# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_exp_1
_database_code_depnum_ccdc_archive 'CCDC 1470715'
_audit_update_record             
;
2016-09-10 deposited with the CCDC.
2016-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H36 N4 P2 Se2 Ti'
_chemical_formula_sum            'C30 H36 N4 P2 Se2 Ti'
_chemical_formula_weight         720.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ti Ti 0.2191 1.8069 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P c '

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

_cell_length_a                   8.9540(3)
_cell_length_b                   14.1215(10)
_cell_length_c                   14.6424(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.519(5)
_cell_angle_gamma                90.00
_cell_volume                     1594.94(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5102
_cell_measurement_theta_min      3.1268
_cell_measurement_theta_max      70.5849

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    6.028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)(compiled Oct 27'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6223
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         70.57
_reflns_number_total             4114
_reflns_number_gt                4062
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.0782P)²+0.0807P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(10)
_refine_ls_number_reflns         4114
_refine_ls_number_parameters     357
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_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
Ti1 Ti 0.45321(10) 0.27931(5) 1.14797(6) 0.02192(17) Uani 1 1 d . . .
Se1 Se 0.29312(6) 0.19281(3) 0.94806(4) 0.02944(13) Uani 1 1 d . . .
Se2 Se 0.99362(5) 0.39817(3) 1.39916(4) 0.03111(14) Uani 1 1 d . . .
P1 P 0.48510(14) 0.09486(7) 1.05488(9) 0.0226(2) Uani 1 1 d . . .
P2 P 0.75212(14) 0.36388(7) 1.38559(9) 0.0228(2) Uani 1 1 d . . .
N1 N 0.5688(5) 0.1502(3) 1.1660(3) 0.0269(8) Uani 1 1 d . . .
N2 N 0.6392(5) 0.2756(3) 1.3070(3) 0.0243(7) Uani 1 1 d . . .
N3 N 0.2454(5) 0.2890(3) 1.1504(3) 0.0289(8) Uani 1 1 d . . .
N4 N 0.5119(6) 0.3915(3) 1.1059(3) 0.0296(9) Uani 1 1 d . . .
C1 C 0.7331(6) 0.1301(3) 1.2622(4) 0.0279(9) Uani 1 1 d . . .
H1A H 0.8297 0.1537 1.2564 0.033 Uiso 1 1 calc R . .
H1B H 0.7478 0.0626 1.2760 0.033 Uiso 1 1 calc R . .
C2 C 0.7211(7) 0.1818(3) 1.3495(4) 0.0283(10) Uani 1 1 d . . .
H2A H 0.6517 0.1454 1.3707 0.034 Uiso 1 1 calc R . .
H2B H 0.8359 0.1901 1.4110 0.034 Uiso 1 1 calc R . .
C3 C 0.6514(6) 0.0652(3) 1.0233(4) 0.0284(10) Uani 1 1 d . . .
C4 C 0.6831(8) 0.1233(4) 0.9578(5) 0.0374(11) Uani 1 1 d . . .
H4 H 0.6107 0.1743 0.9223 0.045 Uiso 1 1 calc R . .
C5 C 0.8250(9) 0.1035(5) 0.9466(6) 0.0501(15) Uani 1 1 d . . .
H5 H 0.8465 0.1409 0.9022 0.060 Uiso 1 1 calc R . .
C6 C 0.9344(8) 0.0292(5) 1.0005(6) 0.0488(15) Uani 1 1 d . . .
H6 H 1.0298 0.0171 0.9931 0.059 Uiso 1 1 calc R . .
C7 C 0.9028(8) -0.0270(4) 1.0651(5) 0.0441(13) Uani 1 1 d . . .
H7 H 0.9774 -0.0769 1.1016 0.053 Uiso 1 1 calc R . .
C8 C 0.7618(8) -0.0104(4) 1.0766(5) 0.0383(12) Uani 1 1 d . . .
H8 H 0.7403 -0.0495 1.1198 0.046 Uiso 1 1 calc R . .
C9 C 0.3954(6) -0.0176(3) 1.0627(4) 0.0247(8) Uani 1 1 d . . .
C10 C 0.4006(6) -0.0430(3) 1.1551(4) 0.0288(9) Uani 1 1 d . . .
