# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Compound1N
_database_code_depnum_ccdc_archive 'CCDC 1858899'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N4 O4 Ti'
_chemical_formula_sum            'C28 H20 N4 O4 Ti'
_chemical_formula_weight         524.38

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'
Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   12.156(3)
_cell_length_b                   22.481(3)
_cell_length_c                   9.293(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.43(3)
_cell_angle_gamma                90
_cell_volume                     2364.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1542
_cell_measurement_theta_min      27.4540
_cell_measurement_theta_max      4.3760

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.407
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79690
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_reflns_number            4534
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.617
_diffrn_reflns_theta_max         28.956
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2700
_reflns_number_gt                2022
_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_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.1337P)²+9.0314P] 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         2700
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0942
_refine_ls_wR_factor_ref         0.2639
_refine_ls_wR_factor_gt          0.2415
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
C1 C -0.1677(3) 0.13296(17) 0.5268(4) 0.0405(9) Uani 1 1 d . . . . .
C2 C -0.2060(3) 0.08574(17) 0.4098(4) 0.0383(8) Uani 1 1 d . . . . .
C3 C -0.1217(4) 0.0473(2) 0.3862(6) 0.0544(11) Uani 1 1 d . . . . .
H3 H -0.041492 0.052747 0.441863 0.065 Uiso 1 1 calc R U . . .
C4 C -0.1595(5) 0.0016(2) 0.2801(6) 0.0625(13) Uani 1 1 d . . . . .
H4 H -0.104202 -0.023259 0.263241 0.075 Uiso 1 1 calc R U . . .
C5 C -0.2770(5) -0.0075(2) 0.1999(6) 0.0618(13) Uani 1 1 d . . . . .
H5 H -0.301299 -0.039314 0.131557 0.074 Uiso 1 1 calc R U . . .
C6 C -0.3597(5) 0.0300(2) 0.2190(5) 0.0592(12) Uani 1 1 d . . . . .
H6 H -0.439656 0.024279 0.161904 0.071 Uiso 1 1 calc R U . . .
C7 C -0.3236(4) 0.0759(2) 0.3233(5) 0.0457(9) Uani 1 1 d . . . . .
H7 H -0.380165 0.101054 0.335834 0.055 Uiso 1 1 calc R U . . .
C8 C -0.2599(3) 0.23731(18) 0.7133(5) 0.0415(9) Uani 1 1 d . . . . .
H8 H -0.340563 0.232078 0.660763 0.050 Uiso 1 1 calc R U . . .
C9 C -0.2224(4) 0.28338(17) 0.8338(4) 0.0403(9) Uani 1 1 d . . . . .
C10 C -0.3091(4) 0.3159(2) 0.8648(5) 0.0532(11) Uani 1 1 d . . . . .
H10 H -0.388710 0.308377 0.809772 0.064 Uiso 1 1 calc R U . . .
C11 C -0.2750(5) 0.3602(2) 0.9801(6) 0.0645(14) Uani 1 1 d . . . . .
H11 H -0.331494 0.382774 1.001063 0.077 Uiso 1 1 calc R U . . .
C12 C -0.1565(5) 0.3694(2) 1.0610(6) 0.0640(14) Uani 1 1 d . . . . .
H12 H -0.133389 0.398121 1.138444 0.077 Uiso 1 1 calc R U . . .
C13 C -0.0712(5) 0.3372(2) 1.0299(6) 0.0674(14) Uani 1 1 d . . . . .
H13 H 0.008410 0.344925 1.084569 0.081 Uiso 1 1 calc R U . . .
C14 C -0.1038(4) 0.29303(19) 0.9171(5) 0.0505(11) Uani 1 1 d . . . . .
N1 N -0.1903(3) 0.20422(14) 0.6758(4) 0.0378(7) Uani 1 1 d . . . . .
N2 N -0.2462(3) 0.16201(15) 0.5596(4) 0.0429(8) Uani 1 1 d . . . . .
O1 O -0.0536(3) 0.14386(15) 0.5933(4) 0.0584(9) Uani 1 1 d . . . . .
O2 O -0.0208(3) 0.26123(16) 0.8886(4) 0.0668(10) Uani 1 1 d . . . . .
Ti1 Ti 0.000000 0.20628(5) 0.750000 0.0500(4) Uani 1 2 d S T P . .


_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 N2 1.281(5) . ?
C1 O1 1.319(5) . ?
C1 C2 1.469(5) . ?
C2 C7 1.378(6) . ?
C2 C3 1.418(6) . ?
C3 C4 1.381(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.267(5) . ?
C8 C9 1.470(6) . ?
C8 H8 0.9300 . ?
C9 C14 1.382(6) . ?
C9 C10 1.396(6) . ?
C10 C11 1.411(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.392(6) . ?
C13 H13 0.9300 . ?
C14 O2 1.339(5) . ?
N1 N2 1.411(5) . ?
N1 Ti1 2.160(3) . ?
O1 Ti1 1.955(3) . ?
O2 Ti1 1.867(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
N2 C1 O1 122.8(4) . . ?
N2 C1 C2 118.8(3) . . ?
O1 C1 C2 118.4(4) . . ?
C7 C2 C3 117.8(4) . . ?
C7 C2 C1 121.9(4) . . ?
C3 C2 C1 120.3(4) . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.7(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C2 121.9(4) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
N1 C8 C9 124.9(3) . . ?
N1 C8 H8 117.6 . . ?
C9 C8 H8 117.6 . . ?
C14 C9 C10 120.9(4) . . ?
C14 C9 C8 120.4(4) . . ?
C10 C9 C8 118.6(4) . . ?
C9 C10 C11 119.5(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 121.6(5) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C14 120.2(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O2 C14 C9 120.8(4) . . ?
O2 C14 C13 120.1(4) . . ?
C9 C14 C13 119.1(4) . . ?
C8 N1 N2 115.0(3) . . ?
C8 N1 Ti1 130.1(3) . . ?
N2 N1 Ti1 114.7(2) . . ?
C1 N2 N1 109.4(3) . . ?
C1 O1 Ti1 119.3(3) . . ?
C14 O2 Ti1 142.3(3) . . ?
O2 Ti1 O2 97.2(3) 2_556 . ?
O2 Ti1 O1 153.70(14) 2_556 2_556 ?
O2 Ti1 O1 93.06(17) . 2_556 ?
O2 Ti1 O1 93.06(17) 2_556 . ?
O2 Ti1 O1 153.70(14) . . ?
O1 Ti1 O1 88.2(2) 2_556 . ?
O2 Ti1 N1 80.52(13) 2_556 2_556 ?
O2 Ti1 N1 101.14(13) . 2_556 ?
O1 Ti1 N1 73.74(12) 2_556 2_556 ?
O1 Ti1 N1 104.43(12) . 2_556 ?
O2 Ti1 N1 101.14(13) 2_556 . ?
O2 Ti1 N1 80.52(13) . . ?
O1 Ti1 N1 104.43(12) 2_556 . ?
O1 Ti1 N1 73.74(12) . . ?
N1 Ti1 N1 177.54(18) 2_556 . ?

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
N2 C1 C2 C7 6.8(6) . . . . ?
O1 C1 C2 C7 -172.9(4) . . . . ?
N2 C1 C2 C3 -171.1(4) . . . . ?
O1 C1 C2 C3 9.2(6) . . . . ?
C7 C2 C3 C4 -0.5(7) . . . . ?
C1 C2 C3 C4 177.4(4) . . . . ?
C2 C3 C4 C5 -1.1(8) . . . . ?
C3 C4 C5 C6 2.4(9) . . . . ?
C4 C5 C6 C7 -1.8(8) . . . . ?
C5 C6 C7 C2 0.1(7) . . . . ?
C3 C2 C7 C6 1.1(6) . . . . ?
C1 C2 C7 C6 -176.9(4) . . . . ?
N1 C8 C9 C14 -0.6(6) . . . . ?
N1 C8 C9 C10 -178.9(4) . . . . ?
C14 C9 C10 C11 1.6(6) . . . . ?
C8 C9 C10 C11 179.9(4) . . . . ?
C9 C10 C11 C12 -1.1(7) . . . . ?
C10 C11 C12 C13 1.1(8) . . . . ?
C11 C12 C13 C14 -1.6(8) . . . . ?
C10 C9 C14 O2 179.1(4) . . . . ?
C8 C9 C14 O2 0.8(6) . . . . ?
C10 C9 C14 C13 -2.0(7) . . . . ?
C8 C9 C14 C13 179.7(4) . . . . ?
C12 C13 C14 O2 -179.1(5) . . . . ?
C12 C13 C14 C9 2.0(8) . . . . ?
C9 C8 N1 N2 178.4(3) . . . . ?
C9 C8 N1 Ti1 -6.5(6) . . . . ?
O1 C1 N2 N1 -1.3(5) . . . . ?
C2 C1 N2 N1 179.0(3) . . . . ?
C8 N1 N2 C1 177.3(3) . . . . ?
Ti1 N1 N2 C1 1.4(4) . . . . ?
N2 C1 O1 Ti1 0.6(5) . . . . ?
C2 C1 O1 Ti1 -179.8(3) . . . . ?
C9 C14 O2 Ti1 8.8(8) . . . . ?
C13 C14 O2 Ti1 -170.1(4) . . . . ?
C14 O2 Ti1 O2 88.7(6) . . . 2_556 ?
C14 O2 Ti1 O1 -115.6(6) . . . 2_556 ?
C14 O2 Ti1 O1 -23.3(8) . . . . ?
C14 O2 Ti1 N1 170.4(5) . . . 2_556 ?
C14 O2 Ti1 N1 -11.4(6) . . . . ?

_refine_diff_density_max         1.909
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_L5N
_database_code_depnum_ccdc_archive 'CCDC 1858905'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N3 O2'
_chemical_formula_sum            'C15 H15 N3 O2'
_chemical_formula_weight         269.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.127(2)
_cell_length_b                   9.0733(12)
_cell_length_c                   13.116(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.543(17)
_cell_angle_gamma                90
_cell_volume                     1305.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1168
_cell_measurement_theta_max      27.1170
_cell_measurement_theta_min      4.3000

