# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_I
_audit_block_doi                 10.5517/cc11c6f1
_database_code_depnum_ccdc_archive 'CCDC 964082'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1107/S1600536813021946 2013
_audit_update_record             
;
2013-10-01 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(E)-3-[5-(Diphenylamino)thiophen-2-yl]-1-(pyridin-3-yl)prop-2-en-1-one
;

_chemical_name_common            ?
_chemical_formula_moiety         'C24 H18 N2 O S'
_chemical_formula_sum            'C24 H18 N2 O S'
_chemical_formula_iupac          'C24 H18 N2 O S'
_chemical_formula_weight         382.46
_chemical_melting_point          ?
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz

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


_cell_length_a                   10.976(5)

_cell_length_b                   18.029(5)

_cell_length_c                   9.697(5)

_cell_angle_alpha                90.000

_cell_angle_beta                 90.728(5)

_cell_angle_gamma                90.000

_cell_volume                     1918.7(14)

_cell_formula_units_Z            4

_cell_measurement_reflns_used    3272

_cell_measurement_theta_min      2.17

_cell_measurement_theta_max      22.81

_cell_measurement_temperature    293(2)

_exptl_crystal_description       block

_exptl_crystal_colour            red

_exptl_crystal_size_max          0.30

_exptl_crystal_size_mid          0.20

_exptl_crystal_size_min          0.20

_exptl_crystal_density_diffrn    1.324

_exptl_crystal_density_meas      ?

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             800

_exptl_absorpt_coefficient_mu    0.186

_exptl_absorpt_correction_type   none

_exptl_absorpt_process_details   ?

_exptl_absorpt_correction_T_min  ?

_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
;


_diffrn_ambient_temperature      293(2)

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71069

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13536

_diffrn_reflns_av_R_equivalents  0.0309

_diffrn_reflns_av_sigmaI/netI    0.0291

_diffrn_reflns_theta_min         1.86

_diffrn_reflns_theta_max         25.00

_diffrn_reflns_theta_full        25.00

_diffrn_measured_fraction_theta_max 0.999

_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_limit_h_min       -13

_diffrn_reflns_limit_h_max       13

_diffrn_reflns_limit_k_min       -21

_diffrn_reflns_limit_k_max       21

_diffrn_reflns_limit_l_min       -11

_diffrn_reflns_limit_l_max       11

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_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 >
σ(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.
;


_reflns_number_total             3388

_reflns_number_gt                2517

_reflns_threshold_expression     I>2sigma(I)

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_R_factor_all          0.0583

_refine_ls_R_factor_gt           0.0388

_refine_ls_wR_factor_gt          0.1170

_refine_ls_wR_factor_ref         0.1377

_refine_ls_goodness_of_fit_ref   0.947

_refine_ls_restrained_S_all      0.947

_refine_ls_number_reflns         3388

_refine_ls_number_parameters     253

_refine_ls_number_restraints     0

_refine_ls_hydrogen_treatment    constr

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         0.135

_refine_diff_density_min         -0.292

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?
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'


_computing_data_collection       'SMART (Bruker, 2007)'

_computing_cell_refinement       'SAINT (Bruker, 2007)'

_computing_data_reduction        'SAINT (Bruker, 2007)'

_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'

_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'

_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group

S S1 0.39364(5) 0.13546(3) 0.84763(5) 0.0520(2) Uani d . 1 1 . .
O O1 0.80534(14) 0.06367(10) 1.13966(15) 0.0628(4) Uani d . 1 1 . .
N N1 0.23384(15) 0.12744(10) 0.63004(17) 0.0518(5) Uani d . 1 1 . .
C C18 0.61524(18) 0.11137(11) 1.0700(2) 0.0471(5) Uani d . 1 1 . .
H H18 0.5526 0.1439 1.0917 0.057 Uiso calc R 1 1 . .
C C14 0.41913(19) 0.04995(12) 0.6381(2) 0.0483(5) Uani d . 1 1 . .
H H14 0.4065 0.0256 0.5546 0.058 Uiso calc R 1 1 . .
C C7 0.13189(17) 0.15100(11) 0.70872(19) 0.0438(5) Uani d . 1 1 . .
C C20 0.70392(18) 0.12875(11) 1.3133(2) 0.0431(5) Uani d . 1 1 . .
C C13 0.33940(17) 0.10074(11) 0.69095(19) 0.0428(5) Uani d . 1 1 . .
C C15 0.52143(18) 0.03859(11) 0.7228(2) 0.0480(5) Uani d . 1 1 . .
H H15 0.5835 0.0058 0.7003 0.058 Uiso calc R 1 1 . .
C C19 0.71424(18) 0.09932(11) 1.1691(2) 0.0448(5) Uani d . 1 1 . .
C C16 0.52275(17) 0.07951(11) 0.8412(2) 0.0428(5) Uani d . 1 1 . .
C C1 0.22037(18) 0.12040(11) 0.4829(2) 0.0444(5) Uani d . 1 1 . .
C C2 0.3006(2) 0.15559(14) 0.3977(2) 0.0576(6) Uani d . 1 1 . .
H H2 0.3623 0.1851 0.4348 0.069 Uiso calc R 1 1 . .
C C12 0.08974(19) 0.10913(13) 0.8175(2) 0.0511(5) Uani d . 1 1 . .
H H12 0.1278 0.0647 0.8410 0.061 Uiso calc R 1 1 . .
C C17 0.61310(18) 0.07655(11) 0.9487(2) 0.0445(5) Uani d . 1 1 . .
H H17 0.6796 0.0461 0.9316 0.053 Uiso calc R 1 1 . .
N N2 0.60796(19) 0.20514(11) 1.4845(2) 0.0666(6) Uani d . 1 1 . .
C C8 0.0729(2) 0.21623(12) 0.6732(2) 0.0561(6) Uani d . 1 1 . .
H H8 0.1001 0.2440 0.5988 0.067 Uiso calc R 1 1 . .
C C11 -0.0099(2) 0.13381(15) 0.8915(2) 0.0644(7) Uani d . 1 1 . .
H H11 -0.0384 0.1059 0.9650 0.077 Uiso calc R 1 1 . .
C C21 0.7850(2) 0.10299(13) 1.4133(2) 0.0559(6) Uani d . 1 1 . .
H H21 0.8449 0.0689 1.3901 0.067 Uiso calc R 1 1 . .
C C6 0.1268(2) 0.07803(13) 0.4276(3) 0.0601(6) Uani d . 1 1 . .
H H6 0.0709 0.0552 0.4850 0.072 Uiso calc R 1 1 . .
C C24 0.61859(19) 0.17992(12) 1.3549(2) 0.0541(5) Uani d . 1 1 . .
H H24 0.5646 0.1983 1.2885 0.065 Uiso calc R 1 1 . .
C C9 -0.0253(2) 0.24017(14) 0.7469(3) 0.0668(7) Uani d . 1 1 . .
H H9 -0.0641 0.2842 0.7225 0.080 Uiso calc R 1 1 . .
C C22 0.7765(3) 0.12783(14) 1.5463(3) 0.0663(7) Uani d . 1 1 . .
H H22 0.8298 0.1110 1.6147 0.080 Uiso calc R 1 1 . .
C C10 -0.0670(2) 0.19950(16) 0.8567(3) 0.0686(7) Uani d . 1 1 . .
H H10 -0.1331 0.2162 0.9071 0.082 Uiso calc R 1 1 . .
C C5 0.1175(3) 0.07000(15) 0.2857(3) 0.0767(8) Uani d . 1 1 . .
H H5 0.0553 0.0412 0.2476 0.092 Uiso calc R 1 1 . .
C C4 0.1995(3) 0.10438(18) 0.2009(3) 0.0751(8) Uani d . 1 1 . .
H H4 0.1934 0.0985 0.1058 0.090 Uiso calc R 1 1 . .
C C3 0.2895(2) 0.14712(17) 0.2569(2) 0.0729(8) Uani d . 1 1 . .
H H3 0.3443 0.1709 0.1993 0.087 Uiso calc R 1 1 . .
C C23 0.6874(2) 0.17810(14) 1.5755(3) 0.0675(7) Uani d . 1 1 . .
H H23 0.6821 0.1946 1.6660 0.081 Uiso calc R 1 1 . .



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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag

S1 C13 . 1.741(2) ?
S1 C16 . 1.741(2) ?
O1 C19 . 1.226(2) ?
N1 C13 . 1.380(3) ?
N1 C7 . 1.427(2) ?
N1 C1 . 1.439(3) ?
C18 C17 . 1.333(3) ?
C18 C19 . 1.458(3) ?
C18 H18 . 0.9300 ?
C14 C13 . 1.371(3) ?
C14 C15 . 1.398(3) ?
C14 H14 . 0.9300 ?
C7 C12 . 1.382(3) ?
C7 C8 . 1.384(3) ?
C20 C24 . 1.378(3) ?
C20 C21 . 1.387(3) ?
C20 C19 . 1.501(3) ?
C15 C16 . 1.365(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.431(3) ?
C1 C2 . 1.371(3) ?
C1 C6 . 1.382(3) ?
C2 C3 . 1.378(3) ?
C2 H2 . 0.9300 ?
C12 C11 . 1.389(3) ?
C12 H12 . 0.9300 ?
C17 H17 . 0.9300 ?
N2 C23 . 1.325(3) ?
N2 C24 . 1.343(3) ?
C8 C9 . 1.371(3) ?
C8 H8 . 0.9300 ?
C11 C10 . 1.380(4) ?
C11 H11 . 0.9300 ?
C21 C22 . 1.369(3) ?
C21 H21 . 0.9300 ?
C6 C5 . 1.387(4) ?
C6 H6 . 0.9300 ?
C24 H24 . 0.9300 ?
C9 C10 . 1.376(4) ?
C9 H9 . 0.9300 ?
C22 C23 . 1.365(4) ?
C22 H22 . 0.9300 ?
C10 H10 . 0.9300 ?
C5 C4 . 1.374(4) ?
C5 H5 . 0.9300 ?
C4 C3 . 1.361(4) ?
C4 H4 . 0.9300 ?
C3 H3 . 0.9300 ?
C23 H23 . 0.9300 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag

