# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_comp-1
_database_code_depnum_ccdc_archive 'CCDC 1554126'
_audit_update_record             
;
2017-06-05 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 Cl2 N2 O2 Ti'
_chemical_formula_sum            'C16 H18 Cl2 N2 O2 Ti'
_chemical_formula_weight         389.12

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'
Ti Ti 0.2776 0.4457 '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           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                   9.0551(7)
_cell_length_b                   9.1409(7)
_cell_length_c                   11.4606(8)
_cell_angle_alpha                105.286(7)
_cell_angle_beta                 90.508(6)
_cell_angle_gamma                104.462(7)
_cell_volume                     883.22(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1192
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      29.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7310
_exptl_absorpt_correction_T_max  0.8198
_exptl_absorpt_process_details   ?

_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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5486
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3127
_reflns_number_gt                1924
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
 Ortep-3 for Windows (Farrugia, 1997)
;
_computing_publication_material  
;
 WinGX (Farrugia, 1999)
;
_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)+(0.0738P)²+0.3219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3127
_refine_ls_number_parameters     210
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1738
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.062
_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
Ti1 Ti 0.85864(9) -0.12084(10) 0.22273(7) 0.0626(3) Uani 1 1 d . . .
N1 N 0.7522(4) 0.0331(4) 0.1438(3) 0.0608(10) Uani 1 1 d . . .
C11 C 0.6752(5) 0.1230(5) 0.2194(4) 0.0595(11) Uani 1 1 d . . .
C12 C 0.6788(5) 0.1193(5) 0.3429(4) 0.0612(12) Uani 1 1 d . . .
C1 C 0.7565(6) 0.0393(6) 0.0285(5) 0.0741(14) Uani 1 1 d . . .
H1 H 0.8096 -0.0212 -0.0244 0.089 Uiso 1 1 calc R . .
C7 C 0.6016(6) 0.2090(6) 0.4253(5) 0.0755(15) Uani 1 1 d . . .
C8 C 0.6143(7) 0.2069(7) 0.5473(6) 0.0893(18) Uani 1 1 d . . .
H8 H 0.5656 0.2659 0.6056 0.107 Uiso 1 1 calc R . .
C4 C 0.5962(6) 0.2181(6) 0.1814(6) 0.0748(14) Uani 1 1 d . . .
C10 C 0.7694(6) 0.0287(6) 0.4908(5) 0.0752(14) Uani 1 1 d . . .
H10 H 0.8254 -0.0329 0.5141 0.090 Uiso 1 1 calc R . .
C9 C 0.6980(7) 0.1182(8) 0.5785(5) 0.097(2) Uani 1 1 d . . .
H9 H 0.7082 0.1168 0.6589 0.116 Uiso 1 1 calc R . .
C3 C 0.6023(6) 0.2207(7) 0.0602(6) 0.0900(18) Uani 1 1 d . . .
H3 H 0.5509 0.2816 0.0309 0.108 Uiso 1 1 calc R . .
C2 C 0.6824(7) 0.1354(7) -0.0143(6) 0.0883(17) Uani 1 1 d . . .
H2 H 0.6889 0.1399 -0.0943 0.106 Uiso 1 1 calc R . .
C6 C 0.5171(7) 0.2994(7) 0.3829(8) 0.097(2) Uani 1 1 d . . .
H6 H 0.4623 0.3564 0.4370 0.116 Uiso 1 1 calc R . .
C5 C 0.5145(7) 0.3046(7) 0.2674(8) 0.099(2) Uani 1 1 d . . .
H5 H 0.4587 0.3655 0.2428 0.119 Uiso 1 1 calc R . .
Cl1 Cl 0.60094(13) -0.28392(15) 0.19332(11) 0.0722(4) Uani 1 1 d . . .
Cl2 Cl 1.07789(13) 0.09269(16) 0.26849(12) 0.0774(4) Uani 1 1 d . . .
O1 O 0.9041(4) -0.2168(5) 0.0754(3) 0.0805(10) Uani 1 1 d . . .
O2 O 0.9094(4) -0.2249(4) 0.3198(3) 0.0811(10) Uani 1 1 d U . .
N2 N 0.7603(4) 0.0284(5) 0.3747(3) 0.0632(10) Uani 1 1 d . . .
C15 C 0.8767(9) -0.3439(9) 0.3807(8) 0.135(3) Uani 1 1 d DU . .
H15A H 0.9115 -0.2969 0.4657 0.162 Uiso 1 1 calc R . .
H15B H 0.7667 -0.3863 0.3756 0.162 Uiso 1 1 calc R . .
C13 C 0.9057(9) -0.3381(11) -0.0101(10) 0.169(4) Uani 1 1 d . . .