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_description       block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_reflns_number            5022
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.455
_diffrn_reflns_theta_max         28.888
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2980
_reflns_number_gt                2027
_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_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0583P)²+0.0931P] 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         2980
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.006
_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 0.84581(16) 0.47097(19) 0.63200(13) 0.0398(4) Uani 1 1 d . . . . .
C2 C 0.71522(16) 0.50128(18) 0.63500(12) 0.0375(4) Uani 1 1 d . . . . .
C3 C 0.68072(16) 0.6331(2) 0.67439(13) 0.0434(4) Uani 1 1 d . . . . .
H3 H 0.739467 0.704382 0.696127 0.052 Uiso 1 1 calc R U . . .
C4 C 0.56010(17) 0.6609(2) 0.68202(13) 0.0455(5) Uani 1 1 d . . . . .
H4 H 0.538536 0.751082 0.707376 0.055 Uiso 1 1 calc R U . . .
C5 C 0.47087(16) 0.5546(2) 0.65200(12) 0.0406(4) Uani 1 1 d . . . . .
C6 C 0.50596(16) 0.4225(2) 0.61373(14) 0.0433(4) Uani 1 1 d . . . . .
H6 H 0.447847 0.349838 0.593941 0.052 Uiso 1 1 calc R U . . .
C7 C 0.62567(16) 0.39658(19) 0.60434(13) 0.0415(4) Uani 1 1 d . . . . .
H7 H 0.646746 0.307479 0.577021 0.050 Uiso 1 1 calc R U . . .
C8 C 1.00399(15) 0.23913(19) 0.48227(12) 0.0367(4) Uani 1 1 d . . . . .
C9 C 1.12466(14) 0.16874(18) 0.49980(12) 0.0349(4) Uani 1 1 d . . . . .
C10 C 1.16041(17) 0.0728(2) 0.42696(13) 0.0456(5) Uani 1 1 d . . . . .
H10 H 1.108464 0.058513 0.364510 0.055 Uiso 1 1 calc R U . . .
C11 C 1.26949(18) -0.0009(2) 0.44446(15) 0.0524(5) Uani 1 1 d . . . . .
H11 H 1.291920 -0.061455 0.393562 0.063 Uiso 1 1 calc R U . . .
C12 C 1.34588(17) 0.0153(2) 0.53826(16) 0.0508(5) Uani 1 1 d . . . . .
H12 H 1.418288 -0.037761 0.551610 0.061 Uiso 1 1 calc R U . . .
C13 C 1.31545(15) 0.1089(2) 0.61133(14) 0.0461(5) Uani 1 1 d . . . . .
H13 H 1.367254 0.118785 0.674313 0.055 Uiso 1 1 calc R U . . .
C14 C 1.20810(15) 0.18933(19) 0.59268(12) 0.0375(4) Uani 1 1 d . . . . .
C15 C 0.91593(17) 0.2098(2) 0.38483(14) 0.0523(5) Uani 1 1 d . . . . .
H15A H 0.865384 0.127226 0.395170 0.078 Uiso 1 1 calc R U . . .
H15B H 0.960215 0.188282 0.329722 0.078 Uiso 1 1 calc R U . . .
H15C H 0.865812 0.295193 0.367221 0.078 Uiso 1 1 calc R U . . .
N1 N 0.97966(13) 0.32226(16) 0.55586(11) 0.0399(4) Uani 1 1 d . . . . .
N2 N 0.86611(13) 0.38228(18) 0.55203(12) 0.0439(4) Uani 1 1 d . . . . .
N3 N 0.34844(15) 0.5827(2) 0.65583(14) 0.0538(5) Uani 1 1 d . . . . .
O1 O 0.92908(12) 0.51773(15) 0.69611(10) 0.0559(4) Uani 1 1 d . . . . .
O2 O 1.18595(12) 0.28653(15) 0.66662(9) 0.0478(3) Uani 1 1 d . . . . .
H2N H 0.807(2) 0.359(2) 0.4999(17) 0.072 Uiso 1 1 d . U . . .
H2O H 1.106(2) 0.326(2) 0.6427(17) 0.072 Uiso 1 1 d . U . . .
H31 H 0.308(2) 0.504(3) 0.6589(18) 0.072 Uiso 1 1 d . U . . .
H32 H 0.3404(19) 0.648(3) 0.7057(18) 0.072 Uiso 1 1 d . 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
C1 O1 1.220(2) . ?
C1 N2 1.370(2) . ?
C1 C2 1.486(2) . ?
C2 C3 1.382(2) . ?
C2 C7 1.387(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 N3 1.395(2) . ?
C6 C7 1.378(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.289(2) . ?
C8 C9 1.470(2) . ?
C8 C15 1.500(2) . ?
C9 C10 1.398(2) . ?
C9 C14 1.416(2) . ?
C10 C11 1.371(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(2) . ?
C13 H13 0.9300 . ?
C14 O2 1.363(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 N2 1.3692(19) . ?
N2 H2N 0.89(2) . ?
N3 H31 0.85(2) . ?
N3 H32 0.90(2) . ?
O2 H2O 0.97(2) . ?

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
O1 C1 N2 121.97(17) . . ?
O1 C1 C2 123.49(16) . . ?
N2 C1 C2 114.52(15) . . ?
C3 C2 C7 118.05(17) . . ?
C3 C2 C1 120.23(16) . . ?
C7 C2 C1 121.62(16) . . ?
C2 C3 C4 121.10(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 120.50(17) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.18(17) . . ?
C6 C5 N3 120.57(17) . . ?
C4 C5 N3 121.19(17) . . ?
C7 C6 C5 121.11(17) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 121.04(17) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
N1 C8 C9 115.91(14) . . ?
N1 C8 C15 123.60(16) . . ?
C9 C8 C15 120.46(15) . . ?
C10 C9 C14 116.72(15) . . ?
C10 C9 C8 121.30(15) . . ?
C14 C9 C8 121.92(15) . . ?
C11 C10 C9 122.24(17) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 119.57(18) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.26(18) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.69(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
O2 C14 C13 117.85(15) . . ?
O2 C14 C9 121.82(15) . . ?
C13 C14 C9 120.33(16) . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 N1 N2 120.83(14) . . ?
N1 N2 C1 118.28(14) . . ?
N1 N2 H2N 119.8(14) . . ?
C1 N2 H2N 121.8(14) . . ?
C5 N3 H31 112.1(15) . . ?
C5 N3 H32 111.3(14) . . ?
H31 N3 H32 114(2) . . ?
C14 O2 H2O 106.1(13) . . ?

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
O1 C1 C2 C3 32.1(3) . . . . ?
N2 C1 C2 C3 -149.40(16) . . . . ?
O1 C1 C2 C7 -144.19(18) . . . . ?
N2 C1 C2 C7 34.3(2) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C4 -177.16(14) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 N3 -177.75(16) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
N3 C5 C6 C7 176.46(15) . . . . ?
C5 C6 C7 C2 1.3(3) . . . . ?
C3 C2 C7 C6 -0.6(2) . . . . ?
C1 C2 C7 C6 175.79(15) . . . . ?
N1 C8 C9 C10 178.18(15) . . . . ?
C15 C8 C9 C10 -0.2(2) . . . . ?
N1 C8 C9 C14 1.0(2) . . . . ?
C15 C8 C9 C14 -177.42(16) . . . . ?
C14 C9 C10 C11 1.4(3) . . . . ?
C8 C9 C10 C11 -175.95(17) . . . . ?
C9 C10 C11 C12 2.2(3) . . . . ?
C10 C11 C12 C13 -2.8(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 O2 -176.68(16) . . . . ?
C12 C13 C14 C9 3.9(3) . . . . ?
C10 C9 C14 O2 176.23(15) . . . . ?
C8 C9 C14 O2 -6.5(2) . . . . ?
C10 C9 C14 C13 -4.4(2) . . . . ?
C8 C9 C14 C13 172.93(16) . . . . ?
C9 C8 N1 N2 -173.89(14) . . . . ?
C15 C8 N1 N2 4.5(3) . . . . ?
C8 N1 N2 C1 -179.38(15) . . . . ?
O1 C1 N2 N1 12.7(3) . . . . ?
C2 C1 N2 N1 -165.77(14) . . . . ?

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
_geom_hbond_publ_flag
C15 H15C N3 0.96 2.60 3.459(3) 148.9 3_666 yes
N2 H2N N3 0.89(2) 2.50(2) 3.328(2) 154.0(19) 3_666 yes
O2 H2O N1 0.97(2) 1.65(2) 2.5256(19) 147.9(19) . yes
N3 H31 O2 0.85(2) 2.40(2) 3.255(2) 178(2) 1_455 yes
N3 H32 O2 0.90(2) 2.15(2) 3.047(2) 174(2) 2_656 yes

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_Compound5N
_database_code_depnum_ccdc_archive 'CCDC 1858903'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 N6 O4 Ti'
_chemical_formula_sum            'C30 H26 N6 O4 Ti'
_chemical_formula_weight         582.47

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'
Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   22.759(2)
_cell_length_b                   9.6698(6)
_cell_length_c                   12.5632(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.870(9)
_cell_angle_gamma                90
_cell_volume                     2659.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2894
_cell_measurement_theta_max      27.3410
_cell_measurement_theta_min      3.8580

_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_description       block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.371
_shelx_estimated_absorpt_T_min   0.913
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_reflns_number            9124
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.376
_diffrn_reflns_theta_max         29.090
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3164
_reflns_number_gt                2253
_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_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1484P)²+5.3911P] 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         3164
_refine_ls_number_parameters     193
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0891
_refine_ls_wR_factor_ref         0.2601
_refine_ls_wR_factor_gt          0.2376
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.42053(18) 0.0372(4) 0.8428(3) 0.0383(8) Uani 1 1 d . . . . .
C2 C 0.36850(17) -0.0550(4) 0.8359(3) 0.0372(8) Uani 1 1 d . . . . .
C3 C 0.3476(2) -0.1434(5) 0.7457(4) 0.0513(10) Uani 1 1 d . . . . .
H3 H 0.367506 -0.146415 0.690255 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2968(2) -0.2272(5) 0.7386(4) 0.0547(11) Uani 1 1 d . . . . .
H4 H 0.283766 -0.287471 0.679123 0.066 Uiso 1 1 calc R U . . .
C5 C 0.2656(2) -0.2222(4) 0.8179(4) 0.0506(10) Uani 1 1 d . . . . .
C6 C 0.2858(2) -0.1331(5) 0.9077(4) 0.0559(11) Uani 1 1 d . . . . .
H6 H 0.264748 -0.127692 0.961390 0.067 Uiso 1 1 calc R U . . .
C7 C 0.3368(2) -0.0533(4) 0.9170(4) 0.0466(10) Uani 1 1 d . . . . .
H7 H 0.350718 0.003287 0.978668 0.056 Uiso 1 1 calc R U . . .
C8 C 0.51351(17) 0.2743(4) 1.0021(3) 0.0353(8) Uani 1 1 d . . . . .
C9 C 0.56285(17) 0.3720(4) 0.9985(3) 0.0364(8) Uani 1 1 d . . . . .
C10 C 0.5886(2) 0.4589(5) 1.0895(4) 0.0510(11) Uani 1 1 d . . . . .
H10 H 0.573494 0.455110 1.151230 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6352(3) 0.5490(5) 1.0896(4) 0.0630(13) Uani 1 1 d . . . . .
H11 H 0.651040 0.605953 1.150327 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6583(2) 0.5544(5) 0.9993(4) 0.0605(13) Uani 1 1 d . . . . .
H12 H 0.691081 0.612589 1.000611 0.073 Uiso 1 1 calc R U . . .
C13 C 0.6336(2) 0.4747(5) 0.9071(4) 0.0517(11) Uani 1 1 d . . . . .
H13 H 0.648619 0.480861 0.845515 0.062 Uiso 1 1 calc R U . . .
C14 C 0.58569(19) 0.3848(4) 0.9069(3) 0.0405(9) Uani 1 1 d . . . . .
C15 C 0.4929(2) 0.2655(5) 1.1060(3) 0.0466(10) Uani 1 1 d . . . . .
H15A H 0.476121 0.352845 1.119296 0.070 Uiso 1 1 calc R U . . .
H15B H 0.527109 0.242983 1.167497 0.070 Uiso 1 1 calc R U . . .
H15C H 0.462243 0.194975 1.097556 0.070 Uiso 1 1 calc R U . . .
N1 N 0.48820(14) 0.1977(3) 0.9168(2) 0.0335(7) Uani 1 1 d . . . . .
N2 N 0.44108(15) 0.1121(3) 0.9307(3) 0.0389(8) Uani 1 1 d . . . . .
N3 N 0.2139(2) -0.3040(5) 0.8093(5) 0.0726(13) Uani 1 1 d D . . . .
O1 O 0.44251(14) 0.0435(3) 0.7571(2) 0.0492(8) Uani 1 1 d . . . . .
O2 O 0.56183(17) 0.3130(3) 0.8135(3) 0.0616(10) Uani 1 1 d . . . . .
Ti1 Ti 0.500000 0.18927(10) 0.750000 0.0385(3) Uani 1 2 d S T P . .
H31N H 0.209(2) -0.376(4) 0.758(3) 0.058 Uiso 1 1 d D U . . .
H32N H 0.1866(19) -0.274(5) 0.850(4) 0.058 Uiso 1 1 d D 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
C1 N2 1.296(5) . ?
C1 O1 1.307(5) . ?
C1 C2 1.465(5) . ?
C2 C3 1.395(6) . ?
C2 C7 1.400(5) . ?
C3 C4 1.395(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(7) . ?
C5 N3 1.397(6) . ?
C6 C7 1.372(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.300(5) . ?
C8 C9 1.478(5) . ?
C8 C15 1.506(5) . ?
C9 C14 1.392(5) . ?
C9 C10 1.411(6) . ?
C10 C11 1.372(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9300 . ?
C14 O2 1.344(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 N2 1.403(4) . ?
N1 Ti1 2.186(3) . ?
N3 H31N 0.936(19) . ?
N3 H32N 0.952(19) . ?
O1 Ti1 1.942(3) . ?
O2 Ti1 1.853(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
N2 C1 O1 123.1(3) . . ?
N2 C1 C2 119.2(3) . . ?
O1 C1 C2 117.7(4) . . ?
C3 C2 C7 118.0(4) . . ?
C3 C2 C1 120.8(4) . . ?
C7 C2 C1 121.2(4) . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.2(4) . . ?
C4 C5 N3 121.0(5) . . ?
C6 C5 N3 119.9(5) . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 121.6(4) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N1 C8 C9 120.6(3) . . ?
N1 C8 C15 120.6(3) . . ?
C9 C8 C15 118.8(3) . . ?
C14 C9 C10 116.9(4) . . ?
C14 C9 C8 122.7(3) . . ?
C10 C9 C8 120.4(3) . . ?
C11 C10 C9 121.9(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.7(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 119.4(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
O2 C14 C9 121.6(3) . . ?
O2 C14 C13 116.9(3) . . ?
C9 C14 C13 121.5(4) . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 N1 N2 114.5(3) . . ?
C8 N1 Ti1 131.9(2) . . ?
N2 N1 Ti1 113.3(2) . . ?
C1 N2 N1 109.5(3) . . ?
C5 N3 H31N 115(3) . . ?
C5 N3 H32N 116(3) . . ?
H31N N3 H32N 129(4) . . ?
C1 O1 Ti1 119.1(2) . . ?
C14 O2 Ti1 141.9(3) . . ?
O2 Ti1 O2 99.6(2) . 2_656 ?
O2 Ti1 O1 92.68(15) . 2_656 ?
O2 Ti1 O1 152.98(13) 2_656 2_656 ?
O2 Ti1 O1 152.98(13) . . ?
O2 Ti1 O1 92.67(15) 2_656 . ?
O1 Ti1 O1 86.91(19) 2_656 . ?
O2 Ti1 N1 80.86(12) . . ?
O2 Ti1 N1 96.34(12) 2_656 . ?
O1 Ti1 N1 109.40(12) 2_656 . ?
O1 Ti1 N1 73.87(11) . . ?
O2 Ti1 N1 96.34(12) . 2_656 ?
O2 Ti1 N1 80.86(12) 2_656 2_656 ?
O1 Ti1 N1 73.87(11) 2_656 2_656 ?
O1 Ti1 N1 109.40(12) . 2_656 ?
N1 Ti1 N1 175.70(16) . 2_656 ?