C13 S1 C16 . . 91.72(9) ?
C13 N1 C7 . . 122.32(17) ?
C13 N1 C1 . . 117.96(16) ?
C7 N1 C1 . . 119.03(16) ?
C17 C18 C19 . . 121.08(19) ?
C17 C18 H18 . . 119.5 ?
C19 C18 H18 . . 119.5 ?
C13 C14 C15 . . 112.96(18) ?
C13 C14 H14 . . 123.5 ?
C15 C14 H14 . . 123.5 ?
C12 C7 C8 . . 119.63(19) ?
C12 C7 N1 . . 121.20(19) ?
C8 C7 N1 . . 119.16(18) ?
C24 C20 C21 . . 116.9(2) ?
C24 C20 C19 . . 124.62(19) ?
C21 C20 C19 . . 118.52(19) ?
C14 C13 N1 . . 127.55(19) ?
C14 C13 S1 . . 110.71(15) ?
N1 C13 S1 . . 121.59(15) ?
C16 C15 C14 . . 114.53(18) ?
C16 C15 H15 . . 122.7 ?
C14 C15 H15 . . 122.7 ?
O1 C19 C18 . . 121.86(19) ?
O1 C19 C20 . . 118.29(18) ?
C18 C19 C20 . . 119.82(18) ?
C15 C16 C17 . . 126.36(19) ?
C15 C16 S1 . . 110.08(15) ?
C17 C16 S1 . . 123.53(15) ?
C2 C1 C6 . . 120.1(2) ?
C2 C1 N1 . . 119.88(19) ?
C6 C1 N1 . . 119.98(19) ?
C1 C2 C3 . . 119.8(2) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C7 C12 C11 . . 119.5(2) ?
C7 C12 H12 . . 120.2 ?
C11 C12 H12 . . 120.2 ?
C18 C17 C16 . . 129.0(2) ?
C18 C17 H17 . . 115.5 ?
C16 C17 H17 . . 115.5 ?
C23 N2 C24 . . 115.7(2) ?
C9 C8 C7 . . 120.4(2) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C10 C11 C12 . . 120.4(2) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C22 C21 C20 . . 119.9(2) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C1 C6 C5 . . 119.2(2) ?
C1 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
N2 C24 C20 . . 124.6(2) ?
N2 C24 H24 . . 117.7 ?
C20 C24 H24 . . 117.7 ?
C8 C9 C10 . . 120.5(2) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C23 C22 C21 . . 118.0(2) ?
C23 C22 H22 . . 121.0 ?
C21 C22 H22 . . 121.0 ?
C9 C10 C11 . . 119.5(2) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C4 C5 C6 . . 120.4(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C3 C4 C5 . . 119.7(2) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C3 C2 . . 120.8(2) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
N2 C23 C22 . . 125.0(2) ?
N2 C23 H23 . . 117.5 ?
C22 C23 H23 . . 117.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag

C13 N1 C7 C12 . . . . -45.5(3) ?
C1 N1 C7 C12 . . . . 124.8(2) ?
C13 N1 C7 C8 . . . . 135.9(2) ?
C1 N1 C7 C8 . . . . -53.9(3) ?
C15 C14 C13 N1 . . . . 176.09(19) ?
C15 C14 C13 S1 . . . . 0.6(2) ?
C7 N1 C13 C14 . . . . 150.3(2) ?
C1 N1 C13 C14 . . . . -20.1(3) ?
C7 N1 C13 S1 . . . . -34.7(3) ?
C1 N1 C13 S1 . . . . 154.93(15) ?
C16 S1 C13 C14 . . . . -0.95(16) ?
C16 S1 C13 N1 . . . . -176.74(17) ?
C13 C14 C15 C16 . . . . 0.2(3) ?
C17 C18 C19 O1 . . . . 8.2(3) ?
C17 C18 C19 C20 . . . . -169.57(19) ?
C24 C20 C19 O1 . . . . 168.2(2) ?
C21 C20 C19 O1 . . . . -12.1(3) ?
C24 C20 C19 C18 . . . . -13.9(3) ?
C21 C20 C19 C18 . . . . 165.80(19) ?
C14 C15 C16 C17 . . . . 177.10(19) ?
C14 C15 C16 S1 . . . . -0.9(2) ?
C13 S1 C16 C15 . . . . 1.05(16) ?
C13 S1 C16 C17 . . . . -177.03(18) ?
C13 N1 C1 C2 . . . . -62.3(3) ?
C7 N1 C1 C2 . . . . 127.0(2) ?
C13 N1 C1 C6 . . . . 117.6(2) ?
C7 N1 C1 C6 . . . . -53.1(3) ?
C6 C1 C2 C3 . . . . -1.6(3) ?
N1 C1 C2 C3 . . . . 178.2(2) ?
C8 C7 C12 C11 . . . . -1.2(3) ?
N1 C7 C12 C11 . . . . -179.87(19) ?
C19 C18 C17 C16 . . . . 177.90(19) ?
C15 C16 C17 C18 . . . . -175.2(2) ?
S1 C16 C17 C18 . . . . 2.6(3) ?
C12 C7 C8 C9 . . . . 1.3(3) ?
N1 C7 C8 C9 . . . . 179.96(19) ?
C7 C12 C11 C10 . . . . 0.2(3) ?
C24 C20 C21 C22 . . . . 0.9(3) ?
C19 C20 C21 C22 . . . . -178.9(2) ?
C2 C1 C6 C5 . . . . 1.8(3) ?
N1 C1 C6 C5 . . . . -178.0(2) ?
C23 N2 C24 C20 . . . . 0.6(3) ?
C21 C20 C24 N2 . . . . -1.1(3) ?
C19 C20 C24 N2 . . . . 178.65(19) ?
C7 C8 C9 C10 . . . . -0.3(4) ?
C20 C21 C22 C23 . . . . -0.3(4) ?
C8 C9 C10 C11 . . . . -0.7(4) ?
C12 C11 C10 C9 . . . . 0.8(4) ?
C1 C6 C5 C4 . . . . -0.7(4) ?
C6 C5 C4 C3 . . . . -0.7(4) ?
C5 C4 C3 C2 . . . . 0.9(4) ?
C1 C2 C3 C4 . . . . 0.2(4) ?
C24 N2 C23 C22 . . . . 0.0(4) ?
C21 C22 C23 N2 . . . . -0.2(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA

C11 H11 O1 1_455 0.93 2.54 3.410(3) 155
C12 H12 O1 3_657 0.93 2.43 3.346(3) 166
####################################################################### 
# 
# 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_C0
_audit_block_doi                 10.5517/cc1j7z91
_database_code_depnum_ccdc_archive 'CCDC 1407843'
_audit_update_record             
;
2015-06-20 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 (E)-3-(5-(diphenylamino)thiophen-2-yl)-1-phenylprop-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          415
_chemical_formula_moiety         'C25 H19 N O S'
_chemical_formula_sum            'C25 H19 N O S'
_chemical_formula_weight         381.47

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   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.145(6)
_cell_length_b                   18.243(9)
_cell_length_c                   9.722(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.995(6)
_cell_angle_gamma                90.00
_cell_volume                     1976.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2466
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      21.50

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_T_max  0.9685
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13845
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3471
_reflns_number_gt                2356
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)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         3471
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
C1 C 0.2964(2) 0.15301(16) -0.0990(2) 0.0757(7) Uani 1 1 d . . .
H1 H 0.3566 0.1829 -0.0624 0.091 Uiso 1 1 calc R . .
C2 C 0.2848(3) 0.1447(2) -0.2391(3) 0.0946(10) Uani 1 1 d . . .
H2 H 0.3374 0.1689 -0.2968 0.114 Uiso 1 1 calc R . .
C3 C 0.1974(3) 0.1015(2) -0.2938(3) 0.0911(10) Uani 1 1 d . . .
H3 H 0.1922 0.0946 -0.3885 0.109 Uiso 1 1 calc R . .
C4 C 0.1169(3) 0.06814(17) -0.2099(3) 0.0900(9) Uani 1 1 d . . .
H4 H 0.0547 0.0403 -0.2476 0.108 Uiso 1 1 calc R . .
C5 C 0.1284(2) 0.07602(14) -0.0680(3) 0.0721(7) Uani 1 1 d . . .
H5 H 0.0741 0.0531 -0.0105 0.087 Uiso 1 1 calc R . .
C6 C 0.21951(19) 0.11749(12) -0.0130(2) 0.0519(5) Uani 1 1 d . . .
C7 C 0.0802(2) 0.21463(13) 0.1801(3) 0.0652(6) Uani 1 1 d . . .
H7 H 0.1082 0.2424 0.1072 0.078 Uiso 1 1 calc R . .
C8 C -0.0152(2) 0.23895(15) 0.2546(3) 0.0779(8) Uani 1 1 d . . .
H8 H -0.0515 0.2834 0.2322 0.093 Uiso 1 1 calc R . .
C9 C -0.0572(2) 0.19818(18) 0.3620(3) 0.0812(9) Uani 1 1 d . . .
H9 H -0.1219 0.2150 0.4124 0.097 Uiso 1 1 calc R . .
C10 C -0.0037(2) 0.13216(17) 0.3955(2) 0.0743(8) Uani 1 1 d . . .
H10 H -0.0323 0.1047 0.4685 0.089 Uiso 1 1 calc R . .
C11 C 0.09267(19) 0.10653(14) 0.3206(2) 0.0600(6) Uani 1 1 d . . .
H11 H 0.1282 0.0618 0.3422 0.072 Uiso 1 1 calc R . .
C12 C 0.13499(18) 0.14845(12) 0.2137(2) 0.0508(5) Uani 1 1 d . . .
C13 C 0.33985(18) 0.09845(12) 0.1936(2) 0.0484(5) Uani 1 1 d . . .
C14 C 0.42117(19) 0.05202(12) 0.1368(2) 0.0578(6) Uani 1 1 d . . .
H14 H 0.4099 0.0296 0.0517 0.069 Uiso 1 1 calc R . .
C15 C 0.52339(19) 0.04175(12) 0.2202(2) 0.0557(6) Uani 1 1 d . . .
H15 H 0.5874 0.0125 0.1940 0.067 Uiso 1 1 calc R . .
C16 C 0.52197(17) 0.07791(11) 0.3424(2) 0.0470(5) Uani 1 1 d . . .
C17 C 0.61217(18) 0.07534(11) 0.4495(2) 0.0494(5) Uani 1 1 d . . .
H17 H 0.6818 0.0502 0.4275 0.059 Uiso 1 1 calc R . .
C18 C 0.61079(19) 0.10369(11) 0.5757(2) 0.0510(5) Uani 1 1 d . . .
H18 H 0.5432 0.1291 0.6041 0.061 Uiso 1 1 calc R . .
C19 C 0.71323(19) 0.09570(12) 0.6706(2) 0.0507(5) Uani 1 1 d . . .
C20 C 0.70651(18) 0.12607(11) 0.8132(2) 0.0476(5) Uani 1 1 d . . .
C21 C 0.6222(2) 0.17649(13) 0.8541(2) 0.0646(6) Uani 1 1 d . . .
H21 H 0.5644 0.1931 0.7914 0.078 Uiso 1 1 calc R . .
C22 C 0.6229(2) 0.20256(14) 0.9884(3) 0.0756(7) Uani 1 1 d . . .
H22 H 0.5660 0.2369 1.0145 0.091 Uiso 1 1 calc R . .
C23 C 0.7062(2) 0.17832(15) 1.0825(3) 0.0738(7) Uani 1 1 d . . .
H23 H 0.7060 0.1959 1.1723 0.089 Uiso 1 1 calc R . .
C24 C 0.7895(3) 0.12832(15) 1.0436(3) 0.0779(8) Uani 1 1 d . . .
H24 H 0.8460 0.1112 1.1075 0.093 Uiso 1 1 calc R . .
C25 C 0.7908(2) 0.10288(13) 0.9104(2) 0.0647(6) Uani 1 1 d . . .
H25 H 0.8494 0.0694 0.8851 0.078 Uiso 1 1 calc R . .
N1 N 0.23405(15) 0.12399(11) 0.13371(16) 0.0577(5) Uani 1 1 d . . .
O1 O 0.80483(14) 0.06383(10) 0.63514(16) 0.0723(5) Uani 1 1 d . . .
S1 S 0.38952(5) 0.12843(3) 0.35456(5) 0.0578(2) 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
C1 C6 1.370(3) . ?
C1 C2 1.374(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.353(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.437(3) . ?
C7 C8 1.370(3) . ?
C7 C12 1.389(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 N1 1.432(3) . ?
C13 C14 1.364(3) . ?
C13 N1 1.386(3) . ?
C13 S1 1.739(2) . ?
C14 C15 1.399(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.435(3) . ?
C16 S1 1.746(2) . ?
C17 C18 1.332(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.463(3) . ?
C18 H18 0.9300 . ?
C19 O1 1.229(2) . ?
C19 C20 1.495(3) . ?
C20 C21 1.379(3) . ?
C20 C25 1.388(3) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.359(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(3) . ?
C24 H24 0.9300 . ?
C25 H25 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
C6 C1 C2 120.2(3) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 N1 120.2(2) . . ?
C1 C6 N1 120.4(2) . . ?
C8 C7 C12 119.9(2) . . ?
C8 C7 H7 120.0 . . ?
C12 C7 H7 120.0 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.1(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C7 120.2(2) . . ?
C11 C12 N1 120.9(2) . . ?
C7 C12 N1 118.9(2) . . ?
C14 C13 N1 127.24(18) . . ?
C14 C13 S1 110.84(16) . . ?
N1 C13 S1 121.81(15) . . ?
C13 C14 C15 112.90(19) . . ?
C13 C14 H14 123.6 . . ?
C15 C14 H14 123.6 . . ?
C16 C15 C14 114.80(19) . . ?
C16 C15 H15 122.6 . . ?
C14 C15 H15 122.6 . . ?
C15 C16 C17 126.83(19) . . ?
C15 C16 S1 109.76(15) . . ?
C17 C16 S1 123.39(16) . . ?
C18 C17 C16 129.5(2) . . ?
C18 C17 H17 115.2 . . ?
C16 C17 H17 115.2 . . ?
C17 C18 C19 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
O1 C19 C18 120.8(2) . . ?
O1 C19 C20 119.38(19) . . ?
C18 C19 C20 119.78(19) . . ?
C21 C20 C25 117.6(2) . . ?
C21 C20 C19 124.04(19) . . ?
C25 C20 C19 118.3(2) . . ?
C20 C21 C22 120.4(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 119.4(2) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.4(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 121.4(2) . . ?
C24 C25 H25 119.3 . . ?
C20 C25 H25 119.3 . . ?
C13 N1 C12 122.33(16) . . ?
C13 N1 C6 117.97(16) . . ?
C12 N1 C6 119.30(16) . . ?
C13 S1 C16 91.68(10) . . ?

