270(9) Uani 1 1 d . . . . .
C3 C 0.4845(4) 0.3160(4) 0.6593(4) 0.0291(9) Uani 1 1 d . . . . .
H3 H 0.4641 0.4132 0.6535 0.035 Uiso 1 1 calc R U . . .
C4 C 0.4374(4) 0.2968(4) 0.5505(4) 0.0311(9) Uani 1 1 d . . . . .
C5 C 0.5155(4) 0.2313(4) 0.4720(4) 0.0344(10) Uani 1 1 d . . . . .
C6 C 0.4116(4) 0.2207(4) 0.7975(4) 0.0291(9) Uani 1 1 d . . . . .
C7 C 0.4257(4) 0.0792(4) 0.8233(4) 0.0325(9) Uani 1 1 d . . . . .
H7 H 0.4762 0.0476 0.7547 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3676(4) -0.0160(5) 0.9469(4) 0.0390(11) Uani 1 1 d . . . . .
H8 H 0.3765 -0.1110 0.9614 0.047 Uiso 1 1 calc R U . . .
C9 C 0.2977(4) 0.0285(5) 1.0469(4) 0.0432(12) Uani 1 1 d . . . . .
H9 H 0.2590 -0.0358 1.1318 0.052 Uiso 1 1 calc R U . . .
C10 C 0.2831(4) 0.1668(5) 1.0251(4) 0.0410(11) Uani 1 1 d . . . . .
C11 C 0.3393(4) 0.2642(5) 0.8997(4) 0.0344(10) Uani 1 1 d . . . . .
C12 C 0.8487(4) 0.1605(5) 0.5524(4) 0.0377(10) Uani 1 1 d . . . . .
H12A H 0.9019 0.2258 0.5577 0.057 Uiso 1 1 calc R U . . .
H12B H 0.8838 0.1483 0.4668 0.057 Uiso 1 1 calc R U . . .
H12C H 0.8537 0.0723 0.6251 0.057 Uiso 1 1 calc R U . . .
C13 C 0.6991(4) 0.3218(4) 0.7241(4) 0.0301(9) Uani 1 1 d . . . . .
C14 C 0.6686(5) 0.4489(5) 0.8640(5) 0.0468(12) Uani 1 1 d . . . . .
H14A H 0.6030 0.5137 0.8943 0.070 Uiso 1 1 calc R U . . .
H14B H 0.7520 0.4945 0.8113 0.070 Uiso 1 1 calc R U . . .
H14C H 0.6861 0.3706 0.9414 0.070 Uiso 1 1 calc R U . . .
C15 C 0.3000(4) 0.3479(4) 0.5372(4) 0.0359(10) Uani 1 1 d . . . . .
C16 C 0.1044(4) 0.4677(5) 0.6135(5) 0.0412(11) Uani 1 1 d . . . . .
H16A H 0.0457 0.3948 0.6299 0.049 Uiso 1 1 calc R U . . .
H16B H 0.1068 0.5368 0.5233 0.049 Uiso 1 1 calc R U . . .
C17 C 0.0523(5) 0.5326(6) 0.7147(5) 0.0595(15) Uani 1 1 d . . . . .
H17A H -0.0382 0.5727 0.7096 0.089 Uiso 1 1 calc R U . . .
H17B H 0.1111 0.6046 0.6976 0.089 Uiso 1 1 calc R U . . .
H17C H 0.0497 0.4632 0.8036 0.089 Uiso 1 1 calc R U . . .
C18 C 0.4797(5) 0.2021(6) 0.3648(5) 0.0472(12) Uani 1 1 d . . . . .
H18A H 0.3998 0.1482 0.4032 0.071 Uiso 1 1 calc R U . . .
H18B H 0.5544 0.1503 0.3260 0.071 Uiso 1 1 calc R U . . .
H18C H 0.4616 0.2887 0.2953 0.071 Uiso 1 1 calc R U . . .
N2 N 0.8213(4) 0.0994(4) 0.2718(4) 0.0427(10) Uani 1 1 d . . . . .
C22 C 0.8532(6) 0.1898(5) 0.1475(5) 0.0554(14) Uani 1 1 d . . . . .
H22 H 0.8267 0.2835 0.1324 0.067 Uiso 1 1 calc R U . . .