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
N2 C1 C2 C3 -176.0(4) . . . . ?
O1 C1 C2 C3 6.6(6) . . . . ?
N2 C1 C2 C7 6.5(6) . . . . ?
O1 C1 C2 C7 -170.8(4) . . . . ?
C7 C2 C3 C4 -0.4(6) . . . . ?
C1 C2 C3 C4 -177.9(4) . . . . ?
C2 C3 C4 C5 1.6(7) . . . . ?
C3 C4 C5 C6 -0.9(7) . . . . ?
C3 C4 C5 N3 178.6(5) . . . . ?
C4 C5 C6 C7 -1.0(7) . . . . ?
N3 C5 C6 C7 179.5(5) . . . . ?
C5 C6 C7 C2 2.3(7) . . . . ?
C3 C2 C7 C6 -1.6(7) . . . . ?
C1 C2 C7 C6 176.0(4) . . . . ?
N1 C8 C9 C14 -1.8(6) . . . . ?
C15 C8 C9 C14 178.5(4) . . . . ?
N1 C8 C9 C10 177.5(4) . . . . ?
C15 C8 C9 C10 -2.3(6) . . . . ?
C14 C9 C10 C11 -1.9(7) . . . . ?
C8 C9 C10 C11 178.8(4) . . . . ?
C9 C10 C11 C12 -0.7(8) . . . . ?
C10 C11 C12 C13 2.7(8) . . . . ?
C11 C12 C13 C14 -1.9(8) . . . . ?
C10 C9 C14 O2 -175.9(4) . . . . ?
C8 C9 C14 O2 3.4(6) . . . . ?
C10 C9 C14 C13 2.8(6) . . . . ?
C8 C9 C14 C13 -178.0(4) . . . . ?
C12 C13 C14 O2 177.8(4) . . . . ?
C12 C13 C14 C9 -0.9(7) . . . . ?
C9 C8 N1 N2 -178.6(3) . . . . ?
C15 C8 N1 N2 1.1(5) . . . . ?
C9 C8 N1 Ti1 -4.5(5) . . . . ?
C15 C8 N1 Ti1 175.2(3) . . . . ?
O1 C1 N2 N1 0.7(5) . . . . ?
C2 C1 N2 N1 -176.5(3) . . . . ?
C8 N1 N2 C1 -177.8(3) . . . . ?
Ti1 N1 N2 C1 6.9(4) . . . . ?
N2 C1 O1 Ti1 -9.4(5) . . . . ?
C2 C1 O1 Ti1 167.8(3) . . . . ?
C9 C14 O2 Ti1 2.5(7) . . . . ?
C13 C14 O2 Ti1 -176.2(4) . . . . ?
C14 O2 Ti1 O2 89.0(5) . . . 2_656 ?
C14 O2 Ti1 O1 -115.1(5) . . . 2_656 ?
C14 O2 Ti1 O1 -26.7(7) . . . . ?
C14 O2 Ti1 N1 -5.9(5) . . . . ?
C14 O2 Ti1 N1 170.8(5) . . . 2_656 ?

_refine_diff_density_max         1.988
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.106

####################################################################### 
# 
# 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_Compound3N
_database_code_depnum_ccdc_archive 'CCDC 1858906'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H28 N4 O4 Ti'
_chemical_formula_sum            'C32 H28 N4 O4 Ti'
_chemical_formula_weight         580.48

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'
Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   12.5941(13)
_cell_length_b                   22.237(2)
_cell_length_c                   10.5358(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.237(12)
_cell_angle_gamma                90
_cell_volume                     2818.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1482
_cell_measurement_theta_max      26.8370
_cell_measurement_theta_min      3.9900

_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_description       plate
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.348
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            5654
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.137
_diffrn_reflns_theta_max         28.904
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3264
_reflns_number_gt                2032
_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_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0962P)²+11.8723P] 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         3264
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0855
_refine_ls_wR_factor_ref         0.2576
_refine_ls_wR_factor_gt          0.2253
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.6469(4) 0.3299(2) 0.4274(4) 0.0387(11) Uani 1 1 d . . . . .
C2 C 0.6743(4) 0.3775(2) 0.5286(5) 0.0413(11) Uani 1 1 d . . . . .
C3 C 0.5911(6) 0.4092(3) 0.5578(6) 0.0646(17) Uani 1 1 d . . . . .
H3 H 0.517215 0.400034 0.514405 0.077 Uiso 1 1 calc R U . . .
C4 C 0.6165(7) 0.4554(3) 0.6525(7) 0.080(2) Uani 1 1 d . . . . .
H4 H 0.559111 0.476800 0.670305 0.096 Uiso 1 1 calc R U . . .
C5 C 0.7251(7) 0.4695(3) 0.7198(6) 0.0631(17) Uani 1 1 d . . . . .
C6 C 0.8074(6) 0.4369(3) 0.6905(5) 0.0586(16) Uani 1 1 d . . . . .
H6 H 0.881258 0.445426 0.735617 0.070 Uiso 1 1 calc R U . . .
C7 C 0.7841(5) 0.3917(2) 0.5961(5) 0.0462(12) Uani 1 1 d . . . . .
H7 H 0.841784 0.370777 0.577739 0.055 Uiso 1 1 calc R U . . .
C8 C 0.7466(3) 0.2382(2) 0.2317(4) 0.0321(10) Uani 1 1 d . . . . .
C9 C 0.7099(4) 0.1939(2) 0.1246(5) 0.0381(11) Uani 1 1 d . . . . .
C10 C 0.7854(5) 0.1690(3) 0.0636(6) 0.0570(15) Uani 1 1 d . . . . .
H10 H 0.859461 0.181000 0.092421 0.068 Uiso 1 1 calc R U . . .
C11 C 0.7530(6) 0.1277(3) -0.0369(6) 0.073(2) Uani 1 1 d . . . . .
H11 H 0.803857 0.113002 -0.077734 0.087 Uiso 1 1 calc R U . . .
C12 C 0.6430(6) 0.1080(3) -0.0774(6) 0.0641(17) Uani 1 1 d . . . . .
H12 H 0.620754 0.079002 -0.143543 0.077 Uiso 1 1 calc R U . . .
C13 C 0.5686(5) 0.1308(3) -0.0209(5) 0.0518(13) Uani 1 1 d . . . . .
H13 H 0.495225 0.117762 -0.050081 0.062 Uiso 1 1 calc R U . . .
C14 C 0.5990(4) 0.1733(2) 0.0795(5) 0.0387(11) Uani 1 1 d . . . . .
C15 C 0.8682(4) 0.2533(3) 0.2812(5) 0.0503(13) Uani 1 1 d . . . . .
H15A H 0.885978 0.281961 0.222483 0.075 Uiso 1 1 calc R U . . .
H15B H 0.911247 0.217398 0.283770 0.075 Uiso 1 1 calc R U . . .
H15C H 0.885146 0.270064 0.368846 0.075 Uiso 1 1 calc R U . . .
C16 C 0.7500(8) 0.5171(3) 0.8263(7) 0.097(3) Uani 1 1 d . . . . .
H16A H 0.828977 0.520716 0.864699 0.146 Uiso 1 1 calc R U . . .
H16B H 0.716801 0.506005 0.894060 0.146 Uiso 1 1 calc R U . . .
H16C H 0.719963 0.554887 0.788023 0.146 Uiso 1 1 calc R U . . .
N1 N 0.6764(3) 0.26411(17) 0.2848(4) 0.0338(9) Uani 1 1 d . . . . .
N2 N 0.7238(3) 0.30784(19) 0.3808(4) 0.0401(9) Uani 1 1 d . . . . .
O1 O 0.5434(3) 0.31044(18) 0.3877(3) 0.0502(9) Uani 1 1 d . . . . .
O2 O 0.5231(3) 0.19329(17) 0.1345(4) 0.0511(10) Uani 1 1 d . . . . .
Ti1 Ti 0.500000 0.25054(6) 0.250000 0.0367(4) Uani 1 2 d S T P . .


_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 N2 1.304(6) . ?
C1 O1 1.319(6) . ?
C1 C2 1.469(7) . ?
C2 C3 1.372(8) . ?
C2 C7 1.391(7) . ?
C3 C4 1.400(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(9) . ?
C5 C16 1.506(8) . ?
C6 C7 1.383(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.311(5) . ?
C8 C9 1.466(7) . ?
C8 C15 1.502(6) . ?
C9 C10 1.410(7) . ?
C9 C14 1.412(7) . ?
C10 C11 1.369(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.349(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(7) . ?
C13 H13 0.9300 . ?
C14 O2 1.331(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.403(5) . ?
N1 Ti1 2.162(4) . ?
O1 Ti1 1.925(4) . ?
O2 Ti1 1.843(4) . ?

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
N2 C1 O1 122.1(4) . . ?
N2 C1 C2 120.2(4) . . ?
O1 C1 C2 117.6(4) . . ?
C3 C2 C7 118.5(5) . . ?
C3 C2 C1 120.2(5) . . ?
C7 C2 C1 121.2(5) . . ?
C2 C3 C4 120.6(6) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 121.1(6) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 117.7(6) . . ?
C6 C5 C16 122.3(7) . . ?
C4 C5 C16 119.9(7) . . ?
C5 C6 C7 122.1(6) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 120.0(5) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N1 C8 C9 121.6(4) . . ?
N1 C8 C15 120.1(4) . . ?
C9 C8 C15 118.3(4) . . ?
C10 C9 C14 117.0(5) . . ?
C10 C9 C8 120.9(4) . . ?
C14 C9 C8 122.1(4) . . ?
C11 C10 C9 121.9(5) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 119.2(5) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.3(6) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 121.6(5) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
O2 C14 C13 119.3(5) . . ?
O2 C14 C9 120.7(4) . . ?
C13 C14 C9 120.0(5) . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N1 N2 114.5(4) . . ?
C8 N1 Ti1 130.9(3) . . ?
N2 N1 Ti1 114.5(3) . . ?
C1 N2 N1 109.1(4) . . ?
C1 O1 Ti1 119.9(3) . . ?
C14 O2 Ti1 142.4(3) . . ?
O2 Ti1 O2 92.6(3) . 2_655 ?
O2 Ti1 O1 155.54(15) . . ?
O2 Ti1 O1 92.61(17) 2_655 . ?
O2 Ti1 O1 92.61(17) . 2_655 ?
O2 Ti1 O1 155.54(15) 2_655 2_655 ?
O1 Ti1 O1 92.4(2) . 2_655 ?
O2 Ti1 N1 81.54(14) . . ?
O2 Ti1 N1 109.87(14) 2_655 . ?
O1 Ti1 N1 74.21(14) . . ?
O1 Ti1 N1 94.53(14) 2_655 . ?
O2 Ti1 N1 109.87(14) . 2_655 ?
O2 Ti1 N1 81.54(14) 2_655 2_655 ?
O1 Ti1 N1 94.53(14) . 2_655 ?
O1 Ti1 N1 74.22(14) 2_655 2_655 ?
N1 Ti1 N1 164.0(2) . 2_655 ?

