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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_130639lt
_database_code_depnum_ccdc_archive 'CCDC 1049885'
_audit_update_record             
;
2015-02-17 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        (E)-10-(10H-phenothiazin-3'-yl)propenal
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N O S'
_chemical_formula_weight         253.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                   16.1120(13)
_cell_length_b                   7.8274(7)
_cell_length_c                   9.5930(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.081(2)
_cell_angle_gamma                90.00
_cell_volume                     1187.27(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3955
_cell_measurement_theta_min      2.9038
_cell_measurement_theta_max      26.3428

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8710
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            8829
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         26.46
_reflns_number_total             2409
_reflns_number_gt                2092
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0404P)²+0.5104P] 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         2409
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.86751(2) 0.83874(4) 0.96166(4) 0.02052(12) Uani 1 1 d . . .
O1 O 0.53173(6) 0.79789(14) 0.32961(10) 0.0240(2) Uani 1 1 d . . .
N1 N 0.71924(7) 0.97377(14) 0.75643(11) 0.0153(2) Uani 1 1 d . . .
C1 C 0.55505(8) 0.83099(18) 0.45605(14) 0.0188(3) Uani 1 1 d . . .
H1 H 0.5142 0.8188 0.5148 0.023 Uiso 1 1 calc R . .
C2 C 0.63768(8) 0.88617(18) 0.52393(13) 0.0167(3) Uani 1 1 d . . .
H2 H 0.6825 0.8970 0.4731 0.020 Uiso 1 1 calc R . .
C3 C 0.64850(8) 0.92200(17) 0.66402(13) 0.0156(3) Uani 1 1 d . . .
H3 H 0.5994 0.9092 0.7043 0.019 Uiso 1 1 calc R . .
C4 C 0.79868(8) 1.00713(17) 0.71555(14) 0.0158(3) Uani 1 1 d . . .
C5 C 0.80383(9) 1.10024(17) 0.59386(14) 0.0182(3) Uani 1 1 d . . .
H5 H 0.7539 1.1439 0.5357 0.022 Uiso 1 1 calc R . .
C6 C 0.88203(9) 1.12933(18) 0.55751(15) 0.0225(3) Uani 1 1 d . . .
H6 H 0.8853 1.1899 0.4729 0.027 Uiso 1 1 calc R . .
C7 C 0.95532(9) 1.07042(19) 0.64397(17) 0.0254(3) Uani 1 1 d . . .
H7 H 1.0085 1.0892 0.6178 0.030 Uiso 1 1 calc R . .
C8 C 0.87297(8) 0.95156(17) 0.80427(14) 0.0181(3) Uani 1 1 d . . .
C9 C 0.78023(8) 0.94626(17) 1.00823(14) 0.0176(3) Uani 1 1 d . . .
C10 C 0.71403(8) 1.00172(17) 0.90239(13) 0.0158(3) Uani 1 1 d . . .
C11 C 0.64346(8) 1.07953(17) 0.93896(14) 0.0180(3) Uani 1 1 d . . .
H11 H 0.5990 1.1209 0.8671 0.022 Uiso 1 1 calc R . .
C12 C 0.63848(9) 1.09628(18) 1.08132(14) 0.0214(3) Uani 1 1 d . . .
H12 H 0.5894 1.1448 1.1068 0.026 Uiso 1 1 calc R . .
C13 C 0.70508(9) 1.04228(19) 1.18642(14) 0.0232(3) Uani 1 1 d . . .
H13 H 0.7017 1.0555 1.2836 0.028 Uiso 1 1 calc R . .
C14 C 0.77618(9) 0.96951(18) 1.15057(14) 0.0218(3) Uani 1 1 d . . .
H14 H 0.8222 0.9355 1.2228 0.026 Uiso 1 1 calc R . .
C15 C 0.95121(9) 0.98436(18) 0.76819(16) 0.0229(3) Uani 1 1 d . . .