C23 C 0.9220(6) 0.1553(5) 0.0408(5) 0.0477(12) Uani 1 1 d . . . . .
H23 H 0.9417 0.2246 -0.0454 0.057 Uiso 1 1 calc R U . . .
C24 C 0.9635(4) 0.0207(4) 0.0565(4) 0.0280(9) Uani 1 1 d . . . . .
C25 C 0.9310(5) -0.0727(5) 0.1848(4) 0.0410(11) Uani 1 1 d . . . . .
H25 H 0.9570 -0.1668 0.2025 0.049 Uiso 1 1 calc R U . . .
C26 C 0.8604(5) -0.0302(5) 0.2883(4) 0.0447(12) Uani 1 1 d . . . . .
H26 H 0.8390 -0.0973 0.3756 0.054 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 C10 1.735(4) . ?
Cl2 C11 1.729(5) . ?
O1 C15 1.218(5) . ?
O2 C15 1.339(5) . ?
O2 C16 1.462(5) . ?
O3 C13 1.221(5) . ?
O4 C13 1.340(5) . ?
O4 C14 1.442(5) . ?
N1 C5 1.380(5) . ?
N1 C1 1.379(6) . ?
N1 H1 0.877(10) . ?
C1 C2 1.354(6) . ?
C1 C12 1.506(6) . ?
C2 C13 1.461(6) . ?
C2 C3 1.529(5) . ?
C3 C4 1.528(6) . ?
C3 C6 1.538(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.351(6) . ?
C4 C15 1.478(6) . ?
C5 C18 1.504(6) . ?
C6 C11 1.385(6) . ?
C6 C7 1.405(6) . ?
C7 C8 1.395(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.364(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.411(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.485(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N2 C26 1.327(6) . ?
N2 C22 1.334(6) . ?
C22 C23 1.365(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(6) . ?
C24 C24 1.473(8) 2_755 ?
C25 C26 1.386(6) . ?
C25 H25 0.9500 . ?
C26 H26 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
C15 O2 C16 114.8(3) . . ?
C13 O4 C14 116.9(3) . . ?
C5 N1 C1 123.5(4) . . ?
C5 N1 H1 115(3) . . ?
C1 N1 H1 121(3) . . ?
C2 C1 N1 120.0(4) . . ?
C2 C1 C12 127.1(4) . . ?
N1 C1 C12 112.9(4) . . ?
C1 C2 C13 121.2(4) . . ?
C1 C2 C3 121.5(4) . . ?
C13 C2 C3 117.3(3) . . ?
C4 C3 C2 111.1(3) . . ?
C4 C3 C6 110.3(3) . . ?
C2 C3 C6 108.2(3) . . ?
C4 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C6 C3 H3 109.1 . . ?
C5 C4 C15 120.5(4) . . ?
C5 C4 C3 121.9(4) . . ?
C15 C4 C3 117.5(4) . . ?
C4 C5 N1 120.0(4) . . ?
C4 C5 C18 127.1(4) . . ?
N1 C5 C18 113.0(4) . . ?
C11 C6 C7 118.0(4) . . ?
C11 C6 C3 124.5(4) . . ?
C7 C6 C3 117.4(3) . . ?
C8 C7 C6 121.8(4) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C9 C8 C7 119.4(4) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.2(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 Cl1 118.6(4) . . ?
C11 C10 Cl1 120.5(4) . . ?
C6 C11 C10 119.7(4) . . ?
C6 C11 Cl2 122.0(3) . . ?
C10 C11 Cl2 118.3(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 . . ?
O3 C13 O4 121.2(4) . . ?
O3 C13 C2 127.4(4) . . ?
O4 C13 C2 111.4(3) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 O2 122.5(4) . . ?
O1 C15 C4 126.1(4) . . ?
O2 C15 C4 111.3(4) . . ?
O2 C16 C17 107.9(4) . . ?
O2 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
O2 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 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 . . ?
C26 N2 C22 116.1(4) . . ?
N2 C22 C23 123.7(5) . . ?
N2 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
C22 C23 C24 120.9(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 115.6(4) . . ?
C25 C24 C24 122.0(5) . 2_755 ?
C23 C24 C24 122.4(4) . 2_755 ?
C24 C25 C26 120.4(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
N2 C26 C25 123.4(4) . . ?