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
N2 C1 C2 C3 166.5(5) . . . . ?
O1 C1 C2 C3 -14.0(7) . . . . ?
N2 C1 C2 C7 -13.1(7) . . . . ?
O1 C1 C2 C7 166.3(5) . . . . ?
C7 C2 C3 C4 0.7(9) . . . . ?
C1 C2 C3 C4 -178.9(5) . . . . ?
C2 C3 C4 C5 -0.9(10) . . . . ?
C3 C4 C5 C6 0.1(10) . . . . ?
C3 C4 C5 C16 -176.8(6) . . . . ?
C4 C5 C6 C7 0.7(9) . . . . ?
C16 C5 C6 C7 177.6(5) . . . . ?
C5 C6 C7 C2 -0.9(8) . . . . ?
C3 C2 C7 C6 0.1(8) . . . . ?
C1 C2 C7 C6 179.8(4) . . . . ?
N1 C8 C9 C10 176.3(5) . . . . ?
C15 C8 C9 C10 -4.1(7) . . . . ?
N1 C8 C9 C14 -4.9(7) . . . . ?
C15 C8 C9 C14 174.7(5) . . . . ?
C14 C9 C10 C11 1.4(9) . . . . ?
C8 C9 C10 C11 -179.8(6) . . . . ?
C9 C10 C11 C12 -2.2(10) . . . . ?
C10 C11 C12 C13 2.1(11) . . . . ?
C11 C12 C13 C14 -1.2(10) . . . . ?
C12 C13 C14 O2 -178.3(5) . . . . ?
C12 C13 C14 C9 0.3(8) . . . . ?
C10 C9 C14 O2 178.2(5) . . . . ?
C8 C9 C14 O2 -0.6(7) . . . . ?
C10 C9 C14 C13 -0.4(7) . . . . ?
C8 C9 C14 C13 -179.2(4) . . . . ?
C9 C8 N1 N2 -176.6(4) . . . . ?
C15 C8 N1 N2 3.9(6) . . . . ?
C9 C8 N1 Ti1 3.8(6) . . . . ?
C15 C8 N1 Ti1 -175.8(4) . . . . ?
O1 C1 N2 N1 1.6(6) . . . . ?
C2 C1 N2 N1 -179.0(4) . . . . ?
C8 N1 N2 C1 -179.2(4) . . . . ?
Ti1 N1 N2 C1 0.5(5) . . . . ?
N2 C1 O1 Ti1 -3.2(6) . . . . ?
C2 C1 O1 Ti1 177.4(3) . . . . ?
C13 C14 O2 Ti1 -171.3(4) . . . . ?
C9 C14 O2 Ti1 10.1(8) . . . . ?
C14 O2 Ti1 O2 -118.8(6) . . . 2_655 ?
C14 O2 Ti1 O1 -16.6(8) . . . . ?
C14 O2 Ti1 O1 85.1(6) . . . 2_655 ?
C14 O2 Ti1 N1 -9.1(6) . . . . ?
C14 O2 Ti1 N1 159.2(5) . . . 2_655 ?

_refine_diff_density_max         1.363
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.310

####################################################################### 
# 
# 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_L3N
_database_code_depnum_ccdc_archive 'CCDC 1858904'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31

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'

_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                   8.4653(7)
_cell_length_b                   10.9589(7)
_cell_length_c                   30.080(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2790.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1644
_cell_measurement_theta_max      27.6640
_cell_measurement_theta_min      4.1210

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_description       plate
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_reflns_number            6815
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.329
_diffrn_reflns_theta_max         28.955
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3151
_reflns_number_gt                2361
_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_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0650P)²+0.3676P] 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         3151
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.003
_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 0.74418(19) 0.10536(15) 0.96093(6) 0.0503(4) Uani 1 1 d . . . . .
C2 C 0.79423(19) 0.06357(14) 1.00572(5) 0.0464(4) Uani 1 1 d . . . . .
C3 C 0.9054(2) 0.13277(14) 1.02803(6) 0.0530(4) Uani 1 1 d . . . . .
H3 H 0.947636 0.201741 1.014503 0.064 Uiso 1 1 calc R U . . .
C4 C 0.9540(2) 0.10056(15) 1.07005(6) 0.0553(4) Uani 1 1 d . . . . .
H4 H 1.028614 0.148584 1.084509 0.066 Uiso 1 1 calc R U . . .
C5 C 0.8945(2) -0.00184(15) 1.09139(6) 0.0521(4) Uani 1 1 d . . . . .
C6 C 0.7844(2) -0.07092(16) 1.06881(6) 0.0600(5) Uani 1 1 d . . . . .
H6 H 0.743285 -0.140462 1.082226 0.072 Uiso 1 1 calc R U . . .
C7 C 0.7340(2) -0.03910(16) 1.02679(6) 0.0581(5) Uani 1 1 d . . . . .
H7 H 0.658919 -0.086886 1.012417 0.070 Uiso 1 1 calc R U . . .
C8 C 0.5397(2) -0.01420(15) 0.86866(6) 0.0540(4) Uani 1 1 d . . . . .
C9 C 0.4840(2) 0.03944(16) 0.82667(6) 0.0532(4) Uani 1 1 d . . . . .
C10 C 0.3954(3) -0.0282(2) 0.79616(7) 0.0737(6) Uani 1 1 d . . . . .
H10 H 0.374552 -0.109832 0.802247 0.088 Uiso 1 1 calc R U . . .
C11 C 0.3378(3) 0.0218(3) 0.75746(8) 0.0891(7) Uani 1 1 d . . . . .
H11 H 0.279913 -0.025840 0.737727 0.107 Uiso 1 1 calc R U . . .
C12 C 0.3662(3) 0.1412(3) 0.74827(8) 0.0867(7) Uani 1 1 d . . . . .
H12 H 0.326092 0.175385 0.722322 0.104 Uiso 1 1 calc R U . . .
C13 C 0.4528(3) 0.2114(2) 0.77669(7) 0.0777(6) Uani 1 1 d . . . . .
H13 H 0.471186 0.293031 0.769934 0.093 Uiso 1 1 calc R U . . .
C14 C 0.5137(2) 0.16211(17) 0.81565(6) 0.0587(5) Uani 1 1 d . . . . .
C15 C 0.4990(3) -0.14307(18) 0.88059(8) 0.0876(7) Uani 1 1 d . . . . .
H15A H 0.581239 -0.196595 0.870473 0.131 Uiso 1 1 calc R U . . .
H15B H 0.401056 -0.165260 0.866664 0.131 Uiso 1 1 calc R U . . .
H15C H 0.488507 -0.149970 0.912265 0.131 Uiso 1 1 calc R U . . .
C16 C 0.9516(3) -0.03562(18) 1.13706(7) 0.0716(6) Uani 1 1 d . . . . .
H16A H 0.878333 -0.091462 1.150463 0.107 Uiso 1 1 calc R U . . .
H16B H 0.959370 0.036558 1.155011 0.107 Uiso 1 1 calc R U . . .
H16C H 1.053524 -0.073539 1.134883 0.107 Uiso 1 1 calc R U . . .
N1 N 0.61919(17) 0.05775(13) 0.89389(5) 0.0543(4) Uani 1 1 d . . . . .
N2 N 0.67223(18) 0.01966(14) 0.93472(5) 0.0564(4) Uani 1 1 d . . . . .
O1 O 0.76273(16) 0.21005(11) 0.94818(4) 0.0646(4) Uani 1 1 d . . . . .
O2 O 0.6038(2) 0.23617(12) 0.84121(5) 0.0786(5) Uani 1 1 d . . . . .
H1O H 0.633(3) 0.186(3) 0.8663(10) 0.118 Uiso 1 1 d . U . . .
H2N H 0.674(4) -0.058(3) 0.9405(9) 0.118 Uiso 1 1 d . 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
C1 O1 1.220(2) . ?
C1 N2 1.369(2) . ?
C1 C2 1.485(2) . ?
C2 C3 1.382(2) . ?
C2 C7 1.388(2) . ?
C3 C4 1.375(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 C16 1.503(3) . ?
C6 C7 1.379(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.285(2) . ?
C8 C9 1.471(2) . ?
C8 C15 1.497(3) . ?
C9 C10 1.398(3) . ?
C9 C14 1.407(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9300 . ?
C14 O2 1.353(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.373(2) . ?
N2 H2N 0.87(3) . ?
O2 H1O 0.97(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
O1 C1 N2 121.43(16) . . ?
O1 C1 C2 122.59(16) . . ?
N2 C1 C2 115.97(15) . . ?
C3 C2 C7 118.23(16) . . ?
C3 C2 C1 117.74(15) . . ?
C7 C2 C1 124.01(15) . . ?
C4 C3 C2 120.61(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.60(16) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 117.47(16) . . ?
C6 C5 C16 122.15(17) . . ?
C4 C5 C16 120.37(17) . . ?
C7 C6 C5 121.44(17) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 120.64(17) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
N1 C8 C9 115.45(15) . . ?
N1 C8 C15 123.93(17) . . ?
C9 C8 C15 120.59(17) . . ?
C10 C9 C14 116.59(17) . . ?
C10 C9 C8 121.59(17) . . ?
C14 C9 C8 121.80(16) . . ?
C11 C10 C9 122.3(2) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C12 C11 C10 119.5(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
O2 C14 C13 117.06(19) . . ?
O2 C14 C9 122.66(16) . . ?
C13 C14 C9 120.26(19) . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N1 N2 120.88(15) . . ?
C1 N2 N1 116.88(15) . . ?
C1 N2 H2N 123.5(19) . . ?
N1 N2 H2N 118.7(19) . . ?
C14 O2 H1O 104.3(17) . . ?

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
O1 C1 C2 C3 -19.8(2) . . . . ?
N2 C1 C2 C3 161.57(15) . . . . ?
O1 C1 C2 C7 158.92(17) . . . . ?
N2 C1 C2 C7 -19.7(2) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 178.50(15) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C16 179.18(17) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C16 C5 C6 C7 -179.57(18) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C3 C2 C7 C6 -0.1(3) . . . . ?
C1 C2 C7 C6 -178.83(16) . . . . ?
N1 C8 C9 C10 -179.62(17) . . . . ?
C15 C8 C9 C10 -1.6(3) . . . . ?
N1 C8 C9 C14 -1.3(2) . . . . ?
C15 C8 C9 C14 176.73(18) . . . . ?
C14 C9 C10 C11 -0.7(3) . . . . ?
C8 C9 C10 C11 177.73(19) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 O2 177.36(19) . . . . ?
C12 C13 C14 C9 -1.3(3) . . . . ?
C10 C9 C14 O2 -176.97(17) . . . . ?
C8 C9 C14 O2 4.6(3) . . . . ?
C10 C9 C14 C13 1.6(3) . . . . ?
C8 C9 C14 C13 -176.86(17) . . . . ?
C9 C8 N1 N2 177.45(14) . . . . ?
C15 C8 N1 N2 -0.5(3) . . . . ?
O1 C1 N2 N1 -1.3(2) . . . . ?
C2 C1 N2 N1 177.38(13) . . . . ?
C8 N1 N2 C1 -174.60(15) . . . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_Compound2N
_database_code_depnum_ccdc_archive 'CCDC 1858902'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 N4 O4 Ti'
_chemical_formula_sum            'C30 H24 N4 O4 Ti'
_chemical_formula_weight         552.43

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'
Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   12.4269(10)
_cell_length_b                   11.126(2)
_cell_length_c                   18.956(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2621.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1188
_cell_measurement_theta_max      26.9130
_cell_measurement_theta_min      3.8900

