# Electronic Supplementary Material (ESI) for Analyst.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1443955'
_audit_update_record             
;
2015-12-22 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        S1
_chemical_name_common            Cinnamaldimine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H27 Cl N2 O'
_chemical_formula_weight         322.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/a

_space_group_crystal_system      ?
_space_group_IT_number           ?
_space_group_name_H-M_alt        ?
_space_group_name_Hall           P_2xa

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

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

_cell_length_a                   14.388
_cell_length_b                   6.189
_cell_length_c                   20.392
_cell_angle_alpha                90
_cell_angle_beta                 98.16
_cell_angle_gamma                90
_cell_volume                     1797.5
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11102
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.2

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      1.19
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Enraf Noniusκ-CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11102
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.166
_diffrn_reflns_theta_max         27.178
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3883
_reflns_number_gt                2637
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.7446P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3883
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1364
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11357(14) 0.9005(3) 1.06998(10) 0.0431(5) Uani 1 1 d . . . . .
C2 C 0.15199(14) 1.1004(3) 1.05494(10) 0.0466(5) Uani 1 1 d . . . . .
H2 H 0.1676 1.2014 1.0885 0.056 Uiso 1 1 calc R U . . .
C2A C 0.09109(15) 0.7538(3) 1.01703(10) 0.0479(5) Uani 1 1 d . . . . .
H2A H 0.0649 0.6206 1.0249 0.057 Uiso 1 1 calc R U . . .
C3 C 0.16671(14) 1.1486(3) 0.99158(10) 0.0449(5) Uani 1 1 d . . . . .
H3 H 0.1914 1.2830 0.9831 0.054 Uiso 1 1 calc R U . . .
C3A C 0.10726(15) 0.8045(3) 0.95430(10) 0.0480(5) Uani 1 1 d . . . . .
H3A H 0.0920 0.7039 0.9206 0.058 Uiso 1 1 calc R U . . .
C4 C 0.14585(13) 1.0022(3) 0.93925(10) 0.0417(5) Uani 1 1 d . . . . .
C5 C 0.16721(14) 1.0558(3) 0.87420(10) 0.0471(5) Uani 1 1 d . . . . .
H5 H 0.1915 1.1932 0.8693 0.057 Uiso 1 1 calc R U . . .
C6 C 0.15615(15) 0.9301(4) 0.81964(10) 0.0485(5) Uani 1 1 d . . . . .
H6 H 0.1327 0.7907 0.8220 0.058 Uiso 1 1 calc R U . . .
C7 C 0.17974(14) 1.0074(3) 0.75882(10) 0.0475(5) Uani 1 1 d . . . . .
H7 H 0.2054 1.1451 0.7578 0.057 Uiso 1 1 calc R U . . .
C8 C 0.19243(15) 0.9747(4) 0.64209(10) 0.0502(5) Uani 1 1 d . . . . .
H8A H 0.1846 1.1304 0.6398 0.060 Uiso 1 1 calc R U . . .
H8B H 0.1497 0.9118 0.6061 0.060 Uiso 1 1 calc R U . . .
C9 C 0.29305(14) 0.9185(3) 0.63302(9) 0.0435(5) Uani 1 1 d . . . . .
C10 C 0.31057(16) 1.0087(4) 0.56629(11) 0.0589(6) Uani 1 1 d . . . . .
H10A H 0.2631 0.9531 0.5319 0.071 Uiso 1 1 calc R U . . .
H10B H 0.3043 1.1647 0.5669 0.071 Uiso 1 1 calc R U . . .
C11 C 0.40716(18) 0.9510(5) 0.54943(13) 0.0721(7) Uani 1 1 d . . . . .
H11A H 0.4124 1.0009 0.5050 0.086 Uiso 1 1 calc R U . . .
H11B H 0.4548 1.0240 0.5799 0.086 Uiso 1 1 calc R U . . .
C12 C 0.42410(18) 0.7097(5) 0.55343(14) 0.0798(9) Uani 1 1 d . . . . .
H12A H 0.4880 0.6797 0.5462 0.096 Uiso 1 1 calc R U . . .
H12B H 0.3821 0.6385 0.5187 0.096 Uiso 1 1 calc R U . . .
C13 C 0.40838(17) 0.6189(4) 0.62014(14) 0.0692(7) Uani 1 1 d . . . . .
H13A H 0.4552 0.6771 0.6545 0.083 Uiso 1 1 calc R U . . .
H13B H 0.4155 0.4631 0.6199 0.083 Uiso 1 1 calc R U . . .
C14 C 0.31053(16) 0.6762(4) 0.63520(12) 0.0565(6) Uani 1 1 d . . . . .
H14A H 0.2640 0.6057 0.6032 0.068 Uiso 1 1 calc R U . . .
H14B H 0.3032 0.6221 0.6788 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1190(2) 1.0001(5) 1.18696(12) 0.0791(8) Uani 1 1 d . . . . .
H15A H 0.1040 0.9352 1.2269 0.119 Uiso 1 1 calc R U . . .
H15B H 0.1844 1.0370 1.1926 0.119 Uiso 1 1 calc R U . . .
H15C H 0.0820 1.1283 1.1774 0.119 Uiso 1 1 calc R U . . .
C15A C 0.0576(2) 0.6438(4) 1.14711(12) 0.0682(7) Uani 1 1 d . . . . .
H15D H 0.0526 0.6367 1.1935 0.102 Uiso 1 1 calc R U . . .
H15E H -0.0037 0.6308 1.1218 0.102 Uiso 1 1 calc R U . . .
H15F H 0.0967 0.5281 1.1357 0.102 Uiso 1 1 calc R U . . .
N1 N 0.09853(14) 0.8483(3) 1.13249(9) 0.0555(5) Uani 1 1 d . . . . .
N2 N 0.16764(12) 0.8975(3) 0.70494(9) 0.0483(4) Uani 1 1 d . . . . .
O1 O 0.34878(10) 1.0263(3) 0.68645(7) 0.0588(4) Uani 1 1 d . . . . .
H1 H 0.4045 1.0084 0.6836 0.088 Uiso 1 1 calc R U . . .
Cl10 Cl 0.07460(4) 0.45625(10) 0.71228(3) 0.0680(2) Uani 1 1 d . . . . .
H100 H 0.1427(16) 0.764(4) 0.7049(11) 0.059(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.362(3) . ?
C1 C2 1.407(3) . ?
C1 C2A 1.412(3) . ?
C2 C3 1.372(3) . ?
C2A C3A 1.369(3) . ?
C3 C4 1.400(3) . ?
C3A C4 1.396(3) . ?
C4 C5 1.442(3) . ?
C5 C6 1.348(3) . ?
C6 C7 1.415(3) . ?
C7 N2 1.283(3) . ?
C8 N2 1.459(3) . ?
C8 C9 1.526(3) . ?
C9 O1 1.424(2) . ?
C9 C14 1.520(3) . ?
C9 C10 1.525(3) . ?
C10 C11 1.521(3) . ?
C11 C12 1.513(4) . ?
C12 C13 1.518(4) . ?
C13 C14 1.525(3) . ?
C15 N1 1.452(3) . ?
C15A N1 1.445(3) . ?