N2 C26 H26 118.3 . . ?
C25 C26 H26 118.3 . . ?

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 6.1(6) . . . . ?
C5 N1 C1 C12 -175.3(4) . . . . ?
N1 C1 C2 C13 -177.1(3) . . . . ?
C12 C1 C2 C13 4.5(6) . . . . ?
N1 C1 C2 C3 6.4(6) . . . . ?
C12 C1 C2 C3 -172.0(4) . . . . ?
C1 C2 C3 C4 -14.9(5) . . . . ?
C13 C2 C3 C4 168.4(3) . . . . ?
C1 C2 C3 C6 106.3(4) . . . . ?
C13 C2 C3 C6 -70.3(4) . . . . ?
C2 C3 C4 C5 13.1(5) . . . . ?
C6 C3 C4 C5 -106.9(4) . . . . ?
C2 C3 C4 C15 -169.3(3) . . . . ?
C6 C3 C4 C15 70.7(4) . . . . ?
C15 C4 C5 N1 179.8(4) . . . . ?
C3 C4 C5 N1 -2.7(6) . . . . ?
C15 C4 C5 C18 0.5(7) . . . . ?
C3 C4 C5 C18 178.0(4) . . . . ?
C1 N1 C5 C4 -8.0(6) . . . . ?
C1 N1 C5 C18 171.4(4) . . . . ?
C4 C3 C6 C11 -124.7(4) . . . . ?
C2 C3 C6 C11 113.5(4) . . . . ?
C4 C3 C6 C7 58.8(4) . . . . ?
C2 C3 C6 C7 -63.0(5) . . . . ?
C11 C6 C7 C8 1.0(6) . . . . ?
C3 C6 C7 C8 177.7(4) . . . . ?
C6 C7 C8 C9 -1.6(6) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C8 C9 C10 C11 0.3(7) . . . . ?
C8 C9 C10 Cl1 -178.0(3) . . . . ?
C7 C6 C11 C10 0.3(6) . . . . ?
C3 C6 C11 C10 -176.2(4) . . . . ?
C7 C6 C11 Cl2 -179.5(3) . . . . ?
C3 C6 C11 Cl2 3.9(6) . . . . ?
C9 C10 C11 C6 -0.9(7) . . . . ?
Cl1 C10 C11 C6 177.3(3) . . . . ?
C9 C10 C11 Cl2 178.9(3) . . . . ?
Cl1 C10 C11 Cl2 -2.9(5) . . . . ?
C14 O4 C13 O3 1.1(6) . . . . ?
C14 O4 C13 C2 -179.1(4) . . . . ?
C1 C2 C13 O3 -7.2(6) . . . . ?
C3 C2 C13 O3 169.5(4) . . . . ?
C1 C2 C13 O4 173.0(3) . . . . ?
C3 C2 C13 O4 -10.4(5) . . . . ?
C16 O2 C15 O1 -2.8(6) . . . . ?
C16 O2 C15 C4 177.8(3) . . . . ?
C5 C4 C15 O1 0.7(7) . . . . ?
C3 C4 C15 O1 -176.9(4) . . . . ?
C5 C4 C15 O2 -179.9(4) . . . . ?
C3 C4 C15 O2 2.4(5) . . . . ?
C15 O2 C16 C17 -179.6(4) . . . . ?
C26 N2 C22 C23 0.0(8) . . . . ?
N2 C22 C23 C24 0.0(9) . . . . ?
C22 C23 C24 C25 -0.2(7) . . . . ?
C22 C23 C24 C24 179.2(5) . . . 2_755 ?
C23 C24 C25 C26 0.4(7) . . . . ?
C24 C24 C25 C26 -179.0(5) 2_755 . . . ?
C22 N2 C26 C25 0.2(7) . . . . ?
C24 C25 C26 N2 -0.4(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.88(1) 2.090(16) 2.943(5) 164(4) .