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.371
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6921
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.817
_diffrn_reflns_theta_max         29.058
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3015
_reflns_number_gt                1604
_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_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.1124P)²+5.5906P] 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         3015
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.1000
_refine_ls_wR_factor_ref         0.2910
_refine_ls_wR_factor_gt          0.2354
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_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 0.6377(4) 0.0288(5) 0.1741(3) 0.0555(13) Uani 1 1 d . . . . .
C2 C 0.6630(4) -0.0700(5) 0.1252(3) 0.0569(14) Uani 1 1 d . . . . .
C3 C 0.5832(5) -0.1153(6) 0.0814(3) 0.0692(16) Uani 1 1 d . . . . .
H3 H 0.514633 -0.081813 0.081363 0.083 Uiso 1 1 calc R U . . .
C4 C 0.6074(7) -0.2104(7) 0.0380(4) 0.090(2) Uani 1 1 d . . . . .
H4 H 0.554226 -0.242249 0.008959 0.108 Uiso 1 1 calc R U . . .
C5 C 0.7070(7) -0.2584(7) 0.0367(4) 0.092(2) Uani 1 1 d . . . . .
H5 H 0.721786 -0.322133 0.006520 0.110 Uiso 1 1 calc R U . . .
C6 C 0.7853(6) -0.2150(6) 0.0787(3) 0.0749(17) Uani 1 1 d . . . . .
H6 H 0.853251 -0.249971 0.077814 0.090 Uiso 1 1 calc R U . . .
C7 C 0.7658(4) -0.1201(5) 0.1228(3) 0.0603(14) Uani 1 1 d . . . . .
H7 H 0.820669 -0.089180 0.150795 0.072 Uiso 1 1 calc R U . . .
C8 C 0.7443(4) 0.2377(5) 0.2802(3) 0.0511(13) Uani 1 1 d . . . . .
C9 C 0.7142(4) 0.3373(5) 0.3275(3) 0.0559(13) Uani 1 1 d . . . . .
C10 C 0.7893(5) 0.4165(6) 0.3553(3) 0.0703(17) Uani 1 1 d . . . . .
H10 H 0.861099 0.405926 0.342918 0.084 Uiso 1 1 calc R U . . .
C11 C 0.7644(6) 0.5091(7) 0.3998(4) 0.085(2) Uani 1 1 d . . . . .
H11 H 0.817859 0.559990 0.416715 0.102 Uiso 1 1 calc R U . . .
C12 C 0.6585(7) 0.5256(6) 0.4192(4) 0.086(2) Uani 1 1 d . . . . .
H12 H 0.639959 0.587320 0.449980 0.103 Uiso 1 1 calc R U . . .
C13 C 0.5799(5) 0.4499(6) 0.3928(3) 0.0714(16) Uani 1 1 d . . . . .
H13 H 0.508482 0.460160 0.406101 0.086 Uiso 1 1 calc R U . . .
C14 C 0.6081(4) 0.3586(5) 0.3463(3) 0.0610(14) Uani 1 1 d . . . . .
C15 C 0.8629(4) 0.2155(7) 0.2672(4) 0.081(2) Uani 1 1 d . . . . .
H15A H 0.877559 0.130977 0.270658 0.121 Uiso 1 1 calc R U . . .
H15B H 0.904561 0.257994 0.301766 0.121 Uiso 1 1 calc R U . . .
H15C H 0.881713 0.243404 0.220887 0.121 Uiso 1 1 calc R U . . .
N1 N 0.6734(3) 0.1714(4) 0.2501(2) 0.0485(10) Uani 1 1 d . . . . .
N2 N 0.7161(3) 0.0806(4) 0.2067(2) 0.0516(11) Uani 1 1 d . . . . .
O1 O 0.5360(2) 0.0581(4) 0.1820(2) 0.0695(12) Uani 1 1 d . . . . .
O2 O 0.5282(3) 0.2895(4) 0.3197(3) 0.0839(14) Uani 1 1 d . . . . .
Ti1 Ti 0.500000 0.17994(14) 0.250000 0.0626(6) Uani 1 2 d S T P . .


_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 N2 1.289(6) . ?
C1 O1 1.314(5) . ?
C1 C2 1.471(8) . ?
C2 C3 1.388(8) . ?
C2 C7 1.395(7) . ?
C3 C4 1.374(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.347(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.347(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(8) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.284(6) . ?
C8 C9 1.474(8) . ?
C8 C15 1.514(7) . ?
C9 C14 1.386(7) . ?
C9 C10 1.388(7) . ?
C10 C11 1.367(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(8) . ?
C13 H13 0.9300 . ?
C14 O2 1.353(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 N2 1.406(6) . ?
N1 Ti1 2.157(3) . ?
O1 Ti1 1.923(4) . ?
O2 Ti1 1.831(4) . ?

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
N2 C1 O1 124.1(5) . . ?
N2 C1 C2 118.3(4) . . ?
O1 C1 C2 117.6(5) . . ?
C3 C2 C7 119.3(5) . . ?
C3 C2 C1 119.7(5) . . ?
C7 C2 C1 121.0(5) . . ?
C4 C3 C2 118.8(6) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 121.1(7) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.7(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 120.6(7) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 119.4(6) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
N1 C8 C9 121.9(4) . . ?
N1 C8 C15 120.1(5) . . ?
C9 C8 C15 118.0(5) . . ?
C14 C9 C10 115.7(6) . . ?
C14 C9 C8 121.8(5) . . ?
C10 C9 C8 122.5(5) . . ?
C11 C10 C9 124.1(6) . . ?
C11 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
C10 C11 C12 118.8(6) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C13 119.8(7) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 119.8(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
O2 C14 C9 120.3(5) . . ?
O2 C14 C13 117.9(5) . . ?
C9 C14 C13 121.8(5) . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 N1 N2 114.5(4) . . ?
C8 N1 Ti1 131.4(4) . . ?
N2 N1 Ti1 114.1(3) . . ?
C1 N2 N1 108.5(4) . . ?
C1 O1 Ti1 118.4(3) . . ?
C14 O2 Ti1 142.0(4) . . ?
O2 Ti1 O2 96.5(3) 4_655 . ?
O2 Ti1 O1 155.24(15) 4_655 4_655 ?
O2 Ti1 O1 91.7(2) . 4_655 ?
O2 Ti1 O1 91.7(2) 4_655 . ?
O2 Ti1 O1 155.24(15) . . ?
O1 Ti1 O1 90.4(3) 4_655 . ?
O2 Ti1 N1 80.67(17) 4_655 4_655 ?
O2 Ti1 N1 102.77(15) . 4_655 ?
O1 Ti1 N1 74.74(16) 4_655 4_655 ?
O1 Ti1 N1 101.58(14) . 4_655 ?
O2 Ti1 N1 102.77(15) 4_655 . ?
O2 Ti1 N1 80.67(17) . . ?
O1 Ti1 N1 101.58(14) 4_655 . ?
O1 Ti1 N1 74.74(15) . . ?
N1 Ti1 N1 174.9(2) 4_655 . ?

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
N2 C1 C2 C3 -170.1(5) . . . . ?
O1 C1 C2 C3 10.3(7) . . . . ?
N2 C1 C2 C7 10.6(7) . . . . ?
O1 C1 C2 C7 -169.0(5) . . . . ?
C7 C2 C3 C4 1.6(8) . . . . ?
C1 C2 C3 C4 -177.7(5) . . . . ?
C2 C3 C4 C5 -1.1(10) . . . . ?
C3 C4 C5 C6 0.8(11) . . . . ?
C4 C5 C6 C7 -1.1(11) . . . . ?
C5 C6 C7 C2 1.6(9) . . . . ?
C3 C2 C7 C6 -1.9(8) . . . . ?
C1 C2 C7 C6 177.4(5) . . . . ?
N1 C8 C9 C14 5.3(7) . . . . ?
C15 C8 C9 C14 -175.3(5) . . . . ?
N1 C8 C9 C10 -174.0(5) . . . . ?
C15 C8 C9 C10 5.5(8) . . . . ?
C14 C9 C10 C11 1.4(9) . . . . ?
C8 C9 C10 C11 -179.3(5) . . . . ?
C9 C10 C11 C12 0.5(10) . . . . ?
C10 C11 C12 C13 -0.9(10) . . . . ?
C11 C12 C13 C14 -0.6(10) . . . . ?
C10 C9 C14 O2 177.3(5) . . . . ?
C8 C9 C14 O2 -2.0(8) . . . . ?
C10 C9 C14 C13 -2.9(8) . . . . ?
C8 C9 C14 C13 177.7(5) . . . . ?
C12 C13 C14 O2 -177.6(6) . . . . ?
C12 C13 C14 C9 2.7(9) . . . . ?
C9 C8 N1 N2 179.9(4) . . . . ?
C15 C8 N1 N2 0.5(6) . . . . ?
C9 C8 N1 Ti1 3.4(7) . . . . ?
C15 C8 N1 Ti1 -176.0(4) . . . . ?
O1 C1 N2 N1 -0.4(7) . . . . ?
C2 C1 N2 N1 -180.0(4) . . . . ?
C8 N1 N2 C1 -173.5(4) . . . . ?
Ti1 N1 N2 C1 3.6(5) . . . . ?
N2 C1 O1 Ti1 -3.4(7) . . . . ?
C2 C1 O1 Ti1 176.1(3) . . . . ?
C9 C14 O2 Ti1 -14.5(10) . . . . ?
C13 C14 O2 Ti1 165.7(5) . . . . ?
C14 O2 Ti1 O2 -84.6(7) . . . 4_655 ?
C14 O2 Ti1 O1 118.8(7) . . . 4_655 ?
C14 O2 Ti1 O1 24.2(10) . . . . ?
C14 O2 Ti1 N1 -166.4(6) . . . 4_655 ?
C14 O2 Ti1 N1 17.4(7) . . . . ?

_refine_diff_density_max         1.055
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_Compound7N
_database_code_depnum_ccdc_archive 'CCDC 1858907'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 N4 O6 Ti, C H2 Cl2'
_chemical_formula_sum            'C27 H22 Cl2 N4 O6 Ti'
_chemical_formula_weight         617.28

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.3453(14)
_cell_length_b                   8.0522(7)
_cell_length_c                   21.858(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.079(10)
_cell_angle_gamma                90
_cell_volume                     2641.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1558
_cell_measurement_theta_max      24.0450
_cell_measurement_theta_min      3.9690