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
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 2.6(5) . . . . ?
C2 C3 C4 C5 -2.9(5) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 2.2(4) . . . . ?
C4 C5 C6 N1 -178.1(2) . . . . ?
C2 C1 C6 C5 -2.5(4) . . . . ?
C2 C1 C6 N1 177.8(2) . . . . ?
C12 C7 C8 C9 -0.2(4) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C7 -1.2(3) . . . . ?
C10 C11 C12 N1 -179.91(19) . . . . ?
C8 C7 C12 C11 0.9(3) . . . . ?
C8 C7 C12 N1 179.62(19) . . . . ?
N1 C13 C14 C15 175.1(2) . . . . ?
S1 C13 C14 C15 -1.3(3) . . . . ?
C13 C14 C15 C16 1.5(3) . . . . ?
C14 C15 C16 C17 177.6(2) . . . . ?
C14 C15 C16 S1 -1.1(2) . . . . ?
C15 C16 C17 C18 -172.9(2) . . . . ?
S1 C16 C17 C18 5.6(3) . . . . ?
C16 C17 C18 C19 -179.4(2) . . . . ?
C17 C18 C19 O1 1.6(3) . . . . ?
C17 C18 C19 C20 -177.88(19) . . . . ?
O1 C19 C20 C21 164.4(2) . . . . ?
C18 C19 C20 C21 -16.1(3) . . . . ?
O1 C19 C20 C25 -14.9(3) . . . . ?
C18 C19 C20 C25 164.6(2) . . . . ?
C25 C20 C21 C22 0.0(3) . . . . ?
C19 C20 C21 C22 -179.3(2) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C24 C25 C20 -1.3(4) . . . . ?
C21 C20 C25 C24 1.0(3) . . . . ?
C19 C20 C25 C24 -179.7(2) . . . . ?
C14 C13 N1 C12 155.7(2) . . . . ?
S1 C13 N1 C12 -28.3(3) . . . . ?
C14 C13 N1 C6 -17.1(3) . . . . ?
S1 C13 N1 C6 158.89(16) . . . . ?
C11 C12 N1 C13 -48.9(3) . . . . ?
C7 C12 N1 C13 132.4(2) . . . . ?
C11 C12 N1 C6 123.8(2) . . . . ?
C7 C12 N1 C6 -54.9(3) . . . . ?
C5 C6 N1 C13 118.4(2) . . . . ?
C1 C6 N1 C13 -62.0(3) . . . . ?
C5 C6 N1 C12 -54.6(3) . . . . ?
C1 C6 N1 C12 125.1(2) . . . . ?
C14 C13 S1 C16 0.56(17) . . . . ?
N1 C13 S1 C16 -176.01(19) . . . . ?
C15 C16 S1 C13 0.29(17) . . . . ?
C17 C16 S1 C13 -178.46(19) . . . . ?

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
C10 H10 O1 0.93 2.56 3.422(3) 153.5 1_455
C11 H11 O1 0.93 2.42 3.336(3) 169.1 3_656
C17 H17 O1 0.93 2.43 2.789(3) 102.7 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_OC0
_audit_block_doi                 10.5517/cc1j7zb2
_database_code_depnum_ccdc_archive 'CCDC 1407844'
_audit_update_record             
;
2015-06-20 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (E)-3-(5-(bis(4-ethoxyphenyl)amino)thiophen-2-yl)-1-phenylprop-2-en-1-one 
;
_chemical_name_common            ?
_chemical_melting_point          411
_chemical_formula_moiety         'C29 H27 N O3 S'
_chemical_formula_sum            'C29 H27 N O3 S'
_chemical_formula_weight         469.58

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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5078(9)
_cell_length_b                   13.846(2)
_cell_length_c                   16.264(3)
_cell_angle_alpha                85.220(2)
_cell_angle_beta                 84.223(2)
_cell_angle_gamma                85.091(2)
_cell_volume                     1226.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2407
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.12