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 994274'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ks1139

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
Felodipine : 4,4'-bipyridine (1:1)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 Cl2 N O4, C10 H8 N2'
_chemical_formula_sum            'C28 H27 Cl2 N3 O4'
_chemical_formula_weight         540.42

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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   36.197(3)
_cell_length_b                   36.436(3)
_cell_length_c                   8.0228(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10581.1(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6429
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      22.06

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             4512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.285
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker Nonius X8APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21047
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.819
_diffrn_reflns_theta_max         25.057
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.911
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.887
_reflns_number_total             4259
_reflns_number_gt                3396
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_max     0.883
_reflns_Friedel_fraction_full    0.860

_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 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2012)'
_computing_publication_material  SHELXL-2013

_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)+(0.0532P)²+9.5754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1334 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4259
_refine_ls_number_parameters     342
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.042

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 0.03703(3) -0.03335(4) 0.52630(19) 0.0571(4) Uani 1 1 d . . . . .
Cl2 Cl 0.06319(3) 0.03988(4) 0.36670(18) 0.0513(4) Uani 1 1 d . . . . .
O1 O 0.18766(12) 0.02955(13) -0.0247(5) 0.0717(13) Uani 1 1 d . . . . .
O2 O 0.13066(10) 0.03446(10) 0.0816(4) 0.0475(9) Uani 1 1 d . . . . .
O3 O 0.14551(9) 0.11447(9) 0.7691(5) 0.0503(9) Uani 1 1 d . . . . .
O4 O 0.10429(8) 0.09601(9) 0.5795(4) 0.0442(9) Uani 1 1 d . . . . .
N1 N 0.22606(11) 0.06295(12) 0.4558(6) 0.0453(11) Uani 1 1 d D . . . .
H1 H 0.2492(8) 0.063(2) 0.487(11) 0.12(3) Uiso 1 1 d D . . . .
C1 C 0.21571(14) 0.04976(14) 0.3031(7) 0.0464(14) Uani 1 1 d . . . . .
C2 C 0.17950(13) 0.04763(12) 0.2588(7) 0.0393(12) Uani 1 1 d . . . . .
C3 C 0.14942(12) 0.05597(11) 0.3885(6) 0.0312(11) Uani 1 1 d . . . . .
H3 H 0.1292 0.0701 0.3332 0.037 Uiso 1 1 calc R U . . .
C4 C 0.16499(12) 0.07887(12) 0.5313(6) 0.0331(11) Uani 1 1 d . . . . .
C5 C 0.20157(13) 0.08042(12) 0.5636(6) 0.0389(12) Uani 1 1 d . . . . .
C6 C 0.13344(11) 0.01995(12) 0.4551(5) 0.0276(10) Uani 1 1 d . . . . .
C7 C 0.15752(11) -0.00525(11) 0.5271(6) 0.0285(10) Uani 1 1 d . . . . .
H7 H 0.1830 0.0006 0.5337 0.034 Uiso 1 1 calc R U . . .
C8 C 0.14553(12) -0.03843(12) 0.5892(6) 0.0344(11) Uani 1 1 d . . . . .
H8 H 0.1629 -0.0555 0.6325 0.041 Uiso 1 1 calc R U . . .
C9 C 0.10843(13) -0.04703(13) 0.5889(6) 0.0366(12) Uani 1 1 d . . . . .
H9 H 0.1000 -0.0695 0.6349 0.044 Uiso 1 1 calc R U . . .
C10 C 0.08376(11) -0.02222(12) 0.5202(6) 0.0344(11) Uani 1 1 d . . . . .
C11 C 0.09606(11) 0.01073(12) 0.4520(6) 0.0310(11) Uani 1 1 d . . . . .
C12 C 0.24860(15) 0.03844(17) 0.1968(8) 0.0630(18) Uani 1 1 d . . . . .
H12A H 0.2402 0.0221 0.1073 0.095 Uiso 1 1 calc R U . . .
H12B H 0.2667 0.0256 0.2664 0.095 Uiso 1 1 calc R U . . .
H12C H 0.2601 0.0603 0.1483 0.095 Uiso 1 1 calc R U . . .
C13 C 0.16759(17) 0.03633(14) 0.0918(7) 0.0478(14) Uani 1 1 d . . . . .
C14 C 0.11578(18) 0.02391(17) -0.0791(7) 0.0582(16) Uani 1 1 d . . . . .
H14A H 0.1251 -0.0006 -0.1113 0.070 Uiso 1 1 calc R U . . .
H14B H 0.1234 0.0418 -0.1654 0.070 Uiso 1 1 calc R U . . .