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.578
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_reflns_number            11351
_diffrn_reflns_av_unetI/netI     0.1359
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.113
_diffrn_reflns_theta_max         29.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6088
_reflns_number_gt                3045
_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_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0517P)²+0.0049P] 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         6088
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1756
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_ref         0.1721
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.2483(3) -0.0153(5) 0.60136(19) 0.0298(10) Uani 1 1 d . . . . .
C2 C 0.2695(3) -0.1708(5) 0.6359(2) 0.0336(11) Uani 1 1 d . . . . .
C3 C 0.3061(3) -0.3117(5) 0.6216(2) 0.0394(11) Uani 1 1 d . . . . .
H3 H 0.327840 -0.333734 0.585828 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3049(3) -0.4219(6) 0.6726(3) 0.0474(13) Uani 1 1 d . . . . .
H4 H 0.326059 -0.530447 0.676493 0.057 Uiso 1 1 calc R U . . .
C5 C 0.2680(3) -0.3405(6) 0.7132(3) 0.0550(15) Uani 1 1 d . . . . .
H5 H 0.258867 -0.384208 0.750708 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1308(3) 0.3428(5) 0.5937(2) 0.0314(10) Uani 1 1 d . . . . .
C7 C 0.0886(3) 0.3197(6) 0.6486(2) 0.0450(12) Uani 1 1 d . . . . .
H7A H 0.026757 0.349406 0.637282 0.068 Uiso 1 1 calc R U . . .
H7B H 0.118013 0.389175 0.682384 0.068 Uiso 1 1 calc R U . . .
H7C H 0.093955 0.205591 0.661606 0.068 Uiso 1 1 calc R U . . .
C8 C 0.1131(3) 0.4944(5) 0.5569(2) 0.0303(10) Uani 1 1 d . . . . .
C9 C 0.0605(3) 0.6201(6) 0.5752(2) 0.0466(13) Uani 1 1 d . . . . .
H9 H 0.035794 0.603843 0.610066 0.056 Uiso 1 1 calc R U . . .
C10 C 0.0449(3) 0.7671(6) 0.5425(3) 0.0552(14) Uani 1 1 d . . . . .
H10 H 0.010818 0.849681 0.555882 0.066 Uiso 1 1 calc R U . . .
C11 C 0.0794(3) 0.7916(6) 0.4905(3) 0.0505(14) Uani 1 1 d . . . . .
H11 H 0.068474 0.890909 0.468520 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1301(3) 0.6707(6) 0.4704(2) 0.0437(13) Uani 1 1 d . . . . .
H12 H 0.152767 0.687954 0.434666 0.052 Uiso 1 1 calc R U . . .
C13 C 0.1473(3) 0.5236(5) 0.5032(2) 0.0332(11) Uani 1 1 d . . . . .
C14 C 0.2284(3) 0.0508(6) 0.3893(2) 0.0422(12) Uani 1 1 d . . . . .
C15 C 0.1736(4) -0.0338(6) 0.3375(2) 0.0516(14) Uani 1 1 d . . . . .
C16 C 0.0851(3) -0.0558(7) 0.3211(3) 0.0581(15) Uani 1 1 d . . . . .
H16 H 0.042429 -0.016935 0.342234 0.070 Uiso 1 1 calc R U . . .
C17 C 0.0696(4) -0.1508(7) 0.2648(3) 0.0668(17) Uani 1 1 d . . . . .
H17 H 0.014658 -0.184683 0.241442 0.080 Uiso 1 1 calc R U . . .
C18 C 0.1486(4) -0.1810(7) 0.2524(3) 0.0693(17) Uani 1 1 d . . . . .
H18 H 0.157312 -0.242129 0.218125 0.083 Uiso 1 1 calc R U . . .
C19 C 0.4381(3) 0.1764(5) 0.4544(2) 0.0322(10) Uani 1 1 d . . . . .
C20 C 0.4850(3) 0.1136(6) 0.4039(2) 0.0561(14) Uani 1 1 d . . . . .
H20A H 0.536453 0.050055 0.422964 0.084 Uiso 1 1 calc R U . . .
H20B H 0.503120 0.206451 0.381999 0.084 Uiso 1 1 calc R U . . .
H20C H 0.444905 0.044844 0.375014 0.084 Uiso 1 1 calc R U . . .
C21 C 0.4902(3) 0.2561(5) 0.5093(2) 0.0383(11) Uani 1 1 d . . . . .
C22 C 0.5832(3) 0.2684(6) 0.5196(2) 0.0444(12) Uani 1 1 d . . . . .
H22 H 0.612027 0.220254 0.490598 0.053 Uiso 1 1 calc R U . . .
C23 C 0.6334(3) 0.3474(6) 0.5699(3) 0.0542(14) Uani 1 1 d . . . . .
H23 H 0.694946 0.352844 0.574570 0.065 Uiso 1 1 calc R U . . .
C24 C 0.5932(3) 0.4188(6) 0.6137(3) 0.0551(14) Uani 1 1 d . . . . .
H24 H 0.627039 0.473567 0.648088 0.066 Uiso 1 1 calc R U . . .
C25 C 0.5027(3) 0.4084(5) 0.6063(2) 0.0431(12) Uani 1 1 d . . . . .
H25 H 0.475433 0.456008 0.636209 0.052 Uiso 1 1 calc R U . . .
C26 C 0.4497(3) 0.3277(5) 0.5545(2) 0.0399(12) Uani 1 1 d . . . . .
C27 C 0.0849(5) 0.3556(9) 0.2477(3) 0.101(2) Uani 1 1 d . . . . .
H27A H 0.100197 0.241105 0.240964 0.122 Uiso 1 1 calc R U . . .
H27B H 0.108269 0.424078 0.218369 0.122 Uiso 1 1 calc R U . . .
N1 N 0.1854(2) 0.2286(4) 0.57963(15) 0.0295(8) Uani 1 1 d . . . . .
N2 N 0.1982(2) 0.0927(4) 0.62117(16) 0.0345(9) Uani 1 1 d . . . . .
N3 N 0.3517(2) 0.1539(4) 0.44618(16) 0.0324(9) Uani 1 1 d . . . . .
N4 N 0.3133(3) 0.0744(5) 0.38965(17) 0.0419(10) Uani 1 1 d . . . . .
O1 O 0.19735(19) 0.4092(4) 0.48258(14) 0.0418(8) Uani 1 1 d . . . . .
O2 O 0.28094(18) 0.0052(3) 0.55111(14) 0.0378(8) Uani 1 1 d . . . . .
O3 O 0.2453(2) -0.1835(4) 0.69246(15) 0.0516(9) Uani 1 1 d . . . . .
O4 O 0.36054(18) 0.3211(4) 0.54967(14) 0.0390(8) Uani 1 1 d . . . . .
O5 O 0.18863(19) 0.1036(4) 0.43390(14) 0.0439(8) Uani 1 1 d . . . . .
O6 O 0.2155(3) -0.1131(5) 0.29524(18) 0.0660(11) Uani 1 1 d . . . . .
Ti1 Ti 0.25988(5) 0.21619(10) 0.50614(4) 0.0338(2) Uani 1 1 d . . . . .
Cl1 Cl 0.13458(15) 0.4121(2) 0.32204(9) 0.1133(7) Uani 1 1 d . . . . .
Cl2 Cl -0.03131(16) 0.3750(3) 0.23231(11) 0.1334(8) 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 N2 1.294(5) . ?
C1 O2 1.309(5) . ?
C1 C2 1.463(6) . ?
C2 C3 1.332(6) . ?
C2 O3 1.366(5) . ?
C3 C4 1.427(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.322(7) . ?
C4 H4 0.9300 . ?
C5 O3 1.363(5) . ?
C5 H5 0.9300 . ?
C6 N1 1.323(5) . ?
C6 C8 1.456(6) . ?
C6 C7 1.489(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.403(6) . ?
C8 C9 1.403(6) . ?
C9 C10 1.377(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(6) . ?
C12 H12 0.9300 . ?
C13 O1 1.336(5) . ?
C14 N4 1.315(6) . ?
C14 O5 1.324(5) . ?
C14 C15 1.433(6) . ?
C15 C16 1.343(6) . ?
C15 O6 1.387(6) . ?
C16 C17 1.426(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.320(8) . ?
C17 H17 0.9300 . ?
C18 O6 1.352(6) . ?
C18 H18 0.9300 . ?
C19 N3 1.312(5) . ?
C19 C21 1.445(6) . ?
C19 C20 1.525(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.397(6) . ?
C21 C22 1.401(6) . ?
C22 C23 1.362(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.367(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.407(6) . ?
C25 H25 0.9300 . ?
C26 O4 1.350(5) . ?
C27 Cl1 1.706(7) . ?
C27 Cl2 1.751(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
N1 N2 1.409(4) . ?
N1 Ti1 2.160(3) . ?
N3 N4 1.407(5) . ?
N3 Ti1 2.174(4) . ?
O1 Ti1 1.842(3) . ?
O2 Ti1 1.956(3) . ?
O4 Ti1 1.841(3) . ?
O5 Ti1 1.946(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
N2 C1 O2 123.7(4) . . ?
N2 C1 C2 119.0(4) . . ?
O2 C1 C2 117.3(4) . . ?
C3 C2 O3 110.9(4) . . ?
C3 C2 C1 131.8(4) . . ?
O3 C2 C1 117.3(4) . . ?
C2 C3 C4 105.8(4) . . ?
C2 C3 H3 127.1 . . ?
C4 C3 H3 127.1 . . ?
C5 C4 C3 107.0(4) . . ?
C5 C4 H4 126.5 . . ?
C3 C4 H4 126.5 . . ?
C4 C5 O3 110.6(5) . . ?
C4 C5 H5 124.7 . . ?
O3 C5 H5 124.7 . . ?
N1 C6 C8 120.5(4) . . ?
N1 C6 C7 120.2(4) . . ?
C8 C6 C7 119.2(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 117.1(4) . . ?
C13 C8 C6 123.0(4) . . ?
C9 C8 C6 119.9(4) . . ?
C10 C9 C8 121.4(5) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C9 120.0(5) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.5(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O1 C13 C12 118.6(4) . . ?
O1 C13 C8 120.6(4) . . ?
C12 C13 C8 120.9(4) . . ?
N4 C14 O5 123.9(4) . . ?
N4 C14 C15 119.3(5) . . ?
O5 C14 C15 116.8(4) . . ?
C16 C15 O6 110.3(5) . . ?
C16 C15 C14 131.8(6) . . ?
O6 C15 C14 117.9(5) . . ?
C15 C16 C17 106.1(5) . . ?
C15 C16 H16 126.9 . . ?
C17 C16 H16 126.9 . . ?
C18 C17 C16 106.3(5) . . ?
C18 C17 H17 126.8 . . ?
C16 C17 H17 126.8 . . ?
C17 C18 O6 112.4(6) . . ?
C17 C18 H18 123.8 . . ?
O6 C18 H18 123.8 . . ?
N3 C19 C21 122.9(4) . . ?
N3 C19 C20 118.1(4) . . ?
C21 C19 C20 119.0(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 . . ?
C26 C21 C22 116.5(4) . . ?
C26 C21 C19 121.3(4) . . ?
C22 C21 C19 122.2(4) . . ?
C23 C22 C21 123.2(5) . . ?
C23 C22 H22 118.4 . . ?
C21 C22 H22 118.4 . . ?
C22 C23 C24 120.0(5) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.1(5) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 121.8(5) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
O4 C26 C21 121.5(4) . . ?
O4 C26 C25 119.1(4) . . ?
C21 C26 C25 119.4(4) . . ?
Cl1 C27 Cl2 113.2(4) . . ?
Cl1 C27 H27A 108.9 . . ?
Cl2 C27 H27A 108.9 . . ?
Cl1 C27 H27B 108.9 . . ?
Cl2 C27 H27B 108.9 . . ?
H27A C27 H27B 107.8 . . ?
C6 N1 N2 113.5(3) . . ?
C6 N1 Ti1 131.7(3) . . ?
N2 N1 Ti1 114.8(2) . . ?
C1 N2 N1 108.6(3) . . ?
C19 N3 N4 114.1(4) . . ?
C19 N3 Ti1 130.4(3) . . ?
N4 N3 Ti1 115.4(3) . . ?
C14 N4 N3 107.7(4) . . ?
C13 O1 Ti1 142.2(3) . . ?
C1 O2 Ti1 118.6(3) . . ?
C5 O3 C2 105.7(4) . . ?
C26 O4 Ti1 141.7(3) . . ?
C14 O5 Ti1 118.7(3) . . ?
C18 O6 C15 104.8(4) . . ?
O4 Ti1 O1 95.11(14) . . ?
O4 Ti1 O5 154.30(14) . . ?
O1 Ti1 O5 89.71(14) . . ?
O4 Ti1 O2 96.10(13) . . ?
O1 Ti1 O2 153.50(13) . . ?
O5 Ti1 O2 90.49(13) . . ?
O4 Ti1 N1 96.40(13) . . ?
O1 Ti1 N1 80.97(13) . . ?
O5 Ti1 N1 109.29(13) . . ?
O2 Ti1 N1 73.98(13) . . ?
O4 Ti1 N3 80.67(13) . . ?
O1 Ti1 N3 113.05(13) . . ?
O5 Ti1 N3 74.24(13) . . ?
O2 Ti1 N3 92.45(12) . . ?
N1 Ti1 N3 165.81(13) . . ?