H10 H 0.4542 -0.0034 1.2140 0.035 Uiso 1 1 calc R . .
C11 C 0.3249(7) -0.1287(4) 1.1607(4) 0.0315(10) Uani 1 1 d . . .
H11 H 0.3301 -0.1465 1.2234 0.038 Uiso 1 1 calc R . .
C12 C 0.2432(7) -0.1858(3) 1.0722(5) 0.0317(10) Uani 1 1 d . . .
H12 H 0.1918 -0.2421 1.0752 0.038 Uiso 1 1 calc R . .
C13 C 0.2369(7) -0.1602(4) 0.9789(4) 0.0330(10) Uani 1 1 d . . .
H13 H 0.1804 -0.1990 0.9195 0.040 Uiso 1 1 calc R . .
C14 C 0.3144(6) -0.0770(4) 0.9738(4) 0.0308(10) Uani 1 1 d . . .
H14 H 0.3128 -0.0607 0.9118 0.037 Uiso 1 1 calc R . .
C15 C 0.7804(6) 0.3336(3) 1.5154(4) 0.0257(9) Uani 1 1 d . . .
C16 C 0.6560(7) 0.2791(3) 1.5217(4) 0.0301(10) Uani 1 1 d . . .
H16 H 0.5578 0.2588 1.4599 0.036 Uiso 1 1 calc R . .
C17 C 0.6784(7) 0.2549(4) 1.6202(4) 0.0344(10) Uani 1 1 d . . .
H17 H 0.5947 0.2187 1.6238 0.041 Uiso 1 1 calc R . .
C18 C 0.8222(7) 0.2840(4) 1.7115(4) 0.0353(11) Uani 1 1 d . . .
H18 H 0.8378 0.2661 1.7769 0.042 Uiso 1 1 calc R . .
C19 C 0.9441(7) 0.3396(4) 1.7067(4) 0.0389(12) Uani 1 1 d . . .
H19 H 1.0400 0.3607 1.7692 0.047 Uiso 1 1 calc R . .
C20 C 0.9254(7) 0.3648(4) 1.6091(4) 0.0334(10) Uani 1 1 d . . .
H20 H 1.0088 0.4021 1.6066 0.040 Uiso 1 1 calc R . .
C21 C 0.6070(6) 0.4647(3) 1.3440(4) 0.0248(9) Uani 1 1 d . . .
C22 C 0.6615(7) 0.5542(3) 1.3323(4) 0.0321(10) Uani 1 1 d . . .
H22 H 0.7727 0.5629 1.3437 0.039 Uiso 1 1 calc R . .
C23 C 0.5471(7) 0.6304(3) 1.3034(5) 0.0349(11) Uani 1 1 d . . .
H23 H 0.5827 0.6902 1.2956 0.042 Uiso 1 1 calc R . .
C24 C 0.3822(8) 0.6182(4) 1.2861(4) 0.0362(12) Uani 1 1 d . . .
H24 H 0.3067 0.6694 1.2659 0.043 Uiso 1 1 calc R . .
C25 C 0.3285(7) 0.5296(3) 1.2988(4) 0.0320(10) Uani 1 1 d . . .
H25 H 0.2176 0.5215 1.2880 0.038 Uiso 1 1 calc R . .
C26 C 0.4400(6) 0.4530(3) 1.3276(4) 0.0296(10) Uani 1 1 d . . .
H26 H 0.4038 0.3936 1.3360 0.036 Uiso 1 1 calc R . .
C27 C 0.6616(8) 0.3840(4) 1.0926(4) 0.0387(12) Uani 1 1 d . . .
H27A H 0.6299 0.4035 1.0222 0.058 Uiso 1 1 calc R . .
H27B H 0.7011 0.3196 1.1035 0.058 Uiso 1 1 calc R . .
H27C H 0.7527 0.4241 1.1433 0.058 Uiso 1 1 calc R . .
C28 C 0.4291(9) 0.4837(4) 1.0748(4) 0.0426(13) Uani 1 1 d . . .
H28A H 0.5145 0.5324 1.1097 0.064 Uiso 1 1 calc R . .
H28B H 0.3425 0.4887 1.0948 0.064 Uiso 1 1 calc R . .