C15 C 0.0741(2) 0.0231(3) -0.0643(10) 0.093(2) Uani 1 1 d . . . . .
H15A H 0.0632 0.0206 -0.1754 0.140 Uiso 1 1 calc R U . . .
H15B H 0.0656 0.0460 -0.0133 0.140 Uiso 1 1 calc R U . . .
H15C H 0.0667 0.0023 0.0054 0.140 Uiso 1 1 calc R U . . .
C16 C 0.13872(13) 0.09830(12) 0.6395(7) 0.0359(12) Uani 1 1 d . . . . .
C17 C 0.07541(15) 0.11387(18) 0.6766(9) 0.0629(17) Uani 1 1 d . . . . .
H17A H 0.0514 0.1098 0.6230 0.094 Uiso 1 1 calc R U . . .
H17B H 0.0804 0.1403 0.6827 0.094 Uiso 1 1 calc R U . . .
H17C H 0.0750 0.1035 0.7894 0.094 Uiso 1 1 calc R U . . .
C18 C 0.21979(14) 0.09876(16) 0.7086(8) 0.0549(16) Uani 1 1 d . . . . .
H18A H 0.2115 0.1243 0.7155 0.082 Uiso 1 1 calc R U . . .
H18B H 0.2467 0.0981 0.6938 0.082 Uiso 1 1 calc R U . . .
H18C H 0.2132 0.0859 0.8116 0.082 Uiso 1 1 calc R U . . .
N2 N 0.30559(10) 0.08036(11) 0.5155(6) 0.0467(11) Uani 1 1 d . . . . .
N3 N 0.50131(12) 0.09715(17) 0.4933(7) 0.0714(16) Uani 1 1 d . . . . .
C22 C 0.32211(13) 0.10622(14) 0.4251(7) 0.0405(12) Uani 1 1 d . . . . .
H22 H 0.3071 0.1221 0.3601 0.049 Uiso 1 1 calc R U . . .
C23 C 0.35995(11) 0.11129(13) 0.4205(6) 0.0340(11) Uani 1 1 d . . . . .
H23 H 0.3702 0.1300 0.3525 0.041 Uiso 1 1 calc R U . . .
C24 C 0.38292(11) 0.08902(12) 0.5151(6) 0.0322(10) Uani 1 1 d . . . . .
C25 C 0.36569(13) 0.06237(14) 0.6124(7) 0.0453(13) Uani 1 1 d . . . . .
H25 H 0.3800 0.0465 0.6805 0.054 Uiso 1 1 calc R U . . .
C26 C 0.32770(14) 0.05907(14) 0.6095(8) 0.0543(15) Uani 1 1 d . . . . .
H26 H 0.3166 0.0408 0.6775 0.065 Uiso 1 1 calc R U . . .
C32 C 0.48357(16) 0.0822(2) 0.6213(9) 0.088(2) Uani 1 1 d . . . . .
H32 H 0.4980 0.0731 0.7111 0.105 Uiso 1 1 calc R U . . .
C33 C 0.44605(15) 0.0789(2) 0.6335(8) 0.070(2) Uani 1 1 d . . . . .
H33 H 0.4353 0.0673 0.7281 0.085 Uiso 1 1 calc R U . . .
C34 C 0.42388(12) 0.09232(13) 0.5083(6) 0.0361(11) Uani 1 1 d . . . . .
C35 C 0.44164(13) 0.11003(13) 0.3796(7) 0.0411(12) Uani 1 1 d . . . . .
H35 H 0.4279 0.1214 0.2929 0.049 Uiso 1 1 calc R U . . .
C36 C 0.47992(13) 0.11106(17) 0.3789(8) 0.0552(15) Uani 1 1 d . . . . .
H36 H 0.4915 0.1229 0.2873 0.066 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 C10 1.740(4) . ?
Cl2 C11 1.735(5) . ?
O1 C13 1.210(6) . ?
O2 C13 1.341(7) . ?
O2 C14 1.449(6) . ?
O3 C16 1.220(6) . ?
O4 C16 1.339(5) . ?
O4 C17 1.457(6) . ?
N1 C1 1.369(7) . ?
N1 C5 1.393(6) . ?
N1 H1 0.874(14) . ?
C1 C2 1.360(7) . ?