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
N2 C1 C2 C3 167.7(4) . . . . ?
O2 C1 C2 C3 -11.5(7) . . . . ?
N2 C1 C2 O3 -9.0(6) . . . . ?
O2 C1 C2 O3 171.8(4) . . . . ?
O3 C2 C3 C4 0.1(5) . . . . ?
C1 C2 C3 C4 -176.7(4) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 O3 -0.3(6) . . . . ?
N1 C6 C8 C13 4.1(6) . . . . ?
C7 C6 C8 C13 -177.6(4) . . . . ?
N1 C6 C8 C9 -175.0(4) . . . . ?
C7 C6 C8 C9 3.3(6) . . . . ?
C13 C8 C9 C10 -1.3(6) . . . . ?
C6 C8 C9 C10 177.9(4) . . . . ?
C8 C9 C10 C11 1.2(7) . . . . ?
C9 C10 C11 C12 -0.2(8) . . . . ?
C10 C11 C12 C13 -0.7(7) . . . . ?
C11 C12 C13 O1 -179.5(4) . . . . ?
C11 C12 C13 C8 0.6(7) . . . . ?
C9 C8 C13 O1 -179.5(4) . . . . ?
C6 C8 C13 O1 1.4(6) . . . . ?
C9 C8 C13 C12 0.4(6) . . . . ?
C6 C8 C13 C12 -178.8(4) . . . . ?
N4 C14 C15 C16 -170.2(5) . . . . ?
O5 C14 C15 C16 8.6(8) . . . . ?
N4 C14 C15 O6 11.2(7) . . . . ?
O5 C14 C15 O6 -170.0(4) . . . . ?
O6 C15 C16 C17 -1.3(6) . . . . ?
C14 C15 C16 C17 180.0(5) . . . . ?
C15 C16 C17 C18 1.2(6) . . . . ?
C16 C17 C18 O6 -0.6(7) . . . . ?
N3 C19 C21 C26 -5.9(6) . . . . ?
C20 C19 C21 C26 174.8(4) . . . . ?
N3 C19 C21 C22 175.2(4) . . . . ?
C20 C19 C21 C22 -4.1(6) . . . . ?
C26 C21 C22 C23 -1.0(7) . . . . ?
C19 C21 C22 C23 177.9(4) . . . . ?
C21 C22 C23 C24 0.4(8) . . . . ?
C22 C23 C24 C25 0.4(8) . . . . ?
C23 C24 C25 C26 -0.6(7) . . . . ?
C22 C21 C26 O4 -179.1(4) . . . . ?
C19 C21 C26 O4 2.0(6) . . . . ?
C22 C21 C26 C25 0.8(6) . . . . ?
C19 C21 C26 C25 -178.1(4) . . . . ?
C24 C25 C26 O4 179.8(4) . . . . ?
C24 C25 C26 C21 0.0(7) . . . . ?
C8 C6 N1 N2 177.6(3) . . . . ?
C7 C6 N1 N2 -0.6(5) . . . . ?
C8 C6 N1 Ti1 -0.9(6) . . . . ?
C7 C6 N1 Ti1 -179.2(3) . . . . ?
O2 C1 N2 N1 0.7(5) . . . . ?
C2 C1 N2 N1 -178.4(3) . . . . ?
C6 N1 N2 C1 176.4(3) . . . . ?
Ti1 N1 N2 C1 -4.7(4) . . . . ?
C21 C19 N3 N4 179.8(4) . . . . ?
C20 C19 N3 N4 -0.8(5) . . . . ?
C21 C19 N3 Ti1 -1.2(6) . . . . ?
C20 C19 N3 Ti1 178.1(3) . . . . ?
O5 C14 N4 N3 3.4(6) . . . . ?
C15 C14 N4 N3 -177.9(4) . . . . ?
C19 N3 N4 C14 176.2(4) . . . . ?
Ti1 N3 N4 C14 -2.9(4) . . . . ?
C12 C13 O1 Ti1 166.2(3) . . . . ?
C8 C13 O1 Ti1 -14.0(7) . . . . ?
N2 C1 O2 Ti1 4.2(5) . . . . ?
C2 C1 O2 Ti1 -176.6(3) . . . . ?
C4 C5 O3 C2 0.4(5) . . . . ?
C3 C2 O3 C5 -0.3(5) . . . . ?
C1 C2 O3 C5 177.0(4) . . . . ?
C21 C26 O4 Ti1 13.1(7) . . . . ?
C25 C26 O4 Ti1 -166.8(3) . . . . ?
N4 C14 O5 Ti1 -2.3(6) . . . . ?
C15 C14 O5 Ti1 179.0(3) . . . . ?
C17 C18 O6 C15 -0.2(6) . . . . ?
C16 C15 O6 C18 1.0(6) . . . . ?
C14 C15 O6 C18 179.8(4) . . . . ?
C26 O4 Ti1 O1 -127.8(5) . . . . ?
C26 O4 Ti1 O5 -27.7(6) . . . . ?
C26 O4 Ti1 O2 76.3(5) . . . . ?
C26 O4 Ti1 N1 150.8(4) . . . . ?
C26 O4 Ti1 N3 -15.2(4) . . . . ?
C13 O1 Ti1 O4 -82.3(4) . . . . ?
C13 O1 Ti1 O5 123.0(4) . . . . ?
C13 O1 Ti1 O2 32.5(6) . . . . ?
C13 O1 Ti1 N1 13.4(4) . . . . ?
C13 O1 Ti1 N3 -164.3(4) . . . . ?

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_Compound6N
_database_code_depnum_ccdc_archive 'CCDC 1858900'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 N4 O6 Ti'
_chemical_formula_sum            'C30 H24 N4 O6 Ti'
_chemical_formula_weight         584.43

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'
Ti Ti 0.2776 0.4457 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   22.427(3)
_cell_length_b                   9.1713(10)
_cell_length_c                   13.1051(13)
_cell_angle_alpha                90
_cell_angle_beta                 105.189(11)
_cell_angle_gamma                90
_cell_volume                     2601.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1201
_cell_measurement_theta_max      25.6410
_cell_measurement_theta_min      3.7960

_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_description       block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.383
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81241
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4980
_diffrn_reflns_av_unetI/netI     0.1198
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.593
_diffrn_reflns_theta_max         29.060
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2978
_reflns_number_gt                1331
_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_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0645P)²] 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         2978
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1886
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.002
_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 0.41278(17) 0.0342(4) 0.8245(3) 0.0467(10) Uani 1 1 d . . . . .
C2 C 0.35912(16) -0.0619(4) 0.8154(3) 0.0419(9) Uani 1 1 d . . . . .
C3 C 0.33740(18) -0.1458(5) 0.7237(3) 0.0562(11) Uani 1 1 d . . . . .
H3 H 0.356841 -0.140145 0.669244 0.067 Uiso 1 1 calc R U . . .
C4 C 0.28701(19) -0.2371(5) 0.7141(4) 0.0625(12) Uani 1 1 d . . . . .
H4 H 0.272620 -0.292533 0.653217 0.075 Uiso 1 1 calc R U . . .
C5 C 0.2584(2) -0.2457(6) 0.7942(4) 0.0692(14) Uani 1 1 d . . . . .
H5 H 0.224922 -0.308002 0.788160 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2790(2) -0.1631(5) 0.8828(4) 0.0697(14) Uani 1 1 d . . . . .
H6 H 0.258999 -0.169383 0.936481 0.084 Uiso 1 1 calc R U . . .
C7 C 0.32817(19) -0.0716(5) 0.8948(3) 0.0559(11) Uani 1 1 d . . . . .
C8 C 0.50994(18) 0.2647(4) 0.9924(3) 0.0450(10) Uani 1 1 d . . . . .
C9 C 0.56155(17) 0.3639(4) 0.9968(3) 0.0432(9) Uani 1 1 d . . . . .
C10 C 0.5893(2) 0.4415(5) 1.0894(3) 0.0578(12) Uani 1 1 d . . . . .
H10 H 0.574297 0.429841 1.148653 0.069 Uiso 1 1 calc R U . . .
C11 C 0.6379(2) 0.5337(6) 1.0946(3) 0.0724(14) Uani 1 1 d . . . . .
H11 H 0.654919 0.585281 1.156467 0.087 Uiso 1 1 calc R U . . .
C12 C 0.66168(19) 0.5504(6) 1.0086(4) 0.0688(13) Uani 1 1 d . . . . .
H12 H 0.695852 0.610047 1.013405 0.083 Uiso 1 1 calc R U . . .
C13 C 0.6350(2) 0.4791(5) 0.9156(3) 0.0607(12) Uani 1 1 d . . . . .
H13 H 0.650465 0.492553 0.857008 0.073 Uiso 1 1 calc R U . . .
C14 C 0.58559(17) 0.3881(4) 0.9091(3) 0.0468(10) Uani 1 1 d . . . . .
C15 C 0.48696(19) 0.2462(5) 1.0902(3) 0.0568(12) Uani 1 1 d . . . . .
H15A H 0.448076 0.295420 1.080432 0.085 Uiso 1 1 calc R U . . .
H15B H 0.516471 0.287172 1.150054 0.085 Uiso 1 1 calc R U . . .
H15C H 0.481729 0.144374 1.102370 0.085 Uiso 1 1 calc R U . . .
N1 N 0.48381(14) 0.1945(4) 0.9065(2) 0.0432(8) Uani 1 1 d . . . . .
N2 N 0.43352(14) 0.1065(4) 0.9119(2) 0.0458(8) Uani 1 1 d . . . . .
O1 O 0.43917(11) 0.0422(3) 0.74582(17) 0.0529(8) Uani 1 1 d . . . . .
O2 O 0.56002(13) 0.3241(3) 0.8160(2) 0.0637(9) Uani 1 1 d . . . . .
O3 O 0.34497(16) 0.0074(5) 0.9839(3) 0.0958(13) Uani 1 1 d D . . . .
Ti1 Ti 0.500000 0.19318(12) 0.750000 0.0512(4) Uani 1 2 d S T P . .
H3O H 0.3817(13) 0.057(4) 0.991(3) 0.077 Uiso 1 1 d D 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
C1 N2 1.299(5) . ?
C1 O1 1.319(4) . ?
C1 C2 1.471(5) . ?
C2 C7 1.396(5) . ?
C2 C3 1.402(5) . ?
C3 C4 1.385(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.362(6) . ?
C6 H6 0.9300 . ?
C7 O3 1.342(5) . ?
C8 N1 1.296(5) . ?
C8 C9 1.461(5) . ?
C8 C15 1.512(5) . ?
C9 C10 1.404(5) . ?
C9 C14 1.410(5) . ?
C10 C11 1.366(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 O2 1.340(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 N2 1.403(4) . ?
N1 Ti1 2.174(3) . ?
O1 Ti1 1.935(3) . ?
O2 Ti1 1.841(3) . ?
O3 H3O 0.925(19) . ?

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
N2 C1 O1 122.0(4) . . ?
N2 C1 C2 118.3(3) . . ?
O1 C1 C2 119.7(3) . . ?
C7 C2 C3 118.3(4) . . ?
C7 C2 C1 122.2(4) . . ?
C3 C2 C1 119.4(3) . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.9(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 121.7(4) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
O3 C7 C6 117.9(4) . . ?
O3 C7 C2 122.2(4) . . ?
C6 C7 C2 119.9(4) . . ?
N1 C8 C9 121.1(3) . . ?
N1 C8 C15 120.3(4) . . ?
C9 C8 C15 118.6(3) . . ?
C10 C9 C14 116.6(4) . . ?
C10 C9 C8 121.1(3) . . ?
C14 C9 C8 122.3(4) . . ?
C11 C10 C9 121.6(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O2 C14 C13 118.0(4) . . ?
O2 C14 C9 120.7(4) . . ?
C13 C14 C9 121.3(4) . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 N1 N2 115.4(3) . . ?
C8 N1 Ti1 132.3(3) . . ?
N2 N1 Ti1 112.3(2) . . ?
C1 N2 N1 110.8(3) . . ?
C1 O1 Ti1 118.4(2) . . ?
C14 O2 Ti1 143.1(2) . . ?
C7 O3 H3O 113(3) . . ?
O2 Ti1 O2 98.6(2) 2_656 . ?
O2 Ti1 O1 91.72(12) 2_656 . ?
O2 Ti1 O1 154.59(10) . . ?
O2 Ti1 O1 154.58(10) 2_656 2_656 ?
O2 Ti1 O1 91.71(12) . 2_656 ?
O1 Ti1 O1 88.59(16) . 2_656 ?
O2 Ti1 N1 80.54(11) 2_656 2_656 ?
O2 Ti1 N1 99.05(11) . 2_656 ?
O1 Ti1 N1 105.54(11) . 2_656 ?
O1 Ti1 N1 74.92(11) 2_656 2_656 ?
O2 Ti1 N1 99.05(11) 2_656 . ?
O2 Ti1 N1 80.54(11) . . ?
O1 Ti1 N1 74.92(11) . . ?
O1 Ti1 N1 105.54(11) 2_656 . ?
N1 Ti1 N1 179.37(18) 2_656 . ?