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8799
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4278
_reflns_number_gt                3107
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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         4278
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1616
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C 1.3555(5) 0.1967(2) -0.18803(17) 0.0672(8) Uani 1 1 d . . .
H1 H 1.3591 0.2554 -0.2202 0.081 Uiso 1 1 calc R . .
C2 C 1.5407(5) 0.1247(2) -0.20158(19) 0.0759(9) Uani 1 1 d . . .
H2 H 1.6684 0.1357 -0.2424 0.091 Uiso 1 1 calc R . .
C3 C 1.5388(5) 0.0381(2) -0.1560(2) 0.0751(8) Uani 1 1 d . . .
H3 H 1.6632 -0.0105 -0.1658 0.090 Uiso 1 1 calc R . .
C4 C 1.3516(6) 0.0232(2) -0.0956(2) 0.0864(10) Uani 1 1 d . . .
H4 H 1.3497 -0.0358 -0.0637 0.104 Uiso 1 1 calc R . .
C5 C 1.1655(5) 0.0949(2) -0.08134(18) 0.0720(8) Uani 1 1 d . . .
H5 H 1.0395 0.0834 -0.0401 0.086 Uiso 1 1 calc R . .
C6 C 1.1632(4) 0.18293(18) -0.12706(14) 0.0509(6) Uani 1 1 d . . .
C7 C 0.9697(5) 0.26395(18) -0.11424(15) 0.0552(6) Uani 1 1 d . . .
C8 C 0.7756(5) 0.25575(18) -0.04627(14) 0.0521(6) Uani 1 1 d . . .
H8 H 0.7764 0.2009 -0.0091 0.062 Uiso 1 1 calc R . .
C9 C 0.5973(4) 0.32679(18) -0.03740(14) 0.0512(6) Uani 1 1 d . . .
H9 H 0.6053 0.3774 -0.0787 0.061 Uiso 1 1 calc R . .
C10 C 0.3967(4) 0.33835(17) 0.02450(13) 0.0473(6) Uani 1 1 d . . .
C11 C 0.2519(4) 0.42205(17) 0.03647(14) 0.0487(6) Uani 1 1 d . . .
H11 H 0.2632 0.4770 -0.0003 0.058 Uiso 1 1 calc R . .
C12 C 0.0862(4) 0.42005(16) 0.10715(14) 0.0464(6) Uani 1 1 d . . .
H12 H -0.0198 0.4727 0.1227 0.056 Uiso 1 1 calc R . .
C13 C 0.0985(4) 0.33050(15) 0.15120(13) 0.0406(5) Uani 1 1 d . . .
C14 C -0.2197(4) 0.36277(16) 0.26505(13) 0.0436(5) Uani 1 1 d . . .
C15 C -0.3955(4) 0.41772(17) 0.22325(14) 0.0477(6) Uani 1 1 d . . .
H15 H -0.3954 0.4145 0.1664 0.057 Uiso 1 1 calc R . .
C16 C -0.5723(4) 0.47774(17) 0.26481(14) 0.0499(6) Uani 1 1 d . . .
H16 H -0.6880 0.5153 0.2356 0.060 Uiso 1 1 calc R . .
C17 C -0.5770(5) 0.48186(18) 0.34957(14) 0.0536(6) Uani 1 1 d . . .
C18 C -0.4042(5) 0.4248(2) 0.39206(15) 0.0623(7) Uani 1 1 d . . .
H18 H -0.4093 0.4253 0.4494 0.075 Uiso 1 1 calc R . .
C19 C -0.2249(5) 0.36729(19) 0.34998(14) 0.0578(7) Uani 1 1 d . . .
H19 H -0.1063 0.3312 0.3789 0.069 Uiso 1 1 calc R . .
C20 C -0.9252(5) 0.5976(2) 0.35529(19) 0.0729(8) Uani 1 1 d . . .
H20A H -1.0104 0.5584 0.3226 0.087 Uiso 1 1 calc R . .
H20B H -0.8503 0.6479 0.3185 0.087 Uiso 1 1 calc R . .
C21 C -1.1022(6) 0.6430(3) 0.4208(2) 0.0989(11) Uani 1 1 d . . .
H21A H -1.1835 0.5929 0.4544 0.148 Uiso 1 1 calc R . .
H21B H -1.2212 0.6866 0.3947 0.148 Uiso 1 1 calc R . .
H21C H -1.0144 0.6783 0.4550 0.148 Uiso 1 1 calc R . .
C22 C 0.0235(4) 0.20519(16) 0.26340(14) 0.0455(6) Uani 1 1 d . . .
C23 C 0.2174(5) 0.18819(18) 0.31139(16) 0.0552(6) Uani 1 1 d . . .
H23 H 0.3205 0.2371 0.3151 0.066 Uiso 1 1 calc R . .
C24 C 0.2588(5) 0.09904(19) 0.35388(16) 0.0598(7) Uani 1 1 d . . .
H24 H 0.3896 0.0878 0.3863 0.072 Uiso 1 1 calc R . .
C25 C 0.1070(5) 0.02681(18) 0.34833(15) 0.0553(7) Uani 1 1 d . . .
C26 C -0.0819(5) 0.04219(18) 0.29758(17) 0.0590(7) Uani 1 1 d . . .
H26 H -0.1799 -0.0078 0.2917 0.071 Uiso 1 1 calc R . .
C27 C -0.1239(4) 0.13165(18) 0.25596(15) 0.0523(6) Uani 1 1 d . . .
H27 H -0.2527 0.1425 0.2226 0.063 Uiso 1 1 calc R . .
C28 C 0.3210(8) -0.0829(2) 0.4445(2) 0.1051(13) Uani 1 1 d . . .
H28A H 0.4777 -0.0717 0.4139 0.126 Uiso 1 1 calc R . .
H28B H 0.2940 -0.0387 0.4883 0.126 Uiso 1 1 calc R . .
C29 C 0.3256(9) -0.1799(3) 0.4795(3) 0.1296(16) Uani 1 1 d . . .
H29A H 0.1699 -0.1911 0.5094 0.194 Uiso 1 1 calc R . .
H29B H 0.4514 -0.1908 0.5167 0.194 Uiso 1 1 calc R . .
H29C H 0.3585 -0.2236 0.4362 0.194 Uiso 1 1 calc R . .
N1 N -0.0336(3) 0.30064(13) 0.22334(11) 0.0486(5) Uani 1 1 d . . .
O1 O 0.1290(4) -0.06383(13) 0.38961(13) 0.0779(6) Uani 1 1 d . . .
O2 O -0.7428(3) 0.53859(14) 0.39633(11) 0.0717(6) Uani 1 1 d . . .
O3 O 0.9753(4) 0.33785(15) -0.16196(12) 0.0875(7) Uani 1 1 d . . .
S1 S 0.31893(11) 0.25005(4) 0.10349(4) 0.0484(2) 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
C1 C2 1.378(4) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.493(3) . ?
C7 O3 1.232(3) . ?
C7 C8 1.463(3) . ?
C8 C9 1.335(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.426(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(3) . ?
C10 S1 1.745(2) . ?
C11 C12 1.394(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 N1 1.369(3) . ?
C13 S1 1.744(2) . ?
C14 C15 1.378(3) . ?
C14 C19 1.385(3) . ?
C14 N1 1.434(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 O2 1.366(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 O2 1.423(3) . ?
C20 C21 1.509(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.376(3) . ?
C22 C23 1.378(3) . ?
C22 N1 1.448(3) . ?
C23 C24 1.376(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(4) . ?
C24 H24 0.9300 . ?
C25 O1 1.375(3) . ?
C25 C26 1.384(4) . ?
C26 C27 1.374(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.413(4) . ?
C28 O1 1.445(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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
C2 C1 C6 121.1(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 117.3(2) . . ?
C5 C6 C7 123.9(2) . . ?
C1 C6 C7 118.8(2) . . ?
O3 C7 C8 120.4(2) . . ?
O3 C7 C6 119.0(2) . . ?
C8 C7 C6 120.6(2) . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 131.1(2) . . ?
C8 C9 H9 114.5 . . ?
C10 C9 H9 114.5 . . ?
C11 C10 C9 125.8(2) . . ?
C11 C10 S1 109.40(17) . . ?
C9 C10 S1 124.49(18) . . ?
C10 C11 C12 115.9(2) . . ?
C10 C11 H11 122.0 . . ?
C12 C11 H11 122.0 . . ?
C13 C12 C11 111.8(2) . . ?
C13 C12 H12 124.1 . . ?
C11 C12 H12 124.1 . . ?
N1 C13 C12 129.0(2) . . ?
N1 C13 S1 119.86(16) . . ?
C12 C13 S1 111.16(16) . . ?
C15 C14 C19 118.8(2) . . ?
C15 C14 N1 122.0(2) . . ?
C19 C14 N1 119.2(2) . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
O2 C17 C16 124.7(2) . . ?
O2 C17 C18 116.1(2) . . ?
C16 C17 C18 119.1(2) . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
O2 C20 C21 107.7(3) . . ?
O2 C20 H20A 110.2 . . ?
C21 C20 H20A 110.2 . . ?
O2 C20 H20B 110.2 . . ?
C21 C20 H20B 110.2 . . ?
H20A C20 H20B 108.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 119.7(2) . . ?
C27 C22 N1 119.4(2) . . ?
C23 C22 N1 120.9(2) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 O1 124.5(2) . . ?
C24 C25 C26 120.1(2) . . ?
O1 C25 C26 115.4(2) . . ?
C27 C26 C25 119.7(2) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C22 120.3(2) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
C29 C28 O1 110.6(3) . . ?
C29 C28 H28A 109.5 . . ?
O1 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
O1 C28 H28B 109.5 . . ?
H28A C28 H28B 108.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C13 N1 C14 122.61(18) . . ?
C13 N1 C22 119.98(17) . . ?
C14 N1 C22 117.29(17) . . ?
C25 O1 C28 117.5(2) . . ?
C17 O2 C20 118.0(2) . . ?
C13 S1 C10 91.71(10) . . ?

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
C6 C1 C2 C3 0.6(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C7 -179.2(3) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
C2 C1 C6 C7 179.0(3) . . . . ?
C5 C6 C7 O3 -175.4(3) . . . . ?
C1 C6 C7 O3 5.4(4) . . . . ?
C5 C6 C7 C8 4.4(4) . . . . ?
C1 C6 C7 C8 -174.8(2) . . . . ?
O3 C7 C8 C9 2.7(4) . . . . ?
C6 C7 C8 C9 -177.1(2) . . . . ?
C7 C8 C9 C10 -176.9(2) . . . . ?
C8 C9 C10 C11 166.7(3) . . . . ?
C8 C9 C10 S1 -6.4(4) . . . . ?
C9 C10 C11 C12 -172.2(2) . . . . ?
S1 C10 C11 C12 1.8(3) . . . . ?
C10 C11 C12 C13 -1.3(3) . . . . ?
C11 C12 C13 N1 179.8(2) . . . . ?
C11 C12 C13 S1 0.2(3) . . . . ?
C19 C14 C15 C16 1.1(4) . . . . ?
N1 C14 C15 C16 -179.5(2) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C15 C16 C17 O2 179.9(2) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
O2 C17 C18 C19 -178.1(2) . . . . ?
C16 C17 C18 C19 2.3(4) . . . . ?
C17 C18 C19 C14 -2.4(4) . . . . ?
C15 C14 C19 C18 0.7(4) . . . . ?
N1 C14 C19 C18 -178.7(2) . . . . ?
C27 C22 C23 C24 -2.1(4) . . . . ?
N1 C22 C23 C24 175.3(2) . . . . ?
C22 C23 C24 C25 0.1(4) . . . . ?
C23 C24 C25 O1 -178.5(2) . . . . ?
C23 C24 C25 C26 2.5(4) . . . . ?
C24 C25 C26 C27 -3.2(4) . . . . ?
O1 C25 C26 C27 177.7(2) . . . . ?
C25 C26 C27 C22 1.2(4) . . . . ?
C23 C22 C27 C26 1.4(4) . . . . ?
N1 C22 C27 C26 -176.0(2) . . . . ?
C12 C13 N1 C14 1.3(4) . . . . ?
S1 C13 N1 C14 -179.12(17) . . . . ?
C12 C13 N1 C22 -174.6(2) . . . . ?
S1 C13 N1 C22 5.0(3) . . . . ?
C15 C14 N1 C13 46.6(3) . . . . ?
C19 C14 N1 C13 -133.9(3) . . . . ?
C15 C14 N1 C22 -137.4(2) . . . . ?
C19 C14 N1 C22 42.0(3) . . . . ?
C27 C22 N1 C13 -102.9(3) . . . . ?
C23 C22 N1 C13 79.7(3) . . . . ?
C27 C22 N1 C14 81.0(3) . . . . ?
C23 C22 N1 C14 -96.4(3) . . . . ?
C24 C25 O1 C28 2.0(4) . . . . ?
C26 C25 O1 C28 -179.0(3) . . . . ?
C29 C28 O1 C25 -177.7(3) . . . . ?
C16 C17 O2 C20 0.3(4) . . . . ?
C18 C17 O2 C20 -179.4(3) . . . . ?
C21 C20 O2 C17 173.1(3) . . . . ?
N1 C13 S1 C10 -179.02(19) . . . . ?
C12 C13 S1 C10 0.65(18) . . . . ?
C11 C10 S1 C13 -1.34(19) . . . . ?
C9 C10 S1 C13 172.7(2) . . . . ?

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
C9 H9 O3 0.93 2.38 2.760(3) 104.2 .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.056
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_OC1
_audit_block_doi                 10.5517/cc1j7zc3
_database_code_depnum_ccdc_archive 'CCDC 1407845'
_audit_update_record             
;
2015-06-20 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (E)-3-(5-(bis(4-ethoxyphenyl)amino)thiophen-2-yl)-1-(pyridin-2-yl)prop-2-en-1-one 
;
_chemical_name_common            ?
_chemical_melting_point          422
_chemical_formula_moiety         'C28 H26 N2 O3 S'
_chemical_formula_sum            'C28 H26 N2 O3 S'
_chemical_formula_weight         470.57

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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.406(5)
_cell_length_b                   11.831(9)
_cell_length_c                   14.142(10)
_cell_angle_alpha                89.231(9)
_cell_angle_beta                 81.249(9)
_cell_angle_gamma                89.949(9)
_cell_volume                     1224.6(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2882
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.46