C1 C12 1.521(7) . ?
C2 C13 1.467(8) . ?
C2 C3 1.536(6) . ?
C3 C4 1.525(7) . ?
C3 C6 1.530(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.351(6) . ?
C4 C16 1.469(7) . ?
C5 C18 1.495(7) . ?
C6 C7 1.392(6) . ?
C6 C11 1.395(6) . ?
C7 C8 1.378(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.512(9) . ?
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 . ?
N2 C22 1.331(7) . ?
N2 C26 1.346(7) . ?
N3 C36 1.303(7) . ?
N3 C32 1.328(8) . ?
C22 C23 1.383(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.394(7) . ?
C24 C34 1.488(6) . ?
C25 C26 1.381(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C32 C33 1.367(8) . ?
C32 H32 0.9500 . ?
C33 C34 1.376(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(7) . ?
C35 C36 1.386(7) . ?
C35 H35 0.9500 . ?
C36 H36 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 116.0(4) . . ?
C16 O4 C17 116.6(4) . . ?
C1 N1 C5 122.8(4) . . ?
C1 N1 H1 121(6) . . ?
C5 N1 H1 115(6) . . ?
C2 C1 N1 121.2(5) . . ?
C2 C1 C12 126.3(5) . . ?
N1 C1 C12 112.5(5) . . ?
C1 C2 C13 122.5(5) . . ?
C1 C2 C3 119.7(5) . . ?
C13 C2 C3 117.8(5) . . ?
C4 C3 C6 110.3(4) . . ?
C4 C3 C2 110.8(4) . . ?
C6 C3 C2 109.5(3) . . ?
C4 C3 H3 108.7 . . ?
C6 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C5 C4 C16 120.0(4) . . ?
C5 C4 C3 122.0(4) . . ?
C16 C4 C3 117.9(4) . . ?
C4 C5 N1 119.1(4) . . ?
C4 C5 C18 126.9(4) . . ?
N1 C5 C18 114.0(4) . . ?
C7 C6 C11 117.1(4) . . ?
C7 C6 C3 118.3(4) . . ?
C11 C6 C3 124.6(4) . . ?
C8 C7 C6 122.1(4) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 118.7(4) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 Cl1 117.6(3) . . ?
C11 C10 Cl1 121.5(4) . . ?
C10 C11 C6 120.7(4) . . ?
C10 C11 Cl2 117.6(3) . . ?
C6 C11 Cl2 121.7(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 122.8(5) . . ?
O1 C13 C2 125.9(5) . . ?
O2 C13 C2 111.3(4) . . ?
O2 C14 C15 107.8(5) . . ?
O2 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O2 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
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 121.6(4) . . ?
O3 C16 C4 127.3(4) . . ?
O4 C16 C4 111.1(4) . . ?
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 . . ?
C22 N2 C26 116.5(4) . . ?
C36 N3 C32 114.6(5) . . ?
N2 C22 C23 123.7(5) . . ?
N2 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
C22 C23 C24 120.0(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 116.5(4) . . ?
C23 C24 C34 122.0(4) . . ?
C25 C24 C34 121.5(4) . . ?
C26 C25 C24 119.8(5) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
N2 C26 C25 123.5(5) . . ?
N2 C26 H26 118.3 . . ?
C25 C26 H26 118.3 . . ?
N3 C32 C33 124.9(6) . . ?
N3 C32 H32 117.6 . . ?
C33 C32 H32 117.6 . . ?
C32 C33 C34 119.7(6) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C33 C34 C35 116.2(4) . . ?
C33 C34 C24 121.7(5) . . ?
C35 C34 C24 122.0(4) . . ?
C34 C35 C36 118.9(5) . . ?
C34 C35 H35 120.6 . . ?
C36 C35 H35 120.6 . . ?
N3 C36 C35 125.5(5) . . ?
N3 C36 H36 117.3 . . ?
C35 C36 H36 117.3 . . ?

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 -10.9(8) . . . . ?
C5 N1 C1 C12 169.3(5) . . . . ?
N1 C1 C2 C13 175.2(5) . . . . ?
C12 C1 C2 C13 -5.0(8) . . . . ?
N1 C1 C2 C3 -7.0(7) . . . . ?