H28C H 0.3755 0.4909 0.9994 0.064 Uiso 1 1 calc R . .
C29 C 0.2053(8) 0.2327(4) 1.2186(5) 0.0438(13) Uani 1 1 d . . .
H29A H 0.1628 0.2734 1.2529 0.066 Uiso 1 1 calc R . .
H29B H 0.3082 0.2010 1.2711 0.066 Uiso 1 1 calc R . .
H29C H 0.1184 0.1866 1.1766 0.066 Uiso 1 1 calc R . .
C30 C 0.0960(7) 0.3422(4) 1.0713(5) 0.0476(14) Uani 1 1 d . . .
H30A H 0.0005 0.2998 1.0320 0.071 Uiso 1 1 calc R . .
H30B H 0.1248 0.3729 1.0237 0.071 Uiso 1 1 calc R . .
H30C H 0.0643 0.3890 1.1060 0.071 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N4 1.868(4) . ?
Ti1 N3 1.884(4) . ?
Ti1 N1 2.046(4) . ?
Ti1 N2 2.064(4) . ?
Ti1 Se1 2.8025(9) . ?
Ti1 P1 3.0199(13) . ?
Se1 P1 2.1409(12) . ?
Se2 P2 2.1245(12) . ?
P1 N1 1.607(4) . ?
P1 C9 1.810(4) . ?
P1 C3 1.818(5) . ?
P2 N2 1.649(4) . ?
P2 C21 1.812(4) . ?
P2 C15 1.835(5) . ?
N1 C1 1.457(6) . ?
N2 C2 1.489(6) . ?
N3 C30 1.456(7) . ?
N3 C29 1.457(7) . ?
N4 C27 1.453(7) . ?
N4 C28 1.453(6) . ?
C1 C2 1.522(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.394(8) . ?
C3 C4 1.398(7) . ?
C4 C5 1.390(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.377(7) . ?
C9 C14 1.402(7) . ?
C10 C11 1.410(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.395(7) . ?
C15 C20 1.398(7) . ?
C16 C17 1.395(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.398(7) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.396(7) . ?
C21 C26 1.398(7) . ?
C22 C23 1.395(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
N4 Ti1 N3 112.96(19) . . ?
N4 Ti1 N1 126.12(19) . . ?
N3 Ti1 N1 120.12(18) . . ?
N4 Ti1 N2 101.12(18) . . ?
N3 Ti1 N2 102.67(17) . . ?
N1 Ti1 N2 76.47(15) . . ?
N4 Ti1 Se1 96.06(13) . . ?
N3 Ti1 Se1 93.73(13) . . ?
N1 Ti1 Se1 72.75(11) . . ?
N2 Ti1 Se1 149.20(11) . . ?
N4 Ti1 P1 118.39(13) . . ?
N3 Ti1 P1 113.07(13) . . ?
N1 Ti1 P1 29.80(11) . . ?
N2 Ti1 P1 106.27(11) . . ?
Se1 Ti1 P1 42.95(3) . . ?
P1 Se1 Ti1 73.95(4) . . ?
N1 P1 C9 110.9(2) . . ?
N1 P1 C3 110.4(2) . . ?
C9 P1 C3 105.1(2) . . ?
N1 P1 Se1 102.37(14) . . ?
C9 P1 Se1 113.32(16) . . ?
C3 P1 Se1 114.87(17) . . ?
N1 P1 Ti1 39.27(14) . . ?
C9 P1 Ti1 125.57(15) . . ?
C3 P1 Ti1 126.20(16) . . ?
Se1 P1 Ti1 63.10(3) . . ?
N2 P2 C21 106.2(2) . . ?
N2 P2 C15 105.0(2) . . ?
C21 P2 C15 103.2(2) . . ?
N2 P2 Se2 118.17(15) . . ?
C21 P2 Se2 111.99(16) . . ?
C15 P2 Se2 110.95(16) . . ?
C1 N1 P1 127.4(3) . . ?
C1 N1 Ti1 119.6(3) . . ?
P1 N1 Ti1 110.9(2) . . ?
C2 N2 P2 112.6(3) . . ?
C2 N2 Ti1 116.0(3) . . ?
P2 N2 Ti1 128.7(2) . . ?