H13A H 0.9489 -0.4037 0.0270 0.203 Uiso 1 1 calc R . .
H13B H 0.9801 -0.3016 -0.0634 0.203 Uiso 1 1 calc R . .
C14 C 0.7851(9) -0.4350(11) -0.0828(8) 0.167(4) Uani 1 1 d . . .
H14A H 0.7241 -0.5022 -0.0397 0.251 Uiso 1 1 calc R . .
H14B H 0.8197 -0.4979 -0.1526 0.251 Uiso 1 1 calc R . .
H14C H 0.7247 -0.3746 -0.1083 0.251 Uiso 1 1 calc R . .
C16 C 0.9418(10) -0.4644(10) 0.3365(11) 0.178(4) Uani 1 1 d D . .
H16A H 0.9027 -0.5167 0.2539 0.267 Uiso 1 1 calc R . .
H16B H 0.9177 -0.5376 0.3846 0.267 Uiso 1 1 calc R . .
H16C H 1.0507 -0.4239 0.3400 0.267 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ti1 O2 1.766(3) . ?
Ti1 O1 1.789(4) . ?
Ti1 N1 2.249(4) . ?
Ti1 N2 2.251(4) . ?
Ti1 Cl2 2.3522(14) . ?
Ti1 Cl1 2.4010(13) . ?
N1 C1 1.337(6) . ?
N1 C11 1.355(6) . ?
C11 C4 1.400(7) . ?
C11 C12 1.425(7) . ?
C12 N2 1.352(6) . ?
C12 C7 1.394(7) . ?
C1 C2 1.407(8) . ?
C1 H1 0.9300 . ?
C7 C8 1.408(8) . ?
C7 C6 1.423(9) . ?
C8 C9 1.347(9) . ?
C8 H8 0.9300 . ?
C4 C3 1.398(8) . ?
C4 C5 1.427(8) . ?
C10 N2 1.332(6) . ?
C10 C9 1.393(8) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C3 C2 1.344(8) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C6 C5 1.337(9) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
O1 C13 1.275(8) . ?
O2 C15 1.415(7) . ?
C15 C16 1.360(9) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C13 C14 1.335(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O2 Ti1 O1 105.02(18) . . ?
O2 Ti1 N1 163.24(16) . . ?
O1 Ti1 N1 90.75(16) . . ?
O2 Ti1 N2 91.45(16) . . ?
O1 Ti1 N2 162.83(17) . . ?
N1 Ti1 N2 72.41(15) . . ?
O2 Ti1 Cl2 97.96(11) . . ?
O1 Ti1 Cl2 97.20(11) . . ?
N1 Ti1 Cl2 85.42(10) . . ?
N2 Ti1 Cl2 85.07(10) . . ?
O2 Ti1 Cl1 90.49(11) . . ?
O1 Ti1 Cl1 92.91(11) . . ?
N1 Ti1 Cl1 82.93(10) . . ?
N2 Ti1 Cl1 81.92(10) . . ?
Cl2 Ti1 Cl1 164.66(6) . . ?
C1 N1 C11 118.3(4) . . ?
C1 N1 Ti1 125.1(4) . . ?
C11 N1 Ti1 116.6(3) . . ?
N1 C11 C4 123.0(5) . . ?
N1 C11 C12 116.9(4) . . ?
C4 C11 C12 120.1(5) . . ?
N2 C12 C7 122.9(5) . . ?
N2 C12 C11 117.4(4) . . ?
C7 C12 C11 119.7(5) . . ?
N1 C1 C2 121.3(5) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C12 C7 C8 117.6(6) . . ?
C12 C7 C6 118.9(6) . . ?
C8 C7 C6 123.6(6) . . ?
C9 C8 C7 119.0(6) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C3 C4 C11 117.0(5) . . ?
C3 C4 C5 124.3(6) . . ?
C11 C4 C5 118.6(6) . . ?
N2 C10 C9 122.2(6) . . ?
N2 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C8 C9 C10 120.3(6) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C2 C3 C4 120.2(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C2 C1 120.1(6) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C5 C6 C7 121.7(6) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C5 C4 121.0(6) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C13 O1 Ti1 153.0(6) . . ?
C15 O2 Ti1 152.8(4) . . ?
C10 N2 C12 117.9(4) . . ?
C10 N2 Ti1 125.7(4) . . ?
C12 N2 Ti1 116.3(3) . . ?
C16 C15 O2 114.6(8) . . ?
C16 C15 H15A 108.6 . . ?
O2 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
O2 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
O1 C13 C14 126.0(8) . . ?
O1 C13 H13A 105.8 . . ?
C14 C13 H13A 105.8 . . ?
O1 C13 H13B 105.8 . . ?