C12 C1 C2 C3 172.8(5) . . . . ?
C1 C2 C3 C4 20.9(6) . . . . ?
C13 C2 C3 C4 -161.2(4) . . . . ?
C1 C2 C3 C6 -101.0(5) . . . . ?
C13 C2 C3 C6 76.9(5) . . . . ?
C6 C3 C4 C5 101.3(5) . . . . ?
C2 C3 C4 C5 -20.2(6) . . . . ?
C6 C3 C4 C16 -76.0(5) . . . . ?
C2 C3 C4 C16 162.5(4) . . . . ?
C16 C4 C5 N1 -177.6(4) . . . . ?
C3 C4 C5 N1 5.2(7) . . . . ?
C16 C4 C5 C18 3.6(8) . . . . ?
C3 C4 C5 C18 -173.6(5) . . . . ?
C1 N1 C5 C4 11.9(7) . . . . ?
C1 N1 C5 C18 -169.2(5) . . . . ?
C4 C3 C6 C7 -65.2(5) . . . . ?
C2 C3 C6 C7 57.0(5) . . . . ?
C4 C3 C6 C11 113.4(5) . . . . ?
C2 C3 C6 C11 -124.4(5) . . . . ?
C11 C6 C7 C8 1.7(6) . . . . ?
C3 C6 C7 C8 -179.6(4) . . . . ?
C6 C7 C8 C9 -3.2(7) . . . . ?
C7 C8 C9 C10 2.1(7) . . . . ?
C8 C9 C10 C11 0.3(7) . . . . ?
C8 C9 C10 Cl1 -178.5(4) . . . . ?
C9 C10 C11 C6 -1.7(7) . . . . ?
Cl1 C10 C11 C6 177.0(3) . . . . ?
C9 C10 C11 Cl2 179.3(4) . . . . ?
Cl1 C10 C11 Cl2 -2.0(6) . . . . ?
C7 C6 C11 C10 0.7(6) . . . . ?
C3 C6 C11 C10 -177.9(4) . . . . ?
C7 C6 C11 Cl2 179.6(3) . . . . ?
C3 C6 C11 Cl2 1.0(6) . . . . ?
C14 O2 C13 O1 -0.3(7) . . . . ?
C14 O2 C13 C2 179.3(4) . . . . ?
C1 C2 C13 O1 -3.8(8) . . . . ?
C3 C2 C13 O1 178.4(5) . . . . ?
C1 C2 C13 O2 176.6(4) . . . . ?
C3 C2 C13 O2 -1.2(6) . . . . ?
C13 O2 C14 C15 179.6(5) . . . . ?
C17 O4 C16 O3 0.2(7) . . . . ?
C17 O4 C16 C4 179.3(4) . . . . ?
C5 C4 C16 O3 -6.0(8) . . . . ?
C3 C4 C16 O3 171.4(5) . . . . ?
C5 C4 C16 O4 174.9(4) . . . . ?
C3 C4 C16 O4 -7.8(6) . . . . ?
C26 N2 C22 C23 1.8(7) . . . . ?
N2 C22 C23 C24 -0.8(7) . . . . ?
C22 C23 C24 C25 -0.5(7) . . . . ?
C22 C23 C24 C34 177.2(4) . . . . ?
C23 C24 C25 C26 0.6(7) . . . . ?
C34 C24 C25 C26 -177.0(5) . . . . ?
C22 N2 C26 C25 -1.6(8) . . . . ?
C24 C25 C26 N2 0.4(8) . . . . ?
C36 N3 C32 C33 4.0(12) . . . . ?
N3 C32 C33 C34 -1.4(12) . . . . ?
C32 C33 C34 C35 -2.8(9) . . . . ?
C32 C33 C34 C24 179.4(6) . . . . ?
C23 C24 C34 C33 160.1(6) . . . . ?
C25 C24 C34 C33 -22.4(7) . . . . ?
C23 C24 C34 C35 -17.7(7) . . . . ?
C25 C24 C34 C35 159.9(5) . . . . ?
C33 C34 C35 C36 4.1(8) . . . . ?
C24 C34 C35 C36 -178.0(4) . . . . ?
C32 N3 C36 C35 -2.4(10) . . . . ?
C34 C35 C36 N3 -1.6(9) . . . . ?

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 994275'