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
N2 C1 C2 C7 3.5(6) . . . . ?
O1 C1 C2 C7 -178.1(4) . . . . ?
N2 C1 C2 C3 -177.4(4) . . . . ?
O1 C1 C2 C3 1.1(5) . . . . ?
C7 C2 C3 C4 -1.0(6) . . . . ?
C1 C2 C3 C4 179.8(3) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.8(7) . . . . ?
C4 C5 C6 C7 -0.5(7) . . . . ?
C5 C6 C7 O3 179.1(4) . . . . ?
C5 C6 C7 C2 -0.6(7) . . . . ?
C3 C2 C7 O3 -178.4(4) . . . . ?
C1 C2 C7 O3 0.8(6) . . . . ?
C3 C2 C7 C6 1.3(6) . . . . ?
C1 C2 C7 C6 -179.5(4) . . . . ?
N1 C8 C9 C10 179.2(4) . . . . ?
C15 C8 C9 C10 -0.3(5) . . . . ?
N1 C8 C9 C14 -0.2(6) . . . . ?
C15 C8 C9 C14 -179.6(3) . . . . ?
C14 C9 C10 C11 -1.1(6) . . . . ?
C8 C9 C10 C11 179.5(4) . . . . ?
C9 C10 C11 C12 -1.3(7) . . . . ?
C10 C11 C12 C13 2.7(7) . . . . ?
C11 C12 C13 C14 -1.7(7) . . . . ?
C12 C13 C14 O2 178.2(4) . . . . ?
C12 C13 C14 C9 -0.8(7) . . . . ?
C10 C9 C14 O2 -176.8(4) . . . . ?
C8 C9 C14 O2 2.5(6) . . . . ?
C10 C9 C14 C13 2.2(6) . . . . ?
C8 C9 C14 C13 -178.5(4) . . . . ?
C9 C8 N1 N2 -178.0(3) . . . . ?
C15 C8 N1 N2 1.5(5) . . . . ?
C9 C8 N1 Ti1 -1.3(6) . . . . ?
C15 C8 N1 Ti1 178.1(3) . . . . ?
O1 C1 N2 N1 2.7(5) . . . . ?
C2 C1 N2 N1 -178.9(3) . . . . ?
C8 N1 N2 C1 -176.3(3) . . . . ?
Ti1 N1 N2 C1 6.4(4) . . . . ?
N2 C1 O1 Ti1 -12.1(5) . . . . ?
C2 C1 O1 Ti1 169.5(2) . . . . ?
C13 C14 O2 Ti1 176.6(3) . . . . ?
C9 C14 O2 Ti1 -4.4(7) . . . . ?
C14 O2 Ti1 O2 100.4(5) . . . 2_656 ?
C14 O2 Ti1 O1 -12.5(6) . . . . ?
C14 O2 Ti1 O1 -102.9(4) . . . 2_656 ?
C14 O2 Ti1 N1 -177.9(4) . . . 2_656 ?
C14 O2 Ti1 N1 2.6(4) . . . . ?

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_Compound4N
_database_code_depnum_ccdc_archive 'CCDC 1858901'
_audit_update_record             
;
2018-07-28 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H22 Cl2 N4 O4 Ti'
_chemical_formula_sum            'C30 H22 Cl2 N4 O4 Ti'
_chemical_formula_weight         621.31

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   12.5348(13)
_cell_length_b                   22.821(2)
_cell_length_c                   10.2744(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.227(11)
_cell_angle_gamma                90
_cell_volume                     2807.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2453
_cell_measurement_theta_max      27.6720
_cell_measurement_theta_min      4.1070

_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_description       block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.539
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_reflns_number            5526
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.177
_diffrn_reflns_theta_max         29.110
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3217
_reflns_number_gt                2231
_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_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0697P)²+0.7636P] 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         3217
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 -0.14597(18) 0.17415(10) 0.0729(2) 0.0346(5) Uani 1 1 d . . . . .
C2 C -0.17241(19) 0.12592(10) -0.0268(2) 0.0380(5) Uani 1 1 d . . . . .
C3 C -0.0865(2) 0.09452(13) -0.0534(3) 0.0600(8) Uani 1 1 d . . . . .
H3 H -0.012769 0.104481 -0.009011 0.072 Uiso 1 1 calc R U . . .
C4 C -0.1093(3) 0.04854(14) -0.1454(4) 0.0763(10) Uani 1 1 d . . . . .
H4 H -0.051310 0.027252 -0.161869 0.092 Uiso 1 1 calc R U . . .
C5 C -0.2182(3) 0.03477(12) -0.2119(3) 0.0629(8) Uani 1 1 d . . . . .
C6 C -0.3040(3) 0.06500(12) -0.1873(3) 0.0550(7) Uani 1 1 d . . . . .
H6 H -0.377553 0.055123 -0.233211 0.066 Uiso 1 1 calc R U . . .
C7 C -0.2815(2) 0.11033(10) -0.0942(2) 0.0421(6) Uani 1 1 d . . . . .
H7 H -0.340167 0.130568 -0.076632 0.050 Uiso 1 1 calc R U . . .
C8 C -0.24662(17) 0.26318(10) 0.2728(2) 0.0326(5) Uani 1 1 d . . . . .
C9 C -0.21016(17) 0.30751(10) 0.3793(2) 0.0340(5) Uani 1 1 d . . . . .
C10 C -0.2850(2) 0.33133(12) 0.4440(3) 0.0518(7) Uani 1 1 d . . . . .
H10 H -0.358665 0.318396 0.417951 0.062 Uiso 1 1 calc R U . . .
C11 C -0.2526(2) 0.37285(14) 0.5437(3) 0.0645(8) Uani 1 1 d . . . . .
H11 H -0.303924 0.387458 0.584862 0.077 Uiso 1 1 calc R U . . .
C12 C -0.1445(2) 0.39314(12) 0.5835(3) 0.0585(7) Uani 1 1 d . . . . .
H12 H -0.123239 0.422063 0.649900 0.070 Uiso 1 1 calc R U . . .
C13 C -0.0682(2) 0.37078(11) 0.5253(3) 0.0466(6) Uani 1 1 d . . . . .
H13 H 0.005309 0.383995 0.553593 0.056 Uiso 1 1 calc R U . . .
C15 C -0.36716(18) 0.24654(11) 0.2266(3) 0.0474(6) Uani 1 1 d . . . . .
H15A H -0.381613 0.222672 0.146343 0.071 Uiso 1 1 calc R U . . .
H15B H -0.412174 0.281304 0.206377 0.071 Uiso 1 1 calc R U . . .
H15C H -0.385213 0.224941 0.297482 0.071 Uiso 1 1 calc R U . . .
C14 C -0.09998(18) 0.32843(10) 0.4241(2) 0.0348(5) Uani 1 1 d . . . . .
N1 N -0.17617(13) 0.23862(8) 0.21709(18) 0.0310(4) Uani 1 1 d . . . . .
N2 N -0.22222(15) 0.19465(8) 0.12129(19) 0.0356(4) Uani 1 1 d . . . . .
O1 O -0.04333(13) 0.19442(8) 0.10929(17) 0.0459(4) Uani 1 1 d . . . . .
O2 O -0.02357(13) 0.30877(7) 0.36812(17) 0.0463(4) Uani 1 1 d . . . . .
Cl1 Cl -0.24547(11) -0.02173(4) -0.33019(10) 0.1024(4) Uani 1 1 d . . . . .
Ti1 Ti 0.000000 0.25292(3) 0.250000 0.03464(19) Uani 1 2 d S T P . .


_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 N2 1.289(3) . ?
C1 O1 1.313(3) . ?
C1 C2 1.472(3) . ?
C2 C7 1.384(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(4) . ?
C5 Cl1 1.735(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N1 1.312(3) . ?
C8 C9 1.461(3) . ?
C8 C15 1.493(3) . ?
C9 C14 1.404(3) . ?
C9 C10 1.409(3) . ?
C10 C11 1.366(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.368(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 O2 1.332(3) . ?
N1 N2 1.404(2) . ?
N1 Ti1 2.1575(16) . ?
O1 Ti1 1.9242(17) . ?
O2 Ti1 1.8431(17) . ?

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
N2 C1 O1 122.6(2) . . ?
N2 C1 C2 119.98(19) . . ?
O1 C1 C2 117.47(19) . . ?
C7 C2 C3 118.6(2) . . ?
C7 C2 C1 121.7(2) . . ?
C3 C2 C1 119.7(2) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 Cl1 120.2(3) . . ?
C4 C5 Cl1 118.7(3) . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
N1 C8 C9 121.41(18) . . ?
N1 C8 C15 120.1(2) . . ?
C9 C8 C15 118.50(19) . . ?
C14 C9 C10 116.3(2) . . ?
C14 C9 C8 122.69(19) . . ?
C10 C9 C8 121.1(2) . . ?
C11 C10 C9 122.0(2) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C14 C13 118.3(2) . . ?
O2 C14 C9 120.5(2) . . ?
C13 C14 C9 121.2(2) . . ?
C8 N1 N2 114.90(17) . . ?
C8 N1 Ti1 131.06(15) . . ?
N2 N1 Ti1 114.02(12) . . ?
C1 N2 N1 109.38(17) . . ?
C1 O1 Ti1 119.56(14) . . ?
C14 O2 Ti1 142.45(15) . . ?
O2 Ti1 O2 92.50(11) 2 . ?
O2 Ti1 O1 92.85(8) 2 . ?
O2 Ti1 O1 155.50(7) . . ?
O2 Ti1 O1 155.49(7) 2 2 ?
O2 Ti1 O1 92.85(8) . 2 ?
O1 Ti1 O1 92.13(11) . 2 ?
O2 Ti1 N1 81.46(7) 2 2 ?
O2 Ti1 N1 110.95(7) . 2 ?
O1 Ti1 N1 93.49(7) . 2 ?
O1 Ti1 N1 74.29(7) 2 2 ?
O2 Ti1 N1 110.95(7) 2 . ?
O2 Ti1 N1 81.46(7) . . ?
O1 Ti1 N1 74.29(7) . . ?
O1 Ti1 N1 93.49(7) 2 . ?
N1 Ti1 N1 162.60(10) 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
N2 C1 C2 C7 15.0(3) . . . . ?
O1 C1 C2 C7 -165.3(2) . . . . ?
N2 C1 C2 C3 -164.3(2) . . . . ?
O1 C1 C2 C3 15.4(3) . . . . ?
C7 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 179.2(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C3 C4 C5 Cl1 178.3(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
Cl1 C5 C6 C7 -179.25(18) . . . . ?
C5 C6 C7 C2 0.9(4) . . . . ?
C3 C2 C7 C6 -0.9(4) . . . . ?
C1 C2 C7 C6 179.9(2) . . . . ?
N1 C8 C9 C14 3.0(3) . . . . ?
C15 C8 C9 C14 -176.3(2) . . . . ?
N1 C8 C9 C10 -176.5(2) . . . . ?
C15 C8 C9 C10 4.2(3) . . . . ?
C14 C9 C10 C11 0.6(4) . . . . ?
C8 C9 C10 C11 -179.9(2) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C10 C11 C12 C13 -1.5(5) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C12 C13 C14 O2 178.6(2) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?
C10 C9 C14 O2 -179.5(2) . . . . ?
C8 C9 C14 O2 1.1(3) . . . . ?
C10 C9 C14 C13 -0.8(3) . . . . ?
C8 C9 C14 C13 179.8(2) . . . . ?
C9 C8 N1 N2 176.83(18) . . . . ?
C15 C8 N1 N2 -3.9(3) . . . . ?
C9 C8 N1 Ti1 -1.8(3) . . . . ?
C15 C8 N1 Ti1 177.49(16) . . . . ?
O1 C1 N2 N1 -1.7(3) . . . . ?
C2 C1 N2 N1 177.98(18) . . . . ?
C8 N1 N2 C1 179.50(19) . . . . ?
Ti1 N1 N2 C1 -1.6(2) . . . . ?
N2 C1 O1 Ti1 4.8(3) . . . . ?
C2 C1 O1 Ti1 -174.92(14) . . . . ?
C13 C14 O2 Ti1 172.59(19) . . . . ?
C9 C14 O2 Ti1 -8.7(4) . . . . ?
C14 O2 Ti1 O2 118.7(3) . . . 2 ?
C14 O2 Ti1 O1 16.3(4) . . . . ?
C14 O2 Ti1 O1 -85.2(3) . . . 2 ?
C14 O2 Ti1 N1 -159.5(2) . . . 2 ?
C14 O2 Ti1 N1 7.9(3) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.056