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 122.14(18) . . ?
N1 C1 C2A 120.92(18) . . ?
C2 C1 C2A 116.94(18) . . ?
C3 C2 C1 120.98(18) . . ?
C3A C2A C1 121.09(19) . . ?
C2 C3 C4 122.16(19) . . ?
C2A C3A C4 122.15(19) . . ?
C3A C4 C3 116.67(18) . . ?
C3A C4 C5 123.18(18) . . ?
C3 C4 C5 120.11(18) . . ?
C6 C5 C4 127.6(2) . . ?
C5 C6 C7 120.9(2) . . ?
N2 C7 C6 123.4(2) . . ?
N2 C8 C9 112.73(16) . . ?
O1 C9 C14 111.53(17) . . ?
O1 C9 C10 111.40(18) . . ?
C14 C9 C10 109.86(18) . . ?
O1 C9 C8 103.97(16) . . ?
C14 C9 C8 112.17(18) . . ?
C10 C9 C8 107.74(16) . . ?
C11 C10 C9 112.82(19) . . ?
C12 C11 C10 111.4(2) . . ?
C11 C12 C13 111.7(2) . . ?
C12 C13 C14 110.7(2) . . ?
C9 C14 C13 112.16(19) . . ?
C1 N1 C15A 121.61(18) . . ?
C1 N1 C15 121.40(19) . . ?
C15A N1 C15 116.93(19) . . ?
C7 N2 C8 123.9(2) . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036

_shelxl_version_number           2014/6