C30 N3 C29 112.3(5) . . ?
C30 N3 Ti1 122.6(4) . . ?
C29 N3 Ti1 124.2(4) . . ?
C27 N4 C28 112.4(4) . . ?
C27 N4 Ti1 114.6(3) . . ?
C28 N4 Ti1 132.8(4) . . ?
N1 C1 C2 104.6(4) . . ?
N1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
N2 C2 C1 107.8(4) . . ?
N2 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
N2 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
C8 C3 C4 120.0(5) . . ?
C8 C3 P1 118.3(4) . . ?
C4 C3 P1 121.2(4) . . ?
C5 C4 C3 118.7(6) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C6 C5 C4 120.8(6) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 120.1(5) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.7(6) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C3 119.7(5) . . ?
C7 C8 H8 120.1 . . ?
C3 C8 H8 120.1 . . ?
C10 C9 C14 120.0(4) . . ?
C10 C9 P1 119.7(4) . . ?
C14 C9 P1 120.2(4) . . ?
C9 C10 C11 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.3(5) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.6(5) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 119.6(5) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
C16 C15 C20 118.9(4) . . ?
C16 C15 P2 120.1(4) . . ?
C20 C15 P2 121.0(4) . . ?
C17 C16 C15 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.1(5) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.7(5) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 119.6(5) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C26 119.7(4) . . ?
C22 C21 P2 121.1(4) . . ?
C26 C21 P2 119.1(4) . . ?
C23 C22 C21 119.1(5) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C24 C23 C22 120.9(5) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.1(5) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.0(5) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.2(5) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
N4 C27 H27A 109.5 . . ?
N4 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N4 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N4 C28 H28A 109.5 . . ?
N4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 H29A 109.5 . . ?
N3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N3 C30 H30A 109.5 . . ?
N3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
N4 Ti1 Se1 P1 126.00(14) . . . . ?
N3 Ti1 Se1 P1 -120.42(13) . . . . ?
N1 Ti1 Se1 P1 0.00(13) . . . . ?
N2 Ti1 Se1 P1 2.2(2) . . . . ?
Ti1 Se1 P1 N1 0.00(16) . . . . ?
Ti1 Se1 P1 C9 119.44(17) . . . . ?
Ti1 Se1 P1 C3 -119.66(17) . . . . ?
N4 Ti1 P1 N1 113.9(3) . . . . ?
N3 Ti1 P1 N1 -110.7(3) . . . . ?
N2 Ti1 P1 N1 1.2(3) . . . . ?
Se1 Ti1 P1 N1 180.0(2) . . . . ?
N4 Ti1 P1 C9 -166.7(2) . . . . ?
N3 Ti1 P1 C9 -31.3(2) . . . . ?
N1 Ti1 P1 C9 79.5(3) . . . . ?
N2 Ti1 P1 C9 80.6(2) . . . . ?
Se1 Ti1 P1 C9 -100.6(2) . . . . ?
N4 Ti1 P1 C3 36.2(3) . . . . ?
N3 Ti1 P1 C3 171.6(2) . . . . ?
N1 Ti1 P1 C3 -77.7(3) . . . . ?
N2 Ti1 P1 C3 -76.5(2) . . . . ?
Se1 Ti1 P1 C3 102.3(2) . . . . ?
N4 Ti1 P1 Se1 -66.13(16) . . . . ?
N3 Ti1 P1 Se1 69.28(15) . . . . ?
N1 Ti1 P1 Se1 180.0(2) . . . . ?
N2 Ti1 P1 Se1 -178.84(12) . . . . ?
C9 P1 N1 C1 75.6(4) . . . . ?
C3 P1 N1 C1 -40.6(5) . . . . ?
Se1 P1 N1 C1 -163.3(4) . . . . ?
Ti1 P1 N1 C1 -163.3(6) . . . . ?
C9 P1 N1 Ti1 -121.2(2) . . . . ?
C3 P1 N1 Ti1 122.7(2) . . . . ?
Se1 P1 N1 Ti1 0.0(2) . . . . ?
N4 Ti1 N1 C1 79.9(4) . . . . ?
N3 Ti1 N1 C1 -111.1(4) . . . . ?
N2 Ti1 N1 C1 -14.1(3) . . . . ?