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_T_max  0.9663
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8991
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.49
_reflns_number_total             4467
_reflns_number_gt                3232
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0453P)²+0.2685P] 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         4467
_refine_ls_number_parameters     338
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.985
_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
C1 C 1.2081(4) 1.0761(2) 0.03536(19) 0.0847(7) Uani 1 1 d . . .
H1 H 1.1944 1.0404 -0.0213 0.102 Uiso 1 1 calc R . .
C2 C 1.3714(4) 1.1276(2) 0.0407(2) 0.0849(7) Uani 1 1 d . . .
H2 H 1.4659 1.1263 -0.0107 0.102 Uiso 1 1 calc R . .
C3 C 1.3926(3) 1.1812(2) 0.1235(2) 0.0864(8) Uani 1 1 d . . .
H3 H 1.5019 1.2170 0.1294 0.104 Uiso 1 1 calc R . .
C4 C 1.2500(3) 1.18101(19) 0.19752(17) 0.0706(6) Uani 1 1 d . . .
H4 H 1.2609 1.2172 0.2544 0.085 Uiso 1 1 calc R . .
C5 C 1.0897(3) 1.12642(16) 0.18662(15) 0.0579(5) Uani 1 1 d . . .
C6 C 0.9339(3) 1.12513(17) 0.26772(16) 0.0608(5) Uani 1 1 d . . .
C7 C 0.7720(3) 1.05775(17) 0.26040(15) 0.0588(5) Uani 1 1 d . . .
H7 H 0.7687 1.0127 0.2073 0.071 Uiso 1 1 calc R . .
C8 C 0.6283(3) 1.06088(17) 0.33014(15) 0.0597(5) Uani 1 1 d . . .
H8 H 0.6388 1.1115 0.3788 0.072 Uiso 1 1 calc R . .
C9 C 0.4624(3) 0.99895(16) 0.34137(14) 0.0557(5) Uani 1 1 d . . .
C10 C 0.3237(3) 1.00406(18) 0.41691(15) 0.0655(6) Uani 1 1 d . . .
H10 H 0.3244 1.0542 0.4669 0.079 Uiso 1 1 calc R . .
C11 C 0.1808(3) 0.92818(18) 0.41322(16) 0.0658(6) Uani 1 1 d . . .
H11 H 0.0779 0.9229 0.4598 0.079 Uiso 1 1 calc R . .
C12 C 0.2089(3) 0.86251(16) 0.33357(14) 0.0518(5) Uani 1 1 d . . .
N2 N 0.0999(2) 0.77635(14) 0.31114(11) 0.0573(4) Uani 1 1 d . . .
C13 C 0.1414(2) 0.71388(16) 0.22482(13) 0.0501(5) Uani 1 1 d . . .
C14 C 0.1462(3) 0.76564(17) 0.13591(14) 0.0560(5) Uani 1 1 d . . .
H14 H 0.1252 0.8429 0.1317 0.067 Uiso 1 1 calc R . .
C15 C 0.1819(3) 0.70299(17) 0.05400(14) 0.0562(5) Uani 1 1 d . . .
H15 H 0.1863 0.7385 -0.0054 0.067 Uiso 1 1 calc R . .
C16 C 0.2112(2) 0.58771(16) 0.05894(14) 0.0515(5) Uani 1 1 d . . .
C17 C 0.2035(3) 0.53558(17) 0.14765(14) 0.0581(5) Uani 1 1 d . . .
H17 H 0.2207 0.4579 0.1521 0.070 Uiso 1 1 calc R . .
C18 C 0.1701(3) 0.59915(17) 0.22920(14) 0.0572(5) Uani 1 1 d . . .
H18 H 0.1668 0.5638 0.2886 0.069 Uiso 1 1 calc R . .
C19 C 0.2743(3) 0.41339(18) -0.02255(15) 0.0643(6) Uani 1 1 d . . .
H19A H 0.1688 0.3761 0.0137 0.077 Uiso 1 1 calc R . .
H19B H 0.3797 0.3975 0.0086 0.077 Uiso 1 1 calc R . .
C20 C 0.3062(3) 0.3710(2) -0.12283(16) 0.0786(7) Uani 1 1 d . . .
H20A H 0.2013 0.3873 -0.1531 0.118 Uiso 1 1 calc R . .
H20B H 0.3259 0.2908 -0.1219 0.118 Uiso 1 1 calc R . .
H20C H 0.4117 0.4076 -0.1579 0.118 Uiso 1 1 calc R . .
C21 C -0.0496(3) 0.73825(16) 0.38117(14) 0.0557(5) Uani 1 1 d . A .
C22 C -0.2242(3) 0.74974(18) 0.36305(16) 0.0662(6) Uani 1 1 d . . .
H22 H -0.2460 0.7831 0.3060 0.079 Uiso 1 1 calc R . .
C23 C -0.3685(4) 0.7121(2) 0.4290(2) 0.0932(9) Uani 1 1 d . A .
H23 H -0.4873 0.7199 0.4160 0.112 Uiso 1 1 calc R . .
C24 C -0.3386(6) 0.6632(3) 0.5134(3) 0.1126(13) Uani 1 1 d . . .
C25 C -0.1637(7) 0.6533(3) 0.5311(2) 0.1225(13) Uani 1 1 d . A .
H25 H -0.1422 0.6212 0.5887 0.147 Uiso 1 1 calc R . .
C26 C -0.0188(4) 0.6895(2) 0.46609(18) 0.0893(8) Uani 1 1 d . . .
H26 H 0.0999 0.6813 0.4792 0.107 Uiso 1 1 calc R A .
O3 O -0.4308(6) 0.6153(3) 0.5971(3) 0.0892(16) Uani 0.566(7) 1 d PD A 1
C27 C -0.6207(8) 0.6211(5) 0.5892(6) 0.093(2) Uani 0.566(7) 1 d PD A 1
H27A H -0.6460 0.5750 0.5365 0.111 Uiso 0.566(7) 1 calc PR A 1
H27B H -0.6546 0.6985 0.5769 0.111 Uiso 0.566(7) 1 calc PR A 1
C28 C -0.7290(13) 0.5784(10) 0.6817(9) 0.097(4) Uani 0.566(7) 1 d PD A 1
H28A H -0.6986 0.5007 0.6918 0.145 Uiso 0.566(7) 1 calc PR A 1
H28B H -0.8571 0.5845 0.6784 0.145 Uiso 0.566(7) 1 calc PR A 1
H28C H -0.7001 0.6228 0.7337 0.145 Uiso 0.566(7) 1 calc PR A 1
C27' C -0.5442(13) 0.6034(6) 0.6496(5) 0.084(2) Uani 0.434(7) 1 d PD A 2
H27C H -0.4993 0.6617 0.6877 0.101 Uiso 0.434(7) 1 calc PR A 2
H27D H -0.4686 0.5367 0.6515 0.101 Uiso 0.434(7) 1 calc PR A 2
O3' O -0.5403(8) 0.6426(4) 0.5522(3) 0.0756(18) Uani 0.434(7) 1 d PD A 2
C28' C -0.741(2) 0.576(2) 0.6873(18) 0.169(11) Uani 0.434(7) 1 d PD A 2
H28E H -0.8157 0.6406 0.6786 0.253 Uiso 0.434(7) 1 calc PR A 2
H28F H -0.7527 0.5572 0.7542 0.253 Uiso 0.434(7) 1 calc PR A 2
H28G H -0.7795 0.5132 0.6532 0.253 Uiso 0.434(7) 1 calc PR A 2
N1 N 1.0672(3) 1.07392(16) 0.10655(14) 0.0713(5) Uani 1 1 d . . .
O1 O 0.9477(2) 1.18154(15) 0.33832(12) 0.0902(5) Uani 1 1 d . . .
O2 O 0.2439(2) 0.53286(12) -0.02616(9) 0.0640(4) Uani 1 1 d . . .
S1 S 0.41248(7) 0.89669(4) 0.26128(4) 0.05605(17) 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
C1 N1 1.336(3) . ?
C1 C2 1.368(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.331(3) . ?
C5 C6 1.498(3) . ?
C6 O1 1.225(2) . ?
C6 C7 1.458(3) . ?
C7 C8 1.337(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.418(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(3) . ?
C9 S1 1.746(2) . ?
C10 C11 1.396(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(3) . ?
C11 H11 0.9300 . ?
C12 N2 1.371(2) . ?
C12 S1 1.733(2) . ?
N2 C13 1.429(2) . ?
N2 C21 1.437(2) . ?
C13 C18 1.376(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9300 . ?
C16 O2 1.364(2) . ?
C16 C17 1.384(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O2 1.433(3) . ?
C19 C20 1.495(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.363(3) . ?
C21 C26 1.375(3) . ?
C22 C23 1.377(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.361(5) . ?
C24 O3 1.388(5) . ?
C24 O3' 1.530(7) . ?
C25 C26 1.368(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
O3 C27 1.429(7) . ?
C27 C28 1.508(9) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C27' O3' 1.443(8) . ?
C27' C28' 1.507(10) . ?
C27' H27C 0.9700 . ?
C27' H27D 0.9700 . ?
C28' H28E 0.9600 . ?
C28' H28F 0.9600 . ?
C28' H28G 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
N1 C1 C2 124.0(3) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.7(2) . . ?
N1 C5 C6 118.00(19) . . ?
C4 C5 C6 119.3(2) . . ?
O1 C6 C7 122.3(2) . . ?
O1 C6 C5 118.29(19) . . ?
C7 C6 C5 119.46(19) . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 130.0(2) . . ?
C7 C8 H8 115.0 . . ?
C9 C8 H8 115.0 . . ?
C10 C9 C8 126.53(19) . . ?
C10 C9 S1 109.66(15) . . ?
C8 C9 S1 123.71(16) . . ?
C9 C10 C11 114.84(19) . . ?
C9 C10 H10 122.6 . . ?
C11 C10 H10 122.6 . . ?
C12 C11 C10 112.51(19) . . ?
C12 C11 H11 123.7 . . ?
C10 C11 H11 123.7 . . ?
C11 C12 N2 127.03(18) . . ?
C11 C12 S1 111.40(15) . . ?
N2 C12 S1 121.52(15) . . ?
C12 N2 C13 122.32(16) . . ?
C12 N2 C21 119.19(16) . . ?
C13 N2 C21 118.09(15) . . ?
C18 C13 C14 118.78(18) . . ?
C18 C13 N2 119.83(17) . . ?
C14 C13 N2 121.34(18) . . ?
C15 C14 C13 120.17(19) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.73(18) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
O2 C16 C15 116.34(17) . . ?
O2 C16 C17 124.46(18) . . ?
C15 C16 C17 119.19(18) . . ?
C18 C17 C16 119.69(19) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C13 C18 C17 121.42(19) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
O2 C19 C20 108.22(18) . . ?
O2 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
O2 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 119.5(2) . . ?
C22 C21 N2 119.65(19) . . ?
C26 C21 N2 120.9(2) . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 118.7(3) . . ?
C25 C24 O3 99.7(4) . . ?
C23 C24 O3 141.6(4) . . ?
C25 C24 O3' 145.7(4) . . ?
C23 C24 O3' 95.6(4) . . ?
O3 C24 O3' 46.0(2) . . ?
C24 C25 C26 121.5(3) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C21 119.6(3) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
C24 O3 C27 106.1(6) . . ?
O3 C27 C28 108.5(8) . . ?
O3 C27 H27A 110.0 . . ?
C28 C27 H27A 110.0 . . ?
O3 C27 H27B 110.0 . . ?
C28 C27 H27B 110.0 . . ?
H27A C27 H27B 108.4 . . ?
O3' C27' C28' 106.3(13) . . ?
O3' C27' H27C 110.5 . . ?
C28' C27' H27C 110.5 . . ?
O3' C27' H27D 110.5 . . ?
C28' C27' H27D 110.5 . . ?
H27C C27' H27D 108.7 . . ?
C27' O3' C24 105.5(6) . . ?
C27' C28' H28E 109.5 . . ?
C27' C28' H28F 109.5 . . ?
H28E C28' H28F 109.5 . . ?
C27' C28' H28G 109.5 . . ?
H28E C28' H28G 109.5 . . ?
H28F C28' H28G 109.5 . . ?
C5 N1 C1 116.9(2) . . ?
C16 O2 C19 117.20(15) . . ?
C12 S1 C9 91.56(10) . . ?