H15 H 1.0017 0.9476 0.8290 0.028 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.02101(19) 0.01774(19) 0.02009(19) 0.00124(13) -0.00285(13) 0.00369(13)
O1 0.0231(5) 0.0317(6) 0.0153(5) -0.0053(4) -0.0012(4) 0.0025(4)
N1 0.0154(5) 0.0183(6) 0.0118(5) -0.0002(4) 0.0016(4) -0.0003(4)
C1 0.0187(6) 0.0210(7) 0.0167(7) -0.0016(5) 0.0031(5) 0.0029(5)
C2 0.0168(6) 0.0178(7) 0.0153(6) 0.0015(5) 0.0027(5) 0.0014(5)
C3 0.0141(6) 0.0161(7) 0.0164(6) 0.0019(5) 0.0022(5) 0.0009(5)
C4 0.0163(6) 0.0136(6) 0.0179(6) -0.0032(5) 0.0041(5) -0.0010(5)
C5 0.0209(7) 0.0149(6) 0.0189(7) -0.0014(5) 0.0043(5) 0.0003(5)
C6 0.0272(7) 0.0172(7) 0.0255(7) -0.0026(6) 0.0109(6) -0.0043(6)
C7 0.0196(7) 0.0206(7) 0.0384(9) -0.0071(6) 0.0115(6) -0.0053(6)
C8 0.0189(6) 0.0141(6) 0.0200(7) -0.0025(5) 0.0003(5) -0.0002(5)
C9 0.0204(7) 0.0136(6) 0.0175(7) 0.0012(5) 0.0007(5) -0.0019(5)
C10 0.0198(6) 0.0150(6) 0.0123(6) 0.0006(5) 0.0023(5) -0.0036(5)
C11 0.0190(6) 0.0187(7) 0.0158(6) 0.0003(5) 0.0023(5) -0.0019(5)
C12 0.0256(7) 0.0209(7) 0.0193(7) -0.0008(5) 0.0085(5) -0.0018(6)
C13 0.0357(8) 0.0218(7) 0.0123(6) -0.0001(5) 0.0053(6) -0.0062(6)
C14 0.0294(7) 0.0166(7) 0.0165(7) 0.0030(5) -0.0029(5) -0.0042(6)
C15 0.0165(6) 0.0182(7) 0.0326(8) -0.0060(6) 0.0011(6) -0.0008(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.7659(14) . ?
S1 C9 1.7683(14) . ?
O1 C1 1.2265(16) . ?
N1 C3 1.3642(16) . ?
N1 C4 1.4329(16) . ?
N1 C10 1.4355(16) . ?
C1 C2 1.4317(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3509(18) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.3921(18) . ?
C4 C8 1.3981(18) . ?
C5 C6 1.3892(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C15 1.381(2) . ?
C7 H7 0.9500 . ?
C8 C15 1.394(2) . ?
C9 C14 1.3915(19) . ?
C9 C10 1.3930(18) . ?
C10 C11 1.3930(19) . ?
C11 C12 1.3895(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C9 98.67(6) . . ?
C3 N1 C4 123.71(11) . . ?
C3 N1 C10 118.75(11) . . ?
C4 N1 C10 117.51(10) . . ?
O1 C1 C2 126.50(13) . . ?
O1 C1 H1 116.8 . . ?
C2 C1 H1 116.8 . . ?
C3 C2 C1 116.49(12) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C2 C3 N1 129.80(12) . . ?
C2 C3 H3 115.1 . . ?
N1 C3 H3 115.1 . . ?
C5 C4 C8 119.44(12) . . ?
C5 C4 N1 121.68(12) . . ?
C8 C4 N1 118.81(12) . . ?
C6 C5 C4 119.96(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 120.34(14) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C15 C7 C6 120.13(13) . . ?
C15 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C15 C8 C4 120.05(13) . . ?
C15 C8 S1 120.04(11) . . ?
C4 C8 S1 119.91(11) . . ?
C14 C9 C10 120.05(13) . . ?
C14 C9 S1 119.98(10) . . ?
C10 C9 S1 119.92(10) . . ?
C9 C10 C11 120.02(12) . . ?
C9 C10 N1 118.90(12) . . ?
C11 C10 N1 121.06(11) . . ?
C12 C11 C10 119.53(13) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.13(13) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.45(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C9 119.73(13) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C7 C15 C8 119.98(13) . . ?
C7 C15 H15 120.0 . . ?
C8 C15 H15 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.46
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042