Se1 Ti1 N1 C1 164.8(4) . . . . ?
P1 Ti1 N1 C1 164.8(5) . . . . ?
N4 Ti1 N1 P1 -84.8(3) . . . . ?
N3 Ti1 N1 P1 84.2(3) . . . . ?
N2 Ti1 N1 P1 -178.9(3) . . . . ?
Se1 Ti1 N1 P1 0.00(17) . . . . ?
C21 P2 N2 C2 -163.4(3) . . . . ?
C15 P2 N2 C2 -54.4(4) . . . . ?
Se2 P2 N2 C2 69.9(3) . . . . ?
C21 P2 N2 Ti1 36.4(3) . . . . ?
C15 P2 N2 Ti1 145.3(3) . . . . ?
Se2 P2 N2 Ti1 -90.3(3) . . . . ?
N4 Ti1 N2 C2 -137.1(3) . . . . ?
N3 Ti1 N2 C2 106.1(3) . . . . ?
N1 Ti1 N2 C2 -12.3(3) . . . . ?
Se1 Ti1 N2 C2 -14.4(5) . . . . ?
P1 Ti1 N2 C2 -12.9(4) . . . . ?
N4 Ti1 N2 P2 22.6(3) . . . . ?
N3 Ti1 N2 P2 -94.3(3) . . . . ?
N1 Ti1 N2 P2 147.4(3) . . . . ?
Se1 Ti1 N2 P2 145.26(17) . . . . ?
P1 Ti1 N2 P2 146.8(2) . . . . ?
N4 Ti1 N3 C30 37.9(5) . . . . ?
N1 Ti1 N3 C30 -132.4(4) . . . . ?
N2 Ti1 N3 C30 146.0(4) . . . . ?
Se1 Ti1 N3 C30 -60.3(4) . . . . ?
P1 Ti1 N3 C30 -99.9(4) . . . . ?
N4 Ti1 N3 C29 -152.9(4) . . . . ?
N1 Ti1 N3 C29 36.8(5) . . . . ?
N2 Ti1 N3 C29 -44.8(4) . . . . ?
Se1 Ti1 N3 C29 109.0(4) . . . . ?
P1 Ti1 N3 C29 69.3(4) . . . . ?
N3 Ti1 N4 C27 -174.0(3) . . . . ?
N1 Ti1 N4 C27 -4.3(4) . . . . ?
N2 Ti1 N4 C27 77.0(4) . . . . ?
Se1 Ti1 N4 C27 -77.4(3) . . . . ?
P1 Ti1 N4 C27 -38.6(4) . . . . ?
N3 Ti1 N4 C28 -0.1(5) . . . . ?
N1 Ti1 N4 C28 169.6(4) . . . . ?
N2 Ti1 N4 C28 -109.2(5) . . . . ?
Se1 Ti1 N4 C28 96.5(5) . . . . ?
P1 Ti1 N4 C28 135.3(4) . . . . ?
P1 N1 C1 C2 -163.0(4) . . . . ?
Ti1 N1 C1 C2 35.0(5) . . . . ?
P2 N2 C2 C1 -128.8(4) . . . . ?
Ti1 N2 C2 C1 34.1(5) . . . . ?
N1 C1 C2 N2 -41.1(5) . . . . ?
N1 P1 C3 C8 76.5(4) . . . . ?
C9 P1 C3 C8 -43.1(5) . . . . ?
Se1 P1 C3 C8 -168.4(4) . . . . ?
Ti1 P1 C3 C8 117.8(4) . . . . ?
N1 P1 C3 C4 -95.5(5) . . . . ?
C9 P1 C3 C4 144.9(4) . . . . ?
Se1 P1 C3 C4 19.6(5) . . . . ?
Ti1 P1 C3 C4 -54.2(5) . . . . ?
C8 C3 C4 C5 0.5(8) . . . . ?
P1 C3 C4 C5 172.4(5) . . . . ?
C3 C4 C5 C6 -1.2(9) . . . . ?
C4 C5 C6 C7 0.8(10) . . . . ?
C5 C6 C7 C8 0.3(10) . . . . ?
C6 C7 C8 C3 -1.0(9) . . . . ?