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
N1 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 N1 -0.3(3) . . . . ?
C3 C4 C5 C6 179.4(2) . . . . ?
N1 C5 C6 O1 -173.7(2) . . . . ?
C4 C5 C6 O1 6.6(3) . . . . ?
N1 C5 C6 C7 6.2(3) . . . . ?
C4 C5 C6 C7 -173.5(2) . . . . ?
O1 C6 C7 C8 3.5(3) . . . . ?
C5 C6 C7 C8 -176.37(19) . . . . ?
C6 C7 C8 C9 -176.1(2) . . . . ?
C7 C8 C9 C10 177.5(2) . . . . ?
C7 C8 C9 S1 1.5(3) . . . . ?
C8 C9 C10 C11 -175.7(2) . . . . ?
S1 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 N2 176.4(2) . . . . ?
C10 C11 C12 S1 -1.1(2) . . . . ?
C11 C12 N2 C13 179.2(2) . . . . ?
S1 C12 N2 C13 -3.5(3) . . . . ?
C11 C12 N2 C21 -8.3(3) . . . . ?
S1 C12 N2 C21 169.00(15) . . . . ?
C12 N2 C13 C18 119.4(2) . . . . ?
C21 N2 C13 C18 -53.2(3) . . . . ?
C12 N2 C13 C14 -63.4(3) . . . . ?
C21 N2 C13 C14 124.0(2) . . . . ?
C18 C13 C14 C15 -1.0(3) . . . . ?
N2 C13 C14 C15 -178.31(17) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 O2 179.42(17) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
O2 C16 C17 C18 179.80(18) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
N2 C13 C18 C17 177.48(18) . . . . ?
C16 C17 C18 C13 0.9(3) . . . . ?
C12 N2 C21 C22 116.6(2) . . . . ?
C13 N2 C21 C22 -70.5(3) . . . . ?
C12 N2 C21 C26 -63.9(3) . . . . ?
C13 N2 C21 C26 109.0(2) . . . . ?
C26 C21 C22 C23 -0.5(3) . . . . ?
N2 C21 C22 C23 179.06(19) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C22 C23 C24 O3 179.8(4) . . . . ?
C22 C23 C24 O3' 179.5(3) . . . . ?
C23 C24 C25 C26 -0.9(5) . . . . ?
O3 C24 C25 C26 179.5(3) . . . . ?
O3' C24 C25 C26 -179.3(4) . . . . ?
C24 C25 C26 C21 0.7(5) . . . . ?
C22 C21 C26 C25 0.0(4) . . . . ?
N2 C21 C26 C25 -179.5(2) . . . . ?
C25 C24 O3 C27 179.4(4) . . . . ?
C23 C24 O3 C27 -0.1(6) . . . . ?
O3' C24 O3 C27 0.4(4) . . . . ?
C24 O3 C27 C28 -175.6(6) . . . . ?
C28' C27' O3' C24 -176.7(11) . . . . ?
C25 C24 O3' C27' 6.0(8) . . . . ?
C23 C24 O3' C27' -172.5(4) . . . . ?
O3 C24 O3' C27' 7.7(4) . . . . ?
C4 C5 N1 C1 -0.1(3) . . . . ?
C6 C5 N1 C1 -179.9(2) . . . . ?
C2 C1 N1 C5 0.6(4) . . . . ?
C15 C16 O2 C19 -179.90(17) . . . . ?
C17 C16 O2 C19 -0.8(3) . . . . ?
C20 C19 O2 C16 179.76(17) . . . . ?
C11 C12 S1 C9 1.29(17) . . . . ?
N2 C12 S1 C9 -176.38(17) . . . . ?
C10 C9 S1 C12 -1.16(16) . . . . ?
C8 C9 S1 C12 175.41(18) . . . . ?

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
C8 H8 O1 0.93 2.42 2.782(3) 103.3 .

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.032
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_OC2
_audit_block_doi                 10.5517/cc1j7zd4
_database_code_depnum_ccdc_archive 'CCDC 1407846'
_audit_update_record             
;
2015-06-20 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (E)-3-(5-(bis(4-ethoxyphenyl)amino)thiophen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one 
;
_chemical_name_common            ?
_chemical_melting_point          435
_chemical_formula_moiety         'C28 H26 N2 O3 S'
_chemical_formula_sum            'C28 H26 N2 O3 S'
_chemical_formula_weight         470.57

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.185(4)
_cell_length_b                   11.757(5)
_cell_length_c                   12.715(5)
_cell_angle_alpha                100.884(6)
_cell_angle_beta                 101.591(5)
_cell_angle_gamma                106.300(5)
_cell_volume                     1246.3(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1046
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      20.63

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9387
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4586
_reflns_number_gt                2156
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0549P)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         4586
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1340
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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
C1 C 1.3442(5) 1.1590(3) 0.9956(3) 0.1001(12) Uani 1 1 d . . .
H1 H 1.4321 1.1612 1.0482 0.120 Uiso 1 1 calc R . .
C2 C 1.3675(4) 1.2050(4) 0.9070(3) 0.1112(14) Uani 1 1 d . . .
H2 H 1.4686 1.2357 0.8992 0.133 Uiso 1 1 calc R . .
C3 C 1.2398(4) 1.2052(3) 0.8298(3) 0.0948(11) Uani 1 1 d . . .
H3 H 1.2533 1.2368 0.7694 0.114 Uiso 1 1 calc R . .
C4 C 1.0916(4) 1.1580(3) 0.8428(2) 0.0649(8) Uani 1 1 d . . .
C5 C 1.0810(4) 1.1106(3) 0.9334(3) 0.0772(9) Uani 1 1 d . . .
H5 H 0.9810 1.0754 0.9415 0.093 Uiso 1 1 calc R . .
C6 C 0.9533(4) 1.1632(3) 0.7614(3) 0.0690(9) Uani 1 1 d . . .
C7 C 0.7950(4) 1.0877(3) 0.7573(2) 0.0672(8) Uani 1 1 d . . .
H7 H 0.7817 1.0330 0.8015 0.081 Uiso 1 1 calc R . .
C8 C 0.6688(4) 1.0970(3) 0.6897(3) 0.0714(9) Uani 1 1 d . . .
H8 H 0.6905 1.1525 0.6470 0.086 Uiso 1 1 calc R . .
C9 C 0.5064(4) 1.0337(3) 0.6746(2) 0.0673(8) Uani 1 1 d . A .
C10 C 0.3796(4) 1.0443(3) 0.6042(3) 0.0828(10) Uani 1 1 d . . .
H10 H 0.3909 1.0974 0.5583 0.099 Uiso 1 1 calc R . .
C11 C 0.2324(4) 0.9703(3) 0.6059(3) 0.0840(10) Uani 1 1 d . . .
H11 H 0.1372 0.9690 0.5624 0.101 Uiso 1 1 calc R . .
C12 C 0.2450(3) 0.8992(3) 0.6796(2) 0.0657(8) Uani 1 1 d . A .
C13 C -0.0343(4) 0.7792(3) 0.6403(3) 0.0671(8) Uani 1 1 d . A .
C14 C -0.0800(4) 0.7371(3) 0.5250(3) 0.0769(10) Uani 1 1 d . . .
H14 H -0.0042 0.7363 0.4863 0.092 Uiso 1 1 calc R . .
C15 C -0.2362(4) 0.6967(3) 0.4681(3) 0.0766(9) Uani 1 1 d . . .
H15 H -0.2654 0.6701 0.3909 0.092 Uiso 1 1 calc R . .
C16 C -0.3507(4) 0.6952(3) 0.5238(3) 0.0651(8) Uani 1 1 d . . .
C17 C -0.3063(4) 0.7379(3) 0.6378(3) 0.0697(9) Uani 1 1 d . . .
H17 H -0.3822 0.7388 0.6762 0.084 Uiso 1 1 calc R . .
C18 C -0.1483(4) 0.7795(3) 0.6953(3) 0.0692(9) Uani 1 1 d . . .
H18 H -0.1191 0.8082 0.7724 0.083 Uiso 1 1 calc R . .
C19 C -0.6248(4) 0.6400(3) 0.5131(3) 0.0890(11) Uani 1 1 d . . .
H19A H -0.6189 0.7207 0.5533 0.107 Uiso 1 1 calc R . .
H19B H -0.6141 0.5911 0.5658 0.107 Uiso 1 1 calc R . .
C20 C -0.7799(4) 0.5797(3) 0.4261(3) 0.0942(11) Uani 1 1 d . . .
H20A H -0.7917 0.6307 0.3765 0.141 Uiso 1 1 calc R . .
H20B H -0.8641 0.5684 0.4614 0.141 Uiso 1 1 calc R . .
H20C H -0.7830 0.5013 0.3849 0.141 Uiso 1 1 calc R . .
C21 C 0.1622(3) 0.7506(3) 0.7843(3) 0.0644(8) Uani 1 1 d . A .
C22 C 0.1535(4) 0.6308(3) 0.7524(3) 0.0776(10) Uani 1 1 d . . .
H22 H 0.1305 0.5928 0.6771 0.093 Uiso 1 1 calc R . .
C23 C 0.1781(4) 0.5648(3) 0.8294(3) 0.0940(11) Uani 1 1 d . A .
H23 H 0.1711 0.4830 0.8066 0.113 Uiso 1 1 calc R . .
C24 C 0.2132(4) 0.6225(4) 0.9402(4) 0.0863(11) Uani 1 1 d . . .
C25 C 0.2228(4) 0.7414(5) 0.9735(3) 0.0897(11) Uani 1 1 d . A .
H25 H 0.2472 0.7798 1.0488 0.108 Uiso 1 1 calc R . .
C26 C 0.1963(4) 0.8051(3) 0.8956(3) 0.0816(10) Uani 1 1 d . . .
H26 H 0.2017 0.8864 0.9187 0.098 Uiso 1 1 calc R A .
C27 C 0.2490(11) 0.5576(13) 1.1072(13) 0.106(4) Uani 0.487(18) 1 d P A 1
H27A H 0.1523 0.5699 1.1179 0.127 Uiso 0.487(18) 1 calc PR A 1
H27B H 0.3358 0.6330 1.1451 0.127 Uiso 0.487(18) 1 calc PR A 1
C28 C 0.274(6) 0.455(3) 1.153(4) 0.134(7) Uani 0.487(18) 1 d P A 1
H28A H 0.3199 0.4092 1.1063 0.200 Uiso 0.487(18) 1 calc PR A 1
H28B H 0.1750 0.4014 1.1554 0.200 Uiso 0.487(18) 1 calc PR A 1
H28C H 0.3439 0.4872 1.2268 0.200 Uiso 0.487(18) 1 calc PR A 1
C27' C 0.2441(14) 0.4678(13) 1.0223(13) 0.116(5) Uani 0.513(18) 1 d P A 2
H27C H 0.3075 0.4540 0.9719 0.139 Uiso 0.513(18) 1 calc PR A 2
H27D H 0.1380 0.4099 0.9905 0.139 Uiso 0.513(18) 1 calc PR A 2
C28' C 0.314(7) 0.454(4) 1.134(3) 0.175(16) Uani 0.513(18) 1 d P A 2
H28D H 0.4246 0.5006 1.1577 0.262 Uiso 0.513(18) 1 calc PR A 2
H28E H 0.2996 0.3694 1.1295 0.262 Uiso 0.513(18) 1 calc PR A 2
H28F H 0.2632 0.4847 1.1865 0.262 Uiso 0.513(18) 1 calc PR A 2
N1 N 1.2048(4) 1.1119(3) 1.0106(2) 0.0899(9) Uani 1 1 d . . .
N2 N 0.1270(3) 0.8147(2) 0.7024(2) 0.0766(8) Uani 1 1 d . . .
O1 O 0.9773(3) 1.2315(2) 0.70022(19) 0.1016(8) Uani 1 1 d . . .
O2 O -0.5029(3) 0.6504(2) 0.45878(17) 0.0824(7) Uani 1 1 d . . .
O3 O 0.2396(10) 0.5258(11) 0.9902(9) 0.098(4) Uani 0.487(18) 1 d P A 1
O3' O 0.2426(8) 0.5910(9) 1.0421(7) 0.083(3) Uani 0.513(18) 1 d P A 2
S1 S 0.43952(9) 0.92713(7) 0.74736(7) 0.0667(3) 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
C1 N1 1.312(4) . ?
C1 C2 1.367(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 C6 1.493(4) . ?
C5 N1 1.338(4) . ?
C5 H5 0.9300 . ?
C6 O1 1.226(3) . ?
C6 C7 1.460(4) . ?
C7 C8 1.342(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.422(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.371(4) . ?
C9 S1 1.743(3) . ?
C10 C11 1.395(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9300 . ?
C12 N2 1.369(4) . ?
C12 S1 1.728(3) . ?
C13 C18 1.372(4) . ?
C13 C14 1.391(4) . ?
C13 N2 1.432(4) . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C16 O2 1.369(3) . ?
C16 C17 1.375(4) . ?
C17 C18 1.385(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O2 1.419(3) . ?
C19 C20 1.504(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.364(4) . ?
C21 C26 1.370(4) . ?
C21 N2 1.433(3) . ?
C22 C23 1.382(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.354(5) . ?
C24 O3' 1.409(10) . ?
C24 O3 1.456(11) . ?
C25 C26 1.374(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 O3 1.44(2) . ?
C27 C28 1.49(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C27' O3' 1.43(2) . ?
C27' C28' 1.49(5) . ?
C27' H27C 0.9700 . ?
C27' H27D 0.9700 . ?
C28' H28D 0.9600 . ?
C28' H28E 0.9600 . ?
C28' H28F 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
N1 C1 C2 123.7(4) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 119.1(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 117.0(3) . . ?
C3 C4 C6 119.1(3) . . ?
C5 C4 C6 123.9(3) . . ?
N1 C5 C4 124.4(3) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
O1 C6 C7 122.3(3) . . ?
O1 C6 C4 118.4(3) . . ?
C7 C6 C4 119.3(3) . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 128.9(3) . . ?
C7 C8 H8 115.6 . . ?
C9 C8 H8 115.6 . . ?
C10 C9 C8 127.7(3) . . ?
C10 C9 S1 109.2(2) . . ?
C8 C9 S1 123.2(2) . . ?
C9 C10 C11 115.5(3) . . ?
C9 C10 H10 122.2 . . ?
C11 C10 H10 122.2 . . ?
C12 C11 C10 111.8(3) . . ?
C12 C11 H11 124.1 . . ?
C10 C11 H11 124.1 . . ?
N2 C12 C11 128.5(3) . . ?
N2 C12 S1 120.1(2) . . ?
C11 C12 S1 111.4(2) . . ?
C18 C13 C14 118.7(3) . . ?
C18 C13 N2 119.8(3) . . ?
C14 C13 N2 121.4(3) . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
O2 C16 C17 124.9(3) . . ?
O2 C16 C15 115.9(3) . . ?
C17 C16 C15 119.2(3) . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 121.0(3) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
O2 C19 C20 108.1(3) . . ?
O2 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
O2 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 118.4(3) . . ?
C22 C21 N2 120.3(3) . . ?
C26 C21 N2 121.2(3) . . ?
C21 C22 C23 121.5(3) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C24 C23 C22 118.5(4) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 O3' 102.1(5) . . ?
C23 C24 O3' 137.0(6) . . ?
C25 C24 O3 138.4(6) . . ?
C23 C24 O3 100.7(6) . . ?
O3' C24 O3 36.7(3) . . ?
C24 C25 C26 119.7(4) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 121.0(3) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
O3 C27 C28 107.8(18) . . ?
O3 C27 H27A 110.2 . . ?
C28 C27 H27A 110.2 . . ?
O3 C27 H27B 110.2 . . ?
C28 C27 H27B 110.2 . . ?
H27A C27 H27B 108.5 . . ?
O3' C27' C28' 105.0(19) . . ?
O3' C27' H27C 110.7 . . ?
C28' C27' H27C 110.7 . . ?
O3' C27' H27D 110.8 . . ?
C28' C27' H27D 110.8 . . ?
H27C C27' H27D 108.8 . . ?
C27' C28' H28D 109.5 . . ?
C27' C28' H28E 109.5 . . ?
H28D C28' H28E 109.5 . . ?
C27' C28' H28F 109.5 . . ?
H28D C28' H28F 109.5 . . ?
H28E C28' H28F 109.5 . . ?
C1 N1 C5 116.5(3) . . ?
C12 N2 C13 122.1(2) . . ?
C12 N2 C21 120.8(2) . . ?
C13 N2 C21 116.9(2) . . ?
C16 O2 C19 117.7(3) . . ?
C27 O3 C24 110.4(12) . . ?
C24 O3' C27' 109.5(11) . . ?
C12 S1 C9 92.03(15) . . ?