C14 C13 H13B 105.8 . . ?
H13A C13 H13B 106.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Ti1 N1 C1 -167.5(5) . . . . ?
O1 Ti1 N1 C1 -7.1(4) . . . . ?
N2 Ti1 N1 C1 176.3(4) . . . . ?
Cl2 Ti1 N1 C1 90.0(3) . . . . ?
Cl1 Ti1 N1 C1 -100.0(3) . . . . ?
O2 Ti1 N1 C11 10.9(6) . . . . ?
O1 Ti1 N1 C11 171.2(3) . . . . ?
N2 Ti1 N1 C11 -5.3(3) . . . . ?
Cl2 Ti1 N1 C11 -91.6(3) . . . . ?
Cl1 Ti1 N1 C11 78.4(3) . . . . ?
C1 N1 C11 C4 2.0(6) . . . . ?
Ti1 N1 C11 C4 -176.5(3) . . . . ?
C1 N1 C11 C12 -177.1(4) . . . . ?
Ti1 N1 C11 C12 4.4(5) . . . . ?
N1 C11 C12 N2 0.9(6) . . . . ?
C4 C11 C12 N2 -178.3(4) . . . . ?
N1 C11 C12 C7 -179.9(4) . . . . ?
C4 C11 C12 C7 1.0(6) . . . . ?
C11 N1 C1 C2 -0.4(7) . . . . ?
Ti1 N1 C1 C2 177.9(3) . . . . ?
N2 C12 C7 C8 2.0(7) . . . . ?
C11 C12 C7 C8 -177.2(4) . . . . ?
N2 C12 C7 C6 -179.2(4) . . . . ?
C11 C12 C7 C6 1.6(7) . . . . ?
C12 C7 C8 C9 -0.7(8) . . . . ?
C6 C7 C8 C9 -179.5(5) . . . . ?
N1 C11 C4 C3 -1.6(7) . . . . ?
C12 C11 C4 C3 177.6(4) . . . . ?
N1 C11 C4 C5 178.1(4) . . . . ?
C12 C11 C4 C5 -2.8(7) . . . . ?
C7 C8 C9 C10 -0.7(8) . . . . ?
N2 C10 C9 C8 1.0(8) . . . . ?
C11 C4 C3 C2 -0.5(8) . . . . ?
C5 C4 C3 C2 179.9(5) . . . . ?
C4 C3 C2 C1 2.0(8) . . . . ?
N1 C1 C2 C3 -1.5(8) . . . . ?
C12 C7 C6 C5 -2.3(8) . . . . ?
C8 C7 C6 C5 176.4(5) . . . . ?
C7 C6 C5 C4 0.4(9) . . . . ?
C3 C4 C5 C6 -178.3(5) . . . . ?
C11 C4 C5 C6 2.2(8) . . . . ?
O2 Ti1 O1 C13 44.2(11) . . . . ?
N1 Ti1 O1 C13 -130.0(11) . . . . ?
N2 Ti1 O1 C13 -118.9(11) . . . . ?
Cl2 Ti1 O1 C13 144.5(11) . . . . ?
Cl1 Ti1 O1 C13 -47.1(11) . . . . ?
O1 Ti1 O2 C15 -92.3(10) . . . . ?
N1 Ti1 O2 C15 67.3(12) . . . . ?
N2 Ti1 O2 C15 82.7(10) . . . . ?
Cl2 Ti1 O2 C15 168.0(10) . . . . ?
Cl1 Ti1 O2 C15 0.8(10) . . . . ?
C9 C10 N2 C12 0.2(7) . . . . ?
C9 C10 N2 Ti1 -176.3(3) . . . . ?
C7 C12 N2 C10 -1.8(6) . . . . ?
C11 C12 N2 C10 177.5(4) . . . . ?
C7 C12 N2 Ti1 175.1(3) . . . . ?
C11 C12 N2 Ti1 -5.7(5) . . . . ?
O2 Ti1 N2 C10 7.0(4) . . . . ?
O1 Ti1 N2 C10 170.7(5) . . . . ?
N1 Ti1 N2 C10 -177.7(4) . . . . ?
Cl2 Ti1 N2 C10 -90.9(3) . . . . ?
Cl1 Ti1 N2 C10 97.2(4) . . . . ?
O2 Ti1 N2 C12 -169.6(3) . . . . ?
O1 Ti1 N2 C12 -5.9(7) . . . . ?
N1 Ti1 N2 C12 5.8(3) . . . . ?
Cl2 Ti1 N2 C12 92.5(3) . . . . ?
Cl1 Ti1 N2 C12 -79.3(3) . . . . ?
Ti1 O2 C15 C16 108.9(10) . . . . ?
Ti1 O1 C13 C14 72.2(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.068