C4 C3 C8 C7 0.6(8) . . . . ?
P1 C3 C8 C7 -171.5(4) . . . . ?
N1 P1 C9 C10 2.1(4) . . . . ?
C3 P1 C9 C10 121.4(4) . . . . ?
Se1 P1 C9 C10 -112.4(4) . . . . ?
Ti1 P1 C9 C10 -39.6(5) . . . . ?
N1 P1 C9 C14 179.4(4) . . . . ?
C3 P1 C9 C14 -61.3(4) . . . . ?
Se1 P1 C9 C14 65.0(4) . . . . ?
Ti1 P1 C9 C14 137.7(3) . . . . ?
C14 C9 C10 C11 0.1(7) . . . . ?
P1 C9 C10 C11 177.4(4) . . . . ?
C9 C10 C11 C12 -1.1(7) . . . . ?
C10 C11 C12 C13 0.8(8) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C12 C13 C14 C9 -1.7(8) . . . . ?
C10 C9 C14 C13 1.3(7) . . . . ?
P1 C9 C14 C13 -176.0(4) . . . . ?
N2 P2 C15 C16 -29.2(4) . . . . ?
C21 P2 C15 C16 81.8(4) . . . . ?
Se2 P2 C15 C16 -158.0(3) . . . . ?
N2 P2 C15 C20 151.0(4) . . . . ?
C21 P2 C15 C20 -97.9(4) . . . . ?
Se2 P2 C15 C20 22.3(4) . . . . ?
C20 C15 C16 C17 -1.2(7) . . . . ?
P2 C15 C16 C17 179.1(4) . . . . ?
C15 C16 C17 C18 -0.2(8) . . . . ?
C16 C17 C18 C19 1.8(8) . . . . ?
C17 C18 C19 C20 -1.9(9) . . . . ?
C16 C15 C20 C19 1.1(8) . . . . ?
P2 C15 C20 C19 -179.2(4) . . . . ?
C18 C19 C20 C15 0.5(9) . . . . ?
N2 P2 C21 C22 -135.2(4) . . . . ?
C15 P2 C21 C22 114.5(4) . . . . ?
Se2 P2 C21 C22 -4.9(4) . . . . ?
N2 P2 C21 C26 47.3(4) . . . . ?
C15 P2 C21 C26 -62.9(4) . . . . ?
Se2 P2 C21 C26 177.7(3) . . . . ?
C26 C21 C22 C23 -0.6(7) . . . . ?
P2 C21 C22 C23 -178.0(4) . . . . ?
C21 C22 C23 C24 -0.2(8) . . . . ?
C22 C23 C24 C25 0.9(8) . . . . ?
C23 C24 C25 C26 -0.8(8) . . . . ?
C24 C25 C26 C21 0.0(8) . . . . ?
C22 C21 C26 C25 0.7(7) . . . . ?
P2 C21 C26 C25 178.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        70.57
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.090
####################################################################### 
# 
# 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_B
_database_code_depnum_ccdc_archive 'CCDC 1495777'
_audit_update_record             
;
2016-09-10 deposited with the CCDC.
2016-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H11 Cl N2 O'
_chemical_formula_sum            'C9 H11 Cl N2 O'
_chemical_formula_weight         198.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ti Ti 0.2191 1.8069 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.1347(3)
_cell_length_b                   11.3629(4)
_cell_length_c                   18.5528(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1925.72(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1873
_cell_measurement_theta_min      3.8870
_cell_measurement_theta_max      71.4541

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    3.201
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3946
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.767
_diffrn_reflns_theta_max         71.596
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1833
_reflns_number_gt                1568
_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       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III & Olex 2.1'
_computing_publication_material  WinGX
_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)+(0.0622P)²+1.5772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1833
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.11848(7) 0.39068(5) 0.47466(3) 0.0313(2) Uani 1 1 d . . . . .
O1 O 0.14591(18) 0.02540(15) 0.19836(9) 0.0265(4) Uani 1 1 d . . . . .
N1 N 0.3572(2) -0.02813(18) 0.14288(11) 0.0248(4) Uani 1 1 d . . . . .
N2 N 0.3644(2) 0.09886(16) 0.23942(10) 0.0209(4) Uani 1 1 d . . . . .