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
N1 C1 C2 C3 1.5(6) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C2 C3 C4 C6 177.4(3) . . . . ?
C3 C4 C5 N1 2.6(5) . . . . ?
C6 C4 C5 N1 -175.9(3) . . . . ?
C3 C4 C6 O1 -15.3(5) . . . . ?
C5 C4 C6 O1 163.2(3) . . . . ?
C3 C4 C6 C7 164.8(3) . . . . ?
C5 C4 C6 C7 -16.7(5) . . . . ?
O1 C6 C7 C8 -4.2(5) . . . . ?
C4 C6 C7 C8 175.7(3) . . . . ?
C6 C7 C8 C9 -179.1(3) . . . . ?
C7 C8 C9 C10 -179.4(3) . . . . ?
C7 C8 C9 S1 0.8(5) . . . . ?
C8 C9 C10 C11 179.7(3) . . . . ?
S1 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C10 C11 C12 N2 -178.9(3) . . . . ?
C10 C11 C12 S1 0.9(4) . . . . ?
C18 C13 C14 C15 -0.1(5) . . . . ?
N2 C13 C14 C15 176.1(3) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C14 C15 C16 O2 -178.5(3) . . . . ?
C14 C15 C16 C17 1.8(5) . . . . ?
O2 C16 C17 C18 179.1(3) . . . . ?
C15 C16 C17 C18 -1.3(5) . . . . ?
C14 C13 C18 C17 0.6(5) . . . . ?
N2 C13 C18 C17 -175.7(3) . . . . ?
C16 C17 C18 C13 0.1(5) . . . . ?
C26 C21 C22 C23 0.0(5) . . . . ?
N2 C21 C22 C23 -176.3(3) . . . . ?
C21 C22 C23 C24 -0.5(5) . . . . ?
C22 C23 C24 C25 0.3(5) . . . . ?
C22 C23 C24 O3' 178.4(5) . . . . ?
C22 C23 C24 O3 -176.4(5) . . . . ?
C23 C24 C25 C26 0.3(6) . . . . ?
O3' C24 C25 C26 -178.3(4) . . . . ?
O3 C24 C25 C26 175.4(6) . . . . ?
C22 C21 C26 C25 0.6(5) . . . . ?
N2 C21 C26 C25 176.9(3) . . . . ?
C24 C25 C26 C21 -0.8(5) . . . . ?
C2 C1 N1 C5 -0.2(6) . . . . ?
C4 C5 N1 C1 -1.9(5) . . . . ?
C11 C12 N2 C13 6.4(5) . . . . ?
S1 C12 N2 C13 -173.3(2) . . . . ?
C11 C12 N2 C21 -178.7(3) . . . . ?
S1 C12 N2 C21 1.6(4) . . . . ?
C18 C13 N2 C12 -130.2(3) . . . . ?
C14 C13 N2 C12 53.7(4) . . . . ?
C18 C13 N2 C21 54.8(4) . . . . ?
C14 C13 N2 C21 -121.4(3) . . . . ?
C22 C21 N2 C12 -104.7(4) . . . . ?
C26 C21 N2 C12 79.1(4) . . . . ?
C22 C21 N2 C13 70.4(4) . . . . ?
C26 C21 N2 C13 -105.8(3) . . . . ?
C17 C16 O2 C19 -4.1(4) . . . . ?
C15 C16 O2 C19 176.2(3) . . . . ?
C20 C19 O2 C16 -175.4(2) . . . . ?
C28 C27 O3 C24 179(2) . . . . ?
C25 C24 O3 C27 15.4(11) . . . . ?
C23 C24 O3 C27 -168.9(6) . . . . ?
O3' C24 O3 C27 5.1(7) . . . . ?
C25 C24 O3' C27' -177.3(6) . . . . ?
C23 C24 O3' C27' 4.3(10) . . . . ?
O3 C24 O3' C27' -4.3(9) . . . . ?
C28' C27' O3' C24 166(2) . . . . ?
N2 C12 S1 C9 178.8(3) . . . . ?
C11 C12 S1 C9 -1.0(3) . . . . ?
C10 C9 S1 C12 0.8(3) . . . . ?
C8 C9 S1 C12 -179.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_a1
_audit_block_doi                 10.5517/cc1k49bb
_database_code_depnum_ccdc_archive 'CCDC 1434101'
_audit_update_record             
;
2015-10-29 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (E)-3-(5-(diphenylamino)thiophen-2-yl)-1-(pyridin-2-yl)prop-2-en-1-one 
;
_chemical_name_common            ?
_chemical_melting_point          425
_chemical_formula_moiety         'C24 H18 N2 O S'
_chemical_formula_sum            'C24 H18 N2 O S'
_chemical_formula_weight         382.46

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   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   10.931(5)
_cell_length_b                   18.464(5)
_cell_length_c                   9.657(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1949.1(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1591
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      18.97