H2 H 0.4580 0.0979 0.2345 0.025 Uiso 1 1 calc R U . . .
C1 C 0.2809(2) 0.03159(19) 0.19351(12) 0.0200(5) Uani 1 1 d . . . . .
C2 C 0.2831(3) -0.1136(2) 0.09759(14) 0.0314(6) Uani 1 1 d . . . . .
H2A H 0.1875 -0.1293 0.1169 0.047 Uiso 1 1 calc R U . . .
H2B H 0.3388 -0.1851 0.0963 0.047 Uiso 1 1 calc R U . . .
H2C H 0.2738 -0.0827 0.0496 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5120(3) -0.0080(2) 0.12903(15) 0.0340(6) Uani 1 1 d . . . . .
H3A H 0.5333 0.0743 0.1342 0.051 Uiso 1 1 calc R U . . .
H3B H 0.5353 -0.0328 0.0809 0.051 Uiso 1 1 calc R U . . .
H3C H 0.5694 -0.0521 0.1629 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3026(2) 0.16956(19) 0.29441(12) 0.0194(5) Uani 1 1 d . . . . .
C5 C 0.3628(3) 0.16327(19) 0.36344(12) 0.0216(5) Uani 1 1 d . . . . .
H5 H 0.4411 0.1131 0.3725 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3055(3) 0.2319(2) 0.41852(12) 0.0229(5) Uani 1 1 d . . . . .
H6 H 0.3457 0.2284 0.4645 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1890(3) 0.30535(19) 0.40471(12) 0.0220(5) Uani 1 1 d . . . . .
C8 C 0.1293(3) 0.31440(19) 0.33613(12) 0.0226(5) Uani 1 1 d . . . . .
H8 H 0.0517 0.3654 0.3273 0.027 Uiso 1 1 calc R U . . .
C9 C 0.1869(2) 0.24639(19) 0.28096(12) 0.0211(5) Uani 1 1 d . . . . .
H9 H 0.1481 0.2521 0.2347 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.744(2) . ?
O1 C1 1.239(3) . ?
N1 C1 1.352(3) . ?
N1 C2 1.451(3) . ?
N1 C3 1.455(3) . ?
N2 C1 1.375(3) . ?
N2 C4 1.416(3) . ?
N2 H2 0.8600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C9 1.393(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 H9 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
C1 N1 C2 119.8(2) . . ?
C1 N1 C3 123.0(2) . . ?
C2 N1 C3 117.1(2) . . ?
C1 N2 C4 122.71(19) . . ?
C1 N2 H2 118.6 . . ?
C4 N2 H2 118.6 . . ?
O1 C1 N1 122.3(2) . . ?
O1 C1 N2 122.6(2) . . ?
N1 C1 N2 115.1(2) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 119.7(2) . . ?
C9 C4 N2 121.9(2) . . ?
C5 C4 N2 118.4(2) . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 121.3(2) . . ?
C6 C7 Cl1 118.96(18) . . ?
C8 C7 Cl1 119.71(18) . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C4 120.3(2) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?

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
C2 N1 C1 O1 -7.5(3) . . . . ?
C3 N1 C1 O1 170.0(2) . . . . ?
C2 N1 C1 N2 172.0(2) . . . . ?
C3 N1 C1 N2 -10.4(3) . . . . ?
C4 N2 C1 O1 -2.2(3) . . . . ?
C4 N2 C1 N1 178.3(2) . . . . ?
C1 N2 C4 C9 -48.9(3) . . . . ?
C1 N2 C4 C5 132.7(2) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
N2 C4 C5 C6 179.6(2) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C5 C6 C7 Cl1 179.87(17) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
Cl1 C7 C8 C9 179.73(17) . . . . ?
C7 C8 C9 C4 0.4(3) . . . . ?
C5 C4 C9 C8 -1.5(3) . . . . ?
N2 C4 C9 C8 -179.9(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
N2 H2 O1 0.86 2.27 2.940(2) 134.2 6_656
C8 H8 O1 0.93 2.61 3.532(3) 174.1 4
C5 H5 O1 0.93 2.49 3.234(3) 136.6 6_656
C2 H2C Cl1 0.96 2.95 3.725(3) 138.5 8_565

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.076