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9643
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11387
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_sigmaI/netI    0.1377
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3057
_reflns_number_gt                1293
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)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         3057
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2062
_refine_ls_wR_factor_gt          0.1775
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_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
C1 C 0.7998(5) 0.1492(4) 0.3994(7) 0.0808(18) Uani 1 1 d . . .
H1 H 0.8635 0.1773 0.4341 0.097 Uiso 1 1 calc R . .
C2 C 0.7869(7) 0.1396(5) 0.2604(7) 0.104(2) Uani 1 1 d . . .
H2 H 0.8426 0.1613 0.2005 0.124 Uiso 1 1 calc R . .
C3 C 0.6950(8) 0.0993(5) 0.2078(7) 0.102(2) Uani 1 1 d . . .
H3 H 0.6890 0.0923 0.1126 0.122 Uiso 1 1 calc R . .
C4 C 0.6109(7) 0.0686(4) 0.2944(8) 0.096(2) Uani 1 1 d . . .
H4 H 0.5472 0.0411 0.2582 0.116 Uiso 1 1 calc R . .
C5 C 0.6204(6) 0.0784(3) 0.4347(6) 0.0736(16) Uani 1 1 d . . .
H5 H 0.5614 0.0590 0.4935 0.088 Uiso 1 1 calc R . .
C6 C 0.7174(5) 0.1170(3) 0.4886(5) 0.0572(13) Uani 1 1 d . . .
C7 C 0.5796(5) 0.2158(3) 0.6807(6) 0.0699(16) Uani 1 1 d . . .
H7 H 0.6104 0.2430 0.6075 0.084 Uiso 1 1 calc R . .
C8 C 0.4816(5) 0.2409(4) 0.7567(7) 0.0812(18) Uani 1 1 d . . .
H8 H 0.4456 0.2850 0.7344 0.097 Uiso 1 1 calc R . .
C9 C 0.4377(6) 0.2015(4) 0.8637(7) 0.0836(19) Uani 1 1 d . . .
H9 H 0.3720 0.2190 0.9150 0.100 Uiso 1 1 calc R . .
C10 C 0.4891(5) 0.1355(4) 0.8979(6) 0.0806(18) Uani 1 1 d . . .
H10 H 0.4573 0.1089 0.9714 0.097 Uiso 1 1 calc R . .
C11 C 0.5880(5) 0.1084(3) 0.8236(6) 0.0666(15) Uani 1 1 d . . .
H11 H 0.6236 0.0642 0.8462 0.080 Uiso 1 1 calc R . .
C12 C 0.6316(5) 0.1500(3) 0.7141(5) 0.0561(13) Uani 1 1 d . . .
C13 C 0.8415(5) 0.0987(3) 0.6974(5) 0.0572(13) Uani 1 1 d . . .
C14 C 0.9226(5) 0.0521(3) 0.6398(5) 0.0589(14) Uani 1 1 d . . .
H14 H 0.9117 0.0300 0.5541 0.071 Uiso 1 1 calc R . .
C15 C 1.0242(5) 0.0410(3) 0.7240(5) 0.0553(13) Uani 1 1 d . . .
H15 H 1.0887 0.0112 0.6978 0.066 Uiso 1 1 calc R . .
C16 C 1.0229(4) 0.0771(3) 0.8487(5) 0.0516(12) Uani 1 1 d . . .
C17 C 1.1132(5) 0.0737(3) 0.9553(5) 0.0536(13) Uani 1 1 d . . .
H17 H 1.1818 0.0458 0.9357 0.064 Uiso 1 1 calc R . .
C18 C 1.1122(4) 0.1054(3) 1.0793(5) 0.0531(12) Uani 1 1 d . . .
H18 H 1.0469 0.1350 1.1042 0.064 Uiso 1 1 calc R . .
C19 C 1.2125(5) 0.0941(3) 1.1761(5) 0.0522(12) Uani 1 1 d . . .
C20 C 1.2056(5) 0.1267(3) 1.3196(5) 0.0545(13) Uani 1 1 d . . .
C21 C 1.2799(5) 0.1029(3) 1.4247(6) 0.0638(14) Uani 1 1 d . . .
H21 H 1.3360 0.0660 1.4079 0.077 Uiso 1 1 calc R . .
C22 C 1.2719(7) 0.1329(3) 1.5537(6) 0.0786(18) Uani 1 1 d . . .
H22 H 1.3222 0.1172 1.6254 0.094 Uiso 1 1 calc R . .
C23 C 1.1881(6) 0.1863(3) 1.5742(7) 0.0788(18) Uani 1 1 d . . .
H23 H 1.1793 0.2079 1.6607 0.095 Uiso 1 1 calc R . .
C24 C 1.1172(5) 0.2077(3) 1.4651(7) 0.0744(16) Uani 1 1 d . . .
H24 H 1.0621 0.2452 1.4804 0.089 Uiso 1 1 calc R . .
N1 N 0.7340(4) 0.1240(2) 0.6355(4) 0.0616(12) Uani 1 1 d . . .
N2 N 1.1209(4) 0.1785(2) 1.3366(5) 0.0666(12) Uani 1 1 d . . .
O1 O 1.3056(3) 0.0596(2) 1.1501(4) 0.0743(11) Uani 1 1 d . . .
S1 S 0.88926(13) 0.12809(8) 0.85761(14) 0.0625(5) 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
C1 C2 1.362(9) . ?
C1 C6 1.380(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.350(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(8) . ?
C5 H5 0.9300 . ?
C6 N1 1.436(6) . ?
C7 C12 1.379(7) . ?
C7 C8 1.380(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.352(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(8) . ?
C11 H11 0.9300 . ?
C12 N1 1.435(6) . ?
C13 C14 1.355(7) . ?
C13 N1 1.399(6) . ?
C13 S1 1.720(5) . ?
C14 C15 1.391(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.428(7) . ?
C16 S1 1.740(5) . ?
C17 C18 1.333(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.456(7) . ?
C18 H18 0.9300 . ?
C19 O1 1.227(6) . ?
C19 C20 1.513(7) . ?
C20 N2 1.342(6) . ?
C20 C21 1.372(7) . ?
C21 C22 1.367(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.361(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(8) . ?
C23 H23 0.9300 . ?
C24 N2 1.353(7) . ?
C24 H24 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
C2 C1 C6 119.4(6) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C3 C2 C1 121.3(7) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.9(7) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0(7) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.9(6) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.3(5) . . ?
C5 C6 N1 121.1(5) . . ?
C1 C6 N1 119.7(5) . . ?
C12 C7 C8 119.4(6) . . ?
C12 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 120.1(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.9(6) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 120.7(6) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 117.3(6) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C7 C12 C11 121.6(5) . . ?
C7 C12 N1 119.5(5) . . ?
C11 C12 N1 118.9(5) . . ?
C14 C13 N1 125.9(5) . . ?
C14 C13 S1 111.8(4) . . ?
N1 C13 S1 122.2(4) . . ?
C13 C14 C15 112.0(5) . . ?
C13 C14 H14 124.0 . . ?
C15 C14 H14 124.0 . . ?
C16 C15 C14 115.6(4) . . ?
C16 C15 H15 122.2 . . ?
C14 C15 H15 122.2 . . ?
C15 C16 C17 127.1(5) . . ?
C15 C16 S1 108.3(4) . . ?
C17 C16 S1 124.6(4) . . ?
C18 C17 C16 128.5(5) . . ?
C18 C17 H17 115.7 . . ?
C16 C17 H17 115.7 . . ?
C17 C18 C19 120.5(5) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
O1 C19 C18 124.6(5) . . ?
O1 C19 C20 115.8(4) . . ?
C18 C19 C20 119.6(5) . . ?
N2 C20 C21 123.1(5) . . ?
N2 C20 C19 115.5(5) . . ?
C21 C20 C19 121.3(5) . . ?
C22 C21 C20 120.4(6) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 118.0(6) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C22 C23 C24 118.6(5) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
N2 C24 C23 125.2(5) . . ?
N2 C24 H24 117.4 . . ?
C23 C24 H24 117.4 . . ?
C13 N1 C12 122.8(4) . . ?
C13 N1 C6 119.8(4) . . ?
C12 N1 C6 117.0(4) . . ?
C20 N2 C24 114.6(5) . . ?
C13 S1 C16 92.3(2) . . ?

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
C6 C1 C2 C3 0.2(11) . . . . ?
C1 C2 C3 C4 1.6(12) . . . . ?
C2 C3 C4 C5 -0.5(11) . . . . ?
C3 C4 C5 C6 -2.4(10) . . . . ?
C4 C5 C6 C1 4.1(9) . . . . ?
C4 C5 C6 N1 -175.9(6) . . . . ?
C2 C1 C6 C5 -3.0(9) . . . . ?
C2 C1 C6 N1 177.0(6) . . . . ?
C12 C7 C8 C9 0.5(8) . . . . ?
C7 C8 C9 C10 -0.5(9) . . . . ?
C8 C9 C10 C11 0.5(9) . . . . ?
C9 C10 C11 C12 -0.4(9) . . . . ?
C8 C7 C12 C11 -0.4(8) . . . . ?
C8 C7 C12 N1 -179.7(5) . . . . ?
C10 C11 C12 C7 0.4(8) . . . . ?
C10 C11 C12 N1 179.6(5) . . . . ?
N1 C13 C14 C15 176.2(5) . . . . ?
S1 C13 C14 C15 -1.0(6) . . . . ?
C13 C14 C15 C16 1.4(7) . . . . ?
C14 C15 C16 C17 178.1(5) . . . . ?
C14 C15 C16 S1 -1.1(6) . . . . ?
C15 C16 C17 C18 -176.8(5) . . . . ?
S1 C16 C17 C18 2.3(8) . . . . ?
C16 C17 C18 C19 178.6(5) . . . . ?
C17 C18 C19 O1 4.2(8) . . . . ?
C17 C18 C19 C20 -176.1(5) . . . . ?
O1 C19 C20 N2 164.0(5) . . . . ?
C18 C19 C20 N2 -15.7(7) . . . . ?
O1 C19 C20 C21 -17.5(7) . . . . ?
C18 C19 C20 C21 162.8(5) . . . . ?
N2 C20 C21 C22 -1.4(8) . . . . ?
C19 C20 C21 C22 -179.8(5) . . . . ?
C20 C21 C22 C23 0.4(9) . . . . ?
C21 C22 C23 C24 -0.5(9) . . . . ?
C22 C23 C24 N2 1.8(9) . . . . ?
C14 C13 N1 C12 156.0(5) . . . . ?
S1 C13 N1 C12 -27.1(7) . . . . ?
C14 C13 N1 C6 -16.8(8) . . . . ?
S1 C13 N1 C6 160.1(4) . . . . ?
C7 C12 N1 C13 130.4(5) . . . . ?
C11 C12 N1 C13 -48.9(7) . . . . ?
C7 C12 N1 C6 -56.6(7) . . . . ?
C11 C12 N1 C6 124.1(5) . . . . ?
C5 C6 N1 C13 120.6(6) . . . . ?
C1 C6 N1 C13 -59.4(7) . . . . ?
C5 C6 N1 C12 -52.7(7) . . . . ?
C1 C6 N1 C12 127.3(6) . . . . ?
C21 C20 N2 C24 2.4(7) . . . . ?
C19 C20 N2 C24 -179.2(5) . . . . ?
C23 C24 N2 C20 -2.6(8) . . . . ?
C14 C13 S1 C16 0.3(4) . . . . ?
N1 C13 S1 C16 -177.0(4) . . . . ?
C15 C16 S1 C13 0.4(4) . . . . ?
C17 C16 S1 C13 -178.8(5) . . . . ?

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
C10 H10 O1 0.93 2.56 3.453(7) 160.7 1_455
C11 H11 O1 0.93 2.41 3.322(7) 165.6 3_757
C18 H18 N2 0.93 2.52 2.829(7) 99.9 .
C17 H17 O1 0.93 2.49 2.834(6) 102.2 .

_diffrn_measured_fraction_theta_max 0.891
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.891
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.064
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent
